CN111886525A - Active energy ray-curable resin composition, polarizing film protective layer, and polarizing plate - Google Patents
Active energy ray-curable resin composition, polarizing film protective layer, and polarizing plate Download PDFInfo
- Publication number
- CN111886525A CN111886525A CN201980020265.9A CN201980020265A CN111886525A CN 111886525 A CN111886525 A CN 111886525A CN 201980020265 A CN201980020265 A CN 201980020265A CN 111886525 A CN111886525 A CN 111886525A
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- China
- Prior art keywords
- meth
- acrylate
- resin composition
- compound
- energy ray
- Prior art date
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- Granted
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- 239000011342 resin composition Substances 0.000 title claims abstract description 127
- 239000011241 protective layer Substances 0.000 title claims abstract description 42
- -1 oxetane compound Chemical class 0.000 claims description 210
- 239000003822 epoxy resin Substances 0.000 claims description 115
- 229920000647 polyepoxide Polymers 0.000 claims description 115
- 150000001875 compounds Chemical class 0.000 claims description 66
- 239000004593 Epoxy Substances 0.000 claims description 46
- 125000002723 alicyclic group Chemical group 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 239000003999 initiator Substances 0.000 claims description 15
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 174
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 33
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000004372 Polyvinyl alcohol Substances 0.000 description 26
- 229920002451 polyvinyl alcohol Polymers 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 23
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- 229920005989 resin Polymers 0.000 description 20
- 125000003700 epoxy group Chemical group 0.000 description 19
- 150000002921 oxetanes Chemical class 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 17
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 16
- 230000010287 polarization Effects 0.000 description 16
- 229930185605 Bisphenol Natural products 0.000 description 15
- 239000004843 novolac epoxy resin Substances 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 13
- 239000004844 aliphatic epoxy resin Substances 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 11
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 11
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 11
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 10
- 229920002799 BoPET Polymers 0.000 description 10
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 10
- 239000004327 boric acid Substances 0.000 description 10
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 7
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 229930003836 cresol Natural products 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 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 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 125000003566 oxetanyl group Chemical group 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920000223 polyglycerol Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 4
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 4
- FDZMLNCJBYFJBH-UHFFFAOYSA-N 2-[(2,3-dibromophenoxy)methyl]oxirane Chemical compound BrC1=CC=CC(OCC2OC2)=C1Br FDZMLNCJBYFJBH-UHFFFAOYSA-N 0.000 description 4
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 4
- SRYOCOFSUBJVQJ-UHFFFAOYSA-N 3-ethyl-3-(oxiran-2-ylmethoxy)oxetane Chemical compound CCC1(COC1)OCC1CO1 SRYOCOFSUBJVQJ-UHFFFAOYSA-N 0.000 description 4
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 239000004820 Pressure-sensitive adhesive Substances 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
- 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
- 125000002947 alkylene group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 3
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- 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 3
- 241000448053 Toya Species 0.000 description 3
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 3
- 238000010306 acid treatment Methods 0.000 description 3
- 150000003926 acrylamides Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- CVDUUPMTIHXQKC-UHFFFAOYSA-N ethene 1,3,5-triazinane-2,4,6-trione Chemical group C=C.O=C1NC(=O)NC(=O)N1 CVDUUPMTIHXQKC-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
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- 230000003595 spectral effect Effects 0.000 description 3
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- 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 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
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- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 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 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 description 2
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 2
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 2
- 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 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 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- FEJVJGYJIPXMJD-UHFFFAOYSA-N 3-(cyclohexyloxymethyl)-3-ethyloxetane Chemical compound C1CCCCC1OCC1(CC)COC1 FEJVJGYJIPXMJD-UHFFFAOYSA-N 0.000 description 2
- JUXZNIDKDPLYBY-UHFFFAOYSA-N 3-ethyl-3-(phenoxymethyl)oxetane Chemical compound C=1C=CC=CC=1OCC1(CC)COC1 JUXZNIDKDPLYBY-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000005619 boric acid group Chemical group 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical group 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
- 238000011161 development Methods 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 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
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Polarising Elements (AREA)
- Epoxy Resins (AREA)
Abstract
The present invention relates to an active energy ray-curable resin composition for protecting a polarizing film. The present invention also relates to a polarizing film protective layer obtained by curing the active energy ray-curable resin composition. The invention also relates to a polarizing plate with the polarizing film protective layer. The polarizing plate of the present invention is excellent in moist heat resistance.
Description
Technical Field
The present invention relates to an active energy ray-curable resin composition, a polarizing film protective layer, and a polarizing plate. More specifically, the present invention relates to an active energy ray-curable resin composition suitable for a protective layer for a polarizing film constituting a polarizing plate used in a liquid crystal display device or the like.
Background
Liquid crystal display devices are widely used as image display devices such as liquid crystal televisions, computer monitors, mobile phones, and digital cameras. The liquid crystal display device has a structure in which polarizing plates are laminated on both sides of a glass substrate in which liquid crystal is sealed, and various optical functional films such as a retardation plate are laminated thereon as necessary.
Conventionally, a polarizing plate has a structure in which a protective film is attached to at least one surface, preferably both surfaces, of a polarizing film made of a polyvinyl alcohol film (hereinafter, polyvinyl alcohol may be abbreviated as "PVA"). Here, as the polarizing film, a uniaxially stretched PVA-based film is widely used, which is obtained by dispersing and adsorbing a dichroic material such as iodine in a PVA-based film formed using a PVA-based resin having a high saponification degree, and preferably further crosslinking the PVA-based film with a crosslinking agent such as boric acid. Such a polarizing film is a uniaxially stretched PVA-based film, and therefore easily shrinks under high humidity. Therefore, a protective film is bonded to the polarizing film for the purpose of compensating for moisture resistance and strength.
As the protective film, thermoplastic resins such as cellulose resins, polycarbonate resins, cyclic polyolefin resins, (meth) acrylic resins, and polyester resins are used because they are excellent in transparency, mechanical strength, thermal stability, moisture barrier properties, isotropy, and the like, and particularly, protective films containing Triacetylcellulose (TAC) resins have been widely used.
These protective films are bonded to the polarizing film with an adhesive. As the adhesive, in view of adhesiveness to a polarizing film having a hydrophilic surface, it is preferable to use an aqueous PVA-based resin solution, and particularly, it is preferable to use an aqueous PVA-based resin solution mainly composed of a PVA-based resin having a high degree of saponification similar to that of the polarizing film.
However, in recent years, a polarizing plate is required to be made thinner, and studies are being made to form a protective film by applying an energy ray curable composition to a polarizing film and then irradiating the polarizing film with an energy ray, without using a Triacetylcellulose (TAC) film which has been most commonly used as a protective film.
For example, patent document 1 proposes a polarizing plate having a light weight film and excellent durability, which is formed by providing a protective film containing an epoxy resin as a main component on at least one surface of a polarizing plate.
Patent document 2 proposes a polarizing plate having excellent adhesiveness and high durability between a polarizing plate and a protective layer formed of a cured product of a resin composition containing an aromatic epoxy compound on at least one surface thereof.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2004-2456924
Patent document 2: japanese patent laid-open publication No. 2016 & 85369
Disclosure of Invention
Problems to be solved by the invention
However, the protective film described in patent document 1 and the protective layer described in patent document 2 have insufficient performance, and the polarizing plate using them may have insufficient moist heat resistance.
Accordingly, an object of the present invention is to provide an active energy ray-curable resin composition capable of forming a polarizing film protective layer that can provide a polarizing plate having excellent moist heat resistance.
Means for solving the problems
That is, the present invention relates to the following <1> to <11 >.
<1> an active energy ray-curable resin composition for protecting a polarizing film, which contains an epoxy resin having an epoxy equivalent of 300 or more.
<2> the active energy ray-curable resin composition according to <1>, wherein the epoxy resin has an aromatic ring or an alicyclic ring skeleton.
<3> the active energy ray-curable resin composition according to <1> or <2>, which contains an oxetane compound.
<4> the active energy ray-curable resin composition according to <3>, wherein the oxetane compound is contained in an amount of 1 to 90 parts by weight based on 100 parts by weight of the total amount of the epoxy resin and the oxetane compound.
<5> an active energy ray-curable resin composition for protecting a polarizing film, which comprises a 2-or more-functional oxetane compound (A1) and a compound (B) having at least 2 unsaturated hydrocarbon groups,
the content ratio of the oxetane compound (A1) is 51 to 99 parts by weight based on 100 parts by weight of the active energy ray-curable resin composition.
<6> the active energy ray-curable resin composition according to <5>, wherein the compound (B) is a radically polymerizable monomer.
<7> an active energy ray-curable resin composition for protecting a polarizing film, which contains a 2-or more-functional oxetane compound (A2) and an epoxy compound (C),
the content ratio of the oxetane compound (A2) is 75 to 99 parts by weight based on 100 parts by weight of the active energy ray-curable resin composition,
the epoxy compound (C) has at least one of an aromatic ring structure and an alicyclic ring structure.
<8> the active energy ray-curable resin composition according to any one of <1> to <7>, which contains a photoacid generator.
<9> the active energy ray-curable resin composition according to any one of <1> to <8>, wherein a photo radical initiator is contained.
<10> a polarizing film protective layer obtained by curing the active energy ray-curable resin composition according to any one of <1> to <9 >.
