JPS6314340B2 - - Google Patents
Info
- Publication number
- JPS6314340B2 JPS6314340B2 JP12877780A JP12877780A JPS6314340B2 JP S6314340 B2 JPS6314340 B2 JP S6314340B2 JP 12877780 A JP12877780 A JP 12877780A JP 12877780 A JP12877780 A JP 12877780A JP S6314340 B2 JPS6314340 B2 JP S6314340B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- examples
- acid
- general formula
- alkyl group
- 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
Links
- 239000000203 mixture Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000003999 initiator Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- -1 prepolymer Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 14
- 230000035945 sensitivity Effects 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 10
- 239000000600 sorbitol Substances 0.000 description 10
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 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
- 238000007033 dehydrochlorination reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012719 thermal polymerization Methods 0.000 description 4
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 235000010724 Wisteria floribunda Nutrition 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 229920006158 high molecular weight polymer Polymers 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 3
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- DVZCOQQFPCMIPO-UHFFFAOYSA-N 2-Methoxyxanthone Chemical compound C1=CC=C2C(=O)C3=CC(OC)=CC=C3OC2=C1 DVZCOQQFPCMIPO-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- GJQLJFUURRPPJN-UHFFFAOYSA-N 3-hydroxy-2-(4-methoxyphenyl)quinazolin-4-one Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=CC=C2C(=O)N1O GJQLJFUURRPPJN-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- YTSFYTDPSSFCLU-UHFFFAOYSA-N 5-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC=NC2=C1 YTSFYTDPSSFCLU-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- UYQKZKVNYKOXHG-UHFFFAOYSA-N Methyl n-acetylanthranilate Chemical compound COC(=O)C1=CC=CC=C1NC(C)=O UYQKZKVNYKOXHG-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 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 2
- 239000002253 acid Substances 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- GKRVGTLVYRYCFR-UHFFFAOYSA-N butane-1,4-diol;2-methylidenebutanedioic acid Chemical compound OCCCCO.OC(=O)CC(=C)C(O)=O.OC(=O)CC(=C)C(O)=O GKRVGTLVYRYCFR-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 239000013078 crystal Substances 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
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 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
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 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
- IKHIDABOCOJWHV-UHFFFAOYSA-N (2-methyl-4-oxoquinazolin-3-yl) benzenesulfonate Chemical compound CC1=NC2=CC=CC=C2C(=O)N1OS(=O)(=O)C1=CC=CC=C1 IKHIDABOCOJWHV-UHFFFAOYSA-N 0.000 description 1
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- LAKGQRZUKPZJDH-GGWOSOGESA-N [2-[[(e)-but-2-enoyl]oxymethyl]-3-hydroxy-2-(hydroxymethyl)propyl] (e)-but-2-enoate Chemical compound C\C=C\C(=O)OCC(CO)(CO)COC(=O)\C=C\C LAKGQRZUKPZJDH-GGWOSOGESA-N 0.000 description 1
- SWHLOXLFJPTYTL-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(COC(=O)C(C)=C)COC(=O)C(C)=C SWHLOXLFJPTYTL-UHFFFAOYSA-N 0.000 description 1
- HSZUHSXXAOWGQY-UHFFFAOYSA-N [2-methyl-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)COC(=O)C=C HSZUHSXXAOWGQY-UHFFFAOYSA-N 0.000 description 1
- IDLJKTNBZKSHIY-UHFFFAOYSA-N [4-(diethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1 IDLJKTNBZKSHIY-UHFFFAOYSA-N 0.000 description 1
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- JPIYZTWMUGTEHX-UHFFFAOYSA-N auramine O free base Chemical compound C1=CC(N(C)C)=CC=C1C(=N)C1=CC=C(N(C)C)C=C1 JPIYZTWMUGTEHX-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- AMTXUWGBSGZXCJ-UHFFFAOYSA-N benzo[e][1,3]benzoselenazole Chemical compound C1=CC=C2C(N=C[se]3)=C3C=CC2=C1 AMTXUWGBSGZXCJ-UHFFFAOYSA-N 0.000 description 1
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical class C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 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
- 125000002619 bicyclic group Chemical group 0.000 description 1
- HSUIVCLOAAJSRE-UHFFFAOYSA-N bis(2-methoxyethyl) benzene-1,2-dicarboxylate Chemical compound COCCOC(=O)C1=CC=CC=C1C(=O)OCCOC HSUIVCLOAAJSRE-UHFFFAOYSA-N 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- OZQCLFIWZYVKKK-UHFFFAOYSA-N butane-1,3-diol 2-methylidenebutanedioic acid Chemical compound CC(O)CCO.OC(=O)CC(=C)C(O)=O.OC(=O)CC(=C)C(O)=O OZQCLFIWZYVKKK-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-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
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940031769 diisobutyl adipate Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-UHFFFAOYSA-N 0.000 description 1
- DAOJMFXILKTYRL-UHFFFAOYSA-N ethane-1,2-diol;2-methylidenebutanedioic acid Chemical compound OCCO.OC(=O)CC(=C)C(O)=O.OC(=O)CC(=C)C(O)=O DAOJMFXILKTYRL-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical class CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- UPTBUUXILDYDDU-UHFFFAOYSA-N methyl 2-(naphthalene-1-carbonylamino)benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC2=CC=CC=C12 UPTBUUXILDYDDU-UHFFFAOYSA-N 0.000 description 1
