CA2531390A1 - Polarizing photochromic devices and methods of making the same - Google Patents
Polarizing photochromic devices and methods of making the same Download PDFInfo
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- CA2531390A1 CA2531390A1 CA002531390A CA2531390A CA2531390A1 CA 2531390 A1 CA2531390 A1 CA 2531390A1 CA 002531390 A CA002531390 A CA 002531390A CA 2531390 A CA2531390 A CA 2531390A CA 2531390 A1 CA2531390 A1 CA 2531390A1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/60—Pleochroic dyes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3016—Polarising elements involving passive liquid crystal elements
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
- Y10T428/24934—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including paper layer
Abstract
Various embodiments disclosed herein relate to optical elements comprising an at least partial coating having a first state and a second state connected to at least a portion of a substrate, the at least partial coating being adapted to switch from the first state to the second state in response to at least actinic radiation, to revert back to the first state in response to thermal energy, and to linearly polarize at least transmitted radiation in at least one of the first state and the second state. Other embodiments relate to optical elements comprising a substrate and at least one at least partially aligned photochromic-dichroic compound connected to at least a portion of the substrate and having an average absorption ratio greater than 2.3 in the activated state as determined according to CELL METHOD. Still other embodiments relate to security devices, liquid crystal cells and methods of making the same.
Claims (181)
1. An optical element comprising an at least partial coating having a first state and a second state connected to at least a portion of a substrate, the at least partial coating being adapted to switch from the first state to the second state in response to at least actinic radiation, to revert back to the first state in response to thermal energy, and to linearly polarize at least transmitted radiation in at least one of the first state and the second state.
2. The optical element of claim 1 wherein the optical element is chosen from ophthalmic elements, display elements, windows, mirrors, and active and passive liquid crystal cell elements.
3. The optical element of claim 2 wherein the ophthalmic element is chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses, and visors.
4. The optical element of claim 2 wherein the display element is chosen from screens, monitors, and security elements.
5. The optical element of claim 1 wherein the substrate is chosen from untinted substrates, tinted substrates, photochromic substrates, tinted-photochromic substrates, and linearly polarizing substrates.
6. The optical element of claim 1 wherein the at least partial coating having the first state and the second state is adapted to be non-polarizing in a first state and linearly polarizing in a second state.
7. The optical element of claim 6 wherein the at least partial coating having the first state and the second state is adapted to linearly polarize at least ultraviolet radiation in the second state.
8. The optical element of claim 6 wherein the at least partial coating having the first state and the second state is adapted to linearly polarize at least visible radiation in the second state.
9. The optical element of claim 1 wherein the at least partial coating having the first state and the second state is adapted to be clear in the first state and colored in the second state.
10. The optical element of claim 1 wherein the at least partial coating having the first state and the second state is adapted to have a first color in the first state and a second color in the second state.
11. The optical element of claim 1 wherein the at least partial coating having the first state and the second state is adapted to linearly polarize visible radiation in both the first state and the second state.
12. The optical element of claim 1 wherein the at least partial coating having the first state and the second state is adapted to linearly polarize ultraviolet radiation in the first state and to linearly polarize visible radiation in the second state.
13. The optical element of claim 1 wherein the at least partial coating having the first state and the second state has an average absorption ratio of at least 1.5 in at least one state.
14. The optical element of claim 14 wherein the at least partial coating having the first state and the second state has an average absorption ratio ranging from 1.5 to 50 in at least one state.
15. The optical element of claim 1 wherein the at least partial coating having the first state and the second state comprises at least one at least partially aligned photochromic-dichroic compound.
16. The optical element of claim 15 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio of at least 1.5 in an activated state as determined according to CELL METHOD.
17. The optical element of claim 15 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
18. The optical element of claim 15 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio ranging from 1.5 to 50 in an activated state as determined according to CELL
METHOD.
METHOD.
19. The optical element of claim 15 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio ranging from 2.5 to 50 in an activated state as determined according to CELL
METHOD.
METHOD.
20. The optical element of claim 15 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio ranging from 3 to 30 in an activated state as determined according to CELL
METHOD.
METHOD.
21. The optical element of claim 15 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio ranging from 4 to 20 in an activated state as determined according to CELL
METHOD.
METHOD.
22. The optical element of claim 15 wherein the at least partial coating having the first state and the second state comprises at least two at least partially aligned thermally reversible photochromic-dichroic compounds, wherein the at least two at least partially aligned photochromic-dichroic compounds have at least one of: complementary absorption spectra and complementary linear polarization states.
23. The optical element of claim 1 wherein the at least partial coating having the first state and the second state comprises a phase-separated polymer comprising an at least partially ordered matrix phase and an at least partially ordered guest phase, wherein at least a portion of the at least partially ordered guest phase comprises at least one thermally reversible photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least partially ordered guest phase.
24. The optical element of claim 1 wherein the at least partial coating having the first state and the second state comprises an interpenetrating polymer network comprising at least one at least partially ordered anisotropic material and at least one polymeric material, wherein at least a portion of the at least partially ordered anisotropic material comprises at least one thermally reversible photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least partially ordered anisotropic material.
25. The optical element of claim 1 wherein the at least partial coating having the first state and the second state further comprises at least one additive chosen from dyes, alignment promoters, kinetic enhancing additives, photoinitiators, thermal initiators, polymerization inhibitors, solvents, light stabilizers, heat stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, and adhesion promoters.
26. The optical element of claim 1 wherein the at least partial coating having the first state and the second state further comprises at least one dichroic material chosen from azomethines, indigoids, thioindigoids, merocyanines, indans, quinophthalonic dyes, perylenes, phthaloperines, triphenodioxazines, indoloquinoxalines, imidazo-triazines, tetrazines, azo and (poly)azo dyes, benzoquinones, naphthoquinones, anthroquinone and (poly)anthroquinones, anthropyrimidinones, iodine and iodates.
27. The optical element of claim 1 further comprising at least one primer coating between the at least a portion of the at least one surface of the substrate and the at least partial coating having the first state and the second state connected to the at least a portion of the at least one surface of the substrate.
28. The optical element of claim 1 further comprising at least one additional at least partial coating chosen from photochromic coatings, anti-reflective coatings, linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, transitional coatings, primer coatings, and protective coatings on at least a portion of a surface of the substrate.
29. An optical element comprising:
a substrate; and at least one at least partially aligned thermally reversible photochromic-dichroic compound connected to at least a portion of the substrate and having an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
a substrate; and at least one at least partially aligned thermally reversible photochromic-dichroic compound connected to at least a portion of the substrate and having an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
30. The optical element of claim 29 wherein the optical element is chosen from ophthalmic elements, display elements, windows, mirrors, and active and passive liquid crystal cell elements.
31. The optical element of claim 30 wherein the ophthalmic element is chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses, and visors.
32. The optical element of claim 30 wherein the display element is chosen from screens, monitors, and security elements.
33. The optical element of claim 29 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio ranging from 2.5 to 50 in the activated state as determined according to CELL
METHOD.
METHOD.
34. The optical element of claim 29 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio ranging from 3 to 30 in the activated state as determined according to CELL
METHOD.
METHOD.
35. The optical element of claim 29 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio ranging from 4 to 20 in the activated state as determined according to CELL
METHOD.
METHOD.
36. The optical element of claim 29 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound is chosen from:
(1) 3-phenyl-3-(4-(4-(3-(1-(2-hydroxyethyl)piperidin-4-yl)propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(2) 3-phenyl-3-(4-(4-(4-butyl-phenylcarbamoyl)-piperidin-1-yl) phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(3) 3-phenyl-3-(4-([1,4']bipiperidinyl-1'-yl)phenyl)-13,13-dimethyl-6-methoxy-([1,4']bipiperidinyl-1'-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(4) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)-piperidin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(5) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(6) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5 dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(7) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(8) 3-phenyl-3-(4-(4-phenylpiperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]
naphtho[1,2-b]pyran;
(9) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4 hexyloxyphenylcarbonyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(10) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(2-fluorobenzoyloxy)benzoyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(11) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-(4-(4 hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(12) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)benzoyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(13) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)benzoyloxy)benzoyloxy)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(14) 3-phenyl-3-(4-(4-methoxyphenyl)-piperazin-1-yl))phenyl)-13,13-dimethyl-6-methoxy-7 (4-(4-(3-phenylprop-2-ynoyloxy)phenyl)piperazin-1-yl)-indeno[2',3':3,4)naphtho[1,2-b]pyran;
(15) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-hydroxy-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(16) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxy]-13-ethyl-6-methoxy-7-(4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperadin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(17) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13-ethyl-13-hydroxy-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(18) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(3-phenyl 3-{4-(pyrrolidin-1-yl)phenyl}-13,13-dimethyl-6-methoxy-indeno[2',3':3,4]naphtho[1,2-b]pyran-7-yl)-piperadin-1-yl)oxycarbonyl)phenyl)phenyl)cabonyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(19) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-methoxycarbonyl-3H-naphtho[2,1-b]pyran;
(20) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-hydroxycarbonyl-3H-naphtho[2,1-b]pyran;
(21) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(4-phenyl-(phen-1-oxy)carbonyl)-3H-naphtho[2,1-b]pyran;
(22) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(N-(4-((4-dimethylamino)phenyl)diazenyl)phenyl)carbamoyl-3H-naphtho[2,1-b]pyran;
(23) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzofuro[3',2':7,8]
benzo[b]pyran;
(24) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzothieno[3',2':7,8]
benzo[b]pyran;
(25) 7-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy)-2-phenyl-2-(4-pyrrolid in-1-yl-phenyl)-6-methoxycarbonyl-2H-benzo[b] pyran;
(26) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-methoxycarbonyl-2H-naphtho[1,2-b]pyran;
(27) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-butyl-phenyl))carbamoyl-2H-naphtho[1,2-b]pyran;
(28) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(29) 1,3,3-trimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine];
(30) 1,3,3-trimethyl-6'-(4-[N-(4-butylphenyl)carbamoyl]-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(31) 1,3,3-trimethyl-6'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(32) 1,3,3-trimethyl-6'-(4-(4-hydroxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(33) 1,3,3,5,6-pentamethyl-7'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(34) 1,3-diethyl-3-methyl-5-methoxy-6'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(35) 1,3-diethyl-3-methyl-5-[4-(4-pentadecafluoroheptyloxy-phenylcarbamoyl)-benzyloxy]-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine];
(36) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(37) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-fluoantheno[1,2-b]pyran;
(38) 2-phenyl-2-{4-(4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-11-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl)-2H-fluoantheno[1,2-b]pyran;
(39) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(40) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-7'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(41) 1,3-diethyl-3-methyl-5-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy}phenyl)-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(42) 1-butyl-3-ethyl-3-methyl-5-methoxy-7'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(43) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-methoxycarbonyl-6-methyl-2H-9-(4-(4-propylphenyl)carbonyloxy)phenyl)(1,2-dihydro-9H-dioxolano[4',5':6,7] naphtho[1,2-b]pyran;
(44) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-hydroxy-6-methoxy-7-(4-(4-propylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":6,7][indeno[2',3':3,4]]naphtho[1,2-b]pyran;
(45) 3-phenyl-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-13-hydroxy-methoxy-7-(4-(4-hexylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":5,6][indeno[2',3':3,4]] naphtho[1,2-b]pyran;
(46) 4-(4-((4-cyclohexylidene-1-ethyl-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(47) 4-(4-((4-adamantan-2-ylidene-1-(4-(4-hexylphenyl)carbonyloxy)phenyl)-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(48) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl (4-propyl)benzoate;
(49) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(50) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy}phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(51) 4-(4-methyl-5,7-dioxo-6-(4-(4-(4-propylphenyl)piperazinyl)phenyl)spiro[8,7a-dihydrothiapheno[4,5-f]isoindole-8,2'-adamentane]-2-yl)phenyl(4-propyl)phenyl benzoate;
(52) N-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl -6,7-dihydro-4-methyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]decane);
(53) N-cyanomethyl-6,7-dihydro-2-(4-(4-(4-propylphenyl)piperazinyl)phenyl)-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(54) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(55) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-cyclopropyl spiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(56) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-cyclopropyl spiro(5,6-benzo[b]furodicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(57) N-cyanomethyl-6,7-dihydro-4-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(58) N-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyl -6,7-dihydro-2-(4-methoxyphenyl)phenyl-4-methylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane);
(59) N-cyanomethyl-2-(4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl -6,7-dihydro-4-cyclopropylspiro(5,6-benzo[b]
thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]decane);
(60) 6,7-dihydro-N-methoxycarbonylmethyl-4-(4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane); and (61) 3-phenyl-3-(4-pyrrolidinylphenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-(6-(4-(4-(4-nonylphenylcabonyloxy)phenyl)oxycarbonyl)phenoxy)hexyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran.
(1) 3-phenyl-3-(4-(4-(3-(1-(2-hydroxyethyl)piperidin-4-yl)propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(2) 3-phenyl-3-(4-(4-(4-butyl-phenylcarbamoyl)-piperidin-1-yl) phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(3) 3-phenyl-3-(4-([1,4']bipiperidinyl-1'-yl)phenyl)-13,13-dimethyl-6-methoxy-([1,4']bipiperidinyl-1'-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(4) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)-piperidin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(5) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(6) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5 dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(7) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(8) 3-phenyl-3-(4-(4-phenylpiperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]
naphtho[1,2-b]pyran;
(9) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4 hexyloxyphenylcarbonyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(10) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(2-fluorobenzoyloxy)benzoyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(11) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-(4-(4 hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(12) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)benzoyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(13) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)benzoyloxy)benzoyloxy)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(14) 3-phenyl-3-(4-(4-methoxyphenyl)-piperazin-1-yl))phenyl)-13,13-dimethyl-6-methoxy-7 (4-(4-(3-phenylprop-2-ynoyloxy)phenyl)piperazin-1-yl)-indeno[2',3':3,4)naphtho[1,2-b]pyran;
(15) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-hydroxy-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(16) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxy]-13-ethyl-6-methoxy-7-(4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperadin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(17) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13-ethyl-13-hydroxy-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(18) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(3-phenyl 3-{4-(pyrrolidin-1-yl)phenyl}-13,13-dimethyl-6-methoxy-indeno[2',3':3,4]naphtho[1,2-b]pyran-7-yl)-piperadin-1-yl)oxycarbonyl)phenyl)phenyl)cabonyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(19) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-methoxycarbonyl-3H-naphtho[2,1-b]pyran;
(20) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-hydroxycarbonyl-3H-naphtho[2,1-b]pyran;
(21) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(4-phenyl-(phen-1-oxy)carbonyl)-3H-naphtho[2,1-b]pyran;
(22) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(N-(4-((4-dimethylamino)phenyl)diazenyl)phenyl)carbamoyl-3H-naphtho[2,1-b]pyran;
(23) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzofuro[3',2':7,8]
benzo[b]pyran;
(24) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzothieno[3',2':7,8]
benzo[b]pyran;
(25) 7-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy)-2-phenyl-2-(4-pyrrolid in-1-yl-phenyl)-6-methoxycarbonyl-2H-benzo[b] pyran;
(26) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-methoxycarbonyl-2H-naphtho[1,2-b]pyran;
(27) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-butyl-phenyl))carbamoyl-2H-naphtho[1,2-b]pyran;
(28) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(29) 1,3,3-trimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine];
(30) 1,3,3-trimethyl-6'-(4-[N-(4-butylphenyl)carbamoyl]-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(31) 1,3,3-trimethyl-6'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(32) 1,3,3-trimethyl-6'-(4-(4-hydroxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(33) 1,3,3,5,6-pentamethyl-7'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(34) 1,3-diethyl-3-methyl-5-methoxy-6'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(35) 1,3-diethyl-3-methyl-5-[4-(4-pentadecafluoroheptyloxy-phenylcarbamoyl)-benzyloxy]-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine];
(36) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(37) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-fluoantheno[1,2-b]pyran;
(38) 2-phenyl-2-{4-(4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-11-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl)-2H-fluoantheno[1,2-b]pyran;
(39) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(40) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-7'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(41) 1,3-diethyl-3-methyl-5-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy}phenyl)-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(42) 1-butyl-3-ethyl-3-methyl-5-methoxy-7'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(43) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-methoxycarbonyl-6-methyl-2H-9-(4-(4-propylphenyl)carbonyloxy)phenyl)(1,2-dihydro-9H-dioxolano[4',5':6,7] naphtho[1,2-b]pyran;
(44) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-hydroxy-6-methoxy-7-(4-(4-propylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":6,7][indeno[2',3':3,4]]naphtho[1,2-b]pyran;
(45) 3-phenyl-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-13-hydroxy-methoxy-7-(4-(4-hexylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":5,6][indeno[2',3':3,4]] naphtho[1,2-b]pyran;
(46) 4-(4-((4-cyclohexylidene-1-ethyl-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(47) 4-(4-((4-adamantan-2-ylidene-1-(4-(4-hexylphenyl)carbonyloxy)phenyl)-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(48) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl (4-propyl)benzoate;
(49) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(50) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy}phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(51) 4-(4-methyl-5,7-dioxo-6-(4-(4-(4-propylphenyl)piperazinyl)phenyl)spiro[8,7a-dihydrothiapheno[4,5-f]isoindole-8,2'-adamentane]-2-yl)phenyl(4-propyl)phenyl benzoate;
(52) N-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl -6,7-dihydro-4-methyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]decane);
(53) N-cyanomethyl-6,7-dihydro-2-(4-(4-(4-propylphenyl)piperazinyl)phenyl)-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(54) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(55) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-cyclopropyl spiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(56) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-cyclopropyl spiro(5,6-benzo[b]furodicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(57) N-cyanomethyl-6,7-dihydro-4-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(58) N-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyl -6,7-dihydro-2-(4-methoxyphenyl)phenyl-4-methylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane);
(59) N-cyanomethyl-2-(4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl -6,7-dihydro-4-cyclopropylspiro(5,6-benzo[b]
thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]decane);
(60) 6,7-dihydro-N-methoxycarbonylmethyl-4-(4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane); and (61) 3-phenyl-3-(4-pyrrolidinylphenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-(6-(4-(4-(4-nonylphenylcabonyloxy)phenyl)oxycarbonyl)phenoxy)hexyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran.
37. The optical element of claim 29 further comprising at least one orientation facility having at least a first general direction connected to at least a portion of the substrate.
