KR20220019654A - Carbamoyloxime compound and polymerization initiator and polymerizable composition containing said compound - Google Patents
Carbamoyloxime compound and polymerization initiator and polymerizable composition containing said compound Download PDFInfo
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- KR20220019654A KR20220019654A KR1020217027837A KR20217027837A KR20220019654A KR 20220019654 A KR20220019654 A KR 20220019654A KR 1020217027837 A KR1020217027837 A KR 1020217027837A KR 20217027837 A KR20217027837 A KR 20217027837A KR 20220019654 A KR20220019654 A KR 20220019654A
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- -1 Carbamoyloxime compound Chemical class 0.000 title claims abstract description 110
- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 229960001330 hydroxycarbamide Drugs 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title claims description 69
- 239000003505 polymerization initiator Substances 0.000 title claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 104
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 57
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 22
- 239000005011 phenolic resin Substances 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 20
- 239000003822 epoxy resin Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229920000647 polyepoxide Polymers 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 239000002585 base Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000010408 film Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000007259 addition reaction Methods 0.000 description 13
- 150000001721 carbon Chemical group 0.000 description 13
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- 238000007142 ring opening reaction Methods 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000049 pigment Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000004593 Epoxy Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 150000002923 oximes Chemical class 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 208000034189 Sclerosis Diseases 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
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- 239000000758 substrate Substances 0.000 description 6
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- 238000006845 Michael addition reaction Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
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- 229910052753 mercury Inorganic materials 0.000 description 5
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- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- 238000006068 polycondensation reaction Methods 0.000 description 5
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- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
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- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 4
- 238000005192 partition Methods 0.000 description 4
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- 239000000243 solution Substances 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical group [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 3
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RFMXKZGZSGFZES-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OC(=O)CS.CCC(CO)(CO)CO RFMXKZGZSGFZES-UHFFFAOYSA-N 0.000 description 3
- SQTMWMRJFVGAOW-UHFFFAOYSA-N 3-[2,3-bis(sulfanyl)propylsulfanyl]propane-1,2-dithiol Chemical compound SCC(S)CSCC(S)CS SQTMWMRJFVGAOW-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
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- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
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- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
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- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
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- 229960000380 propiolactone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
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- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 230000001235 sensitizing effect Effects 0.000 description 1
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- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-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
- 229940036248 turpentine Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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- 239000002966 varnish Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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Abstract
본 발명의 과제는 높은 광염기 발생 효율을 가지는 화합물을 제공하는 것에 있다. 본 발명은 하기 일반식(I)로 표현되는 카르바모일옥심 화합물이다. (식 중 R1은 수소 원자, 시아노기 또는 탄소 원자 수 1~20의 탄화수소기를 나타내고, R2는 수소 원자 또는 탄소 원자 수 1~20의 탄화수소기를 나타내며, R3, R4, R5, R6, R7, R8 및 R9는 각각 독립적으로 수소 원자, 할로겐 원자, 시아노기, 니트로기, 탄소 원자 수 1~20의 탄화수소기, 또는 탄소 원자 수 2~20의 복소환 함유기 등을 나타내고, R3과 R4, R6과 R7, R7과 R8 및 R8과 R9 중 적어도 1세트는 서로 연결되어 벤젠환을 형성하고 있으며, n은 0 또는 1을 나타낸다.)
An object of the present invention is to provide a compound having high photobase generation efficiency. The present invention is a carbamoyloxime compound represented by the following general formula (I). (Wherein, R 1 represents a hydrogen atom, a cyano group, or a hydrocarbon group having 1 to 20 carbon atoms, R 2 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydrocarbon group having 1 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms. and at least one set of R 3 and R 4 , R 6 and R 7 , R 7 and R 8 , and R 8 and R 9 is connected to each other to form a benzene ring, and n represents 0 or 1.)
Description
본 발명은 카르바모일옥심 화합물에 관한 것이다. The present invention relates to carbamoyloxime compounds.
일반적으로 감광성 수지 조성물 등의 중합성 조성물은 감광성 수지 등의 중합성 화합물에 광중합 개시제를 첨가한 것이고, 에너지선(광) 조사(照射)에 의해 중합 경화, 또는 현상시킬 수 있기 때문에 광경화성 잉크, 감광성 인쇄판, 각종 포토레지스트, 광경화성 접착제 등에 사용되고 있다. In general, a polymerizable composition such as a photosensitive resin composition is obtained by adding a photopolymerization initiator to a polymerizable compound such as a photosensitive resin, and because it can be polymerized and cured or developed by irradiation with energy rays (light), a photocurable ink; It is used for photosensitive printing plates, various photoresists, and photocurable adhesives.
광중합 개시제는 에너지선(광) 조사에 의해 발생하는 활성종의 차이로 광 라디칼 발생제, 광산 발생제, 광염기 발생제로 나뉜다. 광 라디칼 발생제는 경화 속도가 빠르고, 경화 후에 활성종이 잔존하지 않는 등의 장점이 있는 한편, 산소에 의한 경화 저해가 일어나기 때문에 박막의 경화에서는 산소를 차단하는 층 등을 마련해야 한다는 단점이 있다. 광산 발생제는 산소에 의한 저해를 받지 않는다는 장점이 있는 한편, 활성종의 산이 잔존함으로써 금속 기판을 부식시키거나 경화 후의 수지를 변성시키는 등의 단점이 있다. 광염기 발생제는 상기 산소에 의한 경화 저해 및 잔존 활성종에 의한 부식과 같은 문제를 발생시키기 어렵기 때문에 주목받고 있지만, 대체로 광산 발생제와 비교하면 저감도(저경화성)라는 문제가 있다. 광염기 발생제는 예를 들면 특허문헌 1 및 2에 기재되어 있다. The photopolymerization initiator is classified into a photo-radical generator, a photo-acid generator, and a photobase generator with a difference in active species generated by energy ray (light) irradiation. The photo-radical generator has advantages such as a fast curing rate and no active species remaining after curing. On the other hand, since curing inhibition by oxygen occurs, there is a disadvantage that a layer that blocks oxygen must be provided in curing the thin film. The photo-acid generator has an advantage that it is not inhibited by oxygen, but has disadvantages such as corrosion of the metal substrate or denaturing the resin after curing due to the residual acid of the active species. The photobase generator is attracting attention because it is difficult to cause problems such as inhibition of curing by oxygen and corrosion by residual active species. A photobase generator is described in patent documents 1 and 2, for example.
그러나 종래의 광염기 발생제는 염기 발생 효율이 낮고, 경화 감도가 충분한 것이 아니었다. However, the conventional photobase generator has a low base generation efficiency, and the curing sensitivity is not sufficient.
따라서, 본 발명의 과제는 높은 광염기 발생 효율을 가지는 화합물을 제공하는 것에 있다. Accordingly, an object of the present invention is to provide a compound having a high photobase generation efficiency.
본 발명자는 예의 검토를 실시하여, 특정 구조의 화합물이 높은 광염기 발생 효율을 가지고 있고, 중합 개시제로서 유용한 것을 찾아냈다. MEANS TO SOLVE THE PROBLEM This inventor earnestly examined, the compound of a specific structure had high photobase generation efficiency, and discovered that it was useful as a polymerization initiator.
즉, 본 발명은 하기 일반식(I)로 표현되는 카르바모일옥심 화합물이다. That is, the present invention is a carbamoyloxime compound represented by the following general formula (I).
(식 중 R1은 수소 원자, 할로겐 원자, 니트로기, 시아노기, 탄소 원자 수 1~20의 탄화수소기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내고, (wherein R 1 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a methylene group in the hydrocarbon group, the number of carbon atoms substituted with a divalent group selected from the following <Group A>) represents a group of 1 to 20,
R2는 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내며, R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a group having 1 to 20 carbon atoms in which a methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <Group A>,
R3, R4, R5, R6, R7, R8 및 R9는 각각 독립적으로 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR10, -COOR10, -CO-R10, -SR10, 탄소 원자 수 1~20의 탄화수소기, 또는 탄소 원자 수 2~20의 복소환 함유기를 나타내고, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 10 , -COOR 10 , -CO-R 10 , -SR 10 , a hydrocarbon group having 1 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
R10은 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 탄소 원자 수 2~20의 복소환 함유기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내고, 분자 중에 R10이 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며, R 10 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a heterocycle-containing group having 2 to 20 carbon atoms, or a methylene group in the hydrocarbon group is the number of carbon atoms substituted with a divalent group selected from the following <Group A> When a group of 1 to 20 is represented and two or more R 10 is present in a molecule, they may be the same or different,
X1은 -NR21R22, 또는 하기 일반식(a) 혹은 하기 일반식(b)로 표현되는 기를 나타내고, X 1 represents -NR 21 R 22 , or a group represented by the following general formula (a) or the following general formula (b),
R21 및 R22는 각각 독립적으로 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내며, R 21 and R 22 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a group having 1 to 20 carbon atoms in which a methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <Group A> ,
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R21 및 R22는 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기, -OR11, -COOR11, -CO-R11 또는 -SR11로 치환된 탄소 원자 수 1~20의 기이어도 되고, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 21 and R 22 are one or more hydrogen atoms in the hydrocarbon group. A group having 1 to 20 carbon atoms may be substituted with an atom, a cyano group, a nitro group, a hydroxyl group, -OR 11 , -COOR 11 , -CO-R 11 or -SR 11 ,
R11은 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기, 또는 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기 또는 수산기로 치환된 탄소 원자 수 1~20의 기를 나타내고, 분자 중에 R11이 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며, R 11 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a group having 1 to 20 carbon atoms in which the methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <Group A>, or a hydrogen atom in the hydrocarbon group 1 or 2 or more represent a group having 1 to 20 carbon atoms substituted with a halogen atom, a cyano group, a nitro group or a hydroxyl group, and when a plurality of R 11 is present in the molecule, they may be the same or different,
<군 A>는 -O-, -CO-, -COO-, -NR12-, -NR12CO- 및 -S-이고, <Group A> is -O-, -CO-, -COO-, -NR 12 -, -NR 12 CO- and -S-,
R12는 수소 원자 또는 탄소 원자 수 1~20의 탄화수소기를 나타내고, 분자 중에 R12가 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며, R 12 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and when two or more R 12 are present in a molecule, they may be the same or different;
R3과 R4, R6과 R7, R7과 R8 및 R8과 R9는 각각 독립적으로 서로 연결되어 수소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 3~10의 환을 형성하고 있어도 되고, R 3 and R 4 , R 6 and R 7 , R 7 and R 8 and R 8 and R 9 may each independently be linked to each other to form a ring having 3 to 10 carbon atoms comprising a hydrogen atom and a carbon atom,
R3과 R4, R6과 R7, R7과 R8 및 R8과 R9 중 적어도 1세트는 서로 연결되어 벤젠환을 형성하고 있으며, At least one set of R 3 and R 4 , R 6 and R 7 , R 7 and R 8 and R 8 and R 9 is connected to each other to form a benzene ring,
R21과 R22는 서로 연결되어 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환, 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환을 형성하고 있어도 되고, R 21 and R 22 are linked to each other to form a ring having 2 to 10 carbon atoms composed of a hydrogen atom, a nitrogen atom and a carbon atom, or a ring having 2 to 10 carbon atoms composed of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom you can do it,
n은 0 또는 1을 나타낸다.) n represents 0 or 1.)
(식 중 R31, R32, R33, R34, R35, R36, R37, R38, R39 및 R40은 각각 독립적으로 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 B>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내며, (Wherein, R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or represents a group having 1 to 20 carbon atoms in which the methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <group B>,
R31, R32, R33, R34, R35, R36, R37, R38, R39 및 R40은 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기, -OR41, -COOR41, -CO-R41 또는 -SR41로 치환된 탄소 원자 수 1~20의 기이어도 되고, R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are one or more of the hydrogen atoms in the hydrocarbon group is a halogen atom, a cyano group, or a nitro group. A group having 1 to 20 carbon atoms may be substituted with a group, a hydroxyl group, -OR 41 , -COOR 41 , -CO-R 41 or -SR 41 ,
R41은 수소 원자 또는 탄소 원자 수 1~20의 탄화수소기를 나타내고, 기 중에 R41이 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며, R 41 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and when two or more R 41 is present in the group, they may be the same or different;
<군 B>는 -O-, -CO-, -COO-, -NR42-, -NR42CO- 및 -S-이고, <Group B> is -O-, -CO-, -COO-, -NR 42 -, -NR 42 CO- and -S-,
R42는 수소 원자 또는 탄소 원자 수 1~20의 탄화수소기를 나타내고, 기 중에 R42가 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며, R 42 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and when a plurality of R 42 is present in the group, they may be the same or different;
R31과 R32, R33과 R34, R35와 R36, R37과 R38, 및 R39와 R40은 각각 독립적으로 서로 연결되어 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환, 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환을 형성하고 있어도 되고, R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R 38 , and R 39 and R 40 are each independently linked to each other to form a hydrogen atom, a nitrogen atom and a carbon atom 2 A ring of ~10 or a ring of 2 to 10 carbon atoms composed of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom may be formed;
*는 결합수(結合手)를 나타낸다.) * indicates the number of bonds (結合手).
이하, 본 발명에 대해 상세하게 설명한다. Hereinafter, the present invention will be described in detail.
본 발명의 카르바모일옥심 화합물은 상기 일반식(I)로 표현되는 것이다. 상기 일반식(I)로 표현되는 카르바모일옥심 화합물에는 옥심의 이중 결합에 의한 기하 이성체가 존재하는데, 이들을 구별하는 것은 아니다. The carbamoyloxime compound of the present invention is represented by the general formula (I). In the carbamoyloxime compound represented by the general formula (I), a geometric isomer formed by a double bond of an oxime exists, but these are not distinguished.
즉, 본 명세서에서 상기 일반식(I)로 표현되는 카르바모일옥심 화합물, 그리고 후술할 상기 화합물의 바람직한 형태인 화합물 및 예시 화합물은 이성체의 혼합물 또는 어느 한쪽을 나타내고 있고, 나타낸 구조의 이성체에 한정하는 것은 아니다. That is, in the present specification, the carbamoyloxime compound represented by the general formula (I), as well as the compounds and exemplary compounds that are preferred forms of the compound to be described later, represent a mixture of isomers or either isomers, and are limited to the isomers of the structures shown. is not doing
이하, 상기 일반식(I)로 표현되는 카르바모일옥심 화합물을 단순히 "일반식(I)로 표현되는 화합물" 또는 "본 발명의 화합물"이라고도 한다. Hereinafter, the carbamoyloxime compound represented by the general formula (I) is also simply referred to as “a compound represented by the general formula (I)” or “a compound of the present invention”.
상기 일반식(I), 상기 일반식(a) 및 상기 일반식(b)에서의 할로겐 원자로는 불소 원자, 염소 원자, 브롬 원자, 요오드 원자를 들 수 있다. A fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned as a halogen atom in the said general formula (I), the said general formula (a), and the said general formula (b).
상기 일반식(I), 상기 일반식(a) 및 상기 일반식(b)에서의 탄소 원자 수 1~20의 탄화수소기로는 탄소 원자 수 1~20의 지방족 탄화수소기 및 탄소 원자 수 6~20의 방향족 탄화수소기를 들 수 있다. As the hydrocarbon group having 1 to 20 carbon atoms in the general formulas (I), (a) and (b), an aliphatic hydrocarbon group having 1 to 20 carbon atoms and an aliphatic hydrocarbon group having 6 to 20 carbon atoms and aromatic hydrocarbon groups.
상기 탄소 원자 수 1~20의 지방족 탄화수소기로는 예를 들면, 메틸기, 에틸기, 프로필기, 이소프로필기, 부틸기, 이소부틸기, s-부틸기, t-부틸기, 아밀기, 이소아밀기, t-아밀기, 헥실기, 헵틸기, 옥틸기, 이소옥틸기, 2-에틸헥실기, t-옥틸기, 노닐기, 이소노닐기, 데실기, 이소데실기, 운데실기, 도데실기, 테트라데실기, 헥사데실기, 옥타데실기, 이코실기 등의 알킬기; 시클로펜틸기, 시클로헥실기 등의 시클로알킬기; 및 시클로헥실메틸기 등의 시클로알킬알킬기, 그리고 이들 기의 탄소-탄소 1중 결합을, 탄소-탄소 2중 결합 또는 탄소-탄소 3중 결합으로 치환한 구조인 불포화 지방족 탄화수소기 등을 들 수 있다. The aliphatic hydrocarbon group having 1 to 20 carbon atoms is, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a s-butyl group, a t-butyl group, an amyl group, an isoamyl group. , t-amyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, t-octyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tetra Alkyl groups, such as a decyl group, a hexadecyl group, an octadecyl group, and an icosyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; and a cycloalkylalkyl group such as a cyclohexylmethyl group, and an unsaturated aliphatic hydrocarbon group having a structure in which a carbon-carbon single bond of these groups is substituted with a carbon-carbon double bond or a carbon-carbon triple bond.
상기 탄소 원자 수 6~20의 방향족 탄화수소기로는 예를 들면, 페닐기, 톨릴기, 크실릴기, 메시틸기, 벤질기, 나프틸기, 페난트릴기, 피레닐기 및 비페닐기 등을 들 수 있다. Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a tolyl group, a xylyl group, a mesityl group, a benzyl group, a naphthyl group, a phenanthryl group, a pyrenyl group, and a biphenyl group.
