JPH03260651A - Photosensitive composition - Google Patents
Photosensitive compositionInfo
- Publication number
- JPH03260651A JPH03260651A JP2060268A JP6026890A JPH03260651A JP H03260651 A JPH03260651 A JP H03260651A JP 2060268 A JP2060268 A JP 2060268A JP 6026890 A JP6026890 A JP 6026890A JP H03260651 A JPH03260651 A JP H03260651A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- polymer compound
- photosensitive composition
- photosensitive
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 229920000642 polymer Polymers 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229920005989 resin Polymers 0.000 abstract description 14
- 239000011347 resin Substances 0.000 abstract description 14
- 150000002989 phenols Chemical class 0.000 abstract description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 6
- 150000001728 carbonyl compounds Chemical class 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000007639 printing Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- -1 0-cresol Chemical compound 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000006068 polycondensation reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229940079877 pyrogallol Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- JTHNLKXLWOXOQK-UHFFFAOYSA-N hex-1-en-3-one Chemical compound CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007788 roughening Methods 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NIUHGYUFFPSEOW-UHFFFAOYSA-N (4-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC=C(OC(=O)C=C)C=C1 NIUHGYUFFPSEOW-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- NFTVTXIQFYRSHF-UHFFFAOYSA-N 1-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)C(C)OC(=O)C=C NFTVTXIQFYRSHF-UHFFFAOYSA-N 0.000 description 1
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- DKHZGIKPBFMBBY-UHFFFAOYSA-N 2-cyano-n-[4-(diethylamino)phenyl]-2-phenylacetamide Chemical compound C1=CC(N(CC)CC)=CC=C1NC(=O)C(C#N)C1=CC=CC=C1 DKHZGIKPBFMBBY-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- CWBAMDVCIHSKNW-UHFFFAOYSA-N 2-iminonaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(=N)CC(=O)C2=C1 CWBAMDVCIHSKNW-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- LLWJPGAKXJBKKA-UHFFFAOYSA-N victoria blue B Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)=C(C=C1)C2=CC=CC=C2C1=[NH+]C1=CC=CC=C1 LLWJPGAKXJBKKA-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、感光性組成物に関する。本発明の感光性組成
物は、例えば、平版印刷版の感光層を構成するために利
用することができる。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a photosensitive composition. The photosensitive composition of the present invention can be used, for example, to constitute a photosensitive layer of a lithographic printing plate.
〔発明の背景］
従来より種々の感光性組成物が提案され、これにより例
えば様々な感光性平版印刷版（以下適宜ＰＳ版と称する
こともある）が構成されている。[Background of the Invention] Various photosensitive compositions have heretofore been proposed, and are used to constitute, for example, various photosensitive lithographic printing plates (hereinafter sometimes referred to as PS plates).
感光性印刷版は一般に、アルミニウム板等の支持体上に
感光性組成物を塗布して製造される。感光性印刷板は、
例えばネガ型の場合、通常、これに陰画等を通して紫外
線等の活性光線を照射し、光が照射された部分を重合あ
るいは架橋等させてこの部分を現像液に不溶な状態とし
、その後現像して光の非照射部分を現像液に溶出させ、
それぞれの部分を、水を反発して油性インキを受容する
画像部、及び水を受容して油性インキを反発する非画像
部とする形で一般に用いられる。Photosensitive printing plates are generally manufactured by coating a photosensitive composition on a support such as an aluminum plate. The photosensitive printing plate is
For example, in the case of a negative type, it is usually irradiated with active light such as ultraviolet rays through a negative image, etc., and the irradiated areas are polymerized or crosslinked to make these areas insoluble in the developer, and then developed. The non-irradiated area is eluted into the developer,
Generally, each portion is used as an image area that repels water and receives oil-based ink, and a non-image area that receives water and repels oil-based ink.
この場合における感光性組成物としては、特にネガ型Ｐ
Ｓ版では、従来より一般に、感光体としてジアゾニウム
樹脂を用いる場合と、エチレン性不飽和結合を有する化
合物と光重合開始剤とを混合して用いる場合とに分類で
きる。後者の感光性組成物は光重合組成物と呼ばれ、−
船釣には、エチレン性不飽和結合を有するモノマー（ま
たはオリゴマー）、光重合開始剤、及び高分子結合剤（
以後単にバインダーと呼ぶ）から成る。光重合組成物の
バインダーとして一般的な高分子化合物としては、ポリ
アクリル系、ポリビニルホルマール系、ポリビニルブチ
ラール系、ポリウレタン系、ポリエステル系等のポリマ
ーを挙げることができる。In this case, the photosensitive composition is particularly negative-type P
Conventionally, S plates can be generally classified into cases where a diazonium resin is used as a photoreceptor, and cases where a mixture of a compound having an ethylenically unsaturated bond and a photopolymerization initiator is used. The latter photosensitive compositions are called photopolymerizable compositions, and -
For boat fishing, monomers (or oligomers) with ethylenically unsaturated bonds, photopolymerization initiators, and polymer binders (
(hereinafter referred to simply as a binder). Examples of polymer compounds commonly used as binders for photopolymerizable compositions include polyacrylic, polyvinyl formal, polyvinyl butyral, polyurethane, and polyester polymers.
〔発明が解決しようとする問題点］
しかしながら上記のポリマーは、ノボラック等の縮合型
樹脂に比べ、高価である。ところで、光重合組成物のバ
インダーとしてノボラック等の安価な縮合型樹脂を用い
た例はほとんど報告が無く、実際には画像形成が不充分
であったり、感度が低い、機械的強度が低い、耐薬品性
が低い等の問題点があった。即ち従来技術にあっては、
安価な縮合型樹脂を用いようとしても、性能上問題があ
って、これは実現できなかったのである。[Problems to be Solved by the Invention] However, the above polymers are more expensive than condensation type resins such as novolak. By the way, there are almost no reports on the use of inexpensive condensation resins such as novolak as binders in photopolymerizable compositions, and in reality, they may result in insufficient image formation, low sensitivity, low mechanical strength, or poor durability. There were problems such as low chemical properties. That is, in the conventional technology,
Even if an attempt was made to use an inexpensive condensation type resin, this could not be realized due to performance problems.
本発明は上記事情に鑑みてなされたもので、その目的は
、ノボラック等の安価な縮合型樹脂をバインダーに用い
るもので、かつ、感度、耐薬品性、耐摩耗性に優れ、か
つ、特にネガ型ＰＳ版に好適に利用できる感光性組成物
を提供することにある。The present invention has been made in view of the above circumstances, and its purpose is to use an inexpensive condensation resin such as novolac as a binder, and to have excellent sensitivity, chemical resistance, and abrasion resistance, and in particular to provide a negative An object of the present invention is to provide a photosensitive composition that can be suitably used for type PS plates.
〔問題点を解決するための手段及び作用〕上記本発明の
目的は、分子内に、後掲の一般式（Ｉ）で表される構造
を繰り返し単位として有する高分子化合物を含有するこ
とを特徴とする感光性組成物（以下適宜「本発明の感光
性組成物」とも称する）によって、達成される。本発明
は一般に、バインダーとして用いる高分子化合物の分子
中に、重合可能なエチレン性不飽和結合を含有せしめる
形で用いることができるものである。[Means and effects for solving the problems] The object of the present invention is to contain a polymer compound having a structure represented by the general formula (I) shown below as a repeating unit in the molecule. This is achieved by a photosensitive composition (hereinafter also referred to as "the photosensitive composition of the present invention" as appropriate). Generally, the present invention can be used in a form in which a polymerizable ethylenically unsaturated bond is contained in the molecule of a polymer compound used as a binder.
