WO2008091050A1 - Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same - Google Patents
Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same Download PDFInfo
- Publication number
- WO2008091050A1 WO2008091050A1 PCT/KR2007/005166 KR2007005166W WO2008091050A1 WO 2008091050 A1 WO2008091050 A1 WO 2008091050A1 KR 2007005166 W KR2007005166 W KR 2007005166W WO 2008091050 A1 WO2008091050 A1 WO 2008091050A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- acrylic
- sensitive adhesive
- adhesive composition
- Prior art date
Links
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 95
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 23
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 60
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 15
- 125000000524 functional group Chemical group 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims description 79
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 70
- -1 acrylic ester Chemical class 0.000 claims description 56
- 239000010410 layer Substances 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 8
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products 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 8
- 239000002253 acid Substances 0.000 claims description 8
- 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 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 6
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 6
- 229940117913 acrylamide Drugs 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 210000002858 crystal cell Anatomy 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000003505 terpenes Chemical class 0.000 claims description 4
- 235000007586 terpenes Nutrition 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 4
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 4
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004593 Epoxy Chemical class 0.000 claims description 3
- 150000001541 aziridines Chemical class 0.000 claims description 3
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- AUZRCMMVHXRSGT-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CC(C)CS(O)(=O)=O AUZRCMMVHXRSGT-UHFFFAOYSA-N 0.000 claims description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 2
- JSZCJJRQCFZXCI-UHFFFAOYSA-N 6-prop-2-enoyloxyhexanoic acid Chemical compound OC(=O)CCCCCOC(=O)C=C JSZCJJRQCFZXCI-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 2
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 102000001708 Protein Isoforms Human genes 0.000 claims description 2
- 108010029485 Protein Isoforms Proteins 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- KJVBXWVJBJIKCU-UHFFFAOYSA-N [hydroxy(2-hydroxyethoxy)phosphoryl] prop-2-enoate Chemical compound OCCOP(O)(=O)OC(=O)C=C KJVBXWVJBJIKCU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 claims description 2
- YKKYHJNXWUHFTR-UHFFFAOYSA-N propane;prop-2-enamide Chemical compound CCC.NC(=O)C=C YKKYHJNXWUHFTR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011241 protective layer Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- 230000003287 optical effect Effects 0.000 abstract description 10
- 230000003578 releasing effect Effects 0.000 abstract description 5
- 230000035882 stress Effects 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 10
- 229920002284 Cellulose triacetate Polymers 0.000 description 9
- 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 9
- 239000011521 glass Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 230000001070 adhesive effect Effects 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
- 239000000853 adhesive Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 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
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 description 1
- RHOOUTWPJJQGSK-UHFFFAOYSA-N 2-phenylsulfanylethyl prop-2-enoate Chemical compound C=CC(=O)OCCSC1=CC=CC=C1 RHOOUTWPJJQGSK-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005250 alkyl acrylate 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
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N5/00—Details of television systems
- H04N5/64—Constructional details of receivers, e.g. cabinets or dust covers
- H04N5/655—Construction or mounting of chassis, e.g. for varying the elevation of the tube
-
- 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
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N21/00—Selective content distribution, e.g. interactive television or video on demand [VOD]
- H04N21/40—Client devices specifically adapted for the reception of or interaction with content, e.g. set-top-box [STB]; Operations thereof
- H04N21/41—Structure of client; Structure of client peripherals
- H04N21/4104—Peripherals receiving signals from specially adapted client devices
- H04N21/4131—Peripherals receiving signals from specially adapted client devices home appliance, e.g. lighting, air conditioning system, metering devices
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N7/00—Television systems
- H04N7/18—Closed-circuit television [CCTV] systems, i.e. systems in which the video signal is not broadcast
- H04N7/183—Closed-circuit television [CCTV] systems, i.e. systems in which the video signal is not broadcast for receiving images from a single remote source
- H04N7/186—Video door telephones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
Definitions
- the present invention relates to an acrylic pressure-sensitive adhesive composition for a polarizing plate. More specifically, the present invention relates to a pressure- sensitive adhesive composition for a polarizing plate having an excellent low light leakage property, without changing major properties under high temperature, or high temperature and humidity conditions svch as endurance reliability and workability, and a polarizing plate and a liquid crystal display device, containing the same.
- liquid crystal cells comprising liquid crystals and polarizing plates are basically required and suitable adhesive layers or pressure-sensitive adhesive layers have to be used for binding them.
- a phase retardation plate, a compensation plate for wide view angle, a brightness enhancement film, and the like may be used, with additionally adhered to the polarizing plate.
- Major structure forming a liquid crystal display device comprises, generally, a uniformly aligned liquid crystal layer; a polarizing plate with a multi-layer structure, incorporated into a pressure-sensitive adhesive layer or an adhesive layer, based on a liquid crystal cell consisted of a transparent glass plate or plastic sheet material containing a transparent electrode layer; a phase retardation plate; and an additional functional film layer and the like.
- the structure of polarizing plate is one comprising an iodine compound or a dichroic polarizing material aligned in a certain direction.
- a protective film such as triacetyl cellulose (TAC).
- TAC triacetyl cellulose
- the polarizing plate may additionally comprise a phase retardation film, or a compensation film for wide view angle svch as a liquid crystal type film, in a shape having a unidirectional molecular alignment.
