JP5229555B2 - Active energy ray-curable resin composition for coating and film substrate - Google Patents
Active energy ray-curable resin composition for coating and film substrate Download PDFInfo
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- JP5229555B2 JP5229555B2 JP2008253241A JP2008253241A JP5229555B2 JP 5229555 B2 JP5229555 B2 JP 5229555B2 JP 2008253241 A JP2008253241 A JP 2008253241A JP 2008253241 A JP2008253241 A JP 2008253241A JP 5229555 B2 JP5229555 B2 JP 5229555B2
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- JP
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- Prior art keywords
- meth
- acrylate
- active energy
- resin composition
- energy ray
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011248 coating agent Substances 0.000 title claims description 40
- 238000000576 coating method Methods 0.000 title claims description 40
- 239000011342 resin composition Substances 0.000 title claims description 37
- 239000000758 substrate Substances 0.000 title claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 132
- 239000005056 polyisocyanate Substances 0.000 claims description 32
- 229920001228 polyisocyanate Polymers 0.000 claims description 32
- 125000005442 diisocyanate group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 16
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 3
- -1 polyethylene terephthalate Polymers 0.000 description 58
- 239000010408 film Substances 0.000 description 43
- 239000000203 mixture Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 18
- 239000000178 monomer Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 239000012948 isocyanate Substances 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000008119 colloidal silica Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- 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 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-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
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- SVIQBUBNVYWIDV-UHFFFAOYSA-N 2-methoxy-2-(2-methoxyphenyl)-1-phenylethanone Chemical compound C=1C=CC=C(OC)C=1C(OC)C(=O)C1=CC=CC=C1 SVIQBUBNVYWIDV-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-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
- BYPFICORERPGJY-UHFFFAOYSA-N 3,4-diisocyanatobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2(N=C=O)C(N=C=O)=CC1C2 BYPFICORERPGJY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- SJIXRGNQPBQWMK-UHFFFAOYSA-N DEAEMA Natural products CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 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
- 239000012965 benzophenone Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000012461 cellulose resin Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 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
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000007756 gravure coating Methods 0.000 description 2
- 150000002596 lactones Chemical class 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 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
- 239000000126 substance Substances 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 1
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-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
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 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
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
本発明は、特に、フィルム基材等の薄膜のプラスチック基材への塗工した際にも硬度が得られ、且つ、硬化の際も低収縮でフィルムの反り（カール）が少ないコーティング用活性エネルギー線硬化型樹脂組成物、及び該組成物を硬化させた硬化層を有するフィルム基材に関する。 In particular, the present invention provides an active energy for coating that can provide hardness even when applied to a plastic substrate of a thin film such as a film substrate, and has low shrinkage and curl of the film even when cured. The present invention relates to a wire curable resin composition and a film substrate having a cured layer obtained by curing the composition.
ポリエチレンテレフタレート樹脂（ＰＥＴ）、アクリル樹脂、ポリカーボネート樹脂、アセチル化セルロース樹脂などを用いて製造されるプラスチックフィルムは、工業用途で多用されている。これらフィルムは、例えば、フラットパネルディスプレイの内部に組み込まれる偏光板保護フィルムとして利用されるが、これらのフィルムには、高い耐擦傷性が求められている。 Plastic films produced using polyethylene terephthalate resin (PET), acrylic resin, polycarbonate resin, acetylated cellulose resin and the like are widely used in industrial applications. These films are used as, for example, a polarizing plate protective film incorporated into a flat panel display, and these films are required to have high scratch resistance.
耐擦傷性を高める方法としては、種々の方法が検討されているが、有機溶剤を使用しない等の環境上の優位性の点から、近年、フィルム上に架橋密度の高い多官能アクリレートを主体とした活性エネルギー線硬化型樹脂組成物を塗布し、紫外線（ＵＶ）や電子線（ＥＢ）等の活性エネルギー線で硬化させハードコート層を形成する方法が実施されるようになってきている。 Various methods have been studied as a method for enhancing the scratch resistance, but in recent years, mainly from polyfunctional acrylates having a high crosslinking density on the film from the viewpoint of environmental superiority such as not using an organic solvent. A method of forming a hard coat layer by applying the active energy ray-curable resin composition and curing it with active energy rays such as ultraviolet rays (UV) or electron beams (EB) has been implemented.
このハードコート層に要求される耐擦傷性としては、例えば、偏光板保護フィルムとして８０μｍ厚ＴＡＣフィルムを基材とする場合、該フィルム上で鉛筆硬度４Ｈレベルの高硬度が要求される。 As the scratch resistance required for the hard coat layer, for example, when a TAC film having a thickness of 80 μm is used as a polarizing plate protective film, a high hardness of 4H pencil hardness is required on the film.
しかしながら、前記活性エネルギー線硬化型樹脂組成物は硬化反応の際に体積収縮が生じ、その結果、フィルムがカールする場合がある。フィルムが薄いほどカールが起こり易いが、近年、例えば、フラットパネルディスプレイの薄型化に伴い、偏光板保護フィルムもより薄いもの、例えば、４０μｍ厚のものを用いる動きがあるなど、カールし易い膜厚のフィルムを用いるようになってきている。従って、硬度が高く、且つ、よりカールしにくい硬化塗膜が得られる活性エネルギー線硬化型樹脂組成物が要求されてきている。 However, the active energy ray-curable resin composition undergoes volume shrinkage during the curing reaction, and as a result, the film may curl. The thinner the film, the more likely it is to curl, but in recent years, for example, with the thinning of flat panel displays, the polarizing plate protective film has become thinner, for example, there is a movement to use a film with a thickness of 40 μm. The film is being used. Therefore, there has been a demand for an active energy ray-curable resin composition that provides a cured film that has high hardness and is less likely to curl.
硬度が高く、カールしにくい硬化塗膜が得られる活性エネルギー線硬化型樹脂組成物としては、例えば、ノルボルナンジイソシアネートと、ビス（２−（メタ）アクリロイルオキシエチル）ヒドロキシエチルイソシアヌレートとの付加反応物であるウレタンアクリレートを含有するフィルム保護層用活性エネルギー線硬化型樹脂組成物が開示されている（例えば、特許文献１参照）。特許文献１で開示されたウレタンアクリレートはその構造中に剛直なノルボルナン構造とヌレート構造とを有する為、硬度が高く、カールしにくい硬化塗膜が得られる。しかしながら、特許文献１で開示された活性エネルギー線硬化型樹脂組成物で用いるウレタンアクリレートでも、剛直なノルボルナン構造とヌレート構造との含有量に限界がある為、硬度と耐カール性が十分でない場合がある。 Examples of the active energy ray-curable resin composition that provides a cured film that has high hardness and is difficult to curl include, for example, an addition reaction product of norbornane diisocyanate and bis (2- (meth) acryloyloxyethyl) hydroxyethyl isocyanurate. An active energy ray-curable resin composition for a film protective layer containing urethane acrylate is disclosed (for example, see Patent Document 1). Since the urethane acrylate disclosed in Patent Document 1 has a rigid norbornane structure and a nurate structure in its structure, a cured coating film having high hardness and hardly curling can be obtained. However, even the urethane acrylate used in the active energy ray-curable resin composition disclosed in Patent Document 1 has a limit in the content of the rigid norbornane structure and the nurate structure, and thus the hardness and curl resistance may not be sufficient. is there.
本発明の課題は、硬度が高く、且つ、よりカールしにくい硬化塗膜が得られるコーティング用活性エネルギー線硬化型樹脂組成物を提供することにある。 An object of the present invention is to provide an active energy ray-curable resin composition for coating that can provide a cured film having high hardness and less curling.
本発明者らは、上記の課題を解決するため、鋭意検討した結果、ウレタン（メタ）アクリレートの製造に用いるイソシアネート化合物としてノルボルナンジイソシアネートをヌレート化して得られるイソシアヌレートを用いることにより、特許文献１で開示されたウレタンアクリレートの３倍数のノルボルネン構造を有するウレタン（メタ）アクリレートが得られる事、これにより該ウレタン（メタ）アクリレートを含有する樹脂組成物を用いることにより硬度が高く、カールしにくい硬化塗膜が得られる事、用いるイソシアネート化合物としては、ノルボルネンジイソシアネートのイソシアヌレートに限定されることなくビシクロ環を有するジイソシアネートのイソシアヌレートであれば硬度が高く、カールしにくい硬化塗膜が得られる事等を見出し、本発明を完成するに至った。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have disclosed in Patent Document 1 that isocyanurate obtained by nurating norbornane diisocyanate as an isocyanate compound used in the production of urethane (meth) acrylate. A urethane (meth) acrylate having a norbornene structure three times that of the disclosed urethane acrylate is obtained, and by using the resin composition containing the urethane (meth) acrylate, a cured coating that has high hardness and is difficult to curl. A film is obtained, and the isocyanate compound to be used is not limited to the isocyanurate of norbornene diisocyanate, but a diisocyanate isocyanurate having a bicyclo ring can provide a cured film that has high hardness and is difficult to curl. The heading, which resulted in the completion of the present invention.
即ち、本発明は、ビシクロ環を含有するジイソシアネートをヌレート化して得られるポリイソシアネート（ａ１）と水酸基を含有する（メタ）アクリレート（ａ２）とを反応させて得られるウレタン（メタ）アクリレート（Ａ）を含有することを特徴とするコーティング用活性エネルギー線硬化型樹脂組成物を提供するものである。 That is, the present invention is a urethane (meth) acrylate (A) obtained by reacting a polyisocyanate (a1) obtained by nucleating a diisocyanate containing a bicyclo ring with a (meth) acrylate (a2) containing a hydroxyl group. An active energy ray-curable resin composition for coating, comprising:
また、本発明は、前記コーティング用活性エネルギー線硬化型樹脂組成物を硬化させて得られる硬化層を有することを特徴とするフィルム基材を提供するものである。 The present invention also provides a film substrate comprising a cured layer obtained by curing the active energy ray-curable resin composition for coating.
本発明のコーティング用活性エネルギー線硬化型樹脂組成物は硬度が高く、また、硬化収縮も少ないことからカールしにくい硬化物が得られる。従って、フィルム基材の保護層を形成させるための組成物として特に好適に用いることができる。 Since the active energy ray-curable resin composition for coating of the present invention has high hardness and less curing shrinkage, a cured product that hardly curls can be obtained. Therefore, it can be particularly suitably used as a composition for forming a protective layer of a film substrate.
