CA1236297A - Recording and information record elements comprising telluropyrylium dyes - Google Patents
Recording and information record elements comprising telluropyrylium dyesInfo
- Publication number
- CA1236297A CA1236297A CA000472367A CA472367A CA1236297A CA 1236297 A CA1236297 A CA 1236297A CA 000472367 A CA000472367 A CA 000472367A CA 472367 A CA472367 A CA 472367A CA 1236297 A CA1236297 A CA 1236297A
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- CA
- Canada
- Prior art keywords
- dye
- group
- recording
- aryl
- binder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/249—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing organometallic compounds
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/146—Laser beam
Abstract
-i-RECORDING AND INFORMATION RECORD ELEMENTS
COMPRISING TELLUROPYRYLIUM DYES
Abstract of the Disclosure Telluropyrylium dyes are useful as infrared absorbing dyes in recording elements.
COMPRISING TELLUROPYRYLIUM DYES
Abstract of the Disclosure Telluropyrylium dyes are useful as infrared absorbing dyes in recording elements.
Description
~36~
RECORDING AND INFORMATION RECORD ELEMENTS
COMPRISING TELLUROPYRYLIUM DYES
Field of the Invention The present invention relates to optical recording and information elements.
Description Relative to the Prior Art Element for recording information by thermally altering the physical structure of a mat fiat are known. One such element comprises a layer ox a solvent-coated plastic material coated on a support. The plastic material can be thermally deformed by a laser beam so that some of the plastic material is displaced in the area illuminated by the beam. This deformation pattern retains its shape after the laser beam is removed. The resulting deformation pattern can be read by projecting the pattern onto a viewing screen.
More recently, elements and means have been provided for rapidly recording large amounts of digital information in a small area. These elements provide a method for recording video information which can be read back with a high carrler-to-noise ratio (CUR). These element employ a thin recording layer of a certain metallic or organic material which is vacuum-deposited on a support. Recording us accomplished by a beam of high-energy density radiation, such as a laser beam. Generally, the laser beam is focused onto the surface of the recording layer of the element. The recording layer is such that it absorbs energy from the laser beam so that small portions of the layer burn, evaporate or are otherwise displaced from these portions.
This technique is usually referred to as "ablative recording". Normally there is continuous motion between the laser and the layer so that, as the laser is pulsed or modulated, discrete pits or holes 2g7 of varying sizes are created in the layer The sizes and spacing of these holes constitute the encoded information. One element of this type is commonly referred to in the art as a video disc.
Optical recording discs of the ablative type can be read back using a laser beam similar to the one used to record the element. In conventional ablative video discs, the reading beam must also be significantly absorbed by the recording layer. A
continuous reading beam is focused on the recording layer and the difference in optical density between pitted and unpitied areas is detected by a photo-detector. The recording layer must absorb signify-gently less energy from the reading beam than it absorb from the writing beam if physical damage to the recording is to be avoided. This is usually accomplished by using a reading beam of much lesser power than the writing beam.
In Research Disclosure, Vol. 194, Item 19412, June 1980, published by Kenneth Mason Publications, lid 7, me Old Harbormasters, 8 North Street, Ems worth, Hampshire POW ODD, England, an element is disclosed for recording information by thermal deformation. The recording element come proses a support and a layer of a radiant energy-absorptive dye in a thermally deformable binder.
Upon exposure to a pulsed beam of high intensity radiant energy, deformations comprising a depression surrounded by a ridge are formed, thus allowing recording with a modulated beam and playback by reflection and/or refraction. Laser beam recording upon such an element has heretofore been accomp-fished with an argon-ion laser which emits at 488 no. A pulsed beam is obtained from the keynote-35 Nazi argon-ion laser beam by modulating the beam with an acousto optic or electro-optic modulator.
Those modulators have low efficiency and the system thus requires a high-power laser.
~23~7 Currently, however, there are diode lasers available which are more suitable for home-use because their output can be modulated directly.
These can function as effectively as much more powerful continuous gas layers for optical recording and feedback. They need no expensive acousto-optic or ~lectro-optic modulators and are becoming avail-able a greatly reduced prices. The earlier con strutted diode lasers emitted at about 800 900 no and newer models emit between 750-850 no. There is a need for soluble, solvent-coatable materials absorbing between 750-900 no, preferably 750-850 no, which are suitable for use in recording elements of the type described in Research Disclosure, Vol. 175, Item 17522, November 1978, designed for recording and playback with a low-power diode laser.
SUMMARY OF THE INVENTION
The present invention provides optical recording and information bearing record elements comprising a support having coated thereon an optical recording layer of an amorphous composition comprising a binder and a dye characterized in that the dye is an infrared absorbing telluropyrylium material. Telluropyrylium includes benzotelluro-25 pyrylium. By infrared absorbing we mean the dyes~bsorb in the 700-900 no range of the spectrum. The recording elements comprising such dyes are useful in optical recording methods employing diode record-in and feedback laser devices. None of the telluropyrylium dyes disclosed for use herein have been previously identified as having infrared absorbing capabilities.
go The present invention also provides method of making a recording element comprising the steps:
1. applying to a support a coating composition comprising a radiation absorptive dye and a compatible binder and
RECORDING AND INFORMATION RECORD ELEMENTS
COMPRISING TELLUROPYRYLIUM DYES
Field of the Invention The present invention relates to optical recording and information elements.
Description Relative to the Prior Art Element for recording information by thermally altering the physical structure of a mat fiat are known. One such element comprises a layer ox a solvent-coated plastic material coated on a support. The plastic material can be thermally deformed by a laser beam so that some of the plastic material is displaced in the area illuminated by the beam. This deformation pattern retains its shape after the laser beam is removed. The resulting deformation pattern can be read by projecting the pattern onto a viewing screen.
More recently, elements and means have been provided for rapidly recording large amounts of digital information in a small area. These elements provide a method for recording video information which can be read back with a high carrler-to-noise ratio (CUR). These element employ a thin recording layer of a certain metallic or organic material which is vacuum-deposited on a support. Recording us accomplished by a beam of high-energy density radiation, such as a laser beam. Generally, the laser beam is focused onto the surface of the recording layer of the element. The recording layer is such that it absorbs energy from the laser beam so that small portions of the layer burn, evaporate or are otherwise displaced from these portions.
This technique is usually referred to as "ablative recording". Normally there is continuous motion between the laser and the layer so that, as the laser is pulsed or modulated, discrete pits or holes 2g7 of varying sizes are created in the layer The sizes and spacing of these holes constitute the encoded information. One element of this type is commonly referred to in the art as a video disc.