- the aforementioned films are made of materials having different molecular structures and compositions, and so have different physical properties. Especially, under high temperature, or high temperature and humidity conditions, the dimensional stability according to shrinkage or expansion of materials having a unidirectional molecular alignment is insufficient. As a result, if the polarizing plate is fixed by a pressure-sensitive adhesive, then stress is concentrated on the TAC layer by shrinkage or expansion under high temperature, or high temperature and humidity conditions, thereby birefringence is developed and light leakage occurs. In this case, a negative birefringence is usually caused over the layer by the shrunk TAC.
- the pressure-sensitive adhesive layer needs high cohesion strength at high temperature to maintain the endurance reliability, for which partially cross-linked visco-elastic materials are used.
- the pressure-sensitive layer has the residual stress under the given stress and the polymer in the cross-linked stricture is aligned in the specific direction to develop birefringence. Under such alignment, general alkyl acrylic pressure-sensitive adhesives develop birefringence of negative values as in TAC.
- sirh As a method that an overall birefringence, including a TAC layer and pressure-sensitive adhesive, under the residual stress is minimized by adding (blending) materials representing birefringence of positive values to the final pressure-sensitive adhesive layer or copolymerizing acrylic monomers having a positive birefringence.
- KR laid-open patent publication No. 2003-0069461 discloses a pressure-sensitive adhesive correcting birefringence of negative values that the acrylic pressure-sensitive adhesive layer represents under the residual stress by incorporating 0.01 to 40 parts by weight of a low molecular weight material representing birefringence of positive values under the residual stress into the acrylic pressure-sensitive adhesive layer.
- the modulus of pressure-sensitive adhesive is lowered, due to the incorporated low molecular weight material therein. Therefore, there is a problem in tailoring property on processing the polarizing plate.
- a method of minimizing birefringence by copolymerizing a monomer representing negative birefringence and a monomer representing positive birefringence under the residual stress is also known (refer to Applied Optics (1997)).
- the degree of birefringence may be regulated under the given stress by copolymerizing an acrylic monomer (negative birefringence) having a side chain of an alkyl group and an acrylic monomer (positive birefringence) having a side chain of an aromatic group.
- JP Unexamined Patent Publication No. 2002-332468 describes a method of improving plastic resistance of the pressure-sensitive adhesive layer by introdudng an acrylic monomer containing an aromatic group in a side chain.
- US Patent No. 6,663,978, and JP Unexamined Patent Publication Nos. 2002-173656 and 2003-013029 describe a method of regulating a refractive index of a pressure-sensitive adhesive layer by introducing an acrylic monomer containing an aromatic group in a side chain.
- JP Unexamined Patent Publication No. 2005-053976 describes a method of improving adhesion performance in even low polar films by introdudng an acrylic monomer containing an aromatic group in a side chain.
- the present invention is intended to solve the above conventional problems, and one object of the present invention is to provide a pressure-sensitive adhesive composition for a polarizing plate having an excellent low light leakage property by regulating birefringence sirh that it has positive values under the residual stress, without changing major properties under high temperature, or high temperature and humidity conditions sirh as endurance reliability and workability, using a (meth)acrylic copolymer having optimal stress releasing property which comprises an optically compensated acrylic copolymer (A) containing a cross-linkable functional group, an optically compensated acrylic copolymer (B) not containing cross-linkable functional group, and a multifunctional cross-linking agent (C), as a pressure-sensitive adhesive layer.
- a (meth)acrylic copolymer having optimal stress releasing property which comprises an optically compensated acrylic copolymer (A) containing a cross-linkable functional group, an optically compensated acrylic copolymer (B) not containing cross-linkable functional group, and a multifunctional cross
- Another object of the present invention is to provide a polarizing plate using the acrylic pressure-sensitive adhesive composition with said characteristics.
- the other object of the present invention is to provide a liquid crystal display device comprising a polarizing plate prepared by the acrylic pressure-sensitive adhesive composition with said characteristics.
- the present invention relates to an acrylic pressure-sensitive adhesive composition which comprises
- an acrylic copolymer (A) containing i) 50 to 75 parts by weight of an alkyl (meth) acrylic acid ester monomer having alkyl of 2 to 14 carbon atoms, ii) 25 to 50 parts by weight of an acrylic ester monomer including an aromatic group copolymerizable with said acrylic monomer, and iii) 0.1 to 10 parts by weight of a vinyl or acrylic ester monomer including a cross-linkable functional group;
- an acrylic copolymer (B) containing i) 50 to 75 parts by weight of an alkyl(meth) acrylic acid ester monomer having alkyl of 2 to 14 carbon atoms, and ii) 25 to 50 parts by weight of an acrylic ester monomer including an aromatic group copolymerizable with said acrylic monomer;
- a negative birefringence is present in the alkyl acrylate pressure-sensitive adhesive layer generally used under such residual stress, which is a major cause that cannot improve the light leakage any longer, together with a negative birefringence present in the contracted TAC layer.
- sirh negative birefringence oxurred in sirh pressure-sensitive adhesive layer it may be allowed to introduce (optically compensate) a pressu res- sensitive adhesive layer copolymerizing acrylic monomer (acrylic monomer containing an aromatic group) representing a positive birefringence into the pressure-sensitive adhesive layer.
- the present invention is characterized by having the optimal cross-linking structure which can minimize the light leakage phenomenon, with maintaining major functions of the pressure-sensitive adhesive, using a mixture of an optically compensated acrylic copolymer (A) containing a cross-linkable functional group and an optically compensated acrylic copolymer (B) containing no cross-linkable functional group.
- a weight ratio of an acrylic copolymer (A) and an acrylic copolymer (B) is preferably 1:9 to 4:1.
- the ratio of acrylic copolymer (A) is less than that of acrylic copolymer (B), it is hard to obtain sufficient cohesion strength. Therefore, said ratio is suitably more than 1:9, and more preferably more than 1:4.
