JP6051856B2 - 光重合性樹脂組成物、及び光学フィルム積層体 - Google Patents
光重合性樹脂組成物、及び光学フィルム積層体 Download PDFInfo
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- JP6051856B2 JP6051856B2 JP2012285811A JP2012285811A JP6051856B2 JP 6051856 B2 JP6051856 B2 JP 6051856B2 JP 2012285811 A JP2012285811 A JP 2012285811A JP 2012285811 A JP2012285811 A JP 2012285811A JP 6051856 B2 JP6051856 B2 JP 6051856B2
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- meth
- photopolymerizable
- dioxane
- vinyl
- film
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- 239000011342 resin composition Substances 0.000 title claims description 76
- 239000012788 optical film Substances 0.000 title claims description 27
- -1 oxirane compound Chemical class 0.000 claims description 318
- 239000010408 film Substances 0.000 claims description 187
- 239000000853 adhesive Substances 0.000 claims description 85
- 230000001070 adhesive effect Effects 0.000 claims description 84
- 150000001923 cyclic compounds Chemical class 0.000 claims description 66
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000011248 coating agent Substances 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 39
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 34
- 239000011347 resin Substances 0.000 claims description 34
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 30
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000004434 sulfur atom Chemical group 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 20
- 239000003999 initiator Substances 0.000 claims description 16
- 150000002596 lactones Chemical group 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- 150000003839 salts Chemical group 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- 229920006267 polyester film Polymers 0.000 claims description 11
- 229920006289 polycarbonate film Polymers 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 7
- 229920000636 poly(norbornene) polymer Polymers 0.000 claims description 7
- 125000000466 oxiranyl group Chemical group 0.000 claims description 6
- 125000000532 dioxanyl group Chemical group 0.000 claims description 5
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000005587 carbonate group Chemical group 0.000 claims description 4
- 229920001155 polypropylene Polymers 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 150000003457 sulfones Chemical group 0.000 claims description 4
- 150000003462 sulfoxides Chemical group 0.000 claims description 4
- 150000007970 thio esters Chemical group 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 150
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 89
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 83
- 239000002253 acid Substances 0.000 description 45
