JP4689166B2 - Adhesive composition, adhesive optical functional member using the same, and liquid crystal display element - Google Patents
Adhesive composition, adhesive optical functional member using the same, and liquid crystal display element Download PDFInfo
- Publication number
- JP4689166B2 JP4689166B2 JP2004001481A JP2004001481A JP4689166B2 JP 4689166 B2 JP4689166 B2 JP 4689166B2 JP 2004001481 A JP2004001481 A JP 2004001481A JP 2004001481 A JP2004001481 A JP 2004001481A JP 4689166 B2 JP4689166 B2 JP 4689166B2
- Authority
- JP
- Japan
- Prior art keywords
- sensitive adhesive
- pressure
- optical functional
- functional member
- adhesive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000003287 optical effect Effects 0.000 title claims description 45
- 239000000203 mixture Substances 0.000 title claims description 30
- 239000000853 adhesive Substances 0.000 title claims description 29
- 230000001070 adhesive effect Effects 0.000 title claims description 29
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 25
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 72
- 229920006311 Urethane elastomer Polymers 0.000 claims description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 210000002858 crystal cell Anatomy 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 claims description 5
- 238000006845 Michael addition reaction Methods 0.000 claims description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
- 239000003522 acrylic cement Substances 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 22
- -1 2-ethylhexyl Chemical group 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 9
- 229920001228 polyisocyanate Polymers 0.000 description 9
- 230000008602 contraction Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 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 description 3
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000010345 tape casting Methods 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KFTHUBZIEMOORC-UHFFFAOYSA-N 2-methylbut-2-enamide Chemical compound CC=C(C)C(N)=O KFTHUBZIEMOORC-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical group OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical class C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- HIBWGGKDGCBPTA-UHFFFAOYSA-N C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 HIBWGGKDGCBPTA-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Chemical class 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl 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
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000009474 hot melt extrusion Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 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 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RASLIQQQAJRCPM-UHFFFAOYSA-N n-methylprop-1-en-1-amine Chemical group CNC=CC RASLIQQQAJRCPM-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A47—FURNITURE; DOMESTIC ARTICLES OR APPLIANCES; COFFEE MILLS; SPICE MILLS; SUCTION CLEANERS IN GENERAL
- A47C—CHAIRS; SOFAS; BEDS
- A47C27/00—Spring, stuffed or fluid mattresses or cushions specially adapted for chairs, beds or sofas
-
- A—HUMAN NECESSITIES
- A47—FURNITURE; DOMESTIC ARTICLES OR APPLIANCES; COFFEE MILLS; SPICE MILLS; SUCTION CLEANERS IN GENERAL
- A47C—CHAIRS; SOFAS; BEDS
- A47C31/00—Details or accessories for chairs, beds, or the like, not provided for in other groups of this subclass, e.g. upholstery fasteners, mattress protectors, stretching devices for mattress nets
- A47C31/12—Means, e.g. measuring means for adapting chairs, beds or mattresses to the shape or weight of persons
- A47C31/123—Means, e.g. measuring means for adapting chairs, beds or mattresses to the shape or weight of persons for beds or mattresses
Description
本発明は粘着剤組成物、それを用いた接着性光学機能部材及び液晶表示素子に関する。 さらに詳しくは、本発明は、高温高湿条件下においても、被着体との密着性及び接着耐久性に優れると共に、被着体の伸縮への対応性を有する粘着剤組成物、偏光板などにこの粘着剤組成物層を設けた接着性光学機能部材及び該粘着剤組成物層を介して液晶セルの両面上に偏光板などの光学機能部材を配設してなる液晶表示素子に関するものである。 The present invention relates to a pressure-sensitive adhesive composition, an adhesive optical functional member using the same, and a liquid crystal display element. More specifically, the present invention is a pressure-sensitive adhesive composition, a polarizing plate, and the like that have excellent adhesion and adhesion durability with an adherend even under high-temperature and high-humidity conditions, and have compatibility with expansion and contraction of the adherend. The present invention relates to an adhesive optical functional member provided with the pressure-sensitive adhesive composition layer and a liquid crystal display element in which optical functional members such as polarizing plates are disposed on both surfaces of the liquid crystal cell via the pressure-sensitive adhesive composition layer. is there.
従来、被着体同士を粘着剤層を介して貼付した物品においては、高温高湿条件下では、粘着剤の接着耐久性が不充分であるため、端部で被着体が剥がれる場合があるという問題があった。
この問題を解決するために、これまで、粘着剤を構成する樹脂成分の分子量を上げたり、架橋度を高めるなどの手段が講じられてきた。しかしながら、このような粘着剤においては、接着耐久性は向上するものの、伸縮の大きな被着体に用いた場合には、その被着体の伸縮に粘着剤が対応できず、様々なトラブル発生の原因となっていた。
Conventionally, in an article in which adherends are pasted together via a pressure-sensitive adhesive layer, the adherend may be peeled off at the end because the adhesive durability of the pressure-sensitive adhesive is insufficient under high temperature and high humidity conditions. There was a problem.
In order to solve this problem, measures such as increasing the molecular weight of the resin component constituting the pressure-sensitive adhesive and increasing the degree of crosslinking have been taken. However, in such an adhesive, although adhesion durability is improved, when used for adherends with large expansion and contraction, the adhesive cannot cope with expansion and contraction of the adherend, and various troubles occur. It was the cause.
一方、液晶表示素子は、一般に配向層を形成した２枚の透明電極基板を、スペーサを介して所定の間隙になるように配向層を内側にして配置し、その周辺をシールして液晶セルを形成すると共に、該電極基板間の間隙に液晶材料を挟持させ、さらに、２枚の電極基板の外側表面に、それぞれ粘着剤層を介して偏光板などの光学機能部材が配設された構造を有している。
このような液晶表示素子に用いられる光学機能部材は、高温高湿条件下において伸縮しやすいが、粘着剤層がこの光学機能部材の伸縮に対し、充分に対応することができず、種々の問題が生じやすくなる。例えば、光学機能部材が偏光板である場合は、偏光板に生ずる内部応力によって偏光板周縁部の吸収軸にゆがみが生じ光の透過率が変化し、いわゆる「白抜け」と呼ばれる現象が発生しやすい。
On the other hand, in a liquid crystal display element, generally, two transparent electrode substrates on which an alignment layer is formed are arranged with a alignment layer inside so as to be a predetermined gap via a spacer, and the periphery is sealed to form a liquid crystal cell. And a structure in which a liquid crystal material is sandwiched between the electrode substrates, and an optical functional member such as a polarizing plate is disposed on the outer surface of each of the two electrode substrates via an adhesive layer. Have.