- the ratio of acrylic copolymer (A) to acrylic copolymer (B) is more than 4:1, the ratio of cross-linkable copolymer is increased. As a result, it is difficult to control the degree of cross-linking and improve the light leakage through the stress release of the pressure-sensitive adhesive in combination with the effect of optical compensation.
- weight average molecular weights of acrylic copolymer (A) and acrylic copolymer (B) are each independently 800,000 to 2,000,000.
- weight average molecular weight is less than 800,000, cohesion strength is so impaired that endurance reliability is poor. If said weight average molecular weight is more than 2,000,000, the effect of stress release is so impaired that the effect of light leakage is slight.
- the acrylic copolymer (A) and the acrylic copolymer (B), a ⁇ jording to the present invention, as major resins include i) 50 to 75 parts by weight of alkyl(meth)acrylic acid ester monomer in which alkyl has 2 to 14 carbon atoms, i) Alkyl (meth) acrylic acid ester monomer included in said acrylic copolymer (A) and acrylic copolymer (B) may be the same or different.
- the final pressure-sensitive adhesive represents high negative birefringence under the residual stress and thus the effect of improving optical light leakage may be slight.
- the amount of said i) alkyl(meth) acrylic acid ester monomer is less than 50 parts by weight, the adhesion property balance of final pressure-sensitive adhesive is deteriorated, the adhesive represents high positive birefringence under the residual stress and thus the effect of improving optical light leakage is deteriorated.
- the i) alkyl(meth)acrylic acid ester monomer in which alkyl has 2 to 14 carbon atoms preferably uses one or more selected from the group consisting of ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate, sec-butyl (meth)acrylate, pentyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, lauryl (meth)acrylate, and tetradecyl (meth)acrylate.
- Tg glass transition temperature
- the acrylic copolymer (A) and the acrylic copolymer (B), a ⁇ jording to the present invention are monomers representing birefringence of positive values under stress, for compensating birefringence of negative values in acrylic copolymer comprising alkyl(meth) acrylic acid ester monomer in which alkyl has 2 to 14 carbon atoms as a principal component, and include ii) 25 to 50 parts by weight of acrylic ester monomer containing an aromatic group copolymerizable with said acrylic monomer alkyl(meth) acrylic acid ester monomer, ii) Acrylic ester monomer containing an aromatic group included in said acrylic copolymer (A) and acrylic copolymer (B) may be the same or different.
- the amount of said (meth) acrylic ester monomer containing aromatic group is suitably 25 to 50 parts by weight in all monomers. If the amount of (meth) acrylic ester monomer containing aromatic group is less than 25 parts by weight in all monomers, the final pressure-sensitive adhesive represents large negative birefringence under the residual stress and thus the effect of improving optical light leakage is slight. If the amount is in excess of 50 parts by weight, the adhesion property balance of final pressure-sensitive adhesive is deteriorated. Especially, the adhesion strength is greatly raised, so that the re-releasability of polarizing plates is much deteriorated.
- the (meth) acrylic acid ester monomer containing a copolymerizable aromatic group according to the present invention uses, preferably, a compound of Formula 1:
- R represents hydrogen or a methyl group
- R represents an alkylene group having 1 to 12 carbon atoms
- n represents an integer of 0 to 3, preferably, 0 or 1
- X represents an oxygen atom, a sulfur atom or an alkylene group having 1 to 4 carbon atoms and
- Ar represents an aromatic group unsubstituted or substituted with halogen, particularly bromo or chloro, or alkyl of 1 to 12 carbon atoms.
- Preferred examples of said compound of Formula 1 include, but not limited to, phenoxy ethyl (meth)acrylate, benzyl (meth)acrylate, 2-phenylthio-l -ethyl (meth)acrylate, 6-(4,6-dibromo-2-isopropylphenoxy)- 1-hexyl (meth)acrylate, 6-(4,6-dibromo-2-sec-butylphenoxy)- 1-hexyl (meth)acrylate, 2,6-dibromo-4-nonylphenyl (meth)acrylate, 2,6-dibromo-4-dodecyl phenyl (meth)acrylate, 2-(l-naphtyloxy)-l-ethyl (meth)acrylate, 2-(2-naphtyloxy)-l -ethyl (meth)acrylate, 6- (1-naphtyloxy)- 1-hexyl
- said compound of Formula 1 is phenoxy ethyl (meth)acrylate, benzyl (meth)acrylate, 2-phenylthio-l -ethyl acrylate, 8-(2-naphtyloxy)-l-octyl acrylate, 2-(l-naphtyloxy)-l-ethyl acrylate and a mixture thereof; and most preferably, phenoxy ethyl (meth) acrylate, benzyl (meth) acrylate or a mixture thereof
- a vinyl or acrylic ester monomer containing a cross-linkable functional group is for regulating adhesion strength and cohesion strength of the acrylic copolymer, and preferably includes an acid group or a hydroxyl group within its stricture.
- the vinyl monomer containing an acid group used herein is a component for reacting with a cross-linking agent and giving the pressure-sensitive adhesive cohesion strength by chemical bonds such that cohesion failure of the adhesive is not occurred on raising temperature.
- Said copolymerizable monomer containing an acid group may include one or more selected from the group consisting of a copolymerizable monomer containing a carboxyl group or anhydride thereof, a copolymerizable monomer containing a sulfonic acid group, and a copolymerizable monomer containing a phosphoric acid group.