Optical recording discs of the ablative type can be read back using a laser beam similar to the one used to record the element. In conventional ablative video discs, the reading beam must also be significantly absorbed by the recording layer. A
continuous reading beam is focused on the recording layer and the difference in optical density between pitted and unpitied areas is detected by a photo-detector. The recording layer must absorb signify-gently less energy from the reading beam than it absorb from the writing beam if physical damage to the recording is to be avoided. This is usually accomplished by using a reading beam of much lesser power than the writing beam.
In Research Disclosure, Vol. 194, Item 19412, June 1980, published by Kenneth Mason Publications, lid 7, me Old Harbormasters, 8 North Street, Ems worth, Hampshire POW ODD, England, an element is disclosed for recording information by thermal deformation. The recording element come proses a support and a layer of a radiant energy-absorptive dye in a thermally deformable binder.
Upon exposure to a pulsed beam of high intensity radiant energy, deformations comprising a depression surrounded by a ridge are formed, thus allowing recording with a modulated beam and playback by reflection and/or refraction. Laser beam recording upon such an element has heretofore been accomp-fished with an argon-ion laser which emits at 488 no. A pulsed beam is obtained from the keynote-35 Nazi argon-ion laser beam by modulating the beam with an acousto optic or electro-optic modulator.
Those modulators have low efficiency and the system thus requires a high-power laser.
~23~7 Currently, however, there are diode lasers available which are more suitable for home-use because their output can be modulated directly.
These can function as effectively as much more powerful continuous gas layers for optical recording and feedback. They need no expensive acousto-optic or ~lectro-optic modulators and are becoming avail-able a greatly reduced prices. The earlier con strutted diode lasers emitted at about 800 900 no and newer models emit between 750-850 no. There is a need for soluble, solvent-coatable materials absorbing between 750-900 no, preferably 750-850 no, which are suitable for use in recording elements of the type described in Research Disclosure, Vol. 175, Item 17522, November 1978, designed for recording and playback with a low-power diode laser.
SUMMARY OF THE INVENTION
The present invention provides optical recording and information bearing record elements comprising a support having coated thereon an optical recording layer of an amorphous composition comprising a binder and a dye characterized in that the dye is an infrared absorbing telluropyrylium material. Telluropyrylium includes benzotelluro-25 pyrylium. By infrared absorbing we mean the dyes~bsorb in the 700-900 no range of the spectrum. The recording elements comprising such dyes are useful in optical recording methods employing diode record-in and feedback laser devices. None of the telluropyrylium dyes disclosed for use herein have been previously identified as having infrared absorbing capabilities.
go The present invention also provides method of making a recording element comprising the steps:
1. applying to a support a coating composition comprising a radiation absorptive dye and a compatible binder and
2. drying the composition to form an amorphous layer; characterized in that the dye is an infrared absorbing telluropyrylium dye.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferred recording and information record elements comprise recording layers which absorb in the 700-900 no region of the spectrum. The layers comprise a telluropyrylium dye of the structures:
Al I.
Jo \ X
R 3/ ye+/ 5 wherein R " R 3 and R 5 each independently represents alkyd, aureole, -~CR6-CH~CR7=Al or -~CH=CH~ 2 provided that one, and only one, of R 1, R 3 and R 5 is -CRY SHAKER AYE or -~CH=CH 2;
R 2 and R 4 each independently represents hydrogen;
or R 2 and R 3, or R 4 and R 5, taken together with the carbon atoms Jo which they are attached, form a 30 mononuclear or polynuclear fused carbocyclîc ring having from about 5 to 20 carbon atoms;
R 6 and R 7 are each independently hydrogen, cyan, alkyd or aureole;
Al represents a monocyclic or polycyclic heterocyclylidene group such as oxazolylidene, thia~olylidene, selenazolylidene~ imidazolylidene, pyranylidene, thiapyranylidene, selenapyranylidene, ~3~2~7 telluropyranylidene, oxoindolazinylidene, benzox-azolylidene a benzothiazolylidene, benzopyrsnylidene, benzothiapyranylidene, benzoselenapyranylidene, or benzotelluropyranylidene;
A 2 represents aureole, amino, dialkylaminoaryl, alkylamino, arylamino, dialkylamino, diarylamino or a monocyclic or polycyclic heterocyclyl group such as oxazolyl, tetrahydroquinolinyl, 9 julolidyl, thiazolyl, selenazolyl, imidazolyl, benzoxazolyl, lo benzo~hiazolyl; or naphthyl;
n represents a number from 0 to 5;
m represents a number from 1 to 5; and X represents an anion such as BY Clue-, CF3S03-, FS03-, PF6-, CHIHUAHUAS-, Of-, Bra, or I-.
These preferred telluropyrylium materials include infrared absorbing benzotelluropyrylium materials when either R2 and R3 or R4 and Us taken together with carbon atoms to which they are attached, form a polynuclear fused carbocyclic ring having 6 carbon atoms. They have the structure:
Al o I Roll II.
i it ; I ;
R8/ eye/ it ~13 Al 4 Rio and R8 each independently represents alkyd, aureole, -~CRs=CH~CR7=Al~ or -~CH=CH 2 provided that one, and only one, of R8 and Rho is -~CRs~CH3nCR7~Al or -~CH=CH 2;
Al and A 2 are as previously defined;
R6 and R 7 are each independently hydrogen, cyan, alkyd, or aureole;
Rug, Roll, Al 2, Rl3 and Al 4 each independently 5 represents hydrogen;
n represents a number from 0 to 5;
m represents a number from 1 to 5; and X represents an anion as previously defined.
"Alkyd" includes a branched- or straight-chain hydrocarbon having up to 16 carbon atoms, such as methyl, bottle dodecyl, nonyl, tertiary-butyl and isobutyl; "aureole" includes phenol, naphthyl, anthryl, alkoxyphenyl and dialkylaminophenyl.
DETAILED DESCRIPTION OF THE INVENTION
The telluropyrylium dyes which are useful in the recording and information bearing elements of this invention can be made according to methods described in U.S. Patent 4,365,017 granted December 21, 1982 in the name of Dotty et at. Exam-20 pies of useful telluropyrylium dyes are presented in Table I.
~3~2~7 TABLE I
Telluropyrylium Dyes for Laser Write- and Read-Application s Shekel 2 Mecca, Dye No. mp,C no log E
NMe2 1. it it 248-250 790 4.97 t OH
If BF4-OH
Phi Jo oh Me me 2. it it foam 795 5.08 OH
If OF 3S0 3-OH
Jo \, Phi Jo oh 362~7 TABLE I (count . ) OH clue 2 Mecca, S p, no log Jo \~/ \.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferred recording and information record elements comprise recording layers which absorb in the 700-900 no region of the spectrum. The layers comprise a telluropyrylium dye of the structures:
Al I.
