US4548895A
Expired / Lapsed
US
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Process for the production of images using a heating step prior to imaging
Assignee: Novartis Corp
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Filing: 1984-03-07
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Granted: 1985-10-22
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Expires: 2004-03-07
Abstract
Abstract A layer of a liquid composition containing (A) a heat-activated polymerizing agent for 1,2-epoxides, (B) a light-sensitive compound having in the same molecule at least one 1,2-epoxide group of formula ##STR1## and at least one unsaturated ester group of formula CH.sub.2 ═C(R.sup.1)COO-- II where R 1 =H, Cl, Br, or C 1 -C 4 alkyl, a mixture of (C) a compound containing at least one 1,2-epoxide group of formula I together with (D) a compound containing at least one unsaturated ester group of formula II, or a mixture of (B) with (C) and/or (D), is heated to solidify the layer, and subsequently it is exposed to actinic radiation in a predetermined pattern and those parts of the layer that have not become photopolymerized are removed by treatment with a suitable solvent. An example of a suitable polymerizing agent (A) is the complex of boron trifluoride with monoethylamine. An example of a light-sensitive compound (B) is glycidyl methacrylate. The epoxide compound (C) may be the diglycidyl ether of 2,2-bis(4-hydroxyphenyl)propane, and the unsaturated ester (D) may be 1,4-bis(2-hydroxy-3-acryloyloxypropoxy)butane.
Inventors
- 👤 Edward Irving
- 👤 Terence J. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 16:54
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/038; G03F7/027
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
224 words
A process for the production of an image comprising (i) heating at a temperature of at least 80° C. a layer, supported on a carrier, of a liquid composition consisting essentially of (A) 1 to 10 parts per 100 parts of light sensitive compound or mixture of a heat-activated latent polymerizing agent for 1,2-epoxides with (B) a light-sensitive compound having in the same molecule at least one 1,2-epoxide group of formula ##STR5## and at least one unsaturated ester group of formula CH.sub.2 ═C(R.sup.1)COO-- II where R 1 is a hydrogen, chlorine, or bromine atom or an alkyl group of 1 to 4 carbon atoms, or with a mixture of (C) a compound containing at least one 1,2-epoxide group of formula I absent the unsaturated ester group of formula II, together with (D) a compound containing at least one unsaturated ester group of formula II absent the 1,2-epoxide group of formula I, or with a mixture of compound (B) and a compound (C) and/or a compound (D), such that the layer solidifies through thermal polymerization and becomes essentially non-tacky but remains photopolymerizable and subsequently (ii) exposing the solidified layer to actinic radiation in a predetermined pattern such that exposed parts of the layer are photopolymerized and (iii) removing those parts of the layer which have not become substantially photopolymerized by treatment with a solvent therefor.
Claim 2
Dependent Claim
224 words
A process for the production of an image comprising (i) heating at a temperature of at least 80° C. a layer, supported on a carrier, of a liquid composition consisting essentially of (A) 1 to 10 parts per 100 parts of light sensitive compound or mixture of a heat-activated latent polymerizing agent for 1,2-epoxides with (B) a light-sensitive compound having in the same molecule at least one 1,2-epoxide group of formula ##STR5## and at least one unsaturated ester group of formula CH.sub.2 ═C(R.sup.1)COO-- II where R 1 is a hydrogen, chlorine, or bromine atom or an alkyl group of 1 to 4 carbon atoms, or with a mixture of (C) a compound containing at least one 1,2-epoxide group of formula I absent the unsaturated ester group of formula II, together with (D) a compound containing at least one unsaturated ester group of formula II absent the 1,2-epoxide group of formula I, or with a mixture of compound (B) and a compound (C) and/or a compound (D), such that the layer solidifies through thermal polymerization and becomes essentially non-tacky but remains photopolymerizable and subsequently (ii) exposing the solidified layer to actinic radiation in a predetermined pattern such that exposed parts of the layer are photopolymerized and (iii) removing those parts of the layer which have not become substantially photopolymerized by treatment with a solvent therefor.
Claim 3
Dependent Claim
43 words
A process according to claim 1, in which the group of formula I is attached to a cycloaliphatic ring through both indicated free valencies, or forms part of a 2,3-epoxypropyl group which is directly attached to an atom of oxygen, nitrogen, or sulphur.
Claim 4
Dependent Claim
27 words
A process according to claim 1, in which R 1 , in the unsaturated ester group of formula II, is a hydrogen atom or a methyl group.
Claim 5
Dependent Claim
38 words
A process according to claim 1, in which compound (B) is present and contains 1 or 2 groups of formula I and 1 to 6 groups of formula II and has a molecular weight of at most 3000.
Claim 6
Dependent Claim
83 words
A process according to claim 4, in which compound (B) is of the formula ##STR6## where R 1 is H, Cl, Br, or an alkyl group of 1 to 4 carbon atoms, R 2 represents the residue of a di or polyglycidyl compound after the removal of two glycidyl groups, R 3 represents the residue of a di or polycarboxylic acid after the removal of two carboxylic acid groups, and R 4 represents an alkylene chain of from 1 to 6 carbon atoms.
Claim 7
Dependent Claim
43 words
A process according to claim 5, in which R 2 is a dihydric phenol residue after removal of two phenolic hydrogen atoms, a glycol residue after removal of two alcoholic hydrogen atoms, or a hydantoin residue after removal of two amidic hydrogen atoms.
