JP2015520793A - ポリエステル系プライマー組成物、これを用いた光学フィルム、及びこれを含む偏光板 - Google Patents
ポリエステル系プライマー組成物、これを用いた光学フィルム、及びこれを含む偏光板 Download PDFInfo
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- JP2015520793A JP2015520793A JP2015514941A JP2015514941A JP2015520793A JP 2015520793 A JP2015520793 A JP 2015520793A JP 2015514941 A JP2015514941 A JP 2015514941A JP 2015514941 A JP2015514941 A JP 2015514941A JP 2015520793 A JP2015520793 A JP 2015520793A
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- polyester
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- resin
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- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 229920000728 polyester Polymers 0.000 title claims abstract description 45
- 239000012788 optical film Substances 0.000 title claims description 24
- 239000011247 coating layer Substances 0.000 claims abstract description 51
- 239000010419 fine particle Substances 0.000 claims abstract description 40
- 229920001225 polyester resin Polymers 0.000 claims abstract description 35
- 239000004645 polyester resin Substances 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000010408 film Substances 0.000 claims description 124
- 239000010410 layer Substances 0.000 claims description 48
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 41
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 35
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 32
- 229920005989 resin Polymers 0.000 claims description 31
- 239000011347 resin Substances 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 22
- 239000004925 Acrylic resin Substances 0.000 claims description 21
- 229920000178 Acrylic resin Polymers 0.000 claims description 21
- -1 alicyclic carboxylic acid Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 11
- 150000003077 polyols Chemical class 0.000 claims description 11
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 11
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 150000007519 polyprotic acids Polymers 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 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 claims description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 239000004640 Melamine resin Substances 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 37
- 230000001070 adhesive effect Effects 0.000 abstract description 37
- 230000001681 protective effect Effects 0.000 abstract description 24
- 239000002904 solvent Substances 0.000 abstract description 19
- 239000000654 additive Substances 0.000 abstract description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000996 additive effect Effects 0.000 abstract description 5
