CN117683491A - Adhesive composition, adhesive layer, optical film with adhesive layer, and display device - Google Patents
Adhesive composition, adhesive layer, optical film with adhesive layer, and display device Download PDFInfo
- Publication number
- CN117683491A CN117683491A CN202311103087.0A CN202311103087A CN117683491A CN 117683491 A CN117683491 A CN 117683491A CN 202311103087 A CN202311103087 A CN 202311103087A CN 117683491 A CN117683491 A CN 117683491A
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- Prior art keywords
- meth
- parts
- mass
- acrylic polymer
- adhesive composition
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- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 239000000853 adhesive Substances 0.000 title claims abstract description 68
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 68
- 239000012790 adhesive layer Substances 0.000 title claims abstract description 56
- 239000012788 optical film Substances 0.000 title claims abstract description 11
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 111
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 97
- 239000000178 monomer Substances 0.000 claims description 92
- -1 isocyanate compound Chemical class 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000000470 constituent Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 15
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 14
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 11
- 239000002216 antistatic agent Substances 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 6
- 239000013522 chelant Substances 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 125000001033 ether group Chemical group 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 238000011156 evaluation Methods 0.000 description 26
- 239000011521 glass Substances 0.000 description 25
- 239000010408 film Substances 0.000 description 22
- 239000000758 substrate Substances 0.000 description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 19
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 17
- 238000005187 foaming Methods 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 239000004973 liquid crystal related substance Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003505 polymerization initiator Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 239000012986 chain transfer agent Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 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 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- ZHCHRKVXJJJZFX-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]-1-phenoxyethanol Chemical compound OCCOCCOCC(O)OC1=CC=CC=C1 ZHCHRKVXJJJZFX-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- 101150000419 GPC gene Proteins 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 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 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing 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
- 125000002347 octyl 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])[H] 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003573 thiols Chemical class 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
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- ZICNIEOYWVIEQJ-UHFFFAOYSA-N (2-methylbenzoyl) 2-methylbenzenecarboperoxoate Chemical compound CC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1C ZICNIEOYWVIEQJ-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical class ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- NKVCQMYWYHDOOF-UHFFFAOYSA-N 1-phenoxyethane-1,2-diol Chemical compound OCC(O)OC1=CC=CC=C1 NKVCQMYWYHDOOF-UHFFFAOYSA-N 0.000 description 1
- COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- MCDBEBOBROAQSH-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl prop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C=C MCDBEBOBROAQSH-UHFFFAOYSA-N 0.000 description 1
- ZCRUJAKCJLCJCP-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]propyl prop-2-enoate Chemical compound CO[Si](C)(C)CCCOC(=O)C=C ZCRUJAKCJLCJCP-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-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
- RTANHMOFHGSZQO-UHFFFAOYSA-N 4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)C#N RTANHMOFHGSZQO-UHFFFAOYSA-N 0.000 description 1
- RRBONVXWAGQXDJ-UHFFFAOYSA-N 4-methoxybutyl 2-sulfanylacetate Chemical compound COCCCCOC(=O)CS RRBONVXWAGQXDJ-UHFFFAOYSA-N 0.000 description 1
- VIQGKXOVPDLASV-UHFFFAOYSA-N 4-methoxybutyl 2-sulfanylpropanoate Chemical compound COCCCCOC(=O)C(C)S VIQGKXOVPDLASV-UHFFFAOYSA-N 0.000 description 1
- JOVCTEPPTIOAPX-UHFFFAOYSA-N 8-trimethoxysilyloctyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCCCCCCOC(=O)C=C JOVCTEPPTIOAPX-UHFFFAOYSA-N 0.000 description 1
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- 239000004925 Acrylic resin Substances 0.000 description 1
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- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- XALVHDZWUBSWES-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;tributyl(methyl)azanium Chemical class CCCC[N+](C)(CCCC)CCCC.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F XALVHDZWUBSWES-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical class NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-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
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 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
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- MADOXCFISYCULS-UHFFFAOYSA-N octyl 2-sulfanylacetate Chemical compound CCCCCCCCOC(=O)CS MADOXCFISYCULS-UHFFFAOYSA-N 0.000 description 1
- SFHANYOFMGEJCT-UHFFFAOYSA-N octyl 2-sulfanylpropanoate Chemical compound CCCCCCCCOC(=O)C(C)S SFHANYOFMGEJCT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003050 poly-cycloolefin Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-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
- JPMBLOQPQSYOMC-UHFFFAOYSA-N trimethoxy(3-methoxypropyl)silane Chemical compound COCCC[Si](OC)(OC)OC JPMBLOQPQSYOMC-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
- C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
- C08L43/04—Homopolymers or copolymers of monomers containing silicon
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/068—Copolymers with monomers not covered by C09J133/06 containing glycidyl groups
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
The invention relates to an adhesive composition, an adhesive layer, an optical film with the adhesive layer and a display device. An adhesive composition which has improved durability in a high-temperature environment. An adhesive composition containing a first (meth) acrylic polymer (A) and a second (meth) acrylic polymer (B) is provided. The weight average molecular weight of the first (meth) acrylic polymer (A) is 30 to 350 ten thousand. The weight average molecular weight of the second (meth) acrylic polymer (B) is 3 to 40 ten thousand. In the adhesive composition, the second (meth) acrylic polymer (B) is contained in an amount of 1 to 50 parts by mass based on 100 parts by mass of the first (meth) acrylic polymer (a).
Description
Technical Field
The invention relates to an adhesive composition, an adhesive layer, an optical film with the adhesive layer and a display device.
Background
In recent years, liquid crystal display devices have been used in a wide variety of applications such as vehicle mounting, outdoor equipment, and personal computers. An adhesive layer composed of the adhesive composition adheres the polarizing plate to a liquid crystal element (glass substrate) of a liquid crystal display device. However, the polarizing plate may be peeled off from the glass substrate because the polarizing plate has a property of stretching in a high-temperature environment.