<11> a polarizing plate comprising the polarizing film protective layer <10 >.
ADVANTAGEOUS EFFECTS OF INVENTION
When the polarizing film protective layer obtained from the active energy ray-curable resin composition for protecting a polarizing film according to embodiment 1 of the present invention is used, a polarizing plate having excellent moist heat resistance can be obtained.
The active energy ray-curable resin composition for protecting a polarizing film according to embodiment 2 of the present invention is excellent in curability. The resin composition can form a polarizing film protective layer having excellent adhesion to a polarizing film. When the polarizing film protective layer is used, a polarizing plate having excellent moist heat resistance can be obtained.
The active energy ray-curable resin composition for protecting a polarizing film according to embodiment 3 of the present invention is excellent in curability. When the polarizing film protective layer obtained from the resin composition is used, a polarizing plate having excellent moist heat resistance can be obtained.
Detailed Description
The present invention will be described in detail below, but these embodiments show an example of an ideal embodiment.
In the present invention, (meth) acrylic acid means acrylic acid or methacrylic acid, (meth) acryloyl means acryloyl or methacryloyl, and (meth) acrylate means acrylate or methacrylate.
The active energy ray-curable resin composition for protecting a polarizing film according to embodiment 1 of the present invention may be simply referred to as "resin composition 1". The active energy ray-curable resin composition for protecting a polarizing film according to embodiment 2 of the present invention may be simply referred to as "resin composition 2". The active energy ray-curable resin composition for protecting a polarizing film according to embodiment 3 of the present invention may be simply referred to as "resin composition 3".
The 1 st resin composition, the 2 nd resin composition, and the 3 rd resin composition may be collectively referred to as "the resin composition of the present invention".
[ embodiment 1]
The 1 st resin composition contains an epoxy resin having an epoxy equivalent of 300 or more.
< epoxy resin >
The epoxy resin used in embodiment 1 of the present invention may have an epoxy equivalent of 300 or more, preferably 500 or more, and more preferably 1,000 or more. The epoxy equivalent is usually 10,000 or less, preferably 9,500 or less, more preferably 9,000 or less.
The epoxy equivalent means the number of grams (g/eq) of the resin containing 1 gram equivalent of epoxy groups. In the present invention, the epoxy equivalent means an epoxy equivalent measured in accordance with JIS K7236.
The reason why the polarizing plate having the polarizing film protective layer obtained by curing the 1 st resin composition containing an epoxy resin having an epoxy equivalent of 300 or more is excellent in moist heat resistance is not clear, but is presumed as follows. Namely, it is presumed that: the final cured product has a higher molecular weight, and the moisture-heat resistance is improved by increasing the glass transition temperature of the epoxy resin and reducing the moisture permeability, and as a result, the reduction in optical characteristics of the polarizing plate after the moisture-heat test is suppressed.
Examples of the epoxy resin having an epoxy equivalent of 300 or more include aliphatic epoxy resins, epoxy resins having an aromatic ring, epoxy resins having an alicyclic skeleton, and polymers having an epoxy group.
Among them, from the viewpoint of improving the moist heat resistance, an epoxy resin having 2 or more epoxy groups is preferable, and an epoxy resin having an aromatic ring and an epoxy resin having an alicyclic skeleton are more preferable.
Examples of the aliphatic epoxy resin include higher alcohol glycidyl ethers, higher alcohol (EO (ethylene oxide)) modified glycidyl ethers, and dibromoneopentyl glycol diglycidyl ethers. Examples thereof include polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, polybutadiene diglycidyl ether, and polyglycerol polyglycidyl ether having an epoxy equivalent of 300 or more.
Examples of the epoxy resin having an aromatic ring include those having an epoxy equivalent of 300 or more in a phenol (EO) -modified glycidyl ether, an alkylphenol glycidyl ether, a dibromophenyl glycidyl ether, a bisphenol epoxy resin, a phenol novolac epoxy resin, a cresol novolac epoxy resin, a bisphenol novolac epoxy resin, a biphenol epoxy resin, a resorcinol epoxy resin, a p-phenylene epoxy resin, a naphthalene epoxy resin, and an anthracene epoxy resin.
Among them, bisphenol epoxy resins, phenol novolac epoxy resins, cresol novolac epoxy resins, and bisphenol novolac epoxy resins are preferable, and bisphenol epoxy resins are particularly preferable.
Examples of the bisphenol epoxy resin include bisphenol a epoxy resin, bisphenol E epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, and the like, and epoxy resins obtained by mixing these bisphenol structures may be used.
Among them, bisphenol a type epoxy resins and bisphenol F type epoxy resins are preferable in terms of ease of handling.
Examples of the epoxy resin having an alicyclic skeleton include a hydrogenated epoxy resin obtained by hydrogenating an aromatic ring of an epoxy resin having an aromatic ring, an (EO) -modified alicyclic epoxy resin, an ester-modified alicyclic epoxy resin, and the like.
As the hydrogenated epoxy resin, a hydrogenated bisphenol epoxy resin is preferable.
Examples of the polymer having an epoxy group include an epoxy group-containing acrylic polymer, an epoxy group-containing acrylic styrene polymer, and an epoxy group-containing polybutadiene polymer.
These epoxy resins may be used alone or in combination of two or more.
The content of the epoxy resin in the 1 st resin composition is preferably 10 to 100% by weight, more preferably 20 to 95% by weight, and still more preferably 40 to 90% by weight, from the viewpoint of moist heat resistance.
< Oxetane Compound >
The 1 st resin composition preferably contains an oxetane compound, because of improved curability and excellent moist heat resistance.
The oxetane compound may be a compound having 1 or more oxetanyl groups in the molecule.
Examples thereof include 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (phenoxymethyl) oxetane, 3-ethyl-3- (cyclohexyloxymethyl) oxetane, 3-ethyl-3- (oxiranylmethoxy) oxetane, oxetane compounds having 1 oxetanyl group in the molecule, such as (3-ethyloxetan-3-yl) methyl (meth) acrylate, 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane, 1, 4-bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] benzene, and the like, And oxetane compounds having 2 or more oxetanyl groups in the molecule, such as 4, 4' -bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] biphenyl.
These oxetane compounds may be used alone or in combination of 2 or more.
Among them, 3-ethyl-3-hydroxymethyloxetane, 1, 4-bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] benzene, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (oxiranylmethoxy) oxetane, (3-ethyloxetan-3-yl) methyl (meth) acrylate, 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane and the like are preferably used from the viewpoint of easy availability, dilutability (low viscosity), excellent compatibility and the like.
Also, an oxetane compound having a molecular weight of 500 or less which is liquid at room temperature (25 ℃) is preferable from the viewpoint of compatibility and adhesiveness, and an oxetane compound having 2 or more oxetanyl groups in the molecule and an oxetane compound having 1 oxetanyl group and 1 (meth) acryloyl group or 1 epoxy group in the molecule are preferable from the viewpoint of excellent curability and durability.
Particular preference is given to using 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane, 3-ethyl-3- (oxiranylmethoxy) oxetane, (3-ethyloxetan-3-yl) methyl (meth) acrylate.
Specific examples of the Oxetane compound include commercially available Aron Oxetane OXT-101, Aron Oxetane OXT-121, Aron Oxetane OXT-212 and Aron Oxetane OXT-221 (all of which are available from Toyo Seisaku-Sho Co., Ltd.). Aron Oxetane OXT-101 and Aron Oxetane OXT-221 are particularly preferred.
The content of the oxetane compound is preferably 1 to 90 parts by weight, more preferably 5 to 80 parts by weight, and still more preferably 10 to 60 parts by weight, based on 100 parts by weight of the total amount of the epoxy resin and the oxetane compound. If the content ratio is too small, curability tends to be poor, and if it is too large, adhesiveness to a polarizing film tends to be easily reduced.
< solvent >
The 1 st resin composition may further comprise a solvent.
By including the solvent in the 1 st resin composition, the viscosity of the 1 st resin composition can be adjusted, the coatability can be improved, a polarizing film protective layer having a uniform thickness can be obtained, and the moist heat resistance of the polarizing plate can be improved.
The viscosity of the 1 st resin composition is preferably adjusted to 20,000mPa or less.
Examples of the solvent include toluene, xylene, ethyl acetate, methyl ethyl ketone, alcohols (methanol, ethanol, butanol, propanol, isopropanol, etc.), and toluene, ethyl acetate, and methyl ethyl ketone can be suitably used.
The content of the solvent in the 1 st resin composition is preferably 50 to 300 parts by weight, more preferably 70 to 250 parts by weight, and still more preferably 90 to 200 parts by weight, based on 100 parts by weight of the total amount of the epoxy resin and the oxetane compound.
If the content of the solvent is too small, the viscosity at the time of coating becomes high, and it is difficult to obtain a polarizing film protective layer having a uniform thickness, and if it is too large, the drying time for removing the solvent tends to be long.
< epoxy resin having an epoxy equivalent of less than 300 >
The 1 st resin composition may contain, in addition to the above components, an aliphatic epoxy resin, an alicyclic epoxy resin having an epoxy group in an alicyclic skeleton, and an epoxy resin having an aromatic ring, which are listed below, as an epoxy resin having an epoxy equivalent of less than 300.
