JP5746966B2 - 粘着剤組成物 - Google Patents
粘着剤組成物 Download PDFInfo
- Publication number
- JP5746966B2 JP5746966B2 JP2011506055A JP2011506055A JP5746966B2 JP 5746966 B2 JP5746966 B2 JP 5746966B2 JP 2011506055 A JP2011506055 A JP 2011506055A JP 2011506055 A JP2011506055 A JP 2011506055A JP 5746966 B2 JP5746966 B2 JP 5746966B2
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- JP
- Japan
- Prior art keywords
- acrylic copolymer
- weight
- compound
- adhesive composition
- sensitive adhesive
- 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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- 239000000203 mixture Substances 0.000 title claims description 124
- 230000001070 adhesive effect Effects 0.000 title claims description 31
- 239000000853 adhesive Substances 0.000 title claims description 29
- 229920006243 acrylic copolymer Polymers 0.000 claims description 159
- -1 isocyanate compound Chemical class 0.000 claims description 131
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 103
- 239000012948 isocyanate Substances 0.000 claims description 79
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Chemical group C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 76
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Chemical group O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 76
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Chemical group OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 74
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 66
- 125000000524 functional group Chemical group 0.000 claims description 42
- 229920001577 copolymer Polymers 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 239000012788 optical film Substances 0.000 claims description 30
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 238000004132 cross linking Methods 0.000 claims description 15
- 239000004973 liquid crystal related substance Substances 0.000 claims description 9
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 8
- 238000013329 compounding Methods 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 5
- 210000002858 crystal cell Anatomy 0.000 claims description 5
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- 239000000178 monomer Substances 0.000 description 49
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 35
- 241000519995 Stachys sylvatica Species 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 20
- 238000011156 evaluation Methods 0.000 description 18
- 239000010408 film Substances 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- 239000004593 Epoxy Substances 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000003431 cross linking reagent Substances 0.000 description 10
