JP6314531B2 - 活性エネルギー線重合性樹脂組成物及び積層体 - Google Patents
活性エネルギー線重合性樹脂組成物及び積層体 Download PDFInfo
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- JP6314531B2 JP6314531B2 JP2014032225A JP2014032225A JP6314531B2 JP 6314531 B2 JP6314531 B2 JP 6314531B2 JP 2014032225 A JP2014032225 A JP 2014032225A JP 2014032225 A JP2014032225 A JP 2014032225A JP 6314531 B2 JP6314531 B2 JP 6314531B2
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- meth
- vinyl
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- 239000011342 resin composition Substances 0.000 title description 92
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
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- 239000000758 substrate Substances 0.000 claims description 25
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 22
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 19
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- 125000000217 alkyl group Chemical group 0.000 claims description 7
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- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 44
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 22
- 238000000576 coating method Methods 0.000 description 22
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 20
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 16
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- 125000003118 aryl group Chemical group 0.000 description 14
- 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 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 13
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 229930185605 Bisphenol Natural products 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
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- 239000000047 product Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 150000003926 acrylamides Chemical class 0.000 description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 7
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 7
- SVTBMSDMJJWYQN-UHFFFAOYSA-N hexylene glycol Natural products CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 239000011976 maleic acid Substances 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 229940070710 valerate Drugs 0.000 description 7
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 238000004080 punching Methods 0.000 description 6
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- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 5
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 5
