JP2017128688A - Active energy ray-curable resin composition, cured product thereof, and lens sheet - Google Patents
Active energy ray-curable resin composition, cured product thereof, and lens sheet Download PDFInfo
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- JP2017128688A JP2017128688A JP2016010425A JP2016010425A JP2017128688A JP 2017128688 A JP2017128688 A JP 2017128688A JP 2016010425 A JP2016010425 A JP 2016010425A JP 2016010425 A JP2016010425 A JP 2016010425A JP 2017128688 A JP2017128688 A JP 2017128688A
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- Prior art keywords
- meth
- acrylate
- resin composition
- energy ray
- active energy
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 49
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 95
- -1 phenoxybenzyl Chemical group 0.000 claims abstract description 53
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 20
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 20
- 239000002105 nanoparticle Substances 0.000 claims abstract description 18
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 15
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims description 20
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 5
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 5
- 230000009477 glass transition Effects 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003827 glycol group Chemical group 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000011347 resin Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 9
- 229910052753 mercury Inorganic materials 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000010419 fine particle Substances 0.000 description 7
- 230000001678 irradiating effect Effects 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229920002799 BoPET Polymers 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 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
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000011162 core material Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 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 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- VQCBHWLJZDBHOS-UHFFFAOYSA-N erbium(iii) oxide Chemical compound O=[Er]O[Er]=O VQCBHWLJZDBHOS-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- PLDDOISOJJCEMH-UHFFFAOYSA-N neodymium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Nd+3].[Nd+3] PLDDOISOJJCEMH-UHFFFAOYSA-N 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- LCDOENXNMQXGFS-UHFFFAOYSA-N phenoxybenzene;prop-2-enoic acid Chemical class OC(=O)C=C.C=1C=CC=CC=1OC1=CC=CC=C1 LCDOENXNMQXGFS-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- ZIKATJAYWZUJPY-UHFFFAOYSA-N thulium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Tm+3].[Tm+3] ZIKATJAYWZUJPY-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- 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 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- BXSPZNVFEYWSLZ-UHFFFAOYSA-N (3-phenoxyphenyl)methyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 BXSPZNVFEYWSLZ-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- LHNVRSJRNUEEAB-UHFFFAOYSA-N 1-(4-nonylphenoxy)ethane-1,2-diol Chemical compound CCCCCCCCCC1=CC=C(OC(O)CO)C=C1 LHNVRSJRNUEEAB-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 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 1
- CZZVAVMGKRNEAT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;3-hydroxy-2,2-dimethylpropanoic acid Chemical class OCC(C)(C)CO.OCC(C)(C)C(O)=O CZZVAVMGKRNEAT-UHFFFAOYSA-N 0.000 description 1
- FUQAGKYWAUZSEJ-UHFFFAOYSA-N 2,3,4,5-tetrabromo-6-(2-hydroxyphenyl)phenol Chemical compound OC1=CC=CC=C1C1=C(O)C(Br)=C(Br)C(Br)=C1Br FUQAGKYWAUZSEJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- ROHFBIREHKPELA-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid;methane Chemical compound C.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O ROHFBIREHKPELA-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- QPXVRLXJHPTCPW-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-propan-2-ylphenyl)propan-1-one Chemical compound CC(C)C1=CC=C(C(=O)C(C)(C)O)C=C1 QPXVRLXJHPTCPW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229920006353 Acrylite® Polymers 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- RYIRPECLIDWKIZ-UHFFFAOYSA-N C(C=C)(=O)O.C(C=C)(=O)OCCOC1=CC=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC=C(C=C1)OCCOC(C=C)=O Chemical compound C(C=C)(=O)O.C(C=C)(=O)OCCOC1=CC=C(C=C1)C1(C2=CC=CC=C2C=2C=CC=CC12)C1=CC=C(C=C1)OCCOC(C=C)=O RYIRPECLIDWKIZ-UHFFFAOYSA-N 0.000 description 1
- RHNOJJHDWQNEAE-UHFFFAOYSA-N CC(=O)CC.[O-2].[O-2].[Zr+4] Chemical compound CC(=O)CC.[O-2].[O-2].[Zr+4] RHNOJJHDWQNEAE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 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
- RSKGXPOKZWCJRD-UHFFFAOYSA-N benzyl prop-2-eneperoxoate Chemical compound C=CC(=O)OOCC1=CC=CC=C1 RSKGXPOKZWCJRD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- ZNAAXKXXDQLJIX-UHFFFAOYSA-N bis(2-cyclohexyl-3-hydroxyphenyl)methanone Chemical compound C1CCCCC1C=1C(O)=CC=CC=1C(=O)C1=CC=CC(O)=C1C1CCCCC1 ZNAAXKXXDQLJIX-UHFFFAOYSA-N 0.000 description 1
- 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
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- 229910052799 carbon Inorganic materials 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- FKTOIHSPIPYAPE-UHFFFAOYSA-N samarium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Sm+3].[Sm+3] FKTOIHSPIPYAPE-UHFFFAOYSA-N 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
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- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C—CHEMISTRY; METALLURGY
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- 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
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
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- 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
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- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2244—Oxides; Hydroxides of metals of zirconium
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本発明は、活性エネルギー線硬化型樹脂組成物、その硬化物及びレンズシートに関する。 The present invention relates to an active energy ray-curable resin composition, a cured product thereof, and a lens sheet.
プラスチックは、加工性、透明性などに加えて種々の特性を備えており、軽量で安価であるなど多くの利点を有していることから、従来から、光学材料として用いられている。
例えば、液晶ディスプレイにおいて積層して使用されるレンズシートは、画像の高精細化及び最終製品の薄型化等に伴い、屈折率の高い材料が望まれている。このために、高屈折率の樹脂を使用し、有機又は無機の高屈折率微粒子を添加する方法が提案されている（特許文献１、２）。
その一方、屈折率の高い材料は高粘度化の問題があり、高屈折率微粒子は凝集又は沈降等の問題があるとともに、樹脂硬化物の柔軟性を低下させ、傷が付きやすくなることがある。
従って、その光学用途に応じた高屈折率、他の部材を損傷しない柔軟性、種々の加工に対応し得る取り扱い性等の特性バランスが図られた樹脂組成物が強く求められている。
Plastics are conventionally used as optical materials because they have various characteristics in addition to processability and transparency, and have many advantages such as light weight and low cost.
For example, a lens sheet used by being laminated in a liquid crystal display is desired to have a material having a high refractive index as the image becomes more precise and the final product is thinner. For this reason, a method of using a high refractive index resin and adding organic or inorganic high refractive index fine particles has been proposed (Patent Documents 1 and 2).
On the other hand, a material with a high refractive index has a problem of increasing viscosity, and a fine particle of high refractive index has a problem such as aggregation or sedimentation, and also reduces the flexibility of the cured resin and may be easily damaged. .
Accordingly, there is a strong demand for a resin composition that has a good balance of properties such as a high refractive index according to the optical application, flexibility that does not damage other members, and handling that can handle various processing.
本発明は、上記課題を解決するためになされたものであって、光学用途に用いられる光学シート等に必要とされる種々の特性のバランスが図られた活性エネルギー線硬化型樹脂組成物及び硬化物を提供することを目的とする。 The present invention has been made in order to solve the above-described problems, and is an active energy ray-curable resin composition and a cured product that balances various properties required for optical sheets and the like used for optical applications. The purpose is to provide goods.