38. The optical element of claim 37 wherein the at least a portion of the at least one at least partially aligned thermally reversible photochromic-dichroic compound is at least partially aligned such that a long-axis of the thermally reversible photochromic-dichroic compound in the activated state is generally parallel to at least the first general direction of the at least one orientation facility.
39. The optical element of claim 38 wherein the at least a portion of the at least one at least partially aligned thermally reversible photochromic-dichroic compound is bound to the at least a portion of the at least one orientation facility.
40. The optical element of claim 37 wherein the at least one orientation facility comprises a plurality of at least partially ordered regions and each region has a general direction that is the same or different from the remaining regions.
41. The optical element of claim 37 wherein the at least one orientation facility comprises at least one of: an at least partial coating comprising an at least partially ordered alignment medium, an at least partially ordered polymeric sheet, an at least partially treated surface, and a Langmuir-Blodgett film.
42. The optical element of claim 37 wherein the at least one orientation facility comprises an at least partial coating comprising an at least partially ordered alignment medium, and the at least one at least partially aligned thermally reversible photochromic-dichroic compound is connected to at least a portion of the at least one at least partial coating comprising the at least partially ordered alignment medium.
43. The optical element of claim 42 wherein the alignment medium is chosen from photo-orientation materials, rubbed-orientation materials, and liquid crystal materials.
44. The optical element of claim 43 wherein the photo-orientation material is a photo-orientable polymer network chosen from azobenzene derivatives, cinnamic acid derivatives, coumarine derivatives, ferulic acid derivatives, and polyimides.
45. The optical element of claim 43 wherein the rubbed-orientation material is chosen from (poly)imides, (poly)siloxanes, (poly)acrylates, and (poly)coumarines.
46. The optical element of claim 43 wherein the liquid crystal material is chosen from liquid crystal polymers, liquid crystal pre-polymers, liquid crystal monomers, and liquid crystal mesogens.
47. The optical element of claim 42 wherein an at least partial coating comprising an at least partially ordered alignment transfer material is connected to at least a portion of the at least partial coating comprising the at least partially ordered alignment medium, and the at least one at least partially aligned thermally reversible photochromic-dichroic compound is connected to at least a portion of the at least one at least partial coating comprising the at least partially ordered alignment transfer material.
48. The optical element of claim 47 wherein the alignment transfer material is a liquid crystal material chosen from at least one of liquid crystal polymers, liquid crystal pre-polymers, liquid crystal monomers, and liquid crystal mesogens.
49. The optical element of claim 48 wherein the liquid crystal material is cross-linkable.
50. The optical element of claim 48 wherein the liquid crystal material is photocross-linkable.
51. The optical element of claim 47 wherein the alignment transfer material is a liquid crystal material having at least one functional group chosen from acrylates, methacrylates, allyl, allyl ethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, and vinyl ethers.
52. The optical element of claim 29 further comprising at least one at least partially ordered anisotropic material connected to at least a portion of the substrate.
53. The optical element of claim 52 wherein the at least a portion of the at least one at least partially aligned thermally reversible photochromic-dichroic compound is at least partially aligned with the at least partially ordered anisotropic material.
54. The optical element of claim 53 wherein the at least a portion of the at least one at least partially aligned thermally reversible photochromic-dichroic compound is bound to the at least partially ordered anisotropic material.
55. The optical element of claim 52 wherein the at least one anisotropic material is a liquid crystal material chosen from at least one of liquid crystal polymers, liquid crystal pre-polymers, liquid crystal monomers, and liquid crystal mesogens.
56. The optical element of claim 55 wherein the liquid crystal material is cross-linkable.
57. The optical element of claim 55 wherein the liquid crystal material is photocross-linkable.
58. The optical element of claim 52 wherein the anisotropic material is a liquid crystal material having at least one functional group chosen from acrylate, methacrylate, allyl, allyl ether, alkyne, amine, anhydride, epoxide, hydroxide, isocyanate, blocked isocyanate, siloxane, thiocyanate, thiol, urea, vinyl, and vinyl ether.
59. The optical element of claim 52 wherein the at least one at least partially ordered anisotropic material and the at least one at least partially aligned thermally reversible photochromic-dichroic compound form an at least partial coating connected to at least a portion of the substrate.
60. The optical element of claim 59 further comprising at least one orientation facility positioned between the at least partial coating formed by the at least one at least partially ordered anisotropic material and the at least one at least partially aligned thermally reversible photochromic-dichroic compound and at least a portion of the substrate.
61. An optical element comprising:
a substrate;
at least one at least partially ordered orientation facility connected to at least a portion of the substrate; and an at least partial coating connected to at least a portion of the at least partially ordered orientation facility, the at least partial coating comprising at least one at least partially ordered anisotropic material and at least one photochromic-dichroic compound is at least partially aligned with at least a portion of the at least partially ordered anisotropic material.
a substrate;
at least one at least partially ordered orientation facility connected to at least a portion of the substrate; and an at least partial coating connected to at least a portion of the at least partially ordered orientation facility, the at least partial coating comprising at least one at least partially ordered anisotropic material and at least one photochromic-dichroic compound is at least partially aligned with at least a portion of the at least partially ordered anisotropic material.
62. The optical element of claim 61 wherein the optical element is chosen from ophthalmic elements, display elements, windows, mirrors, and active and passive liquid crystal cell elements.
63. The optical element of claim 62 wherein the ophthalmic element is chosen from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses, and visors.
64. The optical element of claim 62 wherein the display element is chosen from screens, monitors, and security elements.
65. The optical element of claim 61 wherein the at least one orientation facility has at least a first general direction.
66. The optical element of claim 61 wherein the at least one orientation facility comprises at least one of: an at least partial coating comprising an at least partially ordered alignment medium, an at least partially ordered polymeric sheet, an at least partially treated surface, and a Langmuir-Blodgett film.
67. The optical element of claim 61 wherein the at least one orientation facility comprises an at least partial coating comprising an at least partially ordered alignment medium.
68. The optical element of claim 67 wherein the alignment medium is chosen from photo-orientation materials, rubbed-orientation materials, and liquid crystal materials.
69. The optical element of claim 61 further comprising at least one at least partial coating comprising an at least partially ordered alignment transfer material between the at least a portion of the at least one at least partially ordered orientation facility and the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound.
70. The optical element of claim 61 wherein the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound has a first state and a second state, and is adapted to switch from the first state to the second state in response to actinic radiation and to revert back to the first state in response to thermal energy.
71. The optical element of claim 70 wherein the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound is adapted to be clear in the first state and colored in the second state.
72. The optical element of claim 70 wherein the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound is adapted to have a first color in the first state and a second color in the second state.
73. The optical element of claim 70 wherein the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound is adapted to be non-polarizing in the first state and linearly polarizing in the second state.
74. The optical element of claim 70 wherein the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound is adapted to linearly polarize ultraviolet radiation in the first state and at least visible radiation in the second state.
75. The optical element of claim 70 wherein the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound has an average absorption ratio of at least 1.5 in at least one state.
76. The optical element of claim 70 wherein the at least one at least partially ordered anisotropic material is adapted to allow the at least one photochromic-dichroic compound to switch between the first state and the second state at a desired rate.
77. The optical element of claim 61 wherein at least a portion of the at least one photochromic-dichroic compound is bound to at least a portion of the at least one at least partially ordered anisotropic material.
78. The optical element of claim 61 wherein the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound is a phase-separated polymer coating.
79. The optical element of claim 78 wherein the phase-separated polymer coating comprises:
a matrix phase, and a guest phase comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound distributed within the matrix phase.
a matrix phase, and a guest phase comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound distributed within the matrix phase.
80. The optical element of claim 79 wherein the matrix phase comprises at liquid crystal polymer.
81. The optical element of claim 61 wherein the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound is an interpenetrating polymer network coating.
82. The optical element of claim 81 wherein the interpenetrating polymer network coating comprises a polymeric material that interpenetrates with at least a portion of the at least one at least partially ordered anisotropic material.
83. The optical element of claim 61 wherein the at least one photochromic-dichroic compound has an average absorption ratio of at least 1.5 in an activated state as determined according to CELL METHOD.
84. The optical element of claim 61 wherein the at least one photochromic-dichroic compound has an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
85. The optical element of claim 61 wherein the at least one photochromic-dichroic compound has an average absorption ratio ranging from 2.5 to 50 in an activated state as determined according to CELL METHOD.
86. The optical element of claim 61 wherein the at least one photochromic-dichroic compound is chosen from:
(1) 3-phenyl-3-(4-(4-(3-piperidin-4-yl-propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]-naphtho(1,2-b]pyran;
(2) 3-phenyl-3-(4-(4-(3-(1-(2-hydroxyethyl)piperidin-4-yl)propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(3) 3-phenyl-3-(4-(4-(4-butyl-phenylcarbamoyl)-piperidin-1-yl) phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(4) 3-phenyl-3-(4-([1,4']bipiperidinyl-1'-yl)phenyl)-13,13-dimethyl-6-methoxy-([1,4']bipiperidinyl-1'-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(5) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)-piperidin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(6) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(7) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(8) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(9) 3-phenyl-3-(4-(4-phenylpiperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]
naphtho[1,2-b]pyran;
(10) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexyloxyphenylcarbonyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2 b]pyran;
(11) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(2-fluorobenzoyloxy)benzoyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(12) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(13) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)benzoyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(14) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)benzoyloxy)benzoyloxy)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(15) 3-phenyl-3-(4-(4-methoxyphenyl)-piperazin-1-yl))phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(3-phenylprop-2-ynoyloxy)phenyl)piperazin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(16) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-hydroxy-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(17) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxy]-13-ethyl-6-methoxy-7-(4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]
phenanthren-3-yloxycarbonyloxy]-piperadin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(18) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13-ethyl-13-hydroxy-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(19) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl}-13,13-dimethyl-6-methoxy-indeno[2',3':3,4]naphtho[1,2-b]pyran-7-yl)-piperadin-1-yl)oxycarbonyl)phenyl)phenyl)cabonyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(20) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-methoxycarbonyl-3H-naphtho[2,1-b]pyran;
(21) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-hydroxycarbonyl-3H-naphtho[2,1-b]pyran;
(22) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(4-phenyl-(phen-1-oxy)carbonyl)-3H-naphtho[2,1-b]pyran;
(23) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(N-(4-((4-dimethylamino)phenyl)diazenyl)phenyl)carbamoyl-3H-naphtho[2,1-b]pyran;
(24) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzofuro[3',2':7,8]
benzo[b]pyran;
(25) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzothieno[3',2':7,8]
benzo[b]pyran;
(26) 7-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}-2-phenyl-2-(4-pyrrolidin-1-yl-phenyl)-6-methoxycarbonyl-2H-benzo[b]pyran;
(27) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-methoxycarbonyl-2H-naphtho[1,2-b]pyran;
(28) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-butyl-phenyl))carbamoyl-2H-naphtho[1,2-b]pyran;
(29) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(30) 1,3,3-trimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine];
(31) 1,3,3-trimethyl-6'-(4-[N-(4-butylphenyl)carbamoyl]-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(32) 1,3,3-trimethyl-6'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(33) 1,3,3-trimethyl-6'-(4-(4-hydroxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(34) 1,3,3,5,6-pentamethyl-7'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(35) 1,3-diethyl-3-methyl-5-methoxy-6'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(36) 1,3-diethyl-3-methyl-5-[4-(4-pentadecafluoroheptyloxy-phenylcarbamoyl)-benzyloxy]-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-naphtho[2,1-b](1,4]oxazine];
(37) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(38) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-fluoantheno[1,2-b]pyran;
(39) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl)-5-carbomethoxy-11-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl)-2H-fluoantheno[1,2-b]pyran;
(40) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(41) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-7'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(42) 1,3-diethyl-3-methyl-5-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy}phenyl)-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(43) 1-butyl-3-ethyl-3-methyl-5-methoxy-7'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(44) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-methoxycarbonyl-6-methyl-2H-9-(4-(4-propylphenyl)carbonyloxy)phenyl)(1,2-dihydro-9H-dioxolano[4',5':6,7] naphtho[1,2-b]pyran;
(45) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-hydroxy-6-methoxy-7-(4-(4-propylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":6,7][indeno[2',3':3,4]]naphtho[1,2-b]pyran;
(46) 3-phenyl-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-13-hydroxy-methoxy-7-(4-(4-hexylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":5,6][indeno[2',3':3,4]] naphtho[1,2-b]pyran;
(47) 4-(4-((4-cyclohexylidene-1-ethyl-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(48) 4-(4-((4-adamantan-2-ylidene-1-(4-(4-hexylphenyl)carbonyloxy)phenyl)-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(49) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl (4-propyl)benzoate;
(50) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(51) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy)phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(52) 4-(4-methyl-5,7-dioxo-6-(4-(4-(4-propylphenyl)piperazinyl)phenyl)spiro[8,7a-dihydrothiapheno[4,5-f]isoindole-8,2'-adamentane]-2-yl)phenyl (4-propyl) phenyl benzoate;
(53) N-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl -6,7-dihydro-4-methyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]decane);
(54) N-cyanomethyl-6,7-dihydro-2-(4-(4-(4-propylphenyl)piperazinyl)phenyl)-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(55) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(56) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4 cyclopropyl spiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(57) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4 cyclopropyl spiro(5,6-benzo[b]furodicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(58) N-cyanomethyl-6,7-dihydro-4-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl 2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(59) N-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyl -6,7-dihydro-2-(4-methoxyphenyl)phenyl-4-methylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane);
(60) N-cyanomethyl-2-(4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl -6,7-dihydro-4-cyclopropylspiro(5,6-benzo[b]
thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1 ]decane);
(61) 6,7-dihydro-N-methoxycarbonylmethyl-4-(4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane); and (62) 3-phenyl-3-(4-pyrrolidinylphenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-(6-(4-(4-(4-nonylphenylcabonyloxy)phenyl)oxycarbonyl)phenoxy)hexyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran.
(1) 3-phenyl-3-(4-(4-(3-piperidin-4-yl-propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]-naphtho(1,2-b]pyran;
(2) 3-phenyl-3-(4-(4-(3-(1-(2-hydroxyethyl)piperidin-4-yl)propyl)piperidino)phenyl)-13,13-dimethyl-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(3) 3-phenyl-3-(4-(4-(4-butyl-phenylcarbamoyl)-piperidin-1-yl) phenyl)-13,13-dimethyl-6-methoxy-7-(4-phenyl-piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(4) 3-phenyl-3-(4-([1,4']bipiperidinyl-1'-yl)phenyl)-13,13-dimethyl-6-methoxy-([1,4']bipiperidinyl-1'-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(5) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)-piperidin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(6) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(7) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(8) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13,13-dimethyl-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(9) 3-phenyl-3-(4-(4-phenylpiperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4'-octyloxy-biphenyl-4-carbonyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]
naphtho[1,2-b]pyran;
(10) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexyloxyphenylcarbonyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2 b]pyran;
(11) 3-phenyl-3-(4-(4-phenyl-piperazin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(2-fluorobenzoyloxy)benzoyloxy)phenyl) piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(12) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13-hydroxy-13-ethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(13) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-hexylbenzoyloxy)benzoyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(14) 3-phenyl-3-(4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)benzoyloxy)benzoyloxy)indeno[2',3':3,4] naphtho[1,2-b]pyran;
(15) 3-phenyl-3-(4-(4-methoxyphenyl)-piperazin-1-yl))phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(3-phenylprop-2-ynoyloxy)phenyl)piperazin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(16) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-hydroxy-6-methoxy-7-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(17) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxy]-13-ethyl-6-methoxy-7-(4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]
phenanthren-3-yloxycarbonyloxy]-piperadin-1-yl)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(18) 3-phenyl-3-(4-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy]-piperidin-1-yl}-phenyl)-13-ethyl-13-hydroxy-6-methoxy-7-{4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy]-piperidin-1-yl}-)indeno[2',3':3,4]naphtho[1,2-b]pyran;
(19) 3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(3-phenyl-3-{4-(pyrrolidin-1-yl)phenyl}-13,13-dimethyl-6-methoxy-indeno[2',3':3,4]naphtho[1,2-b]pyran-7-yl)-piperadin-1-yl)oxycarbonyl)phenyl)phenyl)cabonyloxy)-indeno[2',3':3,4]naphtho[1,2-b]pyran;
(20) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-methoxycarbonyl-3H-naphtho[2,1-b]pyran;
(21) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-hydroxycarbonyl-3H-naphtho[2,1-b]pyran;
(22) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(4-phenyl-(phen-1-oxy)carbonyl)-3H-naphtho[2,1-b]pyran;
(23) 3-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-3-phenyl-7-(N-(4-((4-dimethylamino)phenyl)diazenyl)phenyl)carbamoyl-3H-naphtho[2,1-b]pyran;
(24) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzofuro[3',2':7,8]
benzo[b]pyran;
(25) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-benzothieno[3',2':7,8]
benzo[b]pyran;
(26) 7-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}-2-phenyl-2-(4-pyrrolidin-1-yl-phenyl)-6-methoxycarbonyl-2H-benzo[b]pyran;
(27) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-methoxycarbonyl-2H-naphtho[1,2-b]pyran;
(28) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-butyl-phenyl))carbamoyl-2H-naphtho[1,2-b]pyran;
(29) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-9-hydroxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(30) 1,3,3-trimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine];
(31) 1,3,3-trimethyl-6'-(4-[N-(4-butylphenyl)carbamoyl]-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(32) 1,3,3-trimethyl-6'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(33) 1,3,3-trimethyl-6'-(4-(4-hydroxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(34) 1,3,3,5,6-pentamethyl-7'-(4-(4-methoxyphenyl)piperazin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(35) 1,3-diethyl-3-methyl-5-methoxy-6'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(36) 1,3-diethyl-3-methyl-5-[4-(4-pentadecafluoroheptyloxy-phenylcarbamoyl)-benzyloxy]-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-naphtho[2,1-b](1,4]oxazine];
(37) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-naphtho[1,2-b]pyran;
(38) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-carbomethoxy-8-(N-(4-phenyl)phenyl) carbamoyl-2H-fluoantheno[1,2-b]pyran;
(39) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl)-5-carbomethoxy-11-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl)-2H-fluoantheno[1,2-b]pyran;
(40) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-6'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(41) 1-(4-carboxybutyl)-6-(4-(4-propylphenyl)carbonyloxy)phenyl)-3,3-dimethyl-7'-(4-ethoxycarbonyl)-piperidin-1-yl)-spiro[(1,2-dihydro-9H-dioxolano[4',5':6,7]indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(42) 1,3-diethyl-3-methyl-5-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy}phenyl)-6'-(4-(4'-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[2,1-b][1,4]oxazine];
(43) 1-butyl-3-ethyl-3-methyl-5-methoxy-7'-(4-(4'-Hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl)-spiro[indoline-2,3'-3H-naphtho[1,2-b][1,4]oxazine];
(44) 2-phenyl-2-{4-[4-(4-methoxy-phenyl)-piperazin-1-yl]-phenyl}-5-methoxycarbonyl-6-methyl-2H-9-(4-(4-propylphenyl)carbonyloxy)phenyl)(1,2-dihydro-9H-dioxolano[4',5':6,7] naphtho[1,2-b]pyran;
(45) 3-(4-methoxyphenyl)-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-hydroxy-6-methoxy-7-(4-(4-propylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":6,7][indeno[2',3':3,4]]naphtho[1,2-b]pyran;
(46) 3-phenyl-3-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)-13-ethyl-13-hydroxy-methoxy-7-(4-(4-hexylphenyl)carbonyloxy)phenyl)-[1,2-dihydro-9H-dioxolano[4",5":5,6][indeno[2',3':3,4]] naphtho[1,2-b]pyran;
(47) 4-(4-((4-cyclohexylidene-1-ethyl-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(48) 4-(4-((4-adamantan-2-ylidene-1-(4-(4-hexylphenyl)carbonyloxy)phenyl)-2,5-dioxopyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl-(4-propyl)benzoate;
(49) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-2-thienyl)phenyl (4-propyl)benzoate;
(50) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-(4-(4-propylphenyl)piperazinyl)phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(51) 4-(4-((4-adamantan-2-ylidene-2,5-dioxo-1-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-yloxycarbonyloxy)phenyl)pyrrolin-3-ylidene)ethyl)-1-methylpyrrol-2-yl)phenyl (4-propyl)benzoate;
(52) 4-(4-methyl-5,7-dioxo-6-(4-(4-(4-propylphenyl)piperazinyl)phenyl)spiro[8,7a-dihydrothiapheno[4,5-f]isoindole-8,2'-adamentane]-2-yl)phenyl (4-propyl) phenyl benzoate;
(53) N-(4-{17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy}phenyl -6,7-dihydro-4-methyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]decane);
(54) N-cyanomethyl-6,7-dihydro-2-(4-(4-(4-propylphenyl)piperazinyl)phenyl)-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(55) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4-methylspiro(5,6- benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(56) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4 cyclopropyl spiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(57) N-phenylethyl-6,7-dihydro-2-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl-4 cyclopropyl spiro(5,6-benzo[b]furodicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(58) N-cyanomethyl-6,7-dihydro-4-(4-(4-(4-hexylbenzoyloxy)phenyl)piperazin-1-yl)phenyl 2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1]
decane);
(59) N-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyl -6,7-dihydro-2-(4-methoxyphenyl)phenyl-4-methylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane);
(60) N-cyanomethyl-2-(4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl -6,7-dihydro-4-cyclopropylspiro(5,6-benzo[b]
thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1 ]decane);
(61) 6,7-dihydro-N-methoxycarbonylmethyl-4-(4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl-2-phenylspiro(5,6-benzo[b]thiophenedicarboxyimide-7,2-tricyclo[3.3.1.1] decane); and (62) 3-phenyl-3-(4-pyrrolidinylphenyl)-13,13-dimethyl-6-methoxy-7-(4-(4-(4-(4-(6-(4-(4-(4-nonylphenylcabonyloxy)phenyl)oxycarbonyl)phenoxy)hexyloxy)phenyl)piperazin-1-yl)indeno[2',3':3,4] naphtho[1,2-b]pyran.