(aliphatic epoxy resin)
Examples of the aliphatic epoxy resin include aliphatic epoxy resins having 1 epoxy group in the molecule, such as butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, glycidyl (glycyl) alcohol, alcohol glycidyl ether having 11 to 15 carbon atoms, lauryl alcohol glycidyl ether, neopentyl glycol diglycidyl ether, 1, 4-butanediol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, trimethylolpropane polyglycidyl ether, pentaerythritol polyglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, sorbitol polyglycidyl ether, and glycerol polyglycidyl ether, and aliphatic epoxy resins having 2 or more epoxy groups in the molecule. Examples thereof include polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, polybutadiene diglycidyl ether, and polyglycerol polyglycidyl ether having an epoxy equivalent of less than 300.
These aliphatic epoxy resins may be used alone or in combination of 2 or more.
The content of the aliphatic epoxy resin in the 1 st resin composition is preferably 40% by weight or less.
(alicyclic epoxy resin having epoxy group in alicyclic skeleton)
Examples of the alicyclic epoxy resin include 3 ', 4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexanecarboxylate, -caprolactone-modified 3 ', 4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexanecarboxylate, 1, 2-epoxy-4-vinylcyclohexane, and Limonene dioxide (Limonene dioxide). These alicyclic epoxy resins may be used alone or in combination of 2 or more.
The content of the alicyclic epoxy resin in the 1 st resin composition is preferably 40% by weight or less.
(epoxy resin having aromatic Ring)
The 1 st resin composition may further include an epoxy resin having an aromatic ring.
Examples of the epoxy resin having an aromatic ring include phenyl glycidyl ether. Examples of the epoxy resin include epoxy resins having an epoxy equivalent of less than 300, such as phenol (EO) -modified glycidyl ether, alkylphenol glycidyl ether dibromophenyl glycidyl ether, bisphenol epoxy resins, phenol novolac epoxy resins, cresol novolac epoxy resins, bisphenol novolac epoxy resins, biphenol epoxy resins, resorcinol epoxy resins, p-phenylene epoxy resins, naphthalene epoxy resins, and anthracene epoxy resins.
The content of the epoxy resin having an aromatic ring in the 1 st resin composition is preferably 40% by weight or less.
[2 nd embodiment ]
The 2 nd resin composition contains an oxetane compound (A1) having a2 or more functional group and a compound (B) having at least 2 unsaturated hydrocarbon groups.
In general, when an oxetane compound is blended into a curable resin composition, the oxetane compound is blended not as a main component but as a minor component. The reason for this is that: when the oxetane compound is a main component, the glass transition temperature is lowered due to the skeleton of the oxetane compound, and as a result, the moist heat resistance tends to be lowered.
However, by increasing the content of the oxetane compound as described later, combining it with a compound having at least 2 unsaturated hydrocarbon groups, and making the oxetane compound 2-functional or more, it is possible to suppress a decrease in the glass transition temperature and improve the adhesion and the moist heat resistance.
The reason is not clear, and is presumed as follows: when the compound having an unsaturated hydrocarbon group and the oxetane compound are used by being blended, they react at a similar reaction rate, and therefore, the reaction is not greatly controlled by the structure of each other, and the reaction proceeds sufficiently to form a crosslinked structure having a high degree of crosslinking, whereby the moisture permeability of the polarizing film protective layer is suppressed, and the moist heat resistance of the polarizing plate is improved.
<2 Oxetane Compound (A1) having Functions or higher >
The oxetane compound (A1) may have a 2-or more-functional group, and examples thereof include 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane, 1, 4-bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] benzene, 4' -bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] biphenyl, and the like. These oxetane compounds (A1) can be used alone or in combination of 2 or more.
Among them, 1, 4-bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] benzene, 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane and the like are preferably used from the viewpoints of availability, dilutability (low viscosity), excellent compatibility and the like.
In addition, it is preferable to use an oxetane compound having a molecular weight of 500 or less which is liquid at room temperature (25 ℃ C.) from the viewpoint of compatibility and adhesiveness.
As the Oxetane compound (A1), for example, commercially available Aron Oxetane OXT-121 and Aron Oxetane OXT-221 (both manufactured by Toyo chemical Co., Ltd.) can be specifically used. Aron OxetanoXT-221 is particularly preferred.
The content of the oxetane compound (A1) is 51 to 99 parts by weight, preferably 55 to 95 parts by weight, and more preferably 55 to 85 parts by weight, based on 100 parts by weight of the active energy ray-curable resin composition.
If the content ratio is too small, the adhesiveness to the polarizing film tends to be poor, and if it is too large, the curability tends to be easily reduced.
< Compound (B) having at least 2 unsaturated hydrocarbon groups >
The compound (B) is preferably a radical polymerizable monomer from the viewpoint of moist heat resistance.
For example, a vinyl compound having a functional group of 2 or more and a (meth) acrylic compound having a functional group of 2 or more are listed, and from the viewpoint of curability, a (meth) acrylic compound having a functional group of 2 or more is listed.
Examples of the (meth) acrylic compound having a functional group of 2 or more include a 2-functional (meth) acrylic compound and a 3-functional or more (meth) acrylic compound.
Examples of the 2-functional (meth) acrylic compound include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 4-butylene glycol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, glycerin di (meth) acrylate, pentaerythritol di (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, and mixtures thereof, Di (meth) acrylates having a long chain or branched structure such as hydroxypivalic acid-modified neopentyl glycol di (meth) acrylate; di (meth) acrylates having an alicyclic structure such as cyclohexanedimethanol di (meth) acrylate, dimethyloldicyclopentane di (meth) acrylate, tricyclodecanedimethanol di (meth) acrylate, ethylene oxide-modified cyclohexanedimethanol di (meth) acrylate, and the like; alkylene oxide-modified bisphenol a type di (meth) acrylates such as ethylene oxide-modified bisphenol a type di (meth) acrylate and propylene oxide-modified bisphenol a type di (meth) acrylate, di (meth) acrylates having an aromatic ring such as bisphenol a diglycidyl ether di (meth) acrylate and diglycidyl phthalate di (meth) acrylate; di (meth) acrylates having a ring structure such as dioxane glycol di (meth) acrylate and ethylene oxide isocyanurate-modified di (meth) acrylate; and the like.
Examples of the 3-or more-functional (meth) acrylic compound include trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, polyglycerol poly (meth) acrylate; (meth) acrylates having 3 or more functional groups and having a long-chain or branched structure, such as (meth) acrylates having 3 or more functional groups and having an alkyl-modified structure, e.g., caprolactone-modified dipentaerythritol penta (meth) acrylate, caprolactone-modified pentaerythritol tri (meth) acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate, ethylene oxide-modified dipentaerythritol penta (meth) acrylate, ethylene oxide-modified dipentaerythritol hexa (meth) acrylate, ethylene oxide-modified pentaerythritol tri (meth) acrylate, ethylene oxide-modified glycerol tri (meth) acrylate, and the like; a tri (meth) acrylate having a ring structure such as an isocyanuric acid ethylene oxide-modified triacrylate; and the like.
Among these, 2-functional (meth) acrylic compounds are preferable from the viewpoint of balance between adhesiveness and moist heat resistance, more preferred are di (meth) acrylates having a long-chain or branched structure such as 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, glycerol di (meth) acrylate, pentaerythritol di (meth) acrylate, cyclohexanedimethanol di (meth) acrylate, dimethyloldicyclopentane di (meth) acrylate, tricyclodecanedimethanol di (meth) acrylate, ethylene oxide-modified cyclohexanedimethanol di (meth) acrylate and other di (meth) acrylates having an alicyclic structure, dioxane glycol di (meth) acrylate, ethylene oxide isocyanurate-modified di (meth) acrylate and other di (meth) acrylates having a cyclic structure. Among these, (meth) acrylic compounds having an alicyclic structure or a ring structure are more preferable from the viewpoint of further improving the moist heat resistance.
Specifically, tricyclodecane dimethanol diacrylate (LightAcylarte DCP-A, Co., Ltd.), 1, 4-butanediol diacrylate (VISCOAT #195, manufactured by OsakｃA chemical Co., Ltd.), dioxane glycol diacrylate (NK Ester A-DOG, manufactured by Nissan chemical Co., Ltd.) and the like can be mentioned.
The content of the compound (B) is preferably 1 to 49 parts by weight, more preferably 5 to 45 parts by weight, and still more preferably 15 to 45 parts by weight, based on 100 parts by weight of the active energy ray-curable resin composition, from the viewpoint of moisture and heat resistance.
< epoxy resin >
The 2 nd resin composition may include an epoxy-based resin.
Examples of the epoxy resin include aliphatic epoxy resins, alicyclic epoxy resins, epoxy resins having an aromatic ring, epoxy resins having an alicyclic skeleton, and polymers having an epoxy group.
Examples of the aliphatic epoxy resin include aliphatic epoxy resins having 1 epoxy group in the molecule, such as butyl glycidyl ether, 2-ethylhexyl glycidyl ether, allyl glycidyl ether, glycidyl, alcohol glycidyl ether having 11 to 15 carbon atoms, lauryl alcohol glycidyl ether, etc., neopentyl glycol diglycidyl ether, 1, 4-butanediol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, trimethylolpropane polyglycidyl ether, pentaerythritol polyglycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetramethylene glycol diglycidyl ether, polybutadiene diglycidyl ether, sorbitol polyglycidyl ether, glycerol polyglycidyl ether, and polyglycerol polyglycidyl ether, etc., each having 2 or more epoxy groups in the molecule, and each having 2 or more functional aliphatic epoxy resins having 2 or more epoxy groups in the molecule And (3) fat.