- the copolymerizable monomer containing a carboxyl group above is (meth)acrylic acid, carboxyethyl acrylate, carboxypentyl acrylate, itaconic acid, maleic acid, fumaric acid, or crotonic acid;
- the anhydride of copolymerizable monomer containing a carboxyl group is maleic anhydride or itaconic anhydride
- the copolymerizable monomer containing a sulfonic acid group is styrene sulfonic acid, allyl sulfonic acid, 2-(meth)acrylamide-2-methyl propane sulfonic acid, (meth)acrylamide propane sulfonic acid, sulfopropyl (meth)acrylate, (meth) aery loyloxy naphthale sulfonic acid; and
- the copolymerizable monomer containing a phosphoric acid group may be selected from 2-hydroxyethyl acryloyl phosphate, and the like, without limitation.
- the vinyl or acrylic monomer containing a hydroxyl group is preferably one or more selected from the group consisting of 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxyethyleneglyx>l (meth)acrylate, and 2-hydroxypropyleneglyx>l (meth)acrylate.
- the (meth) acrylic copolymers (A) and (B) a ⁇ jording to the present invention each independently, further comprises 0 - 20 parts by weight of functional monomer iv) of Formula 2 based on weight of total monomers as an optional component.
- R represents hydrogen or alkyl
- R represents cyano, phenyl unsubstituted or substituted with alkyl, acetyloxy, or
- R represents amino or gljddyloxy unsubstituted or substituted with alkyl.
- the alkyl of R to R preferably, represents lower alkyl of 1 to 6 carbon atoms, and more preferably, methyl or ethyl.
- Examples of said compound of Formula 2 may include, but not limited to, styrene monomers such as styrene or alpha methyl styrene; carboxylic acid vinyl esters sirh as vinyl acetate; or vinyl monomers containing nitrogen sirh as acrylonitrile, (meth)acryl amide, N-methyl(meth)acryl amide, N-butoxy methyl(meth)acryl amide, or glyddyl(meth)acrylate. Said monomers may be used alone or by mixing two or more thereof
- the method for preparing the acrylic copolymers (A) and (B) according to the present invention is not specifically limited, and the (meth) acrylic copolymer can be prepared by solution polymerization, photo-polymerization, bulk polymerization, suspension polymerization, or emulsion polymerization. Preferably, it is prepared by using solution polymerization.
- the polymerization temperature is preferably 50 to 140?, and the initiator is preferably added in a state that monomers are evenly mixed.
- Sirh polymerization initiator may use an azo-based polymerization initiator sirh as azo-bisisobutyronitrile and azobiscjclohexanecarbonitrile, or peroxide sirh as benzoyl peroxide and acetyl peroxide alone or in a mixture thereof
- the acrylic pressure-sensitive adhesive composition of the present invention may comprises 0.01 to 10 parts by weight of multi-functional cross-linking agent (C) based on 100 parts by weight of the (meth) acrylic copolymer.
- the preferred physical properties may be provided within the above ranges.
- Said multi-functional cross-linking agent (C) is reacted with a carboxylic group and a hydroxyl group, and the like, to serve to increase the cohesion strength of pressure- sensitive adhesive.
- said multi-functional cross-linking agent is one or more selected from the group consisting of isocyanate compounds, epoxy compounds, aziridine compounds, and metal chelate compounds.
- isocyanate compounds is easy to be used for use propose.
- Said isocyanate compounds may be one or more selected from the group consisting of tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isoform diisocyanate, tetramethylxylene diisocyanate, naphthalene diisocyanate, and their reactants with polyol (trimethylolpropane, etc.),
- said epoxy compounds may be one or more selected from the group consisting of ethyleneglyjol diglyddylether, trigljddylether, trimethylolpropane trigljddylether, N,N,N',N'-tetraglyddylethylenediamine, and glycerine diglyddylether,
- said aziridine compounds may be one ore more selected from the group consisting of
- said metal chelate compounds may use, but not limited to, one or more selected from compounds that a multivalent metal such as aluminum, iron, zinc, tin, antimony, magnesium and vanadium is coordinated with acethylacetone or ethyl acetoacetate.
- the multi-functional cross-linking agent may be evenly coated when the functional cross-linking reaction of the cross-linking agent is hardly occurred in the combining process performed for forming the pressure-sensitive adhesive layer. If the coating process is completed followed by drying and aging, the cross-linked stricture may be formed to obtain the pressure-sensitive adhesive layer having elasticity and strong cohesion strength.
- the present composition may further comprises a silane coupling agent for improving adhesion stability and thus more improving heat resistance/moisture resistance.
- sirh silane coupling agent serves to be of help to improve adhesion reliability, which may be used in an amount of 0.005 to 5 parts by weight based on 100 parts by weight of all the acrylic copolymers. If the amount is less than 0.005 parts by weight, the adhesion reliability is not improved. If the amount is in excess of 5 parts by weight, the endurance reliability is lowered.
- the silane coupling compound is g-gljcydoxypropyl trimethoxysilane, g- gljcydoxypropyl methyldiethoxysilane, g-gljcydoxypropyl triethoxysilane, 3-mercaptopropyl trimethoxysilane, vinyl trimethoxysilane, vinyl triethoxysilane, g- methacryloxypropyl trimethoxysilane, g-methacryloxypropyl triethoxysilane, g- aminopropyl triethoxysilane, 3-isocyanatepropyl triethoxysilane, or g- acetoacetatepropyl trimethoxysilane and the like. These may be used alone or in a mixture thereof
- the present invention may further comprise a tackifier resin, which may be used in an amount of 1 to 100 parts by weight based on 100 parts by weight of the acrylic copolymer (A). If the amount is less than 1 part by weight, the tackifying function is poor. If the amount is in excess of 100 parts by weight, the compatibility or the cohesion strength of pressure-sensitive adhesive is often reduced.
