JPS59202458A - Photosensitive composition - Google Patents
Photosensitive compositionInfo
- Publication number
- JPS59202458A JPS59202458A JP7628283A JP7628283A JPS59202458A JP S59202458 A JPS59202458 A JP S59202458A JP 7628283 A JP7628283 A JP 7628283A JP 7628283 A JP7628283 A JP 7628283A JP S59202458 A JPS59202458 A JP S59202458A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- weight
- acid
- photosensitive composition
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- -1 thiophosphate compound Chemical class 0.000 abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 abstract description 11
- 239000001301 oxygen Substances 0.000 abstract description 11
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 229920002379 silicone rubber Polymers 0.000 description 12
- 239000004945 silicone rubber Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- XUVKSPPGPPFPQN-UHFFFAOYSA-N 10-Methyl-9(10H)-acridone Chemical compound C1=CC=C2N(C)C3=CC=CC=C3C(=O)C2=C1 XUVKSPPGPPFPQN-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-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
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- MCKOUAWHQOYKFB-UHFFFAOYSA-N octyl 3-bis[(3-octoxy-3-oxopropyl)sulfanyl]phosphanylsulfanylpropanoate Chemical compound C(=O)(OCCCCCCCC)CCSP(SCCC(=O)OCCCCCCCC)SCCC(=O)OCCCCCCCC MCKOUAWHQOYKFB-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- KLAPGAOQRZTCBI-UHFFFAOYSA-N tris(butylsulfanyl)phosphane Chemical compound CCCCSP(SCCCC)SCCCC KLAPGAOQRZTCBI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- MRERMGPPCLQIPD-NBVRZTHBSA-N (3beta,5alpha,9alpha,22E,24R)-3,5,9-Trihydroxy-23-methylergosta-7,22-dien-6-one Chemical compound C1C(O)CCC2(C)C(CCC3(C(C(C)/C=C(\C)C(C)C(C)C)CCC33)C)(O)C3=CC(=O)C21O MRERMGPPCLQIPD-NBVRZTHBSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- QFDDZIRGHKFRMR-UHFFFAOYSA-N 10-butylacridin-9-one Chemical compound C1=CC=C2N(CCCC)C3=CC=CC=C3C(=O)C2=C1 QFDDZIRGHKFRMR-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- YPKYLZFGWKOVDZ-UHFFFAOYSA-N 6-methylheptane-1,6-diamine Chemical compound CC(C)(N)CCCCCN YPKYLZFGWKOVDZ-UHFFFAOYSA-N 0.000 description 1
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 101100063942 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) dot-1 gene Proteins 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 229920006097 Ultramide® Polymers 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 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 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical group OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- WLYRNHJWOMZNIY-UHFFFAOYSA-N butyl 2-bis[(2-butoxy-2-oxoethyl)sulfanyl]phosphanylsulfanylacetate Chemical compound CCCCOC(=O)CSP(SCC(=O)OCCCC)SCC(=O)OCCCC WLYRNHJWOMZNIY-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- QVRVXSZKCXFBTE-UHFFFAOYSA-N n-[4-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)butyl]-2-(2-fluoroethoxy)-5-methylbenzamide Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1CCCCNC(=O)C1=CC(C)=CC=C1OCCF QVRVXSZKCXFBTE-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920002631 room-temperature vulcanizate silicone Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229960000368 sulisobenzone Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-UHFFFAOYSA-N 0.000 description 1
- ZFVSFOABZDBFRD-UHFFFAOYSA-N tris(octylsulfanyl)phosphane Chemical compound CCCCCCCCSP(SCCCCCCCC)SCCCCCCCC ZFVSFOABZDBFRD-UHFFFAOYSA-N 0.000 description 1
- 125000005289 uranyl group Chemical group 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
Abstract
Description
【発明の詳細な説明】
く技術分野〉
本発明はラジカル重合性のエチレン性不飽和結合を有す
る化合物を光重合成分とする感光性組成物に関し,特に
印刷版等の分野で利用されるものである。[Detailed Description of the Invention] Technical Field The present invention relates to a photosensitive composition containing a compound having a radically polymerizable ethylenically unsaturated bond as a photopolymerizable component, and is particularly used in the fields of printing plates and the like. be.
〈従来技術〉
ラジカル重合性のエチレン性不飽和結合を有する化合物
を光重合成分とする感光性組成物は印刷版(凸版あるい
は平版)、塗料,インキ、フォトレジストなどに広く用
いられているが,ラジカル重合性のエチレン性不飽和結
合を有する化合物の重合が酸素によって阻害されるため
に,酸素存在下での硬化性が良くないという問題点があ
る。<Prior art> Photosensitive compositions containing radically polymerizable ethylenically unsaturated bonds as a photopolymerizable component are widely used in printing plates (letterpress or lithography), paints, inks, photoresists, etc. Since polymerization of radically polymerizable compounds having ethylenically unsaturated bonds is inhibited by oxygen, there is a problem in that curing properties are poor in the presence of oxygen.