本発明の感光性組成物は、一般に好ましい態様として、
上記高分子化合物と、光重合性モノマーと光重合開始剤
とを有する構成で具体化される。Generally preferred embodiments of the photosensitive composition of the present invention include:
It is embodied in a configuration including the above-mentioned polymer compound, a photopolymerizable monomer, and a photopolymerization initiator.
以下、更に本発明を詳説する。The present invention will be further explained in detail below.
（本発明に係る高分子化合物）
まず、本発明の感光性組成物が含有する、一般式（Ｉ）
で表される分子内に重合可能なエチレン性不飽和結合を
有する高分子化合物（以下適宜「本発明に係る高分子化
合物ｊとも称する）について説明する。(Polymer compound according to the present invention) First, the general formula (I) contained in the photosensitive composition of the present invention
A polymer compound having a polymerizable ethylenically unsaturated bond in the molecule represented by (hereinafter also referred to as "polymer compound j according to the present invention") will be described.
本発明に係る高分子化合物は、下記一般式（Ｉ）で表さ
れる構造を分子内に繰り返し単位として含有する。The polymer compound according to the present invention contains a structure represented by the following general formula (I) as a repeating unit in the molecule.
一般式（Ｉ）
但し一般式（Ｉ）中、Ｒ１はエチレン性不飽和結合を有
する置換基を表し、Ｒ２，Ｒ３は水素原子、炭素数１〜
４のアルキル基、炭素数１〜４のアルケニル基、または
フェニル基を表す。ｎはＯ〜２、ｍは１〜３であり、ｎ
＋ｍ＝１〜３である。Ｒ４は水素原子、またはアルキル
基を表す。General formula (I) However, in general formula (I), R1 represents a substituent having an ethylenically unsaturated bond, R2 and R3 are hydrogen atoms, and have 1 to 1 carbon atoms.
4 alkyl group, an alkenyl group having 1 to 4 carbon atoms, or a phenyl group. n is O~2, m is 1~3, n
+m=1 to 3. R4 represents a hydrogen atom or an alkyl group.
上記Ｒ１としては、アクリル、メタクリル、ビニル、置
換ビニル、アリル（ａｌｌｙｌ）、置換アリル、クロチ
ル、バラスチリル等の各基が好ましい（該ビニル、アリ
ルへの置換基としてはアルキル基が好ましい）。As R1, groups such as acrylic, methacryl, vinyl, substituted vinyl, allyl, substituted allyl, crotyl, and valastyryl are preferable (alkyl groups are preferable as substituents for vinyl and allyl).
上記Ｒ２，Ｒ３としては、水素原子、またはメチル、エ
チル、プロピル、プロペニル、フェニルから選ばれたも
のが好ましく、Ｒｚ、 Ｒ３の組み合わせは任意である
。The above R2 and R3 are preferably hydrogen atoms or those selected from methyl, ethyl, propyl, propenyl, and phenyl, and the combination of Rz and R3 is arbitrary.
この高分子化合物は、バインダーとして機能できるもの
であり、かつ分子内に重合可能なエチレン性不飽和結合
を含有するため、露光により分子間の架橋を生し得、ま
た、感光性組成物中に光重合性千ツマ−を含有する場合
、バインダーとモノマー間の架橋により、複雑な３次元
網目構造をとり得るため、感度、耐薬品性、耐摩耗性が
向上するものである。This polymer compound can function as a binder and contains a polymerizable ethylenically unsaturated bond in its molecule, so it can cause intermolecular crosslinking when exposed to light, and can be used in photosensitive compositions. When a photopolymerizable polymer is contained, a complex three-dimensional network structure can be formed due to crosslinking between the binder and the monomer, resulting in improved sensitivity, chemical resistance, and abrasion resistance.
本発明に係る高分子化合物の合成にあたっては、下記一
般式（ｎ）で表されるフェノール誘導体と、下記一般式
（ＩＩＩ）で表されるカルボニル化合物々の重縮合によ
って得られる樹脂のフェノール性ＯＨに、重合可能なエ
チレン性不飽和結合を含有する置換基を導入する方法が
好ましい。In the synthesis of the polymer compound according to the present invention, the phenolic OH of a resin obtained by polycondensation of a phenol derivative represented by the following general formula (n) and carbonyl compounds represented by the following general formula (III) is A method of introducing a substituent containing a polymerizable ethylenically unsaturated bond is preferred.
一般式（ｎ）
４
但しＲ４は水素またはアルキル基。２は１〜３゜一般式
（Ｉ［［）
但しＲ２，Ｒ３は一般式（Ｉ）におけると同義。General formula (n) 4 where R4 is hydrogen or an alkyl group. 2 is 1-3° general formula (I[[) where R2 and R3 have the same meaning as in general formula (I).
一般式（ＩＩ）で表される化合物として好ましいものは
、例えば、フェノール、０−クレゾール、ｍ−クレゾー
ル、ｐ−クレゾール、３．５−キシレノール、カルバク
ロール、チモール、Ｐ−アルキル基（炭素原子数１〜８
個）置換フェノール等の１価フェノール、また、カテコ
ール、レゾルシン、ヒドロキノン等の２価フェノール、
また、ピロガロール、フロログルシン等の３価フェノー
ル等を挙げることができる。これらのうち好ましいのは
、２価、３価の多価フェノールで、更に好ましいのはピ
ロガロールである。Preferred compounds represented by general formula (II) include phenol, 0-cresol, m-cresol, p-cresol, 3.5-xylenol, carvacrol, thymol, P-alkyl group (number of carbon atoms 1-8
monohydric phenols such as substituted phenols, dihydric phenols such as catechol, resorcinol, and hydroquinone,
Further, trihydric phenols such as pyrogallol and phloroglucin can be mentioned. Among these, preferred are divalent and trivalent polyhydric phenols, and more preferred is pyrogallol.
また、一般式（Ｉ［［）で表される化合物として好まし
いのは、ホルムアルデヒド、ベンズアルデヒド、アセト
アルデヒド、クロトンアルデヒド等のアルデヒド、また
は、アセトン、メチルエチルケトン等のケトンである。Also, preferred as the compound represented by the general formula (I[[) are aldehydes such as formaldehyde, benzaldehyde, acetaldehyde, and crotonaldehyde, or ketones such as acetone and methyl ethyl ketone.