87. The optical element of claim 61 further comprising at least one additional at least partial coating chosen from photochromic coatings, anti-reflective coatings, linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, transitional coatings, primer coatings, and protective coatings on at least a portion of the substrate.
88. The optical element of claim 87 wherein the at least one additional at least partial coating is over at least a portion of the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound.
89. The optical element of claim 87 wherein the at least one additional at least partial coating is connected to a first surface of the substrate and the at least partial coating comprising the at least one at least partially ordered anisotropic material and the at least one photochromic-dichroic compound is connected to at least a portion of a second surface of the substrate, wherein the first surface is opposite the second surface.
90. An optical element comprising:
a substrate;
a first at least partial coating comprising an at least partially ordered alignment medium connected to at least a portion of at least one surface of the substrate;
a second at least partial coating comprising an alignment transfer material that is connected to an at least partially aligned with at least a portion of the at least partially ordered alignment medium; and a third at least partial coating connected to at least a portion of the alignment transfer material, the third at least partial coating comprising at least one anisotropic material that is at least partially aligned with at least a portion of the at least partially aligned alignment transfer material and at least one photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least partially aligned anisotropic material.
a substrate;
a first at least partial coating comprising an at least partially ordered alignment medium connected to at least a portion of at least one surface of the substrate;
a second at least partial coating comprising an alignment transfer material that is connected to an at least partially aligned with at least a portion of the at least partially ordered alignment medium; and a third at least partial coating connected to at least a portion of the alignment transfer material, the third at least partial coating comprising at least one anisotropic material that is at least partially aligned with at least a portion of the at least partially aligned alignment transfer material and at least one photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least partially aligned anisotropic material.
91. The optical element of claim 90 wherein the first at least partial coating has a thickness ranging from of at least 0.5 manometers to 10,000 nanometers.
92. The optical element of claim 90 wherein the first at least partial coating has a thickness ranging from of at least 0.5 manometers to 1000 manometers.
93. The optical element of claim 90 wherein the first at least partial coating has a thickness ranging from at least 2 manometers to 500 manometers.
94. The optical element of claim 90 wherein the first at least partial coating has a thickness ranging from at least 100 manometers to 500 manometers.
95. The optical element of claim 90 wherein the first at least partial coating further comprises at least one of: a conventional dichroic material, a conventional photochromic material, and a photochromic-dichroic compound.
96. The optical element of claim 90 wherein the first at least partial coating further comprises at least one additive chosen from dyes, alignment promoters, kinetic enhancing additives, photoinitiators, thermal initiators, polymerization inhibitors, solvents, light stabilizers, heat stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, and adhesion promoters.
97. The optical element of claim 90 wherein the second at least partial coating has a thickness ranging from 0.5 microns to 1000 microns.
98. The optical element of claim 90 wherein the second at least partial coating has a thickness ranging from 1 to 25 microns.
99. The optical element of claim 90 wherein the second at least partial coating has a thickness ranging from 5 to 20 microns.
100. The optical element of claim 90 wherein the second at least partial coating further comprises at least one of: a conventional dichroic material, a conventional photochromic material, and a photochromic-dichroic compound.
101. The optical element of claim 90 wherein the second at least partial coating further comprises at least one additive chosen from dyes, alignment promoters, kinetic enhancing additives, photoinitiators, thermal initiators, polymerization inhibitors, solvents, light stabilizers, heat stabilizers, mold release agents, rheology control agents, leveling agents, free radical scavengers, and adhesion promoters.
102. The optical element of claim 90 wherein the third at least partial coating has an average thickness of at least 5 microns.
103. The optical element of claim 90 wherein the third at least partial coating has a thickness ranging from 0.5 microns to 1000 microns.
104. The optical element of claim 90 wherein the third at least partial coating has a thickness ranging from 1 to 25 microns.
105. The optical element of claim 90 wherein the third at least partial coating has a thickness ranging from 5 to 20 microns.
106. The optical element of claim 90 wherein the at least one photochromic-dichroic compound has an average absorption ratio of at least 1.5 in an activated state as determined according to CELL METHOD.
107. The optical element of claim 90 wherein the at least one photochromic-dichroic compound has an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
108. The optical element of claim 89 wherein the at least one photochromic-dichroic compound has an average absorption ratio ranging from 2.5 to 50 in an activated state as determined according to CELL METHOD.
109. A composite optical element comprising:
a substrate;
an at least partially ordered polymeric sheet connected to at least a portion of the substrate; and at least one thermally reversible photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least partially ordered polymeric sheet and has an average absorption ratio greater than 2.3 in the activated state as determined according to CELL METHOD.
a substrate;
an at least partially ordered polymeric sheet connected to at least a portion of the substrate; and at least one thermally reversible photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least partially ordered polymeric sheet and has an average absorption ratio greater than 2.3 in the activated state as determined according to CELL METHOD.
110. The composite optical element of claim 109 wherein the at least partially ordered polymeric sheet is chosen from a stretched polymer sheet, an at least partially ordered liquid crystal polymer sheet, and a photo-oriented polymer sheet.
111. The composite optical element of claim 109 further comprising a first rigid polymeric sheet interposed between the substrate and the at least partially ordered polymeric sheet and a second rigid polymeric sheet positioned over the at least partially ordered polymeric sheet.
112. The composite optical element of claim 109 further comprising at least one additional at least partially ordered polymeric sheet connected to at least a portion of the substrate.
113. A composite optical element comprising:
a substrate; and at least one sheet connected to at least a portion of the substrate, the at least one sheet comprising:
an at least partially ordered liquid crystal polymer having at least a first general direction;
at least one at least partially ordered liquid crystal material having at least a second general direction that is generally parallel to at least the first general direction distributed within at least a portion of the liquid crystal polymer; and at least one photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least one at least partially ordered liquid crystal material.
a substrate; and at least one sheet connected to at least a portion of the substrate, the at least one sheet comprising:
an at least partially ordered liquid crystal polymer having at least a first general direction;
at least one at least partially ordered liquid crystal material having at least a second general direction that is generally parallel to at least the first general direction distributed within at least a portion of the liquid crystal polymer; and at least one photochromic-dichroic compound that is at least partially aligned with at least a portion of the at least one at least partially ordered liquid crystal material.
114. A method of making an optical element comprising forming an at least partial coating comprising at least one at least partially aligned thermally reversible photochromic-dichroic compound on at least a portion of a substrate.
115. The method of claim 114 wherein the at least partial coating has an average absorption ratio of at least 1.5.
116. The method of claim 114 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio of at least 1.5 in an activated state as determined according to CELL METHOD.
117. The method of claim 114 wherein the at least one at least partially aligned thermally reversible photochromic-dichroic compound has an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
118. The method of claim 114 wherein forming the at least partial coating comprises:
applying at least one anisotropic material to at least a portion of the substrate;
imbibing the at least one thermally reversible photochromic-dichroic compound into at least a portion of the at least one anisotropic material;
at least partially ordering at least a portion of the anisotropic material;
and at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered anisotropic material.
applying at least one anisotropic material to at least a portion of the substrate;
imbibing the at least one thermally reversible photochromic-dichroic compound into at least a portion of the at least one anisotropic material;
at least partially ordering at least a portion of the anisotropic material;
and at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered anisotropic material.
119. The method of claim 118 wherein imbibing the at least one thermally reversible photochromic-dichroic compound into at least a portion of the at least one anisotropic material occurs at least one of: before, during or after at least partially ordering at least a portion of the anisotropic material.
120. The method of claim 114 wherein forming the at least partial coating comprises:
applying at least one thermally reversible photochromic-dichroic compound and at least one anisotropic material to at least a portion of the substrate;
at least partially ordering at least a portion of the anisotropic material;
and at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered anisotropic material.
applying at least one thermally reversible photochromic-dichroic compound and at least one anisotropic material to at least a portion of the substrate;
at least partially ordering at least a portion of the anisotropic material;
and at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered anisotropic material.
121. The method of claim 120 wherein applying the at least one thermally reversible photochromic-dichroic compound and the at least one anisotropic material to the at least a portion of the substrate occurs at least one of: before, during, or after at least partially ordering at least a portion of the anisotropic material and at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound.
122. The method of claim 120 wherein applying the at least one thermally reversible photochromic-dichroic compound and the at least one anisotropic material comprises at least one of spin coating, spray coating, spray and spin coating, curtain coating, flow coating, dip coating, injection molding, casting, roll coating, wire coating, overmolding.
123. The method of claim 120 wherein applying the at least one thermally reversible photochromic-dichroic compound and at least one anisotropic material to at least a portion of the substrate comprises:
applying a phase-separating polymer system comprising a matrix phase forming material comprising a liquid crystal material and a guest phase forming material comprising the at least one anisotropic material and at least one thermally reversible photochromic-dichroic compound to at least a portion of the substrate;
at least partially ordering at least a portion of the matrix phase forming material and at least a portion of the guest phase forming material;
at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered guest phase forming material; and causing at least a portion of the guest phase forming material to separate from at least a portion of the matrix phase forming material by at least one of polymerization induced phase separation and solvent induced phase separation.
applying a phase-separating polymer system comprising a matrix phase forming material comprising a liquid crystal material and a guest phase forming material comprising the at least one anisotropic material and at least one thermally reversible photochromic-dichroic compound to at least a portion of the substrate;
at least partially ordering at least a portion of the matrix phase forming material and at least a portion of the guest phase forming material;
at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered guest phase forming material; and causing at least a portion of the guest phase forming material to separate from at least a portion of the matrix phase forming material by at least one of polymerization induced phase separation and solvent induced phase separation.
124. The method of claim 123 wherein applying the phase-separating polymer system comprises applying a solution comprising the matrix phase forming material, the guest phase forming material, the at least one thermally reversible photochromic-dichroic compound, and at least one common solvent on the at least a portion of the optical substrate.
125. The method of claim 124 wherein:
the matrix phase forming material is a liquid crystal polymer and the guest phase forming material is a liquid crystal polymer that is different from the liquid crystal polymer of the matrix phase forming material; and causing at least a portion of the guest phase forming material to separate from at least a portion of the matrix phase forming material comprises evaporating at least a portion of the at least one common solvent.
the matrix phase forming material is a liquid crystal polymer and the guest phase forming material is a liquid crystal polymer that is different from the liquid crystal polymer of the matrix phase forming material; and causing at least a portion of the guest phase forming material to separate from at least a portion of the matrix phase forming material comprises evaporating at least a portion of the at least one common solvent.
126. The method of claim 123 wherein:
the matrix phase forming material is a liquid crystal monomer and the guest phase forming material is chosen from a liquid crystal mesogen and a low viscosity liquid crystal monomer that is different from the liquid crystal monomer of the matrix phase forming material; and causing at least a portion of the guest phase forming material to separate from at least a portion of the matrix phase forming material comprises polymerizing at least a portion of the liquid crystal monomer of the matrix phase forming material.
the matrix phase forming material is a liquid crystal monomer and the guest phase forming material is chosen from a liquid crystal mesogen and a low viscosity liquid crystal monomer that is different from the liquid crystal monomer of the matrix phase forming material; and causing at least a portion of the guest phase forming material to separate from at least a portion of the matrix phase forming material comprises polymerizing at least a portion of the liquid crystal monomer of the matrix phase forming material.
127. The method of claim 126 wherein polymerizing at least a portion of the liquid crystal monomer of the matrix phase forming material comprises at least one of photo-induced polymerization and thermally-induced polymerization.
128. The method of claim 126 wherein the guest phase forming material is a low viscosity liquid crystal monomer, and wherein at least a portion of the guest phase forming material is at least partially polymerized after polymerizing at least a portion of the liquid crystal monomer of the matrix phase forming material.
129. The method of claim 123 wherein matrix phase forming material comprises a liquid crystal material chosen from liquid crystal monomers, liquid crystal pre-polymers, and liquid crystal polymers.
130. The method of claim 123 wherein guest phase forming material comprises a liquid crystal material chosen from liquid crystal mesogens, liquid crystal monomers, liquid crystal pre-polymers, and liquid crystal polymers.
131. The method of claim 120 wherein ordering at least a portion of the at least one anisotropic material comprises exposing the at least a portion of the anisotropic material to at least of: a magnetic field, an electric field, linearly polarized ultraviolet radiation, linearly polarized infrared radiation, linearly polarized visible radiation, and a shear force.
132. The method of claim 120 further comprising at least partially setting at least a portion of the at least one anisotropic material.
133. The method of claim 132 wherein at least partially setting at least a portion of the at least one anisotropic material comprises at least partially cross-linking at least a portion of the at least one anisotropic material.
134. The method of claim 114 further comprising imparting at least one orientation facility on at least a portion of a substrate prior to forming the at least partial coating comprising at least one at least partially aligned thermally reversible photochromic-dichroic compound on the at least a portion of a substrate such that at least a portion of the at least one orientation facility is between at least a portion of the at least partial coating and at least a portion of the substrate.
135. The method of claim 134 wherein imparting the at least one orientation facility on the at least a portion of the substrate comprises at least one of: forming an at least partial coating comprising an at least partially ordered alignment medium on the at least a portion of the substrate; applying an at least partially ordered polymer sheet to the at least a portion of the substrate; at least partially treating at least a portion of at least one surface of the substrate;
and forming a Langmuir-Blodgett film on at least a portion of the substrate.
and forming a Langmuir-Blodgett film on at least a portion of the substrate.
136. The method of claim 134 wherein imparting the at least one orientation facility on the at least a portion of the substrate comprises forming an at least partial coating comprising an at least partially ordered alignment medium on the at least a portion of the substrate, wherein the alignment medium is chosen from photo-orientation materials, rubbed-orientation materials, and liquid crystal materials.
137. The method of claim 136 wherein forming the at least partial coating comprising the at least partially ordered alignment medium comprises applying an alignment medium to at least a portion of the substrate and at least partially ordering at least a portion of the alignment medium.
138. The method of claim 137 wherein at least partially ordering at least a portion of the alignment medium comprises at least one of: exposing the at least a portion of the alignment medium to linearly polarized ultraviolet radiation; exposing the at least a portion of the alignment medium to linearly polarized infrared radiation; exposing the at least a portion of the alignment medium to linearly polarized visible radiation; exposing the at least a portion of the alignment medium to a magnetic field; exposing the at least a portion of the alignment medium to an electric field; etching the at least a portion of the alignment medium; exposing the at least a portion of the alignment medium to a shear force; and rubbing the at least a portion of the alignment medium.