Examples of the alicyclic epoxy resin include 3 ', 4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, caprolactone-modified 3 ', 4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, 1, 2-epoxy-4-vinylcyclohexane, and limonene dioxide.
Examples of the epoxy resin having an aromatic ring include phenol (EO) -modified glycidyl ether, alkylphenol glycidyl ether dibromophenyl glycidyl ether, bisphenol epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, bisphenol novolac epoxy resin, biphenol epoxy resin, resorcinol epoxy resin, p-phenylene epoxy resin, naphthalene epoxy resin, and anthracene epoxy resin.
Examples of the epoxy resin having an alicyclic skeleton include a hydrogenated epoxy resin obtained by hydrogenating an aromatic ring of an epoxy resin having an aromatic ring, cyclohexanedimethanol diglycidyl ether, and the like.
The content of the epoxy resin in the 2 nd resin composition is preferably 45 parts by weight or less, more preferably 40 parts by weight or less, and still more preferably 35 parts by weight or less, based on 100 parts by weight of the total amount of the oxetane compound (a2) and the compound (B).
< Oxetane Compound (A11) >
The 2 nd resin composition may contain an oxetane compound (a11) other than the oxetane compound (a 1).
As the oxetane compound (a11), an oxetane compound having 1 oxetanyl group in the molecule can be used.
Examples of the compound include 3-ethyl-3-hydroxymethyloxetane, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, 3-ethyl-3- (phenoxymethyl) oxetane, 3-ethyl-3- (cyclohexyloxymethyl) oxetane, 3-ethyl-3- (oxiranylmethoxy) oxetane, (3-ethyloxetan-3-yl) methyl (meth) acrylate and the like.
[ embodiment 3]
The 3 rd resin composition contains an oxetane compound (A2) having a 2-or more-functional group and an epoxy compound (C).
In general, when an oxetane compound is blended into a curable resin composition, the oxetane compound is blended not as a main component but as a minor component. The reason for this is that: when the oxetane compound is a main component, the glass transition temperature is lowered due to the skeleton of the oxetane compound, and as a result, the moist heat resistance tends to be lowered.
However, by increasing the content of the oxetane compound, combining it with an epoxy compound having at least one of an aromatic ring structure and an alicyclic ring structure, and making the oxetane compound 2-functional or more as will be described later, it is possible to suppress a decrease in the glass transition temperature and improve the moist heat resistance and the adhesion.
The reason is not clear, and is presumed as follows: since the oxetane compound has a higher growth rate than the epoxy compound, the polymerization reaction proceeds sufficiently to form a crosslinked structure having a high degree of crosslinking, whereby the moisture permeability of the polarizing film protective layer is suppressed, and the moist heat resistance of the polarizing plate is improved.
<2 Oxetane Compound (A2) having Functions or higher >
The oxetane compound (A2) may have a 2-or more-functional group, and examples thereof include 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane, 1, 4-bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] benzene, 4' -bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] biphenyl, and the like. These oxetane compounds (A2) can be used alone or in combination of 2 or more.
Among them, 1, 4-bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] benzene, 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane and the like are preferably used from the viewpoints of availability, dilutability (low viscosity), excellent compatibility and the like.
In addition, it is preferable to use an oxetane compound having a molecular weight of 500 or less which is liquid at room temperature (25 ℃ C.) from the viewpoint of compatibility and adhesiveness.
As the Oxetane compound (A2), for example, commercially available Aron Oxetane OXT-121 and Aron Oxetane OXT-221 (both manufactured by Toyo chemical Co., Ltd.) can be specifically used. Aron OxetanoXT-221 is particularly preferred.
The content of the oxetane compound (A2) is 75 to 99 parts by weight, preferably 75 to 90 parts by weight, and more preferably 75 to 85 parts by weight, based on 100 parts by weight of the active energy ray-curable resin composition.
If the content ratio is too small, the adhesiveness to the polarizing film tends to be poor, and if it is too large, the curability tends to be easily reduced.
< epoxy Compound (C) >
The epoxy compound (C) may have at least one of an aromatic ring structure and an alicyclic ring structure, and among these, an epoxy compound having 2 or more epoxy groups is preferable in terms of further improving the moist heat resistance.
Examples of the epoxy compound having an aromatic ring structure include phenyl glycidyl ether, phenol (EO) -modified glycidyl ether, alkylphenol glycidyl ether dibromophenyl glycidyl ether, bisphenol-type epoxy resin, phenol novolac-type epoxy resin, cresol novolac-type epoxy resin, bisphenol novolac-type epoxy resin, biphenol-type epoxy resin, resorcinol-type epoxy resin, p-phenylene-type epoxy resin, naphthalene-type epoxy resin, and anthracene-type epoxy resin.
Among them, bisphenol epoxy resins, phenol novolac epoxy resins, cresol novolac epoxy resins, and bisphenol novolac epoxy resins are preferable, and bisphenol epoxy resins are particularly preferable.
Examples of the bisphenol epoxy resin include bisphenol a epoxy resin, bisphenol E epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, and the like, and epoxy resins obtained by mixing these bisphenol structures may be used.
Among them, bisphenol a type epoxy resins and bisphenol F type epoxy resins are preferable in terms of ease of handling.
Examples of the epoxy compound having an alicyclic structure include alicyclic epoxy compounds in which an epoxy resin, which is a polyglycidyl ether of an alicyclic polyol, and an epoxy group are directly bonded to form an alicyclic ring.
Examples of the epoxy resin as the polyglycidyl ether of an alicyclic polyol include a hydrogenated epoxy resin compound obtained by hydrogenating an aromatic epoxy compound such as a bisphenol-type epoxy resin, a phenol novolac-type epoxy resin, or a cresol novolac-type epoxy resin, and 1, 6-cyclohexanedimethanol diglycidyl ether.
Examples of the alicyclic epoxy compound include 3 ', 4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, caprolactone-modified 3 ', 4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexane carboxylate, 1, 2-epoxy-4-vinylcyclohexane, and limonene dioxide.
These epoxy compounds may be used alone or in combination of two or more.
The content of the epoxy compound (C) is preferably 1 to 25 parts by weight, more preferably 10 to 25 parts by weight, and still more preferably 15 to 25 parts by weight, based on 100 parts by weight of the active energy ray-curable resin composition, from the viewpoint of moisture and heat resistance.
[ resin composition of the present invention ]
< photoacid Generator >
The resin composition of the present invention preferably further contains a photoacid generator. By using the photoacid generator, a polymerization reaction proceeds, the adhesiveness with the polarizing film is improved, and a polarizing film protective layer having sufficient strength is obtained.
The photoacid generator is a compound that generates a cationic species or a lewis acid by irradiation of an active energy ray, and examples thereof include an aromatic diazonium salt, an aromatic iodonium salt, an onium salt such as an aromatic sulfonium salt, and an iron-arene complex.
Examples of the aromatic diazonium salt include benzenediazonium hexafluoroantimonate, benzenediazonium hexafluorophosphate, and benzenediazonium hexafluoroborate.
Examples of the aromatic iodonium salt include diphenyliodonium tetrakis (pentafluorophenyl) borate, diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, and bis (4-nonylphenyl) iodonium hexafluorophosphate.
Examples of the aromatic sulfonium salt include triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrakis (pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluorophosphate, 4 '-bis [ diphenylsulfonium ] diphenylsulfide bis-hexafluorophosphate, 4' -bis [ di (. beta. -hydroxyethoxy) phenylsulfonium ] diphenylsulfide bis-hexafluoroantimonate, 4 '-bis [ di (. beta. -hydroxyethoxy) phenylsulfonium ] diphenylsulfide bis-hexafluorophosphate, 7- [ di (. beta. -tolyl) sulfonium ] -2-isopropylthioxanthone hexafluoroantimonate, diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluoroantimonate, 4' -bis [ diphenylsulfonium ] diphenylsulfide bis-hexafluoroantimonate, 7- [ di (p-tolyl) sulfonium ] -2-isopropylthioxanthone tetrakis (pentafluorophenyl) borate, 4-phenylcarbonyl-4 ' -diphenylsulfonium-diphenylsulfide hexafluorophosphate, 4- (p-tert-butylphenylcarbonyl) -4 ' -diphenylsulfonium-diphenylsulfide hexafluoroantimonate, 4- (p-tert-butylphenylcarbonyl) -4 ' -di (p-tolyl) sulfonium-diphenylsulfide tetrakis (pentafluorophenyl) borate, etc.
Examples of the iron-arene complex include ditolyl-cyclopentadienyl iron (II) -hexafluoroantimonate, cumyl-cyclopentadienyl iron (II) -hexafluorophosphate, ditolyl-cyclopentadienyl iron (II) -tris (trifluoromethylsulfonyl) methide, and the like.
Among the above photoacid generators, aromatic iodonium salts and aromatic sulfonium salts are preferably used in view of reacting with a light source of a long wavelength with high sensitivity.
