KR102321823B1 - Active energy ray-curable resin composition for optical article, cured product and optical sheet - Google Patents
Active energy ray-curable resin composition for optical article, cured product and optical sheet Download PDFInfo
- Publication number
- KR102321823B1 KR102321823B1 KR1020197008666A KR20197008666A KR102321823B1 KR 102321823 B1 KR102321823 B1 KR 102321823B1 KR 1020197008666 A KR1020197008666 A KR 1020197008666A KR 20197008666 A KR20197008666 A KR 20197008666A KR 102321823 B1 KR102321823 B1 KR 102321823B1
- Authority
- KR
- South Korea
- Prior art keywords
- active energy
- energy ray
- acrylate
- meth
- formula
- Prior art date
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 48
- 239000011342 resin composition Substances 0.000 title abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 72
- 239000000463 material Substances 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 90
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 abstract description 4
- GSJNBCZKEUYYLK-UHFFFAOYSA-N [phenoxy(phenyl)methyl] prop-2-enoate Chemical compound C=1C=CC=CC=1C(OC(=O)C=C)OC1=CC=CC=C1 GSJNBCZKEUYYLK-UHFFFAOYSA-N 0.000 abstract description 3
- -1 phenoxybenzyl Chemical group 0.000 description 17
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- KSXJRXNHRYSLLC-UHFFFAOYSA-N 9H-fluorene prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.C1=CC=C2CC3=CC=CC=C3C2=C1 KSXJRXNHRYSLLC-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 239000002105 nanoparticle Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000004973 liquid crystal related substance Substances 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000010292 orthophenyl phenol Nutrition 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- FGGRLKWCMJMSKS-UHFFFAOYSA-N (2-phenoxy-2-phenylethyl) prop-2-enoate Chemical compound C=1C=CC=CC=1C(COC(=O)C=C)OC1=CC=CC=C1 FGGRLKWCMJMSKS-UHFFFAOYSA-N 0.000 description 1
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-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
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 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
- 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
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-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
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical class OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SVIQBUBNVYWIDV-UHFFFAOYSA-N 2-methoxy-2-(2-methoxyphenyl)-1-phenylethanone Chemical compound C=1C=CC=C(OC)C=1C(OC)C(=O)C1=CC=CC=C1 SVIQBUBNVYWIDV-UHFFFAOYSA-N 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
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- VAZQKPWSBFZARZ-UHFFFAOYSA-N C=CC(OCCOc(cccc1)c1-c1ccccc1)=O Chemical compound C=CC(OCCOc(cccc1)c1-c1ccccc1)=O VAZQKPWSBFZARZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 229920003006 Polybutadiene acrylonitrile Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 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
- IJVHTTITHMXYTG-UHFFFAOYSA-N benzhydryl prop-2-enoate Chemical compound C=1C=CC=CC=1C(OC(=O)C=C)C1=CC=CC=C1 IJVHTTITHMXYTG-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 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
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004386 diacrylate group Chemical group 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
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- 230000001678 irradiating effect Effects 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
- 238000010030 laminating Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 125000006187 phenyl benzyl group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
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- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
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- 238000007493 shaping process Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
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- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
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- 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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Abstract
높은 굴절률을 가지면서, 내스크래치성이 우수하고, 긁힘이 발생했을 때에도 호적한 자기치유성을 가지며, 또한 우수한 습열밀착성을 갖는 광학물품을 형성할 수 있는 활성 에너지선 경화형 수지 조성물을 제공한다.
장쇄의 알킬렌옥사이드쇄를 갖는 플루오렌계 (메타)아크릴레이트와, 페녹시벤질아크릴레이트를 함유하는 광학물품용 활성 에너지선 경화성 조성물에 의해, 습열밀착성이나 내스크래치성을 확보하면서, 높은 굴절률과, 호적한 자기치유성을 실현할 수 있고, 고굴절률이며 긁힘 내성이 우수한 프리즘 시트를 실현할 수 있다.Provided is an active energy ray-curable resin composition capable of forming an optical article having a high refractive index, excellent scratch resistance, suitable self-healing properties even when scratched, and excellent wet heat adhesion.
By an active energy ray-curable composition for optical articles containing a fluorene-based (meth)acrylate having a long alkylene oxide chain and phenoxybenzyl acrylate, high refractive index and high refractive index and , suitable self-healing properties can be realized, and a prism sheet having a high refractive index and excellent scratch resistance can be realized.
Description
본 발명은, 광학물품에 사용하는 활성 에너지선 경화형 수지 조성물, 당해 조성물을 경화시킨 경화물 및 당해 경화물로 이루어지는 광학 시트에 관한 것이다.The present invention relates to an active energy ray-curable resin composition for use in optical articles, a cured product obtained by curing the composition, and an optical sheet comprising the cured product.
액정 표시 장치 등의 디스플레이에 사용되는 프리즘 시트, 입체 사진이나 투영 스크린 등에 사용되는 렌티큘러 렌즈 시트, 오버헤드 프로젝터의 콘덴서 렌즈 등에 사용되는 프레넬 렌즈 시트, 컬러필터 등에 사용되는 회절 격자 등의 광학 시트에 있어서는, 각종 활성 에너지선 경화형 수지 조성물이 사용되고 있다. 이들 광학 시트는, 각각의 용도에 따른 특성이 요구되며, 예를 들면, 프리즘 시트에 있어서는 디스플레이의 휘도 향상을 위하여, 높은 굴절률이 요구된다.For optical sheets such as prism sheets used for displays such as liquid crystal displays, lenticular lens sheets used for stereoscopic photography and projection screens, Fresnel lens sheets used for condenser lenses of overhead projectors, diffraction gratings used for color filters, etc. In this case, various active energy ray-curable resin compositions are used. These optical sheets are required to have properties according to their respective uses. For example, in a prism sheet, a high refractive index is required to improve the luminance of the display.
광학 재료 용도에 있어서 높은 굴절률을 갖는 재료로서는, 플루오렌 골격을 갖는 (메타)아크릴레이트가 알려져 있으며, 예를 들면, 옥시알킬렌기의 부가수를 크게 한 플루오렌 골격을 갖는 다관능성 (메타)아크릴레이트와, 페녹시벤질(메타)아크릴레이트를 함유하는 경화성 조성물이 개시되어 있다(특허문헌 1 참조).As a material having a high refractive index in optical material applications, (meth)acrylate having a fluorene skeleton is known, for example, polyfunctional (meth)acryl having a fluorene skeleton in which the number of oxyalkylene groups added is large. A curable composition containing a lactate and phenoxybenzyl (meth)acrylate is disclosed (refer to patent document 1).
상기 경화성 조성물은, 플루오렌 골격을 갖는 (메타)아크릴레이트의 옥시알킬렌기의 부가수를 크게 함으로써, 높은 굴절률과 내스크래치성을 양립할 수 있는 것이 개시되어 있다. 그러나, 프리즘 시트에 있어서는, 디스플레이를 구성하는 다른 필름 등과의 중첩에 있어서 긁힘이 발생하면 집광 능력이 저하하므로, 추가적인 내긁힘성이나 자기치유성의 향상이 요구되고 있었다. 또한, 이들 특성과 함께 습열 환경 하에서의 높은 밀착성의 실현도 요구되고 있었다.It is disclosed that the said curable composition is compatible with a high refractive index and scratch resistance by enlarging the addition number of the oxyalkylene group of (meth)acrylate which has a fluorene skeleton. However, in the prism sheet, if scratching occurs in overlapping with other films constituting the display, the light collecting ability is lowered. Moreover, realization of high adhesiveness in a moist heat environment was also calculated|required with these characteristics.
본 발명의 과제는, 높은 굴절률을 가지면서, 내스크래치성이 우수하고, 긁힘이 발생했을 때에도 호적한 자기치유성을 가지며, 또한 우수한 습열밀착성을 갖는 광학물품을 형성할 수 있는 활성 에너지선 경화형 수지 조성물을 제공하는 것에 있다.The object of the present invention is an active energy ray-curable resin capable of forming an optical article having a high refractive index, excellent scratch resistance, suitable self-healing properties even when scratched, and excellent wet heat adhesion to provide a composition.