- IHMUJQKXSXXRSK-UHFFFAOYSA-N methyl 2-[(4-methoxybenzoyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(OC)C=C1 IHMUJQKXSXXRSK-UHFFFAOYSA-N 0.000 description 1
- NOMUELNZAGGIDL-UHFFFAOYSA-N methyl 2-benzamidobenzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1 NOMUELNZAGGIDL-UHFFFAOYSA-N 0.000 description 1
- IWVKTOUOPHGZRX-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(=O)C(C)=C IWVKTOUOPHGZRX-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 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
- YQCFXPARMSSRRK-UHFFFAOYSA-N n-[6-(prop-2-enoylamino)hexyl]prop-2-enamide Chemical compound C=CC(=O)NCCCCCCNC(=O)C=C YQCFXPARMSSRRK-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Polymerisation Methods In General (AREA)
Description
本発明は光重合性組成物に関するものであり、
さらに詳しくは、エチレン性不飽和結合を有する
重合可能な化合物と輝合開始剤と、必要とするな
らば結合剤と、さらに必要とするならば増感剤と
からなる光重合性組成物に関し、特に感光性印刷
版の感光層、フオトレジスト等に有用な光重合性
組成物に関するものである。
エチレン性不飽和結合を有する重合可能な化合
物と光重合開始剤と更に必要に応じて適当な皮膜
形成能を有する結合剤、熱重合禁止剤を混和させ
た感光性組成物を用いて、写真的手法により画像
の複製を行なう方法は現在知られるところであ
る。すなわち、米国特許2927022号、同2902356号
あるいは同3870524号に記載されているように、
この種の感光性組成物は光照射により硬化し不溶
化することから、この感光性組成物を適当な皮膜
となし、所望の画像の陰画を通して光照射を行な
い、適当な溶媒により未露光部のみを除去するこ
とにより所望の光重合性組成物の硬化画像を形成
させることができる。このタイプの感光性組成物
は印刷版あるいはフオトレジスト等を作成するた
めに使用されるものとして極めて有用であること
は論をまたない。
従来、エチレン性不飽和結合を有する重合可能
な化合物のみでは充分な感光性がなく、感光性を
高めるために光重合開始剤を添加することが提唱
されており、かかる光重合開始剤としてはベンジ
ル、ベンゾイン、ベンゾインエチルエーテル、ミ
ヒラーケトン、アントラキノン、アクリジン、フ
エナジン、ベンゾフエノン、２−エチルアントラ
キノン等が用いられてきた。しかしながら、これ
らの光重合開始剤を用いた場合、光重合性組成物
の硬化の感応度が低いので画像形成における像露
光に長時間を要するため、細密な画像の場合には
操作にわずかな振動があると良好な画質の画像が
再現されず、また露光の光源のエネルギー放射量
を増大しなければならないためにそれに伴なう多
大な発熱の放散を考慮する必要があり、さらに熱
による組成物の皮膜の変形および変質も生じ易い
等の問題があつた。
したがつて、本発明の目的は、高感度の光重合
性組成物を提供することである。
本発明の他の目的は広く一般にエチレン性不飽
和結合を有する重合可能な化合物を含む光重合性
組成物の光重合速度を増大させる光重合開始剤を
含んだ光重合性組成物を提供することである。
本発明者は、上記目的を達成すべく精意研究を
重ねていたが、ある特定の光重合開始剤がエチレ
ン性不飽和結合を有する重合可能な化合物の光重
合速度を著しく増大させることを見出し、本発明
に到達したものである。
本発明は、エチレン性不飽和結合を有する重合
可能な化合物と、必要とするならば結合剤と、さ
らに必要とするならば増感剤と、一般式（）
（式中、R1およびR2は各々独立してアルキル基、
置換アルキル基、アリール基、置換アリール基を
表わし、R3、R4、R5およびR6は各々独立して水
素原子、アルキル基、置換アルキル基、アリール
基、置換アリール基、ハロゲン原子、アルコキシ
基を表わし、
R3とR4、R4とR5、R5とR6は互いに結合しベン
ゼン環を形成するのに必要な原子群を表わす。）
で表わされる光重合開始剤を含有する光重合性組
成物に関するものである。
本発明の組成物におけるエチレン性不飽和結合
を有する重合可能な化合物とは、その化学構造中
に少なくとも１個のエチレン性不飽和結合を有す
る化合物であつて、モノマー、プレポリマー、す
なわち２量体、３量体および他のオリゴマーそれ
らの混合物ならびにそれらの共重合体などの化学
的形態をもつものである。それらの例としては不
飽和カルボン酸およびその塩、脂肪族多価アルコ
ール化合物とのエステル、脂肪族多価アミン化合
物とのアミド等があげられる。
不飽和カルボン酸の具体例としては、アクリル
酸、メタクリル酸、イタコン酸、クロトン酸、イ
ソクロトン酸、マレイン酸などがある。
不飽和カルボン酸の塩としては、前述の酸のナ
トリウム塩およびカリウム塩などがある。
脂肪族多価アルコール化合物と不飽和カルボン
酸とのエステルの具体例としてはアクリル酸エス
テルとして、エチレングリコールジアクリレー
ト、トリエチレングリコールアクリレート、１，
３−ブタンジオールジアクリレート、テトラメチ
レングリコールジアクリレート、プロピレングリ
コールジアクリレート、トリメチロールプロパン
トリアクリレート、トリメチロールエタントリア
クリレート、１，４−シクロヘキサンジオールジ
アクリレート、テトラエチレングリコールジアク
リレート、ペンタエリスリトールジアクリレー
ト、ペンタエリスリトールトリアクリレート、ペ
ンタエリスリトールテトラアクリレート、ジペン
タエリスリトールジアクリレート、ジペンタエリ
スリトールトリアクリレート、ジペンタエリスリ
トールテトラアクリレート、ソルビトールトリア
クリレート、ソルビトールテトラアクリレート、
ソルビトールペンタアクリレート、ソルビトール
ヘキサアクリレート、ポリエステルアクリレート
オリゴマー等がある。メタクリル酸エステルとし
ては、テトラメチレングリコールジメタクリレー
ト、トリエチレングリコールジメタクリレート、
トリメチロールプロパントリメタクリレート、ト
リメチロールエタントリメタクリレート、エチレ
ングリコールジメタクリレート、１，３−ブタン
ジオールジメタクリレート、ペンタエリスリトー
ルジメタクリレート、ペンタエリスリトールトリ
メタクリート、ジペンタエリスリトールジメタク
リレート、ソルビトールトリメタクリレート、ソ
ルビトールテトラメタクリレート、ビス−〔ｐ−
（３−メタクリルオキシ−２−ヒドロキシプロポ
キシ）フエニル〕ジメチルメタン、ビス−〔ｐ−
（アクリルオキシエトキシ）フエニル〕ジメチル
メタン等がある。イタコン酸エステルとしては、
エチレングリコールジイタコネート、プロピレン
グリコールジイタコネート、１，３−ブタンジオ
ールジイタコネート、１，４−ブタンジオールジ
イタコネート、テトラメチレングリコールジイタ
コネート、ペンタエリスリトールジイタコネー
ト、ソルビトールテトライタコネート等がある。
クロトン酸エステルとしては、エチレングリコー
ルジクロトネート、テトラメチレングリコールジ
クロトネート、ペンタエリスリトールジクロトネ
ート、ソルビトールテトラクロトネート等があ
る。イソクロトン酸エステルとしては、エチレン
グリコールジイソクロトネート、ペンタエリスリ
トールジイソクロトネート、ソルビトールテトラ
イソクロトネート等がある。マレイン酸エステル
としては、エチレングリコールジマレート、トリ
エチレングリコールジマレート、ペンタエリスリ
トールジマレート、ソルビトールテトラマレート
等がある。さらに、前述のエステルの混合物もあ
げることができる。
脂肪族多価アミン化合物と不飽和カルボン酸と
のアミドの具体例としては、メチレンビス−アク
リルアミド、メチレンビス−メタクリルアミド、
１，６−ヘキサメチレンビス−アクリルアミド、
１，６−ヘキサメチレンビス−メタクリルアミ
ド、ジエチレントリアミントリスアクリルアミ
ド、キシリレンビスアクリルアミド、キシレンビ
スメタクリルアミド等がある。
その他の例としては、特公昭48−41708号公報
中に記載されている１分子に２個以上のイソシア
ネート基を有するポリイソシアネート化合物に、
下記の一般式（）で示される水酸基を含有する
ビニルモノマーを付加せしめた１分子中に２個以
上の重合性ビニル基を含有するビニルウレタン化
合物等があげられる。
CH2＝Ｃ（Ｒ）COOCH2CH（R′）OH （）
（ただし、ＲおよびR′はＨあるいはCH3を示す。）
次に本発明の光重合性組成物において著しい特
微をなす光重合開始剤について説明する。
本発明で用いられる前記の一般式（）で表わ
される光重合開始剤は、ハーリソン（D.
Harrison）ら著、ジヤーナル オブ ザ ケミ
カル ソサエテイー（Journal of the Chemical
Society）、第2157〜2160頁（1960）記載の方法に
従い合成される一般式（）で示される２−置換
−３−ヒドロキシ−４（3H）−キナゾリノン誘導
体
（ここで、R2、R3、R4、R5およびR6は一般式
（）の場合と同義。）とR1−SO2−Cl（ここで、
R1は一般式（）の場合と同義。）で表わされる
有機スルホン酸クロリドとを脱塩化水素剤共存
下、脱塩化水素縮合反応させることにより合成す
ることができる。本反応は、脱塩化水素剤共存下
であれば、水溶媒中、有機溶媒中いずれでも進行
する。水溶媒中の場合、脱塩化水素剤としては水
酸化リチウム、水酸化ナトリウム、水酸化カリウ
ム、炭酸ナトリウム、炭酸カリウム等が好適であ
る。有機溶媒中にて反応を行なう場合、有機溶媒
としてはOH基を有しない、例えばジエチルエー
テル、ジイソプロピルエーテル、アセトン、ジク
ロロメタン、クロロホルム、４塩化炭素、テトラ
ヒドロフラン、ジオキサン、酢酸エチル、ベンゼ
ン、トルエン、アセトニトリル等が好適であり、
脱塩化水素剤としては、ピリジン、ジエチルアミ
ン、トリエチルアミン、Ｎ，Ｎ−ジメチルアニリ
ン、Ｎ，Ｎ−ジエチルアニリン等が好ましい。反
応は、一般式（）の化合物１当量に対して有機
スルホン酸クロリド１〜３当量、脱塩化水素剤を
１〜５当量用いるのが好ましく、反応温度は０℃
〜40℃が好ましい。
一般式（）におけるR1およびR2のアルキル
基は直鎖、分枝、環状のもの、より好ましくは直
鎖のものであり、好ましくは炭素原子数が１〜８
個のものであつて、例えばメチル、エチル、ブチ
ル、ヘキシル、オクチル等の各基が含まれる。ま
た、R1およびR2の置換アルキル基は、上記のよ
うなアルキル基に例えば塩素原子のようなハロゲ
ン原子、例えばメトキシ基のような炭素原子数１
〜２個のアルコキシ基などが置換されたものであ
つて、具体的には２−クロロエチル基、２−メト
キシエチル基などが含まれる。また、R1および
R2のアリール基は好ましくは単環および２環の
ものであつて、例えばフエニル基、α−ナフチル
基、β−ナフチル基などが含まれる。R1および
R2の置換アリール基は、上記のようなアリール
基に、例えばメチル基、エチル基などの炭素原子
