KR20230028143A - Coating agent for cyclic olefin resin, cured product, and laminate - Google Patents
Coating agent for cyclic olefin resin, cured product, and laminate Download PDFInfo
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- KR20230028143A KR20230028143A KR1020220082849A KR20220082849A KR20230028143A KR 20230028143 A KR20230028143 A KR 20230028143A KR 1020220082849 A KR1020220082849 A KR 1020220082849A KR 20220082849 A KR20220082849 A KR 20220082849A KR 20230028143 A KR20230028143 A KR 20230028143A
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- KR
- South Korea
- Prior art keywords
- meth
- group
- acrylate
- poly
- coating agent
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims abstract description 61
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 37
- 229920005672 polyolefin resin Polymers 0.000 title claims abstract description 33
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 97
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 61
- 229920000193 polymethacrylate Polymers 0.000 claims abstract description 58
- 239000003999 initiator Substances 0.000 claims abstract description 27
- -1 oxime ester Chemical group 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 77
- 150000001875 compounds Chemical class 0.000 description 40
- 239000005056 polyisocyanate Substances 0.000 description 26
- 229920001228 polyisocyanate Polymers 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 24
- 239000010408 film Substances 0.000 description 21
- 125000002947 alkylene group Chemical group 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000002245 particle Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 125000005702 oxyalkylene group Chemical group 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 125000002993 cycloalkylene group Chemical group 0.000 description 10
- 125000003700 epoxy group Chemical group 0.000 description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 8
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000000470 constituent Substances 0.000 description 7
- 125000005442 diisocyanate group Chemical group 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920000058 polyacrylate Polymers 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011247 coating layer Substances 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical group [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 4
- 125000005372 silanol group Chemical group 0.000 description 4
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 4
- 229910052727 yttrium Inorganic materials 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 3
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical group CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 0.000 description 2
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical group CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- LOCXTTRLSIDGPS-FVDSYPCUSA-N [(z)-[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(/CCCCCC)=N\OC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-FVDSYPCUSA-N 0.000 description 2
- OFUWNULILNEATR-UHFFFAOYSA-N [[3-cyclopentyl-1-oxo-1-(4-phenylsulfanylphenyl)propan-2-ylidene]amino] benzoate Chemical compound O=C(ON=C(CC1CCCC1)C(=O)C1=CC=C(SC2=CC=CC=C2)C=C1)C1=CC=CC=C1 OFUWNULILNEATR-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical group C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- YPINLRNGSGGJJT-JXMROGBWSA-N (2e)-2-hydroxyimino-1-phenylpropan-1-one Chemical compound O\N=C(/C)C(=O)C1=CC=CC=C1 YPINLRNGSGGJJT-JXMROGBWSA-N 0.000 description 1
- NPENBPVOAXERED-UHFFFAOYSA-N (4-benzoylphenyl)-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 NPENBPVOAXERED-UHFFFAOYSA-N 0.000 description 1
- CTEIIGNQRUSOCG-UHFFFAOYSA-N (7-methyl-1-prop-2-enoyloxyoctyl) prop-2-enoate Chemical compound C(C=C)(=O)OC(CCCCCC(C)C)OC(C=C)=O CTEIIGNQRUSOCG-UHFFFAOYSA-N 0.000 description 1
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 1
- HKJPVPAWUZRISW-UHFFFAOYSA-N 1,4-diisocyanato-3,4-dimethylpentane Chemical compound O=C=NC(C)(C)C(C)CCN=C=O HKJPVPAWUZRISW-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000007760 metering rod coating Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- RBCYCMNKVQPXDR-UHFFFAOYSA-N phenoxysilane Chemical compound [SiH3]OC1=CC=CC=C1 RBCYCMNKVQPXDR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 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
- 238000002411 thermogravimetry Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000005000 thioaryl group Chemical group 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CWLNAJYDRSIKJS-UHFFFAOYSA-N triethoxymethoxyethane Chemical compound CCOC(OCC)(OCC)OCC CWLNAJYDRSIKJS-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 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
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/106—Esters of polycondensation macromers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/32—Compounds containing nitrogen bound to oxygen
- C08K5/33—Oximes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
- C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
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- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
본 개시는 환상 올레핀 수지용 코팅제, 경화물 및 적층물에 관한 것이다.The present disclosure relates to a coating agent for a cyclic olefin resin, a cured product, and a laminate.
종래, 액정 표시 장치에 사용되는 편광판은 폴리비닐 알코올 필름에 요오드 등을 흡착시켜 연신 등에 의해 배향시킨 편광자의 양면에 보호 필름으로서 트리 아세틸 셀룰로오스 필름(TAC 필름)을 맞붙힌 것이다. TAC 필름의 표면에는 투명한 광경화형 수지 조성물을 도포, 경화시켜 고경도의 피막(하드 코팅층)이 형성되어 손상 등으로부터 보호되고 있다. 이러한 경화 피막을 형성시키는 재료로서 다관능 (메타)아크릴레이트 등을 이용한 활성 에너지선 경화형의 수지 조성물이 알려져 있다(특허문헌 1).Conventionally, a polarizing plate used in a liquid crystal display device is one in which iodine or the like is adsorbed on a polyvinyl alcohol film and a triacetyl cellulose film (TAC film) is laminated as a protective film on both sides of a polarizer aligned by stretching or the like. On the surface of the TAC film, a transparent photocurable resin composition is applied and cured to form a high-hardness film (hard coating layer) to protect it from damage. As a material for forming such a cured film, an active energy ray-curable resin composition using polyfunctional (meth)acrylate or the like is known (Patent Document 1).
최근에 액정 장치의 대형화나 고품질화 및 모바일 용도의 확대로부터 보다 심한 사용 환경(예를 들어 고온, 고습 조건 등)에 견디는 것이 요구된다. 결과적으로, TAC 필름은 특성면에서 한계가 있는 것이 명백해졌다. 이러한 중에 TAC 필름에서 환상 올레핀 수지계 필름으로의 대체가 유망시되고 있다. 환상 올레핀 수지계 필름은 투명성, 저복굴절, 치수 안정성 등이 우수하여 광학용 필름으로서 필요한 성능을 갖추고 있다. 나아가 저투습성을 갖는 것도 큰 특징이며, 이 점에서 TAC 필름을 대체하는 큰 요인이 되고 있다. 그러나 환상 올레핀 수지계 필름은 필름 표면에 높은 밀착성을 갖는 하드 코팅층을 형성시키는 것이 어렵다는 문제가 있다.Recently, it is required to withstand more severe use environments (eg, high temperature, high humidity conditions, etc.) due to the increase in size or quality of liquid crystal devices and the expansion of mobile applications. As a result, it became clear that TAC films have limitations in terms of properties. Among these, replacement of the TAC film with a cyclic olefin resin-based film is promising. Cyclic olefin resin-based films are excellent in transparency, low birefringence, dimensional stability, and the like, and have the necessary performance as optical films. Furthermore, it is also a big feature to have low moisture permeability, and it has become a big factor replacing a TAC film from this point. However, the cyclic olefin resin-based film has a problem in that it is difficult to form a hard coating layer having high adhesion on the surface of the film.
종래에는 환상 올레핀 수지계 필름에 대해서는 프라이머층의 도포나 전기적 처리(코로나 방전 처리, 대기압 플라즈마 처리)를 행함으로써 기재와 하드 코팅층의 밀착을 높였었다(특허문헌 2).Conventionally, adhesion between the base material and the hard coating layer has been improved by applying a primer layer or performing electrical treatment (corona discharge treatment, atmospheric pressure plasma treatment) for a cyclic olefin resin-based film (Patent Document 2).
그러나 전술한 방법에서는 도포 필름을 생산할 때에 기재와 밀착성을 높이기 위한 처리 공정이 필요하여 고비용으로 이어진다는 문제가 있었다. 또한, 전기적 처리는 처리면의 경시 변화가 발생하기 때문에 처리 후에 신속하게 하드 코팅층을 도포해야 한다는 제약도 있었다. 또한, 환상 올레핀 수지는 표면 자유 에너지가 낮다. 그 때문에, 코팅제의 도공이 어렵다는 문제도 있었다.However, in the method described above, there is a problem in that a treatment process for increasing adhesion to a substrate is required when producing a coated film, leading to high cost. In addition, since the electrical treatment causes a change in the treated surface with time, there is also a limitation that the hard coating layer must be applied quickly after the treatment. Moreover, cyclic olefin resin has a low surface free energy. Therefore, there was also a problem that coating of the coating agent was difficult.
본 발명이 해결하고자 하는 과제는 코팅제의 경화물과 환상 올레핀 수지 사이의 밀착성 및 환상 올레핀 수지에 대한 도공성이 양호해지는 환상 올레핀 수지용 코팅제를 제공하는 것으로 한다.The problem to be solved by the present invention is to provide a coating agent for cyclic olefin resins in which the adhesion between the cured product of the coating agent and the cyclic olefin resin and the coating property to the cyclic olefin resin are improved.
본 발명자들은 면밀히 검토한 결과, 특정 코팅제에 의해 상기 과제가 해결된다는 것을 발견하였다.As a result of careful examination, the present inventors have found that the above problems are solved by a specific coating agent.
본 개시에 의해 이하의 항목이 제공된다.The following items are provided by this disclosure.
(항목 1)(item 1)
(메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트, (meth)poly(meth)acrylate having 3 or more acryloyl groups;
(메타)아크릴로일기 함유 실리카 입자 및(meth)acryloyl group-containing silica particles and
옥심에스테르 구조 함유 광중합 개시제 Photopolymerization initiator containing oxime ester structure
를 포함하는 환상 올레핀 수지용 코팅제.A coating agent for a cyclic olefin resin comprising a.
(항목 2)(item 2)
옥심에스테르 구조 비함유 광중합 개시제 추가적으로 포함하는 상기 항목에 기재된 환상 올레핀 수지용 코팅제.The coating agent for cyclic olefin resins described in the above item further comprising an oxime ester structure-free photopolymerization initiator.
(항목 3)(item 3)
상기 항목 중 어느 한 항에 기재된 환상 올레핀 수지용 코팅제의 경화물.The hardened|cured material of the coating agent for cyclic olefin resins in any one of the said item.
(항목 4)(item 4)
상기 항목에 기재된 경화물을 포함하는 적층물.A laminate comprising the cured product described in the above item.
본 개시에서 상술한 하나 또는 복수의 특징은 명시된 조합에 더하여 추가적으로 조합하여 제공될 수 있다.One or more features described above in this disclosure may be provided in additional combinations in addition to the specified combinations.
본 개시에 관한 환상 올레핀 수지용 코팅제를 이용함으로써 코팅제의 경화물층과 환상 올레핀 수지 사이의 밀착성이 우수한 적층물을 제조할 수 있다. 또한, 본 개시에 관한 환상 올레핀 수지용 코팅제는 환상 올레핀 수지에 대한 도공성이 우수하다.By using the coating agent for cyclic olefin resins according to the present disclosure, a laminate excellent in adhesion between the cured material layer of the coating agent and the cyclic olefin resin can be produced. In addition, the coating agent for cyclic olefin resins according to the present disclosure is excellent in coating properties for cyclic olefin resins.
본 개시의 전체에 걸쳐 각 물성값, 함유량 등의 수치의 범위는 적절히(예를 들어 하기의 각 항목에 기재된 상한 및 하한의 값으로부터 선택하여) 설정될 수 있다. 구체적으로는 수치 α에 대해 수치 α의 상한 및 하한으로서 A3, A2, A1 (A3 > A2 > A1이라 함) 등이 예시될 경우 수치 α의 범위는 A3 이하, A2 이하, A3 미만, A2 미만, A1 이상, A2 이상, A1보다 큰, A2보다 큰, A1~A2 (A1이상 A2이하), A1~A3, A2~A3, A1이상 A3미만, A1이상 A2미만, A2이상 A3이하, A1보다 크고 A3 미만, A1보다 크고 A2 미만, A2보다 크고 A3 미만, A1보다 크고 A3 이하, A1보다 크고 A2 이하, A2보다 크고 A3 이하 등이 예시된다.Throughout the present disclosure, ranges of numerical values such as each physical property value and content may be appropriately set (for example, by selecting from the upper and lower limit values described in each item below). Specifically, when A3, A2, A1 (referred to as A3 > A2 > A1) are exemplified as the upper and lower limits of the value α for the value α, the range of the value α is A3 or less, A2 or less, less than A3, less than A2, A1 or more, A2 or more, greater than A1, greater than A2, A1 to A2 (A1 to A2 or less), A1 to A3, A2 to A3, A1 to or less than A3, A1 to A2 or more, A2 to A3 or less, greater than A1 Examples include less than A3, greater than A1 and less than A2, greater than A2 and less than A3, greater than A1 and less than A3, greater than A1 and less than A2, greater than A2 and less than A3.
[환상 올레핀 수지용 코팅제: 코팅제라고도 함][Coating agent for cyclic olefin resin: also called coating agent]
본 개시는 (메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트, (메타)아크릴로일기 함유 실리카 입자 및 옥심에스테르 구조 함유 광중합 개시제를 포함하는 환상 올레핀 수지용 코팅제을 제공한다.The present disclosure provides a coating agent for a cyclic olefin resin comprising a poly(meth)acrylate having three or more (meth)acryloyl groups, silica particles containing a (meth)acryloyl group, and a photopolymerization initiator containing an oxime ester structure.
본 개시에서 「(메타)아크릴」은 「아크릴 및 메타크릴로 이루어진 군에서 선택되는 적어도 하나」를 의미한다. 마찬가지로 「(메타)아크릴레이트」는 「아크릴레이트 및 메타크릴레이트로 이루어진 군에서 선택되는 적어도 하나」를 의미한다. 또한 「(메타)아크릴로일」은 「아크릴로일 및 메타크릴로일로 이루어진 군에서 선택되는 적어도 하나」를 의미한다.In the present disclosure, "(meth)acryl" means "at least one selected from the group consisting of acryl and methacryl". Similarly, "(meth)acrylate" means "at least one selected from the group consisting of acrylates and methacrylates". In addition, "(meth)acryloyl" means "at least one selected from the group consisting of acryloyl and methacryloyl".
＜(메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트＞<Poly(meth)acrylate having 3 or more (meth)acryloyl groups>
(메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트는 단독 또는 2 종 이상으로 사용할 수 있다.Poly(meth)acrylates having three or more (meth)acryloyl groups can be used alone or in combination of two or more.
(메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트는 옥시알킬렌 폴리(메타)아크릴레이트, 우레탄폴리(메타)아크릴레이트, 폴리머(메타)아크릴레이트 등이 예시된다.Examples of the poly(meth)acrylate having three or more (meth)acryloyl groups include oxyalkylene poly(meth)acrylate, urethane poly(meth)acrylate, and polymer (meth)acrylate.
＜(메타)아크릴로일기를 3개 이상 갖는 옥시알킬렌 폴리(메타)아크릴레이트＞<Oxyalkylene poly(meth)acrylate having 3 or more (meth)acryloyl groups>
(메타)아크릴로일기를 3개 이상 갖는 옥시알킬렌 폴리(메타)아크릴레이트는 （폴리）펜타에리스리톨 폴리(메타)아크릴레이트, （폴리） 트리메틸올프로판 폴리(메타)아크릴레이트, （폴리）글리세린 폴리(메타)아크릴레이트 등이 예시된다.Oxyalkylene poly(meth)acrylates having three or more (meth)acryloyl groups include (poly)pentaerythritol poly(meth)acrylate, (poly)trimethylolpropane poly(meth)acrylate, and (poly)glycerin. Poly(meth)acrylate etc. are illustrated.
