US3562172A - Photochromic compound and composition containing the same - Google Patents

Photochromic compound and composition containing the same Download PDF

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US3562172A
US3562172A US871872A US3562172DA US3562172A US 3562172 A US3562172 A US 3562172A US 871872 A US871872 A US 871872A US 3562172D A US3562172D A US 3562172DA US 3562172 A US3562172 A US 3562172A
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carbon atoms
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alkyl group
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Hisatake Ono
Chiaki Osada
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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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
    • 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
    • G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances

Definitions

  • R represents (CH ),,COOH, (CH ),,CN or -(CH ),,COOR (wherein R is an alkyl group having 1 to carbon atoms; n is 1 to 4); R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms; a halogen atom, a nitro group, a cyano group, or an alkoxyl group having 1 to 5 carbon atoms or a carboxyl group, and said carboxyl group may be substituted with an alkyl group having 1 to 5 carbon atoms.
  • the present invention relates to photochromic materials.
  • the present invention relates to a photochromic compound represented by the formula wherein R represents -(CH ),,COOH, -(CH ),,CN or -(CH ),,COOR (wherein R is an alkyl group having 1 to 5 carbon atoms; n is 1 to 4); R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms; a halogen atom, a nitro group, a cyano group, or an alkoxyl group having 1 to 5 carbon atoms or a carboxyl group, and said carboxyl group may be substituted with an alkyl group having 1 to 5 carbon atoms.
  • Photochromic composition containing, and photochromic compounds per se, represented by the formula:
  • R represents -(CH ),,COOH, (CH CN or (CH ),,COOR (wherein R is an alkyl group having 1 to 5 carbon atoms; 11 is 1 to 4); R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, a nitro group, a cyano group or an alkoxyl group having 1 to 5 carbon atoms or a carboxyl group, and said carboxyl group may be substituted with an alkyl group having 1 to 5 carbon atoms.
  • An object of the present invention is to obviate the disadvantages discussed above and to provide a novel compound having an oxazine ring to replace the conventional compounds having a pyrane ring.
  • Another object of the present invention is to provide a photochromic compound which is not influenced by the polar nature of the solvent, and which illustrates photochromic action at normal temperatures.
  • the drawing is a plot of density versus wavelength for a compound of the invention before and after irradiation with ultraviolet rays.
  • the present invention relates to a photochromic compound represented by the formula wherein R represents -(CH ),,COOH, (CH CN or (CH ),,COOR (wherein R is an alkyl group having 1 to 5 carbon atoms; is is l to 4); R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms; a halogen atom, a nitro group, a cyano group, or an alkoxyl group having 1 to 5 carbon atoms or a carboxyl group, and said carboxyl group may be substituted with an alkyl group having 1 to 5 carbon atoms.
  • the compound represented by the above formula is dissolved in a solvent such as benzene, toluene, carbon disulfide, ethyl acetate, methyl ethyl ketone, acetone, ethyl alcohol, methyl alcohol, acetonitrile, tetrahydrofurane, dioxane, methyl cellusolve morpholine, ethylene glycol, dimethyl formamide, dimethyl sulfoxide, etc. (at normal temperature) to yield the photochromic composition in a colorlas state. When it is irradiated with ultraviolet rays, the photochromic composition turns blue.
  • a solvent such as benzene, toluene, carbon disulfide, ethyl acetate, methyl ethyl ketone, acetone, ethyl alcohol, methyl alcohol, acetonitrile, tetrahydrofurane, dioxane, methyl cellusolve morph
  • the compound of the present invention can be dissolved in a solution such as polyvinylacetate-acetone solution, nitrocellulose-acetonitrile solution, polyvinylchloride-methyl ethyl ketone solution, polymethylacrylate acetone solution, cellulose acetate-dimethyl formaldehyde solution, polyvinylpyrrolidone-acetonitrile solution, polystyrol-benzene solution, ethyl cellulose-methylene chloride solution, etc., to obtain the photochromic composition in a colorless state, regardless of the kinds of solvents and/ or resins.
  • a solution such as polyvinylacetate-acetone solution, nitrocellulose-acetonitrile solution, polyvinylchloride-methyl ethyl ketone solution, polymethylacrylate acetone solution, cellulose acetate-dimethyl formaldehyde solution, polyvinylpyrrolidone-acetonitrile solution, polystyrol-benzene solution,
  • composition can be coated on a support such as baryta paper, cellulose acetate, polyethylene terephthalate, etc., and then dried, and will still turn blue when irradiated with ultraviolet rays and, if allowed to stand in the dark without exposure to ultraviolet rays, will change to colorless again.
  • a support such as baryta paper, cellulose acetate, polyethylene terephthalate, etc.
  • the compound represented by the above formula is obtained by refluxing a quaternized indolenine derivative, u-nitroso-fi-naphthol and triethylamine in an approximate equimolar ratio in ethyl alcohol while passingnitro gen gas through the system, followed by cooling, filtering and recrystallizing from an appropriate solvent.
  • the photochromic compositions of the present inven tion are employed as photochromic materials for photography and printing, which are obtained by coating the above composition on a high molecular weight film, baryta paper, etc., photochromic materials for furniture usage such as curtains, glass, etc., and photochromic materials for use in filters.
  • the figure is a graph showing the change in the visible absorption spectrum of film, before and after irradiation with ultraviolet rays, which is coated with the photochromic composition of this invention, then dried.
  • EXAMPLE 1 6.2. g. of l-B-carboxyethyl-2,3,3-trimethyl-indolenium bromide and 3.5 g. of u-nitroso-B-naphthol were dissolved in 50 cc. of dehydrated ethanol and, after adding 2 g. of triethylamine thereto, were refluxed in a nitrogen atmosphere for two hours. After the reaction, excess ethanol was distilled out and the mixture was cooled to produce a crystal. A small amount of ethanol was added thereto and filtered. The crude crystal thus obtained was recrystallized from ethanol using active carbon to provide 0.7 g.
  • EXAMPLE 2 3.3 g. of l-/3-carb0xyethyl-2,3,3,S-tetramethyl-indolenium bromide and a-nitroso-p-naphthol were reacted in the same manner as in Example 1 to obtain 1.2 g. of the yellow crystals of l-B-carboxyethyl-3,3,5-trimethyl spiro [indolino 2,3 naphtho[2.1-b] (1.4) oxazine] having a melting point of 188 to 190 C.
  • a benzene solution of this compound was colorless, but, when irradiated with ultraviolet rays, colored greenish blue and, on being al lowed to stand in the dark, turned back to colorless.
  • a baryta paper which 'was coated with a solution of this compound dissolved in ethyl acetate ester-polyvinyl acetate and dried was colorless in the ordinary state, but, when irradiated with ultraviolet rays, immediately colored blue. Upon discontinuing irradiation with ultraviolet rays, this material turned colorless.
  • the absorption curve for this material is shown in FIG. 1. Curve 1 is before irradiation, and curve 2 is after irradiation.
  • EXAMPLE 3 6.8 g. of 1-carboxyethyl-2,3,3-trimethyl-5-methoxyindolenium bromide and 3.5 g. of a-nitroso-B-naphthol were reacted in the same manner as in Example 1 to obtain 2.1 g. of the light yellow crystal of 1-carboxyethyl-3,3-
  • EXAMPLE 4 6.8 g. of 1-'y-cyanopropyl-2,3,3-trimethyl-5-chlorindolenium bromide and 3.5 g. of oc-nitroso-B-naphthol were reacted in the same manner as in Example 1 to obtain 2.1 g. of the light yellow crystals of 1- -cyanopropyl-3,3- dimethyl 5 chlor-spiro[indolino-2,3'-naphtho[2.1 b] (1.4)oxazine] which melts at 158 to 160 C.
  • a polyethylene terephthalate film coated with a solution of this compound dissolved in benzene-polystyrol and dried was colorless and transparent, but, when irradiated with ultraviolet rays, immediately colored blue and, on allowing to stand in the dark turned back to colorless.
  • R2 Ra wherein R represents -(CH COOH, (CH CN, or -(CH COOR; R is an alkyl group having 1 to 5 carbon atoms; n is 1 to 4; R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms; a halogen atom, a nitro group, a cyano group, an alkoxyl group having 1 to 5 carbon atoms, a carboxyl group or a carboxyl group being substituted with an alkyl group having 1 to 5 carbon atoms.
  • the photochromic compound as claimed in claim 1 wherein said compound represented by the general formula is 1- 3-carboxyethyl-3,3-dimethyl-spiro [indolino-2,3 naphtho[2.1-b] (1.4) oxazine] 3.
  • said compound represented by the general formula is l-fi-carboxyethyl-3,3,S-trimethyl-spiro[indolino-2, 3-naphtho[2.1-b] (1.4)oxazine].
  • a photochromic composition comprising a photochromic compound represented by the general formula,
  • R represents (CH ),,COOH, (CH ),,CN or (CH COOR;
  • R is an alkyl group having 1 to 5 carbon atoms; and n is 1 to 4;
  • R and R each represents an alkyl group having 1 to 5 carbon atoms or a phenyl group; and
  • R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkoxy group having 1 to 5 carbon atoms, a carboxyl group or a carboxy group substituted with an alkyl group having 1 to 5 carbon atoms, and a solvent.
  • R represents -(CH COOH, (CH CN or (CH COOR; wherein R is an alkyl group having 1 to 5 carbon atoms; n is 1 to 4; R and R each represents an alkyl group having 1 to 5 carbon atoms; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, a nitro group, a cyano 20 group, an alkoxyl group, a carboxyl group, or a carboxy group substituted with an alkyl group having 1 to 5 carbon atoms, a binder and a solvent.
  • the photochromic composition as claimed in claim 8 wherein said binder is polyvinyl acetate, nitrocellulose, polyvinyl chloride, polymethylmethacrylate, cellulose acetate, polyvinyl pyrrolidone, polystyrene or ethyl cellulose.

