JPH0797213B2 - Photopolymerization initiator composition - Google Patents
Photopolymerization initiator compositionInfo
- Publication number
- JPH0797213B2 JPH0797213B2 JP61277817A JP27781786A JPH0797213B2 JP H0797213 B2 JPH0797213 B2 JP H0797213B2 JP 61277817 A JP61277817 A JP 61277817A JP 27781786 A JP27781786 A JP 27781786A JP H0797213 B2 JPH0797213 B2 JP H0797213B2
- Authority
- JP
- Japan
- Prior art keywords
- photopolymerization initiator
- compound
- carbon atoms
- photopolymerization
- initiator 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.)
- Expired - Lifetime
Links
- 239000003999 initiator Substances 0.000 title claims description 28
- 239000000203 mixture Substances 0.000 title claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- -1 benzoin alkyl ether Chemical class 0.000 description 13
- 239000000975 dye Substances 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 150000001451 organic peroxides Chemical class 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 238000005259 measurement Methods 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
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
- 125000005591 trimellitate group Chemical group 0.000 description 2
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- VDQNOOZIDCTAPX-UHFFFAOYSA-N 3-butylperoxycarbonylbenzenecarboperoxoic acid Chemical group CCCCOOC(=O)C1=CC=CC(C(=O)OO)=C1 VDQNOOZIDCTAPX-UHFFFAOYSA-N 0.000 description 1
- YHHKOCQFUSUCCG-UHFFFAOYSA-N 3-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound OCC(C)C(=O)C1=CC=CC=C1 YHHKOCQFUSUCCG-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group 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
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ITXCLKMRLHBUEP-UHFFFAOYSA-N bis(2-methylbutan-2-yl) 4-[3,4-bis(2-methylbutan-2-ylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)CC)C(C(=O)OOC(C)(C)CC)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)CC)C(C(=O)OOC(C)(C)CC)=C1 ITXCLKMRLHBUEP-UHFFFAOYSA-N 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical group CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 1
- 229960004419 dimethyl fumarate Drugs 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 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
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000008096 xylene Substances 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
Description
【発明の詳細な説明】 〈産業上の利用分野〉 本発明は、不飽和化合物重合用の光重合開始剤組成物に
関するものである。DETAILED DESCRIPTION OF THE INVENTION <Field of Industrial Application> The present invention relates to a photopolymerization initiator composition for unsaturated compound polymerization.
不飽和結合を分子中に含むモノマー、オリゴマー及びポ
リマーは光重合開始剤の存在下で光重合することは良く
知られており、印刷版やプリント基板、IC等を作成する
際に用いられるいわゆるフォトポノマーやフォトレジス
トとして広く利用されている。It is well known that monomers, oligomers and polymers containing an unsaturated bond in the molecule undergo photopolymerization in the presence of a photopolymerization initiator, so-called photoponomers used when making printing plates, printed circuit boards, ICs, etc. Widely used as a photoresist.
〈従来の技術〉 これらに使用する光重合開始剤としては、従来から種々
の物質が報告され、実際に使用されている。例えば、ベ
ンゾイン系化合物としてはベンゾイン、ベンゾインアル
キルエーテル（USP2448282号）等、カルボニル化合物と
してベンジル、ベンゾフェノン、アセトフェノン、ベン
ジルケタール等、アゾ化合物としてアゾビスイソブチロ
ニトリルアゾジベンゾイル等、また硫黄化合物としてジ
ベンゾチアゾリルスルフィド、テトラエチルウラムジス
ルフィド等がある。<Prior Art> As a photopolymerization initiator used for these, various substances have been reported and actually used. For example, benzoin, benzoin alkyl ether (USP2448282) and the like as benzoin compounds, benzyl, benzophenone, acetophenone, benzyl ketal and the like as carbonyl compounds, azobisisobutyronitrile azodibenzoyl etc. as azo compounds, and dibenzo as a sulfur compound. Examples thereof include thiazolyl sulfide and tetraethyluram disulfide.