Examples thereof include diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluorophosphate (CPI-100P manufactured by San-Apro Ltd.), and diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluoroantimonate (CPI-101A manufactured by San-Apro Ltd.).
The photoacid generator may be used alone or in combination of 2 or more.
The content of the photoacid generator in the resin composition 1 is preferably 0.5 to 20 parts by weight, more preferably 1.0 to 15 parts by weight, and still more preferably 1.5 to 10 parts by weight, based on 100 parts by weight of the total amount of the epoxy resin and the oxetane compound.
The content of the photoacid generator in the 2 nd resin composition is preferably 0.5 to 20 parts by weight, more preferably 1.0 to 15 parts by weight, and still more preferably 1.5 to 10 parts by weight, based on 100 parts by weight of the total amount of the oxetane compound (a1) and the compound (B).
The content of the photoacid generator in the 3 rd resin composition is preferably 0.5 to 20 parts by weight, more preferably 1.0 to 15 parts by weight, and still more preferably 1.5 to 10 parts by weight, based on 100 parts by weight of the total amount of the oxetane compound (a2) and the epoxy compound (C).
When the content of the photoacid generator is too large, the solubility tends to be low and the moist heat resistance tends to be low. When the content of the photoacid generator is too small, curing tends to be insufficient, and adhesiveness to the polarizing film and strength of the protective layer of the polarizing film tend to be reduced.
< photo radical initiator >
The resin composition of the present invention preferably further contains a photo radical initiator.
Examples of the photo radical initiator include acetophenones such as diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzildimethylketal, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzil-2-dimethylamino-1- (4-morpholinophenyl) butanone, and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl ] propanone oligomer; benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenones such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 ' -methyl-diphenyl sulfide, 3 ', 4,4 ' -tetrakis (t-butylperoxycarbonyl) benzophenone, 2,4, 6-trimethylbenzophenone, 4-benzoyl-N, N-dimethyl-N- [2- (1-oxo-2-propenyloxy) ethyl ] benzalkonium bromide (benzanemethanaminium bromide), and 4-benzoylbenzyl) trimethylammonium chloride; thioxanthones such as 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and 2- (3-dimethylamino-2-hydroxy) -3, 4-dimethyl-9H-thioxanthone-9-one methylchloride; acylphosphine oxides such as 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethyl-pentylphosphine oxide, and bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide; and the like.
These photo radical initiators may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
In addition, as the auxiliary agent for these photo radical initiators, triethanolamine, triisopropanolamine, 4 '-dimethylaminobenzophenone (michelson), 4' -diethylaminobenzophenone, 2-dimethylaminoethylbenzoic acid, ethyl 4-dimethylaminobenzoate, ethyl (n-butoxy) 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2, 4-diethylthioxanthone, 2, 4-diisopropylthioxanthone, and the like can be used in combination.
Among the above photo radical initiators, acylphosphine oxides such as benzildimethylketal, 1-hydroxycyclohexylphenylketone, benzoylisopropyl ether, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethyl-pentylphosphine oxide, and bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide are preferable.
Specifically, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide (TPO manufactured by IGM Resins) and bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide (Omnirad 819 manufactured by IGM Resins) are preferable.
The content of the photo radical initiator in the 1 st resin composition is preferably 0.3 to 20 parts by weight, more preferably 0.5 to 15 parts by weight, and still more preferably 0.7 to 10 parts by weight, based on 100 parts by weight of the total amount of the epoxy resin and the oxetane compound.
The content of the photo radical initiator in the 2 nd resin composition is preferably 0.3 to 20 parts by weight, more preferably 0.5 to 15 parts by weight, and still more preferably 0.7 to 10 parts by weight, based on 100 parts by weight of the total amount of the oxetane compound (a1) and the compound (B).
The content of the photo radical initiator in the 3 rd resin composition is preferably 0.3 to 20 parts by weight, more preferably 0.5 to 15 parts by weight, and still more preferably 0.7 to 15 parts by weight, based on 100 parts by weight of the total amount of the oxetane compound (a2) and the epoxy compound (C).
If the content of the photo radical initiator is too large, the low molecular weight component tends to be large, the crosslinking density tends to be low, and the moist heat resistance tends to be low, and if the content of the photo radical initiator is too small, the curability tends to be poor, and the physical properties tend to be unstable.
< radical Synthesis portion >
The resin composition of the present invention may contain a radical polymerizable component.
As the radical polymerization component, a compound having at least 1 (meth) acryloyl group in the molecule (hereinafter, sometimes referred to as "(meth) acrylic compound") can be used.
By using a (meth) acrylic compound, the curing rate can be adjusted, and the curability tends to be improved. When a (meth) acrylic compound is used as the radical polymerization component, a photo radical initiator is preferably used.
Examples of the (meth) acrylic compound include a (meth) acrylic compound having 1 (meth) acryloyl group in the molecule (hereinafter, sometimes referred to as a "monofunctional (meth) acrylic compound"), and a (meth) acrylic compound having 2 or more (meth) acryloyl groups in the molecule (hereinafter, sometimes referred to as a "polyfunctional (meth) acrylic compound"). These (meth) acrylic compounds may be used alone or in combination of 2 or more.
Examples of the monofunctional (meth) acrylic compound include alkyl (meth) acrylate compounds, polar group-containing (meth) acrylic compounds, alicyclic (meth) acrylate compounds, aromatic (meth) acrylate compounds, and (meth) acrylic compounds having a (meth) acryloyl group and a reactive functional group other than a (meth) acryloyl group in the molecule.
Examples of the alkyl ester compound of (meth) acrylic acid include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, and stearyl (meth) acrylate.
Examples of the polar group-containing (meth) acrylic compound include a carboxyl group-containing (meth) acrylic compound, a hydroxyl group-containing (meth) acrylic compound, a nitrogen atom-containing (meth) acrylic compound, and an alkoxy group-containing (meth) acrylic compound.
Examples of the carboxyl group-containing (meth) acrylic compound include (meth) acrylic acid, crotonic acid, maleic anhydride, itaconic acid, fumaric acid, acrylamide-N-glycolic acid, cinnamic acid, Michael adducts of (meth) acrylic acid (for example, acrylic acid dimer, methacrylic acid dimer, acrylic acid trimer, methacrylic acid trimer, acrylic acid tetramer, methacrylic acid tetramer and the like), 2- (meth) acryloyloxyethyl dicarboxylic acid monoesters (for example, 2-acryloyloxyethyl succinic acid monoester, 2-methacryloyloxyethyl succinic acid monoester, 2-acryloyloxyethyl phthalic acid monoester, 2-methacryloyloxyethyl phthalic acid monoester, 2-acryloyloxyethyl hexahydrophthalic acid monoester, maleic acid anhydride, itaconic acid, fumaric acid, acrylamide-N-glycolic acid, cinnamic acid, and the like, 2-methacryloyloxyethyl hexahydrophthalic acid monoester, etc.).
Examples of the hydroxyl group-containing (meth) acrylate compound include hydroxyalkyl (meth) acrylate compounds such as 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate, and 6-hydroxyhexyl (meth) acrylate; caprolactone-modified (meth) acrylate compounds such as caprolactone-modified 2-hydroxyethyl (meth) acrylate; mono (meth) acrylate compounds of glycols such as ethylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, pentanediol mono (meth) acrylate, and hexanediol mono (meth) acrylate; polyalkylene glycol mono (meth) acrylate compounds such as diethylene glycol mono (meth) acrylate, triethylene glycol mono (meth) acrylate, tetraethylene glycol mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, tripropylene glycol mono (meth) acrylate, and polypropylene glycol mono (meth) acrylate; primary hydroxyl group-containing (meth) acrylate compounds such as 2-acryloyloxyethyl-2-hydroxyethylphthalate; secondary hydroxyl group-containing (meth) acrylate compounds such as 2-hydroxypropyl (meth) acrylate and 2-hydroxybutyl (meth) acrylate; t-hydroxy ester (meth) acrylates such as 2, 2-dimethyl-2-hydroxyethyl (meth) acrylate; and the like.
Examples of the nitrogen atom-containing (meth) acrylic compound include an amide group-containing (meth) acrylic compound, an amino group-containing (meth) acrylic compound, and other nitrogen atom-containing (meth) acrylic compounds.
Examples of the amide group-containing (meth) acrylic compound include (meth) acrylamide; n, N-dialkyl (meth) acrylamides such as N, N-dimethyl (meth) acrylamide and N, N-diethyl (meth) acrylamide; n-alkoxyalkyl (meth) acrylamides such as N-methoxymethyl (meth) acrylamide, N-ethoxymethyl (meth) acrylamide, N-propoxymethyl (meth) acrylamide, N-isopropoxymethyl (meth) acrylamide, N-N-butoxymethyl (meth) acrylamide, and N-isobutoxymethyl (meth) acrylamide; hydroxyl-containing acrylamides such as N- (hydroxymethyl) (meth) acrylamide; n- (3-N, N-dimethylaminopropyl) (meth) acrylamide, methylenebis (meth) acrylamide, vinylbis (meth) acrylamide, and the like.
Examples of the amino group-containing (meth) acrylic compound include a primary amino group-containing (meth) acrylate such as aminoalkyl (meth) acrylate (e.g., aminomethyl (meth) acrylate and aminoethyl (meth) acrylate), a secondary amino group-containing (meth) acrylate such as t-butylaminoethyl (meth) acrylate, a dialkylaminoalkyl (meth) acrylate (e.g., ethylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate), a tertiary amino group-containing (meth) acrylate, and a heterocyclic amine monomer such as acryloylmorpholine.
