US4937159A
Expired / Lapsed
US
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Photosensitive materials and compositions containing ionic dye compounds as initiators and thiols as autooxidizers
Assignee: Carestream Health Inc
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Filing: 1988-12-07
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Granted: 1990-06-26
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Expires: 2008-12-07
Abstract
Abstract A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound and an ionic dye-counter ion compound, said compound being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said compound; and photosensitive materials incorporating the same.
Inventors
- 👤 Peter Gottschalk
- 👤 Douglas C. Neckers
- 👤 Gary B. Schuster
- 👤 Paul C. Adair
- 👤 S. Peter Pappas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 09:09
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; A; A61; A61K; A61K6/00; A61K6/80; A61K6/884; A61K6/887; G; G03; G03F; G03F7/00; G03F7/002; G03F7/0037; G03F7/004; G03F7/027; G03F7/028; G03F7/029; G03F7/031; A61C; A61C13/00; A61C13/0003; A61C13/0006; A61C13/0013; A61C19/00; A61C19/003; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/115; Y10S430/117
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
63 words
A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound, an ionic dye-reactive counter ion compound and a thiol, said ionic dye-reactive counter ion compound being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound and being a stable non-transient compound prior to exposure to said actinic radiation.
Claim 2
Dependent Claim
63 words
A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound, an ionic dye-reactive counter ion compound and a thiol, said ionic dye-reactive counter ion compound being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound and being a stable non-transient compound prior to exposure to said actinic radiation.
Claim 3
Dependent Claim
14 words
The photohardenable composition of claim 1 wherein said compound is an anionic dye compound.
Claim 4
Dependent Claim
20 words
The composition according to claim 2 wherein said thiol is selected from the group consisting of mercaptobenzoxazoles, mercaptotetrazines and mercaptotriazines.
Claim 5
Dependent Claim
46 words
The composition according to claim 3 wherein said thiol is selected from the group consisting of 2-mercaptobenzothiazole, 6-ethoxy-2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 4-methyl-4H-1,2,4-triazole-3-thiol, 2-mercapto-1-methylimidazole, 2-mercapto-5-methylthio-1,3,4-thiadiazole, 5-n-butylthio-2-mercapto-1,3,4-thiadiazole, 4-methoxybenzenethiol, 1-phenyl-1H-tetrazole-5-thiol, 4-phenyl-4H-1,2,4-triazole-3-thiol, 2-mercaptobenzimidazole, pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis(3-mercaptoproprionate), trimethylolpropane tris (mercapto-acetate), trimethylolpropane tris (3-mercaptopropionate), 4-acetamidothiophenol, mercaptosuccinic acid, dodecanethiol, 2-mercaptopyridine, 4-mercaptopyridine, 2-mercapto-3H-quinazoline, and 2-mercaptothiazoline.
Claim 6
Dependent Claim
19 words
The photohardenable composition of claim 1 wherein said ionic dye-reactive counter ion compound is a cationic dye-borate anion complex.
Claim 7
Dependent Claim
61 words
The photohardenable composition of claim 5 wherein said cationic dye-borate anion complex is represented by the formula (I): ##STR36## where D is a cationic dye moiety; and R 1 , R 2 , R 3 and R 4 are the same or different and selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups.
Claim 8
Dependent Claim
26 words
The photohardenable composition of claim 6 wherein at least one of R 1 , R 2 , R 3 and R 4 is an alkyl group.
Claim 9
Dependent Claim
25 words
The photohardenable composition of claim 7 wherein said cationic dye is selected from the group consisting of cationic cyanine, carbocyanine, hemicyanine, rhodamine, and azamethine dyes.
Claim 10
Dependent Claim
22 words
The composition according to claim 5 wherein said thiol is a thiol selected from the group consisting of mercaptobenzoxazoles, mercaptotetrazines and mercaptotriazines.
Claim 11
Dependent Claim
46 words
The composition according to claim 9 wherein said thiol is selected from the group consisting of 2-mercaptobenzothiazole, 6-ethoxy-2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 4-methyl-4H-1,2,4-triazole-3-thiol, 2-mercapto-1-methylimidazole, 2-mercapto-5-methylthio-1,3,4-thiadiazole, 5-n-butylthio-2-mercapto-1,3,4-thiadiazole, 4-methoxybenzenethiol, 1-phenyl-1H-tetrazole-5-thiol, 4-phenyl-4H-1,2,4-triazole-3-thiol, 2-mercaptobenzimidazole, pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis(3-mercaptoproprionate), trimethylolpropane tris (mercapto-acetate), trimethylolpropane tris (3-mercaptopropionate), 4-acetamidothiophenol, mercaptosuccinic acid, dodecanethiol, 2-mercaptopyridine, 4-mercaptopyridine, 2-mercapto-3H-quinazoline, and 2-mercaptothiazoline.
Claim 12
Dependent Claim
79 words
A photosensitive material comprising a support having a layer of a photohardenable composition on the surface thereof, said composition comprising a free radical addition polymerizable or crosslinkable compound, an ionic dye-reactive counter ion compound and a thiol, said ionic dye-reactive counter ion compound being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound and being a stable non-transient compound prior to exposure to said actinic radiation.
