CN101679826A - 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
- CN101679826A CN101679826A CN200780050255A CN200780050255A CN101679826A CN 101679826 A CN101679826 A CN 101679826A CN 200780050255 A CN200780050255 A CN 200780050255A CN 200780050255 A CN200780050255 A CN 200780050255A CN 101679826 A CN101679826 A CN 101679826A
- Authority
- CN
- China
- Prior art keywords
- methyl
- sensitive adhesive
- pressure sensitive
- vinylformic acid
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 97
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims abstract description 57
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 14
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 59
- 239000000178 monomer Substances 0.000 claims description 77
- -1 (methyl) 2-ethylhexyl Chemical group 0.000 claims description 52
- 239000010410 layer Substances 0.000 claims description 44
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 14
- 238000000576 coating method Methods 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000007334 copolymerization reaction Methods 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 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 6
- 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 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 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 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 5
- 239000004593 Epoxy Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 210000002858 crystal cell Anatomy 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000000007 visual effect Effects 0.000 claims description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
- 239000013522 chelant Substances 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 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
- UBYWYEGPDNYPHZ-UHFFFAOYSA-N 2-hydroxyethyl but-2-enoate Chemical compound CC=CC(=O)OCCO UBYWYEGPDNYPHZ-UHFFFAOYSA-N 0.000 claims description 2
- GWSQQDUFKKYTCA-UHFFFAOYSA-N 2-hydroxypropyl but-2-enoate Chemical compound CC=CC(=O)OCC(C)O GWSQQDUFKKYTCA-UHFFFAOYSA-N 0.000 claims description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 claims description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- FGKORHFSYSZWHM-UHFFFAOYSA-N CC=1C(=C(C2=CC=CC=C2C1)S(=O)(=O)O)OC(C=C)=O Chemical compound CC=1C(=C(C2=CC=CC=C2C1)S(=O)(=O)O)OC(C=C)=O FGKORHFSYSZWHM-UHFFFAOYSA-N 0.000 claims description 2
- OOMOVNJMPPGASZ-UHFFFAOYSA-N CC=CC(=O)OCCC1=CC=CS1 Chemical compound CC=CC(=O)OCCC1=CC=CS1 OOMOVNJMPPGASZ-UHFFFAOYSA-N 0.000 claims description 2
- NFGRGGJYENKYBB-UHFFFAOYSA-N CC=CC(=O)OCCOC1=CC2=CC=CC=C2C=C1 Chemical compound CC=CC(=O)OCCOC1=CC2=CC=CC=C2C=C1 NFGRGGJYENKYBB-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- NYXVMNRGBMOSIY-UHFFFAOYSA-N OCCC=CC(=O)OP(O)(O)=O Chemical compound OCCC=CC(=O)OP(O)(O)=O NYXVMNRGBMOSIY-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- KAKJZWSUVDRWQU-UHFFFAOYSA-N butan-2-yl but-2-enoate Chemical compound CCC(C)OC(=O)C=CC KAKJZWSUVDRWQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- PJJDTHSONOWIIH-UHFFFAOYSA-N dodecyl but-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C=CC PJJDTHSONOWIIH-UHFFFAOYSA-N 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
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N ethyl but-2-enoate Chemical compound CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-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
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- USUBUUXHLGKOHN-UHFFFAOYSA-N methyl 2-methylidenehexanoate Chemical compound CCCCC(=C)C(=O)OC USUBUUXHLGKOHN-UHFFFAOYSA-N 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- CDQCOZRJMSPIBC-UHFFFAOYSA-N n-(butoxymethyl)-n-methylprop-2-enamide Chemical compound CCCCOCN(C)C(=O)C=C CDQCOZRJMSPIBC-UHFFFAOYSA-N 0.000 claims description 2
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims description 2
- LFJIAQOELDZMAR-UHFFFAOYSA-N n-methylprop-2-enamide;propane-1-sulfonic acid Chemical compound CNC(=O)C=C.CCCS(O)(=O)=O LFJIAQOELDZMAR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- HULBECQFWZPEBI-UHFFFAOYSA-N octyl but-2-enoate Chemical compound CCCCCCCCOC(=O)C=CC HULBECQFWZPEBI-UHFFFAOYSA-N 0.000 claims description 2
- 239000005011 phenolic resin Substances 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[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
- AABBHSMFGKYLKE-UHFFFAOYSA-N propan-2-yl but-2-enoate Chemical class CC=CC(=O)OC(C)C AABBHSMFGKYLKE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011241 protective layer Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- QHSPZGZEUDEIQM-UHFFFAOYSA-N tert-butyl but-2-enoate Chemical compound CC=CC(=O)OC(C)(C)C QHSPZGZEUDEIQM-UHFFFAOYSA-N 0.000 claims description 2
- NCYNWQDLQJUTIY-UHFFFAOYSA-N tetradecyl but-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=CC NCYNWQDLQJUTIY-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- HBGPNLPABVUVKZ-POTXQNELSA-N (1r,3as,4s,5ar,5br,7r,7ar,11ar,11br,13as,13br)-4,7-dihydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1h-cyclopenta[a]chrysen-9-one Chemical compound C([C@@]12C)CC(=O)C(C)(C)[C@@H]1[C@H](O)C[C@]([C@]1(C)C[C@@H]3O)(C)[C@@H]2CC[C@H]1[C@@H]1[C@]3(C)CC[C@H]1C(=C)C HBGPNLPABVUVKZ-POTXQNELSA-N 0.000 claims 1
- PFRGGOIBYLYVKM-UHFFFAOYSA-N 15alpha-hydroxylup-20(29)-en-3-one Natural products CC(=C)C1CCC2(C)CC(O)C3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 PFRGGOIBYLYVKM-UHFFFAOYSA-N 0.000 claims 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XGGIQXQJSPURNB-UHFFFAOYSA-N CC=CC(=O)OCCOC1=CC=CC2=CC=CC=C21 Chemical compound CC=CC(=O)OCCOC1=CC=CC2=CC=CC=C21 XGGIQXQJSPURNB-UHFFFAOYSA-N 0.000 claims 1
- SOKRNBGSNZXYIO-UHFFFAOYSA-N Resinone Natural products CC(=C)C1CCC2(C)C(O)CC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 SOKRNBGSNZXYIO-UHFFFAOYSA-N 0.000 claims 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 14
- 230000000694 effects Effects 0.000 abstract description 9
- 230000003578 releasing effect Effects 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract 2
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 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
- 238000004132 cross linking Methods 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 230000005540 biological transmission Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004821 Contact adhesive Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000001771 impaired effect Effects 0.000 description 4
- 238000003475 lamination Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- 239000004902 Softening Agent Substances 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
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- 230000007812 deficiency Effects 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
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- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 description 1
- PQHAQYRBYAWNHV-UHFFFAOYSA-N 2-naphthalen-1-yloxyethyl prop-2-enoate Chemical compound C1=CC=C2C(OCCOC(=O)C=C)=CC=CC2=C1 PQHAQYRBYAWNHV-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-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
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 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
- 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
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical class C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent 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
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 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
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005574 norbornylene group Chemical group 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 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
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZHDCHCTZRODSEN-UHFFFAOYSA-N propyl but-2-enoate Chemical compound CCCOC(=O)C=CC ZHDCHCTZRODSEN-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000012216 screening Methods 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
- 239000003351 stiffener Substances 0.000 description 1
- 238000003860 storage Methods 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
- 239000012745 toughening agent 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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 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
-
- 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
- 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
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Multimedia (AREA)
- Signal Processing (AREA)
- Automation & Control Theory (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
- Adhesive Tapes (AREA)
Abstract
The present invention relates to an acrylic pressure-sensitive adhesive composition, a polarizing plate and a liquid crystal display device, using the same. More specifically, the present invention relates to an acrylic pressure-sensitive adhesive composition 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) containing no cross-linkable functional group, and a multi-functional cross-linking agent (C). A polarizing plate and a liquid crystal displaydevice comprising the pressure-sensitive adhesive composition meets with major properties such as adhesion endurance reliability, with effectively providing optical compensation effect and stress release effect, and has an effect of improving a light leakage phenomenon.