R1~R10, R21 및 R22로 표현되는, 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기, -OR11, -COOR11, -CO-R11 또는 -SR11로 치환된 탄소 원자 수 1~20의 기로는 상기 탄소 원자 수 1~20의 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기, -OR11, -COOR11, -CO-R11 또는 -SR11로 치환된 구조이고, 전체의 탄소 원자 수가 1~20인 기를 들 수 있다. 또한, R11로 표현되는, 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기로 치환된 탄소 원자 수 1~20의 기로는 상기 탄소 원자 수 1~20의 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기로 치환된 구조이고, 전체의 탄소 원자 수가 1~20인 기를 들 수 있다. 1 or 2 or more of the hydrogen atoms in the hydrocarbon group represented by R 1 to R 10 , R 21 and R 22 are a halogen atom, a cyano group, a nitro group, a hydroxyl group, -OR 11 , -COOR 11 , -CO- As the group having 1 to 20 carbon atoms substituted with R 11 or -SR 11 , one or two or more of the hydrogen atoms in the hydrocarbon group having 1 to 20 carbon atoms are a halogen atom, a cyano group, a nitro group, a hydroxyl group, A group having a structure substituted with -OR 11 , -COOR 11 , -CO-R 11 or -SR 11 and having a total number of carbon atoms of 1 to 20 is exemplified. In addition, as a group having 1 to 20 carbon atoms, in which one or two or more of the hydrogen atoms in the hydrocarbon group represented by R 11 are substituted with a halogen atom, a cyano group, a nitro group, or a hydroxyl group, the group having 1 to 20 carbon atoms One or two or more of the hydrogen atoms in the hydrocarbon group of has a structure in which one or more hydrogen atoms are substituted with a halogen atom, a cyano group, a nitro group, or a hydroxyl group, and a group having 1 to 20 carbon atoms in total is mentioned.
R1~R11, R21 및 R22로 표현되는, 탄화수소기 중의 메틸렌기가 상기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기로는 상기 탄소 원자 수 1~20의 탄화수소기 중의 메틸렌기의 1개 또는 2개 이상이 -O-, -CO-, -COO-, -NR12-, -NR12CO- 또는 -S-로 치환된 구조이고, 전체의 탄소 원자 수가 1~20인 기를 들 수 있다. The group having 1 to 20 carbon atoms in which the methylene group in the hydrocarbon group represented by R 1 to R 11 , R 21 and R 22 is substituted with a divalent group selected from <Group A> is the group having 1 to 20 carbon atoms. 1 or 2 or more of the methylene groups in the hydrocarbon group are substituted with -O-, -CO-, -COO-, -NR 12 -, -NR 12 CO- or -S-, and the total number of carbon atoms is 1 to 20 people can be mentioned.
R31~R40으로 표현되는, 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기, -OR41, -COOR41, -CO-R41 또는 -SR41로 치환된 탄소 원자 수 1~20의 기로는 상기 탄소 원자 수 1~20의 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기, -OR41, -COOR41, -CO-R41 또는 -SR41로 치환된 구조이고, 전체의 탄소 원자 수가 1~20인 기를 들 수 있다. 1 or 2 or more of the hydrogen atoms in the hydrocarbon group represented by R 31 to R 40 are a halogen atom, a cyano group, a nitro group, a hydroxyl group, -OR 41 , -COOR 41 , -CO-R 41 or -SR 41 As the group having 1 to 20 carbon atoms substituted with , one or more than one hydrogen atom in the hydrocarbon group having 1 to 20 carbon atoms is a halogen atom, a cyano group, a nitro group, a hydroxyl group, -OR 41 , -COOR 41 , a group having a structure substituted with -CO-R 41 or -SR 41 and having a total number of carbon atoms of 1 to 20 is exemplified.
R31~R40으로 표현되는, 탄화수소기 중의 메틸렌기가 상기 <군 B>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기로는 상기 탄소 원자 수 1~20의 탄화수소기 중의 메틸렌기의 1개 또는 2개 이상이 -O-, -CO-, -COO-, -NR42-, -NR42CO- 또는 -S-로 치환된 구조이고, 전체의 탄소 원자 수가 1~20인 기를 들 수 있다. The group having 1 to 20 carbon atoms in which the methylene group in the hydrocarbon group represented by R 31 to R 40 is substituted with a divalent group selected from <Group B> is a methylene group in the hydrocarbon group having 1 to 20 carbon atoms. 1 or 2 or more are substituted with -O-, -CO-, -COO-, -NR 42 -, -NR 42 CO- or -S-, and the total number of carbon atoms is 1 to 20. can
상기 일반식(I)에서의 탄소 원자 수 2~20의 복소환 함유기로는 예를 들면, 테트라하이드로푸라닐기, 디옥소라닐기, 테트라하이드로피라닐기, 모르폴릴기, 푸라닐기, 티오페닐기, 메틸티오페닐기, 헥실티오페닐기, 벤조티오페닐기, 피롤릴기, 피롤리디닐기, 이미다졸릴기, 이미다졸리닐기, 이미다졸리디닐기, 피라졸리닐기, 피라졸리디닐기, 피페리디닐기 및 피페라지닐기 등의 복소환기, 그리고 이들 기를 함유하는 기 등을 들 수 있다. As the heterocyclic ring-containing group having 2 to 20 carbon atoms in the general formula (I), for example, tetrahydrofuranyl group, dioxolanyl group, tetrahydropyranyl group, morpholyl group, furanyl group, thiophenyl group, methylthio Phenyl group, hexylthiophenyl group, benzothiophenyl group, pyrrolyl group, pyrrolidinyl group, imidazolyl group, imidazolinyl group, imidazolidinyl group, pyrazolinyl group, pyrazolidinyl group, piperidinyl group and piperazinyl group Heterocyclic groups, such as group, and the group containing these groups, etc. are mentioned.
또한, 탄소 원자 수 2~20의 복소환 함유기는 할로겐 원자, 시아노기, 니트로기, 수산기, -OR50, -COOR50, -CO-R50 또는 -SR50 등의 치환기를 가지고 있어도 되고, -O-, -CO-, -COO-, -NR51-, -NR51CO- 또는 -S- 등의 구조를 포함하고 있어도 된다. In addition, the heterocyclic ring-containing group having 2 to 20 carbon atoms may have a substituent such as a halogen atom, a cyano group, a nitro group, a hydroxyl group, -OR 50 , -COOR 50 , -CO-R 50 or -SR 50 , - It may contain structures, such as O-, -CO-, -COO-, -NR 51 -, -NR 51 CO-, or -S-.
여기서, R50 및 R51은 각각 독립적으로 수소 원자 또는 탄소 원자 수 1~20의 탄화수소기를 나타낸다. R50 및 R51로 표현되는 탄소 원자 수 1~20의 탄화수소기는 상기 일반식(I), 상기 일반식(a) 및 상기 일반식(b)에서의 탄소 원자 수 1~20의 탄화수소기와 마찬가지이다. Here, R 50 and R 51 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon group having 1 to 20 carbon atoms represented by R 50 and R 51 is the same as the hydrocarbon group having 1 to 20 carbon atoms in the general formulas (I), (a) and (b). .
상기 일반식(I)에서의 R3과 R4, R6과 R7, R7과 R8 및 R8과 R9가 서로 연결되어 형성하는, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 3~10의 환으로는 벤젠환, 시클로헥센환, 시클로헥산환, 시클로펜타디엔환, 시클로펜탄환 등을 들 수 있다. 또한, 이들 환은 치환기를 가지고 있어도 되고, 그 경우의 치환기로는 상기 탄소 원자 수 2~20의 복소환 함유기가 가지고 있어도 되는 치환기를 들 수 있다. R 3 and R 4 , R 6 and R 7 , R 7 and R 8 , and R 8 and R 9 in the general formula (I) are connected to each other to form a hydrogen atom and a carbon atom number of 3 to 10 carbon atoms Examples of the ring include a benzene ring, a cyclohexene ring, a cyclohexane ring, a cyclopentadiene ring, and a cyclopentane ring. Moreover, these rings may have a substituent, and the substituent which the said C2-C20 heterocyclic-containing group may have as a substituent in that case is mentioned.
상기 일반식(I), 상기 일반식(a) 및 상기 일반식(b)에서의 R21과 R22, R31과 R32, R33과 R34, R35와 R36, R37과 R38, 및 R39와 R40이 서로 연결되어 형성하는, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환으로는 결합하고 있는 질소 원자를 포함시킨 환으로서, 피롤환, 피롤리딘환, 이미다졸환, 이미다졸리딘환, 이미다졸린환, 피라졸환, 피라졸리딘환, 피페리딘환, 피페라진환 등을 들 수 있다. 이들 환은 치환기를 가지고 있어도 되고, 그 경우의 치환기로는 상기 탄소 원자 수 2~20의 복소환 함유기가 가지고 있어도 되는 치환기를 들 수 있다. R 21 and R 22 , R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R in the general formula (I), the general formula (a) and the general formula (b). 38 , and R 39 and R 40 are linked to each other to form a ring containing a nitrogen atom bonded to a ring having 2 to 10 carbon atoms consisting of a hydrogen atom, a nitrogen atom, and a carbon atom, a pyrrole ring, a pyrrole ring A din ring, an imidazole ring, an imidazolidine ring, an imidazoline ring, a pyrazole ring, a pyrazolidine ring, a piperidine ring, a piperazine ring, etc. are mentioned. These rings may have a substituent, and the substituent which the said C2-C20 heterocyclic-containing group may have as a substituent in that case is mentioned.
상기 일반식(I), 상기 일반식(a) 및 상기 일반식(b)에서의 R21과 R22, R31과 R32, R33과 R34, R35와 R36, R37과 R38, 및 R39와 R40이 서로 연결되어 형성하는, 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환으로는 결합하고 있는 질소 원자를 포함시킨 환으로서, 모르폴린환, 옥사졸환, 옥사졸린환, 옥사디아졸환 등을 들 수 있다. 이들 환은 치환기를 가지고 있어도 되고, 그 경우의 치환기로는 상기 탄소 원자 수 2~20의 복소환 함유기가 가지고 있어도 되는 치환기를 들 수 있다. R 21 and R 22 , R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R in the general formula (I), the general formula (a) and the general formula (b). 38 , and R 39 and R 40 are linked to each other to form a ring containing a nitrogen atom bonded to a ring having 2 to 10 carbon atoms consisting of a hydrogen atom, an oxygen atom, a nitrogen atom, and a carbon atom, morpholine A ring, an oxazole ring, an oxazoline ring, an oxadiazole ring, etc. are mentioned. These rings may have a substituent, and the substituent which the said C2-C20 heterocyclic-containing group may have as a substituent in that case is mentioned.
일반식(I) 중의 R1이 탄소 원자 수 6~20의 방향족 탄화수소기인 카르바모일옥심 화합물은 얻어지는 중합성 조성물이 저노광량으로 경화되기 때문에 바람직하고, 특히 벤젠환을 함유하는 탄소 원자 수 6~20의 방향족 탄화수소기인 카르바모일옥심 화합물이 바람직하다. 또한, 상기 R1이 탄소 원자 수 1~20의 지방족 탄화수소기인 것도, 얻어지는 중합성 조성물이 저노광량에서 경화되기 때문에 바람직하다. The carbamoyloxime compound in which R 1 in the general formula (I) is an aromatic hydrocarbon group having 6 to 20 carbon atoms is preferable because the resulting polymerizable composition is cured at a low exposure dose, and in particular, a benzene ring containing 6 to carbon atoms The carbamoyloxime compound which is an aromatic hydrocarbon group of 20 is preferable. Moreover, it is also preferable that said R< 1 > is a C1-C20 aliphatic hydrocarbon group, since the obtained polymerizable composition hardens|cures at a low exposure dose.
본 발명에서는 용제에 대한 용해성이 뛰어나기 때문에, 일반식(I) 중의 R2가 탄소 원자 수 1~10의 지방족 탄화수소기인 카르바모일옥심 화합물이 바람직하고, 특히 탄소 원자 수 1~10의 분기를 가지는 알킬기인 것이 바람직하다. In the present invention, since the solubility to a solvent is excellent, a carbamoyloxime compound in which R 2 in the general formula (I) is an aliphatic hydrocarbon group having 1 to 10 carbon atoms is preferable, and in particular, a branch having 1 to 10 carbon atoms is used. It is preferable that a branch is an alkyl group.
상기 일반식(I) 중의 R3과 R4, 또는 R8과 R9가 서로 연결되어 벤젠환을 형성하고 있는 카르바모일옥심 화합물은 얻어지는 중합성 조성물이 저노광량으로 경화되기 때문에 바람직하다. A carbamoyloxime compound in which R 3 and R 4 or R 8 and R 9 in the general formula (I) are linked to each other to form a benzene ring is preferable because the resulting polymerizable composition is cured with a low exposure dose.
일반식(I) 중의 X1이 -NR21R22이고, R21과 R22가 서로 연결되어 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환을 형성하고 있는 카르바모일옥심 화합물은 염기 발생 효율이 높기 때문에 바람직하고, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~6의 환 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~6의 환을 형성하고 있는 것이 보다 바람직하다. In the general formula (I), X 1 is -NR 21 R 22 , R 21 and R 22 are connected to each other to form a ring having 2 to 10 carbon atoms or a hydrogen atom, an oxygen atom, or a nitrogen atom comprising a hydrogen atom, a nitrogen atom and a carbon atom A carbamoyloxime compound forming a ring of 2 to 10 carbon atoms consisting of atoms and carbon atoms is preferable because of high base generation efficiency, and a ring of 2 to 6 carbon atoms consisting of a hydrogen atom, a nitrogen atom and a carbon atom; or It is more preferable to form a C2-C6 ring which consists of a hydrogen atom, an oxygen atom, a nitrogen atom, and a carbon atom.
특히 R21과 R22가 서로 연결되어 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~6의 환을 형성하고 있는 것이 바람직하고, 피페리딘환 또는 피롤리딘환을 형성하고 있는 것이 더 바람직하다. In particular, it is preferable that R 21 and R 22 are linked to each other to form a ring having 2 to 6 carbon atoms comprising a hydrogen atom, a nitrogen atom and a carbon atom, and more preferably a piperidine ring or a pyrrolidine ring. .
또한, 일반식(I) 중의 X1이 -NR21R22인 카르바모일옥심 화합물에서 R21이 수소 원자이며 R22가 탄소 원자 수 6~20의 방향족 탄화수소기인 것, 그리고 R21 및 R22가 모두 탄소 원자 수 1~20의 지방족 탄화수소기인 것도 염기 발생 효율이 높기 때문에 바람직하다. Further, in the carbamoyloxime compound in which X 1 is -NR 21 R 22 in the general formula (I), R 21 is a hydrogen atom and R 22 is an aromatic hydrocarbon group having 6 to 20 carbon atoms, and R 21 and R 22 It is also preferable that all are aliphatic hydrocarbon groups having 1 to 20 carbon atoms because of high base generation efficiency.
R3, R4, R5, R6, R7, R8 및 R9 중 하나 이상이 -CO-R10이고 R10이 탄소 원자 수 6~20의 방향족 탄화수소기인 카르바모일옥심 화합물은 얻어지는 중합성 조성물이 저노광량으로 경화되기 때문에 바람직하고, R7이 -CO-R10이고 R10이 벤젠환을 함유하는 탄소 원자 수 6~20의 방향족 탄화수소기인 카르바모일옥심 화합물이 특히 바람직하다. A carbamoyloxime compound wherein at least one of R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 is -CO-R 10 and R 10 is an aromatic hydrocarbon group having 6 to 20 carbon atoms is obtained It is preferable because the polymerizable composition is cured at a low exposure dose, and a carbamoyloxime compound in which R 7 is —CO-R 10 and R 10 is an aromatic hydrocarbon group having 6 to 20 carbon atoms containing a benzene ring is particularly preferable.
상기 일반식(I) 중의 n이 0인 카르바모일옥심 화합물은 열에 대한 안정성이 높기 때문에 바람직하다. The carbamoyloxime compound in which n is 0 in the said general formula (I) is preferable since stability with respect to heat|fever is high.
상기 일반식(I) 중의 n이 1인 카르바모일옥심 화합물은 얻어지는 중합성 조성물이 저노광량으로 경화되기 때문에 바람직하다. The carbamoyloxime compound in which n is 1 in the said General formula (I) is preferable since the polymerizable composition obtained hardens|cures with a low exposure dose.
본 발명에서 가장 바람직한 것은 일반식(I) 중의 R1이 탄소 원자 수 6~20의 방향족 탄화수소기이고, R2가 탄소 원자 수 1~10의 분기를 가지는 알킬기이며, R8과 R9가 서로 연결되어 벤젠환을 형성하고 있고, X1이 -NR21R22이며, R21과 R22가 서로 연결되어 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환을 형성하고 있고, R7이 -CO-R10이며, R10이 탄소 원자 수 6~20의 방향족 탄화수소기이고, n이 0인 카르바모일옥심 화합물이다. Most preferred in the present invention is that R 1 in the general formula (I) is an aromatic hydrocarbon group having 6 to 20 carbon atoms, R 2 is an alkyl group having a branch of 1 to 10 carbon atoms, and R 8 and R 9 are each other connected to form a benzene ring, X 1 is -NR 21 R 22 , R 21 and R 22 are connected to each other to form a ring having 2 to 10 carbon atoms consisting of a hydrogen atom, a nitrogen atom, and a carbon atom, R 7 is -CO-R 10 , R 10 is an aromatic hydrocarbon group having 6 to 20 carbon atoms, and n is 0, a carbamoyloxime compound.