본 개시에서 옥시알킬렌 폴리(메타)아크릴레이트는 옥시(메타)아크릴로일기를 복수개 갖는 화합물로서, 이 화합물에서 옥시(메타)아크릴로일기를 제외한 부분이 산소 원자, 탄소 원자 및 수소 원자만을 단결합으로 결합함으로써 구성되어 있는 화합물을 의미한다.In the present disclosure, oxyalkylene poly (meth) acrylate is a compound having a plurality of oxy (meth) acryloyl groups, in which the portion excluding the oxy (meth) acryloyl group contains only oxygen atoms, carbon atoms, and hydrogen atoms. It means a compound composed by combining with a bond.
（(메타)아크릴로일기를 3개 이상 갖는 （폴리）펜타에리스리톨 폴리(메타)아크릴레이트）((Poly)pentaerythritol poly(meth)acrylate having 3 or more (meth)acryloyl groups)
(메타)아크릴로일기를 3개 이상 갖는 （폴리）펜타에리스리톨 폴리(메타)아크릴레이트는 하기 구조식The (poly)pentaerythritol poly(meth)acrylate having three or more (meth)acryloyl groups has the following structural formula
[화학식 1][Formula 1]
（식 중, ｍ은 0 이상의 정수이고, Ｒｂ１～Ｒｂ６은 각각 독립적으로 수소 원자, 또는 (메타)아크릴로일기이며, 또한Ｒｂ１～Ｒｂ６ 중 적어도 3개가 (메타)아크릴로일기이다. 또, Ｒｂ３및Ｒｂ５는 각 구성단위마다 기가 달라도 된다.）(In the formula, m is an integer greater than or equal to 0, Rb1 to Rb6 are each independently a hydrogen atom or a (meth)acryloyl group, and at least three of Rb1 to Rb6 are (meth)acryloyl groups. Also, Rb3 and Rb5 may have different groups for each constituent unit.)
에 의해 나타나는 화합물이다.It is a compound represented by
또한, 「각 구성단위마다 기가 달라도 된다」라는 것은 예를 들어 상기 구조식에서 m이 2일 때,In addition, "the group may be different for each structural unit" means, for example, when m is 2 in the above structural formula,
[화학식 2][Formula 2]
Rb3A와 Rb3B는 다른 기이어도 되고, Rb5A와 Rb5B는 다른 기이어도 되는 것을 의미한다(이하 동일).It means that R b3A and R b3B may be different groups, and R b5A and R b5B may be different groups (the same below).
(메타)아크릴로일기를 3개 이상 갖는 （폴리）펜타에리스리톨 폴리(메타)아크릴레이트는 펜타에리스리톨 트리(메타)아크릴레이트, 펜타에리스리톨 테트라(메타)아크릴레이트, 디펜타에리스리톨 트리(메타)아크릴레이트, 디펜타에리스리톨 테트라(메타)아크릴레이트, 디펜타에리스리톨 펜타(메타)아크릴레이트, 디펜타에리스리톨 헥사(메타)아크릴레이트, 트리펜타에리스리톨 트리(메타)아크릴레이트, 트리펜타에리스리톨 테트라(메타)아크릴레이트, 트리펜타에리스리톨 펜타(메타)아크릴레이트, 트리펜타에리스리톨 헥사(메타)아크릴레이트, 트리펜타에리스리톨 헵타(메타)아크릴레이트, 트리펜타에리스리톨 옥타(메타)아크릴레이트 등이 예시된다.The (poly)pentaerythritol poly(meth)acrylate having three or more (meth)acryloyl groups includes pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and dipentaerythritol tri(meth)acrylate. , dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol tri(meth)acrylate, tripentaerythritol tetra(meth)acrylate , tripentaerythritol penta(meth)acrylate, tripentaerythritol hexa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tripentaerythritol octa(meth)acrylate and the like are exemplified.
（(메타)아크릴로일기를 3개 이상 갖는 （폴리） 트리메틸올 프로판 폴리(메타)아크릴레이트）((Poly) trimethylol propane poly(meth)acrylate having 3 or more (meth)acryloyl groups)
(메타)아크릴로일기를 3개 이상 갖는 （폴리） 트리메틸올프로판 폴리(메타)아크릴레이트는 하기 구조식The (poly) trimethylolpropane poly(meth)acrylate having three or more (meth)acryloyl groups has the following structural formula
[화학식 3][Formula 3]
（식 중, ｐ는 0 이상의 정수이고, Ｒｂ７～Ｒｂ１０은 수소 원자, 또는 (메타)아크릴로일기이며, 또한 Ｒｂ７～Ｒｂ１０ 중 적어도 3개가 (메타)아크릴로일기이다. 또한, Rb9는 각 구성단위마다 기가 달라도 된다.)(In the formula, p is an integer greater than or equal to 0, Rb7 to Rb10 are hydrogen atoms or (meth)acryloyl groups, and at least three of Rb7 to Rb10 are (meth)acryloyl groups. In addition, R b9 may have a different group for each constituent unit.)
에 의해 나타나는 화합물이다.It is a compound represented by
（폴리）트리메틸올프로판 폴리(메타)아크릴레이트는 트리메틸올프로판 트리(메타)아크릴레이트, 디트리메틸올프로판 트리(메타)아크릴레이트등이 예시된다.Examples of the (poly)trimethylolpropane poly(meth)acrylate include trimethylolpropane tri(meth)acrylate and ditrimethylolpropane tri(meth)acrylate.
（(메타)아크릴로일기를 3개 이상 갖는 （폴리）글리세린 폴리(메타)아크릴레이트）((Poly)glycerin poly(meth)acrylate having 3 or more (meth)acryloyl groups)
(메타)아크릴로일기를 3개 이상 갖는 （폴리）글리세린 폴리(메타)아크릴레이트는 하기 구조식(Meth) glycerin poly (meth) acrylate having three or more acryloyl groups has the following structural formula
[화학식 4][Formula 4]
（식 중, ｑ는 0 이상의 정수이고, Ｒｂ１１～Ｒｂ１３는 수소 원자 또는 (메타)아크릴로일기이며, 또한 Ｒｂ１１～Ｒｂ１３ 중 적어도 3개가 (메타)아크릴로일기이다. 또한, Rb12는 각 구성단위마다 기가 달라도 된다.)(In the formula, q is an integer greater than or equal to 0, Rb11 to Rb13 are hydrogen atoms or (meth)acryloyl groups, and at least three of Rb11 to Rb13 are (meth)acryloyl groups. In addition, R b12 may have a different group for each constituent unit.)
에 의해 나타나는 화합물이다.It is a compound represented by
(메타)아크릴로일기를 3개 이상 갖는 （폴리）글리세린 폴리(메타)아크릴레이트는 글리세린 트리(메타)아크릴레이트, 디글리세린 트리(메타)아크릴레이트, 디글리세린 테 트라(메타)아크릴레이트 등이 예시된다.(Poly)glycerol poly(meth)acrylates having three or more (meth)acryloyl groups include glycerol tri(meth)acrylate, diglycerol tri(meth)acrylate, and diglycerol tetra(meth)acrylate. is exemplified
옥시알킬렌 폴리(메타)아크릴레이트는 알킬렌옥사이드 변성 또는 에폭시 변성되어 있어도 된다.The oxyalkylene poly(meth)acrylate may be alkylene oxide-modified or epoxy-modified.
옥시알킬렌 폴리(알킬렌옥사이드 변성 (메타)아크릴레이트)는 상술한 옥시알킬렌 폴리(메타)아크릴레이트의 옥시(메타)아크릴로일기가Oxyalkylene poly (alkylene oxide-modified (meth) acrylate) is the oxy (meth) acryloyl group of the above-mentioned oxyalkylene poly (meth) acrylate
[화학식 5][Formula 5]
(식 중, q는 1~16의 정수이고, R1'~R2'는 각각 독립적으로 수소 원자 또는 알킬기이며, R1'는 각 단위마다 기가 달라도 된다.)(In the formula, q is an integer of 1 to 16, R 1' to R 2' are each independently a hydrogen atom or an alkyl group, and R 1' may have a different group for each unit.)
으로 치환된 화합물이다.is a compound substituted with
옥시알킬렌 폴리(에폭시 변성 (메타)아크릴레이트)는 상술한 옥시알킬렌 폴리(메타)아크릴레이트의 옥시(메타)아크릴로일기가Oxyalkylene poly (epoxy-modified (meth) acrylate) is the oxy (meth) acryloyl group of the above-mentioned oxyalkylene poly (meth) acrylate
[화학식 6][Formula 6]
(식 중, R3'는 각각 독립적으로 수소 원자 또는 알킬기이다.)(In the formula, R 3' is each independently a hydrogen atom or an alkyl group.)
으로 치환된 화합물이다.is a compound substituted with
＜(메타)아크릴로일기를 3개 이상 갖는 우레탄 폴리(메타)아크릴레이트＞<Urethane poly(meth)acrylate having three or more (meth)acryloyl groups>
우레탄 폴리(메타)아크릴레이트는 (메타)아크릴로일기를 3개 이상 갖는 수산기 함유 폴리(메타)아크릴레이트 및 폴리이소시아네이트를 포함하는 화합물 군의 반응물 등이 예시된다.Examples of the urethane poly(meth)acrylate include a hydroxyl group-containing poly(meth)acrylate having three or more (meth)acryloyl groups and a reactant of a compound group including polyisocyanate.
우레탄 폴리(메타)아크릴레이트의 원료가 되는 (메타)아크릴로일기를 3개 이상 갖는 수산기 함유 폴리(메타)아크릴레이트는 상술한 것 등이 예시된다.As for the hydroxyl group-containing poly(meth)acrylate which has 3 or more (meth)acryloyl groups used as the raw material of urethane poly(meth)acrylate, the thing mentioned above etc. are illustrated.
폴리이소시아네이트는 후술하는 화합물등이 예시된다.Examples of the polyisocyanate include compounds described later.
<폴리머 폴리(메타)아크릴레이트><Polymer poly(meth)acrylate>
본 개시에서 「폴리머 폴리(메타)아크릴레이트」란 (메타)아크릴로일기를 2개 이상 갖는 폴리머를 의미한다.In the present disclosure, "polymer poly(meth)acrylate" means a polymer having two or more (meth)acryloyl groups.
폴리머 폴리(메타)아크릴레이트는 공지의 수법을 이용하여 제조될 수 있다. 폴리머 폴리(메타)아크릴레이트의 제조 방법은 에폭시기 함유 (메타)아크릴 폴리머와 α,β-불포화 카르본산을 반응시키는 방법 등이 예시된다.Polymer poly(meth)acrylates can be prepared using known techniques. Examples of the method for producing the polymer poly(meth)acrylate include a method of reacting an epoxy group-containing (meth)acrylic polymer with α,β-unsaturated carboxylic acid.
에폭시기 함유(메타)아크릴 폴리머의 전체 구성단위 1００몰％에서 차지하는 에폭시기 함유 (메타)아크릴레이트 유래의 구성단위의 함유량의 상한 및 하한은 １００, ９５, ９０, ８５, ８０, ７５, ７０, ６５, ６０, ５５, ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０, ７몰% 등이 예시된다. 일 실시형태에서 상기 함유량은 7 ~ 100몰%가 바람직하다.The upper and lower limits of the content of the constituent units derived from the epoxy group-containing (meth)acrylate in 100 mol% of the total constituent units of the epoxy group-containing (meth)acryl polymer are 100, 95, 90, 85, 80, 75, 70, 65, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10, 7 mol% and the like are exemplified. In one embodiment, the content is preferably 7 to 100 mol%.
에폭시기 함유 (메타)아크릴폴리머의 전체 구성단위 1００질량%에서 차지하는 에폭시기 함유 (메타)아크릴레이트 유래의 구성단위의 함유량의 상한 및 하한은 １００, ９５, ９０, ８５, ８０, ７５, ７０, ６５, ６２, ６０, ５５, ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０질량％ 등이 예시된다. 일 실시형태에서 상기 함유량은 10 ~ 100질량%가 바람직하다.The upper and lower limits of the content of the constituent units derived from the epoxy group-containing (meth)acrylate in 100% by mass of all constituent units of the epoxy group-containing (meth)acryl polymer are 100, 95, 90, 85, 80, 75, 70, 65, 62, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10 mass % etc. are illustrated. In one embodiment, the content is preferably 10 to 100% by mass.
에폭시기 함유 (메타)아크릴폴리머의 전체 구성단위 1００몰％에서 차지하는 수산기 비함유 알킬(메타)아크릴레이트 유래의 구성단위의 함유량의 상한 및 하한은 ９３, ９０, ８５, ８０, ７５, ７０, ６５, ６０, ５５, ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０, ５, ０몰% 등이 예시된다. 일 실시형태에서 상기 함유량은 0 ~ 93몰%가 바람직하다.The upper limit and the lower limit of the content of the structural unit derived from the non-hydroxyl group-containing alkyl (meth)acrylate in 100 mol% of the total structural units of the epoxy group-containing (meth)acryl polymer are 93, 90, 85, 80, 75, 70, 65, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10, 5, 0 mol% and the like are exemplified. In one embodiment, the content is preferably 0 to 93 mol%.
에폭시기 함유 (메타)아크릴폴리머의 전체 구성단위 1００질량%에서 차지하는 수산기 비함유 알킬(메타)아크릴레이트 유래의 구성단위의 함유량의 상한 및 하한은 ９０, ８５, ８０, ７５, ７０, ６５, ６０, ５５, ５０, ４５, ４０, ３８, ３５, ３０, ２５, ２０, １５, １０, ５, ０질량％ 등이 예시된다. 일 실시형태에서 상기 함유량은 0 ~ 90질량%가 바람직하다.The upper and lower limits of the content of the structural units derived from non-hydroxyl group-containing alkyl (meth)acrylates in 100% by mass of all structural units of the epoxy group-containing (meth)acryl polymer are 90, 85, 80, 75, 70, 65, 60, 55, 50, 45, 40, 38, 35, 30, 25, 20, 15, 10, 5, 0 mass % etc. are illustrated. In one embodiment, the content is preferably 0 to 90% by mass.
에폭시기 함유 (메타)아크릴레이트 유래의 구성단위 100몰%에 대해 반응시키는 α,β-불포화 카르본산의 양의 상한 및 하한은 １００, ９５, ９０, ８５, ８０, ７５, ７０, ６５, ６０, ５５, ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０몰% 등이 예시된다. 일 실시형태에서 상기 양은 10 ~ 100몰%가 바람직하다.The upper and lower limits of the amount of α,β-unsaturated carboxylic acid reacted with respect to 100 mol% of the structural unit derived from epoxy group-containing (meth)acrylate are 100, 95, 90, 85, 80, 75, 70, 65, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10 mol% etc. are illustrated. In one embodiment, the amount is preferably 10 to 100 mol%.
에폭시기 함유 (메타)아크릴레이트 유래의 구성단위 100질량%에 대해 반응시키는 α,β-불포화 카르본산의 양의 상한 및 하한은 ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０, ５질량％ 등이 예시된다. 일 실시형태에서 상기 양은 5 ~ 50질량%가 바람직하다.The upper and lower limits of the amount of α,β-unsaturated carboxylic acid reacted with respect to 100% by mass of the structural unit derived from epoxy group-containing (meth)acrylate are 50, 45, 40, 35, 30, 25, 20, 15, 10, 5 mass % etc. are illustrated. In one embodiment, the amount is preferably 5 to 50% by mass.
에폭시기 함유 (메타)아크릴 폴리머는 공지의 라디칼 중합법을 이용하여 제조될 수 있다.An epoxy group-containing (meth)acrylic polymer can be prepared using a known radical polymerization method.
일 실시형태에서 옥심 비함유 코팅제에 포함되는 활성 에너지선 경화성 수지 화합물은 옥시알킬렌 폴리(메타)아크릴레이트가 바람직하다.In one embodiment, the active energy ray-curable resin compound included in the oxime-free coating agent is preferably oxyalkylene poly(meth)acrylate.