本願における活性エネルギー線硬化型樹脂組成物は、
金属酸化物ナノ粒子（Ａ）、
フェノキシベンジル（メタ）アクリレート類（Ｂ）及び
（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレート（Ｃ）を含有することを特徴とする。
このような活性エネルギー線硬化型樹脂組成物では、さらに、以下の１以上を備えることが好ましい。
前記金属酸化物ナノ粒子（Ａ）が２０重量％以上７０重量％以下であり、
前記フェノキシベンジル（メタ）アクリレート類（Ｂ）が５重量％以上６０重量％以下であり、
前記（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレート（Ｃ）が１重量％以上３０重量％以下である、
前記金属酸化物ナノ粒子（Ａ）が酸化ジルコニウムを主成分とするナノ粒子である、
前記ポリアルキレングリコール構造を有する二官能（メタ）アクリレート（Ｃ）がポリエチレングリコールジ（メタ）アクリレート又はエトキシ変性ビスフェノールＡジ（メタ）アクリレートである、
硬化後の屈折率が１．６０以上である、
前記活性エネルギー線硬化型樹脂組成物の２５℃における粘度が２０００ｍＰａ・ｓ以下である、
前記活性エネルギー線硬化型樹脂組成物の硬化物のガラス転移温度（Ｔｇ）が２０℃以下である。
また、本願は、上記活性エネルギー線硬化型樹脂組成物の硬化物及びこの硬化物からなるレンズシートである。
The active energy ray-curable resin composition in the present application is
Metal oxide nanoparticles (A),
It contains phenoxybenzyl (meth) acrylates (B) and a bifunctional (meth) acrylate (C) having a (poly) alkylene glycol structure.
Such an active energy ray-curable resin composition preferably further includes one or more of the following.
The metal oxide nanoparticles (A) are 20 wt% or more and 70 wt% or less,
The phenoxybenzyl (meth) acrylates (B) are 5 wt% or more and 60 wt% or less,
The bifunctional (meth) acrylate (C) having the (poly) alkylene glycol structure is 1% by weight to 30% by weight,
The metal oxide nanoparticles (A) are nanoparticles mainly composed of zirconium oxide.
The bifunctional (meth) acrylate (C) having the polyalkylene glycol structure is polyethylene glycol di (meth) acrylate or ethoxy-modified bisphenol A di (meth) acrylate,
The refractive index after curing is 1.60 or more,
The active energy ray-curable resin composition has a viscosity at 25 ° C. of 2000 mPa · s or less,
The glass transition temperature (Tg) of the cured product of the active energy ray-curable resin composition is 20 ° C. or less.
Moreover, this application is the hardened | cured material of the said active energy ray hardening-type resin composition, and the lens sheet which consists of this hardened | cured material.
本発明の活性エネルギー線硬化型樹脂組成物によれば、光学用途に用いられる光学シート等に必要とされる種々の特性のバランスを図ることができ、光学部材として高性能な硬化物を提供することができる。 According to the active energy ray-curable resin composition of the present invention, it is possible to balance various properties required for an optical sheet or the like used for optical applications, and provide a high-performance cured product as an optical member. be able to.
本願の活性エネルギー線硬化型樹脂組成物は、主として、
金属酸化物ナノ粒子（Ａ）、
フェノキシベンジル（メタ）アクリレート類（Ｂ）及び
（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレート（Ｃ）を含有する。
なお、本明細書においては、（メタ）アクリレートとは、アクリレート及びメタクリレートの双方を意味する。また、以下に例示する成分はいずれも、単独で又は２種以上を組み合わせて用いてもよい。
The active energy ray-curable resin composition of the present application is mainly composed of
Metal oxide nanoparticles (A),
It contains phenoxybenzyl (meth) acrylates (B) and a bifunctional (meth) acrylate (C) having a (poly) alkylene glycol structure.
In the present specification, (meth) acrylate means both acrylate and methacrylate. In addition, any of the components exemplified below may be used alone or in combination of two or more.
（Ａ）金属酸化物ナノ粒子
金属酸化物微粒子としては、例えば、粒子径が５ｎｍ〜５０ｎｍのものを使用することが適しており、なかでも、５ｎｍ〜２０ｎｍが好ましく、１０ｎｍ〜２０ｎｍがより好ましい。これにより、樹脂組成物の屈折率を調整することが可能となる。金属酸化物粒子の粒子径は、各種電子顕微鏡観察によって得られた画像を処理することにより得られる平均粒子径により評価することができる。例えば、金属酸化物粒子を透過型電子顕微鏡（ＴＥＭ）、電界放射型透過電子顕微鏡（ＦＥ−ＴＥＭ）、電界放射型走査電子顕微鏡（ＦＥ−ＳＥＭ）等で拡大観察し、無作為に１００個の粒子を選択してその長軸方向の長さを測定し、その算術平均を求めることで決定することができる。
(A) Metal oxide nanoparticles As the metal oxide fine particles, for example, those having a particle diameter of 5 nm to 50 nm are suitable, among which 5 nm to 20 nm are preferable, and 10 nm to 20 nm are more preferable. Thereby, it becomes possible to adjust the refractive index of the resin composition. The particle diameter of the metal oxide particles can be evaluated by an average particle diameter obtained by processing images obtained by various electron microscope observations. For example, the metal oxide particles are enlarged and observed with a transmission electron microscope (TEM), a field emission transmission electron microscope (FE-TEM), a field emission scanning electron microscope (FE-SEM), and the like. It can be determined by selecting a particle, measuring its length in the long axis direction, and calculating its arithmetic average.
金属酸化物粒子は、球状、粒状、楕円球状、立方体状、直方体状、ピラミッド状、針状、柱状、棒状、筒状、りん片状、板状、薄片状等のいずれの形状でもよい。
金属酸化物微粒子としては、酸化ケイ素、酸化ジルコニウム、酸化チタン、酸化亜鉛、五酸化アンチモン、酸化スズ、酸化アルミニウム、酸化インジウム、インジウムスズ酸化物、酸化第二鉄、酸化セリウム、酸化イットリウム、酸化マンガン、酸化ホロミウム、酸化銅、酸化ビスマス、酸化コバルト、四三酸化コバルト、四三酸化鉄、酸化マグネシウム、酸化ランタン、酸化プラセオジム、酸化ネオジム、酸化サマリウム、酸化ユウロビウム、酸化ガドリニウム、酸化テルビウム、酸化ジスプロシウム、酸化エルビウム、酸化ツリウム、酸化イッテルビウム、酸化ルテチウム、酸化スカンジウム、五酸化タンタル、五酸化ニオブ、酸化イリジウム、酸化ロジウム、酸化ルテニウム及びこれらを結合させた複合酸化物を主成分とするナノ粒子が挙げられる。なかでも、酸化ジルコニウム、酸化チタンを主成分とするナノ粒子が好ましく、酸化ジルコニウムを主成分とするナノ粒子がより好ましい。ここで主成分とは、金属酸化物微粒子において最大重量を占める成分を意味する。
The metal oxide particles may have any shape such as a spherical shape, a granular shape, an elliptical spherical shape, a cubic shape, a rectangular parallelepiped shape, a pyramid shape, a needle shape, a column shape, a rod shape, a cylindrical shape, a flake shape, a plate shape, and a flake shape.
As metal oxide fine particles, silicon oxide, zirconium oxide, titanium oxide, zinc oxide, antimony pentoxide, tin oxide, aluminum oxide, indium oxide, indium tin oxide, ferric oxide, cerium oxide, yttrium oxide, manganese oxide , Holmium oxide, copper oxide, bismuth oxide, cobalt oxide, cobalt tetroxide, iron tetroxide, magnesium oxide, lanthanum oxide, praseodymium oxide, neodymium oxide, samarium oxide, europium oxide, gadolinium oxide, terbium oxide, dysprosium oxide, Nanoparticles mainly composed of erbium oxide, thulium oxide, ytterbium oxide, lutetium oxide, scandium oxide, tantalum pentoxide, niobium pentoxide, iridium oxide, rhodium oxide, ruthenium oxide, and composite oxides combining these And the like. Among these, nanoparticles mainly composed of zirconium oxide and titanium oxide are preferable, and nanoparticles mainly composed of zirconium oxide are more preferable. Here, the main component means a component occupying the maximum weight in the metal oxide fine particles.
