US4399211A
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Photopolymerizable compositions
Assignee: Fujifilm Holdings Corp
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Filing: 1980-11-03
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Granted: 1983-08-16
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Expires: 2000-11-03
Abstract
Abstract In a photopolymerizable composition comprising, as essential components, (A) a compound having at least one ethylenically unsaturated double bond capable of undergoing addition polymerization and (B) a photopolymerization initiator, the improvement which comprises that the photopolymerization initiator comprising a combination of (a) a 5-[(arenooxazol-2-ylidene)ethylidene]-2-thiohydantoin compound represented by the general formula (I) (a 5-[(substituted benzoxazol-2'-ylidene)ethylidene]-2-thiohydantoin compound) or (II) (a 5-[substituted naphthol(1,2-D)oxazol-2-ylidene)ethylidene]-2-thiohydantoin compound) and (b) a 2,4,6-substituted-1,3,5-triazine compound represented by the formula (III): ##STR1## wherein X represents a hydrogen atom, an alkyl group, a substituted alkyl group, an alkoxy group, an aryl group, a substituted aryl group, an aryloxy group, an aralkyl group or a halogen atom; R 1 , R 2 and R 3 each represents an alkyl group, a substituted alkyl group, an alkenyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different; and R 4 , R 5 and R 6 each represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different but at least one of which represents a mono-, di- or trihalogenomethyl group.
Inventors
- 👤 Syunichi Kondo
- 👤 Akihiro Matsufuji
- 👤 Akira Umehara
- 👤 Toshinao Ukai
- 👤 Akira Sato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 07:12
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031; C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/106; Y10S430/108; Y10S430/114; Y10S430/116; Y10S430/117; Y10S430/12; Y10S430/121; Y10S430/146
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
173 words
In a photopolymerizable composition comprising, as essential components, (A) a compound having at least one ethylenically unsaturated double bond capable of undergoing addition polymerization and (B) a photopolymerization initiator, the improvement wherein said component (A) is an oligoester acrylate or oligoester methacrylate obtained by esterification of acrylic or methacrylic acid, a polybasic acid and a polyol and said photopolymerization initiator consists essentially of a combination of (a) a 5-(substituted naphthol(1,2-D)oxazol-2-ylidene)ethylidene-2-thiohydantoin compound represented by formula (II) and (b) a 2,4,6-substituted-1,3,5-triazine compound represented by formula (III): ##STR27## wherein R 1 , R 2 and R 3 each represents an alkyl group, a substituted alkyl group, an alkenyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different; and R 4 , R 5 and R 6 each represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different but at least one of which represents a mono-, di- or trihalogenomethyl group.
Claim 2
Dependent Claim
173 words
In a photopolymerizable composition comprising, as essential components, (A) a compound having at least one ethylenically unsaturated double bond capable of undergoing addition polymerization and (B) a photopolymerization initiator, the improvement wherein said component (A) is an oligoester acrylate or oligoester methacrylate obtained by esterification of acrylic or methacrylic acid, a polybasic acid and a polyol and said photopolymerization initiator consists essentially of a combination of (a) a 5-(substituted naphthol(1,2-D)oxazol-2-ylidene)ethylidene-2-thiohydantoin compound represented by formula (II) and (b) a 2,4,6-substituted-1,3,5-triazine compound represented by formula (III): ##STR27## wherein R 1 , R 2 and R 3 each represents an alkyl group, a substituted alkyl group, an alkenyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different; and R 4 , R 5 and R 6 each represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different but at least one of which represents a mono-, di- or trihalogenomethyl group.
Claim 3
Dependent Claim
29 words
A photopolymerizable compositions of claim 1, which additionally contains (C) a polymer material having a film-forming ability and being compatible with the components (A) and (B), as a binder.
Claim 4
Dependent Claim
87 words
The photopolymerizable composition of claim 1 or 2, wherein R 1 , R 2 and R 3 each represents a substituted or unsubstituted straight or branched chain alkyl group containing 1 to 18 carbon atoms, a substituted or unsubstituted aryl group containing 6 to 14 carbon atoms, an aralkyl group the alkyl moiety of which contains 1 to 10 carbon atoms and the aryl moiety of which contains 6 to 10 carbon atoms; and a straight or branched chain alkenyl group containing 2 to 4 carbon atoms.
Claim 5
Dependent Claim
95 words
The photopolymerizable composition of claim 1 or 2, wherein said R 4 , R 5 and R 6 represent a substituted or unsubstituted straight or branched chain alkyl group containing 1 to 18 carbon atoms, a substituted or unsubstituted aryl group containing 6 to 14 carbon atoms; or an aralkyl group the alkyl moiety of which contains 1 to 10 carbon atoms, and the aryl moiety of which contains 6 to 10 carbon atoms provided that at least one of R 4 , R 5 and R 6 represents a mono-, di- or trihalogenomethyl group.
Claim 6
Dependent Claim
25 words
The photopolymerizable composition of claim 1 or 2, wherein said triazine is substituted at R 4 , R 5 and R 6 with a halomethylgroup.
Claim 7
Dependent Claim
32 words
The photopolymerizable composition of claim 1 or 2, wherein the ratio of said thiohydantoin compound (a) to said triazine compound (b) is in a range of from about 1:10 to about 10:1.