상기 일반식(I)로 표현되는 카르바모일옥심 화합물의 구체예로는 이하의 화학식(1)~(52)로 표현되는 화합물을 들 수 있다. 단, 본 발명은 이하의 화합물에 의해 조금도 제한을 받는 것이 아니다. Specific examples of the carbamoyloxime compound represented by the general formula (I) include compounds represented by the following formulas (1) to (52). However, the present invention is not limited in any way by the following compounds.
상기 일반식(I)로 표현되는 본 발명의 카르바모일옥심 화합물의 제조 방법은 특별히 한정되지 않는데, 예를 들면, R8과 R9가 서로 연결되어 벤젠환을 형성하고 있고 X1이 -NR21R22이며 n=0인 경우, 하기 반응식 1에 따라 이하의 방법에 의해 제조할 수 있다. The method for producing the carbamoyloxime compound of the present invention represented by the general formula (I) is not particularly limited, for example, R 8 and R 9 are connected to each other to form a benzene ring, and X 1 is -NR 21 R 22 and when n=0, it may be prepared by the following method according to Scheme 1 below.
즉, 공지인 케톤 화합물과 염산하이드록실아민을 피리딘 등의 염기 존재 하에 반응시킴으로써 옥심 화합물을 얻는다. 계속해서, 옥심 화합물에 클로로포름산4-니트로페닐을 반응시키고, 이어서 아민을 반응시킴으로써, 본 발명의 카르바모일옥심 화합물이 얻어진다. That is, an oxime compound is obtained by making a well-known ketone compound and hydroxylamine hydrochloride react in presence of bases, such as pyridine. Then, the carbamoyl oxime compound of this invention is obtained by making an oxime compound react chloroformic acid 4-nitrophenyl, and then making an amine react.
(식 중 R1~R7, R21 및 R22는 상기 일반식(I)과 동일함.) (Wherein, R 1 to R 7 , R 21 and R 22 are the same as in General Formula (I).)
상기 반응식 1은 X1이 -NR21R22인 경우를 나타내고 있는데, 사용하는 아민을 변경함으로써 X1이 상기 일반식(a) 또는 상기 일반식(b)로 표현되는 기인 화합물도 제조할 수 있다. Scheme 1 shows a case in which X 1 is -NR 21 R 22. By changing the amine to be used, a compound can also be prepared in which X 1 is a group represented by the general formula (a) or (b). .
옥심 화합물은 일본 특허공보 특허제4223071호에 기재된 방법으로도 제조할 수 있다. The oxime compound can also be produced by the method described in Japanese Patent Application Laid-Open No. 4223071.
본 발명의 카르바모일옥심 화합물은 자외선 등의 광조사 또는 가열에 의해 효율적으로 염기 및 라디칼을 발생시키기 때문에 잠재성 염기 발생제 및 중합 개시제로 유용하고, 특히 중합 개시제로 유용하다. The carbamoyloxime compound of the present invention is useful as a latent base generator and a polymerization initiator, especially as a polymerization initiator, because it efficiently generates a base and a radical by irradiation with light such as ultraviolet rays or heating.
본 발명의 잠재성 염기 발생제란 자외선 등의 광을 조사함으로써 효율적으로 염기를 발생시키는 기능을 가진 화합물을 함유하는 조성물을 의미하고, 그 용도로는 pH 조정제, 염기를 이용한 촉매 등을 들 수 있다. The latent base generator of the present invention means a composition containing a compound having a function of efficiently generating a base by irradiating light such as ultraviolet rays, and examples thereof include a pH adjuster, a catalyst using a base, and the like. .
또한, 본 발명의 카르바모일옥심 화합물은 상기 중합 개시제 중에서도 광조사에 의한 염기 및 라디칼의 발생 효율이 높기 때문에 광염기 발생제 및 광 라디칼 중합 개시제로서 유용하고, 염기 발생 효율이 상당히 높기 때문에 특히 광염기 발생제로서 유용하다. In addition, the carbamoyloxime compound of the present invention is useful as a photobase generator and a photoradical polymerization initiator because of its high efficiency of generating a base and radicals by light irradiation among the polymerization initiators, and especially since the base generation efficiency is quite high. It is useful as a base generator.
본 발명의 중합 개시제는 상기 일반식(I)로 표현되는 카르바모일옥심 화합물을 적어도 1종 함유한다. 상기 일반식(I)로 표현되는 카르바모일옥심 화합물과 병용할 수 있는 중합 개시제로는 특별히 제한되는 것은 아니지만, 종래 기지(旣知)의 광염기 발생제 및 광 라디칼 중합 개시제를 들 수 있다. The polymerization initiator of this invention contains at least 1 sort(s) of the carbamoyl oxime compound represented by the said General formula (I). Although it does not restrict|limit especially as a polymerization initiator which can be used together with the carbamoyl oxime compound represented by the said General formula (I), Conventionally well-known photobase generator and photoradical polymerization initiator are mentioned.
상기 중합 개시제 중에서의 상기 일반식(I)로 표현되는 화합물의 함유량은 얻어지는 중합성 조성물이 저노광량으로 경화되기 때문에 바람직하게는 1~100질량%, 보다 바람직하게는 50~100질량%이다. The content of the compound represented by the general formula (I) in the polymerization initiator is preferably 1 to 100% by mass, more preferably 50 to 100% by mass, because the resulting polymerizable composition is cured at a low exposure dose.
본 발명의 중합성 조성물은 상기 일반식(I)로 표현되는 카르바모일옥심 화합물을 적어도 1종 함유하는 중합 개시제(A), 및 중합성 화합물(B)을 함유하는 것이다. The polymerizable composition of the present invention contains a polymerization initiator (A) containing at least one carbamoyloxime compound represented by the general formula (I), and a polymerizable compound (B).
중합 개시제(A)의 함유량은 중합성 화합물(B) 100질량부에 대하여, 얻어지는 중합성 조성물이 저노광량으로 경화되기 때문에 바람직하게는 1~20질량부, 보다 바람직하게는 1~10질량부이다. 중합 개시제(A)의 함유량이 1질량부 이상임으로써 경화 감도 부족에 의한 경화 불량을 방지하기 쉽기 때문에 바람직하고, 20질량부 이하로 함으로써 광조사 시 또는 가열 시의 휘발물을 억제할 수 있기 때문에 바람직하다. The content of the polymerization initiator (A) is preferably 1 to 20 parts by mass, more preferably 1 to 10 parts by mass, because the polymerizable composition obtained is cured at a low exposure dose with respect to 100 parts by mass of the polymerizable compound (B). . When the content of the polymerization initiator (A) is 1 part by mass or more, it is preferable because it is easy to prevent curing failure due to insufficient curing sensitivity, and when the content of the polymerization initiator (A) is 20 parts by mass or less, volatiles during light irradiation or heating can be suppressed. Do.
본 발명에서 사용되는 중합성 화합물(B)로는 음이온 중합성 관능기를 가지는 화합물, 염기가 촉매로서 작용하는 반응 또는 염기가 부가되는 반응에 의해 경화되는 화합물, 및 라디칼 중합성 화합물을 들 수 있고, 자외선 등의 에너지선을 조사함으로써 중합하여 경화되는 감광성 수지 또는 경화 온도가 저온화되는 경화 수지인 것이 얻어지는 중합성 조성물이 저노광량으로 경화되기 때문에 바람직하다. 상기 음이온 중합성 관능기란, 자외선 등의 활성 에너지선에 의해 광염기 발생제로부터 발생하는 염기에 의해 중합할 수 있는 관능기를 의미하고, 예를 들면, 에폭시기, 에피설파이드기, 환상 모노머(σ-발레로락톤, ε-카프로락탐), 말론산에스테르 등을 들 수 있다. 염기가 촉매로서 작용하는 반응 또는 염기가 부가되는 반응으로는 이소시아네이트와 알코올에 의한 우레탄 결합 형성 반응, 에폭시 수지와 수산기를 함유하는 화합물의 부가 반응, 에폭시 수지와 카르복실산기를 함유하는 화합물의 부가 반응, 에폭시 수지와 티올 화합물의 부가 반응, (메타)아크릴기의 마이클 부가 반응, 폴리아믹산의 탈수축합 반응, 알콕시실란의 가수분해·중축합 반응 등을 들 수 있다. Examples of the polymerizable compound (B) used in the present invention include a compound having an anionically polymerizable functional group, a compound cured by a reaction in which a base acts as a catalyst or a reaction in which a base is added, and a radically polymerizable compound, and ultraviolet rays Since the polymerizable composition obtained that it is the photosensitive resin which superposes|polymerizes and hardens|cures by irradiating energy rays, or the cured resin whose curing temperature is lowered|lowered, is hardened|cured with low exposure dose, it is preferable. The anionically polymerizable functional group means a functional group that can be polymerized with a base generated from a photobase generator by active energy rays such as ultraviolet rays, for example, an epoxy group, an episulfide group, a cyclic monomer (σ-valence). Lolactone, ε-caprolactam), malonic acid ester, and the like. A reaction in which a base acts as a catalyst or a reaction in which a base is added includes a urethane bond formation reaction between an isocyanate and an alcohol, an addition reaction between an epoxy resin and a compound containing a hydroxyl group, and an addition reaction between an epoxy resin and a compound containing a carboxylic acid group , addition reaction of an epoxy resin and a thiol compound, Michael addition reaction of a (meth)acrylic group, dehydration condensation reaction of polyamic acid, hydrolysis/polycondensation reaction of alkoxysilane, etc. are mentioned.
음이온 중합성 관능기를 가지는 화합물로는 예를 들면, 에폭시 수지, 옥세탄 수지, 에피설파이드 수지, 환상 아미드(락탐계 화합물), 환상 에스테르(락톤계 화합물), 환상 카보네이트계 화합물, 말론산에스테르 등을 들 수 있다. 염기가 촉매로서 작용하는 반응 또는 염기가 부가되는 반응에 의해 경화되는 화합물로는 예를 들면, 폴리아미드 수지(탈수 환화에 의한 폴리이미드화 반응), 에폭시·수산기계 (개환 부가 반응), 에폭시·카르복실산계(개환 부가 반응), 에폭시·티올계(개환 부가 반응), 에폭시·산무수물계(개환 중축합), 시아네이트에스테르(트리아진환화 반응), 시아네이트에스테르·에폭시계(환화 반응), 시아네이트에스테르·말레이미드계(가교 공중합), 옥세탄·수산기계(개환 부가 반응), 옥세탄·카르복실산계(개환 부가 반응), 옥세탄·티올계(개환 부가 반응), 옥세탄·산무수물계(개환 중축합), 에피설파이드·수산기계(개환 부가 반응), 에피설파이드·카르복실산계(개환 부가 반응), 에피설파이드·티올계(개환 부가 반응), 에피설파이드·산무수물계(개환 중축합), 아크릴·티올계(마이클 부가 반응), 메타크릴·티올계(마이클 부가 반응), 아크릴·아민계(마이클 부가 반응), 메타크릴·아민계(마이클 부가 반응), 카르복실산·수산기계(폴리에스테르화 반응), 카르복실산·아민계(폴리아미드화 반응), 이소시아네이트·수산기계(폴리우레탄화 반응), 이소시아네이트·티올계(폴리티오우레탄화 반응), 알콕시실란계(가수분해·중축합) 등을 들 수 있다. 라디칼에 의해 중합되는 화합물로는 에틸렌성 불포화 화합물을 들 수 있다. 반응성이 높기 때문에 라디칼 중합되는 화합물을 사용하는 것이 바람직하다. 이들 수지는 단독으로 사용해도 되고, 2종 이상을 병용해도 된다. 바람직한 조합으로서, 신속하게 반응이 진행되는 것이나 접착성이 양호하다는 점에서 에폭시 수지와 페놀 수지의 조합, 저온 경화성이 뛰어나기 때문에 에폭시 수지와 티올 화합물의 조합, 반응성이 높기 때문에 에틸렌성 불포화 화합물과 티올 화합물의 조합을 들 수 있다. Examples of the compound having an anionic polymerizable functional group include epoxy resins, oxetane resins, episulfide resins, cyclic amides (lactam compounds), cyclic esters (lactone compounds), cyclic carbonate compounds, malonic acid esters, etc. can be heard As a compound that is cured by a reaction in which a base acts as a catalyst or a reaction in which a base is added, for example, polyamide resin (polyimidization reaction by dehydration cyclization), epoxy/hydroxyl group (ring-opening addition reaction), epoxy/ Carboxylic acid type (ring-opening addition reaction), epoxy/thiol type (ring-opening addition reaction), epoxy/acid anhydride type (ring-opening polycondensation), cyanate ester (triazine cyclization reaction), cyanate ester/epoxy type (cyclization reaction) , cyanate ester maleimide type (cross-linking copolymerization), oxetane/hydroxyl group (ring-opening addition reaction), oxetane/carboxylic acid type (ring-opening addition reaction), oxetane/thiol type (ring-opening addition reaction), oxetane/ Acid anhydride system (ring-opening polycondensation), episulfide hydroxyl system (ring-opening addition reaction), episulfide carboxylic acid system (ring-opening addition reaction), episulfide thiol system (ring-opening addition reaction), episulfide acid anhydride system (ring-opening addition reaction) Ring-opening polycondensation), acrylic thiol system (Michael addition reaction), methacryl thiol system (Michael addition reaction), acrylic amine system (Michael addition reaction), methacryl amine system (Michael addition reaction), carboxylic acid · Hydroxyl group (polyesterification reaction), carboxylic acid/amine type (polyamidation reaction), isocyanate/hydroxyl type (polyurethanation reaction), isocyanate/thiol type (polythiourethanation reaction), alkoxysilane type ( hydrolysis and polycondensation); Examples of the compound polymerized by radicals include ethylenically unsaturated compounds. It is preferable to use a compound that undergoes radical polymerization because of its high reactivity. These resins may be used independently and may use 2 or more types together. As a preferable combination, a combination of an epoxy resin and a phenol resin in terms of rapid reaction and good adhesion, a combination of an epoxy resin and a thiol compound because of excellent low temperature curability, and an ethylenically unsaturated compound and a thiol because of high reactivity and combinations of compounds.
상기 에폭시 수지는 에폭시기를 가지고 있으면 되는데, 본 발명의 카르바모일옥심 화합물을 제외한다. 에폭시 수지로는 예를 들면, 하이드로퀴논, 레조르신, 피로카테콜, 플로로글루쿠시놀 등의 단핵 다가 페놀 화합물의 폴리글리시딜에테르 화합물; 디하이드록시나프탈렌, 비페놀, 메틸렌비스페놀(비스페놀F), 메틸렌비스(오르토크레졸), 에틸리덴비스페놀, 이소프로필리덴비스페놀(비스페놀A), 4,4'-디하이드록시벤조페논, 이소프로필리덴비스(오르토크레졸), 테트라브로모비스페놀A, 1,3-비스(4-하이드록시쿠밀벤젠), 1,4-비스(4-하이드록시쿠밀벤젠), 1,1,3-트리스(4-하이드록시페닐)부탄, 1,1,2,2-테트라(4-하이드록시페닐)에탄, 티오비스페놀, 설포비스페놀, 옥시비스페놀, 페놀노볼락, 오르토크레졸노볼락, 에틸페놀노볼락, 부틸페놀노볼락, 옥틸페놀노볼락, 레조르신노볼락, 테르펜페놀 등의 다핵 다가 페놀 화합물의 폴리글리시딜에테르 화합물; 에틸렌글리콜, 프로필렌글리콜, 부틸렌글리콜, 헥산디올, 폴리글리콜, 티오디글리콜, 글리세린, 트리메틸올프로판, 펜타에리트리톨, 소르비톨, 비스페놀A-에틸렌옥사이드 부가물 등의 다가 알코올류의 폴리글리시딜에테르; 말레산, 푸마르산, 이타콘산, 석신산, 글루타르산, 수베르산, 아디프산, 아젤라산, 세바스산, 다이머산, 트리머산, 프탈산, 이소프탈산, 테레프탈산, 트리멜리트산, 트리메신산, 피로멜리트산, 테트라하이드로프탈산, 헥사하이드로프탈산, 엔드메틸렌테트라하이드로프탈산 등의 지방족, 방향족 또는 지환족 다염기산의 글리시딜에스테르류, 및 글리시딜메타크릴레이트의 단독 중합체 또는 공중합체; N,N-디글리시딜아닐린, 비스(4-(N-메틸-N-글리시딜아미노)페닐)메탄, 디글리시딜오르토톨루이딘 등의 글리시딜아미노기를 가지는 에폭시 화합물; 비닐시클로헥센디에폭시드, 디시클로펜탄디엔디에폭사이드, 3,4-에폭시시클로헥실메틸-3,4-에폭시시클로헥산카르복실레이트, 3,4-에폭시-6-메틸시클로헥실메틸-6-메틸시클로헥산카르복실레이트, 비스(3,4-에폭시-6-메틸시클로헥실메틸)아디페이트 등의 환상 올레핀 화합물의 에폭시화물; 에폭시화폴리부타디엔, 에폭시화아크릴로니트릴-부타디엔 공중합물, 에폭시화스티렌-부타디엔 공중합물 등의 에폭시화 공역디엔 중합체, 트리글리시딜이소시아누레이트 등의 복소환 화합물을 들 수 있다. 또한, 이들 에폭시 수지는 말단 이소시아네이트의 프레폴리머에 의해 내부 가교된 것 혹은 다가의 활성 수소 화합물(다가 페놀, 폴리아민, 카르보닐기 함유 화합물, 폴리인산에스테르 등)로 고분자량화된 것이어도 된다. Although the said epoxy resin should just have an epoxy group, the carbamoyl oxime compound of this invention is excluded. Examples of the epoxy resin include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol, and phloroglucosinol; Dihydroxynaphthalene, biphenol, methylenebisphenol (bisphenol F), methylenebis (orthocresol), ethylidenebisphenol, isopropylidenebisphenol (bisphenol A), 4,4'-dihydroxybenzophenone, isopropylidenebis (orthocresol), tetrabromobisphenol A, 1,3-bis(4-hydroxycumylbenzene), 1,4-bis(4-hydroxycumylbenzene), 1,1,3-tris(4-hydro Roxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfobisphenol, oxybisphenol, phenol novolac, orthocresol novolac, ethylphenol novolac, butylphenol novolac polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as , octylphenol novolac, resorcin novolac, and terpene phenol; Polyglycidyl ether of polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, hexanediol, polyglycol, thiodiglycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, and bisphenol A-ethylene oxide adduct ; Maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, trimeric acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, glycidyl esters of aliphatic, aromatic or alicyclic polybasic acids such as pyromellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, and endmethylenetetrahydrophthalic acid, and homopolymers or copolymers of glycidyl methacrylate; an epoxy compound having a glycidylamino group such as N,N-diglycidylaniline, bis(4-(N-methyl-N-glycidylamino)phenyl)methane, and diglycidylorthotoluidine; Vinylcyclohexene diepoxide, dicyclopentane diene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6- epoxidized products of cyclic olefin compounds such as methylcyclohexanecarboxylate and bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate; and epoxidized conjugated diene polymers such as epoxidized polybutadiene, epoxidized acrylonitrile-butadiene copolymer, and epoxidized styrene-butadiene copolymer, and heterocyclic compounds such as triglycidyl isocyanurate. In addition, these epoxy resins may be internally crosslinked by a prepolymer of terminal isocyanate or high molecular weight with a polyvalent active hydrogen compound (polyhydric phenol, polyamine, carbonyl group-containing compound, polyphosphate ester, etc.).
