JP2012111931A - ハードコート性樹脂組成物及びその硬化物 - Google Patents
ハードコート性樹脂組成物及びその硬化物 Download PDFInfo
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- JP2012111931A JP2012111931A JP2011176310A JP2011176310A JP2012111931A JP 2012111931 A JP2012111931 A JP 2012111931A JP 2011176310 A JP2011176310 A JP 2011176310A JP 2011176310 A JP2011176310 A JP 2011176310A JP 2012111931 A JP2012111931 A JP 2012111931A
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- Prior art keywords
- meth
- group
- resin composition
- acrylate
- monomer
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 69
- 238000000576 coating method Methods 0.000 title claims abstract description 15
- 239000011248 coating agent Substances 0.000 title claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 119
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 114
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 64
- 238000010790 dilution Methods 0.000 claims abstract description 29
- 239000012895 dilution Substances 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- -1 ethylhexyl Chemical group 0.000 description 68
- 239000010408 film Substances 0.000 description 34
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 230000003287 optical effect Effects 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 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 7
- 230000001588 bifunctional effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002220 fluorenes Chemical class 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003504 photosensitizing agent Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000012719 thermal polymerization Methods 0.000 description 4
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical group C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 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 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 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
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 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
- 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000011161 development Methods 0.000 description 2
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- 125000004663 dialkyl amino group Chemical group 0.000 description 2