- 230000001681 protective effect Effects 0.000 description 44
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 37
- 239000012790 adhesive layer Substances 0.000 description 33
- 229920002554 vinyl polymer Polymers 0.000 description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 23
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- 239000010410 layer Substances 0.000 description 21
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 20
- 206010040844 Skin exfoliation Diseases 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 238000000576 coating method Methods 0.000 description 19
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 19
- 239000000178 monomer Substances 0.000 description 18
- 230000003287 optical effect Effects 0.000 description 18
- 238000009472 formulation Methods 0.000 description 15
- 239000011247 coating layer Substances 0.000 description 14
- 229920001451 polypropylene glycol Polymers 0.000 description 14
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 13
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000004973 liquid crystal related substance Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- 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 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- 235000006708 antioxidants Nutrition 0.000 description 9
- 150000004292 cyclic ethers Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- 229940070710 valerate Drugs 0.000 description 7
- KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 150000003926 acrylamides Chemical class 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920003050 poly-cycloolefin Polymers 0.000 description 6
- RISDDVKHYROMNH-UHFFFAOYSA-N prop-1-en-2-yloxybenzene Chemical compound CC(=C)OC1=CC=CC=C1 RISDDVKHYROMNH-UHFFFAOYSA-N 0.000 description 6
- 238000007142 ring opening reaction Methods 0.000 description 6
- FIPBXQBXPNTQAA-UHFFFAOYSA-N 1-ethenyl-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1C=C FIPBXQBXPNTQAA-UHFFFAOYSA-N 0.000 description 5
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 150000005676 cyclic carbonates Chemical class 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 150000004862 dioxolanes Chemical group 0.000 description 5
- 230000001678 irradiating effect Effects 0.000 description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000004080 punching Methods 0.000 description 5
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 5
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 4
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 4
