KR20210148071A - 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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- KR20210148071A KR20210148071A KR1020217019236A KR20217019236A KR20210148071A KR 20210148071 A KR20210148071 A KR 20210148071A KR 1020217019236 A KR1020217019236 A KR 1020217019236A KR 20217019236 A KR20217019236 A KR 20217019236A KR 20210148071 A KR20210148071 A KR 20210148071A
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- carbon atoms
- hydrocarbon group
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- -1 Carbamoyloxime compound Chemical class 0.000 title claims abstract description 132
- 150000001875 compounds Chemical class 0.000 title claims abstract description 90
- 229960001330 hydroxycarbamide Drugs 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 title claims description 59
- 239000003505 polymerization initiator Substances 0.000 title claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 196
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 72
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 75
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 59
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 150000001721 carbon Chemical group 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 239000005011 phenolic resin Substances 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 125000003700 epoxy group Chemical group 0.000 claims description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 16
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 239000003822 epoxy resin Substances 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 229920000647 polyepoxide Polymers 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 13
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 230000001678 irradiating effect Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000002585 base Substances 0.000 description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 27
- 238000001723 curing Methods 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- 239000010408 film Substances 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- 150000002923 oximes Chemical class 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000975 dye Substances 0.000 description 13
- 229920003986 novolac Polymers 0.000 description 13
- 230000035945 sensitivity Effects 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
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- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000004593 Epoxy Substances 0.000 description 9
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000006229 carbon black Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
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- 125000000217 alkyl group Chemical group 0.000 description 6
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- 239000000758 substrate Substances 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 238000006845 Michael addition reaction Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000002484 inorganic compounds Chemical class 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
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- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
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- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 4
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 229920000877 Melamine resin Polymers 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
- 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
- 239000003054 catalyst Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 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
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
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- 229930195729 fatty acid Natural products 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 4
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
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- 230000009257 reactivity Effects 0.000 description 4
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 3
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- 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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- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WGPCGCOKHWGKJJ-UHFFFAOYSA-N sulfanylidenezinc Chemical compound [Zn]=S WGPCGCOKHWGKJJ-UHFFFAOYSA-N 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 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
- 239000010936 titanium Substances 0.000 description 1
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- 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
- 238000002834 transmittance Methods 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 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
- 235000013799 ultramarine blue Nutrition 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
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- C07D401/14—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 three or more hetero rings
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- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
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Abstract
본 발명의 과제는 높은 광염기 발생 효율을 가지는 화합물을 제공하는 것에 있다.
본 발명은 하기 일반식(I)로 나타내는 카르바모일옥심 화합물이다.
(식 중 A는, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향환 함유기를 나타내고, R1 및 R2는, 각각 독립적으로 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 등을 나타내며, X1 및 X2는, 각각 독립적으로 -NR3R4 등을 나타내고, R3 및 R4는, 각각 독립적으로 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 등을 나타내며, n은 0 또는 1을 나타내고, m은 0 또는 1을 나타낸다.)An object of the present invention is to provide a compound having high photobase generation efficiency.
This invention is a carbamoyl oxime compound represented by the following general formula (I).
(In the formula, A represents an aromatic ring-containing group having 6 to 20 carbon atoms which is unsubstituted or substituted, and R 1 and R 2 are each independently an unsubstituted or substituted group having 1 to 20 carbon atoms. represents an aliphatic hydrocarbon group, etc., X 1 and X 2 each independently represents -NR 3 R 4 etc., R 3 and R 4 are each independently unsubstituted or having 1 to 20 carbon atoms having a substituent an aliphatic hydrocarbon group, etc., n represents 0 or 1, m 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 것이며, 에너지 선(광) 조사에 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 can be polymerized and cured or developed by irradiation with energy rays (light). It is used for printing plates, various photoresists, and photocurable adhesives.
광중합 개시제는 에너지 선(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 금속기판을 부식시키거나, 경화 후의 수지를 변성시키는 등의 단점이 있다. 광염기 발생제는 상기의 산소에 의한 경화 저해 및 잔존 활성종에 의한 부식과 같은 문제를 발생시키기 어렵기 때문에 주목받고 있는데, 대체로 광산 발생제와 비교하면 저감도(저경화성)라는 문제가 있다. 광염기 발생제는 예를 들면 특허문헌 1 및 2에 기재되어 있다. The photopolymerization initiator is a difference in active species generated by energy ray (light) irradiation, and is divided into a photoradical generator, a photoacid generator, and a photobase generator. 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, and has disadvantages such as corrosion of the metal substrate or denaturing the resin after curing due to the residual acid of the active species. Photobase generators are attracting attention because they are difficult to cause problems such as inhibition of curing by oxygen and corrosion by residual active species, but generally there is a problem of low sensitivity (low curing) compared to photoacid generators. A photobase generator is described in patent documents 1 and 2, for example.
그러나 종래의 광염기 발생제는 염기 발생 효율이 낮고, 감도가 충분한 것이 아니었다. However, the conventional photobase generator has a low base generation efficiency, and the 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 high photobase generation efficiency.
본 발명자는 예의 검토를 실시하여, 특정 구조의 화합물이 높은 광염기 발생 효율을 가지고 있으며, 중합 개시제로서 유용한 것을 발견했다. MEANS TO SOLVE THE PROBLEM This inventor earnestly examined, and 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 나타내는 카르바모일옥심 화합물이다. That is, the present invention is a carbamoyloxime compound represented by the following general formula (I).
(식 중 A는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향환 함유기를 나타내고, (In the formula, A represents an aromatic ring-containing group having 6 to 20 carbon atoms, which is unsubstituted or substituted,
R1 및 R2는, 각각 독립적으로 수소 원자, 시아노기, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며, R 1 and R 2 are each independently a hydrogen atom, a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon having 6 to 20 carbon atoms represents the flag,
X1 및 X2는, 각각 독립적으로 -NR3R4, 또는 하기 식(a) 혹은 하기 식(b)로 나타내는 기를 나타내고, X 1 and X 2 each independently represent -NR 3 R 4 , or a group represented by the following formula (a) or the following formula (b),
R3 및 R4는, 각각 독립적으로 수소 원자, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며, R 3 and R 4 each independently represent a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R3 및 R4는, 서로 연결되어, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환을 형성하고 있어도 되며, R 3 and R 4 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 may be formed,
R3 및 R4가 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며, When a plurality of R 3 and R 4 exist, they may be the same or different,
n은 0 또는 1을 나타내고, m은 0 또는 1을 나타낸다.) n represents 0 or 1, m represents 0 or 1.)
(식 중 R11, R12, R13, R14, R15, R16, R17, R18, R19 및 R20은, 각각 독립적으로 수소 원자, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고, (Wherein, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are each independently a hydrogen atom, or the number of unsubstituted or substituted carbon atoms. Represents an aliphatic hydrocarbon group of 1 to 20 or an aromatic hydrocarbon group of 6 to 20 carbon atoms having an unsubstituted or substituted group,
R11과 R12, R13과 R14, R15와 R16, R17과 R18 및 R19와 R20은, 서로 연결되어, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환을 형성하고 있어도 되며, R 11 and R 12 , R 13 and R 14 , R 15 and R 16 , R 17 and R 18 , and R 19 and R 20 are connected to each other and the number of carbon atoms consisting of a hydrogen atom, a nitrogen atom and a carbon atom is 2 to 10 A phosphorus ring or a ring having 2 to 10 carbon atoms comprising a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom may be formed;
R11, R12, R13, R14, R15, R16, R17, R18, R19 및 R20이 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며, When a plurality of R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 exist, they may be the same or different,
*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 나타내는 것이다. 상기 일반식(I)로 나타내는 카르바모일옥심 화합물에는 옥심의 이중 결합에 의한 기하이성체가 존재하는데, 이들을 구별하는 것은 아니다. The carbamoyloxime compound of this invention is represented by the said General formula (I). Although the carbamoyloxime compound represented by the said general formula (I) exists by the geometrical isomer by the double bond of an oxime, these are not distinguished.
즉, 본 명세서에서, 상기 일반식(I)로 나타내는 카르바모일옥심 화합물, 그리고 후술할 상기 화합물의 바람직한 형태인 화합물 및 예시 화합물은 이성체의 혼합물 또는 어느 한쪽을 나타내고 있고, 나타낸 구조의 이성체에 한정되는 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. it is not going to be
이하, 상기 일반식(I)로 나타내는 카르바모일옥심 화합물을 간단하게 "일반식(I)로 나타내는 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) 중의 A는 방향환을 함유하는 탄소 원자수 6~20의 기이면 된다. A in the said general formula (I) should just be a C6-C20 group containing an aromatic ring.
상기 일반식(I) 중의 A로 나타내는, 무치환의 탄소 원자수 6~20의 방향환 함유기로는 디페닐설파이드, 카르바졸, 플루오렌, 인돌, 쿠마린 및 비페닐로부터 수소 원자를 2개 제거한 2가의 기를 들 수 있다. As the unsubstituted aromatic ring-containing group having 6 to 20 carbon atoms, represented by A in the general formula (I), 2 hydrogen atoms are removed from diphenylsulfide, carbazole, fluorene, indole, coumarin and biphenyl You can pick up the flag of the family.
탄소 원자수 6~20의 방향환 함유기가 치환기를 가지고 있는 경우의 치환기로는 할로겐 원자, 시아노기, 니트로기, -OR5, -COOR5, -CO-R5, -SR5, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 들 수 있다. When the aromatic ring-containing group having 6 to 20 carbon atoms has a substituent, the substituent includes a halogen atom, a cyano group, a nitro group, -OR 5 , -COOR 5 , -CO-R 5 , -SR 5 , the number of carbon atoms. A 1-20 aliphatic hydrocarbon group, a C6-C20 aromatic hydrocarbon group, or a C2-C20 heterocyclic-containing group is mentioned.
여기서, R5는, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타낸다. Here, R 5 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms.
치환기를 가지고 있는 탄소 원자수 6~20의 방향환 함유기란, 상기 무치환의 탄소 원자수 6~20의 방향환 함유기의 수소 원자의 1개 또는 2개 이상이 상기 치환기로 치환된 기를 의미한다. The aromatic ring-containing group having 6 to 20 carbon atoms having a substituent means a group in which one or two or more hydrogen atoms of the unsubstituted aromatic ring-containing group having 6 to 20 carbon atoms are substituted with the substituent. .
또한, 상기 치환기는, -OR5, -COOR5, -CO-R5, -SR5, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 및 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다. In addition, the substituent is -OR 5 , -COOR 5 , -CO-R 5 , -SR 5 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, and 2 carbon atoms. A hydrogen atom in the heterocycle-containing group of ~20 is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or The contribution substituted with a C2-C20 heterocyclic-containing group may also be sufficient.
더욱이, 상기 치환기는 탄소 원자수 1~20의 지방족 탄화수소기 중의 메틸렌기가, -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO2-, -NR-, -NR-CO-, -CO-NR-, -NR-COO-, -OCO-NR- 또는 -SiRR'-로 치환된 기여도 된다. Furthermore, the substituent is a methylene group in an aliphatic hydrocarbon group having 1 to 20 carbon atoms, -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO 2 Contributions substituted with -, -NR-, -NR-CO-, -CO-NR-, -NR-COO-, -OCO-NR- or -SiRR'- may also be used.
여기서, R 및 R'는 수소 원자 또는 탄소 원자수 1~20의 지방족 탄화수소기를 나타낸다. 상기 치환기가 R 또는 R'를 포함하는 기인 경우도 치환기 전체에 포함되는 탄소 원자수는 1~20이다. Here, R and R' represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms. Even when the substituent is a group containing R or R', the total number of carbon atoms included in the substituent is 1 to 20.
상기 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 said halogen atom.
상기 탄소 원자수 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, 시클로펜틸기, 시클로헥실기 및 시클로헥실메틸기 등의 알킬기, 그리고 이들 알킬기의 탄소-탄소 일중결합을 탄소-탄소 이중결합 또는 탄소-탄소 삼중결합으로 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 decyl group, hexadecyl group, octadecyl group, icosyl group, cyclopentyl group, cyclohexyl group and cyclohexylmethyl group, and a carbon-carbon single bond of these alkyl groups are replaced by a carbon-carbon double bond or a carbon-carbon triple bond and an unsaturated aliphatic hydrocarbon group having a structure substituted with .
상기 탄소 원자수 6~20의 방향족 탄화수소기로는 예를 들면, 페닐기, 나프틸기, 페난톨릴기, 피레닐기 및 비페닐기 등을 들 수 있다. Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a naphthyl group, a phenantholyl group, a pyrenyl group, and a biphenyl group.
상기 탄소 원자수 2~20의 복소환 함유기로는 테트라하이드로푸라닐기, 디옥소라닐기, 테트라하이드로피라닐기, 모르폴릴기, 푸라닐기, 티오페닐기, 메틸티오페닐기, 헥실티오페닐기, 벤조티오페닐기, 피롤릴기, 피롤리디닐기, 이미다졸릴기, 이미다졸리닐기, 이미다졸리디닐기, 피라졸리닐기, 피라졸리디닐기, 피페리디닐기 및 피페라지닐기 등을 들 수 있다. The heterocyclic ring-containing group having 2 to 20 carbon atoms includes a tetrahydrofuranyl group, a dioxolanyl group, a tetrahydropyranyl group, a morpholyl group, a furanyl group, a thiophenyl group, a methylthiophenyl group, a hexylthiophenyl group, a benzothiophenyl group, and a pyrrole. and a ryl group, a pyrrolidinyl group, an imidazolyl group, an imidazolinyl group, an imidazolidinyl group, a pyrazolinyl group, a pyrazolidinyl group, a piperidinyl group, and a piperazinyl group.