Description
Technical field
[1] the present invention relates to a kind of acrylic pressure sensitive adhesive composition that is used for polaroid.More specifically, the present invention relates to a kind of contact adhesive composition that is used for polaroid, described composition has excellent low light leak performance, and under high temperature or hot and humid condition, do not change its salient features for example durable reliability and workability, and the polaroid and the LCD device that contain described composition.
[2]
Background technology
[3] common, when the preparation LCD device, all need to comprise the liquid crystal cell of liquid crystal and polaroid basically, and must use suitable adhesive layer or pressure sensitive adhesive layer that they are combined.In addition, in order to improve the function of LCD device, can use phase delay chip, be used for the compensating gauge, brightness enhancement film at wide visual angle etc., it is additionally adhered on the polaroid.
[4] primary structure of formation LCD device generally includes the consistent liquid crystal layer of orientation; Polaroid with multilayered structure, described polaroid combine with pressure sensitive adhesive layer or bonding coat and the liquid crystal cell to be made up of transparency glass plate that contains transparent electrode layer or plastics sheet materials; Phase delay chip; And additional functional film layer or the like.
[5] structure of polaroid is to be included in the iodine compound that is orientated on a certain direction or the structure of dichroism polarization material.In order to protect these polarizers, the two sides uses the protective membrane of triacetyl cellulose (TAC) for example to form multilayer.In addition, polaroid can comprise phase retardation film or be used for the compensate film as the liquid crystal type film at wide visual angle that its shape has unidirectional molecular orientation extraly.
[6] above-mentioned film is made up of the material that has different molecular structures and form, and therefore has different physicalies.In particular, under high temperature or hot and humid condition, depend on the dimensional stability deficiency of the contraction or expansion of material with unidirectional molecular orientation.As a result of, if polaroid is fixed by pressure sensitive adhesive, the stress that is caused by contraction or expansion under high temperature or hot and humid condition will concentrate on the TAC layer so, thereby cause double refraction and light leak.In this case, on layer, cause negative birefringence by the TAC that shrinks usually.
[7] simultaneously, pressure sensitive adhesive layer at high temperature needs high cohesive strength to keep durable reliability, uses partial cross-linked viscoelastic material for this reason.When introducing partial cross-linked structure in varistor layer, this varistor layer has unrelieved stress under given applied stress, and the polymkeric substance in the crosslinking structure is orientated with form dielectric grid with specific direction.Under this orientation, common alkyl acrylic pressure sensitive adhesive forms the double refraction of negative value, as in TAC.
[8] simultaneously, the monitor dimension of computer etc. is just becoming increasing, and increases rapidly recently for the demand of the LCD TV that uses polaroid.Because it is big that these panels become, polaroid also becomes greatly, causes the unrelieved stress of TAC layer and pressure sensitive adhesive layer to uprise, and makes negative birefringence increase thus, and therefore light leak is significantly increased.
[9] make light leak under such unrelieved stress in the minimized method, can consider a kind of method, for example, have on the occasion of birefringent material or the Acrylic Acid Monomer that has positive birefringence by copolymerization and make the minimized method of total double refraction that under unrelieved stress, comprises TAC layer and pressure sensitive adhesive by in final pressure sensitive adhesive layer, adding (mixing).
[10] the disclosed patent disclosure No.2003-0069461 of Korea S discloses a kind of birefringent pressure sensitive adhesive of negative value of having revised,, described tackiness agent by with 0.01～40 weight part, join revise the negative value double refraction that the acrylic pressure-sensitive adhesive layer shows in this acrylic pressure-sensitive adhesive layer under unrelieved stress showing as low molecular weight material on the occasion of degree of birefringence under the unrelieved stress.Yet, in described pressure sensitive adhesive,, caused reducing the modulus of pressure sensitive adhesive owing to wherein introduced low molecular weight material.Therefore, in processing polaroid process, cut out the aspect of performance existing problems at it.In addition, also exist the long storage low molecular weight material is migrated into the problem in the interface and may produce the problem that is separated with acrylic pressure-sensitive adhesive.
[11] carry out the incompatible minimized method of double refraction also known (referring to Applied Optics (applied optics) (1997)) that makes of copolymerization by monomer that will under residual stress, show as negative birefringence and the monomer that shows as positive birefringence.In an object lesson, the double refraction degree under given applied stress can be adjusted by the Acrylic Acid Monomer (positive birefringence) that copolymerization has the Acrylic Acid Monomer (negative birefringence) of alkyl group side chain and has an aryl side chain.
[12] the patent disclosure No.2002-332468 of Japanese unexamined has described by introducing the method that Acrylic Acid Monomer that side chain contains aryl improves the plastic resistance of pressure sensitive adhesive layer.In addition, U.S. Patent No. 6,663,978 and the patent disclosure Nos.2002-173656 of Japanese unexamined and 2003-013029 described by introducing Acrylic Acid Monomer that side chain contains aryl and regulated the method for the specific refractory power of pressure sensitive adhesive layer.In addition, the patent disclosure No.2005-053976 of Japanese unexamined has described by introducing the Acrylic Acid Monomer that side chain contains aryl and has improved the method for sticking performance in the lower polarity film.
[13]
Summary of the invention
Technical problem
[14] yet, in above-mentioned existing open file, and the technological thought of not mentioned trial optical compensation, promptly when the Acrylic Acid Monomer that contains aryl by the introducing side chain prepared the acrylic pressure-sensitive adhesive that is used for polaroid, the double refraction under the described optical compensation adjustment unrelieved stress was to improve light leakage phenomena.
[15]
Technical scheme
[16] the invention is intended to solve above-mentioned traditional problem, and one object of the present invention is to be provided for the contact adhesive composition of polaroid as pressure sensitive adhesive layer, said composition has on the occasion of having excellent low light leak it by (methyl) acrylic copolymer adjustment double refraction that use has optimal stress releasing property under unrelieved stress, and under high temperature or hot and humid condition, can not change its salient features for example durable reliability and workability,, described (methyl) acrylic copolymer comprises the acrylic copolymer (A) of the optical compensation that contains crosslinkable functionality, the acrylic copolymer (B) that does not contain the optical compensation of crosslinkable functionality, and polyfunctional linking agent (C).