- 239000003431 cross linking reagent Substances 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 36
- 238000000576 coating method Methods 0.000 description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000001723 curing Methods 0.000 description 13
- 238000001035 drying Methods 0.000 description 12
- 239000011230 binding agent Substances 0.000 description 11
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005266 casting Methods 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 239000012790 adhesive layer Substances 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
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- 239000002994 raw material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000008199 coating composition Substances 0.000 description 6
- 238000003851 corona treatment Methods 0.000 description 6
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000003848 UV Light-Curing Methods 0.000 description 5
- 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 5
- 230000000052 comparative effect Effects 0.000 description 5
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- 230000001678 irradiating effect Effects 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
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- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical group OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 4
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- LMVVEHUQNZHZNV-UHFFFAOYSA-N S(=O)(=O)=C1C(C(=O)O)C=CC=C1C(=O)O.[Na] Chemical group S(=O)(=O)=C1C(C(=O)O)C=CC=C1C(=O)O.[Na] LMVVEHUQNZHZNV-UHFFFAOYSA-N 0.000 description 4
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
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- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 4
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 4
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
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- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
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- 0 CC*C(C)C(CCC1)C1C(C)(CC)CC Chemical compound CC*C(C)C(CCC1)C1C(C)(CC)CC 0.000 description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000007611 bar coating method Methods 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
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Abstract
Description
バインダー樹脂としてウレタンアクリレートオリゴマー10g、多官能性アクリレートモノマーとしてジペンタエリスリトールヘキサアクリレート(DPHA)20g、有機微粒子として平均粒径3.5um、屈折率1.59であるポリアクリレート−co−スチレン粒子2g、無機微粒子として平均粒径4μm、屈折率1.43であるシリコン粒子2g、有機溶媒としてエタノール30g及び2−ブタノール30g、及びUV硬化開始剤2gを均一に混合して眩しさ防止層製造用組成物を製造した。ここで、上記バインダー樹脂の屈折率は1.51〜1.53程度であった。