この点を改良するために,ラジカル重合性のエチレン性
不飽和結合を有する化合物に工夫がなされ,分子中にア
ミノ基,ウレタン基などを導入することなどが提案され
ているが,特公昭48−41 708、49−1 38
70など十分なものではない。In order to improve this point, improvements have been made to compounds with radically polymerizable ethylenically unsaturated bonds, and it has been proposed to introduce amino groups, urethane groups, etc. into the molecule. 41 708, 49-1 38
70 is not enough.
〈発明の目的〉
本発明者らは、かかる酸素存在下での硬化性を改良スル
ために鋭意検討した結果9ラジ力ル重合性のエチレン性
不飽和結合を有する化合物を光重合成分とする感光性組
成物にチオホスファイト化合物を含有せしめることによ
り、チオホスファイト化合物が光で活性化された状態に
おいて急速に酸素と反応して、系中の酸素を消費し、そ
の結果ラジカル重合性のエチレン性不飽和結合を有する
化合物の重合が阻害されなくなる。即ち組成物の酸素存
在下での硬化性が著しく高められるという事実を見出し
9本発明に到達した。<Object of the Invention> As a result of intensive studies to improve the curability in the presence of oxygen, the present inventors have developed a photosensitive material using a compound having a 9-radically polymerizable ethylenically unsaturated bond as a photopolymerization component. By containing a thiophosphite compound in a chemical composition, the thiophosphite compound rapidly reacts with oxygen when activated by light and consumes oxygen in the system, resulting in radically polymerizable ethylene. Polymerization of compounds having sexually unsaturated bonds is no longer inhibited. That is, the inventors have discovered the fact that the curability of the composition in the presence of oxygen is significantly enhanced, and have thus arrived at the present invention.
〈発明の構成〉
本発明の構成はラジカル重合性エチレン性不飽和化合物
と9下記一般式で示されるチオホスファイト化合物00
1〜20重量%とを含有することを特徴とする感光性組
成物である。<Configuration of the Invention> The configuration of the present invention includes a radically polymerizable ethylenically unsaturated compound and a thiophosphite compound represented by the following general formula.
It is a photosensitive composition characterized by containing 1 to 20% by weight.
(R,、R,、R,ばC6〜C3゜のアルキル基、アリ
ール基、アラルキル基であり、これらに置換基とシテハ
ロケン、01〜C20のアルコキシ基、アルコキシカル
ボニル基、アシルオキシ基、アルカノイル基、シアノ基
、水酸基、アミン基を有していてもよい。XはOまたは
−CR4R,−を示し、R,、R慰水素、C5〜C2゜
のアルキル基、アリール基、アラルキル基を示す。m、
nは0〜3の整数、pはO〜2の整数を示し、m+n+
p=3である)0本発明に使用できる分子中に1ヶ以上
のラジカル性、エチレン性不飽和結合を有する化合物と
しては次のようなものがある。(R,, R,, R, is a C6 to C3 alkyl group, aryl group, aralkyl group, and these have substituents and halogen, 01 to C20 alkoxy group, alkoxycarbonyl group, acyloxy group, alkanoyl group, It may have a cyano group, a hydroxyl group, or an amine group. ,
n is an integer of 0 to 3, p is an integer of O to 2, m+n+
p=3)0 Compounds having one or more radical or ethylenically unsaturated bonds in the molecule that can be used in the present invention include the following.
(1) 次に示すアルコール類のアクリル酸又はメタ
クリル酸エステル。(1) Acrylic acid or methacrylic acid ester of the following alcohols.
メタノール、エタノール、プロパツール、ヘキサノール
、オクタツール、シクロヘキサノール。Methanol, ethanol, propatool, hexanol, octatool, cyclohexanol.
エチレングリコール、テトラエチレングリコール。Ethylene glycol, tetraethylene glycol.
ポリエチレングリコール、プロピレングリコール。Polyethylene glycol, propylene glycol.
ジプロピレングリコール、グリセリン、トリメチロール
プロパン、ペンタエリスリトール、ビスフェノールAの
エチレンオキシド付力日物など。Dipropylene glycol, glycerin, trimethylolpropane, pentaerythritol, bisphenol A with ethylene oxide, etc.
(2) 次に示すアミン類、カルボン酸類とアクリル
酸グリシジルエステルまたはメタクリル酸グリシジルエ
ステルとの反応生成物。(2) A reaction product of the following amines or carboxylic acids and glycidyl acrylate or glycidyl methacrylate.
メチルアミン、エチルアミン、ブチルアミン。Methylamine, ethylamine, butylamine.
ベンジルアミン、エチレンジアミン、ジエチレントリア
ミン、ヘキサメチレンジアミン、p−キシリレンジアミ
ン、m−キシリレンジアミン、エタノールアミン、ジメ
チルアミン、ジエチルアミン。Benzylamine, ethylenediamine, diethylenetriamine, hexamethylenediamine, p-xylylenediamine, m-xylylenediamine, ethanolamine, dimethylamine, diethylamine.
ジェタノールアミン、アニリンなど。jetanolamine, aniline, etc.