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- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000010724 Wisteria floribunda Nutrition 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- ZIFHFFOAEFKJJL-UHFFFAOYSA-N prop-1-en-2-yloxymethylbenzene Chemical compound CC(=C)OCC1=CC=CC=C1 ZIFHFFOAEFKJJL-UHFFFAOYSA-N 0.000 description 4
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
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- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
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- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 3
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- 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
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- CFFCKUISNHPWOW-UHFFFAOYSA-N thian-2-one Chemical compound O=C1CCCCS1 CFFCKUISNHPWOW-UHFFFAOYSA-N 0.000 description 1
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 description 1
- KYSLXZJXRBTXDF-UHFFFAOYSA-N thietan-2-one Chemical compound O=C1CCS1 KYSLXZJXRBTXDF-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class 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
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-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
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 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
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 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
- NQWBFQXRASPNLB-UHFFFAOYSA-N wine lactone Chemical compound C1CC(C)=CC2OC(=O)C(C)C21 NQWBFQXRASPNLB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
Landscapes
- Laminated Bodies (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
また、FPDは、表示装置として利用するだけではなく、その表面にタッチパネルの機能を設けて、入力装置として利用されることもある。タッチパネルにも、保護フィルム、反射防止フィルムやITO蒸着樹脂フィルムなどが使用されている。
このようなフィルムは、接着剤を介して被着体に貼着して表示装置に使用されている。表示装置に用いられる接着剤は、まず透明性や耐熱性に優れることが要求されるので、アクリル系樹脂を主剤とする溶剤含有の2液硬化型接着剤が一般に使用されている。
このため、偏光フィルムでは、各層を構成する材料の寸法変化特性が異なるため、温度や湿度の変化に伴う寸法変化によるソリが生じやすい。
しかし、特許文献6記載の接着剤は極めて高粘度であり、塗工性に難がある。
さらに、特許文献6記載の接着剤のように水素化ビスフェノール型オキシラン化合物を主成分とすると、ポリエステル系フィルム、ポリ塩化ビニル系フィルム、ポリカーボネート系フィルム、ポリアクリル系フィルム等の保護フィルムを用いた場合、これらの保護フィルムには全く接着しないという問題があった。
特許文献57記載の接着剤を用いると、湿熱暴露しない状態ではPVA系偏光子とTAC系フィルム、PVA系偏光子とポリシクロオレフィン系フィルムとを十分な強度で接着できる。
しかし、特許文献7記載の接着剤を用いた場合、湿熱暴露するとPVA系偏光子といずれか一方の保護フィルムとの間、もしくはPVA系偏光子と両保護フィルムとの間で剥離が発生する。
さらに、特許文献7記載の接着剤のように脂肪族オキシラン化合物を主成分とすると、ポリエステル系フィルム、ポリ塩化ビニル系フィルム、ポリカーボネート系フィルム、ポリアクリル系フィルム等の保護フィルムを用いた場合、これらの保護フィルムには全く接着しないという問題があった。
さらには、脂環式オキシラン樹脂を増やすと、ポリエステル系フィルム、ポリ塩化ビニル系フィルム、ポリカーボネート系フィルム、ポリアクリル系フィルム等の保護フィルムを用いた場合、これらの保護フィルムには全く接着しないという問題があった。
そこで、偏光板(偏光フィルム)形成用の光重合性接着剤には、実質的に有機溶剤を含有しない状態で低粘度であることが求められる。
樹脂組成物を含有する光重合性樹脂組成物により前記目標達成できることを見出し、更に光重合性コーティング剤、光重合性接着剤により本発明を完成するに至った。
前記光重合性オキシラン樹脂組成物中、オキシラン化合物(A)が主成分であり、
前記一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)が、環内にスルホキシド骨格、スルホン骨格、スルファイト骨格、スルフェート骨格、スルホン酸エステル骨格、スルフィン酸エステル骨格、およびチオエステル骨格からなる群より選択される骨格構造を有しており、