[17] another object of the present invention is to provide the polaroid that uses the acrylic pressure sensitive adhesive composition with described feature.
[18] another object of the present invention is to provide the LCD device that comprises the polaroid that utilizes the acrylic pressure sensitive adhesive composition preparation with described feature.
[19]
Embodiment
[20] the present invention relates to a kind of acrylic pressure sensitive adhesive composition, it comprises:
[21] acrylic copolymer (A), it contains i) (methyl) alkyl acrylate monomer of alkyl 50～75 weight parts, that have 2～14 carbon atoms, ii) 25～50 weight parts, can with the acrylate monomer that contains aryl of described Acrylic Acid Monomer copolymerization, vinyl iii) 0.1～10 weight part, that contain crosslinkable functionality or acrylate monomer;
[22] acrylic copolymer (B), it comprises i) (methyl) alkyl acrylate monomer of alkyl 50～75 weight parts, that have 2～14 carbon atoms and ii) 25～50 weight parts, can with the acrylate monomer that contains aryl of described Acrylic Acid Monomer copolymerization; With
[23] multifunctional linking agent (C), described linking agent can be crosslinked with the above-mentioned acrylate monomer that comprises crosslinkable functionality iii).
[24], use usually by in high molecular weight copolymer, adding softening agent or low molecular weight material or adjusting the method that crosslinking structure comes to provide as pressure sensitive adhesive the stress relief function for improving light leakage phenomena.Yet, only by the very difficult light leakage phenomena that suppresses polaroid fully of stress relief.Although this is because partial cross-linked structure can be introduced into tackiness agent to keep the durable reliability of the pressure sensitive adhesive that is used for polaroid, the unrelieved stress that has in the pressure sensitive adhesive layer of this crosslinking structure can not be removed fully.Therefore, under this unrelieved stress, have negative birefringence in the normally used alkyl acrylate pressure sensitive adhesive layer, the negative birefringence that exists in the TAC layer of described negative birefringence and contraction has constituted the major cause that can't further improve light leak together.In order to compensate the negative birefringence that exists in the described pressure sensitive adhesive layer, can allow in pressure sensitive adhesive layer, to introduce (optical compensation) pressure sensitive adhesive layer that shows as positive birefringence by propylene copolymerization acid mono (Acrylic Acid Monomer that contains aryl) preparation.Yet, when utilizing such optical compensation to improve light leak simply, need a large amount of Acrylic Acid Monomers that contains aryl, thus the side effect that exists the adhesion strength of pressure sensitive adhesive significantly to be increased.This has produced negative impact to the separating power again of major function as the pressure sensitive adhesive that is used for polaroid.Therefore, in order to suppress the light leak of polaroid as much as possible, and keep durable reliability and as the separating power again of major function of the pressure sensitive adhesive that is used for polaroid, the optical compensation of suitable degree must be provided simultaneously, and by introducing the stress relief function maximization that best crosslinking structure makes pressure sensitive adhesive.
[25] therefore, the invention is characterized in and have best crosslinking structure, described structure can make light leakage phenomena minimize, and keep the major function of pressure sensitive adhesive, the mixture that it has used the acrylic copolymer (A) of the optical compensation that contains crosslinkable functionality and has not contained the acrylic copolymer (B) of the optical compensation of crosslinkable functionality.
[26] in order to make acrylic pressure sensitive adhesive composition of the present invention have so best crosslinking structure, the weight ratio of acrylic copolymer (A) and acrylic copolymer (B) is preferably 1: 9～and 4: 1.
[27] when the ratio of acrylic copolymer (A) during, be difficult to obtain enough cohesive strengths less than the ratio of acrylic copolymer (B).Therefore, described ratio is suitably greater than 1: 9, more preferably greater than 1: 4.In addition, when the ratio of acrylic copolymer (A) and acrylic copolymer (B) during greater than 4: 1, the ratio of crosslinkable multipolymer increases.As a result of, with very difficult control crosslinking degree with by stress relief and optical compensation improved effect light leak in conjunction with pressure sensitive adhesive.
[28] in addition, the weight-average molecular weight of preferred acrylic copolymer (A) and acrylic copolymer (B) is 800,000～2,000,000 independently of one another in acrylic pressure sensitive adhesive composition of the present invention.
[29] if described weight-average molecular weight less than 800,000, then cohesive strength is weakened so that the durable reliability deficiency.If described weight-average molecular weight is greater than 2,0000,00, then the stress relief effect with weakened so that the light leak effect is slight.
[30] below will explain each composition in this composition in detail.
[31]
[32]
Acrylic copolymer (A) and (B)
[33] (methyl) alkyl acrylate monomer i)
[34], comprise i as the acrylic copolymer (A) and the acrylic copolymer (B) of main resin according to the present invention) (methyl) alkyl acrylate monomers of 50～75 weight parts, wherein alkyl has 2～14 carbon atoms.(methyl) alkyl acrylate monomer i in described acrylic copolymer (A) and acrylic copolymer (B)) can be identical or different.
[35] if described (methyl) alkyl acrylate monomer i) amount surpass 75 weight parts, then final pressure sensitive adhesive shows high negative birefringence under unrelieved stress, the effect that therefore improves the optics light leak may be slight.In addition, if described (methyl) alkyl acrylate monomer i) amount less than 50 weight parts, the adhesivity balance of then final pressure sensitive adhesive is impaired, this tackiness agent shows high positive birefringence under unrelieved stress, the effect that therefore improves the optics light leak is impaired.
[36] wherein alkyl has (methyl) alkyl acrylate monomer i of 2～14 carbon atoms) be preferably and be selected from in the following compounds one or more: (methyl) vinylformic acid ethyl ester, (methyl) vinylformic acid n-propyl ester, (methyl) vinylformic acid isopropyl esters, (methyl) n-butylacrylate, (methyl) vinylformic acid tertiary butyl ester, (methyl) vinylformic acid sec-butyl ester, (methyl) vinylformic acid amyl group ester, (methyl) 2-ethylhexyl acrylate, (methyl) vinylformic acid n-octyl ester, (methyl) isooctyl acrylate ester, the different nonyl ester of (methyl) vinylformic acid, (methyl) vinylformic acid Lauryl Ester, and (methyl) vinylformic acid tetradecyl ester.If the carbon number of alkyl is not in above-mentioned scope, then the second-order transition temperature of pressure sensitive adhesive (Tg) will increase, and it is difficult that perhaps fusible adjustment will become.Therefore, carbon number is limited in 2～14 the scope.
