Claims
- 1. A process for preparing a lithographic priming plate which comprises the steps of providing a presensitized plate comprised of a substrate having a hydrophilic surface provided thereon with a light-sensitive layer containing an alkaline water-soluble or swellable photocrosslinkable polymer having photodimerizable unsaturated double bonds wherein the light-sensitive layer contains a copolycondensed diazo resin having, as structural units, units derived from an aromatic compound having at least one carboxyl group and units derived from an aromatic diazonium compound represented by the following general formula (I): ##STR9## wherein R.sup.1 represents a hydrogen atom, an alkyl group, an alkoxy group, a hydroxy group, a carboxy ester group or a carboxyl group; R.sup.2 and R.sup.3 each represents a hydrogen atom, an alkyl group or an alkoxy group; X.sup.- represents an anion; and Y represents --NH--, --O-- or --S-- wherein the light-sensitive layer is composed so as to be capable of being developed in an aqueous alkaline solution free from an organic solvent; imagewise exposing the presensitized plate and developing the presensitized plate with an aqueous alkaline solution free from an organic solvent so as to remove non-image areas of the light-sensitive layer.
- 2. The process of claim 1 wherein said alkaline solution contains an inorganic alkaline agent selected from the group consisting of sodium silicate, potassium silicate, sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium tertiary phosphate, sodium secondary phosphate, ammonium tertiary phosphate, ammonium secondary phosphate, sodium metasilicate, sodium bicarbonate and aqueous ammonia.
- 3. The process of claim 1 wherein the presensitized plate further comprises at least one of an intermediate layer between the substrate and the light-sensitive layer and the light-sensitive layer and the intermediate layer comprises the copolycondensed diazo resin.
- 4. The process of claim 3 wherein the aromatic compound having at least one carboxyl group includes, in the molecule, an aromatic ring having at least one carboxyl group, provided that a part of the carboxyl group may be bonded to the aromatic ring directly or through an alkylene group having 1 to 4 carbon atoms.
- 5. The process of claim 4 wherein the aromatic ring is an aryl groups and the number of carboxyl groups bonded to the aromatic group ranges from 1 to 3.
- 6. The process of claim 3 wherein the molecular weight of the copolycondensed diazo resin ranges from about 400 to 100,000.
- 7. The process of claim 6 wherein the molecular weight of the copolycondensed diazo resin ranges from about 800 to 5,000.
- 8. The process of claim 3 wherein the light-sensitive layer comprises the copolycondensed diazo resin in an amount ranging from 1 to 10% by weight on the basis of the total weight of the light-sensitive layer.
- 9. The process of claim 3 wherein the intermediate layer comprises the copolycondensed diazo resin in an amount ranging from 60 to 100% by weight on the basis of the total weight of the intermediate layer.
- 10. The process of claim 1 wherein the aromatic compound having, in the molecule, at least one carboxyl group is selected from the group consisting of salicylic acid, 4-methylsalicylic acid, 6-methylsalicylic acid, 4-ethylsalicylic acid, 6-propylsalicylic acid, 6-1aurylsalicylic acid, 6-stearylsalicylic acid, 4,6-dimethylsalicylic acid, p-hydroxybenzoic acid, 2-methyl-4-hydroxybenzoic acid, 6-methyl-4-hydroxybenzoic acid, 2,6-dimethyl-4-hydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,4-dihydroxy-6-methylbenzoic acid, 2,6-dihydroxybenzoic acid, 2,6-dihydroxy-4-methylbenzoic acid, 4-chloro-2,6-dihydroxybenzoic acid, 4-methoxy-2,6-dioxybenzoic acid, gallic acid, fluoroglucincarboxylic acid, 2,4,5-trihydroxybenzoic acid, m-galloylgallic acid, tannic acid, m-benzoylgallic acid, m-(p-toluyl)gallic acid, protocatechuoylgallic acid, 4,6-dihydroxyphthalic acid, (2,4-dihydroxyphenyl)aceticacid, (2,6-dihydroxyphenyl)aceticacid, (3,4,5-trihydroxyphenyl)acetic acid, p-hydroxymethylbenzoic acid, p-hydroxyethylbenzoic acid, 4-(p-hydroxyphenyl)methylbenzoic acid, 4-(o-hydroxybenzoyl)benzoic acid, 4-(2,4-dihydroxybenzoyl)benzoic acid, 4-(p-hydroxyphenoxy)benzoic acid, 4-(p-hydroxyanilino)benzoic acid, bis(3-carboxy-4-hydroxyphenyl)amine, 4-(p-hydroxyphenylsulfonyl)benzoicacid, 4-(p-hydroxyphenylthio)benzoicacid, p-methoxybenzoic acid, 2,4-dimethoxybenzoic acid, 2,4-dimethylbenzoic acid, p-phenoxybenzoic acid, phenoxyacetic acid, p-methoxyphenylacetic acid, 4-anilinobenzoic acid, 4-(m-methoxyanilino)benzoic acid, 4-(p-methoxybenzoyl)benzoic acid, 4-(p-methylanilino)benzoic acid and 4-phenylsulfonylbenzoic acid.
