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US4290870A
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Photopolymerizable compositions
Assignee: Fujifilm Holdings Corp
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Filing: 1979-05-18
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Granted: 1981-09-22
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Expires: 1999-05-18
Abstract
Abstract A photopolymerizable composition comprising (1) an addition-polymerizable compound having at least one ethylenically unsaturated double bond and (2) a photopolymerization initiator as essential components, the improvement which comprises the photopolymerization initiator comprising a combination of (a) a 5-isoxazolone represented by the general formula (1) and (b) an aromatic carbonyl compound, a dialkylamino aromatic carbonyl compound represented by any of formulae (2) to (5), a compound represented by the formula (6) or 2-(α-thioxophenetylidene)-3-methylnaphtho[1,2-d][1,3]-thiazoline: ##STR1## wherein in the formula (1), A 1 and A 2 each represent an alkyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an aryl group, an arylcarbonyl group or a hydrogen atom and may be the same or different; in the formulae (2) to (5) R 1 and R 2 each represent an alkyl group and may be the same or different, R 3 represents an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group or a 5- or 6-membered hetero-aromatic ring, and X represents a substituent having a Hammett's σ value in the range of about -0.9 to +0.7; and in the formula (6) R 4 represents an alkyl group, or an alkenyl group, R 5 represents an alkyl group, an aryl group, a thienyl group or a furyl group, and Z represents an atomic group necessaary to form a nitrogen-containing heterocyclic ring; is disclosed.
Inventors
- 👤 Syunichi Kondoh
- 👤 Akihiro Matsufuji
- 👤 Akira Umehara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:33
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/031
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
222 words
In a photopolymerizable composition comprising (1) an addition-polymerizable compound having at least one ethylenically unsaturated double bond and (2) a photopolymerization initiator as essential components, the improvement which comprises said photopolymerization initiator comprising a combination of (a) a 5-isoxazolone represented by the general formula (1) and (b) an aromatic carbonyl compound, a dialkylamino aromatic carbonyl compound represented by any of formulae (2) to (5), a compound represented by the formula (6) or 2-(α-thioxophenetylidene)-3-methylnaphtho[1,2-d][1,3]thiazoline: ##STR31## wherein in the formula (1) A 1 and A 2 each represent an alkyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an aryl group, an arylcarbonyl group or a hydrogen atom and may be the same or different; in formulae (2) to (5) R 1 and R 2 each represent an alkyl group and may be the same or different, R 3 represents an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group or a 5- or 6-membered heteroaromatic ring, and X represents a substituent having a Hammett's σ value in the range of about -0.9 to +0.7; and in the formula (6) R 4 represents an alkyl group or an alkenyl group, R 5 represents an alkyl group, an aryl group, a thienyl group or a furyl group, and Z represents an atomic group necessary to form a nitrogen containing heterocyclic ring.
Claim 2
Dependent Claim
222 words
In a photopolymerizable composition comprising (1) an addition-polymerizable compound having at least one ethylenically unsaturated double bond and (2) a photopolymerization initiator as essential components, the improvement which comprises said photopolymerization initiator comprising a combination of (a) a 5-isoxazolone represented by the general formula (1) and (b) an aromatic carbonyl compound, a dialkylamino aromatic carbonyl compound represented by any of formulae (2) to (5), a compound represented by the formula (6) or 2-(α-thioxophenetylidene)-3-methylnaphtho[1,2-d][1,3]thiazoline: ##STR31## wherein in the formula (1) A 1 and A 2 each represent an alkyl group, an alkylcarbonyl group, an alkoxycarbonyl group, an aryl group, an arylcarbonyl group or a hydrogen atom and may be the same or different; in formulae (2) to (5) R 1 and R 2 each represent an alkyl group and may be the same or different, R 3 represents an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group or a 5- or 6-membered heteroaromatic ring, and X represents a substituent having a Hammett's σ value in the range of about -0.9 to +0.7; and in the formula (6) R 4 represents an alkyl group or an alkenyl group, R 5 represents an alkyl group, an aryl group, a thienyl group or a furyl group, and Z represents an atomic group necessary to form a nitrogen containing heterocyclic ring.
Claim 3
Dependent Claim
26 words
The photopolymerizable composition of claim 1 which additionally contains (3) a polymer having film-forming ability and compatibility with the components (1) and (2) as a binder.
Claim 4
Dependent Claim
15 words
The photopolymerizable composition of claims 1 or 2, wherein component (a) is 3-phenyl-5-isoxazolone or 4-ethoxycarbonyl-5-isoxazolone.