Optical functional members used in such liquid crystal display elements tend to expand and contract under high-temperature and high-humidity conditions, but the pressure-sensitive adhesive layer cannot sufficiently cope with the expansion and contraction of the optical functional members. Is likely to occur. For example, when the optical functional member is a polarizing plate, the absorption stress at the periphery of the polarizing plate is distorted by the internal stress generated in the polarizing plate, and the light transmittance changes, and a so-called “white spot” phenomenon occurs. Cheap.
このような問題を解決するために、従来、粘着剤に可塑剤や流動パラフィンを添加することで、適度に軟らかくし、応力緩和性を付与することが行なわれている（例えば、特許文献１及び２参照）。
しかしながら、これらの可塑剤や流動パラフィンを含む粘着剤においては、その可塑剤や流動パラフィンがブリードアウトしたり、又は、偏光板を剥離した際にブリードアウトした可塑剤や流動パラフィンで液晶表示素子などの被着体を汚染することがあるなどの問題を生じる。
However, in these pressure-sensitive adhesives including plasticizers and liquid paraffin, the plasticizers and liquid paraffin bleed out, or the plasticizers or liquid paraffin bleed out when the polarizing plate is peeled off, and liquid crystal display elements, etc. This causes problems such as contamination of the adherend.
本発明は、このような状況下で、高温高湿条件下においても、被着体との密着性及び接着耐久性に優れると共に、被着体の伸縮への対応性を有する粘着剤組成物、偏光板などにこの粘着剤組成物層を設けた接着性光学機能部材及び該粘着剤組成物層を介して液晶セルの両面上に偏光板などの光学機能部材を配設してなる液晶表示素子を提供することを目的とするものである。 The present invention, under such circumstances, even under high temperature and high humidity conditions, the adhesive composition having excellent adhesion and adhesion durability with the adherend, and having compatibility with the stretch of the adherend, Adhesive optical functional member provided with this pressure-sensitive adhesive composition layer on a polarizing plate and the like, and a liquid crystal display element comprising optical functional members such as a polarizing plate disposed on both surfaces of the liquid crystal cell via the pressure-sensitive adhesive composition layer Is intended to provide.
本発明者らは、前記目的を達成するために鋭意研究を重ねた結果、アクリル系粘着剤に特定割合のウレタンエラストマーを添加した粘着剤組成物とすることにより、その目的を達成しうることを見出した。本発明は、かかる知見に基づいて完成したものである。 As a result of intensive studies to achieve the above object, the present inventors have found that the object can be achieved by making a pressure sensitive adhesive composition in which a specific proportion of urethane elastomer is added to an acrylic pressure sensitive adhesive. I found it. The present invention has been completed based on such findings.
すなわち、本発明は、
（１）光学機能部材の片面又は両面に、アクリル系粘着剤と該アクリル系粘着剤１００重量部当り０．０１〜１５重量部のウレタンエラストマーとを含む粘着剤組成物からなる層を設けたことを特徴とする接着性光学機能部材、
（２）前記ウレタンエラストマーが構成成分としてポリアミノ化合物に不飽和化合物をマイケル付加させた構造を含むマイケル付加型ウレタンウレア樹脂である上記（１）に記載の接着性光学機能部材、
（３）ウレタンエラストマーの１００％モジュラスが１〜６ＭＰａである上記（１）又は（２）に記載の接着性光学機能部材、
（４）アクリル系粘着剤が重量平均分子量５０万〜２００万の（メタ）アクリル酸エステル単独重合体又は共重合体である上記（１）〜（３）のいずれかに記載の接着性光学機能部材、
（５）アクリル系粘着剤が架橋点を有する重量平均分子量５０万〜２００万の（メタ）アクリル酸エステル共重合体と架橋剤とからなるものである上記（１）〜（３）のいずれかに記載の接着性光学機能部材、
（６）光学機能部材が、偏光板である上記（１）〜（５）のいずれかに記載の接着性光学機能部材及び
（７）液晶セルの両面上に、アクリル系粘着剤と該アクリル系粘着剤１００重量部当り０．０１〜１５重量部のウレタンエラストマーとを含む粘着剤組成物からなる層を介して光学機能部材を配設してなる液晶表示素子
を提供するものである。
That is, the present invention
(1) A layer made of a pressure-sensitive adhesive composition containing an acrylic pressure-sensitive adhesive and 0.01 to 15 parts by weight of a urethane elastomer per 100 parts by weight of the acrylic pressure-sensitive adhesive is provided on one surface or both surfaces of the optical functional member. An adhesive optical functional member characterized by
(2) The adhesive optical functional member according to the above (1), wherein the urethane elastomer is a Michael addition type urethane urea resin including a structure in which an unsaturated compound is added to a polyamino compound as a constituent component.
(3) The adhesive optical functional member according to the above (1) or (2), wherein the 100% modulus of the urethane elastomer is 1 to 6 MPa,
(4) The adhesive optical function according to any one of (1) to (3), wherein the acrylic pressure-sensitive adhesive is a (meth) acrylic acid ester homopolymer or copolymer having a weight average molecular weight of 500,000 to 2,000,000. Parts ,
(5) Any of the above (1) to (3), wherein the acrylic pressure-sensitive adhesive comprises a (meth) acrylic acid ester copolymer having a crosslinking point and a weight average molecular weight of 500,000 to 2,000,000 and a crosslinking agent. Adhesive optical functional member according to
( 6 ) On the both surfaces of the adhesive optical functional member according to any one of the above (1) to ( 5 ), wherein the optical functional member is a polarizing plate, and ( 7 ) an acrylic adhesive and the acrylic The present invention provides a liquid crystal display element in which an optical functional member is disposed through a layer made of an adhesive composition containing 0.01 to 15 parts by weight of urethane elastomer per 100 parts by weight of the adhesive.
