JP5662005B2 - 硬化性樹脂組成物及び当該組成物を用いて作製された多層構造体 - Google Patents
硬化性樹脂組成物及び当該組成物を用いて作製された多層構造体 Download PDFInfo
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- JP5662005B2 JP5662005B2 JP2009036622A JP2009036622A JP5662005B2 JP 5662005 B2 JP5662005 B2 JP 5662005B2 JP 2009036622 A JP2009036622 A JP 2009036622A JP 2009036622 A JP2009036622 A JP 2009036622A JP 5662005 B2 JP5662005 B2 JP 5662005B2
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- meth
- acrylate
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- curable resin
- hard coat
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- 239000011342 resin composition Substances 0.000 title claims description 68
- 239000000203 mixture Substances 0.000 title description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 79
- 239000011347 resin Substances 0.000 claims description 56
- 229920005989 resin Polymers 0.000 claims description 56
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 41
- 239000005056 polyisocyanate Substances 0.000 claims description 38
- 229920001228 polyisocyanate Polymers 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 239000000758 substrate Substances 0.000 claims description 30
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 25
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 22
- 239000004925 Acrylic resin Substances 0.000 claims description 20
- 229920000178 Acrylic resin Polymers 0.000 claims description 20
- 230000005855 radiation Effects 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 14
- 239000004417 polycarbonate Substances 0.000 claims description 11
- 229920000515 polycarbonate Polymers 0.000 claims description 11
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 230000001678 irradiating effect Effects 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 132
- -1 isocyanate compound Chemical class 0.000 description 45
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- 150000001875 compounds Chemical class 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 15
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- 125000002723 alicyclic group Chemical group 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 13
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- 125000003118 aryl group Chemical group 0.000 description 12
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- 125000001424 substituent group Chemical group 0.000 description 12
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- 238000011156 evaluation Methods 0.000 description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 239000011521 glass Substances 0.000 description 6
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
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- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
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- 235000020354 squash Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920006353 Acrylite® Polymers 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 4
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 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
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class 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 3
- 239000002390 adhesive tape Substances 0.000 description 3
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- 238000007865 diluting Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
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- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 3
- 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 2