139. The method of claim 136 wherein the alignment medium is a photo-orientation material, and at least partially ordering at least a portion of the alignment medium comprises exposing at least a portion of the photo-orientation material to linearly polarized ultraviolet radiation.
140. The method of claim 139 wherein forming the at least partial coating comprising that at least partially ordered alignment medium further comprises at least partially setting at least a portion of the alignment medium after at least partially ordering at least a portion of the alignment medium by at least one of at least partially drying the at least a portion of the alignment medium, at least partially cross-linking the at least a portion of the alignment medium, and at least partially curing the at least a portion of the alignment medium.
141. The method of claim 140 wherein at least partially curing the at least a portion of the alignment medium comprises at least one of ultraviolet curing, electron beam curing, and thermal curing.
142. The method of claim 134 wherein forming the at least partial coating comprising the at least one at least partially aligned photochromic-dichroic compound comprises:
applying a polymerizable composition, at least one anisotropic material, and at least one thermally reversible photochromic-dichroic compound to at least a portion of the at least one orientation facility;
aligning at least a portion of the at least one anisotropic material with at least a portion of the at least one orientation facility; and aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially aligned at least one anisotropic material.
applying a polymerizable composition, at least one anisotropic material, and at least one thermally reversible photochromic-dichroic compound to at least a portion of the at least one orientation facility;
aligning at least a portion of the at least one anisotropic material with at least a portion of the at least one orientation facility; and aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially aligned at least one anisotropic material.
143. The method of claim 142 further comprising at least partially setting at least a portion of the at least one anisotropic material by exposing at least a portion of the at least partial coating to ultraviolet radiation and at least partially setting at least a portion of the polymerizable composition by exposing at least a portion of the at least partial coating to thermal energy.
144. The method of claim 143 wherein at least partially setting at least a portion of the at least one anisotropic material occurs at least one of: before, during or after at least partially setting at least a portion of the polymerizable composition.
145. The method of claim 143 wherein the at least one anisotropic material is a liquid crystal material and the polymerizable composition comprises dihydroxy monomers and isocyanate monomers.
146. A method of making an optical element comprising:
(a) forming an at least partial coating on at least a portion of a substrate;
and (b) adapting at least a portion of the at least partial coating to switch from a first state to a second linearly polarizing state in response to actinic radiation and to revert back to the first sate in response to thermal energy.
(a) forming an at least partial coating on at least a portion of a substrate;
and (b) adapting at least a portion of the at least partial coating to switch from a first state to a second linearly polarizing state in response to actinic radiation and to revert back to the first sate in response to thermal energy.
147. The method of claim 146 wherein (a) forming the at least partial coating occurs at least one of: before, during, or after (b) adapting at least a portion of the at least partial coating to switch from a first state to a second linearly polarizing state in response to actinic radiation and to revert back to the first sate in response to thermal energy.
148. The method of claim 146 wherein:
(a) forming the at least partial coating comprises applying at least one anisotropic material and at least one thermally reversible photochromic-dichroic compound on the at least a portion of the substrate; and (b) adapting at least a portion of the at least partial coating to switch from the first state to the second linearly polarizing state in response to actinic radiation and to revert back to the first sate in response to thermal energy comprises at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound.
(a) forming the at least partial coating comprises applying at least one anisotropic material and at least one thermally reversible photochromic-dichroic compound on the at least a portion of the substrate; and (b) adapting at least a portion of the at least partial coating to switch from the first state to the second linearly polarizing state in response to actinic radiation and to revert back to the first sate in response to thermal energy comprises at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound.
149. The method of claim 148 wherein at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound comprises at least partially ordering at least a portion of the anisotropic material and at least partially aligning the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered anisotropic material.
150. The method of claim 146 wherein:
(a) forming the at least partial coating on the at least a portion of the substrate comprises applying an alignment medium to the at least a portion of the substrate; and (b) adapting at least a portion of the at least partial coating to switch from a first state to a second linearly polarizing state in response to actinic radiation and to revert back to the first sate in response to thermal energy comprises:
at least partially ordering at least a portion of the alignment medium, applying at least one thermally reversible photochromic-dichroic compound to at least a portion of the at least partial coating comprising the alignment medium; and at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered alignment medium.
(a) forming the at least partial coating on the at least a portion of the substrate comprises applying an alignment medium to the at least a portion of the substrate; and (b) adapting at least a portion of the at least partial coating to switch from a first state to a second linearly polarizing state in response to actinic radiation and to revert back to the first sate in response to thermal energy comprises:
at least partially ordering at least a portion of the alignment medium, applying at least one thermally reversible photochromic-dichroic compound to at least a portion of the at least partial coating comprising the alignment medium; and at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound with at least a portion of the at least partially ordered alignment medium.
151. The method of claim 150 wherein at least partially ordering the at least a portion of the alignment medium comprises at least one of exposing at least a portion of the alignment medium to linearly polarized ultraviolet radiation, exposing the at least a portion of the alignment medium to an electric field, exposing the at least a portion of the alignment medium to a magnetic field, exposing the at least a portion of the alignment medium to linearly polarized infrared radiation, exposing the at least a portion of the alignment medium to linearly polarized visible radiation, etching the at least a portion of the alignment medium, exposing the at least a portion of the alignment medium to a shear force, and rubbing the at least a portion of the alignment medium.
152. The method of claim 150 further comprising at least partially setting at least a portion of the alignment medium after at least partially ordering the at least a portion of the alignment medium and prior to applying the at least one thermally reversible photochromic-dichroic compound.
153. The method of claim 150 wherein at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound occurs at least one of:
before, during or after applying the at least one thermally reversible photochromic-dichroic compound to at least a portion of the at least partial coating comprising the alignment medium.
before, during or after applying the at least one thermally reversible photochromic-dichroic compound to at least a portion of the at least partial coating comprising the alignment medium.
154. The method of claim 150 wherein applying the at least one thermally reversible photochromic-dichroic compound to the at least a portion of the at least partial coating comprising the alignment medium comprises at least one of spin coating, spray coating, spray and spin coating, curtain coating, flow coating, dip coating, injection molding, casting, roll coating, wire coating, overmolding and imbibing.
155. The method of claim 150 wherein applying the at least one thermally reversible photochromic-dichroic compound comprises forming an at least partial coating comprising the at least one thermally reversible photochromic-dichroic compound and at least one anisotropic material on the at least a portion of the at least partially ordered alignment medium, and at least partially aligning at least a portion of the at least one thermally reversible photochromic-dichroic compound comprises at least partially aligning at least a portion of the at least one anisotropic material with at least a portion of the at least partially ordered alignment medium.
156. A method of making an optical element comprising:
forming an at least partial coating comprising an alignment medium to at least a portion of at least one surface of a substrate and at least partially ordering at least a portion of the alignment medium;
forming at least one at least partial coating comprising an alignment transfer material on at least a portion of the at least partial coating comprising the alignment medium and at least partially aligning at least a portion of the alignment transfer material with at least a portion of the at least partially ordered alignment medium;
and forming an at least partial coating comprising an anisotropic material and at least one photochromic-dichroic compound on at least a portion of the alignment transfer material, at least partially aligning at least a portion of the anisotropic material with at least a portion of the at least partially aligned alignment transfer material, and at least partially aligning at least a portion of the at least one photochromic-dichroic compound with at least a portion of the at least partially aligned anisotropic material.
forming an at least partial coating comprising an alignment medium to at least a portion of at least one surface of a substrate and at least partially ordering at least a portion of the alignment medium;
forming at least one at least partial coating comprising an alignment transfer material on at least a portion of the at least partial coating comprising the alignment medium and at least partially aligning at least a portion of the alignment transfer material with at least a portion of the at least partially ordered alignment medium;
and forming an at least partial coating comprising an anisotropic material and at least one photochromic-dichroic compound on at least a portion of the alignment transfer material, at least partially aligning at least a portion of the anisotropic material with at least a portion of the at least partially aligned alignment transfer material, and at least partially aligning at least a portion of the at least one photochromic-dichroic compound with at least a portion of the at least partially aligned anisotropic material.
157. The method of claim 156 wherein at least partially ordering at least a portion of the alignment medium comprises at least one of exposing the at least a portion of the alignment medium to linearly polarized ultraviolet radiation; exposing the at least a portion of the alignment medium to linearly polarized infrared radiation; exposing the at least a portion of the alignment medium to linearly polarized visible radiation; exposing the at least a portion of the alignment medium to a magnetic field; exposing the at least a portion of the alignment medium to an electric field; drying the at least a portion of the alignment medium; etching the at least a portion of the alignment medium; and rubbing the at least a portion of the alignment medium.
158. The method of claim 156 wherein forming the at least one at least partial coating comprising the alignment transfer material comprises:
forming a first at least partial coating comprising an alignment transfer material on at least a portion of at least one surface of the substrate, the first at least partial coating having a thickness ranging from 2 to 8 microns;
at least partially aligning at least a portion of the alignment transfer material with at least a portion of the at least partially ordered alignment medium;
at least partially setting at least a portion of the alignment transfer material after at least partially aligning the at least a portion of the alignment transfer material;
forming a second at least partial coating comprising an alignment transfer material, the second at least partial coating having a thickness ranging from greater than to 30 microns; and at least partially aligning at least a portion of the alignment transfer material with at least a portion of the at least partially aligned alignment transfer material of the first at least partial coating.
forming a first at least partial coating comprising an alignment transfer material on at least a portion of at least one surface of the substrate, the first at least partial coating having a thickness ranging from 2 to 8 microns;
at least partially aligning at least a portion of the alignment transfer material with at least a portion of the at least partially ordered alignment medium;
at least partially setting at least a portion of the alignment transfer material after at least partially aligning the at least a portion of the alignment transfer material;
forming a second at least partial coating comprising an alignment transfer material, the second at least partial coating having a thickness ranging from greater than to 30 microns; and at least partially aligning at least a portion of the alignment transfer material with at least a portion of the at least partially aligned alignment transfer material of the first at least partial coating.
159. A method of making a composite element comprising connecting an at least partially ordered polymeric sheet to at least a portion of a substrate, the at least partially ordered polymeric sheet comprising at least one at least partially aligned thermally reversible photochromic-dichroic compound connected to at least a portion thereof and having an average absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD.
160. The method of claim 159 wherein the at least partially ordered polymeric sheet is chosen from a stretched polymer sheet, a photo-oriented polymer sheet, an at least partially ordered phase-separated sheet, and combinations thereof.
161. The method of claim 159 wherein the at least partially ordered polymeric sheet is formed by:
applying an at least partial layer of a photo-orientable polymer network on a release layer and subsequently ordering and at least partially curing at least a portion of the photo-orientable polymer network;
forming an at least partial coating of an anisotropic material and at least one thermally reversible photochromic-dichroic compound on at least a portion of at least partial layer comprising the photo-orientable polymer network, at least partially aligning at least a portion of the anisotropic material and the at least one thermally reversible photochromic-dichroic compound with at least a portion of the photo-orientable polymer network, and at least partially curing at least a portion of the anisotropic material; and releasing the at least partial layer of the photo-orientable polymer network from the release layer to form the at least partially ordered polymeric sheet.
applying an at least partial layer of a photo-orientable polymer network on a release layer and subsequently ordering and at least partially curing at least a portion of the photo-orientable polymer network;
forming an at least partial coating of an anisotropic material and at least one thermally reversible photochromic-dichroic compound on at least a portion of at least partial layer comprising the photo-orientable polymer network, at least partially aligning at least a portion of the anisotropic material and the at least one thermally reversible photochromic-dichroic compound with at least a portion of the photo-orientable polymer network, and at least partially curing at least a portion of the anisotropic material; and releasing the at least partial layer of the photo-orientable polymer network from the release layer to form the at least partially ordered polymeric sheet.
162. The method of claim 159 wherein the at least partially ordered polymeric sheet comprises a phase-separated polymer comprising an at least partially ordered matrix phase comprising a liquid crystal material and an at least partially ordered guest phase comprising a liquid crystal material, wherein the at least one thermally reversible photochromic-dichroic compound is connected to and at least partially aligned with at least a portion of the at least partially ordered guest phase.
163. The method of claim 159 wherein connecting the at least partially ordered polymeric sheet to the at least a portion of the substrate comprises at least one of laminating, fusing, in-mold casting, and adhesively bonding the at least partially ordered polymeric sheet to the at least a portion of the substrate.
164. A method of making a composite element comprising:
forming a sheet comprising an at least partially ordered liquid crystal polymer having at least a first general direction, a liquid crystal material having at least a second general direction distributed within at least a portion of the liquid crystal polymer;
and at least one photochromic-dichroic compound that is at least partially aligned with at least a portion of the liquid crystal material; and connecting at least a portion of the sheet to at least a portion of an optical substrate to form the composite element.
forming a sheet comprising an at least partially ordered liquid crystal polymer having at least a first general direction, a liquid crystal material having at least a second general direction distributed within at least a portion of the liquid crystal polymer;
and at least one photochromic-dichroic compound that is at least partially aligned with at least a portion of the liquid crystal material; and connecting at least a portion of the sheet to at least a portion of an optical substrate to form the composite element.
165. The method of claim 164 wherein forming the sheet comprises:
applying a phase-separating polymer system comprising a matrix phase forming material comprising a liquid crystal material, a guest phase forming material comprising a liquid crystal material, and at least one photochromic-dichroic compound on at least a portion of a substrate;
at least partially aligning at least a portion of the at least one photochromic-dichroic compound by at least partially ordering at least a portion of the matrix phase forming material and at least a portion of the guest phase forming material;
causing at least a portion of the guest phase forming material to separate from at least a portion of the matrix phase forming material by at least one of polymerization induced phase-separation and solvent induced phase-separation;
and removing the coating from the substrate.
applying a phase-separating polymer system comprising a matrix phase forming material comprising a liquid crystal material, a guest phase forming material comprising a liquid crystal material, and at least one photochromic-dichroic compound on at least a portion of a substrate;
at least partially aligning at least a portion of the at least one photochromic-dichroic compound by at least partially ordering at least a portion of the matrix phase forming material and at least a portion of the guest phase forming material;
causing at least a portion of the guest phase forming material to separate from at least a portion of the matrix phase forming material by at least one of polymerization induced phase-separation and solvent induced phase-separation;
and removing the coating from the substrate.
166. The method of claim 164 wherein forming the sheet comprises:
forming an at least partially ordered liquid crystal polymer sheet having at least a first general direction; and imbibing at least one liquid crystal mesogen and at least one photochromic-dichroic compound into at least a portion of the at least partially ordered liquid crystal polymer sheet.
forming an at least partially ordered liquid crystal polymer sheet having at least a first general direction; and imbibing at least one liquid crystal mesogen and at least one photochromic-dichroic compound into at least a portion of the at least partially ordered liquid crystal polymer sheet.
167. The method of claim 164 wherein forming the sheet comprises:
forming a liquid crystal polymer sheet;
imbibing at least one liquid crystal mesogen and at least one photochromic-dichroic compound into at least a portion of the liquid crystal polymer sheet; and at feast partially aligning at least a portion of the at least one photochromic-dichroic compound by at least partially ordering at least a portion of the liquid crystal polymer sheet and at least a portion of the at least one liquid crystal mesogen.
forming a liquid crystal polymer sheet;
imbibing at least one liquid crystal mesogen and at least one photochromic-dichroic compound into at least a portion of the liquid crystal polymer sheet; and at feast partially aligning at least a portion of the at least one photochromic-dichroic compound by at least partially ordering at least a portion of the liquid crystal polymer sheet and at least a portion of the at least one liquid crystal mesogen.
168. The method of claim 164 wherein connecting the sheet to at least a portion of the optical substrate comprises at least one of laminating, fusing, in-mold casting, and adhesively bonding at least a portion of the sheet to the optical substrate.
169. A method of making a composite element comprising:
forming a sheet comprising an at least partially ordered liquid crystal polymer having at least a first general direction and a liquid crystal material having at least a second general direction distributed within at least a portion of the liquid crystal polymer;
connecting at least a portion of the sheet to at least a portion of an optical substrate;
and imbibing at least one photochromic-dichroic compound into at least a portion of the sheet.
forming a sheet comprising an at least partially ordered liquid crystal polymer having at least a first general direction and a liquid crystal material having at least a second general direction distributed within at least a portion of the liquid crystal polymer;
connecting at least a portion of the sheet to at least a portion of an optical substrate;
and imbibing at least one photochromic-dichroic compound into at least a portion of the sheet.
170. A method of making an optical element comprising overmolding an at least partial coating comprising an at least partially ordered liquid crystal material and at least one at least partially aligned photochromic-dichroic compound on at least a portion of an optical substrate.
171. The method of claim 170 wherein overmolding comprises:
placing at least a portion of a surface of the optical substrate adjacent a surface of a transparent mold such that the surface of the optical substrate and the surface of the transparent mold define an molding region;
introducing a liquid crystal material and at least one photochromic-dichroic compound into the molding region defined by the surface of the optical substrate and the surface of the transparent mold such that at least a portion of the liquid crystal material coats at least a portion of the surface of the optical substrate;
at least partially ordering at least a portion of the liquid crystal material such that the at least partially ordered portion of the liquid crystal material and at least partially aligning at least a portion of the at least one photochromic-dichroic compound with at least a portion of the at least partially ordered liquid crystal material;
at least partially polymerizing at least a portion of the liquid crystal material; and separating the optical substrate and the liquid crystal material from the transparent mold.
placing at least a portion of a surface of the optical substrate adjacent a surface of a transparent mold such that the surface of the optical substrate and the surface of the transparent mold define an molding region;
introducing a liquid crystal material and at least one photochromic-dichroic compound into the molding region defined by the surface of the optical substrate and the surface of the transparent mold such that at least a portion of the liquid crystal material coats at least a portion of the surface of the optical substrate;
at least partially ordering at least a portion of the liquid crystal material such that the at least partially ordered portion of the liquid crystal material and at least partially aligning at least a portion of the at least one photochromic-dichroic compound with at least a portion of the at least partially ordered liquid crystal material;
at least partially polymerizing at least a portion of the liquid crystal material; and separating the optical substrate and the liquid crystal material from the transparent mold.