Jo \ X
R 3/ ye+/ 5 wherein R " R 3 and R 5 each independently represents alkyd, aureole, -~CR6-CH~CR7=Al or -~CH=CH~ 2 provided that one, and only one, of R 1, R 3 and R 5 is -CRY SHAKER AYE or -~CH=CH 2;
R 2 and R 4 each independently represents hydrogen;
or R 2 and R 3, or R 4 and R 5, taken together with the carbon atoms Jo which they are attached, form a 30 mononuclear or polynuclear fused carbocyclîc ring having from about 5 to 20 carbon atoms;
R 6 and R 7 are each independently hydrogen, cyan, alkyd or aureole;
Al represents a monocyclic or polycyclic heterocyclylidene group such as oxazolylidene, thia~olylidene, selenazolylidene~ imidazolylidene, pyranylidene, thiapyranylidene, selenapyranylidene, ~3~2~7 telluropyranylidene, oxoindolazinylidene, benzox-azolylidene a benzothiazolylidene, benzopyrsnylidene, benzothiapyranylidene, benzoselenapyranylidene, or benzotelluropyranylidene;
A 2 represents aureole, amino, dialkylaminoaryl, alkylamino, arylamino, dialkylamino, diarylamino or a monocyclic or polycyclic heterocyclyl group such as oxazolyl, tetrahydroquinolinyl, 9 julolidyl, thiazolyl, selenazolyl, imidazolyl, benzoxazolyl, lo benzo~hiazolyl; or naphthyl;
n represents a number from 0 to 5;
m represents a number from 1 to 5; and X represents an anion such as BY Clue-, CF3S03-, FS03-, PF6-, CHIHUAHUAS-, Of-, Bra, or I-.
These preferred telluropyrylium materials include infrared absorbing benzotelluropyrylium materials when either R2 and R3 or R4 and Us taken together with carbon atoms to which they are attached, form a polynuclear fused carbocyclic ring having 6 carbon atoms. They have the structure:
Al o I Roll II.
i it ; I ;
R8/ eye/ it ~13 Al 4 Rio and R8 each independently represents alkyd, aureole, -~CRs=CH~CR7=Al~ or -~CH=CH 2 provided that one, and only one, of R8 and Rho is -~CRs~CH3nCR7~Al or -~CH=CH 2;
Al and A 2 are as previously defined;
R6 and R 7 are each independently hydrogen, cyan, alkyd, or aureole;
Rug, Roll, Al 2, Rl3 and Al 4 each independently 5 represents hydrogen;
n represents a number from 0 to 5;
m represents a number from 1 to 5; and X represents an anion as previously defined.
"Alkyd" includes a branched- or straight-chain hydrocarbon having up to 16 carbon atoms, such as methyl, bottle dodecyl, nonyl, tertiary-butyl and isobutyl; "aureole" includes phenol, naphthyl, anthryl, alkoxyphenyl and dialkylaminophenyl.
DETAILED DESCRIPTION OF THE INVENTION
The telluropyrylium dyes which are useful in the recording and information bearing elements of this invention can be made according to methods described in U.S. Patent 4,365,017 granted December 21, 1982 in the name of Dotty et at. Exam-20 pies of useful telluropyrylium dyes are presented in Table I.
~3~2~7 TABLE I
Telluropyrylium Dyes for Laser Write- and Read-Application s Shekel 2 Mecca, Dye No. mp,C no log E
NMe2 1. it it 248-250 790 4.97 t OH
If BF4-OH
Phi Jo oh Me me 2. it it foam 795 5.08 OH
If OF 3S0 3-OH
Jo \, Phi Jo oh 362~7 TABLE I (count . ) OH clue 2 Mecca, S p, no log Jo \~/ \.
3 \-~ \-/ 172 818 5.02 I./
OH
If BY 4 OH
Phi è Pi Name 2
OH
If BY 4 OH
Phi è Pi Name 2
4 Jo I 149-152 870 5.19 ./
OH
If BY 4 -~_~
Phi I/ Pi ~Z3~2~7 TABLE I (cont. ) OH clue 2 Mecca, e No . my, C no E
(OH 3) 3C\ To I (OH 3) 3 I I!
OH
If BY 4 -~_~
Phi I/ Pi ~Z3~2~7 TABLE I (cont. ) OH clue 2 Mecca, e No . my, C no E
(OH 3) 3C\ To I (OH 3) 3 I I!
5. OH 239-240 715 5.11 .~-\.
(SHEA) 3C/ ~;é \C(CH3) 3 (SHEA) 3C\ To /C(CH3) 3 I I!
(SHEA) 3C/ ~;é \C(CH3) 3 (SHEA) 3C\ To /C(CH3) 3 I I!
6 OH 205-208 830 5 . 52 OH
OH
Jo ( OH 3) 3C/ To I (OH 3) 3 :~36i~
TABLE I (cont.) Mecca, e No. mp,~C no lo (SCHICK\ & (SHEA
i! it
OH
Jo ( OH 3) 3C/ To I (OH 3) 3 :~36i~
TABLE I (cont.) Mecca, e No. mp,~C no lo (SCHICK\ & (SHEA
i! it
7. OH 199-202 786 5.45 OH
OH
i if (SCHICK/ Jo \C(CH3)3 (SCHICK\ /C(CH3)3 lo
OH
i if (SCHICK/ Jo \C(CH3)3 (SCHICK\ /C(CH3)3 lo
8. CCH3 214.5-215 800 5.46 OH
OH
(SCHICK/ Jo C(CH3) 3 I
TABLE I (cont. ) Mecca, Dye No . my, C _ no (OH 33 3C~ So I (OH 3) 3 i!, I!
OH
(SCHICK/ Jo C(CH3) 3 I
TABLE I (cont. ) Mecca, Dye No . my, C _ no (OH 33 3C~ So I (OH 3) 3 i!, I!
9 OH 191-l95 803 5.44 Clue OH
1 5 . of \
(SHEA) 3C/ Jo C(CH3) 3 (C~3) 3C~ To /C(CH3) 3 i!, Gil lo . CCH 3 200-202 843 5 .42 ISSUE
OH
off I.
(SHEA) 3cf Jo \C(CH3) 3 ~23~Z5~
TABLE I keynote. ) my Dye No. my, C no (SHEA) 3C\ To /C(CH3) 3 i!, MU
11. CON 141~143 792 5.41 OH
OH
I I \.
SHEA ) C/ Jo \C(CH ) i Jo I
12 . Jo / 178-179 775 5 . 16 710 4.08 o OH
if BY *
OH
(OH 3) 3C/ Jo I (OH 3) 3 ~3~i2~'7 TABLE I (cont. ) OH clue 2 Max dye No . my, C no lo (OH I 3C~ To OUCH 3 it, I I!
