US4062686A
Expired / Lapsed
US
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Sensitizers for photocrosslinkable polymers
Assignee: Eastman Kodak Co
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Filing: 1976-04-21
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Granted: 1977-12-13
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Expires: 1996-04-21
Abstract
Abstract Merocyanine dyes comprising 2-(heterocyclylcarbonylmethylene)thiazolines and selenazolines and 2-[di(heterocyclylcarbonyl)methylene]thiazolines and selenazolines are efficient sensitizers for light-sensitive unsaturated materials such as unsaturated vesiculators which release a gas upon exposure to radiation, photocrosslinkable unsaturated polymers, and azides such as photocrosslinkable polymeric azides used in photomechanical resists and lithographic plates.
Inventors
- 👤 James Albert Van Allan
- 👤 Michael Paul Cunningham
- 👤 Donald Paul Specht
- 👤 Samir Yacoub Farid
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 09:47
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031; C; C09; C09B; C09B23/00; C09B23/10; G03C; G03C5/00; G03C5/60; G03F7/008; G03F7/0085
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
138 words
A photosensitive composition comprising a light-sensitive material selected from nonpolymeric compounds having ethylenic unsaturation and polymers containing in the backbone or in pendant groups, moieties that have ethylenic unsaturation; and a sensitizing amount of a sensitizer of the following formula: ##STR46## wherein X is a sulfur or a selenium atom; R 1 , R 2 , R 3 and R 4 independently represent hydrogen, lower alkoxy of 1 to 4 carbon atoms or taken together R 1 and R 2 , R 2 and R 3 , R 3 and R 4 constitute the atoms needed to complete a fused benzo ring; R 5 represents lower alkyl of 1 to 4 carbon atoms; R 6 represents ##STR47## where R 8 is a heterocyclic group such as furyl or thienyl; R 7 is heterocyclyl such as furyl or thienyl.
Claim 2
Dependent Claim
138 words
A photosensitive composition comprising a light-sensitive material selected from nonpolymeric compounds having ethylenic unsaturation and polymers containing in the backbone or in pendant groups, moieties that have ethylenic unsaturation; and a sensitizing amount of a sensitizer of the following formula: ##STR46## wherein X is a sulfur or a selenium atom; R 1 , R 2 , R 3 and R 4 independently represent hydrogen, lower alkoxy of 1 to 4 carbon atoms or taken together R 1 and R 2 , R 2 and R 3 , R 3 and R 4 constitute the atoms needed to complete a fused benzo ring; R 5 represents lower alkyl of 1 to 4 carbon atoms; R 6 represents ##STR47## where R 8 is a heterocyclic group such as furyl or thienyl; R 7 is heterocyclyl such as furyl or thienyl.
Claim 3
Dependent Claim
23 words
A photosensitive composition of claim 1 in which said material contains from about 0.1 to about 20 percent by weight of said sensitizer.
Claim 4
Dependent Claim
49 words
A photosensitive composition comprising a light-sensitive material selected from nonpolymeric compounds having ethylenic unsaturation and polymers containing in the backbone or in pendant groups, moieties that have ethylenic unsaturation; and a sensitizing amount of a 2-[di(heterocyclylcarbonyl)-methylene]thiazoline or selenazoline having its absorptive maximum between about 340 and about 460 nm.
Claim 5
Dependent Claim
49 words
A photosensitive composition comprising a light-sensitive material selected from nonpolymeric compounds having ethylenic unsaturation and polymers containing in the backbone or in pendant groups, moieties that have ethylenic unsaturation; and a sensitizing amount of a 2-[di(heterocyclylcarbonyl)-methylene]thiazoline or selenazoline having its absorptive maximum between about 340 and about 460 nm.
Claim 6
Dependent Claim
50 words
A photosensitive composition of claim 3 in which said material is selected from the class consisting of cinnamylideneacetate esters of poly(vinyl alcohol), unsaturated vesiculating agents, cinnamic acid esters of poly(vinyl alcohol), cinnamic acid esters of cellulose, cinnamic acid esters of hydroxyalkylcellulose, cinnamoylated polystyrene, cinnamyl vinyl ketone polymers and unsaturated polyesters.
Claim 7
Dependent Claim
15 words
A photosensitive composition of claim 3 in which said material is an unsaturated vesiculating agent.
Claim 8
Dependent Claim
14 words
A photosensitive composition of claim 3 in which said material is an unsaturated polymer.