酢酸、プロピオン酸、安息香酸、アクリル酸。Acetic acid, propionic acid, benzoic acid, acrylic acid.
メタクリル酸、コハク酸、マレ1゛ン酸、フタル酸。Methacrylic acid, succinic acid, maleic acid, phthalic acid.
酒石酸など。such as tartaric acid.
(3) 次に示すようなアミド誘導体。(3) Amide derivatives as shown below.
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 、 N’−メチレンビスアクリル
アミド、ジアセトンアクリルアミドなど。Acrylamide, methacrylamide, N-methylolacrylamide, N,N'-methylenebisacrylamide, diacetone acrylamide, etc.
(4) エポキシ化合物とアクリル酸又はメタクリル
酸との反応物。(4) A reaction product of an epoxy compound and acrylic acid or methacrylic acid.
(5) イノシアネート含有化合物と水酸基含有アク
リル酸エステルあるいはメタクリル酸エステルとの反応
生成物。(5) A reaction product between an inocyanate-containing compound and a hydroxyl group-containing acrylic ester or methacrylic ester.
(6) アクリル酸あるいはメタクリル酸のアンモニウ
ム塩または金属塩。(6) Ammonium salt or metal salt of acrylic acid or methacrylic acid.
本発明においては上記のような分子中に1ヶ以上のラジ
カル性エチレン性不飽和結合を有する化合物を使用する
が、この他に次のような水ないしは通常の有機溶媒に可
溶なポリマを共存させることができる。水ないしは通常
の有機溶媒に可溶なポリマとしては次のようなものがあ
る。In the present invention, a compound having one or more radical ethylenically unsaturated bonds in the molecule as described above is used, but in addition to this, the following polymers soluble in water or ordinary organic solvents may also be used. can be done. Polymers soluble in water or ordinary organic solvents include the following.
(1) アクリル酸、メタクリル酸、アクリル酸エス
テル、メタクリル酸エステル、アクリロニトリルのポリ
マおよびそれらのコポリマ。たとえばポリアクリル酸エ
チル、ポリメタクリル酸メチル。(1) Polymers of acrylic acid, methacrylic acid, acrylic esters, methacrylic esters, acrylonitrile, and copolymers thereof. For example, polyethyl acrylate, polymethyl methacrylate.
ポリアクリル酸ブチルなと。Butyl polyacrylate.
(2) 未加硫ゴム。たとえばポリブタジェン、ポリ
イソブチレンぼスチレン−ブタジェンゴムなど。(2) Unvulcanized rubber. For example, polybutadiene, polyisobutylene and styrene-butadiene rubber.
(3) ポリビニルアルコール誘導体。たとえばポリ
ビニルアルコール、ポリ酢酸ビニル、ポリビニルブチラ
ール、ポリ酢酸ビニルの部分ケン化物など。(3) Polyvinyl alcohol derivative. For example, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, partially saponified polyvinyl acetate, etc.
(4) ポリエーテル。たとえばポリエチレンオキシ
ド、ポリプロピレンオキシドなど。(4) Polyether. For example, polyethylene oxide, polypropylene oxide, etc.
(5) ポリエステル。たとえばフタル酸、イソフタ
ル酸、マレイン酸、アジピン酸などとエチレングリコー
ル、1,4−ブタンジオール、1,6−ヘキサンジオー
ル、ネオペンチルグリコールなどの反応生成物。(5) Polyester. For example, reaction products of phthalic acid, isophthalic acid, maleic acid, adipic acid, etc. with ethylene glycol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, etc.
(6) ポリウレタン。たとえばトルエンジイソシア
坏−ト、ヘキサメチレンシイソシアイ・−トウインホロ
ンジイソシア坏−ト、ジフェニルメタンシインシアイ・
−トなどと1.4−ブタンジオール、1゜6−ヘキサン
ジオール、(4)のポリエーテルポリオール、(5)で
得られるポリエステルポリオールなどとの反応生成物。(6) Polyurethane. For example, toluene diisocyanate, hexamethylene diisocyanate, toinphorone diisocyanate, diphenylmethane diisocyanate,
A reaction product of 1,4-butanediol, 1°6-hexanediol, the polyether polyol of (4), the polyester polyol obtained in (5), etc.
(7) エポキシ樹脂。(7) Epoxy resin.
(8) ポリアミド。たとえばアジピン酸、セパチン
酸、アゼライン酸とへキサメチレンジアミン。(8) Polyamide. For example adipic acid, sepatic acid, azelaic acid and hexamethylene diamine.
l・ジメチルへキサメチレンジアミン、4,4/−ジア
ミノシクロヘキシルメタンなどとの反応生成物。Reaction products with l.dimethylhexamethylene diamine, 4,4/-diaminocyclohexylmethane, etc.
ε−カプロラクタム、ω−アミノウンデカン酸などの重
合物。Polymers such as ε-caprolactam and ω-aminoundecanoic acid.
(9) セルo −スm 導体。fc トエItf、
セルロースアセテート、セルロースアセテートブチレー
トなど。(9) Cell o-sm conductor. fc toe itf,
Cellulose acetate, cellulose acetate butyrate, etc.