SHEA
13 . OH BF4 238-240 870 S. 18 If (doe ) OH
I Jo \.~'\.
- 1 t 1 I
(OH 3) 3C/ Jo I-/ Bach 3 NMe2 Jo \.
!
I./
14 . OH By 4 - 213 748 S .11 If (doe ) OH
(SCHICK/ Jo ~-~ bCH3 ~3~7 TABLE I (cont. ) Max ye No . my C no lo NMe2 I
15. OH BF4- 212 855 5.16 If (doe) OH
(OH 3) 3C/ ~;é / Bach 3 16. I \./ 131 7~4 5.03 doe) OH
If BY 4 -OH
.~-\.~-\.
(OH 3) 3C/ Jo I-/ Bach 3 ~23~2~7 TABLE I keynote . ) Mecca, S Dye No . my, C no log ;/ I/ Jo 17 Jo / 181-183 803 4. 93 1 I 740 4 . 83 OH
If OF 3S0 3 OH
Jo \.~ \.
b SHEA
/. SHEA 3 Jo 18 . i it 139-14~ 79~ 4 . I
./
OH
if OF SO 3 OH
-i// it Eli Lowe TABLE I keynote. ) OH clue 2 Max Dye No . my C no OH 3 \ SHEA 3 owl .
OH/ I I 120-126 786 5.12 19. it/ SHEA 3 OH
If OF 3S0 3 -OH
1 I.
Phi Jo /
(SHEA) 3C\ .= ./ SHEA BF4 20. To + -CH=CH~ N/
. / \ . OH 3 21.T~ CH~CH- I us N/
30 (OH 3) 3C/ OH 3 ~236~ 7 The described dyes are compatible with binders which are useful in making laser recording elements. By "compatible" us meant that the dye can be mixed with the binder in sufficient concentration S to provide a high enough absorption factor to form pits without crystallizing after a layer of the dye and binder is coated and dry. That is, the layers are amorphous. Generally, the described dyes are compatible in dye-binder compositions comprising at least 50 percent dye by weight, although higher concentrations and therefore higher absorption lag-ions are possible. Because of the high extinction coefficient of many of the present dyes at wave-lengths from 700-900 no and their excellent come 15 potability with common binders, these dyes can reincluded in the composition over a very wide range of concentration while maintaining the necessary absorption characteristics.
Useful binders are, for example, cellulose acetate butyrates, cellulose nitrate, polystyrene, polysulfonamides, polycarbonates, cellulose nitrate, hydroabietyl alcohol (sold by the Hercules Chemical Co. as Abitol~ ASK 257), poly(ethyl methacrylate), polyvinyl bitterly) and combinations and derivatives thereof. The preferred binder is an amorphous material comprising a mixture of non-polymeric come pounds. Top mixture is a) amorphous, b) solid at about 20C, and c) comprises at least two different compounds each having at least two linking combo-newts joining one multivalent organic nucleus withal least two organic nuclei wherein at least one of the multivalent organic nuclei is a multi cyclic or aromatic nucleus. Examples of such binders are presented in Table II.
I
TABLE I I
l. Mole t or ; ,\ Jo OOZE
\ ox I By NO 7 i 35%
15 2. owe 70 () O By I \ / \ //-\ No Lowe Al 40%
O Jo \./ \./ I. O By --Of 1 yo-yo/ 30~i _ 30%
~L~3~2~7 TABLE II keynoted 3 Mole %
Hi --NHC_ Of\ 16.67%
SHEA SHEA OWE=./ \.
_ OWE 50%
._ .
_ -Of 16~67% ;
_ -I -By 16.67%
4 Mole %
- COY --OX 35%
Jo I I I.
I Lyle lo NO 30% i 61 Mole % _ Jo Of 35%
O Of\ clue O
.3 ;~.
39 Mole %
\
3~2~
A useful loser recording element comprises a support having coated thereon a layer of the dye and the binder. Depending upon the desired mode of reading the element, the support is either reflect live or transparent. In the case of a reflective support, both sides of the support can be reflective and a recording layer can be provided on both sides.
The support con be any of a wide variety of materials including glues, a self-supporting polymer film such a polyethylene terephthalate) or cell- lose acetate, or metal. The support must have a relatively high molting point in order to avoid deformation of the support during recording. The support is desirably very smooth to minimize noise and dropouts. In certain preferred embodiments, the ; support is coated with a smoothing layer prior to the coating of the reflective surface and the described dye-binder composition.
The composition which is used as a smooth-in layer is preferably a low-viscosity, polymer-sizable fluid which can be coated on the surface of the support. Following coating, polymerization of the fluid produces a micro smooth surface on the support. The support can be made reflective by vacuum metalization no the smooth surface. In pro-furred embodiment, the polymerizable fluid COY -prizes photopolymerizable monomers. Preferably, the monomer or mixtures of monomer are low-viscosity fluids in the absence of a solvent. Useful polymer-icily fluid compositions are described in U.S.PAtents 4,092,17~ and 4,171,979.
I
The recording layer comprising the described dye and binder is coated by a wide variety of methods. Most conveniently, the dye and binder are coated from a common solvent or, alternatively, from a mixture of miscible solvents. The dye-binder composition can be coated by spray coating air-knife cooling, whirl coating or by any other suit-able method. The thickness of the recording layer according to the present invention is not critical;
1 5 . of \
(SHEA) 3C/ Jo C(CH3) 3 (C~3) 3C~ To /C(CH3) 3 i!, Gil lo . CCH 3 200-202 843 5 .42 ISSUE
OH
off I.
(SHEA) 3cf Jo \C(CH3) 3 ~23~Z5~
TABLE I keynote. ) my Dye No. my, C no (SHEA) 3C\ To /C(CH3) 3 i!, MU
11. CON 141~143 792 5.41 OH
OH
I I \.
SHEA ) C/ Jo \C(CH ) i Jo I
12 . Jo / 178-179 775 5 . 16 710 4.08 o OH
if BY *
OH
(OH 3) 3C/ Jo I (OH 3) 3 ~3~i2~'7 TABLE I (cont. ) OH clue 2 Max dye No . my, C no lo (OH I 3C~ To OUCH 3 it, I I!
SHEA
13 . OH BF4 238-240 870 S. 18 If (doe ) OH
I Jo \.~'\.
- 1 t 1 I
(OH 3) 3C/ Jo I-/ Bach 3 NMe2 Jo \.
!