본 발명에서는 염기 발생 효율이 높기 때문에, 상기 일반식(I) 중의 A가, 하기 일반식(A-1)에 기재된 디페닐설파이드 구조, 하기 일반식(A-2)에 기재된 카르바졸 구조, 하기 일반식(A-3)에 기재된 플루오렌 구조, 하기 일반식(A-4)에 기재된 인돌 구조, 하기 일반식(A-5)에 기재된 쿠마린 구조 또는 하기 일반식(A-6)에 기재된 비페닐 구조를 가지는 기인 것이 바람직하고, 특히 하기 일반식(A-1)에 기재된 디페닐설파이드 구조, 하기 일반식(A-2)에 기재된 카르바졸 구조 또는 하기 일반식(A-3)에 기재된 플루오렌 구조를 가지는 기인 것이 바람직하다. In the present invention, since the base generation efficiency is high, A in the general formula (I) is the diphenylsulfide structure described in the following general formula (A-1), the carbazole structure described in the following general formula (A-2), The fluorene structure described in the general formula (A-3), the indole structure described in the following general formula (A-4), the coumarin structure described in the following general formula (A-5), or the ratio described in the following general formula (A-6) It is preferable that it is a group which has a phenyl structure, and especially the diphenyl sulfide structure described in the following general formula (A-1), the carbazole structure described in the following general formula (A-2), or the flu described in the following general formula (A-3) It is preferable that it is a group which has an orene structure.
(식 중, R21, R22, R23, R24, R25, R26, R27, R28, R29 및 R30은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR31, -COOR31, -CO-R31, -SR31, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내고, (wherein, R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 are each independently a number of bonds, a hydrogen atom, a halogen atom, a cyano group; Nitro group, -OR 31 , -COOR 31 , -CO-R 31 , -SR 31 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or an aromatic hydrocarbon group having 2 to 20 carbon atoms represents a heterocycle-containing group,
R21과 R22, R22와 R23, R23과 R24, R24와 R25, R26과 R27, R27과 R28, R28과 R29, R29와 R30은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되며, R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 , R 27 and R 28 , R 28 and R 29 , R 29 and R 30 are each They may be independently linked to each other to form a ring having 3 to 10 carbon atoms comprising a hydrogen atom and a carbon atom,
R21, R22, R23, R24, R25, R26, R27, R28, R29 및 R30 중 어느 2개는 결합수를 나타내고, Any two of R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 represents the number of bonds,
R31은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며, R 31 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R21, R22, R23, R24, R25, R26, R27, R28, R29 및 R30은, -OR31, -COOR31, -CO-R31, -SR31, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.) R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 are -OR 31 , -COOR 31 , -CO-R 31 , -SR 31 , carbon A hydrogen atom in an aliphatic hydrocarbon group having 1 to 20 atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, A contribution substituted with a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocyclic containing group having 2 to 20 carbon atoms may also be used.)
일반식(I) 중의 A가 상기 일반식(A-1)인 화합물은, 중합 개시제로서 사용한 경우, 염기 발생 효율이 높기 때문에 경화 감도가 뛰어나고, 또한 얻어지는 경화물의 투명성도 뛰어나기 때문에 바람직하다. When A in general formula (I) is the said general formula (A-1), when used as a polymerization initiator, since base generation efficiency is high, it is excellent in curing sensitivity, and also excellent in transparency of the hardened|cured material obtained, it is preferable.
일반식(A-1) 중의 R23 및 R28이 결합수인 것이 화합물이 안정적이고 순도 높게 합성할 수 있기 때문에 바람직하다. It is preferable that R 23 and R 28 in the general formula (A-1) represent a bonding number because the compound is stable and can be synthesized with high purity.
특히, 경화 감도가 뛰어나고, 화합물이 안정적이고 순도 높게 합성할 수 있기 때문에, R23 및 R28이 결합수이며, R21, R22, R24, R25, R26, R27, R29 및 R30이 수소 원자인 화합물이 바람직하다. In particular, since the curing sensitivity is excellent, the compound is stable and can be synthesized with high purity, R 23 and R 28 are bonded water, and R 21 , R 22 , R 24 , R 25 , R 26 , R 27 , R 29 and Compounds in which R 30 is a hydrogen atom are preferred.
(식 중 R40은, 수소 원자, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고, ( Wherein, R 40 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R41, R42, R43, R44, R45, R46, R47 및 R48은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR49, -COOR49, -CO-R49, -SR49, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내며, R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 and R 48 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 49 , -COOR 49 , -CO-R 49 , -SR 49 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
R41과 R42, R42와 R43, R43과 R44, R45와 R46, R46과 R47, R47과 R48은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되고, R 41 and R 42 , R 42 and R 43 , R 43 and R 44 , R 45 and R 46 , R 46 and R 47 , R 47 and R 48 are each independently linked to each other and are composed of a hydrogen atom and a carbon atom may form a ring having 3 to 10 carbon atoms,
R41, R42, R43, R44, R45, R46, R47 및 R48 중 어느 2개는 결합수를 나타내며, Any two of R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 and R 48 represents the number of bonds,
R49는, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고, R 49 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms;
R41, R42, R43, R44, R45, R46, R47 및 R48은, -OR49, -COOR49, -CO-R49, -SR49, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.) R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 and R 48 are -OR 49 , -COOR 49 , -CO-R 49 , -SR 49 , having 1 to 20 carbon atoms A hydrogen atom in an aliphatic hydrocarbon group, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, an acryl group Contributions substituted with a loyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocyclic group containing 2 to 20 carbon atoms may also be used.)
일반식(I) 중의 A가 상기 일반식(A-2)로 나타내지는 화합물은, 중합 개시제로서 사용한 경우, 염기 발생 효율이 높기 때문에 경화 감도가 뛰어나고, 장파장의 광이어도 염기 발생 효율이 높기 때문에 바람직하다. When A in the general formula (I) is used as a polymerization initiator, the compound in which A in the general formula (I) is used as a polymerization initiator has excellent curing sensitivity because of high base generation efficiency, and is preferable because of high base generation efficiency even with long wavelength light. do.
일반식(A-2) 중의 R43 및 R46이 결합수인 것이 화합물이 안정적이고 순도 높게 합성될 수 있기 때문에 바람직하다. It is preferable that R 43 and R 46 in the general formula (A-2) are bonding water because the compound can be synthesized stably and with high purity.
특히, 경화 감도가 뛰어나고, 화합물이 안정적이고 순도 높게 합성될 수 있기 때문에, 일반식(A-2) 중의 R40이 탄소 원자수 1~20의 지방족 탄화수소기이고, R43 및 R46이 결합수이며, R41, R42, R44, R45, R47 및 R48이 수소 원자인 화합물이 바람직하고, R40은 탄소 원자수 1~15의 지방족 탄화수소기인 것이 보다 바람직하며, 탄소 원자수 1~8의 지방족 탄화수소기인 것이 특히 바람직하다. In particular, since the curing sensitivity is excellent and the compound can be synthesized stably and with high purity, R 40 in the general formula (A-2) is an aliphatic hydrocarbon group having 1 to 20 carbon atoms, and R 43 and R 46 are the number of bonds and R 41 , R 42 , R 44 , R 45 , R 47 and R 48 are preferably a hydrogen atom, R 40 is more preferably an aliphatic hydrocarbon group having 1 to 15 carbon atoms, and 1 carbon atom It is particularly preferred that it is an aliphatic hydrocarbon group of ˜8.
(식 중, R51 및 R52는, 각각 독립적으로 수소 원자, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고, (Wherein, R 51 and R 52 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R53, R54, R55, R56, R57, R58, R59 및 R60은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR61, -COOR61, -CO-R61, -SR61, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내며, R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 and R 60 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 61 , -COOR 61 , -CO-R 61 , -SR 61 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
R53과 R54, R54와 R55, R55와 R56, R57과 R58, R58과 R59, R59와 R60은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되고, R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 are each independently linked to each other and are composed of a hydrogen atom and a carbon atom may form a ring having 3 to 10 carbon atoms,
R53, R54, R55, R56, R57, R58, R59 및 R60 중 어느 2개는 결합수를 나타내며, Any two of R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 and R 60 represents the number of bonds,
R61은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고, R 61 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R51, R52, R53, R54, R55, R56, R57, R58, R59, R60 및 R61은, -OR61, -COOR61, -CO-R61, -SR61, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.) R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 , R 60 and R 61 are -OR 61 , -COOR 61 , -CO-R 61 , -SR 61 , a hydrogen atom in an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group , carboxy group, methacryloyl group, acryloyl group, epoxy group, vinyl group, vinyl ether group, mercapto group, isocyanate group or a heterocyclic group containing 2 to 20 carbon atoms may be a substituted contribution.)
일반식(I) 중의 A가 상기 일반식(A-3)로 나타내지는 화합물은 염기 발생 효율이 높기 때문에 경화 감도가 뛰어나고, 또한 경화물의 투명성도 뛰어나기 때문에 바람직하다. The compound in which A in the general formula (I) is represented by the general formula (A-3) is preferred because of its high base generation efficiency, excellent curing sensitivity, and excellent transparency of the cured product.
일반식(A-3) 중의 R54 및 R59가 결합수인 것이, 화합물이 안정적이고 순도 높게 합성될 수 있기 때문에 바람직하다. It is preferable that R 54 and R 59 in the general formula (A-3) represent a bonding water, since the compound can be synthesized in a stable and high purity.
특히, 경화 감도가 뛰어나고, 화합물이 안정적이고 순도 높게 합성될 수 있기 때문에 일반식(A-3) 중의 R51 및 R52가 탄소 원자수 1~20의 지방족 탄화수소기이며, R54 및 R59가 결합수이고, R53, R55, R56, R57, R58 및 R60이 수소 원자인 화합물이 바람직하다. In particular, since the curing sensitivity is excellent and the compound can be synthesized stably and with high purity, R 51 and R 52 in the general formula (A-3) are aliphatic hydrocarbon groups having 1 to 20 carbon atoms, and R 54 and R 59 are A compound in which a number of bonds and R 53 , R 55 , R 56 , R 57 , R 58 and R 60 is a hydrogen atom is preferred.
(식 중 R71은, 수소 원자, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고, ( Wherein, R 71 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R71은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 되며, R 71 is a hydrogen atom in an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, acrylo A diyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a contribution substituted with a heterocyclic group containing 2 to 20 carbon atoms,
R72, R73, R74, R75, R76 및 R77은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR78, -COOR78, -CO-R78, -SR78, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내고, R 72 , R 73 , R 74 , R 75 , R 76 and R 77 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 78 , -COOR 78 , -CO-R 78 , -SR 78 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
R74와 R75, R75와 R76, R76과 R77은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되며, R 74 and R 75 , R 75 and R 76 , R 76 and R 77 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,
R72, R73, R74, R75, R76 및 R77 중 어느 2개는 결합수를 나타내고, Any two of R 72 , R 73 , R 74 , R 75 , R 76 and R 77 represents the number of bonds,
R78은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며, R 78 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R72, R73, R74, R75, R76 및 R77은, -OR78, -COOR78, -CO-R78, -SR78, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.) R 72 , R 73 , R 74 , R 75 , R 76 and R 77 are -OR 78 , -COOR 78 , -CO-R 78 , -SR 78 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, a carbon atom A hydrogen atom in an aromatic hydrocarbon group having 6 to 20 atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, vinyl ether group, mercapto group, isocyanate group, or a contribution substituted with a heterocyclic group containing 2 to 20 carbon atoms.)
일반식(I) 중의 A가 상기 일반식(A-4)로 나타내지는 화합물은 중합 개시제로서 사용한 경우, 염기 발생 효율이 높기 때문에 경화 감도가 뛰어나고, 또한 얻어지는 경화물의 투명성도 뛰어나기 때문에 바람직하다. When A in the general formula (I) is used as a polymerization initiator, the compound represented by the general formula (A-4) is preferable because of its high base generation efficiency, excellent curing sensitivity, and excellent transparency of the resulting cured product.
(식 중 R81, R82, R83, R84, R85 및 R86은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR87, -COOR87, -CO-R87, -SR87, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내고, (Wherein, R 81 , R 82 , R 83 , R 84 , R 85 and R 86 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 87 , -COOR 87 , -CO -R 87 , -SR 87 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms;
R83과 R84, R84와 R85, R85와 R86은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되며, R 83 and R 84 , R 84 and R 85 , R 85 and R 86 may be each independently linked to each other to form a ring having 3 to 10 carbon atoms comprising a hydrogen atom and a carbon atom,
R81, R82, R83, R84, R85 및 R86 중 어느 2개는 결합수를 나타내고, Any two of R 81 , R 82 , R 83 , R 84 , R 85 and R 86 represents the number of bonds,
R87은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며, R 87 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R81, R82, R83, R84, R85 및 R86은, -OR87, -COOR87, -CO-R87, -SR87, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.) R 81 , R 82 , R 83 , R 84 , R 85 and R 86 are -OR 87 , -COOR 87 , -CO-R 87 , -SR 87 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, a carbon atom A hydrogen atom in an aromatic hydrocarbon group having 6 to 20 atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, vinyl ether group, mercapto group, isocyanate group, or a contribution substituted with a heterocyclic group containing 2 to 20 carbon atoms.)