本発明で用いる重合体ウレタン（メタ）アクリレート（Ａ）の調製に用いるジイソシアネート（ａ１）は、ビシクロ環を含有するジイソシアネートをヌレート化して得られる。ビシクロ環を含有するジイソシアネートとしては、例えば、２，５−または２，６−ジイソシアナートメチルノルボルナン（ノルボルナンジイソシアネート）、２，５−または２，６−ジイソシアナートメチル−２−イソシネートプロピルノルボルナン、ビシクロヘプタントリイソシアネート等が挙げられる。なかでもノルボルナンジイソシアネートが好ましい。 The diisocyanate (a1) used for the preparation of the polymer urethane (meth) acrylate (A) used in the present invention is obtained by nurating a diisocyanate containing a bicyclo ring. Examples of the diisocyanate containing a bicyclo ring include 2,5- or 2,6-diisocyanatomethylnorbornane (norbornane diisocyanate), 2,5- or 2,6-diisocyanate methyl-2-isocyanatepropyl. Examples include norbornane and bicycloheptane triisocyanate. Of these, norbornane diisocyanate is preferable.
ここで、本発明で用いるポリイソシアネート（ａ１）の調製時にはイソシアネート化合物として、ビシクロ環を含有するジイソシアネートのみを用いるのが、表面硬度が高く、低硬化収縮の硬化塗膜が得られることから好ましいが、本発明の効果を損なわない範囲で前記ビシクロ環を含有するジイソシアネート以外のイソシアネート化合物も使用することができる。前記ビシクロ環を含有するジイソシアネート以外のジイソシアネート化合物を使用する場合の使用量はビシクロ環を含有するジイソシアネート１００重量部に対して０．１〜１０重量部が好ましい。 Here, when preparing the polyisocyanate (a1) used in the present invention, it is preferable to use only a diisocyanate containing a bicyclo ring as the isocyanate compound because the cured film with high surface hardness and low curing shrinkage can be obtained. An isocyanate compound other than the diisocyanate containing the bicyclo ring can be used as long as the effects of the present invention are not impaired. When the diisocyanate compound other than the diisocyanate containing the bicyclo ring is used, the amount used is preferably 0.1 to 10 parts by weight with respect to 100 parts by weight of the diisocyanate containing the bicyclo ring.
前記ビシクロ環を含有するジイソシアネート以外のイソシアネート化合物としては、例えば、ビシクロ環を含有するジイソシアネート以外の脂肪族系ポリイソシアネート、芳香族系ポリイソシアネート等が挙げられる。 Examples of the isocyanate compound other than the diisocyanate containing a bicyclo ring include aliphatic polyisocyanates and aromatic polyisocyanates other than the diisocyanate containing a bicyclo ring.
前記ビシクロ環を含有するジイソシアネート以外の脂肪族系ポリイソシアネートとしては、例えば、直鎖状脂肪族系ポリイソシアネート、環式脂肪族系ポリイソシアネート等が挙げられる。 Examples of the aliphatic polyisocyanate other than the diisocyanate containing a bicyclo ring include linear aliphatic polyisocyanates and cyclic aliphatic polyisocyanates.
前記直鎖状脂肪族系ポリイソシアネートとしては、例えば１，６−ヘキサメチレンジイソシアネート、１，４−テトラメチレンジイソシアネート、１，１２−ドデカメチレンジイソシアネート、２，４，４−トリメチルヘキサメチレンジイソシアネート、リジンジイソシアネート等のジイソシアネート； Examples of the linear aliphatic polyisocyanate include 1,6-hexamethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,12-dodecamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and lysine diisocyanate. Diisocyanates such as;
１，３，６−ヘキサメチレントリイソシアネート、１，８−ジイソシアナート−４−イソシアナートメチルオクタン、２−イソシアナートエチル（２，６−ジイソシアナート）ヘキサノエート等のトリイソシアネート等が挙げられる。 Examples include triisocyanates such as 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanate-4-isocyanate methyloctane, 2-isocyanatoethyl (2,6-diisocyanate) hexanoate, and the like.
環式脂肪族系ポリイソシアネートとしては、例えば、１，３−または１，４−ビス（イソシアナートメチルシクロヘキサン）、１，３−または１，４−ジイソシアナートシクロヘキサン、３，５，５−トリメチル（３−イソシアナートメチル）シクロヘキシルイソシアネート、ジシクロヘキシルメタン−４，４'−ジイソシアネート等のジイソシアネー等が挙げられる。 Examples of the cycloaliphatic polyisocyanate include 1,3- or 1,4-bis (isocyanatomethylcyclohexane), 1,3- or 1,4-diisocyanatocyclohexane, 3,5,5-trimethyl. And diisocyanates such as (3-isocyanatomethyl) cyclohexyl isocyanate and dicyclohexylmethane-4,4′-diisocyanate.
前記芳香族系ポリイソシアネートとしては、例えば、トリレンジイソシアネート、ジフェニルメタンジイソシアネート、１，３−キシレンジイソシアネート、１，４−キシレンジイソシアネート、１，３−テトラメチルキシレンジイソシアネート、１，４−テトラメチルキシレンジイソシアネート、１、５―ナフタレンジイソシアネート、トリジンジイソシアネート、１、４―フェニレンジイソシアネート、１、６―フェニレンジイソシアネート等のジイソシアネート； Examples of the aromatic polyisocyanate include tolylene diisocyanate, diphenylmethane diisocyanate, 1,3-xylene diisocyanate, 1,4-xylene diisocyanate, 1,3-tetramethylxylene diisocyanate, 1,4-tetramethylxylene diisocyanate, Diisocyanates such as 1,5-naphthalene diisocyanate, tolidine diisocyanate, 1,4-phenylene diisocyanate, 1,6-phenylene diisocyanate;
トリフェニルメタントリイソシアネート、トリス（イソシアナートフェニル）チオホスフェート等のトリイソシアネート等が挙げられる。 And triisocyanates such as triphenylmethane triisocyanate and tris (isocyanatophenyl) thiophosphate.
さらに上記脂肪族系ジイソシアネート化合物及び／または芳香族ジイソシアネートと多官能ポリオール化合物から合成されるアダクト型ポリイソシアネート化合物、脂肪族系ジイソシアネート化合物及び／または芳香族ジイソシアネート化合物の３量体からなるイソシアヌレート型ポリイソシアネート等もビシクロ環を含有するジイソシアネート以外のイソシアネート化合物として挙げられる。 Further, an adduct type polyisocyanate compound synthesized from the above aliphatic diisocyanate compound and / or an aromatic diisocyanate and a polyfunctional polyol compound, an isocyanurate type polycrystal comprising a trimer of an aliphatic diisocyanate compound and / or an aromatic diisocyanate compound. Isocyanates and the like are also exemplified as isocyanate compounds other than diisocyanate containing a bicyclo ring.
本発明で用いるポリイソシアネート（ａ１）は、例えば、ビシクロ環を含有するジイソシアネート又は、ビシクロ環を含有するジイソシアネートと必要に応じて使用しても良い他のポリイソシアネートとの混合物にイソシアヌレート化触媒を添加してイソシアヌレート化を進行させる事により得られる。 The polyisocyanate (a1) used in the present invention is, for example, a diisocyanate containing a bicyclo ring, or a mixture of a diisocyanate containing a bicyclo ring and another polyisocyanate that may be used if necessary. It can be obtained by adding and allowing isocyanurate to proceed.
イソシアヌレート化触媒としては、通常用いられるイソシアヌレート化触媒、例えば、Ｎ−ヒドロキシプロピル−トリメチルアンモニウム−ｔ−ブチルベンゾエート、Ｎ−ヒドロキシブチル−トリメチルアンモニウム−ネオペンタン酸、Ｎ−ヒドロキシブチル−トリメチルアンモニウム−ピバリン酸、Ｎ−ヒドロキシプロピル−トリブチルアンモニウム−ネオペンタン酸、Ｎ−ヒドロキシプロピル−トリブチルアンモニウム−オクトエート等を用いることが出来る。 Examples of the isocyanuration catalyst include generally used isocyanuration catalysts such as N-hydroxypropyl-trimethylammonium-t-butylbenzoate, N-hydroxybutyl-trimethylammonium-neopentanoic acid, N-hydroxybutyl-trimethylammonium-pivalin. Acid, N-hydroxypropyl-tributylammonium-neopentanic acid, N-hydroxypropyl-tributylammonium-octate, and the like can be used.
イソシアヌレート化触媒の添加量は、ビシクロ環を含有するジイソシアネート又は、ビシクロ環を含有するジイソシアネートと必要に応じて使用しても良い他のポリイソシアネートとの混合物の重量に対して通常０．００１〜０．１重量％、好ましくは０．００２〜０．０５重量％の範囲である。 The addition amount of the isocyanurate-forming catalyst is usually 0.001 to the weight of a diisocyanate containing a bicyclo ring or a mixture of a diisocyanate containing a bicyclo ring and another polyisocyanate that may be used as necessary. The range is 0.1% by weight, preferably 0.002 to 0.05% by weight.
イソシアヌレート化触媒は通常、触媒を溶解する有機溶媒に希釈して使用することができる。この目的に適した溶媒としては、ジメチルアセトアミド、Ｎ−メチルピロリドン、ブチルセロソルブアセテートなどがあり、また少量であればエチルアルコール、ｎ−ブチルアルコール、２−エチルヘキサノール、ブチルセロソルブ、ベンジルアルコ−ル、３−メチル−３−メトキシ−ブタノール（ＭＭＢ）等のアルコール類を用いてもよい。 The isocyanurate-forming catalyst can usually be used after diluted in an organic solvent that dissolves the catalyst. Suitable solvents for this purpose include dimethylacetamide, N-methylpyrrolidone, butyl cellosolve acetate and the like, and in small amounts, ethyl alcohol, n-butyl alcohol, 2-ethylhexanol, butyl cellosolve, benzyl alcohol, 3- Alcohols such as methyl-3-methoxy-butanol (MMB) may be used.
イソシアヌレート化反応は、通常、３０〜１２０℃の温度範囲、好ましくは４０〜８０℃の温度範囲で実施される。３０〜１２０℃の温度範囲で反応させる事により触媒の活性が損なわれずイソシアヌレート反応が良好に進む、得られるポリイソシアヌレートが着色しにくい等の利点がある。 The isocyanuration reaction is usually performed in a temperature range of 30 to 120 ° C, preferably in a temperature range of 40 to 80 ° C. By reacting in the temperature range of 30 to 120 ° C., there are advantages such that the activity of the catalyst is not impaired and the isocyanurate reaction proceeds well, and the resulting polyisocyanurate is hardly colored.