また、有機過酸化物と各種染料とを組合せてなる光重合
開始剤（特開昭59-189340号公報、特開昭61-213838号公
報）、更にチオキサンテン系染料とアミン類とを組合わ
せてなる光重合開始剤（特開昭60-221403号公報）等が
知られている。Further, a photopolymerization initiator comprising a combination of an organic peroxide and various dyes (JP-A-59-189340, JP-A-61-213838), and a combination of a thioxanthene dye and amines Photopolymerization initiators (JP-A-60-221403) and the like are known.
〈発明が解決しようとする問題点〉 しかしながら、これらの光重合開始剤と種々の不飽和化
合物とからなる光重合組成物はフォトポリマーとして必
ずしも良好な感度を有しているとはいえず、さらに高感
度でしかも安定性の高い光重合開始剤が強く要望されて
いる。<Problems to be Solved by the Invention> However, photopolymerization compositions comprising these photopolymerization initiators and various unsaturated compounds do not necessarily have good sensitivity as photopolymers, and There is a strong demand for a photopolymerization initiator having high sensitivity and high stability.
また過酸化結合を分子中に有する有機過酸化物はハイド
ロ過酸化物、過酸化ジアルキル、過酸化ジアシル、過酸
エステル、過炭酸エステル等の多くの種類の化合物があ
り、これらは熱により分解して活性なラジカルを生成す
ることは周知であり、不飽和化合物の熱重合開始剤、熱
重合触媒、熱重合架橋剤などとして広く用いられてい
る。さらに有機過酸化物は光エネルギーによっても分解
し同様に活性なラジカルを生成することが報告されてい
る。ところがこれらの有機過酸化物は不飽和化合物の光
重合開始剤として用いるには光重合開始能が低く、また
一般に熱安定性も低いことから到底実用に適するもので
はなく、したがって重合型のフォトポリマーの光重合開
始剤として有機過酸化物を使用した例は従来知られてい
ない。Organic peroxides having a peroxide bond in the molecule include many kinds of compounds such as hydroperoxide, dialkyl peroxide, diacyl peroxide, perester ester and percarbonate ester, which are decomposed by heat. It is well known that active radicals are generated, and it is widely used as a thermal polymerization initiator for unsaturated compounds, a thermal polymerization catalyst, a thermal polymerization crosslinking agent, and the like. Furthermore, it has been reported that organic peroxides are decomposed by light energy and similarly generate active radicals. However, these organic peroxides are not suitable for practical use because they have low photopolymerization initiating ability to be used as a photopolymerization initiator for unsaturated compounds, and generally have low thermal stability. No example has been hitherto known in which an organic peroxide is used as the photopolymerization initiator.
〈課題点を解決するための手段〉 このような背景から本発明者らは鋭意研究した結果、特
定構造を有する有機過酸エステル化合物と有機染料化合
物とを組み合わせたものが、極めて良好な光重合開始能
を有しており、不飽和化合物の光重合において初期重合
速度を増大させ、これを用いることにより高感度な感光
性樹脂が得られることを見出して本発明に到達した。<Means for Solving the Problems> As a result of intensive studies conducted by the present inventors from such a background, a combination of an organic peroxyester compound having a specific structure and an organic dye compound is extremely excellent in photopolymerization. The present invention has been accomplished by finding that it has an initiating ability, increases the initial polymerization rate in the photopolymerization of an unsaturated compound, and by using this, a highly sensitive photosensitive resin can be obtained.
すなわち本発明は、分子内にベンゼン骨格またはベンゾ
フェノン骨格を有する有機過酸エステル化合物と、下記
一般式（Ｉ）〜（III）で示される化合物 〔R1は炭素数１〜４のアルキル基を表わす〕 〔R2,R3は炭素数１〜４のアルキル基、R4は炭素数１〜
４のアルキレン基を表わす。〕 〔R5は炭素数１〜４のアルキル基を表わす〕 から選択される１種又は２種以上の有機染料化合物とを
組合せてなる光重合開始剤組成物を提供する。That is, the present invention relates to an organic perester compound having a benzene skeleton or a benzophenone skeleton in the molecule and a compound represented by the following general formulas (I) to (III). [R 1 represents an alkyl group having 1 to 4 carbon atoms] [R 2 and R 3 are alkyl groups having 1 to 4 carbon atoms, R 4 is 1 to 4 carbon atoms
4 represents an alkylene group. ] There is provided a photopolymerization initiator composition comprising a combination of one or more organic dye compounds selected from [R 5 represents an alkyl group having 1 to 4 carbon atoms].