Abstract

WHEREIN R1 REPRESENTS-(CH2)NCOOH,-(CH2ENCN OR -(CH2)NCOOR (WHEREIN R IS AN ALKYL GROUP HAVING 1 TO 5 CARBON ATOMS; N IS 1 TO 4); R2 AND R3 REPRESENT AN ALKYL GROUP HAVING 1 TO 5 CARBON ATOMS OR A PHENYL GROUP; AND R4 REPRESENTS A HYDROGEN ATOM, AN ALKYL GROUP HAVING 1 TO 5 CARBON ATOMS; A HALOGEN ATOM, A NITRO GROUP, A CYANO GROUP, OR AN ALKOXYL GROUP HAVING 1 TO 5 CARBON ATOMS OR A CARBOXYL GROUP, AND SAID CARBOXYL GROUP MAY BE SUBSTITUTED WITH AN ALKYL GROUP HAVING 1 TO 5 CARBON ATOMS.

OXAZINE)

1-R1,3-R2,3-R3,R4-SPIRO(INDOLINE-2,3''-NAPHTH(2,1-B)-1,4-

PHOTOCHROMIC COMPOSITIONS CONTAINING, AND PHOTOCHROMIC COMPOUNDS PER SE, REPRESENTED BY THE FORMULA:

Description

Feb. 9, 1971 v l T 0 0 ETAL 3,562,172
PHOTOCHROMIC COMPOUND AND COMPOSITION CONTAINING THE SAME Filed 001.. 28, 1969 DENSRTY (DI WAVE LENGTH INVENTORS HiSATAKE 0N0 I CHIAKI OSADA s jl w im M ATTORNEYS United States Patent Ofice 3,562,172 Patented Feb. 9, 1971 U.S. Cl. 252-300 10 Claims ABSTRACT OF THE DISCLOSURE Photochromic compositions containing, and photochromic compounds per se, represented by the formula:
wherein R represents (CH ),,COOH, (CH ),,CN or -(CH ),,COOR (wherein R is an alkyl group having 1 to carbon atoms; n is 1 to 4); R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms; a halogen atom, a nitro group, a cyano group, or an alkoxyl group having 1 to 5 carbon atoms or a carboxyl group, and said carboxyl group may be substituted with an alkyl group having 1 to 5 carbon atoms.
BACKGROUND OF THE INVENTION Field of the invention This invention relates to photochromic materials. The present invention relates to a photochromic compound represented by the formula wherein R represents -(CH ),,COOH, -(CH ),,CN or -(CH ),,COOR (wherein R is an alkyl group having 1 to 5 carbon atoms; n is 1 to 4); R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms; a halogen atom, a nitro group, a cyano group, or an alkoxyl group having 1 to 5 carbon atoms or a carboxyl group, and said carboxyl group may be substituted with an alkyl group having 1 to 5 carbon atoms.
Description of the prior art We previously discovered the photochromic compound represented by the above formula, in which R is an alkyl group, as disclosed in Japanese patent application No. 55,662/67. The photochromic action of the compound was remarkable at about 10 C.
SUMMARY OF THE INVENTION Photochromic composition containing, and photochromic compounds per se, represented by the formula:
wherein R represents -(CH ),,COOH, (CH CN or (CH ),,COOR (wherein R is an alkyl group having 1 to 5 carbon atoms; 11 is 1 to 4); R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, a nitro group, a cyano group or an alkoxyl group having 1 to 5 carbon atoms or a carboxyl group, and said carboxyl group may be substituted with an alkyl group having 1 to 5 carbon atoms.
An object of the present invention is to obviate the disadvantages discussed above and to provide a novel compound having an oxazine ring to replace the conventional compounds having a pyrane ring.
Another object of the present invention is to provide a photochromic compound which is not influenced by the polar nature of the solvent, and which illustrates photochromic action at normal temperatures.
BRIEF DESCRIPTION OF THE DRAWINGS The drawing is a plot of density versus wavelength for a compound of the invention before and after irradiation with ultraviolet rays.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention relates to a photochromic compound represented by the formula wherein R represents -(CH ),,COOH, (CH CN or (CH ),,COOR (wherein R is an alkyl group having 1 to 5 carbon atoms; is is l to 4); R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms; a halogen atom, a nitro group, a cyano group, or an alkoxyl group having 1 to 5 carbon atoms or a carboxyl group, and said carboxyl group may be substituted with an alkyl group having 1 to 5 carbon atoms.
The compound represented by the above formula is dissolved in a solvent such as benzene, toluene, carbon disulfide, ethyl acetate, methyl ethyl ketone, acetone, ethyl alcohol, methyl alcohol, acetonitrile, tetrahydrofurane, dioxane, methyl cellusolve morpholine, ethylene glycol, dimethyl formamide, dimethyl sulfoxide, etc. (at normal temperature) to yield the photochromic composition in a colorlas state. When it is irradiated with ultraviolet rays, the photochromic composition turns blue. Further, the compound of the present invention can be dissolved in a solution such as polyvinylacetate-acetone solution, nitrocellulose-acetonitrile solution, polyvinylchloride-methyl ethyl ketone solution, polymethylacrylate acetone solution, cellulose acetate-dimethyl formaldehyde solution, polyvinylpyrrolidone-acetonitrile solution, polystyrol-benzene solution, ethyl cellulose-methylene chloride solution, etc., to obtain the photochromic composition in a colorless state, regardless of the kinds of solvents and/ or resins.
The composition can be coated on a support such as baryta paper, cellulose acetate, polyethylene terephthalate, etc., and then dried, and will still turn blue when irradiated with ultraviolet rays and, if allowed to stand in the dark without exposure to ultraviolet rays, will change to colorless again.
The compound represented by the above formula is obtained by refluxing a quaternized indolenine derivative, u-nitroso-fi-naphthol and triethylamine in an approximate equimolar ratio in ethyl alcohol while passingnitro gen gas through the system, followed by cooling, filtering and recrystallizing from an appropriate solvent.
The photochromic compositions of the present inven tion are employed as photochromic materials for photography and printing, which are obtained by coating the above composition on a high molecular weight film, baryta paper, etc., photochromic materials for furniture usage such as curtains, glass, etc., and photochromic materials for use in filters.
The figure is a graph showing the change in the visible absorption spectrum of film, before and after irradiation with ultraviolet rays, which is coated with the photochromic composition of this invention, then dried.
EXAMPLE 1 6.2. g. of l-B-carboxyethyl-2,3,3-trimethyl-indolenium bromide and 3.5 g. of u-nitroso-B-naphthol were dissolved in 50 cc. of dehydrated ethanol and, after adding 2 g. of triethylamine thereto, were refluxed in a nitrogen atmosphere for two hours. After the reaction, excess ethanol was distilled out and the mixture was cooled to produce a crystal. A small amount of ethanol was added thereto and filtered. The crude crystal thus obtained was recrystallized from ethanol using active carbon to provide 0.7 g. of the yellow crystal of 1- 3-carboxyethyl-3,3-dimethyl spiro[indolino-2,3'-naphtho[2.1-b] (1.4)oxazine] having a melting point of 186 to 187 C. The ethanol solution of this compound was colorless under the light of a room lamp, but, when irradiated with ultraviolet rays, immediately colored blue, and turned back to colorless when allowed to stand in a dark place.
EXAMPLE 2 3.3 g. of l-/3-carb0xyethyl-2,3,3,S-tetramethyl-indolenium bromide and a-nitroso-p-naphthol were reacted in the same manner as in Example 1 to obtain 1.2 g. of the yellow crystals of l-B-carboxyethyl-3,3,5-trimethyl spiro [indolino 2,3 naphtho[2.1-b] (1.4) oxazine] having a melting point of 188 to 190 C. A benzene solution of this compound was colorless, but, when irradiated with ultraviolet rays, colored greenish blue and, on being al lowed to stand in the dark, turned back to colorless. A baryta paper which 'was coated with a solution of this compound dissolved in ethyl acetate ester-polyvinyl acetate and dried was colorless in the ordinary state, but, when irradiated with ultraviolet rays, immediately colored blue. Upon discontinuing irradiation with ultraviolet rays, this material turned colorless. The absorption curve for this material is shown in FIG. 1. Curve 1 is before irradiation, and curve 2 is after irradiation.