光重合性樹脂組成物中、有機溶剤(ただし、オキシラン化合物(A)と、一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)とを除く)の含有量が、5重量%以内であり、
23℃における溶液粘度が1〜1500mPa・sであることを特徴とする光重合性樹脂組成物に関する。
本発明の光重合性オキシラン系樹脂組成物において、オキシラン化合物(A)とは、反応性官能基として分子内に三員環状の環状エーテル基を1つ以上有する化合物であり、特に制限が無く使用できる。
分子内に三員環状の環状エーテル基としては、例えば、オキシラン、メチルオキシラン、フェニルオキシラン、1,2−ジフェニルオキシラン、メチリデンオキシラン、オキシラニルメチル、オキシラニルメタノール、オキシランカルボン酸、(クロロメチル)オキシラン、(ブロモメチル)オキシラン、オキシラニルアセトニトリル等の脂肪族系環状エーテル基;
等の環状化合物中の水素原子を1個また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。
また、(a−1)、(a−2)及び(a−12)のいずれにも属さない(a−3)も問題は無く使用できる。これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。
本発明の光重合性オキシラン系樹脂組成物において、一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)を有することが好ましく、環状化合物(B)が環内にスルホキシド骨格、スルホン骨格、スルファイト骨格、スルフェート骨格、スルホン酸エステル骨格、スルフィン酸エステル骨格、及びチオエステル骨格からなる群より選択される1種の構造を有することが光重合性の点で好ましい。
本発明の光重合性組成物において、二個以上の酸素原子を有する四員環以上の環状化合物(C)は、オキシラン化合物(A)以外の環状化合物である。
さらに、本発明の光重合性オキシラン系樹脂組成物において、二個以上の酸素原子を有する四員環以上の環状化合物(C)を有することが更に好ましく、(C)がラクトン環、カーボネート環、ジオキソラン環、ジオキサン環、及びトリオキサン環からなる群より選択される1種を有することが光重合性の点で好ましい。
ラクトン類でも、1000mJ/cm2以下の光エネルギー量での照射量では、環の歪みエネルギーの小さい5員環や6員環は、ほとんど光開環重合反応を開始しないが、光重合性組成物に、上記、一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)0.5〜60重量部存在させれば、連鎖的に速やかに光開環重合反応を開始する。つまり、上記の環状化合物(B)が存在すれば、ラクトン類のエステル環を構成する炭素数が4〜18の範囲であってもっても、問題無く使用でき、好ましい範囲となる。具体的には、プロピオラクトン、ブチロラクトン、バレロラクトン、カプロラクトンが特に好ましく、使用できる。
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;
また、前記した(d−1)と(d−2)が同一化合物、つまり、水酸基を有し、かつ、環状骨格を有する化合物(d−12)であっても問題は無く使用できる。また、(d−1)、(d−2)および/または(d−12)以外のその他のエチレン性不飽和化合物(d−3)も含有することができる。
例えば、プロペンジオール、ブテンジオール、ヘプテンジオール、オクテンジオール、ジ(メタ)アクリル酸グルセロール、o−ジ(メタ)アリルビスフェノールA等の複数の水酸基を有するエチレン性不飽和単量体類;
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;
等のアルコキシシリル基含有(メタ)アクリル酸エステル類;
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;
また、エチレン性不飽和化合物(D)としては、光学フィルムとの密着性や耐熱性を考慮すると、水酸基含有のエチレン性不飽和化合物(d−1)、あるいは水酸基を有し、かつ、環状構造を有するエチレン性不飽和化合物(d−12)であることが好ましい。
本発明において、前記の光重合性オキシラン系樹脂組成物に光重合開始剤(E)を含有することによって、光重合性樹脂組成物とし、この光重合性樹脂組成物を使用して、光重合性コーティング剤、あるいは光重合性接着剤とすることができる。
上記の光重合開始剤(E)が、光照射によって酸性活性種を発生するA+B−で表される塩であって、特に限定されないが、一般的にはオニウム塩が良く知られている。オニウム塩としてはルイス酸のジアゾニウム塩、ルイス酸のヨードニウム塩、ルイス酸のスルホニウム塩などが挙げられる。この陽イオンA+が、芳香族ヨードニウムイオンおよび/または芳香族スルホニウムイオンであることが本発明では好ましい。
光重合開始剤(E)の配合割合は、光重合性オキシラン系樹脂組成物100重量部に対して、0.5〜20重量部であり、0.5〜10重量部であることが好ましい。
光重合開始剤(B)の配合割合が0.5重量部より少ないと光重合による充分な硬化性が得られない。また、10重量部より多いと光重合による硬化後に残留した光重合開始剤により耐熱性などが劣化する。
上記、光重合開始剤(E)の性能を向上させるために、光増感剤(F)を併用しても良い。光増感剤(F)としては、アントラセン系やベンゾフェノン系、チオキサントン系やペリレン、フェノチアジン、ローズベンガル等が挙げられる。
本発明における光重合性系樹脂組成物は、更に酸化防止剤(J)を含んでも良い。酸化防止剤(J)を含むことによって、光重合反応における硬化後の硬化塗膜層の経時での着色を抑制することができる。酸化防止剤(J)としては、例えば、アデカスタブAO‐50、アデカスタブAO‐80(旭電化工業社製)、などのフェノール系酸化防止剤や、IRGANOX‐PS‐800FD(BASF社製)、などのイオウ系酸化防止剤、TINUBIN622LD、TINUBIN144、TINUBIN765(いずれもBASF社製)等のヒンダードアミン系の光安定剤等が挙げられるが、これらに限定されるものではない。