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- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 230000005865 ionizing radiation Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- LBROROBTVMUJEB-UHFFFAOYSA-N s-[2-[2-(2-methylprop-2-enoylsulfanyl)ethylsulfanyl]ethyl] 2-methylprop-2-enethioate Chemical compound CC(=C)C(=O)SCCSCCSC(=O)C(C)=C LBROROBTVMUJEB-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 description 1
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- RNAOLCPDYNVOTH-UHFFFAOYSA-N 1-(4-butylphenyl)-2-(dimethylamino)-2-methylpropan-1-one Chemical compound CCCCC1=CC=C(C(=O)C(C)(C)N(C)C)C=C1 RNAOLCPDYNVOTH-UHFFFAOYSA-N 0.000 description 1
- ONCICIKBSHQJTB-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=C(N(C)C)C=C1 ONCICIKBSHQJTB-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
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Abstract
【解決手段】分子内に少なくとも1つの(メタ)アクリロイル基を有し、かつ9,9−ビスアリールフルオレン骨格を有するフルオレン含有硬化性モノマーと、分子内に3以上の(メタ)アクリロイル基を有する多官能硬化性モノマーと、分子内に1つの(メタ)アクリロイル基を有する単官能希釈モノマーとを含むハードコート性樹脂組成物を調製する。この組成物の硬化物は、屈折率が1.55以上であり、かつ鉛筆硬度が3H以上である。前記単官能希釈モノマーは、C3−7アルキル(メタ)アクリレート(特に、分岐C4−6アルキル(メタ)アクリレート)であってもよい。
【選択図】なし
Description
本発明のハードコート性樹脂組成物は、分子内に少なくとも1つの(メタ)アクリロイル基を有し、かつ9,9−ビスアリールフルオレン骨格を有するフルオレン含有硬化性モノマーと、分子内に3以上の(メタ)アクリロイル基を有する多官能硬化性モノマーと、分子内に1つの(メタ)アクリロイル基を有する単官能希釈モノマーとを含む。
フルオレン含有硬化性モノマーは、9,9−ビスアリールフルオレン骨格を有し、かつ少なくとも1つの(メタ)アクリロイル基を有していればよいが、重合性(硬化性)の点から、2以上の(メタ)アクリロイル基を有する硬化性モノマーが好ましい。このような化合物は、下記式(1)で表すことができる。
多官能硬化性モノマーは、ハードコート性樹脂組成物の硬度を向上させるために配合され、分子内に3以上の(メタ)アクリロイル基を有している。
単官能希釈モノマーは、ハードコート性樹脂組成物のハンドリング性を向上させるとともに、硬化物の硬度を調整するために配合され、分子内に1つの(メタ)アクリロイル基を有している。単官能希釈モノマーは、(メタ)アクリロイル基とエステル結合する骨格の種類によって、脂肪族モノマー、脂肪族炭化水素環を含有するモノマー、芳香環を含有するモノマーなどに分類できる。
本発明のハードコート性樹脂組成物は重合開始剤を含んでいてもよく、このような重合開始剤は熱重合開始剤(熱ラジカル発生剤)であってもよく光重合開始剤(光ラジカル発生剤)であってもよい。好ましい重合開始剤は光重合開始剤である。
本発明のハードコート性樹脂組成物は、さらに慣用の添加剤、例えば、樹脂成分、溶媒、熱重合禁止剤(ヒドロキノン、ヒドロキノンモノエチルエーテルなど)、消泡剤、塗布性改良剤、増粘剤、滑剤、安定剤(抗酸化剤、熱安定剤、耐光安定剤など)、可塑剤、界面活性剤、溶解促進剤、着色剤、充填剤、帯電防止剤、シランカップリング剤、レベリング剤、分散剤、分散助剤などを含んでいてもよい。添加剤は単独で又は2種以上組み合わせてもよい。
本発明のハードコート性樹脂組成物は、硬化性(特に光硬化性)に優れ、高屈折性を有している。例えば、ハードコート性樹脂組成物(又は樹脂組成物の固形分)の屈折率は、25℃、589nmにおいて、例えば、1.5以上の範囲から選択でき、好ましくは1.50〜1.70、さらに好ましくは1.51〜1.60、さらに好ましくは1.51〜1.55程度である。
本発明のハードコート性樹脂組成物は、活性エネルギーを付与することにより容易に硬化する。そのため、本発明のハードコート性樹脂組成物は、活性エネルギーとして、熱エネルギー及び/又は光エネルギー(特に、光エネルギー)を利用して硬化物を形成するのに有用である。本発明のハードコート性樹脂組成物は、光硬化性に優れている場合が多く、少なくとも光エネルギーを付与することにより硬化させることができる。硬化物は三次元構造を有していてもよく、通常、硬化膜である場合が多い。また、硬化膜は膜パターン(特に薄膜パターン)であってもよい。硬化膜は、樹脂組成物を基材又は基板に塗布し、必要により乾燥した後、加熱又は活性光線を露光することにより形成でき、膜パターンは、基材又は基板に形成した塗膜を活性光線で選択的に露光し、生成した潜像パターンを現像することにより形成できる。