- a tackifier resin which may be used in an amount of 1 to 100 parts by weight based on 100 parts by weight of the acrylic copolymer (A). If the amount is less than 1 part by weight, the tackifying function is poor. If the amount is in excess of 100 parts by weight, the compatibility or the cohesion strength of pressure-sensitive adhesive is often reduced.
- the tackifier resin may use a (hydrogenated) hydrocarbon resin, a (hydrogenated) rosin resin, a (hydrogenated) rosin ester resin, a (hydrogenated) terpene resin, a (hydrogenated) terpene phenol resin, a polymerized rosin resin, or a polymerized rosin ester resin, and the like. These may be used alone or by mixing two or more of the above resins.
- acrylic low molecular weight polymers an epoxy resin, a hardener, etc. may be additionally mixed and used, and for general purposes, a UV stabilizer, an antioxidant, a colorant, a reinforcing agent, a filler, a defoaming agent, a surfactant, a plastidzer, etc. may be properly added and used.
- the present invention relates to a polarizing plate characterized by comprising
- the present polarizing plate comprises a pressure-sensitive adhesive layer formed from the above pressure- sensitive adhesive composition on one side or both sides of the polarizing film.
- Polarizing films or polarizing devices composing the polarizing plate are not specifically limited.
- said polarizing film is a film that a polarizing component sirh as iodine or dichroic dye is contained in polyvinyl alcohol resin film to elongate the resulting product.
- the thickness of these polarizing films is also not specifically limited, and may form usual thickness.
- Said polyvinyl alcohol resin may use polyvinyl alcohol, polyvinyl formal, polyvinyl acetal and saponified ethylene vinyl acetate copolymer, and the like.
- multilayer films may be formed, on which a protective film is laminated, sirh as a cellulose film, for example, triacetyl cellulose, etc.; a polyester film, for example, poljcarbonate, or polyethylene terephthalate, etc.; a polyether film, for example, polyether sulfone; a polyolefin film, for example, polyethylene, polypropylene, polyolefin having cjclo or norbornene structure, or ethylene propylene copolymer.
- the thickness of these protective films is not specifically limited, and may form usual thickness.
- the method of forming the pressure-sensitive adhesive layer on a polarizing film is not specifically limited in the present invention, which may be applied by a method of coating the pressure-sensitive adhesive directly on the surface of a polarizing film, using a bar coater and the like, and drying the adhesive, or a method of coating the pressure-sensitive adhesive on a surface of releasable substrate, drying the adhesive, transferring the pressure-sensitive adhesive layer formed on the surface of said releasable substrate to the surface of polarizing film, and aging the layer.
- the polarizing plate of the present invention may be laminated one or more layers providing additional functions, sirh as protective layer, reflecting layer, anti-glare layer, phase retardation plate, compensation film for wide view angle, and brightness enhancing film.
- Said pressure-sensitive adhesive layer a ⁇ jording to the present invention may also be attached to said functional layers.
- the polarizing plate applied by the pressure-sensitive adhesive of the present invention can be applied to all usual liquid crystal display devices, the kind of which liquid crystal panel is not specifically limited.
- the present invention may constrict liquid crystal display devices comprising a liquid crystal panel binding the pressure-sensitive adhesive polarizing plate to one side or both sides of a liquid crystal cell.
- Example 1 [113]
- Example 1 [114] ⁇ Combination> [115] 20 Parts by weight of the obtained high molecular weight acrylic copolymer in Preparation Example 1 and 80 parts by weight of the obtained high molecular weight acrylic copolymer in Preparation Example 5 were homogenously mixed and 0.1 parts by weight of tolylene diisocyanate addirt of trimethylolpropane (TDI-I) and 0.1 parts by weight of -glyddoxypropyltrimethoxysilane as a multi-functional cross-linking agent were added. The mixture was diluted in a suitable concentration and homogeneously mixed, considering the coating property. The resulting product was coated on a releasing sheet and dried to obtain a 30 microns homogenous pressure-sensitive adhesive layer.
- TDI-I trimethylolpropane
- -glyddoxypropyltrimethoxysilane a multi-functional cross-linking agent
- the polarizing plate coated with the pressure-sensitive adhesive was cut into 90 mm wide and 170 mm long, and then adhered to an alkali-free plate glass by Corning, Inc. using a laminator. Then, the plate glass was left in the Temperature and Humidity Room Chamber for 1 hour, heated at 5O 0 C for 4 hours and left at room temperature for 1 hour, followed by releasing the polarizing plate from the glass.
- the re-releasability was evaluated as follows:
- the polarizing plate (90 mm x 170 mm) coated with the pressure-sensitive adhesive prepared in Example 1 above was attached to both sides of a glass substrate (110 mm x 190 mm x 0.7 mm) with each optical absorbing axis crossed.
- the glass substrate was subjected to a clean room work at the applied pressure of about 5 kg/cm 2 so that bubbles or impurities might not be generated.
- moisture-heat resistance of the specimens they were left at a temperature of 6O 0 C and a relative humidity of 90% for 1,000 hours and then observed about formation of bubbles or releases.
- heat resistance of the specimens they were left at 8O 0 C for 1,000 hours and then observed about formation of bubbles or releases.
- the specimens were left at room temperature for 24 hours immediately before evaluating their states.