상기 에폭시 수지 중에서는, 얻어지는 중합성 조성물의 경화성이 뛰어난 점에서 글리시딜기를 가지는 것이 바람직하고, 2관능 이상의 글리시딜기를 가지는 것이 보다 바람직하다. In the said epoxy resin, it is preferable to have a glycidyl group at the point excellent in sclerosis|hardenability of the polymeric composition obtained, and it is more preferable to have a glycidyl group more than bifunctional.
상기 페놀 수지는 페놀성 수산기를 가지고 있으면 되는데, 상기 카르바모일옥심 화합물 및 에폭시 수지를 제외한다. 페놀 수지로는 1분자 중에 2개 이상의 하이드록시기를 가지는 페놀 수지가, 얻어지는 중합성 조성물의 경화성이 뛰어난 점에서 바람직하고, 일반적으로 공지의 것을 사용할 수 있다. 페놀 수지로는 예를 들면, 비스페놀A형 페놀 수지, 비스페놀E형 페놀 수지, 비스페놀F형 페놀 수지, 비스페놀S형 페놀 수지, 페놀노볼락 수지, 비스페놀A노볼락형 페놀 수지, 글리시딜에스테르형 페놀 수지, 아르알킬노볼락형 페놀 수지, 비페닐아르알킬형 페놀 수지, 크레졸 노볼락형 페놀 수지, 다관능 페놀 수지, 나프톨 수지, 나프톨노볼락 수지, 다관능 나프톨 수지, 안트라센형 페놀 수지, 나프탈렌 골격 변성 노볼락형 페놀 수지, 페놀아르알킬형 페놀 수지, 나프톨아르알킬형 페놀 수지, 디시클로펜타디엔형 페놀 수지, 비페닐형 페놀 수지, 지환식 페놀 수지, 폴리올형 페놀 수지, 인 함유 페놀 수지, 중합성 불포화 탄화수소기 함유 페놀 수지 및, 수산기 함유 실리콘 수지류를 들 수 있는데, 특별히 제한되는 것은 아니다. 이들 페놀 수지는 1종을 단독으로 또는 2종 이상을 조합하여 사용할 수 있다. Although the said phenol resin should just have a phenolic hydroxyl group, the said carbamoyl oxime compound and an epoxy resin are excluded. As a phenol resin, the phenol resin which has two or more hydroxyl groups in 1 molecule is preferable at the point excellent in sclerosis|hardenability of the polymerizable composition obtained, and a generally well-known thing can be used. Examples of the phenol resin include bisphenol A phenol resin, bisphenol E phenol resin, bisphenol F phenol resin, bisphenol S phenol resin, phenol novolac resin, bisphenol A novolak phenol resin, glycidyl ester resin Phenolic resin, aralkyl novolak type phenol resin, biphenyl aralkyl type phenol resin, cresol novolak type phenol resin, polyfunctional phenol resin, naphthol resin, naphthol novolak resin, polyfunctional naphthol resin, anthracene type phenol resin, naphthalene Skeletal-modified novolak type phenol resin, phenol aralkyl type phenol resin, naphthol aralkyl type phenol resin, dicyclopentadiene type phenol resin, biphenyl type phenol resin, alicyclic phenol resin, polyol type phenol resin, phosphorus-containing phenol resin , a polymerizable unsaturated hydrocarbon group-containing phenol resin, and a hydroxyl group-containing silicone resin, but is not particularly limited. These phenol resins can be used individually by 1 type or in combination of 2 or more type.
상기 티올 화합물은 티올기를 가지고 있으면 되는데, 상기 카르바모일옥심 화합물, 에폭시 수지 및 페놀 수지를 제외한다. 티올 화합물 중에서도 얻어지는 중합성 조성물의 경화성이 뛰어난 점에서 1분자 중에 2개 이상의 티올기를 가지는 것이 바람직하다. The thiol compound should just have a thiol group, except for the carbamoyloxime compound, the epoxy resin, and the phenol resin. Among thiol compounds, it is preferable to have two or more thiol groups in one molecule from the viewpoint of excellent curability of the obtained polymerizable composition.
티올 화합물의 바람직한 구체예로는 비스(2-메르캅토에틸)설파이드, 2,5-디메르캅토메틸-1,4-디티안, 1,3-비스(메르캅토메틸)벤젠, 1,4-비스(메르캅토메틸)벤젠, 4-메르캅토메틸-1,8-디메르캅토-3,6-디티아옥탄, 4,8-디메르캅토메틸-1,11-디메르캅토-3,6,9-트리티아운데칸, 4,7-디메르캅토메틸-1,11-디메르캅토-3,6,9-트리티아운데칸, 5,7-디메르캅토메틸-1,11-디메르캅토-3,6,9-트리티아운데칸, 1,2,6,7-테트라메르캅토-4-티아헵탄, 펜타에리트리티올, 1,1,3,3-테트라키스(메르캅토메틸티오)프로판, 펜타에리트리톨테트라키스메르캅토프로피오네이트, 펜타에리트리톨테트라키스티오글리콜레이트, 트리메틸올프로판트리스티오글리콜레이트, 및 트리메틸올프로판트리스메르캅토프로피오네이트이고, 보다 바람직하게는 1,2,6,7-테트라메르캅토-4-티아헵탄, 펜타에리트리티올, 비스(2-메르캅토에틸)설파이드, 2,5-비스(2-메르캅토메틸)-1,4-디티안, 4-메르캅토메틸-1,8-디메르캅토-3,6-디티아옥탄, 1,3-비스(메르캅토메틸)벤젠, 펜타에리트리톨테트라키스메르캅토프로피오네이트, 및 펜타에리트리톨테트라키스티오글리콜레이트를 들 수 있다. Preferred examples of the thiol compound include bis(2-mercaptoethyl)sulfide, 2,5-dimercaptomethyl-1,4-dithiane, 1,3-bis(mercaptomethyl)benzene, 1,4- Bis(mercaptomethyl)benzene, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6 , 9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-di Mercapto-3,6,9-trithiaundecane, 1,2,6,7-tetramercapto-4-thiaheptane, pentaerythrthiol, 1,1,3,3-tetrakis (mercaptomethyl Thio) propane, pentaerythritol tetrakismercaptopropionate, pentaerythritol tetrakisthioglycolate, trimethylolpropane tristhioglycolate, and trimethylolpropane trismercaptopropionate, more preferably 1, 2,6,7-tetramercapto-4-thiaheptane, pentaerythrthiol, bis(2-mercaptoethyl)sulfide, 2,5-bis(2-mercaptomethyl)-1,4-dithiane; 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 1,3-bis(mercaptomethyl)benzene, pentaerythritoltetrakismercaptopropionate, and pentaerythritoltetra Kisthioglycolate is mentioned.
특히 바람직한 화합물은 1,2,6,7-테트라메르캅토-4-티아헵탄, 펜타에리트리티올, 비스(2-메르캅토에틸)설파이드, 2,5-디메르캅토메틸-1,4-디티안, 및 4-메르캅토메틸-1,8-디메르캅토-3,6-디티아옥탄이다. Particularly preferred compounds are 1,2,6,7-tetramercapto-4-thiaheptane, pentaerythrythiol, bis(2-mercaptoethyl)sulfide, 2,5-dimercaptomethyl-1,4-dithi and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane.
티올 화합물은 1종을 단독으로 또는 2종 이상을 조합하여 사용할 수 있다. A thiol compound can be used individually by 1 type or in combination of 2 or more type.
상기 폴리아미드 수지로는 산 이무수물로서 에틸렌테트라카르복실산 이무수물, 1,2,3,4-벤젠테트라카르복실산 이무수물, 1,2,3,4-시클로헥산테트라카르복실산 이무수물, 2,2',3,3'-벤조페논테트라카르복실산 이무수물, 2,2,3,3-비페닐테트라카르복실산 무수물, 1,4,5,8-나프탈렌테트라카르복실산 이무수물 등을, 디아민으로서 (o-, m- 혹은 p-)페닐렌디아민, (3,3'- 혹은 4,4'-)디아미노디페닐에테르, 디아미노벤조페논, (3,3'- 혹은 4,4'-)디아미노디페닐메탄 등을 원료로 하는 수지를 들 수 있다. Examples of the polyamide resin include ethylenetetracarboxylic dianhydride, 1,2,3,4-benzenetetracarboxylic dianhydride, and 1,2,3,4-cyclohexanetetracarboxylic dianhydride as acid dianhydride. , 2,2',3,3'-benzophenonetetracarboxylic dianhydride, 2,2,3,3-biphenyltetracarboxylic anhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride Water, etc. as a diamine, (o-, m- or p-) phenylenediamine, (3,3'- or 4,4'-) diaminodiphenyl ether, diaminobenzophenone, (3,3'- Or resin which uses 4,4'-) diaminodiphenylmethane etc. as a raw material is mentioned.
상기 폴리우레탄 수지로는 톨릴렌디이소시아네이트, 헥사메틸렌디이소시아네이트, 디페닐메탄디이소시아네이트, 이소포론디이소시아네이트 등의 다관능 이소시아네이트와, 폴리에테르폴리올, 폴리에스테르폴리올, 폴리카보네이트폴리올 등의 폴리올(다관능 알코올)을 원료로 하는 수지 등을 들 수 있다. Examples of the polyurethane resin include polyfunctional isocyanates such as tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, and isophorone diisocyanate, and polyols such as polyether polyols, polyester polyols and polycarbonate polyols (polyfunctional alcohols). ) as a raw material, and the like.
또한, 상기 나일론 수지로는 ε-카프로락탐, 라우릴락탐 등의 환상 모노머를 원료로 한 수지 등을 들 수 있다. Moreover, as said nylon resin, resin etc. which used cyclic monomers, such as an epsilon caprolactam and lauryl lactam, as a raw material are mentioned.
또한, 상기 폴리에스테르 수지로는 δ-발레로락톤, β-프로피오락톤 등의 환상 모노머를 원료로 한 수지 등을 들 수 있다. Moreover, as said polyester resin, the resin etc. which used cyclic monomers, such as (delta)-valerolactone and (beta)-propiolactone as a raw material, are mentioned.