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 3
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- URLYGBGJPQYXBN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate Chemical compound OCC1CCC(COC(=O)C=C)CC1 URLYGBGJPQYXBN-UHFFFAOYSA-N 0.000 description 3
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
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- 238000006068 polycondensation reaction Methods 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
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- 229920006295 polythiol Polymers 0.000 description 1
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- RWTNDBYQABFGKZ-UHFFFAOYSA-M potassium;2-ethenoxybenzenesulfonate Chemical compound [K+].[O-]S(=O)(=O)C1=CC=CC=C1OC=C RWTNDBYQABFGKZ-UHFFFAOYSA-M 0.000 description 1
- IZCABQCSROGIGG-UHFFFAOYSA-M potassium;2-methylprop-2-ene-1-sulfonate Chemical compound [K+].CC(=C)CS([O-])(=O)=O IZCABQCSROGIGG-UHFFFAOYSA-M 0.000 description 1
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- WEMQMWWWCBYPOV-UHFFFAOYSA-N s-indacene Chemical compound C=1C2=CC=CC2=CC2=CC=CC2=1 WEMQMWWWCBYPOV-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 239000001384 succinic acid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- XMRZNNGTCUALQE-UHFFFAOYSA-N tert-butyl 3-(4-ethenylphenoxy)propanoate Chemical compound CC(C)(C)OC(=O)CCOC1=CC=C(C=C)C=C1 XMRZNNGTCUALQE-UHFFFAOYSA-N 0.000 description 1
- YQPZJBVEKZISEF-UHFFFAOYSA-N tetracont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C YQPZJBVEKZISEF-UHFFFAOYSA-N 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- NPWJBNPQTPEEGC-UHFFFAOYSA-N tetradecyl 4-ethenylbenzoate Chemical compound C(CCCCCCCCCCCCC)OC(C1=CC=C(C=C1)C=C)=O NPWJBNPQTPEEGC-UHFFFAOYSA-N 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003639 thymyl group Chemical group C1(=CC(C)=CC=C1C(C)C)* 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
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- 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
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- LWLOKSXSAUHTJO-IMJSIDKUSA-N trans-2,3-butylene carbonate Chemical compound C[C@@H]1OC(=O)O[C@H]1C LWLOKSXSAUHTJO-IMJSIDKUSA-N 0.000 description 1
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
- ACWQBUSCFPJUPN-HWKANZROSA-N trans-2-methyl-2-butenal Chemical compound C\C=C(/C)C=O ACWQBUSCFPJUPN-HWKANZROSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