Examples of the alkoxy group-containing (meth) acrylate compound include alkoxy alkyl (meth) acrylate compounds such as 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, and 2-butoxyethyl (meth) acrylate, 2-butoxydiethylene glycol (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxydipropylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, octyloxypolyethylene glycol-polypropylene glycol-mono (meth) acrylate, lauroxypolyethylene glycol mono (meth) acrylate, and stearoxypolyethylene glycol mono (meth) acrylate compounds such as polyether chain-containing (meth) acrylate And the like.
Examples of the alicyclic (meth) acrylate compound include cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, 1, 4-cyclohexanedimethylol mono (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, and 2-adamantyl (meth) acrylate.
Examples of the aromatic (meth) acrylate compound include phenyl (meth) acrylate; benzyl (meth) acrylate; phenoxyalkyl (meth) acrylates such as phenoxyethyl (meth) acrylate and phenoxypropyl (meth) acrylate; phenoxy dialkylene glycol (meth) acrylates such as phenoxy diethylene glycol (meth) acrylate and phenoxy dipropylene glycol (meth) acrylate; phenoxy polyethylene glycol (meth) acrylate; phenoxy polyethylene glycol-polypropylene glycol- (meth) acrylate; (meth) acrylate of an adduct of p-cumylphenol and alkylene oxide, (meth) acrylate of an adduct of o-phenylphenol and alkylene oxide, (meth) acrylate of an adduct of phenol and alkylene oxide, and (meth) acrylate of an adduct of nonylphenol and alkylene oxide.
Examples of the (meth) acrylic compound having a (meth) acryloyl group and a reactive functional group other than a (meth) acryloyl group in the molecule include glycidyl methacrylate, 4-hydroxybutyl acrylate glycidyl ether, epoxy group-containing (meth) acrylate compounds such as 3, 4-epoxycyclohexylmethyl (meth) acrylate, vinyl group-containing (meth) acrylate compounds such as 2- (2-vinyloxyethoxy) ethyl (meth) acrylate, and isocyanate group-containing (meth) acrylate compounds such as 2- (meth) acryloyloxyethyl isocyanate. Further, a (meth) acrylate compound having a cyclic ether structure such as tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, and the like can be mentioned.
Examples of the polyfunctional (meth) acrylic compound include a 2-functional (meth) acrylic compound and a 3-or more-functional (meth) acrylic compound.
As the 2-functional (meth) acrylic compound, for example, examples of the (meth) acrylate include di (meth) acrylates having a long-chain or branched structure such as ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, glycerol di (meth) acrylate, pentaerythritol di (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di (meth) acrylate, hydroxypivalic acid-modified neopentyl glycol di (meth) acrylate; di (meth) acrylates having an alicyclic structure such as cyclohexanedimethanol di (meth) acrylate, dimethyloldicyclopentane di (meth) acrylate, tricyclodecanedimethanol di (meth) acrylate, ethylene oxide-modified cyclohexanedimethanol di (meth) acrylate, and the like; alkylene oxide-modified bisphenol a type di (meth) acrylates such as ethylene oxide-modified bisphenol a type di (meth) acrylate and propylene oxide-modified bisphenol a type di (meth) acrylate, di (meth) acrylates having an aromatic ring such as bisphenol a diglycidyl ether di (meth) acrylate and diglycidyl phthalate di (meth) acrylate; a di (meth) acrylate having a ring structure such as an isocyanuric acid ethylene oxide-modified di (meth) acrylate; and the like.
Examples of the 3-or more-functional (meth) acrylic compound include trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, polyglycerol poly (meth) acrylate; (meth) acrylates having 3 or more functional groups and having a long-chain or branched structure, such as (meth) acrylates having 3 or more functional groups and having an alkyl-modified structure, e.g., caprolactone-modified dipentaerythritol penta (meth) acrylate, caprolactone-modified pentaerythritol tri (meth) acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate, ethylene oxide-modified dipentaerythritol penta (meth) acrylate, ethylene oxide-modified dipentaerythritol hexa (meth) acrylate, ethylene oxide-modified pentaerythritol tri (meth) acrylate, ethylene oxide-modified glycerol tri (meth) acrylate, and the like; a tri (meth) acrylate having a ring structure such as an isocyanuric acid ethylene oxide-modified triacrylate; and the like.
In addition, oligomers such as urethane (meth) acrylate, polyester (meth) acrylate, and epoxy (meth) acrylate can also be used as the (meth) acrylic compound.
The content of the radical polymerizable component in the 1 st resin composition is preferably 40% by weight or less from the viewpoint of moist heat resistance.
The content of the radical polymerizable component other than the compound (B) having at least 2 unsaturated hydrocarbon groups in the 2 nd resin composition is preferably 40% by weight or less from the viewpoint of moist heat resistance.
The content of the radical polymerizable component in the 3 rd resin composition is preferably 20% by weight or less from the viewpoint of moist heat resistance.
< other additives >
The resin composition of the present invention may contain other additives in addition to the above components within a range not impairing the effects of the present invention.
As other additives, for example, photosensitizers; polyols; an antistatic agent; an adhesive; an acrylic resin; a urethane resin; tackifiers such as rosin, rosin ester, hydrogenated rosin ester, phenol resin, aromatic modified terpene resin, aliphatic petroleum resin, alicyclic petroleum resin, styrene resin, and xylene resin; a plasticizer; a colorant; a filler; an anti-aging agent; an ultraviolet absorber; a functional pigment; and compounds which cause color development or discoloration upon irradiation with ultraviolet light or radiation.
The content of the other additive in the resin composition of the present invention is preferably 30% by weight or less, more preferably 20% by weight or less, from the viewpoint of wet heat resistance.
The resin composition of the present invention may contain, in addition to the above additives, a small amount of impurities and the like contained in a raw material for producing a constituent component of the active energy ray-curable resin composition.
< method for producing active energy ray-curable resin composition >
The resin composition of the present invention is obtained by using the above-mentioned respective components and mixing them at a predetermined ratio.
[ polarizing film protective layer ]
The polarizing film protective layer of the present invention is obtained by curing the resin composition of the present invention. The conditions for curing the resin composition of the present invention are described in detail below.
[ polarizing plate ]
The polarizing plate of the present invention has the polarizing film protective layer of the present invention. Specifically, the polarizing plate of the present invention has the polarizing film protective layer of the present invention on a polarizing film.
The polarizing plate of the present invention is obtained by applying or laminating the resin composition of the present invention to at least one side, preferably both sides of a polarizing film, and irradiating the resultant with an active energy ray.
As the polarizing film, a uniaxially stretched film (usually stretched at a ratio of about 2 to 10 times, preferably about 3 to 7 times) obtained by dyeing a film made of a PVA-based resin having an average polymerization degree of 1,500 to 10,000 and a saponification degree of 85 to 100 mol% with an aqueous solution of iodine-potassium iodide or a dichroic dye as a base film is generally used.
The PVA-based resin is usually produced by saponifying polyvinyl acetate obtained by polymerizing vinyl acetate, and may contain a small amount of a component copolymerizable with vinyl acetate, such as an unsaturated carboxylic acid (including salts, esters, amides, nitriles, and the like), olefins, vinyl ethers, and an unsaturated sulfonate. Further, a so-called polyvinyl acetal resin such as a polyvinyl butyral resin and a polyvinyl formal resin, which is obtained by reacting a PVA-based resin with an aldehyde in the presence of an acid, and a PVA derivative may be used.
As the active energy ray, light rays such as far ultraviolet rays, near ultraviolet rays, and infrared rays, electromagnetic waves such as X-rays and γ -rays, electron beams, proton beams, and neutron beams, and the like can be used, and ultraviolet rays are advantageous in terms of curing speed, availability of an irradiation apparatus, price, and the like.
As a light source for ultraviolet irradiation, a high-pressure mercury lamp, an electrodeless lamp, an ultrahigh-pressure mercury lamp, a carbon arc lamp, a xenon lamp, a metal halide lamp, a chemical lamp, a black light lamp, an LED lamp, or the like can be used.
The wavelength of 365nm is usually 2-3000 mJ/cm2Preferably 10 to 2000mJ/cm2Ultraviolet irradiation is performed under the conditions of (1).
Particularly, when the above-mentioned high-pressure mercury lamp is used, it is usually 5 to 3000mJ/cm, for example2Preferably 50 to 2000mJ/cm2Under the conditions of (1).
In addition, when the electrodeless lamp is used, for example, it is usually 2 to 2000mJ/cm2Preferably 10 to 1000mJ/cm2Under the conditions of (1).
The irradiation time varies depending on the kind of the light source, the distance between the light source and the coated surface, the coating thickness, and other conditions, and is usually several seconds to several tens of seconds, and may be a fraction of a second in some cases.
On the other hand, in the case of the electron beam irradiation, for example, an electron beam having an energy in the range of 50 to 1000keV is used, and an irradiation dose of 2 to 50Mrad is preferably used.
The active energy ray (ultraviolet ray, electron beam, or the like) may be irradiated from any appropriate direction, and is preferably irradiated from the side of the application surface of the curable resin composition from the viewpoint of preventing uneven curing.