상기 코팅제 비휘발분 １００질량% 중 (메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트의 함유량의 상한 및 하한은 ９０, ８９, ８５, ８０, ７５, ７４, ７１, ７０, ６９, ６７, ６５, ６３, ６１, ６０, ５９, ５５, ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０질량％ 등이 예시된다. 일 실시형태에서 상기 함유량은 １０ ~ ９０질량％가 바람직하고, ２５ ~ ９０질량%가 더 바람직하다.The upper and lower limits of the content of the poly(meth)acrylate having three or more (meth)acryloyl groups in 100% by mass of the non-volatile matter of the coating agent are 90, 89, 85, 80, 75, 74, 71, 70, 69, 67, 65, 63, 61, 60, 59, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10 mass % etc. are illustrated. In one embodiment, the content is preferably 10 to 90% by mass, more preferably 25 to 90% by mass.
본 개시에서 「비휘발분」은 유기 용매 및 물 이외의 성분의 합계 질량이다. 일 실시형태에서 대상물 Ａ의 비휘발분은 대상물 Ａ １ｇ을 １３０℃에서 가열하여 항량에 도달한 시점에서 잔존한 성분의 합계 질량으로 한다.In the present disclosure, "non-volatile content" is the total mass of components other than the organic solvent and water. In one embodiment, the non-volatile content of the object A is the total mass of the remaining components at the time when the object A 1g is heated at 130°C to reach a constant weight.
＜(메타)아크릴로일기 함유 실리카 입자＞<(meth)acryloyl group-containing silica particles>
(메타)아크릴로일기 함유 실리카 입자는 단독 또는 2종 이상으로 사용될 수 있다.The (meth)acryloyl group-containing silica particles may be used alone or in combination of two or more.
(메타)아크릴로일기 함유 실리카 입자는 실리카 입자와 (메타)아크릴로일기 함유 화합물의 반응물이다.The (meth)acryloyl group-containing silica particles are a reaction product of a silica particle and a (meth)acryloyl group-containing compound.
（실리카 입자）(silica particles)
실리카 입자는 단독 또는 2종 이상으로 사용될 수 있다.Silica particles may be used alone or in combination of two or more.
실리카 입자의 입자지름의 상한 및 하한은１００, ９５, ９０, ８５, ８０, ７５, ７０, ６５, ６０, ５５, ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０, ５ｎｍ등이 예시된다. 일 실시형태에서 실리카 입자의 입자지름은 ５ ~ １００ｎｍ가 바람직하다.The upper and lower limits of the particle diameter of the silica particles are 100, 95, 90, 85, 80, 75, 70, 65, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10, 5 nm, etc. this is exemplified In one embodiment, the particle diameter of the silica particles is preferably 5 to 100 nm.
실리카 입자의 형상은 구상(球狀), 중공상(中空狀), 중실상(中實狀), 다공질상(多孔質狀), 봉상(棒狀), 판상(板狀), 섬유상(纖維狀), 부정형상(不定形狀) 등이 예시된다. 일 실시형태에 있어서, 실리카 입자의 형상은 구상이 바람직하다. 또한, 일 실시형태에서 실리카 입자는 중실 실리카 입자가 바람직하다.The shapes of silica particles are spherical, hollow, solid, porous, rod, plate, and fibrous. ), irregular shapes, etc. are exemplified. In one embodiment, the shape of the silica particles is preferably spherical. Also, in one embodiment, the silica particles are preferably solid silica particles.
일 실시형태에 있어서, 실리카 입자는 분체상 또는 용매분산졸인 것이 바람직하다.In one embodiment, the silica particles are preferably powdery or solvent-dispersed sol.
실리카 입자가 용매 분산졸인 경우에 다른 성분과의 상용성, 분산성의 관점에서 분산매는 유기 용매가 바람직하다.When the silica particles are a solvent dispersion sol, the dispersion medium is preferably an organic solvent from the viewpoint of compatibility with other components and dispersibility.
유기 용매는 단독 또는 2 종 이상으로 사용할 수 있다.An organic solvent can be used individually or in 2 or more types.
유기 용매로는 케톤 용매, 방향족 용매, 알코올 용매, 글리콜 용매, 글리콜에테르 용매, 에스테르 용매, 석유계 용매, 할로알칸 용매, 아미드 용매 등이 예시된다.Examples of the organic solvent include ketone solvents, aromatic solvents, alcohol solvents, glycol solvents, glycol ether solvents, ester solvents, petroleum solvents, haloalkane solvents, and amide solvents.
케톤 용매로는 메틸에틸케톤, 아세틸아세톤, 메틸이소부틸케톤, 시클로펜타논, 시클로헥사논 등이 예시된다.Examples of the ketone solvent include methyl ethyl ketone, acetylacetone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone.
방향족 용매로는 톨루엔, 크실렌 등이 예시된다.Examples of the aromatic solvent include toluene and xylene.
알코올 용매로는 메탄올, 에탄올, n-프로판올, 이소프로판올, 부탄올 등이 예시된다.Examples of the alcohol solvent include methanol, ethanol, n-propanol, isopropanol, and butanol.
글리콜 용매로는 에틸렌글리콜, 프로필렌글리콜, 디에틸렌글리콜, 디프로필렌글리콜, 트리에틸렌글리콜, 트리프로필렌글리콜, 폴리에틸렌글리콜, 폴리프로필렌글리콜 등이 예시된다.Examples of the glycol solvent include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, polyethylene glycol, and polypropylene glycol.
글리콜 에테르 용매는 에틸렌글리콜 디메틸에테르, 에틸렌글리콜 디에틸에테르, 프로필렌글리콜 디메틸에테르, 프로필렌글리콜 디에틸에테르, 디에틸렌글리콜 디메틸에테르, 트리에틸렌글리콜 디메틸에테르, 디에틸렌글리콜 메틸에틸에테르, 디에틸렌글리콜 디에틸에테르, 프로필렌글리콜 모노메틸에테르, 에틸렌글리콜 모노메틸에테르, 에틸렌글리콜 모노에틸에테르, 에틸렌글리콜 모노-n-프로필에테르, 에틸렌글리콜 모노이소프로필에테르, 에틸렌글리콜 모노-n-부틸에테르, 에틸렌글리콜 모노이소부틸에테르, 에틸렌글리콜 모노-t-부틸에테르 등이 예시된다.The glycol ether solvent is ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol methylethyl ether, diethylene glycol diethyl Ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol monoisopropyl ether, ethylene glycol mono-n-butyl ether, ethylene glycol monoisobutyl ether, ethylene glycol mono-t-butyl ether and the like are exemplified.
에스테르 용매로는 아세트산에틸, 아세트산부틸, 메틸셀로솔브 아세테이트, 에틸셀로솔브 아세테이트, 프로필렌글리콜 모노메틸에테르 아세테이트 등이 예시된다.Examples of the ester solvent include ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, and propylene glycol monomethyl ether acetate.
석유계 용매로는 소르벳소 #100 (엑손사 제품), 소르벳소 #150 (엑손사 제품) 등이 예시된다.Examples of the petroleum solvent include Sorvesso #100 (produced by Exxon) and Sorvesso # 150 (produced by Exxon).
할로알칸 용매로는 클로로포름 등이 예시된다.As the haloalkane solvent, chloroform and the like are exemplified.
아미드 용매로는 디메틸포름아미드 등이 예시된다.Dimethylformamide etc. are illustrated as an amide solvent.
실리카 입자(콜로이달 실리카)의 시판품은 닛산 화학(주)(Nissan Chemical Corporation) 제품 상품명 : 메탄올 실리카졸, ＩＰＡ－ＳＴ, ＭＥＫ－ＳＴ, ＮＢＡ－ＳＴ, ＸＢＡ－ＳＴ, ＤＭＡＣ－ＳＴ, ＳＴ－ＵＰ, ＳＴ－ＯＵＰ, ＳＴ－２０, ＳＴ－４０, ＳＴ－Ｃ, ＳＴ－Ｎ, ＳＴ－Ｏ, ＳＴ－５０, ＳＴ－ＯＬ, ＭＥＫ－ＳＴ－Ｌ, ＭＩＢＫ－Ｔ－Ｌ 등이 예시된다.Silica particles (colloidal silica) are commercially available from Nissan Chemical Corporation, trade names: Methanol Silica Sol, IPA-ST, METK-ST, NBA-ST, XBA-ST, DCT-CTC, -CTC. , ST -ｕP, ST -200, ST -40, ST -C, ST -N, ST -ｏ, ST -50, ST -ｏ, MEｋ -ST -L, and ｉ -ｌ.
실리카 입자(분체 실리카)의 시판품은 닛폰 에어로질(주)(NIPPON AEROSIL CO., LTD.) 제품인 상품명: 에어로질 130, 에어로질 300, 에어로질 380, 에어로질 TT600, 에어로질 OX50, 아사히가라스(주)(Asahi Glass Co., Ltd.) 제품인 상품명: 실덱스(Sildex) H31, H32, H51, H52, H121, H122, 닛폰실리카공업(주)(Nippon Silica Industries) 제품인 상품명: E220A, E220, 후지실리시아화학(주)(FUJI SILYSIA CHEMICAL LTD.) 제품인 상품명: SYLYSIA 470, 일본판유리(주)(Nippon Sheet Glass Co., Ltd.) 제품인 상품명: SG 플레이크 등이 예시된다.Commercial products of silica particles (powdered silica) are products of NIPPON AEROSIL CO., LTD. Trade names: Aerosil 130, Aerosil 300, Aerosil 380, Aerosil TT600, Aerosil OX50, Asahi Glass Product names manufactured by Asahi Glass Co., Ltd.: Sildex H31, H32, H51, H52, H121, H122 Product names manufactured by Nippon Silica Industries: E220A, E220, Trade name: SYLYSIA 470 manufactured by Fuji Silysia Chemical Co., Ltd., trade name: SG flake manufactured by Nippon Sheet Glass Co., Ltd., and the like are exemplified.
（(메타)아크릴로일기 함유 화합물）((meth)acryloyl group-containing compound)
(메타)아크릴로일기 함유 화합물은 단독 또는 2종 이상으로 사용될 수 있다.The (meth)acryloyl group-containing compound may be used alone or in combination of two or more.
일 실시형태에 있어서 (메타)아크릴로일기 함유 화합물은 식U로 나타내는 기를 포함한다.In one embodiment, the (meth)acryloyl group-containing compound includes a group represented by formula U.
[화학식 7][Formula 7]
(식 중에서, X는 NH, O 또는 S이고, Y는 O 또는 S이다)(Wherein, X is NH, O or S, and Y is O or S)
상기 기[―X―C(＝Y)―NH―]로 나타내는 구체적인 기는 [―O―C(＝O)―NH―], [―O―C(＝S)―NH―], [―S―C(＝O)―NH―], [―NH―C(＝O)―NH―], [―NH―C(＝S)―NH―], [―S―C(＝S)―NH―]의 6종이다. 이들 기는 1종 단독으로 또는 2종 이상을 조합시켜 사용할 수 있다. 일 실시형태에 있어서, 열안정성의 관점에서 (메타)아크릴로일기 함유 실리카 입자가 [―O―C(＝O)―NH―]와 [―O―C(＝S)―NH―] 및/또는 [―S―C(＝O)―NH―]를 갖는 것이 바람직하다.Specific groups represented by the group [-X-C(=Y)-NH-] are [-O-C(=O)-NH-], [-O-C(=S)-NH-], [-S -C(=O)-NH-], [-NH-C(=O)-NH-], [-NH-C(=S)-NH-], [-S-C(=S)-NH ―] of six species. These groups can be used individually by 1 type or in combination of 2 or more types. In one embodiment, from the viewpoint of thermal stability, (meth)acryloyl group-containing silica particles are [-O-C(=O)-NH-] and [-O-C(=S)-NH-] and/or or [-S-C(=O)-NH-].
상기 기 [―X―C(＝Y)―NH―]는 분자 사이에서 수소결합에 의한 적당한 응집력을 발생시켜 경화물로 한 경우에 우수한 기계적강도, 기재와의 밀착성 및 내열성 등의 특성을 부여하는 것으로 생각된다. 또한 상기는 어디까지나 하나의 설이며, 본 발명이 상기 설에 구속되는 것을 의도하는 것은 아니다.The group [-X-C(=Y)-NH-] generates appropriate cohesive force by hydrogen bonding between molecules to give properties such as excellent mechanical strength, adhesion to substrates and heat resistance when made into a cured product. It is thought to be In addition, the above is only one theory, and it is not intended that the present invention be bound by the above theory.
상기 (메타)아크릴로일기 함유 화합물은 실라놀기를 포함하는 화합물(실라놀기 함유 화합물이라고도 함) 또는 가수분해에 의하여 실라놀기를 생성하는 화합물(실라놀기 생성 화합물이라고도 함)인 것이 바람직하다.The (meth)acryloyl group-containing compound is preferably a compound containing a silanol group (also referred to as a silanol group-containing compound) or a compound that generates a silanol group by hydrolysis (also referred to as a silanol group-generating compound).
실라놀기 생성 화합물은 규소원자 상에 알콕시기, 아릴옥시기, 아세톡시기, 아미노기, 할로겐기 등을 갖는 화합물 등이 예시된다. 일 실시형태에 있어서, 실라놀기 생성 화합물은 알콕시기 또는 아릴옥시기를 포함하는 화합물이 바람직하다.Examples of the silanol group-generating compound include compounds having an alkoxy group, an aryloxy group, an acetoxy group, an amino group, a halogen group and the like on a silicon atom. In one embodiment, the silanol group-generating compound is preferably a compound containing an alkoxy group or an aryloxy group.
실라놀기 또는 실라놀기 생성 화합물의 실라놀기 생성부위는 축합반응 또는 가수분해에 연달아 일어나는 축합반응에 의하여 실리카 입자와 결합하는 구성단위이다.A silanol group or a silanol group-generating site of a silanol-generating compound is a structural unit bonded to silica particles by a condensation reaction or a condensation reaction subsequent to hydrolysis.
일 실시형태에 있어서, (메타)아크릴로일기 함유 화합물은 하기 식S로 나타내는 화합물이 바람직하다.In one embodiment, the (meth)acryloyl group-containing compound is preferably a compound represented by the following formula S.
＜식Ｓ＞<Formula S>
[화학식 8][Formula 8]
（식 중에서, Rs1, Rs2는 각각 독립적으로 수소원자, 알킬기 또는 아릴기이고, Rs3은 알킬렌기 또는 아릴렌기이고, Rs4는 2가의 유기기이고, Rs5는 (s''＋1)가의 유기기이고, Z는 (메타)아크릴로일기이고, s'은 1, 2 또는 3이고, s''은 1 ~ 20의 정수이다）(In the formula, R s1 and R s2 are each independently a hydrogen atom, an alkyl group or an aryl group, R s3 is an alkylene group or an arylene group, R s4 is a divalent organic group, R s5 is (s''+1) A valent organic group, Z is a (meth)acryloyl group, s' is 1, 2 or 3, and s'' is an integer from 1 to 20)
알킬기는 직쇄 알킬기, 분기 알킬기, 시클로알킬기 등이 예시된다.Examples of the alkyl group include a straight-chain alkyl group, a branched alkyl group, and a cycloalkyl group.
직쇄 알킬기는 ―CnH2n＋1(n은 1 이상의 정수)의 일반식으로 나타낸다. 직쇄 알킬기는 메틸기, 에틸기, n-프로필기, n-부틸기, n-펜틸기, n-헥실기, n-헵틸기, n-옥틸기, n-노닐기, n-데실기, 운데실기, 도데실기(라우릴기), 트리데실기, 테트라데실기(미리스틸기), 펜타데실기, 헥사데실기(팔미틸기), 헵타데실기, 옥타데실기(스테아릴기), 노나데실기, 이코실기, 헨이코실기, 도코실기 등이 예시된다.A straight-chain alkyl group is represented by the general formula of —C n H 2n+1 (n is an integer greater than or equal to 1). The straight chain alkyl group is methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, undecyl group, Dodecyl group (lauryl group), tridecyl group, tetradecyl group (myristyl group), pentadecyl group, hexadecyl group (palmityl group), heptadecyl group, octadecyl group (stearyl group), nonadecyl group, An Ikosyl group, a Henikosyl group, a Dokosyl group, etc. are illustrated.