[37]
[38] ii) contain (methyl) Acrylic Acid Monomer of aryl
[39] according to the present invention, comprise (methyl) alkyl acrylate monomer (alkyl that wherein has 2～14 carbon atoms) in order to compensate wherein as the negative birefringence in the acrylic copolymer of principal constituent, acrylic copolymer (A) and acrylic copolymer (B) be for to show the monomer of positive birefringence under stress, and comprise ii) 25～50 weight parts, can with the acrylate monomer that contains aryl of described Acrylic Acid Monomer (methyl) alkyl acrylate monomer copolymerization.It ii) can be identical or different being included in acrylate monomer in described acrylic copolymer (A) and the acrylic copolymer (B), that contain aryl.
[40] the described amount that contains (methyl) acrylate monomer of aryl accounts for all monomeric 25～50 weight parts suitably.If less than 25 weight parts, then final pressure sensitive adhesive shows big negative birefringence to the amount of (methyl) acrylate monomer that contains aryl under unrelieved stress in all monomers, the effect that therefore improves the optics light leak is slight.If amount surpasses 50 weight parts, the adhesivity balance of then final pressure sensitive adhesive is impaired.In particular, adhesion strength significantly increases, so that the separating power again of polaroid is impaired serious.
[41] according to the present invention, but (methyl) acrylate monomer that contains the copolymerization aryl preferably uses the compound of formula 1:
[42]
[43]
[44] wherein,
[45] R
1Be hydrogen or methyl,
[46] R
2For having the alkylidene group of 1～12 carbon atom,
[47] n is 0～3 integer, preferred 0 or 1,
[48] X is Sauerstoffatom, sulphur atom or the alkylidene group with 1～4 carbon atom, and
[49] Ar is unsubstituted or by halogen especially bromine or chlorine or the aryl that replaced by the alkyl of 1～12 carbon atom.
[50]
[51] preferred example of described formula 1 compound includes but not limited to: (methyl) vinylformic acid phenoxy group ethyl ester, (methyl) benzyl acrylate ester, (methyl) vinylformic acid 2-thiophenyl-1-ethyl ester, (methyl) vinylformic acid 6-(4,6-two bromo-2-sec.-propyl phenoxy groups)-the 1-polyhexamethylene, (methyl) vinylformic acid 6-(4,6-two bromo-2-sec-butyl phenoxy groups)-the 1-polyhexamethylene, (methyl) vinylformic acid 2,6-two bromo-4-nonyl phenylesters, (methyl) vinylformic acid 2,6-two bromo-4-dodecylphenyl esters, vinylformic acid 2-(1-naphthyloxy)-1-ethyl (methyl) ester, (methyl) vinylformic acid 2-(2-naphthyloxy)-1-ethyl ester, (methyl) vinylformic acid 6-(1-naphthyloxy)-1-polyhexamethylene, (methyl) vinylformic acid 6-(2-naphthyloxy)-1-polyhexamethylene, (methyl) vinylformic acid 8-(1-naphthyloxy)-1-octyl group ester, (methyl) vinylformic acid 8-(2-naphthyloxy)-1-octyl group ester.Described formula 1 compound can use separately or use with the form of mixture.
[52] more preferably, described formula 1 compound is (methyl) vinylformic acid phenoxy group ethyl ester, (methyl) benzyl acrylate ester, vinylformic acid 2-thiophenyl 1-ethyl ester, vinylformic acid 8-(2-naphthyloxy)-1-octyl group ester, vinylformic acid 2-(1-naphthyloxy)-1-ethyl ester, and their mixture; And most preferably, be (methyl) vinylformic acid phenoxy group ethyl ester, (methyl) benzyl acrylate ester or their mixture.
[53]
[54] iii) crosslinkable monomers
[55] in acrylic copolymer of the present invention (A), contain the vinyl of crosslinkable functionality or adhesion strength and the cohesive strength that acrylate monomer iii) is used to adjust acrylic copolymer, and preferably in its structure, comprise acid group or hydroxyl.
[56] vinyl monomer that contains acid group that herein uses is a kind of like this composition, and it is used for giving the pressure sensitive adhesive cohesive strength with the linking agent reaction and by chemical bond, when making elevated temperature, the cohesive failure of tackiness agent can not take place.
[57] the described copolymerisable monomer that contains acid group can comprise one or more in the following compound: contain comonomer or its acid anhydrides of carboxyl, the copolymerisable monomer that contains sulfonic copolymerisable monomer and contain phosphate.
[58] the above-mentioned copolymerisable monomer that contains carboxyl is (methyl) vinylformic acid, propyloic acrylic ester, carboxylic amyl group acrylate, methylene-succinic acid, toxilic acid, fumaric acid or Ba Dousuan;
[59] acid anhydrides that contains the copolymerisable monomer of carboxyl is maleic anhydride or itaconic anhydride;
[60] containing sulfonic copolymerisable monomer is styrene sulfonic acid, allyl sulphonic acid, 2-(methyl) acrylamide-2-methyl propane sulfonic acid, (methyl) acrylamide propane sulfonic acid, sulfopropyl (methyl) acrylate, (methyl) acryloxy naphthyl sulfonic acid; And
[61] copolymerisable monomer that contains phosphate group can be selected from 2-hydroxyethyl acryloyl phosphoric acid ester etc., but is not limited thereto.
[62] in addition, the vinyl of hydroxyl or Acrylic Acid Monomer are preferably and are selected from (methyl) vinylformic acid 2-hydroxyethyl ester, (methyl) vinylformic acid 2-hydroxypropyl ester, (methyl) vinylformic acid 4-hydroxyl butyl ester, (methyl) vinylformic acid 2-hydroxyl glycol ester and (methyl) vinylformic acid 2-hydroxypropyl diol ester one or more.
[63] too much if described in the acrylic copolymer (A) contains the amount of the vinyl of acid group or hydroxyl or Acrylic Acid Monomer, then adhesivity descends, and release strength descends.Therefore, in all monomers its amount preferably in the scope of 0.01～10 weight part.
[64]
[65] iv) function monomer
[66] for the second-order transition temperature of adjusting pressure sensitive adhesive or other functions are provided, (methyl) preferably of the present invention acrylic copolymer (A) and (B) comprise further that independently of one another formula 2 function monomers based on 0～20 weight part of whole monomer weights are iv) as selectable components.
[67]
[68]
[69] wherein,
[70] R
4Be hydrogen or alkyl,
[71] R
3Be cyano group, unsubstituted or with alkyl, acetoxyl group or COR
5The phenyl that replaces, wherein R
5Be glycidoxypropyl amino, unsubstituted or that replaced by alkyl.
[72] in above-mentioned chemical formula, R
3～R
5The alkyl preferably low alkyl group of 1～6 carbon atom, more preferably methyl or ethyl.
[73] example of described formula 2 compounds can include but not limited to: styrene monomer, for example vinylbenzene or alpha-methyl styrene; Vinyl esters of carboxylic acids class, for example vinyl acetate; Or nitrogenous vinyl monomer class, for example vinyl cyanide, (methyl) acrylamide, N-methyl (methyl) acrylamide, N-butoxymethyl (methyl) acrylamide or (methyl) glycidyl acrylate.Described monomer can use separately or mix use by two or more.