172. The method of claim 170 wherein overmolding comprises:
introducing a liquid crystal material and at least one photochromic-dichroic compound onto the surface of a transparent mold;
contacting at least a portion of the liquid crystal material with at least a portion of a surface of an optical substrate such that at least a portion of the liquid crystal material is caused to flow between the portion of the surface of the optical substrate and a portion of the surface of the transparent mold and to coat at least a portion of the surface of the optical substrate;
at least partially ordering at least a portion of the liquid crystal material such that the at least partially ordered portion of the liquid crystal material and at least partially aligning at least a portion of the at least one photochromic-dichroic compound with at least a portion of the at least partially ordered liquid crystal material;
at least partially polymerizing at least a portion of the liquid crystal material; and separating the optical substrate and the liquid crystal material from the transparent mold.
182. The security element of claim 176 wherein the at least partial coating comprises at least one photochromic-dichroic compound having an average absorption ratio of at least 1.5 in the activated state as determined according to CELL METHOD.
183. The security element of claim 176 further comprising at least one additional at least partial coating chosen from linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, photochromic coatings, reflective coatings, and tinted coatings connected to at least a portion of the substrate.
184. The security element of claim 176 further comprising at least one sheet chosen from linearly polarizing sheets, circularly polarizing sheets, elliptically polarizing sheets, photochromic sheets, reflective sheets, tinted sheets, retarder sheets, and wide-angle view sheets connected to at least a portion of the substrate.
185. A method of making a security element comprising forming an at least partial coating on at least a portion of the substrate, the at least partial coating comprising at least one at least partially aligned thermally reversible photochromic-dichroic compound.
186. The method of claim 185 wherein the at least one thermally reversible photochromic-dichroic compound has an average absorption ratio of at least 1.5 in the activated state as determined according to CELL METHOD.
187. The method of claim 185 further comprising forming at least one additional at least partial coating chosen from linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, photochromic coatings, reflective coatings, tinted coatings, retarder coatings, and wide-angle view coatings on at least a portion of the substrate prior to forming the at least one photochromic-dichroic compound that is at least partially aligned on the at least a portion of the substrate.
188. The method of claim 185 further comprising forming at least one additional at least partial coating chosen from linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, photochromic coatings, reflective coatings, tinted coatings, retarder coatings, and wide-angle view coatings on at least a portion of the substrate after forming the at least one photochromic-dichroic compound that is at least partially aligned on the at least a portion of the substrate.
introducing a liquid crystal material and at least one photochromic-dichroic compound onto the surface of a transparent mold;
contacting at least a portion of the liquid crystal material with at least a portion of a surface of an optical substrate such that at least a portion of the liquid crystal material is caused to flow between the portion of the surface of the optical substrate and a portion of the surface of the transparent mold and to coat at least a portion of the surface of the optical substrate;
at least partially ordering at least a portion of the liquid crystal material such that the at least partially ordered portion of the liquid crystal material and at least partially aligning at least a portion of the at least one photochromic-dichroic compound with at least a portion of the at least partially ordered liquid crystal material;
at least partially polymerizing at least a portion of the liquid crystal material; and separating the optical substrate and the liquid crystal material from the transparent mold.
182. The security element of claim 176 wherein the at least partial coating comprises at least one photochromic-dichroic compound having an average absorption ratio of at least 1.5 in the activated state as determined according to CELL METHOD.
183. The security element of claim 176 further comprising at least one additional at least partial coating chosen from linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, photochromic coatings, reflective coatings, and tinted coatings connected to at least a portion of the substrate.
184. The security element of claim 176 further comprising at least one sheet chosen from linearly polarizing sheets, circularly polarizing sheets, elliptically polarizing sheets, photochromic sheets, reflective sheets, tinted sheets, retarder sheets, and wide-angle view sheets connected to at least a portion of the substrate.
185. A method of making a security element comprising forming an at least partial coating on at least a portion of the substrate, the at least partial coating comprising at least one at least partially aligned thermally reversible photochromic-dichroic compound.
186. The method of claim 185 wherein the at least one thermally reversible photochromic-dichroic compound has an average absorption ratio of at least 1.5 in the activated state as determined according to CELL METHOD.
187. The method of claim 185 further comprising forming at least one additional at least partial coating chosen from linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, photochromic coatings, reflective coatings, tinted coatings, retarder coatings, and wide-angle view coatings on at least a portion of the substrate prior to forming the at least one photochromic-dichroic compound that is at least partially aligned on the at least a portion of the substrate.
188. The method of claim 185 further comprising forming at least one additional at least partial coating chosen from linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, photochromic coatings, reflective coatings, tinted coatings, retarder coatings, and wide-angle view coatings on at least a portion of the substrate after forming the at least one photochromic-dichroic compound that is at least partially aligned on the at least a portion of the substrate.
173. The method of claim 172 wherein of at least one of at least a portion of the surface of the transparent mold and at least a portion of the surface of the optical substrate comprises at least one orientation facility having at least a first general direction.
174. The method of claim 173 wherein the optical substrate is a multi-vision, segmented ophthalmic lens.
175. A method of making an optical element comprising:
overmolding an at least partial coating comprising an at least partially ordered liquid crystal material on at least a portion of an optical substrate; and imbibing at least one photochromic-dichroic compound into at least a portion of the at least partially ordered liquid crystal material.
overmolding an at least partial coating comprising an at least partially ordered liquid crystal material on at least a portion of an optical substrate; and imbibing at least one photochromic-dichroic compound into at least a portion of the at least partially ordered liquid crystal material.
176. A security element connected to at least a portion of a substrate, the security element comprising an at least partial coating having a first state and a second state connected to at least a portion of the substrate, the at least partial coating being adapted to switch from a first state to a second state in response to at least actinic radiation, to revert back to the first state in response to thermal energy, and to linearly polarize at least transmitted radiation in at least one of the first state anal the second state.
177. The security element of claim 176 wherein the security element is at least one of a security mark and an authentication mark.
178. The security element of claim 176 wherein the substrate is chosen from transparent substrates and reflective substrates.
179. The security element of claim 176 wherein the at least a portion of the substrate to which the security mark is connected is coated with a reflective material.
180. The security element of claim 176 wherein the substrate is chosen from untinted substrates, tinted substrates, photochromic substrates, tinted-photochromic substrates, linearly polarizing substrates, circularly polarizing substrates, and elliptically polarizing substrates.
181. The security element of claim 176 wherein the substrate is chosen from access cards and passes; negotiable instruments and non-negotiable instruments; government documents; consumer goods; credit cards; and merchandise tags, labels and packaging.
189. The method of claim 185 further comprising applying a sheet chosen from linearly polarizing sheets, circularly polarizing sheets, elliptically polarizing sheets, photochromic sheets, reflective sheets, tinted sheets, retarder sheets, and wide-angle view sheets to at least a portion of the substrate prior to forming the at least one photochromic-dichroic compound that is at least partially aligned on the at least a portion of the substrate.
190. The method of claim 185 further comprising applying a sheet chosen from linearly polarizing sheets, circularly polarizing sheets, elliptically polarizing sheets, photochromic sheets, reflective sheets, tinted sheets, retarder sheets, and wide-angle view sheets to at least a portion of the substrate after forming the at least one photochromic-dichroic compound that is at least partially aligned on the at least a portion of the substrate.
191. A liquid crystal cell comprising:
a first substrate having a first surface;
a second substrate having a second surface, wherein the second surface of the second substrate is opposite and spaced apart from the first surface of the first substrate so as to define a region; and a liquid crystal material adapted to be at least partially ordered and at least one thermally reversible photochromic-dichroic compound adapted to be at least partially aligned and having an aver age absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD positioned within the region defined by the first surface and the second surface.
192. The liquid crystal cell of claim 191 wherein the liquid crystal cell is a display element chosen from screens, monitors, and security elements.
193. The liquid crystal cell of claim 191 wherein the first substrate and the second substrate are independently chosen from untinted substrates, tinted substrates, photochromic substrates, tinted-photochromic substrates, linearly polarizing substrates, circularly polarizing substrates, and elliptically polarizing substrates.
194. The liquid crystal cell of claim 191 further comprising a first orientation facility positioned adjacent the first surface and a second orientation facility positioned adjacent the second surface.
195. The liquid crystal cell of claim 194 further comprising a first electrode interposed between at least a portion of the first orientation facility and the first surface, and a second electrode interposed between at least a portion of the second orientation facility and the second surface.
196. The liquid crystal cell of claim 195 wherein the liquid crystal cell forms at least a portion .
of an electrical circuit.
197. The liquid crystal cell of claim 191 further comprising a first electrode adjacent the first surface, and a second electrode adjacent the second surface.
198. The liquid crystal cell of claim 191 wherein the liquid crystal cell forms at least a portion of an electrical circuit.
199. The liquid crystal cell of claim 191 further comprising an at least partial coating chosen from linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, photochromic coatings, reflective coatings, tinted coatings, retarder coatings, and wide-angle view coatings connected to at least a portion of a surface of at least one of the first substrate and the second substrate.
200. The liquid crystal cell of claim 191 further comprising at least one sheet chosen from linearly polarizing sheets, circularly polarizing sheets, elliptically polarizing sheets, photochromic sheets, reflective sheets, tinted sheets, retarder sheets, and wide-angle view sheets connected to at feast a portion of a surface of at least one of the first substrate and the second substrate.
201. An optical element comprising:
a substrate; and an at least partial coating having a first state and a second state on at least a portion of the substrate, the at least partial coating being adapted to be circularly polarizing or elliptically polarizing in at least one state-and comprising:
a chiral nematic or cholesteric liquid crystal material having molecules that-are helically arranged through a thickness of the at least partial coating;
and at least one photochromic-dichroic compound that is at least partially aligned with the liquid crystal material such that a long axis of a molecule of the at least one photochromic-dichroic compound is generally parallel to the molecules of the liquid crystal material.
202. An optical element comprising:
a substrate; and an at least partial coating connected to at least a portion of the substrate, the at least partial coating comprising an at least partially ordered anisotropic material and at least one photochromic-dichroic compound that is at least partially aligned with the at least partially ordered anisotropic material, said photochromic-dichroic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by::
-[S1]c-[Q1 -[S2]d]d'-[Q2 -[S3]e]e'-[Q3 -[S4]f]f'-S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C2-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)9-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.-C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d'+e'+f'is at 1.
189. The method of claim 185 further comprising applying a sheet chosen from linearly polarizing sheets, circularly polarizing sheets, elliptically polarizing sheets, photochromic sheets, reflective sheets, tinted sheets, retarder sheets, and wide-angle view sheets to at least a portion of the substrate prior to forming the at least one photochromic-dichroic compound that is at least partially aligned on the at least a portion of the substrate.
190. The method of claim 185 further comprising applying a sheet chosen from linearly polarizing sheets, circularly polarizing sheets, elliptically polarizing sheets, photochromic sheets, reflective sheets, tinted sheets, retarder sheets, and wide-angle view sheets to at least a portion of the substrate after forming the at least one photochromic-dichroic compound that is at least partially aligned on the at least a portion of the substrate.
191. A liquid crystal cell comprising:
a first substrate having a first surface;
a second substrate having a second surface, wherein the second surface of the second substrate is opposite and spaced apart from the first surface of the first substrate so as to define a region; and a liquid crystal material adapted to be at least partially ordered and at least one thermally reversible photochromic-dichroic compound adapted to be at least partially aligned and having an aver age absorption ratio greater than 2.3 in an activated state as determined according to CELL METHOD positioned within the region defined by the first surface and the second surface.
192. The liquid crystal cell of claim 191 wherein the liquid crystal cell is a display element chosen from screens, monitors, and security elements.
193. The liquid crystal cell of claim 191 wherein the first substrate and the second substrate are independently chosen from untinted substrates, tinted substrates, photochromic substrates, tinted-photochromic substrates, linearly polarizing substrates, circularly polarizing substrates, and elliptically polarizing substrates.
194. The liquid crystal cell of claim 191 further comprising a first orientation facility positioned adjacent the first surface and a second orientation facility positioned adjacent the second surface.
195. The liquid crystal cell of claim 194 further comprising a first electrode interposed between at least a portion of the first orientation facility and the first surface, and a second electrode interposed between at least a portion of the second orientation facility and the second surface.
196. The liquid crystal cell of claim 195 wherein the liquid crystal cell forms at least a portion .
of an electrical circuit.
197. The liquid crystal cell of claim 191 further comprising a first electrode adjacent the first surface, and a second electrode adjacent the second surface.
198. The liquid crystal cell of claim 191 wherein the liquid crystal cell forms at least a portion of an electrical circuit.
199. The liquid crystal cell of claim 191 further comprising an at least partial coating chosen from linearly polarizing coatings, circularly polarizing coatings, elliptically polarizing coatings, photochromic coatings, reflective coatings, tinted coatings, retarder coatings, and wide-angle view coatings connected to at least a portion of a surface of at least one of the first substrate and the second substrate.
200. The liquid crystal cell of claim 191 further comprising at least one sheet chosen from linearly polarizing sheets, circularly polarizing sheets, elliptically polarizing sheets, photochromic sheets, reflective sheets, tinted sheets, retarder sheets, and wide-angle view sheets connected to at feast a portion of a surface of at least one of the first substrate and the second substrate.
201. An optical element comprising:
a substrate; and an at least partial coating having a first state and a second state on at least a portion of the substrate, the at least partial coating being adapted to be circularly polarizing or elliptically polarizing in at least one state-and comprising:
a chiral nematic or cholesteric liquid crystal material having molecules that-are helically arranged through a thickness of the at least partial coating;
and at least one photochromic-dichroic compound that is at least partially aligned with the liquid crystal material such that a long axis of a molecule of the at least one photochromic-dichroic compound is generally parallel to the molecules of the liquid crystal material.
202. An optical element comprising:
a substrate; and an at least partial coating connected to at least a portion of the substrate, the at least partial coating comprising an at least partially ordered anisotropic material and at least one photochromic-dichroic compound that is at least partially aligned with the at least partially ordered anisotropic material, said photochromic-dichroic compound comprising:
(a) at least one photochromic group chosen from a pyran, an oxazine, and a fulgide; and (b) at least one lengthening agent L attached to the at least one photochromic group and represented by::
-[S1]c-[Q1 -[S2]d]d'-[Q2 -[S3]e]e'-[Q3 -[S4]f]f'-S5-P
wherein:
(i) each Q1, Q2, and Q3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, thiol, amide, liquid crystal mesogens, halogen, C1-C18 alkoxy, poly(C1-C18 alkoxy), amino, amino(C1-C18)alkylene, C2-C18alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl, C2-C18 alkene, C2-C18 alkyne, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkyl carbonate, aryl carbonate, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, isocyanato, amido, cyano, nitro, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:
(A) -(CH2)9-, -(CF2)h-, -Si(CH2)g-, -(Si[(CH3)2]O)h-, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(B) -N(Z)-, -C(Z)=C(Z)-, -C(Z)=N-, -C(Z')-C(Z')-, wherein Z is independently chosen for each occurrence from hydrogen, C1-C6 alkyl, cycloalkyl and aryl, and Z' is independently chosen for each occurrence from C1-C6 alkyl, cycloalkyl and aryl; and (C) -O-, -C(O)-, -C.ident.-C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo;
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S1 and S5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;
(iii) P is chosen from: aziridinyl, hydrogen, hydroxy, aryl, alkyl, alkoxy, amino, alkylamino, alkylalkoxy, alkoxyalkoxy, nitro, polyalkyl ether, (C1-C6)alkyl(C1-C6)alkoxy(C1-C6)alkyl, polyethyleneoxy, polypropyleneoxy, ethylene, acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acryloylphenylene, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, epoxy, isocyanate, thiol, thioisocyanate, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, siloxane, main-chain and side-chain liquid crystal polymers, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, and substituted and unsubstituted chiral and non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from alkyl, alkoxy, amino, cycloalkyl, alkylalkoxy, fluoroalkyl, cyanoalkyl, cyanoalkoxy and mixtures thereof; and (iv) d', e' and f' are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d'+e'+f'is at 1.