분기 알킬기는 직쇄 알킬기의 적어도 1개의 수소원자가 알킬기에 의하여 치환된 기이다. 분기 알킬기는 i-프로필기, i-부틸기, s-부틸기, t-부틸기, 디에틸펜틸기, 트리메틸부틸기, 트리메틸펜틸기, 트리메틸헥실기, 2-에틸헥실기 등이 예시된다.A branched alkyl group is a group in which at least one hydrogen atom of a straight-chain alkyl group is substituted with an alkyl group. Examples of the branched alkyl group include i-propyl group, i-butyl group, s-butyl group, t-butyl group, diethylpentyl group, trimethylbutyl group, trimethylpentyl group, trimethylhexyl group, and 2-ethylhexyl group.
시클로알킬기는 단환 시클로알킬기, 가교환 시클로알킬기, 축합환 시클로알킬기 등이 예시된다.Examples of the cycloalkyl group include a monocyclic cycloalkyl group, a bridged cycloalkyl group, and a condensed-ring cycloalkyl group.
본 개시에서 단환은 탄소의 공유결합에 의해 형성된 내부에 가교 구조를 가지지 않는 환상 구조를 의미한다. 또한 축합환은 2개 이상의 단환이 2개의 원자를 공유하고 있는(즉, 각각의 고리의 변을서로 1개만 공유(축합)하고 있음) 환상구조를 의미한다. 가교환은 2개 이상의 단환이 3개 이상의 원자를 공유하고 있는 환상구조를 의미한다.In the present disclosure, a monocycle means a cyclic structure formed by covalent bonds of carbon and having no cross-linked structure therein. In addition, the condensed ring means a cyclic structure in which two or more monocycles share two atoms (ie, only one side of each ring is shared (condensed) with each other). Cross-exchange means a cyclic structure in which two or more monocycles share three or more atoms.
단환 시클로알킬기는 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로데실기, 3,5,5-트리메틸시클로헥실기 등이 예시된다.Examples of the monocyclic cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclodecyl group, and a 3,5,5-trimethylcyclohexyl group.
가교환 시클로알킬기는 트리시클로데실기, 아다만틸기, 노르보닐기 등이 예시된다.Examples of the bridged cycloalkyl group include a tricyclodecyl group, an adamantyl group, and a norbornyl group.
축합환 시클로알킬기는 비시클로데실기 등이 예시된다.Examples of the condensed cycloalkyl group include a bicyclodecyl group and the like.
아릴기는 단환 아릴기, 축합환 아릴기 등이 예시된다. 또한아릴기는 1개 이상의 수소원자가 직쇄 또는 분기 알킬기에 의하여 치환되어 있어도 된다.Examples of the aryl group include a monocyclic aryl group and a condensed ring aryl group. In the aryl group, one or more hydrogen atoms may be substituted with a straight-chain or branched alkyl group.
단환 아릴기는 페닐기, 톨릴기, 메시틸기 등이 예시된다.A phenyl group, a tolyl group, a mesityl group etc. are illustrated as a monocyclic aryl group.
축합환 아릴기는 나프틸기 등이 예시된다.A naphthyl group etc. are illustrated as a condensed-ring aryl group.
식 Ｓ 중, （Ｒｓ１Ｏ）ｓ’Ｒｓ２ ３－ｓ’Ｓｉ－로 나타내는 기는 트리메톡시실릴기, 트리에톡시실릴기, 트리페녹시실릴기, 메틸디메톡시실릴기, 디메틸메톡시실릴기 등이 예시된다. 이들 중에서 트리메톡시실릴기 또는 트리에톡시실릴기가 바람직하다.In formula S, the group represented by (R s1 Ｏ) s' R s2 3-s' Si- is a trimethoxysilyl group, a triethoxysilyl group, a triphenoxysilyl group, a methyldimethoxysilyl group, and a dimethylmethoxysilyl group. and the like are exemplified. Among these, a trimethoxysilyl group or a triethoxysilyl group is preferable.
알킬렌기는 직쇄 알킬렌기, 분기 알킬렌기, 시클로알킬렌기 등이 예시된다.Examples of the alkylene group include a straight-chain alkylene group, a branched alkylene group, and a cycloalkylene group.
직쇄 알킬렌기는 -(CH2)n-(n은 1 이상의 정수)의 일반식으로 나타난다. 직쇄 알킬렌기는 메틸렌기, 에틸렌기, n-프로필렌기, n-부틸렌기, n-펜틸렌기, n-헥실렌기, n-헵틸렌기, n-옥틸렌기, n-노닐렌기, n-데카메틸렌기 등이 예시된다.The straight-chain alkylene group is represented by the general formula -(CH 2 ) n - (n is an integer greater than or equal to 1). The straight chain alkylene group is a methylene group, ethylene group, n-propylene group, n-butylene group, n-pentylene group, n-hexylene group, n-heptylene group, n-octylene group, n-nonylene group, n-decamethylene group and the like are exemplified.
분기 알킬렌기는 직쇄 알킬렌기의 적어도 하나의 수소 원자가 알킬기에 의해 치환된 기이다. 분기알킬렌기는 디에틸펜틸렌기, 트리메틸부틸렌기, 트리메틸펜틸렌기, 트리메틸헥실렌기(트리메틸헥사메틸렌기) 등이 예시된다.A branched alkylene group is a group in which at least one hydrogen atom of a straight-chain alkylene group is substituted by an alkyl group. Examples of the branched alkylene group include a diethylpentylene group, a trimethylbutylene group, a trimethylpentylene group, and a trimethylhexylene group (trimethylhexamethylene group).
시클로알킬렌기는 단환 시클로알킬렌기, 가교환 시클로알킬렌기, 축합환 시클로알킬렌기 등이 예시된다. 또한 시클로알킬렌기는 1개 이상의 수소원자가 직쇄 또는 분기 알킬기에 의하여 치환되어 있어도 된다.Examples of the cycloalkylene group include a monocyclic cycloalkylene group, a bridged cycloalkylene group, and a condensed cycloalkylene group. In the cycloalkylene group, one or more hydrogen atoms may be substituted by a straight-chain or branched alkyl group.
단환 시클로알킬렌기는 시클로펜틸렌기, 시클로헥실렌기, 시클로헵틸렌기, 시클로데실렌기, 3,5,5-트리메틸시클로헥실렌기 등이 예시된다.Examples of the monocyclic cycloalkylene group include a cyclopentylene group, a cyclohexylene group, a cycloheptylene group, a cyclodecylene group, and a 3,5,5-trimethylcyclohexylene group.
가교환 시클로알킬렌기는 트리시클로데실렌기, 아다만틸렌기, 노르보닐렌기 등이 예시된다.Examples of the bridged cycloalkylene group include a tricyclodecylene group, an adamantylene group, and a norbornylene group.
축합환 시클로알킬렌기는 비시클로데실렌기 등이 예시된다.Examples of condensed-ring cycloalkylene groups include bicyclodecylene groups and the like.
아릴렌기는 단환 아릴렌기, 축합환 아릴렌기 등이 예시된다. 또한 아릴렌기는 1개 이상의 수소원자가 직쇄 또는 분기 알킬기에 의하여 치환되어 있어도 된다.Examples of the arylene group include a monocyclic arylene group and a condensed arylene group. In the arylene group, one or more hydrogen atoms may be substituted by a straight-chain or branched alkyl group.
단환 아릴렌기는 페닐렌기, 톨릴렌기 등이 예시된다.A phenylene group, a tolylene group, etc. are illustrated as a monocyclic arylene group.
축합환 아릴렌기는 나프틸렌기 등이 예시된다.A naphthylene group etc. are illustrated as a condensed-ring arylene group.
식S 중에서, Rs4는 2가의 유기기이다.In Formula S, R s4 is a divalent organic group.
Rs4의 분자량은 14 내지 1만이 바람직하고, 76 내지 500이 보다 바람직하다.14-10,000 are preferable and, as for the molecular weight of Rs4 , 76-500 are more preferable.
Rs4는 알킬렌기, 아릴렌기 등이 예시된다. Rs4는 탄소원자 및 수소원자 이외의 원소를 포함하고 있어도 되고, 폴리에테르 결합, 폴리에스테르 결합, 폴리아미드 결합, 폴리카보네이트 결합, 나아가서는 상기 식U로 나타내는 기를 포함할 수도 있다.R s4 is exemplified by an alkylene group or an arylene group. R s4 may contain an element other than a carbon atom and a hydrogen atom, and may also contain a polyether bond, a polyester bond, a polyamide bond, a polycarbonate bond, or a group represented by the formula U above.
식 S 중에서, Rs5는 (s''＋1)가의 유기기이고, 바람직하게는 쇄상, 분기상 또는 환상의 포화 탄화수소기, 불포화 탄화수소기 중에서 선택된다.In the formula S, R s5 is an organic group having a valence of (s''+1), and is preferably selected from chain, branched or cyclic saturated hydrocarbon groups and unsaturated hydrocarbon groups.
Rs5는,R s5 is,
[화학식 9][Formula 9]
（ｓ'''은 0∼2의 정수이다）(s''' is an integer from 0 to 2)
등이 예시된다.etc. are exemplified.
식S 중에서, s''은 1 ~ 20의 정수이고, 1 ~ 10이 바람직하고, 1 ~ 5가 더 바람직하다.In formula S, s'' is an integer of 1 to 20, preferably 1 to 10, more preferably 1 to 5.
식 S로 나타내는 (메타)아크릴로일기 함유 화합물의 합성방법은 일본 공개특허 평9-100111호 공보에 기재되어 있는 방법 등이 예시된다. 즉 (메타)아크릴로일기 함유 화합물의 합성방법은 (A) 메르캅토알콕시실란과 폴리이소시아네이트와 활성수소기 함유 (메타)아크릴레이트와의 부가반응, (B) 알콕시실릴기 및 이소시아네이트기를 갖는 화합물과 활성수소기 함유 (메타)아크릴레이트와의 반응, (C) (메타)아크릴로일기 및 이소시아네이트기를 구비하는 화합물과 메르캅토알콕시실란 또는 아미노실란과의 부가반응 등이 예시된다.As for the synthetic method of the (meth)acryloyl group-containing compound represented by Formula S, the method described in Unexamined-Japanese-Patent No. 9-100111, etc. are illustrated. That is, the method for synthesizing a (meth)acryloyl group-containing compound is (A) an addition reaction between mercaptoalkoxysilane, polyisocyanate, and (meth)acrylate containing an active hydrogen group, (B) a compound having an alkoxysilyl group and an isocyanate group, Reaction with active hydrogen group-containing (meth)acrylate, (C) addition reaction of a compound having a (meth)acryloyl group and an isocyanate group with mercaptoalkoxysilane or aminosilane, and the like are exemplified.
일 실시형태에 있어서, 식 S로 나타내는 (메타)아크릴로일기 함유 화합물의 합성방법은 상기 (A)의 방법이 바람직하다. 더 상세하게는,In one embodiment, the method of (A) is preferable for the synthesis method of the (meth)acryloyl group-containing compound represented by Formula S. More specifically,
(A1)법; 먼저 메르캅토알콕시실란과 폴리이소시아네이트를 반응시킴으로써 알콕시실릴기, [―S―C(＝O)NH―]기 및 이소시아네이트기를 포함하는 중간체를 형성하는 공정, 상기 중간체와 수산기 함유 (폴리)(메타)아크릴레이트를 반응시켜, [―O―C(＝O)NH―] 결합을 형성하는 공정을 포함하는 방법,(A1) law; First, a step of forming an intermediate containing an alkoxysilyl group, a [-S-C(=O)NH-] group, and an isocyanate group by reacting a mercaptoalkoxysilane with a polyisocyanate, the intermediate containing a hydroxyl group (poly) (meta) A method including a step of reacting an acrylate to form a [-O-C(=O)NH-] bond;
(A2)법; 먼저 폴리이소시아네이트와 수산기 함유 (폴리)(메타)아크릴레이트를 반응시킴으로써 (메타)아크릴로일기, [―O―C(＝O)NH―]기 및 이소시아네이트기를 포함하는 중간체를 형성하는 공정, 상기 중간체와 메르캅토알콕시실란을 반응시켜 [―S―C(＝O)―NH―] 결합을 형성하는 공정을 포함하는 방법(A2) law; First, a step of forming an intermediate containing a (meth)acryloyl group, a [—O—C(=O)NH—] group, and an isocyanate group by reacting a polyisocyanate with a hydroxyl group-containing (poly)(meth)acrylate, the intermediate and a mercaptoalkoxysilane to react to form a [-S-C(=O)-NH-] bond.
등이 예시된다. 마이클 부가반응에 의한 중합성 불포화기의 감소가 없다는 점에서 (A1)법이 바람직하다.etc. are exemplified. Method (A1) is preferable in that there is no reduction of polymerizable unsaturated groups by Michael addition reaction.
메르캅토알콕시실란은 단독 또는 2종 이상으로 사용될 수 있다.Mercaptoalkoxysilanes may be used alone or in combination of two or more.
메르캅토알콕시실란은 메르캅토프로필트리메톡시실란, 메르캅토프로필트리에톡시실란, 메르캅토프로필메틸디에톡시실란, 메르캅토프로필디메톡시메틸실란, 메르캅토프로필메톡시디메틸실란, 메르캅토프로필트리페녹시실란, 메르캅토프로필트리부톡시실란 등이 예시된다.Mercaptoalkoxysilane is mercaptopropyltrimethoxysilane, mercaptopropyltriethoxysilane, mercaptopropylmethyldiethoxysilane, mercaptopropyldimethoxymethylsilane, mercaptopropylmethoxydimethylsilane, mercaptopropyltriphenone Sisilane, mercaptopropyltributoxysilane, etc. are illustrated.
일 실시형태에 있어서 메르캅토알콕시실란은 메르캅토프로필트리메톡시실란, 메르캅토프로필트리에톡시실란이 바람직하다.In one embodiment, the mercaptoalkoxysilane is preferably mercaptopropyltrimethoxysilane or mercaptopropyltriethoxysilane.
메르캅토알콕시실란의 시판품은 도레이·다우코닝(주)(Dow Corning Toray Co., Ltd.) 제품인 상품명: SH6062 등이 예시된다. 또한 아미노치환 알콕시실란과 에폭시기치환 메르캅탄의 부가생성물, 에폭시실란과 α,ω-디메르캅토 화합물의 부가생성물을 이용할 수도 있다.As for the commercial item of mercaptoalkoxysilane, Dow Corning Toray Co., Ltd. (Dow Corning Toray Co., Ltd.) brand name: SH6062 etc. are illustrated. In addition, adducts of amino-substituted alkoxysilanes and epoxy group-substituted mercaptans, and adducts of epoxysilanes and α,ω-dimercapto compounds can also be used.
폴리이소시아네이트는 단독 또는 2종 이상으로 사용될 수 있다.Polyisocyanates may be used alone or in combination of two or more.
본 개시에 있어서 「폴리이소시아네이트」는 2개 이상의 이소시아네이트기(―N＝C＝O)를 갖는 화합물이다.In the present disclosure, "polyisocyanate" is a compound having two or more isocyanate groups (-N=C=O).
폴리이소시아네이트는 직쇄 지방족 폴리이소시아네이트, 분기 지방족 폴리이소시아네이트, 지환족 폴리이소시아네이트, 방향족 폴리이소시아네이트 및 이들의 뷰렛체, 이소시아누레이트체, 알로파네이트체, 어덕트체 등이 예시된다.Examples of polyisocyanates include straight-chain aliphatic polyisocyanates, branched aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, biurets, isocyanurates, allophanates, and adducts thereof.