EXAMPLE 3 6.8 g. of 1-carboxyethyl-2,3,3-trimethyl-5-methoxyindolenium bromide and 3.5 g. of a-nitroso-B-naphthol were reacted in the same manner as in Example 1 to obtain 2.1 g. of the light yellow crystal of 1-carboxyethyl-3,3-
4 dimethyl-S-methoxy spiro[indolino 2,3'-naphtho[2.l-b]
(1.4)oxane] having a melting point of 165 to 167 C.
The properties thereof were the same as the compound of Example 2.
EXAMPLE 4 6.8 g. of 1-'y-cyanopropyl-2,3,3-trimethyl-5-chlorindolenium bromide and 3.5 g. of oc-nitroso-B-naphthol were reacted in the same manner as in Example 1 to obtain 2.1 g. of the light yellow crystals of 1- -cyanopropyl-3,3- dimethyl 5 chlor-spiro[indolino-2,3'-naphtho[2.1 b] (1.4)oxazine] which melts at 158 to 160 C. A polyethylene terephthalate film coated with a solution of this compound dissolved in benzene-polystyrol and dried was colorless and transparent, but, when irradiated with ultraviolet rays, immediately colored blue and, on allowing to stand in the dark turned back to colorless.
We claim:
1. A photochromic compound represented by the general formula,
R2 Ra wherein R represents -(CH COOH, (CH CN, or -(CH COOR; R is an alkyl group having 1 to 5 carbon atoms; n is 1 to 4; R and R represent an alkyl group having 1 to 5 carbon atoms or a phenyl group; R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms; a halogen atom, a nitro group, a cyano group, an alkoxyl group having 1 to 5 carbon atoms, a carboxyl group or a carboxyl group being substituted with an alkyl group having 1 to 5 carbon atoms.
2. The photochromic compound as claimed in claim 1 wherein said compound represented by the general formula is 1- 3-carboxyethyl-3,3-dimethyl-spiro [indolino-2,3 naphtho[2.1-b] (1.4) oxazine] 3. The photochromic compound as claimed in claim 1 wherein said compound represented by the general formula is l-fi-carboxyethyl-3,3,S-trimethyl-spiro[indolino-2, 3-naphtho[2.1-b] (1.4)oxazine].
4. The photochromic compound as claimed in claim 1 wherein said compound represented by the general formula is 1 carboxyethyl-3,3-dimethyl-5-methoxy-spiro [indolino-2,3'-naphtho [2. l-b] (1.4)oxazine].
5. The photochromic compound as claimed in claim 1 wherein said compound represented by the general formula is l-y-cyanopropyl 3,3 dimethyl-S-chloro-spiro [indolino-2,3 '-naphthol[2.1-b] (1.4)oxazine].
6. A photochromic composition comprising a photochromic compound represented by the general formula,
wherein R represents (CH ),,COOH, (CH ),,CN or (CH COOR; R is an alkyl group having 1 to 5 carbon atoms; and n is 1 to 4; R and R each represents an alkyl group having 1 to 5 carbon atoms or a phenyl group; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, a nitro group, a cyano group, an alkoxy group having 1 to 5 carbon atoms, a carboxyl group or a carboxy group substituted with an alkyl group having 1 to 5 carbon atoms, and a solvent.
7. The photochromic composition as claimed in claim 6 wherein said solvent is benzene, toluene, carbon disulfide, chloroform, ethyl acetate, methyl ethyl ketone,
wherein R represents -(CH COOH, (CH CN or (CH COOR; wherein R is an alkyl group having 1 to 5 carbon atoms; n is 1 to 4; R and R each represents an alkyl group having 1 to 5 carbon atoms; and R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a halogen atom, a nitro group, a cyano 20 group, an alkoxyl group, a carboxyl group, or a carboxy group substituted with an alkyl group having 1 to 5 carbon atoms, a binder and a solvent.
9. The photochromic composition as claimed in claim 8 wherein said binder is polyvinyl acetate, nitrocellulose, polyvinyl chloride, polymethylmethacrylate, cellulose acetate, polyvinyl pyrrolidone, polystyrene or ethyl cellulose.
10. The photochromic composition as claimed in claim 9 wherein said solvent is acetone, acetonitrile, methyl ethyl ketone, dimethyl formamide, acetonitrile, benzene or methylene chloride.
References Cited UNITED STATES PATENTS 3,395,145 7/1968 Hansen et al 260244 GEORGE F. LESMES, Primary Examiner J. P. BRAMMER, Assistant Examiner US. Cl. X.R. 260244
US871872A 1968-10-28 1969-10-28 Photochromic compound and composition containing the same Expired - Lifetime US3562172A (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2936255A1 (en) * 1978-09-08 1980-03-20 American Optical Corp PHOTOCHROMATIC OXAZINE COMPOUNDS AND THEIR USE FOR PHOTOCHROMATIC OPTICAL ELEMENTS
US4342668A (en) * 1978-09-08 1982-08-03 American Optical Corporation Photochromic compounds
DE3310388A1 (en) * 1982-03-22 1983-09-29 American Optical Co., Southbridge, Mass. FATIGUE-RESISTANT PHOTOCHROME COMPOSITIONS AND ITEMS
JPS6084527A (en) * 1983-08-02 1985-05-13 オプテイツシエ．ウエルケ．ゲ−．ロ−デンストツク Phototropic spectacles frame
US4634767A (en) * 1985-09-03 1987-01-06 Ppg Industries, Inc. Method for preparing spiro(indoline)-type photochromic compounds
US4636561A (en) * 1984-12-11 1987-01-13 Unitika Ltd. Spiroindolinenaphthoxadine photochromic compounds
US4637698A (en) * 1983-11-04 1987-01-20 Ppg Industries, Inc. Photochromic compound and articles containing the same
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US4699473A (en) * 1983-08-08 1987-10-13 American Optical Corporation Trifluoromethyl substituted spirooxazine photochromic dyes
US4720547A (en) * 1984-07-30 1988-01-19 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4772700A (en) * 1985-12-19 1988-09-20 Showa Denko Kabushiki Kaisha Spiropiperidinenaphthoxazine compound
US4784474A (en) * 1984-07-06 1988-11-15 Toray Industries, Inc. Spiro-oxazine compounds and preparation thereof and photochromic shaped article
US4785097A (en) * 1986-09-26 1988-11-15 Ppg Industries, Inc. Method for synthesizing spiro-oxazines
US4792224A (en) * 1986-11-28 1988-12-20 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4816584A (en) * 1986-11-12 1989-03-28 Ppg Industries, Inc. Photochromic spiro(indoline)benzoxazines
US4831142A (en) * 1986-09-26 1989-05-16 Ppg Industries, Inc. Spiro indoline-pyranobenzoxazinones
DE3814631A1 (en) * 1988-04-29 1989-11-09 Rodenstock Optik G PHOTOCHROME SUBSTANCES (IV)
US4909963A (en) * 1986-09-26 1990-03-20 Ppg Industries, Inc. Photochromic article
US4931219A (en) * 1987-07-27 1990-06-05 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4931221A (en) * 1988-12-30 1990-06-05 Ppg Industries, Inc. Photochromic spiropyran compounds
US4931220A (en) * 1987-11-24 1990-06-05 Ppg Industries, Inc. Organic photochromic pigment particulates
US4936995A (en) * 1988-05-17 1990-06-26 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4962013A (en) * 1987-10-16 1990-10-09 Nissan Motor Co., Ltd. Yokohama Photochromic material containing a spirooxazine and a nitroxy free radical triplet state quencher
US4968454A (en) * 1988-01-25 1990-11-06 Ppg Industries, Inc. Variable-light transmittance article and method for preparing same
US4980089A (en) * 1989-07-12 1990-12-25 Ppg Industries, Inc. Photochromic spiropyran compounds
US4986934A (en) * 1988-03-25 1991-01-22 Ppg Industries, Inc. Photochromic compound and articles containing the same
US5021196A (en) * 1988-01-25 1991-06-04 Ppg Industries, Inc. Method for preparing variable-light transmittance article
US5055576A (en) * 1989-12-12 1991-10-08 Enichem Synthesis, S.P.A. Photochromatic and thermochromatic spiro-oxazepin-oxazine compounds and the process for their preparation
US5066818A (en) * 1990-03-07 1991-11-19 Ppg Industries, Inc. Photochromic naphthopyran compounds
US5171636A (en) * 1989-12-12 1992-12-15 Enichem Synthesis S.P.A. Photochromatic and thermochromatic spiro-oxazepin-oxazine compounds and the process for their preparation
US5200116A (en) * 1990-07-23 1993-04-06 Ppg Industries, Inc. Photochromic chromene compounds
US5238981A (en) * 1992-02-24 1993-08-24 Transitions Optical, Inc. Photochromic naphthopyrans
US5244602A (en) * 1990-12-03 1993-09-14 Ppg Industries, Inc. Photochromic naphthopyrans