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Families Citing this family (196)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11026768B2 (en) | 1998-10-08 | 2021-06-08 | Align Technology, Inc. | Dental appliance reinforcement |
US7978391B2 (en) * | 2004-05-17 | 2011-07-12 | Transitions Optical, Inc. | Polarizing, photochromic devices and methods of making the same |
US8089678B2 (en) * | 2003-07-01 | 2012-01-03 | Transitions Optical, Inc | Clear to circular polarizing photochromic devices and methods of making the same |
US7632540B2 (en) * | 2003-07-01 | 2009-12-15 | Transitions Optical, Inc. | Alignment facilities for optical dyes |
US8545984B2 (en) | 2003-07-01 | 2013-10-01 | Transitions Optical, Inc. | Photochromic compounds and compositions |
US9096014B2 (en) * | 2003-07-01 | 2015-08-04 | Transitions Optical, Inc. | Oriented polymeric sheets exhibiting dichroism and articles containing the same |
US8582192B2 (en) | 2003-07-01 | 2013-11-12 | Transitions Optical, Inc. | Polarizing photochromic articles |
US7256921B2 (en) * | 2003-07-01 | 2007-08-14 | Transitions Optical, Inc. | Polarizing, photochromic devices and methods of making the same |
US8698117B2 (en) | 2003-07-01 | 2014-04-15 | Transitions Optical, Inc. | Indeno-fused ring compounds |
US7342112B2 (en) * | 2003-07-01 | 2008-03-11 | Ppg Industries Ohio, Inc. | Photochromic compounds |
US8518546B2 (en) | 2003-07-01 | 2013-08-27 | Transitions Optical, Inc. | Photochromic compounds and compositions |
US8211338B2 (en) | 2003-07-01 | 2012-07-03 | Transitions Optical, Inc | Photochromic compounds |
US8545015B2 (en) | 2003-07-01 | 2013-10-01 | Transitions Optical, Inc. | Polarizing photochromic articles |
DE10331798B4 (en) * | 2003-07-14 | 2012-06-21 | Giesecke & Devrient Gmbh | Security element, valuable item, transfer material and manufacturing process |
US7097303B2 (en) * | 2004-01-14 | 2006-08-29 | Ppg Industries Ohio, Inc. | Polarizing devices and methods of making the same |
US9492245B2 (en) | 2004-02-27 | 2016-11-15 | Align Technology, Inc. | Method and system for providing dynamic orthodontic assessment and treatment profiles |
US8563212B2 (en) * | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles, non-aqueous dispersions thereof and articles prepared therewith |
US8563213B2 (en) * | 2004-07-16 | 2013-10-22 | Transitions Optical, Inc. | Methods for producing photosensitive microparticles |
US20070052886A1 (en) * | 2005-03-23 | 2007-03-08 | Bunsen Fan | Contact lenses with selective spectral blocking and method of fabrication thereof |
US7556750B2 (en) * | 2005-04-08 | 2009-07-07 | Transitions Optical, Inc. | Photochromic materials with reactive substituents |
US20060228557A1 (en) * | 2005-04-08 | 2006-10-12 | Beon-Kyu Kim | Photochromic materials having extended pi-conjugated systems and compositions and articles including the same |
US9052438B2 (en) | 2005-04-08 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices comprising photochromic materials with reactive substituents |
US7349140B2 (en) * | 2005-05-31 | 2008-03-25 | Miradia Inc. | Triple alignment substrate method and structure for packaging devices |
US7229740B2 (en) * | 2005-09-08 | 2007-06-12 | Xerox Corporation | Reimageable paper |
US7381506B2 (en) * | 2005-09-08 | 2008-06-03 | Xerox Corporation | Reimageable paper |
US7556751B2 (en) * | 2005-12-21 | 2009-07-07 | Transitions Optical, Inc. | Photochromic materials having electron-withdrawing substituents |
US20070138667A1 (en) * | 2005-12-21 | 2007-06-21 | Dang Hoa T | In-mold coating compositions for optical lenses |
US7644512B1 (en) * | 2006-01-18 | 2010-01-12 | Akrion, Inc. | Systems and methods for drying a rotating substrate |
DE102006023965A1 (en) * | 2006-05-22 | 2007-11-29 | Rodenstock Gmbh | Photochromic plastic article with increased contrast and a reduction of scattering effects and glare |
US20070286969A1 (en) * | 2006-06-08 | 2007-12-13 | Ppg Industries Ohio, Inc. | Polarizing optical elements and method for preparing polyurethane-containing films |
US8697890B2 (en) * | 2006-10-20 | 2014-04-15 | Alphamicron Incorporated | Dichroic-photochromic 2H-naphtho[1,2-b]pyran compounds and devices |
US9102652B2 (en) | 2006-10-20 | 2015-08-11 | Alphamicron Incorporated | Dichroic-photochromic 2H-naphtho[1,2-b]pyran compounds and devices |
JP2008122485A (en) * | 2006-11-09 | 2008-05-29 | Nitto Denko Corp | Polarizer, polarizing plate, circular polarization filter, image display device, and manufacturing method of polarizer |
US8596783B1 (en) | 2006-12-05 | 2013-12-03 | Michael Cain Finley | Light control system and associated methods |
US20080187749A1 (en) * | 2007-01-11 | 2008-08-07 | Ppg Industries Ohio, Inc. | Optical element having light influencing property |
US7906214B2 (en) | 2007-01-26 | 2011-03-15 | Transitions Optical, Inc. | Optical elements comprising compatiblizing coatings and methods of making the same |
US20080273169A1 (en) | 2007-03-29 | 2008-11-06 | Blum Ronald D | Multifocal Lens Having a Progressive Optical Power Region and a Discontinuity |
US7883206B2 (en) * | 2007-03-07 | 2011-02-08 | Pixeloptics, Inc. | Multifocal lens having a progressive optical power region and a discontinuity |
US7878805B2 (en) | 2007-05-25 | 2011-02-01 | Align Technology, Inc. | Tabbed dental appliance |
US7666558B2 (en) * | 2007-06-13 | 2010-02-23 | Xerox Corporation | Inkless reimageable printing paper and method |
US7588878B2 (en) * | 2007-06-13 | 2009-09-15 | Xerox Corporation | Inkless printing paper and method |
US7572569B2 (en) * | 2007-06-13 | 2009-08-11 | Xerox Corporation | Inkless printing paper and method |
US7569316B2 (en) * | 2007-06-13 | 2009-08-04 | Xerox Corporation | Inkless reimageable printing paper and method |
US7541119B2 (en) * | 2007-06-13 | 2009-06-02 | Xerox Corporation | Inkless reimageable printing paper and method |
US7582398B2 (en) * | 2007-06-13 | 2009-09-01 | Xerox Corporation | Inkless reimageable printing paper and method |
US7645558B2 (en) * | 2007-06-13 | 2010-01-12 | Xerox Corporation | Inkless reimageable printing paper and method |
US7655366B2 (en) | 2007-06-13 | 2010-02-02 | Xerox Corporation | Inkless reimageable printing paper and method |
US20080311493A1 (en) * | 2007-06-13 | 2008-12-18 | Xerox Corporation | Inkless reimageable printing paper and method |
US7553603B2 (en) * | 2007-06-13 | 2009-06-30 | Xerox Corporation | Inkless printing paper and method |
US7852366B2 (en) * | 2007-06-13 | 2010-12-14 | Xerox Corporation | System and method for printing reimageable transient documents |
US7572560B2 (en) * | 2007-06-13 | 2009-08-11 | Xerox Corporation | Inkless reimageable printing paper and method |
US7867672B2 (en) * | 2007-06-13 | 2011-01-11 | Xerox Corporation | Reimageable paper protected against UV light |
US7718325B2 (en) * | 2007-06-13 | 2010-05-18 | Xerox Corporation | Photochromic material, inkless reimageable printing paper, and methods |
US8738394B2 (en) | 2007-11-08 | 2014-05-27 | Eric E. Kuo | Clinical data file |
US20090122261A1 (en) * | 2007-11-09 | 2009-05-14 | Insight Equity A.P.X., L.P. | Reflective Polarized Lenses With High Transmission |
US8940219B2 (en) * | 2007-12-31 | 2015-01-27 | Ronald D. Spoor | Ophthalmic device formed by additive fabrication and method thereof |
US8108189B2 (en) | 2008-03-25 | 2012-01-31 | Align Technologies, Inc. | Reconstruction of non-visible part of tooth |
US8092215B2 (en) | 2008-05-23 | 2012-01-10 | Align Technology, Inc. | Smile designer |
US9492243B2 (en) | 2008-05-23 | 2016-11-15 | Align Technology, Inc. | Dental implant positioning |
US8172569B2 (en) | 2008-06-12 | 2012-05-08 | Align Technology, Inc. | Dental appliance |
US20090326186A1 (en) * | 2008-06-27 | 2009-12-31 | Transitions Optical, Inc. | Mesogen containing compounds |
US20100014010A1 (en) * | 2008-06-27 | 2010-01-21 | Transitions Optical, Inc. | Formulations comprising mesogen containing compounds |
US7910019B2 (en) | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Mesogen containing compounds |
US8349210B2 (en) | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
US8431039B2 (en) | 2008-06-27 | 2013-04-30 | Transitions Optical, Inc. | Mesogenic stabilizers |
US8628685B2 (en) | 2008-06-27 | 2014-01-14 | Transitions Optical, Inc | Mesogen-containing compounds |
US8623238B2 (en) | 2008-06-27 | 2014-01-07 | Transitions Optical, Inc. | Mesogenic stabilizers |
US8613868B2 (en) | 2008-06-27 | 2013-12-24 | Transitions Optical, Inc | Mesogenic stabilizers |
US7910020B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Liquid crystal compositions comprising mesogen containing compounds |
US7645560B1 (en) * | 2008-09-08 | 2010-01-12 | Xerox Corporation | Inkless reimageable printing paper and method |
US8152518B2 (en) | 2008-10-08 | 2012-04-10 | Align Technology, Inc. | Dental positioning appliance having metallic portion |
JP2010134424A (en) * | 2008-11-04 | 2010-06-17 | Hoya Corp | Method of manufacturing polarizing lens |
US7811741B2 (en) * | 2009-02-24 | 2010-10-12 | Xerox Corporation | Reverse write erasable paper |
US7935463B2 (en) * | 2009-03-09 | 2011-05-03 | Xerox Corporation | Reusable paper media with compatibility markings and printer with incompatible media sensor |
US8292617B2 (en) | 2009-03-19 | 2012-10-23 | Align Technology, Inc. | Dental wire attachment |
CN102460291B (en) * | 2009-06-11 | 2015-11-25 | 思维奇材料公司 | Variable light transmittance optical filter and application thereof |
US8765031B2 (en) | 2009-08-13 | 2014-07-01 | Align Technology, Inc. | Method of forming a dental appliance |
CN102695528B (en) | 2009-08-21 | 2016-07-13 | 诺万公司 | Wound dressing, its using method and forming method thereof |
CA3062005C (en) | 2009-08-21 | 2022-02-15 | Novan, Inc. | Topical gels comprising nitric oxide-releasing polysiloxane macromolecules and uses thereof |
US9475901B2 (en) * | 2009-12-08 | 2016-10-25 | Transitions Optical, Inc. | Photoalignment materials having improved adhesion |
KR101146986B1 (en) | 2010-03-16 | 2012-05-22 | 삼성모바일디스플레이주식회사 | Optical filter and organic light emitting device having the same |
US8770749B2 (en) | 2010-04-15 | 2014-07-08 | Oakley, Inc. | Eyewear with chroma enhancement |
US9211166B2 (en) | 2010-04-30 | 2015-12-15 | Align Technology, Inc. | Individualized orthodontic treatment index |
US9241774B2 (en) | 2010-04-30 | 2016-01-26 | Align Technology, Inc. | Patterned dental positioning appliance |
KR101676313B1 (en) | 2010-05-31 | 2016-11-16 | 삼성디스플레이 주식회사 | Organic light emitting device |
US8673183B2 (en) | 2010-07-06 | 2014-03-18 | National Research Council Of Canada | Tetrazine monomers and copolymers for use in organic electronic devices |
US8467177B2 (en) | 2010-10-29 | 2013-06-18 | Apple Inc. | Displays with polarizer windows and opaque masking layers for electronic devices |
US8859097B2 (en) * | 2010-12-16 | 2014-10-14 | Transitions Optical, Inc. | Photochromic compounds, compositions and articles |
US8920928B2 (en) | 2010-12-16 | 2014-12-30 | Transitions Optical, Inc. | Photochromic compounds and compositions |
US9034219B2 (en) | 2010-12-16 | 2015-05-19 | Transitions Optical, Inc. | Photochromic compounds and compositions |
US8736992B2 (en) * | 2011-05-11 | 2014-05-27 | KiloLambda Technologies, Inc. | Wavelength-specific wide impinging angle limiter |
MX363607B (en) * | 2011-06-06 | 2019-03-27 | Transitions Optical Inc | Polarizing photochromic articles. |
BR112013031234B1 (en) | 2011-06-06 | 2021-01-26 | Transitions Optical, Inc. | photochromic article |
US9334345B2 (en) | 2011-09-08 | 2016-05-10 | Ppg Industries Ohio, Inc. | Polymerizable compositions containing (meth)acrylate monomers having sulfide linkages |
US9403238B2 (en) | 2011-09-21 | 2016-08-02 | Align Technology, Inc. | Laser cutting |
AU2012336204B2 (en) | 2011-10-20 | 2016-08-25 | Oakley, Inc. | Eyewear with chroma enhancement |
BR112014015418A8 (en) | 2011-12-23 | 2017-07-04 | Johnson & Johnson Vision Care | variable optic ophthalmic device including liquid crystal elements |
US9375300B2 (en) | 2012-02-02 | 2016-06-28 | Align Technology, Inc. | Identifying forces on a tooth |
US9220580B2 (en) | 2012-03-01 | 2015-12-29 | Align Technology, Inc. | Determining a dental treatment difficulty |
WO2013169987A1 (en) | 2012-05-10 | 2013-11-14 | Oakley, Inc. | Eyewear with laminated functional layers |
US9414897B2 (en) | 2012-05-22 | 2016-08-16 | Align Technology, Inc. | Adjustment of tooth position in a virtual dental model |
US9030740B2 (en) | 2012-09-14 | 2015-05-12 | Transitions Optical, Inc. | Photochromic article having at least partially crossed polarized photochromic-dichroic and fixed-polarized layers |
US8649081B1 (en) * | 2012-09-14 | 2014-02-11 | Transitions Optical, Inc. | Photochromic article having two at least partially crossed photochromic-dichroic layers |
CN103013532A (en) * | 2012-11-30 | 2013-04-03 | 浙江工业大学 | Azobenzene photochromic liquid crystal compound and method for synthesizing same |
US10386653B2 (en) | 2012-12-21 | 2019-08-20 | Johnson & Johnson Vision Care, Inc. | Variable optic ophthalmic device including liquid crystal elements |
US9304330B2 (en) | 2013-02-20 | 2016-04-05 | Transitions Optical, Inc. | Experiential optical device |
US9204962B2 (en) | 2013-03-13 | 2015-12-08 | Acufocus, Inc. | In situ adjustable optical mask |
US20140265010A1 (en) * | 2013-03-13 | 2014-09-18 | Transitions Optical, Inc. | Method of preparing photochromic-dichroic films having reduced optical distortion |
US20140264979A1 (en) | 2013-03-13 | 2014-09-18 | Transitions Opticals, Inc. | Method of preparing photochromic-dichroic films having reduced optical distortion |
KR101341072B1 (en) * | 2013-09-04 | 2013-12-19 | 안재광 | Label for identifying genuine article comprising multiple nano structure and stereoscopic lens |
US9869885B2 (en) | 2013-09-17 | 2018-01-16 | Johnson & Johnson Vision Care, Inc. | Method and apparatus for ophthalmic devices including gradient-indexed liquid crystal layers and shaped dielectric layers |
US9541772B2 (en) | 2013-09-17 | 2017-01-10 | Johnson & Johnson Vision Care, Inc. | Methods and apparatus for ophthalmic devices including cycloidally oriented liquid crystal layers |
US9592116B2 (en) | 2013-09-17 | 2017-03-14 | Johnson & Johnson Vision Care, Inc. | Methods and apparatus for ophthalmic devices including cycloidally oriented liquid crystal layers |
US9880398B2 (en) | 2013-09-17 | 2018-01-30 | Johnson & Johnson Vision Care, Inc. | Method and apparatus for ophthalmic devices including gradient-indexed and shaped liquid crystal layers |
US9500882B2 (en) | 2013-09-17 | 2016-11-22 | Johnson & Johnson Vision Care, Inc. | Variable optic ophthalmic device including shaped liquid crystal elements with nano-scaled droplets of liquid crystal |
KR102089663B1 (en) * | 2013-09-27 | 2020-03-16 | 엘지디스플레이 주식회사 | Flexible Display Device and Method of manufacturing the same |
CN103631031B (en) * | 2013-09-30 | 2015-03-25 | 丹阳佰易视光学眼镜有限公司 | Dynamic progressive multi-focal-point lens |
US10688522B2 (en) | 2013-11-20 | 2020-06-23 | Transitions Optical, Inc. | Method of coating a lens and lens support |
US9575335B1 (en) | 2014-01-10 | 2017-02-21 | Oakley, Inc. | Eyewear with chroma enhancement for specific activities |
MX362748B (en) | 2014-03-14 | 2019-02-05 | Ppg Ind Ohio Inc | Electroactive optical device. |
US10871661B2 (en) | 2014-05-23 | 2020-12-22 | Oakley, Inc. | Eyewear and lenses with multiple molded lens components |
US10772506B2 (en) | 2014-07-07 | 2020-09-15 | Align Technology, Inc. | Apparatus for dental confocal imaging |
US9693839B2 (en) | 2014-07-17 | 2017-07-04 | Align Technology, Inc. | Probe head and apparatus for intraoral confocal imaging using polarization-retarding coatings |
US9675430B2 (en) | 2014-08-15 | 2017-06-13 | Align Technology, Inc. | Confocal imaging apparatus with curved focal surface |
US9610141B2 (en) | 2014-09-19 | 2017-04-04 | Align Technology, Inc. | Arch expanding appliance |
US10449016B2 (en) | 2014-09-19 | 2019-10-22 | Align Technology, Inc. | Arch adjustment appliance |
AU2015324313B2 (en) | 2014-09-30 | 2018-11-15 | Transitions Optical, Inc. | Ultraviolet light absorbers |