数１〜２個のアルキル基、例えばメトキシ基、エ
トキシ基などの炭素原子数１〜２個のアルコキシ
基、例えば塩素原子などのハロゲン原子が置換し
たものが含まれ、具体的にはメチルフエニル基、
ジメチルフエニル基、メトキシフエニル基、クロ
ロフエニル基、メトキシナフチル基などがあげら
れる。
一般式（）において、R3、R4、R5およびR6
は各々独立して水素原子、アルキル基、置換アル
キル基、アリール基、置換アリール基、ハロゲン
原子、アルコキシ基を表わすが、アルキル基とし
ては炭素原子数１〜２個のものが好ましく、メチ
ル基、エチル基などが含まれる。R3、R4、R5お
よびR6の置換アルキル基は、上記のようなアル
キル基に例えば塩素原子のようなハロゲン原子、
例えばメトキシ基のような炭素原子数１〜２個の
アルコキシ基などが置換されたものであつて、具
体的には２−クロロエチル基、２−メトキシエチ
ル基などが含まれる。R3、R4、R5およびR6のア
リール基は好ましくは単環のものであつて、例え
ばフエニル基などが含まれる。
R3、R4、R5およびR6の置換アリール基は、上
記のようなアリール基に、例えばメチル基、エチ
ル基などの炭素原子数１〜２個のアルキル基、例
えばメトキシ基、エトキシ基などの炭素原子数１
〜２個のアルコキシ基、例えば塩素原子などのハ
ロゲン原子が置換したものが含まれ、具体的には
メチルフエニル基、ジメチルフエニル基、メトキ
シフエニル基、クロロフエニル基などがあげられ
る。
R3、R4、R5およびR6のハロゲン原子として
は、フツ素原子、塩素原子、臭素原子などがあ
り、アルコキシ基としては炭素原子数１〜２個の
例えばメトキシ基、エトキシ基などが好ましい。
また、R3とR4、R4とR5、R5とR6は互いに結合し
ベンゼン環を形成するのに必要な原子群を表わ
す。
下記に示す構造を有する化合物が本発明に用い
られる光重合開始剤として特に有利である。
本発明における結合剤としては、重合可能なエ
チレン性不飽和化合物および光重合開始剤に対す
る相溶性が組成物の塗布液の調整、塗布および乾
燥に至る感光材料の製造工程の全てにおいて脱混
合を起さない程度に良好であること、感光層ある
いはレジスト層として例えば溶液現像にせよ剥離
現像にせよ像露光後の現像処理が可能であるこ
と、感光層あるいはレジスト層として強靭な皮膜
を形成し得ることなどの特性を有することが要求
されるが、通常線状有機高分子重合体より適宜、
選択される。結合剤の具体的な例としては、塩素
化ポリエチレン、塩素化ポリプロピレン、ポリア
クリル酸アルキルエステル（アルキル基として
は、メチル基、エチル基、ｎ−ブチル基、iso−
ブチル基、ｎ−ヘキシル基、２−エチルヘキシル
基など）、アクリル酸アルキルエステル（アルキ
ル基は同上）とアクリロニトリル、塩化ビニル、
塩化ビニリデン、スチレン、ブタジエンなどのモ
ノマーの少なくとも一種との共重合体、ポリ塩化
ビニル、塩化ビニルとアクリロニトリルとの共重
合体、ポリ塩化ビニリデン、塩化ビニリデンとア
クリロニトリルとの共重合体、ポリ酢酸ビニル、
ポリビニルアルコール、ポリアクリロニトリル、
アクリロニトリルとスチレンとの共重合体、アク
リロニトリルとブタジエンおよびスチレンとの共
重合体、ポリメタアクリル酸アルキルエステル
（アルキル基としては、メチル基、エチル基、ｎ
−プロピル基、ｎ−ブチル基、iso−ブチル基、
ｎ−ヘキシル基、シクロヘキシル基、２−エチル
ヘキシル基など）、メタアクリル酸アルキルエス
テル（アルキル基は同上）とアクリロニトリル、
塩化ビニル、塩化ビニリデン、スチレン、ブタジ
エンなどのモノマーの少なくとも一種との共重合
体、ポリスチレン、ポリ−α−メチルスチレン、
ポリアミド（６−ナイロン、６，６−ナイロンな
ど）、メチルセルロース、エチルセルロース、ア
セチルセルロース、ポリビニルフオルマール、ポ
リビニルブチラールなどが挙げられる。さらに、
水あるいはアルカリ水可溶性有機高分子重合体を
用いると水あるいはアルカリ水現像が可能とな
る。このような高分子重合体としては側鎖にカル
ボン酸を有する付加重合体、たとえばメタクリル
酸共重合体（たとえば、メタクリル酸メチルとメ
タクリル酸との共重合体、メタクリル酸エチルと
メタクリル酸との共重合体、メタクリル酸ブチル
とメタクリル酸との共重合体、アクリル酸エチル
とメタクリル酸との共重合体、メタクリル酸とス
チレンおよびメタクリル酸との共重合体など）、
アクリル酸共重合体（アクリル酸エチルとアクリ
ル酸との共重合体、アクリル酸ブチルとアクリル
酸との共重合体、アクリル酸エチルとスチレンお
よびアクリル酸との共重合体など）、さらにはイ
タコン酸共重合体、クロトン酸共重合体、部分エ
ステル化マレイン酸共重合体などがあり、また同
様に側鎖にカルボン酸を有する酸性セルロース誘
導体がある。
これらの高分子重合体は、単独で結合剤として
用いてもよいが、二種以上の互いに相溶性が、塗
布液の調製から塗布、乾燥に至る製造工程中に脱
混合を起さない程度に良い高分子重合体を適合な
比で混合して結合剤として用いることができる。
結合剤として用いられる高分子重合体の分子量
は、重合体の種類により広範な値をとりうるが、
一般には５千〜200万、より好ましくは１万〜100
万の範囲のものが好適である。
本発明の光重合性組成物に、増感剤を更に含有
させる場合には、一般式（）で表わされる光重
合開始剤との併用により光重合速度を増大させる
増感剤が選択される。このような増感剤の具体例
としては、ベンゾイン、ベンゾインメチルエーテ
ル、ベンゾインエチルエーテル、９−フルオレノ
ン、２−クロロ−９−フルオレノン、２−メチル
−９−フルオレノン、２−アントロン、２−ブロ
モ−９−アントロン、２−エチル−９−アントロ
ン、９，10−アントラキノン、２−エチル−９，
10−アントラキノン、２−ｔ−ブチル−９，10−
アントラキノン、２，６−ジクロロ−９，10−ア
ントラキノン、キサントン、２−メチルキサント
ン、２−メトキシキサントン、チオキサントン、
ベンジル、ジベンザルアセトン、ｐ−（ジメチル
アミノ）フエニルスチリルケトン、ｐ−（ジメチ
ルアミノ）フエニルｐ−メチルスチリルケトン、
ベンゾフエノン、ｐ−（ジメチルアミノ）ベンゾ
フエノン（またはミヒラーケトン）、ｐ−（ジエチ
ルアミノ）ベンゾフエノン、ベンズアントロンな
どをあげることができる。これらの化合物のう
ち、ミヒラーケトンを用いた場合が特に好まし
い。
さらに、本発明における好ましい増感剤として
は、特公昭51−48516号公報中に記載されている
下記一般式（）で表わされる化合物があげられ
る。
式中、R7はアルキル基（例えば、メチル基、
エチル基、プロピル基など）、または置換アルキ
ル基（例えば、２−ヒドロキシエチル基、２−メ
トキシエチル基、カルボキシメチル基、２−カル
ボキシエチル基など）を表わす。
R8アルキル基（例えば、メチル基、エチル基
など）、またアリール基（例えば、フエニル基、
ｐ−ヒドロキシフエニル基、ナフチル基、チエニ
ル基など）を表わす。
Ｚは通常シアニン色素で用いられる窒素を含む
複素環核を形成するのに必要な非金属原子群、例
えばベンゾチアゾール類（ベンゾチアゾール、５
−クロロベンゾチアゾール、６−クロロベンゾチ
アゾールなど）、ナフトチアゾール類（α−ナフ
トチアゾール、β−ナフトチアゾールなど）、ベ
ンゾセレナゾール類（ベンゾセレナゾール、５−
クロロベンゾセレナゾール、６−メトキシベンゾ
セレナゾールなど）、ナフトセレナゾール類（α
−ナフトセレナゾール、β−ナフトセレナゾール
など）、ベンゾオキサゾール類（ベンゾオキサゾ
ール、５−メチルベンゾオキサゾール、５−フエ
ニルベンゾオキサゾールなど）、ナフトオキサゾ
ール類（α−ナフトオキサゾール、β−ナフトオ
キサゾールなど）を表わす。
一般式（）で表わされる化合物の具体例とし
ては、これらＺ、R7およびR8を組合せた化学構
造を有するものであり、多くのものが公知物質と
して存在する。したがつて、これら公知のものか
ら適宜選択して使用することができる。
さらに、本発明における好ましい増感剤として
は、米国特許4062686号記載の増感剤、例えば２
−〔ビス（２−フロイル）メチレン〕−３−メチル
ベンゾチアゾリン、２−〔ビス（２−チノイル）
メチレン〕−３−メチルベンゾチアゾリン、２−
〔ビス（２−フロイル）メチレン〕−３−メチルナ
フト〔１，２−ｄ〕チアゾリンなどが挙げられ
る。
さらに、本発明の組成物の製造中あるいは保存
中においてエチレン性不飽和結合を有する重合可
能な化合物の不要な熱重合を阻止するために熱重
合防止剤を添加することが望ましい。適当な熱重
合防止剤としてはヒドロキノン、ｐ−メトキシフ
エノール、ジ−ｔ−ブチル−ｐ−クレゾール、ピ
ロガロール、ｔ−ブチルカテコール、ベンゾキノ
ン、塩化第一銅、フエノチアジン、クロラニー
ル、ナフチルアミン、β−ナフトール、ニトロベ
ンゼン、ジニトロベンゼンなどがある。
また場合によつては着色を目的として染料もし
くは顔料、例えばメチレンブルー、クリスタルバ
イオレツト、ローダミンＢ、フクシン、オーラミ
ン、アゾ系染料、アントラキノン系染料、酸化チ
タン、カーボンブラツク、酸化鉄、フタロシアニ
ン系顔料、アゾ系顔料などを加えてもよい。
さらに、本発明の光重合性組成物には必要に応
じて可塑剤を添加することができる。可塑剤の例
としては、ジメチルフタレート、ジエチルフタレ
ート、ジブチルフタレート、ジヘキシルフタレー
ト、ジシクロヘキシルフタレート、ジトリデシル
フタレートなどのフタル酸エステル類、ジメチル
グリコールフタレート、エチルフタリルエチルグ
リコレート、ブチルフタリルブチルグリコレート
などのグリコールエステル類、トリクレジルホス
フエート、トリフエニルホスフエートなどのリン
酸エステル類、ジイソブチルアジペート、ジオク
チルアジペート、ジブチルセバケート、ジブチル
マレートなどの脂肪族二塩基酸エステル類などが
ある。
本発明の光重合性組成物は前述の各種構成成分
を溶媒中に溶解せしめ、適当な支持体上に公知の
方法により塗布して用いられる。次に、この場合
の各種構成成分の好ましい比率をエチレン性不飽
和結合を有する重合可能な化合物100重量部に対
する重量部で表わす。
The present invention relates to a photopolymerizable composition,
More specifically, it relates to a photopolymerizable composition comprising a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, a binder if necessary, and a sensitizer if necessary, In particular, it relates to a photopolymerizable composition useful for photosensitive layers of photosensitive printing plates, photoresists, and the like. A photosensitive composition containing a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and, if necessary, a binder having an appropriate film-forming ability and a thermal polymerization inhibitor, is used to produce a photographic effect. Methods of duplicating images using techniques are currently known. That is, as described in U.S. Pat. No. 2,927,022, U.S. Pat. No. 2,902,356 or U.S. Pat.