本発明の粘着剤組成物は、高温高湿条件下においても、被着体との密着性に優れ、かつ接着耐久性にも優れると共に、被着体の伸縮への対応性を有しており、特に液晶セル表面に偏光板などの光学機能部材を貼着させるのに好適に用いられる。
この粘着剤組成物を用いて、液晶セル表面に光学機能部材を配設してなる本発明の液晶表示素子は、高温高湿条件下においても、液晶セルと密着性に優れ、かつ接着耐久性にも優れると共に、光学機能部材の伸縮への対応性を有しており、種々の問題、例えば、偏光板における、いわゆる「白抜け」の現象が発生しにくい。
The pressure-sensitive adhesive composition of the present invention has excellent adhesion to an adherend even under high-temperature and high-humidity conditions, and also has excellent adhesion durability, and is compatible with expansion and contraction of the adherend. In particular, it is suitably used for attaching an optical functional member such as a polarizing plate to the surface of the liquid crystal cell.
The liquid crystal display element of the present invention in which an optical functional member is disposed on the surface of the liquid crystal cell using this pressure-sensitive adhesive composition has excellent adhesion to the liquid crystal cell even under high-temperature and high-humidity conditions, and adhesion durability. In addition, the optical functional member is compatible with expansion and contraction, and various problems such as a so-called “white spot” phenomenon in the polarizing plate are unlikely to occur.
本発明の粘着剤組成物におけるアクリル系粘着剤としては、 (メタ）アクリル酸エステル単独重合体又は共重合体が好ましく用いられる。
これらの (メタ）アクリル酸エステル単独重合体又は共重合体の重量平均分子量は、必要な密着性や接着耐久性を得るには５０万以上が好ましく、必要な被着体の伸縮への対応性を得るには、２００万以下が好ましい。即ち、 (メタ）アクリル酸エステル単独重合体又は共重合体の重量平均分子量としては、５０万〜２００万の範囲が好ましく、８０万〜１８０万の範囲が特に好ましい。
なお、上記重量平均分子量は、標準物質としてポリスチレンを用い、ゲルパーミエーションクロマトグラフィー（ＧＰＣ）法により測定した値である。
As the acrylic pressure-sensitive adhesive in the pressure-sensitive adhesive composition of the present invention, a (meth) acrylic acid ester homopolymer or copolymer is preferably used.
The weight average molecular weight of these (meth) acrylic acid ester homopolymers or copolymers is preferably 500,000 or more in order to obtain the necessary adhesion and adhesion durability, and the necessary adherence to the stretching of the adherend. Is preferably 2 million or less. That is, the weight average molecular weight of the (meth) acrylic acid ester homopolymer or copolymer is preferably in the range of 500,000 to 2,000,000, particularly preferably in the range of 800,000 to 1,800,000.
The weight average molecular weight is a value measured by gel permeation chromatography (GPC) using polystyrene as a standard substance.
前記（メタ）アクリル酸エステル単独重合体に用いられるモノマー又は（メタ）アクリル酸エステル共重合体の主成分として用いられるモノマーとしては、エステルを形成するアルコール成分のアルキル基の炭素数が１〜２０の（メタ）アクリル酸アルキルエステルが好ましく、例えば（メタ）アクリル酸メチル、（メタ）アクリル酸エチル、（メタ）アクリル酸プロピル、（メタ）アクリル酸ｎ−ブチル、（メタ）アクリル酸ｉ−ブチル、（メタ）アクリル酸ペンチル、（メタ）アクリル酸ヘキシル、（メタ）アクリル酸シクロヘキシル、（メタ）アクリル酸２−エチルヘキシル、（メタ）アクリル酸イソオクチル、（メタ）アクリル酸デシル、（メタ）アクリル酸ドデシル、（メタ）アクリル酸ミリスチル、（メタ）アクリル酸パルミチル、（メタ）アクリル酸ステアリルなどが挙げられる。これらのモノマーは単独で用いてもよく、二種以上を組み合わせて用いてもよい。 The monomer used for the (meth) acrylic acid ester homopolymer or the monomer used as the main component of the (meth) acrylic acid ester copolymer has 1 to 20 carbon atoms in the alkyl group of the alcohol component forming the ester. (Meth) acrylic acid alkyl ester is preferable, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate , Pentyl (meth) acrylate, hexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, decyl (meth) acrylate, (meth) acrylic acid Dodecyl, myristyl (meth) acrylate, palmitic acid (meth) acrylate , And (meth) stearyl acrylate. These monomers may be used independently and may be used in combination of 2 or more type.