Based on the above-mentioned problems, patent document 1 discloses an optical pressure-sensitive adhesive composition having an acrylic polymer and an acrylic/silicone graft copolymer having a hydrolyzable silyl group. In addition, patent document 2 and patent document 3 disclose adhesive compositions having an acrylic polymer and an acrylic polymer having a hydrolyzable alkoxysilyl group. Further, patent document 4 discloses an adhesive composition having an acrylic oligomer type silane coupling agent containing a silane compound having an alkoxy group and an acrylic copolymer.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 2014-037502
Patent document 2: japanese patent application laid-open No. 2019-014778
Patent document 3: international publication No. 2017-098870
Patent document 4: japanese patent laid-open No. 2020-002225
Disclosure of Invention
Problems to be solved by the invention
However, the polymer of patent document 1 is not sufficiently durable because it is phase-separated from the acrylic polymer under a high-temperature environment. In addition, the acrylic oligomer of patent document 2 has a weight average molecular weight (Mw) of 400 to 5000, and the acrylic polymer having a hydrolyzable alkoxysilyl group have little interaction and have insufficient durability in a high-temperature environment. The adhesive compositions of patent document 3 and patent document 4 are also insufficient in durability under a high-temperature environment, as described above.
Accordingly, an object of the present invention is to provide an adhesive composition having improved durability under high-temperature environments.
Means for solving the problems
According to the present invention, there is provided an adhesive composition comprising a first (meth) acrylic polymer (a) and a second (meth) acrylic polymer (B), wherein the first (meth) acrylic polymer (a) comprises, as constituent units, 70 parts by mass or more and 100 parts by mass or less of a (meth) acrylic alkyl ester monomer (a 1), 0 parts by mass or more and 30 parts by mass or less of an aromatic group-containing (meth) acrylic ester monomer (a 2), and 0 parts by mass or more and 30 parts by mass or less of an aromatic group-containing (meth) acrylic ester monomer (a 2) relative to the total amount of 100 parts by mass or more of the (meth) acrylic alkyl ester monomer (a 1) and the aromatic group-containing (meth) acrylic ester monomer (a 2), 0.01 parts by mass or more and 10 parts by mass or less of a (meth) acrylic ester monomer (a 3) having a reactive functional group, and the first (meth) acrylic polymer (a) has a weight average molecular weight of 30 ten thousand or more and 350 ten thousand or less, and the second (meth) acrylic polymer (B) comprises, relative to the second (meth) acrylic polymer (B) comprises 0.01 parts by mass or more and 0 parts by mass or less of an aromatic group-containing (meth) acrylic ester monomer (B) from 0 parts by mass or more and 85 parts by mass or more of an aromatic group-containing (meth) acrylic ester monomer (B) from 0 parts by mass or more, and 15 to 70 parts by mass of an alkoxysilyl group-containing monomer (B3) as a constituent unit, wherein the weight average molecular weight of the second (meth) acrylic polymer (B) is 3 to 40 ten thousand, and the adhesive composition contains 1 to 50 parts by mass of the second (meth) acrylic polymer (B) per 100 parts by mass of the first (meth) acrylic polymer (a).
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention can provide an adhesive composition having improved durability in a high-temperature environment.
Detailed Description
Hereinafter, embodiments will be described in detail. The following embodiments are not limited to the inventions according to the patent claims, and all combinations of the features described in the embodiments are not essential to the inventions. Two or more of the features described in the embodiments may be combined arbitrarily.
< adhesive composition >
The adhesive composition of the present invention contains a first (meth) acrylic polymer (a) and a second (meth) acrylic polymer (B).
The adhesive composition according to one embodiment contains 1 to 50 parts by mass, preferably 2 to 25 parts by mass, of the second (meth) acrylic polymer (B) per 100 parts by mass of the first (meth) acrylic polymer (a).
(first (meth) acrylic Polymer (A))
The first (meth) acrylic polymer (a) according to one embodiment contains, as constituent units, 70 to 100 parts by mass of the (meth) acrylic acid alkyl ester monomer (a 1), 0 to 30 parts by mass of the (meth) acrylic acid ester monomer (a 2) having an aromatic group, and 0.01 to 10 parts by mass of the (meth) acrylic acid ester monomer (a 3) having a reactive functional group relative to 100 parts by mass of the total amount of the (meth) acrylic acid alkyl ester monomer (a 1) and the (meth) acrylic acid ester monomer (a 2) having an aromatic group.
The "first (meth) acrylic polymer (a)" in the present specification refers to a polymer obtained by polymerizing a monomer component containing at least (meth) acrylic acid ester as a polymerizable monomer, and has at least a structural unit derived from (meth) acrylic acid ester. In the present specification and the like, the expression "(meth) acrylic acid" means a compound containing both "acrylic acid" and "methacrylic acid". In the same manner, the expression "(meth) acrylate" is meant to include both "acrylate" and "methacrylate".
Examples of the (meth) acrylic acid ester include alkyl (meth) acrylate, hydroxyalkyl (meth) acrylate, alkoxyalkyl (meth) acrylate, aralkyl (meth) acrylate, aryl (meth) acrylate, and other (meth) acrylic acid esters. One or two or more of (meth) acrylic acid esters may be used alone.
((meth) acrylic acid alkyl ester monomer (a 1))
The first (meth) acrylic polymer (a) contains, as a constituent unit, 70 parts by mass or more and 100 parts by mass or less, preferably 80 parts by mass or more and 100 parts by mass or less of the alkyl (meth) acrylate monomer (a 1).
The alkyl group of the alkyl (meth) acrylate monomer (a 1) according to one embodiment is not less than C1 and not more than C14.
The alkyl (meth) acrylate monomer (a 1) includes, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isobornyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, lauryl (meth) acrylate, and the like. One of the alkyl (meth) acrylate monomers (a 1) may be used alone, or two or more of them may be used.
(aromatic group-containing (meth) acrylate monomer (a 2))
The first (meth) acrylic polymer (a) contains, as a constituent unit, 0 to 30 parts by mass, preferably 0 to 25 parts by mass, of an alkyl (meth) acrylate monomer (a 2) having an aromatic group.
The (meth) acrylate monomer (a 2) having an aromatic group includes, for example, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxyethylene glycol (meth) acrylate, phenoxytriethylene glycol (meth) acrylate, nonylphenoxy polyethylene glycol (meth) acrylate, and the like. The (meth) acrylate monomer (a 2) having an aromatic group may be used either alone or in combination of two or more.