본 발명은, 활성 에너지선 중합성 화합물(A) 및 광중합개시제(B)를 함유하는 광학물품용 활성 에너지선 경화성 조성물로서, 활성 에너지선 중합성 화합물(A)로서 하기 식(1)으로 표시되는 화합물 및 하기 식(2)으로 표시되는 화합물을 함유하는 광학물품용 활성 에너지선 경화성 조성물을 제공한다.The present invention is an active energy ray-curable composition for optical articles containing an active energy ray polymerizable compound (A) and a photopolymerization initiator (B), wherein the active energy ray polymerizable compound (A) is represented by the following formula (1) An active energy ray-curable composition for optical articles containing a compound and a compound represented by the following formula (2) is provided.
(식(1) 중, R1 및 R2는, 서로 독립해서 수소 원자 또는 메틸기를 나타내고, X1 및 X2는, 서로 독립해서 탄소 원자수 2 또는 3의 알킬렌기를 나타내고, m 및 n은 서로 독립해서 0 이상의 정수를 나타내고, m+n은 20 이상이다) (In formula (1), R1 and R2 each independently represent a hydrogen atom or a methyl group, X1 and X2 each independently represent an alkylene group having 2 or 3 carbon atoms, and m and n are each independently 0 represents an integer equal to or greater than or equal to, and m+n is 20 or greater)
본 발명의 광학물품용 활성 에너지선 경화성 조성물은, 장쇄의 알킬렌옥사이드쇄를 갖는 플루오렌계 (메타)아크릴레이트와, 페녹시벤질아크릴레이트를 사용함으로써, 습열밀착성이나 내스크래치성을 확보하면서, 높은 굴절률과, 호적한 자기치유성을 실현할 수 있다. 당해 조성물을 경화한 경화물은, 높은 굴절률을 가지면서, 내스크래치성이 우수하며, 또한 긁힘이 발생했을 때에도 호적한 자기치유성을 갖고, 우수한 습열밀착성을 가지므로, 각종 광학물품용, 예를 들면, 액정 표시 장치 등의 디스플레이에 사용되는 프리즘 시트, 입체 사진이나 투영 스크린 등에 사용되는 렌티큘러 렌즈 시트, 오버헤드 프로젝터의 콘덴서 렌즈 등에 사용되는 프레넬 렌즈 시트, 컬러필터 등에 사용되는 회절 격자 등의 각종 광학 시트에 호적하게 적용할 수 있다.The active energy ray-curable composition for an optical article of the present invention uses a fluorene-based (meth)acrylate having a long-chain alkylene oxide chain and phenoxybenzyl acrylate, while securing wet heat adhesion and scratch resistance, A high refractive index and suitable self-healing properties can be realized. The cured product obtained by curing the composition has a high refractive index, has excellent scratch resistance, and has suitable self-healing properties even when scratches occur, and has excellent wet heat adhesion, so For example, a prism sheet used for a display such as a liquid crystal display device, a lenticular lens sheet used for a stereoscopic photograph or a projection screen, a Fresnel lens sheet used for a condenser lens of an overhead projector, a diffraction grating used for a color filter, etc. It can apply suitably to an optical sheet.
(활성 에너지선 중합성 화합물) (Active energy ray polymerizable compound)
본 발명의 광학물품용 활성 에너지선 경화성 조성물은, 활성 에너지선 중합성 화합물(A)로서 하기 식(1)으로 표시되는 화합물을 함유한다. 본 발명에 있어서는, 하기 식(1)으로 표시되는 화합물을 함유함으로써, 얻어지는 경화물의 굴절률을 높게 할 수 있고, 또한, 호적한 내스크래치성이나 자기치유성을 실현할 수 있다.The active-energy-ray-curable composition for optical articles of this invention contains the compound represented by following formula (1) as an active-energy-ray-polymerizable compound (A). In this invention, the refractive index of the hardened|cured material obtained can be made high by containing the compound represented by following formula (1), and suitable scratch resistance and self-healing property can be implement|achieved.
(식(1) 중, R1 및 R2는, 서로 독립해서 수소 원자 또는 메틸기를 나타내고, X1 및 X2는, 서로 독립해서 탄소 원자수 2 또는 3의 알킬렌기를 나타내고, m 및 n은 서로 독립해서 0 이상의 정수를 나타내고, m+n은 20 이상이다) (In formula (1), R1 and R2 each independently represent a hydrogen atom or a methyl group, X1 and X2 each independently represent an alkylene group having 2 or 3 carbon atoms, and m and n are each independently 0 represents an integer equal to or greater than or equal to, and m+n is 20 or greater)
상기 식(1)에 있어서, m 및 n은 서로 독립해서 0 이상의 정수를 나타내고, m+n은 20 이상이다. 본 발명에 있어서는, m+n을 20 이상으로 함으로써, 양호한 습열밀착성을 확보하면서, 우수한 내스크래치성 및 자기치유성을 실현할 수 있다. m+n은 20∼30인 것이 바람직하고, 20∼25인 것이 보다 바람직하다.In the formula (1), m and n each independently represent an integer of 0 or more, and m+n is 20 or more. In the present invention, when m+n is 20 or more, excellent scratch resistance and self-healing properties can be realized while ensuring good wet-heat adhesiveness. It is preferable that it is 20-30, and, as for m+n, it is more preferable that it is 20-25.
본 발명에 사용하는 상기 식(1)으로 표시되는 화합물은, 그 굴절률이 1.50 이상인 것이 바람직하고, 1.53 이상인 것이 보다 바람직하다. 또한, 그 점도는 5000mPa·s 이하인 것이 바람직하고, 3000mPa·s 이하인 것이 보다 바람직하다.It is preferable that the refractive index is 1.50 or more, and, as for the compound represented by the said Formula (1) used for this invention, it is more preferable that it is 1.53 or more. Moreover, it is preferable that it is 5000 mPa*s or less, and, as for the viscosity, it is more preferable that it is 3000 mPa*s or less.
본 발명에 있어서는, 상기 식(1)으로 표시되는 화합물과 함께, 하기 식(2)으로 표시되는 화합물을 함유함으로써, 얻어지는 경화물의 굴절률을 현저하게 떨어트리지 않고, 경화물의 자기치유성을 높일 수 있다.In the present invention, by containing the compound represented by the following formula (2) together with the compound represented by the formula (1), the self-healing property of the cured product can be improved without significantly lowering the refractive index of the obtained cured product. .
본 발명의 광학물품용 활성 에너지선 경화성 조성물에 있어서는, 당해 조성물에 포함되는 활성 에너지선 중합성 화합물(A) 중의 식(1)으로 표시되는 화합물의 함유량이 10∼50질량%인 것이 바람직하고, 20∼40질량%인 것이 보다 바람직하다. 식(1)으로 표시되는 화합물에 의해, 높은 굴절률, 호적한 유연성이나 자기치유성을 실현할 수 있다. 또한, 식(1)으로 표시되는 화합물의 함유량을 상기 상한 이하로 함으로써, 경화물이 너무 유연해지지 않고, 또한 흡수성을 억제하기 쉬워지므로, 습열 처리 후의 기재와의 호적한 밀착성(장기신뢰성)을 얻기 쉬워진다. 또한, 당해 화합물의 함유량을 상기 하한 이하로 함으로써, 높은 굴절률을 확보하기 쉬워진다.In the active energy ray-curable composition for optical articles of the present invention, the content of the compound represented by Formula (1) in the active energy ray-polymerizable compound (A) contained in the composition is preferably 10 to 50 mass%, It is more preferable that it is 20-40 mass %. By the compound represented by Formula (1), a high refractive index, suitable flexibility, and self-healing property can be implement|achieved. In addition, by making the content of the compound represented by the formula (1) below the upper limit, the cured product does not become too soft and absorbency is easily suppressed, so that suitable adhesion (long-term reliability) with the substrate after moist heat treatment is obtained. it gets easier Moreover, when content of the said compound shall be below the said minimum, it becomes easy to ensure a high refractive index.
또한, 활성 에너지선 중합성 화합물(A) 중의 식(2)으로 표시되는 화합물의 함유량이 10∼70질량%인 것이 바람직하고, 20∼60질량%인 것이 보다 바람직하고, 40∼50질량%인 것이 더 바람직하다. 식(2)으로 표시되는 화합물은 폴리머 Tg가 낮고, 경화물에 호적한 유연성을 부여할 수 있고, 당해 식(2)으로 표시되는 화합물의 함유량을 상기 범위로 함으로써, 당해 유연성에 의한 호적한 자기치유성을 가지면서, 경화물의 호적한 강도나 기재와의 양호한 밀착성을 실현하기 쉬워진다.Moreover, it is preferable that content of the compound represented by Formula (2) in an active energy ray-polymerizable compound (A) is 10-70 mass %, It is more preferable that it is 20-60 mass %, It is 40-50 mass % it is more preferable The compound represented by the formula (2) has a low polymer Tg, can impart suitable flexibility to the cured product, and when the content of the compound represented by the formula (2) is within the above range, suitable magnetic properties due to the flexibility It becomes easy to implement|achieve suitable intensity|strength of hardened|cured material, and favorable adhesiveness with a base material, having curable property.