[74] if the function monomer of described formula 2 amount iv) is too high, then the snappiness of pressure sensitive adhesive and stripping strength descend.Therefore, usage quantity is preferably less than whole 20 weight parts of monomer components.
[75]
[76] v) polymerization process
[77] be used to prepare acrylic copolymer of the present invention (A) and method (B) and do not have specific restriction, and described (methyl) acrylic copolymer can prepare by solution polymerization, photopolymerization, mass polymerization, suspension polymerization or letex polymerization.Preferably, by using solution polymerization to prepare.Polymerization temperature is preferably 50～140 ℃, and initiator preferably adds under the mixed uniformly state of monomer.
[78] can to use separately or use azo with the form of mixture be for example Diisopropyl azodicarboxylate and azo two cyclohexanenitriles of polymerization starter to described polymerization starter, or superoxide for example benzoyl peroxide and acetyl peroxide.
[79]
[80]
Polyfunctional linking agent (C)
[81] be crosslink propylene acid copolymer (A), based on (methyl) acrylic copolymer of 100 weight parts, acrylic pressure sensitive adhesive composition of the present invention can comprise the multifunctional linking agent (C) of 0.01～10 weight part.In above-mentioned scope, can provide preferred physicals.
[82] described multifunctional linking agent (C) and the cohesive strength of reactions such as carboxyl and hydroxyl with the increase pressure sensitive adhesive.
[83] preferably, described multifunctional linking agent is to be selected from isocyanate compound, epoxy compounds, aziridine cpd and the metal chelate compound one or more.Wherein, for application target, isocyanate compound is easy to use.
[84] described isocyanate compound can be to be selected from the reactant of tolylene diisocyanate, dimethylbenzene two isocyanic acids, '-diphenylmethane diisocyanate, HDI, paraiodoxyanlsol vulcabond, tetramethylxylene diisocyanate, naphthalene diisocyanate and they and polyvalent alcohol (TriMethylolPropane(TMP) etc.) one or more
[85] described epoxy compounds can be to be selected from ethylene glycol diglycidylether, triglycidyl ether, trihydroxymethylpropanyltri diglycidyl ether, N, N, N ', one or more in N '-four glycidyl group quadrol and the glycerin diglycidyl ether.
[86] described aziridine cpd can be to be selected from N; N '-Toluene-2,4-diisocyanate; 4-two (1-aziridine carboxide), N; N '-ditane-4; in 4 '-two (1-aziridine carboxides), Tretamine, two isophthaloyl base-1-(2-methylaziridine) (bisisoprothaloyl-1-(2-methylaziridine)) and the three-1-'-aziridino phosphine oxide one or more
[87] described metal chelate compound can use but be not limited to: be selected from by polyvalent metal one or more in aluminium, iron, zinc, tin, antimony, magnesium and vanadium and methyl ethyl diketone (acethylacetone) or the methyl aceto acetate coordinate compound for example.
[88] when the sense crosslinking reaction of linking agent in the cohesive process that is forming pressure sensitive adhesive layer took place hardly, multifunctional linking agent can be applied equably.If carry out drying and slaking after coating procedure is finished, can form crosslinking structure to obtain to have the pressure sensitive adhesive layer of elasticity and strong cohesive strength.
[89]
[90]
Additive
[91] in addition, if this composition is adhered on the substrate of glass, it can further comprise silane coupling agent improving adhesion stability, thereby further improves thermotolerance/moistureproofness.When described substrate of glass is placed on high temperature and high humidity environment following time for a long time, this silane coupling agent helps to improve and adheres to reliability, is 0.005～5 weight part based on the usage quantity of the described silane coupling agent of all acrylic copolymer of 100 weight parts.If less than 0.005 weight part, then improving, amount do not adhere to reliability.If amount surpasses 5 weight parts, then durable reliability descends.
[92] described silane coupling compound is γ-epoxypropoxy (g-glycydoxypropyl) Trimethoxy silane, γ-epoxypropoxy (g-glycydoxypropyl) methyldiethoxysilane, γ-epoxypropoxy (g-glycydoxypropyl) triethoxyl silane, 3-sulfydryl propyl trimethoxy silicane, vinyltrimethoxy silane, vinyltriethoxysilane, γ-methacryloxypropyl trimethoxy silane, γ-methacryloxypropyl triethoxyl silane, γ-An Bingjisanyiyangjiguiwan, 3-isocyanic ester propyl-triethoxysilicane, or γ-acetylacetic ester propyl trimethoxy silicane etc.These can use separately or use with mixture.
[93] the present invention can further comprise tackifier resins, and based on 100 parts by weight of acrylic multipolymers (A), its usage quantity can be 1～100 weight part.If amount is less than 1 weight part, then a little less than the tackify function.If amount surpasses 100 weight parts, then the consistency of pressure sensitive adhesive or cohesive strength often reduce.
[94] tackifier resins can use (hydrogenation) hydrocarbon resin, (hydrogenation) Gum Rosin, (hydrogenation) rosin ester resin, (hydrogenation) terpine resin, (hydrogenation) terpene phenolic resin, polymerized rosin resin or polymerized rosin ester resin etc.These can use separately or be used by two or more mixing of above-mentioned resin.
[95] in addition, can additionally mix and use vinylformic acid low-molecular weight polymer, Resins, epoxy, stiffening agent etc. being used for special purpose, and can suitably add and use UV stabilizer, antioxidant, tinting material, toughener, weighting agent, defoamer, tensio-active agent, softening agent etc. to be used for conventional purposes.
[96] in addition, the present invention relates to a kind of polaroid, described polaroid is characterised in that it comprises:
[97] polarizing coating and
[98] pressure sensitive adhesive layer, described pressure sensitive adhesive layer contains acrylic pressure sensitive adhesive composition of the present invention.
[99] this polaroid is included in pressure sensitive adhesive layer on the one or both sides of polarizing coating, that formed by above-mentioned contact adhesive composition.There is no particular limitation to the polarizing coating of forming polaroid or polarising means.
[100] for example, described polarizing coating is that for example iodine or dichroic dye are contained in the polyvinyl alcohol resin film film with the stretching the finished product with polarization component.Also there is no particular limitation for the thickness of these polarizing coatings, can form usual thickness.Described polyvinyl alcohol resin can use polyvinyl alcohol, polyvinyl formal, polyvinylacetal and saponification vinyl-vinyl acetate copolymer etc.
[101] on the two sides of polarizing coating, can form multilayer film, laminated thereon protective membrane, as cellulose membrane, triacetyl cellulose etc. for example; Polyester film, for example polycarbonate or polyethylene terephthalate etc.; Polyester film, for example polyethersulfone; Polyolefin film, for example polyethylene, polypropylene, contain the ring or the polyolefine or the ethylene propylene copolymer of norbornylene structure.There is no particular limitation to the thickness of these protective membranes, can form usual thickness.
[102] there is no particular limitation to the method that forms pressure sensitive adhesive layer among the present invention on polarizing coating, can use following method: utilize direct coating pressure sensitive adhesive on the polarizing coating surface such as scraping strip coating machine, and dry this tackiness agent; Or pressure sensitive adhesive is coated on the surface of separable substrate, dry this tackiness agent is transferred to the pressure sensitive adhesive layer that forms on the described separable substrate surface on the surface of polarizing coating, and the described layer of slaking.