Since this type of photosensitive composition is cured and insolubilized by light irradiation, this photosensitive composition is formed into a suitable film, light is irradiated through the negative of the desired image, and only the unexposed areas are removed using an appropriate solvent. By removing it, a desired cured image of the photopolymerizable composition can be formed. It goes without saying that this type of photosensitive composition is extremely useful for making printing plates, photoresists, and the like. Conventionally, polymerizable compounds having ethylenically unsaturated bonds alone do not have sufficient photosensitivity, and it has been proposed to add a photopolymerization initiator to increase photosensitivity. , benzoin, benzoin ethyl ether, Michler's ketone, anthraquinone, acridine, phenazine, benzophenone, 2-ethylanthraquinone, and the like have been used. However, when these photopolymerization initiators are used, the curing sensitivity of the photopolymerizable composition is low, so it takes a long time for image exposure during image formation. If there is, it will not be possible to reproduce images of good quality, and the amount of energy radiated by the light source for exposure must be increased, so it is necessary to consider the accompanying large amount of heat dissipation. There were problems such as deformation and deterioration of the film. Therefore, it is an object of the present invention to provide a highly sensitive photopolymerizable composition. Another object of the present invention is to generally provide a photopolymerizable composition containing a photopolymerization initiator that increases the rate of photopolymerization of a photopolymerizable composition containing a polymerizable compound having an ethylenically unsaturated bond. It is. The present inventor has conducted extensive research to achieve the above object, and discovered that a certain photopolymerization initiator significantly increases the photopolymerization rate of a polymerizable compound having an ethylenically unsaturated bond. , the present invention has been achieved. The present invention comprises a polymerizable compound having an ethylenically unsaturated bond, a binder if necessary, a sensitizer if necessary, and a general formula () (In the formula, R 1 and R 2 are each independently an alkyl group,
Represents a substituted alkyl group, aryl group, substituted aryl group, and R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a halogen atom, an alkoxy represents a group, and R 3 and R 4 , R 4 and R 5 , and R 5 and R 6 represent an atomic group necessary for bonding with each other to form a benzene ring. )
The present invention relates to a photopolymerizable composition containing a photopolymerization initiator represented by: The polymerizable compound having an ethylenically unsaturated bond in the composition of the present invention is a compound having at least one ethylenically unsaturated bond in its chemical structure, and is a monomer, prepolymer, or dimer. , trimers and other oligomers, mixtures thereof, and copolymers thereof. Examples thereof include unsaturated carboxylic acids and their salts, esters with aliphatic polyhydric alcohol compounds, amides with aliphatic polyhydric amine compounds, and the like. Specific examples of unsaturated carboxylic acids include acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, and maleic acid. Salts of unsaturated carboxylic acids include sodium and potassium salts of the aforementioned acids. Specific examples of esters of aliphatic polyhydric alcohol compounds and unsaturated carboxylic acids include ethylene glycol diacrylate, triethylene glycol acrylate, 1,
3-butanediol diacrylate, tetramethylene glycol diacrylate, propylene glycol diacrylate, trimethylolpropane triacrylate, trimethylolethane triacrylate, 1,4-cyclohexanediol diacrylate, tetraethylene glycol diacrylate, pentaerythritol diacrylate, Pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol diacrylate, dipentaerythritol triacrylate, dipentaerythritol tetraacrylate, sorbitol triacrylate, sorbitol tetraacrylate,
Examples include sorbitol pentaacrylate, sorbitol hexaacrylate, and polyester acrylate oligomers. Examples of methacrylic esters include tetramethylene glycol dimethacrylate, triethylene glycol dimethacrylate,
Trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, ethylene glycol dimethacrylate, 1,3-butanediol dimethacrylate, pentaerythritol dimethacrylate, pentaerythritol trimethacrylate, dipentaerythritol dimethacrylate, sorbitol trimethacrylate, sorbitol tetramethacrylate , bis-[p-
(3-methacryloxy-2-hydroxypropoxy)phenyl]dimethylmethane, bis-[p-
(acryloxyethoxy)phenyl]dimethylmethane, etc. As itaconate ester,
Ethylene glycol diitaconate, propylene glycol diitaconate, 1,3-butanediol diitaconate, 1,4-butanediol diitaconate, tetramethylene glycol diitaconate, pentaerythritol diitaconate, sorbitol tetrataconate, etc. There is.
Examples of crotonic acid esters include ethylene glycol dicrotonate, tetramethylene glycol dicrotonate, pentaerythritol dicrotonate, and sorbitol tetracrotonate. Isocrotonic acid esters include ethylene glycol diisocrotonate, pentaerythritol diisocrotonate, sorbitol tetraisocrotonate, and the like. Examples of maleic esters include ethylene glycol dimaleate, triethylene glycol dimaleate, pentaerythritol dimaleate, and sorbitol tetramaleate. Furthermore, mixtures of the aforementioned esters may also be mentioned. Specific examples of amides of aliphatic polyvalent amine compounds and unsaturated carboxylic acids include methylene bis-acrylamide, methylene bis-methacrylamide,
1,6-hexamethylenebis-acrylamide,
Examples include 1,6-hexamethylenebis-methacrylamide, diethylenetriamine trisacrylamide, xylylenebisacrylamide, xylenebismethacrylamide, and the like. Other examples include polyisocyanate compounds having two or more isocyanate groups in one molecule described in Japanese Patent Publication No. 48-41708,
Examples include vinyl urethane compounds containing two or more polymerizable vinyl groups in one molecule to which a vinyl monomer containing a hydroxyl group represented by the following general formula () is added. CH 2 =C(R)COOCH 2 CH(R')OH () (However, R and R' represent H or CH 3. ) Next, light, which is a remarkable feature of the photopolymerizable composition of the present invention, The polymerization initiator will be explained. The photopolymerization initiator represented by the above general formula () used in the present invention is Harison (D.
Harrison et al., Journal of the Chemical Society.
2-Substituted-3-hydroxy-4(3H)-quinazolinone derivatives represented by the general formula () synthesized according to the method described in J.D. Society), pp. 2157-2160 (1960). (Here, R 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as in the general formula ().) and R 1 −SO 2 −Cl (Here,
R 1 has the same meaning as in the general formula (). ) can be synthesized by carrying out a dehydrochlorination condensation reaction with an organic sulfonic acid chloride represented by the following in the presence of a dehydrochlorinating agent. This reaction proceeds in either an aqueous solvent or an organic solvent as long as it is in the coexistence of a dehydrochlorinating agent. When in an aqueous solvent, suitable dehydrochlorination agents include lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and the like. When carrying out the reaction in an organic solvent, organic solvents that do not have an OH group, such as diethyl ether, diisopropyl ether, acetone, dichloromethane, chloroform, carbon tetrachloride, tetrahydrofuran, dioxane, ethyl acetate, benzene, toluene, acetonitrile, etc. is preferable,
Preferred examples of the dehydrochlorination agent include pyridine, diethylamine, triethylamine, N,N-dimethylaniline, and N,N-diethylaniline. In the reaction, it is preferable to use 1 to 3 equivalents of organic sulfonic acid chloride and 1 to 5 equivalents of a dehydrochlorination agent per equivalent of the compound of general formula (), and the reaction temperature is 0°C.
~40°C is preferred. The alkyl groups of R 1 and R 2 in the general formula () are linear, branched, or cyclic, more preferably linear, and preferably have 1 to 8 carbon atoms.
Examples include methyl, ethyl, butyl, hexyl, octyl, and other groups. In addition, the substituted alkyl group of R 1 and R 2 may include a halogen atom such as a chlorine atom, a carbon atom number such as a methoxy group, etc.