- 238000005187 foaming Methods 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 150000004756 silanes Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin 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
- 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 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- 239000012790 adhesive layer Substances 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 8
- 229910000077 silane Inorganic materials 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 230000001747 exhibiting effect Effects 0.000 description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000001629 suppression Effects 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010382 chemical cross-linking Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 2
- FVCHRIQAIOHAIC-UHFFFAOYSA-N 2-[1-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COC(C)COCC1CO1 FVCHRIQAIOHAIC-UHFFFAOYSA-N 0.000 description 2
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 2
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
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- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- SJPFBRJHYRBAGV-UHFFFAOYSA-N n-[[3-[[bis(oxiran-2-ylmethyl)amino]methyl]phenyl]methyl]-1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC=1C=C(CN(CC2OC2)CC2OC2)C=CC=1)CC1CO1 SJPFBRJHYRBAGV-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
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- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
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- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 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 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- QWOVEJBDMKHZQK-UHFFFAOYSA-N 1,3,5-tris(3-trimethoxysilylpropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound CO[Si](OC)(OC)CCCN1C(=O)N(CCC[Si](OC)(OC)OC)C(=O)N(CCC[Si](OC)(OC)OC)C1=O QWOVEJBDMKHZQK-UHFFFAOYSA-N 0.000 description 1
- ZIZJPRKHEXCVLL-UHFFFAOYSA-N 1,3-bis(6-isocyanatohexyl)-1,3-diazetidine-2,4-dione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C1=O ZIZJPRKHEXCVLL-UHFFFAOYSA-N 0.000 description 1
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- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- KQSMCAVKSJWMSI-UHFFFAOYSA-N 2,4-dimethyl-1-n,1-n,3-n,3-n-tetrakis(oxiran-2-ylmethyl)benzene-1,3-diamine Chemical compound CC1=C(N(CC2OC2)CC2OC2)C(C)=CC=C1N(CC1OC1)CC1CO1 KQSMCAVKSJWMSI-UHFFFAOYSA-N 0.000 description 1