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- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical compound CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- KEDGSDIAPIAOGT-UHFFFAOYSA-N triethoxy-[3-[(3-ethyloxetan-2-yl)methoxy]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1OCC1CC KEDGSDIAPIAOGT-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- NELVVTIEGZVCKM-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.C[N+](C)(C)CCCNC(=O)C=C.C[N+](C)(C)CCCNC(=O)C=C NELVVTIEGZVCKM-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 235000012711 vitamin K3 Nutrition 0.000 description 1
- 239000011652 vitamin K3 Substances 0.000 description 1
- 229940041603 vitamin k 3 Drugs 0.000 description 1
- 230000037303 wrinkles Effects 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
- 125000005023 xylyl group Chemical group 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- CIBGZAYGXFGOFK-UHFFFAOYSA-L zinc;2-phenylethenesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C=CC1=CC=CC=C1.[O-]S(=O)(=O)C=CC1=CC=CC=C1 CIBGZAYGXFGOFK-UHFFFAOYSA-L 0.000 description 1
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Landscapes
- Liquid Crystal (AREA)
- Polymerisation Methods In General (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polarising Elements (AREA)
Description
高温環境下では接着性が弱いとPVA系偏光子と保護フィルムの熱収縮率の違いにより、PVA系偏光子と保護フィルムとが剥がれる問題が発生することがあるが、前記カチオン重合性紫外線硬化型接着剤により形成した偏光板では過酷な環境下における耐久性を満足することはできていなかった。
特許文献5には、水酸基を有しない(メタ)アクリルアミド化合物と、ホウ酸とからなる紫外線硬化型組成物が開示されている。
偏光板に要求される耐久性能は厳しくなっており、高湿下及び高温下において、より過酷な環境下における耐久性が要求されている。しかし、前記偏光板では、前記過酷な環境下における耐久性を満足することはできていなかった。
アルデヒド基含有化合物(B)および/または下記一般式(1)で表される化合物(C)と、
活性エネルギー線開始剤(D)とを含有することを特徴とする活性エネルギー線重合性樹脂組成物に関する。
化合物(C)が、1,3−ジオキセタン、1,3,5−トリオキサン、2,4,6−トリメチル−1,3,5−トリオキサンからなる群れより選択される1以上の化合物であることを特徴とする上記活性エネルギー線重合性樹脂組成物に関する。
該基材(G)の少なくとも一方の主面に設けられた上記樹脂組成物からなる樹脂層とを有する積層体に関する。
該光学フィルムの少なくとも一方の主面に設けられた上記樹脂組成物からなる樹脂層とを有する光学素子用積層体に関する。
<活性エネルギー線重合性樹脂組成物>
本発明の活性エネルギー線重合性組成物はα,β−エチレン性不飽和二重結合基含有化合物(A)と、
アルデヒド基含有化合物(B)および/または下記一般式(1)で表される化合物(C)と、
活性エネルギー線開始剤(D)とを含有することを特徴とする活性エネルギー線重合性樹脂組成物であることを特徴とする。
(A)成分:
α,β−エチレン性不飽和二重結合基含有化合物(A)は、1個以上のα,β−不飽和二重結合基を含有する化合物であれば、特に制限はなく、使用できるが、その構造中に1個以上の水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物(a1)を含有することが好ましい。化合物(a1)には、水酸基を有し、環状構造を有しない化合物(a1−1)と、水酸基を有し、環状構造を有する化合物(a1−2)に分けられるが、いずれも水酸基を有することによって、後述の基材(G)との密着性向上とに大きな効果を示す。
更に、耐熱性、あるいは耐湿熱性等の耐久性向上の点で、1以上の環状構造を有し、水酸基を有しないα,β−エチレン性不飽和二重結合基含化合物(a2)を含有することが好ましい。また、(a1),(a2)以外のα,β−エチレン性不飽和二重結合基含化合物(a3)も含有することができる。
例えば、N−ヒドロキシエチル(メタ)アクリルアミド〔N−ヒドロキシエチルアクリルアミドとN−ヒドロキシエチルメタクリルアミドとを併せて「N−ヒドロキシエチル(メタ)アクリルアミド」と表記する。以下同様。〕、N−ヒドロキシプロピル(メタ)アクリルアミド、N−ヒドロキシブチル(メタ)アクリルアミド、N−ヒドロキシヘキシル(メタ)アクリルアミド、N−ヒドロキシオクチル(メタ)アクリルアミド等の水酸基含有の(メタ)アクリルアミド類;