It is substituted with ~2 alkoxy groups, and specifically includes a 2-chloroethyl group, a 2-methoxyethyl group, and the like. Also, R 1 and
The aryl group for R 2 is preferably monocyclic or bicyclic, and includes, for example, a phenyl group, an α-naphthyl group, a β-naphthyl group, and the like. R 1 and
The substituted aryl group for R 2 is an aryl group as described above, an alkyl group having 1 to 2 carbon atoms such as a methyl group or an ethyl group, or an alkyl group having 1 to 2 carbon atoms such as a methoxy group or an ethoxy group. This includes alkoxy groups substituted with halogen atoms such as chlorine atoms, specifically methylphenyl groups,
Examples include dimethylphenyl group, methoxyphenyl group, chlorophenyl group, and methoxynaphthyl group. In the general formula (), R 3 , R 4 , R 5 and R 6
each independently represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a halogen atom, or an alkoxy group, and the alkyl group preferably has 1 to 2 carbon atoms; Contains ethyl groups, etc. The substituted alkyl groups of R 3 , R 4 , R 5 and R 6 include a halogen atom such as a chlorine atom,
For example, it is substituted with an alkoxy group having 1 to 2 carbon atoms such as a methoxy group, and specifically includes a 2-chloroethyl group, a 2-methoxyethyl group, and the like. The aryl groups of R 3 , R 4 , R 5 and R 6 are preferably monocyclic, and include, for example, a phenyl group. The substituted aryl groups of R 3 , R 4 , R 5 and R 6 include an alkyl group having 1 to 2 carbon atoms such as a methyl group or an ethyl group, such as a methoxy group or an ethoxy group. number of carbon atoms such as 1
It includes those substituted with ~2 alkoxy groups, for example, halogen atoms such as chlorine atoms, and specific examples include methylphenyl group, dimethylphenyl group, methoxyphenyl group, and chlorophenyl group. Halogen atoms for R 3 , R 4 , R 5 and R 6 include fluorine atoms, chlorine atoms, bromine atoms, etc., and alkoxy groups include methoxy groups, ethoxy groups, etc. having 1 to 2 carbon atoms, etc. preferable.
Furthermore, R 3 and R 4 , R 4 and R 5 , and R 5 and R 6 represent atomic groups necessary to bond with each other to form a benzene ring. Compounds having the structure shown below are particularly advantageous as photopolymerization initiators for use in the present invention. The binder used in the present invention has a compatibility with the polymerizable ethylenically unsaturated compound and the photopolymerization initiator, which causes demixing in all the manufacturing steps of the photosensitive material, from preparation of the coating solution of the composition to coating and drying. The photosensitive layer or resist layer should be capable of being developed after image exposure, whether by solution development or peeling development, and a tough film can be formed as the photosensitive layer or resist layer. Generally, linear organic polymers are required to have the following properties.
selected. Specific examples of binders include chlorinated polyethylene, chlorinated polypropylene, polyacrylic acid alkyl ester (alkyl groups include methyl group, ethyl group, n-butyl group, iso-
butyl group, n-hexyl group, 2-ethylhexyl group, etc.), acrylic acid alkyl ester (alkyl group is the same as above) and acrylonitrile, vinyl chloride,
Copolymers with at least one monomer such as vinylidene chloride, styrene, butadiene, polyvinyl chloride, copolymers of vinyl chloride and acrylonitrile, polyvinylidene chloride, copolymers of vinylidene chloride and acrylonitrile, polyvinyl acetate,
polyvinyl alcohol, polyacrylonitrile,
Copolymers of acrylonitrile and styrene, copolymers of acrylonitrile with butadiene and styrene, polymethacrylic acid alkyl esters (alkyl groups include methyl, ethyl, n
-propyl group, n-butyl group, iso-butyl group,
n-hexyl group, cyclohexyl group, 2-ethylhexyl group, etc.), methacrylic acid alkyl ester (alkyl group is the same as above) and acrylonitrile,
Copolymers with at least one monomer such as vinyl chloride, vinylidene chloride, styrene, butadiene, polystyrene, poly-α-methylstyrene,
Examples include polyamide (6-nylon, 6,6-nylon, etc.), methylcellulose, ethylcellulose, acetylcellulose, polyvinyl formal, polyvinyl butyral, and the like. moreover,
When a water or alkaline water soluble organic polymer is used, water or alkaline water development becomes possible. Examples of such polymers include addition polymers having carboxylic acid in the side chain, such as methacrylic acid copolymers (for example, copolymers of methyl methacrylate and methacrylic acid, and copolymers of ethyl methacrylate and methacrylic acid). copolymers of butyl methacrylate and methacrylic acid, copolymers of ethyl acrylate and methacrylic acid, copolymers of methacrylic acid and styrene and methacrylic acid, etc.),
Acrylic acid copolymers (copolymers of ethyl acrylate and acrylic acid, copolymers of butyl acrylate and acrylic acid, copolymers of ethyl acrylate and styrene and acrylic acid, etc.), and even itaconic acid. There are copolymers, crotonic acid copolymers, partially esterified maleic acid copolymers, etc., and similarly there are acidic cellulose derivatives having carboxylic acid in the side chain. These high molecular weight polymers may be used alone as a binder, but two or more types must be compatible with each other to the extent that demixing does not occur during the manufacturing process from preparation of the coating solution to application and drying. Good high molecular weight polymers can be mixed in suitable ratios and used as binders. The molecular weight of the high molecular weight polymer used as a binder can take a wide range of values depending on the type of polymer, but
Generally 5,000 to 2 million, more preferably 10,000 to 100
A range of 10,000 is preferred. When the photopolymerizable composition of the present invention further contains a sensitizer, a sensitizer that increases the photopolymerization rate when used in combination with the photopolymerization initiator represented by the general formula () is selected. Specific examples of such sensitizers include benzoin, benzoin methyl ether, benzoin ethyl ether, 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9-fluorenone, 2-anthrone, 2-bromo- 9-anthrone, 2-ethyl-9-antrone, 9,10-anthraquinone, 2-ethyl-9,
10-anthraquinone, 2-t-butyl-9,10-
Anthraquinone, 2,6-dichloro-9,10-anthraquinone, xanthone, 2-methylxanthone, 2-methoxyxanthone, thioxanthone,
Benzyl, dibenzalacetone, p-(dimethylamino) phenyl styryl ketone, p-(dimethylamino) phenyl p-methyl styryl ketone,
Examples include benzophenone, p-(dimethylamino)benzophenone (or Michler's ketone), p-(diethylamino)benzophenone, and benzanthrone. Among these compounds, it is particularly preferable to use Michler's ketone. Furthermore, preferred sensitizers in the present invention include compounds represented by the following general formula () described in Japanese Patent Publication No. 51-48516. In the formula, R 7 is an alkyl group (e.g. methyl group,
ethyl group, propyl group, etc.), or substituted alkyl group (eg, 2-hydroxyethyl group, 2-methoxyethyl group, carboxymethyl group, 2-carboxyethyl group, etc.). R 8 Alkyl groups (e.g. methyl, ethyl, etc.), and aryl groups (e.g. phenyl,
(p-hydroxyphenyl group, naphthyl group, thienyl group, etc.). Z is a group of nonmetallic atoms necessary to form the nitrogen-containing heterocyclic nucleus normally used in cyanine dyes, such as benzothiazoles (benzothiazole, 5
-chlorobenzothiazole, 6-chlorobenzothiazole, etc.), naphthothiazoles (α-naphthothiazole, β-naphthothiazole, etc.), benzoselenazole (benzoselenazole, 5-chlorobenzothiazole, etc.),
chlorobenzoselenazole, 6-methoxybenzoselenazole, etc.), naphthoselenazole (α
-naphthoselenazole, β-naphthoselenazole, etc.), benzoxazole (benzoxazole, 5-methylbenzoxazole, 5-phenylbenzoxazole, etc.), naphthoxazole (α-naphthoxazole, β-naphthoxazole, etc.) represents. Specific examples of the compound represented by the general formula () include those having a chemical structure that is a combination of Z, R 7 and R 8 , and many of them exist as known substances. Therefore, it is possible to appropriately select and use these known materials. Furthermore, preferred sensitizers in the present invention include the sensitizers described in US Pat. No. 4,062,686, such as 2
-[bis(2-furoyl)methylene]-3-methylbenzothiazoline, 2-[bis(2-thinoyl)
methylene]-3-methylbenzothiazoline, 2-
Examples include [bis(2-furoyl)methylene]-3-methylnaphtho[1,2-d]thiazoline. Furthermore, during the production or storage of the composition of the present invention, it is desirable to add a thermal polymerization inhibitor to prevent unnecessary thermal polymerization of the polymerizable compound having an ethylenically unsaturated bond. Suitable thermal polymerization inhibitors include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, cuprous chloride, phenothiazine, chloranil, naphthylamine, β-naphthol, and nitrobenzene. , dinitrobenzene, etc. In some cases, dyes or pigments may also be used for coloring, such as methylene blue, crystal violet, rhodamine B, fuchsin, auramine, azo dyes, anthraquinone dyes, titanium oxide, carbon black, iron oxide, phthalocyanine pigments, azo Pigments and the like may also be added. Furthermore, a plasticizer can be added to the photopolymerizable composition of the present invention, if necessary. Examples of plasticizers include phthalate esters such as dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dihexyl phthalate, dicyclohexyl phthalate, ditridecyl phthalate, dimethyl glycol phthalate, ethyl phthalyl ethyl glycolate, butyl phthalyl butyl glycolate, etc. Examples include glycol esters, phosphoric acid esters such as tricresyl phosphate and triphenyl phosphate, and aliphatic dibasic acid esters such as diisobutyl adipate, dioctyl adipate, dibutyl sebacate, and dibutyl maleate. The photopolymerizable composition of the present invention is used by dissolving the above-mentioned various components in a solvent and coating it on a suitable support by a known method. Next, preferred ratios of the various constituent components in this case are expressed in parts by weight based on 100 parts by weight of the polymerizable compound having an ethylenically unsaturated bond.