以下、本発明につき更に詳細に説明する。Hereinafter, the present invention will be described in more detail.
本発明に用いる前記有機過酸エステル化合物としては、
10時間半減期温度が70℃以上のものが好ましく、例えば
ターシャリィブチルペルオキシベンゾエート、ターシャ
リィブチルペルオキシメトキシベンゾエート、ターシャ
リィブチルペルオキシニトロベンゾエート、ターシャリ
ィブチルペルオキシエチルベンゾエート、フェニルイソ
プロピルオキシベンゾエート、ジターシャリィブチルジ
ペルオキシイソフタレート、トリターシャリィブチルト
リペルオキシトリテート、トリターシャリィブチルトリ
ペルオキシトリメリテート、トリターシャリィブチルト
リペルオキシトリメシネート、テトラターシャリィブチ
ルテトラペルオキシピロメリテート、2,5−ジメチル−
2,5−ジ（ベンゾイルペルオキシ）ヘキサン、3,3′,4,
4′−テトラ−（ターシャリィブチルペルオキシカルボ
ニル）ベンゾフェノン、3,3′,4,4′−テトラ（ターシ
ャリィアミルペルオキシカルボニル）ベンゾフェノン、
3,3′,4,4′−テトラ（ターシャリィヘキサシルペルオ
キシカルボニル）ベンゾフェノン等がある。The organic perester compound used in the present invention,
It is preferable that the 10-hour half-life temperature is 70 ° C. or higher. Diperoxyisophthalate, tritertiary butyl triperoxy tritate, tritertiary butyl triperoxy trimellitate, tritertiary butyl triperoxy trimesinate, tetratertiary butyl tetraperoxypyromellitate, 2,5-dimethyl-
2,5-di (benzoylperoxy) hexane, 3,3 ', 4,
4′-tetra- (tertiarybutylperoxycarbonyl) benzophenone, 3,3 ′, 4,4′-tetra (tertiaryamylperoxycarbonyl) benzophenone,
Examples include 3,3 ', 4,4'-tetra (tertiary hexasilperoxycarbonyl) benzophenone.
本発明に用いる有機染料化合物としては下記（Ｉ）式に
て示されるメロシアニン系染料、 〔R1は炭素数１〜４のアルキル基を表わす〕 具体的に例えば下記Ａ−１〜Ａ−３の化合物等が挙げら
れる。The organic dye compound used in the present invention is a merocyanine dye represented by the following formula (I), [R 1 represents an alkyl group having 1 to 4 carbon atoms] Specific examples include the following compounds A-1 to A-3.
下記（II）式で示される染料、 〔R2,R3は炭素数１〜４のアルキル基、R4は炭素数１〜
４のアルキレン基を表わす。〕 具体的には例えば下記Ｂ−１、Ｂ−２の化合物等が挙げ
られる。 A dye represented by the following formula (II), [R 2 and R 3 are alkyl groups having 1 to 4 carbon atoms, R 4 is 1 to 4 carbon atoms
4 represents an alkylene group. Specific examples include the following compounds B-1 and B-2.
下記（III）式にて示されるチオキサンテン系染料 〔R5は炭素数１〜４のアルキル基を表わす〕 具体的には例えば下記Ｃ−１〜Ｃ−３の化合物等が挙げ
られる。 Thioxanthene dye represented by the following formula (III) [R 5 represents an alkyl group having 1 to 4 carbon atoms] Specific examples include the following C-1 to C-3 compounds.
これら有機染料化合物は単独でもまた２種以上を混合し
て用いてもよく、いずれも市販されているものを適宜使
用することができる。 These organic dye compounds may be used alone or in admixture of two or more, and any commercially available one may be appropriately used.