(1)ポリエステル樹脂Aの合成例
500mlの丸底フラスコを窒素で置換し、エチレングリコール、2−メチル−1,3プロパンジオール、ソジウムスルホニルイソフタル酸、イソフタル酸を0.5:0.5:0.5:0.5のモル比で投入した後、200℃においてエステル化反応を2時間行って理論量の水を流出させた。触媒としてテトラメチルチタネート、アンチモンアセテート、ジブチルスズオキシドを投入し、安定剤としてトリメチルホスフェートを添加して水を繰り返し流出させた後、255℃において2.5Torr以下の減圧下における縮重合反応を150分間行ってポリエステル樹脂Aを製造した。
500mlの丸底フラスコを窒素で置換し、エチレングリコール、2−メチル−1,3プロパンジオール、ソジウムスルホニルイソフタル酸、イソフタル酸を0.5:0.5:0.5:0.5のモル比で投入した後、200℃においてエステル化反応を2時間行って理論量の水を流出させた。触媒としてテトラメチルチタネート、アンチモンアセテート、ジブチルスズオキシドを投入し、安定剤としてトリメチルホスフェートを添加して水を繰り返し流出させた後、2.5Torr以下の減圧下における縮重合反応を50分間行った。その後、グリシジル(メタ)アクリレート、メチル(メタ)アクリレートを2:1の重量比で投入してから冷却させ、水に高速撹拌させながら反応物及び熱開始剤を投入し、温度を80℃に上昇させて2時間維持してポリエステルアクリル樹脂Bを製造した。
500mlの丸底フラスコを窒素で置換し、エチレングリコール、2−メチル−1,3プロパンジオール、ソジウムスルホニルイソフタル酸、アジピン酸を0.5:0.5:0.5:0.5のモル比で投入し、200℃においてエステル化反応を2時間行って理論量の水を流出させた。触媒としてテトラメチルチタネート、アンチモンアセテート、ジブチルスズオキシドを投入し、安定剤としてトリメチルホスフェートを添加して水を繰り返し流出させた後、2.5Torr以下の減圧下における縮重合反応を50分間行った。その後、グリシジル(メタ)アクリレート、メチル(メタ)アクリレートを2:1の重量比で投入してから冷却させ、水に高速撹拌させながら反応物及び熱開始剤を投入し、温度を80℃に上昇させて2時間維持してポリエステルアクリル樹脂Cを製造した。
500mlの丸底フラスコを窒素で置換し、エチレングリコール、2−メチル−1,3プロパンジオール、ソジウムスルホニルイソフタル酸、シクロヘキサンジカルボン酸を0.5:0.5:0.5:0.5のモル比で投入し、200℃においてエステル化反応を2時間行って理論量の水を流出させた。触媒としてテトラメチルチタネート、アンチモンアセテート、ジブチルスズオキシドを投入し、安定剤としてトリメチルホスフェートを添加して水を繰り返し流出させた後、2.5Torr以下の減圧下における縮重合反応を50分間行った。その後、グリシジル(メタ)アクリレート、メチル(メタ)アクリレートを重量比2:1で投入してから冷却させ、水に高速撹拌させながら反応物及び熱開始剤を投入し、温度を80℃に上昇させて2時間維持してポリエステルアクリル樹脂Dを製造した。
ポリエステル樹脂A48gにメチルエチルケトン60gを添加した後、十分に撹拌して溶解させ、イソホロンジイソシアネート(isophoron diisocyanate)40gを添加した後、75℃において1時間反応させた。反応が完了すると、60℃まで冷却させた後、ジメチロールプロピオン酸12gを添加し、75℃において反応させてプレポリマー溶液を製造した。
ポリカーボネートジオール(Asahi Kasei、分子量2000)48gにメチルエチルケトン60gを添加した後、十分に撹拌して溶解させ、イソホロンジイソシアネート(isophoron diisocyanate)40gを添加してから75℃において1時間反応させた。反応が完了すると、60℃まで冷却させ、ジメチロールプロピオン酸12gを添加し、75℃において反応させてプレポリマー溶液を製造した。
上記のようにして製造されたポリエステル樹脂A40重量部、シリカ3重量部、及び水57重量部を混合してプライマー組成物を製造した後、上記プライマー組成物をコロナ処理したアクリル系フィルムの一面に#7バーでコーティングし、135℃において二軸延伸して600nmの厚さを有するプライマー層が形成されたアクリル系フィルムを製造した。フィルム表面に50W/m2/minの条件でコロナ処理を行った。
上記のようにして製造されたポリエステル樹脂A、ポリウレタン樹脂Eをそれぞれ40重量部、シリカ3重量部、及び水57重量部を混合してプライマー組成物A、Eを製造した後、上記プライマー組成物Aをコロナ処理したアクリル系フィルムの一面に#7バーでコーティングし、100℃において3分間乾燥し、再び他面にプライマー組成物Eを#7でコーティングしてから二軸延伸して、両面に600nmの厚さを有するプライマー層が形成されたアクリル系フィルムを製造した。フィルムの表面には50W/m2/minの条件でコロナ処理を行った。
上記のようにして製造されたポリエステル樹脂A、ポリエステルアクリル樹脂Bをそれぞれ40重量部、シリカ3重量部、及び水57重量部を混合してプライマー組成物A、Bを製造した後、上記プライマー組成物Aをコロナ処理したアクリル系フィルムの一面に#7バーでコーティングし、100℃において3分間乾燥し、再び他面にプライマー組成物Bを#7でコーティングした後、二軸延伸して両面に600nmの厚さを有するプライマー層が形成されたアクリル系フィルムを製造した。フィルムの表面には50W/m2/minの条件でコロナ処理を行った。
ポリエステル樹脂Aの代わりにポリエステルアクリル樹脂Bを用いた点を除いては、実施例1と同一方法で機能性コーティング層が形成されたフィルムを製造した。
ポリエステル樹脂Aの代わりにポリエステルアクリル樹脂Cを用いた点を除いては、実施例1と同一方法で機能性コーティング層が形成されたフィルムを製造した。