I./
14 . OH By 4 - 213 748 S .11 If (doe ) OH
(SCHICK/ Jo ~-~ bCH3 ~3~7 TABLE I (cont. ) Max ye No . my C no lo NMe2 I
15. OH BF4- 212 855 5.16 If (doe) OH
(OH 3) 3C/ ~;é / Bach 3 16. I \./ 131 7~4 5.03 doe) OH
If BY 4 -OH
.~-\.~-\.
(OH 3) 3C/ Jo I-/ Bach 3 ~23~2~7 TABLE I keynote . ) Mecca, S Dye No . my, C no log ;/ I/ Jo 17 Jo / 181-183 803 4. 93 1 I 740 4 . 83 OH
If OF 3S0 3 OH
Jo \.~ \.
b SHEA
/. SHEA 3 Jo 18 . i it 139-14~ 79~ 4 . I
./
OH
if OF SO 3 OH
-i// it Eli Lowe TABLE I keynote. ) OH clue 2 Max Dye No . my C no OH 3 \ SHEA 3 owl .
OH/ I I 120-126 786 5.12 19. it/ SHEA 3 OH
If OF 3S0 3 -OH
1 I.
Phi Jo /
(SHEA) 3C\ .= ./ SHEA BF4 20. To + -CH=CH~ N/
. / \ . OH 3 21.T~ CH~CH- I us N/
30 (OH 3) 3C/ OH 3 ~236~ 7 The described dyes are compatible with binders which are useful in making laser recording elements. By "compatible" us meant that the dye can be mixed with the binder in sufficient concentration S to provide a high enough absorption factor to form pits without crystallizing after a layer of the dye and binder is coated and dry. That is, the layers are amorphous. Generally, the described dyes are compatible in dye-binder compositions comprising at least 50 percent dye by weight, although higher concentrations and therefore higher absorption lag-ions are possible. Because of the high extinction coefficient of many of the present dyes at wave-lengths from 700-900 no and their excellent come 15 potability with common binders, these dyes can reincluded in the composition over a very wide range of concentration while maintaining the necessary absorption characteristics.
Useful binders are, for example, cellulose acetate butyrates, cellulose nitrate, polystyrene, polysulfonamides, polycarbonates, cellulose nitrate, hydroabietyl alcohol (sold by the Hercules Chemical Co. as Abitol~ ASK 257), poly(ethyl methacrylate), polyvinyl bitterly) and combinations and derivatives thereof. The preferred binder is an amorphous material comprising a mixture of non-polymeric come pounds. Top mixture is a) amorphous, b) solid at about 20C, and c) comprises at least two different compounds each having at least two linking combo-newts joining one multivalent organic nucleus withal least two organic nuclei wherein at least one of the multivalent organic nuclei is a multi cyclic or aromatic nucleus. Examples of such binders are presented in Table II.
I
TABLE I I
l. Mole t or ; ,\ Jo OOZE
\ ox I By NO 7 i 35%
15 2. owe 70 () O By I \ / \ //-\ No Lowe Al 40%
O Jo \./ \./ I. O By --Of 1 yo-yo/ 30~i _ 30%
~L~3~2~7 TABLE II keynoted 3 Mole %
Hi --NHC_ Of\ 16.67%
SHEA SHEA OWE=./ \.
_ OWE 50%
._ .
_ -Of 16~67% ;
_ -I -By 16.67%
4 Mole %
- COY --OX 35%
Jo I I I.
I Lyle lo NO 30% i 61 Mole % _ Jo Of 35%
O Of\ clue O
.3 ;~.
39 Mole %
\
3~2~
A useful loser recording element comprises a support having coated thereon a layer of the dye and the binder. Depending upon the desired mode of reading the element, the support is either reflect live or transparent. In the case of a reflective support, both sides of the support can be reflective and a recording layer can be provided on both sides.
The support con be any of a wide variety of materials including glues, a self-supporting polymer film such a polyethylene terephthalate) or cell- lose acetate, or metal. The support must have a relatively high molting point in order to avoid deformation of the support during recording. The support is desirably very smooth to minimize noise and dropouts. In certain preferred embodiments, the ; support is coated with a smoothing layer prior to the coating of the reflective surface and the described dye-binder composition.
The composition which is used as a smooth-in layer is preferably a low-viscosity, polymer-sizable fluid which can be coated on the surface of the support. Following coating, polymerization of the fluid produces a micro smooth surface on the support. The support can be made reflective by vacuum metalization no the smooth surface. In pro-furred embodiment, the polymerizable fluid COY -prizes photopolymerizable monomers. Preferably, the monomer or mixtures of monomer are low-viscosity fluids in the absence of a solvent. Useful polymer-icily fluid compositions are described in U.S.PAtents 4,092,17~ and 4,171,979.
I
The recording layer comprising the described dye and binder is coated by a wide variety of methods. Most conveniently, the dye and binder are coated from a common solvent or, alternatively, from a mixture of miscible solvents. The dye-binder composition can be coated by spray coating air-knife cooling, whirl coating or by any other suit-able method. The thickness of the recording layer according to the present invention is not critical;
10 however, best results are obtained when the thick-news of the layer is between about 0.1 and about 10 microns.
The described recording compositions having an absorption factor of at least 20 are capable of producing depressions or holes surrounded by sharply defined ridges. This type of deformation can be read back using a read beam which is not signify-gently absorbed by the recording layer. By "sharply defined ridge" is meant that the ridge and hole/-20 depression have noticeable boundaries and that, as measured in the plane of the undeformed outer sun-face of the layer, the width of the ridge is less than or equal to the breadth of the hole depress soon. These dimensions can be measured with an electron micro graph.
The thickness, absorption factor and index of refraction of the recording compositions of the present invention can be optimized by a method which is described on Research Disclosure, Item 20635, Vol. 206, Jut 1981.
The following examples are presented.
Examples 1~6 Table I dyes 6, 7, 8, 11, 20 and 21 were evaluated for utility in optical recording elements with A static pit tester.
~3~Z~7 The static pit tester provides automated facilities for exposing standard test patterns on 2"
by 2" glass slides or film samples with a laser. A
microcomputer using FORTH language was used to con-5 trot the sample position and the laser power.
Six different coating compositions were prepared by mixing 0.03 gym dye, 0.03 gym of the binder (Compound 3, Table III) in 0.2 ml of 1,2,3-trichloropropane, 2.0 ml of bromobenæene, 3 drops of a fluorinated surfactant (1% solution in - bromobenzene).
fourteen different coating compositions were prepared on glass slides or films by dip coat-in.
lo Each coating was then exposed, in the static pit tester, Jo a power series array of ten pits on 4 micron centers at each of six power levels (2, 3, 4, 6, 8 and 10 milliwatts) on the sample with a 50 nanosecond pulse duration from an 830 20 nanometer diode laser. This pattern was repeated at 2 mm intervals across the sample for a total of thirteen test patches. These test patches were examined with a Nomarsky differential interference contrast microscope to determine the presence or absence of pits in a particular coating. A dye is considered useful when a pit is formed at any of the six power levels at any position of the coating.