- JJZYPAHZQPAADA-UHFFFAOYSA-N 2-(2,5-dioxooxolan-3-yl)-4-triethoxysilylbutanoic acid Chemical compound CCO[Si](OCC)(OCC)CCC(C(O)=O)C1CC(=O)OC1=O JJZYPAHZQPAADA-UHFFFAOYSA-N 0.000 description 1
- RTWQQWAWHUMBRA-UHFFFAOYSA-N 2-(3-diethoxysilylpropyl)-3-methylbutanedioic acid Chemical compound CC(C(C(=O)O)CCC[SiH](OCC)OCC)C(=O)O RTWQQWAWHUMBRA-UHFFFAOYSA-N 0.000 description 1
- RTVBWUXFULQISX-UHFFFAOYSA-N 2-(3-dimethoxysilylpropyl)-3-methylbutanedioic acid Chemical compound CC(C(C(=O)O)CCC[SiH](OC)OC)C(=O)O RTVBWUXFULQISX-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
- FSCQZUXYTLYEIR-UHFFFAOYSA-N 2-(3-triethoxysilylpropyl)butanedioic acid Chemical compound CCO[Si](OCC)(OCC)CCCC(CC(O)=O)C(O)=O FSCQZUXYTLYEIR-UHFFFAOYSA-N 0.000 description 1
- AHNLTPNNRFETEC-UHFFFAOYSA-N 2-(3-trimethoxysilylpropyl)butanedioic acid Chemical compound CO[Si](OC)(OC)CCCC(C(O)=O)CC(O)=O AHNLTPNNRFETEC-UHFFFAOYSA-N 0.000 description 1
- JJRUAPNVLBABCN-UHFFFAOYSA-N 2-(ethenoxymethyl)oxirane Chemical compound C=COCC1CO1 JJRUAPNVLBABCN-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- RQZUWSJHFBOFPI-UHFFFAOYSA-N 2-[1-[1-(oxiran-2-ylmethoxy)propan-2-yloxy]propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COC(C)COCC1CO1 RQZUWSJHFBOFPI-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- AGXAFZNONAXBOS-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethyl)phenyl]methyl]oxirane Chemical compound C=1C=CC(CC2OC2)=CC=1CC1CO1 AGXAFZNONAXBOS-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- C08F220/10—Esters
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Description
(1)カルボキシル基を含有するアクリル系共重合体(A)と、イソシアネート化合物(B)と、水酸基とロジン骨格とを有する化合物(C)とを含み、架橋構造及び多量体が形成された後におけるゲル分が45重量%以上であり、水酸基とロジン骨格とを有する前記化合物(C)と、前記イソシアネート化合物(B)との配合量比率が重量基準で0.3以上3以下であることを特徴とする、光学フィルムを液晶セルに貼着する際に用いる粘着剤組成物。
(2)カルボキシル基と水酸基とを含有するアクリル系共重合体(D)を更に含む上記(1)に記載の粘着剤組成物(前記カルボキシル基を含有するアクリル系共重合体(A)が水酸基を含有するものは除く)。
(3)水酸基とロジン骨格とを有する前記化合物(C)が、分子内に下記式(1)で示す骨格を有する化合物である上記(1)または(2)に記載の粘着剤組成物。
(5)前記アクリル系共重合体の合計量100重量部に対し、水酸基とロジン骨格を有する前記化合物(C)を1重量部以上20重量部以下含む上記(1)〜(4)の何れかに記載の粘着剤組成物。
(6)前記イソシアネート化合物(B)のイソシアネート基と架橋反応する前記アクリル系共重合体の反応性官能基の合計1当量に対するイソシアネート基の当量の比率が1より大きく5以下であり、前記反応性官能基は、カルボキシル基、水酸基、グリシジル基、アミド基,N−置換アミド基、三級アミノ基のいずれか1種又は2種以上である上記(1)〜(5)の何れか一項に記載の粘着剤組成物。
(7)前記アクリル系共重合体(D)が、共重合体成分としてt−ブチルアクリレートを含む上記(2)〜(6)の何れかに記載の粘着剤組成物。
(単独系粘着剤組成物)
本発明の第1の実施の形態に係る粘着剤組成物は、反応性官能基を含有するアクリル系共重合体(A)と、イソシアネート化合物(B)と、水酸基とロジン骨格とを有する化合物(C)とを含有する。第1の実施の形態に係る粘着剤組成物は、アクリル系共重合体(A)の反応性官能基とイソシアネート化合物(B)とが架橋反応すると共に、イソシアネート化合物(B)の架橋反応に寄与しなかったイソシアネート基が養生環境中の水や、水酸基とロジン骨格とを有する化合物(C)と反応することで多量体を形成し、それにより良好な粘着特性を有すると考えられる。
(重量平均分子量(Mw)の測定方法)
下記(1)〜(3)に従って測定する。
(1)アクリル系共重合体溶液を剥離紙に塗布し、100℃で2分間乾燥し、フィルム状のアクリル系共重合体を得る。