本発明の光重合開始剤組成物は、前記の（Ａ）有機過酸
エステル化合物と（Ｂ）有機染料化合物とからなるもの
であり、（Ａ）と（Ｂ）両者の配合割合は、重量比で
（Ａ）：（Ｂ）が1:100〜100:1が好ましく、さらに好ま
しくは1:30〜10:1であるのが望ましい。The photopolymerization initiator composition of the present invention comprises the above-mentioned (A) organic perester compound and (B) organic dye compound, and the mixing ratio of both (A) and (B) is a weight ratio. It is preferable that (A) :( B) is 1:10 to 100: 1, and more preferably 1:30 to 10: 1.
本発明の光重合開始剤組成物が不飽和化合物の良好な光
重合開始剤となり得るのは、有機過酸エステル化合物の
有機染料化合物による有効な増感光分解に帰因するもの
と考えられる。そして有機染料化合物を選択することに
より紫外光から可視光までの範囲で光重合開始能を発現
することができるのであらゆる光源が使用でき、さらに
可視光レーザー用の感光材料の光重合開始剤としても利
用できる。The reason why the photopolymerization initiator composition of the present invention can be a good photopolymerization initiator for unsaturated compounds is considered to be due to effective photosensitized decomposition of an organic perester compound by an organic dye compound. And by selecting an organic dye compound, it is possible to express the photopolymerization initiating ability in the range from ultraviolet light to visible light, so any light source can be used, and also as a photopolymerization initiator for the photosensitive material for visible light laser. Available.
本発明の光重合開始剤はほとんどすべての不飽和化合物
を光重合することができる。すなわち不飽和化合物とし
て重合性のエチレン系不飽和結合を有するモノマー、オ
リゴマーまたはポリマーに適用することができ、例えば
アクリル酸、メタクリル酸、イタコン酸、マレイン酸及
びその無水物、フタル酸及びその無水物、フマル酸等の
不飽和酸や（メタ）アクリル酸メチル、（メタ）アクリ
ル酸エチル、（メタ）アクリル酸ブチル、（メタ）アク
リル酸グリシジル、（メタ）アクリル酸ヒドロキシエチ
ル、マレイン酸ジメチル、マレイン酸ジエチル、フマル
酸ジメチル、ペンタエリスリトールトリ（メタ）アクリ
レート、トリメチロールプロパントリ（メタ）アクリレ
ート、エチレングリコールジ（メタ）アクリレート、プ
ロピレングリコールジ（メタ）アクリレート等の不飽和
酸エステル化合物、及びアクリルアミド、アクリロニト
リル、Ｎ−ビニルピロリドン、酢酸ビニル等の単量体、
さらに不飽和ポリエステル、不飽和ポリエーテル、不飽
和ポリウレタンやエポキシ（メタ）アクリレート化合物
等の光重合に用いることができる。The photopolymerization initiator of the present invention can photopolymerize almost all unsaturated compounds. That is, it can be applied to a monomer, oligomer or polymer having a polymerizable ethylenically unsaturated bond as an unsaturated compound, for example acrylic acid, methacrylic acid, itaconic acid, maleic acid and its anhydride, phthalic acid and its anhydride. Unsaturated acids such as fumaric acid, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, glycidyl (meth) acrylate, hydroxyethyl (meth) acrylate, dimethyl maleate, malein Unsaturated acid ester compounds such as diethyl acid, dimethyl fumarate, pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, and acrylamide; Ak Ronitoriru, N- vinylpyrrolidone, a monomer such as vinyl acetate,
Further, it can be used for photopolymerization of unsaturated polyester, unsaturated polyether, unsaturated polyurethane, epoxy (meth) acrylate compound and the like.
これらの不飽和化合物の単独かもしくは二種以上の混合
物に本発明の光重合開始剤組成物を添加し必要に応じて
適当な希釈溶媒を加えて光重合組成物とする。The photopolymerization initiator composition of the present invention is added to one of these unsaturated compounds or a mixture of two or more thereof, and an appropriate diluting solvent is added if necessary to obtain a photopolymerization composition.