【表】
本発明の光重合性組成物を塗布するときに用い
られる溶媒としては、エチレンジクロリド、シク
ロヘキサノン、メチルエチルケトン、メチルセロ
ソルブ、エチルセロソルブ、酢酸メチルセロソル
ブ、モノクロルベンゼン、トルエン、キシレン、
酢酸エチル、酢酸ブチルなどである。これらの溶
媒は単独または混合して使用される。
感光性平版印刷板を製造する場合の塗布量は、
一般に固形分として0.1〜10.0ｇ／m2が適当であ
り、特に好ましくは0.5〜5.0ｇ／m2である。
本発明の光重合性組成物は感光性平版印刷板の
感光層として好適である。感光性平版印刷板に適
した支持体としては、親水化処理したアルミニウ
ム板、たとえばシリケート処理アルミニウム板、
陽極酸化アルミニウム板、シリケート電着したア
ルミニウム板があり、その他亜鉛板、ステンレス
板、クローム処理銅板、親水化処理したプラスチ
ツクフイルムや紙を挙げることができる。
また本発明の組成物をフオトレジストとして使
用する場合には銅板または銅メツキ板、ステンレ
ス板、ガラス板等の種々のものを支持体として用
いることができる。
以下、本発明に使用される光重合開始剤の合成
例と本発明の実施例を記すが、本発明はこれに限
定されるものではない。
合成例 １
２−メチル−３−エタンスルホニルオキシ−４
（3H）−キナゾリノン（光重合開始剤No.２）の
製法：
ヒドロキシルアミン塩酸塩11.8ｇを水20mlに溶
解させ、これに20重量％水酸化ナトリウム水溶液
65mlを加えた。この溶液の50mlをＮ−アセチルア
ントラニル酸メチルエステル9.7ｇをメタノール
40mlに溶解させた溶液に加え、室温にて48時間撹
拌した。減圧下にて溶媒を除去させた後水100ml
を加え溶解させ、これに濃塩酸５mlを加え析出し
た結晶を集し、エタノール、水混合溶媒より再
結晶し、２−メチル−３−ヒドロキシ−４（3H）
−キナゾリノン7.5ｇを得た。
２−メチル−３−ヒドロキシ−４（3H）−キナ
ゾリノン4.2ｇおよびエタンスルホニルクロリド
3.1ｇをアセトン50ml中に加え、撹拌しながら液
温を０〜20℃に保ちつつトリエチルアミン2.8ｇ
を滴下した。さらに、20〜30℃にて３時間撹拌を
続けた後、減圧下にて溶媒を除去した。残留物に
水100mlを加え沈殿物を集し、エタノール、ベ
ンゼン混合溶媒より再結晶し、２−メチル−３−
エタンスルホニルオキシ−４（3H）−キナゾリノ
ン5.0ｇ（融点111〜112℃）を得た。
合成例 ２
２−メチル−３−ベンゼンスルホニルオキシ−
４（3H）−キナゾリノン（光重合開始剤No.３）
の製法：
合成例１において得られた中間体２−メチル−
３−ヒドロキシ−４（3H）−キナゾリノン4.2ｇお
よびベンゼンスルホニルクロリド4.2ｇをアセト
ン70mlに加え、これを撹拌しながら反応温度を０
〜20℃に保ちつつトリエチルアミン2.8ｇを滴下
した。さらに、反応温度20〜30℃にて撹拌を３時
間続けた後、減圧下にて溶媒を除去した。残留物
に水100mlを加え沈殿物を集し、これをエタノ
ール、ヘキサン混合溶媒より再結晶し、２−メチ
ル−３−ベンゼンスルホニルオキシ−４（3H）−
キナゾリノン5.1ｇ（融点117〜118℃）を得た。
合成例 ３
２−フエニル−３−（ｐ−トルエンスルホニル
オキシ）−４（3H）−キナゾリノン（光重合開始
剤No.９）の製法：
ヒドロキシルアミン塩酸塩7.0ｇを水10mlに溶
解させこれに20重量％水酸化ナトリウム水溶液40
mlを加えこの溶液の30mlをＮ−ベンゾイルアント
ラニル酸メチルエステル7.7ｇのメタノール25ml
に溶解させた溶液に添加し、室温にて撹拌、反応
を３時間続けた。生成した沈殿を集しこれを水
50mlに溶解させた後濃塩酸５mlを加え生成した沈
殿を集した。エタノール100mlより再結晶し２
−フエニル−３−ヒドロキシ−４（3H）−キナゾ
リノン5.5ｇを得た。
炭酸ナトリウム1.9ｇを水30mlに溶解させた溶
液に２−フエニル−３−ヒドロキシ−４（3H）−
キナゾリノン1.9ｇを加え５〜15℃に冷却しなが
らｐ−トルエンスルホニルクロリド3.0ｇを添加
した。添加後、反応温度15〜30℃にて５時間撹拌
を続け、生成した沈殿物を集した。ヘキサン80
mlにて沈殿物を洗浄した後、ベンゼン、エタノー
ル混合溶媒より再結晶し、２−フエニル−３−
（ｐ−トルエンスルホニルオキシ）−４（3H）−キ
ナゾリノン2.5ｇ（融点169〜170℃）を得た。
合成例 ４
２−（ｐ−メトキシフエニル）−３−エタンスル
ホニルオキシ−４（3H）−キナゾリノン（光重
合開始剤No.11）の製法：
ヒドロキシアミン塩酸塩13.9ｇを水20mlに溶解
させ、これに20重量％水酸化ナトリウム水溶液80
mlを加え、この溶液の60mlをＮ−（ｐ−メトキシ
ベンゾイル）アントラニル酸メチルエステル17.1
ｇのメタノール50mlに溶解させた溶液に添加し、
室温にて撹拌、反応を３時間続けた。生成した沈
殿を過しこれを水200mlに溶解させた後濃塩酸
５mlを加え生成した沈殿を再び集した。エタノ
ール、水混合溶媒より再結晶し２−（ｐ−メトキ
シフエニル）−３−ヒドロキシ−４（3H）−キナゾ
リノン9.5ｇを得た。
２−（ｐ−メトキシフエニル）−３−ヒドロキシ
−４（3H）−キナゾリノン4.0ｇとエタンスルホニ
ルクロリド2.6ｇをテトラヒドロフラン50mlに加
え、０〜10℃冷却しながらトリエチルアミン2.0
ｇを滴下した。０〜10℃にてさらに１時間反応さ
せた後、不溶物を別し、液を減圧下にて濃縮
した。濃縮物をエタノール、ベンゼン混合物溶媒
より再結晶し、２−（ｐ−メトキシフエニル）−３
−エタンスルホニルオキシ−４（3H）−キナゾリ
ノン4.0ｇ（融点141〜142℃）を得た。
合成例 ５
２−（α−ナフチル）−３−ベンゼンスルホニル
オキシ−４（3H）−キナゾリノン（光重合開始
剤No.15）の製法：
ヒドロキシルアミン塩酸塩24.3ｇを水30mlに溶
解させ、これに重量％水酸化ナトリウム溶液135
mlを加え、この溶液の100mlをＮ−（α−ナフトイ
ル）アントラニル酸メチルエステル32.1ｇのメタ
ノール80mlに溶解させた溶液に添加し、室温にて
撹拌、反応を24時間続けた。不溶物を別した
後、濃塩酸20mlを加え生成する沈殿を集した。
水、エタノール混合溶媒より再結晶し、２−（α
−ナフチル）−３−ヒドロキシ−４（3H）−キナゾ
リノン21.5ｇを得た。
２−（α−ナフチル）−３−ヒドロキシ−４
（3H）−キナゾリノン3.5ｇおよびベンゼンスルホ
ニルクロリド3.5ｇをテトラヒドロフラン50mlに
加え、０〜10℃冷却しながらトリエチルアミン
2.0ｇを滴下した。０〜10℃にて１時間、さらに
20〜30℃にて１時間反応を続けた後不溶物を別
し、液を減圧下にて濃縮した。濃縮物をベンゼ
ン、エタノール混合物溶媒より再結晶して２−
（α−ナフチル）−３−ベンゼンスルホニルオキシ
−４（3H）−キナゾリノン4.5ｇ（融点189〜191
℃）を得た。
実施例 １〜４
ナイロンブラシで砂目立て後シリケート処理し
たアルミニウム板に回転塗布機を用いて下記感光
液を塗布し、100℃、３分間乾燥し、感光層を形
成させ感光板を作製した。
メタクリル酸メチル−メタクリル酸（モル比85／
15）共重合体（MEK中、30℃における極限粘度
0.166） 62ｇ
トリメチロールプロパントリアクリレート 38ｇ
一般式（）の化合物 ２ｇ
トリフエニルフオスフエート 10ｇ
エチルセロソルブ 650ml
塩化メチレン 350ml
露光は真空焼ワク装置を用いて感光板上にステ
ツプ・ウエツジ（濃度段差0.15。濃度段数０〜15
段）を置き、メタルハライドランプ（0.5kW）を
５分間照射し、露光後下記処方の現像液を用いて
現像した。
現像液
リン酸三ナトリウム 25ｇ
リン酸−ナトリウム ５ｇ
ブチルセロソルブ 70ｇ
活性剤 ２ml
水 １
現出した画像の対応するステツプ・ウエツジの
最高段数を試料の感光として第１表に示した。段
数が高いほど感度も高いことを意味する。また、
一般式（）の光重合開始剤の無添加時の感度を
比較例１として第１表に示した。[Table] Solvents used when applying the photopolymerizable composition of the present invention include ethylene dichloride, cyclohexanone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, methyl cellosolve acetate, monochlorobenzene, toluene, xylene,
These include ethyl acetate and butyl acetate. These solvents may be used alone or in combination. The coating amount when manufacturing a photosensitive lithographic printing plate is:
Generally, a suitable solid content is 0.1 to 10.0 g/m 2 , particularly preferably 0.5 to 5.0 g/m 2 . The photopolymerizable composition of the present invention is suitable as a photosensitive layer of a photosensitive lithographic printing plate. Suitable supports for photosensitive lithographic printing plates include hydrophilized aluminum plates, such as silicate-treated aluminum plates,
Examples include anodized aluminum plates and silicate electrodeposited aluminum plates, as well as zinc plates, stainless steel plates, chromium-treated copper plates, and hydrophilized plastic films and papers. Further, when the composition of the present invention is used as a photoresist, various materials such as a copper plate, a copper plated plate, a stainless steel plate, a glass plate, etc. can be used as a support. Synthesis examples of the photopolymerization initiator used in the present invention and Examples of the present invention will be described below, but the present invention is not limited thereto. Synthesis example 1 2-methyl-3-ethanesulfonyloxy-4
Production method of (3H)-quinazolinone (photopolymerization initiator No. 2): Dissolve 11.8 g of hydroxylamine hydrochloride in 20 ml of water, and add 20% by weight aqueous sodium hydroxide solution to this.
