KR20090077685A - Pressure-sensitive adhesive composition, polarizing plate and liquid crystal display including the above - Google Patents
Pressure-sensitive adhesive composition, polarizing plate and liquid crystal display including the above Download PDFInfo
- Publication number
- KR20090077685A KR20090077685A KR1020080137897A KR20080137897A KR20090077685A KR 20090077685 A KR20090077685 A KR 20090077685A KR 1020080137897 A KR1020080137897 A KR 1020080137897A KR 20080137897 A KR20080137897 A KR 20080137897A KR 20090077685 A KR20090077685 A KR 20090077685A
- Authority
- KR
- South Korea
- Prior art keywords
- meth
- acrylate
- sensitive adhesive
- pressure
- weight
- 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 79
- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 32
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 41
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 23
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 110
- -1 2-ethylhexyl Chemical group 0.000 claims description 69
- 239000000178 monomer Substances 0.000 claims description 41
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000000524 functional group Chemical group 0.000 claims description 16
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 16
- 239000010410 layer Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 10
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 210000002858 crystal cell Anatomy 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 claims description 2
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 claims description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims description 2
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 claims description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 2
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 claims description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 claims description 2
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 claims description 2
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 claims description 2
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 claims description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 claims description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 2
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 claims description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- YJQMXVDKXSQCDI-UHFFFAOYSA-N 2-ethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3SC2=C1 YJQMXVDKXSQCDI-UHFFFAOYSA-N 0.000 claims description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 claims description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 claims description 2
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 claims description 2
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 claims description 2
- 244000028419 Styrax benzoin Species 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 2
- 229960002130 benzoin Drugs 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 2
- QDVNNDYBCWZVTI-UHFFFAOYSA-N bis[4-(ethylamino)phenyl]methanone Chemical compound C1=CC(NCC)=CC=C1C(=O)C1=CC=C(NCC)C=C1 QDVNNDYBCWZVTI-UHFFFAOYSA-N 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 235000019382 gum benzoic Nutrition 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 39
- 239000000853 adhesive Substances 0.000 abstract description 37
- 230000000694 effects Effects 0.000 abstract description 6
- 238000005520 cutting process Methods 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 229940048053 acrylate Drugs 0.000 description 85
- 229920001577 copolymer Polymers 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 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 12
- 239000012790 adhesive layer Substances 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229940117969 neopentyl glycol Drugs 0.000 description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 4
- 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 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 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 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000035882 stress Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- ZNAAXKXXDQLJIX-UHFFFAOYSA-N bis(2-cyclohexyl-3-hydroxyphenyl)methanone Chemical compound C1CCCCC1C=1C(O)=CC=CC=1C(=O)C1=CC=CC(O)=C1C1CCCCC1 ZNAAXKXXDQLJIX-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
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- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
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- 238000009826 distribution Methods 0.000 description 2
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
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- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- 239000007787 solid Substances 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- 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 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/141—Feedstock
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
Abstract
본 발명은 (A) 아세토아세틸기 함유 아크릴계 공중합체 및 (B) 다관능성 가교제를 포함하고, 경화 상태에서 상호침투 네트워크 구조를 구현할 수 있는 점착제 조성물, 상기를 포함하는 점착 편광판 및 액정표시장치에 관한 것이다. 본 발명은 고온 및/또는 고습 조건 하에서 탁월한 내구신뢰성을 가지고, 절단성, 재박리성 및 작업성 등의 제반 물성이 우수하면서도, 빛샘 현상을 효과적으로 방지할 수 있는 점착제 조성물을 제공할 수 있다. 특히 본 발명에서는, 대형 표시 장치에서도 탁월한 빛샘 억제 효과를 나타낼 수 있는 점착제 조성물, 편광판 및 액정표시장치가 제공된다.The present invention relates to an adhesive composition comprising (A) an acetoacetyl group-containing acrylic copolymer and (B) a polyfunctional crosslinking agent, and capable of implementing an interpenetrating network structure in a cured state, an adhesive polarizing plate including the above, and a liquid crystal display device. will be. The present invention can provide a pressure-sensitive adhesive composition having excellent durability under high temperature and / or high humidity conditions, excellent in various properties such as cutting property, re-peelability, and workability, and which can effectively prevent light leakage. In particular, the present invention provides a pressure-sensitive adhesive composition, a polarizing plate, and a liquid crystal display device capable of exhibiting an excellent light leakage suppressing effect even in a large display device.
Description
본 발명은 고온 및/또는 고습 조건 하에서 우수한 내구신뢰성 및 제반 물성(ex. 절단성, 재박리성 및 작업성 등)을 나타내고, 탁월한 저빛샘 특성을 가지는 점착제 조성물, 상기를 포함하는 편광판 및 액정표시장치에 관한 것이다.The present invention exhibits excellent durability and various physical properties (eg cutting property, re-peelability, workability, etc.) under high temperature and / or high humidity conditions, and has an excellent low light leakage property, a polarizing plate and a liquid crystal display including the same. Relates to a device.
액정표시장치(liquid crystal display)는 두 장의 얇은 유리 기판 사이에 액체 결정을 넣어 화면을 표시하는 장치이다. 상기 장치에서는 액정에 연결된 전극을 통해 전압을 가하면 액체 결정의 분자배열 방식이 달라지고, 이에 따라 액정을 통과하는 빛의 통과율이 달라져서 그림이나 색을 표시할 수 있다. 이와 같은 액정표시장치는 전력 소모가 적고, 평면적으로 얇게 만들 수 있다는 장점을 가져 현재 여러 분야에서 각광을 받고 있는 표시장치이다.A liquid crystal display is a device that displays a screen by inserting a liquid crystal between two thin glass substrates. In the device, when a voltage is applied through an electrode connected to the liquid crystal, the molecular arrangement of the liquid crystal is changed, and thus, the rate of light passing through the liquid crystal is changed, thereby displaying a picture or color. Such a liquid crystal display device is a display device that is currently in the spotlight in various fields because of the advantages of low power consumption and flatness.
액정표시장치를 제조하기 위해서는, 기본적으로 액정과 투명 전극층을 갖는 유리 기판 등을 포함하는 액정셀 및 편광판이 필요하며, 이들을 접합하기 위한 접착층 또는 점착층이 필요하다. In order to manufacture a liquid crystal display, a liquid crystal cell and a polarizing plate including a glass substrate having a liquid crystal and a transparent electrode layer and the like are basically required, and an adhesive layer or an adhesive layer for bonding them is required.
상기에서 편광판은 일정 방향으로 배열된 요오드계 화합물 또는 이색성 편광물질을 포함하고, 양면에 편광소자를 보호하기 위한 TAC(triacetyl cellulose)계 보호 필름 등을 포함하는 다층 구조로 구성된다. 또한, 편광판은 일방성 분자배열을 갖는 위상차 필름 또는 액정형 필름과 같은 광시야각 보상 필름을 부가적으로 포함할 수 있다. 이와 같이 다층의 편광판을 구성하는 각각의 필름들은 서로 다른 분자구조 및 조성을 가지는 재료로 만들어지고, 이에 따라 서로 상이한 물리적 특성을 가진다. 따라서, 특히 고온 및/또는 고습 조건 하에서는 일방성 분자 배열을 가진 재료들의 수축 또는 팽창 거동의 차이에 따라 치수안정성이 부족하다. 그러므로 편광판이 점착제에 의해 고정되어 있는 경우에 고온 및/또는 고습 조건 하에서의 수축 또는 팽창에 의해 TAC층에 응력이 집중되어, 복굴절이 발생되고 빛샘 현상이 발생하는 문제가 있다.The polarizing plate includes an iodine-based compound or a dichroic polarizing material arranged in a predetermined direction, and has a multi-layered structure including a triacetyl cellulose (TAC) -based protective film for protecting the polarizer on both sides. In addition, the polarizing plate may additionally include a wide viewing angle compensation film such as a retardation film or a liquid crystal film having a unidirectional molecular array. As described above, each film constituting the multilayer polarizing plate is made of a material having a different molecular structure and composition, and thus has different physical properties from each other. Thus, under high temperature and / or high humidity conditions, dimensional stability is lacking due to the difference in shrinkage or expansion behavior of materials with unidirectional molecular arrangements. Therefore, when the polarizing plate is fixed by the pressure-sensitive adhesive, stress is concentrated in the TAC layer due to shrinkage or expansion under high temperature and / or high humidity conditions, thereby causing birefringence and light leakage phenomenon.
상기와 같은 문제점을 해결하기 위한 대표적인 방법으로는, 점착제를 외부 응력에 대한 어긋남량(creep)이 크고, 변형되기 쉽도록 설계하여 응력 완화 특성을 부여하는 방법이 있다. 예를 들면, 가교제와 반응할 수 있는 관능기를 포함하는 고분자량 중합체에 가교성 관능기를 소량 포함하거나 또는 포함하지 않는 저분자량체를 혼합하는 방법(대한민국 특허공개공보 제1998-79266호, 일본 특허공개공보 제2002-47468호 및 일본 특허공개공보 제2003-49141호 등)이 알려져 있다.As a representative method for solving the above problems, there is a method of providing a stress relaxation characteristic by designing the pressure-sensitive adhesive to be large, easy to deform the creep to the external stress. For example, a method of mixing a high molecular weight polymer containing a functional group capable of reacting with a crosslinking agent and a low molecular weight material containing or not containing a small amount of a crosslinkable functional group (Korean Patent Publication No. 1998-79266, Japanese Patent Publication) 2002-47468 and Japanese Patent Laid-Open No. 2003-49141 and the like are known.
그러나, 상기 기술에서 개시하는 점착제 조성물은 재단성이 떨어져서, 편광 판 제조 시에 점착제의 삐짐 또는 눌림 현상 등이 발생하여 수율이 크게 떨어지는 문제점이 있다.However, the pressure-sensitive adhesive composition disclosed in the above technique is inferior in cutting property, so that a squeezing or squeezing phenomenon of the pressure-sensitive adhesive occurs during the production of a polarizing plate, and thus the yield is greatly reduced.
빛샘 현상을 방지하기 위한 다른 기술로는, 점착제를 매우 하드(hard)하게 설계하는 방법이 있다. 이와 같이 점착제가 딱딱한 물성을 갖는 경우, 고온 및/또는 고습 조건에서의 편광판의 수축 및 팽창을 최대한 억제함으로써, 발생되는 응력을 최소화하고, 편광판의 최외각에 집중시켜 비교적 우수한 광학적 물성을 구현할 수 있다.Another technique for preventing light leakage is to design the adhesive very hard. As described above, when the pressure-sensitive adhesive has hard physical properties, by minimizing the shrinkage and expansion of the polarizing plate under high temperature and / or high humidity conditions, the generated stress can be minimized and a relatively excellent optical property can be realized by focusing on the outermost part of the polarizing plate. .
예를 들어, 일본 특허공개공보 제2007-197659호 및 제2007-212995호는 카복실기 함유 아크릴계 공중합체, 다관능 아크릴레이트, 다관능 이소시아네이트 가교제 및 광개시제를 포함하는 점착제 조성물을 개시한다. For example, Japanese Patent Laid-Open Nos. 2007-197659 and 2007-212995 disclose an adhesive composition comprising a carboxyl group-containing acrylic copolymer, a polyfunctional acrylate, a polyfunctional isocyanate crosslinking agent and a photoinitiator.
그러나, 상기 공보에서 개시하는 점착제 조성물의 경우, 모니터 등의 표시 장치가 소형인 경우 어느 정도 성능을 발휘하나, 20인치 이상의 대형 모니터 등에서는 빛샘 제어 성능이 떨어지는 문제점이 있다.However, in the case of the pressure-sensitive adhesive composition disclosed in the above publication, when the display device such as a monitor is small in size, it exhibits a certain degree of performance, but in a large monitor of 20 inches or more, the light leakage control performance is inferior.