US5288877A (en) * 1991-07-03 1994-02-22 Ppg Industries, Inc. Continuous process for preparing indolenine compounds
JPH0666003B2 (en) 1986-07-15 1994-08-24 呉羽化学工業株式会社 Method for manufacturing optical member made of polarizing resin having dimming effect
US5384077A (en) * 1993-06-21 1995-01-24 Transitions Optical, Inc. Photochromic naphthopyran compounds
US5391327A (en) * 1992-09-25 1995-02-21 Transitions Optical, Inc. Photochromic compositions of improved fatigue resistance
US5405958A (en) * 1992-12-21 1995-04-11 Transitions Optical, Inc. Photochromic spiro(indoline)naphthoxazine compounds
US5411679A (en) * 1993-03-12 1995-05-02 Transitions Optical, Inc. Benzopyrans
US5458814A (en) * 1993-12-09 1995-10-17 Transitions Optical, Inc. Substituted naphthopyrans
US5466398A (en) * 1993-06-21 1995-11-14 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
WO1996011926A1 (en) * 1994-10-13 1996-04-25 Ppg Industries, Inc. Photochromic naphthoxazine compounds
US5531940A (en) * 1993-12-10 1996-07-02 Innotech, Inc. Method for manufacturing photochromic lenses
US5552090A (en) * 1993-06-21 1996-09-03 Ppg Industries, Inc. Photochromic naphthopyran compounds
US5552091A (en) * 1993-03-12 1996-09-03 Ppg Industries, Inc. Benzopyran compounds
US5565147A (en) * 1994-04-08 1996-10-15 Transitions Optical, Inc. Photochromic naphthopyran compounds
US5578252A (en) * 1993-06-21 1996-11-26 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5585042A (en) * 1992-02-24 1996-12-17 Transitions Optical, Inc. Photochromic naphthopyrans
US5645767A (en) * 1994-11-03 1997-07-08 Transitions Optical, Inc. Photochromic indeno-fused naphthopyrans
US5650098A (en) * 1993-12-09 1997-07-22 Transitions Optical, Inc. Substituted naphthopyrans
US5651923A (en) * 1993-12-09 1997-07-29 Transitions Optical, Inc. Substituted naphthopyrans
US5656206A (en) * 1995-06-14 1997-08-12 Transitions Optical, Inc. Substituted naphthopyrans
US5658501A (en) * 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
US5658500A (en) * 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
US5699182A (en) * 1995-05-25 1997-12-16 Xytronyx, Inc. Light fatigue resistant photochromic formulations
US5698141A (en) * 1996-06-17 1997-12-16 Ppg Industries, Inc. Photochromic heterocyclic fused indenonaphthopyrans
US5723072A (en) * 1996-06-17 1998-03-03 Ppg Industries, Inc. Photochromic heterocyclic fused indenonaphthopyrans
US5730908A (en) * 1991-07-24 1998-03-24 Enichem Synthesis S.P.A. Photochromatic and thermochromatic compounds and their application in polymeric materials
US5739243A (en) * 1996-11-27 1998-04-14 Ppg Industries, Inc. Polymerizable composition
US5744070A (en) * 1995-12-20 1998-04-28 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5783116A (en) * 1997-10-16 1998-07-21 Ppg Industries, Inc. Derivatives of carbocyclic fused naphthopyrans
US5789015A (en) * 1996-06-26 1998-08-04 Innotech, Inc. Impregnation of plastic substrates with photochromic additives
US5801243A (en) * 1993-06-28 1998-09-01 Optische Werke G. Rodenstock Photochromic compounds (7)
US5808063A (en) * 1997-10-01 1998-09-15 Ppg Industries, Inc. Photochromic spiro(indoline) fluoranthenoxazine compounds
US5811034A (en) * 1997-10-23 1998-09-22 Ppg Industries, Inc. 7-methylidene-5-oxo-furo fused naphthopyrans
US5869658A (en) * 1997-12-15 1999-02-09 Ppg Industries, Inc. Photochromic indeno-fused naptho 2,1-b!pyrans
US5879592A (en) * 1997-12-10 1999-03-09 Ppg Industries, Inc. Water soluble photochromic compounds, compositions and optical elements comprising the compounds
US5891368A (en) * 1997-10-01 1999-04-06 Ppg Industries, Inc. Fluoranthenopyrans
US5914174A (en) * 1996-12-05 1999-06-22 Innotech, Inc. Lens or semi-finished blank comprising photochromic resin compositions
US5917006A (en) * 1998-01-16 1999-06-29 Ppg Industries Ohio, Inc. Optical resin composition
US5932681A (en) * 1998-03-09 1999-08-03 Ppg Industries Ohio, Inc. Method of preparing an optical polymerizate
US5942158A (en) * 1998-03-09 1999-08-24 Ppg Industries Ohio, Inc. One-component optical resin composition
US5955520A (en) * 1996-06-17 1999-09-21 Ppg Industries, Inc. Photochromic indeno-fused naphthopyrans
US5965680A (en) * 1996-11-27 1999-10-12 Ppg Industries Ohio, Inc. Optical resin composition from polyol((meth)acryloyl carbonate) monomer
US5973093A (en) * 1996-11-27 1999-10-26 Ppg Industries Ohio, Inc. Polymerizable polyol (allyl carbonate) composition
US5976422A (en) * 1998-03-09 1999-11-02 Ppg Industries Ohio, Inc. Optical resin composition
US5981634A (en) * 1996-11-27 1999-11-09 Ppg Industries Ohio, Inc. Method of preparing photochromic articles
US5998520A (en) * 1997-07-02 1999-12-07 Bayer Corporation Photochromic compositions having improved fade rate
US6034193A (en) * 1995-07-12 2000-03-07 Corning Incorporated Photochromic organic materials
US6068797A (en) * 1998-12-11 2000-05-30 Ppg Industries Ohio, Inc. Method of preparing a shaped article having a photochromic coating thereon
US6106744A (en) * 1997-12-03 2000-08-22 Ppg Industries Ohio, Inc. Photochromic pyrano-fused naphthopyrans
US6286423B1 (en) 1997-02-11 2001-09-11 Geoffrey A. Mccue Method and apparatus for preparing a screen printing screen using an image carrier
US6296785B1 (en) 1999-09-17 2001-10-02 Ppg Industries Ohio, Inc. Indeno-fused photochromic naphthopyrans
WO2001081352A1 (en) * 2000-04-20 2001-11-01 Great Lakes Chemical (Europe) Gmbh Photochromatic pyrano-1,3-oxazinonaphthalene derivatives
US6316570B1 (en) 1999-06-23 2001-11-13 Ppg Industries Ohio, Inc. Polymerizable composition of aliphatic polyol (allyl carbonate)
US6342571B1 (en) 1999-08-20 2002-01-29 Ppg Industries Ohio, Inc. High refractive index optical resin composition
US6348604B1 (en) 1999-09-17 2002-02-19 Ppg Industries Ohio, Inc. Photochromic naphthopyrans
US6478989B1 (en) 1997-09-19 2002-11-12 Transitions Optical, Inc. Aromatic substituted naphthopyrans
US6500245B1 (en) 1998-11-06 2002-12-31 Geoffrey A. Mccue Thermoresponsive coloring formulation for use on reimageable image carrier
US6506864B1 (en) 2000-04-10 2003-01-14 Ppg Industries Ohio, Inc. Polymerizable composition of allyl functional monomers
US20030045612A1 (en) * 2000-11-28 2003-03-06 Misura Michael S. Organic photochromic compositions of improved kinetic performance
US20030096935A1 (en) * 2001-11-16 2003-05-22 Nagpal Vidhu J. Impact resistant polyureaurethane and method of preparation
US20030105265A1 (en) * 2001-11-16 2003-06-05 Mcdonald William H. Impact resistant polyureaurethane and polyureaurethane prepolymer having low NCO/OH ratio
US20030136948A1 (en) * 2001-11-01 2003-07-24 Cletus N. Welch Photochromic polymerizable compositions
US20030149217A1 (en) * 2001-11-16 2003-08-07 Bojkova Nina V. High impact poly (urethane urea) polysulfides
US20030164481A1 (en) * 2002-01-09 2003-09-04 Havens Thomas G. Ophthalmic filter materials
US20030173551A1 (en) * 1999-12-13 2003-09-18 Nagpal Vidhu J. Polymerizable polyol (allyl carbonate) compositions
US6630597B1 (en) 1997-12-15 2003-10-07 Transitions Optical, Inc. Photochromic 6-aryl substituted 3H-naphtho(2,1-b)pyrans
US6631021B2 (en) 2000-03-20 2003-10-07 Ppg Industries Ohio, Inc. Polyfunctional thiirane compounds
US6669873B1 (en) 1999-04-22 2003-12-30 Ppc Industries Ohio, Inc. Optical resin composition comprising thiol-ene prepolymer
US6686466B2 (en) 2001-11-13 2004-02-03 Johnson & Johnson Vision Care, Inc. Photochromic oxazine compounds and methods for their manufacture
US20040021133A1 (en) * 2002-07-31 2004-02-05 Nagpal Vidhu J. High refractive index polymerizable composition
US20040138401A1 (en) * 2002-11-05 2004-07-15 Nina Bojkova High impact poly (urethane urea) polysulfides
US20050168689A1 (en) * 2004-01-30 2005-08-04 Knox Carol L. Photochromic optical element
US20050282991A1 (en) * 2001-11-16 2005-12-22 Bojkova Nina V High impact poly (urethane urea) polysulfides
US20060025563A1 (en) * 2002-12-20 2006-02-02 Nina Bojkova Sulfide-containing polythiols