上記一般式（ＩＩ） （Ｉ［Ｉ）で示される化合物か
ら重縮合樹脂を得るには、酸性触媒を用いる重合による
合成法によることができる。この際に用いることができ
る酸性触媒としては、塩酸、しゅう酸、硫酸、リン酸、
オキシ塩化リン等の無機酸や、あるいは有機酸を挙げる
ことができる。フェノール類とアルデヒドまたはケトン
との配合比は、フェノール類１モル部に対しアルデヒド
またはケトンが０．７〜１．０モル部が好ましい。但し
、反応溶媒としてアルデヒドまたはケトンが用いられる
場合は、上記配合比に限定されない。反応溶媒としては
、例えば、メタノール、エタノール等のアルコール類、
アセトン、水、テトラヒドロフラン等を用いることがで
きる。In order to obtain a polycondensation resin from the compound represented by the above general formula (II) (I[I), a synthesis method by polymerization using an acidic catalyst can be used. Acidic catalysts that can be used at this time include hydrochloric acid, oxalic acid, sulfuric acid, phosphoric acid,
Examples include inorganic acids such as phosphorus oxychloride, and organic acids. The blending ratio of phenols and aldehydes or ketones is preferably 0.7 to 1.0 parts by mole per 1 part by mole of phenols. However, when aldehyde or ketone is used as the reaction solvent, the mixing ratio is not limited to the above. Examples of reaction solvents include alcohols such as methanol and ethanol;
Acetone, water, tetrahydrofuran, etc. can be used.
反応生成物は、所定温度（例えば−５〜１２０°Ｃ）、
所定時間（例えば３〜４８時間）反応後、減圧上加熱し
、水洗して脱水させて得るか、または水結析させて得る
ことができる。The reaction product is heated to a predetermined temperature (e.g. -5 to 120°C),
After reaction for a predetermined period of time (for example, 3 to 48 hours), it can be obtained by heating under reduced pressure, washing with water to dehydrate it, or by precipitating water.
得られた重縮合樹脂にエチレン性不飽和結合を有する置
換機を導入すれば本発明に係る高分子化合物を得ること
ができるが、この手段としては、エチレン性不飽和結合
を有する有機酸、酸無水物、酸塩化物を該重縮合樹脂に
反応させる手段を用いることができる。これにより、本
発明に係る高分子化合物を合成することができる。The polymer compound according to the present invention can be obtained by introducing a substitution machine having an ethylenically unsaturated bond into the obtained polycondensation resin. A method of reacting an anhydride or acid chloride with the polycondensation resin can be used. Thereby, the polymer compound according to the present invention can be synthesized.
この場合のエチレン性不飽和結合を有する有機酸、酸無
水物、酸塩化物の中で好ましいものとしては、アクリル
酸、メタクリル酸、マレイン酸、イタコン酸、無水マレ
イン酸、無水イタコン酸、アクリル酸クロライド、メタ
クリル酸クロライド等を挙げることができる。これらの
中では、アクリル酸クロライド、メタクリル酸クロライ
ドが特に好ましい。In this case, preferred organic acids, acid anhydrides, and acid chlorides having ethylenically unsaturated bonds include acrylic acid, methacrylic acid, maleic acid, itaconic acid, maleic anhydride, itaconic anhydride, and acrylic acid. Examples include chloride, methacrylic acid chloride, and the like. Among these, acrylic acid chloride and methacrylic acid chloride are particularly preferred.
上述のようにして合成し得る本発明に係る高分子化合物
の平均分子量Ｍｗは、１ 、０００から３０，０００の
間が好ましい。また、より好ましくは、３，０００から
２０，０００の間である。The average molecular weight Mw of the polymer compound according to the present invention which can be synthesized as described above is preferably between 1,000 and 30,000. Moreover, it is more preferably between 3,000 and 20,000.
また、本発明に係る高分子化合物の感光性組成物中にお
ける含有量は、２０〜９８重景％が好ましく、より好ま
しくは３０〜９０重量％である。Further, the content of the polymer compound according to the present invention in the photosensitive composition is preferably 20 to 98% by weight, more preferably 30 to 90% by weight.
次に本発明に係る高分子化合物の合成法の一例を示す。Next, an example of a method for synthesizing a polymer compound according to the present invention will be described.
（合成例−１）
ｍ−クレゾール１００ ｇ、 ｐ−クレゾール６６．８
ｇ、フェノール３６．０ｇ、３７％ホルムアルデヒド水
溶液１０５ｇ及びシュウ酸２．０ｇを、オイルバスにセ
ットした３頭コルベン中に投入し、撹拌しながら昇温し
た。９０°Ｃ付近で激しく発泡し一時的に冷却した後再
び昇温し、内温を１０５°Ｃにした。約３時間反応後２
００°Ｃに昇温するとともに１００ｍｍＨｇまで減圧し
、残留上ツマ−を留去した。１０分後反応を止め、反応
物をテフロン・バットへ流し出し、固化させ、高分子化
合物Ａを得た。この高分子化合物Ａの分子量をＧＰＣで
ポリスチレンを標準として測定した。このＧＰＣ（ゲル
パーミェーションクロマトグラフィー法）による数平均
分子量Ｍｎ及び重量平均分子量Ｍｗの算出は、柘植盛男
、宮林達也、田中誠之著“日本化学会誌” ８００頁〜
８０５頁（Ｉ９７２年）に記載の方法により、オリゴマ
ー領域のピークを均す（ピークの山と谷の中心線を結ぶ
）方法にて行った。その結果、Ｍｎは１１００、ＭＷは
６０００であった。この高分子化合物Ａは、エチレン性
不飽和結合を有する基を有していないので、比較の高分
子化合物である。(Synthesis Example-1) m-cresol 100 g, p-cresol 66.8
g, 36.0 g of phenol, 105 g of a 37% aqueous formaldehyde solution, and 2.0 g of oxalic acid were placed in a three-headed Kolben set in an oil bath, and the temperature was raised while stirring. It foamed violently at around 90°C, and after being temporarily cooled, the temperature was raised again to bring the internal temperature to 105°C. After about 3 hours of reaction 2
The temperature was raised to 00°C, and the pressure was reduced to 100 mmHg to distill off the residual zimmer. After 10 minutes, the reaction was stopped, and the reaction product was poured into a Teflon vat and solidified to obtain a polymer compound A. The molecular weight of this polymer compound A was measured by GPC using polystyrene as a standard. Calculation of the number average molecular weight Mn and weight average molecular weight Mw by this GPC (gel permeation chromatography method) is described in Morio Tsuge, Tatsuya Miyabayashi, and Masayuki Tanaka, "Journal of the Chemical Society of Japan," p. 800~
The measurement was carried out according to the method described on page 805 (I972), in which the peaks of the oligomer region were leveled (the center lines of the peaks and valleys were connected). As a result, Mn was 1100 and MW was 6000. This polymer compound A is a comparative polymer compound because it does not have a group having an ethylenically unsaturated bond.
次いでこの高分子化合物Ａをジオキサン１０００ ｇに
溶解し、ピリジン１２３ｇを加え、水冷上強撹拌しなが
ら、メタクリル酸クロライド１６２ｇを徐々に滴下した
。滴下後２時間撹拌した後、塩酸１００−を含む水１０
！に反応混合物をあけて、沈澱したポリマーを濾取、乾
燥して高分子化合物Ｂ（本発明に係る高分子化合物）を
得た。Next, this polymer compound A was dissolved in 1000 g of dioxane, 123 g of pyridine was added, and 162 g of methacrylic acid chloride was gradually added dropwise while cooling with water and stirring vigorously. After stirring for 2 hours after dropping, add 10% of water containing 100% of hydrochloric acid.
! The reaction mixture was opened, and the precipitated polymer was collected by filtration and dried to obtain a polymer compound B (a polymer compound according to the present invention).