상술한 바와 같이 식(1)으로 표시되는 화합물과 식(2)으로 표시되는 화합물을 소정의 배합량을 최적화함에 의해, 고굴절률과 자기치유성과 습열 처리 후의 기재와의 밀착성(장기신뢰성)을 겸비하기 쉬워진다. 또한, 점도의 조정 등, 다른 물성 밸런스를 갖게 하기 위해서, 타성분을 배합하는 것이 가능하지만, 상기한 효과를 발현하기 위해서는, 활성 에너지선 중합성 화합물(A)에 포함되는 식(1)으로 표시되는 화합물과, 식(2)으로 표시되는 화합물의 합계의 함유량이, 40∼90질량%인 것이 바람직하고, 50∼80질량%인 것이 보다 바람직하다.As described above, by optimizing a predetermined compounding amount of the compound represented by the formula (1) and the compound represented by the formula (2), to combine high refractive index and self-healing properties and adhesion (long-term reliability) to the substrate after moist heat treatment it gets easier In addition, in order to have other physical property balance, such as adjustment of a viscosity, it is possible to mix|blend other components, In order to express the said effect, it is represented by Formula (1) contained in an active-energy-ray-polymerizable compound (A). It is preferable that it is 40-90 mass %, and, as for content of the total of the compound used and the compound represented by Formula (2), it is more preferable that it is 50-80 mass %.
본 발명의 광학물품용 활성 에너지선 경화성 조성물은, 상기 식(1) 및 식(2)으로 표시되는 화합물 이외의 다른 활성 에너지선 중합성 화합물을 함유해도 된다. 당해 다른 활성 에너지선 중합성 화합물로서는, 활성 에너지선 중합성기를 하나 갖는 단관능의 화합물, 당해 중합성기를 둘 이상 갖는 다관능의 화합물을 적의(適宜) 사용할 수 있다.The active energy ray-curable composition for optical articles of this invention may contain other active energy ray-polymerizable compounds other than the compound represented by said Formula (1) and Formula (2). As said other active energy ray-polymerizable compound, the monofunctional compound which has one active energy ray-polymerizable group, and the polyfunctional compound which has two or more of the said polymerizable groups can be used suitably.
단관능의 화합물로서는, 예를 들면, n-부틸(메타)아크릴레이트, 이소부틸(메타)아크릴레이트, tert-부틸(메타)아크릴레이트, n-펜틸(메타)아크릴레이트, n-헥실(메타)아크릴레이트, n-옥틸(메타)아크릴레이트, 이소옥틸(메타)아크릴레이트, 2-에틸헥실(메타)아크릴레이트, 벤질(메타)아크릴레이트, 페닐벤질(메타)아크릴레이트, 페녹시에틸(메타)아크릴레이트, 페녹시디에틸렌글리콜(메타)아크릴레이트, 글리시딜(메타)아크릴레이트, 모르폴린(메타)아크릴레이트, 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 디에틸렌글리콜모노(메타)아크릴레이트, 트리에틸렌글리콜모노(메타)아크릴레이트, 디프로필렌글리콜모노(메타)아크릴레이트, 2-메톡시에틸(메타)아크릴레이트, 메톡시디에틸렌글리콜(메타)아크릴레이트, 메톡시트리에틸렌글리콜(메타)아크릴레이트, 메톡시폴리에틸렌글리콜(메타)아크릴레이트, 2-부톡시에틸(메타)아크릴레이트, 부톡시트리에틸렌글리콜(메타)아크릴레이트, 2-에톡시에틸(메타)아크릴레이트, 2-(2-에톡시에톡시)에틸(메타)아크릴레이트, 에톡시폴리에틸렌글리콜(메타)아크릴레이트, 4-노닐페녹시에틸렌글리콜(메타)아크릴레이트, 테트라히드로푸르푸릴(메타)아크릴레이트, 카프로락톤 변성 테트라히드로푸르푸릴(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 이소보르닐(메타)아크릴레이트, 2-히드록시-3-페녹시프로필(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 시클로헥실메틸(메타)아크릴레이트, 시클로헥실에틸(메타)아크릴레이트, 디시클로펜타닐(메타)아크릴레이트, 디시클로펜타닐옥시에틸(메타)아크릴레이트, 디시클로펜테닐(메타)아크릴레이트, 디시클로펜테닐옥시에틸(메타)아크릴레이트, 페닐페녹시에틸아크릴레이트 등의 단관능 (메타)아크릴레이트를 바람직하게 사용할 수 있다. 이들 단관능 (메타)아크릴레이트는, 1종을 사용해도 되고 복수 종을 사용해도 된다.Examples of the monofunctional compound include 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, phenylbenzyl (meth) acrylate, phenoxyethyl ( Meth) acrylate, phenoxydiethylene glycol (meth) acrylate, glycidyl (meth) acrylate, morpholine (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) ) acrylate, 4-hydroxybutyl (meth) acrylate, diethylene glycol mono (meth) acrylate, triethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, 2-methoxyethyl (meth)acrylate, methoxydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, 2-butoxyethyl (meth)acrylate, butoxy Triethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-(2-ethoxyethoxy) ethyl (meth) acrylate, ethoxy polyethylene glycol (meth) acrylate, 4-nonyl Phenoxyethylene 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, cyclohexylmethyl (meth) acrylate, cyclohexylethyl (meth) acrylate, dicyclopentanyl (meth) acrylate , dicyclopentanyloxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, monofunctional (meth) acrylates such as phenylphenoxyethyl acrylate It can be used preferably. These monofunctional (meth)acrylates may use 1 type or may use multiple types.
본 발명에 사용하는 단관능 화합물로서는, 25℃에 있어서의 점도가 300mPa·s 이하인 화합물을 사용하는 것이 바람직하고, 200mPa·s 이하인 화합물인 것이 보다 바람직하다. 또한, 그 굴절률이 25℃, 589㎚에 있어서, 1.4 이상인 것이 바람직하고, 1.5 이상인 것이 보다 바람직하고, 1.55 이상인 것이 더 바람직하다.As a monofunctional compound used for this invention, it is preferable to use the compound whose viscosity in 25 degreeC is 300 mPa*s or less, and it is more preferable that it is a compound whose viscosity is 200 mPa*s or less. Moreover, it is preferable that the refractive index is 1.4 or more in 25 degreeC and 589 nm, It is more preferable that it is 1.5 or more, It is more preferable that it is 1.55 or more.
상기한 단관능 화합물 중에서도, 하기 식(3)으로 표시되는 o-페닐페놀의 에틸렌옥사이드 변성 아크릴레이트는, 조성물의 점도를 호적하게 유지하면서, 얻어지는 경화물의 굴절률을 향상시키기 쉽기 때문에 바람직하다.Among the above-described monofunctional compounds, ethylene oxide-modified acrylate of o-phenylphenol represented by the following formula (3) is preferable because it is easy to improve the refractive index of the resulting cured product while maintaining the viscosity of the composition suitably.
식(3)으로 표시되는 화합물을 사용하는 경우에는, 본 발명의 광학물품용 활성 에너지선 경화성 조성물에 포함되는 활성 에너지선 중합성 화합물(A) 중의 식(3)으로 표시되는 화합물의 함유량이 5∼30질량%인 것이 바람직하고, 15∼25질량%인 것이 보다 바람직하다.When the compound represented by Formula (3) is used, content of the compound represented by Formula (3) in the active energy ray polymeric compound (A) contained in the active energy ray-curable composition for optical articles of this invention is 5 It is preferable that it is -30 mass %, and it is more preferable that it is 15-25 mass %.
또한, 하기 식(4)으로 표시되는 페닐벤질아크릴레이트는, 조성물의 점도를 호적하게 유지하면서, 얻어지는 경화물의 굴절률을 향상시키기 쉽기 때문에 바람직하다.Moreover, since it is easy to improve the refractive index of the hardened|cured material obtained, phenylbenzyl acrylate represented by following formula (4) maintaining the viscosity of a composition suitably, it is preferable.