일반식(I) 중의 A가 상기 일반식(A-5)로 나타내는 화합물은, 중합 개시제로서 사용한 경우, 염기 발생 효율이 높기 때문에 경화 감도가 뛰어나고, 장파장의 광이어도 염기 발생 효율이 높기 때문에 바람직하다. When A in the general formula (I) is used as a polymerization initiator, the compound represented by the general formula (A-5) is preferable because of its high base generation efficiency, excellent curing sensitivity, and high base generation efficiency even with long-wavelength light. .
(식 중 R91, R92, R93, R94, R95, R96, R97, R98, R99 및 R100은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR101, -COOR101, -CO-R101, -SR101, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내고, (Wherein, R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 and R 100 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, or a nitro group. group, -OR 101 , -COOR 101 , -CO-R 101 , -SR 101 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a double carbon group having 2 to 20 carbon atoms represents a summoning containing group,
R91과 R92, R92와 R93, R93과 R94, R94와 R95, R96과 R97, R97과 R98, R98과 R99, R99와 R100은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되며, R 91 and R 92 , R 92 and R 93 , R 93 and R 94 , R 94 and R 95 , R 96 and R 97 , R 97 and R 98 , R 98 and R 99 , R 99 and R 100 are each They may be independently linked to each other to form a ring having 3 to 10 carbon atoms comprising a hydrogen atom and a carbon atom,
R91, R92, R93, R94, R95, R96, R97, R98, R99 및 R100 중 어느 2개는 결합수를 나타내고, any two of R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 and R 100 represents the number of bonds;
R101은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며, R 101 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R91, R92, R93, R94, R95, R96, R97, R98, R99 및 R100은, -OR101, -COOR101, -CO-R101, -SR101, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.) R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 and R 100 are -OR 101 , -COOR 101 , -CO-R 101 , -SR 101 , carbon A hydrogen atom in an aliphatic hydrocarbon group having 1 to 20 atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, A contribution substituted with a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocyclic containing group having 2 to 20 carbon atoms may also be used.)
일반식(I) 중의 A가 상기 일반식(A-6)으로 나타내지는 화합물은 중합 개시제로서 사용한 경우, 염기 발생 효율이 높아 경화 감도가 뛰어나기 때문에 바람직하다. When A in the general formula (I) is used as a polymerization initiator, the compound represented by the general formula (A-6) is preferred because of its high base generation efficiency and excellent curing sensitivity.
일반식(A-1)~(A-6) 중의 할로겐 원자, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기로는, 상기 일반식(I) 중의 A의 설명에서 예시한 기를 들 수 있다. A halogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms in the general formulas (A-1) to (A-6) is the group exemplified in the description of A in the general formula (I).
일반식(A-1) 중의 R21과 R22, R22와 R23, R23과 R24, R24와 R25, R26과 R27, R27과 R28, R28과 R29, R29와 R30, 일반식(A-2) 중의 R41과 R42, R42와 R43, R43과 R44, R45와 R46, R46과 R47, R47과 R48, 일반식(A-3) 중의 R53과 R54, R54와 R55, R55와 R56, R57과 R58, R58과 R59, R59와 R60, 일반식(A-4) 중의 R74와 R75, R75와 R76, R76과 R77, 일반식(A-5) 중의 R83과 R84, R84와 R85, R85와 R86, 및 일반식(A-6) 중의 R91과 R92, R92와 R93, R93과 R94, R94와 R95, R96과 R97, R97과 R98, R98과 R99, R99와 R100이, 서로 연결되어 형성하는, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환으로는, 벤젠환, 시클로헥센환, 시클로헥산환, 시클로펜타디엔환, 시클로펜탄환 등을 들 수 있다. R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 , R 27 and R 28 , R 28 and R 29 in the general formula (A-1), R 29 and R 30 , R 41 and R 42 , R 42 and R 43 , R 43 and R 44 , R 45 and R 46 , R 46 and R 47 , R 47 and R 48 in formula (A-2), R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 , general formula (A-4) in formula (A-3) ) in R 74 and R 75 , R 75 and R 76 , R 76 and R 77 , R 83 and R 84 in general formula (A-5), R 84 and R 85 , R 85 and R 86 , and general formula ( In A-6), R 91 and R 92 , R 92 and R 93 , R 93 and R 94 , R 94 and R 95 , R 96 and R 97 , R 97 and R 98 , R 98 and R 99 , R 99 and Examples of the ring comprising a hydrogen atom and a carbon atom and having 3 to 10 carbon atoms, which R 100 is connected to each other, includes a benzene ring, a cyclohexene ring, a cyclohexane ring, a cyclopentadiene ring, and a cyclopentane ring. have.
상기 일반식(I) 중의 R1 및 R2는, 각각 독립적으로 수소 원자, 시아노기, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기를 나타낸다. 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기로는 상기 일반식(I) 중의 A의 설명에서 예시한 기를 들 수 있다. R 1 and R 2 in the general formula (I) are each independently a hydrogen atom, a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted carbon atom The number 6-20 aromatic hydrocarbon group is shown. Examples of the unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or the unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms include the groups exemplified in the description of A in the above general formula (I). can be heard
R1 및/또는 R2가, 탄소 원자수 2 이상의 알킬기, 또는 탄소 원자수 6 이상의 시클로알킬알킬기인 화합물은 용제에 대한 용해성이 높기 때문에 바람직하고, R1 및/또는 R2는 탄소 원자수 2~15의 알킬기, 또는 탄소 원자수 6~15의 시클로알킬알킬기인 것이 보다 바람직하며, 탄소 원자수 2~10의 알킬기, 또는 탄소 원자수 6~10의 시클로알킬알킬기인 것이 특히 바람직하다. The R 1 and / or R 2, a compound of carbon atoms of 2 or more alkyl groups, or a carbon atom number of 6 or more cycloalkyl group is preferred because of its high solubility in solvents, R 1 and / or R 2 is the carbon atom 2 It is more preferable that it is a -15 alkyl group or a C6-C15 cycloalkylalkyl group, and it is especially preferable that it is a C2-C10 alkyl group or a C6-C10 cycloalkylalkyl group.
상기 일반식(I) 중의 X1 및 X2는, 각각 독립적으로 -NR3R4, 또는 상기 식(a) 혹은 상기 식(b)로 나타내는 기이다. X 1 and X 2 in the general formula (I) are each independently —NR 3 R 4 , or a group represented by the formula (a) or the formula (b).
R3 및 R4로 나타내는, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기로는, 상기 일반식(I) 중의 A의 설명에서 예시한 기를 들 수 있다. As the unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or the unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R 3 and R 4 , the general formula (I ) of the groups exemplified in the description of A.
R3 및 R4가 복수 존재하는 경우, 그들은 동일해도 되도 달라도 된다. 즉, X1 및 X2가 -NR3R4인 경우, X1 중의 R3 및 R4와 X2 중의 R3 및 R4는 각각 동일해도 되고 달라도 된다. When two or more R 3 and R 4 exist, they may be the same or different. That is, X 1 and X 2 is -NR 3 R 4 in the case, X 1 of R 3 and R 4 and X 2 of R 3 and R 4 may be the same or different, respectively.
상기 식(a) 및 상기 식(b) 중의 R11~R20으로 나타내는, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기로는 상기 일반식(I) 중의 A의 설명에서 예시한 기를 들 수 있다. An unsubstituted or substituted C1-C20 aliphatic hydrocarbon group represented by R 11 to R 20 in the formulas (a) and (b), or an unsubstituted or substituted C6-C6 group Examples of the aromatic hydrocarbon group represented by 20 include the groups exemplified in the description of A in the general formula (I).
R3과 R4, R11과 R12, R13과 R14, R15와 R16, R17과 R18 및 R19와 R20이, 서로 연결되어 형성하는, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환으로는 결합되어 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 일반식(I) 중의 A의 설명에서 예시한 기를 들 수 있다. R 3 and R 4 , R 11 and R 12 , R 13 and R 14 , R 15 and R 16 , R 17 and R 18 and R 19 and R 20 are connected to each other to form a hydrogen atom, a nitrogen atom and a carbon A ring having 2 to 10 carbon atoms composed of atoms is a ring containing a nitrogen atom to which it is bonded, and is a pyrrole ring, a pyrrolidine 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 as a substituent in that case, the group illustrated by description of A in the said general formula (I) is mentioned.
R3과 R4, R11과 R12, R13과 R14, R15와 R16, R17과 R18 및 R19와 R20이, 서로 연결되어 형성하는, 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환으로는 결합되어 있는 질소 원자를 포함시킨 환으로서, 모르폴린환, 옥사졸환, 옥사졸린환, 옥사디아졸환 등을 들 수 있다. 이들 환은 치환기를 가지고 있어도 되고, 그 경우의 치환기로는 상기 일반식(I) 중의 A의 설명에서 예시한 기를 들 수 있다. R 3 and R 4 , R 11 and R 12 , R 13 and R 14 , R 15 and R 16 , R 17 and R 18 and R 19 and R 20 are connected to each other to form a hydrogen atom, an oxygen atom, and a nitrogen Examples of the ring containing an atom and a carbon atom having 2 to 10 carbon atoms include a morpholine ring, an oxazole ring, an oxazoline ring, and an oxadiazole ring. These rings may have a substituent, and as a substituent in that case, the group illustrated by description of A in the said general formula (I) is mentioned.
본 발명에서는 상기 일반식(I) 중의 X1 및 X2가 -NR3R4이며, R3과 R4가 서로 연결되어, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환을 형성하고 있는 것이 바람직하고, X1에서의 환과 X2에서의 환이 동일한 것이 바람직하다. In the present invention, in the general formula (I), X 1 and X 2 are -NR 3 R 4 , R 3 and R 4 are connected to each other, and a ring having 2 to 10 carbon atoms consisting of a hydrogen atom, a nitrogen atom and a carbon atom Alternatively, a ring having 2 to 10 carbon atoms comprising a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom is preferably formed, and the ring in X 1 is preferably the same as the ring in X 2 .
상기 일반식(I) 중의 X1 및 X2가 이와 같은 구조인 화합물은 중합 개시제로서 사용한 경우, 발생하는 염기의 반응성이 높기 때문에 바람직하다. A compound having such a structure in which X 1 and X 2 in the general formula (I) is used as a polymerization initiator is preferable because of the high reactivity of the generated base.
특히, 상기 일반식(I) 중의 X1이 -NR3R4이며, R3과 R4가 서로 연결되어, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환을 형성하고 있는 것이, 발생하는 염기의 반응성이 높기 때문에 바람직하다. In particular, X 1 in the general formula (I) is —NR 3 R 4 , and R 3 and R 4 are connected to each other to form a ring having 2 to 10 carbon atoms comprising a hydrogen atom, a nitrogen atom, and a carbon atom. This is preferable because the reactivity of the generated base is high.
본 발명에서는 상기 일반식(I) 중의 X1 및 X2가 -NR3R4이며, R3 및 R4가, 각각 독립적으로 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기인 것도 바람직하고, 무치환의 탄소 원자수 2~10의 지방족 탄화수소기인 것이 보다 바람직하며, 특히 무치환의 탄소 원자수 2~6의 지방족 탄화수소기인 것이 바람직하고, X1 및 X2가 동일한 기인 것이 바람직하다. In the present invention, X 1 and X 2 in the general formula (I) are —NR 3 R 4 , and R 3 and R 4 are each independently an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. It is also preferable, and it is more preferably an unsubstituted aliphatic hydrocarbon group having 2 to 10 carbon atoms, particularly preferably an unsubstituted aliphatic hydrocarbon group having 2 to 6 carbon atoms, and it is preferable that X 1 and X 2 are the same group. do.
더욱이, 상기 일반식(I) 중의 X1 및 X2가 -NR3R4이며, R3이 수소 원자이고, R4가 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기인 것도 바람직하고, 특히 R4가 무치환의 탄소 원자수 6~10의 방향족 탄화수소기인 것이 바람직하다. Further, in the general formula (I), X 1 and X 2 are -NR 3 R 4 , R 3 is a hydrogen atom, and R 4 is an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms. It is preferable, and it is especially preferable that R<4> is an unsubstituted C6-C10 aromatic hydrocarbon group.
상기 일반식(I) 중의 X1 및 X2가 이와 같은 구조인 화합물은 중합 개시제로서 사용한 경우, 가열 시의 휘발물 억제의 관점에서 바람직하다. When X 1 and X 2 in the general formula (I) have such a structure, when used as a polymerization initiator, it is preferable from a viewpoint of suppressing volatile matter at the time of heating.
상기 일반식(I) 중의 n은 0 또는 1을 나타내고, m은 0 또는 1을 나타낸다. In the general formula (I), n represents 0 or 1, and m represents 0 or 1.
n 및 m이 0인 화합물은 열에 대하여 안정성이 높기 때문에 바람직하다. Compounds in which n and m are 0 are preferred because of their high thermal stability.
n 및 m이 1인 화합물은 경화 감도가 높은 화합물이 되기 때문에 바람직하다. The compound in which n and m are 1 is preferable because it becomes a compound with high curing sensitivity.
상기 일반식(I)로 나타내는 화합물의 구체예로는 이하의 화학식(1)~(216)으로 나타내는 화합물을 들 수 있다. 단, 본 발명은 이하의 화합물에 의해 하등 제한을 받는 것은 아니다. Specific examples of the compound represented by the general formula (I) include compounds represented by the following formulas (1) to (216). However, the present invention is not limited in any way by the following compounds.