光重合開始剤組成物の添加量は不飽和化合物100重量部
に対して0.1〜30重量部、好ましくは0.5〜20重量部が望
ましい。The photopolymerization initiator composition is added in an amount of 0.1 to 30 parts by weight, preferably 0.5 to 20 parts by weight, based on 100 parts by weight of the unsaturated compound.
また適当な希釈溶媒とは本発明の光重合開始剤組成物及
び不飽和化合物を溶解するものならすべて使用できる。
例えば、水、メタノール、エタノール、プロパノール、
ブタノール、アセトン、メチルエチルケトン、メチルイ
ソブチルケトン、トルエン、キシレン、酢酸エチル、酢
酸ブチル、セロソルブ、テトラヒドロフラン、ジオキサ
ン、ジクロルメタン、クロロホルム、四塩化炭素、トリ
クロルエチレン、ジメチルホルムアミド、ジメチルスル
ホキシド等である。Any suitable diluting solvent can be used as long as it dissolves the photopolymerization initiator composition of the present invention and the unsaturated compound.
For example, water, methanol, ethanol, propanol,
Butanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, toluene, xylene, ethyl acetate, butyl acetate, cellosolve, tetrahydrofuran, dioxane, dichloromethane, chloroform, carbon tetrachloride, trichloroethylene, dimethylformamide, dimethyl sulfoxide and the like.
このようにして得られる光重合組成物は紫外線または可
視光線などの活性光線を照射することにより重合反応が
達せられる。光源としては超高圧、高圧、中圧および低
圧の各種水銀灯、ケミカルランプ、カーボンアーク灯、
キセノン灯、メタルハライドランプ、蛍光灯、タングス
テン灯、太陽光、及び各種レーザーランプ等が使用でき
る。The photopolymerizable composition thus obtained can be subjected to a polymerization reaction by irradiating with actinic rays such as ultraviolet rays or visible rays. As the light source, ultra-high pressure, high pressure, medium and low pressure mercury lamps, chemical lamps, carbon arc lamps,
A xenon lamp, a metal halide lamp, a fluorescent lamp, a tungsten lamp, sunlight, and various laser lamps can be used.
〈発明の効果〉 本発明の光重合開始剤組成物は、前記有機過酸エステル
化合物と有機染料化合物とを組み合わせて用いているた
め、従来の光重合開始剤よりも著しく高感度であり、弱
い光源でも充分に感光するため作業性や経済性の点でも
優れている。<Effects of the Invention> The photopolymerization initiator composition of the present invention uses the organic peroxyester compound and the organic dye compound in combination, and thus has significantly higher sensitivity than conventional photopolymerization initiators and is weak. It is also excellent in workability and economical efficiency because it is fully exposed to light.
本発明の光重合開始剤組成物は通常の光重合反応に使用
できる他、光硬化型の塗料、印刷インキ、接着剤や、印
刷版作製、さらにフォトレジスト等の多方面に適用する
ことが可能であり、またその効果も非常に良好で、最高
感度のものを得ることができる。The photopolymerization initiator composition of the present invention can be used for ordinary photopolymerization reactions, and can be applied to various fields such as photocurable coatings, printing inks, adhesives, printing plate preparation, and photoresists. In addition, the effect is very good, and the highest sensitivity can be obtained.
〈実施例〉 以下実施例及び比較例によって本発明をさらに詳細に説
明する。なお、部は重量部を示す。<Example> The present invention will be described in more detail with reference to Examples and Comparative Examples. In addition, a part shows a weight part.
実施例１〜24 ポリ（メタクリル酸メチル／アクリル酸エチル／メタク
リル酸）（モル比5/4/1:分子量10万）100部と、ペンタ
エリスリトールトリアクリレート（新中村化学（株）
製:A−TMM-3L）100部に表−１に示す本発明の光重合開
始剤組成物を表−１の割合で添加し、さらにこれを1000
部のエチルセロソルブに均一に溶解して感光液を得た。Examples 1 to 24 100 parts of poly (methyl methacrylate / ethyl acrylate / methacrylic acid) (molar ratio 5/4/1: molecular weight 100,000) and pentaerythritol triacrylate (Shin-Nakamura Chemical Co., Ltd.)