化合物(a1−1)としては、化合物(B)および/または化合物(C)の溶解性と後述の基材(G)との密着性の面より、(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピル、(メタ)アクリル酸4−ヒドロキシブチル、ε−カプロラクトン1〜2mol付加(メタ)アクリル酸2−ヒドロキシエチル等の炭素数2〜18であるα,β−エチレン性不飽和二重結合基含有化合物が特に好ましい。
化合物(a1−2)としては、その構造中に水酸基と環状構造の双方を有するものであれば特に制限はなく、例えば、(メタ)アクリル酸1,2−シクロヘキサンジメタノール、(メタ)アクリル酸1,3−シクロヘキサンジメタノール、(メタ)アクリル酸1,4−シクロヘキサンジメタノール、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシメチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシエチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシプロピル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシブチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシデシル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシオクタデシル、(メタ)アクリル酸モノヒドロキシエチルフタレート、(メタ)アクリル酸2−(4−ベンゾイル−3−ヒドロキシフェノキシ)エチル等の水酸基とヘテロ環以外の環状構造を有する(メタ)アクリル酸エステル類;
4−ビニル安息香酸メチルポリ(エチレンオキサイド)、4−ビニル安息香酸エチルポリ(エチレンオキサイド)、4−イソプロペニル安息香酸メチルポリ(プロピレンオキサイド)、4−イソプロペニル安息香酸エチルポリ(プロピレンオキサイド)などのポリアルキレンオキサイド部位を有するビニル安息香酸エステル系またはイソプロペニル安息香酸エステル系単量体類;
スチレンスルホン酸ナトリウム、スチレンスルホン酸カリウム、スチレンスルホン酸リチウム、スチレンスルホン酸マグネシウム、スチレンスルホン酸亜鉛、スチレンスルホン酸鉄等のスチレンスルホン酸の金属塩類;
ビニルオキシベンゼンスルホン酸アンモニウム、ビニルオキシベンゼンスルホン酸ナトリウム、ビニルオキシベンゼンスルホン酸カリウム等のアルケニル基含有ビニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類;
2−メチル−2−プロペニルオキシベンゼンスルホン酸アンモニウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸ナトリウム、2−メチル−2−プロペニルオキシベンゼンスルホン酸カリウム等の2−メチル−2−プロペニルオキシベンゼンスルホン酸の金属塩やアンモニウム塩類等が挙げられる。
2−メチル−2−プロペニルスルホン酸アンモニウム、2−メチル−2−プロペニルスルホン酸ナトリウム、2−メチル−2−プロペニルスルホン酸カリウム等の2−メチル−2−プロペニルスルホン酸の金属塩やアンモニウム塩類;
例えば、(メタ)アクリロニトリル、α−クロロアクリロニトリル、クロトンニトリル、マレインニトリル、フマロニトリル、メサコンニトリル、シトラコンニトリル、イタコンニトリル、2−プロペンニトリル、(メタ)アクリル酸2−シアノエチルなどのニトリル基含有α,β−不飽和二重結合基含有化合物類;
比較的高分子量のポリオール類としては、より具体的には、例えば、高分子量ポリエステルポリオール、高分子量ポリアミドポリオール、高分子量ポリカーボネートポリオール及び高分子量ポリウレタンポリオールが挙げられる。高分子量ポリカーボネートポリオールは、上記の比較的低分子量のジオールと炭酸エステル又はホスゲンとの反応によって得られる。
上記高分子量ポリアミドポリオールの市販品としては、富士化成工業社製のTPAE617等を使用できる。
上記高分子量ポリカーボネートポリオールの市販品としては、例えば、パーストープ社製のオキシマーN112、旭化成ケミカルズ社製のPCDLシリーズ、クラレ社製のクラレポリオールPMHCシリーズ、クラレポリオールCシリーズ等が挙げられる。
その他に、ポリカプロラクトンジオール、ポリ(β−メチル−γ−バレロラクトン)ジオール、ポリバレロラクトンジオール等のラクトン類を開環重合して得られるポリエステルポリオール等も、上記高分子量ポリオールとして使用できる高分子量ポリオールに含まれる。
芳香脂肪族ポリイソシアネートとしては、ω,ω’−ジイソシアネート−1,3−ジメチルベンゼン、ω,ω’−ジイソシアネート−1,4−ジメチルベンゼン、ω,ω’−ジイソシアネート−1,4−ジエチルベンゼン、1,4−テトラメチルキシリレンジイソシアネート、1,3−テトラメチルキシリレンジイソシアネート等を挙げることができる。
フェニレンジアミン、キシリレンジアミン、2,4−トリレンジアミン、2,6−トリレンジアミン、ジエチルトルエンジアミン,3,3’−ジクロロ−4,4’−ジアミノジフェニルメタン、4,4’−ビス−(sec−ブチル)ジフェニルメタン等の芳香族ジアミン;
トリメチルシリルジメチルアミン等の単官能のシリルアミノ基を保有するシリルアミン類;
1,1,3,3−テトラメチルジシラザン等の2官能のシリルアミノ基を保有するシリルアミン類が使用できる。