また、本発明の感光性組成物は、本発明に係る高分子化
合物の他に、種々の高分子化合物を併用して用いること
ができる。本発明に係る高分子化合物と併用して好まし
く用いることのできる高分子化合物としては、ポリアミ
ド、ポリエーテル、ポリエステル、ポリカーボネート、
ポリスチレン、ポリウレタン、ポリビニルクロリド及び
そのコポリマー、ポリビニルブチラール樹脂、ポリビニ
ルホルマール樹脂、シェラツク、エポキシ樹脂、フェノ
ール樹脂、アクリル樹脂等を挙げることができる。Moreover, the photosensitive composition of the present invention can be used in combination with various polymer compounds in addition to the polymer compound according to the present invention. Examples of polymer compounds that can be preferably used in combination with the polymer compound according to the present invention include polyamide, polyether, polyester, polycarbonate,
Examples include polystyrene, polyurethane, polyvinyl chloride and copolymers thereof, polyvinyl butyral resin, polyvinyl formal resin, shellac, epoxy resin, phenol resin, acrylic resin, and the like.
好ましくは、下記（Ｉ）〜（Ｉ２）に示す七ツマ−の共
重合体であって、アルカリ可溶・膨潤性高分子化合物で
ある共重合体が挙げられる。Preferable examples include copolymers of heptads as shown in (I) to (I2) below, which are alkali-soluble and swellable polymer compounds.
（Ｉ）芳香族水酸基を有するモノマー、例えばＮ（４−
ヒドロキシフェニル）アクリルアミドまたはＮ−（４−
ヒドロキシフェニル）メタクリルアミド、ｏ−、ｍ−、
ｐ−ヒドロキシスチレン、ｏ −、ｍ−＋ ｐ−ヒド
ロキシフェニル−アクリレートまたは一メタクリレート
。(I) A monomer having an aromatic hydroxyl group, such as N(4-
hydroxyphenyl)acrylamide or N-(4-
hydroxyphenyl) methacrylamide, o-, m-,
p-hydroxystyrene, o-, m-+ p-hydroxyphenyl-acrylate or monomethacrylate.
（２）脂肪族水酸基を有する千ツマ−１例えば２ヒドロ
キシエチルアクリレートまたは２，２ヒドロキシエチル
メタクリレート。(2) 100% aliphatic hydroxyl groups such as 2-hydroxyethyl acrylate or 2,2-hydroxyethyl methacrylate.
（３）アクリル酸、メタアクリル酸、無水マレイン酸等
のα、β−不飽和カルボン酸。(3) α,β-unsaturated carboxylic acids such as acrylic acid, methacrylic acid, and maleic anhydride.
（４）アクリル酸メチル、アクリル酸エチル、アクリル
酸プロピル、アクリル酸ブチル、アクリル酸アミル、ア
クリル酸ヘキシル、アクリル酸オクチル、アクリル酸−
２−クロロエチル、２−ヒドロキシエチルアクリレート
、グリシジルアクリレート、Ｎ−ジメチルアミノエチル
アクリレート等の（置換）アルキルアクリレート。(4) Methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, amyl acrylate, hexyl acrylate, octyl acrylate, acrylic acid-
(Substituted) alkyl acrylates such as 2-chloroethyl, 2-hydroxyethyl acrylate, glycidyl acrylate, and N-dimethylaminoethyl acrylate.
（５）メチルメタクリレート、エチルメタクリレート、
プロピルメタクリレート、プチルメタクリレート、アミ
ルメタクリレート、シクロへキシルメタクリレート、２
−ヒドロキシエチルメタクリレート、４−ヒドロキシブ
チルメタクリレート、グリシジルメタクリレート、Ｎ−
ジメチルアミノエチルメタクリレート等の（Ｗｔ換）ア
ルキルメタクリレート。(5) Methyl methacrylate, ethyl methacrylate,
Propyl methacrylate, butyl methacrylate, amyl methacrylate, cyclohexyl methacrylate, 2
-Hydroxyethyl methacrylate, 4-hydroxybutyl methacrylate, glycidyl methacrylate, N-
(Wt-substituted) alkyl methacrylates such as dimethylaminoethyl methacrylate.
（６）アクリルアミド、メタクリルアミド、Ｎ−メチロ
ールアクリルアミド、Ｎ−メチロールメタクリアミド、
Ｎ−エチルアクリルアミド、Ｎ−ヘキシルアクリルアミ
ド、Ｎ−シクロヘキシルアクリルアミド、Ｎ−ヒドロキ
シエチルアクリルアミド、Ｎ−フェニルアクリルアミド
、Ｎ−ニトロフェニルアミド、Ｎ−エチル−Ｎ−フェニ
ルアクリルアミド等のアクリルアミドもしくはメタクリ
ルアミド類。(6) Acrylamide, methacrylamide, N-methylol acrylamide, N-methylol methacrylamide,
Acrylamides or methacrylamides such as N-ethylacrylamide, N-hexylacrylamide, N-cyclohexylacrylamide, N-hydroxyethylacrylamide, N-phenylacrylamide, N-nitrophenylamide, and N-ethyl-N-phenylacrylamide.
（７）エチルビニルエーテル、２−クロロエチルビニル
エーテル、ヒドロキシエチルビニルエーテル、プロピル
ビニルエーテル、ブチルビニルエーテル、オクチルビニ
ルエーテル、フェニルビニルエーテル等のビニルエーテ
ル類。(7) Vinyl ethers such as ethyl vinyl ether, 2-chloroethyl vinyl ether, hydroxyethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, octyl vinyl ether, and phenyl vinyl ether.
（８）ビニルアセテート、ビニルクロロアセテート、ビ
ニルブチレート、安息香酸ビニル等のビニルエステル類
。(8) Vinyl esters such as vinyl acetate, vinyl chloroacetate, vinyl butyrate, and vinyl benzoate.
（９）スチレン、α−メチルスチレン、メチルスチレン
、クロロメチルスチレン等のスチレン類。(9) Styrenes such as styrene, α-methylstyrene, methylstyrene, and chloromethylstyrene.
（Ｉ０）メチルビニルケトン、エチルビニルケトン、プ
ロピルビニルケトン、フェニルビニルケトン等のビニル
ケトン類。(I0) Vinyl ketones such as methyl vinyl ketone, ethyl vinyl ketone, propyl vinyl ketone, and phenyl vinyl ketone.
（Ｉ１）エチレン、プロピレン、イソブチレン、ブタジ
ェン、イソプレン等のオレフィン類。(I1) Olefins such as ethylene, propylene, isobutylene, butadiene, and isoprene.
（Ｉ２） Ｎ−ビニルピロリドン、Ｎ−ビニルカルバゾ
ール、４−ビニルピリジン、アクリロニトリル、メタク
リルアミド等。(I2) N-vinylpyrrolidone, N-vinylcarbazole, 4-vinylpyridine, acrylonitrile, methacrylamide, etc.
更に、上記モノマーと共重合し得る七ツマ−を共重合さ
せてもよい。また、上記モノマーの共重合によって得ら
れる共重合対を、例えば、グリシジルメタクリレート、
グリシジルアクリレート等によって修飾したものも含ま
れるが、これらに限られるものではない。Furthermore, a heptamer that can be copolymerized with the above monomer may be copolymerized. Further, the copolymerization pair obtained by copolymerization of the above monomers may be, for example, glycidyl methacrylate,
It also includes, but is not limited to, those modified with glycidyl acrylate and the like.