Pits were formed in each of the six coated compositions, Examples 7-8 Recording elements were prepared with Table I dyes 6 and 18. The results of this example con-firm the effectiveness of the static pit test in 35 evaluating dyes for utility in optical recording elements.
;~31~Z~317 Two different recording elements were pro-pared as follows:
270~mm-d}ameter circular glass substrates were whirl-coated with a surface-smoothing composition by S flooding the glass substrates with the smoothing composition it low rum (about 80-100 rum) and then leveling the coatings by advancing the speed to about 500 rum. The surface-smoothing composition comprised:
pentaerythritol tetraacrylate20 g a low-viscosity urethane-acrylate20 g monomer Uncurable Topcoat 874-C-2002, Fuller O'Brien Corp.) 2-ethoxyethanol 60 g a Cameron sensitizer composition 3 g surfactant 3 drops 20 The coated and dried surface-smoothing composition was cured by irradiating with a 3000-watt pulsed xenon arc lamp at 45.72 mm for 4 minutes.
The thus smoothed surface of the substrates were then coated with a 0.05~m thick reflecting layer of aluminum by vapor deposition.
Two different recording layers were whirl-coated on the reflecting layers by flooding the reflecting layers with dye-binder-solvent coating solutions and then leveling the coatings at about 500 rum for coatings 1 and 2. The composition of each coating solution is given in Table III.
3~2g'7 I
o o Us o o Us o o o o Us Us o TV o Kiwi I:
, owe .,~
a 3 c:, a o lo N id H a x o Jo I:
En H
So So O
I
a U
I
H o Z
a I
Cal 3i~2~
After drying, tracks were recorded in the recording layers of each element using a diode laser-light emitting at about 810 no and focused with a numerical aperture Nag = 0.525 while the elements were rotating at 1800 rum. The term "Nag"
represents the numerical aperture of the focused Gaussian beam of light measured to its en 2 irradiance diameter. The recorded trucks were read back with the same laser. The 50% Institute of Radio Engineers flat field video signal-to-noise ratios were determined. Results are presented in Table IV.
I
Us Us Jo Jo Jo o o .
CO
a Jo I Eye The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.
The described recording compositions having an absorption factor of at least 20 are capable of producing depressions or holes surrounded by sharply defined ridges. This type of deformation can be read back using a read beam which is not signify-gently absorbed by the recording layer. By "sharply defined ridge" is meant that the ridge and hole/-20 depression have noticeable boundaries and that, as measured in the plane of the undeformed outer sun-face of the layer, the width of the ridge is less than or equal to the breadth of the hole depress soon. These dimensions can be measured with an electron micro graph.
The thickness, absorption factor and index of refraction of the recording compositions of the present invention can be optimized by a method which is described on Research Disclosure, Item 20635, Vol. 206, Jut 1981.
The following examples are presented.
Examples 1~6 Table I dyes 6, 7, 8, 11, 20 and 21 were evaluated for utility in optical recording elements with A static pit tester.
~3~Z~7 The static pit tester provides automated facilities for exposing standard test patterns on 2"
by 2" glass slides or film samples with a laser. A
microcomputer using FORTH language was used to con-5 trot the sample position and the laser power.
Six different coating compositions were prepared by mixing 0.03 gym dye, 0.03 gym of the binder (Compound 3, Table III) in 0.2 ml of 1,2,3-trichloropropane, 2.0 ml of bromobenæene, 3 drops of a fluorinated surfactant (1% solution in - bromobenzene).
fourteen different coating compositions were prepared on glass slides or films by dip coat-in.
lo Each coating was then exposed, in the static pit tester, Jo a power series array of ten pits on 4 micron centers at each of six power levels (2, 3, 4, 6, 8 and 10 milliwatts) on the sample with a 50 nanosecond pulse duration from an 830 20 nanometer diode laser. This pattern was repeated at 2 mm intervals across the sample for a total of thirteen test patches. These test patches were examined with a Nomarsky differential interference contrast microscope to determine the presence or absence of pits in a particular coating. A dye is considered useful when a pit is formed at any of the six power levels at any position of the coating.
Pits were formed in each of the six coated compositions, Examples 7-8 Recording elements were prepared with Table I dyes 6 and 18. The results of this example con-firm the effectiveness of the static pit test in 35 evaluating dyes for utility in optical recording elements.
;~31~Z~317 Two different recording elements were pro-pared as follows:
270~mm-d}ameter circular glass substrates were whirl-coated with a surface-smoothing composition by S flooding the glass substrates with the smoothing composition it low rum (about 80-100 rum) and then leveling the coatings by advancing the speed to about 500 rum. The surface-smoothing composition comprised:
pentaerythritol tetraacrylate20 g a low-viscosity urethane-acrylate20 g monomer Uncurable Topcoat 874-C-2002, Fuller O'Brien Corp.) 2-ethoxyethanol 60 g a Cameron sensitizer composition 3 g surfactant 3 drops 20 The coated and dried surface-smoothing composition was cured by irradiating with a 3000-watt pulsed xenon arc lamp at 45.72 mm for 4 minutes.
The thus smoothed surface of the substrates were then coated with a 0.05~m thick reflecting layer of aluminum by vapor deposition.
Two different recording layers were whirl-coated on the reflecting layers by flooding the reflecting layers with dye-binder-solvent coating solutions and then leveling the coatings at about 500 rum for coatings 1 and 2. The composition of each coating solution is given in Table III.
3~2g'7 I
o o Us o o Us o o o o Us Us o TV o Kiwi I:
, owe .,~
a 3 c:, a o lo N id H a x o Jo I:
En H
So So O
I
a U
I
H o Z
a I
Cal 3i~2~
After drying, tracks were recorded in the recording layers of each element using a diode laser-light emitting at about 810 no and focused with a numerical aperture Nag = 0.525 while the elements were rotating at 1800 rum. The term "Nag"
represents the numerical aperture of the focused Gaussian beam of light measured to its en 2 irradiance diameter. The recorded trucks were read back with the same laser. The 50% Institute of Radio Engineers flat field video signal-to-noise ratios were determined. Results are presented in Table IV.
I
Us Us Jo Jo Jo o o .
CO
a Jo I Eye The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.
Claims (11)
1. A recording element comprising a sup-port having coated thereon an optical recording layer of an amorphous composition comprising a dye and a binder and characterized in that the dye is an infrared absorbing telluropyrylium material.