본 발명은 전술한 종래 기술의 문제점을 고려하여 이루어진 것으로, 고온 및/또는 고습 조건 하에서 우수한 내구신뢰성 및 제반 물성(ex. 절단성, 재박리성 및 작업성 등)을 나타내고, 탁월한 저빛샘 특성을 가지는 점착제 조성물, 상기를 사용한 편광판 및 액정표시장치를 제공하는 것을 목적으로 한다.The present invention has been made in consideration of the above-mentioned problems of the prior art, and shows excellent durability and physical properties (eg cutting property, re-peelability, workability, etc.) under high temperature and / or high humidity conditions, and excellent low light leakage characteristics. An object is to provide an adhesive composition, the polarizing plate using the above, and a liquid crystal display device.
본 발명은 상기 과제를 해결하기 위한 수단으로서, (A) 아세토아세틸기 함유 아크릴계 공중합체 및 (B) 다관능성 가교제를 포함하고,The present invention includes (A) an acetoacetyl group-containing acrylic copolymer and (B) a polyfunctional crosslinking agent as means for solving the above problems,
경화 상태에서 상호침투 네트워크 구조를 구현할 수 있는 점착제 조성물을 제공한다.Provided is a pressure-sensitive adhesive composition capable of implementing an interpenetrating network structure in a cured state.
본 발명은 상기 과제를 해결하기 위한 다른 수단으로서, 편광 필름; 및 상기 편광 필름의 일면 또는 양면에 형성되고, 본 발명에 따른 점착제 조성물의 경화물을 함유하는 점착층을 포함하는 점착 편광판을 제공한다.The present invention is another means for solving the above problems, a polarizing film; And a pressure-sensitive adhesive layer formed on one or both surfaces of the polarizing film, the pressure-sensitive adhesive layer containing a cured product of the pressure-sensitive adhesive composition according to the present invention.
본 발명은 상기 과제를 해결하기 위한 또 다른 수단으로서, 상기 본 발명에 따른 점착 편광판이 액정셀의 일면 또는 양면에 접합되어 있는 액정 패널을 포함하는 액정표시장치를 제공한다.As another means for solving the above problems, the present invention provides a liquid crystal display device comprising a liquid crystal panel in which the adhesive polarizer according to the present invention is bonded to one side or both sides of a liquid crystal cell.
본 발명은 고온 및/또는 고습 조건 하에서 탁월한 내구신뢰성을 가지고, 절단성, 재박리성 및 작업성 등의 제반 물성이 우수하면서도, 빛샘 현상을 효과적으로 방지할 수 있는 점착제 조성물을 제공할 수 있다. 특히 본 발명에서는, 대형 표시 장치에서도 탁월한 빛샘 억제 효과를 나타낼 수 있는 점착제 조성물, 편광판 및 액정표시장치가 제공된다.The present invention can provide a pressure-sensitive adhesive composition having excellent durability under high temperature and / or high humidity conditions, excellent in various properties such as cutting property, re-peelability, and workability, and which can effectively prevent light leakage. In particular, the present invention provides a pressure-sensitive adhesive composition, a polarizing plate, and a liquid crystal display device capable of exhibiting an excellent light leakage suppressing effect even in a large display device.
본 발명은, (A) 아세토아세틸기 함유 아크릴계 공중합체; 및 (B) 다관능성 가교제를 포함하고,The present invention, (A) acetoacetyl group-containing acrylic copolymer; And (B) a multifunctional crosslinking agent,
경화 상태에서 상호침투 네트워크(Interpenetrating Polymer Network, 이하 『IPN』이라 칭하는 경우가 있다.) 구조를 구현할 수 있는 점착제 조성물에 관한 것이다.The present invention relates to an adhesive composition capable of realizing an interpenetrating polymer network (hereinafter, referred to as "IPN") structure in a cured state.
본 발명은 또한, 편광 필름; 및The present invention also provides a polarizing film; And
상기 편광 필름의 일면 또는 양면에 형성되고, 본 발명에 따른 점착제 조성물의 경화물을 함유하는 점착층을 포함하는 점착 편광판에 관한 것이다.The present invention relates to an adhesive polarizing plate formed on one or both surfaces of the polarizing film and including an adhesive layer containing a cured product of the adhesive composition according to the present invention.
본 발명은 또한, 상기 본 발명의 점착 편광판이 액정셀의 일면 또는 양면에 접합되어 있는 액정 패널을 포함하는 액정표시장치에 관한 것이다.The present invention also relates to a liquid crystal display device comprising a liquid crystal panel in which the adhesive polarizing plate of the present invention is bonded to one side or both sides of a liquid crystal cell.
이하, 본 발명의 점착제 조성물을 보다 상세히 설명한다.Hereinafter, the adhesive composition of this invention is demonstrated in detail.
본 발명의 점착제 조성물에 포함되는 (A) 아크릴계 공중합체는 중량평균분자 량(Mw)이 100만 이상인 것이 바람직하다. (A) 아크릴계 공중합체의 중량평균분자량이 100만 미만이면, 응집력 저하로 인해 고온 및/또는 고습 조건 하에서 기포 또는 박리 현상이 발생하는 등 조성물의 내구신뢰성이 저하될 우려가 있다. 본 발명에서 (A) 아크릴계 공중합체의 중량평균분자량은, 100만 이상인 한, 그 상한은 특별히 한정되지 않는다. 다만, 상기 중량평균분자량이 지나치게 증가할 경우 점도 상승으로 인해 코팅성이 저하될 우려가 있으므로, 예를 들면, 250만 이하의 범위에서 적절하게 조절될 수 있다.(A) acrylic copolymer included in the pressure-sensitive adhesive composition of the present invention is preferably at least one million weight average molecular amount (M w). When the weight average molecular weight of the (A) acrylic copolymer is less than 1 million, there is a fear that the durability of the composition may be deteriorated, such as bubble or peeling phenomenon under high temperature and / or high humidity conditions due to the decrease in cohesive force. As long as the weight average molecular weight of the (A) acrylic copolymer in this invention is 1 million or more, the upper limit is not specifically limited. However, if the weight average molecular weight is excessively increased, there is a fear that the coating property is lowered due to the viscosity increase. For example, the weight average molecular weight may be appropriately adjusted in the range of 2.5 million or less.
본 발명에서 사용되는 (A) 공중합체의 구체적인 조성은 아세토아세틸기를 함유하는 한, 특별히 한정되는 것은 아니다. 예를 들면, 본 발명에서는 (A) 아크릴계 공중합체로서, (메타)아크릴산 에스테르계 단량체 80 중량부 내지 99.8 중량부, 가교성 관능기 함유 단량체 0.01 중량부 내지 10 중량부; 및 아세토아세틸기 함유 단량체 0.01 중량부 내지 10 중량부를 포함하는 공중합체를 사용할 수 있다.The specific composition of the copolymer (A) used in the present invention is not particularly limited as long as it contains an acetoacetyl group. For example, in this invention, as an acrylic copolymer (A), 80 weight part-99.8 weight part of (meth) acrylic acid ester monomers, 0.01 weight part-10 weight part of crosslinkable functional group containing monomers; And 0.01 to 10 parts by weight of acetoacetyl group-containing monomer may be used.
상기에서 (메타)아크릴산 에스테르계 단량체의 종류는 특별히 한정되지 않으며, 예를 들면, 알킬 (메타)아크릴레이트를 사용할 수 있다. 이 때, 상기 단량체에 포함되는 알킬기가 지나치게 장쇄가 되면, 점착제의 응집력이 저하되고, 유리전이온도(Tg) 및 점착성의 조절이 어려워질 우려가 있으므로, 탄소수가 2 내지 14인 알킬기를 갖는 (메타)아크릴산 에스테르계 단량체를 사용하는 것이 바람직하다. 이와 같은 단량체의 예로는 에틸 (메타)아크릴레이트, n-프로필 (메타)아크릴레이트, 이소프로필 (메타)아크릴레이트, n-부틸 (메타)아크릴레이트, t-부틸 (메타)아 크릴레이트, sec-부틸 (메타)아크릴레이트, 펜틸 (메타)아크릴레이트, 2-에틸헥실 (메타)아크릴레이트, 2-에틸부틸 (메타)아크릴레이트, n-옥틸 (메타)아크릴레이트, 이소옥틸 (메타)아크릴레이트, 이소노닐 (메타)아크릴레이트, 라우릴 (메타)아크릴레이트 및 테트라데실 (메타)아크릴레이트를 들 수 있고, 본 발명에서는 상기 중 일종 또는 이종 이상의 혼합을 사용할 수 있다. 상기와 같은 (메타)아크릴산 에스테르계 단량체는 (A) 공중합체 내에 80 중량부 내지 99.8 중량부의 양으로 포함되는 것이 바람직하다. 상기 함량이 80 중량부보다 작으면, 점착제의 초기 접착력이 저하될 우려가 있고, 99.8 중량부를 초과하면, 응집력 저하로 인해 내구성에 문제가 발생할 우려가 있다.The type of the (meth) acrylic acid ester monomer is not particularly limited, and alkyl (meth) acrylate can be used, for example. At this time, when the alkyl group contained in the monomer is too long, the cohesive force of the pressure-sensitive adhesive is lowered, and the glass transition temperature (T g ) and the adhesiveness may be difficult to control, and thus the alkyl group having 2 to 14 carbon atoms ( It is preferable to use a meta) acrylic acid ester monomer. Examples of such monomers include ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, sec -Butyl (meth) acrylate, pentyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylic Elate, isononyl (meth) acrylate, lauryl (meth) acrylate, and tetradecyl (meth) acrylate can be mentioned, In the present invention, one kind or a mixture of two or more kinds thereof can be used. The (meth) acrylic acid ester monomer as described above is preferably included in an amount of 80 parts by weight to 99.8 parts by weight in the (A) copolymer. If the content is less than 80 parts by weight, there is a fear that the initial adhesive strength of the pressure-sensitive adhesive is lowered, if it exceeds 99.8 parts by weight, there is a fear that a problem in durability due to the decrease in cohesion.
상기 가교성 관능기 함유 단량체는 (A) 아크릴계 공중합체에 가교성 관능기를 부여하여, (B) 다관능성 가교제와의 반응을 위한 가교점을 제공하거나, 실란계 커플링제와 반응하여, 고온 및/또는 고습 조건 하에서의 내구신뢰성, 점착력 및 응집력을 조절하는 역할을 할 수 있다.The crosslinkable functional group-containing monomer imparts a crosslinkable functional group to the (A) acrylic copolymer, thereby providing a crosslinking point for reaction with the (B) polyfunctional crosslinking agent, or reacting with a silane coupling agent, thereby causing high temperature and / or It may serve to adjust the durability, cohesion and cohesion under high humidity conditions.
본 발명에서 사용할 수 있는 가교성 관능기 함유 단량체의 예로는 히드록시기 함유 단량체, 카복실기 함유 단량체, 질소 함유 단량체 및 글리시딜기 함유 단량체 등을 들 수 있다. 본 발명에서는 상기 중 히드록시기 함유 단량체를 사용하여, (A) 아크릴계 공중합체가 히드록시기 및 아세토아세틸기를 동시에 포함하도록 하는 것이 바람직하지만, 이에 제한되는 것은 아니다. 상기에서 히드록시기 함유 단량체의 예로는, 2-히드록시에틸 (메타)아크릴레이트, 2-히드록시프로필 (메타)아크릴레이트, 4-히드록시부틸 (메타)아크릴레이트, 6-히드록시헥실 (메타)아크릴레 이트, 8-히드록시옥틸 (메타)아크릴레이트, 2-히드록시에틸렌글리콜 (메타)아크릴레이트 또는 2-히드록시프로필렌글리콜 (메타)아크릴레이트를 들 수 있고; 카복실기 함유 단량체의 예로는 아크릴산, 메타크릴산, 2-(메타)아크릴로일옥시 아세트산, 3-(메타)아크릴로일옥시 프로필산, 4-(메타)아크릴로일옥시 부틸산, 아크릴산 이중체, 이타콘산, 말레산 또는 말레산 무수물 등을 들 수 있으며; 질소 함유 단량체의 예로는 2-이소시아네이토에틸 (메타)아크릴레이트, 3-이소시아네이토프로필 (메타)아크릴레이트, 4-이소시아네이토부틸 (메타)아크릴레이트, (메타)아크릴아미드, N-비닐 피롤리돈 또는 N-비닐 카프로락탐 등을 들 수 있고, 글리시딜기 함유 단량체의 예로는 글리시딜 (메타)아크릴레이트 등을 들 수 있으나, 이에 제한되는 것은 아니다. Examples of the crosslinkable functional group-containing monomer that can be used in the present invention include hydroxy group-containing monomers, carboxyl group-containing monomers, nitrogen-containing monomers and glycidyl group-containing monomers. In the present invention, it is preferable to use a hydroxy group-containing monomer in the above, so that the (A) acrylic copolymer includes a hydroxy group and an acetoacetyl group at the same time, but is not limited thereto. Examples of the hydroxy group-containing monomers above include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) Acrylate, 8-hydroxyoctyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate or 2-hydroxypropylene glycol (meth) acrylate; Examples of the carboxyl group-containing monomers include acrylic acid, methacrylic acid, 2- (meth) acryloyloxy acetic acid, 3- (meth) acryloyloxy propyl acid, 4- (meth) acryloyloxy butyl acid, and acrylic acid double. Sieve, itaconic acid, maleic acid or maleic anhydride; Examples of nitrogen-containing monomers include 2-isocyanatoethyl (meth) acrylate, 3-isocyanatopropyl (meth) acrylate, 4-isocyanatobutyl (meth) acrylate, (meth) acrylamide , N-vinyl pyrrolidone or N-vinyl caprolactam, and the like, and examples of the glycidyl group-containing monomer include glycidyl (meth) acrylate, but are not limited thereto.