（光重合開始剤）
本発明の感光性組成物は、前記したとおりその好ましい
態様として光重合開始剤を含有する。以下本発明に用い
ることができる光重合開始剤について述べる。本発明に
おいて、光重合開始剤としては、公知の種々のものを任
意に用いることができるが、特に好ましいものは、チオ
キサントン系、アントラキノン系、ヘンシフエノン系、
ベンゾイン系、安息香酸エステル系、トルハロメチル系
の重合開始剤である。具体的には、下記のような化合物
を好ましく用いることができる。(Photopolymerization initiator) As described above, the photosensitive composition of the present invention contains a photopolymerization initiator as a preferred embodiment. Photopolymerization initiators that can be used in the present invention will be described below. In the present invention, various known photopolymerization initiators can be used, but particularly preferred are thioxanthone-based, anthraquinone-based, hesiphenone-based,
It is a benzoin-based, benzoic acid ester-based, and tolhalomethyl-based polymerization initiator. Specifically, the following compounds can be preferably used.
また、光重合開始剤として、ジアゾ化合物を用いること
もできる。ジアゾ化合物のうち、好ましく用いられるも
のは、ｐ−ジアゾジフェニルアミン誘導体の有機及び無
機酸塩であり、中でも好ましいのが、ジアゾジフェニル
アミンスルホン酸塩、ジアゾジフェニルアミントリフル
オロリン酸塩である。Moreover, a diazo compound can also be used as a photopolymerization initiator. Among the diazo compounds, those preferably used are organic and inorganic acid salts of p-diazodiphenylamine derivatives, and among them, diazodiphenylamine sulfonate and diazodiphenylamine trifluorophosphate are preferred.
また、これらジアゾ化合物をカルボニル化合物と重縮合
させて得られるジアゾ樹脂も、好ましく用いることがで
きる。中でも好ましいのは、ジアゾジフェニルアミント
リフルオロリン酸塩とホルムアルデヒドとの重縮金物で
ある。またこの重縮合の際、他の芳香族を加え、共縮合
体としたものも好ましい。Furthermore, diazo resins obtained by polycondensing these diazo compounds with carbonyl compounds can also be preferably used. Among them, a polycondensate of diazodiphenylamine trifluorophosphate and formaldehyde is preferred. It is also preferable to add other aromatics during this polycondensation to form a co-condensate.
以下にジアゾ化合物として好ましいジアゾ樹脂の合成の
１例を示す。An example of the synthesis of a diazo resin preferable as a diazo compound is shown below.
ジアゾ１２１の人
ｐ−ジアゾジフェルニルアミン硫酸塩 １４．５ｇを、
水冷下で４０ｇの濃硫酸に溶解した。この反応溶液に１
．０５ｇのバラホルムアルデヒドをゆっくり添加した。Diazo 121 human p-diazodiphenylamine sulfate 14.5g,
It was dissolved in 40 g of concentrated sulfuric acid under water cooling. 1 in this reaction solution
．． 0.5 g of rose formaldehyde was slowly added.
この際、反応温度が１０°Ｃを超えないように添加して
いった。その後、２時間水冷下で撹拌を続けた。この反
応混合液を、水冷下、５００ｍ ｌのエタノールに滴下
し、生じた沈澱を濾別した。At this time, the addition was carried out so that the reaction temperature did not exceed 10°C. Thereafter, stirring was continued for 2 hours under water cooling. This reaction mixture was added dropwise to 500 ml of ethanol under water cooling, and the resulting precipitate was filtered off.
エタノールで沈澱を洗浄した後、この沈澱を１００ｄの
純水に溶解し、この液に、６．８ｇの塩化亜鉛を溶解し
た水溶液を加えた。生じた沈澱をろ別した後、エタノー
ルで洗い、１５０ｃａ ｌの純水に熔解させた。この液
に、８ｇのへキサフルオロリン酸アンモニウムを溶解し
た水溶液を加え、生じた沈澱を濾別し、水、エタノール
で洗った後、２５°Ｃで３日間乾燥して、ジアゾ樹脂１
を得た。After washing the precipitate with ethanol, the precipitate was dissolved in 100 d of pure water, and an aqueous solution containing 6.8 g of zinc chloride was added to this solution. The resulting precipitate was filtered, washed with ethanol, and dissolved in 150 cal of pure water. An aqueous solution in which 8 g of ammonium hexafluorophosphate was dissolved was added to this solution, and the resulting precipitate was filtered, washed with water and ethanol, and dried at 25°C for 3 days.
I got it.
本発明においては、上記した各種光重合開始剤とともに
、重合禁止剤、例えば、ハイドロキノン、ｐ−メトキシ
フェノール、ジ−ｔ−ブチル−ｐクレゾール、ピロガロ
ール、ｔ −７”チルカテコール、ベンゾキノン、４，
４”−チオビス（３−メチル−６−ｔ−ブチルフェノー
ル）、２．２′メチレンビス（４−メチル−６−１−７
’チルフエノール）、２−メルカプトベンゾイミダゾー
ルなどを併用してもよい。In the present invention, in addition to the various photopolymerization initiators described above, polymerization inhibitors such as hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-7'' tilcatechol, benzoquinone, 4,
4''-thiobis(3-methyl-6-t-butylphenol), 2,2'methylenebis(4-methyl-6-1-7
'Tilphenol), 2-mercaptobenzimidazole, etc. may be used in combination.
（光重合性上ツマー等）
次に、本発明の感光性組成物は光重合性モノマー等を含
有することがその一つの好ましい態様であるが、本発明
の感光性組成物中に、含有される好ましい光重合性モノ
マー及び／またはオリゴマーとしては、次のようなもの
がある。(Photopolymerizable monomer, etc.) Next, one preferred embodiment of the photosensitive composition of the present invention is that it contains a photopolymerizable monomer. Preferred photopolymerizable monomers and/or oligomers include the following.