更に本発明においては上記可溶性ポリマに既知の方法で
ラジカル重合性のエチレン性不飽和結合を導入したもの
ヲ、「分子中に1ケ以」二のラジカル重合性エチレン性
不飽和結合を有する化合物」として用いることもできる
。このような化合物としては次のようなものがある。Furthermore, in the present invention, a compound in which a radically polymerizable ethylenically unsaturated bond is introduced into the above-mentioned soluble polymer by a known method is a compound having "one or more" two radically polymerizable ethylenically unsaturated bonds in the molecule. It can also be used as Examples of such compounds include the following.
(1)(メタ)アクリル酸グリシジルエステルのポリマ
あるいは他の(メタ)アクリル酸エステルとのコポリマ
と(メタ)アクリル酸との反応生成物。(1) A reaction product of a polymer of (meth)acrylic acid glycidyl ester or a copolymer with another (meth)acrylic acid ester and (meth)acrylic acid.
+21 水酸基含有(メタ)アクリル酸エステルのポ
リマあるいは他の(メタ)アクリル酸エステルとのコポ
リマとイソシアイ・−ト基含有(メタ)アクリル酸エス
テルとの反応生成物。+21 A reaction product of a polymer of a (meth)acrylic ester containing a hydroxyl group or a copolymer with another (meth)acrylic ester and a (meth)acrylic ester containing an isocyanate group.
(3) エポキシ化ポリブタジェンと(メタ)アクリ
ル酸との反応生成物。(3) A reaction product between epoxidized polybutadiene and (meth)acrylic acid.
(4) 分子内にイソシアイ・−ト基を有するポリウ
レタンと水酸基含有(メタ)アクリル酸エステルの反応
生成物。(4) A reaction product of a polyurethane having an isocyanate group in its molecule and a hydroxyl group-containing (meth)acrylic ester.
(5) 分子内に水酸基を有するポリウレタンとイソ
シアイ・−ト基含有(メタ)アクリル酸エステルとの反
応生成物。(5) A reaction product of a polyurethane having a hydroxyl group in its molecule and a (meth)acrylic acid ester having an isocyanate group.
(G) エポキシ樹脂と(メタ)アクリル酸との反応
生成物。(G) A reaction product between an epoxy resin and (meth)acrylic acid.
(7)N−オキシあるいはN−アルコキシポリアミドと
(メタ)アクリル酸との反応生成物。(7) Reaction product of N-oxy or N-alkoxy polyamide and (meth)acrylic acid.
(8) ポリアミドと(メタ)アクリル酸グリシジル
エステルとの反応生成物。(8) A reaction product of polyamide and (meth)acrylic acid glycidyl ester.
これらのポリマは1分子中に2ヶ以上のラジカル重合性
のエチレン性不飽和結合を含むものが好ましい。These polymers preferably contain two or more radically polymerizable ethylenically unsaturated bonds in one molecule.
本発明の感光性樹脂組成物は上記必須成分の他に光重合
開始剤、光増感剤、熱重合禁止剤などの安定化剤9相溶
性向上剤、染料、顔料、充填剤などを含有していてもよ
い。光重合開始剤、光増感剤を添加することにより高感
度な感光性樹脂組成物が得られる。かかる光重合開始剤
、光増感剤としては9次のようなものを使用することが
できる。In addition to the above-mentioned essential components, the photosensitive resin composition of the present invention contains stabilizers such as photopolymerization initiators, photosensitizers, and thermal polymerization inhibitors, compatibility improvers, dyes, pigments, fillers, etc. You can leave it there. By adding a photopolymerization initiator and a photosensitizer, a highly sensitive photosensitive resin composition can be obtained. As such photopolymerization initiators and photosensitizers, the following can be used.
ベンゾインメチルエーテル、ペンゾインイソフ。Benzoin methyl ether, penzoin isof.
ロビルエーテル、α、a−ジメトキシ−α−フェニルア
セトフェノンなどのベンゾイン誘導体、ベンゾフェノン
、2.4−ジクロルベンゾフェノン。Lobil ether, benzoin derivatives such as α,a-dimethoxy-α-phenylacetophenone, benzophenone, 2,4-dichlorobenzophenone.
O−ベンゾイル安息香酸メチル、4,4/−ビス(ジメ
チルアミノ)ベンゾフェノン、4.4/−ビス(ジエチ
ルアミン)ベンゾフェノンなどのベンゾフェノン誘導体
、2−クロルチオキサントン、2−インプロピルチオキ
サントンなどのチオキサントン誘導体、2−クロルアン
トラキノン、2−メチルアントラキノンなどのアントラ
キノン誘導体、N−メチルアクリドン、N−ブチルアク
1]トンなどのアクリドン誘導体、a、α−ジェトキシ
アセトフェノン、ベンジル、フルオレノン、キサントン
。Benzophenone derivatives such as methyl O-benzoylbenzoate, 4,4/-bis(dimethylamino)benzophenone, 4.4/-bis(diethylamine)benzophenone, thioxanthone derivatives such as 2-chlorothioxanthone, 2-inpropylthioxanthone, 2 - Anthraquinone derivatives such as chloranthraquinone and 2-methylanthraquinone, acridone derivatives such as N-methylacridone and N-butylacridone, a,α-jethoxyacetophenone, benzyl, fluorenone, and xanthone.