(2)前記(1)で得られたフィルム状のアクリル系共重合体をテトラヒドロフランにて固形分0.2%になるように溶解させる。
(3)下記条件にて、ゲルパーミエーションクロマトグラフィー(GPC)を用いて、アクリル系共重合体の重量平均分子量(Mw)を測定する。
(条件)
GPC:HLC−8220 GPC〔東ソー(株)製〕
カラム:TSK−GEL GMHXL4本使用
移動相溶媒:テトラヒドロフラン
標準試料:標準ポリスチレン
流速:0.6ml/minカラム温度:40℃
式1 1/Tg=M1/Tg1+M2/Tg2+M3/Tg3+・・・・+Mn/Tgn
式中、Tg1、Tg2、Tg3・・・及びTgnは、成分1、成分2、成分3・・・及び成分nそれぞれのホモポリマーのガラス転移温度(K)を示す。また、式中、M1、M2、M3・・・及びMnは各種成分のモル分率を示す。
(粘着剤組成物のゲル分の測定)
下記(1)〜(6)に従って測定する。
(1)粘着剤組成物の溶液をシリコーン系離型剤で表面処理された剥離シートに、乾燥後の塗工量が25g/m 2 となるように塗布し、100℃で90秒間熱風循環式乾燥機にて乾燥し、フィルム状の感圧接着剤層を形成する。
(2)形成された感圧接着剤層を23℃、湿度65%RHで10日間養生する。
(3)精秤した250メッシュの金網(100mm×100mm)に(2)で得られたフィルム状粘着剤層を約0.25g貼付し、ゲル分が漏れないように包む。その後、精密天秤にて重量を正確に測定して試料を作製する。
(4)前記の金網を酢酸エチル溶液に3日間浸漬する。
(5)浸漬後、金網を取り出して少量の酢酸エチルにて洗浄し、120℃で24時間乾燥させる。その後、精密天秤にて重量を正確に測定する。
(6)下式によりゲル分を計算する。
ゲル分(重量%)=(C−A)/(B−A)×100
但し、Aは金網の重量(g)、Bは粘着剤を貼付した金網の重量(B−Aは粘着剤重量)(g)、Cは浸漬後、乾燥させた金網の重量(C−Aはゲル樹脂重量)(g)である。
第1の実施の形態に係る粘着剤組成物、この粘着剤組成物からなる粘着剤層を備える光学フィルムは、上述した構成を備えるので、アクリル系共重合体(A)の反応性官能基と架橋剤の反応による化学架橋と、イソシアネート化合物(B)の架橋反応に寄与していないイソシアネート基が養生環境にある水や、水酸基とロジン骨格とを有する化合物(C)と反応することで生成する反応物としての多量体を形成し、アクリル系共重合体の分子鎖の動きを拘束する物理架橋とにより高い凝集力を有していると考えられる為、耐久性が良好であり、分子鎖の動きを拘束している物理架橋部分には流動性もあるために応力緩和性にも優れていると考えられ、耐久性と白抜けの抑制とを高い水準で併せ持つことができる。
(混合系粘着剤組成物)
第2の実施の形態に係る粘着剤組成物は、反応性官能基を含有するアクリル系共重合体(A)と、アクリル系共重合体(A)とは異なる、反応性官能基を含有するアクリル系共重合体(D)と、イソシアネート化合物(B)と、水酸基とロジン骨格とを有する化合物(C)とを含有する。すなわち、第2の実施の形態に係る粘着剤組成物は、アクリル系共重合体(D)を更に含有する点を除き第1の実施の形態に係る粘着剤組成物と略同一の構成を備える。したがって、相違点を除き、詳細な説明は省略する。なお、第2の実施の形態に係る粘着剤組成物においても、アクリル系共重合体(A)及びアクリル系共重合体(D)の反応性官能基とイソシアネート化合物(B)とが架橋反応すると共に、イソシアネート化合物(B)のうち架橋反応に寄与しなかったイソシアネート化合物(B)のイソシアネート基が養生環境中の水や、水酸基とロジン骨格とを有する化合物(C)と反応することで生成する反応物としての多量体を形成し、それにより良好な粘着特性を有すると考えられる。
式2 溶解性パラメーター=√[ΣEcoh/ΣV]
式2中、Ecohは凝集エネルギー密度、Vはモル分子容である。原子団ごとに決められたEcoh、及びVに基づき、高分子の繰り返し単位におけるEcoh、及びVの総和ΣEcoh、並びにΣVを求めることによって、溶解性パラメーターを算出することができる。共重合体の溶解性パラメーターは、上記式2によりその共重合体を構成する各構成単位のそれぞれの単独重合体の溶解性パラメーターを算出し、これらのSP値のそれぞれに各構成単位のモル分率を乗じたものを合算して算出される。
光学フィルムの一例として偏光フィルムを使用し粘着剤層を有する偏光フィルムを作製した。シリコーン系離型剤で表面処理された剥離フィルム上に、乾燥後の塗工量が25g/cm2となるように、粘着剤組成物を塗布した。次に、100℃で90秒間熱風循環式乾燥機にて乾燥して粘着剤層を形成した。続いて、偏光ベースフィルム〔ポリビニルアルコール(PVA)フィルムを主体とする偏光子の両面にセルローストリアセテート(TAC)フィルムをラミネートしたもの;約190μm〕の裏面に粘着剤層面を貼り合せ、加圧ニップロールに通して圧着した。圧着後、23℃、65%RHで10日間養生させて粘着剤層を有する偏光フィルムを得た。
「(1)試験用光学フィルムの作製」において作製した偏光フィルムを、光の吸収軸に対して長辺が45゜になるようにカットした140mm×260mm(長辺)の試験片を用い、0.7mmコーニング社製無アルカリガラス板「#1737」の片面にラミネーターを用いて貼付した。次に、このサンプルにオートクレーブ処理(50℃、5kg/cm2、20分)を施し、23℃、65%RHの条件下で24時間放置した。その後、80℃DRY、105℃DRY、及び60℃90%RHの環境下にそれぞれ1000時間放置し、発泡、剥れの状態を目視観察にて評価した。評価基準は次の通りである。
a)発泡
○:発泡が全く見られない
△:発泡がほとんど見られない
×:発泡が顕著に見られる
○:4辺において、剥がれが無いもの。
△:4辺において、外周端部から0.3mm以上の位置に剥がれが無いもの。
×:4辺のいずれか1辺に、外周端部から0.3mm以上の位置に剥がれがあるもの。