Claim 8
Dependent Claim
46 words
A process according to claim 5, in which R 3 is a saturated or unsaturated aliphatic or aromatic dicarboxylic acid residue or an aromatic tri- or tetracarboxylic acid residue, after removal of two carboxylic acid groups, and R 4 is an ethylene, propylene, or butylene group.
Claim 9
Dependent Claim
50 words
A process according to claim 5, in which compound (B) is glycidyl acrylate, glycidyl methacrylate, PG,40 2-(4-glycidyloxyphenyl)-2-(4-(3-acryloyloxy-2-hydroxypropoxy)phenyl)propane, 2-(4-(glycidyloxyphenyl)-2-(4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl)propane, 1-(2-methacryloyloxyethoxycarbonyl)-2,4- and 2,5-bis(glycidyloxycarbonyl)benzene, 1-(2-acryloyloxyethoxycarbonyl)-2,4- and 2,5-bis(glycidyloxycarbonyl)benzene, 2-acryloyloxyethoxy glycidyl succinate, 2-methacryloyloxyethoxy glycidyl succinate, 1-glycidyl-3-(3-acryloyloxy-2-hydroxypropyl)-5,5-dimethylhydantoin, 1-glycidyl-3-(2-hydroxy-3-methacryloyloxypropyl)-5,5-dimethylhydantoin, 1-glycidyloxy-4-(3-acryloyloxy-2-hydroxypropoxy)butane, 1-glycidyloxy-4-(2-hydroxy-3-methacryloyloxypropoxy)butane or the reaction product of 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate with 1 equivalent of acrylic acid or methacrylic acid.
Claim 10
Dependent Claim
30 words
A process according to claim 1, in which compound (C) is present and contains one or two groups of formula I and has a molecular weight of at most 3000.
Claim 11
Dependent Claim
43 words
A process according to claim 1, in which compound (C) is present and is a mono or polyglycidyl ester, a mono or polyglycidyl ether, a poly(N-glycidyl) compound, or an epoxide resin in which some or all of the epoxide groups are not terminal.
Claim 12
Dependent Claim
31 words
A process according to claim 10, in which compound (C) is 2,2,4-trimethylpentyl glycidyl ether, phenyl glycidyl ether, butyl glycidyl ether, a diglycidyl ether of 2,2-bis(hydroxyphenyl)propane, bis(4-hydroxyphenyl)methane or butane-1,4-diol, 1,3-diglycidyl-5,5-dimethylhydantoin, or 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate.
Claim 13
Dependent Claim
30 words
A process according to claim 1, in which compound (D) is present and contains at least two groups of formula II and has a molecular weight of at most 3000.
Claim 14
Dependent Claim
89 words
A process according to claim 1, in which compound (D) is present and is an acrylate or methacrylate of a monohydric alcohol, a full or partial ester of acrylic or methacrylic acid with an aliphatic glycol or higher functional polyol, an ester formed by reaction of a compound containing one or more glycidyl groups with acrylic or methacrylic acid, or an ester formed by reaction of a polyepoxide with an equivalent amount of an adduct of a hydroxyalkyl acrylate or methacrylate with a saturated or unsaturated dicarboxylic acid anhydride.
Claim 15
Dependent Claim
36 words
A process according to claim 13, in which compound (D) is 1,4-bis(2-hydroxy-3-acryloyloxypropoxy)butane, a poly(2-hydroxy-3-acryloyloxypropyl)ether of a bisphenol or a phenol-formaldehyde novolak, 2,2-bis(4-(2-hydroxy-3-(2-acryloyloxyethoxy)succinyloxypropoxy)phenyl)propane, 1-(2-hydroxy-3-acryloyloxypropoxy)-butane, -octane, or -decane, bis(2-hydroxy-3-acryloyloxypropyl)adipate, 2-hydroxy-3-acryloyloxypropyl propionate, 3-phenoxy-2-hydroxypropyl acrylate, or a corresponding methacrylic compound.
Claim 16
Dependent Claim
79 words
A process according to claim 1, in which (A) is a complex of boron trichloride or of boron trifluoride, a boron difluoride chelate, dicyandiamide, an imidazole, or a mixture of an aromatic onium salt or aromatic iodosyl salt of a metal halogenide acid or a metalloid halogenide acid with a catalyst which is a salt or complex of a d-block transition metal, a stannous salt, an organic peroxide, or an activated α-hydroxy compound which forms free radicals on heating.
Claim 17
Dependent Claim
105 words
A process according to claim 15, in which the polymerizing agent (A) is a complex of boron trichloride with a tertiary amine or of boron trifluoride with a primary amine, piperidine or a triaryl phosphine, or is a diphenyl iodosyl salt, in which the phenyl groups may be substituted by an alkyl group of to 4 carbon atoms, a nitro group or a halogen atom, and the anion is Sb(OH)F 5 - , AsF 6 - , SbCl 6 - , BiCl 6 - , SbF 6 - , SnCl 5 - , FeCl 4 - , BF 4 - or PF 6 - .
Claim 18
Dependent Claim
24 words
A process according to claim 1, in which the layer of liquid composition is heated at a temperature of 100° C. to 200° C.
Claim 19
Dependent Claim
20 words
A process according to claim 1, in which the solidified layer is exposed to actinic radiation of wavelength 200-600 nm.
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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) | 1988-10-21 | 1989-04-22 | 1989-10-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-21 | 1993-04-22 | 1993-10-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-21 | 1997-04-22 | 1997-10-22 | $7700.00 | Window Closed / Lapsed |