ウラニル化合物、ノ・ロゲン化合物など。Uranyl compounds, norogen compounds, etc.
本発明で酸素の存在下での硬化性を改良する目的で添加
するチオホスファイト化合物・ハ1次の一般式(I)の
構造を有するものである。In the present invention, the thiophosphite compound added for the purpose of improving curability in the presence of oxygen has the structure of the first-order general formula (I).
(R,、R,、R,はC1〜C20のアルキル基、アリ
ール基、アラルキル基であり、これらに置換基としてハ
ロゲン、C3〜C2゜のアルコキシ基、アルコキシカル
ボニル基、アシルオキシ基、アルカノイル基、シアノ基
、水酸基、アミノ基を有していてもよい。−X−は−0
−、−CR,R,−を示し、’ R,+ Rsは水素、
01〜Ctoのアルキル基、アリール基、アラルキル基
を示す。H,nは0〜3の整数、pr。(R,, R,, R, is a C1-C20 alkyl group, aryl group, aralkyl group, and substituents for these include halogen, C3-C2° alkoxy group, alkoxycarbonyl group, acyloxy group, alkanoyl group, May have a cyano group, hydroxyl group, or amino group. -X- is -0
-, -CR,R,-, 'R, + Rs is hydrogen,
The alkyl group, aryl group, and aralkyl group of 01 to Cto are shown. H, n is an integer of 0 to 3, pr.
〜2の整数を示し、m+n+p=3である)。2, where m+n+p=3).
これらの化合物の例としては次のようなものがあげられ
る。トリブチルトリチオホスファイト。Examples of these compounds include the following: Tributyltrithiophosphite.
トリオクチルトリチオホスファイト、トリラウリルトリ
チオホスファイト、トリブチルトリチオホスファイト、
トリ(o−1リル)トリチオホスファイト、トリベンジ
ルトリチオホスファイト。Trioctyl trithiophosphite, trilauryl trithiophosphite, tributyl trithiophosphite,
Tri(o-1lyl)trithiophosphite, tribenzyltrithiophosphite.
トリ(2−メトキシエチル)トリチオホスファイト、ト
リ(エトキシカルボニルメチル)トリチオホスファイト
、トリ(ブトキシカルボニルメチル)トリチオホスファ
イト、トリ(オクチルオキシカルボニルメチル)トリチ
オホスファイト、トリ(ろ−メトキシブチルオキシカル
ボニルメチル)トリチオホスファイト、トリ(β−エト
キシカルボニルエニル)トリチオホスファイト、トリ(
β−ブトキシカルボニルエチル)トリチオホスファイト
、トリ(β−オクチルオキシカルボニルエチル)トリチ
オホスファイト、トリ(β−6−メドキシブチルオキシ
カルポニルエチル)トリチオホスファイト、トリ(β−
アセトキシエチル)トリチオホスファイト、トリ(β−
シアンエチル)トリチオホスファイト、ジラウリルジチ
オブチルホスファイト、エチル亜チオホスホン酸ジブチ
ル、ジプチル亜チオホスフィン酸ラウリルなど。Tri(2-methoxyethyl)trithiophosphite, tri(ethoxycarbonylmethyl)trithiophosphite, tri(butoxycarbonylmethyl)trithiophosphite, tri(octyloxycarbonylmethyl)trithiophosphite, tri(ro-methoxybutyloxycarbonyl) methyl)trithiophosphite, tri(β-ethoxycarbonylenyl)trithiophosphite, tri(
β-butoxycarbonylethyl)trithiophosphite, tri(β-octyloxycarbonylethyl)trithiophosphite, tri(β-6-medoxybutyloxycarbonylethyl)trithiophosphite, tri(β-
acetoxyethyl)trithiophosphite, tri(β-
cyanethyl) trithiophosphite, dilauryl dithiobutyl phosphite, dibutyl ethyl thiophosphonite, lauryl diptyl thiophosphinate, etc.
これらのチオホスファイト化合物の添加量は。What is the amount of these thiophosphite compounds added?
感光性組成物に対して001〜20重量係、好ましくは
05〜10重量係である。0.01重量係未満では酸素
存在下での硬化性改良効果が小さく。The amount is 0.001 to 20% by weight, preferably 0.05 to 10% by weight, based on the photosensitive composition. If the weight ratio is less than 0.01, the effect of improving curability in the presence of oxygen is small.
また20重量係を越えると形態保時が困難となる。Moreover, if the weight exceeds 20, it becomes difficult to maintain the shape.
本発明が改良の対象としている感光性組成物は。The photosensitive composition that is the subject of improvement in the present invention.