The thickness of the polarizing film protective layer in the polarizing plate of the present invention obtained by the above-mentioned operation is usually 0.1 to 30 μm, preferably 0.2 to 25 μm, particularly preferably 0.3 to 20 μm, and further preferably 0.5 to 15 μm. If the thickness is too small, the moist heat resistance tends to be insufficient, and if the thickness is too large, the workability of the polarizing plate tends to be lowered by cracking or the like at the time of punching.
The resin composition of the present invention exhibits very excellent moist heat resistance when used for protecting various polarizing films.
In addition, the present invention relates to a method for protecting a polarizing film using the resin composition of the present invention.
Examples
The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to the following examples as long as the invention does not exceed the gist thereof. In the examples, "part" means a weight basis.
[ test example 1]
Prior to examples and comparative examples, respective components of the curable resin compositions shown below were prepared.
[ epoxy resin ]
1-1 of epoxy resin: bisphenol A type epoxy resin (JeR 1256, Mitsubishi chemical corporation, epoxy equivalent: 8000)
1-2 parts of epoxy resin: bisphenol A type epoxy resin (JeR 1004, Mitsubishi chemical Co., Ltd., epoxy equivalent: 925)
1-3 of epoxy resin: bisphenol A type epoxy resin (JeR 828 manufactured by Mitsubishi chemical Co., Ltd., epoxy equivalent: 190)
[ Oxetane Compound ]
The compound name was 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane (OXT-221, manufactured by Toya Synthesis Co., Ltd.)
[ photoacid generators ]
Compound name Diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluorophosphate (San-Apro Ltd. CPI-100P)
[ examples 1-1 to 1-3 and comparative examples 1-1 to 1-2 ]
< preparation of active energy ray-curable resin composition >
The active energy ray-curable resin compositions were prepared by mixing the above components at the ratios shown in table 1.
< preparation of polarizing film >
First, a 60 μm PVA film was immersed in a water bath at a water temperature of 30 ℃ and stretched by a factor of 1.5.
Next, the PVA film was immersed in a dyeing bath (30 ℃ C.) containing 0.2g/L of iodine and 15g/L of potassium iodide for 240 seconds and stretched by a factor of 1.3.
Further, the PVA film was immersed in a boric acid treatment bath (50 ℃ C.) composed of 50g/L boric acid and 30g/L potassium iodide, and simultaneously uniaxially stretched at 3.08 times and boric acid-treated for 5 minutes.
Thereafter, the PVA film was dried at 90 ℃ to produce a polarizing film having a total draw ratio of 6 times.
< preparation of polarizing plate test piece >
The curable resin composition obtained above was applied to one surface of the polarizing film obtained above using a bar coater so that the film thickness after drying became 15 μm.
As for the composition containing the solvent, the solvent was removed by drying at 80 ℃ for 3 minutes.
Using an ultraviolet irradiation apparatus equipped with a high-pressure mercury lamp, the peak illuminance: 1,000mW/cm2Cumulative exposure amount: 500mJ/cm2The coated surface was irradiated with ultraviolet light (365 nm wavelength), and the curable resin composition was cured to form a protective layer, thereby producing a polarizing plate.
The obtained polarizing plate was cut to a size of 40mm × 40mm, and the surface of the polarizing plate opposite to the protective layer was bonded to glass with a pressure-sensitive adhesive having a thickness of 20 μm.
< evaluation of Properties >
(moist-heat resistance)
The obtained polarizing plate with glass was left in a constant temperature and humidity apparatus of 60 ℃ and 90% for 500 hours, and then the polarization degree of the polarizing plate was measured by an automatic polarizing film measuring apparatus VAP-7070S (manufactured by Nippon spectral Co., Ltd.). The polarization degree of the polarizing plate was evaluated in accordance with the following criteria. The results are shown in Table 1.
O: the polarization degree after 500 hours of standing was 99.9% or more.
And (delta): the polarization degree after 500 hours of standing was 99.0% or more and less than 99.9%.
X: the polarization degree after 500 hours of standing was less than 99.0%.
[ Table 1]
TABLE 1
From the above results, it is clear that the polarizing plates of examples 1-1 to 1-3 have high polarization degree and excellent moist heat resistance after being left at high temperature and high humidity.
[ test example 2]
Prior to examples and comparative examples, respective components of the curable resin compositions shown below were prepared.
[ Oxetane Compound ]
Oxetane compound 2-1(2 functional): the compound name was 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } Oxetane (Aron Oxetane OXT-221, manufactured by Toyo chemical Co., Ltd.)
Oxetane compound 2-2 (monofunctional): the compound name was 3-ethyl-3-hydroxymethyloxetane (Aron Oxetane OXT-101, manufactured by Toya Synthesis Co., Ltd.)
[ Compound having an unsaturated hydrocarbon group ]
Radical polymerizable compound 2-1(2 functional): compound name tricyclodecane dimethanol diacrylate (LightAcrylate DCP-A, KyoeishｃA chemical Co., Ltd.)
Radical polymerizable compound 2-2 (2-functional): compound name 1, 4-butanediol diacrylate (VISCOAT #195, Osaka organic chemical industry Co., Ltd.)
Radical polymerizable compound 2-3 (2-functional): compound name dioxane ethylene glycol diacrylate (NK Ester A-DOG, product of Xinzhongcun chemical industry Co., Ltd.)
Radical polymerizable compound 2-4 (monofunctional): compound name dicyclopentyl acrylate (Hitachi Kasei, FANCRYL FA-513AS)
[ photoacid generators ]
Compound name Diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluorophosphate (San-Apro Ltd. CPI-100P)
[ photo radical initiator ]
Compound name 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide (Omnirad TPO, manufactured by IGM Resins Co., Ltd.)
[ examples 2-1 to 2-4 and comparative examples 2-1 to 2-4 ]
< preparation of active energy ray-curable resin composition >
The active energy ray-curable resin compositions were prepared by mixing the above components at the ratios shown in table 2.
< preparation of polarizing film >
First, a 60 μm PVA film was immersed in a water bath at a water temperature of 30 ℃ and stretched by a factor of 1.5.
Next, the PVA film was immersed in a dyeing bath (30 ℃ C.) containing 0.2g/L of iodine and 15g/L of potassium iodide for 240 seconds and stretched by a factor of 1.3.
Further, the PVA film was immersed in a boric acid treatment bath (50 ℃ C.) having a composition of boric acid 50g/L and potassium iodide 30g/L, and simultaneously uniaxially stretched at 3.08 times and boric acid-treated for 5 minutes.
Thereafter, the PVA film was dried at 90 ℃ to produce a polarizing film having a total draw ratio of 6 times.
< preparation of polarizing plate test piece >
The curable resin composition obtained above was applied to one surface of the polarizing film obtained above using a bar coater so that the film thickness after drying became 15 μm.
A release PET film (SPPET 3801BU made by Mitsui Chemicals Tohcello Inc. with a thickness of 38 μm) was attached to the coated surface.
With an ultraviolet irradiation apparatus equipped with a high-pressure mercury lamp, the peak illuminance: 1,000mW/cm2Cumulative exposure amount: 500mJ/cm2(365 nm in wavelength) from the release PET film surface, ultraviolet irradiation, so that the curable resin composition is cured to form a protective layer, thereby producing a polarizing plate.
The curable resin composition obtained above was applied to the other surface of the polarizing film using a bar coater so that the film thickness after drying became 15 μm, and the release PET film was laminated on the applied surface.
The curable resin composition was cured by ultraviolet irradiation under the same conditions as described above to form a protective layer.
The releasing PET films were peeled off, respectively, to produce a polarizing plate having protective layers formed by curing the curable resin composition on both surfaces of the polarizing film.
< evaluation of Properties >
(curing Property)
The tackiness of the curable resin composition was confirmed with a finger immediately after the irradiation with ultraviolet light when the release PET film was peeled off. The tackiness was evaluated according to the following criteria. The results are shown in Table 2.
O: no tackiness remained.
X: the tackiness remained.
(Adhesivity)
The obtained polarizing plate was cut into a size of 40mm × 40mm, and bonded to glass with a pressure-sensitive adhesive. The obtained polarizing plate with glass was cut into 100 checkerboards at intervals of 2mm in length and width by a cutter, and adhesion between the polarizing film and the resin composition was confirmed. The adhesion was evaluated according to the following criteria. The results are shown in Table 2.
O: completely without peeling.
X: has a peeling part.
(moist-heat resistance)
The obtained polarizing plate was cut into a size of 40mm × 40mm, and bonded to glass with a pressure-sensitive adhesive having a thickness of 20 μm.
The obtained polarizing plate with glass was left in a constant temperature and humidity apparatus of 60 ℃ and 90% for 500 hours, and then the polarization degree of the polarizing plate was measured by an automatic polarizing film measuring apparatus VAP-7070S (manufactured by Nippon spectral Co., Ltd.). The polarization degree of the polarizing plate was evaluated in accordance with the following criteria. The results are shown in Table 2.
O: the polarization degree after 500 hours of standing was 99.9% or more.
And (delta): the polarization degree after 500 hours of standing was 98.0% or more and less than 99.9%.
X: the polarization degree after 500 hours of standing was less than 98.0%.