본 발명에서 상기와 같은 가교성 관능기 함유 단량체는 (A) 아크릴계 공중합체 내에 0.01 중량부 내지 10 중량부의 양으로 포함되는 것이 바람직하다. 상기 함량이 0.01 중량부 미만이면, 고온 및/또는 고습 조건 하에서 내구신뢰성 등의 물성이 악화될 우려가 있고, 10 중량부를 초과하면, 점착성 및/또는 박리력이 저하될 우려가 있다.In the present invention, the crosslinkable functional group-containing monomer as described above is preferably contained in an amount of 0.01 to 10 parts by weight in the (A) acrylic copolymer. If the content is less than 0.01 part by weight, physical properties such as durability and the like may deteriorate under high temperature and / or high humidity conditions. If the content is more than 10 parts by weight, adhesiveness and / or peeling force may be lowered.
본 발명에서 사용될 수 있는 아세토아세틸기 함유 단량체의 예로는 아세토아세틸 (메타)아크릴레이트; 아세토아세틸메틸 (메타)아크릴레이트, 아세토아세틸에틸 (메타)아크릴레이트, 아세토아세틸프로필 (메타)아크릴레이트, 아세토아세틸부틸 (메타)아크릴레이트 또는 아세토아세틸헥실 (메타)아크릴레이트 등의 아세토아 세틸알킬 (메타)아크릴레이트; 아세토아세톡시에틸 (메타)아크릴레이트 또는 아세토아세톡시프로필 (메타)아크릴레이트 등의 아세토아세톡시알킬 (메타)아크릴레이트; 스티릴 아세토아세테이트(styryl acetoacetate), 이소프로페닐 아세토아세테이트(isopropenyl acetoacetate), 헥스-5-에닐 아세토아세테이트(hex-5-enyl acetoacetate), 알릴 아세토아세테이트 또는 비닐 아세토아세테이트 등의 아세토아세테이트 화합물; 또는 아세토아세톡시에틸 크로토네이트(acetoacetoxyethyl crotonate) 또는 아세토아세톡시프로필 크로토네이트(acetoacetoxypropyl crotonate) 등의 아세토아세톡시알킬 크로토네이트 등의 일종 또는 이종 이상을 들 수 있으나, 이에 제한되는 것은 아니다.Examples of acetoacetyl group-containing monomers that can be used in the present invention include acetoacetyl (meth) acrylate; Acetoacetylalkyl, such as acetoacetylmethyl (meth) acrylate, acetoacetylethyl (meth) acrylate, acetoacetylpropyl (meth) acrylate, acetoacetylbutyl (meth) acrylate or acetoacetylhexyl (meth) acrylate (Meth) acrylates; Acetoacetoxyalkyl (meth) acrylates such as acetoacetoxyethyl (meth) acrylate or acetoacetoxypropyl (meth) acrylate; Acetoacetate compounds such as styryl acetoacetate, isopropenyl acetoacetate, hex-5-enyl acetoacetate, allyl acetoacetate or vinyl acetoacetate; Or acetoacetoxyalkyl crotonate such as acetoacetoxyethyl crotonate or acetoacetoxypropyl crotonate, and the like, or a heterogeneous compound, but is not limited thereto.
상기와 같은 아세토아세틸기 함유 단량체는 본 발명의 (A) 아크릴계 공중합체 내에 0.01 중량부 내지 10 중량부, 바람직하게는 0.1 중량부 내지 10 중량부의 양으로 포함될 수 있다. 상기 함량이 0.01 중량부 미만이면, 고온 및/또는 고습 조건 하에서 내구 신뢰성 등의 물성이 저하될 우려가 있고, 10 중량부를 초과하면, 점착성 및/또는 박리력이 저하될 우려가 있다.The acetoacetyl group-containing monomer as described above may be included in an amount of 0.01 to 10 parts by weight, preferably 0.1 to 10 parts by weight, in the acrylic copolymer (A) of the present invention. If the content is less than 0.01 part by weight, there is a fear that physical properties such as durability reliability under high temperature and / or high humidity conditions may be lowered. If the content is more than 10 parts by weight, the adhesion and / or peeling force may be lowered.
본 발명의 (A) 아크릴계 공중합체는 또한 전술한 성분에 추가로 (메타)아크릴산 알킬렌 옥시드 부가물을 포함할 수 있다. 상기 단량체는 (A) 아크릴계 공중합체 내에 알킬렌 옥시드기를 부여할 수 있으며, 상기 알킬렌 옥시드기는 (A) 아크릴계 공중합체 및 후술하는 다관능성 아크릴레이트와의 혼화성을 증진시켜, 최종 점착제의 헤이즈를 감소시키고, 동량의 다관능성 아크릴레이트의 사용 시에도 점착 제 벌크 모듈러스를 증가시켜 빛샘 현상을 억제할 수 있게 하는 역할을 할 수 있다. 또한, 상기 알킬렌 옥시드기는 점착제 벌크의 모듈러스가 크게 증가한 상태에서도 점착력을 유지할 수 있게 하여, 점착제의 내구성을 향상시킬 수 있다. 상기 알킬렌 옥시드기는 특히 3개 이상의 관능기를 가지고, 분자 구조 중 고리상 구조를 포함하는 아크릴레이트와 탁월한 혼화성을 나타낸다.The (A) acrylic copolymer of the present invention may also contain (meth) acrylic acid alkylene oxide adducts in addition to the above-mentioned components. The monomer may impart an alkylene oxide group in the (A) acrylic copolymer, and the alkylene oxide group may improve miscibility with the (A) acrylic copolymer and the polyfunctional acrylate described later, It can serve to reduce haze and to suppress light leakage by increasing the adhesive bulk modulus even when using the same amount of multifunctional acrylate. In addition, the alkylene oxide group can maintain the adhesive force even in a state where the modulus of the adhesive bulk is greatly increased, thereby improving the durability of the adhesive. The alkylene oxide group has in particular three or more functional groups and exhibits excellent miscibility with acrylates including cyclic structures in molecular structure.
본 발명에서 사용할 수 있는 (메타)아크릴산 알킬렌 옥시드 부가물의 예로는, 알콕시 에틸렌글리콜 (메타)아크릴산 에스테르 또는 알콕시 프로필렌글리콜 (메타)아크릴산 에스테르 등의 알콕시 알킬렌글리콜 (메타)아크릴산 에스테르; 알콕시 디에틸렌글리콜 (메타)아크릴산 에스테르 또는 알콕시 디프로필렌글리콜 (메타)아크릴산 에스테르 등의 알콕시 디알킬렌글리콜 (메타)아크릴산 에스테르; 알콕시 트리에틸렌글리콜 (메타)아크릴산 에스테르 또는 알콕시 트리프로필렌글리콜 (메타)아크릴산 에스테르 등의 알콕시 트리알킬렌글리콜 (메타)아크릴산 에스테르; 알콕시 테트라에틸렌글리콜 (메타)아크릴산 에스테르 또는 알콕시 테트라프로필렌글리콜 (메타)아크릴산 에스테르 등의 알콕시 테트라알킬렌글리콜 (메타)아크릴산 에스테르; 페녹시 에틸렌글리콜 (메타)아크릴산 에스테르 또는 페녹시 프로필렌글리콜 (메타)아크릴산 에스테르 등의 페녹시 알킬렌글리콜 (메타)아크릴산 에스테르; 페녹시 디에틸렌글리콜 (메타)아크릴산 에스테르 또는 페녹시 디프로필렌글리콜 (메타)아크릴산 에스테르 등의 페녹시 디알킬렌글리콜 (메타)아크릴산 에스테르; 페녹시 트리에틸렌글리콜 (메타)아크릴산 에스테르 또는 페녹시 트리프로필렌글리콜 (메타)아크릴산 에스테르 등의 페녹시 트리알킬렌글리콜 (메타)아크릴산 에 스테르; 및 페녹시 테트라에틸렌글리콜 (메타)아크릴산 에스테르 또는 페녹시 테트라프로필렌글리콜 (메타)아크릴산 에스테르 등의 페녹시 테트라알킬렌글리콜 (메타)아크릴산 에스테르 등의 일종 또는 이종 이상을 들 수 있으나, 이에 제한되는 것은 아니다. 상기에서 『알콕시』는 탄소수 1 내지 8의 알콕시를 나타내며, 보다 바람직하게는 메톡시, 에톡시, 프로폭시 또는 부톡시이다.As an example of the (meth) acrylic-acid alkylene oxide adduct which can be used by this invention, Alkoxy alkylene glycol (meth) acrylic acid ester, such as the alkoxy ethylene glycol (meth) acrylic acid ester or the alkoxy propylene glycol (meth) acrylic acid ester; Alkoxy dialkylene glycol (meth) acrylic acid esters such as alkoxy diethylene glycol (meth) acrylic acid ester or alkoxy dipropylene glycol (meth) acrylic acid ester; Alkoxy trialkylene glycol (meth) acrylic acid esters such as alkoxy triethylene glycol (meth) acrylic acid ester or alkoxy tripropylene glycol (meth) acrylic acid ester; Alkoxy tetraalkylene glycol (meth) acrylic acid esters such as alkoxy tetraethylene glycol (meth) acrylic acid ester or alkoxy tetrapropylene glycol (meth) acrylic acid ester; Phenoxy alkylene glycol (meth) acrylic acid esters such as phenoxy ethylene glycol (meth) acrylic acid ester or phenoxy propylene glycol (meth) acrylic acid ester; Phenoxy dialkylene glycol (meth) acrylic acid esters such as phenoxy diethylene glycol (meth) acrylic acid ester or phenoxy dipropylene glycol (meth) acrylic acid ester; Phenoxy trialkylene glycol (meth) acrylic acid esters such as phenoxy triethylene glycol (meth) acrylic acid ester or phenoxy tripropylene glycol (meth) acrylic acid ester; And phenoxy tetraalkylene glycol (meth) acrylic acid esters such as phenoxy tetraethylene glycol (meth) acrylic acid ester or phenoxy tetrapropylene glycol (meth) acrylic acid ester, and the like. no. In the above, "alkoxy" represents alkoxy having 1 to 8 carbon atoms, more preferably methoxy, ethoxy, propoxy or butoxy.
위와 같은 (메타)아크릴산 알킬렌 옥시드 부가물의 함량은 전술한 특성을 고려하여 적절히 선택될 수 있으며, 예를 들면, (A) 아크릴계 공중합체 내에 2 중량부 내지 40 중량부의 양으로 포함될 수 있다.The content of the (meth) acrylic acid alkylene oxide adduct as described above may be appropriately selected in consideration of the above-described properties, for example, may be included in an amount of 2 parts by weight to 40 parts by weight in the (A) acrylic copolymer.