印刷版(凸版あるいは平版)、塗料、インキ、フォトレ
ジストなどの材料として用いられるが、特に薄膜性の被
膜に好ましく用いられる。更にこの感光性組成物の被膜
の上層または下層にシリコーンゴム層を0.5〜50μ
の膜厚で設けることによシ湿し水不要平版用感光性版材
を得ることができる0
湿し水不要平版感光性版材で用いられるシリコーンゴム
は、適当な分子量を有する線状ジオルガノポリシロキサ
ン(好ましくはジメチルポリシロキサン)を、まばらに
架橋することによυ得られる。代表的なシリコーンゴム
は9次のようなくり返し単位を有する。It is used as a material for printing plates (letterpress or lithography), paints, inks, photoresists, etc., and is particularly preferably used for thin films. Furthermore, a silicone rubber layer of 0.5 to 50 μm is applied as an upper or lower layer of the film of this photosensitive composition.
A photosensitive plate material for lithographic printing that does not require dampening water can be obtained by providing the film with a film thickness of It is obtained by sparsely crosslinking a polysiloxane (preferably dimethylpolysiloxane). A typical silicone rubber has nine repeating units.
ここでnは2以上の整数である。Here, n is an integer of 2 or more.
R,R’は水素、炭素数1〜10のアルキル基。R and R' are hydrogen and an alkyl group having 1 to 10 carbon atoms.
アリール基、ビニル基である。このようなシリコーンゴ
ムは、有機過酸化物の添加によりまばらに架橋させるこ
とができるが、網台型の架橋を行なうシリコーンゴム(
RTV、LTV型シリコーンゴム)を用いることにより
、さらに好ましいシリコーンゴム膜が得られる。かかる
網台型のシリコーンゴムは1通常次のような末端基同志
の縮合によって架橋する。これにさらに過剰の架橋剤を
存在させる場合もある。They are an aryl group and a vinyl group. Such silicone rubbers can be sparsely crosslinked by adding organic peroxides, but silicone rubbers that undergo net crosslinking (
A more preferable silicone rubber film can be obtained by using a silicone rubber (RTV, LTV type silicone rubber). Such mesh type silicone rubber is usually crosslinked by the following condensation of end groups. In some cases, an excess of crosslinking agent may be present.
(R′2C=N−O+Si−〇−
Rは水素、炭素数1〜10のアルキル基、アリール基、
ビニル基を示し R/は炭素数1〜10のアルキル基で
ある。ACはアセチル基を示す。(R'2C=N-O+Si-〇-R is hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl group,
It represents a vinyl group, and R/ is an alkyl group having 1 to 10 carbon atoms. AC represents an acetyl group.
以下実施例をあげて本発明の詳細な説明する。The present invention will be described in detail below with reference to Examples.
実施例1.比較例1
次の組成を有するチオホスファイト化合物を含有する感
光性樹脂組成物とチオホスファイト化合物を含まない感
光性樹脂組成物を、ブリキ板上にアプリケーターを用い
10ミクロンの厚さで塗布した。Example 1. Comparative Example 1 A photosensitive resin composition containing a thiophosphite compound and a photosensitive resin composition not containing a thiophosphite compound having the following compositions were applied onto a tin plate using an applicator to a thickness of 10 microns. .
(a)「パンデツクスT−5201J(大日本インキ化
学工業■製ポリウレタン樹脂 52重量部(b) ト
リメチロールプロパントリアクリレート45重量部
(c) 2−クロルチオキサントン 6重量部(
d) チオホスファイト化合物 6重量部この
被膜に、空気下で、3kW高圧水銀燈の光i1mの距離
から照射し、被膜の粘着性がなくなった秒数をもって硬
化性の尺度とした。(a) 52 parts by weight of Pandex T-5201J (polyurethane resin manufactured by Dainippon Ink and Chemicals) (b) 45 parts by weight of trimethylolpropane triacrylate (c) 6 parts by weight of 2-chlorothioxanthone (
d) Thiophosphite compound 6 parts by weight This film was irradiated with light from a 3 kW high-pressure mercury lamp from a distance of 1 m in air, and the number of seconds until the film lost its tackiness was taken as a measure of curability.
結果を第1表に示す。The results are shown in Table 1.
第 1 表
第1表から明らかなように、チオホスファイト化合物を
添加していない組成物1と比較して、チオホスファイト
化合物を添加した組成物2〜7は。Table 1 As is clear from Table 1, compositions 2 to 7 to which a thiophosphite compound was added were compared to composition 1 to which no thiophosphite compound was added.
空気下での硬化性が良好である。Good curability under air.
実施例2.比較例2
次の組成を有する感光性樹脂組成物のシートラアルミ板
上に0.5noの厚みで積層し、感光性樹脂板を得た。Example 2. Comparative Example 2 A photosensitive resin composition having the following composition was laminated on a sheet la aluminum plate to a thickness of 0.5 mm to obtain a photosensitive resin plate.