[ Table 2]
From the above results, it was found that the active energy ray-curable resin compositions of examples 2-1 to 2-4 were excellent in curability.
It is also found that the resin composition can form a polarizing film protective layer having excellent adhesion to a polarizing film, and that a polarizing plate having excellent moist heat resistance can be obtained by using the polarizing film protective layer.
[ test example 3]
Prior to examples and comparative examples, respective components of the curable resin compositions shown below were prepared.
[ Oxetane Compound ]
Oxetane compound (2-functional): the compound name was 3-ethyl-3 { [ (3-ethyloxetan-3-yl) methoxy ] methyl } oxetane (OXT-221, manufactured by Toya Synthesis Co., Ltd.)
[ epoxy compound ]
Epoxy Compound 3-1 (alicyclic group): compound name 3 ', 4' -epoxycyclohexylmethyl-3, 4-epoxycyclohexanecarboxylate (CEL 2021P, product of Daicel corporation)
Epoxy compound 3-2 (containing an alicyclic structure): compound name hydrogenated bisphenol A type epoxy resin (YX 8000, Mitsubishi chemical Co., Ltd.)
Epoxy compound 3-3 (containing an aromatic ring structure): compound name bisphenol A type epoxy resin (JER 1009, Mitsubishi chemical Co., Ltd.)
Epoxy compound 3-4 (aliphatic): compound name 1, 4-butanediol diglycidyl ether (Nagase ChemteXCorption, Ex-214L)
[ photoacid generators ]
Compound name Diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluorophosphate (San-Apro Ltd. CPI-100P)
[ examples 3-1 to 3-3 and comparative examples 3-1 to 3-3 ]
< preparation of active energy ray-curable resin composition >
The active energy ray-curable resin compositions were prepared by mixing the above components at the ratios shown in table 3.
< preparation of polarizing film >
First, a 60 μm PVA film was immersed in a water bath at a water temperature of 30 ℃ and stretched by a factor of 1.5.
Next, the PVA film was immersed in a dyeing bath (30 ℃ C.) containing 0.2g/L of iodine and 15g/L of potassium iodide for 240 seconds and stretched by a factor of 1.3.
Further, the PVA film was immersed in a boric acid treatment bath (50 ℃ C.) composed of 50g/L boric acid and 30g/L potassium iodide, and simultaneously uniaxially stretched at 3.08 times and boric acid-treated for 5 minutes.
Thereafter, the PVA film was dried at 90 ℃ to produce a polarizing film having a total draw ratio of 6 times.
< preparation of polarizing plate test piece >
The curable resin composition obtained above was applied to one surface of the polarizing film obtained above using a bar coater so that the film thickness after drying became 15 μm.
A release PET film (SPPET 3801BU made by Mitsui Chemicals Tohcello Inc. with a thickness of 38 μm) was attached to the coated surface.
With an ultraviolet irradiation apparatus equipped with a high-pressure mercury lamp, the peak illuminance: 1,000mW/cm2Cumulative exposure amount: 500mJ/cm2(365 nm in wavelength) from the release PET film surface, ultraviolet irradiation, so that the curable resin composition is cured to form a protective layer, thereby producing a polarizing plate.
The curable resin composition obtained above was applied to the other surface of the polarizing film using a bar coater so that the film thickness after drying became 15 μm, and the release PET film was laminated on the applied surface.
The curable resin composition was cured by ultraviolet irradiation under the same conditions as described above to form a protective layer.
The releasing PET films were peeled off, respectively, to produce a polarizing plate having protective layers formed by curing the curable resin composition on both surfaces of the polarizing film.
< evaluation of Properties >
(curing Property)
The tackiness of the curable resin composition was confirmed with a finger immediately after the irradiation with ultraviolet light when the release PET film was peeled off. The tackiness was evaluated according to the following criteria. The results are shown in Table 3.
O: no tackiness remained.
X: the tackiness remained.
(moist-heat resistance)
The obtained polarizing plate was cut into a size of 40mm × 40mm, and bonded to glass with a pressure-sensitive adhesive having a thickness of 20 μm.
The obtained polarizing plate with glass was left in a constant temperature and humidity apparatus of 60 ℃ and 90% for 500 hours, and then the polarization degree of the polarizing plate was measured by an automatic polarizing film measuring apparatus VAP-7070S (manufactured by Nippon spectral Co., Ltd.). The polarization degree of the polarizing plate was evaluated in accordance with the following criteria. The results are shown in Table 3.
O: the polarization degree after 500 hours of standing was 99.9% or more.
And (delta): the polarization degree after 500 hours of standing was 98.0% or more and less than 99.9%.
X: the polarization degree after 500 hours of standing was less than 98.0%.
[ Table 3]
From the above results, it was found that the active energy ray-curable resin compositions of examples 3-1 to 3-3 were excellent in curability.
Further, it is found that when a polarizing film protective layer obtained from the resin composition is used, a polarizing plate having excellent moist heat resistance can be obtained.
The present invention is described in detail or with reference to specific embodiments, but it is apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present invention.
The present application is based on japanese patent applications filed on 3/22/2018 (japanese application 2018-.
Industrial applicability
The resin composition of the present invention, a polarizing film protective layer obtained by curing the resin composition, and a polarizing plate having the protective layer are excellent in moist heat resistance and can be suitably used for an image display device such as a liquid crystal display device.
Claims (11)
1. An active energy ray-curable resin composition for protecting a polarizing film, which contains an epoxy resin having an epoxy equivalent of 300 or more.
2. The active energy ray-curable resin composition according to claim 1, wherein the epoxy resin has an aromatic ring or alicyclic ring skeleton.
3. The active energy ray-curable resin composition according to claim 1 or 2, wherein an oxetane compound is contained.
4. The active energy ray-curable resin composition according to claim 3, wherein the oxetane compound is contained in an amount of 1 to 90 parts by weight based on 100 parts by weight of the total amount of the epoxy resin and the oxetane compound.
5. An active energy ray-curable resin composition for protecting a polarizing film, which comprises a 2-or more-functional oxetane compound (A1) and a compound (B) having at least 2 unsaturated hydrocarbon groups,
the content ratio of the oxetane compound (A1) is 51 to 99 parts by weight based on 100 parts by weight of the active energy ray-curable resin composition.
6. The active energy ray-curable resin composition according to claim 5, wherein the compound (B) is a radical polymerizable monomer.
7. An active energy ray-curable resin composition for protecting a polarizing film, which comprises a 2-or more-functional oxetane compound (A2) and an epoxy compound (C),
the content ratio of the oxetane compound (A2) is 75 to 99 parts by weight based on 100 parts by weight of the active energy ray-curable resin composition,
the epoxy compound (C) has at least one of an aromatic ring structure and an alicyclic ring structure.
8. The active energy ray-curable resin composition according to any one of claims 1 to 7, which contains a photoacid generator.
9. The active energy ray-curable resin composition according to any one of claims 1 to 8, which contains a photo radical initiator.
10. A polarizing film protective layer obtained by curing the active energy ray-curable resin composition according to any one of claims 1 to 9.
11. A polarizing plate comprising the polarizing film protective layer according to claim 10.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018-054226 | 2018-03-22 | ||
| JP2018054226A JP2019168500A (en) | 2018-03-22 | 2018-03-22 | Active energy ray-curable resin composition, polarizing film protection layer, and polarizing plate using the same |
| JP2018140748 | 2018-07-26 | ||
| JP2018140747 | 2018-07-26 | ||
| JP2018-140747 | 2018-07-26 | ||
| JP2018-140748 | 2018-07-26 | ||
| PCT/JP2019/012235 WO2019182146A1 (en) | 2018-03-22 | 2019-03-22 | Active energy ray-curable resin composition, polarizing film protective layer, and polarizing plate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111886525A true CN111886525A (en) | 2020-11-03 |
| CN111886525B CN111886525B (en) | 2023-03-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201980020265.9A Active CN111886525B (en) | 2018-03-22 | 2019-03-22 | Active energy ray-curable resin composition, polarizing film protective layer, and polarizing plate |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR20200135339A (en) |
| CN (1) | CN111886525B (en) |
| WO (1) | WO2019182146A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021065107A1 (en) * | 2019-09-30 | 2021-04-08 | 日東電工株式会社 | Retardation-layer-equipped polarizing plate and image display device using same |
| US11971532B2 (en) | 2020-10-19 | 2024-04-30 | Korea Advanced Institute Of Science And Technology | Microlens array-based ultrathin microscope |
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| KR101845081B1 (en) * | 2014-11-28 | 2018-04-04 | 삼성에스디아이 주식회사 | Composition for window film, flexible window film prepared using the same and flexible display apparatus comprising the same |
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- 2019-03-22 KR KR1020207026648A patent/KR20200135339A/en not_active Application Discontinuation
- 2019-03-22 CN CN201980020265.9A patent/CN111886525B/en active Active
- 2019-03-22 WO PCT/JP2019/012235 patent/WO2019182146A1/en active Application Filing
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| JP2011236389A (en) * | 2010-05-13 | 2011-11-24 | Toyo Ink Sc Holdings Co Ltd | Photosetting adhesive for forming polarizing plate, and polarizing plate |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN111886525B (en) | 2023-03-28 |
| WO2019182146A1 (en) | 2019-09-26 |
| KR20200135339A (en) | 2020-12-02 |
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