イソシアヌレート化反応は、通常のイソシアヌレート型ポリイソシアネートの生成が、最初に存在したイソシアネート基の１５〜２５重量％、好ましくは８〜１７％の範囲内に入るように設定された転化率で反応を終了させる。転化率を１５〜２５重量％とすることにより、生成したポリイソシアネート（ａ１）の分子量が高くなり過ぎず、分子量分布がブロードとなりにくく、その結果十分な性能を発揮しやすくなる。また、転化率を１５〜２５重量％とすることにより、生成時のポリイソシアネート（ａ１）のゲル化を防ぐことができる。 The isocyanuration reaction is performed at a conversion set so that the formation of the usual isocyanurate type polyisocyanate falls within the range of 15 to 25% by weight, preferably 8 to 17%, of the initially present isocyanate groups. End. By setting the conversion rate to 15 to 25% by weight, the molecular weight of the produced polyisocyanate (a1) does not become too high, and the molecular weight distribution is hardly broadened. As a result, sufficient performance is easily exhibited. Moreover, gelatinization of the polyisocyanate (a1) at the time of production | generation can be prevented by making a conversion rate into 15 to 25 weight%.
反応終了後のイソシアヌレート化触媒は、モノクロロ酢酸、ドデシルベンゼンスルホン酸、モノフルオロ酢酸もしくはリン酸のごとき各種酸類、または塩化ベンゾイルのごとき各種有機酸のハロゲン化物などの失効剤（失活剤）により、容易に失活される。 After completion of the reaction, the isocyanurate conversion catalyst is composed of various acids such as monochloroacetic acid, dodecylbenzenesulfonic acid, monofluoroacetic acid or phosphoric acid, or a deactivator (deactivator) such as halides of various organic acids such as benzoyl chloride. Easily deactivated.
イソシアヌレート化反応後、得られる化合物は、通常ポリイソシアネート（ａ１）と未反応のイソシアネート化合物（ビシクロ環を含有するジイソシアネート等）との混合物となる。この混合物から通常は未反応のイソシアネート化合物を除去しポリイソシアネート（ａ１）を得るが、未反応のイソシアネート化合物が入っていてもその量が本発明の効果を損なわない範囲であれば、前記混合物をポリイソシアネート（ａ１）として使用することができる。未反応のイソシアネート化合物の除去は、例えば、通常の蒸留または抽出等の方法により、容易に行うことができる。 After the isocyanuration reaction, the resulting compound is usually a mixture of polyisocyanate (a1) and an unreacted isocyanate compound (such as a diisocyanate containing a bicyclo ring). Usually, unreacted isocyanate compound is removed from this mixture to obtain polyisocyanate (a1). However, even if unreacted isocyanate compound is contained, the amount of the mixture is within the range that does not impair the effect of the present invention. It can be used as polyisocyanate (a1). Removal of the unreacted isocyanate compound can be easily performed by, for example, a usual method such as distillation or extraction.
本発明で用いる水酸基を含有する（メタ）アクリレート（ａ２）としては、例えば、２−ヒドロキシエチル（メタ）アクリレート、ヒドロキシプロピル（メタ）アクリレート、ヒドロキシブチル（メタ）アクリレート、前記各アクリレートのカプロラクトンまたは酸化アルキレン付加物、グリセリンモノ（メタ）アクリレート、グリセリンジ（メタ）アクリレート、グリシジルメタクリレート−アクリル酸付加物、トリメチロールプロパンモノ（メタ）アクリレート、トリメチロールジ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ジペンタエリスリトールペンタ（メタ）アクリレート、ジトリメチロールプロパントリ（メタ）アクリルレート、トリメチロールプロパン−酸化アルキレン付加物−ジ（メタ）アクリレート等が挙げられる。 Examples of the (meth) acrylate (a2) containing a hydroxyl group used in the present invention include 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, caprolactone or oxidation of each acrylate. Alkylene adduct, glycerin mono (meth) acrylate, glycerin di (meth) acrylate, glycidyl methacrylate-acrylic acid adduct, trimethylolpropane mono (meth) acrylate, trimethylol di (meth) acrylate, pentaerythritol tri (meth) acrylate , Dipentaerythritol penta (meth) acrylate, ditrimethylolpropane tri (meth) acrylate, trimethylolpropane-alkylene oxide adduct-di (meth) acrylate Rate, and the like.
前記水酸基を含有する（メタ）アクリレート（ａ２）の中でも、水酸基を２個以上有する化合物を用いるとウレタン（メタ）アクリレート（Ａ）として１分子当たりの官能基数（エチレン性不飽和二重結合の数）が多いウレタン（メタ）アクリレートが得られ、その結果、高硬度の硬化塗膜が得られる活性エネルギー線硬化型アクリル樹脂組成物となることから好ましく、水酸基を２〜５個有する化合物を用いるのがより好ましい。 Among the (meth) acrylates (a2) containing hydroxyl groups, when a compound having two or more hydroxyl groups is used, the number of functional groups per molecule (number of ethylenically unsaturated double bonds) as urethane (meth) acrylate (A) ) Is obtained, and as a result, an active energy ray-curable acrylic resin composition from which a high-hardness cured coating film is obtained is preferable, and a compound having 2 to 5 hydroxyl groups is used. Is more preferable.
更に、水酸基を２〜５個有する化合物の中でもペンタエリスリトールトリ（メタ）アクリレートまたはジペンタエリスリトールペンタ（メタ）アクリレートが高い架橋密度が達成でき、その結果高硬度を達成できるという効果を有することから好ましい。 Furthermore, among the compounds having 2 to 5 hydroxyl groups, pentaerythritol tri (meth) acrylate or dipentaerythritol penta (meth) acrylate is preferable because it has the effect of achieving a high crosslink density and consequently achieving high hardness. .
ポリイソシアネート（ａ１）と（メタ）アクリレート（ａ２）との反応は、種々の方法を採用することができる。具体的には、例えば、ポリイソシアネート（ａ１）と（メタ）アクリレート（ａ２）とを混合して、５０〜１２０℃、より好ましくは７０〜９０℃に加熱すれば良い。なお、ポリイソシアネート（ａ１）と（メタ）アクリレート（ａ２）の使用量は特に限定されないが、通常、（ａ１）のイソシアネート基：（ａ２）の水酸基＝１．０：１．０〜１．０：２．０である。である。使用量を当該範囲にすることで、組成物の安定性を高めることができる。 Various methods can be employed for the reaction between the polyisocyanate (a1) and the (meth) acrylate (a2). Specifically, for example, polyisocyanate (a1) and (meth) acrylate (a2) may be mixed and heated to 50 to 120 ° C., more preferably 70 to 90 ° C. In addition, although the usage-amount of polyisocyanate (a1) and (meth) acrylate (a2) is not specifically limited, Usually, the isocyanate group of (a1): The hydroxyl group of (a2) = 1.0: 1.0-1.0 : 2.0. It is. The stability of a composition can be improved by making the usage-amount into the said range.
本発明用いるウレタン（メタ）アクリレート（Ａ）の（メタ）アクリロイル基当量としては特に制限されるものではないが、一分子中にシクロ環構造またはビシクロ環構造を有しつつ、アクリロイル基等量が１５０〜６００ｇ／ｅｑであれば、硬度が高く、且つ、硬化収縮の少ない硬化塗膜が得られることから好ましい。 Although it does not restrict | limit especially as a (meth) acryloyl group equivalent of the urethane (meth) acrylate (A) used for this invention, An acryloyl group equivalent is having a cyclo ring structure or a bicyclo ring structure in 1 molecule. If it is 150-600 g / eq, since hardness is high and a cured coating film with little cure shrinkage is obtained, it is preferable.
本発明のコーティング用活性エネルギー線硬化型樹脂組成物はウレタン（メタ）アクリレート（Ａ）を含有する組成物であるが、更に、コロイダルシリカ（Ｂ）を含有させるのが好ましい。本発明で用いるコロイダルシリカ（Ｂ）は、硬化塗膜の硬度を向上させ、耐擦り傷性を著しく改善する。コロイダルシリカ（Ｂ）の平均粒径（一次粒子径）としては、硬度に対する効果と塗膜の透明性の観点から１〜１００ｎｍが好ましく、１０〜５０ｎｍがより好ましい。 The active energy ray-curable resin composition for coating of the present invention is a composition containing urethane (meth) acrylate (A), but preferably further contains colloidal silica (B). The colloidal silica (B) used in the present invention improves the hardness of the cured coating film and remarkably improves the scratch resistance. The average particle diameter (primary particle diameter) of the colloidal silica (B) is preferably 1 to 100 nm, more preferably 10 to 50 nm, from the viewpoint of the effect on hardness and the transparency of the coating film.
また、本発明のコーティング用活性エネルギー線硬化型樹脂組成物中のコロイダルシリカ（Ｂ）の含有率としては、硬度に対する効果と硬化性の観点から該組成分中の塗膜形成成分の重量を基準として１５〜６０重量％が好ましく、２０〜５０重量％がより好ましい The content of colloidal silica (B) in the active energy ray-curable resin composition for coating of the present invention is based on the weight of the coating film-forming component in the composition from the viewpoint of hardness and curability. Is preferably 15 to 60% by weight, more preferably 20 to 50% by weight.
本発明のコーティングコーティング用活性エネルギー線硬化型樹脂組成物には、また、本発明の効果を損なわない範囲で種々の化合物を添加することができる。これらの化合物としては、例えば、前記ウレタン（メタ）アクリレート（Ａ）以外の重合性不飽和二重結合を有する単量体、紫外線吸収剤、酸化防止剤、シリコン系添加剤、フッ素系添加剤、レオロジーコントロール剤、脱泡剤、離型剤、シランカップリング剤、帯電防止剤、防曇剤、着色剤等が挙げられる。 Various compounds can be added to the active energy ray-curable resin composition for coating coating of the present invention as long as the effects of the present invention are not impaired. Examples of these compounds include monomers having a polymerizable unsaturated double bond other than the urethane (meth) acrylate (A), ultraviolet absorbers, antioxidants, silicon-based additives, fluorine-based additives, Examples include rheology control agents, defoaming agents, mold release agents, silane coupling agents, antistatic agents, antifogging agents, and coloring agents.