상기 일반식(I)로 나타내는 본 발명의 카르바모일옥심 화합물의 제조 방법은 특별히 한정되지 않지만, 예를 들면, 일반식(I) 중의 A가 일반식(A-2)로 나타내지고, n 및 m이 0인 경우, 하기 반응식 1에 따라, 이하의 방법에 의해 제조할 수 있다. Although the manufacturing method of the carbamoyl oxime compound of this invention represented by the said general formula (I) is not specifically limited, For example, A in general formula (I) is represented by general formula (A-2), n and When m is 0, according to the following Scheme 1, it can be prepared by the following method.
즉, 케톤 화합물A와 하이드록시암모늄클로라이드를 피리딘 등의 염기 존재 하에서 반응시킴으로써, 옥심 화합물A를 얻는다. 이어서, 옥심 화합물A에, 클로로포름산4-니트로페닐을 반응시키고, 이어서 필요에 따라 아민을 반응시킴으로써, 본 발명의 카르바모일옥심 화합물A가 얻어진다. That is, the oxime compound A is obtained by making the ketone compound A and hydroxyammonium chloride react in presence of bases, such as a pyridine. Next, the carbamoyloxime compound A of this invention is obtained by making the oxime compound A react with 4-nitrophenyl chloroformic acid, and then making an amine react as needed.
(식 중 R40~R48, R1~R4는 상기 일반식(A-2)와 동일하다.) (Wherein, R 40 to R 48 , R 1 to R 4 are the same as in General Formula (A-2).)
일반식(I) 중의 A가 일반식(A-2)로 나타내지고, n=1인 경우는 하기 반응식 2에 따라, 산성 조건 하에서 케톤체B에 아질산이소부틸을 반응시켜서 옥심 화합물B를 얻는다. 이어서, 옥심 화합물B에, 클로로포름산4-니트로페닐을 반응시키고, 이어서 필요에 따라 아민을 반응시킴으로써, 본 발명의 카르바모일옥심 화합물B를 얻는다. When A in the general formula (I) is represented by the general formula (A-2) and n = 1, the ketone body B is reacted with isobutyl nitrite under acidic conditions to obtain the oxime compound B according to the following Scheme 2. Next, the carbamoyloxime compound B of this invention is obtained by making the oxime compound B react with chloroformic acid 4-nitrophenyl, and then, by making an amine react as needed.
(식 중 R40~R48, R1~R4는 상기 일반식(A-2)와 동일하다.) (Wherein, R 40 to R 48 , R 1 to R 4 are the same as in General Formula (A-2).)
상기 반응식 1 및 반응식 2는 모두 X1 및 X2가 -NR3R4인 경우를 나타내고 있는데, 사용하는 아민을 변경함으로써, X1 및 X2가 상기 식(a) 또는 상기 식(b)로 나타내는 기인 화합물도 제조할 수 있다. Scheme 1 and Scheme 2 both show the case where X 1 and X 2 are -NR 3 R 4 , and by changing the amine used, X 1 and X 2 can be converted into Formula (a) or Formula (b). A compound of the group shown can also be produced.
또한, 상기 반응식 1 및 반응식 2는 모두 R43 및 R46이 결합수인 경우를 나타내고 있는데, 카르바졸환 형성 시에 R41~R48 중 원하는 위치에 케톤기를 도입함으로써, R41~R48 중 어느 2개가 결합수인 화합물을 얻을 수 있다. In addition, Scheme 1 and Scheme 2 both show a case in which R 43 and R 46 are a bonded number. By introducing a ketone group at a desired position among R 41 to R 48 during the formation of a carbazole ring, among R 41 to R 48 A compound in which any two of them is a bonding number can be obtained.
옥심 화합물A는 일본 특허공보 특허제4223071호에 기재된 방법으로도 제조할 수 있다. The oxime compound A can also be produced by the method described in Japanese Patent Application Laid-Open No. 4223071.
본 발명의 카르바모일옥심 화합물은 자외선 등의 광 조사 또는 가열에 의해 효율적으로 염기 및 라디칼을 발생시키기 때문에, 잠재성 염기 발생제 및 라디칼 중합 개시제로서 유용하고, 특히 잠재성 염기 발생제로서 유용하다. The carbamoyloxime compound of the present invention is useful as a latent base generator and a radical polymerization initiator, and is particularly useful as a latent base generator 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 의미하고, 그 용도로는 PH 조정제, 염기를 사용한 촉매 등을 들 수 있다. The latent base generator of the present invention means 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 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 high base and radical generation efficiency among the polymerization initiators, and has a fairly high base generation efficiency, particularly as a photobase generator useful.
본 발명의 중합 개시제는 상기 일반식(I)로 나타내는 카르바모일옥심 화합물을 적어도 1종 함유한다. 상기 일반식(I)로 나타내는 카르바모일옥심 화합물과 병용할 수 있는 중합 개시제로는 특별히 제한되는 것은 아니지만, 종래 기지의 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), A conventionally well-known photobase generator and a radical photopolymerization initiator are mentioned.
상기 중합 개시제 중에서의 상기 일반식(I)로 나타내는 화합물의 함유량은 바람직하게는 1~100질량%, 보다 바람직하게는 50~100질량%이다. Content of the compound represented by the said General formula (I) in the said polymerization initiator becomes like this. Preferably it is 1-100 mass %, More preferably, it is 50-100 mass %.
본 발명의 중합성 조성물은, 상기 일반식(I)로 나타내는 카르바모일옥심 화합물을 적어도 1종 함유하는 중합 개시제(A), 및 중합성 화합물(B)을 함유하는 것이다. The polymerizable composition of this invention contains the polymerization initiator (A) which contains at least 1 sort(s) of the carbamoyl oxime compound represented by the said general formula (I), and a polymeric compound (B).
중합 개시제(A)의 함유량은 중합성 화합물(B) 100질량부에 대하여, 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 광 조사 시 또는 가열 시의 휘발물을 억제할 수 있기 때문에 바람직하다. To [ content of a polymerization initiator (A) / 100 mass parts of polymeric compound (B)), Preferably it is 1-20 mass parts, More preferably, it is 1-10 mass parts. 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. do.
본 발명에서 사용되는 중합성 화합물(B)로는 음이온 중합성 관능기를 가지는 화합물, 염기가 촉매로서 작용하는 반응 또는 염기가 부가하는 반응에 의해 경화하는 화합물, 및 라디칼 중합성 화합물을 들 수 있고, 자외선 등의 에너지 선을 조사함으로써 중합하여 경화하는 감광성 수지 또는 경화 온도가 저온화되는 경화 수지인 것이 바람직하다. 상기 음이온 중합성 관능기란, 자외선 등의 활성 에너지 선에 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 부가하는 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 탈수 축합 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 It is preferable that it is the photosensitive resin which superposes|polymerizes and hardens|cures by irradiating such energy rays, or the cured resin by which the curing temperature is lowered. 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. Examples of a reaction in which a base acts as a catalyst or a reaction in which a base is added include a urethane bond formation reaction with an isocyanate and an alcohol, an addition reaction of an epoxy resin and a compound containing a hydroxyl group, and addition of an epoxy resin and a compound containing a carboxylic acid group Reaction, addition reaction of an epoxy resin and a thiol compound, Michael addition reaction of a (meth)acryl group, dehydration condensation reaction of a polyamic acid, hydrolysis/polycondensation reaction of an 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 부가하는 반응에 의해 경화하는 화합물로는 예를 들면, 폴리아미드 수지(탈수 환화(環化)에 의한 폴리이미드화 반응), 에폭시·수산기계(개환(開環) 부가 반응), 에폭시·카르복실산계(개환 부가 반응), 에폭시·티올계(개환 부가 반응), 에폭시·산무수물계(개환 부가 반응), 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), 알콕시실란계(가수분해·중축합) 등을 들 수 있다. 라디칼에 의해 중합하는 화합물로는 에틸렌성 불포화 화합물을 들 수 있다. 반응성이 높기 때문에 라디칼 중합하는 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 hardens 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)環) addition reaction), epoxy/carboxylic acid type (ring-opening addition reaction), epoxy/thiol type (ring-opening addition reaction), epoxy/acid anhydride type (ring-opening addition reaction), acrylic/thiol type (Michael addition reaction), methacryl -thiol type (Michael addition reaction), acryl/amine type (Michael addition reaction), methacryl/amine type (Michael addition reaction), carboxylic acid/hydroxyl type (polyesterification reaction), carboxylic acid/amine type ( polyamidation reaction), isocyanate/hydroxyl type (polyurethanation reaction), alkoxysilane type (hydrolysis/polycondensation), and the like. 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 because of high reactivity and combinations of thiol compounds.
상기 에폭시 수지로는 예를 들면, 하이드로퀴논, 레조르신, 피로카테콜, 플로로글루시놀 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, 푸말산, 이타콘산, 석신산, 글루타르산, 수베르산, 아디프산, 아젤라산, 세바스산, 다이머산, 트리머산, 프탈산, 이소프탈산, 테레프탈산, 트리멜리트산, 트리메스산, 피로멜리트산, 테트라하이드로프탈산, 헥사하이드로프탈산, 엔도메틸렌테트라하이드로프탈산 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; 비닐시클로헥센디에폭사이드, 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 공역 디엔 중합체, 트리글리시딜이소시아누레이트 등의 복소환 화합물을 들 수 있다. 또한, 이들 에폭시 수지는 말단 이소시아네이트의 프리폴리머에 의해 내부 가교된 것 혹은 다가의 활성 수소 화합물(다가 페놀, 폴리아민, 카르보닐기 함유 화합물, 폴리인산에스테르 등)로 고분자량화한 것이어도 된다. Examples of the epoxy resin include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol, and phloroglucinol; 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, trimer 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 endomethylenetetrahydrophthalic 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, dicyclopentanediene 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; 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 with 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 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, and it is more preferable to have a glycidyl group more than bifunctional.
상기 페놀 수지로는, 1분자 중에 2개 이상의 하이드록시기를 가지는 페놀 수지가 바람직하고, 일반적으로 공지의 것을 사용할 수 있다. 페놀 수지로는 예를 들면, 비스페놀A형 페놀 수지, 비스페놀E형 페놀 수지, 비스페놀F형 페놀 수지, 비스페놀S형 페놀 수지, 페놀 노볼락 수지, 비스페놀A노볼락형 페놀 수지, 글리시딜에스테르형 페놀 수지, 아르알킬노볼락형 페놀 수지, 비페닐아르알킬형 페놀 수지, 크레졸노볼락형 페놀 수지, 다관능 페놀 수지, 나프톨 수지, 나프톨노볼락 수지, 다관능나프톨 수지, 안트라센형 페놀 수지, 나프탈렌 골격변성 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 한정되는 것은 아니다. 이들 페놀 수지는 1종을 단독으로 또는 2종 이상을 조합하여 사용할 수 있다. As said phenol resin, the phenol resin which has two or more hydroxyl groups in 1 molecule is preferable, 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, and 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 , polymerizable unsaturated hydrocarbon group-containing phenol resins, and hydroxyl group-containing silicone resins, but are not particularly limited. These phenol resins can be used individually by 1 type or in combination of 2 or more type.
상기 티올 화합물은 특별히 제한되지 않고, 모든 티올 화합물을 포함하는데, 1분자 중에 2개 이상의 티올기를 가지는 것이 바람직하다. The thiol compound is not particularly limited, and includes all thiol compounds, preferably having two or more thiol groups in one molecule.
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 트리메틸올프로판트리스메르캅토프로피오네이트이며, 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 specific 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- Dimercapto-3,6,9-trithiaundecane, 1,2,6,7-tetramercapto-4-thiaheptane, pentaerythrthiol, 1,1,3,3-tetrakis (mercapto Methylthio) 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-dithi An, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 1,3-bis(mercaptomethyl)benzene, pentaerythritol tetrakismercaptopropionate, and pentaeryth and ritol tetrakisthioglycolate.
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- dithiane, 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 산2무수물로서, 에틸렌테트라카르복실산2무수물, 1,2,3,4-벤젠테트라카르복실산2무수물, 1,2,3,4-시클로헥산테트라카르복실산2무수물, 2,2',3,3'-벤조페논테트라카르복실산2무수물, 2,2,3,3-비페닐테트라카르복실산무수물, 1,4,5,8-나프탈렌테트라카르복실산2무수물 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. As the polyamide resin, as acid dianhydride, ethylene tetracarboxylic dianhydride, 1,2,3,4-benzenetetracarboxylic dianhydride, 1,2,3,4-cyclohexanetetracarboxylic acid 2 Anhydride, 2,2',3,3'-benzophenonetetracarboxylic dianhydride, 2,2,3,3-biphenyltetracarboxylic anhydride, 1,4,5,8-naphthalenetetracarboxylic acid A dianhydride, etc. as a diamine, (o-, m- or p-) phenylenediamine, (3,3'- or 4,4'-) diaminodiphenyl ether, diaminobenzophenone, (3,3 and resins using '- or 4,4'-) diaminodiphenylmethane as a raw material.