본 발명의 (A) 아크릴계 공중합체에는 또한 하기 화학식 1로 표시되는 기능성 단량체가 추가로 공중합되어 있을 수 있다. 이와 같은 기능성 단량체는 점착제의 유리전이온도의 조절 및 기타 기능성 부여를 목적으로 부가될 수 있다.In the acrylic copolymer (A) of the present invention, a functional monomer represented by the following Chemical Formula 1 may be further copolymerized. Such functional monomers may be added for the purpose of controlling the glass transition temperature of the pressure-sensitive adhesive and providing other functionalities.
[화학식 1][Formula 1]
상기 식에서, R1 내지 R3는 각각 독립적으로 수소 또는 알킬을 나타내고, R4는 시아노; 알킬로 치환 또는 비치환된 페닐; 아세틸옥시; 또는 COR5를 나타내며, 이 때 R5는 알킬 또는 알콕시알킬로 치환 또는 비치환된 아미노 또는 글리시딜옥시 를 나타낸다.Wherein R 1 to R 3 each independently represent hydrogen or alkyl, and R 4 represents cyano; Phenyl unsubstituted or substituted with alkyl; Acetyloxy; Or COR 5, wherein R 5 represents amino or glycidyloxy unsubstituted or substituted with alkyl or alkoxyalkyl.
상기 식의 R1 내지 R5의 정의에서 알킬 또는 알콕시는 탄소수 1 내지 8의 알킬 또는 알콕시를 의미하며, 바람직하게는 메틸, 에틸, 메톡시, 에톡시, 프로폭시 또는 부톡시이다. Alkyl or alkoxy in the definition of R1 to R5 in the above formula means alkyl or alkoxy having 1 to 8 carbon atoms, preferably methyl, ethyl, methoxy, ethoxy, propoxy or butoxy.
상기 화학식 1로 나타나는 단량체의 구체적인 종류로는 (메타)아크릴로니트릴, (메타)아크릴아미드, N-메틸 (메타)아크릴아미드 또는 N-부톡시 메틸 (메타)아크릴아미드와 같은 질소 함유 단량체; 스티렌 또는 메틸 스티렌과 같은 스티렌계 단량체; 글리시딜 (메타)아크릴레이트; 또는 비닐 아세테이트와 같은 카르본산 비닐 에스테르 등의 일종 또는 이종 이상을 들 수 있으나, 이에 제한되는 것은 아니다. 상기와 같은 기능성 단량체가 본 발명의 아크릴계 공중합체에 포함될 경우에는, 그 함량이 20 중량부 이하인 것이 바람직하다. 상기 함량이 20 중량부를 초과하면, 점착제 조성물의 유연성 및/또는 박리력이 저하될 우려가 있다.Specific examples of the monomer represented by Formula 1 include nitrogen-containing monomers such as (meth) acrylonitrile, (meth) acrylamide, N-methyl (meth) acrylamide or N-butoxy methyl (meth) acrylamide; Styrene-based monomers such as styrene or methyl styrene; Glycidyl (meth) acrylate; Or a carboxylic acid vinyl ester such as vinyl acetate, or the like, or a heterogeneous compound, but is not limited thereto. When the functional monomer as described above is included in the acrylic copolymer of the present invention, the content is preferably 20 parts by weight or less. When the content exceeds 20 parts by weight, there is a fear that the flexibility and / or peeling force of the pressure-sensitive adhesive composition is lowered.
상기 각각의 성분을 포함하는 (A) 공중합체를 제조하는 방법은 특별히 한정되지 않으며, 예를 들면 용액 중합, 광중합, 벌크 중합, 서스펜션 중합 또는 에멀션 중합과 같은 일반적인 중합법을 통하여 제조할 수 있다. 본 발명에서는 특히 용액 중합법을 사용하는 것이 바람직하며, 용액 중합은 각각의 단량체가 균일하게 혼합된 상태에서 개시제를 혼합하여, 50℃ 내지 140℃의 중합 온도로 수행하는 것이 바람직하다. 이 때 사용될 수 있는 개시제로는 아조비스 이소부티로니트릴 또는 아조비스시클로헥산 카르보니트릴과 같은 아조계 중합 개시제; 및/또는 과산화 벤조일 또는 과산화 아세틸과 같은 과산화물 등의 통상의 개시제를 들 수 있다.The method for producing the (A) copolymer including the respective components is not particularly limited, and can be prepared, for example, through a general polymerization method such as solution polymerization, photopolymerization, bulk polymerization, suspension polymerization or emulsion polymerization. In the present invention, it is particularly preferable to use a solution polymerization method, and solution polymerization is preferably performed at a polymerization temperature of 50 ° C to 140 ° C by mixing an initiator in a state where each monomer is uniformly mixed. Initiators which can be used at this time include azo polymerization initiators such as azobis isobutyronitrile or azobiscyclohexane carbonitrile; And / or conventional initiators such as peroxides such as benzoyl peroxide or acetyl peroxide.
본 발명의 점착제 조성물은 전술한 (A) 아크릴계 공중합체에 포함된 가교성 관능기와 반응하여, 가교 구조를 형성할 수 있는 (B) 다관능성 가교제를 포함한다. The adhesive composition of this invention contains the (B) polyfunctional crosslinking agent which can react with the crosslinkable functional group contained in the above-mentioned (A) acrylic copolymer, and can form a crosslinked structure.
본 발명에서 사용될 수 있는 가교제의 종류는 특별히 한정되지 않으며, 예를 들면, 이소시아네이트계 화합물, 에폭시계 화합물, 아지리딘계 화합물 및 금속 킬레이트계 화합물과 같은 일반적인 가교제를 사용할 수 있는데, 상기 (A) 아크릴계 공중합체가 가교성 관능기로서 히드록시기를 포함할 경우, 상기 중 이소시아네이트계 화합물을 사용하는 것이 바람직하지만, 이에 제한되는 것은 아니다. The type of crosslinking agent that can be used in the present invention is not particularly limited, and for example, general crosslinking agents such as an isocyanate compound, an epoxy compound, an aziridine compound, and a metal chelate compound can be used. When the copolymer contains a hydroxyl group as the crosslinkable functional group, it is preferable to use the above isocyanate compound, but is not limited thereto.
상기 이소시아네이트계 화합물의 예로는 톨리렌 디이소시아네이트, 크실렌 디이소시아네이트, 디페닐메탄 디이소시아네이트, 헥사메틸렌 디이소시아네이트, 이소포름 디이소시아네이트, 테트라메틸크실렌 디이소시아네이트, 나프탈렌 디이소시아네이트 및 상기 중 어느 하나의 폴리올(ex. 트리메틸롤 프로판)과의 반응물로 이루어진 군으로부터 선택된 하나 이상을 들 수 있고; 에폭시계 화합물의 예로는 에틸렌글리콜 디글리시딜에테르, 트리글리시딜에테르, 트리메틸올프로판 트리글리시딜에테르, N,N,N',N'-테트라글리시딜 에틸렌디아민 및 글리세린 디글리시딜에테르로 이루어진 군으로부터 선택된 하나 이상을 들 수 있으며; 아지리딘계 화합물의 예로는 N,N'-톨루엔-2,4-비스(1-아지리딘카르복사미드), N,N'-디페닐메탄-4,4'-비스(1-아지리딘카르복사미드), 트리에틸렌 멜라민, 비스이소프로탈로일-1-(2-메틸아지리딘) 및 트리-1-아지리디닐포스핀옥시드로 이루어진 군으로부터 선택된 하나 이상을 들 수 있다. 또한, 상기 금속 킬레이트계 화합물의 예로는, 알루미늄, 철, 아연, 주석, 티탄, 안티몬, 마그네슘 및/또는 바나듐과 같은 다가 금속이 아세틸 아세톤 또는 아세토초산 에틸 등에 배위하고 있는 화합물을 사용할 수 있으나, 이에 제한되는 것은 아니다. Examples of the isocyanate compound include tolylene diisocyanate, xylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, isoform diisocyanate, tetramethylxylene diisocyanate, naphthalene diisocyanate and any one of the above polyols (ex One or more selected from the group consisting of reactants with trimethylol propane); Examples of epoxy compounds include ethylene glycol diglycidyl ether, triglycidyl ether, trimethylolpropane triglycidyl ether, N, N, N ', N'-tetraglycidyl ethylenediamine and glycerin diglycidyl ether. One or more selected from the group consisting of; Examples of aziridine compounds include N, N'-toluene-2,4-bis (1-aziridinecarboxamide), N, N'-diphenylmethane-4,4'-bis (1-aziridinecarboxes) Mid), triethylene melamine, bisisoprotaloyl-1- (2-methylaziridine), and tri-1-aziridinylphosphine oxide. In addition, examples of the metal chelate-based compound may be a compound in which a polyvalent metal such as aluminum, iron, zinc, tin, titanium, antimony, magnesium, and / or vanadium is coordinated with acetyl acetone, ethyl acetoacetate, or the like. It is not limited.
상기 (B) 다관능성 가교제는 전술한 (A) 아크릴계 공중합체 100 중량부에 대하여 0.1 중량부 내지 5 중량부의 양으로 포함되는 것이 바람직하다. 상기 함량이 0.1 중량부보다 작으면, 가교 반응이 잘 진행되지 않아, 점착제의 응집력이 떨어질 우려가 있고, 5 중량부를 초과하면, 가교 반응이 지나치게 진행되어, 층간 박리나 들뜸 현상이 발생하는 등 내구신뢰성이 저하될 우려가 있다.It is preferable that the said (B) polyfunctional crosslinking agent is contained in the quantity of 0.1 weight part-5 weight part with respect to 100 weight part of said (A) acrylic copolymers. If the content is less than 0.1 part by weight, the crosslinking reaction may not proceed well, and the cohesive force of the pressure-sensitive adhesive may be lowered. If the content is more than 5 parts by weight, the crosslinking reaction may proceed excessively, resulting in delamination or lifting. There is a fear that the reliability is lowered.
본 발명의 점착제 조성물은 위와 같은 성분을 포함하고, 또한 경화 상태에서 IPN 구조를 형성하는 것을 특징으로 한다. 상기에서 사용된 용어 『점착제 조성물의 경화 상태』는 가열 또는 UV 조사 공정 등을 거쳐 본 발명의 조성물이 점착제의 형태로 제조된 상태를 의미하며, 용어 『IPN 구조』는 점착제가 상기 (A) 아크릴계 공중합체 및 (B) 가교제의 반응을 통해 형성된 가교 구조와 함께, 다른 성분에 의해 형성된 제 2 가교 구조를 포함하는 상태를 의미한다. 본 발명에서 상기 제 2 가교 구조를 형성하는 성분의 종류는 특별히 한정되지 않으며, 그 하나의 예로는 후술하는 다관능성 아크릴레이트 및 광개시제를 들 수 있다. 특히 본 발명에서는 점착제 조성물이 전술한 특징적인 성분을 포함함으로 인해, IPN 구조를 통해 증진된 벌크 모듈러스를 가지면서도, 점착력 상승으로 인한 재박리성, 내구성 및 점착력의 저하 또는 헤이즈 현상 등을 억제할 수 있게 되는 장점이 있다.The pressure-sensitive adhesive composition of the present invention includes the above components, and is characterized in that it forms an IPN structure in a cured state. As used herein, the term "cured state of the adhesive composition" refers to a state in which the composition of the present invention is prepared in the form of a pressure-sensitive adhesive through a heating or UV irradiation process, and the term "IPN structure" means that the pressure-sensitive adhesive is the (A) acrylic type. It means the state containing the 2nd crosslinked structure formed by the other component with the crosslinked structure formed through reaction of a copolymer and (B) crosslinking agent. The kind of the component which forms the second crosslinked structure in the present invention is not particularly limited, and examples thereof include polyfunctional acrylates and photoinitiators described below. In particular, in the present invention, since the pressure-sensitive adhesive composition contains the above-mentioned characteristic components, while having the bulk modulus enhanced through the IPN structure, it is possible to suppress re-peelability, durability and decrease in adhesive strength or haze phenomenon due to the increase in adhesive strength. There is an advantage to being there.