상기 에틸렌성 불포화 화합물은 에틸렌성 불포화 결합을 가지고 있으면 되는데, 상기 카르바모일옥심 화합물, 에폭시 수지, 페놀 수지 및 티올 화합물을 제외한다. 에틸렌성 불포화 화합물로는 예를 들면, 에틸렌, 프로필렌, 부틸렌, 이소부틸렌, 염화비닐, 염화비닐리덴, 불화비닐리덴, 테트라플루오로에틸렌 등의 불포화 지방족 탄화수소; (메타)아크릴산, α-클로르아크릴산, 이타콘산, 말레산, 시트라콘산, 푸마루산, 하이믹산, 크로톤산, 이소크로톤산, 비닐아세트산, 알릴아세트산, 계피산, 소르브산, 메사콘산, 석신산모노[2-(메타)아크릴로일옥시에틸], 프탈산모노[2-(메타)아크릴로일옥시에틸], ω-카르복시폴리카프로락톤모노(메타)아크릴레이트 등의 양 말단에 카르복시기와 수산기를 가지는 폴리머의 모노(메타)아크릴레이트; 하이드록시에틸(메타)아크릴레이트·말레이트, 하이드록시프로필(메타)아크릴레이트·말레이트, 디시클로펜타디엔·말레이트 혹은 1개의 카르복실기와 2개 이상의 (메타)아크릴로일기를 가지는 다관능(메타)아크릴레이트 등의 불포화 다염기산; (메타)아크릴산-2-하이드록시에틸, (메타)아크릴산-2-하이드록시프로필, (메타)아크릴산글리시딜, (메타)아크릴산메틸, (메타)아크릴산부틸, (메타)아크릴산이소부틸, (메타)아크릴산-t-부틸, (메타)아크릴산시클로헥실, (메타)아크릴산n-옥틸, (메타)아크릴산이소옥틸, (메타)아크릴산이소노닐, (메타)아크릴산스테아릴, (메타)아크릴산라우릴, (메타)아크릴산메톡시에틸, (메타)아크릴산디메틸아미노메틸, (메타)아크릴산디메틸아미노에틸, (메타)아크릴산아미노프로필, (메타)아크릴산디메틸아미노프로필, (메타)아크릴산에톡시에틸, (메타)아크릴산폴리(에톡시)에틸, (메타)아크릴산부톡시에톡시에틸, (메타)아크릴산에틸헥실, (메타)아크릴산페녹시에틸, (메타)아크릴산테트라하이드로푸릴, (메타)아크릴산비닐, (메타)아크릴산알릴, (메타)아크릴산벤질, 에틸렌글리콜디(메타)아크릴레이트, 디에틸렌글리콜디(메타)아크릴레이트, 트리에틸렌글리콜디(메타)아크릴레이트, 폴리에틸렌글리콜디(메타)아크릴레이트, 프로필렌글리콜디(메타)아크릴레이트, 1,4-부탄디올디(메타)아크릴레이트, 1,6-헥산디올디(메타)아크릴레이트, 트리메틸올에탄트리(메타)아크릴레이트, 트리메틸올프로판트리(메타)아크릴레이트, 디펜타에리트리톨헥사(메타)아크릴레이트, 디펜타에리트리톨펜타(메타)아크릴레이트, 펜타에리트리톨테트라(메타)아크릴레이트, 펜타에리트리톨트리(메타)아크릴레이트, 트리시클로데칸디메틸올디(메타)아크릴레이트, 트리[(메타)아크릴로일에틸]이소시아누레이트, 폴리에스테르(메타)아크릴레이트올리고머 등의 불포화 일염기산 및 다가 알코올 또는 다가 페놀의 에스테르; (메타)아크릴산아연, (메타)아크릴산마그네슘 등의 불포화 다염기산의 금속염; 말레산 무수물, 이타콘산 무수물, 시트라콘산 무수물, 메틸테트라하이드로 무수프탈산, 테트라하이드로 무수프탈산, 트리알킬테트라하이드로 무수프탈산, 5-(2,5-디옥소테트라하이드로푸릴)-3-메틸-3-시클로헥센-1,2-디카르복실산 무수물, 트리알킬테트라하이드로 무수프탈산-무수말레산 부가물, 도데세닐 무수석신산, 무수메틸하이믹산 등의 불포화 다염기산의 산 무수물; (메타)아크릴아미드, 메틸렌비스-(메타)아크릴아미드, 디에틸렌트리아민트리스(메타)아크릴아미드, 크실릴렌비스(메타)아크릴아미드, α-클로로아크릴아미드, N-2-하이드록시에틸(메타)아크릴아미드 등의 불포화 일염기산 및 다가 아민의 아미드; 아크롤레인 등의 불포화 알데히드; (메타)아크릴로니트릴, α-클로로아크릴로니트릴, 시안화비닐리덴, 시안화알릴 등의 불포화 니트릴; 스티렌, 4-메틸스티렌, 4-에틸스티렌, 4-메톡시스티렌, 4-하이드록시스티렌, 4-클로로스티렌, 디비닐벤젠, 비닐톨루엔, 비닐안식향산, 비닐페놀, 비닐설폰산, 4-비닐벤젠설폰산, 비닐벤질메틸에테르, 비닐벤질글리시딜에테르 등의 불포화 방향족 화합물; 메틸비닐케톤 등의 불포화 케톤; 비닐아민, 알릴아민, N-비닐피롤리돈, 비닐피페리딘 등의 불포화 아민 화합물; 알릴알코올, 크로틸알코올 등의 비닐알코올; 비닐메틸에테르, 비닐에틸에테르, n-부틸비닐에테르, 이소부틸비닐에테르, 알릴글리시딜에테르 등의 비닐에테르; 말레이미드, N-페닐말레이미드, N-시클로헥실말레이미드 등의 불포화 이미드류; 인덴, 1-메틸인덴 등의 인덴류; 1,3-부타디엔, 이소프렌, 클로로프렌 등의 지방족 공역디엔류; 폴리스티렌, 폴리메틸(메타)아크릴레이트, 폴리-n-부틸(메타)아크릴레이트, 폴리실록산 등의 중합체 분자쇄의 말단에 모노(메타)아크릴로일기를 가지는 매크로모노머류; 비닐클로라이드, 비닐리덴클로라이드, 디비닐석시네이트, 디알릴프탈레이트, 트리알릴포스파이트, 트리알릴이소시아누레이트, 비닐티오에테르, 비닐이미다졸, 비닐옥사졸린, 비닐카르바졸, 비닐피롤리돈, 비닐피리딘, 수산기 함유 비닐 모노머 및 폴리이소시아네이트 화합물의 비닐우레탄 화합물, 수산기 함유 비닐 모노머 및 폴리에폭시 화합물의 비닐에폭시 화합물을 들 수 있다. Although the said ethylenically unsaturated compound should just have an ethylenically unsaturated bond, the said carbamoyl oxime compound, an epoxy resin, a phenol resin, and a thiol compound are excluded. Examples of the ethylenically unsaturated compound include unsaturated aliphatic hydrocarbons such as ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene chloride, vinylidene fluoride, and tetrafluoroethylene; (meth)acrylic acid, α-chloracrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinylacetic acid, allylacetic acid, cinnamic acid, sorbic acid, mesaconic acid, succinic acid A carboxyl group and a hydroxyl group at both terminals of mono[2-(meth)acryloyloxyethyl], mono[2-(meth)acryloyloxyethyl] phthalate, ω-carboxypolycaprolactone mono(meth)acrylate, etc. Mono (meth) acrylate of a polymer having; Hydroxyethyl (meth)acrylate maleate, hydroxypropyl (meth)acrylate maleate, dicyclopentadiene maleate, or polyfunctional (meth) having one carboxyl group and two or more (meth)acryloyl groups unsaturated polybasic acids such as meth)acrylate; (meth)acrylic acid-2-hydroxyethyl, (meth)acrylic acid-2-hydroxypropyl, (meth)acrylate glycidyl, (meth)acrylate methyl, (meth)acrylate butyl, (meth)acrylate isobutyl, ( meth)acrylic acid-t-butyl, (meth)acrylic acid cyclohexyl, (meth)acrylic acid n-octyl, (meth)acrylic acid isooctyl, (meth)acrylic acid isononyl, (meth)acrylic acid stearyl, (meth)acrylic acid la Uryl, (meth) acrylate methoxyethyl, (meth) acrylate dimethylaminomethyl, (meth) acrylate dimethyl aminoethyl, (meth) acrylate aminopropyl, (meth) acrylate dimethylaminopropyl, (meth) acrylate ethoxyethyl, ( (meth)acrylic acid poly(ethoxy)ethyl, (meth)acrylic acid butoxyethoxyethyl, (meth)acrylic acid ethylhexyl, (meth)acrylic acid phenoxyethyl, (meth)acrylic acid tetrahydrofuryl, (meth)acrylic acid vinyl, ( meth) allyl acrylate, (meth) benzyl acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene Glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolpropane tri(meth) Acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, pentaerythritol tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, tricyclodecanedimethyloldi esters of unsaturated monobasic acids and polyhydric alcohols or polyhydric phenols such as (meth)acrylate, tri[(meth)acryloylethyl]isocyanurate, and polyester (meth)acrylate oligomer; metal salts of unsaturated polybasic acids such as zinc (meth)acrylate and magnesium (meth)acrylate; Maleic anhydride, itaconic anhydride, citraconic anhydride, methyltetrahydrophthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3 - acid anhydrides of unsaturated polybasic acids such as cyclohexene-1,2-dicarboxylic acid anhydride, trialkyltetrahydrophthalic anhydride-maleic anhydride adduct, dodecenyl succinic anhydride, and methyl hymic anhydride; (meth)acrylamide, methylenebis-(meth)acrylamide, diethylenetriaminetris(meth)acrylamide, xylylenebis(meth)acrylamide, α-chloroacrylamide, N-2-hydroxyethyl ( amides of unsaturated monobasic acids and polyvalent amines such as meth)acrylamide; unsaturated aldehydes such as acrolein; unsaturated nitriles such as (meth)acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide, and allyl cyanide; Styrene, 4-methylstyrene, 4-ethylstyrene, 4-methoxystyrene, 4-hydroxystyrene, 4-chlorostyrene, divinylbenzene, vinyltoluene, vinylbenzoic acid, vinylphenol, vinylsulfonic acid, 4-vinylbenzene Unsaturated aromatic compounds, such as sulfonic acid, vinylbenzylmethyl ether, and vinylbenzyl glycidyl ether; unsaturated ketones such as methyl vinyl ketone; unsaturated amine compounds such as vinylamine, allylamine, N-vinylpyrrolidone and vinylpiperidine; vinyl alcohol such as allyl alcohol and crotyl alcohol; vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, n-butyl vinyl ether, isobutyl vinyl ether, and allyl glycidyl ether; unsaturated imides such as maleimide, N-phenylmaleimide, and N-cyclohexylmaleimide; indene, such as indene and 1-methylindene; aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; macromonomers having a mono(meth)acryloyl group at the terminal of the polymer molecular chain, such as polystyrene, polymethyl(meth)acrylate, poly-n-butyl(meth)acrylate, and polysiloxane; Vinyl chloride, vinylidene chloride, divinyl succinate, diallyl phthalate, triallyl phosphite, triallyl isocyanurate, vinyl thioether, vinylimidazole, vinyl oxazoline, vinyl carbazole, vinyl pyrrolidone , vinyl pyridine, vinyl urethane compounds of hydroxyl group-containing vinyl monomers and polyisocyanate compounds, vinyl epoxy compounds of hydroxyl group-containing vinyl monomers and polyepoxy compounds.
에틸렌성 불포화 화합물은 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다. An ethylenically unsaturated compound can be used individually or in mixture of 2 or more types.
상기 에틸렌성 불포화 화합물로는 시판품을 사용할 수도 있고, 예를 들면, 카야라드 DPHA, DPEA-12, PEG400DA, THE-330, RP-1040, NPGDA, PET30, R-684(이상, 니폰 카야쿠 제품); 아로닉스 M-215, M-350(이상, 도아고세이 제품); NK에스테르A-DPH, A-TMPT, A-DCP, A-HD-N, TMPT, DCP, NPG 및 HD-N(이상, 신나카무라 가가꾸 고교 제품); SPC-1000, SPC-3000(이상, 쇼와덴코 제품) 등을 들 수 있다. Commercially available products may be used as the ethylenically unsaturated compound, for example, Kayarad DPHA, DPEA-12, PEG400DA, THE-330, RP-1040, NPGDA, PET30, R-684 (above, manufactured by Nippon Kayaku) ; Aronix M-215, M-350 (above, manufactured by Toagosei); NK ester A-DPH, A-TMPT, A-DCP, A-HD-N, TMPT, DCP, NPG and HD-N (above, Shin-Nakamura Chemical Co., Ltd.); SPC-1000, SPC-3000 (above, Showa Denko product), etc. are mentioned.
중합성 조성물(B)의 함유량은 그 사용 목적에 따라 적합한 양이면 되는데, 경화 불량을 막기 위해 중합성 조성물 중의 고형분(용제 이외의 전성분) 중 50질량부 이상이 되도록 함유시키는 것이 바람직하고, 60질량부 이상이 보다 바람직하며, 70질량부 이상이 특히 바람직하다. The content of the polymerizable composition (B) may be a suitable amount depending on the purpose of use, but in order to prevent curing failure, it is preferable to contain 50 parts by mass or more of the solid content (all components other than the solvent) in the polymerizable composition, 60 A mass part or more is more preferable, and 70 mass part or more is especially preferable.
본 발명의 중합성 조성물에는 임의 성분으로서 무기 화합물, 색재, 잠재성 에폭시 경화제, 연쇄 이동제, 증감제, 용제 등의 첨가제를 사용할 수 있다. Additives, such as an inorganic compound, a color material, a latent epoxy curing agent, a chain transfer agent, a sensitizer, and a solvent, can be used for the polymerizable composition of this invention as an arbitrary component.
상기 무기 화합물로는 예를 들면, 산화니켈, 산화철, 산화이리듐, 산화티탄, 산화아연, 산화마그네슘, 산화칼슘, 산화칼륨, 실리카, 알루미나 등의 금속산화물; 층상 점토 광물, 밀로리 블루, 탄산칼슘, 탄산마그네슘, 코발트계, 망간계, 유리 분말(특히 유리 플릿), 마이카, 탤크, 카올린, 페로시안화물, 각종 금속황산염, 황화물, 셀렌화물, 알루미늄실리케이트, 칼슘실리케이트, 수산화알루미늄, 백금, 금, 은 구리 등을 들 수 있다. 이들 무기 화합물은 예를 들면, 충전제, 반사 방지제, 도전재, 안정제, 난연제, 기계적 강도 향상제, 특수 파장 흡수제, 잉크 반발제 등으로 사용된다. Examples of the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; Layered clay mineral, Milori blue, calcium carbonate, magnesium carbonate, cobalt type, manganese type, glass powder (especially glass frit), mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfide, selenide, aluminum silicate, Calcium silicate, aluminum hydroxide, platinum, gold, silver copper, etc. are mentioned. These inorganic compounds are used, for example, as fillers, antireflection agents, conductive materials, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellents, and the like.
상기 색재로는 안료, 염료, 천연 색소 등을 들 수 있다. 이들 색재는 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다. Examples of the color material include pigments, dyes, and natural dyes. These color materials can be used individually or in mixture of 2 or more types.
상기 안료로는 예를 들면, 니트로소 화합물; 니트로 화합물; 아조 화합물; 디아조 화합물; 크산텐 화합물; 퀴놀린 화합물; 안트라퀴논 화합물; 쿠마린 화합물; 프탈로시아닌 화합물; 이소인돌리논 화합물; 이소인돌린 화합물; 퀴나크리돈 화합물; 안탄트론 화합물; 페리논 화합물; 페릴렌 화합물; 디케토피롤로피롤 화합물; 티오인디고 화합물; 디옥사진 화합물; 트리페닐메탄 화합물; 퀴노프탈론 화합물; 나프탈렌테트라카르복실산; 아조 염료, 시아닌 염료의 금속 착체 화합물; 레이크 안료; 퍼니스법, 채널법 또는 서멀법에 의해 얻어지는 카본블랙, 혹은 아세틸렌 블랙, 케첸블랙 또는 램프블랙 등의 카본블랙; 상기 카본블랙을 에폭시 수지로 조정 또는 피복한 것, 상기 카본블랙을 미리 용매 중에 수지로 분산 처리하고, 20~200mg/g의 수지를 흡착시킨 것, 상기 카본블랙을 산성 또는 알카리성 표면처리한 것, 평균 입경이 8nm 이상이고 DBP 흡유량이 90㎖/100g 이하인 카본블랙, 950℃에서의 휘발분 중의 CO 및 CO2로부터 산출한 전체 산소량이 표면적 100㎡당 9mg 이상인 카본블랙; 흑연, 흑연화 카본블랙, 활성탄, 탄소섬유, 카본나노튜브, 카본마이크로코일, 탄소나노혼, 카본에어로겔, 풀러렌; 아닐린 블랙, 피그먼트 블랙7, 티탄 블랙; 산화크롬 그린, 밀로리 블루, 코발트 그린, 코발트 블루, 망간계, 페로시안화물, 인산염 군청, 감청, 울트라마린, 세룰리안 블루, 피리디안, 에메랄드 그린, 황산납, 황색 납, 아연황, 벵갈라(적색 산화철(III)), 카드뮴 레드, 합성 철흑, 앰버 등의 유기 또는 무기 안료를 사용할 수 있다. 이들 안료는 단독으로, 혹은 복수를 혼합하여 사용할 수 있다. The pigment includes, for example, a nitroso compound; nitro compounds; azo compounds; diazo compounds; xanthene compounds; quinoline compounds; anthraquinone compounds; coumarin compounds; phthalocyanine compounds; isoindolinone compounds; isoindoline compounds; quinacridone compounds; ananthrone compounds; perinone compounds; perylene compounds; diketopyrrolopyrrole compounds; thioindigo compounds; dioxazine compounds; triphenylmethane compounds; quinophthalone compounds; naphthalenetetracarboxylic acid; metal complex compounds of azo dyes and cyanine dyes; lake pigment; carbon black obtained by the furnace method, the channel method, or the thermal method, or carbon black such as acetylene black, Ketjen black or lamp black; The carbon black is adjusted or coated with an epoxy resin, the carbon black is previously dispersed in a solvent with a resin, and 20 to 200 mg/g of the resin is adsorbed, the carbon black is surface-treated with an acidic or alkaline surface; carbon black having an average particle diameter of 8 nm or more and a DBP oil absorption of 90 ml/100 g or less, carbon black having a total oxygen content calculated from CO and CO 2 in volatile matter at 950° C. of 9 mg or more per 100 m 2 of surface area; graphite, graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon airgel, fullerene; Aniline Black, Pigment Black 7, Titanium Black; Chromium oxide green, milory blue, cobalt green, cobalt blue, manganese-based, ferrocyanide, phosphate ultramarine, royal blue, ultramarine, cerulean blue, pyridian, emerald green, lead sulfate, yellow lead, zinc sulfur, bengala ( Organic or inorganic pigments, such as red iron(III) oxide), cadmium red, synthetic iron black, and amber, can be used. These pigments can be used individually or in mixture of plurality.
상기 안료로는 시판의 안료를 사용할 수도 있고, 예를 들면, 피그먼트 레드 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90, 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; 피그먼트 오렌지 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; 피그먼트 옐로우 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; 피그먼트 그린 7, 10, 36; 피그먼트 블루 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 22, 24, 56, 60, 61, 62, 64; 피그먼트 바이올렛 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 등을 들 수 있다. A commercially available pigment may be used as the pigment, for example, Pigment Red 1, 2, 3, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48, 49, 88, 90 , 97, 112, 119, 122, 123, 144, 149, 166, 168, 169, 170, 171, 177, 179, 180, 184, 185, 192, 200, 202, 209, 215, 216, 217, 220 , 223, 224, 226, 227, 228, 240, 254; Pigment Orange 13, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 65, 71; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114 , 117, 120, 125, 126, 127, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 166, 168, 175, 180, 185; Pigment Green 7, 10, 36; Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 22, 24, 56, 60, 61, 62, 64; Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 50, etc. are mentioned.
상기 염료로는 아조 염료, 안트라퀴논 염료, 인디고이드 염료, 트리아릴메탄 염료, 크산텐 염료, 알리자린 염료, 아크리딘 염료, 스틸벤 염료, 티아졸 염료, 나프톨 염료, 퀴놀린 염료, 니트로 염료, 인다민 염료, 옥사진 염료, 프탈로시아닌 염료, 시아닌 염료 등의 염료 등을 들 수 있고, 이들은 복수를 혼합하여 사용해도 된다. Examples of the dye include azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes, stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, inda Dyes, such as min dye, an oxazine dye, a phthalocyanine dye, and a cyanine dye, are mentioned, These may mix and use plurality.
상기 잠재성 에폭시 경화제로는 예를 들면, 디시안디아미드, 변성 폴리아민, 하이드라지드류, 4,4'-디아미노디페닐설폰, 3불화붕소아민착염, 이미다졸류, 구아나민류, 이미다졸류, 우레아류 및 멜라민 등을 들 수 있다. As the latent epoxy curing agent, for example, dicyandiamide, modified polyamine, hydrazide, 4,4'-diaminodiphenylsulfone, boron trifluoride amine complex salt, imidazole, guanamine, imidazole , ureas, and melamine.