酸化防止剤(J)の配合割合は、重合性成分100重量部に対して、0〜5重量部であり、0.01〜3重量部であることが好ましい。
本発明の光重合性樹脂組成物は、オキシラン化合物(A)を主成分とし、さらに、一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)を必須成分とし、必要に応じて、二個以上の酸素原子を有する四員環以上の環状化合物(C)、及び/またはエチレン性不飽和化合物(D)を有した光重合性オキシラン系樹脂組成物に光重合開始剤(E)を含有した樹脂組成物であり、さらに該光重合性樹脂組成物には、増感剤(F)、及び/あるいは酸化防止剤(J)を有する事も可能である。
本発明の光重合性樹脂組成物は、後述の光重合性樹脂組成物を光重合性コーティング剤、あるいは光重合性接着剤として使用可能である。
光重合性樹脂組成物の粘度は、光重合性オキシラン系樹脂組成物の粘度で殆ど決定されるため、光重合性オキシラン系樹脂組成物の粘度を1〜1500mPa・sの範囲で管理することにより、光重合性樹脂組成物の粘度も管理が可能である。
光重合性コーティング層、あるいは光重合性接着層の厚さは、0.1〜6μmの薄膜塗工であることが好ましく、0.1μm〜3μmであることがより好ましい。0.1μm未満では十分な密着力や接着力が得られないことがあり、6μmを超えても密着力や接着力等の特性はそれ以上向上しない場合が多い。
光照射強度がとしては10〜500mW/cm2であることが好ましい。光照射強度が10mW/cm2未満であると、硬化に長時間を必要とし、500mW/cm2を超えると、ランプから輻射される熱により、各種基材(G)における基材劣化が生じる可能性があるため、好ましくない。照射強度と照射時間の積として表される積算光量は50〜5000mJ/cm2とであることが好ましい。積算光量が50mJ/cm2より少ないと、硬化に長時間を必要とし、5000mJ/cm2より大きいと、照射時間が非常に長くなり、生産性が劣るため、好ましくない。
本発明の光重合性樹脂組成物は、さらに光学用の光重合性コーティング剤、または光重合性接着剤として好適である。
即ち、光重合性コーティング剤、または光重合性接着剤として、各種基材(G)に適用することが可能である。
基材(G)としては、光重合性樹脂組成物を光重合コーティング剤として基材(G)一層の片面や両面に使用した場合には、布、木材、金属板、プラスチック板、フィルム状基材、ガラス板、紙加工品等、特に制限無く使用できる。一方、光重合性樹脂組成物を二つ以上の基材(G)を貼り合わせる光重合性接着剤として使用する場合には、紫外線等の活性エネルギー線を照射して重合させるために、活性エネルギー線を透過し易い基材を使用する必要があり、特に透明フィルム(H)や透明ガラス板を使用する事が好ましい。片方を活性エネルギー線が透過し難い基材、例えば、木材、金属板、プラスチック板、紙加工品等を使用した場合でも、もう片方を透明フィルム(H)や透明ガラス板を使用し、透明フィルム(H)や透明ガラス板側から照射し、光重合反応(光硬化)を行えば使用は可能である。
光重合性樹脂組成物の活性エネルギー線による光重合反応を使用する場合は、即ち、前記した基材(G)のうち、フィルム状基材である透明フィルム(H)と該透明フィルム(H)の少なくとも一方の面に位置する光重合性樹脂組成物層とを具備する積層体の形成に使用されることが好ましい。
透明フィルム(H)の積層体は、以下のようにして得ることができる。
光重合性樹脂組成物を光重合性コーティング剤として使用した場合には、フィルム状基材である透明フィルム(H)の片面に光重合性コーティング剤を塗工することによって、積層体を得ることができる。この際、コート層は、易接着化のためのプライマー層としても使用される。
また、酸素などによる光重合阻害を防ぐため活性エネルギー線光を照射した時に光重合性コーティング剤層表面を乾燥窒素等で満たすことが好ましい。
光重合性コーティング剤、または重合性接着剤の活性エネルギー線による光重合反応は、コーティング剤、または接着剤の塗工時、あるいは積層する際、さらには積層した後に活性エネルギー線を照射して進行するが、積層した後に活性エネルギー線を照射して光重合反応を進めることが好ましい。
尚、透明フィルム(H)は、ディスプレイやタッチパネル等の情報通信機器等に使用されている光学フィルム(I)に使用する事ができる。
光重合性コーティング剤、または光重合性接着剤は、光学用積層体を形成するために用いられることが可能である。
光学用積層体の基本的積層構成は、光重合性樹脂組成物を、光重合性コーティング剤として使用した場合には、透明フィルム/コート層、あるいはコート層/透明フィルム/コート層のようなシート状の光学コート積層体である。
また、光重合性接着剤として使用した場合には、透明フィルム/接着層/透明フィルム、あるいは透明フィルム/接着層/透明フィルム/接着層/透明フィルムのようなシート状の両面の光重合性接着積層体である。さらには、透明フィルム/接着層/透明フィルム/接着層/透明フィルム/接着層/透明フィルム、ガラス、あるいは光学成形体のような多層の光学フィルムを光学部材に固定化した光学用積層体として使用される。
各種フィルム状基材(H)としては、各種プラスチックシートともいわれ、例えば、ポリビニルアルコールフィルムやポリトリアセチルセルロースフィルム、ポリプロピレン、ポリエチレン、ポリシクロオレフィン、エチレン−酢酸ビニル共重合体などのポリオレフィン系フィルム、ポリエチレンテレフタレートやポリブチレンテレフタレートなどのポリエステル系フィルム、ポリカーボネート系フィルム、ポリノルボルネン系フィルム、ポリアリレート系フィルム、ポリアクリル系フィルム、ポリフェニレンサルファイド系フィルム、ポリスチレン系フィルム、ポリビニル系フィルム、ポリアミド系フィルム、ポリイミド系フィルム、ポリオキシラン系フィルムなどが挙げられる。