식(4)으로 표시되는 화합물을 사용하는 경우에는, 본 발명의 광학물품용 활성 에너지선 경화성 조성물에 포함되는 활성 에너지선 중합성 화합물(A) 중의 식(4)으로 표시되는 화합물의 함유량이 5∼30질량%인 것이 바람직하고, 10∼20질량%인 것이 보다 바람직하다.When the compound represented by Formula (4) is used, content of the compound represented by Formula (4) in the active energy ray-polymerizable compound (A) contained in the active energy ray-curable composition for optical articles of this invention is 5 It is preferable that it is -30 mass %, and it is more preferable that it is 10-20 mass %.
다관능의 화합물로서는, 예를 들면, 에틸렌글리콜디(메타)아크릴레이트, 디에틸렌글리콜디(메타)아크릴레이트, 트리에틸렌글리콜디(메타)아크릴레이트, 폴리에틸렌글리콜디(메타)아크릴레이트, 프로필렌글리콜디(메타)아크릴레이트, 디프로필렌글리콜디(메타)아크릴레이트, 트리프로필렌글리콜디(메타)아크릴레이트, 부틸렌글리콜디(메타)아크릴레이트, 테트라부틸렌글리콜디(메타)아크릴레이트, 1,4-부탄디올디(메타)아크릴레이트, 1,6-헥산디올디(메타)아크릴레이트, 1,9-노난디올디(메타)아크릴레이트, 네오펜틸글리콜디(메타)아크릴레이트, As the polyfunctional compound, for example, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol Di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, tetrabutylene 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,
비스페놀A의 에틸렌옥사이드 부가물의 디(메타)아크릴레이트, 비스페놀A의 프로필렌옥사이드 부가물의 디(메타)아크릴레이트, 비스페놀F의 에틸렌옥사이드 부가물의 디(메타)아크릴레이트, 비스페놀F의 프로필렌옥사이드 부가물의 디(메타)아크릴레이트, 디시클로펜타닐디(메타)아크릴레이트, 글리세롤디(메타)아크릴레이트, 네오펜틸글리콜히드록시피발산에스테르디(메타)아크릴레이트, 카프로락톤 변성 히드록시피발산네오펜틸글리콜디(메타)아크릴레이트, 테트라브로모비스페놀A디(메타)아크릴레이트, 히드로피발알데히드 변성 트리메틸올프로판디(메타)아크릴레이트, 1,4-시클로헥산디메탄올디(메타)아크릴레이트, 트리메틸올프로판트리(메타)아크릴레이트, 트리메틸올프로판의 에틸렌옥사이드 부가물의 트리(메타)아크릴레이트, 트리메틸올프로판의 프로필렌옥사이드 부가물의 트리(메타)아크릴레이트, 펜타에리트리톨트리(메타)아크릴레이트, 글리세롤트리(메타)아크릴레이트, 알킬 변성한 디펜타에리트리톨의 트리(메타)아크릴레이트, 디트리메틸올프로판테트라(메타)아크릴레이트, 디트리메틸올프로판의 에틸렌옥사이드 부가물의 테트라(메타)아크릴레이트, 디트리메틸올프로판의 프로필렌옥사이드 부가물의 테트라(메타)아크릴레이트 등의 다관능 (메타)아크릴레이트를 예시할 수 있다.Di(meth)acrylate of ethylene oxide adduct of bisphenol A, di(meth)acrylate of propylene oxide adduct of bisphenol A, di(meth)acrylate of ethylene oxide adduct of bisphenol F, di of propylene oxide adduct of bisphenol F (meth)acrylate, dicyclofentanyl di(meth)acrylate, glycerol di(meth)acrylate, neopentyl glycol hydroxypivalate di(meth)acrylate, caprolactone-modified hydroxypivalate neopentyl glycol di (meth)acrylate, tetrabromobisphenol A di(meth)acrylate, hydropivalaldehyde-modified trimethylolpropane di(meth)acrylate, 1,4-cyclohexanedimethanol di(meth)acrylate, trimethylolpropane Tri(meth)acrylate, tri(meth)acrylate of ethylene oxide adduct of trimethylolpropane, tri(meth)acrylate of propylene oxide adduct of trimethylolpropane, pentaerythritol tri(meth)acrylate, glycerol tri( meth)acrylate, tri(meth)acrylate of alkyl-modified dipentaerythritol, ditrimethylolpropanetetra(meth)acrylate, tetra(meth)acrylate of ethylene oxide adduct of ditrimethylolpropane, ditrimethylol Polyfunctional (meth)acrylates, such as the tetra (meth)acrylate of the propylene oxide adduct of propane, can be illustrated.
또한, 다관능 (메타)아크릴레이트로서는, 예를 들면 우레탄(메타)아크릴레이트, 폴리에스테르(메타)아크릴레이트, 에폭시(메타)아크릴레이트 등의 아크릴로일기를 갖는 다관능 올리고머도 포함된다.Moreover, as polyfunctional (meth)acrylate, the polyfunctional oligomer which has acryloyl groups, such as urethane (meth)acrylate, polyester (meth)acrylate, and epoxy (meth)acrylate, is also contained, for example.
이들은, 1종을 사용해도 되고 복수 종을 사용해도 된다.These may use 1 type and may use multiple types.
또한, 높은 굴절률의 경화물을 얻는데 있어서는, 상기 식(1)으로 표시되는 구조에 있어서 m+n이 20 미만인 (메타)아크릴레이트를 병용해도 된다. 당해 (메타)아크릴레이트를 사용하는 경우에는, 활성 에너지선 중합성 화합물 중의 20질량% 이하로 사용하는 것이 바람직하고, 10질량% 이하로 사용하는 것이 바람직하다.Moreover, in obtaining the hardened|cured material of a high refractive index, in the structure represented by the said Formula (1), you may use together the (meth)acrylate whose m+n is less than 20. When using the said (meth)acrylate, it is preferable to use at 20 mass % or less in an active energy ray polymeric compound, and it is preferable to use at 10 mass % or less.
또한, 본 발명의 활성 에너지선 경화형 수지 조성물에 있어서는, 상기 (메타)아크릴레이트 이외의 활성 에너지선 중합성기를 갖는 화합물을 사용할 수도 있다. 또한, 이들 (메타)아크릴레이트 이외의 화합물을 사용하는 경우에는, 활성 에너지선 중합성 화합물 중의 20질량% 이하로 사용하는 것이 바람직하고, 10질량% 이하로 사용하는 것이 보다 바람직하다.Moreover, in the active energy ray-curable resin composition of this invention, you can also use the compound which has active energy ray-polymerizable groups other than the said (meth)acrylate. Moreover, when using compounds other than these (meth)acrylates, it is preferable to use at 20 mass % or less in an active energy ray polymeric compound, and it is more preferable to use at 10 mass % or less.
(광중합개시제) (Photoinitiator)
본 발명에 사용하는 광중합개시제는, 활성 에너지선 경화형 수지 조성물에 사용되는 각종 개시제를 사용할 수 있으며, 예를 들면, 1-히드록시시클로헥실페닐케톤, 2-히드록시-2-메틸-1-페닐프로판-1-온, 1-〔4-(2-히드록시에톡시)페닐〕-2-히드록시-2-메틸-1-프로판-1-온, 티오잔톤 및 티오잔톤 유도체, 2,2'-디메톡시-1,2-디페닐에탄-1-온, 2,4,6-트리메틸벤조일디페닐포스핀옥사이드, 비스(2,4,6-트리메틸벤조일)페닐포스핀옥사이드, 2-메틸-1-[4-(메틸티오)페닐]-2-모르폴리노-1-프로판온, 2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐)-부탄-1-온 등을 바람직하게 사용할 수 있다. 이들 개시제는 1종만을 사용해도 되고 2종 이상을 혼합해서 사용해도 된다.As the photopolymerization initiator used in the present invention, various initiators used in the active energy ray-curable resin composition can be used, for example, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl Propan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2' -Dimethoxy-1,2-diphenylethan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-methyl- 1-[4-(methylthio)phenyl]-2-morpholino-1-propanone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. It can be used preferably. These initiators may use only 1 type, and may mix and use 2 or more types.