2. An information bearing record element comprising a support having coated thereon an optical recording layer of an amorphous composition comprising a dye and a binder and characterized in that the dye is an infrared absorbing telluropyrylium material.
3. The element of claim 1 wherein the layer absorbs in the 700-900 nm region of the spect-rum and the dye has the structure wherein R1, R3 and R5 each independently represents alkyl, aryl, or provided that one, and only one, of R1, R3 and R5 is or ;
wherein R2 and R4 each independently represents hydrogen; or R2 and R3, or R4 and R5, taken together with the carbon atoms to which they are attached, form a mononuclear or polynuclear fused carbocyclic ring having from about 5 to 20 carbon atoms;
R6 and R7 are each independently hydrogen, cyano, alkyl or aryl;
A1 represents a monocyclic or polycyclic heterocyclylidene group;
A2 represents aryl, amino, dialkylaminoaryl, alkylamino, arylamino, dialkylamino, diarylamino or a monocyclic or polycyclic heterocyclyl group;
n represents a number from 0 to 5;
m represents a number from 1 to 5; and X represents an anion.
wherein R2 and R4 each independently represents hydrogen; or R2 and R3, or R4 and R5, taken together with the carbon atoms to which they are attached, form a mononuclear or polynuclear fused carbocyclic ring having from about 5 to 20 carbon atoms;
R6 and R7 are each independently hydrogen, cyano, alkyl or aryl;
A1 represents a monocyclic or polycyclic heterocyclylidene group;
A2 represents aryl, amino, dialkylaminoaryl, alkylamino, arylamino, dialkylamino, diarylamino or a monocyclic or polycyclic heterocyclyl group;
n represents a number from 0 to 5;
m represents a number from 1 to 5; and X represents an anion.
4. The element of claim 3 wherein the dye has the structure wherein R10 and R8 each independently represents alkyl, aryl, or provided that one, and only one, of R10 and R8 is or A1 represents a monocyclic or polycyclic hetero-cyclydine group;
A2 represents aryl, amino, dialkylaminoaryl, alkylamino, arylamino, dialkylamino, diarylamino or a monocyclic or polycyclic heterocyclyl group;
R6 and R7 are each independently hydrogen, cyano, alkyl or aryl;
R9, R11, R12, R13 and R14 each independently represents hydrogen;
n represents a number from 0 to 5;
m represents a number from 1 to 5; and X represents an anion.
A2 represents aryl, amino, dialkylaminoaryl, alkylamino, arylamino, dialkylamino, diarylamino or a monocyclic or polycyclic heterocyclyl group;
R6 and R7 are each independently hydrogen, cyano, alkyl or aryl;
R9, R11, R12, R13 and R14 each independently represents hydrogen;
n represents a number from 0 to 5;
m represents a number from 1 to 5; and X represents an anion.
5. The element of claim 3 wherein R1, R3 and R5 each independently represents methyl, ethyl, t-butyl, phenyl, p-N,N-dimethylaminophenyl, p-anisyl and ;
A1 represents a nucleus selected from the group consisting of oxazolylidene, thiazolylidene, selenazolylidene, imidazolylidene, pyranylidene, thiapyranylidene, selenapyranylidene, telluro-pyranylidene, oxoindolazinylidene, benzoxazolyl-idene, benzothiazolylidene, benzopyranylidene, benzothiapyranylidene, benzoselenapyranylidene, or benzotelluropyranylidene, A2 represents phenyl, dimethylaminophenyl, dimethylamino or a nucleus selected from the group consisting of oxazolyl, 9-julolidyl, thiazolyl, selenazolyl, tetrahydroquinolinyl, imidazolyl, benzoxazolyl, benzothiazolyl or naphthyl; and X represents BF4?, ClO4?, CF3SO3?, FS03?, PF6?, CH3SO3?, Cl?, Br?, or I?.
A1 represents a nucleus selected from the group consisting of oxazolylidene, thiazolylidene, selenazolylidene, imidazolylidene, pyranylidene, thiapyranylidene, selenapyranylidene, telluro-pyranylidene, oxoindolazinylidene, benzoxazolyl-idene, benzothiazolylidene, benzopyranylidene, benzothiapyranylidene, benzoselenapyranylidene, or benzotelluropyranylidene, A2 represents phenyl, dimethylaminophenyl, dimethylamino or a nucleus selected from the group consisting of oxazolyl, 9-julolidyl, thiazolyl, selenazolyl, tetrahydroquinolinyl, imidazolyl, benzoxazolyl, benzothiazolyl or naphthyl; and X represents BF4?, ClO4?, CF3SO3?, FS03?, PF6?, CH3SO3?, Cl?, Br?, or I?.
6. The element of claim 4 wherein R8 and R10 each independently represents methyl, ethyl, t-butyl, phenyl, p-anisyl, 2,5-dimethoxy-phenyl, p-N,N-dimethylaminophenyl and or;
A1 represents a nucleus selected from the group consisting of oxazolylidene, thiazolylidene, selenazolylidene, imidazolylidene, pyranylidene, thiapyranylidene, selenapyranylidene, telluropyran-ylidene, oxoindolazinylidene, benzoxazolylidene, benzothiazolylidene, benzopyranylidene, benzothia-pyranylidene, benzoselenapyranylidene, or benzo-telluropyranylidene;
A2 represents phenyl, dimethylaminophenyl, dimethylamino or a nucleus selected from the group consisting of oxazolyl, 9-julolidyl, thiazolyl, selenazolyl, tetrahydroquinolinyl, imidazolyl, benzoxazolyl, benzothiazolyl or naphthyl; and X represents BF4?, ClO4?, CF3SO3?, FSO3?, PF6?, CH3SO3?, Cl?, Br?, or I?.
A1 represents a nucleus selected from the group consisting of oxazolylidene, thiazolylidene, selenazolylidene, imidazolylidene, pyranylidene, thiapyranylidene, selenapyranylidene, telluropyran-ylidene, oxoindolazinylidene, benzoxazolylidene, benzothiazolylidene, benzopyranylidene, benzothia-pyranylidene, benzoselenapyranylidene, or benzo-telluropyranylidene;
A2 represents phenyl, dimethylaminophenyl, dimethylamino or a nucleus selected from the group consisting of oxazolyl, 9-julolidyl, thiazolyl, selenazolyl, tetrahydroquinolinyl, imidazolyl, benzoxazolyl, benzothiazolyl or naphthyl; and X represents BF4?, ClO4?, CF3SO3?, FSO3?, PF6?, CH3SO3?, Cl?, Br?, or I?.