Claim 5
Dependent Claim
16 words
The photopolymerizable composition of claims 1 or 2, wherein component (b) is an aromatic carbonyl compound.
Claim 6
Dependent Claim
17 words
The photopolymerizable composition of claim 4, wherein the aromatic carbonyl compound is a benzanthrone or an anthrone.
Claim 7
Dependent Claim
15 words
The photopolymerizable composition of claim 4, wherein the aromatic carbonyl compound is 1,2-benzo-9,10-anthraquinone or 2-methyl-9,10-anthraquinone.
Claim 8
Dependent Claim
26 words
The photopolymerizable composition of claims 1 or 2, wherein component (b) is a dialkylamino aromatic carbonyl compound represented by any of the formulae (2) to (5).
Claim 9
Dependent Claim
24 words
The photopolymerizable composition of claim 7, wherein the dialkylamino aromatic carbonyl compound is a compound having a p-dialkylaminocinnamoyl group represented by the formula (2).
Claim 10
Dependent Claim
21 words
The photopolymerizable composition of claim 7, wherein the dialkylamino aromatic carbonyl compound is a p-dialkylaminochalcone derivative represented by the formula (3).
Claim 11
Dependent Claim
12 words
The photopolymerizable composition of claim 9, wherein the p-dialkylaminochalcone derivative is p-dimethylaminochalcone.
Claim 12
Dependent Claim
21 words
The photopolymerizable composition of claim 7, wherein the dialkylamino aromatic carbonyl compound is a chalcone derivative represented by the formula (4).
Claim 13
Dependent Claim
22 words
The photopolymerizable composition of claim 7, wherein the dialkylamino aromatic carbonyl compound is p-dialkylaminostyryl styryl ketone derivative represented by the formula (5).
Claim 14
Dependent Claim
23 words
The photopolymerizable composition of claim 12, wherein the p-dialkylaminosytyrl styryl ketone derivative is p-dimethylaminostyryl styryl ketone, p-dimethylaminostyryl m-chlorostyryl ketone or p-dimethylaminostyryl p-methoxystyryl ketone.
Claim 15
Dependent Claim
19 words
The photopolymerizable composition of claims 1 or 2, wherein component (b) is a compound represented by the formula (6).
Claim 16
Dependent Claim
16 words
The photopolymerizable composition of claim 14, wherein the compound represented by the formula (6) is ##STR32##
Claim 17
Dependent Claim
16 words
The photopolymerizable composition of claim 14, wherein the compound represented by the formula (6) is ##STR33##
Claim 18
Dependent Claim
13 words
The photopolymerizable composition of claims 1 or 2, wherein component (b) is 2-(α-thioxophenetylidene)-3-methylnaphtho[1,2-d][1,3]thiazoline.
Claim 19
Dependent Claim
24 words
The photopolymerizable composition of claims 1 or 2, wherein said 5-isoxazolone is selected from the group consisting of 3-methyl-3-phenyl-5-isoxazolone, 5-isoxazolone, 3-ethyl-5-isoxazolone, 3-acetyl-5-isoxazolone and 4-ethoxycarbonyl-5-isoxazolone.
Claim 20
Dependent Claim
17 words
The photopolymerizable composition of claim 4, wherein said aromatic carbonyl compound contains one or two oxo-oxygen atoms.
Claim 21
Dependent Claim
28 words
The photopolymerizable composition of claim 4, wherein said aromatic carbonyl compound is an aromatic acyloin, an aromatic acyloin ether, an aromatic ketone or a polynuclear condensation type quinone.
Claim 22
Dependent Claim
15 words
The photopolymerizable composition of claim 20, wherein said quinone is an anthraquinone or a phenanthraquinone.
Claim 23
Dependent Claim
48 words
The photopolymerizable composition of claims 1 or 2, wherein X is selected from the group consisting of a hydrogen atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group, a dimethylamino group, a diethylamino group, a chlorine atom, a bromine atom and a cyano group.
Claim 24
Dependent Claim
61 words
The photopolymerizable composition of claim 8, wherein said compound of the formula (2) is selected from the group consisting of p-dimethylaminostyryl methyl ketone, p-dimethylaminostyryl ethyl ketone, p-dimethylaminostyryl propyl ketone, p-dimethylaminostyryl butyl ketone, p-dimethylaminostyryl isobutyl ketone, p-dimethylaminostyryl tert-butyl ketone, p-dimethylaminostyryl cyclohexyl ketone, p-dimethylaminostyryl phenetyl ketone, methyl p-dimethylaminocinnamate, ethyl p-dimethylaminocinnamate, p-dimethylaminostyryl 2-pyridyl ketone, p-dimethylaminostyryl 4-pyridyl ketone, p-dimethylaminostyryl 2-thienyl ketone, and p-dimethylaminostyryl 9-anthryl ketone.