광중합개시제의 사용량은 특히 제한은 없지만, 호적한 경화성이나, 얻어지는 경화물의 호적한 내스크래치성이나 자기치유성 등을 얻기 쉬우므로, 광학물품용 활성 에너지선 경화형 수지 조성물 중의 활성 에너지선 중합성 화합물 100질량부에 대해서 0.05∼20질량부인 것이 바람직하고, 0.1∼10질량부인 것이 특히 바람직하다.The amount of the photoinitiator used is not particularly limited, but suitable curability and suitable scratch resistance and self-healing properties of the resulting cured product are easy to be obtained. It is preferable that it is 0.05-20 mass parts with respect to a mass part, and it is especially preferable that it is 0.1-10 mass parts.
(활성 에너지선 경화형 수지 조성물) (Active energy ray-curable resin composition)
본 발명의 광학물품용 활성 에너지선 경화형 수지 조성물은, 상기 식(1)으로 표시되는 쇄장이 긴 옥시알킬렌기를 갖는 플루오렌 골격의 (메타)아크릴레이트와, 식(2)으로 표시되는 폴리머 Tg가 낮고 비교적 굴절률이 높은 페녹시벤질아크릴레이트를 함유함으로써, 고굴절률과 함께, 호적한 자기치유성이나 기계 강도를 실현할 수 있으며, 또한 양호한 습열밀착성을 겸비할 수 있다.The active energy ray-curable resin composition for an optical article of the present invention comprises a (meth)acrylate having a fluorene skeleton having a long oxyalkylene group represented by the formula (1), and a polymer Tg represented by the formula (2) By containing phenoxybenzyl acrylate with a low , relatively high refractive index, suitable self-healing properties and mechanical strength can be realized along with a high refractive index, and good wet-heat adhesiveness can be achieved.
본 발명의 활성 에너지선 경화형 수지 조성물은, 각종 광학물품 용도에 있어서 원하는 형상이나 두께로의 도포·성형이 하기 쉬우므로, 25℃에서의 점도가 50∼5000mPa·s인 것이 바람직하고, 100∼2000mPa·s인 것이 보다 바람직하다. 특히, 프리즘 시트 용도에 적용하는 경우에는, 프리즘 시트의 모형(母型)에 균일하게 도포하기 쉽고, 또한 미세 요철 구조를 갖는 모형의 복제가 하기 쉬우므로(라인 스피드를 빠르게 하는 것이 가능하므로), 50∼500mPa·s인 것이 바람직하다.Since the active energy ray-curable resin composition of the present invention is easy to apply and mold to a desired shape or thickness in various optical article applications, the viscosity at 25°C is preferably 50 to 5000 mPa·s, and 100 to 2000 mPa It is more preferable that it is s. In particular, when applied to a prism sheet use, it is easy to apply uniformly to the model of the prism sheet, and it is easy to duplicate the model having a fine concavo-convex structure (since it is possible to increase the line speed), It is preferable that it is 50-500 mPa*s.
본 발명의 활성 에너지선 경화형 수지 조성물에 있어서는, 상기 활성 에너지선 중합성 화합물 이외의 성분을 함유해도 되며, 예를 들면, 점도나 투명 기판에의 접착성 개량 등을 목적으로 수지 등을 병용해도 된다. 당해 수지로서는, 예를 들면, 메틸메타크릴레이트 수지, 메틸메타크릴레이트계 공중합물 등의 아크릴 수지; 폴리스티렌, 메틸메타크릴레이트-스티렌계 공중합물; 폴리에스테르 수지; 폴리우레탄 수지; 폴리부타디엔이나 부타디엔-아크릴로니트릴계 공중합물 등의 폴리부타디엔 수지; 비스페놀형 에폭시 수지, 페녹시 수지나 노볼락형 에폭시 수지 등의 에폭시 수지 등을 들 수 있다. 이들 활성 에너지선 중합성 화합물 이외의 성분을 사용하는 경우에는, 활성 에너지선 중합성 화합물 100질량부에 대해서 20질량부 이하로 사용하는 것이 바람직하고, 10질량부 이하로 사용하는 것이 바람직하다.In the active energy ray-curable resin composition of this invention, you may contain components other than the said active energy ray-polymerizable compound, For example, you may use resin etc. together for the purpose of viscosity, adhesive improvement to a transparent substrate, etc. . As said resin, For example, Acrylic resins, such as a methyl methacrylate resin and a methyl methacrylate type copolymer; polystyrene, methyl methacrylate-styrene-based copolymer; polyester resin; polyurethane resin; polybutadiene resins such as polybutadiene and butadiene-acrylonitrile copolymers; Epoxy resins, such as a bisphenol-type epoxy resin, a phenoxy resin, and a novolak-type epoxy resin, etc. are mentioned. When using components other than these active energy ray-polymerizable compounds, it is preferable to use at 20 mass parts or less with respect to 100 mass parts of active energy ray-polymerizable compounds, and it is preferable to use at 10 mass parts or less.
(무기 필러) (inorganic filler)
본 발명에 있어서는, 필요에 따라서 무기 재료(나노 입자)를 배합하는 것이 가능하다.In this invention, it is possible to mix|blend an inorganic material (nanoparticle) as needed.
굴절률이 높은 무기 나노 입자로서는, 알루미나, 지르코니아, 티타니아, 그들의 화합물, 혹은 그들의 혼합 산화물을 포함하거나, 또는 그들의 금속 산화물을 들 수 있다. 이들 무기 나노 입자(필러)는, 일반적인 유기 재료보다도 굴절률이 높으므로 경화물의 굴절률을 높이는 수단으로서는 유효하지만, 성형물의 강도나 기재밀착성과의 밸런스를 고려할 필요가 있고, 배합량으로서는, 활성 에너지선 중합성 화합물(A)과 무기 나노 입자의 합계량에 대해서, 무기 나노 입자가 20∼60질량%로 되는 범위가 실용적이다. 또한, 그 중에서도, 고굴절률과 자기치유성을 더 겸비하기 위해서는, 30∼50질량%가 보다 바람직하다.Examples of inorganic nanoparticles having a high refractive index include alumina, zirconia, titania, compounds thereof, or mixed oxides thereof, or metal oxides thereof. Since these inorganic nanoparticles (fillers) have a higher refractive index than general organic materials, they are effective as a means of increasing the refractive index of the cured product. With respect to the total amount of the compound (A) and the inorganic nanoparticles, the range in which the inorganic nanoparticles are 20 to 60% by mass is practical. Moreover, especially, in order to have a high refractive index and self-healing property further, 30-50 mass % is more preferable.
(첨가제) (additive)
또한, 본 발명의 활성 에너지선 경화형 수지 조성물에 있어서는, 각종 첨가제를 사용해도 된다. 당해 첨가제로서는, 예를 들면, 자외선 흡수제, 산화방지제, 실리콘계 첨가제, 불소계 첨가제, 레올로지컨트롤제, 탈포제, 이형제, 실란커플링제, 대전방지제, 방담제, 착색제 등을 들 수 있다. 이들 첨가제는, 광학물품용 활성 에너지선 경화형 수지 조성물 중의 활성 에너지선 중합성 화합물 100질량부에 대해서 0.05∼20질량부인 것이 바람직하고, 0.1∼10질량부인 것이 특히 바람직하다.In addition, in the active energy ray-curable resin composition of this invention, you may use various additives. Examples of the additive include a UV absorber, antioxidant, silicone additive, fluorine-based additive, rheology control agent, defoaming agent, mold release agent, silane coupling agent, antistatic agent, antifogging agent, and colorant. It is preferable that it is 0.05-20 mass parts with respect to 100 mass parts of active energy ray-polymerizable compounds in the active-energy-ray-curable resin composition for optical articles, and, as for these additives, it is especially preferable that it is 0.1-10 mass parts.
본 발명의 광학물품용 활성 에너지선 경화형 수지 조성물에는 필요에 따라서 용제를 함유시켜도 되지만, 용제의 함유율은 적은 편이 작업 환경을 오염하기 어려운 광학물품용 활성 에너지선 경화형 수지 조성물이 얻어지므로 바람직하다. 구체적으로는, 본 발명의 광학물품용 활성 에너지선 경화형 수지 조성물 중의 용제 함유율은 1질량% 이하가 바람직하고, 실질적으로 함유하지 않는 것이 바람직하다.Although the active energy ray-curable resin composition for optical articles of the present invention may contain a solvent as needed, the lower content of the solvent is preferable because the active energy ray-curable resin composition for optical articles is less likely to contaminate the working environment. Specifically, as for the solvent content in the active energy ray-curable resin composition for optical articles of this invention, 1 mass % or less is preferable, and it is preferable not to contain substantially.