[103] in addition, can lamination on polaroid of the present invention one or more layers to be to provide extra function, for example protective layer, reflecting layer, antiglare layer, phase delay chip, the compensate film that is used for wide visual angle and brightness enhancement film.Also pressure sensitive adhesive layer according to the present invention can be adhered to described functional layer.
[104] polaroid of having used pressure sensitive adhesive of the present invention can be used for all LCD device commonly used, and there is no particular limitation to the kind of liquid crystal panel.Preferably, the present invention can constitute LCD device, and this liquid crystal indicator contains the liquid crystal panel that the pressure sensitive adhesive polaroid is attached to the one or both sides of liquid crystal cell.
[105] the present invention will explain in more detail by following embodiment and comparative example.These examples are provided to help to concrete understanding of the present invention, but scope of the present invention is not limited to these examples.
[106]
[107] preparation embodiment 1
[108] form shown in the following tabulation 1, to be joined in the reactor of 1L by the monomer mixture that the hydroxyl-metacrylate and the 30 parts by weight of acrylic benzyl esters of 68 parts by weight of acrylic n-butyl (BA), 2.0 weight parts are formed, described reactor is equipped with and is used for nitrogen reflux and convenient thermoregulator cooling system.Then, to the ethyl acetate of wherein adding 150 weight parts (EAc) as solvent.In order to remove oxygen, use nitrogen purge 60 minutes, and temperature is remained on 60 ℃.To the reaction initiator Diisopropyl azodicarboxylate (AIBN) that wherein adds 0.03 weight part and reacted 8 hours.After the reaction, with preparation acrylic copolymer (A-1), described acrylic copolymer (A-1) has the solid content of 20 weight % with ethyl acetate (EAc) dilution final product, and weight-average molecular weight is 1,200,000.
[109] preparation embodiment 2～8
[110] as shown in following table 1,, prepared the high-molecular weight acrylic copolymer not adding or partly adding under the situation of the part component among the preparation embodiment 1.They the results are shown in Table 1.
[111] table 1
[table 1]
[table]
[112]
[113] embodiment 1
[114]＜in conjunction with
[115] the high-molecular-weight propylene acid copolymer uniform mixing that obtains among the preparation embodiment 5 of high-molecular-weight propylene acid copolymer that obtains among the preparation embodiment 1 with 20 weight parts and 80 weight parts, the glycidoxy-propyltrimethoxy silane that adds the tolylene diisocyanate adducts (TDI-1) of TriMethylolPropane(TMP) of 0.1 weight part and 0.1 weight part is as multifunctional linking agent.Consider screening characteristics, mixture is diluted to suitable concentration and uniform mixing.Final product is painted on separable and goes up and be dried, to obtain 30 microns homogeneous pressure sensitive adhesive layer.
[116]＜lamination step 〉
[117] pressure sensitive adhesive layer with above-mentioned preparation adheres on the iodine polaroid of 185 micron thickness.The gained polaroid is cut into suitable size and estimates.2 evaluation results that provided the polaroid of having used described pressure sensitive adhesive on it of tabulating down.
[118]
[119] embodiment 2～3
[120] acrylic copolymer is carried out combination and lamination step through the method identical with embodiment 1, wherein, in the following tabulation 2 in conjunction with shown in the ratio, based on the combination of embodiment 1, some not in conjunction with or the part combination.Then, durable reliability and light transmission homogeneity are estimated with the method identical with embodiment 1, the results are shown in following table 2.
[121]
[122] comparative example 1～4
[123] acrylic copolymer is carried out combination and lamination step through the method identical with embodiment 1, wherein, in the following tabulation 2 in conjunction with shown in the ratio, based on the combination of embodiment 1, some not in conjunction with or the part combination.Then, durable reliability and light transmission homogeneity are estimated with the method identical with embodiment 1, the results are shown in following table 2.
[124]
[125] EXPERIMENTAL EXAMPLE
[126] 1. separating power again
The polaroid that [1 27] will scribble pressure sensitive adhesive is divided into 90 mm wides and 170 millimeters long, utilizes doubler that it is adhered on the alkali-free sheet glass of Corning Inc. production then.Then, this sheet glass was placed in the temperature and humidity chamber 1 hour,, and placed room temperature following 1 hour 50 ℃ of heating 4 hours, subsequently with polaroid from separation on glass.Separating power is estimated by following again:
[128] zero: separate easily
[129] △: be difficult to separate
[130] *: be difficult to separate, so that substrate or glass fragmentation
[131]
[132] 2. durable reliability
[133] form that the polaroid that scribbles pressure sensitive adhesive (90mmx170mm) of preparation in the foregoing description 1 is intersected with optical absorption axle separately is attached to the both sides of substrate of glass (110mmx190mmx0.7mm).It is about 5kg/cm that substrate of glass is placed applying pressure
2The decontamination chamber in, to avoid the generation of bubble or impurity.For the humidity resistance of assess sample, they were placed 1000 hours under the relative humidity of 60 ℃ temperature and 90%, observe the formation or the separation of bubble then.And, for the thermotolerance of assess sample, it was placed 1000 hours at 80 ℃, observe the formation or the separation of bubble then.Sample is placed at room temperature 24 hours, immediately their state is estimated then.And, the pressure sensitive adhesive polaroid of above-mentioned preparation was placed 5 months or more of a specified duration, estimate its reliability according to aforesaid method then.The judgement criteria of durable reliability is as follows:
[134] zero: do not observe bubble and produce or separation phenomenon.
[135] △: produce a small amount of bubble or separation phenomenon.
[136] *: a large amount of bubbles or separation phenomenon produced.
[137]
[138] 3. light transmissive homogeneity (light leak)
[139], in the darkroom, utilize sight glass substrate backlight whether light leak is arranged in order to study light transmissive homogeneity.The form that the polaroid that scribbles pressure sensitive adhesive (310mmx385mm) of preparation in the foregoing description 1 is intersected with separately optical absorption axle is attached to the both sides of substrate of glass.These samples are stored under the environment of 60 ℃ of temperature and relative humidity 90%, and placed 500 hours, estimate light transmissive homogeneity then 80 ℃ temperature.Light transmissive homogeneity is estimated by following standard:
[140] ⊙: be difficult to the naked eye determine light transmission ununiformity phenomenon.
[141] zero: a little light transmission ununiformity phenomenon occurs.
[142] △: some light transmission ununiformity phenomenons occur.
[143] *: a large amount of light transmission ununiformity phenomenons appear.
[144] table 2
[table 2]
[table]
[145]
[146] shown in the result of table 2, embodiments of the invention 1～3 show excellent durable reliability and workability (separating power again), and show excellent low light leak.On the other hand, under comparative example 1 situation, the very low so that low light leak excellence of the quantity of crosslinkable polymer, but separating power and durable reliability are poor again.Under comparative example 2 situation, introduced excessive aromatic series and acrylate monomer, so that low light leak excellence, but separating power and durable reliability are poor again.In addition, under comparative example 3 situation, the amount of aromatic series and acrylate is very low, so that low light leak is poor.Under comparative example 4 situation, used crosslinkable polymer separately, so that the non-constant of separating power again.