((meth) acrylate monomer (a 3) having a reactive functional group)
The first (meth) acrylic polymer (a) contains, as a constituent unit, 0.01 to 10 parts by mass, preferably 0.1 to 7 parts by mass of a (meth) acrylate monomer (a 3) having a reactive functional group, based on 100 parts by mass of the total amount of the alkyl (meth) acrylate monomer (a 1) and the (meth) acrylate monomer (a 2) having an aromatic group. The first (meth) acrylic polymer (a) can form an adhesive layer excellent in durability under a high-temperature environment by containing the (meth) acrylate monomer (a 3) having a reactive functional group that reacts with the crosslinking agent (C) described later as a constituent unit in the above-described mass part range.
On the other hand, when the first (meth) acrylic polymer (a) contains the (meth) acrylate monomer (a 3) having a reactive functional group as a constituent unit in a smaller amount than the above-mentioned mass part range, the cohesive force of the adhesive layer is reduced and the adhesive layer foams in a high-temperature environment. In addition, when the first (meth) acrylic polymer (a) contains a (meth) acrylate monomer (a 3) having a reactive functional group in an amount larger than the above-mentioned range of parts by mass as a constituent unit, the cohesive force of the adhesive layer is too high, and the adhesion of the adhesive layer to the coating body and the substrate is lowered, and the adhesive layer may be peeled off from the coating body (for example, a glass substrate of a liquid crystal display device) or the substrate (for example, a polarizing plate).
The reactive functional group of the (meth) acrylate monomer (a 3) having a reactive functional group according to one embodiment is at least one of a hydroxyl group, an epoxy group, and a nitrogen-containing group.
Here, a transparent conductive layer (a thin film layer (such as an ITO layer) made of an oxide semiconductor) is sometimes formed on a glass substrate of a liquid crystal panel. The transparent conductive layer has a function as an antistatic layer for preventing malfunction due to static electricity and a function as a sensor electrode of the electrostatic capacitive touch screen. When the first (meth) acrylic polymer (a) contains the (meth) acrylate monomer (a 3) having a carboxyl group, the transparent conductive layer may be corroded or damaged by the adhesive composition. Therefore, the first (meth) acrylic polymer (a) may be selected according to the use of the adhesive composition, as long as it contains the (meth) acrylate monomer (a 3) having a carboxyl group as a constituent unit.
The (meth) acrylate monomer (a 3) having a reactive functional group contains, for example, a hydroxyl group-containing (meth) acrylate monomer such as 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, a carboxyl group-containing monomer such as (meth) acrylic acid and β -carboxyethyl (meth) acrylate, an epoxy group-containing monomer such as glycidyl (meth) acrylate or 4-hydroxybutyl (meth) acrylate glycidyl ether, and an amide-based monomer such as (meth) acrylamide or dimethylaminopropyl (meth) acrylamide. The (meth) acrylate monomer (a 3) having a reactive functional group may be used singly or in combination of one or more of the above.
(physical Properties)
The weight average molecular weight (GP C measurement, standard polystyrene conversion) of the first (meth) acrylic polymer (a) according to one embodiment is 30 to 350 ten thousand, preferably 120 to 250 ten thousand. In the case where the weight average molecular weight of the first (meth) acrylic polymer (a) is less than 30 ten thousand, sufficient durability cannot be imparted to the adhesive layer. On the other hand, when the weight average molecular weight of the first (meth) acrylic polymer (a) exceeds 350 ten thousand, the viscosity of the first (meth) acrylic polymer (a) becomes extremely high, and the coatability of the adhesive composition is deteriorated.
The first (meth) acrylic polymer (a) can be produced by usual solution polymerization, bulk polymerization, emulsion polymerization, suspension polymerization, or the like. In particular, the first (meth) acrylic polymer (a) is preferably produced using solution polymerization capable of obtaining the first (meth) acrylic polymer (a) in a solution manner. Thus, the first (meth) acrylic polymer (a) in a solution state can be directly used in the production of the adhesive composition of the present invention. The solvent used in the solution polymerization includes, for example, an organic solvent such as ethyl acetate, toluene, n-hexane, acetone, and methyl ethyl ketone.
(polymerization initiator)
Examples of the polymerization initiator used for polymerizing the above-mentioned components (a 1) to (a 3) include: oil-soluble organic peroxides such as 2, 4-dichlorobenzoyl peroxide, t-butyl perpivalate, benzoyl peroxide, o-methylbenzoyl peroxide, bis-3, 5-trimethylhexanoyl peroxide, octanoyl peroxide, t-butyl peroxy-2-ethylhexanoate, cyclohexanone peroxide, methylethyl ketone peroxide, dicumyl peroxide, lauroyl peroxide, hydroxydiisopropylbenzene peroxide, t-butyl hydroperoxide, and t-butyl peroxide, and oil-soluble azo compounds such as 2,2' -azobisisobutyronitrile, 2' -azobis (2, 4-dimethylpentanenitrile), and 2,2' - (2, 4-dimethyl-4-methoxypentanenitrile. The oil-soluble polymerization initiator is preferably an oil-soluble azo compound. The oil-soluble polymerization initiator may be used either singly or as combination of two or more.
(chain transfer agent)
In order to adjust the molecular weight of the first (meth) acrylic polymer (a), a chain transfer agent may be suitably used. The chain transfer agent includes, for example, thiols such as octyl mercaptoacetate, methoxybutyl mercaptoacetate, octyl mercaptopropionate, methoxybutyl mercaptopropionate, stearyl mercaptan, and lauryl mercaptan, and α -methylstyrene dimer, and the like, and one or two or more of them may be used alone. On the other hand, the first (meth) acrylic polymer (a) may be produced without using a conventionally known chain transfer agent.
(second (meth) acrylic Polymer (B))
The second (meth) acrylic polymer (B) according to one embodiment contains, as constituent units, from 0 to 85 parts by mass of the alkyl (meth) acrylate monomer (B1), from 0 to 85 parts by mass of the aromatic group-containing (meth) acrylate monomer (B2), and from 15 to 70 parts by mass of the alkoxysilyl group-containing monomer (B3) in 100 parts by mass of the second (meth) acrylic polymer (B).
The "second (meth) acrylic polymer (B)" in the present specification means a polymer obtained by polymerizing a monomer component containing at least (meth) acrylic acid ester as a polymerizable monomer, and has at least a structural unit derived from (meth) acrylic acid ester. In the present specification and the like, the expression "(meth) acrylic acid" means a compound including both "acrylic acid" and "methacrylic acid". In the same manner, the expression "(meth) acrylate" is meant to include both "acrylate" and "methacrylate".