一方、（メタ）アクリル酸エステル共重合体に用いられるコモノマーとしては、例えば（メタ）アクリル酸２−ヒドロキシエチル、（メタ）アクリル酸２−ヒドロキシプロピル、（メタ）アクリル酸３−ヒドロキシプロピル、（メタ）アクリル酸２−ヒドロキシブチル、（メタ）アクリル酸３−ヒドロキシブチル、（メタ）アクリル酸４−ヒドロキシブチルなどの（メタ）アクリル酸ヒドロキシアルキルエステル；アクリルアミド、メタクリルアミド、Ｎ−メチルアクリルアミド、Ｎ−メチルメタクリルアミド、Ｎ−メチロールアクリルアミド、Ｎ−メチロールメタクリルアミドなどのアクリルアミド；（メタ）アクリル酸モノメチルアミノエチル、（メタ）アクリル酸モノエチルアミノエチル、（メタ）アクリル酸モノメチルアミノプロピル、（メタ）アクリル酸モノエチルアミノプロピルなどの（メタ) アクリル酸モノアルキルアミノアルキルエステル；（メタ) アクリル酸ジアルキルアミノアルキルエステル；アクリル酸、メタクリル酸、クロトン酸、マレイン酸、イタコン酸、シトラコン酸、無水マレイン酸などのエチレン性不飽和カルボン酸やその酸無水物；酢酸ビニル、プロピオン酸ビニルなどのビニルエステル；エチレン、プロピレン、イソブチレンなどのオレフィン；塩化ビニル、ビニリデンクロリドなどのハロゲン化オレフィン；スチレン、α−メチルスチレンなどのスチレン系単量体；ブタジエン、イソプレン、クロロプレンなどのジエン系単量体；アクリロニトリル、メタクリロニトリルなどのニトリル系単量体；Ｎ, Ｎ−ジメチルアクリルアミド、Ｎ, Ｎ−ジメチルメタクリルアミドなどのＮ, Ｎ−ジアルキル置換アクリルアミドなどが挙げられる。 これらのコモノマーは単独で用いてもよく、二種以上を組み合わせて用いてもよい。
（メタ）アクリル酸エステル共重合体における前記コモノマー由来の単位の含有量は、通常０．１〜２０重量％、好ましくは０．５〜１０重量％の範囲で選定される。
On the other hand, examples of the comonomer used in the (meth) acrylate copolymer include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, ( (Meth) acrylic acid hydroxyalkyl esters such as 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate; acrylamide, methacrylamide, N-methylacrylamide, N -Acrylamide such as methylmethacrylamide, N-methylolacrylamide, N-methylolmethacrylamide; monomethylaminoethyl (meth) acrylate, monoethylaminoethyl (meth) acrylate, monomethylaminopropylene (meth) acrylate (Meth) acrylic acid monoalkylaminoalkyl esters such as (meth) acrylic acid monoethylaminopropyl; (meth) acrylic acid dialkylaminoalkyl esters; acrylic acid, methacrylic acid, crotonic acid, maleic acid, itaconic acid, citraconic acid Ethylenically unsaturated carboxylic acids such as maleic anhydride and acid anhydrides thereof; vinyl esters such as vinyl acetate and vinyl propionate; olefins such as ethylene, propylene and isobutylene; halogenated olefins such as vinyl chloride and vinylidene chloride; styrene Styrene monomers such as α-methylstyrene; diene monomers such as butadiene, isoprene and chloroprene; nitrile monomers such as acrylonitrile and methacrylonitrile; N, N-dimethylacrylamide, N, N— The N, such as chill methacrylamide, etc. N- dialkyl substituted acrylamide. These comonomers may be used alone or in combination of two or more.
The content of the unit derived from the comonomer in the (meth) acrylic acid ester copolymer is usually selected in the range of 0.1 to 20% by weight, preferably 0.5 to 10% by weight.
本発明の粘着剤組成物においては、架橋性官能基を有するコモノマーを共重合成分とする（メタ）アクリル酸エステル共重合体を用い、更に、架橋剤を含ませることにより、凝集力を高め、被着体との密着性及び接着耐久性を向上させることができる。
この場合の架橋性官能基を有するコモノマーとしては、前記のコモノマーの内の、（メタ）アクリル酸ヒドロキシアルキルエステル、アクリルアミド、（メタ) アクリル酸モノアルキルアミノアルキルエステル及びエチレン性不飽和カルボン酸やその酸無水物が好ましい。
In the pressure-sensitive adhesive composition of the present invention, by using a (meth) acrylic acid ester copolymer having a comonomer having a crosslinkable functional group as a copolymerization component, and further including a crosslinking agent, the cohesive force is increased, Adhesion with the adherend and adhesion durability can be improved.
Examples of the comonomer having a crosslinkable functional group in this case include (meth) acrylic acid hydroxyalkyl ester, acrylamide, (meth) acrylic acid monoalkylaminoalkyl ester, ethylenically unsaturated carboxylic acid, and the like. Acid anhydrides are preferred.
一方、架橋剤としては、ポリイソシアネート化合物、エポキシ化合物、金属キレート化合物、金属アルコキシド、金属塩、アミン化合物、ヒドラジン化合物、アルデヒド化合物を挙げることができる。
ポリイソシアネート化合物としては、トリレンジイソシアネート、ジフェニルメタンジイソシアネート、キシリレンジイソシアネートなどの芳香族ポリイソシアネート、ヘキサメチレンジイソシアネートなどの脂肪族ポリイソシアネート、イソホロンジイソシアネート、水素添加ジフェニルメタンジイソシアネートなどの脂環式ポリイソシアネートなど；エポキシ化合物としては、ソルビトールポリグリシジルエーテル、ポリグリセロールポリグリシジルエーテル、ペンタエリスリトールポリグリシジルエーテル、ジグリセロールポリグリシジルエーテル、グリセロールポリグリシジルエーテル、トリメチロールプロパンポリグリシジルエーテル、レゾルシノールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、１, ６−ヘキサンジオールジグリシジルエーテル、水素化ビスフェノールＡジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテルなどを挙げることができる。
On the other hand, examples of the crosslinking agent include polyisocyanate compounds, epoxy compounds, metal chelate compounds, metal alkoxides, metal salts, amine compounds, hydrazine compounds, and aldehyde compounds.
Examples of the polyisocyanate compound include aromatic polyisocyanates such as tolylene diisocyanate, diphenylmethane diisocyanate and xylylene diisocyanate, aliphatic polyisocyanates such as hexamethylene diisocyanate, alicyclic polyisocyanates such as isophorone diisocyanate and hydrogenated diphenylmethane diisocyanate; Compounds include sorbitol polyglycidyl ether, polyglycerol polyglycidyl ether, pentaerythritol polyglycidyl ether, diglycerol polyglycidyl ether, glycerol polyglycidyl ether, trimethylolpropane polyglycidyl ether, resorcinol diglycidyl ether, neopentyl glycol diglycidyl ether 1, - hexanediol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, polyethylene glycol diglycidyl ether, and polypropylene glycol diglycidyl ether.