Claim 25
Dependent Claim
36 words
The photopolymerizable composition of claim 9, wherein said compound of the formula (3) is selected from the group consisting of p-dimethylaminochalcone, p-dimethylamino-m'-chlorochalcone, p-dimethylamino-p'-chlorochalcone, p-dimethylamino-m'-bromochalcone, p-dimethylamino-p'-bromochalcone, p-dimethylamino-p'-cyanochalcone, p-dimethylamino-p'-methoxychalcone, p-dimethylamino-p'-methylchalcone, p-dimethylamino-m'-methylchalcone, p-dimethylamino-p'-ethylchalcone, p-dimethylamino-m'-ethylchalcone, p-diethylamino-p'-bromochalcone, p-diethylamino-m'-bromochalcone, p-diethylamino-p'-chlorochalcone and p-diethylamino-m'-chlorochalcone.
Claim 26
Dependent Claim
35 words
The photopolymerizable composition of claim 11, wherein said compound represented by the formula (4) is selected from the group consisting of p'-dimethylaminochalcone, p-cyano-p'-dimethylaminochalcone, m-chloro-p'-dimethylaminochalcone, p-chloro-p'-dimethylaminochalcone, m-bromo-p'-dimethylaminochalcone, p-bromo-p'-dimethylaminochalcone, m-methyl-p'-dimethylaminochalcone, p-methyl-p'-dimethylaminochalcone, p-ethyl-p'-dimethylaminochalcone, m-ethyl-p'-dimethylaminochalcone, p-ethyl-p'-dimethylaminochalcone, p-methoxy-p'-dimethylaminochalcone and p,p'-bis(dimethylamino)chalcone.
Claim 27
Dependent Claim
57 words
The photopolymerizable composition of claim 12, wherein said compound represented by the formula (5) is selected from the group consisting of p-dimethylaminostyryl p-methylstyryl ketone, p-dimethylaminostyryl p-ethylstyryl ketone, p-dimethylaminostyryl p-chlorostyryl ketone, p-dimethylaminostyryl m-chlorostyryl ketone, p-dimethylaminostyryl p-bromostyryl ketone, p-dimethylaminostyryl m-bromostyryl ketone, p-dimethylaminostyryl p-methoxystyryl ketone, p-dimethylaminostyryl p-ethoxystyryl ketone, p-dimethylaminostyryl p-cyanostyryl ketone, p-dimethylaminostyryl m-methylstyryl ketone, p-dimethylaminostyryl m-ethylstyryl ketone, bis(p-dimethylaminostyryl)ketone and bis(p-diethylaminostyryl)ketone.
Claim 28
Dependent Claim
24 words
The photopolymerizable composition of claims 1 or 2, wherein the weight ratio of compound (a) to compound (b) is about 1:30 to about 30:1.
Claim 29
Dependent Claim
33 words
The photopolymerizable composition of claims 1 or 2, wherein said component (2) is present in an amount of about 0.1 to 20% by weight based on the weight of said ethylenic compound (1).
Claim 30
Dependent Claim
22 words
The photopolymerizable composition of claim 2, wherein said composition is developable by stripping, by water, or by a weak aqueous alkali solution.
Claim 31
Dependent Claim
31 words
The photopolymerizable composition of claim 2, wherein said polymer is present in an amount of about 10% to about 50% by weight based on the weight of said ethylenic compound (1).
Claim 32
Dependent Claim
84 words
The photopolymerizable composition of claim 1, wherein in Formula I the alkyl group represented by A 1 and A 2 is a straight or branched chain alkyl group having 1 to 5 carbon atoms, the alkyl carbonyl group has 2 to 6 carbon atoms, the alkoxy carbonyl group is one in which the alkyl group is straight or branched chain having 1 to 5 carbon atoms, the aryl group is phenyl, p-tolyl, m-tolyl or o-tolyl and the arylcarbonyl group is benzoyl, m-tolyoly or o-tolyoly.
References Cited (Backward Citations)
US3870524A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-21 | 1985-03-23 | 1985-09-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-21 | 1989-03-23 | 1989-09-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-21 | 1993-03-23 | 1993-09-22 | $7700.00 | Window Closed / Lapsed |