- the prepared pressure-sensitive adhesive polarizing plates above were left for 5 or more months and then the reliability was evaluated in accordance with the above method.
- the evaluation standard of endurance reliability was as follows:
- Examples 1 to 3 of the present invention represented an excellent endurance reliability and workability (re-releasability), and represented an excellent low light leakage property.
- the amount of cross-linkable polymer is so low that the low light leakage property is excellent, but the re-releasability and the endurance reliability are poor.
- the aromatic and acrylic ester monomers are introduced in too large quantity, so that the low light leakage property is excellent, but the re-releas ability and the endurance reliability are poor.
- the amounts of aromatic and acrylic esters are so low that the low light leakage property is poor.
- the cross- linkable polymer is used alone, so that the re-releas ability is very poor.
- the present invention relates to an acrylic pressure-sensitive adhesive composition for a polarizing plate, and has an excellent low light leakage property, without changing major properties such as endurance reliability and re-workability under a high temperature condition and a high temperature and humidity condition. Therefore, if said pressure-sensitive adhesive composition is applied to a polarizing plate of liquid crystal display device, the light leakage phenomenon occurred after using for a long time may be prevented.
Landscapes
- Engineering & Computer Science (AREA)
- Multimedia (AREA)
- Signal Processing (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Automation & Control Theory (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
- Adhesive Tapes (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009547158A JP5095756B2 (ja) | 2007-01-23 | 2007-10-22 | 光学補償されたアクリル系粘着剤組成物、それを含む偏光板及び液晶表示素子 |
| US12/449,066 US9469663B2 (en) | 2006-12-20 | 2007-10-22 | Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same |
| CN2007800502557A CN101679826B (zh) | 2007-01-23 | 2007-10-22 | 光学补偿的丙烯酸压敏粘合剂组合物以及含有该组合物的偏振片和液晶显示器装置 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2007-0006966 | 2007-01-23 | ||
| KR1020070006966A KR100948778B1 (ko) | 2007-01-23 | 2007-01-23 | 광학 보상된 아크릴계 점착제 조성물, 이를 포함하는편광판 및 액정표시소자 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2008091050A1 true WO2008091050A1 (en) | 2008-07-31 |
Family
ID=39644611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2007/005166 WO2008091050A1 (en) | 2006-12-20 | 2007-10-22 | Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP5095756B2 (ko) |
| KR (1) | KR100948778B1 (ko) |
| CN (1) | CN101679826B (ko) |
| TW (1) | TWI381031B (ko) |
| WO (1) | WO2008091050A1 (ko) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010121009A (ja) * | 2008-11-18 | 2010-06-03 | Nitto Denko Corp | 光学部材用粘着剤組成物、光学部材用粘着剤層、粘着型光学部材および画像表示装置 |
| US20110043737A1 (en) * | 2008-01-14 | 2011-02-24 | Lg Chem, Ltd. | Acrylic adhesive composition |
| EP2386616A1 (en) * | 2009-01-09 | 2011-11-16 | Soken Chemical & Engineering Co., Ltd. | Pressure-sensitive adhesive composition for polarizer and polarizer formed using same |
| CN102597088A (zh) * | 2009-09-11 | 2012-07-18 | 艾利丹尼森公司 | 双交联增粘压敏粘合剂 |
| US20120274881A1 (en) * | 2009-11-27 | 2012-11-01 | Ki Seok Jang | Pressure-sensitive adhesive composition |
| CN103764782A (zh) * | 2011-08-29 | 2014-04-30 | 日东电工株式会社 | 光学用粘合粘接剂组合物、光学用粘合粘接剂层、光学构件、偏光板、和图像显示装置 |
| CN108276933A (zh) * | 2018-01-11 | 2018-07-13 | 湘潭大学 | 一种环保型水性贴合胶黏剂及其制备方法与粘结工艺 |
| US10526511B2 (en) | 2016-12-22 | 2020-01-07 | Avery Dennison Corporation | Convertible pressure sensitive adhesives comprising urethane (meth)acrylate oligomers |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101304592B1 (ko) * | 2010-06-08 | 2013-09-05 | 주식회사 엘지화학 | 내열성·고강도 아크릴계 공중합체, 및 이를 포함하는 광학필름 |
| JP5595321B2 (ja) * | 2011-03-31 | 2014-09-24 | リンテック株式会社 | 粘着性組成物、粘着剤および粘着シート |
| JP2013114198A (ja) * | 2011-11-30 | 2013-06-10 | Keio Gijuku | 光学フィルム、光学フィルム用樹脂材料及び画像表示装置 |