化合物(a1)が1重量部より少ないと、後述の化合物(B)および/または化合物(C)の溶解性を低下させるだけで無く、後述の基材(G)との密着性が低下する。化合物(a1)が45重量部より多いと、耐水性が劣るため好ましくない。化合物(a2)が1重量部より少ないと、塗膜の耐熱性や耐湿熱性が低下する。化合物(a2)が45重量部より多いと、塗膜の柔軟性が失われ、脆くなったりするため好ましくない。
化合物(B)は、α,β−エチレン性不飽和二重結合基含有化合物(A)と相互作用して水や有機溶剤を含まずとも安定で均一な活性エネルギー線重合性樹脂組成物の液を形成できることを可能とし、当該組成物の液を活性エネルギー線で硬化後は、化合物(A)と結合した塗膜を形成する。また、後述の基材(G)の表面官能基と結合を形成して密着性を良くするだけでなく、抜き打ち加工性や耐熱性、耐湿熱性を向上させる。化合物(B)は単独又は混合して使用可能である。
アセトアルデヒド、プロピオンアルデヒド、ピバルアルデヒド、ブチルアルデヒド、イソブチルアルデヒド、ペンチルアルデヒド、イソペンチルアルデヒド、ヘキシルアルデヒド、カプリルアルデヒド(オクタナール)、ペラルゴンアルデヒド、カプリンアルデヒド、ウンデシルアルデヒド、ラウリンアルデヒド(ドデカナール)、トリデシルアルデヒド、ミリスチンアルデヒド、ペンタデシルアルデヒド、パルミチンアルデヒド、マルガリンアルデヒド、ステアリンアルデヒド、パラホルムアルデヒド等の脂肪族飽和アルデヒド、
例えば、2−ヒドロキシベンズアルデヒド、3−ヒドロキシベンズアルデヒド、4−ヒドロキシベンズアルデヒド、2−フェネチルアルデヒド、1−フェネチルアルデヒド等の水酸基含有芳香族アルデヒド、
例えば、シンナムアルデヒド、4-(ジメチルアミノ)-シンナムアルデヒド、2'-ニトロシンナムアルデヒド、ホルミルメチレントリフェニルホスホラン、α-メチルシンナムアルデヒド等の不飽和基含有芳香族アルデヒド、
更に、ブチルアルデヒド、1,3,5−トリオキサンおよび2,4,6−トリメチル−1,3,5−トリオキサンが反応性に優れ、取扱いが容易である点で特に好ましい。
化合物(B)および/または化合物(C)が0.1重量%部未満であると所望の接着力発現に至らず、10重量%以上であると、時間の経過で析出してきたり、樹脂成分が減ることで密着力が低下するなどの問題が生じる場合がある。
活性エネルギー線重合開始剤(D)としては例えば活性エネルギー線ラジカル重合開始剤(d1)や活性エネルギー線カチオン開始剤(d2)を使うことができる。本発明の樹脂組成物は、各種活性化エネルギー線の照射によって重合反応が進行し、硬化可能である。そのため樹脂組成物には、活性エネルギー線重合開始剤(D)を含む必要がある。活性エネルギー線重合開始剤(D)を使用することによって、重合反応を促進することができる。本発明の一実施形態において、上記活性化エネルギーは紫外線であることが好ましい。
具体例として、例えば、以下が挙げられる。2,2−ジメトキシ−2−フェニルアセトフェノン、アセトフェノン、ベンゾフェノン、キサントフルオレノン、ベンズアルデヒド、アントラキノン、3−メチルアセトフェノン、4−クロロベンゾフェノン、4,4’−ジアミノベンゾフェノン、ベンゾインプロピルエーテル、ベンゾインエチルエーテル、ベンジルジメチルケタール、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、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン、4−チオキサントン、カンファーキノン、及び2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1−オン等。
また、市販品としては、例えば、以下が挙げられる。イルガキュアー184,907,651,1700,1800,819,369,及び261(BASF社製)、DAROCUR−TPO(BASF社製、2,4,6−トリメチルベンゾイル−ジフェニル−ホスフィンオキサイド)、ダロキュア−1173(メルク社製)、エザキュアーKIP150,及びTZT(日本シイベルヘグナー社製)、カヤキュアBMS,及びカヤキュアDMBI(日本化薬社製)等。
また、分子内に少なくとも1個の(メタ)アクリロイル基を有する光重合開始剤を使用することもできる。
本発明では、上記成分(D)として、上述の化合物を単独で、又は2種類以上組合せて使用することができる。本発明では、上記成分(D)として、上述の化合物を単独で、又は2種類以上組合せて使用することができる。
ここに例示したオキシラン化合物は、それぞれ単独で使用してもよいし、また複数のオキシラン化合物を混合して使用してもよい。
等の環状化合物中の水素原子を1個又は複数個取り除いた形の基が他の化学構造に結合し得る芳香環が挙げられる。
オキソラン−4−イル)エトキシ]−2H−1−ベンゾピラン−2−オン、7−[2−(2−オキソ−4−メチル−1,3−ジオキソラン−4−イル)エトキシ]−2H−1−ベンゾピラン−2−オン、5−(ベンジルオキシ)−1,3−ジオキソラン−2−オン、4−(イソブトキシメチル)−1,3−ジオキソラン−2−オン、4−(4−ノニルベンジルオキシメチル)−1,3−ジオキソラン−2−オン、4−(4−クロロフェニルチオメチル)−1,3−ジオキソラン−2−オン、4−[3−(クロロメチル)フェニル]−1,3−ジオキソラン−2−オン、4−[4−(クロロメチル)フェニル]−1,3−ジオキソラン−2−オン、4,4−ジプロピル−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4,4−ジペンチル−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4,4−ジイソプロピル−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4,4−ジフェネチル−