偏光フィルムは、偏光板とも呼ばれ、ポリビニルアルコール系偏光子の両面を2枚のポリアセチルセルロース系フィルムであるポリトリアセチルセルロース系保護フィルム(以下、「TACフィルム」という)や、ポリビニルアルコール系偏光子の片面や両面をポリノルボルネン系フィルムであるポリシクロオレフィ系フィルム、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等で挟んだ多層構造のシート状の光学用積層体である。
(I)第1の保護フィルムの一方の面に、光重合性接着剤を塗工し、第1の光重合性接着
剤層(2’)を形成し、
第2の保護フィルムの一方の面に、光重合性接着剤を塗工し、第2の光重合性接着剤層を形成し、
次いで、ポリビニルアルコール系偏光子の各面に、第1の光重合性接着剤層及び第2の光重合性接着剤層を、同時に/または順番に重ね合わせた後、活性エネルギー線を照射し、第1の光重合性接着剤層及び第2の光重合性接着剤層を光重合反応することによって製造する方法。
重合性接着剤層を形成し、形成された第1の光重合性接着剤層の表面を第1の保護フィルムで覆い、次いでポリビニルアルコール系偏光子の他方の面に、光重合性接着剤を塗工し、第2の光重合性接着剤層を形成し、形成された第2の光重合性接着剤層の表面を第2の保護フィルムで覆い、活性エネルギー線を照射し、第1の光重合性接着剤層及び第2の光重合性接着剤層を光重合することによって製造する方法。
重ねた端部および、ポリビニルアルコール系偏光子の第1の保護フィルムがない面に重ねた第2の保護フィルムの端部に光重合性接着剤をたらした後、ロールの間を通過させ各層間に接着剤を広げる。次に活性エネルギー線を照射し、光重合性接着剤を硬化させることによって製造する方法等があるが、特に限定するものではない。
酸素濃度が10%以下に置換された遮光された300ccのマヨネーズ瓶に、オキシラン化合物(A)、一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)、二個以上の酸素原子を有する四員環以上の環状化合物(C)、エチレン性不飽和化合物(D)、光重合開始剤(E)、増感剤(F)、及び酸化防止剤(J)を表1に示す比率で仕込み、エアモーターにて十分に攪拌を行い、十分に脱泡を行った後、配合例に示す光重合性樹脂組成物を得た。
各配合例で得られた光重合性樹脂組成物の液体外観を目視にて評価した。
各配合例で得られた光重合性樹脂組成物を23℃の雰囲気下でE型粘度計(東機産業社製 TV−22)にて、約1.2mlを測定用試料とし、回転速度0.5〜100rpm、1分間回転の条件で測定し、溶液粘度(mPa・s)とした。
配合例1で得られた光重合性組成物を光重合性接着剤として使用して、以下の積層体を作成した。
保護フィルム(1)として、富士フィルム社製の紫外線吸収剤含有ポリトリアセチルセルロース系フィルム:商品名「フジタック:80μm」を用い、保護フィルム(2)として、富士フィルムビジネスサプライ社製の紫外線吸収剤を含有しないポリトリアセチルセルロース系フィルム:商品名「TAC50μ」(厚み50μm)を使用し、それぞれその表面に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、配合例1に示す光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、光重合性接着剤層を形成し、前記光重合性接着剤層との間に上記のポリビニルアルコール系偏光子を挟み、保護フィルム(1)/光重合性接着剤層/PVA系偏光子/光重合性接着剤層/保護フィルム(2)からなる積層体を得た。
保護フィルム(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。
UV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の紫外線を保護フィルム(2)側から照射して、偏光板を作製した。
実施例1で光重合性接着剤(配合例1)の代わりに、一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)を使用しない配合例26に示す光重合性接着剤に変更した以外は、実施例1と同様にして偏光板を作製した。
[比較例2]
実施例1で光重合性接着剤(配合例1)の代わりに、オキシラン化合物(A)を使用しない配合例27に示す光重合性接着剤に変更した以外は、実施例1と同様にして偏光板を作製した。
実施例1で光重合性接着剤(配合例1)の代わりに、オキシラン化合物(A)を使用しない配合例28に示す光重合性接着剤に変更した以外は、実施例1と同様にして偏光板を作製した。
実施例1で光重合性接着剤(配合例1)の代わりに、表1に示すような配合例2〜25に変更した以外は、実施例1と同様にして偏光板を作製した。
実施例15で使用した保護フィルム(2)を、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(実施例26)、三菱レイヨン社製のアクリル系フィルム(商品名「HDB−002:50μm」)に(実施例27)、カネカ社製のポリカーボネート系フィルム(商品名「R−140:43μm」に(実施例28)、それぞれ変更した以外は、実施例1と同様にして偏光板を得、同様に評価した。
実施例15で使用した保護フィルム(1)を、東セロ社製のポリプロピレン系フィルム(商品名「OPU−1:50μm」に(実施例29)、東セロ社製のポリエチレン系フィルム(商品名「TUX−HZ:50μm」)に(実施例30)、ユニチカ社製のポリエステル系フィルム(商品名「エンブレットS:50μm」に(実施例31)、それぞれ変更した以外は、実施例1と同様にして偏光板を得、同様に評価した。
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(東洋インキ製造株式会社製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。
◎: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、配合例1に示す光重合樹脂組成物を光重合性接着剤として使用し、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、光重合性接着剤層を形成した。さらに光重合性接着剤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、UV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の紫外線を照射し光重合性接着剤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。