이에 따라, 본 발명의 점착제 조성물은 전술한 (A) 아크릴계 공중합체 및 (B) 다관능성 가교제와 함께, 다관능성 아크릴레이트를 추가로 포함할 수 있다. 상기 아크릴레이트는 후술하는 광개시제와 반응하여 점착제의 내구신뢰성 등의 물성을 개선하는 역할을 한다. 본 발명에서는 이와 같은 다관능성 아크릴레이트로서 분자량이 1,000 미만인 것으로, 2개 이상의 관능기를 함유하는 것을 사용할 수 있으며, 3개 이상의 관능기를 함유하는 다관능 아크릴레이트를 사용하는 것이 보다 바람직하지만, 이에 제한되는 것은 아니다. 상기 다관능성 아크릴레이트의 구체적인 예로는, 1,4-부탄디올 디(메타)아크릴레이트, 1,6-헥산디올 디(메타)아크릴레이트, 네오펜틸글리콜 디(메타)아크릴레이트, 폴리에틸렌글리콜 디(메타)아크릴레이트, 네오펜틸글리콜아디페이트(neopentylglycol adipate) 디(메타)아크릴레이트, 히드록시피발산(hydroxyl puivalic acid) 네오펜틸글리콜 디(메타)아크릴레이트, 디시클로펜타닐(dicyclopentanyl) 디(메타)아크릴레이트, 카프로락톤 변성 디시클로펜테닐 디(메타)아크릴레이트, 에틸렌옥시드 변성 디(메타)아크릴레이트, 디(메타)아크릴록시 에틸 이소시아누레이트, 알릴(allyl)화 시클로헥실 디(메타)아크릴레이트, 트리시클로데칸디메탄올(메타)아크릴레이트, 디메틸롤 디시클로펜탄 디(메타)아크릴레이트, 에틸렌옥시드 변성 헥사히드로프탈산 디(메타)아크릴레이트, 트리시클로데칸 디메탄올(메타)아크릴레이트, 네오펜틸글리콜 변성 트리메틸프로판 디(메타)아크릴레이트, 아다만탄(adamantane) 디(메타)아크릴레이트 또는 9,9-비스[4-(2-아크릴로일옥시에톡시)페닐]플루오렌(fluorine) 등의 2관능형; 트리메틸롤 프로판 트리(메타)아크릴레이트, 디펜타에리쓰리톨 트리(메타)아크릴레이트, 프로피온산 변성 디펜타에리쓰리톨 트리(메타)아크릴레이트, 펜타에리쓰리톨 트리(메타)아크릴레이트, 프로필렌옥시드 변성 트리메틸롤프로판 트리(메타)아크릴레이트, 3관능형 우레탄 (메타)아크릴레이트 또는 트리스(메타)아크릴록시에틸이소시아누레이트 등의 3관능형; 디글리세린 테트라(메타)아크릴레이트 또는 펜타에리쓰리톨 테트라(메타)아크릴레이트 등의 4관능형; 프로피온산 변성 디펜타에리쓰리톨 펜타(메타)아크릴레이트 등의 5관능형; 및 디펜타에리쓰리톨 헥사(메타)아크릴레이트, 카프로락톤 변성 디펜타에리쓰리톨 헥사(메타)아크릴레이트 또는 우레탄 (메타)아크릴레이트(ex. 이소시아네이트 단량체 및 트리메틸롤프로판 트리(메타)아크릴레이트의 반응물 등)(ex. Kyoeisha(사)의 UA-306I 또는 UA-306T) 등의 6관능형 등을 들 수 있으나, 이에 제한되는 것은 아니다.Accordingly, the pressure-sensitive adhesive composition of the present invention may further include a polyfunctional acrylate together with the aforementioned (A) acrylic copolymer and (B) the polyfunctional crosslinking agent. The acrylate serves to improve physical properties such as durability of the pressure-sensitive adhesive by reacting with a photoinitiator described later. In the present invention, as the multifunctional acrylate having a molecular weight of less than 1,000, those containing two or more functional groups can be used, and it is more preferable to use a multifunctional acrylate containing three or more functional groups, but the present invention is limited thereto. It is not. Specific examples of the multifunctional acrylate include 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and polyethylene glycol di (meth). ) Acrylate, neopentylglycol adipate di (meth) acrylate, hydroxyl puivalic acid neopentylglycol di (meth) acrylate, dicyclopentanyl di (meth) acrylic Latex, caprolactone modified dicyclopentenyl di (meth) acrylate, ethylene oxide modified di (meth) acrylate, di (meth) acryloxy ethyl isocyanurate, allylated cyclohexyl di (meth) Acrylate, tricyclodecane dimethanol (meth) acrylate, dimethylol dicyclopentane di (meth) acrylate, ethylene oxide modified hexahydrophthalic acid di (meth) acrylate, Cyclodecane dimethanol (meth) acrylate, neopentylglycol modified trimethylpropane di (meth) acrylate, adamantane di (meth) acrylate or 9,9-bis [4- (2-acryloyl Bifunctional types such as oxyethoxy) phenyl] fluorine; Trimethylol propane tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, propionic acid modified dipentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, propylene oxide Trifunctional types such as modified trimethylolpropane tri (meth) acrylate, trifunctional urethane (meth) acrylate or tris (meth) acryloxyethyl isocyanurate; Tetrafunctional types such as diglycerin tetra (meth) acrylate or pentaerythritol tetra (meth) acrylate; 5-functional types, such as propionic acid modified dipentaerythritol penta (meth) acrylate; And dipentaerythritol hexa (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate or urethane (meth) acrylate (ex. Isocyanate monomers and trimethylolpropane tri (meth) acrylate Reactants, etc.) (eg, UA-306I or UA-306T of Kyoeisha Co., Ltd.) and the like, and the like, but are not limited thereto.
본 발명에서는 상기와 같은 다관능성 아크릴레이트 중 일종 또는 이종 이상을 혼합하여 사용할 수 있는데, 특히 골격 구조 중에 고리상 구조를 갖는 것을 사용하는 것이 바람직하다. 이와 같은 아크릴레이트를 사용할 경우, 점착제를 보다 하드한 상태로 형성할 수 있고, 이에 따라 빛샘 억제 효과를 보다 증진시킬 수 있다. 상기에서 고리상 구조는 탄소환식 구조 또는 복소환식 구조; 또는 단환식 또는 다환식 구조의 어느 것이어도 된다. 이와 같이 고리상 구조를 포함하는 다관능성 아크릴레이트의 예로는, 디(메타)아크릴록시에틸 이소시아누레이트 및 트리스(메타)아크릴록시 에틸 이소시아누레이트 등의 이소시아누레이트 구조를 갖는 단량체, 디메틸롤디시클로펜탄 디(메타)아크릴레이트, 에틸렌옥시드 변성 헥사히드로프 탈산 디(메타)아크릴레이트, 트리시클로데칸 디메탄올(메타)아크릴레이트, 네오펜틸글리콜 변성 트리메틸롤프로판 디(메타)아크릴레이트 또는 아다만탄 디(메타)아크릴레이트 등을 들 수 있으나, 이에 제한되는 것은 아니다.In the present invention, it is possible to use one kind or a mixture of two or more kinds of the above-described multifunctional acrylates, and it is particularly preferable to use one having a cyclic structure in the skeleton structure. When using such an acrylate, the pressure-sensitive adhesive can be formed in a harder state, thereby further improving the light leakage suppressing effect. The cyclic structure is a carbocyclic structure or heterocyclic structure; Or any of a monocyclic or polycyclic structure. Examples of the polyfunctional acrylate containing a cyclic structure include monomers having an isocyanurate structure such as di (meth) acryloxyethyl isocyanurate and tris (meth) acryloxy ethyl isocyanurate, Dimethyloldicyclopentane di (meth) acrylate, ethylene oxide modified hexahydrophthalic acid di (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, neopentyl glycol modified trimethylolpropane di (meth) acrylic Acrylate or adamantane di (meth) acrylate, and the like, but is not limited thereto.
상기와 같은 (B) 다관능성 아크릴레이트는, (A) 아크릴계 공중합체 100 중량부에 대하여, 5 중량부 내지 40 중량부의 양으로 점착제 조성물에 포함되는 것이 바람직하다. 상기 함량이 5 중량부 미만이면, 고온 및/또는 고습 조건 하에서 내구 신뢰성 등의 물성이 저하될 우려가 있고, 40 중량부를 초과하면 박리력이 저하 및 고온 및/또는 고습 조건 하에서의 내구신뢰성이 저하될 우려가 있다.It is preferable that such (B) polyfunctional acrylate is contained in an adhesive composition in the quantity of 5 weight part-40 weight part with respect to 100 weight part of (A) acrylic copolymers. If the content is less than 5 parts by weight, there is a risk that physical properties such as durability reliability under high temperature and / or high humidity conditions may be lowered, while if the content exceeds 40 parts by weight, the peeling force is lowered and the durability reliability under high temperature and / or high humidity conditions There is concern.
본 발명의 점착제 조성물은 또한 상기 다관능성 아크릴레이트와 반응할 수 있는 광개시제를 추가로 포함할 수 있다. 상기 광개시제는 전술한 다관능성 아크릴레이트와 반응하여, 점착제의 물성을 개선하는 역할을 한다. 본 발명에서 사용될 수 있는 광개시제의 종류는 특별히 한정되지 않으며, 예를 들면, 벤조인, 벤조인 메틸에테르, 벤조인 에틸에테르, 벤조인 이소프로필에테르, 벤조인 n-부틸에테르, 벤조인 이소부틸에테르, 아세토페논, 디메틸아니노 아세토페논, 2,2-디메톡시-2-페닐아세토페논, 2,2-디에톡시-2-페닐아세토페논, 2-히드록시-2-메틸-1-페닐프로판-1온, 1-히드록시시클로헥실페닐케톤, 2-메틸-1-[4-(메틸티오)페닐]-2-몰포리노-프로판-1-온, 4-(2-히드록시에톡시)페닐-2-(히드록시-2-프로필)케톤, 벤조페논, p-페닐벤조페논, 4,4'-디에틸아미노벤조페논, 디클로로벤조페논, 2-메틸안트라퀴논, 2-에틸안트라퀴논, 2-t-부틸안트라퀴논, 2-아미노안트라퀴논, 2-메틸티오잔 톤(thioxanthone), 2-에틸티오잔톤, 2-클로로티오잔톤, 2,4-디메틸티오잔톤, 2,4-디에틸티오잔톤, 벤질디메틸케탈, 아세토페논 디메틸케탈, p-디메틸아미노 안식향산 에스테르, 올리고[2-히드록시-2-메틸-1-[4-(1-메틸비닐)페닐]프로판논] 및 2,4,6-트리메틸벤조일-디페닐-포스핀옥시드 등을 들 수 있다. 본 발명에서는 상기 중 일종 또는 이종 이상을 사용할 수 있다.The pressure-sensitive adhesive composition of the present invention may also further include a photoinitiator capable of reacting with the multifunctional acrylate. The photoinitiator reacts with the above-mentioned multifunctional acrylate, and serves to improve physical properties of the pressure-sensitive adhesive. The kind of photoinitiator that can be used in the present invention is not particularly limited, and for example, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether , Acetophenone, dimethylanino acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropane- 1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propane-1-one, 4- (2-hydroxyethoxy) phenyl 2- (hydroxy-2-propyl) ketone, benzophenone, p-phenylbenzophenone, 4,4'-diethylaminobenzophenone, dichlorobenzophenone, 2-methylanthraquinone, 2-ethylanthraquinone, 2 t-butylanthraquinone, 2-aminoanthraquinone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthio Xanthone, Benzyldimethyl Dea, acetophenone dimethyl ketal, p-dimethylamino benzoic acid ester, oligo [2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propanone] and 2,4,6-trimethylbenzoyl -Diphenyl-phosphine oxide, etc. are mentioned. In the present invention, one or more kinds of the above can be used.