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4,4−ビス(2−シクロヘキシルエチル)−5−[1−(4−メトキシフェノキシ)エテニル]−1,3−ジオキソラン−2−オン、4−[1−(フェニルチオ)シクロヘキシル]−1,3−ジオキソラン−2−オン、4−(3−メトキシ−4−エトキシフェニル)−5−(ヒドロキシメチル)−1,3−ジオキソラン−2−オン、4−(フェノキシカルボニルオキシメチル)−1,3−ジオキソラン−2−オン、4−ベンジリデン−5,5−ジメチル−1,3−ジオキソラン−2−オン、4−[(2−ナフチル)メチレン]−5,5−ジメチル−1,3−ジオキソラン−2−オン、4−(4−クロロベンジリデン)−5,5−ジメチル−1,3−ジオキソラン−2−オン、5−メチル−5−フェニル−4−(3−フェニルプロピリデン)−1,3−ジオキソラン−2−オン、5,5−ジメチル−4−(3−フェニルプロピリデン)−1,3−ジオキソラン−2−オン、4−[4−(クロロカルボニルオキシ)ブチル]−1,3−ジオキソラン−2−オン、4−クロロ−1,3−ジオキソラン−2−オン、4−クロロ−4,5−ジメチル−1,3−ジオキソラン−2−オン、4−(クロロカルボニルオキシメチル)−1,3−ジオキソラン−2−オン、4−(p−クロロフェノキシメチル)−1,3−ジオキソラン−2−オン、4−(クロロメチル)−1,3−ジオキソラン−2−オン、4,5−ジクロロ−1,3−ジオキソラン−2−オン、(4S,5R)−4,5−ジフェニル−1,3−ジオキソラン−2−オン、4α,5α−ジメチル−1,3−ジオキソラン−2−オン、(4R,5R)−4,5−ジメチル−1,3−ジオキソラン−2−オン、(4S,5S)−4,5−ジメチル−1,3−ジオキソラン−2−オン、(4S)−4β−メチル−1,3−ジオキソラン−2−オン、(R)−4−メチル−1,3−ジオキソラン−2−オン、(S)−5−エチル−1,3−ジオキソラン−2−オン、4−[(トリフェニルシリル)メチル]−5,5−ジメチル−1,3−ジオキソラン−2−オン、4−[9−(3−チエニル)ノニル]−1,3−ジオキソラン−2−オン、4−(メチルアミノメチル)−1,3−ジオキソラン−2−オン、4−(4−クロロフェニルチオ)−1,3−ジオキソラン−2−オン、4−(フェニルチオ)−1,3−ジオキソラン−2−オン、4−(4−メトキシフェニルチオ)−1,3−ジオキソラン−2−オン、4−(4−ブロモフェニルチオ)−1,3−ジオキソラン−2−オン4−(フェニルチオメチル)−1,3−ジオキソラン−2−オン、4,4′−[スルホニルビス(p−フェニレンオキシメチレン)]ビス(1,3−ジオキソラン−2−オン)、4−(4−メチルフェニルチオ)−1,3−ジオキソラン−2−オン、4,4,5,5−テトラメチル−2−(フェニルスルホニルオキシイミノ)−1,3−ジオキソラン、2−(4−ニトロフェノキシ)−4−メチル−2−ホスファ(V)−1,3−ジオキソラン−2−オン、4−(グリシジルオキシメチル)−1,3−ジオキソラン−2−オン、グリシジルカルバミド酸(2−オキソ−1,3−ジオキソラン−4−イル)メチル、4−(ノルボルナ−5−エン−2−イル)−1,3−ジオキソラン−2−オン、4−[2−(2−ナフチル)エチル]−5−メトキシ−1,3−ジオキソラン−2−オン、4−[2−(1−ナフチル)エチル]−5−メトキシ−1,3−ジオキソラン−2−オン、4,4−ジメチル−5−(3−チエニルメチレン)−1,3−ジオキソラン−2−オン、4−[2−[ジメチル(トリメチルシリルオキシ)シリル]エチル]−1,3−ジオキソラン−2−オン、4−[2−[(メチル)ビス(トリメチルシリルオキシ)シリル]エチル]−1,3−ジオキソラン−2−オン、4−[2−(トリメチルシリル)エチル]−1,3−ジオキソラン−2−オン、4−[4−(グリシジルカルバモイルオキシ)ブチル]−1,3−ジオキソラン−2−オン、4−[4−(2−オキソ−1,3−ジオキソラン−4−イルメチルカルバモイルオキシ)ブチル]−1,3−ジオキソラン−2−オン、4−[4−(グリシジルカルバモイルオキシ)ブチル]−1,3−ジオキソラン−2−オン、4−(2−オキソ−1,3−ジオキソラン−4−イルメチルカルバモイルオキシメチル)−1,3−ジオキソラン−2−オンなどの5員環カーボネート類;
化合物(e1)が1重量部より少ないと、化合物(B)および/または化合物(C)の溶解性を低下させるだけで無く、後述の基材(G)との密着性が低下する。化合物(e1)が60重量部より多いと、耐水性が劣るため好ましくない。
2-ヒドロキシエチルビニルエーテル、ジエチレングリコールモノビニルエーテル、4−ヒドロキシブチルビニルエーテルが特に好ましい。
本発明の樹脂組成物は、本発明による効果を損なわない範囲であれば、各種添加剤を適宜配合することも可能である。例えば、重合硬化収縮率低減、熱膨張率低減、寸法安定性向上、弾性率向上、粘度調整、熱伝導率向上、強度向上、靭性向上、及び着色向上等の観点から、有機又は無機の充填剤を配合することができる。このような充填剤は、ポリマー、セラミックス、金属、金属酸化物、金属塩、及び染顔料等の材料から構成されるものであってよい。また、その形状については、特に限定されず、例えば、粒子状及び繊維状等であってよい。なお、上記ポリマー系の材料を配合する場合には、シランカップリング剤、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、酸化防止剤、紫外線吸収剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、及び消泡剤等の、独立した充填剤としてではなく、ポリマーブレンド又はポリマーアロイとして、樹脂組成物中に、溶解、半溶解又はミクロ分散させることも可能である。