상기 연쇄 이동제 또는 증감제로는 일반적으로 황 원자 함유 화합물이 사용된다. 예를 들면 티오글리콜산, 티오말산, 티오살리실산, 2-메르캅토프로피온산, 3-메르캅토프로피온산, 3-메르캅토부티르산, N-(2-메르캅토프로피오닐)글리신, 2-메르캅토니코틴산, 3-[N-(2-메르캅토에틸)카르바모일]프로피온산, 3-[N-(2-메르캅토에틸)아미노]프로피온산, N-(3-메르캅토프로피오닐)알라닌, 2-메르캅토에탄설폰산, 3-메르캅토프로판설폰산, 4-메르캅토부탄설폰산, 도데실(4-메틸티오)페닐에테르, 2-메르캅토에탄올, 3-메르캅토-1,2-프로판디올, 1-메르캅토-2-프로판올, 3-메르캅토-2-부탄올, 메르캅토페놀, 2-메르캅토에틸아민, 2-메르캅토이미다졸, 2-메르캅토벤조이미다졸, 2-메르캅토-3-피리디놀, 2-메르캅토벤조티아졸, 메르캅토아세트산, 트리메틸올프로판트리스(3-메르캅토프로피오네이트), 펜타에리트리톨테트라키스(3-메르캅토프로피오네이트) 등의 메르캅토 화합물, 상기 메르캅토 화합물을 산화하여 얻어지는 디설파이드 화합물, 요오드아세트산, 요오드프로피온산, 2-요오드에탄올, 2-요오드에탄설폰산, 3-요오드프로판설폰산 등의 요오드화 알킬 화합물, 트리메틸올프로판트리스(3-메르캅토이소부티레이트), 부탄디올비스(3-메르캅토이소부티레이트), 헥산디티올, 데칸디티올, 1,4-디메틸메르캅토벤젠, 부탄디올비스티오프로피오네이트, 부탄디올비스티오글리콜레이트, 에틸렌글리콜비스티오글리콜레이트, 트리메틸올프로판트리스티오글리콜레이트, 부탄디올비스티오프로피오네이트, 트리메틸올프로판트리스티오프로피오네이트, 트리메틸올프로판트리스티오글리콜레이트, 펜타에리트리톨테트라키스티오프로피오네이트, 펜타에리트리톨테트라키스티오글리콜레이트, 트리스하이드록시에틸트리스티오프로피오네이트, 디에틸티옥산톤, 디이소프로필티옥산톤, 하기 화합물 No.C1, 트리메르캅토프로피온산트리스(2-하이드록시에틸)이소시아누레이트 등의 지방족 다관능 티올 화합물, 쇼와덴코사 제품 카렌즈 MT BD1, PE1, NR1 등을 들 수 있다. A compound containing a sulfur atom is generally used as the chain transfer agent or sensitizer. For example, thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N-(2-mercaptopropionyl)glycine, 2-mercaptonicotinic acid, 3 -[N-(2-mercaptoethyl)carbamoyl]propionic acid, 3-[N-(2-mercaptoethyl)amino]propionic acid, N-(3-mercaptopropionyl)alanine, 2-mercaptoethane Sulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio)phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1- Mercapto-2-propanol, 3-mercapto-2-butanol, mercaptophenol, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercaptobenzoimidazole, 2-mercapto-3- Mercapto compounds such as pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropanetris(3-mercaptopropionate), and pentaerythritoltetrakis(3-mercaptopropionate); A disulfide compound obtained by oxidizing a mercapto compound, an alkyl iodide compound such as iodoacetic acid, iodopropionic acid, 2-iodethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid, trimethylolpropanetris(3-mercaptoy) Sobutyrate), butanediolbis(3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4-dimethyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthiol Glycolate, trimethylolpropane tristhioglycolate, butanediolbisthiopropionate, trimethylolpropane tristhiopropionate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakis Thioglycolate, trishydroxyethyltristhiopropionate, diethylthioxanthone, diisopropylthioxanthone, the following compound No.C1, trimercaptopropionate tris(2-hydroxyethyl)isocyanurate, etc. of aliphatic polyfunctional thiol compounds, Carenz MT BD1, PE1, NR1 manufactured by Showa Denko Corporation, and the like.
상기 용제로는 통상, 상기의 각 성분(중합 개시제(A) 및 중합성 화합물(B) 등)을 용해 또는 분산할 수 있는 용제, 예를 들면, 메틸에틸케톤, 메틸아밀케톤, 디에틸케톤, 아세톤, 메틸이소프로필케톤, 메틸이소부틸케톤, 시클로헥사논, 2-헵타논 등의 케톤류; 에틸에테르, 디옥산, 테트라하이드로푸란, 1,2-디메톡시에탄, 1,2-디에톡시에탄, 디프로필렌글리콜디메틸에테르 등의 에테르계 용제; 아세트산메틸, 아세트산에틸, 아세트산-n-프로필, 아세트산이소프로필, 아세트산n-부틸, 아세트산시클로헥실, 락트산에틸, 석신산디메틸, 텍사놀 등의 에스테르계 용제; γ-카프로락톤, δ-카프로락톤, γ-부티로락톤 등의 락톤계 용제; 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르 등의 셀로솔브계 용제; 메탄올, 에탄올, 이소- 또는 n-프로판올, 이소- 또는 n-부탄올, 아밀알코올 등의 알코올계 용제; 에틸렌글리콜모노메틸아세테이트, 에틸렌글리콜모노에틸아세테이트, 프로필렌글리콜-1-모노메틸에테르-2-아세테이트, 디프로필렌글리콜모노메틸에테르아세테이트, 3-메톡시부틸아세테이트, 에톡시에틸프로피오네이트 등의 에테르에스테르계 용제; 벤젠, 톨루엔, 크실렌 등의 BTX계 용제; 헥산, 헵탄, 옥탄, 시클로헥산 등의 지방족 탄화수소계 용제; 테레빈유, D-리모넨, 피넨 등의 테르펜계 탄화수소유; 미네랄 스피릿, 스와졸 #310(코스모 마쓰야마세키유(주)), 솔벳소 #100(엑손 카가쿠(주)) 등의 파라핀계 용제; 사염화탄소, 클로로포름, 트리클로로에틸렌, 염화메틸렌, 1,2-디클로로에탄 등의 할로겐화 지방족 탄화수소계 용제; 클로로벤젠 등의 할로겐화 방향족 탄화수소계 용제; 카르비톨계 용제; 아닐린; 트리에틸아민; 피리딘; 아세트산; 아세토니트릴; 이황화탄소; N,N-디메틸포름아미드; N,N-디메틸아세트아미드; N-메틸피롤리돈; 디메틸설폭시드; 물 등을 사용할 수 있고, 이들 용제는 1종으로 또는 2종 이상의 혼합 용제로 하여 사용할 수 있다. The solvent is usually a solvent capable of dissolving or dispersing each of the above components (such as the polymerization initiator (A) and the polymerizable compound (B)), for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone; ketones such as acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; ether solvents such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, and dipropylene glycol dimethyl ether; ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; lactone solvents such as γ-caprolactone, δ-caprolactone and γ-butyrolactone; cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol, and amyl alcohol; Ether esters such as ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate, dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, and ethoxyethyl propionate solvent based; BTX solvents, such as benzene, toluene, and xylene; aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane; terpene hydrocarbon oils such as turpentine, D-limonene, and pinene; Paraffinic solvents, such as mineral spirit, Swasol #310 (Cosmo Matsuyama Sekiyu Co., Ltd.), and Solvesso #100 (Exxon Chemical Co., Ltd.); halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichloroethylene, methylene chloride and 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol-based solvents; aniline; triethylamine; pyridine; acetic acid; acetonitrile; carbon disulfide; N,N-dimethylformamide; N,N-dimethylacetamide; N-methylpyrrolidone; dimethyl sulfoxide; Water or the like can be used, and these solvents can be used singly or as a mixed solvent of two or more kinds.
이들 중에서도 알칼리 현상성, 패터닝성, 제막성(製膜性), 용해성의 점에서 케톤류 또는 에테르에스테르계 용제, 특히, 프로필렌글리콜-1-모노메틸에테르-2-아세테이트(이하, "PGMEA"라고도 함.) 또는 시클로헥사논이 바람직하게 사용된다. Among these, ketones or ether ester solvents, particularly propylene glycol-1-monomethyl ether-2-acetate (hereinafter also referred to as “PGMEA”), from the viewpoint of alkali developability, patterning properties, film forming properties, and solubility. .) or cyclohexanone is preferably used.
본 발명의 중합성 조성물에서 용제의 함유량은 특별히 제한되지 않으며, 각 성분이 균일하게 분산 또는 용해되고, 또한 본 발명의 중합성 조성물이 각 용도에 적합한 액상 내지 페이스트상을 보이는 양이면 되는데, 통상, 본 발명의 중합성 조성물 중의 고형분(용제 이외의 전성분)의 양이 10~90질량%가 되는 범위에서 용제를 함유시키는 것이 균일한 경화물이 얻어지기 때문에 바람직하다. The content of the solvent in the polymerizable composition of the present invention is not particularly limited, and each component is uniformly dispersed or dissolved, and the polymerizable composition of the present invention may be an amount showing a liquid or paste suitable for each use, usually, It is preferable to contain a solvent in the range from which the quantity of solid content (all components other than a solvent) in the polymerizable composition of this invention will be 10-90 mass %, since uniform hardened|cured material is obtained.
또한, 본 발명의 중합성 조성물은 유기 중합체를 사용함으로써 경화물의 특성을 개선할 수도 있다. 상기 유기 중합체로는 예를 들면, 폴리스티렌, 폴리메틸메타크릴레이트, 메틸메타크릴레이트-에틸아크릴레이트 공중합체, 폴리(메타)아크릴산, 스티렌-(메타)아크릴산 공중합체, (메타)아크릴산-메틸메타크릴레이트 공중합체, 에틸렌-염화비닐 공중합체, 에틸렌-비닐 공중합체, 폴리염화비닐 수지, ABS 수지, 나일론6, 나일론66, 나일론12, 우레탄 수지, 폴리카보네이트폴리비닐부티랄, 셀룰로오스에스테르, 폴리아크릴아미드, 포화 폴리에스테르, 페놀 수지, 페녹시 수지 등을 들 수 있다. In addition, the polymerizable composition of the present invention may improve the properties of the cured product by using an organic polymer. Examples of the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene-(meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate. Crylate copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylic Amide, saturated polyester, phenol resin, phenoxy resin, etc. are mentioned.
상기 유기 중합체를 사용하는 경우, 그 함유량은 중합성 화합물(B) 100질량부에 대하여 얻어지는 중합성 조성물의 경화성이 뛰어난 점에서 바람직하게는 10~500질량부이다. When using the said organic polymer, the content is excellent in sclerosis|hardenability of the polymeric composition obtained with respect to 100 mass parts of polymeric compound (B), Preferably it is 10-500 mass parts.
본 발명의 중합성 조성물에는 추가로 계면활성제, 실란 커플링제, 멜라민 화합물 등을 병용할 수 있다. A surfactant, a silane coupling agent, a melamine compound, etc. can be used together with the polymerizable composition of this invention further.
상기 계면활성제로는 퍼플루오로알킬인산에스테르, 퍼플루오로알킬카르복실산염 등의 불소계 계면활성제; 고급 지방산 알칼리염, 알킬설폰산염, 알킬황산염 등의 음이온계 계면활성제; 고급 아민할로겐산염, 제4급 암모늄염 등의 양이온계 계면활성제; 폴리에틸렌글리콜알킬에테르, 폴리에틸렌글리콜 지방산 에스테르, 소르비탄 지방산 에스테르, 지방산 모노글리세리드 등의 비이온 계면활성제; 양성(兩性) 계면활성제; 실리콘계 계면활성제 등의 계면활성제를 사용할 수 있고, 이들은 조합하여 사용해도 된다. Examples of the surfactant include fluorine-based surfactants such as perfluoroalkyl phosphate esters and perfluoroalkyl carboxylates; Anionic surfactants, such as a higher fatty acid alkali salt, an alkyl sulfonate, and an alkyl sulfate; cationic surfactants such as higher amine halides and quaternary ammonium salts; nonionic surfactants such as polyethylene glycol alkyl ether, polyethylene glycol fatty acid ester, sorbitan fatty acid ester, and fatty acid monoglyceride; amphoteric surfactants; Surfactants, such as a silicone type surfactant, can be used, and these may be used in combination.
상기 실란 커플링제로는 예를 들면 신에쓰 가가꾸사 제품 실란 커플링제를 사용할 수 있고, 그 중에서도 KBE-9007, KBM-502, KBE-403 등의, 이소시아네이트기, 메타크릴로일기 또는 에폭시기를 가지는 실란 커플링제가 알맞게 사용된다. As the silane coupling agent, for example, a silane coupling agent manufactured by Shin-Etsu Chemical can be used, and among them, KBE-9007, KBM-502, KBE-403, etc. having an isocyanate group, a methacryloyl group or an epoxy group A silane coupling agent is suitably used.
상기 멜라민 화합물로는 (폴리)메틸올멜라민, (폴리)메틸올글리콜우릴, (폴리)메틸올벤조구아나민, (폴리)메틸올우레아 등의 질소 화합물 중의 활성 메틸올기(CH2OH기)의 전부 또는 일부(적어도 2개)가 알킬에테르화된 화합물 등을 들 수 있다. As the melamine compound, an active methylol group (CH 2 OH group) in a nitrogen compound such as (poly) methylolmelamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea) and compounds in which all or part (at least two) are alkyletherified.
여기서, 알킬에테르를 구성하는 알킬기로는 메틸기, 에틸기 또는 부틸기를 들 수 있으며, 서로 동일해도 되고, 달라도 된다. 또한, 알킬에테르화되어 있지 않은 메틸올기는 1분자 중에서 자기축합하고 있어도 되고, 2분자 간에서 축합하여, 그 결과 올리고머 성분이 형성되어 있어도 된다. Here, as the alkyl group constituting the alkyl ether, a methyl group, an ethyl group, or a butyl group is mentioned, and may be the same as or different from each other. In addition, the methylol group which is not alkyl-etherified may self-condensate in 1 molecule, and may condense between 2 molecules, and an oligomer component may be formed as a result.
구체적으로는 헥사메톡시메틸멜라민, 헥사부톡시메틸멜라민, 테트라메톡시메틸글리콜우릴, 테트라부톡시메틸글리콜우릴 등을 사용할 수 있다. Specifically, hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril, or the like can be used.
이들 중에서도 용제에 대한 용해성, 중합성 조성물로부터 결정 석출되기 어렵다는 점에서 헥사메톡시메틸멜라민, 헥사부톡시메틸멜라민 등의 알킬에테르화된 멜라민이 바람직하다. Among these, from the viewpoint of solubility in a solvent and difficulty in crystallization from the polymerizable composition, alkyl etherified melamines such as hexamethoxymethylmelamine and hexabutoxymethylmelamine are preferable.
본 발명의 중합성 조성물에서 중합 개시제(A) 및 중합성 화합물(B) 이외의 임의 성분(단, 무기 화합물, 색재, 및 용제는 제외함)의 함유량은 그의 사용 목적에 따라 적절히 선택되고 특별히 제한되지 않는데, 얻어지는 중합성 조성물의 경화성이 뛰어난 점에서 바람직하게는 중합성 화합물(B) 100질량부에 대하여 합계로 50질량부 이하로 한다. In the polymerizable composition of the present invention, the content of optional components other than the polymerization initiator (A) and the polymerizable compound (B) (however, inorganic compounds, color materials, and solvents are excluded) are appropriately selected according to the purpose of use and are particularly limited However, since it is excellent in sclerosis|hardenability of the polymeric composition obtained, Preferably it is set as 50 mass parts or less in total with respect to 100 mass parts of polymeric compound (B).
본 발명의 중합성 조성물은 에너지선을 조사하여 경화물로 할 수 있다. 상기 경화물은 용도에 따른 적절한 형상으로서 형성된다. 예를 들면 막 형상의 경화물을 형성하는 경우에는 본 발명의 중합성 조성물은 스핀 코터, 롤 코터, 바 코터, 다이 코터, 커튼 코터, 각종의 인쇄, 침지 등의 공지의 수단으로 소다 유리, 석영 유리, 반도체 기판, 금속, 종이, 플라스틱 등의 지지 기체 상에 적용할 수 있다. 또한, 일단 필름 등의 지지 기체 상에 실시한 후, 다른 지지 기체 상으로 전사(轉寫)할 수도 있고, 그 적용 방법에 제한은 없다. The polymerizable composition of this invention can be irradiated with an energy ray and it can be set as hardened|cured material. The cured product is formed in an appropriate shape according to the use. For example, in the case of forming a film-shaped cured product, the polymerizable composition of the present invention can be prepared by using a known means such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various types of printing, immersion, etc. It can be applied on supporting substrates such as glass, semiconductor substrates, metals, papers, and plastics. Moreover, after carrying out once on support bases, such as a film, it can also transfer on another support base body, and there is no restriction|limiting in the application method.
