JP5912370B2 - 粘着剤組成物及びこれを用いた光学部材 - Google Patents
粘着剤組成物及びこれを用いた光学部材 Download PDFInfo
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- JP5912370B2 JP5912370B2 JP2011210719A JP2011210719A JP5912370B2 JP 5912370 B2 JP5912370 B2 JP 5912370B2 JP 2011210719 A JP2011210719 A JP 2011210719A JP 2011210719 A JP2011210719 A JP 2011210719A JP 5912370 B2 JP5912370 B2 JP 5912370B2
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- Prior art keywords
- meth
- acrylate
- weight
- sensitive adhesive
- adhesive composition
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 52
- 230000003287 optical effect Effects 0.000 title claims description 26
- 239000000853 adhesive Substances 0.000 title claims description 21
- 230000001070 adhesive effect Effects 0.000 title claims description 21
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 48
- 239000003431 cross linking reagent Substances 0.000 claims description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 40
- 230000009477 glass transition Effects 0.000 claims description 39
- 239000004925 Acrylic resin Substances 0.000 claims description 38
- 239000000178 monomer Substances 0.000 claims description 26
- 229920001577 copolymer Polymers 0.000 claims description 19
- 229920001187 thermosetting polymer Polymers 0.000 claims description 18
- 239000012948 isocyanate Substances 0.000 claims description 16
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 239000010410 layer Substances 0.000 claims description 13
- 239000012788 optical film Substances 0.000 claims description 10
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 8
- 238000003860 storage Methods 0.000 claims description 8
- 150000001718 carbodiimides Chemical class 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims 1
- 239000010408 film Substances 0.000 description 27
- -1 iodo compound Chemical class 0.000 description 15
- 235000019557 luminance Nutrition 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000003949 imides Chemical class 0.000 description 9
- 230000035882 stress Effects 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 5
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000012790 adhesive layer Substances 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004299 exfoliation Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000005728 strengthening Methods 0.000 description 3
- 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 3
- 238000012546 transfer Methods 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- 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
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 241001448862 Croton Species 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 239000002518 antifoaming agent Substances 0.000 description 1
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- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012939 laminating adhesive Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
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- 230000035939 shock Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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Description
本発明の(メタ)アクリレート共重合体は、(A1)ガラス転移温度が200K以上250K未満の(メタ)アクリレート樹脂と、(A2)ガラス転移温度が250K以上300K以下の(メタ)アクリレート樹脂を含むことが好ましい。
前記架橋剤としては、イソシアネート架橋剤とイミド系架橋剤の組み合わせを用いることができる。
たは、これらの混合物を使用することができる。
本発明では、接着安定性と接着信頼性をより向上させるために通常のシランカップリング剤を用いることができる。
(A)(メタ)アクリレート共重合体
(A1)ガラス転移温度が200K以上250K未満の(メタ)アクリレート樹脂
窒素ガスで1次パージング(purging)しながら1L反応器にn−ブチルアクリレートを98.5重量部投入し、ヒドロキシエチルメタアクリレート1重量部とアクリル酸0.5重量部をさらに反応器に投入した。溶剤はエチルアセテートを一定量投入し、一定時間窒素パージングを行った後、重合開始剤である2,2’−アゾビス イソブチロニトリル(AIBN)を0.05重量部投入した。温度は60℃±2程度に管理し、反応半ばで重合開始剤を0.001重量部を2回に亘って投入して未反応単量体を最小化し、8時間反応させた。製造された(メタ)アクリレート樹脂(A1)は、重量平均分子量が1400,000g/molで、分子量分布は3.8、ガラス転移温度が227K、固形分15%だった。