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 alcohol) 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 화합물로는 예를 들면, 에틸렌, 프로필렌, 부틸렌, 이소부틸렌, 염화비닐, 염화비닐리덴, 불화비닐리덴, 테트라플루오로에틸렌 등의 불포화 지방족 탄화수소; (메타)아크릴산, α-클로르아크릴산, 이타콘산, 말레산, 시트라콘산, 푸말산, 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 카르복시기와 2개 이상의 (메타)아크릴로일기를 가지는 다관능(메타)아크릴레이트 등의 불포화 다염기산; (메타)아크릴산-2-하이드록시에틸, (메타)아크릴산-2-하이드록시프로필, (메타)아크릴산글리시딜, 하기 아크릴 화합물 No.1~No.4, (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)아크릴레이트 올리고머 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 무수 프탈산, 테트라하이드로 무수 프탈산, 트리알킬테트라하이드로 무수 프탈산, 5-(2,5-디옥소테트라하이드로푸릴)-3-메틸-3-시클로헥센-1,2-디카르복실산 무수물, 트리알킬테트라하이드로 무수 프탈산-무수 말레산 부가물, 도데세닐 무수 석신산, 무수 메틸하이믹산 등의 불포화 다염기산의 산무수물; (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 공역 디엔류; 폴리스티렌, 폴리메틸(메타)아크릴레이트, 폴리-n-부틸(메타)아크릴레이트, 폴리실록산 등의 중합체 분자쇄의 말단에 모노(메타)아크릴로일기를 가지는 매크로 모노머류; 비닐클로라이드, 비닐리덴클로라이드, 디비닐석시네이트, 디알릴프탈레이트, 트리알릴포스페이스, 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. 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, monosuccinic acid [2-(meth)acryloyloxyethyl], monophthalic acid [2-(meth)acryloyloxyethyl], ω-carboxypolycaprolactone mono(meth)acrylate having a carboxyl group and a hydroxyl group at both terminals mono(meth)acrylates of polymers; 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)acrylic acid glycidyl, the following acrylic compounds No. 1 to No. 4, (meth) methyl acrylate, (meth) butyl acrylate, (meth) acrylate isobutyl, (meth) acrylic acid-t-butyl, (meth) acrylic acid cyclohexyl, (meth) acrylate n-octyl, (meth) acrylate isooctyl, (meth) acrylate isononyl, ( Stearyl (meth)acrylate, lauryl (meth)acrylate, methoxyethyl (meth)acrylate, dimethylaminomethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, aminopropyl (meth)acrylate, dimethylamino (meth)acrylate Propyl, (meth)acrylic acid ethoxyethyl, (meth)acrylic acid poly(ethoxy)ethyl, (meth)acrylic acid butoxyethoxyethyl, (meth)acrylate ethylhexyl, (meth)acrylic acid phenoxyethyl, (meth)acrylic acid Tetrahydrofuryl, (meth) vinyl acrylate, (meth) allyl acrylate, (meth) acrylate benzyl, 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 Unsaturated monobasic acids and polyhydric alcohols, such as (meth)acrylate, tricyclodecanedimethyloldi(meth)acrylate, tri[(meth)acryloylethyl]isocyanurate, polyester (meth)acrylate oligomer, or esters of polyhydric phenols; 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, 카야랏드 DPHA, DPEA-12, PEG400DA, THE-330, RP-1040, NPGDA, PET30, R-684(이상, 니혼카야쿠 제품); 아로닉스 M-215, M-350(이상, 도아고세이 제품); NK 에스테르 A-DPH, A-TMPT, A-DCP, A-HD-N, TMPT, DCP, NPG 및 HD-N(이상, 신나카무라 가가꾸 고교 제품); SPC-1000, SPC-3000(이상, 쇼와 덴코 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 esters A-DPH, A-TMPT, A-DCP, A-HD-N, TMPT, DCP, NPG and HD-N (above, manufactured by Shin-Nakamura Chemical Co., Ltd.); SPC-1000, SPC-3000 (above, manufactured by Showa Denko); and the like.
본 발명의 중합성 조성물에는 임의 성분으로서, 무기 화합물, 색재, 잠재성 에폭시 경화제, 연쇄이동제, 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 polymeric composition of this invention as an optional component.
상기 무기 화합물로는 예를 들면, 산화니켈, 산화철, 산화이리듐, 산화티탄, 산화아연, 산화마그네슘, 산화칼슘, 산화칼륨, 실리카, 알루미나 등의 금속 산화물; 층상 점토광물, 밀로리블루, 탄산칼슘, 탄산마그네슘, 코발트계, 망간계, 유리 분말(특히 유리 플릿), 마이카, 탤크, 카올린, 페로시안화물, 각종 금속 황산염, 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, 특수파장 흡수제, 발잉크제 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 minerals, milory blue, calcium carbonate, magnesium carbonate, cobalt, manganese, 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 a filler, an antireflection agent, a conductive material, a stabilizer, a flame retardant, a mechanical strength improver, a special wavelength absorber, an ink repellent agent, 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 카본 블랙, 혹은 아세틸렌 블랙, 케첸 블랙 또는 램프 블랙 등의 카본 블랙; 상기 카본 블랙을 에폭시 수지로 조정 또는 피복한 것, 상기 카본 블랙을 미리 용매 중에 수지로 분산 처리하고, 20~200㎎/g의 수지를 흡착시킨 것, 상기 카본 블랙을 산성 또는 알카리성 표면처리한 것, 평균 입경이 8㎚ 이상이고 DBP 흡유량이 90㎖/100g 이하인 카본 블랙, 950℃에서의 휘발분 중의 CO 및 CO2로부터 산출한 전체 산소량이 표면적 100㎡당 9㎎ 이상인 카본 블랙; 흑연, 흑연화 카본 블랙, 활성탄, 탄소섬유, 카본 나노튜브, 카본 마이크로코일, 카본 나노혼, 카본 에어로겔, 풀러렌; 아닐린 블랙, 피그먼트 블랙7, 티탄 블랙; 산화크롬그린, 밀로리블루, 코발트그린, 코발트블루, 망간계, 페로시안화물, 인산염군청, 감청, 울트라마린, 셀룰리안 블루, 비리디언, 에메랄드그린, 황산납, 황색납, 아연황, 벵갈라(적색산화철(III)), 카드뮴레드, 합성 철흑, 엄버 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 a resin is adsorbed, and 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 of 9 mg or more per 100 m 2 of surface area calculated from CO and CO 2 in volatile matter at 950°C; 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 blue, wire blue, ultramarine, cellulian blue, viridian, emerald green, lead sulfate, yellow lead, zinc sulfur, Bengal ( Organic or inorganic pigments such as red iron (III) oxide), cadmium red, synthetic iron black, and umber 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. As said pigment, a commercially available pigment can also be used, 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 dyes 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. The latent epoxy curing agent includes, for example, dicyandiamide, modified polyamine, hydrazide, 4,4'diaminodiphenylsulfone, boron trifluoride amine complex salt, imidazole, guanamine, imidazole, Ureas, melamine, etc. are mentioned.
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-프로파놀, 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 요오드화알킬 화합물, 트리메틸올프로판트리스(3-메르캅토이소부티레이트), 부탄디올비스(3-메르캅토이소부티레이트), 헥산디티올, 데칸디티올, 1,4-디메틸메르캅토벤젠, 부탄디올비스티오프로피오네이트, 부탄디올비스티오글리콜레이트, 에틸렌글리콜비스티오글리콜레이트, 트리메틸올프로판트리스티오글리콜레이트, 부탄디올비스티오프로피오네이트, 트리메틸올프로판트리스티오프로피오네이트, 트리메틸올프로판트리스티오글리콜레이트, 펜타에리트리톨테트라키스티오프로피오네이트, 펜타에리트리톨테트라키스티오글리콜레이트, 트리스하이드록시에틸트리스티오프로피오네이트, 디에틸티오크산톤, 디이소프로필티오크산톤, 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 pentaerythritol tetrakis (3-mercaptopropionate); A disulfide compound obtained by oxidizing the mercapto compound, an alkyl iodide compound such as iodoacetic acid, iodopropionic acid, 2-iodethanol, 2-iodoethanesulfonic acid, and 3-iodopropanesulfonic acid, trimethylolpropanetris(3-mercap) Toisobutyrate), butanediol bis (3-mercapto isobutyrate), hexanedithiol, decanedithiol, 1,4-dimethyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisti Oglycolate, trimethylolpropane tristhioglycolate, butanediolbisthiopropionate, trimethylolpropane tristhiopropionate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetra Kisthioglycolate, trishydroxyethyltristhiopropionate, diethylthioxanthone, diisopropylthioxanthone, the following compound No.C1, trimercaptopropionate tris(2-hydroxyethyl)isocyanurate Aliphatic polyfunctional thiol compounds, such as Showa Denko Corporation Karenz MT BD1, PE1, NR1, etc. are mentioned.
상기 용제로는 통상, 상기의 각 성분(중합 개시제(A) 및 중합성 화합물(B) 등)을 용해 또는 분산시킬 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; 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; 미네랄스피릿, 스와졸 #310(코스모 마쓰야마 세키유(주)), 솔벳소 #100(엑손 가가쿠(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 용제로서 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; 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, 제막(製膜)성, 용해성의 점에서, 케톤류 또는 에테르에스테르계 용제, 특히, 프로필렌글리콜-1-모노메틸에테르-2-아세테이트(이하, "PGMEA"라고도 함.) 또는 시클로헥사논이 바람직하게 사용된다. Among these, from the viewpoint of alkali developability, patterning property, film forming property, and solubility, ketones or ether ester solvents, particularly propylene glycol-1-monomethyl ether-2-acetate (hereinafter also referred to as “PGMEA”) .) or cyclohexanone is preferably used.
본 발명의 중합성 조성물에서 용제의 함유량은 특별히 제한되지 않고, 각 성분이 균일하게 분산 또는 용해되고, 또한 본 발명의 중합성 조성물이 각 용도에 적합한 액상 내지 페이스트 형상을 띠는 양이면 되는데, 통상 본 발명의 중합성 조성물 중의 고형분(용제 이외의 전성분)의 양이 10~90질량%가 되는 범위에서 용제를 함유시키는 것이 바람직하다. The content of the solvent in the polymerizable composition of the present invention is not particularly limited, each component is uniformly dispersed or dissolved, and the polymerizable composition of the present invention may be in an amount suitable for each use in a liquid or paste form, usually It is preferable to contain a solvent in the range used as 10-90 mass % of quantity of solid content (all components other than a solvent) in the polymeric composition of this invention.
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 can 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 사용량은 중합성 화합물(B) 100질량부에 대하여 바람직하게는 10~500질량부이다. When using the said organic polymer, the usage-amount becomes like this. Preferably it is 10-500 mass parts with respect to 100 mass parts of polymeric compound (B).
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 지방산알칼리염, 알킬설폰산염, 알킬황산염 등의 음이온계 계면활성제; 고급 아민할로겐산염, 제4급 암모늄염 등의 양이온계 계면활성제; 폴리에틸렌글리콜알킬에테르, 폴리에틸렌글리콜지방산에스테르, 소르비탄지방산에스테르, 지방산모노글리세라이드 등의 비이온 계면활성제; 양성 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 가가쿠사 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, silane having an isocyanate group, a methacryloyl group or an epoxy group, such as KBE-9007, KBM-502, and KBE-403 A 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 있고, 서로 동일해도 되고, 달라도 된다. 또한, 알킬에테르화되지 않은 메틸올기는 1분자 내에서 자기 축합되어 있어도 되고, 2분자 사이에서 축합하여, 그 결과 올리고머 성분이 형성되어 있어도 된다. Here, a methyl group, an ethyl group, or a butyl group is mentioned as an alkyl group which comprises an alkyl ether, It may mutually be same or different. In addition, the methylol group which is not alkyl-etherified may be self-condensed within 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, hexamethoxymethylmelamine, hexabutoxymethylmelamine, tetramethoxymethylglycoluril, tetrabutoxymethylglycoluril, or the like can be used.
이들 중에서도 용제에 대한 용해성, 중합성 조성물로부터 결정 석출(析出)하기 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 사용량은 그 사용 목적에 따라 적절히 선택되고 특별히 제한되지 않는데, 바람직하게는 중합성 화합물(B) 100질량부에 대하여 합계 50질량부 이하로 할 수 있다. In the polymerizable composition of the present invention, the amount of optional components other than the polymerization initiator (A) and the polymerizable compound (B) (provided that inorganic compounds, color materials, and solvents are excluded) are appropriately selected according to the purpose of use, and especially Although it does not restrict|limit, Preferably, it can be set as 50 mass parts or less in total with respect to 100 mass parts of polymeric compound (B).
본 발명의 중합성 조성물은 에너지 선을 조사하여 경화물로 할 수 있다. 상기 경화물은 용도에 따른 적절한 형상으로 형성된다. 예를 들면 막 형상의 경화물을 형성하는 경우에는 본 발명의 중합성 조성물은 스핀 코터, 롤 코터, 바 코터, 다이 코터, 커튼 코터, 각종 인쇄, 침지 등의 공지의 수단으로, 소다 유리, 석영 유리, 반도체기판, 금속, 종이, 플라스틱 등의 지지 기체 상에 적용할 수 있다. 또한, 일단 필름 등의 지지 기체 상에 실시한 후, 다른 지지 기체 상에 전사(轉寫)할 수도 있고, 그 적용 방법에 제한은 없다. The polymerizable composition of the present invention can be made into a cured product by irradiating an energy ray. 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 a known means such as a spin coater, a roll coater, a bar coater, a die coater, a curtain coater, various types of printing and immersion, soda glass, quartz It can be applied on supporting substrates such as glass, semiconductor substrates, metals, papers, and plastics. Moreover, after implementing once on support bases, such as a film, it can also be transcribe|transferred on another support base, and there is no restriction|limiting in the application method.