Claim 13
Dependent Claim
79 words
A photosensitive material comprising a support having a layer of a photohardenable composition on the surface thereof, said composition comprising a free radical addition polymerizable or crosslinkable compound, an ionic dye-reactive counter ion compound and a thiol, said ionic dye-reactive counter ion compound being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said polymerizable or crosslinkable compound and being a stable non-transient compound prior to exposure to said actinic radiation.
Claim 14
Dependent Claim
14 words
The photosensitive material of claim 11 wherein said complex is an anionic dye complex.
Claim 15
Dependent Claim
23 words
The photosensitive material according to claim 12 wherein said thiol is a thiol selected from the group consisting of mercaptobenzoxazoles, mercaptotetrazines and mercaptotriazines.
Claim 16
Dependent Claim
47 words
The photosensitive material according to claim 13 wherein said thiol is selected from the group consisting of 2-mercaptobenzothiazole, 6-ethoxy-2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 4-methyl-4H-1,2,4-triazole-3-thiol, 2-mercapto-1-methylimidazole, 2-mercapto-5-methylthio-1,3,4-thiadiazole, 5-n-butylthio-2-mercapto-1,3,4-thiadiazole, 4-methoxybenzenethiol, 1-phenyl-1H-tetrazole-5-thiol, 4-phenyl-4H-1,2,4-triazole-3-thiol, 2-mercaptobenzimidazole, pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis(3-mercaptoproprionate), trimethylolpropane tris (mercapto-acetate), trimethylolpropane tris (3-mercaptopropionate), 4-acetamidothiophenol, mercaptosuccinic acid, dodecanethiol, 2-mercaptopyridine, 4-mercaptopyridine, 2-mercapto-3H-quinazoline, and 2-mercaptothiazoline.
Claim 17
Dependent Claim
19 words
The photosensitive material of claim 11 wherein said ionic dye-reactive counter ion compound is a cationic dye-borate anion complex.
Claim 18
Dependent Claim
62 words
The photosensitive material of claim 15 wherein said cationic dye-borate anion complex is represented by the formula (I) ##STR37## where D is a cationic dye moiety; and R 1 , R 2 , and R 3 and R 4 are the same or different and selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups.
Claim 19
Dependent Claim
34 words
The photosensitive material of claim 16 wherein at least one of R 1 , R 2 , R 3 and R 4 is an alkyl group and at least one is an aryl group.
Claim 20
Dependent Claim
25 words
The photosensitive material of claim 17 wherein said cationic dye is selected from the group consisting of cationic cyanine, carbocyanine, hemicyanine, rhodamine, and azamethine dyes.
Claim 21
Dependent Claim
22 words
The composition according to claim 15 wherein said thiol is a thiol selected from the group consisting of mercaptobenzoxazoles, mercaptotetrazines and mercaptotriazines.
Claim 22
Dependent Claim
46 words
The composition according to claim 19 wherein said thiol is selected from the group consisting of 2-mercaptobenzothiazole, 6-ethoxy-2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 4-methyl-4H-1,2,4-triazole-3-thiol, 2-mercapto-1-methylimidazole, 2-mercapto-5-methylthio-1,3,4-thiadiazole, 5-n-butylthio-2-mercapto-1,3,4-thiadiazole, 4-methoxybenzenethiol, 1-phenyl-1H-tetrazole-5-thiol, 4-phenyl-4H-1,2,4-triazole-3-thiol, 2-mercaptobenzimidazole, pentaerythritol tetrakis(mercaptoacetate), pentaerythritol tetrakis(3-mercaptoproprionate), trimethylolpropane tris (mercapto-acetate), trimethylolpropane tris (3-mercaptopropionate), 4-acetamidothiophenol, mercaptosuccinic acid, dodecanethiol, 2-mercaptopyridine, 4-mercaptopyridine, 2-mercapto-3H-quinazoline, and 2-mercaptothiazoline.
Claim 23
Dependent Claim
12 words
The photosensitive material of claim 12 wherein said photohardenable composition is microencapsulated.
Claim 24
Dependent Claim
12 words
The photosensitive material of claim 15 wherein said photohardenable composition is microencapsulated.
Claim 25
Dependent Claim
79 words
The photosensitive material of claim 21 wherein said material is useful in forming full color images and said microcapsules include a first set of microcapsules having a cyan image-forming agent associated therewith, a second set of microcapsules having a magenta image-forming agent associated therewith and a third set of microcapsules having a yellow image-forming agent associated therewith, at least one of said first, second and third sets of microcapsules containing said photohardenable composition contain said ionic dye-counter ion compound.
Claim 26
Dependent Claim
79 words
The photosensitive material of claim 22 wherein said material is useful in forming full color images and said microcapsules include a first set of microcapsules having a cyan image-forming agent associated therewith, a second set of microcapsules having a magenta image-forming agent associated therewith and a third set of microcapsules having a yellow image-forming agent associated therewith, at least one of said first, second and third sets of microcapsules containing said photohardenable composition contain said ionic dye-counter ion compound.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-06-25 | 1993-12-25 | 1994-06-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-06-25 | 1997-12-25 | 1998-06-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-06-25 | 2001-12-25 | 2002-06-26 | $7700.00 | Window Closed / Lapsed |