n−ブチルアクリレート98.5重量部の代わりに、n−ブチルアクリレート60重量部、メチルアクリレート23.5重量部、メチルメタアクリレート15重量部、ヒドロキシエチルメタアクリレート1重量部及びアクリル酸0.5重量部を使用したことを除いては、前記(A1)と同様に(メタ)アクリレート樹脂を製造した。製造された(メタ)アクリレート樹脂(A2)は、重量平均分子量が800,000g/molで、分子量分布は4.7、ガラス転移温度は265K、固形分25%だった。
(B1)イソシアネート系架橋剤として、トリメチロールプロパン変性トルエンジイソシアネート(コロネート−L:日本ポリウレタン社製)を使用した。
γ−グリシトキシプロピルメトキシシラン(KBM−403:信越化学工業社製)を使用した。
前記の各成分を下記表1の組成で混合し、エチルアセテート30重量部を加えて20分間攪拌して均一な混合液を製造した。製造された混合液は、偏光板に25μmの厚さにコーティングして72時間熟成した後、下記の方法で物性評価を行った。
(1)ゲル分率:下記数式1のように、常温(23℃)でサンプル1.0〜2.0gを48時間トルエン(20ml)に溶かし、24時間乾燥した後残った残量に対する質量を初期質量に対する百分率で表した。
△:切断面の粘着剤の取れが多少あり(リワーク時の転写多少あり)
×:切断面の粘着剤の取れがあり(リワーク時の転写あり)
(5)光漏れ:偏光板を設置した液晶表示装置を駆動させた後、輝度測定装置を使用して1mの高さで表示パネル全面の輝度を測定した。そのうち、中央部と光漏れが表れるエッジ部の輝度の差により光漏れの程度を定量化した。下記式によるエッジ部と中心部間の輝度差(ΔL)を求めた。ΔL値が低いほど光漏れの防止に優れる。
△:気泡や剥離現象多少あり
×:気泡や剥離現象あり
(9)貯蔵弾性率(dyne/cm2):粘着層を積層して、直径8mm、厚さ1mmの試片を製作し、レオメーターを利用して温度を20℃から120℃まで5℃/minの速度で上温しながら10rad/sで貯蔵弾性率を測定した。
b 光学部材一辺の端部から全体の面積の1/16の面積に該当する位置の平均輝度、
c 光学部材中央部の1/32の面積の平均輝度、
d 光学部材一辺の端部から全体の面積の1/16の面積に該当する位置の平均輝度、
e 光学部材一辺の端部から全体の面積の1/16の面積に該当する位置の平均輝度。
Claims (11)
- (メタ)アクリレート共重合体100重量部;架橋剤1〜10重量部;及びシランカップリング剤0.01〜5重量部を含み、
前記(メタ)アクリレート共重合体は、(A1)ガラス転移温度が200K以上250K未満の(メタ)アクリレート樹脂を必須に含み、
前記(メタ)アクリレート樹脂(A1)は、(メタ)アクリレート、ヒドロキシ基を有する単量体及びカルボキシル基を有する単量体を含む単量体混合物由来の重合体であり、
前記架橋剤はイソシアネート架橋剤及びカルボジイミド系架橋剤を含み、
熱硬化した後の硬化物の貯蔵弾性率が8×105〜1×108dyne/cm2で、下記数式1で表される熱硬化した後の硬化物のゲル分率が83〜95%の熱硬化性粘着剤組成物:
- 前記熱硬化性粘着剤組成物は、(メタ)アクリレート共重合体及び架橋剤を含み、前記(メタ)アクリレート共重合体は、(A1)ガラス転移温度が200K以上250K未満の(メタ)アクリレート樹脂を必須に含み、更に必要に応じて(A2)ガラス転移温度が250K以上300K以下の(メタ)アクリレート樹脂を含んでなることを特徴とする請求項1に記載の熱硬化性粘着剤組成物。
- 前記(メタ)アクリレート共重合体は、(A1)ガラス転移温度が200K以上250K未満の(メタ)アクリレート樹脂50〜100重量%と、(A2)ガラス転移温度が250K以上300K以下の(メタ)アクリレート樹脂0〜50重量%を含んでなることを特徴とする請求項2に記載の熱硬化性粘着剤組成物.
- 前記(メタ)アクリレート樹脂(A2)は、ガラス転移温度が253.15〜423.15Kのモノマーが共重合されたことを特徴とする請求項3に記載の熱硬化性粘着剤組成物。
- 前記ガラス転移温度が253.15〜423.15Kのモノマーは、メチルメタクリレート、メチルアクリレート、ブチルメタアクリレート、イソブチルメタアクリレートからなる群から選択された一つ以上を含むことを特徴とする請求項4に記載の熱硬化性粘着剤組成物。
- 前記ガラス転移温度が200K以上250K未満の(メタ)アクリレート樹脂(A1)は、重量平均分子量が800,000〜3,000,000g/molであり、前記ガラス転移温度が250K以上300K以下の(メタ)アクリレート樹脂(A2)は、重量平均分子量が100,000〜1,200,000g/molであることを特徴とする請求項2〜5のいずれか一項に記載の熱硬化性粘着剤組成物。
- 前記ガラス転移温度が250K以上300K以下の(メタ)アクリレート樹脂(A2)は、重量平均分子量が500,000〜1,200,000g/molであることを特徴とする請求項6に記載の熱硬化性粘着剤組成物。
- 前記イソシアネート架橋剤と前記カルボジイミド系架橋剤の比率は、100〜350:1であることを特徴とする請求項1〜7のいずれか1項に記載の熱硬化性粘着剤組成物。
- 前記架橋剤は、イソシアネート架橋剤3〜9重量部及びカルボジイミド系架橋剤0.01〜1重量部を含むことを特徴とする請求項1〜8のいずれか1項に記載の熱硬化性粘着剤組成物。
- 請求項1〜9のいずれかに記載の熱硬化性粘着剤組成物を光学フィルムの片面又は両面の粘着剤層として含むことを特徴とする光学部材。
- 前記光学部材は、下記式によるエッジ部と中心部間の輝度差(ΔL)が1未満であることを特徴とする請求項10に記載の光学部材:
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CN102159332A (zh) * | 2008-08-12 | 2011-08-17 | 关西涂料株式会社 | 用于形成多层涂膜的方法 |
EP2330170A4 (en) | 2008-09-01 | 2012-12-05 | Nippon Carbide Kogyo Kk | STICKER ADHESIVE COMPOSITION, STICKER ADHESIVE AND OPTICAL FILM |
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KR100983026B1 (ko) * | 2008-12-18 | 2010-09-17 | 주식회사 엘지화학 | 점착제 조성물, 편광판 및 액정표시장치 |
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JP2010189545A (ja) * | 2009-02-18 | 2010-09-02 | Nitto Denko Corp | 両面粘着シートおよび粘着型光学部材 |
JP2011028251A (ja) * | 2009-06-26 | 2011-02-10 | Fujifilm Corp | 位相差フィルム、偏光板及び液晶表示装置 |
JP5089667B2 (ja) * | 2009-10-01 | 2012-12-05 | リンテック株式会社 | 光情報記録媒体用粘着シート、光情報記録媒体ならびに光情報記録媒体再生方法および装置 |
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JP2012140587A (ja) | 2012-07-26 |
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US9464212B2 (en) | 2016-10-11 |
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