(a)[ウルトラミツドICJ(BASF社製アルコー
ル可溶性ナイロン 60重量部(b) N、N
、N’、N’−テトラキス−2−ヒドロキシ−6−メタ
クロイルオキシプロビル−
キシリレンジアミン(メタクリル酸グIJシジルエステ
ルとm−キシリレンジアミントノ4/1モル比反応物
28重量部(C) メタクリル酸−2−
ヒドロキシエチル10重量部
(d)ベンゾフェノン 2重量部(e)
)す(オクチルオキシカルボニルメチルトリチオホ
スファイト 2重量部この感光性樹脂板に
Stouffer 社製21段グレースケールを置き5
00w超高圧水銀燈に上り。(a) [Ultramid ICJ (BASF alcohol-soluble nylon 60 parts by weight) (b) N, N
, N',N'-tetrakis-2-hydroxy-6-methacroyloxypropyl-xylylenediamine (4/1 molar ratio reaction product of methacrylic acid glycidyl ester and m-xylylenediamine amine)
28 parts by weight (C) methacrylic acid-2-
Hydroxyethyl 10 parts by weight (d) Benzophenone 2 parts by weight (e)
) (2 parts by weight of octyloxycarbonylmethyltrithiophosphite) A 21-level gray scale manufactured by Stouffer was placed on this photosensitive resin plate.
Climb to 00w super high pressure mercury lamp.
4’Ocmの距離から1分間露光した。これをメタノー
ル/トリクレン( 80/20 )で2分間噴射するこ
とにより未露光部を洗浄.除去したところグレースケー
ルの部分はN119まで硬化していた。Exposure was performed for 1 minute from a distance of 4'Ocm. Clean the unexposed areas by spraying this with methanol/triclene (80/20) for 2 minutes. When removed, the gray scale part was hardened to N119.
これと同様の方法で,チオホスファイト化合物を含まな
い感光性樹脂板を作製し,露光,洗浄を行なったところ
,系中に存在する酸素による重合阻害をうけて,グレー
スケールのN1111までしか硬化していなかった。When a photosensitive resin plate containing no thiophosphite compound was prepared using a similar method, exposed to light, and washed, the polymerization was inhibited by the oxygen present in the system, and it was only cured up to N1111 on the gray scale. I hadn't.
実施例3,比較例6
アルミ板に,次の組成を有する厚さ6ミクロンの感光性
樹脂被膜をもうけた。Example 3, Comparative Example 6 A 6 micron thick photosensitive resin film having the following composition was formed on an aluminum plate.
(a) アクリル酸エチルとメタクリル酸メチルとの
コポリマ(モル比7:3,平均分子量5万)50重量部
(1)) N, N, N’,N’−テトラキス−2
−ヒドロキシ−3−メタクロイルオキシ−m−キンリレ
ンジアミン 60重量部(c)ト
リエチレングリコールジメタクリレート14重量部
(a) 4,4’−ビス(ジエチルアミノ)ベンゾフ
ェノン 4重量部(e)
フルオレノン 2重量部(f)トリ
(β−オクチルオキシカルボニルエチル)トリチオホス
ファイト 5重量部この感光性樹脂被膜の上に「
yg、−3085J(東芝シリコーン■製RTVンリコ
ーンガムデイスパーション)をn−へブタンで希釈して
塗布。(a) Copolymer of ethyl acrylate and methyl methacrylate (molar ratio 7:3, average molecular weight 50,000) 50 parts by weight (1)) N, N, N', N'-tetrakis-2
-Hydroxy-3-methacroyloxy-m-quinrylenediamine 60 parts by weight (c) Triethylene glycol dimethacrylate 14 parts by weight (a) 4,4'-bis(diethylamino)benzophenone 4 parts by weight (e)
2 parts by weight of fluorenone (f) 5 parts by weight of tri(β-octyloxycarbonylethyl)trithiophosphite
yg, -3085J (RTV Silicone Gum Dispersion manufactured by Toshiba Silicone ■) was diluted with n-hebutane and applied.
乾燥し、厚さ25ミクロンのシリコーンゴムiをもうけ
た。本実施例で使用したシリコーンガムは末端にアセト
キシ基を有する線状ジオルガノポリシロキサンであり、
空気中の水分の作用により。After drying, a silicone rubber i having a thickness of 25 microns was obtained. The silicone gum used in this example is a linear diorganopolysiloxane having an acetoxy group at the end.
Due to the action of moisture in the air.
酢酸を放出して架橋し、ゴム状被膜を与える。このよう
にしてもうけたシリコーンゴム層の表面に厚さ12ミク
ロンのポリエチレンテレフタレートフィルム「ルミラー
」(束し■製)fカレンダーローラーでラミイ、−トし
、湿し水不要平版用感光性版材とした。Crosslinking occurs with the release of acetic acid, giving a rubbery coating. The surface of the silicone rubber layer thus obtained was laminated with a 12 micron thick polyethylene terephthalate film "Lumirror" (manufactured by Bunshishi ■) with a calendar roller to form a photosensitive plate material for lithography that does not require dampening water. did.