[147]
Industrial applicibility
[148] the present invention relates to a kind of acrylic pressure sensitive adhesive composition that is used for polaroid, it has excellent low light leak, does not change its salient features for example durable reliability and workability again under hot conditions and hot and humid condition.Therefore, if described contact adhesive composition is used for the polaroid of LCD device, can avoid the long-time light leakage phenomena of using the back to occur.
[149] with reference to above-mentioned embodiment, the present invention has been described in detail.For a person skilled in the art, can in scope of the present invention and technical spirit, carry out various modifications and variations obviously.Such modifications and variations should belong in the appended claims institute restricted portion.
Claims (21)
1, a kind of acrylic pressure sensitive adhesive composition, it comprises
Acrylic copolymer (A), described acrylic copolymer (A) contains i) (methyl) alkyl acrylate monomers of 50～75 weight parts, this monomer has the alkyl of 2～14 carbon atoms, ii) 25～50 weight parts, can with acrylate monomer described Acrylic Acid Monomer copolymerization, that contain aryl, vinyl iii) 0.1～10 weight part, that contain crosslinkable functionality or acrylate monomer;
Acrylic copolymer (B), described acrylic copolymer (B) contains i) (methyl) alkyl acrylate monomers of 50～75 weight parts, this monomer have the alkyl of 2～14 carbon atoms and ii) 25～50 weight parts, can with acrylate monomer described Acrylic Acid Monomer copolymerization, that contain aryl; And
Multifunctional linking agent (C), described linking agent can be crosslinked with the above-mentioned acrylate monomer that contains crosslinkable functionality iii).
2, the acrylic pressure sensitive adhesive composition described in claim 1, wherein the weight ratio of acrylic copolymer (A) and acrylic copolymer (B) is 1: 9～4: 1.
3, the acrylic pressure sensitive adhesive composition described in claim 1, wherein the weight-average molecular weight of acrylic copolymer (A) and acrylic copolymer (B) is 800,000～2,000,000 independently of one another.
4, acrylic pressure sensitive adhesive composition described in claim 1, wherein (methyl) alkyl acrylate monomer i in acrylic copolymer (A) and acrylic copolymer (B)) independently of one another for being selected from the following compound one or more: (methyl) vinylformic acid ethyl ester, (methyl) vinylformic acid just-propyl diester, (methyl) vinylformic acid isopropyl esters, (methyl) n-butylacrylate, (methyl) vinylformic acid tertiary butyl ester, (methyl) vinylformic acid sec-butyl ester, (methyl) vinylformic acid amyl group ester, (methyl) 2-ethylhexyl acrylate, (methyl) vinylformic acid n-octyl ester, (methyl) isooctyl acrylate ester, the different nonyl ester of (methyl) vinylformic acid, (methyl) vinylformic acid Lauryl Ester, (methyl) vinylformic acid tetradecyl ester.
5, the acrylic pressure sensitive adhesive composition described in claim 1, wherein the acrylate monomer that contains aryl in acrylic copolymer (A) and acrylic copolymer (B) ii) is formula 1 compound independently of one another:
Wherein,
R
1Be hydrogen or methyl,
R
2For having the alkylidene group of 1～12 carbon atom,
N is 0～3 integer,
X is Sauerstoffatom, sulphur atom or the alkylidene group with 1～4 carbon atom, and
Ar is unsubstituted or by the aryl that alkyl replaced of halogen or 1～12 carbon atom.
6, acrylic pressure sensitive adhesive composition described in claim 5, wherein said formula 1 compound is to be selected from the following compound one or more: (methyl) vinylformic acid phenoxy group ethyl ester, (methyl) benzyl acrylate ester, (methyl) vinylformic acid 2-thiophenyl-1-ethyl ester, (methyl) vinylformic acid 6-(4,6-two bromo-2-sec.-propyl phenoxy groups)-the 1-polyhexamethylene, (methyl) vinylformic acid 6-(4,6-two bromo-2-sec-butyl phenoxy groups)-the 1-polyhexamethylene, (methyl) vinylformic acid 2,6-two bromo-4-nonyl phenylesters, (methyl) vinylformic acid 2,6-two bromo-4-dodecylphenyl esters, (methyl) vinylformic acid 2-(1-naphthyloxy)-1-ethyl ester, (methyl) vinylformic acid 2-(2-naphthyloxy)-1-ethyl ester, (methyl) vinylformic acid 6-(1-naphthyloxy)-1-polyhexamethylene, (methyl) vinylformic acid 6-(2-naphthyloxy)-1-polyhexamethylene, (methyl) vinylformic acid 8-(1-naphthyloxy)-1-octyl group ester, (methyl) vinylformic acid 8-(2-naphthyloxy)-1-octyl group ester.
7, the acrylic pressure sensitive adhesive composition described in claim 1, wherein vinyl that contains crosslinkable functionality in acrylic copolymer (A) or acrylate monomer iii) contain acid group or hydroxyl in its structure.
8, acrylic pressure sensitive adhesive composition described in claim 7, wherein said vinyl that contains acid group or Acrylic Acid Monomer are to be selected from the following compounds one or more: (methyl) vinylformic acid, acrylic acid dimer, propyloic acrylic ester, carboxylic amyl group acrylate, methylene-succinic acid, toxilic acid, fumaric acid, Ba Dousuan, maleic anhydride, itaconic anhydride, styrene sulfonic acid, allyl sulphonic acid, the amp-2-methyl propane sulfonic acid of 2-(methyl) acryloyl, (methyl) acrylamide propane sulfonic acid, sulfopropyl (methyl) acrylate, (methyl) acryloxy naphthyl sulfonic acid, with 2-hydroxyethyl acryloyl phosphoric acid ester.
9, the acrylic pressure sensitive adhesive composition described in claim 7, wherein said vinyl that contains hydroxyl or Acrylic Acid Monomer are to be selected from the following compounds one or more: (methyl) vinylformic acid 2-hydroxyethyl ester, (methyl) vinylformic acid 2-hydroxypropyl ester, (methyl) vinylformic acid 4-hydroxyl butyl ester, (methyl) vinylformic acid 2-hydroxyl glycol ester and (methyl) vinylformic acid 2-hydroxypropyl diol ester.
10, the acrylic pressure sensitive adhesive composition described in claim 1, wherein acrylic copolymer (A) and acrylic copolymer (B) further comprise formula 2 function monomers based on 0～20 weight part of whole monomer weights independently of one another:
Wherein,
R
4Be hydrogen or alkyl,
R
3Be cyano group, unsubstituted or with alkyl, acetoxyl group or COR
5The phenyl that replaces, wherein R
5Be glycidoxypropyl amino, unsubstituted or that replaced by alkyl.