US20060159925A1 (en) * 2004-12-20 2006-07-20 Satish Agrawal High-intensity, persistent thermochromic compositions and objects, and methods for creating the same
US7087698B1 (en) 1999-11-18 2006-08-08 Ppg Industries Ohio, Inc. Method of preparing an optical polymerizate
US7098290B1 (en) 1999-11-18 2006-08-29 Ppg Industries Ohio, Inc. Method of preparing an optical polymerizate
US20060241273A1 (en) * 2001-11-16 2006-10-26 Bojkova Nina V High impact poly (urethane urea) polysulfides
WO2007070627A2 (en) 2005-12-16 2007-06-21 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070142605A1 (en) * 2005-12-16 2007-06-21 Bojkova Nina V Sulfur-containing oligomers and high index polyurethanes prepared therefrom
US20070142604A1 (en) * 2005-12-16 2007-06-21 Nina Bojkova Polyurethanes and sulfur-containing polyurethanes and methods of preparation
US20070142602A1 (en) * 2005-12-16 2007-06-21 Rukavina Thomas G Polyurethanes and sulfur-containing polyurethanes and methods of preparation
US20070142603A1 (en) * 2005-12-16 2007-06-21 Rukavina Thomas G Polyurethane(urea) and sulfur-containing polyurethane(urea) and methods of preparation
US20070149748A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US20070148471A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Impact resistant polyurethane and poly(ureaurethane) articles and methods of making the same
US20070149747A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US20070149749A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Polyurethanes prepared from polycarbonate polyols, articles and coatings prepared therefrom and methods of making the same
US20070155936A1 (en) * 2004-09-01 2007-07-05 Rukavina Thomas G Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070155942A1 (en) * 2004-09-01 2007-07-05 Rukavina Thomas G Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070155895A1 (en) * 2004-09-01 2007-07-05 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US20070155935A1 (en) * 2004-09-01 2007-07-05 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US20070167601A1 (en) * 2004-09-01 2007-07-19 Rukavina Thomas G Polyurethanes prepared from polycarbonate polyols, articles and coatings prepared therefrom and methods of making the same
US20070167600A1 (en) * 2004-09-01 2007-07-19 Rukavina Thomas G Polyurethanes prepared from polycaprolactone polyols, articles and coatings prepared therefrom and methods of making the same
US20070173601A1 (en) * 2004-09-01 2007-07-26 Rukavina Thomas G Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070173582A1 (en) * 2004-09-01 2007-07-26 Rukavina Thomas G Reinforced polyurethanes and poly(ureaurethane)s, methods of making the same and articles prepared therefrom
US20070173627A1 (en) * 2004-09-01 2007-07-26 Rukavina Thomas G Poly(ureaurethanes)s, articles and coatings prepared therefrom and methods of making the same
US20070225468A1 (en) * 2004-09-01 2007-09-27 Rukavina Thomas G Polyurethanes prepared from polyester polyols and/or polycaprolactone polyols, articles and coatings prepared therefrom and methods of making the same
US20070248827A1 (en) * 2004-09-01 2007-10-25 Rukavina Thomas G Multilayer laminated articles including polyurethane and/or poly(ureaurethane) layers and methods of making the same
US20070251421A1 (en) * 2004-09-01 2007-11-01 Rukavina Thomas G Powder coatings prepared from polyurethanes and poly(ureaurethane)s, coated articles and methods of making the same
US20070256597A1 (en) * 2004-09-01 2007-11-08 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
CN100371364C (en) * 1999-11-18 2008-02-27 Ppg工业俄亥俄公司 Method of preparing optical polymerizate
US20080071016A1 (en) * 2006-09-14 2008-03-20 Ppg Industries Ohio, Inc. Polyureaurethane composition having improved color stability
US20080125570A1 (en) * 2006-05-05 2008-05-29 Ppg Industries Ohio, Inc. Thioether functional oligomeric polythiols and articles prepared therefrom
US20080121818A1 (en) * 2006-09-15 2008-05-29 Satish Agrawal Phosphorescent compositions for identification
US20080121815A1 (en) * 2006-09-15 2008-05-29 Satish Agrawal Phosphorescent compositions and methods for identification using the same
US20080195072A1 (en) * 2007-02-08 2008-08-14 The Procter & Gamble Company Disposable absorbent articles having photochromic ink based graphics
US7473754B1 (en) 2000-10-17 2009-01-06 Ppg Industries Ohio, Inc. Optical resin composition
US20090071365A1 (en) * 2007-09-13 2009-03-19 Satish Agrawal Tissue marking compositions
US20090076535A1 (en) * 2007-09-13 2009-03-19 Satish Agrawal Tissue markings and methods for reversibly marking tissue employing the same
US20090280329A1 (en) * 2004-09-01 2009-11-12 Ppg Industries Ohio, Inc. Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same
US20090281268A1 (en) * 2004-09-01 2009-11-12 Ppg Industries Ohio, Inc. Methods for preparing polyurethanes
US20090280709A1 (en) * 2004-09-01 2009-11-12 Ppg Industries Ohio, Inc. Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same
US20100124649A1 (en) * 2004-09-01 2010-05-20 Rukavina Thomas G Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20110071257A1 (en) * 2009-09-22 2011-03-24 David Henry Photochromic compositions, resins and articles obtained therefrom
EP2325234A2 (en) 2002-12-20 2011-05-25 PPG Industries Ohio, Inc. High impact poly(urethane urea) polysulfides
US20110140056A1 (en) * 2003-07-01 2011-06-16 Transitions Optical, Inc. Indeno-fused ring compounds
US20110140002A1 (en) * 2004-12-20 2011-06-16 Performance Indicator, Llc Photoluminescent Compositions, Methods of Manufacture and Novel Uses
EP2385075A1 (en) 2005-12-16 2011-11-09 PPG Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
WO2012082560A1 (en) 2010-12-16 2012-06-21 Transitions Optical, Inc. Methods of making fused ring compounds
WO2012082837A1 (en) 2010-12-16 2012-06-21 Transitions Optical, Inc. Method of making indeno-fused naphthol materials
WO2013032608A1 (en) 2011-08-31 2013-03-07 Transitions Optical, Inc. Indeno-fused ring compounds
WO2013036774A1 (en) 2011-09-08 2013-03-14 Ppg Industries Ohio, Inc. Polymerizable compositions containing (meth)acrylate monomers having sulfide linkages
US8779168B2 (en) 2010-12-16 2014-07-15 Transitions Optical, Inc. Lactone compounds and materials made therefrom
WO2014152819A1 (en) 2013-03-14 2014-09-25 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US9464169B2 (en) 2004-09-01 2016-10-11 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US9568643B2 (en) 2012-12-13 2017-02-14 Ppg Industries Ohio, Inc. Polyurethane urea-containing compositions and optical articles and methods for preparing them
US10000472B2 (en) 2003-07-01 2018-06-19 Transitions Optical, Inc. Photochromic compounds
US11008418B2 (en) 2004-09-01 2021-05-18 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
WO2021181341A1 (en) 2020-03-11 2021-09-16 Alcon Inc. Photochromic polydiorganosiloxane vinylic crosslinkers
US11149107B2 (en) 2004-09-01 2021-10-19 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
WO2021245551A1 (en) 2020-06-02 2021-12-09 Alcon Inc. Method for making photochromic contact lenses
US11248083B2 (en) 2004-09-01 2022-02-15 Ppg Industries Ohio, Inc. Aircraft windows
WO2022090967A1 (en) 2020-10-28 2022-05-05 Alcon Inc. Method for making photochromic contact lenses
WO2022097048A1 (en) 2020-11-04 2022-05-12 Alcon Inc. Method for making photochromic contact lenses
WO2022097049A1 (en) 2020-11-04 2022-05-12 Alcon Inc. Method for making photochromic contact lenses
WO2022189940A1 (en) 2021-03-08 2022-09-15 Alcon Inc. Method for making photofunctional contact lenses
WO2022208450A1 (en) 2021-04-01 2022-10-06 Alcon Inc. Method for making photochromic contact lenses
US11591436B2 (en) 2004-09-01 2023-02-28 Ppg Industries Ohio, Inc. Polyurethane article and methods of making the same
WO2023209631A1 (en) 2022-04-28 2023-11-02 Alcon Inc. Method for making uv and hevl-absorbing ophthalmic lenses