- 11. The process of claim 10 wherein the aromatic compound having at least one carboxyl group is at least one member selected from the group consisting of 2,4-dimethoxybenzoic acid, p-phenoxybenzoic acid, 4-anilinobenzoic acid, 4-(m-methoxyanilino) benzoic acid, 4-(p-methylanilino)benzoic acid, salicylic acid, p-hydroxybenzoic acid, 2,4-dihydroxybenzoic acid, gallic acid, fluoroglucincarboxylic acid, phenoxyacetic acid and 4-(p-hydroxyanilino)benzoic acid.
- 12. The process plate of claim 1 wherein the aromatic diazonium compound is selected from the group consisting of compounds represented by the general formula: ##STR10## wherein R.sup.1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group; R.sup.2 and R.sup.3 each represents a hydrogen atom, X.sup.- represents an anion derived from an inorganic or organic acid having a pKa of not more than 4 and Y represents --NH--.
- 13. The process of claim 1 wherein the aromatic diazonium compound represented by the general formula (I) is selected from the group consisting of salts of 4-diazodiphenylamine, 4'-hydroxy-4-diazodiphenylamine, 4'-methyl-4-diazodiphenylamine, 4'-ethyl-4-diazodiphenylamine, 4'-n-propyl-4-diazodiphenylamine, 4'-i-propyl-4-diazodiphenylamine, 4'-n-butyl-4-diazodiphenylamine, 4'-hydroxymethyl-4-diazodiphenylamine, 4'-.beta.-hydroxyethyl-4-diazodiphenylamine, 4'-.gamma.-hydroxypropyl-4-diazodiphenylamine, 4'-methoxymethyl-4-diazodiphenylamine, 4'-ethoxymethyl-4-diazodiphenylamine, 4'-.beta.-methoxyethyl-4-diazodiphenylamine, 4'-.beta.-ethoxyethyl-4-diazodiphenylamine, 4'-carboxy-4-diazodiphenylamine, 3-methoxy-4-diazodiphenylamine, 3-methylamino-4-diazodiphenylamine, 3-methyl-4-diazodiphenylamine, 3-ethyl-4-diazodiphenylamine, 3'-methyl-4-diazodiphenylamine, 3,3'-dimethyl-4-diazodiphenylamine, 2'-carboxy-4-diazodiphenylamine, 4-diazodiphenyl ether, 4'-methyl-4-diazodiphenyl ether, 3,4'-dimethyl-4-diazodiphenyl ether, 4'-carboxy-4-diazodiphenyl ether, 3,3'-dimethyl-4-diazodiphenyl ether, 4-diazodiphenyl sulfide and 4'-methyl-4-diazodiphenyl sulfide.
- 14. The process of claim 13 wherein the aromatic diazonium compound represented by the general formula (I) is selected from the group consisting of salts of 4-diazodiphenylamine and 3-methoxy-4-diazodiphenylamine.
- 15. The process of claim 1 wherein the copolycondensed diazo resin is a resin obtained by copolycondensing an aromatic diazonium compound, an aromatic compound carrying at least one carboxyl group and an aldehhyde or a ketone in sulfuric acid, phosphoric acid or hydrochloric acid.
- 16. The process of claim 15 wherein in the copolycondensation, the molar ratio of the aromatic compound carrying at least one carboxyl group to the aromatic diazonium compound ranges from 1:0.1 to 0.1:1 and the molar ratio of the sum of the aromatic compound carrying at least one carboxyl group and the aromatic diazonium compound to the aldehyde or ketone ranges from 1:0.6 to 1.2.
- 17. The process of claim 16 wherein in the copolycondensation, the molar ratio of the aromatic compound carrying at least one carboxyl group to the aromatic diazonium compound ranges from 1:0.2 to 0.2:1 and the molar ratio of the sum of the aromatic compound carrying at least one carboxyl group and the aromatic diazonium compound to the aldehyde or ketone ranges from 1:0.7 to 1.5.