Examples of the (meth) acrylic acid ester include alkyl (meth) acrylate, hydroxyalkyl (meth) acrylate, alkoxyalkyl (meth) acrylate, aralkyl (meth) acrylate, aryl (meth) acrylate, and other (meth) acrylic acid esters other than these. The (meth) acrylic acid ester may be used either as one of the above or as two or more of them.
((meth) acrylic acid alkyl ester monomer (b 1))
In the second (meth) acrylic polymer (B) according to one embodiment, 100 parts by mass of the second (meth) acrylic polymer (B) contains 0 to 85 parts by mass of the alkyl (meth) acrylate monomer (B1) as a constituent unit.
The alkyl group of the alkyl (meth) acrylate monomer (b 1) according to one embodiment is not less than C1 and not more than C14.
The alkyl (meth) acrylate monomer (b 1) includes, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isobornyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, lauryl (meth) acrylate, and the like. The alkyl (meth) acrylate monomer (a 1) may be used alone or in combination of two or more of the above.
(aromatic group-containing (meth) acrylate monomer (b 2))
The second (meth) acrylic polymer (B) having an aromatic group according to one embodiment contains, as a constituent unit, 0 to 85 parts by mass, preferably 0 to 70 parts by mass of the (meth) acrylic acid ester monomer (B2) having an aromatic group in 100 parts by mass of the second (meth) acrylic polymer (B).
The (meth) acrylate monomer (b 2) having an aromatic group includes, for example, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxytriethylene glycol (meth) acrylate, nonylphenoxy polyethylene glycol (meth) acrylate, and the like. The (meth) acrylate monomer (b 2) having an aromatic group may be used singly or in combination of two or more.
(monomer having alkoxysilyl group (b 3))
In the second (meth) acrylic polymer (B) according to one embodiment, the monomer (B3) having an alkoxysilyl group is contained in an amount of 15 to 70 parts by mass as a constituent unit in 100 parts by mass of the second (meth) acrylic polymer (B). The second (meth) acrylic polymer (B) contains the alkoxysilyl group-containing monomer (B3) in the above-described mass part range, and thus can improve adhesion to a coating or a substrate, and has good compatibility with the first (meth) acrylic polymer (a), and thus, sufficient interaction with the first (meth) acrylic polymer (a) occurs, and thus, durability of the adhesive layer in a high-temperature environment is improved. On the other hand, when the second (meth) acrylic polymer (B) contains less than 15 parts by mass of the monomer (B3) having an alkoxysilyl group, the alkoxysilyl group that reacts with the coating or the substrate becomes small, and therefore the adhesion to the coating or the substrate is insufficient, and the durability of the adhesive layer in a high-temperature environment is reduced. In addition, when the second (meth) acrylic polymer (B) contains more than 70 parts by mass of the monomer (B3) having an alkoxysilyl group, the compatibility with the first (meth) acrylic polymer (a) decreases, and thus the interaction with the first (meth) acrylic polymer (a) becomes small, and the durability of the adhesive layer in a high-temperature environment decreases.
The monomer (b 3) having an alkoxysilyl group includes, for example, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (. Beta. -methoxyethoxy) silane, 3- (meth) acryloxypropyl trimethoxysilane, 3- (meth) acryloxypropyl methyldimethoxysilane, 3- (meth) acryloxypropyl dimethylmethoxysilane, 3- (meth) acryloxypropyl triethoxysilane, 3- (meth) acryloxyoctyl trimethoxysilane, and the like. The monomer (b 3) having an alkoxysilyl group may be used either singly or as combination of two or more.
(other monomers)
The second (meth) acrylic polymer (B) may contain a vinyl monomer, a monomer having an ether group, and a monomer containing an amide group or a substituted amide group in addition to (B1) to (B3). The second (meth) acrylic polymer (B) according to one embodiment contains, as a constituent unit, any one of a vinyl monomer, an ether group-containing monomer, and an amide group-or substituted amide group-containing monomer in an amount of 5 to 50 parts by mass, preferably 10 to 35 parts by mass, per 100 parts by mass of the second (meth) acrylic polymer (B).
Examples of the vinyl monomer include conjugated diene monomers such as styrene, α -methylstyrene, vinyltoluene, divinylbenzene, vinylpyridine, vinylpyrrolidone, vinylcarbazole, vinyl acetate and acrylonitrile, butadiene, isoprene and chloroprene, halogenated ethylenes such as vinyl chloride and vinyl bromide, halogenated vinylidene chloride and the like.
The ether group-containing monomer includes, for example, methoxypolyethylene glycol (meth) acrylate, ethoxypolyethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, and the like.
The amide group-containing or substituted amide group-containing monomer includes, for example, (meth) acrylamide, N-dimethyl (meth) acrylamide, N-methyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, and the like.
(physical Properties)
The weight average molecular weight (GP C measurement, converted to standard polystyrene) of the second (meth) acrylic polymer (B) according to one embodiment is 3 to 40 tens of thousands, preferably 3 to 36 tens of thousands. Since the second (meth) acrylic polymer (B) has a weight average molecular weight in the above range, the interaction between the first (meth) acrylic polymer (a) and the second (meth) acrylic polymer (B) is properly generated, and the durability of the adhesive layer in a high-temperature environment is improved. On the other hand, when the weight average molecular weight of the second (meth) acrylic polymer (B) is less than 3 ten thousand, the interaction with the first (meth) acrylic polymer (a) decreases, and the durability of the adhesive layer in a high-temperature environment decreases. When the weight average molecular weight of the second (meth) acrylic polymer (B) is more than 40 ten thousand, the compatibility with the first (meth) acrylic polymer (a) decreases, the interaction with the first (meth) acrylic polymer (a) decreases, and the durability of the adhesive layer in a high-temperature environment decreases.
The second (meth) acrylic polymer (B) is produced by usual solution polymerization, bulk polymerization, emulsion polymerization, suspension polymerization, or the like. In particular, it is preferable to produce the second (meth) acrylic polymer (B) using solution polymerization that can obtain the second (meth) acrylic polymer (B) in a solution manner. Thus, the second (meth) acrylic polymer (B) in a solution state can be used directly in the production of the adhesive composition of the present invention. The solvent used in the solution polymerization includes, for example, an organic solvent such as ethyl acetate, toluene, n-hexane, acetone, and methyl ethyl ketone.