「(2)耐久性の評価」と同様のサイズの粘着剤層を有する偏光フィルムを0.7mmコーニング社製無アルカリガラス板「#1737」の両面に、偏光軸が互いに直交するように貼付した試験サンプルを作製した。次に、このサンプルにオートクレーブ処理(50℃、5kg/cm2、20分)を施し、23℃、50%RHの条件下で24時間放置した。その後、80℃、ドライの条件下に500時間、放置した。放置後、23℃、50%RHの条件下で均一光源(株式会社アイ・システム製)を使用し、EyeScale−3W(株式会社アイ・システム製)にて17×31点(527点)の輝度を測定し、それらの最大輝度値(cd/m2)と輝度が6cd/m2以上である測定点の個数を数え、下記式3により白抜け評価指数を求め、以下の評価基準により白抜け状態を評価した。
式3 白抜け評価指数=最大輝度値×(輝度が6cd/m2以上である測定点数)
(白抜け評価基準)
◎:白抜け評価指数が0以上100未満。
○:白抜け評価指数が100以上400未満。
×:白抜け評価指数が400以上。
(製造例1)
温度計、攪拌機、窒素導入管、及び還流冷却管を備えた反応器内に、n−ブチルアクリレート(BA)99重量部、アクリル酸(AA)1重量部、酢酸エチル(EAc)100重量部、及びアゾビスイソブチロニトリル(AIBN)0.1重量部を入れ、反応容器の空気を窒素ガスで置換した。その後、攪拌下、窒素雰囲気中で、反応容器の内容物温度を65℃に昇温させて8時間反応させた。反応終了後、反応混合物を酢酸エチルで希釈し、固形分16.8重量%のアクリル系共重合体溶液を得た。アクリル系重合体の重量平均分子量は167万であった。
製造例1で使用した共重合体組成の代わりに、共重合体組成を表1の各製造例に示した単量体組成とした以外は製造例1と同様にして重合した。表1に、各製造例の共重合体組成、固形分、ガラス転移点(Tg)、溶解性パラメーター(SP値)、重量平均分子量(Mw)を示した。
(製造例4)
温度計、攪拌機、窒素導入管、及び還流冷却管を備えた反応器内に、n−ブチルアクリレート(BA)99重量部、アクリル酸(AA)1重量部、酢酸エチル(EAc)92重量部、及びアゾビスイソブチロニトリル(AIBN)0.1重量部を入れ、反応容器の空気を窒素ガスで置換した。その後、攪拌下、窒素雰囲気中で、反応容器の内容物温度を65℃に昇温させて8時間反応させた。反応終了後、反応混合物を酢酸エチルで希釈し、固形分18.9重量%のアクリル系共重合体溶液を得た。アクリル系重合体の重量平均分子量は214万であった。
製造例4で使用した共重合体組成の代わりに、共重合体組成を表1の製造例5に示した単量体組成とした以外は製造例4と同様にして重合した。
(実施例1)
アクリル系共重合体(A)として製造例1で合成したアクリル共重合体溶液を506重量部(アクリル系共重合体(A)として85重量部)、アクリル系共重合体(D)として製造例2で合成したアクリル系共重合体溶液を76重量部(アクリル共重合体(D)として15重量部)、イソシアネート化合物(B)としてコロネートL9.3重量部(日本ポリウレタン社製イソシアネート系化合物、有効成分7重量部)、エポキシ化合物としてTETRAD−X0.02重量部(三菱瓦斯化学社製のエポキシ化合物、有効成分0.02重量部)、水酸基とロジン骨格とを有する化合物(C)としてD−6011 5重量部(荒川化学工業社製のロジン含有ジオール、有効成分5重量部)、シラン化合物としてKBM−403 0.1重量部(信越化学工業社製シランカップリング剤、有効成分0.1重量部)を十分に攪拌混合して粘着剤組成物を得た。アクリル系共重合体(A)とアクリル系共重合体(D)の反応性官能基の合計1当量に対するイソシアネート基の当量(表2及び表3に、「NCO/樹脂官能基」として記載)は2.01当量であった。得られた粘着剤組成物を使用して、前記のゲル分の測定方法により試験を行い、その結果を表2に示す。更に、得られた粘着剤組成物を使用して、前記の試験用光学フィルムの作製方法により試験用光学フィルムを作製し、前記の各種測定を行い、その結果を表4に示す。
実施例1における配合組成の代わりに、表2及び表3に示した各実施例、及び比較例の配合組成を採用する以外は実施例1と同様にして粘着剤組成物(実施例2乃至15に係る粘着剤組成物、及び比較例1乃至4に係る粘着剤組成物)を作製した。得られた粘着剤組成物を使用して、前記のゲル分の測定方法により試験を行い、その結果を表2及び表3に示す。更に、得られた粘着剤組成物を使用して、前記の試験用光学フィルムの作製方法により試験用光学フィルムを作製し、前記の各種測定を行い、その結果を表4及び表5に示す。
(a)コロネートL「日本ポリウレタン社製のイソシアネート系化合物」
商品名;コロネートL、有効成分75%
トリメチロールプロパン変性トリレンジイソシアネート
イソシアネート化合物(B)成分
(b)TETRAD−X「三菱瓦斯化学社製のエポキシ化合物」
商品名;TETRAD−X、有効成分100%
化学名;N、N、N’、N’−テトラグリシジル−m−キシレンジアミン
エポキシ化合物
(c)D−6011「荒川化学工業社製のロジン含有ジオール」
商品名;パインクリスタルD−6011、有効成分100%
式(2)で示される水酸基とロジン骨格とを有する化合物(C)成分
(d)KE−359「荒川化学工業社製の水酸基含有ロジンエステル」
商品名;パインクリスタルKE−359、有効成分100%
水酸基とロジン骨格とを有する化合物(C)成分
(e)FTR−6100「三井化学社製 石油系粘着付与樹脂」
商品名;FTR−6100、有効成分100%
(f)KBM−403「信越化学工業社製のシランカップリング剤」
商品名;KBM−403、有効成分100%
化学名;3−グリシドキシプロピルトリメトキシシラン、
シラン化合物成分
KE−100「荒川化学工業社製ロジンエステル」
商品名;パインクリスタルKE−100
Claims (7)
- カルボキシル基を含有するアクリル系共重合体(A)と、イソシアネート化合物(B)と、水酸基とロジン骨格とを有する化合物(C)とを含み、