(경화물) (cured product)
본 발명의 활성 에너지선 경화형 수지 조성물은, 목적 용도에 따라서 기재에의 도포나, 성형한 후, 활성 에너지선을 조사해서 경화물로 할 수 있다. 활성 에너지선으로서는, 전자선, 자외선, 가시광선 등을 들 수 있다. 활성 에너지선으로서, 전자선을 사용하는 경우에는, 코크로프트 월턴형 가속기, 밴더 그래프형 전자 가속기, 공진 변압기형 가속기, 절연 코어 변압기형, 다이나미트론형, 리니어 필라멘트형 및 고주파형 등의 전자선 발생 장치를 사용해서 본 발명의 경화성 조성물을 경화시킬 수 있다. 또한, 활성 에너지선으로서 자외선을 사용하는 경우는, 초고압 수은등, 고압 수은등, 저압 수은등 등의 수은등, 제논 램프, 카본 아크, 메탈 할라이드 램프, 고출력의 LED-UV 램프 등에 의해 조사하여, 경화시킬 수 있다.The active energy ray-curable resin composition of this invention can be irradiated with an active energy ray, and can be set as hardened|cured material after application|coating to a base material and shaping|molding according to the objective use. As an active energy ray, an electron beam, an ultraviolet-ray, a visible ray, etc. are mentioned. When an electron beam is used as an active energy ray, electron beam generators, such as a Cockcroft Walton type accelerator, a Vandergraph type electron accelerator, a resonance transformer type accelerator, an insulated core transformer type, a dynamtron type, a linear filament type, and a high frequency type can be used to cure the curable composition of the present invention. In addition, when ultraviolet rays are used as active energy rays, mercury lamps such as ultra-high pressure mercury lamps, high pressure mercury lamps, low pressure mercury lamps, xenon lamps, carbon arcs, metal halide lamps, high output LED-UV lamps, etc. can be irradiated and cured. .
본 발명의 활성 에너지선 경화형 수지 조성물의 경화물은, 굴절률이 1.5 이상인 것이 바람직하고, 1.54 이상인 것이 보다 바람직하다. 당해 경화물은, 높은 굴절률을 갖고, 또한 호적한 내스크래치성 등을 가지므로, 각종 광학물품에 호적하게 적용할 수 있다.It is preferable that refractive index is 1.5 or more, and, as for the hardened|cured material of the active-energy-ray-curable resin composition of this invention, it is more preferable that it is 1.54 or more. Since the said hardened|cured material has a high refractive index and has suitable scratch resistance etc., it can apply suitably to various optical articles.
본 발명의 경화물의 경도는, 각종 용도에 따라서 적의 설계하면 되지만, 예를 들면, 프리즘 시트에 사용하는 경우에는, 25℃에 있어서의 탄성률이 5∼500MPa인 것이 바람직하고, 10∼100MPa인 것이 보다 바람직하다. 탄성률을 당해 범위로 함으로써 기계 강도와 인성(신장)의 밸런스가 양호하게 되고, 자기치유성에 필요한 복원력을 발현하기 쉬워진다.The hardness of the cured product of the present invention may be appropriately designed according to various uses. For example, when used for a prism sheet, the elastic modulus at 25°C is preferably 5 to 500 MPa, and more preferably 10 to 100 MPa. desirable. By setting the elastic modulus within the range, the balance between mechanical strength and toughness (elongation) becomes good, and the restoring force necessary for self-healing properties is easily developed.
또, 당해 탄성률은, 점탄성 측정 장치로서 Rheometoric Scientific사제의 「RSAII」를 사용해서, 측정 조건으로서, 승온 스피드 3℃/Min, 주파수는 3.5Hz의 조건에서 동적 점탄성 측정해서 얻어지는 값으로 한다.In addition, the said elastic modulus is a value obtained by using "RSAII" manufactured by Rheometoric Scientific as a viscoelasticity measuring device, performing dynamic viscoelasticity measurement under conditions of a temperature increase speed of 3°C/Min as measurement conditions and a frequency of 3.5 Hz.
본 발명에 있어서는, 경화물의 유리 전이 온도 Tg가 40℃ 이하인 것이 바람직하고, 30℃ 이하인 것이 보다 바람직하고, 25℃ 이하인 것이 특히 바람직하다. 당해 유리 전이 온도로 함으로써, 높은 굴절률과 양호한 자기치유성을 겸비하기 쉬워진다. Tg의 하한은 특히 제한되는 것은 아니지만, 5℃ 이상인 것이 바람직하고, 10℃ 이상인 것이 보다 바람직하고, 15℃ 이상인 것이 특히 바람직하다. 또, 본 발명에 있어서는, 상기 식(1)이나 식(2)으로 표시되는 화합물의 사용이나 호적한 범위에서의 배합에 의해, 당해 Tg의 범위로 조정하기 쉬워진다.In this invention, it is preferable that the glass transition temperature Tg of hardened|cured material is 40 degrees C or less, It is more preferable that it is 30 degrees C or less, It is especially preferable that it is 25 degrees C or less. By setting it as the said glass transition temperature, it becomes easy to have a high refractive index and favorable self-healing property. Although the lower limit in particular of Tg is not restrict|limited, It is preferable that it is 5 degreeC or more, It is more preferable that it is 10 degreeC or more, It is especially preferable that it is 15 degreeC or more. Moreover, in this invention, it becomes easy to adjust to the said range of Tg by use of the compound represented by said Formula (1) or Formula (2), or mixing|blending in a suitable range.
또, 당해 유리 전이 온도는, 점탄성 측정에서 얻어지는 저장 탄성률 E'와 복소 탄성률 E"의 비로 나타나는 tanδ의 피크 위치의 온도를 Tg로서 판독한 값의 것이다.In addition, the said glass transition temperature is the thing of the value which read as Tg the temperature of the peak position of tan-delta represented by the ratio of the storage elastic modulus E' obtained by viscoelasticity measurement, and complex elastic modulus E".
(광학 시트) (optical sheet)
본 발명의 광학 시트는, 상기 광학물품용 활성 에너지선 경화형 수지 조성물의 경화물로 이루어지는 층을 갖는 광학 시트이다. 당해 광학 시트는, 투명한 수지 필름 상에, 상기 경화물로 이루어지는 프리즘이나 렌즈가 적층된 광학 시트이고, 구체적으로는, 액정 표시 장치 등의 디스플레이에 사용되는 프리즘 시트, 입체 사진이나 투영 스크린 등에 사용되는 렌티큘러 렌즈 시트, 오버헤드 프로젝터의 콘덴서 렌즈 등에 사용되는 프레넬 렌즈 시트, 컬러필터 등에 사용되는 회절 격자 등의 광학 시트를 예시할 수 있다.The optical sheet of this invention is an optical sheet which has a layer which consists of a hardened|cured material of the said active-energy-ray-curable resin composition for optical articles. The optical sheet is an optical sheet in which a prism or a lens made of the cured product is laminated on a transparent resin film, specifically, a prism sheet used in displays such as liquid crystal displays, stereoscopic photography, projection screens, etc. Optical sheets, such as a lenticular lens sheet, a Fresnel lens sheet used for the condenser lens of an overhead projector, etc., a diffraction grating used for a color filter, etc. can be illustrated.
이들 광학 시트의 제조 방법으로서는, 상기 광학물품용 활성 에너지선 경화형 수지 조성물을 각종 용도에 따라서 필요한 미세 형상을 갖는 모형 상에 충전한 후, 충전된 당해 수지 조성물 상에 기재를 공기가 혼입하지 않도록 가압 적층해서 밀착시키고, 기재측으로부터 자외선 등의 활성 에너지선을 조사해서 당해 수지 조성물을 경화시킨 후, 모형으로부터 이형하는 방법 등을 들 수 있다. 또한 예를 들면, 롤상의 모형에 당해 수지 조성물을 연속적으로 충전한 후, 충전된 당해 수지 조성물 상에 기재를 공기가 혼입하지 않도록 연속적으로 밀착시키고, 기재측으로부터 자외선 등의 활성 에너지선을 조사해서 당해 수지 조성물을 경화시킨 후, 롤상의 모형으로부터 이형하는 연속 제조 방법 등을 들 수 있다.As a method for producing these optical sheets, the active energy ray-curable resin composition for optical articles is filled onto a model having a required fine shape according to various uses, and then the base material is pressed onto the filled resin composition so as not to mix with air. After laminating|stacking and making it adhere|attach, irradiating active energy rays, such as an ultraviolet-ray, from the base material side, and hardening the said resin composition, the method of releasing from a model|model etc. are mentioned. Further, for example, after the resin composition is continuously filled in the roll-shaped model, the base material is continuously adhered to the filled resin composition so that air does not mix, and active energy rays such as ultraviolet rays are irradiated from the base material side. After hardening the said resin composition, the continuous manufacturing method etc. which release from a roll-shaped model are mentioned.