金属酸化物ナノ粒子は、表面処理されていてもよい。表面処理は、公知の方法で行うことができる。例えば、シランカップリング剤、重合性官能基を有するイソシアネート化合物、有機スルホニルオキシ基を有する化合物、カルボキシル基を有する化合物等で表面処理したものが挙げられる。なお、表面処理された金属酸化物ナノ粒子とは、金属酸化物微粒子の表面に存在する水酸基によって、上述した化合物におけるアルコキシ基、イソシアネート基、スルホニル基、カルボキシル基等が化学結合するか、水素原子又はカチオン性原子とともに塩を形成して、その表面に物理的に付着した状態の双方を意味する。 The metal oxide nanoparticles may be surface-treated. The surface treatment can be performed by a known method. Examples thereof include those that have been surface-treated with a silane coupling agent, an isocyanate compound having a polymerizable functional group, a compound having an organic sulfonyloxy group, a compound having a carboxyl group, or the like. In addition, the surface-treated metal oxide nanoparticle means that an alkoxy group, an isocyanate group, a sulfonyl group, a carboxyl group or the like in the above-described compound is chemically bonded by a hydroxyl group present on the surface of the metal oxide fine particle, or a hydrogen atom Alternatively, it means both a state in which a salt is formed with a cationic atom and is physically attached to the surface.
活性エネルギー線硬化型樹脂組成物において、（Ａ）成分の含有量は、得ようとする特性のバランスによって適宜調整することができる。例えば、（Ａ）〜（Ｃ）成分の総重量に対して２０重量％以上７０重量％以下が好ましく、３０重量％以上７０重量％以下がより好ましく、３０重量％以上６０重量％以下がさらに好ましい。 In the active energy ray-curable resin composition, the content of the component (A) can be appropriately adjusted depending on the balance of characteristics to be obtained. For example, it is preferably 20% by weight or more and 70% by weight or less, more preferably 30% by weight or more and 70% by weight or less, and further preferably 30% by weight or more and 60% by weight or less with respect to the total weight of the components (A) to (C). .
（Ｂ）フェノキシベンジル（メタ）アクリレート類
フェノキシベンジル（メタ）アクリレート類は、式（１）で表される構造を有する化合物である。
（式中、Ｒは水素原子又はメチル基を表し、ａは０〜４の整数を表す。）
式（１）で表される化合物としては、具体的には、
等が挙げられる。なかでも、ｏ位又はｍ位置換体であるフェノキシベンジル（メタ）アクリレート化合物、特に、式（Ｂ−１）の化合物が好ましく、ｍ位置換体であるフェノキシベンジル（メタ）アクリレート化合物がより好ましい。
これらの化合物は、粘度が低く、屈折率が比較的高い。また、これらの化合物を用いる場合には、活性エネルギー線硬化型樹脂組成物の硬化物自体に外力が付加されて形状が変化したとしても、自己形状を復元し得る優れた復元性を付与することができる。
(B) Phenoxybenzyl (meth) acrylates Phenoxybenzyl (meth) acrylates are compounds having a structure represented by formula (1).
(In the formula, R represents a hydrogen atom or a methyl group, and a represents an integer of 0 to 4.)
As the compound represented by the formula (1), specifically,
Etc. Especially, the phenoxy benzyl (meth) acrylate compound which is o-position or m-position substitution body, especially the compound of Formula (B-1) is preferable, and the phenoxy benzyl (meth) acrylate compound which is m-position substitution body is more preferable.
These compounds have a low viscosity and a relatively high refractive index. In addition, when these compounds are used, even if an external force is applied to the cured product of the active energy ray-curable resin composition itself to change the shape, it imparts excellent resilience capable of restoring the self-shape. Can do.
活性エネルギー線硬化型樹脂組成物において、（Ｂ）成分の含有量は、得ようとする特性のバランスによって適宜調整することができるが、（Ａ）〜（Ｃ）成分の総重量に対して５重量％以上６０重量％以下が好ましく、１０重量％以上６０重量％以下がより好ましく、１０重量％以上５５重量％以下がさらに好ましい。 In the active energy ray-curable resin composition, the content of the component (B) can be appropriately adjusted depending on the balance of the properties to be obtained, but is 5 with respect to the total weight of the components (A) to (C). The weight is preferably from 60% by weight to 60% by weight, more preferably from 10% by weight to 60% by weight, and even more preferably from 10% by weight to 55% by weight.
（Ｃ）（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレート
（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレートとしては、炭素数１〜１０のアルキレングリコール構造を有する化合物が挙げられ、好ましくは、炭素数２〜４のアルキレングリコール構造を有する化合物が挙げられる。この化合物におけるアルキレングリコールの数は、２〜２０が挙げられ、５〜１５が好ましい。アルキレングリコール構造は、同一分子において、単独又は２種以上を組み合わせた構造のいずれでもよい。
(C) Bifunctional (meth) acrylate having a (poly) alkylene glycol structure As the bifunctional (meth) acrylate having a (poly) alkylene glycol structure, a compound having an alkylene glycol structure having 1 to 10 carbon atoms may be mentioned, Preferably, the compound which has a C2-C4 alkylene glycol structure is mentioned. As for the number of alkylene glycol in this compound, 2-20 are mentioned, and 5-15 are preferable. The alkylene glycol structure may be either a single molecule or a combination of two or more types in the same molecule.
また、（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレートは、（ポリ）アルキレングリコール構造及び２つの（メタ）アクリレートに加えて、エーテル結合を介した、炭素数１〜６のアルカンジイル基、２価の炭素数３〜１０の環状炭化水素基（芳香族炭化水素基及び脂環式炭化水素基）、これらを組み合わせた基に等をさらに有していてもよい。
アルカンジイル基としては、メチレン、エチレン、ｎ−プロピレン、イソプロピレン、ｎ−ブチレン、イソブチレン、tert−ブチレン、sec−ブチレン、ｎ−ペンチレン、２−メチルブチレン、３−メチルブチレン、２−エチルプロピレン、ｎ−ヘキシレン、２−メチルペンチレン、３−メチルペンチレン、２−エチルブチレン、３−エチルブチレン等が挙げられる。
芳香族炭化水素基としては、ベンゼン、トルエン、キシレン、ナフタリン等から水素原子を２個取り除いた基が挙げられる。
脂環式炭化水素基としては、シクロプロパン、シクロブタン、シクロペンタン、シクロヘキサン等から水素原子を２個取り除いた基が挙げられる。
In addition to the (poly) alkylene glycol structure and two (meth) acrylates, the bifunctional (meth) acrylate having a (poly) alkylene glycol structure is an alkanediyl group having 1 to 6 carbon atoms via an ether bond. A divalent cyclic hydrocarbon group having 3 to 10 carbon atoms (aromatic hydrocarbon group and alicyclic hydrocarbon group), a group obtained by combining these, and the like may further be included.
Examples of the alkanediyl group include methylene, ethylene, n-propylene, isopropylene, n-butylene, isobutylene, tert-butylene, sec-butylene, n-pentylene, 2-methylbutylene, 3-methylbutylene, 2-ethylpropylene, Examples include n-hexylene, 2-methylpentylene, 3-methylpentylene, 2-ethylbutylene, 3-ethylbutylene.
Examples of the aromatic hydrocarbon group include groups in which two hydrogen atoms have been removed from benzene, toluene, xylene, naphthalene and the like.
Examples of the alicyclic hydrocarbon group include groups in which two hydrogen atoms have been removed from cyclopropane, cyclobutane, cyclopentane, cyclohexane or the like.