本発明の粘着剤組成物におけるウレタンエラストマーとしては、ウレタンエラストマー、及び変性ウレタンエラストマーなどが挙げられる。変性ウレタンエラストマーとしては、構成成分としてポリアミノ化合物に不飽和化合物をマイケル付加させて種々の官能基を導入した構造を含むマイケル付加型ウレタンウレア樹脂が好ましい。
ウレタンエラストマーは、高分子ポリオールを主成分とするソフトセグメントとジイソシアネートなどのポリイソシアネートと鎖延長剤からなるハードセグメントで構成されたものである。ウレタンエラストマーの種類としては、高分子ポリオールとトリレンジイソシアネート（ＴＤＩ）、４，４’−ジフェニルメタンジイソシアネート（ＭＤＩ）などのジイソシアネートなどのポリイソシアネートを高分子化して得られる熱可塑性ウレタンエラストマーを有機溶剤で希釈した一液型のもの、あるいはポリイソシアネートを別系にて塗工前にさらに添加して硬化させる二液型のものが挙げられる。その他、空気中の湿気でイソシアネートを反応させる湿気硬化型、熱溶融押出タイプのホットメルト型のウレタンエラストマーでも良い。
Examples of the urethane elastomer in the pressure-sensitive adhesive composition of the present invention include urethane elastomers and modified urethane elastomers. As the modified urethane elastomer, a Michael addition type urethane urea resin having a structure in which various functional groups are introduced by Michael addition of an unsaturated compound to a polyamino compound as a constituent component is preferable.
The urethane elastomer is composed of a soft segment mainly composed of a polymer polyol and a hard segment composed of a polyisocyanate such as diisocyanate and a chain extender. As a kind of urethane elastomer, thermoplastic urethane elastomer obtained by polymerizing polyisocyanate such as diisocyanate such as polymer polyol and tolylene diisocyanate (TDI), 4,4'-diphenylmethane diisocyanate (MDI) with organic solvent. A diluted one-component type or a two-component type in which polyisocyanate is further added and cured before coating in a separate system can be mentioned. In addition, a moisture-curing type or hot-melt extrusion type hot-melt type urethane elastomer in which isocyanate is reacted with moisture in the air may be used.
ウレタンエラストマーは、被着体に対する適度な粘着力と剥離する際の被着体の損傷、汚染の観点からは、１００％モジュラスが１ＭＰａ以上であるものが好ましく、被着体に対する適度な粘着力と被着体への貼付性の観点からは、１００％モジュラスが６ＭＰａ以下であるものが好ましい。 Urethane elastomers, damage of the adherend during peeling an appropriate adhesive force to adherends, from the viewpoint of contamination, preferably those of 100% modulus is 1MPa or more, and moderate adhesive strength to adherends From the viewpoint of stickability to an adherend, those having a 100% modulus of 6 MPa or less are preferable.
本発明の粘着剤組成物におけるウレタンエラストマーの配合量は、アクリル系粘着剤１００重量部当り０．００５〜２０重量部の範囲であることが必要であり、０．００５重量部未満では、必要な被着体の伸縮への対応性が得られず、２０重量部を超えると粘着剤組成物の相溶性の問題から、粘着剤が白化する原因となる。
ウレタンエラストマーの好ましい配合量の範囲は、アクリル系粘着剤の種類、即ち、（メタ）アクリル酸エステル重合体が単独重合体、共重合体のいずれであるか、官能基の種類、架橋剤の有無等によって異なり一概には決められないが、好ましくはアクリル系粘着剤１００重量部当り０．０１〜１５重量部の範囲である。
The compounding amount of the urethane elastomer in the pressure-sensitive adhesive composition of the present invention needs to be in the range of 0.005 to 20 parts by weight per 100 parts by weight of the acrylic pressure-sensitive adhesive, and is necessary if it is less than 0.005 parts by weight. If the adherence to the expansion and contraction of the adherend cannot be obtained, and the amount exceeds 20 parts by weight, the pressure-sensitive adhesive is whitened due to the compatibility problem of the pressure-sensitive adhesive composition.
The range of the preferable blending amount of the urethane elastomer is the type of the acrylic pressure-sensitive adhesive, that is, whether the (meth) acrylic acid ester polymer is a homopolymer or a copolymer, the type of functional group, the presence or absence of a crosslinking agent. However, it is preferably in the range of 0.01 to 15 parts by weight per 100 parts by weight of the acrylic pressure-sensitive adhesive.
本発明の粘着剤組成物には、本発明の目的が損なわれない範囲で、所望により、公知の各種添加剤、例えば粘着付与剤、可塑剤、酸化防止剤、紫外線吸収剤、耐熱安定剤、充填剤、シランカップリング剤などを適宜含有させることができる。 In the pressure-sensitive adhesive composition of the present invention, various known additives such as tackifiers, plasticizers, antioxidants, ultraviolet absorbers, heat stabilizers, and the like, as long as the object of the present invention is not impaired. A filler, a silane coupling agent, and the like can be appropriately contained.
次に、本発明の接着性光学機能部材は、光学機能部材の両面又は片面に、本発明の粘着剤組成物からなる層（以下、粘着剤層と略称する。）を設けたものである。
粘着剤層は、粘着剤組成物を光学機能部材の両面又は片面に塗工することにより形成してもよいし、粘着剤組成物を剥離処理された剥離シートの剥離処理面に塗工し、光学機能部材の両面又は片面に接合することにより形成することができる。
塗工する粘着剤組成物（以下、粘着剤液と略称する。）は、有機溶剤系、エマルション系、無溶剤系のいずれであってもよい。
有機溶剤系の粘着剤液で用いられる有機溶剤としては、例えばトルエン、キシレン、メタノール、エタノール、イソブタノール、ｎ−ブタノール、アセトン、メチルエチルケトン、酢酸エチル、テトラヒドロフラン等が挙げられる。これらは一種を単独で用いてもよく、二種以上を組み合わせて用いてもよい。
Next, the adhesive optical functional member of the present invention is provided with a layer made of the pressure-sensitive adhesive composition of the present invention (hereinafter abbreviated as a pressure-sensitive adhesive layer) on both surfaces or one surface of the optical functional member.