(polymerization initiator)
The polymerization initiator used for polymerizing the above-mentioned (b 1) to (b 3) and other monomers includes conventionally known oil-soluble organic peroxides, oil-soluble azo compounds, and the like, similarly to the case of producing the first (meth) acrylic polymer (a). The oil-soluble polymerization initiator is preferably an oil-soluble azo compound. The oil-soluble polymerization initiator may be used singly or in combination of two or more.
(chain transfer agent)
In order to adjust the molecular weight of the second (meth) acrylic polymer (B), a conventionally known chain transfer agent can be suitably used in the same manner as in the production of the first (meth) acrylic polymer (a). The chain transfer agent includes thiols, α -methylstyrene dimer, etc., and one of the above may be used alone, or two or more may be used. On the other hand, the second (meth) acrylic polymer (B) may be produced without using a conventionally known chain transfer agent.
(crosslinking agent (C))
The adhesive composition according to one embodiment contains 0.01 to 10 parts by mass, preferably 0.01 to 4 parts by mass of the crosslinking agent (C) per 100 parts by mass of the first (meth) acrylic polymer (a).
The crosslinking agent (C) according to one embodiment includes at least one of an isocyanate compound, a metal chelate compound, an epoxy compound, an aziridine compound, and a melamine compound. That is, the crosslinking agent (C) may be used singly or in combination of two or more.
The amount of the crosslinking agent (C) contained in the adhesive composition may be determined according to the amount and type of the (meth) acrylate monomer having a reactive functional group. When the blending amount of the crosslinking agent (C) is less than the above-mentioned range of parts by mass, the cohesive force of the adhesive layer is reduced, and the adhesive layer foams in a high-temperature environment. On the other hand, when the blending amount of the crosslinking agent (C) exceeds the above range of the mass part, the cohesive force of the adhesive layer is too high, and the polarizing plate attached to the glass substrate of the liquid crystal display device is peeled off from the glass substrate.
The isocyanate compound is a polyisocyanate compound having two or more isocyanate groups in 1 molecule. Examples of the polyisocyanate compound include adducts of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, toluene diisocyanate, isophorone diisocyanate and the like with trimethylolpropane and the like, isocyanurate compounds, biuret compounds and the like. The polyisocyanate compound is preferably toluene diisocyanate or a compound of xylylene diisocyanate.
The metal chelate includes metal chelates such as aluminum chelate, zirconium chelate, titanium chelate, and the like.
The epoxy compound includes epoxy resins having two or more epoxy groups in the molecule, in addition to bisphenol compounds, aliphatic glycidyl ether compounds, and biphenyl compounds.
(antistatic agent (D))
The adhesive composition according to one embodiment contains 1 to 200 parts by mass, preferably 1 to 25 parts by mass, of the antistatic agent (D) per 100 parts by mass of the first (meth) acrylic polymer (a).
The antistatic agent (D) according to one embodiment is a compound containing either fluorine or silicon (wherein M is an alkali metal and M is excluded + [(FSO 2 ) 2 N] － The case of the indicated compounds).
The antistatic agent (D) includes, for example, ethylmethylimidazolium bis (trifluoromethanesulfonyl) imide salt, ethylmethylimidazolium bis (fluorosulfonyl) imide salt, 4-methyl-1-octylpyridinium bis (trifluoromethanesulfonyl) imide salt, 4-methyl-1-octylpyridinium bis (fluorosulfonyl) imide salt, tributyl methylammonium bis (trifluoromethanesulfonyl) imide salt, tributyl benzylammonium bis (fluorosulfonyl) imide salt, lauryl trimethylammonium bis (fluorosulfonyl) imide salt, 1-octyl-4-methylpyridinium hexafluorophosphate, and the like. The antistatic agent (D) may be used singly or in combination of two or more of the above.
(other additives)
The adhesive composition may further contain a silane coupling agent (E). On the other hand, the adhesive composition may not contain the silane coupling agent (E). The silane coupling agent (E) may be a known silane coupling agent. The adhesive composition according to one embodiment contains 0.05 to 3.0 parts by mass, preferably 0.1 to 1.5 parts by mass of the silane coupling agent (E) per 100 parts by mass of the first (meth) acrylic polymer (a).
Examples of the silane coupling agent (E) include epoxy group-containing silane coupling agents such as gamma-glycidoxypropyl trimethoxysilane, gamma-glycidoxypropyl triethoxysilane, gamma-glycidoxypropyl methyl dimethoxysilane, gamma-glycidoxypropyl methyl diethoxysilane, beta- (3, 4-epoxycyclohexyl) ethyl trimethoxysilane, epoxy group-containing alkoxysilane oligomer, etc., amino group-containing silane coupling agents such as gamma-mercaptopropyl trimethoxysilane, gamma-mercaptopropyl triethoxysilane, gamma-mercaptopropyl methyl dimethoxysilane, gamma-mercaptopropyl methyl diethoxysilane, mercapto group-containing alkoxysilane oligomer, etc., gamma-aminopropyl trimethoxysilane, gamma-aminopropyl triethoxysilane, N-beta- (aminoethyl) -gamma-aminopropyl trimethoxysilane, N-beta- (aminoethyl) -gamma-aminopropyl methyl dimethoxysilane, N-phenyl-gamma-aminopropyl trimethoxysilane, etc., and coupling agents such as gamma-aminopropyl trimethoxysilane, gamma-isocyanate-triethoxysilane, etc. The silane coupling agent (E) may be used singly or in combination of two or more of the above.
The adhesive composition may further contain various additives depending on the desired properties such as adjustment of adhesion. Examples of the additives include terpene-based, terpene-phenol-based, coumarone indene-based, styrene-based, rosin-based, xylene-based, phenol-based, petroleum-based and other tackifying resins, antioxidants, ultraviolet absorbers, fillers, pigments and the like. One or two or more of the above additives may be used singly.
< adhesive layer >)
The pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition of the present invention can be obtained by applying a predetermined amount of the pressure-sensitive adhesive composition to a release film, and curing and drying the pressure-sensitive adhesive composition. The thickness of the adhesive layer according to one embodiment is preferably 10 to 50. Mu.m, more preferably 10 to 25. Mu.m. By setting the thickness of the pressure-sensitive adhesive layer to be within the above-described range, a pressure-sensitive adhesive sheet which is excellent in durability and antistatic property can be formed. Further, with the adhesive sheet of the present invention, for example, by attaching a polarizing plate to a glass substrate of a liquid crystal display device, the glass substrate and the polarizing plate can be firmly attached. The pressure-sensitive adhesive layer can adhere the coating materials made of any organic material, the coating materials made of any inorganic material, or the coating materials made of any organic material and the coating materials made of any inorganic material to each other.