(Manufactured by: A-TMM-3L) 100 parts of the photopolymerization initiator composition of the present invention shown in Table-1 was added at a ratio of Table-1, and further 1000
Part of the solution was uniformly dissolved in ethyl cellosolve to obtain a photosensitive solution.
これらの感光液を陽極酸化処理したアルミニウム板上に
乾燥塗膜厚が２μｍとなるようにホアラーを用いて塗布
し、乾燥させたものをそれぞれ感光性試験板とした。こ
の感光性試験板にグレイスケール（コダック社製ステッ
プタブレットNo.2）を真空密着し、60cmの距離からKWの
超高圧水銀灯を用いて1.5秒間露光した後、市販のアル
カリ現像液（富士写真フィルム（株）製DN-3C）で現像
を行い硬化部分のグレイスケールの段数を読みとること
で感度を測定した。結果を表−１に示す。なおステップ
段数は、２段差があると感度が２倍になることを示し、
数値が大きいほど高感度である。These sensitizing solutions were applied onto anodized aluminum plates using a wahler so that the dry coating film thickness was 2 μm, and dried to obtain photosensitive test plates. A gray scale (Kodak Step Tablet No. 2) was vacuum-adhered to this photosensitive test plate and exposed for 1.5 seconds using a KW ultra-high pressure mercury lamp from a distance of 60 cm, and then a commercially available alkaline developer (Fuji Photo Film Sensitivity was measured by developing with DN-3C manufactured by Co., Ltd. and reading the number of gray scale steps in the cured part. The results are shown in Table-1. Note that the number of steps indicates that the sensitivity doubles when there are two steps,
The larger the value, the higher the sensitivity.
比較例１〜９ 比較のため、本発明の光重合開始剤組成物に代えて、表
−２に示す市販の光重合開始剤、有機染料化合物または
有機過酸エステル化合物を用いて実施例と同様の方法に
て感光液を得、実施例と同様の測定を行った。結果を表
−２に示す。Comparative Examples 1 to 9 For comparison, a commercially available photopolymerization initiator, an organic dye compound or an organic perester compound shown in Table 2 was used instead of the photopolymerization initiator composition of the present invention, and the same as the examples. A photosensitive solution was obtained by the method of 1. and the same measurement as that of the example was performed. The results are shown in Table-2.
比較例10〜15 更に比較のため、本発明の光重合開始剤組成物に代え
て、表−３に示す光重合開始剤組成物を用いて実施例と
同様の方法にて感光液を得、実施例と同様の測定を行っ
た、結果を表３に示す。Comparative Examples 10 to 15 For further comparison, instead of the photopolymerization initiator composition of the present invention, a photopolymerization solution was obtained in the same manner as in Examples using the photopolymerization initiator composition shown in Table-3, The same measurement as that of the example was performed, and the results are shown in Table 3.
PBZ:ターシャリィブチルペルオキシベンゾエート PBIF:ジターシャリィブチルジペルオキシイソフタレー
ト BTTB:3,3′,4,4′−テトラ（ターシャリィブチルペルオ
キシカルボニル）ベンゾフェノン TMT:トリターシャリィブチルトリペルオキシトリメリテ
ート BIBE:ベンゾインイソブチルエーテル イルガキュア651:ジメトキシフェニルアセトフェノン
（チバガイギー社製）イルガキュア907:2−メチル−１
−〔４−（メチルチオ）フェニル〕−２−モルホリノー
プロパノン−１（チバガイギー社製） ダロキュア1173:3−ヒドロキシ−２−メチル−１−フェ
ニル−プロパン−１−オン（メルク社製） 他の略号は表−１と同じ Ｄ−3:4−（４−ブトキシフェニル）−2,6−ジ（４−メ
トキシフェニル）チオピリリウムフルオロボレート BPO:ベンゾイルペルオキシド PDA:p−ジメチルアミノ安息香酸イソアミルエステル XT:2,4−ジイソプロピルチオキサントン 他の略号は表−１と同じ 表−1,表−2,表−３の結果から、実施例のものは比較例
のものに比べて極めて高感度であることが明らかであ
る。 PBZ: Tertiary butyl peroxybenzoate PBIF: Ditertiary butyl diperoxyisophthalate BTTB: 3,3 ′, 4,4′-Tetra (tertiary butyl peroxycarbonyl) benzophenone TMT: Tritertiary butyl triperoxy trimellitate BIBE: benzoin isobutyl ether Irgacure 651: dimethoxyphenylacetophenone (manufactured by Ciba-Geigy) Irgacure 907: 2-methyl-1