ポリエステル樹脂Aの代わりにポリエステルアクリル樹脂Dを用いた点を除いては、実施例1と同一方法で機能性コーティング層が形成されたフィルムを製造した。
機能性コーティング層のためのプライマー層はポリエステルアクリル樹脂B、UV接着剤のためのプライマー層はポリエステルアクリル樹脂Cを用いた点を除いては、実施例3と同一方法で偏光板を製造した。
ポリエステル樹脂Aの代わりにポリウレタン樹脂Eを用いた点を除いては、実施例1と同一方法で機能性コーティング層が形成されたフィルムを製造した。
ポリエステル樹脂Aの代わりにポリウレタン樹脂Fを用いた点を除いては、実施例1と同一方法で機能性コーティング層が形成されたフィルムを製造した。
上記実施例1〜7及び比較例1〜2によって製造されたフィルムまたは偏光板の機能性コーティング層の付着力、耐溶剤性、及び接着剤層との付着力を以下のような方法で測定した。測定結果は、下表1に示されている。
機能性コーティング層に幅1mmを有する10X10の切れ目を入れ、テープを貼って剥がした時に機能性コーティング層がどの程度剥がれるかによって付着程度を評価した。剥がれる面積が0〜20%以下の場合はOK、剥がれる面積が20%を超過するとNGと評価した。
上記実施例1〜7及び比較例1〜2において、機能性コーティング層の形成前のプライマー層にアルコール(IPA、EtOH、2−BuOH)を一滴落とし、20秒後にティッシュで10回刷り込んだ後、剥がれない場合はOK、混濁して剥がれる場合はNGと評価した。
実施例2及び3によって製造された偏光板をTA.XT.Plus(Stable Micro Systems)texture analyserを用いて90°剥離力を測定した。幅2cm、長さ8cmの紙片を製造し、アクリルフィルム面を測定器の下面に固定し、90°ピール(peel)剥離力を測定しており、測定距離は5cmであった。剥離力の測定結果、2N以上の場合はOK、2N未満の場合はNGと示した。
Claims (16)
- ポリエステル樹脂100重量部と、
水分散性微粒子1〜20重量部と、
残余の水と、を含む、ポリエステル系プライマー組成物。 - 前記ポリエステル樹脂は、下記[化学式1]で示される繰り返し単位を含む、請求項1に記載のポリエステル系プライマー組成物。
- 前記ポリエステル樹脂は、多塩基酸とポリオールの反応によって形成されるポリエステルグリコールを含む、請求項1または2に記載のポリエステル系プライマー組成物。
- 前記多塩基酸は、芳香族カルボキシ酸、脂肪族カルボキシ酸、脂環族カルボキシ酸、これらの酸無水物、これらのアルキルエステル、及びこれらの酸ハライドからなる群より選択された1種である、請求項3に記載のポリエステル系プライマー組成物。
- 前記ポリオールは、エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、ネオペンチルグリコール、ペンタンジオール、1,6−ヘキサンジオール、1,8−オクタンジオール、1,10−デカンジオール、4,4'−ジヒドロキシフェニルプロパン、4,4'−ジヒドロキシメチルメタン、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール(PEG)、ジプロピレングリコール、ポリテトラメチレングリコール(PTMG)、ポリプロピレングリコール(PPG)、1,4−シクロヘキサンジメタノール、1,4−シクロヘキサンジオール、ビスフェノールA、ビスフェノールF、グリセリン、1,1,1−トリメチロールプロパン、1,2,5−ヘキサトリオール、ペンタエリスリトール、グルコース、スクロース、及びソルビトールからなる群より選択された少なくとも1種である、請求項3または4に記載のポリエステル系プライマー組成物。
- 前記ポリエステル樹脂は、アクリル系単量体をさらに含む、請求項3から5のいずれか一項に記載のポリエステル系プライマー組成物。
- 前記アクリル系単量体は、アルキル(メタ)アクリレート、アルキルアクリレート、アルキル(メタ)アクリル酸、アルキルアクリル酸、エポキシアクリレート、ヒドロキシアルキルアクリレートからなる群より選択された1種以上である、請求項6に記載のポリエステル系プライマー組成物。
- 前記ポリエステル樹脂は、ポリエステルグリコールとアクリル系単量体を1:9〜9:1の重量比で含む、請求項6または7に記載のポリエステル系プライマー組成物。
- 前記水分散性微粒子は平均直径が10〜200nmである、請求項1から8のいずれか一項に記載のポリエステル系プライマー組成物。
- 前記水分散性微粒子は、シリカ、チタニア、アルミナ、ジルコニア、及びアンチモン系微粒子からなる群より選択された1種以上の無機系微粒子と、シリコン系樹脂、フッ素系樹脂、(メタ)アクリル系樹脂、架橋ポリビニルアルコール、及びメラミン系樹脂からなる群より選択された1種以上の有機系微粒子と、またはこれらの組み合わせである、請求項1から9のいずれか一項に記載のポリエステル系プライマー組成物。
- 基材フィルムと、
前記基材フィルムの少なくとも一面に請求項1から10のいずれか一項に記載のポリエステル系プライマー組成物によって形成されたプライマー層と、を含む、光学フィルム。 - 前記プライマー層上に機能性コーティング層が積層される、請求項11に記載の光学フィルム。
- 前記基材フィルムはアクリル系フィルムである、請求項11または12に記載の光学フィルム。
- 前記アクリル系フィルムは、アルキル(メタ)アクリレート系単位と少なくとも一つのカルボニル基で置換された3〜6元ヘテロ環単位を含む共重合体を含む、請求項13に記載の光学フィルム。
- 前記アクリル系フィルムは、主鎖にカーボネート部を有する芳香族系樹脂をさらに含む、請求項13または14に記載の光学フィルム。
- 偏光子と、
前記偏光子の少なくとも一面に請求項11から15のいずれか一項に記載の光学フィルムと、を含む、偏光板。
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