（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレートとしては、ポリメチレングリコールジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、ポリプロピレングリコールジ（メタ）アクリレート、ポリテトラメチレングリコールジ（メタ）アクリレート、ポリメチレンポリエチレングリコールジ（メタ）アクリレート、ポリプロピレンポリエチレングリコールジ（メタ）アクリレート、メトキシ変性ビスフェノールＡジ（メタ）アクリレート、エトキシ変性ビスフェノールＡジ（メタ）アクリレート、プロポキシ変性ビスフェノールＡジ（メタ）アクリレート、メトキシエトキシ変性ビスフェノールＡジ（メタ）アクリレート、プロポキシエトキシ変性ビスフェノールＡジ（メタ）アクリレート等が挙げられる。なかでも、ポリエチレングリコールジ（メタ）アクリレート又はエトキシ変性ビスフェノールＡジ（メタ）アクリレートが好ましい。 Examples of the bifunctional (meth) acrylate having a (poly) alkylene glycol structure include polymethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and polytetramethylene glycol di (meth). Acrylate, polymethylene polyethylene glycol di (meth) acrylate, polypropylene polyethylene glycol di (meth) acrylate, methoxy modified bisphenol A di (meth) acrylate, ethoxy modified bisphenol A di (meth) acrylate, propoxy modified bisphenol A di (meth) acrylate , Methoxyethoxy modified bisphenol A di (meth) acrylate, propoxyethoxy modified bisphenol A di (meth) acrylate, etc. And the like. Of these, polyethylene glycol di (meth) acrylate or ethoxy-modified bisphenol A di (meth) acrylate is preferable.
この化合物は、比較的粘度が高く、分子量が大きくなると、分子量あたりのアクリロイル基の含有量が小さくなるために、硬度が低くなる傾向がある。よって、この化合物の数平均分子量（ゲルパーミエーションクロマトグラフによるポリスチレン換算値）は、例えば、２００〜２０００程度が挙げられ、５００〜１０００程度が好ましい。
また、この化合物は、ポリアルキレンオキサイドの付加モル数が大きくなると、柔軟性及び／又は復元性が向上する傾向がある。従って、これらの付加モル数は、２〜２０程度が好ましく、５〜１５程度がより好ましい。
This compound has a relatively high viscosity, and when the molecular weight is increased, the content of acryloyl groups per molecular weight is decreased, so that the hardness tends to decrease. Therefore, the number average molecular weight (polystyrene conversion value by gel permeation chromatograph) of this compound is, for example, about 200 to 2000, and preferably about 500 to 1000.
Further, this compound tends to improve flexibility and / or resilience when the number of added moles of polyalkylene oxide increases. Accordingly, the number of added moles is preferably about 2 to 20, and more preferably about 5 to 15.
活性エネルギー線硬化型樹脂組成物において、（Ｃ）成分の含有量は、得ようとする特性のバランスによって適宜調整することができるが、（Ａ）〜（Ｃ）成分の総重量に対して１重量％以上３０重量％以下程度が好ましく、５重量％以上３０重量％以下程度がより好ましい。 In the active energy ray-curable resin composition, the content of the component (C) can be appropriately adjusted depending on the balance of characteristics to be obtained, but is 1 with respect to the total weight of the components (A) to (C). The weight is preferably about 30% by weight or more and more preferably about 30% by weight or less.
本発明の活性エネルギー線硬化型樹脂組成物には（Ａ）〜（Ｃ）成分以外の（メタ）アクリレート化合物を含んでいてもよい。このような化合物としては、単官能および二官能以上の（メタ）アクリレートが挙げられる。 The active energy ray-curable resin composition of the present invention may contain a (meth) acrylate compound other than the components (A) to (C). Examples of such a compound include monofunctional and bifunctional or higher (meth) acrylates.
単官能（メタ）アクリレートとしては、例えば、ｎ−ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｔｅｒｔ−ブチル（メタ）アクリレート、ｎ−ペンチル（メタ）アクリレート、ｎ−ヘキシル（メタ）アクリレート、ｎ−オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、ベンジル（メタ）アクリレート、フェノキシエチル（メタ）アクリレート、フェノキシジエチレングリコール（メタ）アクリレート、グリシジル（メタ）アクリレート、モルホリン（メタ）アクリレート、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、ジエチレングリコールモノ（メタ）アクリレート、トリエチレングリコールモノ（メタ）アクリレート、ジプロピレングリコールモノ（メタ）アクリレート、２−メトキシエチル（メタ）アクリレート、メトキシジエチレングリコール（メタ）アクリレート、メトキシトリエチレングリコール（メタ）アクリレート、メトキシポリエチレングリコール（メタ）アクリレート、２−ブトキシエチル（メタ）アクリレート、ブトキシトリエチレングリコール（メタ）アクリレート、２−エトキシエチル（メタ）アクリレート、２−（２−エトキシエトキシ）エチル（メタ）アクリレート、エトキシポリエチレングリコール（メタ）アクリレート、４−ノニルフェノキシエチレングリコール（メタ）アクリレート、
テトラヒドロフルフリル（メタ）アクリレート、カプロラクトン変性テトラヒドロフルフリル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、イソボルニル（メタ）アクリレート、２−ヒドロキシ−３−フェノキシプロピル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、シクロヘキシルメチル（メタ）アクリレート、シクロヘキシルエチル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート、ジシクロペンタニロキシエチル（メタ）アクリレート、ジシクロペンテニル（メタ）アクリレート、ジシクロペンテニロキシエチル（メタ）アクリレート、ｏ−フェニルフェノキシエチル（メタ）アクリレート、エトキシ化Ｏ−フェニルフェノールアクリレート、ベンジルオキシアクリレート等が挙げられる。
As monofunctional (meth) acrylate, for example, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n -Octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, glycidyl (meth) acrylate, morpholine (meta) ) Acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, diethylene glycol mono (meth) Chryrate, triethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypolyethylene glycol (meta ) Acrylate, 2-butoxyethyl (meth) acrylate, butoxytriethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2- (2-ethoxyethoxy) ethyl (meth) acrylate, ethoxy polyethylene glycol (meth) Acrylate, 4-nonylphenoxyethylene glycol (meth) acrylate,
Tetrahydrofurfuryl (meth) acrylate, caprolactone-modified tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, cyclohexyl Methyl (meth) acrylate, cyclohexylethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) Acrylate, o-phenylphenoxyethyl (meth) acrylate, ethoxylated O-phenylphenol acrylate, benzyloxy acrylate, etc. It is.
二官能（メタ）アクリレートとしては、例えば、エチレングリコールジ（メタ）アクリレート、プロピレングリコールジ（メタ）アクリレート、ブチレングリコールジ（メタ）アクリレート、１，４−ブタンジオールジ（メタ）アクリレート、１，６−ヘキサンジオールジ（メタ）アクリレート、１，９−ノナンジオールジ（メタ）アクリレート、ネオペンチルグリコールジ（メタ）アクリレート、ビスフェノキシエタノールフルオレンジ（メタ）アクリレート、ジシクロペンタニルジ（メタ）アクリレート、グリセロールジ（メタ）アクリレート、ネオペンチルグリコールヒドロキシピバリン酸エステルジ（メタ）アクリレート、カプロラクトン変性ヒドロキシピバリン酸ネオペンチルグリコールジ（メタ）アクリレート、テトラブロモビスフェノールＡジ（メタ）アクリレート、ヒドロピバルアルデヒド変性トリメチロールプロパンジ（メタ）アクリレート、１，４−シクロヘキサンジメタノールジ（メタ）アクリレート９，９−ビス（４−アクリロキシエトキシフェニル）−フルオレン等の特開２０１０−２４８３５８号公報に記載されているフルオレン骨格を有するジ（メタ）アクリレート等が挙げられる。 Examples of the bifunctional (meth) acrylate include ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6 -Hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, bisphenoxyethanol full orange (meth) acrylate, dicyclopentanyl di (meth) acrylate, glycerol Di (meth) acrylate, neopentyl glycol hydroxypivalate ester di (meth) acrylate, caprolactone-modified hydroxypivalate neopentyl glycol di (meth) acrylate, tetrabromobi Phenol A di (meth) acrylate, hydropivalaldehyde-modified trimethylolpropane di (meth) acrylate, 1,4-cyclohexanedimethanol di (meth) acrylate 9,9-bis (4-acryloxyethoxyphenyl) -fluorene, etc. And di (meth) acrylate having a fluorene skeleton described in JP-A-2010-248358.