본 발명의 중합성 조성물을 경화시킬 때에 사용되는 에너지선의 광원으로는 초고압 수은램프, 고압 수은램프, 중압 수은램프, 저압 수은램프, 수은증기 아크등, 크세논 아크등, 카본 아크등, 메탈할라이드 램프, 형광등, 텅스텐 램프, 엑시머 램프, 살균등, 발광 다이오드, CRT 광원 등으로부터 얻어지는 2000옹스트롬~7000옹스트롬의 파장을 가지는 전자파 에너지나 전자선, X선, 방사선 등의 고에너지선을 이용할 수 있는데, 얻어지는 중합성 조성물의 경화성이 뛰어난 점에서 바람직하게는 파장 300~450㎚의 광을 발광하는 초고압 수은램프, 수은증기 아크등, 카본 아크등, 크세논 아크등 등이 이용된다. Examples of light sources of energy ray used when curing the polymerizable composition of the present invention include ultra-high pressure mercury lamps, high pressure mercury lamps, medium pressure mercury lamps, low pressure mercury lamps, mercury vapor arc lamps, xenon arc lamps, carbon arc lamps, metal halide lamps, Electromagnetic energy having a wavelength of 2000 angstroms to 7000 angstroms obtained from fluorescent lamps, tungsten lamps, excimer lamps, germicidal lamps, light emitting diodes, CRT light sources, etc. From the viewpoint of excellent curability of the composition, an ultra-high pressure mercury lamp emitting light having a wavelength of 300 to 450 nm, a mercury vapor arc lamp, a carbon arc lamp, a xenon arc lamp, etc. are preferably used.
더욱이, 노광 광원에 레이저광을 이용함으로써, 마스크를 이용하지 않고 컴퓨터 등의 디지털 정보로부터 직접 화상을 형성하는 레이저 직접 묘화법이, 생산성뿐만 아니라 해상성이나 위치 정밀도 등의 향상도 도모할 수 있기 때문에 유용하며, 그 레이저광으로는 340~430㎚의 파장의 광이 알맞게 사용되는데, 엑시머 레이저, 질소 레이저, 아르곤이온 레이저, 헬륨카드뮴 레이저, 헬륨네온 레이저, 크립톤이온 레이저, 각종 반도체 레이저 및 YAG 레이저 등의 가시에서 적외 영역의 광을 발하는 것도 이용할 수 있다. 이들 레이저광을 사용하는 경우에는 얻어지는 중합성 조성물의 경화성이 뛰어난 점에서 바람직하게는 가시에서 적외의 상기 영역을 흡수하는 증감 색소가 첨가된다. Furthermore, by using laser light as the exposure light source, the laser direct drawing method in which an image is formed directly from digital information such as a computer without using a mask can not only improve productivity but also improve resolution and positional accuracy. It is useful, and light with a wavelength of 340 to 430 nm is suitably used as the laser light. Excimer laser, nitrogen laser, argon ion laser, helium cadmium laser, helium neon laser, krypton ion laser, various semiconductor lasers, YAG laser, etc. It can also be used to emit light in the visible to infrared region of When these laser beams are used, a sensitizing dye which preferably absorbs the above-mentioned region from visible to infrared is added from the viewpoint of excellent sclerosis of the obtained polymerizable composition.
또한, 본 발명의 중합성 조성물의 경화에는 상기 에너지선 조사 후 가열하는 것이 통상 필요하고, 40~150℃ 정도의 가열이 경화율의 점에서 바람직하다. In addition, heating after the said energy-beam irradiation is normally required for hardening of the polymeric composition of this invention, and heating at about 40-150 degreeC is preferable at the point of a hardening rate.
본 발명의 중합성 조성물은 광경화성 도료 또는 바니시; 광경화성 접착제; 금속용 코팅제; 프린트 기판; 컬러 TV, PC 모니터, 휴대정보 단말, 디지털 카메라 등의 컬러 표시의 액정 표시 소자에서의 컬러 필터; CCD 이미지 센서의 컬러 필터; 플라즈마 표시 패널용 전극 재료; 분말 코팅; 인쇄 잉크; 인쇄판; 접착제; 치과용 조성물; 겔 코트; 전자 공학용 포토레지스트; 전기도금 레지스트; 에칭 레지스트; 드라이 필름; 땜납 레지스트; 다양한 표시 용도용 컬러 필터를 제조하기 위한 혹은 플라즈마 표시 패널, 전기 발광 표시장치, 및 LCD의 제조 공정에서 그들의 구조를 형성하기 위한 레지스트; 전기 및 전자 부품을 봉입하기 위한 조성물; 솔더 레지스트; 자기(磁氣)기록 재료; 미소(微小) 기계 부품; 도파로; 광 스위치; 도금용 마스크; 에칭 마스크; 컬러 시험계; 유리 섬유 케이블 코팅; 스크린 인쇄용 스텐실; 스테레오리소그래피에 의해 삼차원 물체를 제조하기 위한 재료; 홀로그래피 기록용 재료; 화상기록 재료; 미세 전자회로; 탈색 재료; 화상기록 재료를 위한 탈색 재료; 마이크로캡슐을 사용하는 화상기록 재료용 탈색 재료; 인쇄 배선판용 포토 레지스트 재료; UV 및 가시 레이저 직접 화상계용 포토 레지스트 재료; 프린트 회로 기판의 축차(逐次) 적층에서의 유전체층 형성에 사용하는 포토 레지스트 재료 또는 보호막 등의 각종 용도에 사용할 수 있고, 그 용도에 특별히 제한은 없다.The polymerizable composition of the present invention may include a photocurable paint or varnish; photocurable adhesives; coatings for metals; printed board; color filters in liquid crystal display elements for color display, such as color TVs, PC monitors, portable information terminals, and digital cameras; color filter of CCD image sensor; electrode materials for plasma display panels; powder coating; printing ink; printing plate; glue; dental compositions; gel coat; photoresists for electronics; electroplating resist; etching resist; dry film; solder resist; resists for manufacturing color filters for various display uses or for forming their structures in the manufacturing process of plasma display panels, electroluminescent displays, and LCDs; compositions for encapsulating electrical and electronic components; solder resist; magnetic recording material; small machine parts; waveguide; optical switch; mask for plating; etching mask; color test system; fiberglass cable coating; stencils for screen printing; materials for manufacturing three-dimensional objects by stereolithography; materials for holographic recording; image recording material; microelectronic circuits; bleaching material; decolorizing material for image recording material; discoloration materials for image recording materials using microcapsules; photoresist materials for printed wiring boards; photoresist materials for UV and visible laser direct imaging; It can be used for various uses, such as a photoresist material used for dielectric layer formation in the successive lamination|stacking of a printed circuit board, or a protective film, There is no restriction|limiting in particular in the use.
본 발명의 중합성 조성물은 액정표시 패널용 스페이서를 형성하는 목적 및 수직 배향형 액정표시 소자용 돌기를 형성하는 목적으로 사용할 수도 있다. 특히 수직 배향형 액정표시 소자용 돌기와 스페이서를 동시에 형성하기 위한 감광성 수지 조성물로서 유용하다. The polymerizable composition of the present invention may be used for the purpose of forming a spacer for a liquid crystal display panel and for the purpose of forming a projection for a vertically aligned liquid crystal display device. In particular, it is useful as a photosensitive resin composition for simultaneously forming a protrusion and a spacer for a vertically aligned liquid crystal display device.
상기 액정표시 패널용 스페이서는 (1) 본 발명의 중합성 조성물의 도막(塗膜)을 기판 상에 형성하는 공정, (2) 상기 도막에 소정의 패턴 형상을 가지는 마스크를 통해 에너지선(광)을 조사하는 공정, (3) 노광 후의 베이킹 공정, (4) 노광 후의 피막을 현상하는 공정, (5) 현상 후의 상기 피막을 가열하는 공정에 의해 바람직하게 형성된다. The spacer for the liquid crystal display panel is formed by (1) a process of forming a coating film of the polymerizable composition of the present invention on a substrate, (2) energy rays (light) through a mask having a predetermined pattern shape on the coating film It is preferably formed by a step of irradiating (3) a baking step after exposure, (4) a step of developing the coating film after exposure, and (5) a step of heating the coating film after development.
색재를 첨가한 본 발명의 중합성 조성물은 컬러 필터에서의 RGB 등의 각 화소를 구성하는 레지스트나, 각 화소의 격벽을 형성하는 블랙 매트릭스용 레지스트로서 알맞게 사용된다. 더욱이, 잉크 반발제를 첨가하는 블랙 매트릭스용 레지스트의 경우, 프로파일각이 50° 이상인 잉크젯 방식 컬러 필터용 격벽에 바람직하게 사용된다. 상기 잉크 반발제로는 불소계 계면활성제 및 불소계 계면활성제를 함유하는 조성물이 알맞게 사용된다. The polymerizable composition of the present invention to which a colorant is added is suitably used as a resist constituting each pixel such as RGB in a color filter, or a resist for a black matrix forming a barrier rib of each pixel. Moreover, in the case of a resist for a black matrix to which an ink repellant is added, it is preferably used for a partition wall for an inkjet type color filter having a profile angle of 50° or more. As the ink repellant, a fluorine-based surfactant and a composition containing a fluorine-based surfactant are suitably used.
상기 잉크젯 방식 컬러 필터용 격벽에 사용한 경우, 본 발명의 중합성 조성물로부터 형성된 격벽이 피(被)전사체 상을 구획하고, 구획된 피전사체 상의 오목부에 잉크젯법에 의해 액적을 부여하여 화상 영역을 형성하는 방법에 의해 광학 소자가 제조된다. 이 때, 상기 액적이 착색제를 함유하고, 상기 화상 영역이 착색되어 있는 것이 바람직하며, 그 경우에는 상기 제조 방법에 의해 제작된 광학 소자는 기판 상에 복수의 착색 영역으로 이루어지는 화소군과 상기 화소군의 각 착색 영역을 격리하는 격벽을 적어도 가지는 것이 된다. When used for the partition wall for an inkjet type color filter, the partition wall formed from the polymerizable composition of the present invention partitions an image to be transferred, and droplets are applied to the concave portion on the partitioned object by the inkjet method to form an image area An optical element is manufactured by a method of forming At this time, it is preferable that the droplet contains a colorant and the image region is colored. At least a barrier rib for isolating each colored area of .
본 발명의 중합성 조성물은 보호막 또는 절연막용 조성물로도 사용할 수 있다. 이 경우, 자외선 흡수제, 알킬화 변성 멜라민 및/또는 아크릴 변성 멜라민, 분자 중에 알코올성 수산기를 함유하는 1 또는 2관능의 (메타)아크릴레이트모노머 및/또는 실리카졸을 함유할 수 있다. The polymerizable composition of the present invention can also be used as a composition for a protective film or an insulating film. In this case, it may contain an ultraviolet absorber, alkylation-modified melamine and/or acryl-modified melamine, a monofunctional or bifunctional (meth)acrylate monomer containing an alcoholic hydroxyl group in the molecule, and/or silica sol.
상기 절연막은 박리가 가능한 지지 기재 상에 절연 수지층이 마련된 적층체에서의 상기 절연 수지층에 사용되고, 상기 적층체는 알칼리 수용액에 의한 현상이 가능한 것이며, 절연 수지층의 막 두께가 10~100㎛인 것이 바람직하다. The insulating film is used for the insulating resin layer in a laminate in which an insulating resin layer is provided on a peelable supporting substrate, and the laminate can be developed with an aqueous alkali solution, and the insulating resin layer has a thickness of 10 to 100 μm. It is preferable to be
본 발명의 중합성 조성물은 무기 화합물을 함유시킴으로써, 감광성 페이스트 조성물로 사용할 수 있다. 상기 감광성 페이스트 조성물은 플라즈마 디스플레이 패널의 격벽 패턴, 유전체 패턴, 전극 패턴 및 블랙 매트릭스 패턴 등의 소성물 패턴을 형성하기 위해 사용할 수 있다. The polymerizable composition of the present invention can be used as a photosensitive paste composition by containing an inorganic compound. The photosensitive paste composition may be used to form a fired pattern such as a barrier rib pattern, a dielectric pattern, an electrode pattern, and a black matrix pattern of a plasma display panel.
실시예 Example
이하, 실시예 및 비교예를 들어 본 발명을 더 상세하게 설명하겠는데, 본 발명은 이들 실시예 등에 한정되는 것은 아니다. Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
〔실시예 1〕 [Example 1]
이하에 나타낸 스킴에 따라 화합물 1을 합성했다. Compound 1 was synthesized according to the scheme shown below.
100㎖ 4구 플라스크에 옥심체 1을 1.0eq., 디클로로메탄(이론 수량의 600중량%), 트리에틸아민 3.0eq.를 첨가하고, 빙욕 상 5℃에서 교반을 실시했다. 이에 클로로포름산4-니트로페닐 1.1eq.를 디클로로메탄에 녹인 것을 적하하여 첨가했다. 적하 종료 후, 빙욕 상 0℃까지 냉각하고, 피페리딘 1.1eq.를 적하하여 첨가했다. 혼합액을 실온에서 1.5시간 교반하고, 감압 용매 증류제거했다. 농축 후의 잔사를 아세트산에틸로 용해하고, 1질량% NaOH 수용액으로 2회 세정 후, 이온 교환수에 의한 세정을 추가로 3회 실시했다. 유기층을 황산마그네슘에 의해 건조시키고, 농축했다. 잔사를 실리카겔 컬럼 크로마토그래피(용리제=아세트산에틸:헥산=1:4→1:3)에 의해 정제하고, 목적물을 담갈색 분말상 화합물로 하여 수율 41%로 얻었다. 1H-NMR 측정 결과를 표 1에 나타낸다. 1.0eq. of oxime body 1, dichloromethane (600 weight% of a theoretical amount), and triethylamine 3.0eq. were added to a 100 ml four-necked flask, and it stirred at 5 degreeC on the ice bath. To this, 1.1 eq. of 4-nitrophenyl chloroformate dissolved in dichloromethane was added dropwise. After completion|finish of dripping, it cooled to 0 degreeC on an ice bath, and piperidine 1.1eq. was dripped and added. The mixture was stirred at room temperature for 1.5 hours, and the solvent was distilled off under reduced pressure. The residue after concentration was dissolved in ethyl acetate, washed twice with 1 mass % NaOH aqueous solution, and then washed with ion-exchanged water three more times. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent=ethyl acetate:hexane=1:4→1:3) to obtain the target product as a pale brown powdery compound in a yield of 41%. 1 H-NMR measurement results are shown in Table 1.
〔실시예 2 및 비교예 1〕 중합성 조성물의 조제 [Example 2 and Comparative Example 1] Preparation of polymerizable composition
표 2에 기재된 배합을 실시하여 중합성 조성물 1 및 비교 중합성 조성물 1을 얻었다. 한편, 표 중의 배합 수치는 질량부를 나타낸다. The compounding|blending of Table 2 was implemented, and the polymeric composition 1 and the comparative polymeric composition 1 were obtained. In addition, the compounding numerical value in a table|surface represents a mass part.
또한, 표 중의 각 성분의 부호는 하기의 성분을 나타낸다. In addition, the code|symbol of each component in a table|surface shows the following component.
A-1: 화합물 1 A-1: compound 1
A'-2: 비교 화합물 1 A'-2: Comparative compound 1
B-1: EPPN-201(페놀노볼락형 에폭시 수지, 에폭시 등량 193g/eq., 니폰 카야쿠사 제품) B-1: EPPN-201 (phenol novolak type epoxy resin, epoxy equivalent 193 g/eq., manufactured by Nippon Kayaku)
B-2: H-3M(페놀 수지, 수산기 등량 105~109g/eq., 메이와가세이사 제품) B-2: H-3M (phenolic resin, hydroxyl equivalent weight of 105 to 109 g/eq., manufactured by Meiwa Gassei Co., Ltd.)
C-1: FZ-2122(폴리에테르 변성 폴리실록산, 도레이 다우코닝사 제품, 1중량% PGMEA 용액) C-1: FZ-2122 (polyether-modified polysiloxane, Toray Dow Corning Co., Ltd., 1 wt% PGMEA solution)
D-1: 시클로펜타논(용제) D-1: cyclopentanone (solvent)
〔평가예 1 그리고 비교 평가예 1〕 [Evaluation Example 1 and Comparative Evaluation Example 1]
중합성 조성물 1 및 비교 중합성 조성물 1의 경화물에 대해, 잔막의 유무를 하기 순서대로 확인했다. 결과를 표 4에 나타낸다. About the hardened|cured material of the polymeric composition 1 and the comparative polymeric composition 1, the presence or absence of a residual film was confirmed in the following order. A result is shown in Table 4.
중합성 조성물 1 및 비교 중합성 조성물 1을 각각 유리 기재(10㎝×10㎝)에 스핀 코터를 이용하여 도포하고(500rpm×2초→1000rpm×10초→슬로프×0.5초, 도포량 약 2㎖), 오븐 중에서 프리베이킹(90℃×90초)을 실시하고, 제막했다. Polymerizable composition 1 and comparative polymerizable composition 1 were respectively applied to a glass substrate (10 cm × 10 cm) using a spin coater (500 rpm × 2 sec → 1000 rpm × 10 sec → slope × 0.5 sec, application amount about 2 ml) , pre-baking (90 degreeC x 90 second) was performed in oven, and it formed into a film.
각 막에 대하여, 연속적으로 투과율이 변화되는 그라데이션을 가지는 스텝 태블릿(33단형, OD값 0~3, 표 3)을 마스킹하고, UV-LED(365㎚)를 이용하여 자외광을 소정량 조사했다(조도 20mW/㎠, 노광 시간 150초, 적산 노광량 3000mJ/㎠). For each film, a step tablet (33-stage type, OD value 0 to 3, Table 3) having a gradation of continuously changing transmittance was masked, and a predetermined amount of ultraviolet light was irradiated using UV-LED (365 nm). (illuminance 20 mW/cm 2 , exposure time 150 sec, cumulative exposure dose 3000 mJ/cm 2 ).