前記ウレタン（メタ）アクリレート（Ａ）以外の重合性不飽和二重結合を有する単量体としては、例えば、芳香環を有する重合性単量体、環状脂肪族構造を有する重合性単量体、複素環構造を有する重合性単量体、スチレン系化合物、直鎖状脂肪族構造を有する重合性単量体等が挙げられる。 As the monomer having a polymerizable unsaturated double bond other than the urethane (meth) acrylate (A), for example, a polymerizable monomer having an aromatic ring, a polymerizable monomer having a cyclic aliphatic structure, Examples thereof include a polymerizable monomer having a heterocyclic structure, a styrene compound, and a polymerizable monomer having a linear aliphatic structure.
前記芳香環を有する重合性単量体としては、例えば、芳香環を有する（メタ）アクリル酸エステル類等が挙げられる。芳香環を有する（メタ）アクリル酸エステル類としては、例えば、ベンゾイルオキシエチル（メタ）アクリレート、ベンジル（メタ）アクリレート、フェニルエチル（メタ）アクリレート、フェノキシエチル（メタ）アクリレート、フェノキシジエチレングリコール（メタ）アクリレート、２−ヒドロキシ−３−フェノキシプロピル（メタ）アクリレート、２−フェニル−２−（４−アクリロイルオキシフェニル）プロパン、２−フェニル−２−（４−アクリロイルオキシアルコキシフェニル）プロパン、２,４,６−トリクロロフェニル（メタ）アクリレート、２,４,６−トリブロモフェニル（メタ）アクリレート、２,４,６−トリクロロベンジル（メタ）アクリレート、２,４,６−トリブロモベンジル（メタ）アクリレート、２,４,６−トリクロロフェノキシエチル（メタ）アクリレート、２,４,６−トリブロモフェノキシエチル（メタ）アクリレート、ｏ−フェニルフェノール（ポリ）エトキシ（メタ）アクリレート、ｐ−フェニルフェノール（ポリ）エトキシ（メタ）アクリレート； Examples of the polymerizable monomer having an aromatic ring include (meth) acrylic acid esters having an aromatic ring. Examples of (meth) acrylic acid esters having an aromatic ring include benzoyloxyethyl (meth) acrylate, benzyl (meth) acrylate, phenylethyl (meth) acrylate, phenoxyethyl (meth) acrylate, and phenoxydiethylene glycol (meth) acrylate. 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2-phenyl-2- (4-acryloyloxyphenyl) propane, 2-phenyl-2- (4-acryloyloxyalkoxyphenyl) propane, 2,4,6 -Trichlorophenyl (meth) acrylate, 2,4,6-tribromophenyl (meth) acrylate, 2,4,6-trichlorobenzyl (meth) acrylate, 2,4,6-tribromobenzyl (meth) acrylate, 2 , 4,6-tric Borophenoxyethyl (meth) acrylate, 2,4,6-tribromophenoxyethyl (meth) acrylate, o-phenylphenol (poly) ethoxy (meth) acrylate, p-phenylphenol (poly) ethoxy (meth) acrylate;
ビスフェノールＡのアルキレンオキシド付加物構造を含む単量体、具体的には、例えば、下記一般式（１）で表される２官能（メタ）アクリレート A monomer containing an alkylene oxide adduct structure of bisphenol A, specifically, for example, a bifunctional (meth) acrylate represented by the following general formula (1)
ビスフェノールＦのエチレンオキシド付加物、ビスフェノールＦのプロピレンオキシド付加物、ハロゲン化ビスフェノールＦのエチレンオキシド付加物、ハロゲン化ビスフェノールＦのプロピレンオキシド付加物等のビスフェノールＦのアルキレンオキサイド付加物に（メタ）アクリル酸がエステル結合したビスフェノールＦのアルキレンオキサイド付加物構造を有する単量体； Ethylene oxide adduct of bisphenol F, propylene oxide adduct of bisphenol F, ethylene oxide adduct of halogenated bisphenol F, propylene oxide adduct of halogenated bisphenol F, etc. (meth) acrylic acid ester to alkylene oxide adduct of bisphenol F A monomer having a bonded bisphenol F alkylene oxide adduct structure;
ビスフェノールＳのエチレンオキシド付加物、ビスフェノールＳのプロピレンオキシド付加物、ハロゲン化ビスフェノールＳのエチレンオキシド付加物、ハロゲン化ビスフェノールＳのプロピレンオキシド付加物等のビスフェノールＳのアルキレンオキサイド付加物に（メタ）アクリル酸がエステル結合したビスフェノールＳのアルキレンオキサイド付加物構造を有する単量体； Ethylene oxide adduct of bisphenol S, propylene oxide adduct of bisphenol S, ethylene oxide adduct of halogenated bisphenol S, propylene oxide adduct of halogenated bisphenol S, etc. (meth) acrylic acid ester to alkylene oxide adduct of bisphenol S A monomer having an alkylene oxide adduct structure of bound bisphenol S;
２,２′−ジ（ヒドロキシプロポキシフェニル）プロパン及びそれらのハロゲン化物、２,２′−ジ（ヒドロキシエトキシフェニル）プロパン及びそれらのハロゲン化物に（メタ）アクリル酸がエステル結合した化合物； 2,2′-di (hydroxypropoxyphenyl) propane and their halides, 2,2′-di (hydroxyethoxyphenyl) propane and their halides with (meth) acrylic acid ester-bonded;
ビス［４−（メタ）アクリロイルオキシフェニル］−スルフィド、ビス［４−（メタ）アクリロイルオキシエトキシフェニル］−スルフィド、ビス［４−（メタ）アクリロイルオキシペンタエトキシフェニル］−スルフィド、ビス［４−（メタ）アクリロイルオキシエトキシ−３−フェニルフェニル］−スルフィド、ビス［４−（メタ）アクリロイルオキシエトキシ−３,５−ジメチルフェニル］−スルフィド、ビス（４−（メタ）アクリロイルオキシエトキシフェニル）スルフォン； Bis [4- (meth) acryloyloxyphenyl] -sulfide, bis [4- (meth) acryloyloxyethoxyphenyl] -sulfide, bis [4- (meth) acryloyloxypentaethoxyphenyl] -sulfide, bis [4- ( (Meth) acryloyloxyethoxy-3-phenylphenyl] -sulfide, bis [4- (meth) acryloyloxyethoxy-3,5-dimethylphenyl] -sulfide, bis (4- (meth) acryloyloxyethoxyphenyl) sulfone;
ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、一部ハロゲン置換されたビスフェノールＡ型エポキシ樹脂、一部ハロゲン置換されたビスフェノールＦ型エポキシ樹脂、水添ビスフェノールＡ型エポキシ樹脂、及びそれらの混合物からなる群から選ばれる１種以上のエポキシ樹脂と（メタ）アクリル酸との反応で得られるビスフェノール型のエポキシ（メタ）アクリレートやフェノールノボラック型のエポキシ（メタ）アクリレート、クレゾールノボラック型のエポキシ（メタ）アクリレート、ナフタレン骨格のエポキシ（メタ）アクリレートまたはこれらの混合物； Bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, partially halogen-substituted bisphenol A-type epoxy resin, partially halogen-substituted bisphenol F-type epoxy resin, hydrogenated bisphenol A-type epoxy resin, and mixtures thereof Bisphenol type epoxy (meth) acrylate, phenol novolac type epoxy (meth) acrylate, cresol novolac type epoxy (meth) acrylate obtained by reaction of one or more epoxy resins selected from the group with (meth) acrylic acid , Epoxy (meth) acrylate of naphthalene skeleton or a mixture thereof;
ポリオールと環状構造を有する有機ポリイソシアネートと水酸基含有（メタ）アクリレートの反応により得られるウレタン（メタ）アクリレート、環状構造を有するジオールと有機ポリイソシアネートと水酸基含有（メタ）アクリレートの反応により得られるウレタン（メタ）アクリレート、環状構造を有する有機ポリイソシアネートと水酸基含有（メタ）アクリレートの反応により得られるウレタン（メタ）アクリレート等が挙げられる。 Urethane (meth) acrylate obtained by reaction of polyol and organic polyisocyanate having a cyclic structure and hydroxyl group-containing (meth) acrylate, urethane obtained by reaction of diol having cyclic structure, organic polyisocyanate and hydroxyl group-containing (meth) acrylate ( Examples thereof include (meth) acrylate, urethane (meth) acrylate obtained by a reaction of an organic polyisocyanate having a cyclic structure and a hydroxyl group-containing (meth) acrylate.
前記環状脂肪族構造を有する重合性単量体としては、例えば、環状脂肪族を有する（メタ）アクリル酸エステル類等が挙げられる。環状脂肪族を有する（メタ）アクリル酸エステル類としては、例えば、シクロヘキシル（メタ）アクリレート、イソボロニル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート、ジシクロペンテニルオキシエチル（メタ）アクリレート、テトラヒドロフルフリル（メタ）アクリレート、グリシジルシクロカーボネート（メタ）アクリレート、トリシクロデカンジメチロールジ（メタ）アクリレート等が挙げられる。 Examples of the polymerizable monomer having a cycloaliphatic structure include (meth) acrylic acid esters having a cycloaliphatic group. Examples of (meth) acrylic acid esters having a cycloaliphatic group include cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and tetrahydroflurane. Examples include furyl (meth) acrylate, glycidyl cyclocarbonate (meth) acrylate, and tricyclodecane dimethylol di (meth) acrylate.
前記スチレン系化合物としては、例えば、スチレン、α−メチルスチレン、クロロスチレン等が挙げられる。 Examples of the styrene compound include styrene, α-methylstyrene, chlorostyrene, and the like.
前記複素環系化合物としては、例えば、Ｎ−ビニルピロリドン、Ｎ−ビニルカプロラクトン、アクリロイルホルモリン； Examples of the heterocyclic compound include N-vinylpyrrolidone, N-vinylcaprolactone, acryloylformoline;
トリス（２−ヒドロキシエチル）イソシアヌレート、トリス（ヒドロキシプロピル）イソシアヌレート、およびそれらに１〜２０モルのアルキレンオキサイドあるいはεカプロラクトンを開環付加させた水酸基含有化合物などの水酸基を有する化合物に（メタ）アクリル酸がエステル結合したイソシアヌル酸構造を有する化合物等が挙げられる。 To compounds having a hydroxyl group such as tris (2-hydroxyethyl) isocyanurate, tris (hydroxypropyl) isocyanurate, and a hydroxyl group-containing compound obtained by ring-opening addition of 1 to 20 moles of alkylene oxide or ε-caprolactone to (meth) Examples include compounds having an isocyanuric acid structure in which acrylic acid is ester-bonded.