多波長アッベ屈折計(アタゴ製、DR−M2<循環式恒温水槽60−C3使用>)を用い、温度25℃を保持し、589nmでの屈折率を測定した。
厚み100μmのポリエチレンテレフタレートフィルム(東洋紡(株)製「A4300」)上に作製した硬化膜を鉛筆硬度計(新東科学(株)製「HEIDON−14」)に設置し、各種鉛筆を750gの加重をかけつつ、45度の角度で押しつけ、1mm/秒の速度で硬化膜上を移動させ、硬化膜に生じた傷の有無を目視にて確認することにより、鉛筆硬度を測定した。
無溶剤下でのハンドリング性として、25℃におけるハードコート性樹脂組成物の粘度を以下の基準で評価した。なお、粘度は、TV−22形粘度計(コーンプレートタイプ、東機産業(株)製「TVE−22L」)を用い、測定粘度に応じたオプションロータ(01:1゜34×R24、07:3゜×R7.7)にて、1.0〜20rpm(粘度によって選択)で測定した。
×:5000mPa・s以上。
ハードコート性樹脂組成物の着色性について、目視で観察し、以下の基準で評価した。
×:着色あり。
ハードコート性樹脂組成物の保存安定性について、組成物を配合した後、常温で1週間静置し、組成物の状態を目視で観察し、以下の基準で評価した。
×:沈殿又はゲル化している。
(フルオレン含有アクリレート)
フルオレン含有アクリレート(EA−0200):大阪ガスケミカル(株)製「オグソールEA−0200」、エチレンオキシド平均付加モル数約2モル)
フルオレン含有アクリレート(EA−1000):大阪ガスケミカル(株)製「オグソールEA−1000」)。
フェノキシエチルアクリレート(PO−A):共栄社化学(株)製「ライトアクリレート PO−A」
ベンジルアクリレート(BZA):日立化成工業(株)製「FA−BZA」)
イソボルニルアクリレート(IBOA):(株)日本触媒社製「IBOA」
イソアミルアクリレート(IAA):日油(株)製。
ジペンタエリスリトールヘキサアクリレート(DPHA−2C):日本化薬(株)製「KAYARAD DPHA−2C」、6官能
ジペンタエリスリトールヘキサアクリレート(DPHA):ダイセルサイテック(株)製「DPHA」、6官能、平均官能基数5.5、平均分子量524〜547
ペンタエリスリトールテトラアクリレート(PETA):ダイセルサイテック(株)製「PETA」、4官能。
ビス[(2−メタクリロイルチオ)エチル]スルフィド(S2EG):住友精化(株)製「S2EG」。
ポリエチレングリコールジアクリレート(TEGDA):東亜合成(株)製「M−240」、2官能
ビスフェノールAジアクリレート(BisA−DA):日立化成工業(株)製「FA−324A」、2官能。
メチルエチルケトン(MEK)
(光重合開始剤)
光重合開始剤(イルガキュア184):チバ・ジャパン(株)製「IRGACURE 184」。
表1に示す成分を表1に示す割合(重量部)で振騰機において十分に混合し、ハードコート性樹脂組成物を調製した。ポリエチレンテレフタレートフィルム(膜厚100μm)の片面に、前記ハードコート性樹脂組成物を塗布し、カーボンアークの紫外線照射機で積算光量500mJ/cm2の紫外線を照射し、塗膜の膜厚(ハ−ドコ−ト層の厚さ)が約100μmの積層フィルムを得た。なお、比較例6の樹脂組成物は、配合してから2日後にゲル化した。得られた結果を表1に示す。
Claims (13)
- 分子内に少なくとも1つの(メタ)アクリロイル基を有し、かつ9,9−ビスアリールフルオレン骨格を有するフルオレン含有硬化性モノマーと、分子内に3以上の(メタ)アクリロイル基を有する多官能硬化性モノマーと、分子内に1つの(メタ)アクリロイル基を有する単官能希釈モノマーとを含むハードコート性樹脂組成物であって、硬化物の屈折率が1.55以上であり、かつ鉛筆硬度が3H以上であるハードコート性樹脂組成物。
- 単官能希釈モノマーが、直鎖又は分岐鎖状C3−7アルキル(メタ)アクリレートである請求項1記載のハードコート性樹脂組成物。
- 単官能希釈モノマーが、分岐鎖状C4−6アルキル(メタ)アクリレートである請求項2記載のハードコート性樹脂組成物。
- 単官能希釈モノマーが、屈折率1.50以上であり、かつ芳香環を有する(メタ)アクリレートである請求項1記載のハードコート性樹脂組成物。
- 単官能希釈モノマーが、橋架け環式(メタ)アクリレートである請求項1記載のハードコート性樹脂組成物。
- 単官能希釈モノマーが、25℃の粘度が20mPa・s以下である請求項1〜5のいずれかに記載のハードコート性樹脂組成物。
- フルオレン含有硬化性モノマーが、下記式(1)で表される化合物である請求項1〜6のいずれかに記載のハードコート性樹脂組成物。
- 式(1)において、nが2〜10の整数である請求項7記載のハードコート性樹脂組成物。
- フルオレン含有硬化性モノマー及び多官能硬化性モノマーの合計量と、単官能希釈モノマーとの割合(重量比)が、前者/後者=99/1〜50/50である請求項1〜8のいずれかに記載のハードコート性樹脂組成物。
- 請求項1〜9のいずれかに記載のハードコート性樹脂組成物に活性エネルギーを付与して硬化させる硬化物の製造方法。
- 光透過基材の上にハードコート性樹脂組成物を塗布した後、活性光線を照射して硬化させる請求項10記載の硬化物の製造方法。
- 請求項10又は11記載の製造方法により得られた硬化物。
- 鉛筆硬度が3H以上である請求項12記載の硬化物。
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