Claim 9
Dependent Claim
172 words
A photosensitive composition of claim 6 in which said material has incorporated into a light-sensitive polymer molecule disulfonamido units having the structural formula: ##STR48## wherein a. R is selected from the group consisting of --H and an alkali metal, b. X and Y are the same or different radicals selected from the group consisting of arylene radicals of 6 to about 12 carbons and said radicals being unsubstituted or substituted with chlorine atoms, and c. A and B are the same or different and are selected from the group consisting of ##STR49## wherein R" is selected from the group consisting of --H, alkyl of from 1 to about 8 carbon atoms, alkylene of from 2 to about 8 carbon atoms, and aryl of from 6 to about 14 carbon atoms; R 1 is hydrogen or alkyl of from 1 to about 8 carbon atoms and R 2 is hydrogen, alkyl of from 1 to about 8 carbon atoms so that at least one of A and B has a valence of 1.
Claim 10
Dependent Claim
17 words
A photosensitive composition of claim 3 in which said material is a cinnamylideneacetate ester of poly(vinyl alcohol).
Claim 11
Dependent Claim
15 words
A photosensitive composition of claim 3 in which said material is a cinnamic acid ester.
Claim 12
Dependent Claim
13 words
A photosensitive composition of claim 3 in which said sensitizer is a 2-[di-(heterocyclylcarbonyl)methylene]thiazoline.
Claim 13
Dependent Claim
13 words
A photosensitive composition of claim 3 in which said sensitizer is a 2-[di(heterocyclylcarbonyl)methylene]selenazoline.
Claim 14
Dependent Claim
12 words
A photosensitive composition of claim 3 in which said sensitizer is 2-[bis(2-furoyl)methylene]-1-methylnaphtho[1,2-d]thiazoline.
Claim 15
Dependent Claim
12 words
A photosensitive composition of claim 3 in which said sensitizer is 2-[bis(2-furoyl)methylene]-3-methylbenzoselenazoline.
Claim 16
Dependent Claim
146 words
A photographic element comprising a support having thereon a photosensitive composition comprising a light-sensitive material selected from nonpolymeric compounds having ethylenic unsaturation and polymers containing in the backbone or in pendant groups, moieties that have ethylenic unsaturation; and a sensitizing amount of a sensitizer of the following formula: ##STR50## wherein X is a sulfur or a selenium atom; R 1 , R 2 , R 3 and R 4 independently represent hydrogen, lower alkoxy of 1 to 4 carbon atoms or taken together R 1 and R 2 , R 2 and R 3 , R 3 and R 4 constitute the atoms needed to complete a fused benzo ring; R 5 represents lower alkyl or 1 to 4 carbon atoms; R 6 represents ##STR51## where R 8 is a heterocyclic group such as furyl or thienyl; R 7 is heterocyclyl such as furyl or thienyl.
Claim 17
Dependent Claim
146 words
A photographic element comprising a support having thereon a photosensitive composition comprising a light-sensitive material selected from nonpolymeric compounds having ethylenic unsaturation and polymers containing in the backbone or in pendant groups, moieties that have ethylenic unsaturation; and a sensitizing amount of a sensitizer of the following formula: ##STR50## wherein X is a sulfur or a selenium atom; R 1 , R 2 , R 3 and R 4 independently represent hydrogen, lower alkoxy of 1 to 4 carbon atoms or taken together R 1 and R 2 , R 2 and R 3 , R 3 and R 4 constitute the atoms needed to complete a fused benzo ring; R 5 represents lower alkyl or 1 to 4 carbon atoms; R 6 represents ##STR51## where R 8 is a heterocyclic group such as furyl or thienyl; R 7 is heterocyclyl such as furyl or thienyl.
Claim 18
Dependent Claim
11 words
An element of claim 21 in which said sensitizer is 2-[bis(2-furoyl)methylene]-1-methylnaphtho[1,2-d]thiazoline.
Claim 19
Dependent Claim
11 words
An element of claim 14 in which said sensitizer is 2-[bis(2-furoyl)methylene]-3-methylbenzose]enazoline.
Claim 20
Dependent Claim
12 words
An element of claim 14 in which said sensitizer is a 2-[di(heterocyclylcarbonyl)methylene]selenazoline.
Claim 21
Dependent Claim
12 words
An element of claim 14 in which said sensitizer is a 2-[di(heterocyclylcarbonyl)methylene]thiazoline.
Claim 22
Dependent Claim
53 words
A photographic element comprising a support having thereon a photosensitive composition comprising a light-sensitive material selected from nonpolymeric compounds having ethylenic unsaturation and polymers containing in the backbone or in pendant groups, moieties that have ethylenic unsaturation; and a 2-[di(heterocyclylcarbonyl)methylene]thiazoline or selenazoline having its absorptive maximum between about 340 to about 460 nm.