직쇄지방족 폴리이소시아네이트로는 메틸렌 디이소시아네이트, 디메틸렌 디이소시아네이트, 트리메틸렌 디이소시아네이트, 테트라메틸렌 디이소시아네이트, 펜타메틸렌 디이소시아네이트, 헥사메틸렌 디이소시아네이트, 헵타메틸렌 디이소시아네이트, 옥타메틸렌 디이소시아네이트, 노나메틸렌 디이소시아네이트, 데카메틸렌 디이소시아네이트 등이 예시된다.As the straight-chain aliphatic polyisocyanate, methylene diisocyanate, dimethylene diisocyanate, trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, nonamethylene diisocyanate, Decamethylene diisocyanate etc. are illustrated.
분기지방족 폴리이소시아네이트로는 디에틸펜틸렌 이소시아네이트, 트리메틸부티렌 디이소시아네이트, 트리메틸펜틸렌 디이소시아네이트, 트리메틸헥사메틸렌 디이소시아네이트 등이 예시된다.Examples of the branched aliphatic polyisocyanate include diethylpentylene isocyanate, trimethylbutylene diisocyanate, trimethylpentylene diisocyanate, and trimethylhexamethylene diisocyanate.
지환족 폴리이소시아네이트로는 단환지환족 폴리이소시아네이트, 가교환지환족 폴리이소시아네이트, 축합환지환족 폴리이소시아네이트 등이 예시된다.Examples of the alicyclic polyisocyanates include monocyclic alicyclic polyisocyanates, bridged alicyclic polyisocyanates, and condensed alicyclic polyisocyanates.
단환지환족 폴리이소시아네이트로는 수소첨가크실렌 디이소시아네이트, 이소포론 디이소시아네이트, 시클로펜틸렌 디이소시아네이트, 시클로헥실렌 디이소시아네이트, 시클로헵틸렌 디이소시아네이트, 시클로데실렌 디이소시아네이트, 3,5,5-트리메틸시클로헥실렌 디이소시아네이트, 디시클로헥실메탄 디이소시아네이트 등이 예시된다.Monocyclic alicyclic polyisocyanates include hydrogenated xylene diisocyanate, isophorone diisocyanate, cyclopentylene diisocyanate, cyclohexylene diisocyanate, cycloheptylene diisocyanate, cyclodecylene diisocyanate, 3,5,5-trimethylcyclo Hexylene diisocyanate, dicyclohexylmethane diisocyanate and the like are exemplified.
가교환지환족 폴리이소시아네이트로는 트리시클로데실렌 디이소시아네이트, 아다만탄 디이소시아네이트, 노르보넨 디이소시아네이트 등이 예시된다.Examples of bridged alicyclic polyisocyanates include tricyclodecylene diisocyanate, adamantane diisocyanate, and norbornene diisocyanate.
축합환지환족 폴리이소시아네이트로는 비시클로데실렌 디이소시아네이트 등이 예시된다.Bicyclodecylene diisocyanate etc. are illustrated as condensed cycloaliphatic polyisocyanate.
방향족 폴리이소시아네이트로는 단환방향족 폴리이소시아네이트, 축합환 방향족 폴리이소시아네이트 등이 예시된다.Monocyclic aromatic polyisocyanate, condensed-ring aromatic polyisocyanate, etc. are illustrated as aromatic polyisocyanate.
단환방향족 폴리이소시아네이트로는 4,4'-디페닐디메틸메탄 디이소시아네이트 등의 디알킬디페닐메탄 디이소시아네이트, 4,4'-디페닐테트라메틸메탄 디이소시아네이트 등의 테트라알킬디페닐메탄 디이소시아네이트, 4,4'-디페닐메탄 디이소시아네이트, 4, 4'-디벤질이소시아네이트, 1,3-페닐렌 디이소시아네이트, 1,4-페닐렌 디이소시아네이트, 톨릴렌 디이소시아네이트, 크실릴렌 디이소시아네이트, m-테트라메틸크실릴렌 디이소시아네이트 등이 예시된다.Monocyclic aromatic polyisocyanates include dialkyldiphenylmethane diisocyanates such as 4,4'-diphenyldimethylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanates such as 4,4'-diphenyltetramethylmethane diisocyanate, and 4 ,4'-diphenylmethane diisocyanate, 4,4'-dibenzyl isocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, m- Tetramethylxylylene diisocyanate etc. are illustrated.
축합환방향족 폴리이소시아네이트로는 1,5-나프틸렌디이소시아네이트 등이 예시된다.Examples of condensed cyclic aromatic polyisocyanates include 1,5-naphthylene diisocyanate and the like.
수산기 함유 (폴리)(메타)아크릴레이트는 단독 또는 2종 이상으로 사용될 수 있다.The hydroxyl group-containing (poly)(meth)acrylates may be used alone or in combination of two or more.
수산기 함유 (폴리)(메타)아크릴레이트는 수산기 함유 (메타)아크릴레이트, 수산기 함유 폴리(메타)아크릴레이트 등이 예시된다.Examples of the hydroxyl group-containing (poly)(meth)acrylate include hydroxyl group-containing (meth)acrylate and hydroxyl group-containing poly(meth)acrylate.
수산기 함유 (메타)아크릴레이트는 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 3-히드록시프로필(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 6-히드록시헥실(메타)아크릴레이트, 8-히드록시옥틸(메타)아크릴레이트, 1,4-시클로헥산디메탄올모노(메타)아크릴레이트 등이 예시된다.Hydroxyl group-containing (meth)acrylates include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate. rate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate and the like are exemplified.
일 실시형태에 있어서 수산기 함유 폴리(메타)아크릴레이트는 트리메틸올프로판디(메타)아크릴레이트, 트리메틸올에탄디(메타)아크릴레이트, 펜타에리스리톨트리(메타)아크릴레이트, 디펜타에리스리톨펜타(메타)아크릴레이트가 바람직하다.In one embodiment, the hydroxyl group-containing poly(meth)acrylate is trimethylolpropanedi(meth)acrylate, trimethylolethanedi(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, Acrylates are preferred.
일 실시형태에 있어서 수산기 함유 (폴리)(메타)아크릴레이트는 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 펜타에리스리톨트리(메타)아크릴레이트가 바람직하다.In one embodiment, the hydroxyl group-containing (poly)(meth)acrylate is preferably 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, or pentaerythritol tri(meth)acrylate.
일 실시형태에 있어서, (메타)아크릴로일기 함유 화합물은 식U로 나타내는 기를 포함하지 않는다.In one embodiment, the (meth)acryloyl group-containing compound does not contain a group represented by formula U.
＜식 Ｕ＞<Formula U>
[화학식 10][Formula 10]
（식 중에서, X는 NH, O 또는 S이고, Y는 O 또는 S이다.）(In the formula, X is NH, O or S, and Y is O or S.)
식 U로 나타내는 기를 포함하지 않는 (메타)아크릴로일기 함유화합물은 식U1 등이 예시된다.Formula U1 etc. are illustrated as a (meth)acryloyl group containing compound which does not contain the group represented by Formula U.
＜식Ｕ１＞<Formula U1>
[화학식 11][Formula 11]
（식 중에서, Zu는 (메타)아크릴로일기이고, Ru1은 알킬렌기 또는 아릴렌기이고, Ru2는 알킬기 또는 아릴기이고, u는 1 ~ 3의 정수이다）(Wherein, Z u is a (meth)acryloyl group, R u1 is an alkylene group or an arylene group, R u2 is an alkyl group or an aryl group, and u is an integer of 1 to 3)
식 U1로 나타내는 화합물은 트리(메타)아크릴옥시에틸모노메톡시실란, 디(메타)아크릴옥시에틸디메톡시실란, (메타)아크릴옥시에틸트리메톡시실란, 트리(메타)아크릴옥시프로필모노메톡시실란, 디(메타)아크릴옥시프로필디메톡시실란, (메타)아크릴옥시프로필트리메톡시실란, 트리(메타)아크릴옥시프로필모노에톡시실란, 디(메타)아크릴옥시프로필디에톡시실란, (메타)아크릴옥시프로필트리에톡시실란, 트리(메타)아크릴옥시프로필모노페녹시실란, 디(메타)아크릴옥시프로필디페녹시실란, (메타)아크릴옥시프로필트리페녹시실란 등이 예시된다.The compound represented by formula U1 is tri(meth)acryloxyethyl monomethoxysilane, di(meth)acryloxyethyl dimethoxysilane, (meth)acryloxyethyl trimethoxysilane, tri(meth)acryloxypropylmonomethoxy Silane, di(meth)acryloxypropyldimethoxysilane, (meth)acryloxypropyltrimethoxysilane, tri(meth)acryloxypropylmonoethoxysilane, di(meth)acryloxypropyldiethoxysilane, (meth) Acryloxypropyl triethoxysilane, tri(meth)acryloxypropyl monophenoxysilane, di(meth)acryloxypropyl diphenoxysilane, (meth)acryloxypropyltriphenoxysilane, etc. are illustrated.
(메타)아크릴로일기 함유 실리카 입자의 제조방법은 알콕시실란을 가수분해하여 알콕시실란 가수분해물을 얻는 공정, 알콕시실란 가수분해물과 분체 실리카 입자 또는 실리카 입자의 용매 분산졸을 혼합하고, 가열, 교반조작을 실시하는 공정을 포함하는 방법, 알콕시실란의 가수분해를 실리카 입자의 존재하에서 행하는 방법 등이 예시된다. 일 실시형태에 있어서, (메타)아크릴로일기 함유 실리카 입자의 제조방법은 알콕시실란의 가수분해를 실리카 입자의 존재하에서 실시하는 방법이 바람직하다.The method for producing (meth)acryloyl group-containing silica particles is a step of hydrolyzing an alkoxysilane to obtain an alkoxysilane hydrolyzate, mixing the alkoxysilane hydrolyzate with powdered silica particles or a solvent dispersion sol of silica particles, heating and stirring operation A method including a step of performing, a method of hydrolyzing an alkoxysilane in the presence of silica particles, and the like are exemplified. In one embodiment, the method for producing (meth)acryloyl group-containing silica particles is preferably a method in which hydrolysis of an alkoxysilane is performed in the presence of silica particles.
(메타)아크릴로일기 함유 실리카 입자를 제조할 때에 그 온도는 0 ~ 150℃가 바람직하고, 20 ~ 100℃가 보다 바람직하다. 또한 반응시간은 5분 ~ 24시간이 바람직하다.When producing the (meth)acryloyl group-containing silica particles, the temperature is preferably 0 to 150°C, more preferably 20 to 100°C. In addition, the reaction time is preferably 5 minutes to 24 hours.
(메타)아크릴로일기 함유 실리카 입자를 제조할 때에 있어서, 반응을 원활·균일하게 진행시킬 목적으로 물과 균일하게 상용(相溶)하는 유기용매를 첨가하여도 된다. 유기용매의 첨가량은 반응을 원활, 균일하게 행한다는 목적에 부합하는 이상 특별한 제한은 없다.When producing (meth)acryloyl group-containing silica particles, an organic solvent that is uniformly compatible with water may be added for the purpose of smoothly and uniformly advancing the reaction. The addition amount of the organic solvent is not particularly limited as long as it meets the purpose of performing the reaction smoothly and uniformly.
(메타)아크릴로일기 함유 실리카 입자 제조시에 있어서, 반응을 촉진하기 위하여 촉매로서 산, 염 또는 염기를 첨가하여도 된다.In the production of (meth)acryloyl group-containing silica particles, an acid, salt or base may be added as a catalyst to promote the reaction.
(메타)아크릴로일기 함유 실리카 입자 제조시에 있어서, 반응을 촉진하기 위하여 탈수제를 첨가하여도 된다.During production of (meth)acryloyl group-containing silica particles, a dehydrating agent may be added to promote the reaction.
탈수제는 제올라이트, 무수 실리카, 무수 알루미나 등의 무기탈수제, 오르토포름산메틸, 오르토포름산에틸, 테트라에톡시메탄, 테트라부톡시메탄 등의 유기 탈수제 등이 예시된다. 일 실시형태에 있어서, 탈수제는 유기 탈수제가 바람직하고, 오르토포름산메틸, 오르토포름산에틸 등의 오르토에스테르류가 보다 바람직하다.Examples of the dehydrating agent include inorganic dehydrating agents such as zeolite, anhydrous silica, and anhydrous alumina, and organic dehydrating agents such as orthomethyl formate, ethyl orthoformate, tetraethoxymethane, and tetrabutoxymethane. In one embodiment, the dehydrating agent is preferably an organic dehydrating agent, and orthoesters such as methyl orthoformate and ethyl orthoformate are more preferred.
(메타)아크릴로일기 함유 실리카 입자에 결합한 알콕시실란의 양은 건조분체를 공기 중에서 완전히 연소시킨 경우의 질량감소％의 항량값으로서, 공기 중에서의 110℃에서 800℃까지의 열중량분석에 의하여 구할 수 있다.The amount of alkoxysilane bonded to the (meth)acryloyl group-containing silica particles is a constant value of mass loss% when the dry powder is completely burned in air, and can be obtained by thermogravimetric analysis from 110 ° C to 800 ° C in air. there is.
(메타)아크릴로일기 함유 실리카 입자의 입자지름의 상한 및 하한은 １５０, １４５, １４０, １３５, １３０, １２５, １２０, １１５, １１０, １０５, １００, ９５, ９０, ８５, ８０, ７５, ７０, ６５, ６０, ５５, ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０, ５ｎｍ등이 예시된다. 일 실시형태에 있어서, (메타)아크릴로일기 함유 실리카 입자의 입자지름은 ５ ~ １５０ｎｍ가 바람직하다.The upper and lower limits of the particle diameter of the (meth)acryloyl group-containing silica particles are 150, 145, 140, 135, 130, 125, 120, 115, 110, 105, 100, 95, 90, 85, 80, 75, 70 , 65, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10, 5 nm and the like are exemplified. In one embodiment, the particle size of the (meth)acryloyl group-containing silica particles is preferably 5 to 150 nm.
본 개시에 있어서 입자지름의 측정은 JIS Z8828 : 2013에 준거하여 시판되는 측정기(제품명 「DYNAMIC LIGHT SCATTERING NANOPARTICLE SIZE ANALYZER LB-550」, (주)호리바제작소(HORIBA, Ltd.))를 사용한 동적 광산란법에 의한 입도분포측정에 의하여 행한다.In the present disclosure, the particle diameter is measured by a dynamic light scattering method using a commercially available measuring instrument (product name: "DYNAMIC LIGHT SCATTERING NANOPARTICLE SIZE ANALYZER LB-550", HORIBA, Ltd.) in accordance with JIS Z8828: 2013 It is carried out by particle size distribution measurement by
일 실시형태에 있어서, (메타)아크릴로일기 함유 실리카 입자는 식U로 나타내는 기를 포함한다.In one embodiment, the (meth)acryloyl group-containing silica particle includes a group represented by formula U.
<식 U><Formula U>
[화학식 12][Formula 12]
（식 중에서, X는 NH, O 또는 S이고, Y는 O 또는 S이다）(In the formula, X is NH, O or S, and Y is O or S)
일 실시형태에 있어서, (메타)아크릴로일기 함유 실리카 입자는 식 U로 나타내는 기를 포함하지 않는다.In one embodiment, the (meth)acryloyl group-containing silica particles do not contain a group represented by the formula U.
<식 U><Formula U>
[화학식 13][Formula 13]
(식 중에서 X는 NH, O 또는 S이고, Y는 O 또는 S이다)(In the formula, X is NH, O or S, and Y is O or S)
상기 코팅제 비휘발분 100질량％ 중의 (메타)아크릴로일기 함유 실리카 입자의 함유량의 상한 및 하한은 ７０, ６９, ６７, ６５, ６０, ５５, ５０, ４５, ４０, ３５, ３０, ２９, ２７, ２６, ２５, ２４, ２２, ２０, １５, １０, ５질량％ 등이 예시된다. 일 실시형태에서 상기 함유량은 ５ ~ ７０질량％가 바람직하다.The upper and lower limits of the content of the (meth)acryloyl group-containing silica particles in 100% by mass of the non-volatile matter of the coating agent are 70, 69, 67, 65, 60, 55, 50, 45, 40, 35, 30, 29, 27, 26, 25, 24, 22, 20, 15, 10, 5 mass % etc. are illustrated. In one embodiment, the content is preferably 5 to 70% by mass.