直鎖状脂肪族構造を有する重合性単量体としては、例えば、アルキル基を有する（メタ）アクリル酸エステル類等が挙げられる。アルキル基を有する（メタ）アクリル酸エステル類としては、例えば、（メタ）アクリル酸メチル、（メタ）アクリル酸エチル、（メタ）アクリル酸プロピル、（メタ）アクリル酸ブチル、（メタ）アクリル酸ヘキシル、（メタ）アクリル酸ヘプシル、（メタ）アクリル酸オクチル、（メタ）アクリル酸ノニル、（メタ）アクリル酸デシル、（メタ）アクリル酸ドデシル、（メタ）アクリル酸テトラデシル、（メタ）アクリル酸ヘキサデシル、（メタ）アクリル酸ステアリル、（メタ）アクリル酸オクタデシル、（メタ）アクリル酸ドコシル等の炭素数１〜２２のアルキル基を持つ（メタ）アクリル酸エステル類；（メタ）アクリル酸ヒドロキエチル、（メタ）アクリル酸ヒドロキシプロピル、（メタ）アクリル酸グリセロール、ラクトン変性（メタ）アクリル酸ヒドロキシエチル、（メタ）アクリル酸ポリエチレングリコール、（メタ）アクリル酸ポリプロピレングリコール等のヒドロキシアルキル基を有するアクリル酸エステル類等が挙げられる。 Examples of the polymerizable monomer having a linear aliphatic structure include (meth) acrylic acid esters having an alkyl group. Examples of (meth) acrylic acid esters having an alkyl group include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, and hexyl (meth) acrylate. , Heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, tetradecyl (meth) acrylate, hexadecyl (meth) acrylate, (Meth) acrylic acid esters having an alkyl group having 1 to 22 carbon atoms such as stearyl (meth) acrylate, octadecyl (meth) acrylate, docosyl (meth) acrylate; hydroxyethyl (meth) acrylate, (meta ) Hydroxypropyl acrylate, glycerol (meth) acrylate, lactone modification (Meth) acrylate, hydroxypropyl (meth) polyethylene glycol acrylate, acrylic acid esters having a (meth) hydroxyalkyl group, such as acrylic acid polypropylene glycol.
また、以下の重合性単量体も本発明で用いる重合性不飽和二重結合を有する単量体として例示する事ができる。例えば、（メタ）アクリル酸グリシジル、α−エチル（メタ）アクリル酸グリシジル、α−ｎ−プロピル（メタ）アクリル酸グリシジル、α−ｎ−ブチル（メタ）アクリル酸グリシジル、（メタ）アクリル酸−３,４−エポキシブチル、（メタ）アクリル酸−４,５−エポキシペンチル、（メタ）アクリル酸−６,７−エポキシペンチル、α−エチル（メタ）アクリル酸−６,７−エポキシペンチル、βーメチルグリシジル（メタ）アクリレート、（メタ）アクリル酸−３,４−エポキシシクロヘキシル、ラクトン変性（メタ）アクリル酸−３,４−エポキシシクロヘキシル、ビニルシクロヘキセンオキシド等の重合性不飽和二重結合及びエポキシ基を有する重合性単量体； The following polymerizable monomers can also be exemplified as monomers having a polymerizable unsaturated double bond used in the present invention. For example, glycidyl (meth) acrylate, glycidyl α-ethyl (meth) acrylate, glycidyl α-n-propyl (meth) acrylate, glycidyl α-n-butyl (meth) acrylate, (meth) acrylic acid-3 , 4-epoxybutyl, (meth) acrylic acid-4,5-epoxypentyl, (meth) acrylic acid-6,7-epoxypentyl, α-ethyl (meth) acrylic acid-6,7-epoxypentyl, β- Polymerizable unsaturated double bonds such as methyl glycidyl (meth) acrylate, (meth) acrylic acid-3,4-epoxycyclohexyl, lactone-modified (meth) acrylic acid-3,4-epoxycyclohexyl, vinylcyclohexene oxide and epoxy groups A polymerizable monomer having:
（メタ）アクリル酸；β−カルボキシエチル（メタ）アクリレート、２ーアクリロイルオキシエチルコハク酸、２ーアクリロイルオキシエチルフタル酸、２ーアクリロイルオキシエチルヘキサヒドロフタル酸及びこれらのラクトン変性物等エステル結合を有する不飽和モノカルボン酸；マレイン酸等の重合性不飽和二重結合及びカルボキシル基を有する重合性単量体； (Meth) acrylic acid; β-carboxyethyl (meth) acrylate, 2-acryloyloxyethyl succinic acid, 2-acryloyloxyethyl phthalic acid, 2-acryloyloxyethyl hexahydrophthalic acid and ester bonds such as lactone modified products thereof An unsaturated monocarboxylic acid having a polymerizable monomer having a polymerizable unsaturated double bond and a carboxyl group such as maleic acid;
フマル酸ジメチル、フマル酸ジエチル、フマル酸ジブチル、イタコン酸ジメチル、イタコン酸ジブチル、フマル酸メチルエチル、フマル酸メチルブチル、イタコン酸メチルエチルなどの不飽和ジカルボン酸エステル類； Unsaturated dicarboxylic esters such as dimethyl fumarate, diethyl fumarate, dibutyl fumarate, dimethyl itaconate, dibutyl itaconate, methyl ethyl fumarate, methyl butyl fumarate, methyl ethyl itaconate;
スチレン、α−メチルスチレン、クロロスチレンなどのスチレン誘導体類；ブタジエン、イソプレン、ピペリレン、ジメチルブタジエンなどのジエン系化合物類；塩化ビニル、臭化ビニルなどのハロゲン化ビニルやハロゲン化ビニリデン類；メチルビニルケトン、ブチルビニルケトンなどの不飽和ケトン類；酢酸ビニル、酪酸ビニルなどのビニルエステル類；メチルビニルエーテル、ブチルビニルエーテルなどのビニルエーテル類；アクリロニトリル、メタクリロニトリル、シアン化ビニリデンなどのシアン化ビニル類；アクリルアミドやそのアルキド置換アミド類；Ｎ−フェニルマレイミド、Ｎ−シクロヘキシルマレイミドなどのＮ−置換マレイミド類； Styrene derivatives such as styrene, α-methylstyrene and chlorostyrene; diene compounds such as butadiene, isoprene, piperylene and dimethylbutadiene; vinyl halides and vinylidene halides such as vinyl chloride and vinyl bromide; methyl vinyl ketone Unsaturated vinyls such as butyl vinyl ketone; vinyl esters such as vinyl acetate and vinyl butyrate; vinyl ethers such as methyl vinyl ether and butyl vinyl ether; vinyl cyanides such as acrylonitrile, methacrylonitrile and vinylidene cyanide; acrylamide and Its alkyd substituted amides; N-substituted maleimides such as N-phenylmaleimide, N-cyclohexylmaleimide;
フッ化ビニル、フッ化ビニリデン、トリフルオロエチレン、クロロトリフルオロエチレン、ブロモトリフルオロエチレン、ペンタフルオロプロピレンもしくはヘキサフルオロプロピレンの如きフッ素含有α−オレフィン類；またはトリフルオロメチルトリフルオロビニルエーテル、ペンタフルオロエチルトリフルオロビニルエーテルもしくはヘプタフルオロプロピルトリフルオロビニルエーテルの如き（パー）フルオロアルキル基の炭素数が１から１８なる（パー）フルオロアルキル・パーフルオロビニルエーテル類；２，２，２−トリフルオロエチル（メタ）アクリレート、２，２，３，３−テトラフルオロプロピル（メタ）アクリレート、１Ｈ，１Ｈ，５Ｈ−オクタフルオロペンチル（メタ）アクリレート、１Ｈ，１Ｈ，２Ｈ，２Ｈ−ヘプタデカフルオロデシル（メタ）アクリレートもしくはパーフルオロエチルオキシエチル（メタ）アクリレートの如き（パー）フルオロアルキル基の炭素数が１から１８なる（パー）フルオロアルキル（メタ）アクリレート類等のフッ素含有エチレン性不飽和単量体類； Fluorine-containing α-olefins such as vinyl fluoride, vinylidene fluoride, trifluoroethylene, chlorotrifluoroethylene, bromotrifluoroethylene, pentafluoropropylene or hexafluoropropylene; or trifluoromethyl trifluorovinyl ether, pentafluoroethyltri (Per) fluoroalkyl perfluorovinyl ethers having a (per) fluoroalkyl group such as fluorovinyl ether or heptafluoropropyl trifluorovinyl ether having 1 to 18 carbon atoms; 2,2,2-trifluoroethyl (meth) acrylate; 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (meth) acrylate, 1H, 1H, 2H, 2H-he Fluorine-containing ethylenic compounds such as (per) fluoroalkyl (meth) acrylates having a (per) fluoroalkyl group of 1 to 18 carbon atoms such as tadecafluorodecyl (meth) acrylate or perfluoroethyloxyethyl (meth) acrylate Unsaturated monomers;
γ−メタクリロキシプロピルトリメトキシシラン等のシリル基含有（メタ）アクリレート類；Ｎ，Ｎ−ジメチルアミノエチル（メタ）アクリレート、Ｎ，Ｎ−ジエチルアミノエチル（メタ）アクリレートもしくはＮ，Ｎ−ジエチルアミノプロピル（メタ）アクリレート等のＮ，Ｎ−ジアルキルアミノアルキル（メタ）アクリレート； Silyl group-containing (meth) acrylates such as γ-methacryloxypropyltrimethoxysilane; N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate or N, N-diethylaminopropyl (meth) ) N, N-dialkylaminoalkyl (meth) acrylates such as acrylates;
（メタ）アクリル酸フォスフォエチル、Ｎ，Ｎ−ジメチルアミノエチル（メタ）アクリレート、Ｎ，Ｎ−ジエチルアミノエチル（メタ）アクリレートもしくはＮ，Ｎ−ジエチルアミノプロピル（メタ）アクリレート、ジ[（メタ）アクリロイルオキシエチル］フォスフェート、トリ［（メタ）アクリロイルオキシエチル］フォスフェート、エチレングリコールジ（メタ）アクリレート、プロピレングリコールジ（メタ）アクリレート；ジエチレングリコールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、テトラエチレングリコールジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、 Phosphoethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate or N, N-diethylaminopropyl (meth) acrylate, di [(meth) acryloyloxy Ethyl] phosphate, tri [(meth) acryloyloxyethyl] phosphate, ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate; diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetra Ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate,
ジプロピレングリコールジ（メタ）アクリレート、トリプロピレングリコールジ（メタ）アクリレート、テトラプロピレングリコールジ（メタ）アクリレート、ポリプロピレングリコールジ（メタ）アクリレート、１,３−ブチレングリコールジ（メタ）アクリレート、１,４−ブチレングリコールジ（メタ）アクリレート、１,６−ヘキサメチレングリコールジ（メタ）アクリレート、１，９−ノナンジオールジ（メタ）アクリレート、ネオペンチルグリコールジ（メタ）アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールジ（メタ）アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールにカプロラクトン付加した化合物のジ（メタ）アクリレート、ネオペンチルグリコールアジペートジ（メタ）アクリレート、 Dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, tetrapropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, 1,4 -Butylene glycol di (meth) acrylate, 1,6-hexamethylene glycol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, hydroxypivalate neopentyl glycol di (Meth) acrylate, di (meth) acrylate of a compound obtained by adding caprolactone to neopentyl glycol hydroxypivalate, neopentyl glycol adipate di (meth) acrylate,
トリメチロールプロパン、ジトリメチロールプロパン、ペンタエリスリトール、ジペンタエリスリトール、テトラメチロールメタン、およびそれらに１〜２０モルのアルキレンオキサイドを付加させた水酸基含有化合物などの水酸基を３つ以上有する化合物に（メタ）アクリル酸が３分子以上エステル結合した化合物等が挙げられる。 (Meth) acrylic to compounds having 3 or more hydroxyl groups such as trimethylolpropane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, tetramethylolmethane, and a hydroxyl group-containing compound in which 1 to 20 mol of alkylene oxide is added thereto. Examples include compounds in which three or more molecules of acid are ester-bonded.