(I)第1の透明フィルム(第1の保護フィルム)の一方の主面に、接着剤として本発明の樹脂組成物を塗工し、第1の重合性接着層を形成する。また、第2の透明フィルム(第2の保護フィルム)の一方の主面に、接着剤として本発明の樹脂組成物を塗工し、第2の重合性接着層を形成する。次いで、ポリビニルアルコール系偏光子の両主面に、上記第1の重合性接着層と第2の重合性接着層とを、同時に/又は順番に、重ね合わせる。次いで、得られた積層体に活性エネルギー線を照射し、第1及び第2の接着層を重合硬化させる。
酸素濃度が10%以下に置換された遮光された300mlのマヨネーズ瓶に、表1〜表2に示す比率(重量部)で仕込み、ディスパーにて十分に攪拌を行い、十分に脱泡を行った後、活性エネルギー線重合性樹脂組成物をそれぞれ得た。この活性エネルギー線重合性樹脂組成物をそれぞれ、以下の手法によって積層体を作成し評価した。
4HBA:アクリル酸4−ヒドロキシブチル
2HEA:アクリル酸2−ヒドロキシエチル
CHDMMA:アクリル酸1,4−シクロヘキサンジメタノール
DCPA:アクリル酸ジシクロペンタニル
IBXA:アクリル酸イソボルニル
BPADA:エチレンオキサイド変性ビスフェノールAジアクリレート(日立化成製 ファンクリルFA−324A)
nBA:アクリル酸ブチル
NPDA:ジアクリル酸ネオペンチルグリコール
紫光UV3000B:日本合成化学工業社製 ポリウレタン系オリゴマー(ウレタンアクリレート)
JER828:2,2'−(ジメチルメチレン)ビス[(p−フェニレン)オキシメチレン]ビスオキシラン (三菱化学社製)
CEP−01:1,3−フェニレンビス(メチレン)ビス(7−オキサビシクロ[4.1.0]ヘプタン−3−カルボキシレイト)
2021P:3,4−エポキシシクロヘキシルメチル 3,4−エポキシシクロヘキサンカルボキシレート (ダイセル社製 セロキサイド2021P)
GCDG:グリセリンジグリシジルエーテル
OXT−101:3−エチル−3−ヒドロキシメチルオキセタン(東亞合成社製 アロンオキセタンOXT−101)
GC:グリセリンカーボネート
DEGVE:ジエチレングリコールモノビニルエーテル
ph−CHO:ベンズアルデヒド
CH2O−aq:ホルムアルデヒド(37%)水溶液
Bu−CHO:ブチルアルデヒド
DOX:1,3−ジオキソラン
TOX:1,3,5−トリオキサン
MTOX:2,4,6−トリメチル−1,3,5−トリオキサン
TPO:2,4,6−トリメチルベンゾイル-ジフェニル-フォスフィンオキサイト゛(BASF社製,DAROCUR TPO)
CPI110P:トリアリールスルホニウム塩タイプの光酸発生剤(サンアプロ社製)
透明フィルム(1)、(2)として、表1〜2に示すフィルムを使用し、以下の方法で積層体を作成した。
透明フィルム(1)、(2)の表面に300W・min/m2 の放電量でコロナ処理を行い、表面処理後1時間以内に、表1〜表2に示す活性エネルギー線重合性接着剤をワイヤーバーコーターを用いて膜厚4μmとなるように塗工し、活性エネルギー線重合性接着層を形成し、前記活性エネルギー線重合性接着層との間にポリビニルアルコール系偏光子を挟み、透明フィルム(1)/接着層/PVA系偏光子/接着層/透明フィルム(2)からなる積層体を得た。透明フィルム(1)がブリキ板に接するように、この積層体の四方をセロハンテープで固定し、ブリキ板に固定した。
TAC80μm:ポリトリアセチルセルロース系フィルム(紫外線吸収剤含有、膜厚80μm) 富士フィルム社製
TAC50μm:ポリトリアセチルセルロース系フィルム(紫外線吸収剤を含有していない、膜厚50μm)富士フィルムビジネスサプライ社製
ZF−14:ポリノルボルネン系フィルム(紫外線吸収剤を含有していない、膜厚100μm)日本ゼオン社製
HBD−002:ポリアクリル系フィルム(紫外線吸収剤を含有していない、膜厚50μm)三菱レーヨン社製
接着力は、JIS K6 854−4 接着剤−剥離接着強さ試験方法−第4部:浮動ローラー法に準拠して測定した。
即ち、得られた偏光板を、25mm×150mmのサイズにカッターを用いて裁断して測定用サンプルとした。サンプルを両面粘着テープ(トーヨーケム社製DF8712S)を使用して、ラミネータを用いて金属板上に貼り付けて、偏光板と金属板との測定用の積層体を得た。測定用の積層体の偏光板には、保護フィルムと偏光子の間に予め剥離のキッカケを設けておき、この測定用の積層体を23℃、相対湿度50%の条件下で、300mm/分の速度で引き剥がし、剥離力とした。この際、ポリビニルアルコール系偏光子と保護フィルム(1)、及びポリビニルアルコール系偏光子と保護フィルム(2)との双方の剥離力を測定した。この剥離力を接着力として4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:剥離不可、あるいは偏光板破壊
○:剥離力が2.0(N/25mm)以上〜5.0(N/25mm)未満。
△:剥離力が1.0(N/25mm)以上〜2.0(N/25mm)未満。
×:剥離力が1.0(N/25mm)未満。
コロナ処理を施していない日本ゼオン社製のポリノルボルネン系フィルム(商品名「ゼオノア ZF−14:100μm」に、活性エネルギー線重合性接着剤を、ワイヤーバーコーターを用いて膜厚20〜25μmとなるように塗工し、活性エネルギー線重合性接着層を形成した。さらに活性エネルギー線重合性接着層の上にコロナ処理を施していないゼオノア ZF−14を重ね、3層からなる積層体を得た後、活性エネルギー線照射装置(東芝社製 高圧水銀灯)で最大照度300mW/cm2、積算光量300mJ/cm2の活性エネルギー線を照射し活性エネルギー線重合性接着層を重合硬化させた。3層からなる積層体のゼオノア ZF−14を剥離し接着剤層を得た。