< adhesive sheet >
An adhesive sheet having an adhesive layer formed of the adhesive composition according to one embodiment is used to attach a polarizing plate to a coating body. The pressure-sensitive adhesive sheet has a release film or the like and a pressure-sensitive adhesive layer formed on the release film or the like. One of the adhesive surfaces of the adhesive layer is attached to the polarizing plate, and the other adhesive surface is attached to a release film or the like. The release film or the like attached to the other adhesive surface of the adhesive sheet can be peeled off and attached to the coating body.
In addition, the adhesive sheet of the present invention has an effect of excellent durability under severe environmental conditions. For example, in a severe environment of high temperature (105 ℃ C. Or 115 ℃) or high temperature and high humidity, the polarizing plate attached to the glass substrate using the adhesive sheet does not peel off from the glass substrate, and the adhesive layer does not foam. This can suppress degradation of the display quality of the liquid crystal display device. The polarizing plate to which the adhesive sheet of the present invention can be applied is a conventionally known polarizing plate. Examples of the polarizing plate include a polarizing plate using an untreated TAC film, a polarizing plate coated or uncoated with discotic liquid crystal, a polarizing plate having a stretched film (for example, a stretched triacetyl cellulose film, a stretched polycycloolefin film, or a stretched cellulose acetate propionate film) as a base material, and the like.
The pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer formed on a release film or the like can be produced by the following steps. A prescribed amount of the adhesive composition is applied to a release film such as a polyethylene terephthalate film (PET film) coated with a release agent such as silicone resin on the surface thereof by using a general coating device (for example, a roll coating device) and dried. Thus, an adhesive sheet having an adhesive layer formed on the release film was obtained. The surface of the pressure-sensitive adhesive layer on the side not in contact with the release film may be directly bonded to the polarizing plate. Alternatively, the pressure-sensitive adhesive sheet may be stored in a state where the release film is present on both sides of the pressure-sensitive adhesive layer, and the release film may be peeled off as needed to attach the pressure-sensitive adhesive layer to the polarizing plate. In addition, depending on the constituent material of the adhesive composition, the adhesive layer may be formed on the release film by heat crosslinking or photo-curing with ultraviolet rays or the like.
Optical film with adhesive layer
The optical film with an adhesive layer of the present invention includes an adhesive layer on at least one surface of the optical film. The optical film according to one embodiment includes, for example, a plastic film such as polystyrene, styrene-acrylic copolymer, acrylic resin, polyethylene terephthalate, polycarbonate, polyether ether ketone, or triacetyl cellulose, an antireflection film, an electromagnetic wave shielding film, or the like.
< display device >)
The display device of the present invention includes the optical film with an adhesive layer described above, and is, for example, a liquid crystal display device or an organic EL display. The liquid crystal display device is formed by bonding a polarizing plate, a laminate of a polarizing plate and a phase difference plate, or the like, to an outer surface of a glass substrate of a liquid crystal element (formed by sandwiching a liquid crystal component aligned in a predetermined direction between two glass substrates) via an adhesive layer formed of an adhesive composition. The organic EL display includes a transparent substrate (glass) on which a plurality of organic EL elements are arranged in a matrix.
< production of adhesive composition >
Table 1 shows an explanation of abbreviations of tables 2 to 9. Table 2 shows the raw material formulations of the (meth) first (meth) acrylic polymers (a) of examples 1 to 17 and comparative examples 1 to 7. Tables 3 to 4 show the raw material formulations of the (meth) second (meth) acrylic polymers (B) of examples 1 to 17. Table 5 shows the raw material formulations of the (meth) second (meth) acrylic polymers (B) of comparative examples 1 to 7. Tables 6 to 8 show the raw material formulations of the adhesive compositions of examples 1 to 17. Table 9 shows the raw material formulations of the adhesive compositions of comparative examples 1 to 7.
[ Table 1 ]
[ Table 2 ]
The numerical values in the table indicate the parts by mass of the active ingredient.
[ Table 3 ]
The numerical values in the table indicate the parts by mass of the active ingredient.
[ Table 4 ]
The numerical values in the table indicate the parts by mass of the active ingredient.
[ Table 5 ]
The numerical values in the table indicate the parts by mass of the active ingredient.
[ Table 6 ]
The numerical values in the table indicate the parts by mass of the active ingredient.
[ Table 7 ]
The numerical values in the table indicate the parts by mass of the active ingredient.
[ Table 8 ]
The numerical values in the table indicate the parts by mass of the active ingredient.
[ Table 9 ]
The numerical values in the table indicate the parts by mass of the active ingredient.
Example 1
[ (meth) first (meth) acrylic Polymer (A) production ]
Based on the raw material formulation of production example 1 of table 2, 140 parts of ethyl acetate, 80 parts of n-butyl acrylate, 20 parts of methacrylate, 2 parts of 2-hydroxyethyl acrylate and 0.05 part of a polymerization initiator (2, 2' -azobisisobutyronitrile) were added to a reaction apparatus equipped with a stirrer, a thermometer, a reflux condenser and a nitrogen inlet tube, after which nitrogen was filled. This was allowed to react at 55℃for 7 hours under stirring in a stream of nitrogen. After the completion of the reaction, the mixture was diluted with ethyl acetate to obtain a solution A1 of the (meth) first (meth) acrylic polymer (A) having a solid content of 15.0% by mass and a weight average molecular weight of 200 ten thousand.
[ production of the second (meth) acrylic Polymer (B) ]
Based on the raw material formulation of production example 1 of table 3, 80 parts of toluene, 20 parts of methyl ethyl ketone, and 0.3 part of polymerization initiator (2, 2' -azobisisobutyronitrile) were added after filling nitrogen gas into a reaction apparatus equipped with a stirrer, a thermometer, a sequential dropping apparatus, a reflux condenser, and a nitrogen gas introduction pipe. In another vessel, a monomer mixture composed of 35 parts of n-butyl acrylate, 20 parts of methacrylate, 15 parts of phenoxyethyl acrylate, 15 parts of 3-methoxypropyl trimethoxysilane and 15 parts of 3-methacryloxypropyl methyl dimethoxy silane was prepared. The reaction apparatus was warmed to 90℃in a nitrogen stream, and the monomer mixture metered in the other vessel was added dropwise over 120 minutes, and polymerization was carried out at 90℃for 7 hours. After the completion of the reaction, the mixture was diluted with toluene to obtain a second (meth) acrylic polymer (B) solution B1 having a solid content of 50% by mass and a weight average molecular weight of 72,000.