前記ウレタン（メタ）アクリレート（Ａ）以外の重合性不飽和二重結合を有する単量体を使用する場合、その使用量としては、塗膜形成成分の重量を基準として０〜５０重量％が好ましい。 When using the monomer which has polymerizable unsaturated double bonds other than the said urethane (meth) acrylate (A), as the usage-amount, 0 to 50 weight% is preferable on the basis of the weight of a coating-film formation component. .
前記紫外線吸収剤としては、例えば、２−［４−｛（２−ヒドロキシ−３−ドデシルオキシプロピル）オキシ｝−２−ヒドロキシフェニル］−４，６−ビス（２，４−ジメチルフェニル）−１，３，５−トリアジン、２−［４−｛（２−ヒドロキシ−３−トリデシルオキシプロピル）オキシ｝−２−ヒドロキシフェニル］−４，６−ビス（２，４−ジメチルフェニル）−１，３，５−トリアジン等のトリアジン誘導体、２−（２′−キサンテンカルボキシ−５′−メチルフェニル）ベンゾトリアゾール、２−（２′−ｏ−ニトロベンジロキシ−５′−メチルフェニル）ベンゾトリアゾール、２−キサンテンカルボキシ−４−ドデシロキシベンゾフェノン、２−ｏ−ニトロベンジロキシ−４−ドデシロキシベンゾフェノン等が挙げられる。 Examples of the ultraviolet absorber include 2- [4-{(2-hydroxy-3-dodecyloxypropyl) oxy} -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1 , 3,5-triazine, 2- [4-{(2-hydroxy-3-tridecyloxypropyl) oxy} -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1, Triazine derivatives such as 3,5-triazine, 2- (2′-xanthenecarboxy-5′-methylphenyl) benzotriazole, 2- (2′-o-nitrobenzyloxy-5′-methylphenyl) benzotriazole, 2 -Xanthenecarboxy-4-dodecyloxybenzophenone, 2-o-nitrobenzyloxy-4-dodecyloxybenzophenone and the like.
前記酸化防止剤としては、例えば、ヒンダードフェノール系酸化防止剤、ヒンダードアミン系酸化防止剤、有機硫黄系酸化防止剤、リン酸エステル系酸化防止剤等が挙げられる。 Examples of the antioxidant include hindered phenol-based antioxidants, hindered amine-based antioxidants, organic sulfur-based antioxidants, and phosphate ester-based antioxidants.
前記シリコン系添加剤としては、例えば、ジメチルポリシロキサン、メチルフェニルポリシロキサン、環状ジメチルポリシロキサン、メチルハイドロゲンポリシロキサン、ポリエーテル変性ジメチルポリシロキサン共重合体、ポリエステル変性ジメチルポリシロキサン共重合体、フッ素変性ジメチルポリシロキサン共重合体、アミノ変性ジメチルポリシロキサン共重合体など如きアルキル基やフェニル基を有するポリオルガノシロキサン類が挙げられる。 Examples of the silicon-based additive include dimethylpolysiloxane, methylphenylpolysiloxane, cyclic dimethylpolysiloxane, methylhydrogenpolysiloxane, polyether-modified dimethylpolysiloxane copolymer, polyester-modified dimethylpolysiloxane copolymer, and fluorine-modified. Examples thereof include polyorganosiloxanes having an alkyl group or a phenyl group, such as a dimethylpolysiloxane copolymer and an amino-modified dimethylpolysiloxane copolymer.
上記した如き種々の添加剤の使用量としては、その効果を十分発揮し、また紫外線硬化を阻害しない範囲であることから、該注型重合用活性エネルギー線硬化型樹脂組成物１００重量部に対し、それぞれ０．０１〜１０重量部の範囲であることが好ましい。 The amount of the various additives as described above is sufficient to exert its effect and does not hinder ultraviolet curing, so that the active energy ray-curable resin composition for casting polymerization is 100 parts by weight. , Each preferably in the range of 0.01 to 10 parts by weight.
本発明の注型重合用活性エネルギー線硬化型樹脂組成物には必要に応じて溶剤を含有させても良いが、溶剤の含有率は少ないほうが作業環境を汚染しにくい注型重合用活性エネルギー線硬化型樹脂組成物が得られることから好ましい。具体的には、本発明の注型重合用活性エネルギー線硬化型樹脂組成物中の溶剤含有率は１重量％以下が好ましい。 The active energy ray-curable resin composition for cast polymerization of the present invention may contain a solvent as necessary, but the active energy beam for cast polymerization is less likely to contaminate the working environment if the solvent content is lower. It is preferable because a curable resin composition is obtained. Specifically, the solvent content in the active energy ray-curable resin composition for cast polymerization of the present invention is preferably 1% by weight or less.
本発明のコーティング用活性エネルギー線硬化型樹脂組成物に加えることができる光重合開始剤（Ｃ）としては、例えば、ベンゾフェノン、３，３′−ジメチル−４−メトキシベンゾフェノン、４，４′−ビスジメチルアミノベンゾフェノン、４，４′−ビスジエチルアミノベンゾフェノン、４，４′−ジクロロベンゾフェノン、ミヒラーズケトン、３，３′，４，４′-テトラ（ｔ-ブチルパーオキシカルボニル）ベンゾフェノンなどのベンゾフェノン類； Examples of the photopolymerization initiator (C) that can be added to the active energy ray-curable resin composition for coating of the present invention include benzophenone, 3,3′-dimethyl-4-methoxybenzophenone, and 4,4′-bis. Benzophenones such as dimethylaminobenzophenone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, Michler's ketone, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone;
キサントン、チオキサントン、２−メチルチオキサントン、２−クロロチオキサントン、２，４−ジエチルチオキサントンなどのキサントン、チオキサントン類；ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテルなどのアシロインエーテル類； Xanthones such as xanthone, thioxanthone, 2-methylthioxanthone, 2-chlorothioxanthone, and 2,4-diethylthioxanthone; thioxanthones; acyloin ethers such as benzoin, benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether;
ベンジル、ジアセチルなどのα-ジケトン類；テトラメチルチウラムジスルフィド、ｐ−トリルジスルフィドなどのスルフィド類；４−ジメチルアミノ安息香酸、４−ジメチルアミノ安息香酸エチルなどの安息香酸類； Α-diketones such as benzyl and diacetyl; sulfides such as tetramethylthiuram disulfide and p-tolyl disulfide; benzoic acids such as 4-dimethylaminobenzoic acid and ethyl 4-dimethylaminobenzoate;
３，３′-カルボニル-ビス（７-ジエチルアミノ）クマリン、１−ヒドロキシシクロへキシルフェニルケトン、２，２′−ジメトキシ−１，２−ジフェニルエタン−１−オン、２−メチル−１−〔４−（メチルチオ）フェニル〕−２−モルフオリノプロパン−１−オン、２−ベンジル−２−ジメチルアミノ−１−（４−モルフォリノフェニル）−ブタン−１−オン、２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン、２，４，６−トリメチルベンゾイルジフェニルホスフィンオキシド、ビス（２，４，６−トリメチルベンゾイル）フェニルホスフィンオキシド、１−〔４−（２−ヒドロキシエトキシ）フェニル〕−２−ヒドロキシ−２−メチル−１−プロパン−１−オン、１−（４−イソプロピルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、１−（４−ドデシルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、４−ベンゾイル−４′−メチルジメチルスルフィド、２，２′−ジエトキシアセトフェノン、ベンジルジメチルケタ−ル、ベンジル−β−メトキシエチルアセタール、ｏ−ベンゾイル安息香酸メチル、ビス（４−ジメチルアミノフェニル）ケトン、ｐ−ジメチルアミノアセトフェノン、α，α−ジクロロ−４−フェノキシアセトフェノン、ペンチル−４−ジメチルアミノベンゾエート、２−（ｏ−クロロフェニル）−４，５−ジフェニルイミダゾリルニ量体、２，４−ビス−トリクロロメチル−６−［ジ−（エトキシカルボニルメチル）アミノ］フェニル−Ｓ−トリアジン、２，４−ビス−トリクロロメチル−６−（４−エトキシ）フェニル−S−トリアジン、２，４−ビス−トリクロロメチル−６−（３−ブロモ−４−エトキシ）フェニル−Ｓ−トリアジンアントラキノン、２−ｔ−ブチルアントラキノン、２−アミルアントラキノン、β−クロルアントラキノン等が挙げられる。 3,3′-carbonyl-bis (7-diethylamino) coumarin, 1-hydroxycyclohexyl phenyl ketone, 2,2′-dimethoxy-1,2-diphenylethane-1-one, 2-methyl-1- [4 -(Methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-hydroxy-2-methyl -1-phenylpropan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 1- [4- (2-hydroxyethoxy) phenyl] 2-hydroxy-2-methyl-1-propan-1-one, 1- (4-isopropylphenyl) -2-hydroxy- -Methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy-2-methylpropan-1-one, 4-benzoyl-4'-methyldimethylsulfide, 2,2'-diethoxyacetophenone, Benzyldimethylketal, benzyl-β-methoxyethyl acetal, methyl o-benzoylbenzoate, bis (4-dimethylaminophenyl) ketone, p-dimethylaminoacetophenone, α, α-dichloro-4-phenoxyacetophenone, pentyl- 4-dimethylaminobenzoate, 2- (o-chlorophenyl) -4,5-diphenylimidazolyl dimer, 2,4-bis-trichloromethyl-6- [di- (ethoxycarbonylmethyl) amino] phenyl-S-triazine 2,4-bis-trichloromethyl-6- (4-eth C) Phenyl-S-triazine, 2,4-bis-trichloromethyl-6- (3-bromo-4-ethoxy) phenyl-S-triazine anthraquinone, 2-t-butylanthraquinone, 2-amylanthraquinone, β-chloro Anthraquinone etc. are mentioned.