상기와 같은 광개시제는 상기 (A) 아크릴계 공중합체 100 중량부에 대하여 0.1 중량부 내지 5 중량부의 양으로 포함되는 것이 바람직하고, 보다 바람직하게는 상기 다관능성 아크릴레이트 100 중량부에 대하여 0.2 중량부 내지 20 중량부이 양으로 포함되는 것이 바람직하다. 광개시제의 함량이 상기 범위를 초과하면, 성분 다관능성 아크릴레이트와의 반응이 원활히 이루어지지 않거나, 반응 후 잔존 성분으로 인해 점착제 물성이 악화될 우려가 있다.The photoinitiator as described above is preferably included in an amount of 0.1 parts by weight to 5 parts by weight based on 100 parts by weight of the (A) acrylic copolymer, and more preferably 0.2 part by weight to 100 parts by weight of the multifunctional acrylate. It is preferably included in an amount of 20 parts by weight. When the content of the photoinitiator exceeds the above range, the reaction with the component multifunctional acrylate may not be performed smoothly, or the adhesive properties may deteriorate due to the remaining components after the reaction.
본 발명의 점착제 조성물은 또한 전술한 성분에 추가로 실란계 커플링제를 추가로 포함할 수 있다. 이와 같은 커플링제는 점착제와 유리 기판 사이의 밀착성 및 접착 안정성을 향상시켜, 내열성 및 내습성을 개선하고, 또한 점착제가 고온 및/또는 고습 하에서 장기간 방치되었을 경우에 접착 신뢰성을 향상시키는 작용을 한다. 본 발명에서는 특히, (A) 아크릴계 공중합체가 가교성 관능기로서 히드록시기를 함유할 경우, 상기와 반응할 수 있는 특정 구조의 실란계 커플링제로서 아세토아세테이트기 또는 β-시아노아세틸기를 갖는 실란계 커플링제를 사용하는 것이 바람직하다. 이와 같은 커플링제의 예로는 γ-아세토아세테이트 프로필 트리메톡시 실란, γ-아세토아세테이트 프로필 트리에톡시 실란, β-시아노아세틸 트리메톡시 실란 및 β-시아노아세틸 트리에톡시 실란 등을 들 수 있으며, 본 발명에서는 상기 중 일종 또는 이종 이상을 혼합하여 사용할 수 있다. 이와 같은 실란계 커플링제는 (A) 아크릴계 공중합체 100 중량부에 대하여 0.01 중량부 내지 5 중량부의 양으로 조성물에 포함되는 것이 바람직하고, 0.01 중량부 내지 1 중량부의 양으로 포함되는 것이 보다 바람직하다. 상기 함량이 0.01 중량부보다 작으면, 점착력 증가 효과가 미미할 우려가 있고, 5 중량부를 초과하면, 기포 또는 박리 현상이 발생하는 등 내구신뢰성이 저하될 우려가 있다.The pressure-sensitive adhesive composition of the present invention may also further include a silane coupling agent in addition to the aforementioned components. Such a coupling agent improves the adhesion and adhesion stability between the pressure-sensitive adhesive and the glass substrate, thereby improving heat resistance and moisture resistance, and also improves the adhesion reliability when the pressure-sensitive adhesive is left for a long time under high temperature and / or high humidity. In the present invention, in particular, when the (A) acrylic copolymer contains a hydroxy group as a crosslinkable functional group, a silane coupler having an acetoacetate group or a β-cyanoacetyl group as a silane coupling agent having a specific structure which can react with the above. Preference is given to using ring agents. Examples of such coupling agents include γ-acetoacetate propyl trimethoxy silane, γ-acetoacetate propyl triethoxy silane, β-cyanoacetyl trimethoxy silane, β-cyanoacetyl triethoxy silane, and the like. In the present invention, one or more of the above can be mixed and used. Such a silane coupling agent is preferably included in the composition in an amount of 0.01 parts by weight to 5 parts by weight with respect to 100 parts by weight of the (A) acrylic copolymer, and more preferably contained in an amount of 0.01 parts by weight to 1 part by weight. . If the content is less than 0.01 part by weight, the effect of increasing the adhesive force may be insignificant. If the content is more than 5 parts by weight, the durability may be lowered, such as bubble or peeling phenomenon.
본 발명의 점착제 조성물은 또한, 점착 성능의 조절의 관점에서, (A) 아크릴계 공중합체 100 중량부에 대하여 1 중량부 내지 100 중량부의 점착성 부여 수지를 추가로 포함할 수 있다. 이와 같은 점착성 부여 수지의 종류는 특별히 한정되지 않으며, 예를 들면 (수첨) 히드로카본계 수지, (수첨) 로진 수지, (수첨) 로진 에스테르 수지, (수첨) 테르펜 수지, (수첨) 테르펜 페놀 수지, 중합 로진 수지 또는 중합 로진 에스테르 수지 등의 일종 또는 이종 이상의 혼합물을 사용할 수 있다. 상기 점착성 부여 수지의 함량이 1 중량부보다 작으면, 첨가 효과가 미미할 우려가 있고, 100 중량부를 초과하면, 상용성 및/또는 응집력 향상 효과가 저하될 우려가 있다. The pressure-sensitive adhesive composition of the present invention may further include 1 part by weight to 100 parts by weight of a tackifying resin with respect to 100 parts by weight of the (A) acrylic copolymer from the viewpoint of controlling the adhesion performance. The kind of such tackifying resin is not specifically limited, For example, (hydrogenated) hydrocarbon type resin, (hydrogenated) rosin resin, (hydrogenated) rosin ester resin, (hydrogenated) terpene resin, (hydrogenated) terpene phenol resin, One kind or a mixture of two or more kinds of a polymeric rosin resin or a polymeric rosin ester resin can be used. If the content of the tackifying resin is less than 1 part by weight, the effect of addition may be insignificant. If it exceeds 100 parts by weight, the compatibility and / or cohesion improvement effect may be lowered.
본 발명의 점착제 조성물은 또한, 발명의 효과에 영향을 미치지 않는 범위에 서, 에폭시 수지, 가교제, 자외선 안정제, 산화 방지제, 조색제, 보강제, 충진제, 소포제, 계면 활성제 및 가소제로 이루어진 군으로부터 선택된 하나 이상의 첨가제를 추가로 추가로 포함할 수 있다.The pressure-sensitive adhesive composition of the present invention may also include at least one selected from the group consisting of epoxy resins, crosslinkers, ultraviolet stabilizers, antioxidants, colorants, reinforcing agents, fillers, antifoaming agents, surfactants, and plasticizers. It may further include an additive.
본 발명은 또한, 편광 필름; 및The present invention also provides a polarizing film; And
상기 편광 필름의 일면 또는 양면에 형성되고, 전술한 본 발명에 따른 점착제 조성물의 경화물을 함유하는 점착층을 포함하는 점착 편광판에 관한 것이다. It relates to an adhesive polarizing plate formed on one side or both sides of the polarizing film and comprising an adhesive layer containing a cured product of the pressure-sensitive adhesive composition according to the present invention described above.
본 발명의 점착 편광판을 구성하는 편광 필름(또는 편광 소자)의 종류는 특별히 제한되지 않는다. 예를 들면, 상기 편광 필름으로서, 폴리비닐알코올계 수지로 되는 필름에 요오드 또는 이색성 염료 등의 편광 성분을 함유시키고, 연신하여 제조되는 필름을 사용할 수 있다. 상기에서 폴리비닐알코올계 수지로는 폴리비닐알코올, 폴리비닐포르말, 폴리비닐아세탈 또는 에틸렌 초산 비닐 공중합체의 검화물 등을 사용할 수 있다. 또한, 상기 편광 필름의 두께 역시 특별히 제한되지 않으며, 통상적인 두께로 형성하면 된다.The kind of polarizing film (or polarizing element) which comprises the adhesive polarizing plate of this invention is not specifically limited. For example, as said polarizing film, the film manufactured by extending | stretching and manufacturing polarizing components, such as iodine or a dichroic dye, in the film which consists of polyvinyl alcohol-type resins can be used. As the polyvinyl alcohol-based resin, polyvinyl alcohol, polyvinyl formal, polyvinyl acetal or saponified product of ethylene vinyl acetate copolymer may be used. In addition, the thickness of the polarizing film is also not particularly limited, and may be formed in a conventional thickness.
본 발명의 점착 편광판에서는 또한 상기 편광 필름의 일면 또는 양면에 트리아세틸 셀룰로오스와 같은 셀룰로오스계 필름; 폴리카보네이트 필름 또는 폴리에틸렌테레프탈레이트 필름과 같은 폴리에스테르계 필름; 폴리에테르설폰계 필름; 및/또는 폴리에틸렌 필름, 폴리프로필렌 필름 또는 시클로계나 노르보르넨 구조를 갖는 폴리올레핀 필름 또는 에틸렌 프로필렌 공중합체와 같은 폴리올레핀계 필름 등의 보호 필름이 적층된 다층 필름으로 형성될 수 있다. 이 때 상기 보호 필름의 두께 역시 특별히 제한되지 않으며, 통상적인 두께로 형성할 수 있다.In the pressure-sensitive adhesive polarizing plate of the present invention, there is also a cellulose film such as triacetyl cellulose on one side or both sides of the polarizing film; Polyester film such as polycarbonate film or polyethylene terephthalate film; Polyether sulfone-based film; And / or a protective film such as a polyethylene film, a polypropylene film, or a polyolefin film having a cyclo or norbornene structure or a polyolefin film such as an ethylene propylene copolymer. At this time, the thickness of the protective film is also not particularly limited, and may be formed in a conventional thickness.
상기와 같은 편광 필름 상에 점착제층을 형성하는 방법은 특별히 제한되지 않으며, 예를 들면 상기 필름에 바코터 등의 일반적인 수단으로 점착제 조성물을 포함하는 코팅액을 도포하고 경화시키는 방법, 또는 일단 박리성 기재의 표면에 코팅액을 도포하여 점착제층을 형성시킨 후에, 상기 박리성 기재를 사용하여 점착제층을 편광 필름 표면에 전사하는 방법 등을 사용할 수 있다.The method for forming the pressure-sensitive adhesive layer on the polarizing film as described above is not particularly limited, and for example, a method of coating and curing the coating liquid containing the pressure-sensitive adhesive composition on the film by a general means such as a bar coater, or a peelable base material once. After apply | coating a coating liquid to the surface of and forming an adhesive layer, the method etc. which transfer the adhesive layer to the polarizing film surface using the said peelable base material can be used.
본 발명에서는 위와 같은 과정에서 점착층의 형성 시에는 코팅액 내에 포함되는 다관능성 가교제의 작용기의 가교 반응이 진행되지 않도록 제어되는 것이 균일한 코팅 수행의 관점에서 바람직하다. 즉, 상기 다관능성 가교제는 코팅 작업 후의 건조 및 숙성 과정에서 가교구조를 형성하여 응집력을 향상시키고, 이에 따라 점착 제품의 점착 물성 및 절단성(cuttability) 등이 향상될 수 있다. 또한, 본 발명에서는 상기 점착층 형성 시에 조성물 내부의 휘발 성분 또는 반응 잔류물과 같은 기포 유발 성분을 충분히 제거한 후 사용하는 것이 바람직하다. 만약, 가교 밀도 또는 분자량 등이 지나치게 낮아 탄성률이 떨어질 경우에, 고온 상태에서 유리판 및 점착제층 사이에 존재하는 작은 기포들이 커져 내부에서 산란체를 형성할 우려가 있다.In the present invention, when the adhesive layer is formed in the above process, it is preferable to control the crosslinking reaction of the functional group of the multifunctional crosslinking agent included in the coating solution from the viewpoint of performing uniform coating. That is, the multifunctional crosslinking agent forms a crosslinked structure in the drying and aging process after the coating operation to improve cohesion, thereby improving adhesive properties and cuttability of the adhesive product. In addition, in the present invention, it is preferable to use after removing the bubble-inducing components such as volatile components or reaction residues inside the composition when forming the adhesive layer. If the crosslinking density or molecular weight is too low and the modulus of elasticity falls, there is a concern that small bubbles existing between the glass plate and the pressure-sensitive adhesive layer in the high temperature state become large to form scatterers therein.