To 100 parts of the solid portion of the first (meth) acrylic polymer (A) solution A1 obtained above, 5.0 parts of the second (meth) acrylic polymer (B) solution B1 in terms of the solid portion, 0.3 parts of Takenate D-262 (trade name, sanjing chemical Co., ltd.) as a crosslinking agent (C) in terms of the solid portion, and 0.75 parts of X-41-1810 (trade name, xinyue chemical Co., ltd.) as a silane coupling agent (E) were added, and the mixture was thoroughly mixed to obtain an adhesive composition.
Based on the raw material formulations of tables 2 to 9, adhesive compositions of examples 2 to 17 and comparative examples 1 to 7 were obtained in the same manner as in example 1.
Test method
The following test examples 1 to 5 were conducted to evaluate the performances using the adhesive compositions of examples 1 to 17 and comparative examples 1 to 7.
(preparation of test polarizing plate)
After the adhesive composition was coated on a silicone-coated PET film (release substrate), the solvent was removed by drying at 90 ℃ to form an adhesive layer having a thickness of 20 μm. After a polarizing film (TAC) having a thickness of 110 μm was bonded to the surface on which the pressure-sensitive adhesive layer was formed, the film was cured at 23 ℃ under 50% rh for 7 days to prepare a sample for evaluation having a size of 80mm×150 mm.
Test example 1 evaluation of durability at 105 ℃ C
After attaching the evaluation sample (i.e., polarizing plate) to glass, the test sample was left for 500 hours in an atmosphere of 105 ℃ (dry), and then foaming and peeling of the evaluation sample were visually confirmed, and durability was evaluated based on the following evaluation criteria.
[ evaluation criterion ]
(1) Foaming
O: no foaming was confirmed on the polarizing plate.
Delta: only a small amount of foaming was confirmed on the polarizing plate.
X: foaming was confirmed on the polarizing plate.
(2) Stripping off
O: no peeling was observed on the polarizing plate.
Delta: a small amount of peeling was confirmed on the polarizing plate.
X: peeling was confirmed on the polarizing plate.
Test example 2 evaluation of durability at 115 ℃C
After attaching the evaluation sample (i.e., polarizing plate) to glass, the test sample was left to stand in an atmosphere of 115 ℃ (dry) for 500 hours, and then foaming and peeling of the evaluation sample were visually confirmed, and durability was evaluated based on the following evaluation criteria.
[ evaluation criterion ]
(1) Foaming
O: no foaming was confirmed on the polarizing plate.
Delta: only a small amount of foaming was confirmed on the polarizing plate.
X: foaming was confirmed on the polarizing plate.
(2) Stripping off
O: no peeling was observed on the polarizing plate.
Delta: only a small amount of peeling was confirmed on the polarizing plate.
X: peeling was confirmed on the polarizing plate.
Test example 3 evaluation of durability at 65℃95% RH
After attaching the sample for evaluation (i.e., polarizing plate) to glass, the sample was left to stand in an atmosphere of 95% RH at 65℃for 500 hours, and then foaming and peeling of the sample for evaluation were visually confirmed, and durability was evaluated based on the following evaluation criteria.
[ evaluation criterion ]
(1) Foaming
O: no foaming was confirmed on the polarizing plate.
Delta: only a small amount of foaming was confirmed on the polarizing plate.
X: foaming was confirmed on the polarizing plate.
(2) Stripping off
O: no peeling was observed on the polarizing plate.
Delta: only a small amount of peeling was confirmed on the polarizing plate.
X: peeling was confirmed on the polarizing plate.
Test example 4 evaluation of reworkability
After the sample for evaluation (i.e., polarizing plate) was attached to the glass and left to stand in an atmosphere of 50 ℃ (drying) or 60 ℃ 90% rh for 72 hours (3 days), the residual state of the adhesive layer on the glass at the time of peeling the sample for evaluation was visually confirmed, and reworkability was evaluated based on the following evaluation criteria. The reworkability here means a property that after the sample for evaluation is attached to the glass, the sample for evaluation can be peeled off from the glass even after a long period of time has elapsed, and after the sample for evaluation is peeled off from the glass, no adhesive layer remains on the glass. Reworkability is a property required to enable the operation of reattaching the polarizing plate to the liquid crystal element.
[ evaluation criterion ]
O: no adhesive layer remained on the glass.
Delta: a portion of the adhesive layer remains on the glass.
X: a substantial portion of the adhesive layer remains on the glass.
Test example 5 evaluation of adhesion to a substrate
The adhesive layer of the sample for evaluation (i.e., polarizing plate) was rubbed with a finger, and the number of times until the adhesive layer was peeled off from the polarizing plate was counted, and the adhesion of the adhesive layer to the substrate was evaluated.
[ description of test results ]
1 to 9: the adhesive layer is peeled off from the polarizing plate by rubbing with a finger 1 to 9 times.
Not less than 10: even if rubbing with a finger is performed 10 times or more, the adhesive layer does not come off from the polarizing plate.
< test results >
Tables 10 to 12 show the test results of examples 1 to 17. Table 13 shows the test results of comparative examples 1 to 7.
[ Table 10 ]
[ Table 11 ]
[ Table 12 ]
[ Table 13 ]
As shown in the results of tables 10 to 13, the adhesive layers formed from the adhesive compositions of examples 1 to 17 were excellent in durability under high temperature environments (105 ℃ or 115 ℃) and high temperature and high humidity environments (65 ℃ 95% rh). Here, the reason why the durability of the adhesive layer in a high-temperature environment and a high-temperature and high-humidity environment is improved is presumed to be due to: the second (meth) acrylic polymer (B) contains the alkoxysilyl group-containing monomer (B3) and at least one of the specified amounts of the present invention.
On the other hand, the adhesive layers formed from the adhesive compositions of comparative examples 1 to 7 were inferior in durability under high temperature environment (105 ℃ C. Or 115 ℃ C.) and high temperature and high humidity environment (65 ℃ C. 95% RH).