US9744001B2 (en) | 2014-11-13 | 2017-08-29 | Align Technology, Inc. | Dental appliance with cavity for an unerupted or erupting tooth |
CN207704150U (en) | 2014-11-13 | 2018-08-07 | 奥克利有限公司 | Variable optical attenuation eyewear with color enhancing |
US9905022B1 (en) | 2015-01-16 | 2018-02-27 | Oakley, Inc. | Electronic display for demonstrating eyewear functionality |
WO2016118130A1 (en) | 2015-01-22 | 2016-07-28 | Transitions Optical, Inc. | Optical article having a photoluminescent mark |
US10504386B2 (en) | 2015-01-27 | 2019-12-10 | Align Technology, Inc. | Training method and system for oral-cavity-imaging-and-modeling equipment |
JP6647753B2 (en) * | 2015-04-17 | 2020-02-14 | 日東電工株式会社 | Polarizing plate and manufacturing method thereof |
WO2016187772A1 (en) | 2015-05-25 | 2016-12-01 | 华为技术有限公司 | Photochromic lens, camera and terminal device |
WO2016200394A1 (en) | 2015-06-12 | 2016-12-15 | Transitions Optical, Inc. | Alignment polymers |
EP3307798B1 (en) | 2015-06-12 | 2020-08-05 | Transitions Optical, Inc. | Alignment compounds |
US10248883B2 (en) | 2015-08-20 | 2019-04-02 | Align Technology, Inc. | Photograph-based assessment of dental treatments and procedures |
CN107924116B (en) * | 2015-09-03 | 2021-06-15 | 光学转变公司 | Multilayer photochromic articles |
CN108351451B (en) | 2015-10-30 | 2021-08-31 | 光学转变公司 | Optical article having gradient light influencing properties and method of making same |
CA3003496C (en) | 2015-10-30 | 2023-07-11 | Transitions Optical, Inc. | Optical articles and method of preparing the same |
EP3368926B1 (en) | 2015-10-30 | 2024-03-06 | Transitions Optical Ltd. | A method of making an optical article with an inkjet printing device |
US11554000B2 (en) | 2015-11-12 | 2023-01-17 | Align Technology, Inc. | Dental attachment formation structure |
US11931222B2 (en) | 2015-11-12 | 2024-03-19 | Align Technology, Inc. | Dental attachment formation structures |
US11103330B2 (en) | 2015-12-09 | 2021-08-31 | Align Technology, Inc. | Dental attachment placement structure |
US11596502B2 (en) | 2015-12-09 | 2023-03-07 | Align Technology, Inc. | Dental attachment placement structure |
US10227374B2 (en) | 2016-04-21 | 2019-03-12 | Ohara Pharmaceutical Co., Ltd. | Silyl etherified derivatives of 5-azacytidines in carbohydrate moiety |
US10383705B2 (en) | 2016-06-17 | 2019-08-20 | Align Technology, Inc. | Orthodontic appliance performance monitor |
WO2017218947A1 (en) | 2016-06-17 | 2017-12-21 | Align Technology, Inc. | Intraoral appliances with sensing |
KR102546050B1 (en) | 2016-07-27 | 2023-06-22 | 얼라인 테크널러지, 인크. | Intraoral scanner with dental diagnostics capabilities |
US10507087B2 (en) | 2016-07-27 | 2019-12-17 | Align Technology, Inc. | Methods and apparatuses for forming a three-dimensional volumetric model of a subject's teeth |
CN109922754B (en) | 2016-11-04 | 2021-10-01 | 阿莱恩技术有限公司 | Method and apparatus for dental images |
US11376101B2 (en) | 2016-12-02 | 2022-07-05 | Align Technology, Inc. | Force control, stop mechanism, regulating structure of removable arch adjustment appliance |
EP3824843A1 (en) | 2016-12-02 | 2021-05-26 | Align Technology, Inc. | Palatal expanders and methods of expanding a palate |
AU2017366755B2 (en) | 2016-12-02 | 2022-07-28 | Align Technology, Inc. | Methods and apparatuses for customizing rapid palatal expanders using digital models |
WO2018102702A1 (en) | 2016-12-02 | 2018-06-07 | Align Technology, Inc. | Dental appliance features for speech enhancement |
US10548700B2 (en) | 2016-12-16 | 2020-02-04 | Align Technology, Inc. | Dental appliance etch template |
CN110087869A (en) | 2016-12-23 | 2019-08-02 | 光学转变有限公司 | There is the method for the lens of graded properties using the manufacture of imbibition technology |
EP3562655A1 (en) | 2016-12-28 | 2019-11-06 | Transitions Optical, Ltd. | Method for imparting an optical element with a light influencing property in a gradient pattern |
US10456043B2 (en) | 2017-01-12 | 2019-10-29 | Align Technology, Inc. | Compact confocal dental scanning apparatus |
US10779718B2 (en) | 2017-02-13 | 2020-09-22 | Align Technology, Inc. | Cheek retractor and mobile device holder |
CN106773126A (en) * | 2017-03-08 | 2017-05-31 | 黄世杰 | A kind of Electrocontrolled color change glasses |
US10613515B2 (en) | 2017-03-31 | 2020-04-07 | Align Technology, Inc. | Orthodontic appliances including at least partially un-erupted teeth and method of forming them |
EP3396439A1 (en) * | 2017-04-26 | 2018-10-31 | Essilor International | Hybrid glass and plastic laminated lenses and method of making same |
US11045283B2 (en) | 2017-06-09 | 2021-06-29 | Align Technology, Inc. | Palatal expander with skeletal anchorage devices |
US10639134B2 (en) | 2017-06-26 | 2020-05-05 | Align Technology, Inc. | Biosensor performance indicator for intraoral appliances |
US10885521B2 (en) | 2017-07-17 | 2021-01-05 | Align Technology, Inc. | Method and apparatuses for interactive ordering of dental aligners |
WO2019018784A1 (en) | 2017-07-21 | 2019-01-24 | Align Technology, Inc. | Palatal contour anchorage |
US11633268B2 (en) | 2017-07-27 | 2023-04-25 | Align Technology, Inc. | Tooth shading, transparency and glazing |
EP3658067B1 (en) | 2017-07-27 | 2023-10-25 | Align Technology, Inc. | System and methods for processing an orthodontic aligner by means of an optical coherence tomography |
US10859868B2 (en) | 2017-08-11 | 2020-12-08 | Coopervision International Limited | Flexible liquid crystal cells and lenses |
US11116605B2 (en) | 2017-08-15 | 2021-09-14 | Align Technology, Inc. | Buccal corridor assessment and computation |
WO2019036677A1 (en) | 2017-08-17 | 2019-02-21 | Align Technology, Inc. | Dental appliance compliance monitoring |
US10813720B2 (en) | 2017-10-05 | 2020-10-27 | Align Technology, Inc. | Interproximal reduction templates |
US10866455B2 (en) | 2017-10-19 | 2020-12-15 | Ppg Industries Ohio, Inc. | Display devices including photochromic-dichroic compounds and dichroic compounds |
CN111565668B (en) | 2017-10-27 | 2022-06-07 | 阿莱恩技术有限公司 | Substitute occlusion adjusting structure |
EP3703608B1 (en) | 2017-10-31 | 2023-08-30 | Align Technology, Inc. | Determination of a dental appliance having selective occlusal loading and controlled intercuspation |
CN111315315B (en) | 2017-11-01 | 2022-08-23 | 阿莱恩技术有限公司 | Automated therapy planning |
WO2019100022A1 (en) | 2017-11-17 | 2019-05-23 | Align Technology, Inc. | Orthodontic retainers |
EP3716885B1 (en) | 2017-11-30 | 2023-08-30 | Align Technology, Inc. | Orthodontic intraoral appliances comprising sensors |
WO2019110102A1 (en) | 2017-12-07 | 2019-06-13 | Transitions Optical, Ltd. | Controllable tint photochromic article |
WO2019118876A1 (en) | 2017-12-15 | 2019-06-20 | Align Technology, Inc. | Closed loop adaptive orthodontic treatment methods and apparatuses |
EP3732533A1 (en) | 2017-12-27 | 2020-11-04 | Transitions Optical, Ltd. | System and method for customization of a photochromic article |
US10980613B2 (en) | 2017-12-29 | 2021-04-20 | Align Technology, Inc. | Augmented reality enhancements for dental practitioners |
CA3086553A1 (en) | 2018-01-26 | 2019-08-01 | Align Technology, Inc. | Diagnostic intraoral scanning and tracking |
US11112622B2 (en) | 2018-02-01 | 2021-09-07 | Luxottica S.R.L. | Eyewear and lenses with multiple molded lens components |
US11937991B2 (en) | 2018-03-27 | 2024-03-26 | Align Technology, Inc. | Dental attachment placement structure |
KR20200141498A (en) | 2018-04-11 | 2020-12-18 | 얼라인 테크널러지, 인크. | Releasable palate dilator |
US11003016B2 (en) | 2018-09-21 | 2021-05-11 | Coopervision International Limited | Flexible, adjustable lens power liquid crystal cells and lenses |
JP7113962B2 (en) * | 2019-03-28 | 2022-08-05 | 富士フイルム株式会社 | Manufacturing method of cholesteric liquid crystal film |
EP3795602B1 (en) | 2019-09-19 | 2024-02-07 | Essilor International | 2k pu-dual cure adhesive for lamination |
KR20210082320A (en) * | 2019-12-24 | 2021-07-05 | 삼성디스플레이 주식회사 | Display decvice |
CN111575097B (en) * | 2020-06-15 | 2021-04-16 | 清华大学 | Solution with optically variable viscosity and method for regulating fluid viscosity |
CA3195726A1 (en) | 2020-11-10 | 2022-05-19 | Henry Nguyen | Photochromic-dichroic articles |
EP4244304A1 (en) | 2020-11-10 | 2023-09-20 | Transitions Optical, Ltd. | Method for preparing a coated article |
CN113314851B (en) * | 2021-05-19 | 2022-10-18 | 中南大学 | Polarization insensitive frequency reconfigurable super surface wave absorber |
US20230066064A1 (en) | 2021-08-31 | 2023-03-02 | Ppg Industries Ohio, Inc. | Electroactive optical device |
Family Cites Families (177)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2475921A (en) | 1940-06-26 | 1949-07-12 | Polaroid Corp | Glare reduction filter comprising light polarizing area merging gradually with transparent nonpolarizing area |
GB583842A (en) | 1941-01-21 | 1947-01-01 | Polaroid Corp | Improvements in or relating to combined light-filtering and light-polarizing means |
US2319826A (en) | 1941-10-10 | 1943-05-25 | Gen Electric | Adhesive composition |
US2334446A (en) | 1941-12-26 | 1943-11-16 | Polaroid Corp | Polarizing goggles |
US2315826A (en) | 1942-02-27 | 1943-04-06 | Kearney James R Corp | Wire attaching device |
US2544659A (en) | 1946-05-14 | 1951-03-13 | John F Dreyer | Dichroic light-polarizing sheet materials and the like and the formation and use thereof |
US2481830A (en) | 1946-05-14 | 1949-09-13 | Gen Polarizing Company | Optically polarizing dichroic film and method of preparing the same |
US3276316A (en) | 1961-08-02 | 1966-10-04 | Polaroid Corp | Process for polarizing ultraviolet light utilizing oriented polymer sheet with incorporated dichroic fluorescent dye |
US3361706A (en) | 1964-03-06 | 1968-01-02 | American Cyanamid Co | Control of the photochromic return rate of (arylazo) thioformic arylhydrazidates |
US3653863A (en) | 1968-07-03 | 1972-04-04 | Corning Glass Works | Method of forming photochromic polarizing glasses |
US3661706A (en) * | 1970-11-06 | 1972-05-09 | Allis Chalmers Mfg Co | Air loaded headbox for a papermaking machine having vertically aligned vanes therein |
US4043637A (en) | 1973-06-15 | 1977-08-23 | American Optical Corporation | Photochromic light valve |
US4049338A (en) | 1974-11-19 | 1977-09-20 | Texas Instruments Incorporated | Light polarizing material method and apparatus |
US4166043A (en) | 1974-12-23 | 1979-08-28 | American Optical Corporation | Stabilized photochromic materials |
US4367170A (en) | 1975-01-24 | 1983-01-04 | American Optical Corporation | Stabilized photochromic materials |
US4080051A (en) * | 1976-03-18 | 1978-03-21 | American Optical Corporation | Preparation of photochromic gradient lenses of cosmetically improved color |
US4039254A (en) | 1976-05-27 | 1977-08-02 | Mack Gordon | Electro-optic welding lens assembly using multiple liquid crystal light shutters and polarizers |
US4125404A (en) * | 1976-11-05 | 1978-11-14 | Corning Glass Works | Photochromic glasses exhibiting dichroism, birefringence and color adaptation |
US4190330A (en) | 1977-12-27 | 1980-02-26 | Bell Telephone Laboratories, Incorporated | Variable focus liquid crystal lens system |
US4279474A (en) | 1980-03-25 | 1981-07-21 | Belgorod Barry M | Spectacle lens having continuously variable controlled density and fast response time |
US4459662A (en) * | 1980-09-29 | 1984-07-10 | Texas Instruments Incorporated | Microcomputer having ROM mass memory for downloading main RAM memory with microcomputer instructions |
FR2531235B1 (en) | 1982-07-27 | 1985-11-15 | Corning Glass Works | POLARIZING TRANSPARENT LAMINATE GLASSES AND PROCESS FOR OBTAINING SAME |
US4556605A (en) | 1982-09-09 | 1985-12-03 | Kabushiki Kaisha Suwa Seikosha | Photochromic coating composition and photochromic synthetic resin ophthalmic lens |
US4637896A (en) | 1982-12-15 | 1987-01-20 | Armstrong World Industries, Inc. | Polymeric liquid crystals |
US4685783A (en) | 1983-09-07 | 1987-08-11 | The Plessey Company P.L.C. | Polychromic tetracyclo-spiro-adamatylidene derivatives, and polychromic lens incorporating said compounds |
US4549330A (en) * | 1983-09-30 | 1985-10-29 | Devro, Inc. | Apparatus for preparing sausage links |
SE464264B (en) | 1984-02-24 | 1991-03-25 | Esab Ab | OPTICAL FILTER FOR WELDING GLASS |
US4549894A (en) | 1984-06-06 | 1985-10-29 | Corning Glass Works | Ultraviolet absorbing photochromic glass of low silver content |
FR2568568A1 (en) | 1984-08-01 | 1986-02-07 | Corning Glass Works | IMPROVEMENT IN THE MANUFACTURE OF POLARIZING TRANSPARENT LAMINATE LENSES AND LENSES THUS OBTAINED |
GB2169417A (en) | 1984-12-28 | 1986-07-09 | Olympus Optical Co | Liquid crystal lens having a variable focal length |
US4756605A (en) | 1985-02-01 | 1988-07-12 | Olympus Optical Co., Ltd. | Liquid crystal spectacles |
AU564689B2 (en) | 1985-07-09 | 1987-08-20 | Kureha Kagaku Kogyo K.K. | Photochromic lens |
FR2590889B1 (en) | 1985-08-13 | 1988-01-22 | Corning Glass Works | IMPROVEMENTS IN THE MANUFACTURE OF POLARIZING TRANSPARENT LAMINATED GLASSES AND GLASSES OBTAINED THEREBY |
DE3531923A1 (en) | 1985-09-07 | 1987-03-12 | Bayer Ag | METHOD FOR PRODUCING 1-AMINONAPHTHALINE-2,4,7-TRISULFONIC ACID AND 1-AMINONAPHTHALINE-7-SULPHONIC ACID |
US4810433A (en) | 1985-09-25 | 1989-03-07 | Fuji Photo Film Co., Ltd. | Process for producing oriented film |
IT1190508B (en) | 1986-03-24 | 1988-02-16 | Daniele Senatore | ADJUSTABLE TRANSPARENCY GLASSES |
US5036890A (en) * | 1986-04-01 | 1991-08-06 | Whaley H Dean | Hose reinforcement device |
DE3774437D1 (en) | 1986-07-08 | 1991-12-12 | Nissan Motor | SPIROOXAZINE COMPOUNDS, PHOTO-SENSITIVE MATERIALS CONTAINING THEM AND METHOD FOR THE PRODUCTION THEREOF. |
GB8620430D0 (en) * | 1986-08-22 | 1986-10-01 | Plessey Co Plc | Marking of articles |
CA1340939C (en) | 1987-02-02 | 2000-03-28 | Ryojiro Akashi | Photochromic compound |
US4838673A (en) | 1987-04-27 | 1989-06-13 | J. R. Richards, Inc. | Polarized lens and method of making the same |
JP2578442B2 (en) | 1987-07-13 | 1997-02-05 | 三菱化学株式会社 | Molecularly oriented thin film |
US4873029A (en) | 1987-10-30 | 1989-10-10 | Blum Ronald D | Method for manufacturing lenses |
US4931220A (en) | 1987-11-24 | 1990-06-05 | Ppg Industries, Inc. | Organic photochromic pigment particulates |
JPH01170904A (en) * | 1987-12-25 | 1989-07-06 | Toray Ind Inc | Polarizing sheet having photochromic property |
NL8802832A (en) | 1988-02-29 | 1989-09-18 | Philips Nv | METHOD OF MANUFACTURING A LAYERED ELEMENT AND THE ELEMENT OBTAINED THEREFORE. |
EP0330733B1 (en) | 1988-03-04 | 1994-01-26 | GAO Gesellschaft für Automation und Organisation mbH | Thread- or strip-like security element to be included in a security document, and a method of manufacturing same |
GB2219098A (en) * | 1988-05-25 | 1989-11-29 | Plessey Co Plc | Optically anisotropic materials and applications |
US5130058A (en) | 1988-07-01 | 1992-07-14 | Tokuyama Soda Kabushiki Kaisha | Photochromic compound, process for production thereof, use thereof and composition containing said photochromic compound |
DE3825066A1 (en) | 1988-07-23 | 1990-01-25 | Roehm Gmbh | METHOD FOR PRODUCING THICKNESS, ANISOTROPIC LAYERS ON SURFACE-STRUCTURED CARRIERS |
JP2780180B2 (en) * | 1989-01-20 | 1998-07-30 | 三井化学株式会社 | Light modulation element |
US4974941A (en) | 1989-03-08 | 1990-12-04 | Hercules Incorporated | Process of aligning and realigning liquid crystal media |
NL8901167A (en) | 1989-05-10 | 1990-12-03 | Philips Nv | METHOD FOR MANUFACTURING A POLARIZATION FILTER, A POLARIZATION FILTER SO OBTAINED AND A DISPLAY EQUIPPED WITH THE POLARIZATION FILTER. |
US5180470A (en) | 1989-06-05 | 1993-01-19 | The Regents Of The University Of California | Deposition of highly-oriented PTFE films and uses therefor |
FR2647789B1 (en) | 1989-06-05 | 1994-07-22 | Essilor Int | INDOLINO-SPIRO-OXAZINE PHOTOCHROMIC COMPOUNDS, PROCESS FOR THEIR PREPARATION, PHOTOCHROMIC COMPOSITIONS AND ARTICLES CONTAINING SUCH COMPOUNDS |
ATE130850T1 (en) | 1989-07-28 | 1995-12-15 | Wako Pure Chem Ind Ltd | FULGIMIDE DERIVATIVES. |
JP2692290B2 (en) * | 1989-08-31 | 1997-12-17 | ソニー株式会社 | Disc recording and / or playback device |