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 2
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 2
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-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
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 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
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 2
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- 150000004056 anthraquinones Chemical class 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 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
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- ZZXXBDPXXIDUBP-UHFFFAOYSA-N hydroxymethyl prop-2-enoate Chemical compound C(C=C)(=O)OCO.C(C=C)(=O)OCO ZZXXBDPXXIDUBP-UHFFFAOYSA-N 0.000 description 2
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- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 2
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- YYJIYUNJTKCRHL-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC(=O)C=C YYJIYUNJTKCRHL-UHFFFAOYSA-N 0.000 description 1
- LBDSQNRQXIKAGX-UHFFFAOYSA-N (2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical class C=CC(=O)OCC(C)COC(=O)C=C LBDSQNRQXIKAGX-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 239000004566 building material Substances 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
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 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 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- TZAMQIAPGYOUKF-UHFFFAOYSA-N diethoxyphosphoryl(phenyl)methanone Chemical compound CCOP(=O)(OCC)C(=O)C1=CC=CC=C1 TZAMQIAPGYOUKF-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000009826 distribution Methods 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000005329 float glass Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- LULWTBQRAIOSQN-UHFFFAOYSA-N hydroxymethyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCO.C(C(=C)C)(=O)OCO LULWTBQRAIOSQN-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 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
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000847 nonoxynol Polymers 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
- 239000012766 organic filler Substances 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Images
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Laminated Bodies (AREA)
Description
アロニックス(登録商標)M−313(東亞合成株式会社):ビス(アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレート及びトリス(アクリロイルオキシエチル)イソシアヌレートの混合物。このうち、ビス(アクリロイルオキシエチル)ヒドロキシエチルイソシアヌレートの含有率は、30〜40質量%(カタログ値による)である。
KAYARAD R−684(日本化薬株式会社):トリシクロデカンジメチロールジアクリレート
TMPTA:トリメチロールプロパントリアクリレート(ライトアクリレート(登録商標)TMP−A(共栄社化学株式会社))
D−TMPTA:ジトリメチロールプロパンテトラアクリレート(NKエステル AD−TMP(新中村化学工業株式会社))
DPHA:ジペンタエリスリトールヘキサアクリレート(NKエステル A−DPH(新中村化学工業株式会社))
デュラネート(商品名)22A−100(旭化成ケミカルズ株式会社):ヘキサメチレンジイソシアネート由来ポリイソシアネート、ビウレット体、イソシアネート含有率 22.0質量%
デュラネート(商品名)24A−100(旭化成ケミカルズ株式会社):ヘキサメチレンジイソシアネート由来ポリイソシアネート、ビウレット体、イソシアネート含有率 23.5質量%
デュラネート(商品名)TPA−100(旭化成ケミカルズ株式会社):ヘキサメチレンジイソシアネート由来ポリイソシアネート、イソシアヌレート体、イソシアネート含有率 23.1質量%
デュラネート(商品名)TSE−100(旭化成ケミカルズ株式会社):ヘキサメチレンジイソシアネート由来ポリイソシアネート、イソシアヌレート体、イソシアネート含有率 12.0質量%
デュラネート(商品名)D201(旭化成ケミカルズ株式会社):2官能型プレポリマーのイソシアネート、イソシアネート含有率 15.8質量%
IRGACURE 907(チバ・ジャパン株式会社):光重合開始剤
HEA:2−ヒドロキシエチルアクリレート(大阪有機化学工業株式会社)
IBXA:イソボルニルアクリレート(共栄社化学株式会社)
紫光(登録商標)UV−7600B(日本合成化学工業株式会社):ウレタンアクリレート
EBECRYL 4858(ダイセル・サイテック株式会社):ウレタンアクリレート
溶液の粘度は、ブルックフィールド型回転粘度計を用いて室温で測定した。測定条件は下記の通りである。
種類:B形(形式BM、東機産業株式会社)
ローター番号:No.2
回転数:30rpm