본 발명의 중합성 조성물을 경화시킬 때에 사용되는 에너지 선의 광원으로는 초고압 수은 램프, 고압 수은 램프, 중압 수은 램프, 저압 수은 램프, 수은 증기 아크등, 크세논 아크등, 카본 아크등, 메탈할라이드 램프, 형광등, 텅스텐 램프, 엑시머 램프, 살균등, 발광 다이오드, CRT 광원 등에서 얻어지는 2000옹스트롬~7000옹스트롬의 파장을 가지는 전자파 에너지나 전자선, X선, 방사선 등의 고에너지 선을 이용할 수 있는데, 바람직하게는 파장 300~450㎚의 광을 발광하는 초고압 수은 램프, 수은 증기 아크등, 카본 아크등, 크세논 아크등 등이 사용된다. Examples of light sources of energy rays 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, It is possible to use 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., or high energy rays such as electron beams, X-rays, and radiation Ultra-high pressure mercury lamps, mercury vapor arc lamps, carbon arc lamps, and xenon arc lamps that emit light of 300 to 450 nm are used.
더욱이, 노광 광원에 레이저광을 사용함으로써, 마스크를 사용하지 않고, 컴퓨터 등의 디지털 정보로부터 직접 화상을 형성하는 레이저 직접 묘화법이, 생산성뿐만 아니라, 해상성이나 위치 정밀도 등의 향상도 도모할 수 있기 때문에 유용하고, 그 레이저광으로는 340~430nm의 파장의 광이 알맞게 사용되는데, 엑시머 레이저, 질소 레이저, 아르곤 이온 레이저, 헬륨 카드뮴 레이저, 헬륨 네온 레이저, 크립톤 이온 레이저, 각종 반도체 레이저 및 YAG 레이저 등의 가시부터 적외 영역의 광을 발하는 것도 사용할 수 있다. 이들 레이저광을 사용하는 경우에는 바람직하게는 가시부터 적외의 해당 영역을 흡수하는 증감색소가 첨가된다. Furthermore, by using laser light as the exposure light source, the laser direct drawing method, which forms an image directly from digital information such as a computer without using a mask, can improve not only productivity but also resolution and positional accuracy. As the laser light, light with a wavelength of 340 to 430 nm is suitably used. Excimer laser, nitrogen laser, argon ion laser, helium cadmium laser, helium neon laser, krypton ion laser, various semiconductor lasers and YAG lasers What emits light in the visible to infrared region of the back can also be used. In the case of using these laser beams, a sensitizing dye that absorbs the relevant region from visible to infrared is preferably added.
또한, 본 발명의 중합성 조성물의 경화에는 상기 에너지 선의 조사 후, 가열하는 것이 통상 필요하고, 40~150℃ 정도의 가열이 경화율의 점에서 바람직하다. Moreover, it is normally necessary to heat after irradiation of the said energy ray 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; 휴대정보단말, 디지털 카메라 등의 컬러 표시의 액정 표시 소자에서의 컬러 필터; CCD 이미지 센서의 컬러 필터; 플라스마 표시 패널용 전극 재료; 분말 코팅; 인쇄 잉크; 인쇄판; 접착제; 치과용 조성물; 겔코트; 전자공학용 포토레지스트; 전기 도금 레지스트; 에칭 레지스트; 드라이 필름; 땜납 레지스트; 다양한 표시 용도용의 컬러 필터를 제조하기 위한 혹은 플라스마 표시 패널, 전기 발광 표시 장치, 및 LCD의 제조 공정에서 그들의 구조를 형성하기 위한 레지스트; 전기 및 전자부품을 봉입하기 위한 조성물; 솔더 레지스트; 자기 기록 재료; 미소 기계부품; 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; 화상 기록 재료; 미세 전자회로; 탈색 재료; 화상 기록 재료를 위한 탈색 재료; 마이크로캡슐을 사용하는 화상 기록 재료용 탈색 재료; 인쇄 배선판용 포토레지스트 재료; UV 및 가시 레이저 직접 화상계용 포토레지스트 재료; 프린트 회로 기판의 축차 적층에서의 유전체층 형성에 사용하는 포토레지스트 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 TV; PC monitor; color filters in liquid crystal display elements for color display such as 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; photoresist for electronics; electroplating resist; etching resist; dry film; solder resist; resists for manufacturing color filters for various display applications or for forming their structures in the manufacturing process of plasma display panels, electroluminescent display devices, and LCDs; compositions for encapsulating electrical and electronic components; solder resist; magnetic recording material; micro 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; discoloration 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 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.
상기의 액정표시 패널용 스페이서는 (1) 본발명의 중합성 조성물의 도막을 기판 상에 형성하는 공정, (2) 상기 도막에 소정 패턴 형상을 가지는 마스크를 통해 에너지 선(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 a liquid crystal display panel is formed by (1) forming a coating film of the polymerizable composition of the present invention on a substrate, (2) irradiating energy rays (light) to the coating film through a mask having a predetermined pattern shape , (3) a baking process after exposure, (4) a process of developing the coating film after exposure, and (5) a process 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, 발잉크제를 첨가하는 블랙 매트릭스용 레지스트의 경우, 프로파일 각이 50° 이상인 잉크젯 방식 컬러 필터용 격벽에 바람직하게 사용된다. 상기 발잉크제로는 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 black matrix resist to which an ink repellent agent is added, it is preferably used for the partition wall for inkjet system color filters whose profile angle is 50 degrees or more. As the ink repellent agent, a composition containing a fluorine-based surfactant and a fluorine-based surfactant is 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 액적(液滴)을 부여하여 화상 영역을 형성하는 방법에 의해 광학소자가 제조된다. 이 때, 상기 액적이 착색제를 함유하고, 상기 화상 영역이 착색되어 있는 것이 바람직하고, 그 경우에는 상기의 제조 방법에 의해 제작된 광학소자는 기판 상에 복수의 착색 영역으로 이루어지는 화소군과 상기 화소군의 각 착색 영역을 이격하는 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. An optical element is manufactured by a method of forming an image region by imparting. At this time, it is preferable that the droplet contains a colorant and the image region is colored. It becomes a thing which has at least a partition which separates each colored area|region of a group.
본 발명의 중합성 조성물은 보호막 또는 절연막용 조성물로서도 사용할 수 있다. 이 경우, 자외선흡수제, 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 be used also as a composition for a protective film or an insulating film. In this case, it may contain a UV absorber, alkylation-modified melamine and/or acrylic-modified melamine, a monofunctional or bifunctional (meth)acrylate monomer containing an alcoholic hydroxyl group in the molecule, and/or silica sol.
상기 절연막은 박리 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
본 발명의 중합성 조성물은 무기 화합물을 함유시킴으로써, 감광성 페이스트 조성물로서 사용할 수 있다. 상기 감광성 페이스트 조성물은 플라스마 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 material 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 설명하겠지만, 본 발명은 이들 실시예 등에 한정되는 것이 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 and the like.
〔실시예 1〕 화합물 1의 합성 [Example 1] Synthesis of compound 1
이하에 나타낸 스킴에 따라 화합물 1을 합성했다. Compound 1 was synthesized according to the scheme shown below.
(옥심체 1의 합성) (Synthesis of oxime 1)
100㎖ 4구 플라스크에, 1-(6-(3-시클로헥실프로파노일)-9-에틸-9H-카르바졸-3-일)옥탄-1-온 1.0eq.을 첨가하고, 디메틸포름아미드(이론 수량의 350중량%)에 용해했다. 거기에 4M·HCl-아세트산에틸 2.0eq.과 아질산이소부틸 2.2eq.을 첨가하고, 35℃에서 1시간 교반했다. 반응액에 메틸이소부틸케톤을 첨가하고, 이온 교환수로 3회 세정한 후, 황산마그네슘에 의해 건조시켜, 농축했다. 잔사를 아세트산에틸에 용해하고, 헥산 첨가에 의해 정석(晶析)함으로써, 옥심체 1을 백색 분말상 화합물로서 수율 79%로 얻었다. To a 100 ml four-necked flask, 1.0 eq. of 1-(6-(3-cyclohexylpropanoyl)-9-ethyl-9H-carbazol-3-yl)octan-1-one was added, and dimethylformamide (350% by weight of the theoretical amount). 2.0eq. of 4M*HCl-ethyl acetate and 2.2eq. of isobutyl nitrite were added there, and it stirred at 35 degreeC for 1 hour. Methyl isobutyl ketone was added to the reaction solution, washed with ion-exchanged water 3 times, dried over magnesium sulfate, and concentrated. The residue was dissolved in ethyl acetate and crystallized by addition of hexane to obtain oxime body 1 as a white powdery compound in a yield of 79%.
(화합물 1의 합성) (Synthesis of compound 1)
100㎖ 4구 플라스크에, 옥심체 1을 1.0eq., 디클로로메탄(이론 수량의 500중량%), 트리에틸아민 4.0eq.을 첨가하고, 빙욕상(氷浴上) 5℃에서 교반을 실시했다. 거기에 클로로포름산4-니트로페닐 2.2eq.을 디클로로메탄에 녹인 것을 적하하여 첨가했다. 적하 종료 후, 실온에서 30분간 교반했다. 다시 빙욕상 5℃까지 냉각 후, 피페리딘 2.2eq.을 적하하여 첨가했다. 실온에서 3시간 교반하고, 감압 용매 증류제거했다. 거기에 톨루엔과 5질량% NaOH 수용액을 첨가하고, 유수분리를 실시했다. 추가로 유기층을 이온 교환수로 3회 세정한 후, 농축을 실시했다. 잔사를 실리카겔 칼럼 크로마토그래피(용리제:톨루엔 및 아세트산에틸=5:1)에 의해 정제하고, 화합물 1을 황색 점조 액상 화합물로서 수율 11%로 얻었다. 화합물 1은 대기압하, 25℃에서 액상이었다. 얻어진 화합물의 1H-NMR 분석 결과를 표 2에 나타낸다. 1.0eq., dichloromethane (500 weight% of theoretical quantity), and triethylamine 4.0eq. for the oxime body 1 were added to a 100 mL four neck flask, and it stirred at 5 degreeC on an ice bath. . Thereto, 2.2 eq. of 4-nitrophenyl chloroformate dissolved in dichloromethane was added dropwise. After completion|finish of dripping, it stirred at room temperature for 30 minutes. After cooling to 5°C on an ice bath again, piperidine 2.2eq. was added dropwise. The mixture was stirred at room temperature for 3 hours, and the solvent was distilled off under reduced pressure. Toluene and 5 mass % NaOH aqueous solution were added there, and oil-water separation was performed. Furthermore, after washing|cleaning the organic layer 3 times with ion-exchange water, it concentrated. The residue was purified by silica gel column chromatography (eluent: toluene and ethyl acetate = 5:1) to obtain compound 1 as a yellow viscous liquid compound in a yield of 11%. Compound 1 was liquid at 25°C under atmospheric pressure. Table 2 shows the results of 1 H-NMR analysis of the obtained compound.
〔실시예 2〕 화합물 2의 합성 [Example 2] Synthesis of compound 2
이하에 나타낸 스킴에 따라 화합물 2를 합성했다. Compound 2 was synthesized according to the scheme shown below.
(옥심체 2의 합성) (Synthesis of oxime 2)
100㎖ 4구 플라스크에, 1,1'-(9-에틸-9H-카르바졸-3,6-디일)비스(옥탄-1-온) 1.0eq.을 첨가하고, 디메틸아세트아미드(이론 수량의 300중량%)에 용해했다. 용액에 하이드록시암모늄클로라이드 6.4eq. 및 수산화나트륨 6.4eq.을 첨가했다. 반응 혼합물을 75℃에서 6시간 교반했다. 반응액에 클로로포름을 첨가하고, 이온 교환수로 3회 세정했다. 유기층을 냉각함으로써 재결정화하고, 옥심체 2를 백색 분말상 화합물로서 수율 78%로 얻었다. To a 100 ml four-necked flask, 1.0 eq. of 1,1'-(9-ethyl-9H-carbazole-3,6-diyl)bis(octan-1-one) was added, and dimethylacetamide (theoretical quantity 300% by weight). 6.4eq. of hydroxyammonium chloride in the solution. and 6.4 eq. of sodium hydroxide. The reaction mixture was stirred at 75° C. for 6 hours. Chloroform was added to the reaction solution, and the mixture was washed 3 times with ion-exchanged water. Recrystallization was carried out by cooling the organic layer, and the oxime body 2 was obtained as a white powdery compound with a yield of 78%.
(화합물 2의 합성) (Synthesis of compound 2)
실시예 1에 기재된 옥심체 1을 옥심체 2로 변경한 것 이외에는 실시예 1과 동일한 조작으로 수세 공정까지 실시했다. 농축 후의 잔사에 에탄올을 첨가하고 정석을 실시하고, 목적물을 백색 분말상 화합물로서 수율 20%로 얻었다. 얻어진 화합물의 TG-DTA(융점) 및 1H-NMR 분석을 실시했다. 결과를 표 1 및 표 2에 나타낸다. Except having changed the oxime body 1 of Example 1 into the oxime body 2, it implemented to the water washing process by operation similar to Example 1. Ethanol was added to the concentrated residue for crystallization, and the target product was obtained as a white powdery compound in a yield of 20%. TG-DTA (melting point) and 1 H-NMR analysis of the obtained compound were performed. A result is shown in Table 1 and Table 2.
〔실시예 3〕 화합물 3의 합성 [Example 3] Synthesis of compound 3
이하에 나타낸 스킴에 따라 화합물 3을 합성했다. Compound 3 was synthesized according to the scheme shown below.