この活性エネルギー線硬化型樹脂組成物は、本来の機能を損なわない限り、当該分野で公知の添加剤を含有させてもよい。添加剤としては、光重合開始剤／重合開始剤、希釈剤、金属酸化物微粒子、レベリング剤、潤滑性付与剤、その他の樹脂等が挙げられる。 This active energy ray-curable resin composition may contain an additive known in the art as long as the original function is not impaired. Examples of the additive include a photopolymerization initiator / polymerization initiator, a diluent, metal oxide fine particles, a leveling agent, a lubricity imparting agent, and other resins.
光重合開始剤としては、例えば、ヒドロキシシクロヘキシルフェニルケトン、シクロヘキシルフェニルケトン、１−フェニル−２−ヒドロキシ−２−メチルプロパン−１−オン、２，２−ジメトキシ−２−フェニルアセトフェノン、べンゾフェノン、２−メチル［４−（メチルチオ）フェニル］−２−モルフォリノ−１−プロパノン、２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン、１−（４−イソプロピルフェニル）−２−ヒドロキシ−２−メチルプロパン−１−オン、４−（２−ヒドロキシエトキシ）フェニル−（２−ヒドロキシ−２−プロピル）ケトン、４−（２−アクリロイルオキシエトキシ）フェニル−（２−ヒドロキシ−２−プロピル）ケトン、４−（２−メタクリロイルオキシエトキシ）フェニル−（２−ヒドロキシ−２−プロピル）ケトン、２，４，６−トリメチルべンゾイルジフェニルフォスフィンオキサイドが挙げられる。
光重合開始剤は、（Ａ）〜（Ｃ）成分１００重量部に対して、０．１〜２０重量部程度含有させることが好ましく、１〜１０重量部がより好ましい。
Examples of the photopolymerization initiator include hydroxycyclohexyl phenyl ketone, cyclohexyl phenyl ketone, 1-phenyl-2-hydroxy-2-methylpropan-1-one, 2,2-dimethoxy-2-phenylacetophenone, benzophenone, 2 -Methyl [4- (methylthio) phenyl] -2-morpholino-1-propanone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2 -Methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 4- (2-acryloyloxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone 4- (2-Methacryloyloxyethoxy) phenyl- (2-H Proxy-2-propyl) ketone, and 2,4,6-trimethyl base down benzoyl diphenyl phosphine oxide.
The photopolymerization initiator is preferably contained in an amount of about 0.1 to 20 parts by weight and more preferably 1 to 10 parts by weight with respect to 100 parts by weight of the components (A) to (C).
希釈剤としては、アルキレングリコールのモノアルキルエーテル類、アルキルアルコール類、アルキレングリコールモノアルキルアルコールのアルキルカルボン酸エステル類、ケトン類、アルキルアルコールのアルキルカルボン酸エステル類等が挙げられる。これらは、例えば、特開２００４−４３７９０号に記載のものが例示される。 Examples of the diluent include monoalkyl ethers of alkylene glycol, alkyl alcohols, alkyl carboxylic acid esters of alkylene glycol monoalkyl alcohol, ketones, alkyl carboxylic acid esters of alkyl alcohol, and the like. For example, those described in JP-A-2004-43790 are exemplified.
レベリング剤及び潤滑性付与剤としては、例えば、ポリオキシアルキレンとポリジメチルシロキサンとの共重合体、ポリオキシアルキレンとフルオロカーボンとの共重合体等が挙げられる。
その他の樹脂としては、例えば、ポリウレタン樹脂、ポリエピスルフィド樹脂、ポリメチルメタクリレート（ＰＭＭＡ）のような（メタ）アクリル系重合体、アリル系重合体、ジエチレングリコールビスアリルカーボネート、ポリカーボネート、ＭＳ樹脂、環状ポリオレフィン等各種合成樹脂が挙げられる。
その他の樹脂を含む場合、その他の樹脂は、（Ａ）〜（Ｃ）成分１００重量部に対して、０．１〜１０重量部程度含有させることが好ましく、０．５〜５重量部がより好ましい。
Examples of the leveling agent and the lubricity-imparting agent include a copolymer of polyoxyalkylene and polydimethylsiloxane, a copolymer of polyoxyalkylene and fluorocarbon, and the like.
Examples of other resins include polyurethane resins, polyepisulfide resins, (meth) acrylic polymers such as polymethyl methacrylate (PMMA), allyl polymers, diethylene glycol bisallyl carbonate, polycarbonate, MS resin, cyclic polyolefin, and the like. Various synthetic resins are mentioned.
When other resins are included, the other resins are preferably contained in an amount of about 0.1 to 10 parts by weight with respect to 100 parts by weight of the components (A) to (C), more preferably 0.5 to 5 parts by weight. preferable.
また、ビス（１，２，２，６，６−ペンタメチル−４−ピペリジル）セバケート、ビス（２，２，６，６−テトラメチル−４−ピペリジル）セバケート、テトラ（１，２，２，６，６−ペンタメチル−４−ピペリジル）−１，２，３，４−ブタンテトラカルボン酸エステル等の１，２，２，６，６−ペンタメチル−４−ピペリジル残基を有するヒンダードアミン系光安定剤；テトラキス〔メチレン−３−（３，５−ジ−ｔ−ブチル−４−ヒドロキシフェニル）プロピオネート〕メタン、ｎ−オクチル−３−（３，５−ジ−ｔ−ブチル−４−ヒドロキシフェニル）プロピオネート、４，４’−チオビス（３−メチル−６−ｔ−ブチルフェノール）等のヒンダードフェノール系あるいはジトリデシル−３，３’−チオジプロピオネート、ジラウリル−３，３’−チオジプロピオネート、ビス〔２−メチル−４−｛３−ｎ−アルキル（Ｃ１２またはＣ１４）チオプロピオニルオキシ｝−５−ｔ−ブチルフェニル〕スルフィド等の硫黄系等の３，５−ジ−ｔ−ブチル−４−ヒドロキシフェニル残基あるいは３−メチル−６−ｔ−ブチルフェニル残基を有する酸化防止剤；亜リン酸エステル系の脱色剤；シリコーンオイル等の消泡剤；シランカップリング剤；難燃剤；充填剤；艶消し剤；光増感剤；紫外線吸収剤；帯電防止剤；離型剤等の当該分野で公知の添加剤を配合してもよい。 Also, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, tetra (1,2,2,6) Hindered amine light stabilizer having 1,2,2,6,6-pentamethyl-4-piperidyl residue, such as 1,6-pentamethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylic acid ester; Tetrakis [methylene-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] methane, n-octyl-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate, Hindered phenols such as 4,4′-thiobis (3-methyl-6-tert-butylphenol) or ditridecyl-3,3′-thiodipropionate, dilauryl 3,3'-thiodipropionate, bis [2-methyl-4-{3-n-alkyl (C 12 or C 14) thio propionyloxy} -5-t-butylphenyl] sulfur system such as the sulfides Antioxidant having 3,5-di-t-butyl-4-hydroxyphenyl residue or 3-methyl-6-t-butylphenyl residue; Phosphite-based decoloring agent; Antifoaming of silicone oil, etc. Additives known in the art such as agents, silane coupling agents, flame retardants, fillers, matting agents, photosensitizers, ultraviolet absorbers, antistatic agents, and release agents may be blended.