Added 65ml. Add 50ml of this solution to 9.7g of N-acetylanthranilic acid methyl ester in methanol.
It was added to a solution dissolved in 40 ml and stirred at room temperature for 48 hours. 100 ml of water after removing the solvent under reduced pressure
Add and dissolve 5 ml of concentrated hydrochloric acid, collect the precipitated crystals, recrystallize from a mixed solvent of ethanol and water, and obtain 2-methyl-3-hydroxy-4 (3H).
- 7.5 g of quinazolinone were obtained. 4.2 g of 2-methyl-3-hydroxy-4(3H)-quinazolinone and ethanesulfonyl chloride
Add 3.1g to 50ml of acetone, and add 2.8g of triethylamine while stirring and keeping the liquid temperature between 0 and 20℃.
was dripped. Furthermore, after continuing stirring at 20 to 30°C for 3 hours, the solvent was removed under reduced pressure. Add 100 ml of water to the residue, collect the precipitate, and recrystallize it from a mixed solvent of ethanol and benzene to obtain 2-methyl-3-
5.0 g of ethanesulfonyloxy-4(3H)-quinazolinone (melting point 111-112°C) was obtained. Synthesis example 2 2-methyl-3-benzenesulfonyloxy-
4(3H)-quinazolinone (photoinitiator No. 3)
Production method: Intermediate 2-methyl- obtained in Synthesis Example 1
Add 4.2 g of 3-hydroxy-4(3H)-quinazolinone and 4.2 g of benzenesulfonyl chloride to 70 ml of acetone, and reduce the reaction temperature to 0 while stirring.
2.8 g of triethylamine was added dropwise while maintaining the temperature at ~20°C. Furthermore, after stirring was continued for 3 hours at a reaction temperature of 20 to 30°C, the solvent was removed under reduced pressure. Add 100 ml of water to the residue, collect the precipitate, recrystallize it from a mixed solvent of ethanol and hexane, and obtain 2-methyl-3-benzenesulfonyloxy-4(3H)-
5.1 g of quinazolinone (melting point 117-118°C) was obtained. Synthesis Example 3 Method for producing 2-phenyl-3-(p-toluenesulfonyloxy)-4(3H)-quinazolinone (photopolymerization initiator No. 9): Dissolve 7.0 g of hydroxylamine hydrochloride in 10 ml of water and add 20 g of hydroxylamine hydrochloride to 10 ml of water. Weight% sodium hydroxide aqueous solution 40
Add 30 ml of this solution to 25 ml of methanol containing 7.7 g of N-benzoylanthranilic acid methyl ester.
and the reaction was continued for 3 hours with stirring at room temperature. Collect the formed precipitate and add it to water.
After dissolving in 50 ml, 5 ml of concentrated hydrochloric acid was added and the resulting precipitate was collected. Recrystallize from 100ml of ethanol 2
5.5 g of -phenyl-3-hydroxy-4(3H)-quinazolinone was obtained. 2-phenyl-3-hydroxy-4(3H)- was added to a solution of 1.9 g of sodium carbonate dissolved in 30 ml of water.
1.9 g of quinazolinone was added, and 3.0 g of p-toluenesulfonyl chloride was added while cooling to 5 to 15°C. After the addition, stirring was continued for 5 hours at a reaction temperature of 15 to 30°C, and the generated precipitate was collected. hexane 80
After washing the precipitate with ml of water, it was recrystallized from a mixed solvent of benzene and ethanol to obtain 2-phenyl-3-
2.5 g of (p-toluenesulfonyloxy)-4(3H)-quinazolinone (melting point 169-170°C) was obtained. Synthesis Example 4 Method for producing 2-(p-methoxyphenyl)-3-ethanesulfonyloxy-4(3H)-quinazolinone (photopolymerization initiator No. 11): Dissolve 13.9 g of hydroxyamine hydrochloride in 20 ml of water, Add to this 20% by weight sodium hydroxide aqueous solution 80
17.1 ml of N-(p-methoxybenzoyl)anthranilic acid methyl ester and 60 ml of this solution
g dissolved in 50 ml of methanol,
Stirring and reaction continued at room temperature for 3 hours. After filtering the formed precipitate and dissolving it in 200 ml of water, 5 ml of concentrated hydrochloric acid was added to collect the formed precipitate again. Recrystallization from a mixed solvent of ethanol and water yielded 9.5 g of 2-(p-methoxyphenyl)-3-hydroxy-4(3H)-quinazolinone. Add 4.0 g of 2-(p-methoxyphenyl)-3-hydroxy-4(3H)-quinazolinone and 2.6 g of ethanesulfonyl chloride to 50 ml of tetrahydrofuran, and add 2.0 g of triethylamine while cooling at 0 to 10°C.
g was added dropwise. After reacting for an additional 1 hour at 0 to 10°C, insoluble materials were separated and the liquid was concentrated under reduced pressure. The concentrate was recrystallized from a mixed solvent of ethanol and benzene to give 2-(p-methoxyphenyl)-3
4.0 g of -ethanesulfonyloxy-4(3H)-quinazolinone (melting point 141-142°C) was obtained. Synthesis Example 5 Method for producing 2-(α-naphthyl)-3-benzenesulfonyloxy-4(3H)-quinazolinone (photopolymerization initiator No. 15): Dissolve 24.3 g of hydroxylamine hydrochloride in 30 ml of water, and add wt% sodium hydroxide solution 135
100 ml of this solution was added to a solution of 32.1 g of N-(α-naphthoyl)anthranilic acid methyl ester dissolved in 80 ml of methanol, and the reaction was continued with stirring at room temperature for 24 hours. After separating the insoluble matter, 20 ml of concentrated hydrochloric acid was added and the resulting precipitate was collected.
Recrystallized from a mixed solvent of water and ethanol, 2-(α
21.5 g of -naphthyl)-3-hydroxy-4(3H)-quinazolinone were obtained. 2-(α-naphthyl)-3-hydroxy-4
Add 3.5 g of (3H)-quinazolinone and 3.5 g of benzenesulfonyl chloride to 50 ml of tetrahydrofuran, and add triethylamine while cooling from 0 to 10°C.