점착 편광판의 제조 시에 본 발명의 점착제 조성물을 경화시키는 방법 역시 특별히 한정되지 않고, 이 분야의 일반적인 방법을 적용할 수 있으나, 자외선 또는 전자선과 같은 활성 에너지선 조사를 통한 경화 방식이 바람직하고, 이중 자외선 조사를 통한 경화 방식이 보다 바람직하다. 이와 같은 자외선 조사는, 예를 들면, 고압수은 램프, 무전극 램프 또는 크세논 램프(xenon lamp) 등의 수단을 사용하여 수행할 수 있다.The method of curing the pressure-sensitive adhesive composition of the present invention in the manufacture of the pressure-sensitive adhesive polarizing plate is also not particularly limited, but general methods in this field may be applied, but a curing method through irradiation of active energy rays such as ultraviolet rays or electron beams is preferable, and a double The curing method through ultraviolet irradiation is more preferable. Such ultraviolet irradiation can be performed using means, such as a high pressure mercury lamp, an electrodeless lamp, or a xenon lamp, for example.
자외선 경화 방식에서 조사량은, 점착제층의 제반 물성을 훼손하지 않으면서 충분한 경화가 이루어질 정도로 제어된다면 특별히 제한되지 않으며, 예를 들면, 조도가 50 mW/cm2 내지 1,000 mW/cm2이고, 광량 50 mJ/cm2 내지 1,000 mJ/cm2일 수 있다.In the ultraviolet curing method, the irradiation amount is not particularly limited as long as it is controlled to such a degree that sufficient curing is achieved without impairing the overall physical properties of the pressure-sensitive adhesive layer, for example, the illuminance is 50 mW / cm 2 to 1,000 mW / cm 2 , and the light amount 50 mJ / cm 2 to 1,000 mJ / cm 2 .
본 발명의 편광판에 포함되는 점착제층은 또한 하기 일반식 1로 표시되는 겔(gel) 함량이 80% 내지 99%인 것이 바람직하고, 90% 내지 99%인 것이 보다 바람직하다.In the pressure-sensitive adhesive layer included in the polarizing plate of the present invention, the gel content represented by the following general formula (1) is preferably 80% to 99%, more preferably 90% to 99%.
[일반식 1][Formula 1]
겔 함량(%) = B/A × 100Gel content (%) = B / A × 100
상기 일반식 1에서, A는 점착제의 질량을 나타내고, B는 상온에서 에틸 아세테이트로 48 시간 침적 후의 점착제의 불용해분의 건조 질량을 나타낸다. In Formula 1, A represents the mass of the pressure-sensitive adhesive, B represents the dry mass of the insoluble fraction of the pressure-sensitive adhesive after 48 hours immersed in ethyl acetate at room temperature.
상기 겔 함량이 80% 미만이면, 고온 및/또는 고습 조건 하에서 내구신뢰성이 저하될 우려가 있고, 99%를 초과하면, 점착제의 응력 완화 특성이 저하될 우려가 있다.If the gel content is less than 80%, the durability and reliability may be lowered under high temperature and / or high humidity conditions. If the gel content is more than 99%, the stress relaxation characteristics of the pressure-sensitive adhesive may be lowered.
본 발명의 편광판에는 또한 보호층, 반사층, 방현층, 위상차판, 광시야각 보상 필름 및 휘도 향상 필름으로 이루어진 군으로부터 선택된 하나 이상의 기능성층 을 추가로 포함할 수 있으며, 본 발명에 따른 점착제 조성물을 함유하는 점착제가 상기 기능성층 각각에 부착되어 있을 수 있다.The polarizing plate of the present invention may further include at least one functional layer selected from the group consisting of a protective layer, a reflective layer, an antiglare layer, a retardation plate, a wide viewing angle compensation film, and a brightness enhancing film, and contains an adhesive composition according to the present invention. An adhesive may be attached to each of the functional layers.
본 발명은 또한, 전술한 본 발명에 따른 점착 편광판이 액정셀의 일면 또는 양면에 접합되어 있는 액정 패널을 포함하는 액정표시장치에 관한 것이다. The present invention also relates to a liquid crystal display device comprising a liquid crystal panel in which the above-described adhesive polarizing plate according to the present invention is bonded to one side or both sides of a liquid crystal cell.
상기와 같은 본 발명의 액정표시장치를 구성하는 액정셀의 종류는 특별히 한정되지 않으며, TN(Twisted Neumatic), STN(Super Twisted Neumatic), IPS(In Plane Switching) 또는 VA(Vertical Alignment) 방식과 같은 일반적인 액정셀을 모두 포함한다. 또한, 본 발명의 액정표시장치에 포함되는 그 외의 기타 구성의 종류 및 그 제조 방법도 특별히 한정되지 않으며, 이 분야의 일반적인 구성을 제한 없이 채용하여 사용할 수 있다.The type of liquid crystal cell constituting the liquid crystal display device of the present invention as described above is not particularly limited, such as TN (Twisted Neumatic), STN (Super Twisted Neumatic), IPS (In Plane Switching) or VA (Vertical Alignment) method It includes all common liquid crystal cells. In addition, the kind and other manufacturing method of the other structure contained in the liquid crystal display device of this invention are not specifically limited, either, The general structure of this field can be employ | adopted and used without a restriction | limiting.
이하, 본 발명에 따르는 실시예 및 본 발명에 따르지 않는 비교예를 통하여 본 발명을 보다 상세히 설명하나, 본 발명의 범위가 하기 제시된 실시예에 의해 제한되는 것은 아니다.Hereinafter, the present invention will be described in more detail through examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not limited to the examples given below.
실시예 1Example 1
아크릴계 공중합체의 제조Preparation of Acrylic Copolymer
질소 가스가 환류되고, 온도 조절이 용이하도록 냉각 장치를 설치한 1L 반응 기에 n-부틸 아크릴레이트(n-BA) 94 중량부, 아세토아세틸 메타크릴레이트(AAMA) 5중량부 및 히드록시에틸 아크릴레이트(HEA) 1.0 중량부를 포함하는 단량체 혼합물을 투여하였다. 이어서, 용제로서 에틸 아세테이트(EAc) 120 중량부를 투입하고, 산소를 제거하기 위하여 질소 가스를 60분 동안 퍼징(purging)하였다. 이어서 온도를 60℃로 유지하고, 반응 개시제로서 아조비스이소부티로니트릴(AIBN) 0.03 중량부를 투입한 후, 8 시간 동안 반응시켰다. 반응 후 에틸아세테이트(EAc)로 희석하여, 고형분 농도가 15 중량%이고, 중량평균분자량이 160만이며, 분자량 분포가 4.9인 아크릴계 공중합체를 제조하였다.94 parts by weight of n-butyl acrylate (n-BA), 5 parts by weight of acetoacetyl methacrylate (AAMA) and hydroxyethyl acrylate in a 1 L reactor equipped with a refrigeration device for easy reflux of nitrogen gas and controlling temperature A monomer mixture comprising 1.0 part by weight of (HEA) was administered. Subsequently, 120 parts by weight of ethyl acetate (EAc) was added as a solvent, and nitrogen gas was purged for 60 minutes to remove oxygen. Subsequently, the temperature was maintained at 60 ° C., 0.03 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and then reacted for 8 hours. After the reaction, the mixture was diluted with ethyl acetate (EAc) to prepare an acrylic copolymer having a solid content concentration of 15 wt%, a weight average molecular weight of 1.6 million, and a molecular weight distribution of 4.9.
점착제 조성물의 제조Preparation of pressure-sensitive adhesive composition
상기 제조된 아크릴계 공중합체 100 중량부에 대하여, 6관능 아크릴레이트(이소시아네이트 변성 우레탄 아크릴레이트; 이소시아네이트와 펜타에리쓰리톨 트리아크릴레이트의 반응물) 10 중량부, XDI계 이소시아네이트 가교제(일본 미쯔이 타케다, D110N) 1.0 중량부, 광개시제로서 히드록시 시클로헥실페닐 케톤(스위스 시바스페셜티 케미컬제) 0.5 중량부 및 β-시아노아세틸기 함유 실란계 커플링제(LG 화학제) 0.2 중량부를 혼합하여, 코팅액 고형분 농도가 15%가 되도록 조절함으로써 점착제 조성물을 제조하였다.10 parts by weight of a 6-functional acrylate (isocyanate-modified urethane acrylate; a reactant of isocyanate and pentaerythritol triacrylate) with respect to 100 parts by weight of the acrylic copolymer prepared above, an XDI-based isocyanate crosslinking agent (Takeda, Mitsui, Japan, D110N) 1.0 weight part, 0.5 weight part of hydroxy cyclohexylphenyl ketone (made by Swiss Chivas Specialty Chemical) as a photoinitiator, and 0.2 weight part of a beta-cyanoacetyl group containing silane coupling agent (LG chemical agent) were mixed, and the coating liquid solid content concentration was 15 The adhesive composition was prepared by adjusting to%.
점착 편광판의 제조Preparation of Adhesion Polarizer
상기 제조된 점착제 조성물을 박리 시트로서 이형 처리된 두께 38 미크론의 폴리에틸렌테레프탈레이트(PET)(미쯔비시사제, MRF-38) 필름 상에 건조 후 두께가 25 미크론이 되도록 코팅한 후, 상기 필름을 110℃의 오븐에서 3분 동안 건조시켰다. 이어서, 건조된 점착층을 약 1일 동안 항온항습실(23℃, 55% RH)에서 보관한 후, 편면에 WV(Wide View) 액정층이 코팅된 편광판의 WV 코팅층에 상기 점착층을 라미네이션 처리하였다. 이어서, 점착층에 하기 조건으로 자외선 처리를 하여, 점착 편광판을 제조하였다.After coating the prepared pressure-sensitive adhesive composition on a 38 micron-thick polyethylene terephthalate (PET) (MRF-38, Mitsubishi Corp.) film subjected to a release treatment as a release sheet, so that the thickness is 25 microns, the film is 110 ℃ Dried in an oven for 3 minutes. Subsequently, the dried adhesive layer was stored in a constant temperature and humidity chamber (23 ° C., 55% RH) for about 1 day, and then the adhesive layer was laminated on the WV coating layer of the polarizing plate coated with a WV (Wide View) liquid crystal layer on one side. . Subsequently, the pressure-sensitive adhesive layer was subjected to ultraviolet treatment under the following conditions to prepare a pressure-sensitive adhesive polarizing plate.
자외선 조사기: 고압 수은 램프UV irradiator: high pressure mercury lamp
조사 조건: 조도 = 600 mW/cm2, 광량 = 150 mJ/cm2 Irradiation condition: Illuminance = 600 mW / cm 2 , Light quantity = 150 mJ / cm 2
실시예 2 내지 6및 비교예 1 내지 3Examples 2-6 and Comparative Examples 1-3
아크릴계 공중합체의 제조Preparation of Acrylic Copolymer
공중합체 제조 시에 하기 표 1에 나타난 바와 같은 원료를 사용한 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 아크릴계 공중합체를 제조하였다(하기 표 1에서 아크릴계 공중합체 A는 실시예 1에서 제조된 공중합체와 동일하다).An acrylic copolymer was prepared in the same manner as in Example 1, except that raw materials as shown in Table 1 were used to prepare the copolymer (acrylic copolymer A in Table 1 was prepared in Example 1). Same as the copolymer).
[표 1]TABLE 1
점착제 조성물의 제조Preparation of pressure-sensitive adhesive composition
상기 제조된 아크릴계 공중합체에 하기 표 2 및 3에 나타난 바와 같은 성분을 혼합한 것을 제외하고는, 실시예 1과 동일한 방법으로 점착제 조성물을 제조하였다.An adhesive composition was prepared in the same manner as in Example 1, except that the components as shown in Tables 2 and 3 were mixed with the acrylic copolymer prepared above.
[표 2]TABLE 2
[표 3]TABLE 3
점착 편광판의 제조Preparation of Adhesion Polarizer
상기 각각의 점착제 조성물을 사용하여 실시예 1과 동일한 방법으로 점착 편광판을 제조하였다.An adhesive polarizing plate was prepared in the same manner as in Example 1 using the respective pressure-sensitive adhesive compositions.