광학 시트의 형성에 사용되는 기재로서는, 필름상, 시트상, 판상의 투명 기재를 사용할 수 있다. 당해 기재의 재료는 용도 등에 따라서 적의 선택하면 되며, 예를 들면, 폴리에틸렌테레프탈레이트(PET), 폴리에틸렌나프탈레이트(PEN) 등의 폴리에스테르 수지, 트리아세틸셀룰로오스, 폴리카보네이트 수지, 메틸메타크릴레이트계 공중합물 등의 아크릴 수지, 스티렌 수지, 폴리설폰 수지, 폴리에테르설폰 수지, 폴리카보네이트 수지, 염화비닐 수지, 폴리메타크릴이미드 수지 등을 들 수 있다. 또한, 유리 기재 등의 무기 기재도 마찬가지로 사용하는 것이 가능하다.As a base material used for formation of an optical sheet, a film form, a sheet form, and a plate-shaped transparent base material can be used. The material of the base material may be appropriately selected according to the use, for example, polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), triacetyl cellulose, polycarbonate resin, methyl methacrylate copolymer Acrylic resins, such as water, styrene resin, polysulfone resin, polyether sulfone resin, polycarbonate resin, vinyl chloride resin, polymethacrylimide resin, etc. are mentioned. Moreover, it is possible to use inorganic base materials, such as a glass base material, similarly.
본 발명의 광학물품용 활성 에너지선 경화형 수지 조성물은, 각종 광학 시트 중에서도 각종 디스플레이에 사용되는 프리즘 시트에 호적하게 적용할 수 있다. 당해 프리즘 시트는, 시트상 성형체의 편면에 미세한 프리즘 형상부를 복수 갖는 것이며, 통상적으로, 액정 표시 소자의 배면(광원측)에, 당해 소자측에 프리즘면이 향하도록 배설(配設)된다.The active energy ray-curable resin composition for optical articles of the present invention can be suitably applied to a prism sheet used for various displays among various optical sheets. The prism sheet has a plurality of fine prism-shaped portions on one surface of the sheet-like molded body, and is usually disposed on the back surface (light source side) of a liquid crystal display element so that the prism surface faces toward the element side.
당해 프리즘 시트는, 투명 필름 상에 상기 광학물품용 활성 에너지선 경화형 수지 조성물의 경화물로 이루어지는 프리즘층을 갖는 시트이고, 당해 프리즘층의 형상은, 프리즘 정각의 각도 θ가 70∼110°인 것이, 집광성이 우수하고 휘도가 향상하는 점으로부터 바람직하고, 75∼100°인 것이 보다 바람직하고, 80∼95°인 것이 특히 바람직하다.The prism sheet is a sheet having a prism layer made of a cured product of the active energy ray-curable resin composition for an optical article on a transparent film, and the shape of the prism layer is that the angle θ of the prism angle is 70 to 110°. It is preferable from the point which is excellent in light condensing property and a brightness|luminance improves, It is more preferable that it is 75-100 degrees, It is especially preferable that it is 80-95 degrees.
또한, 프리즘의 피치는, 100㎛ 이하인 것이 바람직하고, 특히 70㎛ 이하인 것이, 화면의 무아레 모양의 발생 방지나, 화면의 정세도(精細度)가 보다 향상하는 점으로부터 바람직하다. 또한, 프리즘의 요철의 높이는, 프리즘 정각의 각도 θ와 프리즘의 피치의 값에 따라서 결정되지만, 바람직하게는 50㎛ 이하인 것이 바람직하다. 또한, 프리즘 렌즈의 시트 두께는, 강도면으로부터는 두꺼운 편이 바람직하지만, 광학적으로는 광의 흡수를 억제하기 위하여 얇은 편이 바람직하고, 이들의 밸런스의 점으로부터 50㎛∼1000㎛인 것이 바람직하다.Moreover, it is preferable that the pitch of a prism is 100 micrometers or less, and it is especially preferable that it is 70 micrometers or less from the point of prevention of generation|occurrence|production of a moire pattern on a screen, and the point which improves the detail of a screen more. In addition, although the height of the unevenness|corrugation of a prism is determined according to the value of the angle (theta) of the prism normal angle and the pitch of a prism, it is preferable that it is 50 micrometers or less preferably. The sheet thickness of the prism lens is preferably thicker in terms of strength, but is preferably thinner in order to suppress light absorption optically, and is preferably 50 µm to 1000 µm in terms of balance.
(실시예)(Example)
이하에 실시예 및 비교예를 들어서, 본 발명을 보다 구체적으로 설명한다. 예 중의 부 및 %는, 특히 기재되지 않는 한, 모두 질량 기준이다. 또, 실시예 및 비교예에 있어서의 특성 등의 측정 및 평가는, 이하와 같이 행했다.The present invention will be described more specifically by giving examples and comparative examples below. All parts and % in the examples are by mass unless otherwise specified. In addition, the measurement and evaluation of characteristics, etc. in an Example and a comparative example were performed as follows.
<굴절률 측정> <Measurement of refractive index>
실시예 및 비교예에서 조제한 수지 조성물의 굴절률을, ATAGO사제 다파장 압베 굴절률계(DR-M2)를 사용해서, 기준 파장(589㎚)에서 측정했다. 표의 수치는, 배합 조성물의 굴절률을 나타냈다.The refractive index of the resin composition prepared in the Example and the comparative example was measured at the reference wavelength (589 nm) using the multi-wavelength Abbe refractometer (DR-M2) made by ATAGO. The numerical value in the table showed the refractive index of the compounding composition.
<점도 측정> <Viscosity Measurement>
실시예 및 비교예에서 조제한 수지 조성물의 25℃에 있어서의 점도를, BROOKFIELD사제 E형 점도계(DV-II+VISCOMETER)를 사용해서 측정했다.The viscosity at 25 degreeC of the resin composition prepared by the Example and the comparative example was measured using the Brookfield company E-type viscometer (DV-II+VISCOMETER).
<자기치유성> <Self-Healing>
프리즘의 피치 간격 50㎛, 프리즘 높이 25㎛의 프리즘 모형에, 실시예 및 비교예에서 조제한 수지 조성물을 충전하고, 120㎛의 PET 필름을 중첩하고, 롤러로 압력을 가하면서 첩합한 후, PET 필름측으로부터 메탈 할라이드 램프에서 적산 광량 1000mJ/㎠의 조사량으로, 수지 조성물을 경화시켜, 프리즘 시트를 작성했다.After filling the resin composition prepared in Examples and Comparative Examples into a prism model having a pitch interval of 50 µm and a prism height of 25 µm, superimposing a 120 µm PET film and bonding it while applying pressure with a roller, the PET film The resin composition was hardened by the irradiation amount of 1000 mJ/cm<2> of accumulated light quantity with a metal halide lamp from the side, and the prism sheet was created.
얻어진 프리즘 시트를 송곳으로 약 3㎝ 긁고, 그때 생긴 흠집(선)이 사라질 때까지의 시간을 목시로 관찰했다.The obtained prism sheet was scraped by about 3 cm with an awl, and the time until the scratches (lines) generated at that time disappeared was visually observed.
평가 기준은 하기와 같다.The evaluation criteria are as follows.