ゲル分率(%)={1−(重量1−重量2)/重量1}}×100
◎:ゲル分率が90%以上
○:ゲル分率が80%以上〜90%未満
△:ゲル分率が60%以上〜80%未満
×:ゲル分率が60%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。
◎:0mm
○:1mm以下
△:1〜3mm
×:3mm以上
実施例1〜31、比較例1〜3で得られた偏光板を、50mm×40mmの大きさに裁断し、60℃−90%RHの条件下で500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4段階で評価をした。
○: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。
表1及び2に示した光重合性樹脂組成物を光重合性コーティング剤として使用して、以下の積層体を作成した。
光学フィルムとして、富士フィルム社製の紫外線吸収剤含有ポリトリアセチルセルロース系フィルム:商品名「フジタック:80μm」を用いた。光学フィルム表面を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、配合例1に示す樹脂組成物を光重合性コーティング剤として、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、光重合性コーティング剤層を形成した。
光学フィルム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、ブリキ板に固定した。
UV照射装置(東芝社製 高圧水銀灯)内を乾燥窒素で置換後、波長365nmの最大照度300mW/cm2、積算光量300mJ/cm2の紫外線を活性エネルギー線重合性コート剤層側から照射して、光重合性コーティング剤層を有する積層体を作製した。
JIS K5400に従い碁盤目剥離試験を実施した。100マス中の剥離したマス数を4段階評価した。
◎:0マス
○:1〜10マス
△:11〜30マス
×:31マス以上
実施例41〜70、比較例4〜6で得られた積層体を、50mm×40mmの大きさに裁断し、80℃−ドライの条件下で1000時間暴露した。暴露後積層体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。
○:剥がれが全く無し
△:1mm未満の剥がれあり
×:1mm以上の剥がれあり
Claims (14)
- オキシラン化合物(A)と、一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)とを含む光重合性オキシラン樹脂組成物を含有する光重合性樹脂組成物において、
前記光重合性オキシラン樹脂組成物中、オキシラン化合物(A)が主成分であり、
前記一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)が、環内にスルホキシド骨格、スルホン骨格、スルファイト骨格、スルフェート骨格、スルホン酸エステル骨格、スルフィン酸エステル骨格、およびチオエステル骨格からなる群より選択される骨格構造を有しており、
前記一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)の含有量は、オキシラン化合物(A)100重量部に対して、0.5〜60重量部であり、
光重合性樹脂組成物中、有機溶剤(ただし、オキシラン化合物(A)と、一個以上の酸素原子及び硫黄原子を有する四員環以上の環状化合物(B)とを除く)の含有量が、5重量%以内であり、
23℃における溶液粘度が1〜1500mPa・sであることを特徴とする光重合性樹脂組成物。 - オキシラン化合物(A)が、芳香環を有する化合物(a−1)を含有することを特徴とする請求項1記載の光重合性樹脂組成物。
- オキシラン化合物(A)が、オキシラン環を二個以上有する化合物(a−2)を含有することを特徴とする請求項1または2記載の光重合性樹脂組成物。
- さらに、二個以上の酸素原子を有する四員環以上の環状化合物(C)を含有する請求項1〜3いずれか記載の光重合性樹脂組成物。
- 二個以上の酸素原子を有する四員環以上の環状化合物(C)が、ラクトン環、カーボネート環、ジオキソラン環、ジオキサン環およびトリオキサン環からなる群より選択される環状構造を有することを特徴とする請求項4記載の光重合性樹脂組成物。
- さらに光重合開始剤を含む、請求項1〜5のいずれか記載の光重合性樹脂組成物。
- 光重合開始剤が光照射によって酸性活性種を発生するA+B−で表される塩であって、
この陽イオンA+が、芳香族ヨードニウムイオンおよび芳香族スルホニウムイオンからなる群より選ばれることを特徴とする請求項6記載の光重合性樹脂組成物。 - 光重合性コーティング剤用であることを特徴とする請求項1〜7いずれか記載の光重合性樹脂組成物。
- 光重合性接着剤用であることを特徴とする請求項1〜7いずれか記載の光重合性樹脂組成物。
- 請求項8、または9記載の光重合性樹脂組成物からなる層を、基材(G)の片面、又は両面に積層してなることを特徴とする積層体。
- 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10記載の積層体。
- 透明フィルム(H)が光学フィルム(I)であることを特徴とする請求項11記載の積層体。
- 光学フィルム(I)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またはポリイミド系フィルムであることを特徴とする請求項12記載の積層体。
- 請求項11〜13のいずれかに記載の積層体を用いてポリビニルアルコール系偏光子の片面または両面に接着してなることを特徴とする偏光板。
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