＜옥심에스테르 구조 함유 광중합 개시제＞<Oxime ester structure-containing photopolymerization initiator>
옥심에스테르 구조 함유 광중합 개시제는 단독 또는 2종 이상으로 사용할 수 있다.An oxime ester structure containing photoinitiator can be used individually or in 2 or more types.
일 실시형태에서 옥심에스테르 구조 함유 광중합 개시제는 하기 구조식:In one embodiment, the photopolymerization initiator containing an oxime ester structure has the following structural formula:
[화학식 14][Formula 14]
(식 중, Ro1은 아릴기 또는 알킬기이고, Ro2는 알킬기이며, Ro3은 아릴기이다.)(In the formula, R o1 is an aryl group or an alkyl group, R o2 is an alkyl group, and R o3 is an aryl group.)
로 표시되는 화합물이 바람직하고, 하기 구조식:A compound represented by is preferred, and the following structural formula:
[화학식 15][Formula 15]
(식 중, Ro1은 아릴기 또는 알킬기이고, Ro2는 알킬기이며, Ro3은 아릴기이다.)(In the formula, R o1 is an aryl group or an alkyl group, R o2 is an alkyl group, and R o3 is an aryl group.)
으로 나타나는 화합물이 보다 바람직하다.A compound represented by is more preferable.
상기 구조식 중의 아릴기는 치환되어 있어도 된다. 아릴기의 치환기는 알킬기, 티오알킬기, 티오아릴기, 카르보닐아릴기 등이 예시된다.The aryl group in the above structural formula may be substituted. Examples of the substituent of the aryl group include an alkyl group, a thioalkyl group, a thioaryl group, and a carbonylaryl group.
치환 아릴기는A substituted aryl group
[화학식 16][Formula 16]
등이 예시된다.etc. are exemplified.
옥심에스테르 구조 함유 광중합 개시제는 1.2-옥탄디온, 1-[4-(페닐티오)-, 2-(O-벤조일옥심)](즉 2-((벤조일옥시)이미노)-1-(4-(페닐티오)페닐)옥탄-1-온); The photopolymerization initiator containing an oxime ester structure is 1.2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] (i.e. 2-((benzoyloxy)imino)-1-(4- (phenylthio)phenyl)octan-1-one);
에타논, 1-[9-에틸-6-(2-메틸벤조일)-9H-카르바졸-3-일]-, 1-(O-아세틸옥심)(즉 1-(((1-(9-에틸-6-(2-메틸벤조일)-9H-카르바졸-3-일)에틸리덴)아미노)옥시)에탄-1-온), ５－（４－이소프로필페닐티오）―１，２－인단디온，２－Ｏ－아세틸）옥심, １－［４－（페닐티오）페닐］－３－시클로펜틸프로판－１，２－디온－２－（Ｏ－벤조일옥심）등이 예시된다.Ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (i.e. 1-(((1-(9- Ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl)ethylidene)amino)oxy)ethan-1-one), 5-(4-isopropylphenylthio)-1,2-indane Dione, 2-O-acetyl) oxime, 1-[4-(phenylthio)phenyl]-3-cyclopentylpropane-1,2-dione-2-(O-benzoyloxime) etc. are illustrated.
옥심에스테르 구조 함유 광중합 개시제의 시판품은 Ｉｒｇａｃｕｒｅ ＯＸＥ ０１, Ｉｒｇａｃｕｒｅ ＯＸＥ ０２, Ｉｒｇａｃｕｒｅ ＯＸＥ ０３, Ｉｒｇａｃｕｒｅ ＯＸＥ ０４（이상, ＢＡＳＦ재팬(주) 제품）, 아데카옥토머 Ｎ－１９１９, 아데카아클루즈 ＮＣＩ－８３１, 아데카아클루즈 ＮＣＩ－９３０（이상, （주）ＡＤＥＫＡ제품）, Ｏｍｎｉｒａｄ１３１２, Ｏｍｎｉｒａｄ１３１４, Ｏｍｎｉｒａｄ１３１６（이상, ＩＧＭ Ｒｅｇｉｎｓ（주）제품）, ＴＲ－ＰＢＧ－３０５, ＴＲ－ＰＢＧ－３０５７, ＴＲ－ＰＢＧ－３０４, ＴＲ－ＰＢＧ－３１４（이상, 샹조우강력전자신재료유한공사 제품）등이 예시된다.The commercial product of the optic ester structure containing light initiative is ｘ ｘ ｘ ｘ ｘ ｘ ０ ０ ０ ０ ０ ０ , Adeca Kluz NCI — ９ 30 (or more, (() ADA product), ｏNIIRAD 13, ｏNI ｉ113, ｏNI ｒ116 (or more, ｉM ｒ) 304, Tv-PBG-314 (above, product of Xiangzhou Strong Electric New Material Co., Ltd.), etc. are exemplified.
상기 코팅제 비휘발분１００질량% 중 옥심에스테르 구조 함유 광중합 개시제의 함유량의 상한 및 하한은 １０, ９, ８, ７, ６, ５, ４, ３．５, ３．４, ３．２, ３．１, ３, ２．９, ２．７, ２．５, ２．４, ２, １, ０．９, ０．７, ０．６, ０．５, ０．４, ０．２, ０．１질량％ 등이 예시된다. 일 실시형태에서 상기 함유량은 ０．１ ~ １０질량％가 바람직하고, １ ~ ５질량%가 보다 바람직하다.The upper and lower limits of the content of the oxime ester structure-containing photopolymerization initiator in 100% by mass of the non-volatile content of the coating agent are 10, 9, 8, 7, 6, 5, 4, 3.5, 3.4, 3.2, 3.1 , 3, 2.9, 2.7, 2.5, 2.4, 2, 1, 0.9, 0.7, 0.6, 0.5, 0.4, 0.2, 0.1 Mass % etc. are illustrated. In one embodiment, the content is preferably 0.1 to 10% by mass, and more preferably 1 to 5% by mass.
＜옥심에스테르 구조 비함유 광중합 개시제＞<Oxime ester structure-free photopolymerization initiator>
일 실시형태에서 상기 코팅제는 옥심에스테르 구조 비함유 광중합 개시제를 포함할 수 있다. 옥심에스테르 구조 비함유 광중합 개시제는 단독 또는 2종 이상으로 사용할 수 있다.In one embodiment, the coating agent may include a photopolymerization initiator that does not contain an oxime ester structure. The oxime ester structure-free photopolymerization initiator can be used alone or in combination of two or more.
옥심에스테르 구조 비함유 광중합 개시제는 α-히드록시알킬페논, 무치환 또는 치환 알킬페논, 무치환 또는 치환 벤질, 무치환 또는 치환 벤조페논, 아실포스핀옥시드, 옥심에스테르, 치환 티옥산톤 등이 예시된다.Examples of the photopolymerization initiator without an oxime ester structure include α-hydroxyalkyl phenone, unsubstituted or substituted alkyl phenone, unsubstituted or substituted benzyl, unsubstituted or substituted benzophenone, acylphosphine oxide, oxime ester, substituted thioxanthone, and the like. do.
α-히드록시알킬페논은 1-히드록시시클로헥실페닐케톤, 2-히드록시-2-메틸프로피오페논, 2-히드록시-4'-(2-히드록시에톡시)-2-메틸프로피오페논(1-[4-(2-히드록시에톡실)-페닐]-2-히드록시-메틸프로파논)), 2-히드록시-1-(4-(4-(2-히드록시-2-메틸프로피오닐)벤질)페닐)-2-메틸프로판-1-온) 등이 예시된다.α-Hydroxyalkylphenone is 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methylpropiophenone, 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Non(1-[4-(2-hydroxyethoxyl)-phenyl]-2-hydroxy-methylpropanone)), 2-hydroxy-1-(4-(4-(2-hydroxy-2 -methylpropionyl)benzyl)phenyl)-2-methylpropan-1-one) and the like.
무치환 또는 치환 알킬페논은 벤조인메틸에테르, 벤조인이소프로필에테르, 벤조인이소부틸에테르, 벤조인에틸에테르, 아세토페논, 2,2-디에톡시아세토페논, 2,2-디메톡시-2-페닐아세토페논, 2-페닐-2-(p-톨루엔술포닐옥시)아세토페논, 벤조인, 2-벤질-2-(디메틸아미노)-4'-모르폴리노부티로페논, 2-메틸-4'-(메틸티오)-2-모르폴리노프로피오페논, 2-이소니트로소프로피오페논, 2,2-디메톡시-1,2-디페닐에탄-1-온 등이 예시된다.Unsubstituted or substituted alkylphenones are benzoin methyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin ethyl ether, acetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2- Phenylacetophenone, 2-phenyl-2-(p-toluenesulfonyloxy)acetophenone, benzoin, 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone, 2-methyl-4 '-(methylthio)-2-morpholinopropiophenone, 2-isonitrosopropiophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one, etc. are illustrated.
무치환 또는 치환 벤질은 벤질, p-아니실 등의 무치환 또는 치환 벤질 등이 예시된다.Examples of unsubstituted or substituted benzyl include unsubstituted or substituted benzyl such as benzyl and p-anisyl.
무치환 또는 치환 벤조페논은 벤조페논, 4,4'-비스(디에틸아미노)벤조페논, 4,4'-비스(디메틸아미노)벤조페논, 4,4'-디클로로벤조페논, 1,4-디벤조일벤젠, 2-벤조일 안식향산, 4-벤조일안식향산, 2-벤조일안식향산메틸 등이 예시된다.Unsubstituted or substituted benzophenones include benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-dichlorobenzophenone, 1,4- Dibenzoylbenzene, 2-benzoylbenzoic acid, 4-benzoylbenzoic acid, methyl 2-benzoylbenzoate, etc. are illustrated.
아실포스핀옥시드는 2,4,6-트리메틸벤조일-디페닐-포스핀옥시드, 비스(2,4,6-트리메틸벤조일)-페닐포스핀옥시드 등이 예시된다.Examples of the acylphosphine oxide include 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.
치환 티옥산톤은 2-클로로티옥산톤, 2-이소프로필티옥산톤, 2,4-디에틸티옥산톤 등이 예시된다.Examples of the substituted thioxanthone include 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
상기 코팅제 비휘발분１００질량% 중 옥심에스테르 구조 비함유 광중합 개시제의 함유량의 상한 및 하한은 １０, ９, ８, ７, ６, ５, ４, ３．５, ３．４, ３．２, ３．１, ３, ２．９, ２．７, ２．５, ２．４, ２．２, ２, １．９, １．７．１．５, １．３, １．１, １, ０．９, ０．７, ０．６, ０．５, ０．４, ０．２, ０．１, ０질량％ 등이 예시된다. 일 실시형태에서 상기 함유량은 ０ ~ １０질량％가 바람직하고, ０ ~ ３질량%가 보다 바람직하다.The upper and lower limits of the content of the oxime ester structure-free photopolymerization initiator in 100% by mass of the non-volatile content of the coating agent are 10, 9, 8, 7, 6, 5, 4, 3.5, 3.4, 3.2, 3. 1, 3, 2.9, 2.7, 2.5, 2.4, 2.2, 2, 1.9, 1.7.1.5, 1.3, 1.1, 1, 0. 9, 0.7, 0.6, 0.5, 0.4, 0.2, 0.1, 0% by mass and the like are exemplified. In one embodiment, the content is preferably 0 to 10% by mass, and more preferably 0 to 3% by mass.
＜(메타)아크릴로일기를 2개 이하 갖는 폴리(메타)아크릴레이트＞<Poly (meth)acrylate having two or less (meth)acryloyl groups>
일 실시형태에 있어서, 상기 코팅제는 (메타)아크릴로일기를 2개 이하 갖는 폴리(메타)아크릴레이트을 포함할 수 있다. (메타)아크릴로일기를 2개 이하 갖는 폴리(메타)아크릴레이트는 단독 또는 2 종 이상으로 사용할 수 있다.In one embodiment, the coating agent may include poly(meth)acrylate having two or less (meth)acryloyl groups. Poly(meth)acrylates having two or less (meth)acryloyl groups can be used alone or in combination of two or more.
(메타)아크릴로일기를 2개 이하 갖는 폴리(메타)아크릴레이트는 알킬렌 디(메타)아크릴레이트, 옥시알킬렌 디(메타)아크릴레이트 등이 예시된다.Examples of the poly(meth)acrylate having two or less (meth)acryloyl groups include alkylene di(meth)acrylate and oxyalkylene di(meth)acrylate.
본 개시에서, 알킬렌 디(메타)아크릴레이트는 옥시(메타)아크릴로일기를 2개 갖는 화합물로서, 이 화합물에서 옥시(메타)아크릴로일기를 제외한 부분이 알킬렌기만으로 구성되는 화합물을 의미한다.In the present disclosure, alkylene di (meth) acrylate is a compound having two oxy (meth) acryloyl groups, and means a compound in which the portion excluding the oxy (meth) acryloyl group is composed of only alkylene groups do.
알킬렌 디(메타)아크릴레이트는 하기 구조식Alkylene di(meth)acrylates have the following structural formula
[화학식 17][Formula 17]
(식 중, Ra1은 수소 원자 또는 메틸기이고, Ra2는 알킬렌기이며, Ra3은 수소 원자 또는 메틸기이다.)(In the formula, R a1 is a hydrogen atom or a methyl group, R a2 is an alkylene group, and R a3 is a hydrogen atom or a methyl group.)
으로 나타난다.appears as
직쇄 알킬렌 디(메타)아크릴레이트는 에틸렌글리콜 디(메타)아크릴레이트, 1,3-프로필렌글리콜 디(메타)아크릴레이트, 1,4-부탄디올 디(메타)아크릴레이트, 1,5-펜탄디올 디(메타)아크릴레이트, 1,6-헥산디올 디(메타)아크릴레이트, 1,7-헵탄디올 디(메타)아크릴레이트, 1,8-옥탄디올 디(메타)아크릴레이트, 1,9-노난디올 디(메타)아크릴레이트, 1,10-데칸디올 디(메타)아크릴레이트 등이 예시된다.Straight-chain alkylene di(meth)acrylates include ethylene glycol di(meth)acrylate, 1,3-propylene glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,5-pentanediol Di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,7-heptanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9- Nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate and the like are exemplified.
분기 알킬렌 디(메타)아크릴레이트는 1,2-프로필렌글리콜 디(메타)아크릴레이트, 1,2-부탄디올 디(메타)아크릴레이트, 1,3-부탄디올 디(메타)아크릴레이트, 2-메틸-1,3-프로필렌글리콜 디(메타)아크릴레이트, 1,1-디메틸-1,2-에틸렌글리콜 디(메타)아크릴레이트, 1,4-펜탄디올 디(메타)아크릴레이트, 1,3-펜탄디올 디(메타)아크릴레이트, 1,2-펜탄디올 디(메타)아크릴레이트, 네오펜틸글리콜 디(메타)아크릴레이트, 3-메틸-1,5-펜탄디올 디(메타)아크릴레이트, 이소노난디올 디아크릴레이트 등이 예시된다.Branched alkylene di(meth)acrylates are 1,2-propylene glycol di(meth)acrylate, 1,2-butanediol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 2-methyl -1,3-propylene glycol di(meth)acrylate, 1,1-dimethyl-1,2-ethylene glycol di(meth)acrylate, 1,4-pentanediol di(meth)acrylate, 1,3- Pentanediol di(meth)acrylate, 1,2-pentanediol di(meth)acrylate, neopentylglycol di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, iso Nonanediol diacrylate etc. are illustrated.