(옥심체 3의 합성) (Synthesis of oxime 3)
100㎖ 4구 플라스크에, 1,1'-(9H-플루오렌-2,7-디일)비스(헥산-1-온) 1.0eq.을 첨가하고, 디메틸아세트아미드(이론 수량의 300중량%)에 용해했다. 용액에 하이드록시암모늄클로라이드 2.5eq. 및 피리딘 2.2eq.을 첨가했다. 반응 혼합물을 80℃에서 5시간 교반했다. 반응액에 아세트산에틸을 첨가하고, 이온 교환수로 3회 세정했다. 농축 후의 잔사에 메탄올을 첨가하고 정석을 실시하고, 목적물을 백색 분말상 화합물로서 수율 80%로 얻었다. To a 100 ml four-necked flask, 1.0 eq. of 1,1'-(9H-fluorene-2,7-diyl)bis(hexan-1-one) was added, and dimethylacetamide (300% by weight of theoretical amount) dissolved in 2.5eq. of hydroxyammonium chloride in the solution. and 2.2 eq. of pyridine. The reaction mixture was stirred at 80° C. for 5 hours. Ethyl acetate was added to the reaction solution, and the mixture was washed 3 times with ion-exchanged water. Methanol was added to the residue after concentration to perform crystallization, and the target product was obtained as a white powdery compound in a yield of 80%.
(화합물 3의 합성) (Synthesis of compound 3)
실시예 1에 기재된 옥심체 1을 옥심체 3으로 변경한 것 이외에는 실시예 1과 동일한 조작으로 수세 공정까지 실시했다. 농축 후의 잔사에 메탄올을 첨가하고 정석을 실시하고, 목적물을 옅은 황색 분말상 화합물로서 수율 74%로 얻었다. 얻어진 화합물의 TG-DTA(융점) 및 1H-NMR 분석을 실시했다. 결과를 표 1 및 표 2에 나타낸다. Except having changed the oxime body 1 of Example 1 into the oxime body 3, it implemented to the water washing process by operation similar to Example 1. Methanol was added to the residue after concentration for crystallization, and the target product was obtained as a pale yellow powdery compound in a yield of 74%. TG-DTA (melting point) and 1 H-NMR analysis of the obtained compound were performed. A result is shown in Table 1 and Table 2.
〔실시예 4 및 비교예 1〕 중합성 조성물의 조제 [Example 4 and Comparative Example 1] Preparation of polymerizable composition
표 3에 기재된 배합을 실시하고, 중합성 조성물 1 및 비교 중합성 조성물 1을 얻었다. 한편, 표 중의 배합 수치는 질량부를 나타낸다. The compounding|blending of Table 3 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-2: 화합물 2 A-2: compound 2
A'-1: 비교 화합물 1 A'-1: Comparative compound 1
B-1: EPPN-201(페놀노볼락형 에폭시 수지, 에폭시 등량 193g/eq., 니혼카야쿠사 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, 도레 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 순서로 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 procedure. A result is shown in Table 4.
중합성 조성물 1 및 비교 중합성 조성물 1을 각각 유리 기재(10㎝×10㎝)에 스핀 코터(500rpm×2초→1000rpm×10초→슬로프×0.5초)를 이용하여 도막하고(도포량 약 2㎖), 오븐 중에서 프리베이킹(90℃×90초)을 실시하고, 제막했다. Polymerizable composition 1 and comparative polymerizable composition 1 were respectively coated on a glass substrate (10 cm × 10 cm) using a spin coater (500 rpm × 2 seconds → 1000 rpm × 10 seconds → slope × 0.5 seconds) (application amount about 2 ml) ), prebaking (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)을 마스킹하고, 365㎚ 환산 조도 20㎽/㎠의 수은 램프를 이용하여, 소정량의 자외광을 조사했다. For each film, a step tablet (33-stage type, OD value 0-3) having a gradation in which the transmittance is continuously changed is masked, and a predetermined amount of ultraviolet light is investigated
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, 잔존하는 막의 단수를 육안으로 확인했다. About the obtained cured film sample, the number of stages of the film|membrane which remained was confirmed visually.
상기 표 4의 결과로부터, 본원 발명의 중합성 조성물은 비교 중합성 조성물과 비교하여 잔단(殘段) 수가 많기(경화성이 높기)때문에, UV-LED 광원에 대하여 고감도라고 할 수 있고, 본 발명의 화합물이 중합 개시제로서 뛰어난 것은 명백하다. From the results in Table 4, the polymerizable composition of the present invention has a large number of residues (high curability) compared to the comparative polymerizable composition, so it can be said that it is highly sensitive to a UV-LED light source, and the It is clear that the compound is excellent as a polymerization initiator.
〔평가예 2〕 경화막의 외관 확인 [Evaluation example 2] Appearance confirmation of cured film
실시예 4에 나타낸 배합에서, 화합물 2를 화합물 1로 바꿔 놓은 것을 조제했다(중합성 조성물 2). 이것을 평가예 1의 순서로 제막하고, 스텝 태블릿 없이 막 앞면의 UV 경화를 실시했다. 동일한 처리를 실시한 비교 중합성 조성물 1의 막이 황변하는 것에 반해, 중합성 조성물 2는 노광 시의 착색이 없고 무색 투명의 경화막이 얻어졌다. 따라서, 본원 발명의 중합성 조성물은 비교 중합성 조성물과 비교하여 착색성이 낮고(광 퇴색성을 가짐), 경화 재료로서 뛰어난 특성을 가지는 것이다. In the formulation shown in Example 4, the compound 2 replaced with the compound 1 was prepared (polymerizable composition 2). This was formed into a film by the procedure of Evaluation Example 1, and UV curing of the front surface of a film|membrane was performed without a step tablet. Whereas the film of the comparative polymerizable composition 1 subjected to the same treatment yellowed, the polymerizable composition 2 had no coloration upon exposure and a colorless and transparent cured film was obtained. Accordingly, the polymerizable composition of the present invention has low colorability (having photobleaching properties) and excellent properties as a cured material compared with the comparative polymerizable composition.
〔실시예 5〕 화합물 4의 합성 [Example 5] Synthesis of compound 4
이하에 나타낸 스킴에 따라 화합물 4를 합성했다. Compound 4 was synthesized according to the scheme shown below.
(옥심체 4의 합성) (Synthesis of oxime 4)
100㎖ 4구 플라스크에, 1,1'-(티오비스(4,1-페닐렌))비스(헥산-1-온) 1.0eq.을 첨가하고, 디메틸포름아미드(이론 수량의 400중량%)에 용해했다. 용액에 하이드록시암모늄클로라이드 2.6eq. 및 피리딘 2.6eq.을 첨가했다. 반응 혼합물을 55℃에서 7시간 가열 교반한 후, 이온 교환수를 첨가하고, 아세트산에틸로 추출했다. 유기층을 이온 교환수로 3회 세정하고, 황산마그네슘에 의해 건조시켜, 농축했다. 이것에 1,2-디클로로에탄(이론 수량의 2000중량%)을 첨가하고 재결정하여, 옥심체 4를 백색 분체로 수율 77%로 얻었다. To a 100 ml four-necked flask, 1.0 eq. of 1,1'-(thiobis(4,1-phenylene))bis(hexan-1-one) was added, and dimethylformamide (400% by weight of theoretical amount) dissolved in 2.6eq of hydroxyammonium chloride in the solution. and 2.6 eq. of pyridine. After the reaction mixture was heated and stirred at 55°C for 7 hours, ion-exchanged water was added, followed by extraction with ethyl acetate. The organic layer was washed 3 times with ion-exchanged water, dried over magnesium sulfate, and concentrated. 1,2-dichloroethane (2000% by weight of the theoretical amount) was added thereto and recrystallized to obtain oxime body 4 as a white powder in a yield of 77%.
(화합물 4의 합성) (Synthesis of compound 4)
100㎖ 4구 플라스크에, 옥심체 4를 1.0eq., 디클로로에탄(이론 수량의 600중량%), 트리에틸아민 4.0eq.을 첨가하고, 빙욕상 5℃에서 교반을 실시했다. 거기에 클로로포름산4-니트로페닐 3.0eq.을 디클로로에탄(이론 수량의 300중량%)에 녹인 것을 적하하여 첨가했다. 적하 종료 후, 실온에서 1시간 교반했다. 다시 빙욕상 5℃까지 냉각 후, 아닐린 3.0eq.을 적하하여 첨가했다. 실온에서 1시간 교반하고, 감압 용매 증류제거했다. 거기에 아세트산에틸과 이온 교환수를 첨가하고, 유수분리를 실시했다. 추가로 유기층을 1질량% 수산화나트륨 수용액으로 3회, 이온 교환수로 2회 세정하고, 황산마그네슘에 의해 건조시켜, 농축했다. 잔사를 실리카겔 칼럼 크로마토그래피(용리제=아세트산에틸:톨루엔=1:25)에 의해 정제하고, 목적물을 백색 분말상 화합물로서 수율 57%로 얻었다. 얻어진 화합물의 TG-DTA(융점) 및 1H-NMR 분석을 실시했다. 결과를 표 5 및 표 6에 나타낸다. 1.0eq., dichloroethane (600 weight% of theoretical quantity), and triethylamine 4.0eq. for the oxime body 4 were added to a 100 ml four neck flask, and it stirred at 5 degreeC on the ice bath. Thereto, 3.0 eq. of 4-nitrophenyl chloroformate dissolved in dichloroethane (300 wt% of the theoretical amount) was 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, 3.0 eq. of aniline was added dropwise. The mixture was stirred at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. Ethyl acetate and ion-exchange water were added thereto, and oil-water separation was performed. Furthermore, the organic layer was washed 3 times with 1 mass % sodium hydroxide aqueous solution and twice with ion-exchanged water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent = ethyl acetate : toluene = 1:25) to obtain the target product as a white powdery compound in a yield of 57%. TG-DTA (melting point) and 1 H-NMR analysis of the obtained compound were performed. The results are shown in Tables 5 and 6.
〔실시예 6〕 [Example 6]
(화합물 5의 합성) (Synthesis of compound 5)
실시예 5에 기재된 아닐린을 4-메틸피페리딘으로 변경한 것 이외에는 실시예 5와 동일한 조작으로 수세 공정까지 실시했다. 농축 후의 잔사를 실리카겔 칼럼 크로마토그래피(용리제=아세트산에틸:톨루엔=1:5)에 의해 정제하고, 목적물을 옅은 황색 점조 액상 화합물로서 수율 80%로 얻었다. 얻어진 화합물의 1H-NMR 분석을 실시했다. 결과를 표 6에 나타낸다. Except for changing the aniline described in Example 5 to 4-methylpiperidine, the same operation as in Example 5 was carried out, up to the water washing step. The concentrated residue was purified by silica gel column chromatography (eluent=ethyl acetate:toluene=1:5) to obtain the target product as a pale yellow viscous liquid compound in a yield of 80%. 1 H-NMR analysis of the obtained compound was performed. A result is shown in Table 6.
〔실시예 7〕 [Example 7]
이하에 나타낸 스킴에 따라 화합물 6을 합성했다. Compound 6 was synthesized according to the scheme shown below.
(옥심체 6의 합성) (Synthesis of oxime 6)
100㎖ 4구 플라스크에, 1,1'-(티오비스(4,1-페닐렌))비스(헥산-1-온) 1.0eq.을 첨가하고, 디메틸포름아미드(이론 수량의 350중량%)에 용해했다. 거기에 4M·HCl-아세트산에틸 2.0eq.과 아질산이소부틸 2.5eq.을 첨가하고, 45℃에서 3시간 교반했다. 반응액에 아세트산에틸을 첨가하고, 이온 교환수로 4회 세정한 후, 황산마그네슘에 의해 건조시키고, 농축했다. 잔사를 실리카겔 칼럼 크로마토그래피(용리제=아세트산에틸:헥산=1:5)에 의해 정제하고, 목적물을 옅은 황색 고체로 수율 72%로 얻었다. To a 100 ml four-necked flask, 1.0 eq. of 1,1'-(thiobis(4,1-phenylene))bis(hexan-1-one) was added, and dimethylformamide (350% by weight of theoretical amount) dissolved in 2.0eq. of 4M*HCl-ethyl acetate and 2.5eq. of isobutyl nitrite were added there, and it stirred at 45 degreeC for 3 hours. Ethyl acetate was added to the reaction solution, washed with ion-exchanged water 4 times, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent = ethyl acetate: hexane = 1:5) to obtain the target product as a pale yellow solid in a yield of 72%.
(화합물 6의 합성) (Synthesis of compound 6)
실시예 5에 기재된 옥심체 4를 옥심체 6으로, 아닐린을 디부틸아민으로 각각 변경한 것 이외에는 실시예 5와 동일한 조작으로 수세 공정까지 실시했다. 농축 후의 잔사를 실리카겔 칼럼 크로마토그래피(용리제=아세트산에틸:톨루엔=1:20)에 의해 정제하고, 목적물을 옅은 황색 점조 액상 화합물로서 수율 5%로 얻었다. 얻어진 화합물의 1H-NMR 분석을 실시했다. 결과를 표 6에 나타낸다. Except having changed the oxime body 4 described in Example 5 into the oxime body 6, and aniline into dibutylamine, respectively, it carried out to the water washing process by operation similar to Example 5. The concentrated residue was purified by silica gel column chromatography (eluent=ethyl acetate:toluene=1:20) to obtain the target product as a pale yellow viscous liquid compound in a yield of 5%. 1 H-NMR analysis of the obtained compound was performed. A result is shown in Table 6.
본 발명의 카르바모일옥심 화합물은 높은 광염기 발생 효율을 가지고 있고, 중합 개시제로서 사용한 경우, 종래의 광염기 발생제보다도 효율적으로 염기를 발생시킬 수 있기 때문에, 낮은 노광량에서도 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 high photobase generation efficiency, and when used as a polymerization initiator, it can generate a base more efficiently than conventional photobase generators, so that the polymerizable compound can be cured even at a low exposure dose. can In particular, when it uses for curable resin composition containing an epoxy resin or a phenol resin, high sclerosis|hardenability is shown.