即ち、このような七ツマ−は、オリゴマーとして具体的
には、
ポリエチレングリコールモノ（メタ）アクリレート、ポ
リプロピレングリコールモノ（メタ）アクリレート、フ
ェノキシエチル（メタ）アクリレート等の単官能のアク
リレートやメタクリレート；ポリプロレングリコールジ
（メタ）アクリレート、ポリプロピレンジ（メタ）アク
リレート、トリメチロールエタントリ（メタ）アクリレ
ート、ネオベンチルグリコールジ（メタ）アクリレート
、ペンタエリストリールトリ （メタ）アクリレート、
ペンタエリスリトールテトラ（メタ）アクリレート、ジ
ペンタエリストリールヘキサ（メタ）アクリレート、ヘ
キサンジオールジ（メタ）アクリレート、トリ（アクリ
ロイルオキシエチル）イソシアヌレート、グリセリンや
トリメチロールエタン等の多価アルコールにエチレンオ
キサイドやプロピレンオキサイドを付加させた後（メタ
）アクリレート化したもの、特公昭４８−４１７０８号
、特公昭５０−６０３４号、特開昭５１−３７１９３号
各明細明細記載されているようなウレタンアクリレート
類、特開昭４８−６４１８３号、特公昭４９−４３１９
１号、特公昭５２３０４９０号各公報に記明細れている
ポリエステルアクリレート類、エポキシ樹脂と（メタ）
アクリル酸反応させたエポキシアクリレート類等の多官
能のアクリレートやメタクリレート
を例示できる。更に、詳細には日本接着協会Ｖｏ１．２
０． Ｎａ ７ 、３００〜３０８頁に光硬化性モノマ
ー及びオリゴマーとして紹介されている重合性化合物を
用いることもできる。That is, such 7-mers include monofunctional acrylates and methacrylates such as oligomers such as polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, and phenoxyethyl(meth)acrylate; polyprolene Glycol di(meth)acrylate, polypropylene di(meth)acrylate, trimethylolethane tri(meth)acrylate, neobentyl glycol di(meth)acrylate, pentaerythryl tri(meth)acrylate,
Pentaerythritol tetra(meth)acrylate, dipentaerythryl hexa(meth)acrylate, hexanediol di(meth)acrylate, tri(acryloyloxyethyl)isocyanurate, polyhydric alcohols such as glycerin and trimethylolethane, and ethylene oxide and (Meth)acrylates after adding propylene oxide, urethane acrylates as described in the specifications of JP-B No. 48-41708, JP-B No. 50-6034, and JP-A-51-37193; Kai No. 48-64183, Special Publication No. 49-4319
Polyester acrylates, epoxy resins and (meth) described in Patent Publication No. 1 and Japanese Patent Publication No. 5230490
Examples include polyfunctional acrylates and methacrylates such as epoxy acrylates reacted with acrylic acid. Furthermore, for details, see the Japan Adhesive Association Vo1.2
0. Polymerizable compounds introduced as photocurable monomers and oligomers in Na 7 , pages 300 to 308 can also be used.
（その他の成分）
本発明の感光性組成物には、以上に説明した成分のほか
、必要に応して更に染料、顔料、塗布性向上剤、可塑剤
などを添加することができる。(Other Components) In addition to the components described above, dyes, pigments, coatability improvers, plasticizers, and the like can be further added to the photosensitive composition of the present invention, if necessary.
前記の染料としては、例えばビクトリアピュアブルーＢ
ＯＨ（採土ケ谷化学社製）、オイルブルー４６０３（オ
リエント化学社製）、パテントピュアブルー（住友三国
化学社製）、クリスタルバイオレット、ブリリアントグ
リーン、エチルバイオレット、メチルグリーン、エリス
ロシンＢ、ヘイシックツクシン、マラカイトグリーン、
オイルレッド、ｍ−クレゾールパープル、ローダミンＢ
、オーラミン、４−ｐ−ジエチルアミノフェニルイミノ
ナフトキノン、シアノ−ｐ−ジエチルアミノフェニルア
セトアニリド等に代表されるトリフェニルメタン系、ジ
フェニルメタン系、オキサジン系、キサンチン系、イミ
ノナフトキノン系、アゾメチン系またはアントラキノン
系の色素を挙げることができる。Examples of the dye include Victoria Pure Blue B.
OH (manufactured by Odugaya Chemical Co., Ltd.), Oil Blue 4603 (manufactured by Orient Chemical Co., Ltd.), Patent Pure Blue (manufactured by Sumitomo Mikuni Chemical Co., Ltd.), Crystal Violet, Brilliant Green, Ethyl Violet, Methyl Green, Erythrosin B, Heisik Tsukusin, malachite green,
Oil red, m-cresol purple, Rhodamine B
, auramine, 4-p-diethylaminophenylimino naphthoquinone, cyano-p-diethylaminophenyl acetanilide, and other triphenylmethane, diphenylmethane, oxazine, xanthine, iminonaphthoquinone, azomethine, or anthraquinone pigments. can be mentioned.
染料はこれを添加する場合、感光性組成物中に通常好ま
しくは約０．５〜約１０重量％、より好ましくは約１〜
５重量％含有させる。When the dye is added, it is usually preferably about 0.5 to about 10% by weight, more preferably about 1 to about 10% by weight in the photosensitive composition.
Contain 5% by weight.
塗布性向上剤としては、アルキルエーテル類（例えばエ
チルセルロース、メチルセルロース）、フッ素系界面活
性剤類や、ノニオン系界面活性剤〔例えば、プルロニッ
クＬ−６４（旭電化社製）〕を挙げることができる。塗
膜の柔軟性、耐摩耗性を賦与するための可塑剤としては
、例えばブチルフタリル、ポリエチレングリコール、ク
エン酸トリブチル、フタル酸ジエチル、フタル酸ジブチ
ル、フタル酸ジヘキシル、フタル酸ジオクチル、リン酸
トリクレジル、リン酸トリブチル、リン酸トリオクチル
、オレイン酸テトラヒドロフルフリル、アクリル酸また
はメタクリル酸のオリゴマーを挙げることができる。画
像部の感脂性を向上させるための感脂化剤としては、例
えば、特開昭５５−５２７号公報記載のスチレン−無水
マレイン酸共重合体のアルコールによるハーフエステル
化物等を挙げることができる。安定剤としては、例えば
、ポリアクリル酸、酒石酸、リン酸、亜リン酸、有機酸
（アクリル酸、メタクリル酸、クエン酸、シュウ酸、ベ
ンゼンスルホン酸、ナフタレンスルホン酸、４−メトキ
シ−２−ヒドロキシ−ベンゾフェノン−５−スルホン酸
等）等を挙げることができる。これらの添加剤の添加量
は、その使用対象や目的によって異なるが、一般に全固
形分に対して０．０１〜３０ｗｔ％程度で用いるのが好
ましい。Examples of the coating property improver include alkyl ethers (eg, ethyl cellulose, methyl cellulose), fluorine-based surfactants, and nonionic surfactants (eg, Pluronic L-64 (manufactured by Asahi Denka)). Examples of plasticizers for imparting flexibility and abrasion resistance to coating films include butylphthalyl, polyethylene glycol, tributyl citrate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, dioctyl phthalate, tricresyl phosphate, and phosphorus. Mention may be made of tributyl acid, trioctyl phosphate, tetrahydrofurfuryl oleate, oligomers of acrylic acid or methacrylic acid. As a liposensitizing agent for improving the liposensitivity of the image area, there may be mentioned, for example, a half ester of a styrene-maleic anhydride copolymer with alcohol described in JP-A-55-527. Examples of stabilizers include polyacrylic acid, tartaric acid, phosphoric acid, phosphorous acid, organic acids (acrylic acid, methacrylic acid, citric acid, oxalic acid, benzenesulfonic acid, naphthalenesulfonic acid, 4-methoxy-2-hydroxy -benzophenone-5-sulfonic acid, etc.). The amount of these additives added varies depending on the object and purpose of use, but it is generally preferable to use them in an amount of about 0.01 to 30 wt% based on the total solid content.
（感光性平版印刷版への適用）
本発明の感光性組成物は、これを支持体表面に塗布乾燥
させることにより、感光性平版印刷版を得ることができ
る。(Application to Photosensitive Planographic Printing Plate) A photosensitive planographic printing plate can be obtained by applying the photosensitive composition of the present invention onto the surface of a support and drying it.