前記光重合開始剤は、単独あるいは２種以上を組み合わせて用いることもできる。その使用量は特に制限はないが、感度を良好に保ち、結晶の析出、塗膜物性の劣化等防止するため、本発明のコーティング用活性エネルギー線硬化型樹脂組成物１００重量部に対して０．０５〜２０重量部用いることが好ましく、なかでも０．１〜１０重量部が特に好ましい。 The photopolymerization initiators can be used alone or in combination of two or more. The amount used is not particularly limited, but is 0 with respect to 100 parts by weight of the active energy ray-curable resin composition for coating of the present invention in order to maintain good sensitivity and prevent precipitation of crystals and deterioration of physical properties of the coating film. It is preferable to use 0.05 to 20 parts by weight, and 0.1 to 10 parts by weight is particularly preferable.
前記光重合開始剤としては、１−ヒドロキシシクロヘキシルフェニルケトン、２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン、１−〔４−（２−ヒドロキシエトキシ）フェニル〕−２−ヒドロキシ−２−メチル−１−プロパン−１−オン、チオキサントン及びチオキサントン誘導体、２，２′−ジメトキシ−１，２−ジフェニルエタン−１−オン、２，４，６−トリメチルベンゾイルジフェニルホスフィンオキシド、ビス（２，４，６−トリメチルベンゾイル）フェニルホスフィンオキシド、２−メチル−１−［４−（メチルチオ）フェニル］−２−モルホリノ−１−プロパノン、２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）−ブタン−１−オンの群から選ばれる１種または２種類以上の混合系が、硬化性が高いコーティング用活性エネルギー線硬化型樹脂組成物が得られるため特に好ましい。 Examples of the photopolymerization initiator include 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy- 2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2′-dimethoxy-1,2-diphenylethane-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2 , 4,6-trimethylbenzoyl) phenylphosphine oxide, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-propanone, 2-benzyl-2-dimethylamino-1- (4-morpholino One or more mixed systems selected from the group of phenyl) -butan-1-one High curable coating for the active energy ray curable resin composition is particularly preferred because the resulting.
前記光重合開始剤の市販品としては、例えば、Ｉｒｇａｃｕｒｅ−１８４、同１４９、同２６１、同３６９、同５００、同６５１、同７５４、同７８４、同８１９、同９０７、同１１１６、同１６６４、同１７００、同１８００、同１８５０、同２９５９、同４０４３、Ｄａｒｏｃｕｒ−１１７３（チバスペシャルティーケミカルズ社製）、ルシリンＴＰＯ（ＢＡＳＦF社製）、ＫＡＹＡＣＵＲＥ−ＤＥＴＸ、同ＭＢＰ、同ＤＭＢＩ、同ＥＰＡ、同ＯＡ〔日本化薬(株)製〕、ＶＩＣＵＲＥ−１０、同５５（ＳＴＡＵＦＦＥＲ Ｃｏ．ＬＴＤ製）、ＴＲＩＧＯＮＡＬＰ１（ＡＫＺＯ Ｃｏ．ＬＴＤ製）、ＳＡＮＤＯＲＹ １０００（ＳＡＮＤＯＺ Ｃｏ．ＬＴＤ製）、ＤＥＡＰ（ＡＰＪＯＨＮ Ｃｏ．ＬＴＤ製）、ＱＵＡＮＴＡＣＵＲＥ−ＰＤＯ、同ＩＴＸ、同ＥＰＤ（ＷＡＲＤ ＢＬＥＫＩＮＳＯＰ Ｃｏ．ＬＴＤ製）等が挙げられる。 Examples of commercially available photopolymerization initiators include Irgacure-184, 149, 261, 369, 500, 651, 754, 784, 819, 907, 1116, 1664, 1700, 1800, 1850, 2959, 4043, Darocur-1173 (manufactured by Ciba Specialty Chemicals), Lucirin TPO (manufactured by BASF), KAYACURE-DETX, MBP, DMBI, EPA, OA [Nippon Kayaku Co., Ltd.], VICURE-10, 55 (manufactured by STAUFER Co. LTD), TRIGONALP1 (manufactured by AKZO Co. LTD), SANDORY 1000 (manufactured by SANDOZ Co. LTD), DEAP (manufactured by APJOHN Co. LTD) ), QUANTACURE-PDO, the same ITX, EPD (manufactured by WARD BLEKINSOP Co. LTD), and the like.
さらに、本発明のコーティング用活性エネルギー線硬化型樹脂組成物では、前記光重合開始剤に種々の光増感剤を併用することができる。光増感剤としては、例えば、アミン類、尿素類、含硫黄化合物、含燐化合物、含塩素化合物またはニトリル類もしくはその他の含窒素化合物等が挙げられる。 Furthermore, in the active energy ray-curable resin composition for coating of the present invention, various photosensitizers can be used in combination with the photopolymerization initiator. Examples of the photosensitizer include amines, ureas, sulfur-containing compounds, phosphorus-containing compounds, chlorine-containing compounds, nitriles, and other nitrogen-containing compounds.
本発明のコーティング用活性エネルギー線硬化型樹脂組成物を用いた物品の製造では、紫外線等の活性エネルギー線は、支持体となる透明基材面を通して照射される場合が多い。そのため、光重合開始剤は、長波長領域に吸光能力を有する開始剤が好ましく、例えば、紫外線が３６０〜４５０ｎｍの範囲において光開始能力を発揮する光重合開始剤が好ましい。 In the manufacture of an article using the active energy ray-curable resin composition for coating of the present invention, active energy rays such as ultraviolet rays are often irradiated through the transparent substrate surface serving as a support. Therefore, the photopolymerization initiator is preferably an initiator having a light-absorbing ability in the long wavelength region, and for example, a photopolymerization initiator that exhibits the photoinitiating ability in the range of 360 to 450 nm is preferable.
更に本発明のコーティング用活性エネルギー線硬化型樹脂組成物は、粘度や基板への接着性改良等を目的として、他の樹脂を併用することができる。 Furthermore, the active energy ray-curable resin composition for coating of the present invention can be used in combination with other resins for the purpose of improving viscosity and adhesion to a substrate.
前記他の樹脂としては、例えば、メチルメタクリレート樹脂、メチルメタクリレート系共重合物等のアクリル樹脂；ポリスチレン、メチルメタクリレート−スチレン系共重合物；ポリエステル樹脂；ポリウレタン樹脂；ポリブタジエンやブタジエン−アクリロニトリル系共重合物などのポリブタジエン樹脂；ビスフェノール型エポキシ樹脂、フェノキシ樹脂やノボラック型エポキシ樹脂などのエポキシ樹脂等が挙げられる。 Examples of the other resins include acrylic resins such as methyl methacrylate resin and methyl methacrylate copolymer; polystyrene, methyl methacrylate-styrene copolymer; polyester resin; polyurethane resin; polybutadiene and butadiene-acrylonitrile copolymer. Polybutadiene resins such as bisphenol type epoxy resins, epoxy resins such as phenoxy resins and novolac type epoxy resins, and the like.
本発明のフィルム基材は、本発明のコーティング用活性エネルギー線硬化型樹脂組成物を硬化させて得られる硬化層を有することを特徴とする。具体的には、各種フィルム基材に公知の方法でコーティング用活性エネルギー線硬化型樹脂組成物を塗布、乾燥後、活性エネルギー線を照射することにより硬化させて得られるものである。 The film base material of the present invention has a cured layer obtained by curing the active energy ray-curable resin composition for coating of the present invention. Specifically, the active energy ray-curable resin composition for coating is applied to various film substrates by a known method, dried, and then cured by irradiation with active energy rays.
コーティング用活性エネルギー線硬化型樹脂組成物の塗布量としては、例えば、各種フィルム基材上に、乾燥後の重量が０．１〜３０ｇ／ｍ２、好ましくは１〜２０ｇ／ｍ２になるように塗布するのが好ましい。 The coating amount of the active energy ray-curable resin composition for coating is, for example, such that the weight after drying is 0.1 to 30 g / m 2 , preferably 1 to 20 g / m 2 on various film substrates. It is preferable to apply to.
本発明のコーティング用活性エネルギー線硬化型樹脂組成物を塗布するフィルム基材としては、各種公知の基材にもちいることができる。具体的には、例えば、プラスチック（ポリカーボネート、ポリメチルメタクリレート、ポリスチレン、ポリエステル、ポリオレフィン、エポキシ樹脂、メラミン樹脂、トリアセチルセルロース樹脂、ＡＢＳ樹脂、ＡＳ樹脂、ノルボルネン系樹脂等）等が挙げられる。 As a film substrate on which the active energy ray-curable resin composition for coating of the present invention is applied, various known substrates can be used. Specifically, for example, plastic (polycarbonate, polymethyl methacrylate, polystyrene, polyester, polyolefin, epoxy resin, melamine resin, triacetyl cellulose resin, ABS resin, AS resin, norbornene resin, etc.) and the like can be mentioned.