실시예 및 비교예에서 제조된 점착 편광판을 사용하여 하기 제시된 방법으로 겔 분율, 점착력, 재박리성 및 내구신뢰성을 측정하였다.Using the pressure-sensitive adhesive polarizing plates prepared in Examples and Comparative Examples, gel fraction, adhesion, re-peelability, and durability were measured by the methods shown below.
1. 겔 분율의 측정1. Measurement of gel fraction
자외선 조사 후 제조된 점착층을 약 7일간 항온항습실(23℃, 60% RH)에 방치하였다. 이어서, 약 0.3 g의 점착제를 스테인리스 200 메쉬 철망에 넣은 후, 에틸 아세테이트로 침적하고, 상온의 암실에서 3일 동안 보관하였다. 이어서, 불용해분을 분리하고 70℃의 오븐에서 4 시간 동안 건조하여 질량을 측정한 후, 이를 사용 하여 겔 분율을 측정하였다.The adhesive layer prepared after UV irradiation was left in a constant temperature and humidity room (23 ° C., 60% RH) for about 7 days. Subsequently, about 0.3 g of the pressure-sensitive adhesive was placed in a stainless steel 200 mesh wire mesh, which was then deposited with ethyl acetate and stored for 3 days in a dark room at room temperature. Subsequently, the insoluble fraction was separated and dried in an oven at 70 ° C. for 4 hours to measure mass, and then the gel fraction was measured using it.
2. 점착력 및 재박리성 평가2. Evaluation of adhesion and re-peelability
제조된 점착 편광판을 25 mm × 100 mm (폭 × 길이)의 크기로 재단하여 샘플을 제조하고, 박리시트를 제거한 후, 무알칼리 유리에 라미네이터를 이용하여 부착하였다. 이어서, 오토클레이브(50℃, 5 기압)에서 약 20분 동안 압착 처리하고, 항온항습 조건(23℃, 50% RH)에 24 시간 동안 보관하였다. 그 후 물성 측정기(Texture analyzer, 영국 스테이블 마이크로 시스템)를 이용하여, 300 mm/min의 박리 속도 및 180도 박리 각도의 조건으로 점착력을 측정하고, 이를 통해 하기 기준으로 재박리성을 평가하였다.The prepared pressure-sensitive adhesive polarizing plate was cut into a size of 25 mm × 100 mm (width × length) to prepare a sample, and after removing the release sheet, it was attached to an alkali-free glass using a laminator. It was then compressed for about 20 minutes in an autoclave (50 ° C., 5 atmospheres) and stored for 24 hours in constant temperature and humidity conditions (23 ° C., 50% RH). Then, using a physical property analyzer (Texture analyzer, British Stable Microsystem), the adhesive force was measured under conditions of a peel rate of 300 mm / min and 180 ° peel angle, and through this to evaluate the re-peelability.
○: 1일 후 점착력이 800 이하○: after 1 day the adhesion is 800 or less
△: 1일 후 점착력이 1,000 이상(Triangle | delta): After 1 day, adhesive force is 1,000 or more
×: 1일 후 점착력이 2,000 이상X: adhesiveness 2,000 or more after 1 day
3. 내구신뢰성 평가3. Durability Reliability Evaluation
제조된 점착 편광판을 180 mm × 250 mm (폭 × 길이)의 크기로 재단하여 샘플을 제조하고, 상기 샘플을 19인치 시판 패널에 라미네이터를 이용하여 부착하였다. 이어서, 오토클레이브(50℃, 5 기압)에서 약 20분 동안 압착 처리하고, 항온항습 조건(23℃, 50% RH)에서 24 시간 동안 보관하여 시편을 제조하였다. 그 후, 제조된 시편들의 내습열 내구성을 평가하기 위하여, 60℃의 온도 및 90% RH의 상대 습도 조건에서 500 시간 동안 방치한 후 기포 및 박리의 발생 여부를 평가하였다. 또한, 내열 내구성은 90℃ 및 105℃의 온도에서 500 시간 방치한 후, 기포 및 박리의 발생 여부를 평가하였으며, 시편의 상태를 평가하기 직전에 상온에서 24 시간 동안 방치한 후 평가를 실시하였다. 내습열 및 내열 특성의 평가 기준은 하기와 같다.The prepared adhesive polarizing plate was cut to a size of 180 mm × 250 mm (width × length) to prepare a sample, and the sample was attached to a 19 inch commercial panel using a laminator. Subsequently, the specimen was prepared by pressing for about 20 minutes in an autoclave (50 ° C., 5 atmospheres), and stored for 24 hours at constant temperature and humidity conditions (23 ° C., 50% RH). Thereafter, in order to evaluate the heat and moisture resistance of the prepared specimens, the mixture was allowed to stand for 500 hours at a temperature of 60 ° C. and a relative humidity of 90% RH, and then evaluated for the occurrence of bubbles and peeling. In addition, after the heat resistance was left for 500 hours at a temperature of 90 ℃ and 105 ℃, and evaluated the occurrence of bubbles and peeling, it was evaluated after standing for 24 hours at room temperature immediately before evaluating the state of the specimen. Evaluation criteria of the heat-resistant and heat-resistant characteristics are as follows.
○: 기포 및 박리 현상 없음○: no bubble and peeling phenomenon
△: 기포 및/또는 박리 현상이 약하게 발생(Triangle | delta): A bubble and / or peeling phenomenon generate | occur | produce weakly
×: 기포 및/또는 박리 현상이 다량 발생X: A lot of bubble and / or peeling phenomenon generate | occur | produces
4. 광투과 균일성4. Light transmission uniformity
광투과 균일성의 평가는 내구신뢰성 평가에서와 동일한 시편을 사용하여 수행하였다. 광투과 균일성을 시험하는 방법으로는 점착층이 부착된 편광판을 22인치 모니터(LG Philips LCD사(제))에 부착하고, 항온항습 조건에서 1일 동안 보관한 후, 80℃의 오븐에서 240 시간 동안 방치한 다음, 모니터의 사각 네변 주변부 및 중심부의 광투과 균일성을 평가하였다. 광투과 균일성의 평가는 스펙트로래디오미터 CS-2000(일본 코니카미놀타社)을 사용하여, 모니터 중심부를 기준으로 상하 좌우 일정 간격으로 휘도를 측정한 후, 모니터 중심부에 대한 휘도 상승비를 계산하여 수행하였다. 이 때, 상하 또는 좌우의 휘도 상승 비율이 클수록 빛샘 현상이 심하게 발생하게 된다. The evaluation of light transmission uniformity was carried out using the same specimen as in the durability reliability evaluation. In order to test the uniformity of light transmission, a polarizing plate with an adhesive layer was attached to a 22-inch monitor (manufactured by LG Philips LCD, Inc.), stored for 1 day in a constant temperature and humidity condition, and then 240 in an oven at 80 ° C. After standing for a period of time, the light transmission uniformity of the periphery and the center of the square four sides of the monitor was evaluated. Evaluation of the light transmission uniformity was performed by measuring the luminance at a predetermined interval of up, down, left and right with respect to the center of the monitor using a spectroradiometer CS-2000 (Konica Minolta, Japan), and then calculating the luminance increase ratio with respect to the center of the monitor. . At this time, the light leakage phenomenon occurs more severely as the ratio of the increase in brightness of the up, down, left, or right.
이상의 방법으로 측정된 물성은 하기 표 4 및 5에 나타나 있다.Physical properties measured by the above method are shown in Tables 4 and 5 below.
[표 4]TABLE 4
[표 5]TABLE 5
상기 표 3의 결과로부터 알 수 있는 바와 같이, 아세토아세틸기를 포함하는 공중합체 및 가교제를 포함하여, IPN 구조를 구현한 실시예 1 내지 6의 경우, 내구 신뢰성 및 점착 특성(재박리성) 등이 우수할 뿐만 아니라, 대형 모니터에 적용되었을 경우에도 탁월한 광투과 균일성을 나타내는 것을 확인할 수 있다. 반면, 표 4의 결과로부터 알 수 있는 바와 같이, 아세토아세틸기를 포함하지 않는 공중합체를 사용한 비교예 1 및 2의 경우에는 모니터의 상하 및 좌우 방향에서 다량의 빛샘이 유발될 뿐만 아니라, 점착제의 내열 및 내습열 내구성도 열악한 것으로 나타났으며, 아크릴계 공중합체가 아세토아세틸기를 함유하되, IPN 구조를 가지지 않는 비교예 3의 경우, 빛샘 억제 효과는 여타의 비교예에 비해 다소 우수하나, 점착 특성(재박리성)이 크게 저하되는 것을 확인할 수 있었다.As can be seen from the results of Table 3, in Examples 1 to 6 including the copolymer and the crosslinking agent containing an acetoacetyl group, the durability and adhesion characteristics (re-peelability) and the like Not only is it excellent, it can be seen that it shows excellent light transmission uniformity even when applied to a large monitor. On the other hand, as can be seen from the results in Table 4, in Comparative Examples 1 and 2 using a copolymer containing no acetoacetyl group, not only a large amount of light leakage was induced in the vertical and horizontal directions of the monitor, but also the heat resistance of the adhesive. And it was also shown that the heat resistance and moisture resistance is poor, in the case of Comparative Example 3 in which the acryl-based copolymer contains acetoacetyl group, but does not have an IPN structure, the light leakage inhibitory effect is somewhat better than other comparative examples, It was confirmed that the peelability) greatly decreased.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010008231A3 (en) * | 2008-07-16 | 2010-05-14 | (주)Lg화학 | Pressure-sensitive adhesive composition, polarization plate, and liquid crystal display |
| KR20180032040A (en) * | 2016-09-21 | 2018-03-29 | 동우 화인켐 주식회사 | Adhesive Composition and Adhesive Sheet Using the Same |
| WO2018062775A1 (en) * | 2016-09-30 | 2018-04-05 | 동우 화인켐 주식회사 | Adhesive composition and adhesive sheet utilizing same |
| KR20190080264A (en) | 2017-12-28 | 2019-07-08 | 동우 화인켐 주식회사 | Adhesive composition, adhesive layer, optical member and image display device comprising the same |
| WO2020067613A1 (en) * | 2018-09-28 | 2020-04-02 | 주식회사 엘지화학 | Acrylic adhesive composition, polarizing plate, and display device |
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| US20070092733A1 (en) | 2005-10-26 | 2007-04-26 | 3M Innovative Properties Company | Concurrently curable hybrid adhesive composition |
| JP5000940B2 (en) | 2006-01-13 | 2012-08-15 | リンテック株式会社 | Adhesive for polarizing plate, adhesive sheet, polarizing plate with adhesive and method for producing the same, and optical film and method for producing the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010008231A3 (en) * | 2008-07-16 | 2010-05-14 | (주)Lg화학 | Pressure-sensitive adhesive composition, polarization plate, and liquid crystal display |
| KR20180032040A (en) * | 2016-09-21 | 2018-03-29 | 동우 화인켐 주식회사 | Adhesive Composition and Adhesive Sheet Using the Same |
| WO2018062775A1 (en) * | 2016-09-30 | 2018-04-05 | 동우 화인켐 주식회사 | Adhesive composition and adhesive sheet utilizing same |
| KR20190080264A (en) | 2017-12-28 | 2019-07-08 | 동우 화인켐 주식회사 | Adhesive composition, adhesive layer, optical member and image display device comprising the same |
| WO2020067613A1 (en) * | 2018-09-28 | 2020-04-02 | 주식회사 엘지화학 | Acrylic adhesive composition, polarizing plate, and display device |
| KR20200036619A (en) * | 2018-09-28 | 2020-04-07 | 주식회사 엘지화학 | Acryl-based adhesive composition, polarizing plate and display device |
| US20210095169A1 (en) * | 2018-09-28 | 2021-04-01 | Lg Chem, Ltd. | Acryl-Based Adhesive Composition, Polarizing Plate, and Display Device |
| US11492523B2 (en) | 2018-09-28 | 2022-11-08 | Lg Chem, Ltd. | Acryl-based adhesive composition, polarizing plate, and display device |
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