塗布溶媒としては、メチルセロソルブ、メチルセロソル
ブアセテート、エチルセロソルブ、エチルセロソルブア
セテート等のセロソルブ類、ジメチルジグリコール、ジ
メチルホルムアミド、ジメチルスルホキシド、ジオキサ
ン、アセトン、シクロヘキサノン、トリクロロエチレン
、メチルエチルケトン、４−ヒドロキシブタノン等を挙
げることができる。これら溶媒は、単独であるいは２種
以上混合して使用する。Examples of coating solvents include cellosolves such as methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve, and ethyl cellosolve acetate, dimethyl diglycol, dimethyl formamide, dimethyl sulfoxide, dioxane, acetone, cyclohexanone, trichloroethylene, methyl ethyl ketone, 4-hydroxybutanone, and the like. be able to. These solvents may be used alone or in combination of two or more.
塗布方法は、従来公知の方法、たとえば、回転塗布、ワ
イヤーバー塗布、デイツプ塗布、エアーナイフ塗布、ロ
ール塗布、ブレード塗布及びカーテン塗布等が使用可能
である。塗布量は固形分として０．２〜１０ｇ／ｒｔｆ
が好ましい。As the coating method, conventionally known methods such as spin coating, wire bar coating, dip coating, air knife coating, roll coating, blade coating, and curtain coating can be used. Application amount is 0.2-10g/rtf as solid content
is preferred.
感光性平版印刷版の支持体にはアルミニウム板を用いる
ことが好ましい。硝酸または硝酸を主成分とする電解溶
液中、もしくは塩酸または塩酸を主成分とする電解溶液
中で電解粗面化することにより砂目立て処理し、好まし
くは、更に陽極酸化処理及び必要に応じて封孔処理等の
表面処理したものを使用するのが望ましい。It is preferable to use an aluminum plate as the support for the photosensitive lithographic printing plate. The surface is grained by electrolytic roughening in nitric acid or an electrolytic solution containing nitric acid as a main component, or in hydrochloric acid or an electrolytic solution containing hydrochloric acid as a main component, preferably further anodized and sealed if necessary. It is desirable to use one that has undergone surface treatment such as hole treatment.
電解粗面化は、好ましくは０．１〜１．０モル／１、よ
り好ましくは０．２〜０．６モル／ｌの硝酸もしくは塩
酸を含有する浴中にアルミニウム板を浸漬し、好ましく
は２０〜５０°Ｃ１より好ましくは２５〜４０°Ｃの温
度で、好ましい電流密度２０〜２００Ａ／ｄボで、１０
秒〜３分程度電解エツチングすることが好ましい。この
砂目立て処理の後、必要に応じてアルカリあるいは酸の
水溶液によってデスマット処理を行って中和し、水洗す
る。Electrolytic surface roughening is carried out by immersing the aluminum plate in a bath containing nitric acid or hydrochloric acid at a concentration of preferably 0.1 to 1.0 mol/l, more preferably 0.2 to 0.6 mol/l. At a temperature of 20 to 50 °C, more preferably 25 to 40 °C, and a preferred current density of 20 to 200 A/d, 10
It is preferable to carry out electrolytic etching for about seconds to three minutes. After this graining treatment, if necessary, desmut treatment is performed with an aqueous alkali or acid solution to neutralize it, and then washed with water.
陽極酸化処理は、電解液として硫酸、クロム酸、シュウ
酸、リン酸、マロン酸等を１種または２種以上含む溶液
を用い、アルミニウム板を陽極にして電解することによ
り行うのが好ましい。形成された陽極酸化皮膜量は、１
〜５０■／ｄボが一般に適当で好ましく、より好ましく
は１０〜４０■／ｄｎ（である。ここで陽極酸化皮膜量
は、例えばアルミニウム液をリン酸クロム酸溶液（８５
％リン酸水溶液３５ｍＺと、酸化クロム（ＩＶ）２０ｇ
とを１１の水に溶解して生成）に浸漬して酸化皮膜を溶
解し、板の皮膜溶解前後の重量変化を測定することによ
り求めることができる。The anodizing treatment is preferably carried out by electrolyzing using an aluminum plate as an anode using a solution containing one or more of sulfuric acid, chromic acid, oxalic acid, phosphoric acid, malonic acid, etc. as an electrolytic solution. The amount of anodic oxide film formed was 1
~50 μ/dn is generally suitable and preferred, and more preferably 10 ~ 40 μ/dn.
% phosphoric acid aqueous solution 35mZ and chromium (IV) oxide 20g
It can be determined by immersing the plate in 11 (produced by dissolving it in water) to dissolve the oxide film and measuring the change in weight of the plate before and after the film is dissolved.
封孔処理としては、沸騰水処理、水蒸気処理、ケイ酸ソ
ーダ処理、重クロム酸塩水溶液処理等がある。この他に
アルミニウム支持体に対して、水溶性高分子化合物や、
フン化ジルコン酸等の金属塩の水溶液により下引処理を
施すこともできる。Pore sealing treatments include boiling water treatment, steam treatment, sodium silicate treatment, dichromate aqueous solution treatment, and the like. In addition, water-soluble polymer compounds,
Subbing treatment can also be performed using an aqueous solution of a metal salt such as fluorinated zirconate.
このようにして得られた感光性平版印刷版は公知の方法
により使用することがきできる。典型的には、感光性印
刷版にネガ型フィルムを密着させ、超高圧水銀灯、メタ
ルハライドランプ等で露光し、公知の様々な現像液を用
いて現像し、印刷版とする。このようにして作製された
平版印刷版は枚葉、オフ輪用印刷機おいて使用すること
ができる。The photosensitive lithographic printing plate thus obtained can be used by a known method. Typically, a negative film is brought into close contact with a photosensitive printing plate, exposed to light using an ultra-high pressure mercury lamp, metal halide lamp, etc., and developed using various known developers to obtain a printing plate. The lithographic printing plate produced in this manner can be used in sheet-fed and off-wheel printing presses.
即ち、線画像、網点画像等を有する透明原画を通して感
光し、次いで、水性現像液で現像することにより原画に
対してネガのレリーフ像が得られる。露光に好適な光源
としては、カーボンアーク灯、水銀灯、キセノンランプ
、メタルハライドランプ、ストロボ等が挙げられる。That is, a negative relief image is obtained with respect to the original image by exposing the transparent original image having line images, halftone images, etc. to light, and then developing with an aqueous developer. Light sources suitable for exposure include carbon arc lamps, mercury lamps, xenon lamps, metal halide lamps, strobes, and the like.
感光性平版印刷版の現像処理に用いられる現像液は公知
のいずれであってもよいが、例えばベンジルアルコール
やエチレングリコールモノフェニルエーテルに代表され
る有機溶媒、アルカリ金属のケイ酸塩や有機アミンの化
合物のようなアルカリ剤、及び水を主成分として含有す
るものや、あるいは、有機溶媒を含まず、上記アルカリ
剤、高級アルコール硫酸エステル塩類やアルキルアＩＪ
−ルスルホン酸塩類に代表されるアニオン型界面活性剤
、及び有機カルボン酸を主成分として含有するものを用
いることが好ましい。The developer used in the development of the photosensitive lithographic printing plate may be any known developer, but for example, organic solvents such as benzyl alcohol and ethylene glycol monophenyl ether, alkali metal silicates, and organic amines may be used. Alkaline agents such as compounds, and those containing water as a main component, or those that do not contain organic solvents, the above-mentioned alkaline agents, higher alcohol sulfate ester salts, and alkylar IJ
- It is preferable to use an anionic surfactant typified by sulfonic acid salts and one containing an organic carboxylic acid as a main component.