- 18. The process of claim 1 wherein the anion of the copolycondensed diazo resin is selected from the group consisting of anions derived from hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, orthophosphoric acid, phosphotungstic acid, phosphomolybdic acid, aliphatic or aromatic phosphonic acids or half-ester thereof, arsonic acid, phosphinic acid, fluorocarboxylic acids, amidosulfonic acid, selenic acid, borofluoric acid, hexafluorophosphoric acid, perchloric acid, methanesulfonic acid, fluoroalkanesulfonic acid, laurylsulfonic acid, dioctylsulfosuccinic acid, dicyclohexylsulfosuccinic acid, camphorsulfonic acid, tolyloxy-3-propanesulfonic acid, nonylphenoxy-3-propanesulfonicacid, nonylphenoxy-4-butanesulfonicac id, dibutylphenoxy- 3-propanesulfonic acid, diamylphenoxy-3-propanesulfonic acid, dinonylphenoxy-3-propanesulfonicacid, dibutylphenoxy-4-butanesulfonicacid, dinonylphenoxy-4-butanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, mesitylenesulfonic acid, p-chlorobenzenesulfonic acid, 2,5-dichlorobenzenesulfonic acid, sulfosalicylic acid, 2,5-dimethylbenzenesulfonic acid, p-acetylbenzenesulfonic acid, 5-nitro-o-toluenesulfonic acid, 2-nitrobenzenesulfonic acid, 3-chlorobenzenesulfonic acid, 3-bromobenzenesulfonic acid, 2-chloro-5-nitrobenzenesulfonic acid, butylbenzenesulfonic acid, octylbenzenesulfonic acid, dodecylbenzenesulfonic acid, butoxybenzenesulfonic acid, dodecyloxybenzenesulfonic acid, 2-methoxy-4-hydroxy-5-benzoylbenzenesulfonic acid, isopropylnaphthalenesulfonic acid, butylnaphthalenesulfonic acid, hexylnaphthalenesulfonic acid, octylnaphthalenesulfonic acid, butoxynaphthalenesulfonic acid, dodecyloxynaphthalenesulfonic acid, dibutylnaphthalenesulfonic acid, dioctylnaphthalenesulfonic acid, triisopropylnaphthalenesulfonic acid, tributylnaphthalenesulfonic acid, 1-naphthol-5-sulfonic acid, naphthalene-1-sulfonic acid, naphthalene-2-sulfonic acid, 1,8-dinitronaphthalene-3,6-disulfonic acid, 4,4'-diazidostilbene-3,3'-disulfonic acid, 1,2-naphthoquinone-2-diazido-4-sulfonic acid, 1,2-n-aphthoquinone-2-diazido-5-sulfonic acid and 1,2-naphthoquinone-1-diazido-4-sulfonic acid.
- 19. The process of claim 1 wherein the copolycondensed diazo resin is a member selected from the group consisting of salicylic acid/4-diazodiphenylamine .multidot. 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid salt/formaldehyde resin, p-methoxybenzoic acid/4-diazodiphenylamine .multidot. hexafluorophosphate/formaldehyde resin, phenoxyacetic acid/3-methoxy-4-diazodiphenylamine .multidot. dodecylbenzene sulfonic acid/formaldehyde resin, phenoxyacetic acid/4-diazodiphenylamine .multidot. dibutyl naphthalene sulfonic acid/formaldehyde resin, 2,4-dimethoxybenzoic acid/4-diazodiphenylamine .multidot. 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid salt/formaldehyde resin, 4-anilinobenzoic acid/4-diazodiphenylamine .multidot. methanesulfonic acid salt/formaldehyde resin, p-phenoxybenzoic acid/4-diazo-4'-methyldiphenylamine .multidot. hexafluorophosphate/formaldehyde resin, 2,4-dihydroxybenzoic acid/4-diazodiphenylamine .multidot. dibutylnaphthalenesulfonic acid salt/formaldehyde resin, 4-carboxydiphenylamine/4-diazodiphenylamine .multidot. methanesulfonic acid salt/formaldehyde resin and 4-carboxy-4'-methoxydiphenylamine/4-diazodiphenylamine .multidot. 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid salt/formaldehyde resin.
- 20. The process of claim 1 wherein the photocrosslinkable polymer is selected from polymers carrying, on the side chains, maleimido groups represented by the following general formula (A): ##STR11## and the acid value of 50 to 250.
- 21. The process of claim 20 wherein the photocrosslinkable polymer is a copolymer of N-[6-(methacryloyloxy)hexyl]-2, 3-dimethylmaleimide with methacrylic acid.
- 22. The process of claim 1 wherein the aqueous alkaline solution contains a surfactant.
- 23. The process of claim 1 wherein the aqueous alkaline solution contains a reducing agent.
- 24. The process of claim 23 wherein the reducing agent is selected from the group consisting of sulfites, methylresorcin and pyrazolone compounds.
Priority Claims (1)
Number |
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Kind |
2-37786 |
Feb 1990 |
JPX |
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Parent Case Info
This application is a divisional of application Ser. No. 08/177,790, filed Jan. 5, 1994, which is a continuation of application Ser. No. 07/654,510, filed on Feb. 13,1991 now both abandoned.
US Referenced Citations (7)
Foreign Referenced Citations (3)
Number |
Date |
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3633456 |
Apr 1987 |
DEX |
1102457 |
Apr 1989 |
JPX |
1254949 |
Oct 1989 |
JPX |
Non-Patent Literature Citations (2)
Entry |
Patent Abstracts of Japan, vol. 13, No. 342, Aug. 2, 1989, p. 908. |
Patent Abstracts of Japan, vol. 13, No. 1, Jan. 8, 1990, p. 985. |
Divisions (1)
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Number |
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Parent |
177790 |
Jan 1994 |
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Continuations (1)
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Number |
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654510 |
Feb 1991 |
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