本発明のコーティング用活性エネルギー線硬化型樹脂組成物の塗布方法としては、特に限定されず公知の方法を採用することができ、例えばバーコーター塗工、メイヤーバー塗工、エアナイフ塗工、グラビア塗工、リバースグラビア塗工、オフセット印刷、フレキソ印刷、スクリーン印刷法等が挙げられる。 The application method of the active energy ray-curable resin composition for coating of the present invention is not particularly limited, and a known method can be adopted, for example, bar coater coating, Mayer bar coating, air knife coating, gravure coating. And the like, reverse gravure coating, offset printing, flexographic printing, screen printing method and the like.
照射する活性エネルギー線としては、例えば、紫外線や電子線が挙げられる。紫外線により硬化させる場合、光源としてキセノンランプ、高圧水銀灯、メタルハライドランプを有する紫外線照射装置が使用され、必要に応じて光量、光源の配置などが調整されるが、高圧水銀灯を使用する場合、通常８０〜１６０W／ｃｍの光量を有したランプ１灯に対して搬送速度５〜５０ｍ/分で硬化させるのが好ましい。一方、電子線により硬化させる場合、通常１０〜３００ｋＶの加速電圧を有する電子線加速装置にて、搬送速度５〜５０ｍ/分で硬化させるのが好ましい。 Examples of the active energy rays to be irradiated include ultraviolet rays and electron beams. In the case of curing with ultraviolet rays, an ultraviolet irradiation device having a xenon lamp, a high-pressure mercury lamp, and a metal halide lamp is used as a light source, and the amount of light and the arrangement of the light source are adjusted as necessary. It is preferable to cure at a conveyance speed of 5 to 50 m / min with respect to one lamp having a light quantity of ˜160 W / cm. On the other hand, in the case of curing with an electron beam, it is preferably cured with an electron beam accelerator having an accelerating voltage of usually 10 to 300 kV at a conveyance speed of 5 to 50 m / min.
以下に実施例及び比較例を挙げて、本発明をより具体的に説明する。例中の部及び％は、特に記載のない限り、すべて重量基準である。 Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples. All parts and percentages in the examples are by weight unless otherwise specified.
実施例１
攪拌装置、冷却管、窒素導入管を備えた反応装置に、酢酸ブチルを１７．５重量部、ノルボルネンジイソシアネート（三井化学ポリウレタン株式会社製「コスモネートＮＢＤＩ」）７０重量部を仕込み、攪拌しながら系内温度が６０℃になるまで昇温した。これに４級アンモニウム塩系触媒であるバーノックＢＤＰ−２５（ＤＩＣ株式会社製）を、発熱に注意しながら８回に分割して合計０．２１重量部加え、反応時間１０時間で、ビシクロ環を含有するジイソシアネートをヌレート化して得られるポリイソシアネート中間体を得た。得られた中間体の不揮発分は７９．１％、ＮＣＯ％＝１４．４であった。
この中間体を攪拌装置、冷却管、空気導入管を備えた反応装置に１４．６重量部仕込み、メトキノン０．０２重量部、ジブチル錫アセテート（日東化成株式会社製「ネオスタンＵ−２００」０．０２重量部、を加えて８０℃まで昇温した。これにペンタエリスリトールトリアクリレート（東亞合成株式会社製「アロニックスＭ−３０５」）２６重量部滴下し、滴下終了後６時間ホールドしてビシクロ環を含有するジイソシアネートをヌレート化して、不揮発分８０．９％のポリイソシアネートと水酸基を含有する（メタ）アクリレートとを反応させて得られるウレタン（メタ）アクリレートを得た。
得られたビシクロ環を含有するジイソシアネートをヌレート化して得られるポリイソシアネートと水酸基を含有する（メタ）アクリレート（Ａ１）１２４重量部（固形分換算１００重量部）、１−ヒドロキシ−シクロヘキシル−フェニル−ケトン（チバスペシャルティケミカルズ社製「Ｉｒｇａｃｕｒｅ１８４」）４重量部、酢酸ブチル８０重量部を攪拌混合してハードコート用活性エネルギー線硬化型組成物を調整した。得られた組成物を、トリアセチルセルロースフィルム（８０μｍ厚）に膜厚１０μｍになるように塗布し、８０℃で１分乾燥させ、窒素雰囲気下で高圧水銀灯を用いて２５０ｍＪ／ｃｍ２照射して硬化させた。得られた塗膜の鉛筆硬度は３Ｈ、５ｃｍ角のフィルムの４頂点の浮き平均で表されるカール値は４ｍｍであった。尚、カール値は小さい程フィルムのカールが小さいことを表す。
Example 1
17.5 parts by weight of butyl acetate and 70 parts by weight of norbornene diisocyanate (“Cosmonate NBDI” manufactured by Mitsui Chemicals Polyurethane Co., Ltd.) are charged into a reactor equipped with a stirrer, a cooling tube, and a nitrogen introduction tube, and the system is stirred. The temperature was raised until the internal temperature reached 60 ° C. To this, Vernock BDP-25 (manufactured by DIC Corporation), which is a quaternary ammonium salt catalyst, was divided into 8 portions while paying attention to heat generation, and a total of 0.21 parts by weight was added. A polyisocyanate intermediate obtained by nurating the contained diisocyanate was obtained. The non-volatile content of the obtained intermediate was 79.1% and NCO% = 14.4.
14.6 parts by weight of this intermediate was charged into a reactor equipped with a stirrer, a cooling pipe, and an air introduction pipe, 0.02 part by weight of methoquinone, dibutyltin acetate (“Neostan U-200” manufactured by Nitto Kasei Co., Ltd.). 02 parts by weight was added, and the temperature was raised to 80 ° C. 26 parts by weight of pentaerythritol triacrylate (“Aronix M-305” manufactured by Toagosei Co., Ltd.) was added dropwise thereto, and held for 6 hours after completion of the addition to form a bicyclo ring. The diisocyanate contained was nurated to obtain a urethane (meth) acrylate obtained by reacting a polyisocyanate having a nonvolatile content of 80.9% with a (meth) acrylate containing a hydroxyl group.
124 parts by weight (100 parts by weight in terms of solid content) of 1-hydroxy-cyclohexyl-phenyl-ketone containing (meth) acrylate (A1) containing a polyisocyanate and a hydroxyl group obtained by nucleating the resulting diisocyanate containing a bicyclo ring ("Irgacure 184" manufactured by Ciba Specialty Chemicals Co., Ltd.) 4 parts by weight and 80 parts by weight of butyl acetate were stirred and mixed to prepare an active energy ray-curable composition for hard coat. The obtained composition was applied to a triacetyl cellulose film (80 μm thickness) so as to have a film thickness of 10 μm, dried at 80 ° C. for 1 minute, and irradiated with 250 mJ / cm 2 using a high-pressure mercury lamp in a nitrogen atmosphere. Cured. The resulting coating film had a pencil hardness of 3 mm, and a curl value represented by a floating average of 4 apexes of a 5 cm square film was 4 mm. The smaller the curl value, the smaller the curl of the film.
比較例１
攪拌機、ガス導入管、冷却管、及び温度計を備えたフラスコに、酢酸ブチル２５２部、ノルボルナンジイソシアネート２０６部、メトキシハイドロキノン０．５部、ジブチル錫ジアセテート０．５部を仕込み、空気を吹き込みながら、７０℃に昇温した後、ビス（２−アクリロイルオキシエチル）ヒドロキシエチルイソシアヌレート／トリス（２−アクリロイルオキシエチル）イソシアヌレート（ＴＡＩＣ）混合物（質量比５６／４４の混合物）１３１８部を１時間かけて滴下した。滴下終了後、７０℃で３時間反応させ、さらにイソシアネート基を示す２２５０ｃｍ−１の赤外線吸収スペクトルが消失するまで反応を行い、ウレタンアクリレート／ＴＡＩＣ混合物（質量比６２／３８の混合物、不揮発分８０％の酢酸ブチル溶液）を得た。
Comparative Example 1
To a flask equipped with a stirrer, a gas introduction tube, a cooling tube, and a thermometer, 252 parts of butyl acetate, 206 parts of norbornane diisocyanate, 0.5 part of methoxyhydroquinone and 0.5 part of dibutyltin diacetate were charged, and air was blown into the flask. , After heating to 70 ° C., 1318 parts of bis (2-acryloyloxyethyl) hydroxyethyl isocyanurate / tris (2-acryloyloxyethyl) isocyanurate (TAIC) mixture (mixture of mass ratio 56/44) for 1 hour It was dripped over. After completion of the dropwise addition, the mixture was reacted at 70 ° C. for 3 hours, and further reacted until the infrared absorption spectrum of 2250 cm −1 indicating an isocyanate group disappeared, and a urethane acrylate / TAIC mixture (mixture with a mass ratio of 62/38, non-volatile content 80% Of butyl acetate).
このウレタンアクリレート／ＴＡＩＣ混合物３７．５部、ジペンタエリスリトールヘキサアクリレート／ジペンタエリスリトールペンタアクリレート混合物（質量比７０／３０の混合物）７０部、Ｉｒｇａｃｕｒｅ１８４ ２部、ビス（２，４，６−トリメチルベンゾイル）−フェニルホスフィンオキサイド１部、酢酸エチル３３部、及び酢酸ブチル５９．５部を混合し、４０℃に加熱後混合して均一にし、活性エネルギー線硬化型樹脂組成物を得た。実施例１と同様にして硬化塗膜を得た。得られた塗膜の鉛筆硬度は３Ｈ、５ｃｍ角のフィルムの４頂点の浮き平均で表されるカール値は＞１０ｍｍであった。 37.5 parts of this urethane acrylate / TAIC mixture, 70 parts of dipentaerythritol hexaacrylate / dipentaerythritol pentaacrylate mixture (mixture with a mass ratio of 70/30), 2 parts of Irgacure 184, bis (2,4,6-trimethylbenzoyl) -1 part of phenylphosphine oxide, 33 parts of ethyl acetate, and 59.5 parts of butyl acetate were mixed and heated to 40 ° C and mixed to obtain an active energy ray-curable resin composition. A cured coating film was obtained in the same manner as in Example 1. The resulting coating film had a pencil hardness of 3H and a curl value represented by a floating average of 4 apexes of a 5 cm square film> 10 mm.
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