活性エネルギー線硬化型樹脂組成物は、種々の方法によって調製することができる。例えば、分散液に分散された金属酸化物ナノ粒子（Ａ）に、フェノキシベンジル（メタ）アクリレート類（Ｂ）及び（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレート（Ｃ）、任意に添加剤を添加し、混合する方法、さらにこの混合物における水又は共溶媒（使用する場合）を蒸発除去することにより、粒子を（Ｂ）及び（Ｃ）成分中に分散させる方法、粉末状態の金属酸化物ナノ粒子、任意に添加剤を、直接（Ｂ）及び（Ｃ）成分中に分散させる方法等が挙げられる。 The active energy ray-curable resin composition can be prepared by various methods. For example, phenoxybenzyl (meth) acrylates (B) and a bifunctional (meth) acrylate (C) having a (poly) alkylene glycol structure are optionally added to the metal oxide nanoparticles (A) dispersed in the dispersion A method of adding and mixing an agent, and a method of dispersing particles in the components (B) and (C) by evaporating and removing water or a co-solvent (if used) in the mixture, metal oxidation in a powder state For example, a method of dispersing the product nanoparticles, optionally additives, directly in the components (B) and (C).
このようにして組成された活性エネルギー線硬化型樹脂組成物は、２５℃における粘度が２０００ｍＰａ・ｓ以下であり、さらに、１０００ｍＰａ・ｓ以下であることが好ましい。このような粘度とすることにより、室温において取り扱い及び加工性を向上させることができる。 The active energy ray-curable resin composition thus composed has a viscosity at 25 ° C. of 2000 mPa · s or less, and preferably 1000 mPa · s or less. By setting it as such a viscosity, handling and workability can be improved at room temperature.
活性エネルギー線硬化型樹脂組成物の硬化物のガラス転移温度（Ｔｇ）は、２０℃以下であることが好ましく、１４℃以下であることがより好ましい。このようなＴｇとすることにより、室温で柔軟かつ復元性の良好な物性を得ることができ、耐スクラッチ性、耐衝撃性の良好な塗膜となる。Ｔｇの調整は、例えば、原料成分の配合比により、任意に調整することができる。 The glass transition temperature (Tg) of the cured product of the active energy ray-curable resin composition is preferably 20 ° C. or less, and more preferably 14 ° C. or less. By setting it as such Tg, the physical property which is flexible and has a favorable restorability at room temperature can be obtained, and it becomes a coating film with favorable scratch resistance and impact resistance. The adjustment of Tg can be arbitrarily adjusted by, for example, the mixing ratio of the raw material components.
さらに、活性エネルギー線硬化型樹脂組成物の硬化物の屈折率は、２５℃で１．６０以上であることが適しており、１．６２以上であることが好ましい。屈折率は、例えば、アッベ屈折率計にて測定することができる。このような屈折率にすることにより、正面輝度等をより向上させることができる。なお、このような屈折率の調整は、例えば、原料成分の配合比により、任意に調整することができる。 Furthermore, the refractive index of the cured product of the active energy ray-curable resin composition is suitably 1.60 or more at 25 ° C., and preferably 1.62 or more. The refractive index can be measured by, for example, an Abbe refractometer. By using such a refractive index, the front luminance and the like can be further improved. In addition, such adjustment of a refractive index can be arbitrarily adjusted with the compounding ratio of a raw material component, for example.
本発明の活性エネルギー線硬化型樹脂組成物は、紫外線、放射線、赤外線、Ｘ線、電子線の活性エネルギー線、特に紫外線を照射することにより硬化させることができ、硬化物を得ることができる。ここで、硬化物としては、かならずしも特定の形状に成形加工したもののみならず、種々の形態を有するものが包含される。例えば、レンズと基材との間に活性エネルギー線硬化型樹脂組成物を流し込み、活性エネルギー線を照射して硬化させ、特定の形状に成形したものも包含される。
活性エネルギー線の光源としては、例えば、キセノンランプ、カーボンアーク、殺菌灯、紫外線用蛍光灯、複写用高圧水銀灯、中圧水銀灯、高圧水銀灯、超高圧水銀灯、無電極ランプ、メタルハライドランプ、走査型又はカーテン型電子線加速路による電子線等を挙げることができる。
このような光源を用いて硬化させる場合、活性エネルギー線照射量は３００〜３０００ｍＪ／ｃｍ2程度が適している。なお、樹脂組成物を十分に硬化させるために、紫外線等の活性エネルギー線を照射することが好ましい。
The active energy ray-curable resin composition of the present invention can be cured by irradiation with active energy rays such as ultraviolet rays, radiation, infrared rays, X-rays, and electron beams, particularly ultraviolet rays, and a cured product can be obtained. Here, as a hardened | cured material, what has not only what was shape-processed by the specific shape but what has various forms is included. For example, the active energy ray-curable resin composition is poured between the lens and the base material, irradiated with active energy rays and cured, and molded into a specific shape.
Examples of light sources for active energy rays include xenon lamps, carbon arcs, germicidal lamps, fluorescent lamps for ultraviolet rays, high pressure mercury lamps for copying, medium pressure mercury lamps, high pressure mercury lamps, ultrahigh pressure mercury lamps, electrodeless lamps, metal halide lamps, scanning types or Examples thereof include an electron beam by a curtain type electron beam acceleration path.
In the case of curing using such a light source, the active energy ray dose is suitably about 300 to 3000 mJ / cm 2 . In addition, in order to fully cure the resin composition, it is preferable to irradiate active energy rays such as ultraviolet rays.
本発明の硬化物としては、プラスチックレンズ等のような成形物が挙げられる。
成形物の作製法としては、ポリ塩化ビニル、エチレン酢酸ビニル共重合体等からなるガスケットと所望の形状の２つの鋳型の間に、樹脂組成物を注入した後、紫外線等の活性エネルギー線を照射して本発明の樹脂組成物を硬化させ、硬化物を型より剥離する方法等が挙げられる。
Examples of the cured product of the present invention include molded products such as plastic lenses.
The molded product can be made by injecting a resin composition between a gasket made of polyvinyl chloride, ethylene vinyl acetate copolymer, etc. and two molds of the desired shape, and then irradiating with active energy rays such as ultraviolet rays. And a method of curing the resin composition of the present invention and peeling the cured product from the mold.
また、本発明の硬化物は、シート状に成形してもよい。シートの形成は、当該分野で公知の方法、例えば、押し出し成形等、あるいは、適当な基材上に、上述した方法を用いて塗布膜を形成し、硬化させた後に基材を剥離する方法等が例示される。
なお、後述するように、レンズシート、プリズムシート等の光学シートとする場合には、例えば、硬化後の厚みが０．０１μｍ〜１０ｍｍ程度とすることが適しており、０．０１〜１０００μｍ程度とすることが好ましく、０．０１〜１００μｍ程度とすることがより好ましい。
Moreover, you may shape | mold the hardened | cured material of this invention in a sheet form. Sheet formation is a method known in the art, such as extrusion molding, or a method of forming a coating film on an appropriate substrate using the method described above and curing the substrate, and then peeling the substrate. Is exemplified.
As will be described later, when an optical sheet such as a lens sheet or a prism sheet is used, for example, the thickness after curing is suitably about 0.01 μm to 10 mm, and about 0.01 to 1000 μm. It is preferable to set it to about 0.01 to 100 μm.
さらに、本発明の硬化物は、基材に対する積層層として形成してもよい。具体的には、基材に、刷毛塗り、バーコーター、アプリケーター、ロールコーターあるいはローラーブラシ等により直接塗布する方法、エアースプレーまたはエアーレススプレー塗装機等によるスプレー塗布法、シャワーコーターまたはカーテンフローコーター等により流し塗りする方法（フローコート）、浸漬法、キャスティング法、スピンコート法を用いる方法などによって、積層することができる。
基材としては、ポリエチレンテレフタレート（ＰＥＴ）、ポリエチレンナフテート（ＰＥＮ）などのポリエステル樹脂、ポリウレタン樹脂、ポリエピスルフィド樹脂、ポリメチルメタクリレート（ＰＭＭＡ）のような（メタ）アクリル系重合体、アリル系重合体、ジエチレングリコールビスアリルカーボネート、ポリカーボネート、ＭＳ樹脂、環状ポリオレフィン、トリアセチルセルロース（ＴＡＣ）等各種合成樹脂からなる基材が挙げられる。基材は、平板状、曲板状、フィルム状等のいずれの形状であってもよい。
Furthermore, you may form the hardened | cured material of this invention as a laminated layer with respect to a base material. Specifically, methods such as brush coating, bar coater, applicator, roll coater or roller brush directly applied to the substrate, spray coating using an air spray or airless spray coater, shower coater or curtain flow coater, etc. The film can be laminated by a flow coating method (flow coating), a dipping method, a casting method, a method using a spin coating method, or the like.