接着剤層の重量を測定した後(重量1)を金属メッシュと金属メッシュの間に挟み接着剤層同士が重ならないようにし、メチルエチルケトン(MEK)中で3時間還流した。さらに80℃−30分乾燥し、接着剤層の重量を測定した(重量2)。下記式よりゲル分率を求め、3段階評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
ゲル分率(%)={1−(重量1−重量2)/重量1)}×100
(評価基準)
○:ゲル分率が90%以上
△:ゲル分率が80%以上〜90%未満
×:ゲル分率が80%未満
ダンベル社製の100mm×100mmの刃を用い、作製した偏光板を保護フィルム(1)側から打ち抜いた。
打ち抜いた偏光板の、周辺の剥離距離を定規で測定し、以下の4段階で評価した。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:0mm
○:1mm以下
△:1〜3mm
×:3mm以上
上記偏光板小片を80℃−dryと60℃−90RH%の恒温恒湿機中に放置し、60時間後の延伸方向の縮み量を測定し、元の長さ(100mm)に対する縮み量の割合を収縮率とし求め、以下の3段階で評価をした。
なお、「dry」とは、湿度調整機能付のオーブンで、温度のみコントロールし、湿度のコントロールを行わなかった場合の試験条件である。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
○:収縮率が0.2%以下
△:収縮率が0.2%より大きくて0.4%以下
×:収縮率が0.4%を超える。
各実施例と比較例で得られた偏光板を、50mm×40mmの大きさに裁断し、80℃−dry、及び100℃dryの条件下で、それぞれ1000時間暴露した。暴露後偏光板の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:100℃−dryの条件下でも剥がれが全く無し。
○:80℃−dry条件下で剥がれが全く無し。
△:80℃−dry条件下で1mm未満の剥がれあり。
×:80℃−dry条件下で1mm以上の剥がれあり。
各実施例と比較例で得られた偏光板を、50mm×40mmの大きさに裁断し、60℃−90%RHの条件下、及び85℃−85%RHの条件下で1000時間暴露した。暴露後偏光板の端部の剥がれの有無を目視にて、以下の3段階で評価をした。「△」評価以上の場合、実際の使用時に特に問題ない。
(評価基準)
◎:85℃−85%RHの条件下でも剥がれが全く無し。
○:60℃−90%RHの条件下で剥がれが全く無し。
△:60℃−90%RHの条件下で1mm未満の剥がれあり。
×:60℃−90%RHの条件下で1mm以上の剥がれあり。
さらに、化合物(B)、(C)が請求項2の範囲でない場合は、諸物性が実用範囲内ではあるが若干劣る(実施例16〜18、43〜45)。
また、化合物(B)、(C)の添加量は0.1重量%〜10重量%が好適であることが解る(実施例3〜9、24〜30)
Claims (10)
- その構造中に1個以上の水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物(a1)、および分子内にヘテロ原子を含有しない環構造を有するα,β−エチレン性不飽和二重結合基含化合物(a2−1)からなる群より選択される1種以上を含むα,β−エチレン性不飽和二重結合基含有化合物(A)と、
アルデヒド基含有化合物(B)および/または下記一般式(1)で表される化合物(C)と、
活性エネルギー線重合開始剤(D)とを含有することを特徴とする活性エネルギー線重合性接着剤。
一般式(1)
(一般式(1)中、iは1から5の整数、jは1から8の整数、kは0から5の整数、R1、R2、R3およびR4は独立に水素原子または炭素数1から8のアルキル基をあらわす) - アルデヒド基含有化合物(B)が、下記一般式(2)で表される化合物、
化合物(C)が、1,3−ジオキセタン、1,3,5−トリオキサン及び2,4,6−トリメチル−1,3,5−トリオキサンからなる群より選択される1以上の化合物であることを特徴とする請求項1記載の活性エネルギー線重合性接着剤。
一般式(2)
(一般式(2)中、R5は水素原子または炭素数1から5のアルキル基をあらわす) - 活性エネルギー線重合性接着剤全量中、化合物(B)および化合物(C)を0.1〜10重量%含有することを特徴とする請求項1又は2記載の活性エネルギー線重合性接着剤。
- 化合物(A)が、水酸基を有するα,β−エチレン性不飽和二重結合基含有化合物(a1)を含むことを特徴とする請求項1〜3いずれか記載の活性エネルギー線重合性接着剤。
- 化合物(A)が、1以上の環状構造を有し、水酸基を有しないα,β−エチレン性不飽和二重結合基含有化合物(a2)を含むことを特徴とする請求項1〜4いずれか記載の活性エネルギー線重合性接着剤。
- カチオン重合性化合物(E)を含有することを特徴とする請求項1〜5いずれか記載の活性エネルギー線重合性接着剤。
- 基材(G)と、
該基材(G)の少なくとも一方の主面に設けられた請求項1〜6いずれか記載の活性エネルギー線重合性接着剤からなる樹脂層とを有する積層体。 - 基材(G)が、透明フィルム(H)であることを特徴とする請求項7記載の積層体。
- 前記透明フィルム(H)が、ポリアセチルセルロース系フィルム、ポリノルボルネン系フィルム、ポリプロピレン系フィルム、ポリアクリル系フィルム、ポリカーボネート系フィルム、ポリエステル系フィルム、ポリビニルアルコール系フィルム及びポリイミド系フィルムからなる群から選択される少なくとも1種であることを特徴とする請求項8記載の積層体。
- 光学フィルムと、
該光学フィルムの少なくとも一方の主面に設けられた請求項1〜6いずれか記載の活性エネルギー線重合性接着剤からなる樹脂層とを有する光学素子用積層体。
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