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61263982A (en) * 1985-01-25 1986-11-21 Mitsubishi Chem Ind Ltd 3,3-dimethyl-spiro(indolino-2,3'-naphtho(2,1-b)-(1,4) oxazine) compound
DE3525891A1 (en) * 1985-07-19 1987-01-22 Rodenstock Optik G PHOTOCHROME COMPOUNDS (III)
GB8620430D0 (en) * 1986-08-22 1986-10-01 Plessey Co Plc Marking of articles
DE19643773A1 (en) * 1996-10-23 1998-04-30 Tschochner Rolfheinz Photo:chromic spiro:oxazine compounds

Cited By (264)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4215010A (en) * 1978-09-08 1980-07-29 American Optical Corporation Photochromic compounds
US4342668A (en) * 1978-09-08 1982-08-03 American Optical Corporation Photochromic compounds
DE2936255A1 (en) * 1978-09-08 1980-03-20 American Optical Corp PHOTOCHROMATIC OXAZINE COMPOUNDS AND THEIR USE FOR PHOTOCHROMATIC OPTICAL ELEMENTS
DE3310388A1 (en) * 1982-03-22 1983-09-29 American Optical Co., Southbridge, Mass. FATIGUE-RESISTANT PHOTOCHROME COMPOSITIONS AND ITEMS
JPS6084527A (en) * 1983-08-02 1985-05-13 オプテイツシエ．ウエルケ．ゲ−．ロ−デンストツク Phototropic spectacles frame
US4699473A (en) * 1983-08-08 1987-10-13 American Optical Corporation Trifluoromethyl substituted spirooxazine photochromic dyes
US4637698A (en) * 1983-11-04 1987-01-20 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4784474A (en) * 1984-07-06 1988-11-15 Toray Industries, Inc. Spiro-oxazine compounds and preparation thereof and photochromic shaped article
US4720547A (en) * 1984-07-30 1988-01-19 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4636561A (en) * 1984-12-11 1987-01-13 Unitika Ltd. Spiroindolinenaphthoxadine photochromic compounds
US4756973A (en) * 1985-07-09 1988-07-12 Kureha Kagaku Kogyo Kabushiki Kaisha Photochromic lens
GB2179174B (en) * 1985-07-09 1989-07-19 Kureha Chemical Ind Co Ltd Photochromic resin lens
GB2179174A (en) * 1985-07-09 1987-02-25 Kureha Chemical Ind Co Ltd Photochromic resin lens
DE3629624A1 (en) * 1985-09-03 1987-03-19 Ppg Industries Inc METHOD FOR PRODUCING SPIRO (INDOLIN) -LIKE CONNECTIONS
US4634767A (en) * 1985-09-03 1987-01-06 Ppg Industries, Inc. Method for preparing spiro(indoline)-type photochromic compounds
US4772700A (en) * 1985-12-19 1988-09-20 Showa Denko Kabushiki Kaisha Spiropiperidinenaphthoxazine compound
JPH0666003B2 (en) 1986-07-15 1994-08-24 呉羽化学工業株式会社 Method for manufacturing optical member made of polarizing resin having dimming effect
US4831142A (en) * 1986-09-26 1989-05-16 Ppg Industries, Inc. Spiro indoline-pyranobenzoxazinones
US4785097A (en) * 1986-09-26 1988-11-15 Ppg Industries, Inc. Method for synthesizing spiro-oxazines
US4909963A (en) * 1986-09-26 1990-03-20 Ppg Industries, Inc. Photochromic article
US4816584A (en) * 1986-11-12 1989-03-28 Ppg Industries, Inc. Photochromic spiro(indoline)benzoxazines
US4792224A (en) * 1986-11-28 1988-12-20 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4931219A (en) * 1987-07-27 1990-06-05 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4962013A (en) * 1987-10-16 1990-10-09 Nissan Motor Co., Ltd. Yokohama Photochromic material containing a spirooxazine and a nitroxy free radical triplet state quencher
US4931220A (en) * 1987-11-24 1990-06-05 Ppg Industries, Inc. Organic photochromic pigment particulates
US4968454A (en) * 1988-01-25 1990-11-06 Ppg Industries, Inc. Variable-light transmittance article and method for preparing same
US5021196A (en) * 1988-01-25 1991-06-04 Ppg Industries, Inc. Method for preparing variable-light transmittance article
US4986934A (en) * 1988-03-25 1991-01-22 Ppg Industries, Inc. Photochromic compound and articles containing the same
DE3814631A1 (en) * 1988-04-29 1989-11-09 Rodenstock Optik G PHOTOCHROME SUBSTANCES (IV)
US4936995A (en) * 1988-05-17 1990-06-26 Ppg Industries, Inc. Photochromic compound and articles containing the same
US4931221A (en) * 1988-12-30 1990-06-05 Ppg Industries, Inc. Photochromic spiropyran compounds
US4980089A (en) * 1989-07-12 1990-12-25 Ppg Industries, Inc. Photochromic spiropyran compounds
US5055576A (en) * 1989-12-12 1991-10-08 Enichem Synthesis, S.P.A. Photochromatic and thermochromatic spiro-oxazepin-oxazine compounds and the process for their preparation
US5110922A (en) * 1989-12-12 1992-05-05 Enichem Synthesis S.P.A. Photochromatic and thermochromatic spiro-oxazepin-oxazine compounds and the process for their preparation
US5171636A (en) * 1989-12-12 1992-12-15 Enichem Synthesis S.P.A. Photochromatic and thermochromatic spiro-oxazepin-oxazine compounds and the process for their preparation
US5066818A (en) * 1990-03-07 1991-11-19 Ppg Industries, Inc. Photochromic naphthopyran compounds
US5200116A (en) * 1990-07-23 1993-04-06 Ppg Industries, Inc. Photochromic chromene compounds
US5244602A (en) * 1990-12-03 1993-09-14 Ppg Industries, Inc. Photochromic naphthopyrans
US5340857A (en) * 1990-12-03 1994-08-23 Ppg Industries, Inc. Photochromic naphthopyrans
US5288877A (en) * 1991-07-03 1994-02-22 Ppg Industries, Inc. Continuous process for preparing indolenine compounds
US5730908A (en) * 1991-07-24 1998-03-24 Enichem Synthesis S.P.A. Photochromatic and thermochromatic compounds and their application in polymeric materials
US5238981A (en) * 1992-02-24 1993-08-24 Transitions Optical, Inc. Photochromic naphthopyrans
US5369158A (en) * 1992-02-24 1994-11-29 Transitions Optical, Inc. Photochromic naphthopyrans
US5585042A (en) * 1992-02-24 1996-12-17 Transitions Optical, Inc. Photochromic naphthopyrans
US5391327A (en) * 1992-09-25 1995-02-21 Transitions Optical, Inc. Photochromic compositions of improved fatigue resistance
US5405958A (en) * 1992-12-21 1995-04-11 Transitions Optical, Inc. Photochromic spiro(indoline)naphthoxazine compounds
US5411679A (en) * 1993-03-12 1995-05-02 Transitions Optical, Inc. Benzopyrans
US5552091A (en) * 1993-03-12 1996-09-03 Ppg Industries, Inc. Benzopyran compounds
US5429774A (en) * 1993-03-12 1995-07-04 Transitions Optical, Inc. Benzopyran compounds
US5552090A (en) * 1993-06-21 1996-09-03 Ppg Industries, Inc. Photochromic naphthopyran compounds
US5466398A (en) * 1993-06-21 1995-11-14 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5458815A (en) * 1993-06-21 1995-10-17 Transitions Optical, Inc. Photochromic naphthopyran compounds
US5384077A (en) * 1993-06-21 1995-01-24 Transitions Optical, Inc. Photochromic naphthopyran compounds
US5578252A (en) * 1993-06-21 1996-11-26 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5637262A (en) * 1993-06-21 1997-06-10 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5801243A (en) * 1993-06-28 1998-09-01 Optische Werke G. Rodenstock Photochromic compounds (7)
US5458814A (en) * 1993-12-09 1995-10-17 Transitions Optical, Inc. Substituted naphthopyrans
US5573712A (en) * 1993-12-09 1996-11-12 Transitions Optical, Inc. Substituted naphthopyrans
US5650098A (en) * 1993-12-09 1997-07-22 Transitions Optical, Inc. Substituted naphthopyrans
US5651923A (en) * 1993-12-09 1997-07-29 Transitions Optical, Inc. Substituted naphthopyrans
US5531940A (en) * 1993-12-10 1996-07-02 Innotech, Inc. Method for manufacturing photochromic lenses
US5565147A (en) * 1994-04-08 1996-10-15 Transitions Optical, Inc. Photochromic naphthopyran compounds
US5674432A (en) * 1994-04-08 1997-10-07 Transitions Optical, Inc. Photochromic naphthopyran compounds
WO1996011926A1 (en) * 1994-10-13 1996-04-25 Ppg Industries, Inc. Photochromic naphthoxazine compounds
US5645767A (en) * 1994-11-03 1997-07-08 Transitions Optical, Inc. Photochromic indeno-fused naphthopyrans
US5699182A (en) * 1995-05-25 1997-12-16 Xytronyx, Inc. Light fatigue resistant photochromic formulations
US5656206A (en) * 1995-06-14 1997-08-12 Transitions Optical, Inc. Substituted naphthopyrans
US5658501A (en) * 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
US5658500A (en) * 1995-06-14 1997-08-19 Transitions Optical, Inc. Substituted naphthopyrans
US6034193A (en) * 1995-07-12 2000-03-07 Corning Incorporated Photochromic organic materials
US5744070A (en) * 1995-12-20 1998-04-28 Transitions Optical, Inc. Photochromic substituted naphthopyran compounds
US5955520A (en) * 1996-06-17 1999-09-21 Ppg Industries, Inc. Photochromic indeno-fused naphthopyrans
US5723072A (en) * 1996-06-17 1998-03-03 Ppg Industries, Inc. Photochromic heterocyclic fused indenonaphthopyrans
US5698141A (en) * 1996-06-17 1997-12-16 Ppg Industries, Inc. Photochromic heterocyclic fused indenonaphthopyrans
US5789015A (en) * 1996-06-26 1998-08-04 Innotech, Inc. Impregnation of plastic substrates with photochromic additives
US5851585A (en) * 1996-06-26 1998-12-22 Innotech, Inc. Impregnation of plastic substrates with photochromic additives
US5739243A (en) * 1996-11-27 1998-04-14 Ppg Industries, Inc. Polymerizable composition
US5973093A (en) * 1996-11-27 1999-10-26 Ppg Industries Ohio, Inc. Polymerizable polyol (allyl carbonate) composition
US5965680A (en) * 1996-11-27 1999-10-12 Ppg Industries Ohio, Inc. Optical resin composition from polyol((meth)acryloyl carbonate) monomer
US5981634A (en) * 1996-11-27 1999-11-09 Ppg Industries Ohio, Inc. Method of preparing photochromic articles
US5914174A (en) * 1996-12-05 1999-06-22 Innotech, Inc. Lens or semi-finished blank comprising photochromic resin compositions
US6286423B1 (en) 1997-02-11 2001-09-11 Geoffrey A. Mccue Method and apparatus for preparing a screen printing screen using an image carrier
US5998520A (en) * 1997-07-02 1999-12-07 Bayer Corporation Photochromic compositions having improved fade rate
US6478989B1 (en) 1997-09-19 2002-11-12 Transitions Optical, Inc. Aromatic substituted naphthopyrans
US5891368A (en) * 1997-10-01 1999-04-06 Ppg Industries, Inc. Fluoranthenopyrans
US5808063A (en) * 1997-10-01 1998-09-15 Ppg Industries, Inc. Photochromic spiro(indoline) fluoranthenoxazine compounds
US5783116A (en) * 1997-10-16 1998-07-21 Ppg Industries, Inc. Derivatives of carbocyclic fused naphthopyrans
US5811034A (en) * 1997-10-23 1998-09-22 Ppg Industries, Inc. 7-methylidene-5-oxo-furo fused naphthopyrans
US6106744A (en) * 1997-12-03 2000-08-22 Ppg Industries Ohio, Inc. Photochromic pyrano-fused naphthopyrans
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
US5917006A (en) * 1998-01-16 1999-06-29 Ppg Industries Ohio, Inc. Optical resin composition