真空焼枠を用いて、この版材上に150線/インチで0
5〜995係の網点面積率を有するポジフィルムを密着
し、3kw高圧水銀燈の光Kl−1mの距離から60秒
照射した。保護フィルム「ルミラー」を剥離し、n−へ
ブタン中に浸漬してガーゼで軽くこすって現像を行なっ
た。光重合が起った感光性被膜の部分のみがシリコーン
ゴム層と強く接着(光接着という)するために剥ぎとら
れず。Using a vacuum printing frame, print 0 on this plate at 150 lines/inch.
A positive film having a dot area ratio of 5 to 995 was placed in close contact with the film, and irradiated with light from a 3 kW high-pressure mercury lamp for 60 seconds from a distance of Kl-1 m. The protective film "Lumirror" was peeled off, and the film was developed by immersing it in n-hebutane and rubbing it lightly with gauze. Only the part of the photosensitive coating where photopolymerization has occurred is strongly adhered to the silicone rubber layer (known as photoadhesion) and cannot be peeled off.
これ以外の部分(光接着性の起っていない部分)のシリ
コーンゴム層だけが剥ぎとられ、感光性被膜が露出して
くる。現像した版の網点+lS男性を評価したところ、
05〜995%の網点る一円現していた。Only the silicone rubber layer other than this (the part where photoadhesion has not occurred) is peeled off, and the photosensitive coating is exposed. When evaluating the halftone + lS male of the developed version,
Halftone dots of 0.05 to 995% were visible.
これと同様の方法で、チオホスファイト化合物を含寸な
い湿し水不要平版用感光性版材を作製し。Using a method similar to this, a photosensitive plate material for lithographic printing that does not contain a thiophosphite compound and does not require dampening water was prepared.
露光、現像を行なった。現像した版の網点再現1」ユを
評価したところ、系中に存在する酸素による重合阻害を
うけて、0,5〜95%の網点1でし力・41)現して
いなかった。Exposure and development were performed. When the halftone dot reproduction 1'' of the developed plate was evaluated, it was found that 0.5 to 95% of the halftone dot 1 did not appear due to polymerization inhibition due to oxygen present in the system.
Claims (1)
で示されるチオホスファイト化合物0.01〜20重量
係とを含有することを特徴とする感光性組成物。 (R1,R2,R,はC,、−+C,。のアルキルル基
,アラルキル基であり,これらに置換基としてハロゲン
I Cl〜C,。のアルコキシ基,アルコキシカルボニ
ル基,アシルオキシ基,アルカノイル基,シアン基,水
酸基,アミン基を有していてもよい。Xは0または一C
R,R,−を示し, R4, R, は水素.C1
〜C,。のアルキル基,アリール基,アラルキル基を示
す。m,nはO〜ろの整数,pは0〜2の整数を示し,
m+ n + p = 3である)。[Scope of Claims] A photosensitive composition comprising a radically polymerizable ethylenically unsaturated compound and a thiophosphite compound represented by the following general formula in an amount of 0.01 to 20% by weight. (R1, R2, R are C,, -+C, .alkyl group, aralkyl group, and as substituents to these, halogen I Cl to C, .alkoxy group, alkoxycarbonyl group, acyloxy group, alkanoyl group, May have a cyan group, hydroxyl group, or amine group.X is 0 or 1C
R, R, -, and R4, R, are hydrogen. C1
~C,. Indicates an alkyl group, an aryl group, and an aralkyl group. m, n are integers from 0 to ro, p is an integer from 0 to 2,
m+n+p=3).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7628283A JPS59202458A (en) | 1983-05-02 | 1983-05-02 | Photosensitive composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7628283A JPS59202458A (en) | 1983-05-02 | 1983-05-02 | Photosensitive composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59202458A true JPS59202458A (en) | 1984-11-16 |
JPH0336212B2 JPH0336212B2 (en) | 1991-05-30 |
Family
ID=13600930
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP7628283A Granted JPS59202458A (en) | 1983-05-02 | 1983-05-02 | Photosensitive composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59202458A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000029453A1 (en) * | 1998-11-18 | 2000-05-25 | Taiyo Ink Manufacturing Co., Ltd. | Photocurable composition |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5018913A (en) * | 1973-06-13 | 1975-02-27 | ||
JPS53109703A (en) * | 1977-03-08 | 1978-09-25 | Teijin Ltd | Improved supporting plate |
JPS5699210A (en) * | 1980-01-14 | 1981-08-10 | Asahi Chem Ind Co Ltd | Photosensitive resin composition |
-
1983
- 1983-05-02 JP JP7628283A patent/JPS59202458A/en active Granted
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5018913A (en) * | 1973-06-13 | 1975-02-27 | ||
JPS53109703A (en) * | 1977-03-08 | 1978-09-25 | Teijin Ltd | Improved supporting plate |
JPS5699210A (en) * | 1980-01-14 | 1981-08-10 | Asahi Chem Ind Co Ltd | Photosensitive resin composition |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000029453A1 (en) * | 1998-11-18 | 2000-05-25 | Taiyo Ink Manufacturing Co., Ltd. | Photocurable composition |
Also Published As
Publication number | Publication date |
---|---|
JPH0336212B2 (en) | 1991-05-30 |
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