7. The element of claim 1 or 2 wherein the dye is selected from the group consisting of
8. The element of claim 1 or 2 wherein the optical recording layer has an absorption factor of at least 20.
9. The recording element of claim 1 or 2 wherein the support is reflecting.
10. the recording element of claim 1 or 2 wherein the binder is selected from the group con-sisting of
11. A method of making a recording element comprising the steps:
a. applying to a support a coating composition comprising a radiation absorptive dye and a compatible binder and b. drying the composition to form an amorphous layer; characterized in that the dye is a telluropyrylium material.
a. applying to a support a coating composition comprising a radiation absorptive dye and a compatible binder and b. drying the composition to form an amorphous layer; characterized in that the dye is a telluropyrylium material.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US672,013 | 1984-11-16 | ||
| US06/672,013 US4584258A (en) | 1984-11-16 | 1984-11-16 | Recording and information record elements comprising telluropyrlium dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1236297A true CA1236297A (en) | 1988-05-10 |
Family
ID=24696801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000472367A Expired CA1236297A (en) | 1984-11-16 | 1985-01-18 | Recording and information record elements comprising telluropyrylium dyes |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4584258A (en) |
| EP (1) | EP0182594B1 (en) |
| JP (1) | JPS61130090A (en) |
| CA (1) | CA1236297A (en) |
| DE (1) | DE3573962D1 (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0264198B1 (en) * | 1986-09-18 | 1993-03-03 | Canon Kabushiki Kaisha | Optical information recording medium |
| US4839260A (en) * | 1987-06-30 | 1989-06-13 | Eastman Kodak Company | Novel polymethine dyes and UV absorbers and imaging materials for their use |
| US4839274A (en) * | 1987-06-30 | 1989-06-13 | Eastman Kodak Company | Novel polymethine dyes and UV absorbers containing a triarylborylisocyano group and imaging compositions containing these dyes |
| US5024927A (en) * | 1988-10-06 | 1991-06-18 | Ricoh Company, Ltd. | Information recording medium |
| US4916127A (en) * | 1988-10-24 | 1990-04-10 | Eastman Kodak Company | Mixed chalcogenide pyrylium salts of a Lewis base |
| US5047419A (en) * | 1988-10-24 | 1991-09-10 | Eastman Kodak Company | Photodynamic therapy of glioma or mammary carcinoma using seleno- or telluropyrylium salts |
| EP0371428A3 (en) * | 1988-11-29 | 1991-10-16 | Kabushiki Kaisha Toshiba | Information storage medium |
| US5082771A (en) * | 1989-06-27 | 1992-01-21 | Eastman Kodak Company | Detecting cells using tellurapyrylium dihydroxides |
| US4963669A (en) * | 1989-06-27 | 1990-10-16 | Eastman Kodak Company | Purification of tellurapyrylium dyes |
| US5891602A (en) * | 1992-05-29 | 1999-04-06 | Eastman Kodak Company | Dye donor binder for laser-induced thermal dye transfer |
| US5356685A (en) * | 1993-02-19 | 1994-10-18 | Eastman Kodak Company | Recordable optical element having a leuco dye |
| US5326677A (en) * | 1993-02-19 | 1994-07-05 | Eastman Kodak Company | Optical retrieval apparatus using a tellurium (IV) leuco dye |
| US5362536A (en) * | 1993-02-19 | 1994-11-08 | Eastman Kodak Company | Recordable optical element having a leuco dye |
| US5386002A (en) * | 1993-12-03 | 1995-01-31 | The Dow Chemical Company | Fluorene based bisimides and thermoplastic polymers thereof |
| US6841270B2 (en) * | 2003-04-17 | 2005-01-11 | Canon Kabushiki Kaisha | Organic light-emitting device having pyrylium salt as charge transport material |
| US20070020560A1 (en) * | 2005-05-27 | 2007-01-25 | Larson Lief C | Limited play optical discs |
| US20090075015A1 (en) * | 2007-07-24 | 2009-03-19 | Detty Michael R | Limited Play Optical Discs |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51130218A (en) * | 1975-05-07 | 1976-11-12 | Fuji Photo Film Co Ltd | Non-silver salt type photosensitive materials sensitized by colloidal elments |
| JPH0114038B2 (en) * | 1977-12-19 | 1989-03-09 | Eastman Kodak Co | |
| US4355097A (en) * | 1978-04-10 | 1982-10-19 | Eastman Kodak Company | Tellurium (IV) compounds and compositions |
| US4281058A (en) * | 1979-09-10 | 1981-07-28 | Energy Conversion Devices, Inc. | Tellurium imaging composition |
| NL7906728A (en) * | 1979-09-10 | 1981-03-12 | Philips Nv | OPTICAL REGISTRATION DISC. |
| US4415621A (en) * | 1980-02-25 | 1983-11-15 | Eastman Kodak Company | Use of α,α-bis(dialkylaminobenzylidene) ketone dyes in optical recording elements |
| JPS5933320B2 (en) * | 1981-04-03 | 1984-08-15 | 株式会社東芝 | optical information recording medium |
| US4365017A (en) * | 1981-07-01 | 1982-12-21 | Eastman Kodak Company | Telluropyrylium electron accepting dye sensitizers for electron donating photoconductive compositions |
| US4446223A (en) * | 1982-06-24 | 1984-05-01 | Eastman Kodak Company | Recording and information record elements comprising oxoindolizine and oxoindolizinium dyes |
| US4501808A (en) * | 1982-08-30 | 1985-02-26 | Canon Kabushiki Kaisha | Recording medium and process employing a photosensitive organic film |
| NL8300155A (en) * | 1983-01-17 | 1984-08-16 | Philips Nv | REGISTRATION ELEMENT WITH A PYRYLIUM OR THIOPYRYLIUM SQUARYLIUM DYE LAYER AND NEW PYRYLIUM OR THIOPYRYLIUM SQUARYLIUM COMPOUNDS. |
| US4499165A (en) * | 1983-03-09 | 1985-02-12 | Eastman Kodak Company | Amorphous compositions of dyes and binder-mixtures in optical recording elements and information recorded elements |
-
1984
- 1984-11-16 US US06/672,013 patent/US4584258A/en not_active Expired - Lifetime
-
1985
- 1985-01-18 CA CA000472367A patent/CA1236297A/en not_active Expired
- 1985-11-13 DE DE8585308241T patent/DE3573962D1/en not_active Expired
- 1985-11-13 EP EP85308241A patent/EP0182594B1/en not_active Expired
- 1985-11-14 JP JP60255810A patent/JPS61130090A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0182594B1 (en) | 1989-10-25 |
| EP0182594A1 (en) | 1986-05-28 |
| DE3573962D1 (en) | 1989-11-30 |
| US4584258A (en) | 1986-04-22 |
| JPS61130090A (en) | 1986-06-17 |
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