ハードコート層を有する基材の表面に硬化性樹脂組成物を用いて形成した樹脂層(硬化被膜)の密着性は、JIS K5600−5−6(1999年)に概ね基づき、以下のように評価した。樹脂層がハードコート層の表面に形成された基材に、カッターナイフで1mm間隔の25個の碁盤目を作り、住友スリーエム製粘着テープ(メンディングテープ810)を室温にて圧着した。その後、テープを基材から約60度の角度で素早く引き剥がして、碁盤目の状態を観察した。評価は下記の通りとした。
A(密着性非常に良好):樹脂層が残った碁盤目の数が25(剥離全くなし)。
B(密着性良好):樹脂層が残った碁盤目の数が23〜24。
NG(密着性不良):剥離した碁盤目の数が3以上。
<硬化性樹脂組成物の調製>
表2に従い、分子中に1個以上の水酸基を有するアクリレートを含む原料(A1、A2)(A2は希釈性モノマーとしても機能する)、分子中に2個以上のアクリロイル基を有する多官能アクリレート(B1、B2)、任意成分の希釈性モノマー(C)、分子中に3個以上のイソシアネート基を有するポリイソシアネート(D)、及び光重合開始剤(E)をよく混合して、硬化性樹脂組成物を調製した。以下、組成に関する表中の数値は、特別断らない限り、全て質量部で表す。
ハードコート層を有する基材として、アクリライト(登録商標)MR−200(三菱レイヨン株式会社製)アクリル樹脂シート(40mm×60mm、厚さ0.8mm)を使用した。このシートの短辺に、粘着テープ「透明美色」(登録商標)(住友スリーエム株式会社製)を幅約2mmにして貼り付けてスペーサーとした。このときの粘着テープの厚みは約50マイクロメートルである。このシートに、表2に記載の硬化性樹脂組成物を塗布し、この上からフロートガラスを押し付け(55mm×100mm、厚さ2.0mm)、塗液を充分に濡れ広がせた後、フュージョンUVシステムズ・ジャパン株式会社製の紫外線照射装置F−300(D−バルブ、120W/cm)を用いて紫外線照射を行った。硬化条件は60m/分×20パスとした。照射時に、EIT社製光量計UV POWER PUCK(登録商標)IIで測定した1パスあたりのUVAの光量は、86mJ/cm2であった。その後、ガラスを剥がすことにより、平滑な表面を有する紫外線硬化被膜(樹脂層)がハードコート層の上に形成されたアクリル樹脂シートを得た。
ハードコート層を有する基材として、アクリライト(登録商標)MR−200に代えて表3に示したアクリル樹脂シート又はポリカーボネート複合板を使用した以外は、例1及び比較例1と同様の硬化性樹脂組成物を使用して、それぞれ例12〜15及び比較例12〜15を行った。表3に例1及び比較例1と併せて評価結果を示す。
熱処理によって、ハードコート層を有するアクリル樹脂シート上で硬化性樹脂組成物に含まれる水酸基とイソシアネート基からウレタン結合を形成する代わりに、既にウレタン結合を有するモノマー、すなわちウレタンアクリレート(F)を使用した以外は例1と同様に比較例16〜17を行った。表4に評価結果を示す。
ポリイソシアネート化合物であるデュラネート(商品名)24A−100(旭化成ケミカル株式会社製)をトルエンとメチルエチルケトン(MEK)の混合溶媒(トルエン/MEK=50質量%/50質量%)で3質量%になるように調製した。この塗布液を、アクリライト(登録商標)MR−200上に、日本シーダースサービス社製バーコーター(ROD No.4)でコーティングした後、溶剤を乾燥させた。
20 基材
30 ハードコート層
40 樹脂層
50 印刷層
60 接着層
70 画像表示装置又は光学部材
本発明の実施態様の一部を以下の項目1−9に列記する。
[1]
少なくとも1つの表面にアクリル系ハードコート層を有する基材と、
前記アクリル系ハードコート層上に形成された樹脂層と
を含む多層構造体であって、
前記樹脂層が、
(i)分子中に1個以上の水酸基を有する(メタ)アクリレート、
(ii)分子中に2個以上の(メタ)アクリロイル基を有する(メタ)アクリレート、
(iii)分子中に3個以上のイソシアネート基を有するポリイソシアネート、及び
(iv)光重合開始剤
を含む硬化性樹脂組成物の重合生成物を含む、多層構造体。
[2]
前記基材が(メタ)アクリル樹脂層及び/又はポリカーボネート層を含む、項目1に記載の多層構造体。
[3]
前記ポリイソシアネート(iii)がビウレット体のポリイソシアネートである、項目1又は2のいずれかに記載の多層構造体。
[4]
前記分子中に1個以上の水酸基を有する(メタ)アクリレート(i)と前記分子中に2個以上の(メタ)アクリロイル基を有する(メタ)アクリレート(ii)が同一の分子である、項目1〜3のいずれか1つに記載の多層構造体。
[5]
前記アクリル系ハードコート層上への前記硬化性樹脂組成物の重合生成物を含む樹脂層の形成が、前記硬化性樹脂組成物の前記アクリル系ハードコート層上での放射線照射及び熱処理によって行われる、項目1〜4のいずれか1つに記載の多層構造体。
[6]
少なくとも1つの表面にアクリル系ハードコート層を有する基材を用意する工程と、
(i)分子中に1個以上の水酸基を有する(メタ)アクリレート、
(ii)分子中に2個以上の(メタ)アクリロイル基を有する多官能(メタ)アクリレート、
(iii)分子中に3個以上のイソシアネート基を有するポリイソシアネート、及び
(iv)光重合開始剤
を含む硬化性樹脂組成物を用意する工程と、
前記硬化性樹脂組成物を前記アクリル系ハードコート層上に適用する工程と、
前記硬化性樹脂組成物に放射線を照射する工程と、
前記硬化性樹脂組成物を熱処理する工程と
を含む、多層構造体の製造方法。
[7]
(i)分子中に1個以上の水酸基を有する(メタ)アクリレート、
(ii)分子中に2個以上の(メタ)アクリロイル基を有する多官能(メタ)アクリレート、
(iii)分子中に3個以上のイソシアネート基を有するポリイソシアネート、及び
(iv)光重合開始剤
を含む硬化性樹脂組成物。
[8]
前記ポリイソシアネート(iii)がビウレット体のポリイソシアネートである、項目7に記載の硬化性樹脂組成物。
[9]
前記分子中に1個以上の水酸基を有する(メタ)アクリレート(i)と前記分子中に2個以上の(メタ)アクリロイル基を有する(メタ)アクリレート(ii)が同一分子である、項目7又は8のいずれかに記載の硬化性樹脂組成物。
Claims (6)
- 少なくとも1つの表面にアクリル系ハードコート層を有する基材と、
前記アクリル系ハードコート層上に形成された樹脂層と
を含む多層構造体であって、
前記樹脂層が、
(i)分子中に1個以上の水酸基を有する(メタ)アクリレート、
(ii)分子中に2個以上の(メタ)アクリロイル基を有する(メタ)アクリレート、
(iii)分子中に3個以上のイソシアネート基を有するポリイソシアネート、及び
(iv)光重合開始剤
を含む硬化性樹脂組成物の重合生成物を含む、多層構造体。 - 前記基材が(メタ)アクリル樹脂層及び/又はポリカーボネート層を含む、請求項1に記載の多層構造体。
- 前記ポリイソシアネート(iii)がビウレット体のポリイソシアネートである、請求項1又は2のいずれかに記載の多層構造体。
- 前記分子中に1個以上の水酸基を有する(メタ)アクリレート(i)と前記分子中に2個以上の(メタ)アクリロイル基を有する(メタ)アクリレート(ii)が同一の分子である、請求項1〜3のいずれか1つに記載の多層構造体。
- 前記アクリル系ハードコート層上への前記硬化性樹脂組成物の重合生成物を含む樹脂層の形成が、前記硬化性樹脂組成物の前記アクリル系ハードコート層上での放射線照射及び熱処理によって行われる、請求項1〜4のいずれか1つに記載の多層構造体。
- 少なくとも1つの表面にアクリル系ハードコート層を有する基材を用意する工程と、
(i)分子中に1個以上の水酸基を有する(メタ)アクリレート、
(ii)分子中に2個以上の(メタ)アクリロイル基を有する多官能(メタ)アクリレート、
(iii)分子中に3個以上のイソシアネート基を有するポリイソシアネート、及び
(iv)光重合開始剤
を含む硬化性樹脂組成物を用意する工程と、
前記硬化性樹脂組成物を前記アクリル系ハードコート層上に適用する工程と、
前記硬化性樹脂組成物に放射線を照射する工程と、
前記硬化性樹脂組成物を熱処理する工程と
を含む、多層構造体の製造方法。
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