11, the acrylic pressure sensitive adhesive composition described in claim 10, the function monomer of its Chinese style 2 are to be selected from the following compounds one or more: vinyl cyanide, (methyl) acrylamide, N-methyl (methyl) acrylamide, N-butoxymethyl (methyl) acrylamide, vinylbenzene, vinyl toluene, (methyl) glycidyl acrylate and vinyl acetate.
12, the acrylic pressure sensitive adhesive composition described in claim 1, the content of wherein multifunctional linking agent (C) is 0.01～10 weight part based on acrylic copolymer (A).
13, the acrylic pressure sensitive adhesive composition described in claim 12, wherein polyfunctional linking agent (C) is for being selected from isocyanate compound, epoxy compounds, aziridine cpd and the metal chelate compound one or more.
14, the acrylic pressure sensitive adhesive composition described in claim 13, wherein multifunctional linking agent (C) is one or more isocyanate compounds, and described isocyanate compound is selected from the reactant of tolylene diisocyanate, Xylene Diisocyanate, diphenylmethanediisocyanate, HDI, paraiodoxyanlsol vulcabond, tetramethylxylene diisocyanate, naphthalene diisocyanate and they and polyvalent alcohol.
15, the acrylic pressure sensitive adhesive composition described in claim 1, wherein, based on whole acrylic copolymer of 100 weight parts, described acrylic pressure sensitive adhesive composition further comprises the silane coupling agent of 0.005～5 weight part.
16, acrylic pressure sensitive adhesive composition described in claim 15, wherein said silane coupling agent is to be selected from the following compounds one or more: γ-Huan Yangbingyangbingjisanjiayangjiguiwan, γ-epoxypropoxy methyldiethoxysilane, γ-epoxypropoxy triethoxyl silane, 3-sulfydryl propyl trimethoxy silicane, vinyltrimethoxy silane, vinyltriethoxysilane, γ-methacryloxypropyl trimethoxy silane, γ-methacryloxypropyl triethoxyl silane, γ-An Bingjisanyiyangjiguiwan, 3-isocyanic ester propyl-triethoxysilicane, and γ-acetylacetic ester propyl trimethoxy silicane.
17, the acrylic pressure sensitive adhesive composition described in claim 1, wherein, based on whole acrylic copolymer of 100 weight parts, described acrylic pressure sensitive adhesive composition further comprises the tackifier resins of 1～100 weight part.
18, the acrylic pressure sensitive adhesive composition described in claim 17, wherein said tackifier resins is for being selected from (hydrogenation) hydrocarbon resin, (hydrogenation) Gum Rosin, (hydrogenation) rosin ester resin, (hydrogenation) terpine resin, (hydrogenation) terpene phenolic resin, polymerized rosin resin and the polymerized rosin ester resin one or more.
19, a kind of polaroid, it comprises
Polarizing coating; With
Pressure sensitive adhesive layer, described pressure sensitive adhesive layer contain each described acrylic pressure sensitive adhesive composition among the with good grounds claim 1-16.
20, the polaroid described in claim 19, it further comprises one or more layers, described layer is selected from protective layer, reflecting layer, phase delay chip, the compensate film that is used for wide visual angle and brightness enhancement film.
21, a kind of LCD device that comprises liquid crystal panel wherein sticks to polaroid according to claim 19 the one or both sides of liquid crystal cell.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020070006966 | 2007-01-23 | ||
| KR1020070006966A KR100948778B1 (en) | 2007-01-23 | 2007-01-23 | Optically Compensated Acrylic Pressure-Sensitive Adhesive Composition, Polarizing Plate and Liquid Crystal Display Device containing the same |
| KR10-2007-0006966 | 2007-01-23 | ||
| PCT/KR2007/005166 WO2008091050A1 (en) | 2007-01-23 | 2007-10-22 | Optically compensated acrylic pressure-sensitive adhesive composition, polarizing plate and liquid crystal display device containing the same |
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| CN101679826A true CN101679826A (en) | 2010-03-24 |
| CN101679826B CN101679826B (en) | 2013-02-27 |
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| Country | Link |
|---|---|
| JP (1) | JP5095756B2 (en) |
| KR (1) | KR100948778B1 (en) |
| CN (1) | CN101679826B (en) |
| TW (1) | TWI381031B (en) |
| WO (1) | WO2008091050A1 (en) |
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| CN104011162A (en) * | 2011-12-21 | 2014-08-27 | Lg化学株式会社 | Adhesive composition |
| CN105452413A (en) * | 2013-08-08 | 2016-03-30 | 东友精细化工有限公司 | Adhesive composition and composite polarizing plate using same |
| CN108699285A (en) * | 2016-02-16 | 2018-10-23 | 德莎欧洲股份公司 | It is particularly used for the adhesive substance of curved surface |
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2007
- 2007-01-23 KR KR1020070006966A patent/KR100948778B1/en active IP Right Grant
- 2007-10-22 WO PCT/KR2007/005166 patent/WO2008091050A1/en active Application Filing
- 2007-10-22 JP JP2009547158A patent/JP5095756B2/en active Active
- 2007-10-22 CN CN2007800502557A patent/CN101679826B/en active Active
-
2008
- 2008-01-21 TW TW097102206A patent/TWI381031B/en active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102933624A (en) * | 2010-06-08 | 2013-02-13 | Lg化学株式会社 | Acryl-based copolymers with heatresistance and high strength, and an optical film comprising the same |
| US8765896B2 (en) | 2010-06-08 | 2014-07-01 | Lg Chem, Ltd. | Acrylic copolymer with high heat resistance and high strength, and optical film comprising the same |
| CN102933624B (en) * | 2010-06-08 | 2015-11-25 | Lg化学株式会社 | There is the acrylic copolymer of high heat resistance and high strength and comprise the blooming of this acrylic copolymer |
| CN104011097A (en) * | 2011-11-30 | 2014-08-27 | 学校法人庆应义塾 | Optical film, resin material for optical film, and image display device |
| CN104011162A (en) * | 2011-12-21 | 2014-08-27 | Lg化学株式会社 | Adhesive composition |
| CN104011162B (en) * | 2011-12-21 | 2016-04-13 | Lg化学株式会社 | Binder composition |
| CN105452413A (en) * | 2013-08-08 | 2016-03-30 | 东友精细化工有限公司 | Adhesive composition and composite polarizing plate using same |
| CN108699285A (en) * | 2016-02-16 | 2018-10-23 | 德莎欧洲股份公司 | It is particularly used for the adhesive substance of curved surface |
| CN108699285B (en) * | 2016-02-16 | 2021-06-08 | 德莎欧洲股份公司 | Adhesive substance, in particular for curved surfaces |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5095756B2 (en) | 2012-12-12 |
| CN101679826B (en) | 2013-02-27 |
| JP2010516855A (en) | 2010-05-20 |
| KR100948778B1 (en) | 2010-03-24 |
| WO2008091050A1 (en) | 2008-07-31 |
| KR20080069355A (en) | 2008-07-28 |
| TWI381031B (en) | 2013-01-01 |
| TW200902660A (en) | 2009-01-16 |
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