感光性平版印刷版は、像様露光した後、上述の現像液に
接触させたり、あるいはこすったりすれば、約１０°Ｃ
〜４０°Ｃにて１０〜６０秒後には、感光層の露光部に
悪影響を及ぼすことなく、非露光部の感光性組成物が完
全に除去されるので、このように［実施例］
以下本発明を実施例により更に具体的に説明するが、当
然のことながら本発明はこれら実施例に限定されない。After imagewise exposure, the photosensitive lithographic printing plate can be heated to about 10°C by contacting it with the above-mentioned developer or by rubbing it.
After 10 to 60 seconds at ~40°C, the photosensitive composition in the non-exposed areas of the photosensitive layer is completely removed without adversely affecting the exposed areas. The invention will be explained in more detail with reference to Examples, but it goes without saying that the invention is not limited to these Examples.
実施例１，２．３及び比較例１
アルミニウム板を１０ｗｔ％水酸化ナトリウム水溶液に
て脱脂し、これを１．８％塩酸浴中で２５°Ｃ１３０Ａ
／ｄｒｒ？、３０秒の電流密度条件で電解エツチングし
、水洗後、３０％硫酸浴中で３０°Ｃ１６，５Ａ／ｄボ
の条件で３０秒間陽極酸化処理した。次に１ｗｔ％メタ
ケイ酸ナトリウム水溶液により、８５°Ｃ１３０秒間封
孔処理し、水洗乾燥して、平版印刷版用支持体としての
アルミニウム板を得た。Examples 1, 2.3 and Comparative Example 1 An aluminum plate was degreased with a 10 wt% aqueous sodium hydroxide solution, and heated at 25°C at 130A in a 1.8% hydrochloric acid bath.
/drr? , electrolytically etched at a current density of 30 seconds, washed with water, and anodized in a 30% sulfuric acid bath at 30° C. and 5 A/d for 30 seconds. Next, the pores were sealed with a 1 wt % aqueous sodium metasilicate solution at 85° C. for 130 seconds, washed with water and dried to obtain an aluminum plate as a support for a lithographic printing plate.
このアルミニウム板に表−１のような組成の感光性組成
物液を、乾燥後の膜重量が１．７ ｇ ／ｒｄとなるよ
うに塗布して、感光性平服印刷版試料を得た。A photosensitive composition liquid having the composition shown in Table 1 was applied to this aluminum plate so that the film weight after drying was 1.7 g/rd to obtain a photosensitive plain printing plate sample.
表
上記のようにして得られた各側の試料に、ネガ透明原画
及びステップウェッジ（Ｉ度差０．１５にて増加）を置
いて、２に−のメタルハライドランプで６０ｃｍの距離
から３０秒露光した後、ｒＳＤＮ−２１現像液」 （コ
ニカ社製、１：３に希釈）に、２５°Ｃ１４０秒間浸漬
し、その後、脱脂綿で軽くこすって現像した。A negative transparent original and a step wedge (increased by an I degree difference of 0.15) were placed on the sample on each side obtained as above, and exposed for 30 seconds from a distance of 60 cm using a metal halide lamp of -2. After that, it was immersed in rSDN-21 developer (manufactured by Konica, diluted 1:3) at 25°C for 140 seconds, and then developed by rubbing lightly with absorbent cotton.
現像後のステップウェッジのベタ段数は、第２表の通り
であった。The number of solid steps of the step wedge after development was as shown in Table 2.
更に、各試料をウルトラプレートクリーナーに１時間浸
漬した後、水洗してスポンジで軽くこすった後の版面上
の画像部の侵され方を調べたところ、第２表に併示の結
果を得た。同表中、○は浸漬前と変化がほとんどない、
×は画像部の所々が欠けていることを示す。Furthermore, after immersing each sample in Ultra Plate Cleaner for 1 hour, washing with water and rubbing lightly with a sponge, we examined the corrosion of the image area on the plate, and obtained the results shown in Table 2. . In the same table, ○ means there is almost no change from before immersion.
× indicates that some parts of the image area are missing.
また、画像部の被膜強度は、ハイデルベルグＧＴＯ印刷
機で印刷を行い、版の画像部にキズが見られた時点の耐
刷枚数により、評価した。結果は表−２に併示する。Further, the film strength of the image area was evaluated by printing with a Heidelberg GTO printing machine and the number of sheets printed at the time when scratches were observed in the image area of the plate. The results are also shown in Table-2.
表−２から、本発明の実施例については、比較例に比べ
て、感度、耐薬品性、耐摩耗性（耐剛力）が向上してい
るのが判る。From Table 2, it can be seen that the examples of the present invention have improved sensitivity, chemical resistance, and abrasion resistance (stiffness resistance) compared to the comparative examples.
上述の如く、本発明により、感度・被膜強度・耐薬品性
に優れた感光性組成物を得ることができた。As described above, according to the present invention, a photosensitive composition excellent in sensitivity, film strength, and chemical resistance could be obtained.
Claims (1)
り返し単位として有する高分子化合物を含有することを
特徴とする感光性組成物。 一般式（ I ） ▲数式、化学式、表等があります▼ 但し一般式（ I ）中、Ｒ＾１はエチレン性不飽和結合
を有する置換基を表し、Ｒ＾２、Ｒ＾３は水素原子、炭
素数１〜４のアルキル基、炭素数１〜４のアルケニル基
、またはフェニル基を表す。Ｒ＾４は水素原子、または
アルキル基を表す。ｎは０〜２、ｍは１〜３であり、ｎ
＋ｍ＝１〜３である。[Claims] 1. A photosensitive composition containing a polymer compound having a structure represented by the following general formula (I) as a repeating unit in its molecule. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ However, in the general formula (I), R^1 represents a substituent having an ethylenically unsaturated bond, R^2 and R^3 are hydrogen atoms, It represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 1 to 4 carbon atoms, or a phenyl group. R^4 represents a hydrogen atom or an alkyl group. n is 0 to 2, m is 1 to 3, and n
+m=1 to 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2060268A JPH03260651A (en) | 1990-03-12 | 1990-03-12 | Photosensitive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2060268A JPH03260651A (en) | 1990-03-12 | 1990-03-12 | Photosensitive composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03260651A true JPH03260651A (en) | 1991-11-20 |
Family
ID=13137227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2060268A Pending JPH03260651A (en) | 1990-03-12 | 1990-03-12 | Photosensitive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03260651A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5672463A (en) * | 1993-02-16 | 1997-09-30 | Sumitomo Chemical Company, Limited | Polyfunctional vinyl ether compound and photoresist resin composition containing the same |
| US5719008A (en) * | 1994-09-12 | 1998-02-17 | Sumitomo Chemical Company, Limited | Photoresist composition comprising a polyfunctional vinyl ether compound |
-
1990
- 1990-03-12 JP JP2060268A patent/JPH03260651A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5672463A (en) * | 1993-02-16 | 1997-09-30 | Sumitomo Chemical Company, Limited | Polyfunctional vinyl ether compound and photoresist resin composition containing the same |
| US5719008A (en) * | 1994-09-12 | 1998-02-17 | Sumitomo Chemical Company, Limited | Photoresist composition comprising a polyfunctional vinyl ether compound |
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