Claim 23
Dependent Claim
53 words
A photographic element comprising a support having thereon a photosensitive composition comprising a light-sensitive material selected from nonpolymeric compounds having ethylenic unsaturation and polymers containing in the backbone or in pendant groups, moieties that have ethylenic unsaturation; and a 2-[di(heterocyclylcarbonyl)methylene]thiazoline or selenazoline having its absorptive maximum between about 340 to about 460 nm.
Claim 24
Dependent Claim
15 words
An element as defined in claim 19, wherein said light-sensitive material is an unsaturated polyester.
Claim 25
Dependent Claim
25 words
A photosensitive composition comprising an unsaturated polyester and a sensitizing amount of a 2-(heterocyclylcarbonylmethylene)thiazoline having its absorptive maximum between about 340 and about 460 nm.
Claim 26
Dependent Claim
25 words
A photosensitive composition comprising an unsaturated polyester and a sensitizing amount of a 2-(heterocyclylcarbonylmethylene)thiazoline having its absorptive maximum between about 340 and about 460 nm.
Claim 27
Dependent Claim
12 words
A photosensitive composition of claim 21 in which said sensitizer is 2-[(2-thenoyl)methylene]-1-methylnaphtho[1,2-d]thiazoline.
Claim 28
Dependent Claim
33 words
A photographic element comprising a support having thereon a photosensitive composition comprising an unsaturated polyester and a sensitizing amount of a 2-(heterocyclylcarbonylmethylene)thiazoline having its absorptive maximum between about 340 and about 460 nm.
Claim 29
Dependent Claim
33 words
A photographic element comprising a support having thereon a photosensitive composition comprising an unsaturated polyester and a sensitizing amount of a 2-(heterocyclylcarbonylmethylene)thiazoline having its absorptive maximum between about 340 and about 460 nm.
Claim 30
Dependent Claim
101 words
A photographic element comprising a support having thereon a photosensitive composition comprising an unsaturated polyester and a sensitizing amount of a sensitizer of the following formula: ##STR52## wherein R 1 , R 2 , R 3 and R 4 independently represent hydrogen, lower alkoxy of 1 to 4 carbon atoms or taken together R 1 and R 2 , R 2 and R 3 , R 3 and R 4 constitute the atoms needed to complete a fused benzo ring; R 5 represents lower akyl of 1 to 4 carbon atoms; and R 7 is heterocyclyl such as furyl or thienyl.
Claim 31
Dependent Claim
101 words
A photographic element comprising a support having thereon a photosensitive composition comprising an unsaturated polyester and a sensitizing amount of a sensitizer of the following formula: ##STR52## wherein R 1 , R 2 , R 3 and R 4 independently represent hydrogen, lower alkoxy of 1 to 4 carbon atoms or taken together R 1 and R 2 , R 2 and R 3 , R 3 and R 4 constitute the atoms needed to complete a fused benzo ring; R 5 represents lower akyl of 1 to 4 carbon atoms; and R 7 is heterocyclyl such as furyl or thienyl.
Claim 32
Dependent Claim
11 words
An element of cliam 24 in which said sensitizer is 2-[(2-thenoyl)methylene]benzothiazoline.
Claim 33
Dependent Claim
11 words
An element of cliam 24 in which said sensitizer is 2-[(2-thenoyl)methylene]benzothiazoline.
Claim 34
Dependent Claim
93 words
A photosensitive composition comprising an unsaturated polyester and a sensitizing amount of a sensitizer of the following formula: ##STR53## wherein R 1 , R 2 , R 3 and R 4 independently represent hydrogen, lower alkoxy of 1 to 4 carbon atoms or taken together R 1 and R 2 , R 2 and R 3 , R 3 and R 4 constitute the atoms needed to complete a fused benzo ring; R 5 represents lower alkyl of 1 to 4 carbon atoms; and R 7 is heterocyclyl such as furyl or thienyl.
Claim 35
Dependent Claim
93 words
A photosensitive composition comprising an unsaturated polyester and a sensitizing amount of a sensitizer of the following formula: ##STR53## wherein R 1 , R 2 , R 3 and R 4 independently represent hydrogen, lower alkoxy of 1 to 4 carbon atoms or taken together R 1 and R 2 , R 2 and R 3 , R 3 and R 4 constitute the atoms needed to complete a fused benzo ring; R 5 represents lower alkyl of 1 to 4 carbon atoms; and R 7 is heterocyclyl such as furyl or thienyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-12 | 1981-06-13 | 1981-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-12 | 1985-06-13 | 1985-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-12 | 1989-06-13 | 1989-12-13 | $7700.00 | Window Closed / Lapsed |