US5976422A (en) * 1998-03-09 1999-11-02 Ppg Industries Ohio, Inc. Optical resin composition
US5942158A (en) * 1998-03-09 1999-08-24 Ppg Industries Ohio, Inc. One-component optical resin composition
US5932681A (en) * 1998-03-09 1999-08-03 Ppg Industries Ohio, Inc. Method of preparing an optical polymerizate
US6500245B1 (en) 1998-11-06 2002-12-31 Geoffrey A. Mccue Thermoresponsive coloring formulation for use on reimageable image carrier
US6068797A (en) * 1998-12-11 2000-05-30 Ppg Industries Ohio, Inc. Method of preparing a shaped article having a photochromic coating thereon
US6669873B1 (en) 1999-04-22 2003-12-30 Ppc Industries Ohio, Inc. Optical resin composition comprising thiol-ene prepolymer
US6316570B1 (en) 1999-06-23 2001-11-13 Ppg Industries Ohio, Inc. Polymerizable composition of aliphatic polyol (allyl carbonate)
US6342571B1 (en) 1999-08-20 2002-01-29 Ppg Industries Ohio, Inc. High refractive index optical resin composition
US6348604B1 (en) 1999-09-17 2002-02-19 Ppg Industries Ohio, Inc. Photochromic naphthopyrans
US6296785B1 (en) 1999-09-17 2001-10-02 Ppg Industries Ohio, Inc. Indeno-fused photochromic naphthopyrans
US7098290B1 (en) 1999-11-18 2006-08-29 Ppg Industries Ohio, Inc. Method of preparing an optical polymerizate
CN100535026C (en) * 1999-11-18 2009-09-02 Ppg工业俄亥俄公司 Method of preparing optical polymerizate
CN100371364C (en) * 1999-11-18 2008-02-27 Ppg工业俄亥俄公司 Method of preparing optical polymerizate
US7087698B1 (en) 1999-11-18 2006-08-08 Ppg Industries Ohio, Inc. Method of preparing an optical polymerizate
US7214754B2 (en) 1999-12-13 2007-05-08 Ppg Industries Ohio, Inc. Polymerizable polyol (allyl carbonate) compositions
US20030173551A1 (en) * 1999-12-13 2003-09-18 Nagpal Vidhu J. Polymerizable polyol (allyl carbonate) compositions
US6631021B2 (en) 2000-03-20 2003-10-07 Ppg Industries Ohio, Inc. Polyfunctional thiirane compounds
US6506864B1 (en) 2000-04-10 2003-01-14 Ppg Industries Ohio, Inc. Polymerizable composition of allyl functional monomers
US7262294B2 (en) 2000-04-20 2007-08-28 Great Lakes Chemical (Europe) Gmbh Photochromatic pyrano-1,3-oxazinonaphthalene derivatives
WO2001081352A1 (en) * 2000-04-20 2001-11-01 Great Lakes Chemical (Europe) Gmbh Photochromatic pyrano-1,3-oxazinonaphthalene derivatives
US20030164482A1 (en) * 2000-04-20 2003-09-04 William Giroldini Photochromatic pyrano-1,3-oxazinonaphthalene derivatives
US7473754B1 (en) 2000-10-17 2009-01-06 Ppg Industries Ohio, Inc. Optical resin composition
US6713536B2 (en) 2000-11-28 2004-03-30 Transitions Optical, Inc. Removable imbibition composition of photochromic compound and epoxy and polyol kinetic enhancing additives
US20040149966A1 (en) * 2000-11-28 2004-08-05 Misura Michael S. Organic photochromic compositions of improved kinetic performance
US7147889B2 (en) 2000-11-28 2006-12-12 Transition Optical, Inc. Organic photochromic compositions of improved kinetic performance
US20030045612A1 (en) * 2000-11-28 2003-03-06 Misura Michael S. Organic photochromic compositions of improved kinetic performance
US20030136948A1 (en) * 2001-11-01 2003-07-24 Cletus N. Welch Photochromic polymerizable compositions
US6686466B2 (en) 2001-11-13 2004-02-03 Johnson & Johnson Vision Care, Inc. Photochromic oxazine compounds and methods for their manufacture
US7144969B2 (en) 2001-11-16 2006-12-05 Ppg Industries Ohio, Inc. Impact resistant polyureaurethane and polyureaurethane prepolymer having low NCO/OH ratio
US20030096935A1 (en) * 2001-11-16 2003-05-22 Nagpal Vidhu J. Impact resistant polyureaurethane and method of preparation
US20100048852A1 (en) * 2001-11-16 2010-02-25 Ppg Industries Ohio, Inc. High impact poly(urethane urea) polysulfides
US20050282991A1 (en) * 2001-11-16 2005-12-22 Bojkova Nina V High impact poly (urethane urea) polysulfides
US20030105265A1 (en) * 2001-11-16 2003-06-05 Mcdonald William H. Impact resistant polyureaurethane and polyureaurethane prepolymer having low NCO/OH ratio
US20060241273A1 (en) * 2001-11-16 2006-10-26 Bojkova Nina V High impact poly (urethane urea) polysulfides
US20070155940A1 (en) * 2001-11-16 2007-07-05 Ppg Industries Ohio, Inc. Impact resistant polyureaurethane lens
US20030149217A1 (en) * 2001-11-16 2003-08-07 Bojkova Nina V. High impact poly (urethane urea) polysulfides
US20030164481A1 (en) * 2002-01-09 2003-09-04 Havens Thomas G. Ophthalmic filter materials
US6811727B2 (en) 2002-01-09 2004-11-02 Corning Incorporated Ophthalmic filter materials
US20040021133A1 (en) * 2002-07-31 2004-02-05 Nagpal Vidhu J. High refractive index polymerizable composition
US20040138401A1 (en) * 2002-11-05 2004-07-15 Nina Bojkova High impact poly (urethane urea) polysulfides
US7491790B2 (en) 2002-12-20 2009-02-17 Ppg Industries Ohio, Inc. Sulfide-containing polythiols
US20060025563A1 (en) * 2002-12-20 2006-02-02 Nina Bojkova Sulfide-containing polythiols
US7411034B2 (en) 2002-12-20 2008-08-12 Ppg Industries Ohio, Inc. Sulfide-containing polythiols
US20080161528A1 (en) * 2002-12-20 2008-07-03 Ppg Industries Ohio, Inc. Sulfide-containing polythiols
EP2325233A2 (en) 2002-12-20 2011-05-25 PPG Industries Ohio, Inc. High impact poly(urethane urea) polysulfides
EP2325234A2 (en) 2002-12-20 2011-05-25 PPG Industries Ohio, Inc. High impact poly(urethane urea) polysulfides
US9309455B2 (en) 2003-07-01 2016-04-12 Transitions Optical, Inc. Indeno-fused ring compounds
US8698117B2 (en) 2003-07-01 2014-04-15 Transitions Optical, Inc. Indeno-fused ring compounds
US20110140056A1 (en) * 2003-07-01 2011-06-16 Transitions Optical, Inc. Indeno-fused ring compounds
US10532998B2 (en) 2003-07-01 2020-01-14 Transitions Optical, Inc. Photochromic compounds
US10000472B2 (en) 2003-07-01 2018-06-19 Transitions Optical, Inc. Photochromic compounds
US10005763B2 (en) 2003-07-01 2018-06-26 Transitions Optical, Inc. Photochromic compounds
US10501446B2 (en) 2003-07-01 2019-12-10 Transitions Optical, Inc. Photochromic compounds
US10532997B2 (en) 2003-07-01 2020-01-14 Transitions Optical, Inc. Photochromic compounds
US20070177100A1 (en) * 2004-01-30 2007-08-02 Transitions Optical, Inc. Photochromic opitcal element
US20050168689A1 (en) * 2004-01-30 2005-08-04 Knox Carol L. Photochromic optical element
US9822211B2 (en) 2004-09-01 2017-11-21 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US11149107B2 (en) 2004-09-01 2021-10-19 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070149747A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US20070225468A1 (en) * 2004-09-01 2007-09-27 Rukavina Thomas G Polyurethanes prepared from polyester polyols and/or polycaprolactone polyols, articles and coatings prepared therefrom and methods of making the same
US20070248827A1 (en) * 2004-09-01 2007-10-25 Rukavina Thomas G Multilayer laminated articles including polyurethane and/or poly(ureaurethane) layers and methods of making the same
US20070251421A1 (en) * 2004-09-01 2007-11-01 Rukavina Thomas G Powder coatings prepared from polyurethanes and poly(ureaurethane)s, coated articles and methods of making the same
US20070256597A1 (en) * 2004-09-01 2007-11-08 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US10533068B2 (en) 2004-09-01 2020-01-14 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070148471A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Impact resistant polyurethane and poly(ureaurethane) articles and methods of making the same
US20070173582A1 (en) * 2004-09-01 2007-07-26 Rukavina Thomas G Reinforced polyurethanes and poly(ureaurethane)s, methods of making the same and articles prepared therefrom
US20070173601A1 (en) * 2004-09-01 2007-07-26 Rukavina Thomas G Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070167600A1 (en) * 2004-09-01 2007-07-19 Rukavina Thomas G Polyurethanes prepared from polycaprolactone polyols, articles and coatings prepared therefrom and methods of making the same
US20070167601A1 (en) * 2004-09-01 2007-07-19 Rukavina Thomas G Polyurethanes prepared from polycarbonate polyols, articles and coatings prepared therefrom and methods of making the same
US9994670B2 (en) 2004-09-01 2018-06-12 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070149748A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US20070155935A1 (en) * 2004-09-01 2007-07-05 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US9951173B2 (en) 2004-09-01 2018-04-24 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US10590230B2 (en) 2004-09-01 2020-03-17 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US11008418B2 (en) 2004-09-01 2021-05-18 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070155936A1 (en) * 2004-09-01 2007-07-05 Rukavina Thomas G Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US9657134B2 (en) 2004-09-01 2017-05-23 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US9598527B2 (en) 2004-09-01 2017-03-21 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US9464169B2 (en) 2004-09-01 2016-10-11 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070173627A1 (en) * 2004-09-01 2007-07-26 Rukavina Thomas G Poly(ureaurethanes)s, articles and coatings prepared therefrom and methods of making the same
US11248083B2 (en) 2004-09-01 2022-02-15 Ppg Industries Ohio, Inc. Aircraft windows
US20090280329A1 (en) * 2004-09-01 2009-11-12 Ppg Industries Ohio, Inc. Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same
US20090281268A1 (en) * 2004-09-01 2009-11-12 Ppg Industries Ohio, Inc. Methods for preparing polyurethanes
US20090280709A1 (en) * 2004-09-01 2009-11-12 Ppg Industries Ohio, Inc. Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same
US11472912B2 (en) 2004-09-01 2022-10-18 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US9296920B2 (en) 2004-09-01 2016-03-29 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US8933166B2 (en) 2004-09-01 2015-01-13 Ppg Industries Ohio, Inc. Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US20100124649A1 (en) * 2004-09-01 2010-05-20 Rukavina Thomas G Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US8927675B2 (en) 2004-09-01 2015-01-06 Ppg Industries Ohio, Inc. Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US8889815B2 (en) 2004-09-01 2014-11-18 Ppg Industries Ohio, Inc. Reinforced polyurethanes and poly(ureaurethane)s, methods of making the same and articles prepared therefrom