시클로알킬렌 디(메타)아크릴레이트는 디메틸올-트리시클로데칸 디(메타)아크릴레이트, 비스(4-(메타)아크릴옥시시클로헥실)메탄, 2,2-비스(4-(메타)아크릴옥시시클로헥실)프로판, 2,2-비스(4-(메타)아크릴옥시시클로헥실)부탄, 1,4-디(메타)아크릴옥시메틸시클로헥산, 시클로헥산(메타)아크릴레이트, 수소화 비스페놀 A 디(메타)아크릴레이트(2,2-비스(4-(메타)아크릴옥시시클로헥실)프로판), 수소화 비스페놀 B 디(메타)아크릴레이트(2,2-비스(4-(메타)아크릴옥시시클로헥실)부탄) 등이 예시된다.Cycloalkylene di(meth)acrylate is dimethylol-tricyclodecane di(meth)acrylate, bis(4-(meth)acryloxycyclohexyl)methane, 2,2-bis(4-(meth)acryloxy Cyclohexyl)propane, 2,2-bis(4-(meth)acryloxycyclohexyl)butane, 1,4-di(meth)acryloxymethylcyclohexane, cyclohexane(meth)acrylate, hydrogenated bisphenol A di( meth)acrylate (2,2-bis(4-(meth)acryloxycyclohexyl)propane), hydrogenated bisphenol B di(meth)acrylate (2,2-bis(4-(meth)acryloxycyclohexyl) butane), etc. are exemplified.
옥시알킬렌 디(메타)아크릴레이트는 디펜타에리스리톨 디(메타)아크릴레이트, 트리펜타에리스리톨 디(메타)아크릴레이트, 디트리메틸올 디(메타)아크릴레이트, 디글리세린 디(메타)아크릴레이트 등이 예시된다.Oxyalkylene di(meth)acrylates include dipentaerythritol di(meth)acrylate, tripentaerythritol di(meth)acrylate, ditrimethylol di(meth)acrylate, and diglycerin di(meth)acrylate. is exemplified
상기 코팅제 비휘발분１００질량% 중 (메타)아크릴로일기를 2개 이하 갖는 폴리(메타)아크릴레이트의 함유량의 상한 및 하한은 ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０, ５, ４, ２, １, ０질량％ 등이 예시된다. 일 실시형태에 있어서, 상기 함유량은 ０～５０질량％가 바람직하고, ０～３５질량%가 보다 바람직하다.The upper and lower limits of the content of the poly(meth)acrylate having two or less (meth)acryloyl groups in 100% by mass of the non-volatile content of the coating agent are 50, 45, 40, 35, 30, 25, 20, 15, 10, 5, 4, 2, 1, 0 mass % etc. are illustrated. In one embodiment, the content is preferably 0 to 50% by mass, and more preferably 0 to 35% by mass.
<유기 용매><Organic Solvent>
일 실시형태에 있어서, 상기 코팅제는 유기 용매을 포함할 수 있다. 유기 용매는 단독 또는 2 종 이상으로 사용할 수 있다.In one embodiment, the coating agent may include an organic solvent. An organic solvent can be used individually or in 2 or more types.
유기 용매로는 상술한 것 등이 예시된다.Examples of the organic solvent include those described above.
상기 코팅제 비휘발분１００질량% 중 유기 용매의 상한 및 하한은 ９０, ８５, ８０, ７５, ７０, ６５, ６０, ５５, ５０, ４５, ４０, ３５, ３０, ２５, ２０, １５, １０, ５, ４, ２, １, ０질량％ 등이 예시된다. 일 실시형태에서 상기 함유량은 ０ ~ ９０질량％가 바람직하고, ０ ~ ７０질량%가 보다 바람직하다.The upper and lower limits of the organic solvent in 100% by mass of the non-volatile content of the coating agent are 90, 85, 80, 75, 70, 65, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10, 5 , 4, 2, 1, 0 mass %, etc. are illustrated. In one embodiment, the content is preferably 0 to 90% by mass, and more preferably 0 to 70% by mass.
<첨가제><Additives>
상기 코팅제에는 (메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트, (메타)아크릴로일기 함유 실리카 입자, 옥심에스테르 구조 함유 광중합 개시제, 옥심에스테르 구조 비함유 광중합 개시제, (메타)아크릴로일기를 2개 이하 갖는 폴리(메타)아크릴레이트, 유기 용매의 어느 것에도 해당하지 않는 제제를 첨가제로서 포함할 수 있다.The coating agent includes a poly(meth)acrylate having three or more (meth)acryloyl groups, a silica particle containing a (meth)acryloyl group, a photopolymerization initiator containing an oxime ester structure, a photopolymerization initiator without an oxime ester structure, and a (meth)acryloyl group. A poly(meth)acrylate having two or less royl groups and an agent that does not correspond to any of the organic solvents may be included as additives.
첨가제는 광 증감제, 산화 방지제, 광 안정제, 레벨링제, 안료 등이 예시된다.Examples of additives include photosensitizers, antioxidants, light stabilizers, leveling agents, and pigments.
일 실시형태에 있어서, 첨가제의 함유량은 상기 코팅제 100질량부에 대해 1질량부 미만, 0.1질량부 미만, 0.01질량부 미만, 0질량부 등이 예시된다. 또한, (메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트, (메타)아크릴로일기 함유 실리카 입자, 옥심에스테르 구조 함유 광중합 개시제, 옥심에스테르 구조 비함유 광중합 개시제, (메타)아크릴로일기를 2개 이하 갖는 폴리(메타)아크릴레이트, 유기 용매 중 어느 하나의 100질량부에 대해 １질량부 미만, ０．１질량부 미만, ０．０１질량부 미만, ０질량부 등이 예시된다.In one embodiment, the content of the additive is exemplified by less than 1 part by mass, less than 0.1 part by mass, less than 0.01 part by mass, 0 part by mass and the like with respect to 100 parts by mass of the coating agent. In addition, poly(meth)acrylates having three or more (meth)acryloyl groups, (meth)acryloyl group-containing silica particles, oxime ester structure-containing photopolymerization initiators, oxime ester structure-free photopolymerization initiators, (meth)acryloyl groups Examples include less than 1 part by mass, less than 0.1 part by mass, less than 0.01 part by mass, 0 part by mass, etc. with respect to 100 parts by mass of any one of the poly(meth)acrylate having two or less groups and the organic solvent. .
상기 코팅제는 (메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트, (메타)아크릴로일기 함유 실리카 입자, 옥심에스테르 구조 함유 광중합 개시제와 필요에 따라 옥심에스테르 구조 비함유 광중합 개시제, (메타)아크릴로일기를 2개 이하 갖는 폴리(메타)아크릴레이트, 유기용매 성분 및 첨가제가 각종 공지의 수단에 의해 분산·혼합됨으로써 제조될 수 있다. 또한, 각 성분의 첨가 순서는 특별히 한정되지 않는다. 또한, 분산·혼합 수단은 각종 공지의 장치(유화 분산기, 초음파 분산 장치 등)가 사용될 수 있다.The coating agent is a poly(meth)acrylate having three or more (meth)acryloyl groups, (meth)acryloyl group-containing silica particles, an oxime ester structure-containing photopolymerization initiator and optionally an oxime ester structure-free photopolymerization initiator, ( It can be prepared by dispersing and mixing poly(meth)acrylate having two or less meth)acryloyl groups, organic solvent components and additives by various known means. In addition, the order of addition of each component is not specifically limited. In addition, various known devices (emulsification disperser, ultrasonic dispersion device, etc.) can be used as the dispersion/mixing means.
상기 코팅제에서의 (메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트와 (메타)아크릴로일기 함유 실리카 입자의 질량비 （(메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트의 질량／(메타)아크릴로일기 함유 실리카 입자의 질량）의 상한 및 하한은 １８, １７, １５, １４, １２, １０, ９, ７, ５, ４, ２, １, ０．９, ０．７, ０．５, ０．３, ０．２, ０．１４ 등이 예시된다.Mass ratio of poly(meth)acrylate having 3 or more (meth)acryloyl groups in the coating agent and silica particles containing (meth)acryloyl groups (poly(meth)acryloyl having 3 or more (meth)acryloyl groups) The upper and lower limits of mass of rate / mass of (meth)acryloyl group-containing silica particles) are 18, 17, 15, 14, 12, 10, 9, 7, 5, 4, 2, 1, 0.9, 0 .7, 0.5, 0.3, 0.2, 0.14 and the like are exemplified.
일 실시형태에 있어서, 상기 질량비는 ０．１４ ~ １８이 바람직하다.In one embodiment, the mass ratio is preferably 0.14 to 18.
상기 코팅제에서의 (메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트와 옥심에스테르 구조 함유 광중합 개시제의 질량비 （(메타)아크릴로일기를 3개 이상 갖는 폴리(메타)아크릴레이트의 질량／옥심에스테르 구조 함유 광중합 개시제의 질량）의 상한 및 하한은 ９００, ７００, ５００, ２５０, １００, ９０, ７５, ５０, ２５, ２０, １９, １５, １４, １２, １０, ９, ７, ５, ４, ２, １ 등이 예시된다. 일 실시형태에 있어서, 상기 질량비는 １ ~ ９００가 바람직하다.Mass ratio of the poly(meth)acrylate having 3 or more (meth)acryloyl groups in the coating agent and the photopolymerization initiator containing an oxime ester structure (Mass of poly(meth)acrylate having 3 or more (meth)acryloyl groups) The upper and lower limits of / the mass of the photopolymerization initiator containing an oxime ester structure) are 900, 700, 500, 250, 100, 90, 75, 50, 25, 20, 19, 15, 14, 12, 10, 9, 7, 5 , 4, 2, 1, etc. are exemplified. In one embodiment, the mass ratio is preferably 1 to 900.
상기 코팅제에서의 (메타)아크릴로일기 함유 실리카 입자와 옥심에스테르 구조 함유 광중합 개시제의 질량비 （(메타)아크릴로일기 함유 실리카 입자의 질량／옥심에스테르 구조 함유 광중합 개시제의 질량）의 상한 및 하한은 ７００, ５００, ２５０, １００, ９０, ７５, ５０, ２５, ２０, １９, １５, １４, １２, １０, ９, ７, ５, ４, ２, １, ０．９, ０．７, ０．５ 등이 예시된다. 일 실시형태에 있어서, 상기 질량비는 ０．５ ~ ７００가 바람직하다.The upper and lower limits of the mass ratio of (meth)acryloyl group-containing silica particles and oxime ester structure-containing photopolymerization initiator (mass of (meth)acryloyl group-containing silica particles / oxime ester structure-containing photopolymerization initiator) in the coating agent are 700 , 500, 250, 100, 90, 75, 50, 25, 20, 19, 15, 14, 12, 10, 9, 7, 5, 4, 2, 1, 0.9, 0.7, 0.5 etc. are exemplified. In one embodiment, the mass ratio is preferably 0.5 to 700.
상기 코팅제는 용이접착 처리를 행하지 않은 환상 올레핀수지용 코팅제, 용이접착 처리를 행하지 않은 환상 올레핀수지에 직접 도포되는 환상 올레핀수지용 코팅제로서 사용될 수 있다.The coating agent can be used as a coating agent for cyclic olefin resins not subjected to an easy adhesion treatment, or a coating agent for cyclic olefin resins directly applied to a cyclic olefin resin that has not been subjected to an easy adhesion treatment.
[경화물][cured material]
본 개시는 상기 환상 올레핀수지용 코팅제 또는 상기 코팅제 키트의 경화물을 제공한다.The present disclosure provides a cured product of the coating agent for the cyclic olefin resin or the coating agent kit.
경화 조건은 후술하는 것 등이 예시된다.As for hardening conditions, what is mentioned later etc. are illustrated.
[적층물][Laminate]
본 개시는 상기 경화물을 포함하는 적층물을 제공한다.The present disclosure provides a laminate including the cured product.
환상 올레핀수지 기재의 두께는 특별히 한정되지 않지만, １０~２０００μｍ정도가 바람직하다. 또한, 경화물층의 두께는 특별히 한정되지 않지만 0.1~5μm 정도가 바람직하다.The thickness of the cyclic olefin resin substrate is not particularly limited, but is preferably about 10 to 2000 μm. In addition, the thickness of the cured material layer is not particularly limited, but is preferably about 0.1 to 5 μm.
일 실시형태에서 상기 환상 올레핀수지 기재는 용이접착 처리를 행하지 않은 환상 올레핀 수지 기재이다.In one embodiment, the cyclic olefin resin substrate is a cyclic olefin resin substrate that has not been subjected to an easy adhesion treatment.
상기 적층물은 각종 공지의 방법으로 제조된다. 일 실시형태에서 적층물의 제조 방법은 코팅제를 기재의 적어도 한쪽 면에 도공하는 공정(도공 공정), 활성 에너지선을 조사함으로써 활성 에너지선 경화성수지 경화물층을 형성하는 공정(활성 에너지선 경화 공정)을 포함한다.The laminate is manufactured by various known methods. In one embodiment, the method for manufacturing a laminate includes a step of applying a coating agent to at least one side of a substrate (coating step), and a step of forming an active energy ray-curable resin cured material layer by irradiating active energy rays (active energy ray curing step). includes
(도공 공정)(coating process)
도공 방법은 바코터 도공, 와이어바 도공, 메이어바 코팅, 에어나이프 도공, 그라비아 도공, 리버스그라비아 도공, 플로우코트 도공, 오프셋인쇄, 플렉소인쇄, 스크린인쇄법 등이 예시된다.Examples of the coating method include bar coater coating, wire bar coating, Meyer bar coating, air knife coating, gravure coating, reverse gravure coating, flow coat coating, offset printing, flexographic printing, screen printing, and the like.
도공량은 특별히 한정되지 않는다. 도공량은 건조 후의 질량이 0.1 ~ 30g/㎡ 정도가 바람직하고, 1 ~ 20g/㎡ 정도가 보다 바람직하다.The coating amount is not particularly limited. The mass after drying is preferably about 0.1 to 30 g/m 2 , and more preferably about 1 to 20 g/m 2 .
(활성 에너지선 경화 공정)(active energy ray curing process)
활성 에너지선 경화 반응에 사용하는 활성 에너지선은 자외선이나 전자선 등이 예시된다.An ultraviolet ray, an electron beam, etc. are illustrated as an active energy ray used for an active energy ray hardening reaction.
자외선의 광원은 크세논 램프, 고압수은 램프, 메탈할라이드 램프를 갖는 자외선 조사 장치 등이 예시된다. 또한, 광량 및 광원 배치, 반송속도 등은 필요에 따라 조정할 수 있다.Examples of the ultraviolet light source include a xenon lamp, a high-pressure mercury lamp, and an ultraviolet irradiation device having a metal halide lamp. In addition, the amount of light, the arrangement of the light sources, the transport speed, etc. can be adjusted as needed.
고압수은등을 사용하는 경우에는 80 ~ 160W/cm 정도의 광량을 갖는 램프 1 등에 대해 반송속도 2 ~ 50m/분 정도로 경화시키는 것이 바람직하다.In the case of using a high-pressure mercury lamp, it is preferable to cure at a transport speed of about 2 to 50 m/min with respect to lamp 1 having a light intensity of about 80 to 160 W/cm.
전자선을 사용하는 경우에는 10 ~ 300kV 정도의 가속 전압을 갖는 전자선 가속 장치에 의해 반송 속도 5 ~ 50m/분 정도의 조건으로 경화시키는 것이 바람직하다.In the case of using an electron beam, it is preferable to cure the film under conditions of a conveyance speed of about 5 to 50 m/min with an electron beam accelerator having an accelerating voltage of about 10 to 300 kV.