Claims (9)
(식 중 A는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향환 함유기를 나타내고,
R1 및 R2는, 각각 독립적으로 수소 원자, 시아노기, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며,
X1 및 X2는, 각각 독립적으로 -NR3R4, 또는 하기 식(a) 혹은 하기 식(b)로 나타내는 기를 나타내고,
R3 및 R4는, 각각 독립적으로 수소 원자, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며,
R3 및 R4는, 서로 연결되어, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환을 형성하고 있어도 되고,
R3 및 R4가 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며,
n은 0 또는 1을 나타내고, m은 0 또는 1을 나타낸다.)
(식 중 R11, R12, R13, R14, R15, R16, R17, R18, R19 및 R20은, 각각 독립적으로 수소 원자, 무치환 혹은 치환기를 가지고 있는 탄소 원자수 1~20의 지방족 탄화수소기 또는 무치환 혹은 치환기를 가지고 있는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고,
R11과 R12, R13과 R14, R15와 R16, R17과 R18 및 R19와 R20은, 서로 연결되어, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환을 형성하고 있어도 되며,
R11, R12, R13, R14, R15, R16, R17, R18, R19 및 R20이 복수 존재하는 경우, 그들은 동일해도 되고 달라도 되며,
*는 결합수(結合手)를 나타낸다.)A carbamoyloxime compound represented by the following general formula (I).
(In the formula, A represents an aromatic ring-containing group having 6 to 20 carbon atoms, which is unsubstituted or substituted,
R 1 and R 2 are each independently a hydrogen atom, a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon having 6 to 20 carbon atoms represents the flag,
X 1 and X 2 each independently represent -NR 3 R 4 , or a group represented by the following formula (a) or the following formula (b),
R 3 and R 4 each independently represent a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 3 and R 4 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 may be formed,
When a plurality of R 3 and R 4 exist, they may be the same or different,
n represents 0 or 1, m represents 0 or 1.)
(Wherein, R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are each independently a hydrogen atom, or the number of unsubstituted or substituted carbon atoms. Represents an aliphatic hydrocarbon group of 1 to 20 or an aromatic hydrocarbon group of 6 to 20 carbon atoms having an unsubstituted or substituted group,
R 11 and R 12 , R 13 and R 14 , R 15 and R 16 , R 17 and R 18 , and R 19 and R 20 are connected to each other and the number of carbon atoms consisting of a hydrogen atom, a nitrogen atom and a carbon atom is 2 to 10 A phosphorus ring or a ring having 2 to 10 carbon atoms comprising a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom may be formed;
When a plurality of R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 and R 20 exist, they may be the same or different,
* indicates the number of bonds (結合手).
일반식(I) 중의 A가 하기 일반식(A-1), (A-2), (A-3), (A-4), (A-5) 또는 (A-6)으로 나타내는 기인 카르바모일옥심 화합물.
(식 중 R21, R22, R23, R24, R25, R26, R27, R28, R29 및 R30은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR31, -COOR31, -CO-R31, -SR31, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내고,
R21과 R22, R22와 R23, R23과 R24, R24와 R25, R26과 R27, R27과 R28, R28과 R29, R29와 R30은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되며,
R21, R22, R23, R24, R25, R26, R27, R28, R29 및 R30 중 어느 2개는 결합수를 나타내고,
R31은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며,
R21, R22, R23, R24, R25, R26, R27, R28, R29 및 R30은, -OR31, -COOR31, -CO-R31, -SR31, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.)
(식 중 R40은, 수소 원자, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고,
R41, R42, R43, R44, R45, R46, R47 및 R48은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR49, -COOR49, -CO-R49, -SR49, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내며,
R41과 R42, R42와 R43, R43과 R44, R45와 R46, R46과 R47, R47과 R48은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되고,
R41, R42, R43, R44, R45, R46, R47 및 R48 중 어느 2개는 결합수를 나타내며,
R49는, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고,
R41, R42, R43, R44, R45, R46, R47 및 R48은, -OR49, -COOR49, -CO-R49, -SR49, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.)
(식 중 R51 및 R52는, 각각 독립적으로 수소 원자, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고,
R53, R54, R55, R56, R57, R58, R59 및 R60은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR61, -COOR61, -CO-R61, -SR61, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내며,
R53과 R54, R54와 R55, R55와 R56, R57과 R58, R58과 R59, R59와 R60은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되고,
R53, R54, R55, R56, R57, R58, R59 및 R60 중 어느 2개는 결합수를 나타내며,
R61은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고,
R51, R52, R53, R54, R55, R56, R57, R58, R59, R60 및 R61은, -OR61, -COOR61, -CO-R61, -SR61, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.)
(식 중 R71은, 수소 원자, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내고,
R71은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 되며,
R72, R73, R74, R75, R76 및 R77은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR78, -COOR78, -CO-R78, -SR78, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내고,
R74와 R75, R75와 R76, R76과 R77은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되며,
R72, R73, R74, R75, R76 및 R77 중 어느 2개는 결합수를 나타내고,
R78은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며,
R72, R73, R74, R75, R76 및 R77은, -OR78, -COOR78, -CO-R78, -SR78, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.)
(식 중 R81, R82, R83, R84, R85 및 R86은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR87, -COOR87, -CO-R87, -SR87, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내고,
R83과 R84, R84와 R85, R85와 R86은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되며,
R81, R82, R83, R84, R85 및 R86 중 어느 2개는 결합수를 나타내고,
R87은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며,
R81, R82, R83, R84, R85 및 R86은, -OR87, -COOR87, -CO-R87, -SR87, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.)
(식 중 R91, R92, R93, R94, R95, R96, R97, R98, R99 및 R100은, 각각 독립적으로 결합수, 수소 원자, 할로겐 원자, 시아노기, 니트로기, -OR101, -COOR101, -CO-R101, -SR101, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기를 나타내고,
R91과 R92, R92와 R93, R93과 R94, R94와 R95, R96과 R97, R97과 R98, R98과 R99, R99와 R100은, 각각 독립적으로 서로 연결되어, 수소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 3~10인 환을 형성하고 있어도 되며,
R91, R92, R93, R94, R95, R96, R97, R98, R99 및 R100 중 어느 2개는 결합수를 나타내고,
R101은, 탄소 원자수 1~20의 지방족 탄화수소기 또는 탄소 원자수 6~20의 방향족 탄화수소기를 나타내며,
R91, R92, R93, R94, R95, R96, R97, R98, R99 및 R100은, -OR101, -COOR101, -CO-R101, -SR101, 탄소 원자수 1~20의 지방족 탄화수소기, 탄소 원자수 6~20의 방향족 탄화수소기 또는 탄소 원자수 2~20의 복소환 함유기 중의 수소 원자가 할로겐 원자, 니트로기, 시아노기, 수산기, 아미노기, 카르복시기, 메타크릴로일기, 아크릴로일기, 에폭시기, 비닐기, 비닐에테르기, 메르캅토기, 이소시아네이트기 또는 탄소 원자수 2~20의 복소환 함유기로 치환된 기여도 된다.)According to claim 1,
A in the general formula (I) is a group represented by the following general formulas (A-1), (A-2), (A-3), (A-4), (A-5) or (A-6) Bamoyloxime compound.
(Wherein, R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 are each independently a number of bonds, a hydrogen atom, a halogen atom, a cyano group, or nitro group, -OR 31 , -COOR 31 , -CO-R 31 , -SR 31 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a compound having 2 to 20 carbon atoms represents a summoning containing group,
R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 , R 27 and R 28 , R 28 and R 29 , R 29 and R 30 are each They may be independently linked to each other to form a ring having 3 to 10 carbon atoms comprising a hydrogen atom and a carbon atom,
Any two of R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 represents the number of bonds,
R 31 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 and R 30 are -OR 31 , -COOR 31 , -CO-R 31 , -SR 31 , carbon A hydrogen atom in an aliphatic hydrocarbon group having 1 to 20 atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, A contribution substituted with a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocyclic containing group having 2 to 20 carbon atoms may also be used.)
( Wherein, R 40 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 and R 48 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 49 , -COOR 49 , -CO-R 49 , -SR 49 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
R 41 and R 42 , R 42 and R 43 , R 43 and R 44 , R 45 and R 46 , R 46 and R 47 , R 47 and R 48 are each independently linked to each other and are composed of a hydrogen atom and a carbon atom may form a ring having 3 to 10 carbon atoms,
Any two of R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 and R 48 represents the number of bonds,
R 49 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms;
R 41 , R 42 , R 43 , R 44 , R 45 , R 46 , R 47 and R 48 are -OR 49 , -COOR 49 , -CO-R 49 , -SR 49 , having 1 to 20 carbon atoms A hydrogen atom in an aliphatic hydrocarbon group, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, an acryl group Contributions substituted with a loyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocyclic group containing 2 to 20 carbon atoms may also be used.)
( Wherein, R 51 and R 52 each independently represent a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 and R 60 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 61 , -COOR 61 , -CO-R 61 , -SR 61 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
R 53 and R 54 , R 54 and R 55 , R 55 and R 56 , R 57 and R 58 , R 58 and R 59 , R 59 and R 60 are each independently linked to each other and are composed of a hydrogen atom and a carbon atom may form a ring having 3 to 10 carbon atoms,
Any two of R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 and R 60 represents the number of bonds,
R 61 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 59 , R 60 and R 61 are -OR 61 , -COOR 61 , -CO-R 61 , -SR 61 , a hydrogen atom in an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group , carboxy group, methacryloyl group, acryloyl group, epoxy group, vinyl group, vinyl ether group, mercapto group, isocyanate group or a heterocyclic group containing 2 to 20 carbon atoms may be a substituted contribution.)
( Wherein, R 71 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 71 is a hydrogen atom in an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, acrylo A diyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a contribution substituted with a heterocyclic group containing 2 to 20 carbon atoms,
R 72 , R 73 , R 74 , R 75 , R 76 and R 77 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 78 , -COOR 78 , -CO-R 78 , -SR 78 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms,
R 74 and R 75 , R 75 and R 76 , R 76 and R 77 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,
Any two of R 72 , R 73 , R 74 , R 75 , R 76 and R 77 represents the number of bonds,
R 78 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 72 , R 73 , R 74 , R 75 , R 76 and R 77 are -OR 78 , -COOR 78 , -CO-R 78 , -SR 78 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, a carbon atom A hydrogen atom in an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group group, vinyl ether group, mercapto group, isocyanate group, or a contribution substituted with a heterocyclic group containing 2 to 20 carbon atoms.)
(Wherein, R 81 , R 82 , R 83 , R 84 , R 85 and R 86 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR 87 , -COOR 87 , -CO -R 87 , -SR 87 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocycle-containing group having 2 to 20 carbon atoms;
R 83 and R 84 , R 84 and R 85 , R 85 and R 86 may be each independently linked to each other to form a ring having 3 to 10 carbon atoms comprising a hydrogen atom and a carbon atom,
Any two of R 81 , R 82 , R 83 , R 84 , R 85 and R 86 represents the number of bonds,
R 87 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 81 , R 82 , R 83 , R 84 , R 85 and R 86 are -OR 87 , -COOR 87 , -CO-R 87 , -SR 87 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, a carbon atom A hydrogen atom in an aromatic hydrocarbon group having 6 to 20 atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, vinyl ether group, mercapto group, isocyanate group, or a contribution substituted with a heterocyclic group containing 2 to 20 carbon atoms.)
(Wherein, R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 and R 100 are each independently a bond number, a hydrogen atom, a halogen atom, a cyano group, or a nitro group. group, -OR 101 , -COOR 101 , -CO-R 101 , -SR 101 , an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a double carbon group having 2 to 20 carbon atoms represents a summoning containing group,
R 91 and R 92 , R 92 and R 93 , R 93 and R 94 , R 94 and R 95 , R 96 and R 97 , R 97 and R 98 , R 98 and R 99 , R 99 and R 100 are each They may be independently linked to each other to form a ring having 3 to 10 carbon atoms comprising a hydrogen atom and a carbon atom,
any two of R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 and R 100 represents the number of bonds;
R 101 represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms,
R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 and R 100 are -OR 101 , -COOR 101 , -CO-R 101 , -SR 101 , carbon A hydrogen atom in an aliphatic hydrocarbon group having 1 to 20 atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms or a heterocycle-containing group having 2 to 20 carbon atoms is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a carboxy group, A contribution substituted with a methacryloyl group, an acryloyl group, an epoxy group, a vinyl group, a vinyl ether group, a mercapto group, an isocyanate group, or a heterocyclic containing group having 2 to 20 carbon atoms may also be used.)
상기 일반식(I) 중의 X1 및 X2 중 적어도 하나가 -NR3R4이며, R3 및 R4가, 서로 연결되어, 수소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환 또는 수소 원자, 산소 원자, 질소 원자 및 탄소 원자로 이루어지는 탄소 원자수가 2~10인 환을 형성하고 있는 카르바모일옥심 화합물. 3. The method of claim 1 or 2,
At least one of X 1 and X 2 in the general formula (I) is —NR 3 R 4 , R 3 and R 4 are connected to each other and the number of carbon atoms composed of a hydrogen atom, a nitrogen atom and a carbon atom is 2 to 10 A carbamoyloxime compound forming a ring or a ring having 2 to 10 carbon atoms comprising a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom.
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. 7. The method of claim 6,
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. composition.
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