The pressure-sensitive adhesive layer may be formed by coating the pressure-sensitive adhesive composition on both sides or one side of the optical functional member, or the pressure-sensitive adhesive composition is applied to the release-treated surface of the release sheet subjected to the release treatment, It can be formed by bonding to both surfaces or one surface of the optical function member.
The pressure-sensitive adhesive composition to be applied (hereinafter abbreviated as pressure-sensitive adhesive liquid) may be any of an organic solvent system, an emulsion system, and a solventless system.
Examples of the organic solvent used in the organic solvent-based pressure-sensitive adhesive liquid include toluene, xylene, methanol, ethanol, isobutanol, n-butanol, acetone, methyl ethyl ketone, ethyl acetate, and tetrahydrofuran. These may be used individually by 1 type, and may be used in combination of 2 or more types.
粘着剤液は、塗工の利便さから、これらの有機溶剤を使用して、固形分濃度が１０〜５０重量％の範囲になるように調製するのが好ましい。
粘着剤の塗工は、例えばバーコート法、ロールコート法、ナイフコート法、ロールナイフコート法、ダイコート法、グラビアコート法、エアドクターコート法、ドクターブレードコート法など、従来公知の塗工方法により行なうことができる。
この粘着剤層の厚さは、通常５〜１５０μｍの範囲が好ましく、特に１０〜１００μｍの範囲が好ましい。
For the convenience of coating, the pressure-sensitive adhesive liquid is preferably prepared using these organic solvents so that the solid content concentration is in the range of 10 to 50% by weight.
The pressure-sensitive adhesive is applied by a conventionally known coating method such as a bar coating method, a roll coating method, a knife coating method, a roll knife coating method, a die coating method, a gravure coating method, an air doctor coating method, or a doctor blade coating method. Can be done.
The thickness of this pressure-sensitive adhesive layer is usually preferably in the range of 5 to 150 μm, particularly preferably in the range of 10 to 100 μm.
本発明の接着性光学機能部材に用いられる光学機能部材としては、例えば偏光板、反射防止板、位相差板、視野角拡大フィルムなどを挙げることができるが、これらの中で偏光板が特に好適である。
上記偏光板としては、通常透明高分子フィルムを一軸方向に延伸配向させ、配向分子間隙にヨウ素及び／又は二色性染料などを吸着配向させてなる偏光フィルムの両面を保護フィルムでカバーしたものが用いられる。上記透明高分子フィルムは、現在ポリビニルアルコールフィルムがほとんどあり、そして保護フィルムとしては、トリアセチルセルロースフィルムが多用されている。
この偏光板には、偏光フィルムとして、例えばヨウ素系偏光フィルム、染料系偏光フィルム、カラー偏光フィルム、ポリビニレン偏光フィルム、赤外偏光フィルム、紫外偏光フィルムなどを用いたものがあるが、本発明においては、特に制限はなくいずれのものも用いることができる。
Examples of the optical functional member used in the adhesive optical functional member of the present invention include a polarizing plate, an antireflection plate, a retardation plate, and a viewing angle widening film. Among these, a polarizing plate is particularly preferable. It is.
As the polarizing plate, usually a transparent polymer film is stretched and oriented in a uniaxial direction, and a polarizing film formed by adsorbing and orienting iodine and / or a dichroic dye in the orientation molecular gap is covered with a protective film. Used. Currently, the transparent polymer film is mostly a polyvinyl alcohol film, and a triacetyl cellulose film is frequently used as a protective film.
In this polarizing plate, for example, an iodine polarizing film, a dye polarizing film, a color polarizing film, a polyvinylene polarizing film, an infrared polarizing film, an ultraviolet polarizing film, and the like are used as the polarizing film. There is no particular limitation, and any one can be used.
また、該偏光板は、用途別では、液晶表示素子用（デジタル時計、電卓、計測器系ディスプレイ、壁掛けテレビ、光学的欠陥検出器用など）、反射光の除去用（サングラス、写真フィルム用など）、光量調整用（写真用フィルター、濃度可変フィルター用など）、光ロックへの応用（自動車のヘッドライトの防眩用、透視防止用など）、偏光干渉利用装置用（歪みの検査器、舞台照明、広告用ディスプレイ用など）などがあるが、いずれの用途の偏光板も用いることができる。これらの用途の中で液晶表示素子用の偏光板が好ましく用いられる。 In addition, the polarizing plate is used for liquid crystal display elements (digital clocks, calculators, measuring instrument displays, wall-mounted televisions, optical defect detectors, etc.), and reflected light removal (sunglasses, photographic films, etc.) according to applications. , For light intensity adjustment (for photographic filters, variable density filters, etc.), application to optical lock (for anti-glare of automobile headlights, prevention of see-through, etc.), for polarized light interference device (distortion inspection device, stage lighting) , Etc.), but any polarizing plate can be used. Among these uses, a polarizing plate for a liquid crystal display element is preferably used.
本発明の液晶表示素子は、液晶セルの両面上に、前記本発明の粘着剤組成物層を介して光学機能部材を配設したものである。
光学機能部材としては、前記接着性光学機能部材に用いられる光学機能部材が挙げられるが、これらの中でも、偏光板が特に好適である。
液晶セルの面上に複数の光学機能部材を配設したものでは、すべての光学機能部材において本発明の粘着剤組成物層を介して接合を行うことができる。もちろん、すべての光学機能部材において本発明の粘着剤組成物層を介して接合を行う必要はないが、少なくとも偏光板の接合は本発明の粘着剤組成物層を介して行うのが好ましい。
例えば、複屈折を補償する為に液晶セルと偏光板の間に位相差板を設ける態様の場合は少なくとも位相差板と偏光板との接合は本発明の粘着剤組成物層を介して行なうことが好ましく、更に必要に応じて、液晶セルと位相差板との接合に使用してもよい。
In the liquid crystal display element of the present invention, optical functional members are disposed on both surfaces of a liquid crystal cell via the pressure-sensitive adhesive composition layer of the present invention.