US8865853B2 (en) 2004-09-01 2014-10-21 Ppg Industries Ohio, Inc. Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US8859680B2 (en) 2004-09-01 2014-10-14 Ppg Industries Ohio, Inc Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US11591436B2 (en) 2004-09-01 2023-02-28 Ppg Industries Ohio, Inc. Polyurethane article and methods of making the same
US20070155895A1 (en) * 2004-09-01 2007-07-05 Rukavina Thomas G Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US20070155942A1 (en) * 2004-09-01 2007-07-05 Rukavina Thomas G Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US8835592B2 (en) 2004-09-01 2014-09-16 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US8734951B2 (en) 2004-09-01 2014-05-27 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20070149749A1 (en) * 2004-09-01 2007-06-28 Rukavina Thomas G Polyurethanes prepared from polycarbonate polyols, articles and coatings prepared therefrom and methods of making the same
US8653220B2 (en) 2004-09-01 2014-02-18 Ppg Industries Ohio, Inc. Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US8604153B2 (en) 2004-09-01 2013-12-10 Ppg Industries Ohio, Inc. Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US8399559B2 (en) 2004-09-01 2013-03-19 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US8399094B2 (en) 2004-09-01 2013-03-19 Ppg Industries Ohio, Inc. Multilayer laminated articles including polyurethane and/or poly(ureaurethane) layers and methods of making the same
US8349986B2 (en) 2004-09-01 2013-01-08 Ppg Industries Ohio, Inc. Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US8207286B2 (en) 2004-09-01 2012-06-26 Ppg Industries Ohio, Inc Methods for preparing polyurethanes
US8287757B2 (en) 2004-12-20 2012-10-16 Performance Indicator, Llc High-intensity, persistent photoluminescent formulations and objects, and methods for creating the same
US20110140002A1 (en) * 2004-12-20 2011-06-16 Performance Indicator, Llc Photoluminescent Compositions, Methods of Manufacture and Novel Uses
US8293136B2 (en) 2004-12-20 2012-10-23 Performance Indicator, Llc High-intensity, persistent photoluminescent formulations and objects, and methods for creating the same
US20060159925A1 (en) * 2004-12-20 2006-07-20 Satish Agrawal High-intensity, persistent thermochromic compositions and objects, and methods for creating the same
US20060172135A1 (en) * 2004-12-20 2006-08-03 Satish Agrawal Layered envirochromic materials, applications and methods of preparation thereof
US8282858B2 (en) 2004-12-20 2012-10-09 Performance Indicator, Llc High-intensity, persistent photoluminescent formulations and objects, and methods for creating the same
US8409662B2 (en) 2004-12-20 2013-04-02 Performance Indicator, Llc High-intensity, persistent photoluminescent formulations and objects, and methods for creating the same
US20070142604A1 (en) * 2005-12-16 2007-06-21 Nina Bojkova Polyurethanes and sulfur-containing polyurethanes and methods of preparation
US20070142605A1 (en) * 2005-12-16 2007-06-21 Bojkova Nina V Sulfur-containing oligomers and high index polyurethanes prepared therefrom
WO2007070627A2 (en) 2005-12-16 2007-06-21 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20090176945A1 (en) * 2005-12-16 2009-07-09 Ppg Industries Ohio, Inc. Sulfur-containing polyurethane
EP2385075A1 (en) 2005-12-16 2011-11-09 PPG Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
WO2007139586A2 (en) 2005-12-16 2007-12-06 Ppg Industries Ohio, Inc. Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same
US8017720B2 (en) 2005-12-16 2011-09-13 Ppg Industries Ohio, Inc. Sulfur-containing oligomers and high index polyurethanes prepared therefrom
US20070142602A1 (en) * 2005-12-16 2007-06-21 Rukavina Thomas G Polyurethanes and sulfur-containing polyurethanes and methods of preparation
US20070142603A1 (en) * 2005-12-16 2007-06-21 Rukavina Thomas G Polyurethane(urea) and sulfur-containing polyurethane(urea) and methods of preparation
US7687597B2 (en) 2006-05-05 2010-03-30 Ppg Industries Ohio, Inc. Thioether functional oligomeric polythiols and articles prepared therefrom
US7553925B2 (en) 2006-05-05 2009-06-30 Ppg Industries Ohio, Inc. Thioether functional oligomeric polythiols and articles prepared therefrom
US7696296B2 (en) 2006-05-05 2010-04-13 Ppg Industries Ohio, Inc. Compositions and articles prepared from the thioether functional oligomeric polythiols
US20080125570A1 (en) * 2006-05-05 2008-05-29 Ppg Industries Ohio, Inc. Thioether functional oligomeric polythiols and articles prepared therefrom
US20080125525A1 (en) * 2006-05-05 2008-05-29 Ppg Industries Ohio, Inc. Thioether functional oligomeric polythiols and articles prepared therefrom
US20080071016A1 (en) * 2006-09-14 2008-03-20 Ppg Industries Ohio, Inc. Polyureaurethane composition having improved color stability
US20080121815A1 (en) * 2006-09-15 2008-05-29 Satish Agrawal Phosphorescent compositions and methods for identification using the same
USRE44254E1 (en) 2006-09-15 2013-06-04 Performance Indicator, Llc Phosphorescent compositions and methods for identification using the same
US7910022B2 (en) 2006-09-15 2011-03-22 Performance Indicator, Llc Phosphorescent compositions for identification
US7547894B2 (en) 2006-09-15 2009-06-16 Performance Indicator, L.L.C. Phosphorescent compositions and methods for identification using the same
US20080121818A1 (en) * 2006-09-15 2008-05-29 Satish Agrawal Phosphorescent compositions for identification
US20080195072A1 (en) * 2007-02-08 2008-08-14 The Procter & Gamble Company Disposable absorbent articles having photochromic ink based graphics
US8039193B2 (en) 2007-09-13 2011-10-18 Performance Indicator Llc Tissue markings and methods for reversibly marking tissue employing the same
US7842128B2 (en) 2007-09-13 2010-11-30 Performance Indicatior LLC Tissue marking compositions
US20090076535A1 (en) * 2007-09-13 2009-03-19 Satish Agrawal Tissue markings and methods for reversibly marking tissue employing the same
US20090071365A1 (en) * 2007-09-13 2009-03-19 Satish Agrawal Tissue marking compositions
US8188181B2 (en) 2009-09-22 2012-05-29 Corning Incorporated Photochromic compositions, resins and articles obtained therefrom
US20110071257A1 (en) * 2009-09-22 2011-03-24 David Henry Photochromic compositions, resins and articles obtained therefrom
EP2305768A1 (en) 2009-09-22 2011-04-06 Corning Incorporated Photochromic compositions, resins and articles obtained therefrom
US9878971B2 (en) 2010-12-16 2018-01-30 Transitions Optical, Inc. Methods of making fused ring compounds
WO2012082381A1 (en) 2010-12-16 2012-06-21 Transitions Optical, Inc. Indeno- fused ring compounds having photochromic properties
WO2012082837A1 (en) 2010-12-16 2012-06-21 Transitions Optical, Inc. Method of making indeno-fused naphthol materials
US9487499B2 (en) 2010-12-16 2016-11-08 Transitions Optical, Inc. Methods of making fused ring compounds
WO2012082560A1 (en) 2010-12-16 2012-06-21 Transitions Optical, Inc. Methods of making fused ring compounds
US9139571B2 (en) 2010-12-16 2015-09-22 Transitions Optical, Inc. Methods of making fused ring compounds
US9073838B2 (en) 2010-12-16 2015-07-07 Transitions Optical, Inc. Method of making indeno-fused naphthol materials
US10689317B2 (en) 2010-12-16 2020-06-23 Transitions Optical, Inc. Methods of making fused ring compounds
US8779168B2 (en) 2010-12-16 2014-07-15 Transitions Optical, Inc. Lactone compounds and materials made therefrom
US8765978B2 (en) 2010-12-16 2014-07-01 Transitions Optical, Inc. Method of making indeno-fused naphthol materials
WO2013032608A1 (en) 2011-08-31 2013-03-07 Transitions Optical, Inc. Indeno-fused ring compounds
WO2013036774A1 (en) 2011-09-08 2013-03-14 Ppg Industries Ohio, Inc. Polymerizable compositions containing (meth)acrylate monomers having sulfide linkages
EP3838935A2 (en) 2011-09-08 2021-06-23 PPG Industries Ohio, Inc. Polymerizable compositions containing (meth)acrylate monomers having sulfide linkages
EP3957661A1 (en) 2011-09-08 2022-02-23 PPG Industries Ohio, Inc. Polymerizable compositions containing (meth)acrylate monomers having sulfide linkages
US9891349B2 (en) 2012-12-13 2018-02-13 Ppg Industries Ohio, Inc. Optical articles and methods for preparation of same
US10012773B2 (en) 2012-12-13 2018-07-03 Ppg Industries Ohio, Inc. Methods for preparing optical articles and optical articles prepared therefrom
US9568643B2 (en) 2012-12-13 2017-02-14 Ppg Industries Ohio, Inc. Polyurethane urea-containing compositions and optical articles and methods for preparing them
WO2014152819A1 (en) 2013-03-14 2014-09-25 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
WO2021181307A1 (en) 2020-03-11 2021-09-16 Alcon Inc. Photochromic polydiorganosiloxane vinylic crosslinkers
WO2021181341A1 (en) 2020-03-11 2021-09-16 Alcon Inc. Photochromic polydiorganosiloxane vinylic crosslinkers
US11945895B2 (en) 2020-03-11 2024-04-02 Alcon Inc. Photochromic polydiorganosiloxane vinylic crosslinkers
WO2021245551A1 (en) 2020-06-02 2021-12-09 Alcon Inc. Method for making photochromic contact lenses
WO2022090967A1 (en) 2020-10-28 2022-05-05 Alcon Inc. Method for making photochromic contact lenses
US11945181B2 (en) 2020-10-28 2024-04-02 Alcon Inc. Method for making photochromic contact lenses
US11886045B2 (en) 2020-11-04 2024-01-30 Alcon Inc. Method for making photochromic contact lenses
WO2022097048A1 (en) 2020-11-04 2022-05-12 Alcon Inc. Method for making photochromic contact lenses
WO2022097049A1 (en) 2020-11-04 2022-05-12 Alcon Inc. Method for making photochromic contact lenses
WO2022189941A1 (en) 2021-03-08 2022-09-15 Alcon Inc. Method for making photochromic contact lenses
WO2022189940A1 (en) 2021-03-08 2022-09-15 Alcon Inc. Method for making photofunctional contact lenses
US11833771B2 (en) 2021-04-01 2023-12-05 Alcon Inc. Method for making photochromic contact lenses
WO2022208450A1 (en) 2021-04-01 2022-10-06 Alcon Inc. Method for making photochromic contact lenses
WO2023209631A1 (en) 2022-04-28 2023-11-02 Alcon Inc. Method for making uv and hevl-absorbing ophthalmic lenses

Also Published As

Publication number Publication date
BE740580A (en) 1970-04-01
JPS4948631B1 (en) 1974-12-23
GB1227713A (en) 1971-04-07
FR2021692A1 (en) 1970-07-24
DE1954220A1 (en) 1970-05-06

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