Claim 8
Dependent Claim
25 words
The photopolymerizable composition of claim 1 or 2, wherein the total amount of said photopolymerization initiators is from about 0.1% to about 20% by weight.
Claim 9
Dependent Claim
56 words
The photopolymerizable composition of claim 2, wherein said binder is selected from the group consisting of chlorinated polyethylene, chlorinated polypropylene, polymethyl methacrylate, polyvinyl chloride, vinyl chloride-vinylidene chloride copolymer, vinylidene chloride-acrylonitrile copolymer, vinyl chloride-acrylonitrile copolymer, polystyrene, polyvinyl butyral, polyvinyl acetate, polyvinyl formal, ethyl cellulose, acetyl cellulose, vinyl chloride-vinyl acetate copolymer, polychloroprene, polyisoprene, chlorinated rubber and chlorosulfonated polyethylene.
Claim 10
Dependent Claim
64 words
The photopolymerizable composition of claim 1, wherein said oligoester is represented by the formula: ##STR28## wherein R represents a hydrogen atom or a methyl group, Q represents an ester residue having a molecular weight of less than 10,000 composed of a polyhydric alcohol and a polybasic carboxylic acid which contains at least one ester bond, and p is an integer of 1 to 6.
Claim 11
Dependent Claim
49 words
The photopolymerizable composition of claim 1, wherein said polyol is selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,4-butanediol, 1,6-hexanediol, trimethylolpropane, trimethylolethane, 1,2,6-hexanetriol, glycerine, pentaerythritol, sorbitol, diethylene glycol, triethylene glycol, tetraethylene glycol, decaethylene glycol, tetradecaethylene glycol, polyethylene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol, and polypropylene glycol.
Claim 12
Dependent Claim
31 words
The photopolymerizable composition of claim 1 wherein said polybasic carboxylic acid is selected from the group consisting of aromatic polybasic carboxylic acids, unsaturated aliphatic polycarboxylic acids, and saturated aliphatic polybasic acids.
Claim 13
Dependent Claim
62 words
The photopolymerizable composition of claim 11 wherein said polybasic carboxylic acid is selected from the group consisting of phthalic acid, isophthalic acid, terephthalic acid, tetrachlorophthalic acid, tetrabromophthalic acid, trimellitic acid, pyromellitic acid, benzophenone dicarboxylic acid, maleic acid, fumaric acid, 2-tetrahydrophthalic acid, 4-tetrahydrophthalic acid, 5-norbornene-2,3-dicarboxylic acid, itaconic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, sebacic acid, and dodecanoic acid.
Claim 14
Dependent Claim
27 words
The photopolymerizable composition of claim 1 wherein said oligoester is selected from the group consisting of ##STR29## wherein Y represents one of the following two groups: ##STR30##
Claim 15
Dependent Claim
12 words
The photopolymerizable composition of claim 2 wherein said binder is chlorinated polyethylene.
Claim 16
Dependent Claim
12 words
The photopolymerizable composition of claim 2 wherein said binder is polymethyl methacrylate.
Claim 17
Dependent Claim
177 words
An imaging process for photopolymerizing a photopolymerizable composition comprising an oligoester acrylate or oligoester methacrylate obtained by the esterification of acrylic or methacrylic acid, a polybasic acid and a polyol and a photopolymerization initiator which consists essentially of a combination of (a) (a 5-(substituted naphthol(1,2-D)oxazol-2-ylidene)ethylidene-2-thiohydantoin compound) represented by formula (II) and (b) a 2,4,6-substituted-1,3,5-triazine compound represented by formula (III): ##STR31## wherein R 1 , R 2 and R 3 each represents an alkyl group, a substituted alkyl group, an alkenyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different; and R 4 , R 5 and R 6 each represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different but at least one of which represents a mono-, di- or trihalogenomethyl group, wherein said process comprises imagewise exposing to an Argon laser beam a layer of said photopolymerizable composition on a substrate, whereby the exposed areas of said layer are polymerized.
Claim 18
Dependent Claim
177 words
An imaging process for photopolymerizing a photopolymerizable composition comprising an oligoester acrylate or oligoester methacrylate obtained by the esterification of acrylic or methacrylic acid, a polybasic acid and a polyol and a photopolymerization initiator which consists essentially of a combination of (a) (a 5-(substituted naphthol(1,2-D)oxazol-2-ylidene)ethylidene-2-thiohydantoin compound) represented by formula (II) and (b) a 2,4,6-substituted-1,3,5-triazine compound represented by formula (III): ##STR31## wherein R 1 , R 2 and R 3 each represents an alkyl group, a substituted alkyl group, an alkenyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different; and R 4 , R 5 and R 6 each represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group or an aralkyl group, which may be the same or different but at least one of which represents a mono-, di- or trihalogenomethyl group, wherein said process comprises imagewise exposing to an Argon laser beam a layer of said photopolymerizable composition on a substrate, whereby the exposed areas of said layer are polymerized.
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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) | 1986-08-15 | 1987-02-14 | 1987-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-08-15 | 1991-02-14 | 1991-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-08-15 | 1995-02-14 | 1995-08-16 | $7700.00 | Window Closed / Lapsed |