Base materials include polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthate (PEN), polyurethane resins, polyepisulfide resins, (meth) acrylic polymers such as polymethyl methacrylate (PMMA), and allyl polymers. , Base materials made of various synthetic resins such as diethylene glycol bisallyl carbonate, polycarbonate, MS resin, cyclic polyolefin, and triacetyl cellulose (TAC). The substrate may have any shape such as a flat plate shape, a curved plate shape, and a film shape.
このように、本発明の活性エネルギー線硬化型樹脂組成物は、任意な形状に硬化させることにより、例えば、プリズムレンズシート、非球面レンズ、フレネルレンズ、レンチキュラーレンズ、眼鏡レンズ、液晶ディスプレイ用パネル及びカラーフィルター用保護膜、光ディスク用コーティング剤及び接着剤、光ファイバー用コア材及びクラッド材、光ファイバー接続用接着剤、光導波路用コア材及びクラッド材等の種々の物品に応用することが可能である。 Thus, the active energy ray-curable resin composition of the present invention is cured into an arbitrary shape, for example, a prism lens sheet, an aspheric lens, a Fresnel lens, a lenticular lens, a spectacle lens, a liquid crystal display panel, and It can be applied to various articles such as color filter protective films, optical disk coatings and adhesives, optical fiber core materials and clad materials, optical fiber connection adhesives, optical waveguide core materials and clad materials.
以下に、本発明の活性エネルギー線硬化型樹脂組成物及び硬化物の実施例により、本発明を具体的に説明するが、本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be specifically described by way of examples of the active energy ray-curable resin composition and the cured product of the present invention, but the present invention is not limited thereto.
実施例及び比較例
表１に示した成分を、所定の比率で均一になるまで混合・攪拌し、溶剤を蒸発させて、除去する方法により、活性エネルギー線硬化型樹脂組成物を得た。なお、表における成分の単位は重量部で表した。
Examples and Comparative Examples The components shown in Table 1 were mixed and stirred at a predetermined ratio until uniform, and the solvent was evaporated to remove the active energy ray-curable resin composition. In addition, the unit of the component in a table | surface was represented by the weight part.
得られた活性エネルギー線硬化型樹脂組成物をガラス板上に膜厚が１００μｍになるよう塗布し、基材として未処理ＰＥＴフィルム（東レ（株）製ルミラー）を接着させ、更にその上から高圧水銀ランプで１０００ｍＪ／ｃｍ２の照射量の紫外線を照射して硬化させた。その後、樹脂硬化膜のみを剥離して、屈折率測定およびＴｇ測定用の硬化物を得た。 The obtained active energy ray-curable resin composition was applied on a glass plate so as to have a film thickness of 100 μm, and an untreated PET film (Lumirror manufactured by Toray Industries, Inc.) was adhered as a base material. Curing was performed by irradiating with 1000 mJ / cm 2 of ultraviolet rays with a mercury lamp. Thereafter, only the cured resin film was peeled off to obtain a cured product for refractive index measurement and Tg measurement.
プリズム形状の型の上に膜厚が５０μｍになるように塗布し、その上に基材として易接着処理ＰＥＴフィルム（東洋紡績（株）コスモシャインＡ４１００）を接着させ、更にその上から高圧水銀ランプで１０００ｍＪ／ｃｍ２の照射量の紫外線を照射して硬化させた。その後、金型より剥離して、本発明の硬化物を得た。 It is coated on a prism-shaped mold so that the film thickness is 50 μm, and an easy-adhesion-treated PET film (Toyobo Co., Ltd. Cosmo Shine A4100) is adhered thereon as a base material. And then cured by irradiating with an ultraviolet ray of 1000 mJ / cm 2 . Then, it peeled from the metal mold | die and obtained the hardened | cured material of this invention.
各樹脂組成物について、以下の評価を行った。
密着性：プリズム形状の型の上に膜厚が５０μｍになるように塗布し、その上に基材として易接着処理ＰＥＴフィルム（東洋紡績（株）コスモシャインＡ４１００を接着させ、更にその上から高圧水銀ランプで１０００ｍＪ／ｃｍ２の照射量の紫外線を照射して硬化させた後、金型より剥離してテストピースを作成し、ＪＩＳ Ｋ５６００−５−６に準じた碁盤目セロハンテープ剥離試験を行った。評価結果は０〜２を○とし、３〜５を×とした。
屈折率：硬化した活性エネルギー線硬化型樹脂組成物を、アッベ屈折率計（ＤＲ−Ｍ２：（株）アタゴ製）にて５８９ｎｍ波長（Ｄ線）における屈折率を測定した。
粘度：活性エネルギー線硬化型樹脂組成物を、ビスメトロン粘度計（ＶＤＡ２：芝浦システム（株）製）にて測定した。
Each resin composition was evaluated as follows.
Adhesion: coated onto a prism-shaped mold so as to have a film thickness of 50 μm, and an easy-adhesion-treated PET film (Toyobo Co., Ltd. Cosmo Shine A4100) is adhered thereon as a substrate, and then high pressure is applied from above. After curing by irradiating with a 1000 mJ / cm 2 ultraviolet ray with a mercury lamp, the test piece was peeled off from the mold and a cellophane tape peeling test according to JIS K5600-5-6 was conducted. In the evaluation results, 0 to 2 were evaluated as ○, and 3 to 5 as ×.
Refractive index: The refractive index at a wavelength of 589 nm (D line) of the cured active energy ray-curable resin composition was measured with an Abbe refractometer (DR-M2: manufactured by Atago Co., Ltd.).
Viscosity: The active energy ray-curable resin composition was measured with a bismetholone viscometer (VDA2: manufactured by Shibaura System Co., Ltd.).
耐スクラッチ性：プリズム形状の型の上に膜厚が５０μｍになるように塗布し、その上に基材として易接着処理ＰＥＴフィルム（東洋紡績（株）コスモシャインＡ４１００を接着させ、更にその上から高圧水銀ランプで１０００ｍＪ／ｃｍ２の照射量の紫外線を照射して硬化させた後、金型より剥離して得られたテストピースの上にガラス棒を当て、横方向に引きずった時の、傷のつき方を観察した。
○：傷がつかず、外観に問題がない状態
×：傷がつき、外観に問題がある状態
Scratch resistance: coated onto a prism-shaped mold so as to have a film thickness of 50 μm, and an easy-adhesion-treated PET film (Toyobo Co., Ltd. Cosmo Shine A4100 as a base material is adhered thereon, and further from above Scratches when a glass rod is placed on a test piece that is peeled off from a mold after being cured by irradiating with a 1000 mJ / cm 2 ultraviolet ray with a high-pressure mercury lamp and then dragged in the horizontal direction. Observed how to attach.