JP2795352B2 (en) * | 1989-09-11 | 1998-09-10 | 呉羽化学工業株式会社 | Polarizing resin optical member having light control action |
US5130353A (en) | 1990-03-07 | 1992-07-14 | Ppg Industries, Inc. | Method for preparing photochromic plastic article |
US5073294A (en) | 1990-03-07 | 1991-12-17 | Hercules Incorporated | Process of preparing compositions having multiple oriented mesogens |
US5185390A (en) | 1990-03-07 | 1993-02-09 | Ppg Industries, Inc. | Water strippable photochromic resin composition |
JPH063528B2 (en) | 1990-03-16 | 1994-01-12 | 富士ゼロックス株式会社 | Light modulation display element and display method |
US5204053A (en) * | 1990-07-10 | 1993-04-20 | General Electric Company | Bi-level fuel management method for boiling-water nuclear reactor |
US5200116A (en) | 1990-07-23 | 1993-04-06 | Ppg Industries, Inc. | Photochromic chromene compounds |
US5532320A (en) * | 1990-08-24 | 1996-07-02 | University Of Massachusetts Lowell | Second order nonlinear optical interpenetrating polymer networks |
JPH04199024A (en) | 1990-11-29 | 1992-07-20 | Hitachi Ltd | Liquid crystal display element and display device using the same |
US5202053A (en) | 1991-02-22 | 1993-04-13 | Hercules Incorporated | Polymerizable nematic monomer compositions |
DE59209499D1 (en) | 1991-07-26 | 1998-10-22 | Rolic Ag | Oriented photopolymers and processes for their manufacture |
US5189448A (en) | 1991-08-08 | 1993-02-23 | Katsumi Yaguchi | Unit for searching for a lost contact lens |
US5608567A (en) | 1991-11-05 | 1997-03-04 | Asulab S.A. | Variable transparency electro-optical device |
DE4138386A1 (en) * | 1991-11-22 | 1993-05-27 | Basf Ag | FLAME RESISTANT THERMOPLASTIC MOLDS |
EP0543678A1 (en) | 1991-11-22 | 1993-05-26 | Nippon Oil Company, Limited | Process for producing heat-resistant optical elements |
US5644416A (en) | 1991-11-26 | 1997-07-01 | Fuji Xerox Co., Ltd. | Light modulation device and method of light modulation using the same |
US5289547A (en) | 1991-12-06 | 1994-02-22 | Ppg Industries, Inc. | Authenticating method |
US5238981A (en) | 1992-02-24 | 1993-08-24 | Transitions Optical, Inc. | Photochromic naphthopyrans |
JP3016533B2 (en) | 1992-03-03 | 2000-03-06 | 株式会社トクヤマ | Photochromic composition |
US6160597A (en) * | 1993-02-17 | 2000-12-12 | Rolic Ag | Optical component and method of manufacture |
EP0611981B1 (en) | 1993-02-17 | 1997-06-11 | F. Hoffmann-La Roche Ag | Optical device |
EP0622789B1 (en) | 1993-03-30 | 2002-08-07 | Bayer Ag | Sheet-like structures containing side chain polymers |
KR970000356B1 (en) | 1993-09-18 | 1997-01-08 | 엘지전자 주식회사 | Light polymer alignment film forming method of liquid crystal display element |
US5625427A (en) * | 1993-12-15 | 1997-04-29 | Corning Incorporated | Ophthalmic lens |
EP0770116B1 (en) | 1994-07-11 | 1999-09-22 | Optische Werke G. Rodenstock | Diaryl-2h-naphthopyranes |
DE4434966A1 (en) | 1994-09-30 | 1996-04-04 | Bayer Ag | New side group polymers and their use for optical components |
US5645767A (en) | 1994-11-03 | 1997-07-08 | Transitions Optical, Inc. | Photochromic indeno-fused naphthopyrans |
US6049428A (en) | 1994-11-18 | 2000-04-11 | Optiva, Inc. | Dichroic light polarizers |
US5962617A (en) | 1995-02-02 | 1999-10-05 | Simula Inc. | Impact resistant polyurethane and method of manufacture thereof |
US5757459A (en) * | 1995-03-03 | 1998-05-26 | Vision-Ease Lens, Inc. | Multifocal optical elements |
US5846452A (en) | 1995-04-06 | 1998-12-08 | Alliant Techsystems Inc. | Liquid crystal optical storage medium with gray scale |
US5658501A (en) | 1995-06-14 | 1997-08-19 | Transitions Optical, Inc. | Substituted naphthopyrans |
US5641416A (en) * | 1995-10-25 | 1997-06-24 | Micron Display Technology, Inc. | Method for particulate-free energy beam cutting of a wafer of die assemblies |
US5903330A (en) | 1995-10-31 | 1999-05-11 | Rolic Ag | Optical component with plural orientation layers on the same substrate wherein the surfaces of the orientation layers have different patterns and direction |
US5746949A (en) | 1995-11-21 | 1998-05-05 | Hoechst Celanese Corp. | Polarizer films comprising aromatic liquid crystalline polymers comprising dichroic dyes in their main chains |
AUPN718195A0 (en) * | 1995-12-18 | 1996-01-18 | Sola International Holdings Ltd | Laminate wafers |
US5723072A (en) | 1996-06-17 | 1998-03-03 | Ppg Industries, Inc. | Photochromic heterocyclic fused indenonaphthopyrans |
US5955520A (en) * | 1996-06-17 | 1999-09-21 | Ppg Industries, Inc. | Photochromic indeno-fused naphthopyrans |
US5698141A (en) | 1996-06-17 | 1997-12-16 | Ppg Industries, Inc. | Photochromic heterocyclic fused indenonaphthopyrans |
FR2751971B1 (en) | 1996-07-31 | 1998-11-20 | Essilor Int | NOVEL HOMOAZAADAMANTANE SPIROOXAZINES AND THEIR USE IN THE FIELD OF OPHTHALMIC OPTICS |
AU718471B2 (en) | 1997-02-21 | 2000-04-13 | Ppg Industries Ohio, Inc. | Photochromic polyurethane coating and articles having such a coating |
US5943104A (en) | 1997-03-25 | 1999-08-24 | University Technology Corporation | Liquid crystal eyewear with two identical guest host subcells and tilted homeotropic alignment |
AUPO625797A0 (en) | 1997-04-17 | 1997-05-15 | Sola International Holdings Ltd | Spectacles bearing sunglass lenses |
US6025026A (en) | 1997-06-30 | 2000-02-15 | Transitions Optical, Inc. | Process for producing an adherent polymeric layer on polymeric substrates and articles produced thereby |
US5896232A (en) * | 1997-08-07 | 1999-04-20 | International Business Machines Corporation | Highly efficient and compact frontlighting for polarization-based reflection light valves |
RU2124746C1 (en) * | 1997-08-11 | 1999-01-10 | Закрытое акционерное общество "Кванта Инвест" | Dichroic polarizer |
US6268055B1 (en) | 1997-12-08 | 2001-07-31 | Ppg Industries Ohio, Inc. | Photochromic epoxy resin coating composition and articles having such a coating |
US5879592A (en) | 1997-12-10 | 1999-03-09 | Ppg Industries, Inc. | Water soluble photochromic compounds, compositions and optical elements comprising the compounds |
US6630597B1 (en) | 1997-12-15 | 2003-10-07 | Transitions Optical, Inc. | Photochromic 6-aryl substituted 3H-naphtho(2,1-b)pyrans |
US5869658A (en) * | 1997-12-15 | 1999-02-09 | Ppg Industries, Inc. | Photochromic indeno-fused naptho 2,1-b!pyrans |
JP2000008031A (en) | 1998-06-18 | 2000-01-11 | Tokuyama Corp | Photochromic composition |
US6239778B1 (en) | 1998-06-24 | 2001-05-29 | Alphamicron, Inc. | Variable light attentuating dichroic dye guest-host device |
DE69903042T2 (en) | 1998-07-10 | 2003-08-07 | Transitions Optical Inc | PHOTOCHROME SIX-LINKED HETEROCYCLIC-CONDENSED NAPHTHOPYRANE |
US6022497A (en) | 1998-07-10 | 2000-02-08 | Ppg Industries Ohio, Inc. | Photochromic six-membered heterocyclic-fused naphthopyrans |
US5961892A (en) * | 1998-09-11 | 1999-10-05 | Ppg Industries Ohio, Inc. | Polyalkoxylated naphthopyrans |
US6555028B2 (en) | 1998-09-11 | 2003-04-29 | Transitions Optical, Inc. | Polymeric matrix compatibilized naphthopyrans |
BR9913869A (en) | 1998-09-11 | 2004-12-28 | Ppg Ind Ohio Inc | Naphthoopyran Compound and Photochromic Articles |
US6276632B1 (en) * | 1998-09-16 | 2001-08-21 | Bobby W. Sanders | Axi-symmetric mixed compression inlet with variable geometry centerbody |
GB9821121D0 (en) * | 1998-09-29 | 1998-11-25 | James Robinson Ltd | Grey colouring photochromic fused pyrans |
US6245399B1 (en) | 1998-10-14 | 2001-06-12 | 3M Innovative Properties Company | Guest-host polarizers |
AU1722700A (en) | 1998-11-16 | 2000-06-05 | Cambridge Scientific, Inc. | Biopolymer-based holographic optical element |
US6436525B1 (en) | 1998-12-11 | 2002-08-20 | Ppg Industries Ohio, Inc. | Polyanhydride photochromic coating composition and photochromic articles |
US6060001A (en) | 1998-12-14 | 2000-05-09 | Ppg Industries Ohio, Inc. | Alkoxyacrylamide photochromic coatings compositions and photochromic articles |
KR100706157B1 (en) | 1998-12-15 | 2007-04-11 | 롤리크 아게 | Orientation layer for a liquid crystal material and liquid crystal cell comprising the same |
US6506488B1 (en) | 1998-12-18 | 2003-01-14 | Ppg Industries Ohio, Inc. | Aminoplast resin photochromic coating composition and photochromic articles |
US6432544B1 (en) | 1998-12-18 | 2002-08-13 | Ppg Industries Ohio, Inc. | Aminoplast resin photochromic coating composition and photochromic articles |
US6338808B1 (en) | 1999-03-31 | 2002-01-15 | Fuji Photo Film Co., Ltd. | Liquid crystal composition comprising liquid crystal molecules and alignment promoter |
US7009751B2 (en) * | 1999-05-14 | 2006-03-07 | Gentex Corporation | Electrochromic rearview mirror incorporating a third surface partially transmissive reflector |
JP2000351280A (en) * | 1999-06-11 | 2000-12-19 | Toppan Printing Co Ltd | Image forming apparatus and thermal transfer recording medium |
WO2001002449A2 (en) | 1999-07-02 | 2001-01-11 | Ppg Industries Ohio, Inc. | Poly(meth)acrylic photochromic coating |
US6150430A (en) | 1999-07-06 | 2000-11-21 | Transitions Optical, Inc. | Process for adhering a photochromic coating to a polymeric substrate |
EP1115268A1 (en) * | 1999-07-07 | 2001-07-11 | Sony Corporation | Method and apparatus for manufacturing flexible organic el display |
FR2796077B1 (en) | 1999-07-08 | 2001-10-05 | Essilor Int | NAPHTO (2,1-B) PYRANIC PHOTOCHROMIC COMPOUNDS WITH BI OR TERTHIENYL SUBSTITUTIONS, PROCESS FOR PRODUCING SAME, MATERIALS AND PHOTOCHROMIC ARTICLES OBTAINED |
JP3756019B2 (en) * | 1999-08-20 | 2006-03-15 | 太陽誘電株式会社 | Polarizing unit, manufacturing method thereof, remote indication position detection method, remote position indication device, remote indication position detection device, and pointing device |
US6296785B1 (en) * | 1999-09-17 | 2001-10-02 | Ppg Industries Ohio, Inc. | Indeno-fused photochromic naphthopyrans |
US6348604B1 (en) | 1999-09-17 | 2002-02-19 | Ppg Industries Ohio, Inc. | Photochromic naphthopyrans |
US7151626B2 (en) * | 1999-11-03 | 2006-12-19 | Optodot Corporation | Reflective organic layers |
US6353102B1 (en) * | 1999-12-17 | 2002-03-05 | Ppg Industries Ohio, Inc. | Photochromic naphthopyrans |
US6759090B2 (en) * | 1999-12-29 | 2004-07-06 | Younger Mfg. Co. | Method for improved adhesion of an optical coating to a polarizing film |
US6531076B2 (en) | 2000-02-04 | 2003-03-11 | Ppg Industries Ohio, Inc. | Photochromic organic resin composition |
US6281366B1 (en) | 2000-02-29 | 2001-08-28 | Essilor International Compagnie Generale D'optique | Photochromic [3H]naphtho[2,1-b]pyran compounds containing an acetylenic substituent, process for their manufacture, and photochromic materials and articles obtained |
ATE279492T1 (en) | 2000-03-02 | 2004-10-15 | Merck Patent Gmbh | MULTI-LAYER REFLECTIVE FILM OR PIGMENT HAVING VIEWING ANGLE DEPENDENT REFLECTIVE PROPERTIES |
US6788449B2 (en) * | 2000-03-03 | 2004-09-07 | Sipix Imaging, Inc. | Electrophoretic display and novel process for its manufacture |
DE60111617T2 (en) * | 2000-03-22 | 2006-06-08 | Transitions Optical, Inc., Pinellas Park | HYDROXYLATED / CARBOXYLATED NAPHTHOPYRANEES |
ES2245366T3 (en) * | 2000-05-31 | 2006-01-01 | Tokuyama Corporation | ENDURECIBLE COMPOSITION AND PHOTOCROMIC HARDENED PRODUCT. |
JP4586953B2 (en) * | 2000-06-09 | 2010-11-24 | 三菱瓦斯化学株式会社 | Synthetic resin laminate with both polarization and photochromic properties |
TW534869B (en) * | 2000-06-09 | 2003-06-01 | Mitsubishi Gas Chemical Co | Synthetic resin laminate having both polarization characteristic and photochromism characteristic, and molded article obtained therefrom |
EP1170353B1 (en) * | 2000-07-06 | 2005-11-02 | Fuji Photo Film Co., Ltd. | Liquid crystal composition comprising liquid crystal molecules and aligment promoter |
DE10040763A1 (en) * | 2000-08-19 | 2002-02-28 | Bosch Gmbh Robert | Electromagnetically actuated valve, in particular for hydraulic brake systems in motor vehicles |
JP4455743B2 (en) | 2000-09-12 | 2010-04-21 | 山本光学株式会社 | Manufacturing method of polarizing lens |
US6690495B1 (en) * | 2000-10-03 | 2004-02-10 | Alphamicron, Inc. | Device exhibiting photo-induced dichroism for adaptive anti-glare vision protection |
US6565222B1 (en) * | 2000-11-17 | 2003-05-20 | Sony Corporation | High performance, low cost mirror for a rear projection television |
US6433043B1 (en) * | 2000-11-28 | 2002-08-13 | Transitions Optical, Inc. | Removable imbibition composition of photochromic compound and kinetic enhancing additive |
GB2374081B (en) | 2001-04-06 | 2004-06-09 | Central Research Lab Ltd | A method of forming a liquid crystal polymer layer |
DE10122188B4 (en) * | 2001-05-08 | 2007-04-12 | Ems-Chemie Ag | Polyamide molding compounds for the production of optical lenses |
WO2002099513A1 (en) * | 2001-06-01 | 2002-12-12 | Mitsubishi Gas Chemical Company, Inc. | Plastic molded product having photochromic characteristics and/or polarizing characteristics |
AU2002355836B8 (en) * | 2001-07-27 | 2008-02-21 | Insight Equity, A.P.X, LP | Light polarizing film with melanin |
JP2003057440A (en) * | 2001-08-09 | 2003-02-26 | Konica Corp | Polarizing plate, method and instrument for measuring moving body, and ink jet inspecting device |
KR100399250B1 (en) * | 2001-08-30 | 2003-09-26 | 김수진 | Photochromic power of sunglasses lens for light-polarizing and method of making same |
JP2003073669A (en) * | 2001-08-31 | 2003-03-12 | Fuji Photo Film Co Ltd | Liquid crystal composition, display and optical film |
BR0213012A (en) | 2001-10-05 | 2004-12-28 | E Vision Llc | Hybrid Electroactive Lenses |
DE60332784D1 (en) * | 2002-02-13 | 2010-07-15 | Merck Patent Gmbh | A method of making an anisotropic polymer film on a substrate having a structured surface |
US7198374B2 (en) * | 2002-07-31 | 2007-04-03 | Seiko Epson Corporation | Prism structure and projector |
US20040046927A1 (en) * | 2002-08-27 | 2004-03-11 | Montgomery Mark E. | Polarized and non-polarized bifocal spectacles |
US6863848B2 (en) * | 2002-08-30 | 2005-03-08 | Signet Armorlite, Inc. | Methods for preparing composite photochromic ophthalmic lenses |
WO2004023173A1 (en) * | 2002-09-09 | 2004-03-18 | Nitto Denko Corporation | Polarizer, optical film and image display |
US7036932B2 (en) * | 2002-10-04 | 2006-05-02 | Vision-Ease Lens | Laminated functional wafer for plastic optical elements |
US6958860B2 (en) * | 2002-10-07 | 2005-10-25 | Eastman Kodak Company | Voided polymer film containing layered particulates |
US20040223221A1 (en) | 2002-12-20 | 2004-11-11 | Vision-Ease Lens, Inc. | Polarizing plate and eyewear plastic article containing the same |
US7004583B2 (en) * | 2003-01-29 | 2006-02-28 | East Bay Technologies | Eyewear lenses and methods of manufacturing |
US6874888B1 (en) * | 2003-04-21 | 2005-04-05 | Wendy Dudai | Polarized contact lenses with a clear peripheral portion |
US7256921B2 (en) * | 2003-07-01 | 2007-08-14 | Transitions Optical, Inc. | Polarizing, photochromic devices and methods of making the same |
US7632540B2 (en) * | 2003-07-01 | 2009-12-15 | Transitions Optical, Inc. | Alignment facilities for optical dyes |
US7978391B2 (en) * | 2004-05-17 | 2011-07-12 | Transitions Optical, Inc. | Polarizing, photochromic devices and methods of making the same |
US7342112B2 (en) * | 2003-07-01 | 2008-03-11 | Ppg Industries Ohio, Inc. | Photochromic compounds |
US9096014B2 (en) * | 2003-07-01 | 2015-08-04 | Transitions Optical, Inc. | Oriented polymeric sheets exhibiting dichroism and articles containing the same |
US6844686B1 (en) * | 2003-07-28 | 2005-01-18 | Michael M. Schneck | Jewelry gift box with illuminated display |
US7128414B2 (en) * | 2003-12-24 | 2006-10-31 | Essilor International Compagnie Cenerale D'optique | Methods for coating lenses |
ATE432127T1 (en) | 2004-03-02 | 2009-06-15 | Essilor Int | METHOD FOR COATING CURVED SURFACES WITH A POLARIZING LIQUID AND DEVICE |
WO2005085912A1 (en) | 2004-03-02 | 2005-09-15 | Essilor International(Compagnie Generale D'optique) | Ophthalmic lens with an optically transparent composite film exhibiting both impact-resistance property and polarizing property, and a process for its manufacture |
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