2.0g was added dropwise. 1 hour at 0-10℃, then
After continuing the reaction at 20 to 30°C for 1 hour, insoluble materials were separated and the liquid was concentrated under reduced pressure. The concentrate was recrystallized from a benzene and ethanol mixture solvent to obtain 2-
(α-Naphthyl)-3-benzenesulfonyloxy-4(3H)-quinazolinone 4.5 g (melting point 189-191
°C) was obtained. Examples 1 to 4 After graining with a nylon brush, a silicate-treated aluminum plate was coated with the following photosensitive solution using a spin coating machine, and dried at 100°C for 3 minutes to form a photosensitive layer to produce a photosensitive plate. Methyl methacrylate - methacrylic acid (molar ratio 85/
15) Copolymer (in MEK, intrinsic viscosity at 30℃
0.166) 62 g Trimethylolpropane triacrylate 38 g Compound of general formula () 2 g Triphenyl phosphate 10 g Ethyl cellosolve 650 ml Methylene chloride 350 ml Exposure was performed using a vacuum baking device on the photosensitive plate using a step wedge (density step 0.15. Number of stages 0-15
A metal halide lamp (0.5 kW) was placed on the plate, and the plate was irradiated with a metal halide lamp (0.5 kW) for 5 minutes. After exposure, the plate was developed using a developer having the following formulation. Developer Trisodium phosphate 25 g Sodium phosphate 5 g Butyl cellosolve 70 g Activator 2 ml Water 1 The highest number of step wedges corresponding to the developed image is shown in Table 1 as the sensitivity of the sample. The higher the number of stages, the higher the sensitivity. Also,
The sensitivity without the addition of the photopolymerization initiator of general formula () is shown in Table 1 as Comparative Example 1.
【表】
第１表に示したように、一般式（）の光重合
開始剤を用いた場合、これを用いない比較例１に
比較して、より高い感度を示し、本発明の所期の
効果が十分に認められた。
実施例 ５〜11
実施例１〜４と同一処方にて調液した塗布液に
増感剤としてミヒラーケトン1.6ｇを添加溶解さ
せ、実施例１〜４と同様にして感光板を作製し
た。
この感光板をプラノPSプリンタ−A3（富士写
真フイルム製）を用いてステツプ・ウエツジを通
して露光した後、実施例１〜４と同一処方の現像
液を用いて現像した。現出した画像の対応するス
テツプ・ウエツジの最高段数を試料の感度として
第２表に示した。また、ミヒラーケトン単独使用
時の感度を比較例２として第２表に示した。[Table] As shown in Table 1, when the photopolymerization initiator of the general formula () is used, higher sensitivity is shown compared to Comparative Example 1 which does not use this, and the desired result of the present invention is achieved. The effects were fully recognized. Examples 5 to 11 Photosensitive plates were prepared in the same manner as in Examples 1 to 4 by adding and dissolving 1.6 g of Michler's ketone as a sensitizer to a coating solution prepared using the same formulation as in Examples 1 to 4. This photosensitive plate was exposed to light through a step wedge using a Plano PS printer A3 (manufactured by Fuji Photo Film), and then developed using a developer having the same formulation as in Examples 1 to 4. The highest number of step wedges corresponding to the developed image is shown in Table 2 as the sensitivity of the sample. Furthermore, the sensitivity when using Michler's ketone alone is shown in Table 2 as Comparative Example 2.
【表】【table】
【表】
第２表に示したように、ミヒラーケトン単独使
用の比較例２に比較し、一般式（）にて示され
る光重合開始剤に増感剤としてミヒラーケトンを
添加した場合には感度が大幅に上昇する。
実施例 12〜24
実施例１〜４と同一処方にて調液した感光液に
増感剤として一般式（）の化合物2.0ｇを添加
溶解させ、実施例１〜４と同様にして感光板を作
製した。
この感光板をプラノPSプリンターA3（富士写
真フイルム製）を用いてステツプ・ウエツジを通
して露光した後、実施例１〜４と同一処方の現像
液を用いて現像した。ここで用いた一般式（）
の化合物を第３表に示した。試料の感度は現出し
た画像の対応するステツプ・ウエツジの最高段数
として第４表に示した。
また、一般式（）の化合物の単独使用時の感
度を比較例３〜８として第４表に示した。[Table] As shown in Table 2, compared to Comparative Example 2 in which Michler's ketone was used alone, the sensitivity was significantly increased when Michler's ketone was added as a sensitizer to the photopolymerization initiator represented by the general formula (). rise to Examples 12-24 2.0 g of the compound of general formula () as a sensitizer was added and dissolved in a photosensitive solution prepared with the same formulation as in Examples 1-4, and a photosensitive plate was prepared in the same manner as in Examples 1-4. Created. This photosensitive plate was exposed to light through a step wedge using a Plano PS printer A3 (manufactured by Fuji Photo Film), and then developed using a developer having the same formulation as in Examples 1 to 4. General formula used here ()
The compounds are shown in Table 3. The sensitivity of the sample is shown in Table 4 as the highest number of steps and wedges corresponding to the resulting image. Furthermore, the sensitivity when using the compound of general formula () alone is shown in Table 4 as Comparative Examples 3 to 8.
【表】【table】
【表】
第４表に示したように、一般式（）の化合物
を単独で使用した場合に比較して、本発明による
一般式（）の化合物を組合せることにより感度
は大幅に上昇し、本発明の所期の効果が十分に認
められた。
実施例 25〜28
実施例１〜４と同一処方にて調液した感光液に
増感剤として２−〔ビス（２−フロイル）メチレ
ン〕−３−メチルナフト〔１，２−ｄ〕チアゾリ
ン2.0ｇを添加溶解させ、実施例１〜４と同様に
感光板を作製した。
この感光板をプラノPSプリンターA3（富士写
真フイルム製）を用いてステツプ・ウエツジを通
して露光した後、実施例１〜４と同一処方の現像
液を用いて現像した。試料の感度は現出した画像
の対応するステツプ・ウエツジの最高段数として
第５表に示した。また、２−〔ビス（２−フロイ
ル）メチレン〕−３−メチルナフト〔１，２−ｄ〕
チアゾリン単独使用時の感度を比較例９として第
５表に示した。[Table] As shown in Table 4, the sensitivity is significantly increased by combining the compounds of the general formula () according to the present invention, compared to when the compound of the general formula () is used alone. The intended effects of the present invention were fully observed. Examples 25 to 28 2.0 g of 2-[bis(2-furoyl)methylene]-3-methylnaphtho[1,2-d]thiazoline was added as a sensitizer to a photosensitive solution prepared using the same formulation as Examples 1 to 4. was added and dissolved, and a photosensitive plate was produced in the same manner as in Examples 1 to 4. This photosensitive plate was exposed to light through a step wedge using a Plano PS printer A3 (manufactured by Fuji Photo Film), and then developed using a developer having the same formulation as in Examples 1 to 4. The sensitivity of the sample is shown in Table 5 as the highest number of steps and wedges corresponding to the resulting image. Also, 2-[bis(2-furoyl)methylene]-3-methylnaphtho[1,2-d]
The sensitivity when using thiazoline alone is shown in Table 5 as Comparative Example 9.
【表】
第５表に示したように、一般式（）で示され
る化合物を用いることにより感度が飛躍的に向上
し、本発明の効果が認められた。[Table] As shown in Table 5, the sensitivity was dramatically improved by using the compound represented by the general formula (), and the effects of the present invention were recognized.
Claims (1)
合物と光重合開始剤と、必要とするならば結合剤
と、さらに必要とするならば増感剤とからなる光
重合性組成物において、光重合開始剤として少な
くとも１種の下記一般式（）： （式中、R1およびR2は各々独立してアルキル基、
置換アルキル基、アリール基、置換アリール基を
表わし、R3、R4、R5およびR6は各々独立して水
素原子、アルキル基、置換アルキル基、アリール
基、置換アリール基、ハロゲン原子、アルコキシ
基を表わし、 R3とR4、R4とR5、R5とR6は互いに結合しベン
ゼン環を形成するのに必要な原子群を表わす。） で表わされる化合物を用いることを特徴とする光
重合性組成物。[Scope of Claims] 1. A photopolymerizable composition comprising a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, a binder if necessary, and a sensitizer if necessary. In the product, at least one kind of the following general formula () as a photopolymerization initiator: (In the formula, R 1 and R 2 are each independently an alkyl group,
Represents a substituted alkyl group, aryl group, substituted aryl group, and R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a halogen atom, an alkoxy represents a group, and R 3 and R 4 , R 4 and R 5 , and R 5 and R 6 represent an atomic group necessary for bonding with each other to form a benzene ring. ) A photopolymerizable composition characterized by using a compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12877780A JPS5753747A (en) | 1980-09-17 | 1980-09-17 | Photopolymerizing composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12877780A JPS5753747A (en) | 1980-09-17 | 1980-09-17 | Photopolymerizing composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5753747A JPS5753747A (en) | 1982-03-30 |
| JPS6314340B2 true JPS6314340B2 (en) | 1988-03-30 |
Family
ID=14993203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12877780A Granted JPS5753747A (en) | 1980-09-17 | 1980-09-17 | Photopolymerizing composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5753747A (en) |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59174831A (en) * | 1983-03-24 | 1984-10-03 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
-
1980
- 1980-09-17 JP JP12877780A patent/JPS5753747A/en active Granted
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Also Published As
| Publication number | Publication date |
|---|---|
| JPS5753747A (en) | 1982-03-30 |
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