실시예Example
이하, 실시예 및 비교예를 통하여 본 발명을 구체적으로 설명한다. 단, 상술한 바람직한 실시형태에서의 설명 및 이하의 실시예는 예시의 목적으로만 제공되며, 본 발명을 한정하는 목적으로 제공하는 것은 아니다. 따라서, 본 발명의 범위는 본 명세서에 구체적으로 기재된 실시형태에도 실시예에도 한정되지 않고, 청구범위에 의해서만 한정된다. 또한, 각 실시예 및 비교예에서 특별히 설명이 없는 한 부, % 등의 수치는 질량 기준이다.Hereinafter, the present invention will be described in detail through Examples and Comparative Examples. However, the description of the above preferred embodiment and the following examples are provided only for the purpose of illustration, and are not provided for the purpose of limiting the present invention. Accordingly, the scope of the present invention is not limited to the embodiments or examples specifically described herein, but is limited only by the claims. In addition, in each Example and Comparative Example, unless otherwise specified, numerical values such as parts and % are based on mass.
실시예 1Example 1
교반기, 온도계, 적하 로트, 냉각관 및 공기 도입구를 구비한 반응 용기에 아로닉스 Ｍ―３０５（토아고세이(주) 제품）를 비휘발분으로서 ７０질량부, ＰＧＭ－ＡＣ－２１４０Ｙ（닛산화학(주) 제품）를 비휘발분으로서 ２７질량부, Ｉｒｇａｃｕｒｅ ＯＸＥ０１（BASF재팬(주) 제품）를 비휘발분으로서 ３질량부 혼합하고, 메틸에틸케톤으로 비휘발분이 ３０％가 되도록 조정하여 환상 올레핀수지용 코팅제를 얻었다. 제조한 환상 올레핀수지용 코팅제를 바코터를 이용하여 두께 100μm의 제오노아 필름 ZF-16(니폰제온(주) 제품) 상에 건조 후의 막두께가 1μm가 되도록 도포하고, 80℃ 60초로 시판의 온풍 건조기에서 건조시켰다. 그 후, 질소 분위기하에서 메탈할라이드 램프를 이용하여 300mJ/㎠의 자외선을 조사하여 적층물을 얻었다.Aronix M-305 (manufactured by Toagosei Co., Ltd.) was added as a non-volatile content in 70 parts by mass, PGM-AC-2140Y (Nissan Chemical Co., Ltd.) ) product) as a non-volatile content, 27 parts by mass of Irggaca, and 3 parts by mass of OxE01 (manufactured by BASF Japan Co., Ltd.) as a non-volatile content, and adjusting the non-volatile content to 30% with methyl ethyl ketone to obtain a coating agent for a cyclic olefin resin. Got it. The prepared coating agent for cyclic olefin resin was applied using a bar coater on Zeonoa film ZF-16 (manufactured by Nippon Zeon Co., Ltd.) having a thickness of 100 μm so that the film thickness after drying was 1 μm, and commercially available warm air at 80 ° C. for 60 seconds dried in a dryer. Thereafter, a laminate was obtained by irradiating ultraviolet rays of 300 mJ/cm 2 using a metal halide lamp in a nitrogen atmosphere.
특별한 언급이 없는 한 실시예 1이외의 실시예 및 비교예는 하기 표와 같이 변경한 것 이외에는 실시예 1과 마찬가지로 행하였다.Unless otherwise specified, Examples and Comparative Examples other than Example 1 were carried out in the same manner as in Example 1 except for changes as shown in the table below.
<약칭의 설명><Description of abbreviation>
아로닉스 Ｍ－３０５： 펜타에리스리톨트리 및 테트라아크릴레이트（토아고세이(주) 제품）Aronix M-305: Pentaerythritol tri and tetraacrylate (manufactured by Toagosei Co., Ltd.)
아로닉스 Ｍ－４００： 디펜타에리스리톨펜타 및 헥사아크릴레이트（토아고세이(주) 제품）Aronics M-400: dipentaerythritol penta and hexaacrylate (manufactured by Toagosei Co., Ltd.)
비스코트 ＃８０２： 트리펜타에리스리톨 폴리아크릴레이트, 모노 및 디펜타에리스리톨 폴리아크릴레이트, 폴리펜타에리스리톨 폴리아크릴레이트의 혼합물（모두 아크릴로일기를 3개 이상 포함）（오사카유기화학공업(주) 제품）Biscott #802: A mixture of tripentaerythritol polyacrylate, mono- and dipentaerythritol polyacrylate, and polypentaerythritol polyacrylate (all containing three or more acryloyl groups) (manufactured by Osaka Organic Chemical Industry Co., Ltd.)
아로닉스 Ｍ－４０８： 디트리메틸올프로판 테트라아크릴레이트（토아고세이(주) 제품）Aronics M-408: Ditrimethylolpropane tetraacrylate (manufactured by Toagosei Co., Ltd.)
데나콜아크릴레이트 ＤＡ－３１４： 글리세롤 폴리글리시딜에테르의 아크릴산 부가물（아크릴로일기를 3개 이상 포함）（나가세켐텍스 (주) 제품）Denacol Acrylate DAA-314: Acrylic acid adduct of glycerol polyglycidyl ether (contains 3 or more acryloyl groups) (manufactured by Nagase ChemteX Co., Ltd.)
ＭｉｒａｍｅｒＰＵ６１０： 지방족우레탄 헥사아크릴레이트（Ｍｉｗｏｎ Ｓｐｅｃｉａｌｔｙ Ｃｈｅｍｉｃａｌ사 제품）ＭｉｒａムｅｒＰＵ６１０: Aliphatic urethane hexaacrylate (product made by ＭｉｗｏｎＳｐｅｃｉａｌｔｙ ＣｈｅｅｉｃａｏｎＳｐｅｃｉａｌｔｙ Ｃｈｅｅ）
아로닉스 Ｍ－７１００： 폴리에스테르 폴리아크릴레이트（아크릴로일기를 3개 이상 포함）（토아고세이(주) 제품）Aronix M-7100: Polyester polyacrylate (containing 3 or more acryloyl groups) (manufactured by Toagosei Co., Ltd.)
HDDA: 1,6-헥산디올 디아크릴레이트(다이셀 · 올넥스(주) 제품)HDDA: 1,6-hexanediol diacrylate (made by Daicel Allnex Co., Ltd.)
라이트아크릴레이트３ＥＧ－Ａ： 트리에틸렌글리콜 디아크릴레이트（쿄에이샤화학(주) 제품）Light Acrylate 3EG-A: Triethylene glycol diacrylate (manufactured by Kyoeisha Chemical Co., Ltd.)
비스코트＃５４０： 아크릴산과 2-(클로로메틸)옥시란 · 4,4'-(이소프로필리덴)비스페놀 중합체의 반응물인 디아크릴레이트（오사카유기화학공업(주) 제품）Biscott #540: Diacrylate, a reaction product of acrylic acid and 2-(chloromethyl)oxirane/4,4'-(isopropylidene)bisphenol polymer (manufactured by Osaka Organic Chemical Industry Co., Ltd.)
ＰＧＭ－ＡＣ－２１４０Ｙ： 프로필렌글리콜 모노메틸에테르 분산실리카 졸［３－（메타크릴로일옥시）프로필］트리메톡시실란 표면 개질 등급（입자지름 １０ ~ １５ｎｍ）（닛산화학(주) 제품）PGM-AC-2140Y: propylene glycol monomethyl ether dispersed silica sol [3- (methacryloyloxy) propyl] trimethoxysilane surface modification grade (particle diameter 10 to 15 nm) (manufactured by Nissan Chemical Industries, Ltd.)
ＭＥＫ－ＡＣ－２１４０Ｚ： 메틸에틸케톤 분산 실리카 졸의 ［３－（메타크릴로일옥시）프로필］트리메톡시실란 표면 개질 등급（입자지름 １０ ~ １５ｎｍ）（닛산화학(주) 제품）MEK-AC-2140Z: [3-(methacryloyloxy)propyl] trimethoxysilane surface modification grade of silica sol dispersed in methyl ethyl ketone (particle size: 10 to 15 nm) (manufactured by Nissan Chemical Industries, Ltd.)
ＰＧＭ－ＡＣ－４１３０Ｙ： 프로필렌글리콜 모노메틸에테르 분산 실리카 졸의 ［３－（메타크릴로일옥시）프로필］트리메톡시실란 표면 개질 등급（입자지름 ４０ ~ ５０ｎｍ）（닛산화학(주) 제품）PGM-AC-4130Y: [3-(methacryloyloxy)propyl] trimethoxysilane surface modification grade of propylene glycol monomethyl ether dispersed silica sol (particle size: 40 to 50 nm) (manufactured by Nissan Chemical Industries, Ltd.)
Irgacure OXE01: 1.2-옥탄디온, 1-[4-(페닐티오)-, 2-(O-벤조일옥심)](즉 2-((벤조일옥시)이미노)-1-(4-(페닐티오)페닐)옥탄-1-온)(BASF 재팬(주) 제품)Irgacure OXE01: 1.2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] (i.e. 2-((benzoyloxy)imino)-1-(4-(phenylthio) Phenyl)octan-1-one) (manufactured by BASF Japan Co., Ltd.)
Irgacure OXE04: 옥심에스테르 구조 함유 광중합 개시제(BASF 재팬(주) 제품)Irgacure OXE04: Photopolymerization initiator containing oxime ester structure (manufactured by BASF Japan Co., Ltd.)
ＯＭＮＩＲＡＤ １３１６： 옥심에스테르 구조 함유 광중합 개시제 (IGM Regins(주) 제품)ＯＭＮＩＲＡＤ １３１６： photopolymerization initiator containing oxime ester structure (manufactured by IGM Regins Co., Ltd.)
ＴＲ－ＰＢＧ－３０５： １－［４－（페닐티오）페닐］－３－시클로펜틸프로판－１，２－디온－２－（Ｏ－벤조일옥심）（샹조우강력전자신재료유한공사 제품）TBG-305: 1-[4-(phenylthio)phenyl]-3-cyclopentylpropane-1,2-dione-2-(O-benzoyloxime) (manufactured by Xiangzhou Strong Electronic New Materials Co., Ltd.)
OMNIRAD 184: 1-히드록시시클로헥실-페닐케톤(IGM Regins(주) 제품)OMNIRAD 184: 1-hydroxycyclohexyl-phenylketone (manufactured by IGM Regins Co., Ltd.)
OMNIRAD 127: 2-히드록시-1-(4-(4-(2-히드록시-2-메틸프로피오닐)벤질)페닐)-2-메틸프로판-1-온(IGM Regins(주) 제품)OMNIRAD 127: 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)benzyl)phenyl)-2-methylpropan-1-one (manufactured by IGM Regins Co., Ltd.)
OMNIRAD 754: 옥시페닐아세트산 2-[2-옥소-2-페닐-아세톡시-에톡시]에틸에스테르와 옥시페닐아세트산 2-[2-히드록시-에톡시]에틸에스테르의 혼합물(IGM Regins(주) 제품)OMNIRAD 754: mixture of oxyphenylacetic acid 2-[2-oxo-2-phenyl-acetoxy-ethoxy]ethyl ester and oxyphenylacetic acid 2-[2-hydroxy-ethoxy]ethyl ester (IGM Regins Co., Ltd.) product)
OMNIRAD 907: 2-메틸-1-[4-(메틸티오)페닐]-2-모르폴리노프로판-1-온(IGM Regins(주) 제품)OMNIRAD 907: 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one (manufactured by IGM Regins Co., Ltd.)
SpeedcureTPO: 2,4,6-트리메틸벤조일디페닐포스핀옥시드(LAMBSON사 제품)SpeedcureTPO: 2,4,6-trimethylbenzoyldiphenylphosphine oxide (made by LAMBSON)
Esacure One: 2관능 알파 히드록시케톤(IGM Regins(주) 제품)Esacure One: Bifunctional alpha hydroxyketone (manufactured by IGM Regins Co., Ltd.)
＜기재밀착성＞<Substrate Adhesion>
상기에서 얻어진 적층물에 대해 JIS K5600-5-4에 준하여 100칸 바둑판 박리 시험에 의해 밀착성을 평가하였다. 결과의 표시는 (박리 시험으로 남은 칸의 수/100)이다.Adhesion of the laminate obtained above was evaluated by a 100 square checkerboard peel test according to JIS K5600-5-4. The display of the result is (the number of squares left by the peel test/100).
＜도공성＞<coating>
상기에서 얻어진 적층물에 대하여 육안으로 평가하였다.The laminate obtained above was visually evaluated.
○：코팅제를 라미네이트 상에 도포한 후에 라미네이트 표면에서 코팅제가 튀어나오지 않고, 필름 상의 코팅제를 도포한 면적의 100%가 코팅제로 코팅되어 있다.○: After the coating agent was applied on the laminate, the coating agent did not protrude from the surface of the laminate, and 100% of the area to which the coating agent was applied on the film was coated with the coating agent.
×：코팅제가 라미네이트 상에 도포된 후에 라미네이트 표면에서 코팅제가 튀어나오고, 필름 상의 코팅제가 도포된 면적의 100%가 코팅제로 코팅되어 있지 않았다.x: After the coating agent was applied on the laminate, the coating agent protruded from the surface of the laminate, and 100% of the area to which the coating agent was applied on the film was not coated with the coating agent.
Claims (4)
(메타)아크릴로일기 함유 실리카 입자 및
옥심에스테르 구조 함유 광중합 개시제
를 포함하는 환상 올레핀 수지용 코팅제.(meth)poly(meth)acrylate having 3 or more acryloyl groups;
(meth)acryloyl group-containing silica particles and
Photopolymerization initiator containing oxime ester structure
A coating agent for a cyclic olefin resin comprising a.
A laminate comprising the cured product according to claim 3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021134481A JP7020579B1 (en) | 2021-08-20 | 2021-08-20 | Coating agent for cyclic olefin resin, cured product and laminate |
| JPJP-P-2021-134481 | 2021-08-20 |
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| Publication Number | Publication Date |
|---|---|
| KR20230028143A true KR20230028143A (en) | 2023-02-28 |
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| KR1020220082849A KR20230028143A (en) | 2021-08-20 | 2022-07-06 | Coating agent for cyclic olefin resin, cured product, and laminate |
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| Country | Link |
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| JP (1) | JP7020579B1 (en) |
| KR (1) | KR20230028143A (en) |
| CN (1) | CN115707741A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009286924A (en) | 2008-05-30 | 2009-12-10 | Jsr Corp | Curable composition |
| JP2014189566A (en) | 2013-03-26 | 2014-10-06 | Dic Corp | Active energy ray-curable composition for cyclic olefin resin and cyclic olefin resin film using the composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006160802A (en) | 2004-12-03 | 2006-06-22 | Mitsubishi Chemicals Corp | Stain resistance-imparting agent, cured product and article |
| JP5472692B2 (en) | 2009-07-06 | 2014-04-16 | 日立化成株式会社 | Photosensitive resin composition capable of alkali development and photosensitive film using the same |
| JP2013234217A (en) | 2012-05-07 | 2013-11-21 | Toagosei Co Ltd | Active energy ray-curing coating agent composition |
| JP7375343B2 (en) | 2019-06-25 | 2023-11-08 | 味の素株式会社 | resin composition |
| WO2021059977A1 (en) | 2019-09-26 | 2021-04-01 | 富士フイルム株式会社 | Curable composition, cured film, color filter, solid-state imaging element, and image display device |
-
2021
- 2021-08-20 JP JP2021134481A patent/JP7020579B1/en active Active
-
2022
- 2022-07-06 KR KR1020220082849A patent/KR20230028143A/en unknown
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009286924A (en) | 2008-05-30 | 2009-12-10 | Jsr Corp | Curable composition |
| JP2014189566A (en) | 2013-03-26 | 2014-10-06 | Dic Corp | Active energy ray-curable composition for cyclic olefin resin and cyclic olefin resin film using the composition |
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| Publication number | Publication date |
|---|---|
| JP2023028646A (en) | 2023-03-03 |
| JP7020579B1 (en) | 2022-02-16 |
| CN115707741A (en) | 2023-02-21 |
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