노광 후, 오븐 중에서 포스트베이킹(100℃×20분)하고, 현상(PGMEA, 30초)과 린스(이소프로필알코올, 10초)를 실시했다. After exposure, it post-baked (100 degreeC x 20 minutes) in oven, and performed image development (PGMEA, 30 second) and rinse (isopropyl alcohol, 10 second).
얻어진 경화막 샘플에 대해, 잔존 단수를 육안에 의해 확인했다. 잔존 단수란 경화막이 잔존하는 최대 단수를 의미한다. 잔존 단수로부터 표 3에 의해 투과율을 결정하고, 하기 식을 이용함으로써 환산 감도를 산출했다. About the obtained cured film sample, the number of remaining stages was visually confirmed. The number of remaining stages means the maximum number of stages in which the cured film remains. The transmittance was determined according to Table 3 from the number of remaining stages, and the conversion sensitivity was calculated by using the following formula.
환산 감도(mJ/㎠)=적산 노광량(3000mJ/㎠)×투과율(%) Conversion sensitivity (mJ/cm2)=accumulated exposure dose (3000mJ/cm2)×transmittance (%)
잔존 단수와 환산 감도를 표 4에 나타낸다. Table 4 shows the number of remaining stages and the converted sensitivity.
상기 표 4의 결과로부터, 본 발명의 카르바모일옥심 화합물을 함유하는 중합성 조성물은 비교 중합성 조성물과 비교하여 잔존 단수가 많기(경화성이 높기) 때문에, 광염기 발생 효율이 높고 저노광량으로 경화 가능하며 UV-LED 광원에 대하여 고감도이다. 따라서, 본 발명의 화합물이 중합 개시제로서 뛰어난 것은 명백하다. From the results in Table 4, the polymerizable composition containing the carbamoyloxime compound of the present invention has a high photobase generation efficiency and is cured at a low exposure dose because the number of residual stages is higher (higher curability) than the comparative polymerizable composition. It is possible and highly sensitive to UV-LED light source. Therefore, it is clear that the compound of the present invention is excellent as a polymerization initiator.
〔실시예 3〕 [Example 3]
이하에 나타낸 스킴에 따라 화합물 2를 합성했다. Compound 2 was synthesized according to the scheme shown below.
(옥심체 2의 합성) (Synthesis of oxime 2)
플라스크에 8-(3-시클로펜틸프로필)-11-(2-에틸헥실)-11H-벤조[a]카르바졸 1.0eq.를 첨가하고, 디메틸포름아미드(이론 수량의 500중량%)로 용해했다. 용액에 하이드록시암모늄클로라이드 2.2eq. 및 피리딘 2.2eq.를 첨가했다. 반응 혼합물을 60℃에서 9시간 가열 교반한 후, 이온 교환수를 첨가하고, 클로로포름으로 추출했다. 유기층을 이온 교환수로 2회 세정하고, 황산마그네슘에 의해 건조시키고, 농축했다. 잔사를 실리카겔 컬럼 크로마토그래피(용리제=헥산:아세트산에틸=94:6)에 의해 정제하고, 목적물을 백색 분말상 화합물로 하여 수율 28%로 얻었다. 1.0eq. of 8-(3-cyclopentylpropyl)-11-(2-ethylhexyl)-11H-benzo[a]carbazole was added to the flask, and it was dissolved in dimethylformamide (500% by weight of the theoretical amount). . 2.2eq of hydroxyammonium chloride in the solution. and 2.2 eq. of pyridine. After the reaction mixture was heated and stirred at 60°C for 9 hours, ion-exchanged water was added, followed by extraction with chloroform. The organic layer was washed twice with ion-exchanged water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent = hexane : ethyl acetate = 94 : 6), and the target product was obtained as a white powdery compound in a yield of 28%.
(화합물 2의 합성) (Synthesis of compound 2)
플라스크에 옥심체 2를 1.0eq., 클로로포름(이론 수량의 500중량%), 트리에틸아민 2.0eq.를 첨가하고, 빙욕 상 5℃에서 교반을 실시했다. 이에 클로로포름산4-니트로페닐 1.1eq.를 클로로포름(이론 수량의 500중량%)으로 녹인 것을 적하하여 첨가했다. 적하 종료 후, 실온에서 1시간 교반했다. 다시 빙욕 상 5℃까지 냉각 후, 아닐린 1.1eq.를 적하하여 첨가했다. 실온에서 2시간 교반한 후, 1질량% 수산화나트륨 수용액으로 3회, 이온 교환수로 3회 세정하고, 황산마그네슘에 의해 유기층을 건조시키고, 농축했다. 잔사를 실리카겔 컬럼 크로마토그래피(용리제=헥산:아세트산에틸=94:6)에 의해 정제하고, 목적물을 황색 부정형 고체 화합물로 하여 수율 35%로 얻었다. 얻어진 화합물의 1H-NMR 측정 결과를 표 5에 나타냈다. 1.0eq. of oxime body 2, chloroform (500 weight% of theoretical quantity), and triethylamine 2.0eq. were added to the flask, and it stirred at 5 degreeC on the ice bath. To this, 1.1 eq. of 4-nitrophenyl chloroformate was dissolved in chloroform (500 wt% of the theoretical amount) and added dropwise. After completion|finish of dripping, it stirred at room temperature for 1 hour. After cooling to 5°C on an ice bath again, 1.1 eq. of aniline was added dropwise. After stirring at room temperature for 2 hours, it washed 3 times with 1 mass % sodium hydroxide aqueous solution and 3 times with ion-exchanged water, and the organic layer was dried with magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent = hexane : ethyl acetate = 94: 6), and the target product was obtained as a yellow amorphous solid compound in a yield of 35%. Table 5 shows the results of 1 H-NMR measurement of the obtained compound.
〔실시예 4〕 [Example 4]
이하에 나타낸 스킴에 따라 화합물 3을 합성했다. Compound 3 was synthesized according to the scheme shown below.
(옥심체 3의 합성) (Synthesis of oxime 3)
플라스크에 1-(11-(2-에틸헥실)-11H-벤조[a]카르바졸-8-일)옥탄-1-온 1.0eq.를 첨가하고, 디메틸포름아미드(이론 수량의 400중량%)로 용해했다. 이에 4M·HCl-아세트산에틸 1.1eq.와 아질산이소부틸 1.1eq.를 첨가하고, 45℃에서 1시간 교반했다. 반응액에 클로로포름을 첨가하고, 이온 교환수로 4회 세정하고, 황산마그네슘에 의해 유기층을 건조 후, 농축했다. 잔사를 실리카겔 컬럼 크로마토그래피(용리제=헥산:아세트산에틸=91:9)에 의해 정제하고, 목적물을 백색 분말상 화합물로 하여 수율 18%로 얻었다. To a flask was added 1-(11-(2-ethylhexyl)-11H-benzo[a]carbazol-8-yl)octan-1-one 1.0eq. and dimethylformamide (400% by weight of theoretical quantity) was dissolved with To this, 1.1 eq. of 4M·HCl-ethyl acetate and 1.1 eq. of isobutyl nitrite were added, and the mixture was stirred at 45°C for 1 hour. Chloroform was added to the reaction solution, washed with ion-exchanged water 4 times, and the organic layer was dried with magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (eluent = hexane : ethyl acetate = 91:9), and the target product was obtained as a white powdery compound in a yield of 18%.
(화합물 3의 합성) (Synthesis of compound 3)
실시예 3의 옥심체 2를 옥심체 3으로 변경한 것 이외에는 동일한 절차로, 수세 후의 농축까지 진행시켰다. 잔사를 실리카겔 컬럼 크로마토그래피(용리제=헥산:아세트산에틸=95:5)에 의해 정제하고, 화합물 2를 황색 부정형 고체 화합물로 하여 수율 27%로 얻었다. 얻어진 화합물의 1H-NMR 측정 결과를 표 5에 나타냈다. Except for changing the oxime body 2 of Example 3 to the oxime body 3, the same procedure was followed until concentration after washing with water. The residue was purified by silica gel column chromatography (eluent = hexane : ethyl acetate = 95: 5) to obtain compound 2 as a yellow amorphous solid compound in a yield of 27%. Table 5 shows the results of 1 H-NMR measurement of the obtained compound.
본 발명의 카르바모일옥심 화합물은 높은 광염기 발생 효율을 가지고 있고, 중합 개시제로서 사용한 경우 종래의 광염기 발생제보다도 효율적으로 염기를 발생시킬 수 있기 때문에, 저노광량에서도 중합성 화합물을 경화시킬 수 있다. 특히, 에폭시 수지 또는 페놀 수지를 함유하는 경화성 수지 조성물에 사용한 경우, 높은 경화성을 나타낸다. The carbamoyloxime compound of the present invention has a high photobase generation efficiency, and when used as a polymerization initiator, it can generate a base more efficiently than a conventional photobase generator, so that the polymerizable compound can be cured even at a low exposure dose there is. In particular, when it uses for curable resin composition containing an epoxy resin or a phenol resin, high sclerosis|hardenability is shown.
Claims (10)
(식 중 R1은 수소 원자, 할로겐 원자, 니트로기, 시아노기, 탄소 원자 수 1~20의 탄화수소기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내고,
R2는 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내며,
R3, R4, R5, R6, R7, R8 및 R9는 각각 독립적으로 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR10, -COOR10, -CO-R10, -SR10, 탄소 원자 수 1~20의 탄화수소기, 또는 탄소 원자 수 2~20의 복소환 함유기를 나타내고,
R10은 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 탄소 원자 수 2~20의 복소환 함유기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내고, 분자 중에 R10이 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며,
X1은 -NR21R22, 또는 하기 일반식(a) 혹은 하기 일반식(b)로 표현되는 기를 나타내고,
R21 및 R22는 각각 독립적으로 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내며,
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R21 및 R22는 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기, -OR11, -COOR11, -CO-R11 또는 -SR11로 치환된 탄소 원자 수 1~20의 기이어도 되고,
R11은 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 탄화수소기 중의 메틸렌기가 하기 <군 A>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기, 또는 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기 또는 수산기로 치환된 탄소 원자 수 1~20의 기를 나타내고, 분자 중에 R11이 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며,
<군 A>는 -O-, -CO-, -COO-, -NR12-, -NR12CO- 및 -S-이고,
R12는 수소 원자 또는 탄소 원자 수 1~20의 탄화수소기를 나타내고, 분자 중에 R12가 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며,
R3과 R4, R6과 R7, R7과 R8 및 R8과 R9는 각각 독립적으로 서로 연결되어 수소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 3~10의 환을 형성하고 있어도 되고,
R3과 R4, R6과 R7, R7과 R8 및 R8과 R9 중 적어도 1세트는 서로 연결되어 벤젠환을 형성하고 있으며,
R21과 R22는 서로 연결되어 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환, 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환을 형성하고 있어도 되고,
n은 0 또는 1을 나타낸다.)
(식 중 R31, R32, R33, R34, R35, R36, R37, R38, R39 및 R40은 각각 독립적으로 수소 원자, 탄소 원자 수 1~20의 탄화수소기, 또는 탄화수소기 중의 메틸렌기가 하기 <군 B>에서 선택되는 2가의 기로 치환된 탄소 원자 수 1~20의 기를 나타내며,
R31, R32, R33, R34, R35, R36, R37, R38, R39 및 R40은 탄화수소기 중의 수소 원자의 1개 또는 2개 이상이 할로겐 원자, 시아노기, 니트로기, 수산기, -OR41, -COOR41, -CO-R41 또는 -SR41로 치환된 탄소 원자 수 1~20의 기이어도 되고,
R41은 수소 원자 또는 탄소 원자 수 1~20의 탄화수소기를 나타내고, 기 중에 R41이 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며,
<군 B>는 -O-, -CO-, -COO-, -NR42-, -NR42CO- 및 -S-이고,
R42는 수소 원자 또는 탄소 원자 수 1~20의 탄화수소기를 나타내고, 기 중에 R42가 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며,
R31과 R32, R33과 R34, R35와 R36, R37과 R38, 및 R39와 R40은 각각 독립적으로 서로 연결되어 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환, 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자 수 2~10의 환을 형성하고 있어도 되고,
*는 결합수(結合手)를 나타낸다.) A carbamoyloxime compound represented by the following general formula (I).
(wherein R 1 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydrocarbon group having 1 to 20 carbon atoms, or a methylene group in the hydrocarbon group, the number of carbon atoms substituted with a divalent group selected from the following <Group A>) represents a group of 1 to 20,
R 2 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a group having 1 to 20 carbon atoms in which a methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <Group A>,
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 10 , -COOR 10 , -CO-R 10 , -SR 10 , a hydrocarbon group having 1 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
R 10 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a heterocycle-containing group having 2 to 20 carbon atoms, or a methylene group in the hydrocarbon group is the number of carbon atoms substituted with a divalent group selected from the following <Group A> When a group of 1 to 20 is represented and two or more R 10 is present in a molecule, they may be the same or different,
X 1 represents -NR 21 R 22 , or a group represented by the following general formula (a) or the following general formula (b),
R 21 and R 22 each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a group having 1 to 20 carbon atoms in which a methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <Group A> ,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 21 and R 22 are one or more hydrogen atoms in the hydrocarbon group. A group having 1 to 20 carbon atoms may be substituted with an atom, a cyano group, a nitro group, a hydroxyl group, -OR 11 , -COOR 11 , -CO-R 11 or -SR 11 ,
R 11 is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a group having 1 to 20 carbon atoms in which the methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <Group A>, or a hydrogen atom in the hydrocarbon group 1 or 2 or more represent a group having 1 to 20 carbon atoms substituted with a halogen atom, a cyano group, a nitro group or a hydroxyl group, and when a plurality of R 11 is present in the molecule, they may be the same or different,
<Group A> is -O-, -CO-, -COO-, -NR 12 -, -NR 12 CO- and -S-,
R 12 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and when two or more R 12 are present in a molecule, they may be the same or different;
R 3 and R 4 , R 6 and R 7 , R 7 and R 8 and R 8 and R 9 may each independently be linked to each other to form a ring having 3 to 10 carbon atoms comprising a hydrogen atom and a carbon atom,
At least one set of R 3 and R 4 , R 6 and R 7 , R 7 and R 8 and R 8 and R 9 is connected to each other to form a benzene ring,
R 21 and R 22 are linked to each other to form a ring having 2 to 10 carbon atoms composed of a hydrogen atom, a nitrogen atom and a carbon atom, or a ring having 2 to 10 carbon atoms composed of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom you can do it,
n represents 0 or 1.)
(Wherein, R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are each independently a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or represents a group having 1 to 20 carbon atoms in which the methylene group in the hydrocarbon group is substituted with a divalent group selected from the following <group B>,
R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are one or more of the hydrogen atoms in the hydrocarbon group is a halogen atom, a cyano group, or a nitro group. A group having 1 to 20 carbon atoms may be substituted with a group, a hydroxyl group, -OR 41 , -COOR 41 , -CO-R 41 or -SR 41 ,
R 41 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and when two or more R 41 is present in the group, they may be the same or different;
<Group B> is -O-, -CO-, -COO-, -NR 42 -, -NR 42 CO- and -S-,
R 42 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and when a plurality of R 42 is present in the group, they may be the same or different;
R 31 and R 32 , R 33 and R 34 , R 35 and R 36 , R 37 and R 38 , and R 39 and R 40 are each independently linked to each other to form a hydrogen atom, a nitrogen atom and a carbon atom 2 A ring of ~10 or a ring of 2 to 10 carbon atoms composed of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom may be formed;
* indicates the number of bonds (結合手).
일반식(I) 중의 R3과 R4, 또는 R8과 R9가 서로 연결되어 벤젠환을 형성하고 있는 카르바모일옥심 화합물. According to claim 1,
A carbamoyloxime compound in which R 3 and R 4 or R 8 and R 9 in the general formula (I) are linked to each other to form a benzene ring.
일반식(I) 중의 X1이 -NR21R22인 카르바모일옥심 화합물. 3. The method of claim 1 or 2,
A carbamoyloxime compound, wherein X 1 in the general formula (I) is —NR 21 R 22 .
일반식(I) 중의 R2가 탄소 원자 수 1~10의 지방족 탄화수소기인 카르바모일옥심 화합물. 4. The method according to any one of claims 1 to 3,
The carbamoyloxime compound whose R< 2 > in general formula (I) is a C1-C10 aliphatic hydrocarbon group.
상기 중합성 화합물이 에폭시 수지 혹은 에틸렌성 불포화 화합물, 또는 에폭시 수지와 페놀 수지를 포함하는 혼합물, 에폭시 수지와 티올 화합물을 포함하는 혼합물, 혹은 에틸렌성 불포화 화합물과 티올 화합물을 포함하는 혼합물인 중합성 조성물. 8. The method of claim 7,
A polymerizable composition wherein the polymerizable compound is an epoxy resin or an ethylenically unsaturated compound, or a mixture containing an epoxy resin and a phenol resin, a mixture containing an epoxy resin and a thiol compound, or a mixture containing an ethylenically unsaturated compound and a thiol compound .
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