架橋構造及び多量体が形成された後におけるゲル分が45重量%以上であり、
水酸基とロジン骨格とを有する前記化合物(C)と、前記イソシアネート化合物(B)との配合量比率が重量基準で0.3以上3以下であることを特徴とする、光学フィルムを液晶セルに貼着する際に用いる粘着剤組成物。 - カルボキシル基と水酸基とを含有するアクリル系共重合体(D)を更に含む請求項1に記載の粘着剤組成物(前記カルボキシル基を含有するアクリル系共重合体(A)が水酸基を含有するものは除く)。
- 前記アクリル系共重合体の合計量100重量部に対し、前記イソシアネート化合物(B)を5重量部以上20重量部以下含む請求項1〜3のいずれか一項に記載の粘着剤組成物。
- 前記アクリル系共重合体の合計量100重量部に対し、水酸基とロジン骨格とを有する前記化合物(C)を1重量部以上20重量部以下含む請求項1〜4のいずれか一項に記載の粘着剤組成物。
- 前記イソシアネート化合物(B)のイソシアネート基と架橋反応する前記アクリル系共重合体の反応性官能基の合計1当量に対するイソシアネート基の当量の比率が1より大きく5以下であり、
前記反応性官能基は、カルボキシル基、水酸基、グリシジル基、アミド基,N−置換アミド基、三級アミノ基のいずれか1種又は2種以上である請求項1〜5のいずれか一項に記載の粘着剤組成物。 - 前記アクリル系共重合体(D)が、共重合体成分としてt−ブチルアクリレートを含む請求項2〜6のいずれか一項に記載の粘着剤組成物。
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JP4744262B2 (ja) | 2005-10-18 | 2011-08-10 | 日東電工株式会社 | 粘着剤組成物、粘着剤層およびその製造方法、ならびに粘着剤付光学部材 |
KR100932888B1 (ko) * | 2006-07-21 | 2009-12-21 | 주식회사 엘지화학 | 광학 보상된 아크릴계 점착제 조성물, 이를 포함하는편광판 및 액정표시소자 |
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2010
- 2010-03-23 KR KR1020117025028A patent/KR101718558B1/ko active IP Right Grant
- 2010-03-23 EP EP10756050A patent/EP2412776A4/en not_active Withdrawn
- 2010-03-23 WO PCT/JP2010/054957 patent/WO2010110254A1/ja active Application Filing
- 2010-03-23 US US13/258,010 patent/US9309348B2/en active Active
- 2010-03-23 JP JP2011506055A patent/JP5746966B2/ja active Active
- 2010-03-23 CN CN201080013098.4A patent/CN102361948B/zh active Active
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Patent Citations (6)
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JPH07228852A (ja) * | 1994-02-17 | 1995-08-29 | Sekisui Chem Co Ltd | 粘着剤組成物及び粘着加工品 |
JPH09263742A (ja) * | 1996-03-28 | 1997-10-07 | Sekisui Chem Co Ltd | 粘着剤組成物及びそれを用いた粘着加工品 |
JPH10204399A (ja) * | 1997-01-24 | 1998-08-04 | Sekisui Chem Co Ltd | アクリル系粘着剤組成物 |
JPH10298528A (ja) * | 1997-04-30 | 1998-11-10 | Arakawa Chem Ind Co Ltd | ポリエステル系接着剤用粘着付与樹脂およびポリエステル系接着剤組成物 |
JP2005146231A (ja) * | 2003-11-20 | 2005-06-09 | Sanyo Chem Ind Ltd | 反応性ホットメルト接着剤 |
WO2008111412A1 (ja) * | 2007-03-09 | 2008-09-18 | Sekisui Chemical Co., Ltd. | 粘着剤、両面粘着シート及び表示装置 |
Also Published As
Publication number | Publication date |
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TW201041993A (en) | 2010-12-01 |
JPWO2010110254A1 (ja) | 2012-09-27 |
US20120010341A1 (en) | 2012-01-12 |
EP2412776A1 (en) | 2012-02-01 |
CN102361948B (zh) | 2016-01-06 |
KR20120011855A (ko) | 2012-02-08 |
TWI522436B (zh) | 2016-02-21 |
KR101718558B1 (ko) | 2017-03-21 |
WO2010110254A1 (ja) | 2010-09-30 |
EP2412776A4 (en) | 2013-03-13 |
US9309348B2 (en) | 2016-04-12 |
CN102361948A (zh) | 2012-02-22 |
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