Examples of the optical functional member include optical functional members used for the adhesive optical functional member, and among these, a polarizing plate is particularly suitable.
In the case where a plurality of optical function members are arranged on the surface of the liquid crystal cell, bonding can be performed through the pressure-sensitive adhesive composition layer of the present invention in all the optical function members. Of course, it is not necessary for all optical functional members to be bonded via the pressure-sensitive adhesive composition layer of the present invention, but at least the polarizing plate is preferably bonded via the pressure-sensitive adhesive composition layer of the present invention.
For example, in the case where a retardation plate is provided between the liquid crystal cell and the polarizing plate in order to compensate for birefringence, at least the bonding between the retardation plate and the polarizing plate is preferably performed through the pressure-sensitive adhesive composition layer of the present invention. Further, if necessary, the liquid crystal cell and the retardation plate may be used for bonding.
次に、本発明を実施例によりさらに詳しく説明するが、本発明は、これらの例によってなんら限定されるものではない。 EXAMPLES Next, although an Example demonstrates this invention further in detail, this invention is not limited at all by these examples.
実施例１
アクリル酸ブチル単位９９重量％とアクリル酸４−ヒドロキシブチル単位１重量％からなる重量平均分子量１７０万のアクリル酸エステル共重合体１００重量部、重量平均分子量１０万、１００％モジュラス２ＭＰａのウレタンエラストマー（東洋インキ製造社製、商品名：ＨＰ−Ｈ）１０重量部及びポリイソシアナート化合物からなる架橋剤（総研化学社製、商品名：ＴＤ−７５）０．２重量部をメチルエチルケトンに溶解し、固形分含有量３０重量％の粘着剤溶液とした。
この粘着剤溶液を、片面にシリコーン系剥離処理をしたポリエチレンテレフタレート剥離シ−ト（リンテック社製、商品名：ＳＰ−ＰＥＴ３８１１）の剥離処理面にナイフコーターによって塗工し、９０℃で１分間乾燥させて厚さ２５μｍの粘着剤層を形成した。
その後偏光板（トリアセチルセルロースフィルム／ポリビニルアルコールフィルム／トリアセチルセルロースフィルム（視野角拡大機能を含む）の３層積層体、厚さ２００μｍ）を前記粘着剤層上に積層して、粘着剤層付きの偏光板を得た。
Example 1
100 parts by weight of an acrylate copolymer having a weight average molecular weight of 1,700,000 consisting of 99% by weight of butyl acrylate units and 1% by weight of 4-hydroxybutyl acrylate units, a urethane elastomer having a weight average molecular weight of 100,000 and 100% modulus of 2 MPa ( Toyo Ink Mfg. Co., Ltd., trade name: HP-H) 10 parts by weight and a polyisocyanate compound cross-linking agent (Soken Chemical Co., Ltd., trade name: TD-75) 0.2 parts by weight are dissolved in methyl ethyl ketone and solid. A pressure-sensitive adhesive solution having a content of 30% by weight was obtained.
This pressure-sensitive adhesive solution was applied to a release-treated surface of a polyethylene terephthalate release sheet (product name: SP-PET3811, manufactured by Lintec Co., Ltd.) having a silicone release treatment on one side, and dried at 90 ° C. for 1 minute. Thus, an adhesive layer having a thickness of 25 μm was formed.
Thereafter, a polarizing plate (triacetyl cellulose film / polyvinyl alcohol film / triacetyl cellulose film (including a viewing angle expansion function) three-layer laminate, thickness 200 μm) is laminated on the pressure-sensitive adhesive layer, with a pressure-sensitive adhesive layer. A polarizing plate was obtained.
実施例２
粘着剤溶液におけるウレタンエラストマーの配合量を１０重量部から１重量部に変えた（粘着剤溶液の固形分含有量は３０重量％）以外は実施例１と同様に実施して、粘着剤層付き偏光板を得た。
Example 2
The same procedure as in Example 1 was carried out except that the amount of the urethane elastomer in the pressure-sensitive adhesive solution was changed from 10 parts by weight to 1 part by weight (the solid content of the pressure-sensitive adhesive solution was 30% by weight). A polarizing plate was obtained.
実施例３
粘着剤溶液におけるウレタンエラストマーの配合量を１０重量部から０．０５重量部に変えた（粘着剤溶液の固形分含有量は３０重量％）以外は実施例１と同様に実施して、粘着剤層付き偏光板を得た。
Example 3
The pressure-sensitive adhesive was carried out in the same manner as in Example 1 except that the amount of the urethane elastomer in the pressure-sensitive adhesive solution was changed from 10 parts by weight to 0.05 parts by weight (the solid content of the pressure-sensitive adhesive solution was 30% by weight). A polarizing plate with a layer was obtained.
比較例１
粘着剤溶液におけるウレタンエラストマーの配合量を１０重量部から５０重量部に変えた（粘着剤溶液の固形分含有量は３０重量％）以外は実施例１と同様に実施して、粘着剤層付き偏光板を得た。
Comparative Example 1
The same procedure as in Example 1 was carried out except that the amount of the urethane elastomer in the pressure-sensitive adhesive solution was changed from 10 parts by weight to 50 parts by weight (the solid content of the pressure-sensitive adhesive solution was 30% by weight). A polarizing plate was obtained.
比較例２
粘着剤溶液におけるウレタンエラストマーの配合量を１０重量部から０．０００５重量部に変えた（粘着剤溶液の固形分含有量は３０重量％）以外は実施例１と同様に実施して、粘着剤層付き偏光板を得た。
Comparative Example 2
The pressure-sensitive adhesive was carried out in the same manner as in Example 1 except that the amount of the urethane elastomer in the pressure-sensitive adhesive solution was changed from 10 parts by weight to 0.0005 parts by weight (the solid content of the pressure-sensitive adhesive solution was 30% by weight). A polarizing plate with a layer was obtained.