| TWI521030B (zh) * | 2011-12-21 | 2016-02-11 | Ｌｇ化學股份有限公司 | 壓感性黏著劑組成物 |
| KR20150017858A (ko) * | 2013-08-08 | 2015-02-23 | 동우 화인켐 주식회사 | 점착제 조성물 및 이를 이용한 복합 편광판 |
| JP6209077B2 (ja) * | 2013-12-19 | 2017-10-04 | 日本カーバイド工業株式会社 | 粘着剤組成物、粘着剤付偏光板、及び表示装置 |
| KR102145534B1 (ko) | 2015-09-02 | 2020-08-18 | 주식회사 엘지화학 | 점착력이 상이한 점착 코팅부들을 포함하는 분리막 및 이를 포함하는 전극조립체 |
| KR102337694B1 (ko) * | 2015-11-20 | 2021-12-09 | 동우 화인켐 주식회사 | 플렉서블 터치스크린 패널 모듈 및 이를 포함하는 플렉서블 디스플레이 장치 |
| KR102047288B1 (ko) * | 2015-12-10 | 2019-11-21 | 주식회사 엘지화학 | 점착제 조성물 |
| DE102016202353A1 (de) * | 2016-02-16 | 2017-08-17 | Tesa Se | Klebemasse insbesondere für gekrümmte Oberflächen |
| KR102364788B1 (ko) * | 2016-03-24 | 2022-02-18 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 포함하는 컬러필터 및 표시장치 |
| WO2018110967A1 (ko) * | 2016-12-13 | 2018-06-21 | 삼성에스디아이 주식회사 | 광학 필름용 점착제 조성물, 점착제층, 광학 부재 및 화상표시장치 |
| JP7044516B2 (ja) * | 2016-12-13 | 2022-03-30 | 三星エスディアイ株式会社 | 光学フィルム用粘着剤組成物、粘着剤層、光学部材、および画像表示装置 |
| JP6943726B2 (ja) * | 2016-12-13 | 2021-10-06 | 三星エスディアイ株式会社Samsung SDI Co., Ltd. | 光学フィルム用粘着剤組成物、粘着剤層、光学部材、および画像表示装置 |
| JP6970814B2 (ja) | 2017-09-13 | 2021-11-24 | 杉金光電（蘇州）有限公司 | 光学積層体 |
| KR102651810B1 (ko) * | 2021-03-16 | 2024-03-28 | 동우 화인켐 주식회사 | 점착제 조성물, 이를 이용하여 제조된 점착 시트, 광학 부재 및 표시 장치 |
| KR102345035B1 (ko) * | 2021-06-14 | 2021-12-31 | 김학돈 | 친환경 흙콘크리트 조성물 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5310835A (en) * | 1993-09-30 | 1994-05-10 | National Starch And Chemical Investment Holding Corporation | Transparent two-part acrylic adhesive composition and the method of use thereof |
| KR20000067624A (ko) * | 1999-04-30 | 2000-11-25 | 성재갑 | 재박리성이 우수한 광학용 아크릴계 감압 점착제 조성물 및 그를이용한 라미네이트 |
| US6602944B2 (en) * | 2000-02-22 | 2003-08-05 | Moore North America, Inc. | Pressure sensitive cohesive |
| KR20050102997A (ko) * | 2004-04-23 | 2005-10-27 | 주식회사 엘지화학 | 편광판용 아크릴계 점착제 조성물 |
| WO2006009250A1 (ja) * | 2004-07-22 | 2006-01-26 | Soken Chemical & Engineering Co., Ltd. | 偏光板用粘着剤組成物および偏光板 |
| KR20060108515A (ko) * | 2005-04-13 | 2006-10-18 | 주식회사 엘지화학 | 내충격성이 우수한 아크릴계 점착제 조성물, 이를 이용한광학필름, 및 상기 광학필름을 포함하는 액정표시장치 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3533589B2 (ja) * | 1997-04-09 | 2004-05-31 | 綜研化学株式会社 | 偏光板用粘着剤組成物および偏光板 |
| JP4640740B2 (ja) * | 2000-12-04 | 2011-03-02 | 日東電工株式会社 | 感圧性接着剤組成物、感圧性接着シート及び光学フィルム |
| JP2004078171A (ja) * | 2002-06-18 | 2004-03-11 | Nitto Denko Corp | 光学補償層付偏光板およびそれを用いた画像表示装置 |
| JP4177077B2 (ja) * | 2002-10-25 | 2008-11-05 | 日東電工株式会社 | 光学補償板、それを用いた光学補償層付偏光板、前記光学補償板の製造方法、および、それらを用いた液晶表示装置 |
| US7285313B2 (en) * | 2004-01-20 | 2007-10-23 | Lg Chem Ltd. | Acrylic pressure-sensitive adhesive composition for polarizing film |
| JP4635151B2 (ja) * | 2004-04-14 | 2011-02-16 | 綜研化学株式会社 | 光学部材用粘着剤組成物および光学部材用粘着フィルム、ならびにこれらを用いた光学部材 |
| JP2005314453A (ja) * | 2004-04-27 | 2005-11-10 | Sumitomo Chemical Co Ltd | アクリル樹脂及び該樹脂を含有する粘着剤 |
| JP4780647B2 (ja) * | 2004-12-02 | 2011-09-28 | 日東電工株式会社 | 光学フィルム用粘着剤、光学フィルム用粘着剤層およびその製造方法、粘着型光学フィルム、ならびに画像表示装置 |
| JP5523650B2 (ja) * | 2005-04-28 | 2014-06-18 | リンテック株式会社 | 粘着剤付き光学機能性部材の製造方法 |
-
2007
- 2007-01-23 KR KR1020070006966A patent/KR100948778B1/ko active IP Right Grant
- 2007-10-22 JP JP2009547158A patent/JP5095756B2/ja active Active
- 2007-10-22 WO PCT/KR2007/005166 patent/WO2008091050A1/en active Application Filing
- 2007-10-22 CN CN2007800502557A patent/CN101679826B/zh active Active
-
2008
- 2008-01-21 TW TW097102206A patent/TWI381031B/zh active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5310835A (en) * | 1993-09-30 | 1994-05-10 | National Starch And Chemical Investment Holding Corporation | Transparent two-part acrylic adhesive composition and the method of use thereof |
| KR20000067624A (ko) * | 1999-04-30 | 2000-11-25 | 성재갑 | 재박리성이 우수한 광학용 아크릴계 감압 점착제 조성물 및 그를이용한 라미네이트 |
| US6602944B2 (en) * | 2000-02-22 | 2003-08-05 | Moore North America, Inc. | Pressure sensitive cohesive |
| KR20050102997A (ko) * | 2004-04-23 | 2005-10-27 | 주식회사 엘지화학 | 편광판용 아크릴계 점착제 조성물 |
| WO2006009250A1 (ja) * | 2004-07-22 | 2006-01-26 | Soken Chemical & Engineering Co., Ltd. | 偏光板用粘着剤組成物および偏光板 |