In addition, the adhesive layers of examples 1 to 17 have high adhesion to the polarizing plate as an example of the base material, and therefore can suppress degradation of the display quality of the display device.
As described above, the adhesive composition of the present invention has a remarkable effect of improving the durability of the adhesive layer under a high-temperature environment.
The present invention is not limited to the above-described embodiments, and various modifications and changes can be made within the scope of the gist of the present invention.
Claims (10)
1. An adhesive composition comprising a first (meth) acrylic polymer (A) and a second (meth) acrylic polymer (B),
the first (meth) acrylic polymer (A) contains, as constituent units, 70 to 100 parts by mass of an alkyl (meth) acrylate monomer (a 1), 0 to 30 parts by mass of an aromatic group-containing (meth) acrylate monomer (a 2), and 0.01 to 10 parts by mass of a reactive functional group-containing (meth) acrylate monomer (a 3) relative to 100 parts by mass of the total amount of the alkyl (meth) acrylate monomer (a 1) and the aromatic group-containing (meth) acrylate monomer (a 2),
the first (meth) acrylic polymer (A) has a weight average molecular weight of 30 to 350 ten thousand,
the second (meth) acrylic polymer (B) contains, as constituent units, from 0 to 85 parts by mass of an alkyl (meth) acrylate monomer (B1), from 0 to 85 parts by mass of an aromatic group-containing (meth) acrylate monomer (B2), and from 15 to 70 parts by mass of an alkoxysilyl group-containing monomer (B3) in 100 parts by mass of the second (meth) acrylic polymer (B),
the weight average molecular weight of the second (meth) acrylic polymer (B) is 3 to 40 ten thousand,
the adhesive composition contains 1 to 50 parts by mass of the second (meth) acrylic polymer (B) per 100 parts by mass of the first (meth) acrylic polymer (a).
2. The adhesive composition according to claim 1, wherein the alkyl (meth) acrylate monomer (a 1) contained in the first (meth) acrylic polymer (a) and the alkyl (meth) acrylate monomer (B1) contained in the second (meth) acrylic polymer (B) have an alkyl group of not less than C1 and not more than C14.
3. The adhesive composition according to claim 1, wherein the second (meth) acrylic polymer (B) contains, as a constituent unit, any one of a vinyl monomer, an ether group-containing monomer, and an amide group-or substituted amide group-containing monomer in an amount of 5 parts by mass or more and 50 parts by mass or less in 100 parts by mass of the second (meth) acrylic polymer (B).
4. The adhesive composition according to claim 1, wherein the reactive functional group of the (meth) acrylate monomer (a 3) having a reactive functional group is at least one of a hydroxyl group, an epoxy group, and a nitrogen-containing group.
5. The adhesive composition according to claim 1, wherein the adhesive composition contains 0.01 to 10 parts by mass of a crosslinking agent (C) per 100 parts by mass of the first (meth) acrylic polymer (A),
the crosslinking agent (C) contains at least one of an isocyanate compound, a metal chelate compound, an epoxy compound, an aziridine compound, and a melamine compound.
6. The adhesive composition according to claim 1, wherein the adhesive composition contains 1 to 200 parts by mass of an antistatic agent (D) per 100 parts by mass of the first (meth) acrylic polymer (A),
the antistatic agent (D) is a compound containing either fluorine or silicon, wherein M is an alkali metal, excluding M + [(FSO 2 ) 2 N] － Representing the case of the compound.
7. The adhesive composition according to claim 1, wherein the adhesive composition contains 0.05 parts by mass or more and 3.0 parts by mass or less of a silane coupling agent (E) per 100 parts by mass of the first (meth) acrylic polymer (a).
8. An adhesive layer comprising the adhesive composition of any one of claims 1 to 7.
9. An optical film with an adhesive layer comprising the adhesive layer according to claim 8 on at least one side.
10. A display device provided with the adhesive layer-attached optical film according to claim 9.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022143893A JP7212911B1 (en) | 2022-09-09 | 2022-09-09 | Adhesive composition, adhesive layer, optical film with adhesive layer, and display device |
| JP2022-143893 | 2022-09-09 |
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| CN117683491A true CN117683491A (en) | 2024-03-12 |
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|---|---|---|---|
| CN202311103087.0A Pending CN117683491A (en) | 2022-09-09 | 2023-08-30 | Adhesive composition, adhesive layer, optical film with adhesive layer, and display device |
Country Status (3)
| Country | Link |
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| JP (1) | JP7212911B1 (en) |
| KR (1) | KR20240035698A (en) |
| CN (1) | CN117683491A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4072309B2 (en) | 2000-10-13 | 2008-04-09 | 日本カーバイド工業株式会社 | Adhesive composition for polarizing film and polarizing film |
| KR100932887B1 (en) | 2005-12-14 | 2009-12-21 | 주식회사 엘지화학 | Acrylic pressure-sensitive adhesive composition |
| KR100932888B1 (en) | 2006-07-21 | 2009-12-21 | 주식회사 엘지화학 | Optically compensated acrylic pressure sensitive adhesive composition, polarizing plate and liquid crystal display device comprising the same |
| KR100947970B1 (en) * | 2007-12-11 | 2010-03-15 | 주식회사 에이스 디지텍 | Acrylic adhesive composition |
| TWI381033B (en) | 2009-10-09 | 2013-01-01 | Nanya Plastics Corp | An adhesive composition for use in a conformable polarizing plate |
| JP5765303B2 (en) | 2012-08-20 | 2015-08-19 | 信越化学工業株式会社 | Optical pressure-sensitive adhesive composition |
| WO2017098870A1 (en) | 2015-12-10 | 2017-06-15 | 綜研化学株式会社 | Adhesive composition, method for producing same, adhesive sheet, polarizing plate with adhesive layer, and laminate |
| KR101988117B1 (en) | 2017-08-03 | 2019-06-11 | 민후 오 | Non-inverter type portable cooking and heating |
| KR20200002225A (en) | 2018-06-29 | 2020-01-08 | 한국전력공사 | Scheduling method for driving appliance |
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2022
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- 2023-08-07 KR KR1020230103046A patent/KR20240035698A/en unknown
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| JP7212911B1 (en) | 2023-01-26 |
| KR20240035698A (en) | 2024-03-18 |
| JP2024039380A (en) | 2024-03-22 |
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