-[4- (Methylthio) phenyl] -2-morpholinopropanone-1 (manufactured by Ciba Geigy) Darocur 1173: 3-hydroxy-2-methyl-1-phenyl-propan-1-one (manufactured by Merck) and others Symbol is the same as in Table-1 D-3: 4- (4-butoxyphenyl) -2,6-di (4-methoxyphenyl) thiopyrylium fluoroborate BPO: benzoyl peroxide PDA: p-dimethylaminobenzoic acid isoamyl ester XT: 2,4-diisopropylthioxanthone Other abbreviations are the same as in Table-1, Table-1, Table-2, Table-3 It is clear that is much more sensitive than that of the comparative example.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭60−221403（ＪＰ，Ａ) 特開 昭61−213838（ＪＰ，Ａ) 特開 昭59−189340（ＪＰ，Ａ) 特開 昭52−129791（ＪＰ，Ａ) 特公 昭61−9621（ＪＰ，Ｂ２) ─────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-60-221403 (JP, A) JP-A 61-213838 (JP, A) JP-A 59-189340 (JP, A) JP-A 52- 129791 (JP, A) Japanese Patent Publication Sho 61-9621 (JP, B2)
Claims (1)
ン骨格を有する有機過酸エステル化合物と、下記一般式
（Ｉ）〜（III）で示される化合物 〔R1は炭素数１〜４のアルキル基を表わす〕 〔R2,R3は炭素数１〜４のアルキル基、R4は炭素数１〜
４のアルキレン基を表わす。〕 〔R5は炭素数１〜４のアルキル基を表わす〕 から選択される１種又は２種以上の有機染料化合物とを
組合せてなる光重合開始剤組成物。1. An organic peroxyester compound having a benzene skeleton or a benzophenone skeleton in the molecule and a compound represented by the following general formulas (I) to (III) [R 1 represents an alkyl group having 1 to 4 carbon atoms] [R 2 and R 3 are alkyl groups having 1 to 4 carbon atoms, R 4 is 1 to 4 carbon atoms
4 represents an alkylene group. ] [R 5 represents an alkyl group having 1 to 4 carbon atoms] A photopolymerization initiator composition which is combined with one or more organic dye compounds selected from
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61277817A JPH0797213B2 (en) | 1986-11-22 | 1986-11-22 | Photopolymerization initiator composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61277817A JPH0797213B2 (en) | 1986-11-22 | 1986-11-22 | Photopolymerization initiator composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63132902A JPS63132902A (en) | 1988-06-04 |
| JPH0797213B2 true JPH0797213B2 (en) | 1995-10-18 |
Family
ID=17588678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61277817A Expired - Lifetime JPH0797213B2 (en) | 1986-11-22 | 1986-11-22 | Photopolymerization initiator composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0797213B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63144342A (en) * | 1986-12-09 | 1988-06-16 | Nippon Oil & Fats Co Ltd | Dry film photoresist |
| JP2598994B2 (en) * | 1988-11-14 | 1997-04-09 | 富士写真フイルム株式会社 | Photosensitive composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59189340A (en) * | 1983-04-13 | 1984-10-26 | Nippon Oil & Fats Co Ltd | Photopolymerization initiator composition having high sensitivity |
| JPS60221403A (en) * | 1984-04-18 | 1985-11-06 | Nippon Kayaku Co Ltd | Polymerizable resin composition |
| JPS61213838A (en) * | 1985-03-20 | 1986-09-22 | Nippon Oil & Fats Co Ltd | Photosensitive lithographic printing plate |
-
1986
- 1986-11-22 JP JP61277817A patent/JPH0797213B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63132902A (en) | 1988-06-04 |
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