○: Scratch not found, no problem with appearance ×: Scratch, appearance with problem
耐衝撃性：プリズム形状の型の上に膜厚が５０μｍになるように塗布し、その上に基材として易接着処理ＰＥＴフィルム（東洋紡績（株）コスモシャインＡ４１００を接着させ、更にその上から高圧水銀ランプで１０００ｍＪ／ｃｍ２の照射量の紫外線を照射して硬化させた後、金型より剥離してテストピースを得た。２ｍｍ厚みのアクリル板（三菱レイヨン（株）アクリライト）の上に、得られたテストピース、アクリル板の順に載せ、２０ｃｍの高さから直径６０ｍｍφ、重さ１３０ｇｆのアクリル樹脂製の球を落下させた。表面のアクリル板を取り外し、テストピースの落下部分の痕のつき方を観察した。
○：痕がつかず、外観に問題がない状態
×：痕がみえ、時間が経過しても消えず、外観に問題がある状態
Impact resistance: coated on a prism-shaped mold so as to have a film thickness of 50 μm, and an easy-adhesion treated PET film (Toyobo Co., Ltd. Cosmo Shine A4100 as a base material is adhered thereon, and further from above The test piece was peeled off from the mold after being cured by irradiating with an ultraviolet ray of 1000 mJ / cm 2 with a high pressure mercury lamp, and a test piece was obtained on the 2 mm thick acrylic plate (Mitsubishi Rayon Co., Ltd. Acrylite). Then, the test piece and the acrylic plate obtained were placed in this order, and an acrylic resin ball having a diameter of 60 mmφ and a weight of 130 gf was dropped from a height of 20 cm. Observed how to attach.
○: No marks are observed and there is no problem with the appearance. ×: Marks are observed, the marks do not disappear over time, and there is a problem with the appearance.
硬化後のガラス転移温度（Ｔｇ）：得られた活性エネルギー線硬化型樹脂組成物をガラス板上に膜厚が１００μｍになるよう塗布し、基材として未処理ＰＥＴフィルム（東レ（株）製ルミラー）を接着させ、更にその上から高圧水銀ランプで１０００ｍＪ／ｃｍ２の照射量の紫外線を照射して硬化させた後、樹脂硬化膜のみを剥離してテストピースを得た。得られたテストピースを動的粘弾性測定装置（ＴＡインスツルメンツ社製 Ｑ８００）を用いて、引張正弦波、１Ｈｚの周波数、毎分５℃の昇温速度で測定した。得られた結果の貯蔵弾性率と損失弾性率との損失正接（ｔａｎδ）の極大時温度をＴｇとした。 Glass transition temperature (Tg) after curing: The obtained active energy ray-curable resin composition was applied on a glass plate so as to have a film thickness of 100 μm, and an untreated PET film (Lumirror manufactured by Toray Industries, Inc.) was used as a substrate. Then, the resin was cured by irradiating it with ultraviolet rays of 1000 mJ / cm 2 with a high-pressure mercury lamp, and then only the resin cured film was peeled off to obtain a test piece. The obtained test piece was measured using a dynamic viscoelasticity measuring apparatus (Q800 manufactured by TA Instruments) at a tensile sine wave, a frequency of 1 Hz, and a temperature rising rate of 5 ° C. per minute. The maximum temperature at the loss tangent (tan δ) between the storage elastic modulus and the loss elastic modulus as a result was defined as Tg.
なお、表１の成分は、以下のとおりである。
（Ａ）成分：商品名ジルコスターＺＰ−１５３Ａ（株式会社日本触媒製、ナノ酸化ジルコニウムメチルエチルケトン分散液（固形分７０％））
（Ｂ）成分１：商品名ライトアクリレートＰＯＢ−Ａ（共栄社化学株式会社製、ｍ−フェノキシベンジルアクリレート）
（ｂ）成分１：商品名ＮＫエステルＡ−ＬＥＮ−１０(新中村化学工業株式会社製、エトキシ化Ｏ−フェニルフェノールアクリレート）
（ｂ）成分２：商品名ライトアクリレートＰＯ−Ａ（共栄社化学株式会社製、フェノキシエチルアクリレート）
In addition, the component of Table 1 is as follows.
(A) component: Trade name Zircoster ZP-153A (manufactured by Nippon Shokubai Co., Ltd., nano zirconium oxide methyl ethyl ketone dispersion (solid content 70%))
(B) Component 1: Trade name light acrylate POB-A (manufactured by Kyoeisha Chemical Co., Ltd., m-phenoxybenzyl acrylate)
(B) Component 1: Trade name NK ester A-LEN-10 (manufactured by Shin-Nakamura Chemical Co., Ltd., ethoxylated O-phenylphenol acrylate)
(B) Component 2: Trade name Light acrylate PO-A (Kyoeisha Chemical Co., Ltd., phenoxyethyl acrylate)
（Ｃ）成分１：商品名ライトアクリレート１４ＥＧ−Ａ（共栄社化学株式会社製、ポリエチレングリコールジアクリレート ｎ＝１４）
（Ｃ）成分２：商品名ライトアクリレートＢＰ−１０ＥＡ（共栄社化学株式会社製、エトキシ化ビスフェノールＡジアクリレート 付加モル数は合計１０モル）
（Ｃ）成分３：商品名エポキシエステル３０００Ａ（共栄社化学株式会社製、ビスフェノールＡジグリシジルエーテルとアクリル酸との反応生成物）
(C) Component 1: Trade name light acrylate 14EG-A (manufactured by Kyoeisha Chemical Co., Ltd., polyethylene glycol diacrylate n = 14)
(C) Component 2: Trade name light acrylate BP-10EA (manufactured by Kyoeisha Chemical Co., Ltd., ethoxylated bisphenol A diacrylate added in a total of 10 moles)
(C) Component 3: Trade name epoxy ester 3000A (Kyoeisha Chemical Co., Ltd., reaction product of bisphenol A diglycidyl ether and acrylic acid)
（Ｄ）成分：商品名イルガキュア１８４（ＢＡＳＦ社製、１−ヒドロキシシクロヘキシルフェニルケトン） Component (D): trade name Irgacure 184 (BASF, 1-hydroxycyclohexyl phenyl ketone)
表１から、実施例は、比較例に対して、耐スクラッチ性及び耐衝撃性、屈折率、Ｔｇにおいてバランスを図ることができ、これらの特性の全てにおいて、意図する満足のいく結果を得ることができたことが確認された。また、粘度が比較的低く、加工しやすいことが確認された。 From Table 1, the Examples can achieve a balance in scratch resistance and impact resistance, refractive index, and Tg with respect to the Comparative Examples, and obtain the intended satisfactory results in all of these characteristics. It was confirmed that It was also confirmed that the viscosity was relatively low and it was easy to process.
本発明の活性エネルギー線硬化型樹脂組成物は、上述したように、プリズムシート等の種々の光学用部材に応用することが可能である。 As described above, the active energy ray-curable resin composition of the present invention can be applied to various optical members such as a prism sheet.
Claims (9)
フェノキシベンジル（メタ）アクリレート類（Ｂ）及び
（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレート（Ｃ）を含有することを特徴とする活性エネルギー線硬化型樹脂組成物。 Metal oxide nanoparticles (A),
An active energy ray-curable resin composition comprising a phenoxybenzyl (meth) acrylate (B) and a bifunctional (meth) acrylate (C) having a (poly) alkylene glycol structure.
前記フェノキシベンジル（メタ）アクリレート類（Ｂ）が５重量％以上６０重量％以下であり、
前記（ポリ）アルキレングリコール構造を有する二官能（メタ）アクリレート（Ｃ）が１重量％以上３０重量％以下である請求項１記載の活性エネルギー線硬化型樹脂組成物。 The metal oxide nanoparticles (A) are 20 wt% or more and 70 wt% or less,
The phenoxybenzyl (meth) acrylates (B) are 5 wt% or more and 60 wt% or less,
2. The active energy ray-curable resin composition according to claim 1, wherein the bifunctional (meth) acrylate (C) having the (poly) alkylene glycol structure is 1% by weight or more and 30% by weight or less.
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| TW106101389A TW201736464A (en) | 2016-01-22 | 2017-01-16 | Active energy ray curable resin composition, cured product thereof and lens sheet |
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Also Published As
| Publication number | Publication date |
|---|---|
| JP6022094B1 (en) | 2016-11-09 |
| CN106995515A (en) | 2017-08-01 |
| TW201736464A (en) | 2017-10-16 |
| KR20170088295A (en) | 2017-08-01 |
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