比較例３
粘着剤溶液において、ウレタンエラストマーを配合しなかった（粘着剤溶液の固形分含有量は３０重量％）以外は実施例１と同様に実施して、粘着剤層付き偏光板を得た。
Comparative Example 3
In the pressure-sensitive adhesive solution, a polarizing plate with a pressure-sensitive adhesive layer was obtained in the same manner as in Example 1 except that the urethane elastomer was not blended (the solid content of the pressure-sensitive adhesive solution was 30% by weight).
実施例１〜３及び比較例１〜３で得られた粘着剤層付き偏光板について、次の方法により耐久性及び明度差ΔＬ* を測定し、その結果を表１に示す。
（１）耐久性
１５インチ（２３３ｍｍ×３０９ｍｍ）の粘着剤層付き偏光板を、剥離シートを剥がしガラス板に貼付し、８０℃・ドライ又は６０℃・９０％ＲＨの環境条件に１２０時間放置した後、外観を目視観察し、次の基準で評価した。
○：浮き剥がれなし ×：浮き剥がれあり
（２）明度差ΔＬ*
無アルカリガラス板の両面にクロスニコルで１５インチ（２３３ｍｍ×３０９ｍｍ）の粘着剤層付き偏光板を、剥離シートを剥がし貼付し、８０℃・ドライの環境条件に１２０時間放置した後、周縁部の各辺中央の端から１ｃｍの範囲における明度と中央における明度とを測定し、各辺の明度の平均値と、偏光板中央における明度値との差を求めた。
明度は、大塚電子社製の測定装置（ＭＣＰＤ−２０００）を使用し、２３℃・６５％ＲＨの条件にて測定した。
明度差ΔＬ* が大きいほど、粘着剤層の対応性が悪いことを示す。
About the polarizing plate with an adhesive layer obtained in Examples 1-3 and Comparative Examples 1-3, durability and brightness difference (DELTA ) L * were measured with the following method, and the result is shown in Table 1.
(1) Durability A 15-inch (233 mm × 309 mm) pressure-sensitive adhesive layer-attached polarizing plate was peeled off and attached to a glass plate, and allowed to stand at 80 ° C./dry or 60 ° C./90% RH for 120 hours. Thereafter, the appearance was visually observed and evaluated according to the following criteria.
○: No peeling off ×: Lifting off (2) Lightness difference ΔL *
A 15-inch (233 mm x 309 mm) pressure-sensitive adhesive layer polarizing plate with crossed Nicols on both sides of an alkali-free glass plate was peeled off and adhered, and left at 80 ° C / dry environmental conditions for 120 hours. The brightness in the range of 1 cm from the edge of the center of each side and the brightness at the center were measured, and the difference between the average value of the brightness of each side and the brightness value at the center of the polarizing plate was determined.
The brightness was measured using a measuring device (MCPD-2000) manufactured by Otsuka Electronics Co., Ltd. under the conditions of 23 ° C. and 65% RH.
It shows that the correspondence of an adhesive layer is so bad that brightness difference (DELTA ) L * is large.
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| JP2004001481A JP4689166B2 (en) | 2004-01-06 | 2004-01-06 | Adhesive composition, adhesive optical functional member using the same, and liquid crystal display element |
| TW093140855A TWI248526B (en) | 2004-01-06 | 2004-12-28 | Adhesive composition, adhesive optical function member and liquid crystal display element using it |
| CNB200510004032XA CN1325593C (en) | 2004-01-06 | 2005-01-05 | Adhesive composition, optical functional component and liquid crystal display device therewith |
| KR1020050000894A KR100702732B1 (en) | 2004-01-06 | 2005-01-05 | Adhesive composition, adhesive optical member and liquid crystal display device using the same |
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| JP4953717B2 (en) * | 2006-05-19 | 2012-06-13 | リンテック株式会社 | Optical functional film bonding adhesive, optical functional film and method for producing the same |
| JP5060744B2 (en) * | 2006-07-26 | 2012-10-31 | リンテック株式会社 | Optical functional film bonding adhesive, optical functional film and method for producing the same |
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- 2004-01-06 JP JP2004001481A patent/JP4689166B2/en not_active Expired - Lifetime
- 2004-12-28 TW TW093140855A patent/TWI248526B/en active
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- 2005-01-05 CN CNB200510004032XA patent/CN1325593C/en active Active
- 2005-01-05 KR KR1020050000894A patent/KR100702732B1/en active IP Right Grant
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| JPS58173177A (en) * | 1982-04-06 | 1983-10-12 | Bando Chem Ind Ltd | Adhesive composition |
| JPS62230715A (en) * | 1986-03-31 | 1987-10-09 | Hisamitsu Pharmaceut Co Inc | Novel plaster preparation |
| JPH03294378A (en) * | 1990-04-11 | 1991-12-25 | Toyoda Gosei Co Ltd | Tacky tape |
| JPH09227841A (en) * | 1996-02-22 | 1997-09-02 | Sekisui Chem Co Ltd | Preparation of pressure-sensitive adhesive polarizing plate |
| JPH09324163A (en) * | 1996-06-07 | 1997-12-16 | Nippon Kayaku Co Ltd | Tacky agent for optical use |
| JPH10204401A (en) * | 1997-01-24 | 1998-08-04 | Nippon Synthetic Chem Ind Co Ltd:The | Pressure sensitive adhesive composition |
| WO1999014283A1 (en) * | 1997-09-16 | 1999-03-25 | Teijin Limited | Gel-form pressure-sensitive adhesive, and adhesive material and adhesive medicinal preparation both containing the same |
| JP2000328035A (en) * | 1999-05-24 | 2000-11-28 | Toyo Ink Mfg Co Ltd | Pressure-sensitive adhesive composition |
| JP2001342447A (en) * | 2000-06-05 | 2001-12-14 | Nitto Denko Corp | Tacky agent for polarizing plate and optical member |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1325593C (en) | 2007-07-11 |
| JP2005194366A (en) | 2005-07-21 |
| CN1644643A (en) | 2005-07-27 |
| KR20050072682A (en) | 2005-07-12 |
| KR100702732B1 (en) | 2007-04-03 |
| TWI248526B (en) | 2006-02-01 |
| TW200527011A (en) | 2005-08-16 |
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