| KR20060108515A (ko) * | 2005-04-13 | 2006-10-18 | 주식회사 엘지화학 | 내충격성이 우수한 아크릴계 점착제 조성물, 이를 이용한광학필름, 및 상기 광학필름을 포함하는 액정표시장치 |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110043737A1 (en) * | 2008-01-14 | 2011-02-24 | Lg Chem, Ltd. | Acrylic adhesive composition |
| US9798185B2 (en) * | 2008-01-14 | 2017-10-24 | Lg Chem, Ltd. | Acrylic adhesive composition |
| US20140093662A1 (en) * | 2008-01-14 | 2014-04-03 | Lg Chem, Ltd. | Acrylic adhesive composition |
| US9482896B2 (en) * | 2008-01-14 | 2016-11-01 | Lg Chem, Ltd. | Acrylic adhesive composition |
| JP2010121009A (ja) * | 2008-11-18 | 2010-06-03 | Nitto Denko Corp | 光学部材用粘着剤組成物、光学部材用粘着剤層、粘着型光学部材および画像表示装置 |
| EP2386616A1 (en) * | 2009-01-09 | 2011-11-16 | Soken Chemical & Engineering Co., Ltd. | Pressure-sensitive adhesive composition for polarizer and polarizer formed using same |
| CN102272255A (zh) * | 2009-01-09 | 2011-12-07 | 综研化学株式会社 | 偏光片用压敏粘合剂组合物及使用其的偏光片 |
| EP2386616A4 (en) * | 2009-01-09 | 2012-07-04 | Soken Kagaku Kk | AUTOCOLLATING ADHESIVE COMPOSITION FOR POLARIZER AND POLARIZER FORMED USING THE SAME |
| TWI495697B (zh) * | 2009-01-09 | 2015-08-11 | Soken Kagaku Kk | Adhesive polarizing plate polarizing plate using this composition and the composition |
| CN102597088A (zh) * | 2009-09-11 | 2012-07-18 | 艾利丹尼森公司 | 双交联增粘压敏粘合剂 |
| US9321938B2 (en) | 2009-09-11 | 2016-04-26 | Avery Dennison Corporation | Dual crosslinked tackified pressure sensitive adhesive |
| US9389455B2 (en) * | 2009-11-27 | 2016-07-12 | Lg Chem, Ltd. | Pressure-sensitive adhesive composition |
| US20120274881A1 (en) * | 2009-11-27 | 2012-11-01 | Ki Seok Jang | Pressure-sensitive adhesive composition |
| CN103764782B (zh) * | 2011-08-29 | 2016-07-06 | 日东电工株式会社 | 光学用粘合粘接剂组合物、光学用粘合粘接剂层、光学构件、偏光板、和图像显示装置 |
| CN103764782A (zh) * | 2011-08-29 | 2014-04-30 | 日东电工株式会社 | 光学用粘合粘接剂组合物、光学用粘合粘接剂层、光学构件、偏光板、和图像显示装置 |
| US10526511B2 (en) | 2016-12-22 | 2020-01-07 | Avery Dennison Corporation | Convertible pressure sensitive adhesives comprising urethane (meth)acrylate oligomers |
| CN108276933A (zh) * | 2018-01-11 | 2018-07-13 | 湘潭大学 | 一种环保型水性贴合胶黏剂及其制备方法与粘结工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200902660A (en) | 2009-01-16 |
| CN101679826B (zh) | 2013-02-27 |
| JP2010516855A (ja) | 2010-05-20 |
| KR20080069355A (ko) | 2008-07-28 |
| TWI381031B (zh) | 2013-01-01 |
| JP5095756B2 (ja) | 2012-12-12 |
| KR100948778B1 (ko) | 2010-03-24 |
| CN101679826A (zh) | 2010-03-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2044162B1 (en) | Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same | |
| WO2008091050A1 (en) | Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same | |
| US9469663B2 (en) | Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same | |
| EP2233546B1 (en) | Acrylic adhesive composition | |
| US8318852B2 (en) | Acrylic pressure-sensitive adhesive composition for polarizing film | |
| US7285313B2 (en) | Acrylic pressure-sensitive adhesive composition for polarizing film | |
| US7462390B2 (en) | Acrylic pressure-sensitive adhesive composition for polarizing film | |
| KR101171977B1 (ko) | 아크릴계 점착제 조성물, 이를 포함하는 편광판 및액정표시장치 | |
| US9017778B2 (en) | Adhesive composition, and polarizing plates and LCDs utilizing the adhesive composition | |
| KR20100003689A (ko) | 점착제 조성물, 이를 포함하는 편광판 및 액정표시장치 | |
| US9790408B2 (en) | Polarizing plate having pressure sensitive adhesive layer with improved light leakage property |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WWE | Wipo information: entry into national phase |
Ref document number: 200780050255.7 Country of ref document: CN |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 07833475 Country of ref document: EP Kind code of ref document: A1 |
|
| ENP | Entry into the national phase |
Ref document number: 2009547158 Country of ref document: JP Kind code of ref document: A |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 07833475 Country of ref document: EP Kind code of ref document: A1 |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 12449066 Country of ref document: US |