5 : 순식간에 복원(흠집 소실) 5: Instantly restore (disappears scratches)
4 : 10초 이내에 복원(흠집 소실) 4: Restoration within 10 seconds (scratches disappear)
3 : 1분 이내에 복원(흠집 소실) 3: Restoration within 1 minute (scratches disappear)
2 : 5분 이내에 복원(흠집 소실) 2: Restoration within 5 minutes (scratches disappear)
1 : 15분 이상에서 복원(흠집 소실) 1: Restoration in 15 minutes or longer (scratches disappear)
0 : 복원하지 않음 0 : do not restore
<내스크래치성> <Scratch resistance>
상기와 마찬가지로 해서 얻어진 8㎝×12.5㎝의 프리즘 시트 상에, 1.5㎝각의 편광 필름(44% Pol)을 재치(載置)하고, 편광 필름에 하중을 가하고, 5㎝ 폭의 거리를 10㎝/초 마찰해서, 표면의 긁힘을 목시로 관찰했다. 하중을 50g씩 증가해 가고, 긁힘이 관찰되지 않는 최대 하중을 측정값으로 했다. 시험기는, 가부시키가이샤이모토세이사쿠죠제의 내마모 시험기(IMC-15FA형)를 사용했다.On the prism sheet of 8 cm x 12.5 cm obtained by carrying out similarly to the above, a 1.5 cm square polarizing film (44% Pol) was mounted, a load was applied to the polarizing film, and the distance of 5 cm width was 10 cm. It rubbed/sec, and the scratch on the surface was visually observed. The load was increased by 50 g, and the maximum load in which a scratch was not observed was made into a measured value. As the testing machine, an abrasion resistance testing machine (IMC-15FA type) manufactured by Moto Seisakujo Co., Ltd. was used.
<밀착성> <Adhesiveness>
상기와 마찬가지로 해서 얻어진 프리즘 시트를 온도 60℃, 습도 90% RH의 조건 하에 100시간 정치한 후, 커터 나이프로 10×10의 크로스컷을 행하고, 크로스컷부를 점착 테이프로 박리하는 기반목(基盤目) 시험을 행했다. 모눈칸 100에 대해서, 점착 테이프 박리 후의 잔존 모눈수를 측정했다.After the prism sheet obtained in the same manner as described above was left still for 100 hours under conditions of a temperature of 60°C and a humidity of 90% RH, a 10×10 cross-cut was performed with a cutter knife, and the cross-cut portion was peeled off with an adhesive tape. ) was tested. For the grid column 100, the number of remaining grids after peeling the adhesive tape was measured.
(실시예 1∼6, 비교예 1∼5) (Examples 1 to 6, Comparative Examples 1 to 5)
하기 표 1에 나타낸 배합으로 화합물을 용융 혼합하여, 수지 조성물을 조정했다. 얻어진 수지 조성물에 대하여, 상기 평가를 행했다. 또, 표 중의 조성물 배합량의 수치는 질량%이다.The compounds were melt-mixed in the formulation shown in Table 1 below to prepare a resin composition. The said evaluation was performed about the obtained resin composition. In addition, the numerical value of the composition compounding quantity in a table|surface is mass %.
[표 1] [Table 1]
[표 2] [Table 2]
상기 표 중에 기재된 화합물은 하기와 같다.The compounds described in the table above are as follows.
플루오렌계 디아크릴레이트(1) : 상기 식(1) 중의 R1 및 R2가 수소 원자, X1 및 X2가 에틸렌기, m+n=20의 화합물(MIWON제 Miramer HR-6200).Fluorene diacrylate (1): A compound in which R1 and R2 in the formula (1) are hydrogen atoms, X1 and X2 are ethylene groups, and m+n=20 (Mirmer HR-6200 manufactured by MIWON).
플루오렌계 디아크릴레이트(2) : 상기 식(1) 중의 R1 및 R2가 수소 원자, X1 및 X2가 에틸렌기, m+n=2의 화합물(MIWON제 Miramer HR-6042). Fluorene diacrylate (2): A compound in the formula (1) in which R1 and R2 are hydrogen atoms, X1 and X2 are ethylene groups, and m+n=2 (Miramer HR-6042 manufactured by MIWON).
플루오렌계 디아크릴레이트(3) : 상기 식(1) 중의 R1 및 R2가 수소 원자, X1 및 X2가 에틸렌기, m+n=10의 화합물(MIWON제 Miramer HR-6100).Fluorene diacrylate (3): A compound in the formula (1) in which R1 and R2 are hydrogen atoms, X1 and X2 are ethylene groups, and m+n=10 (Miramer HR-6100 manufactured by MIWON).
BPA(EO 변성) 디아크릴레이트 : 에틸렌옥사이드 변성 비스페놀A디메타크릴레이트(에틸렌옥사이드 변성량 20몰)(MIWON제 Miramer M-2200) BPA (EO modified) diacrylate: ethylene oxide modified bisphenol A dimethacrylate (ethylene oxide modified amount 20 mol) (Miramer M-2200 manufactured by MIWON)
BPA형 에폭시아크릴레이트 : 비스페놀A 골격을 갖는 에폭시아크릴레이트 BPA-type epoxy acrylate: Epoxy acrylate having a bisphenol A skeleton
o-페닐페놀의 EO 변성 아크릴레이트 : o-페닐페놀의 에틸렌옥사이드 변성(n≒1) 아크릴레이트(교에이샤가가쿠제 라이트아크릴레이트 POB-A) EO-modified acrylate of o-phenylphenol: Ethylene oxide-modified (n≒1) acrylate of o-phenylphenol (light acrylate POB-A manufactured by Kyoei Chemicals)
상기 표로부터 명백한 바와 같이, 본 발명의 수지 조성물은 높은 굴절률을 가지면서도, 자기치유성이나 내스크래치성이 우수한 호적한 내긁힘성을 갖고, 또한, 밀착성도 우수한 것이었다.As is clear from the above table, the resin composition of the present invention had a high refractive index, and had a suitable scratch resistance excellent in self-healing properties and scratch resistance, and was also excellent in adhesiveness.
Claims (8)
(식(1) 중, R1 및 R2는, 서로 독립해서 수소 원자 또는 메틸기를 나타내고, X1 및 X2는, 서로 독립해서 탄소 원자수 2 또는 3의 알킬렌기를 나타내고, m 및 n은 서로 독립해서 0 이상의 정수를 나타내고, m+n은 20 이상이다)
An active energy ray-curable composition for optical articles containing an active energy ray polymerizable compound (A) and a photoinitiator (B), wherein the active energy ray polymerizable compound (A) is a compound represented by the following formula (1) and the following formula An active energy ray-curable composition for optical articles, comprising the compound represented by (2).
(in formula (1), R1 and R2 each independently represent a hydrogen atom or a methyl group, X1 and X2 each independently represent an alkylene group having 2 or 3 carbon atoms, and m and n are each independently 0 represents an integer equal to or greater than or equal to, and m+n is 20 or greater)
활성 에너지선 중합성 화합물(A) 중의 식(1)으로 표시되는 화합물의 함유량이 10∼50질량%, 또한 식(2)으로 표시되는 화합물의 함유량이 10∼70질량%의 범위이고, 또한 식(1)으로 표시되는 화합물 및 식(2)으로 표시되는 화합물의 합계가 40∼90질량%인 광학물품용 활성 에너지선 경화성 조성물.According to claim 1,
Content of the compound represented by Formula (1) in an active energy ray-polymerizable compound (A) is 10-50 mass %, and content of the compound represented by Formula (2) is the range of 10-70 mass %, and The active energy ray-curable composition for optical articles whose sum total of the compound represented by (1) and the compound represented by Formula (2) is 40-90 mass %.
활성 에너지선 중합성 화합물(A)로서 하기 식(3)으로 표시되는 화합물을 함유하는 광학물품용 활성 에너지선 경화성 조성물.
3. The method of claim 1 or 2,
The active energy ray-curable composition for optical articles containing the compound represented by following formula (3) as an active-energy-ray-polymerizable compound (A).
활성 에너지선 중합성 화합물(A) 중의 식(3)으로 표시되는 화합물의 함유량이 5∼50질량%인 광학물품용 활성 에너지선 경화성 조성물.4. The method of claim 3,
The active energy ray-curable composition for optical articles whose content of the compound represented by Formula (3) in an active-energy-ray-polymerizable compound (A) is 5-50 mass %.
활성 에너지선 중합성 화합물(A)로서 하기 식(4)으로 표시되는 화합물을 함유하는 광학물품용 활성 에너지선 경화성 조성물.
3. The method of claim 1 or 2,
The active energy ray-curable composition for optical articles containing the compound represented by following formula (4) as an active energy ray-polymerizable compound (A).
활성 에너지선 중합성 화합물(A) 중의 식(4)으로 표시되는 화합물의 함유량이 5∼30질량%인 광학물품용 활성 에너지선 경화성 조성물.6. The method of claim 5,
The active energy ray-curable composition for optical articles whose content of the compound represented by Formula (4) in an active-energy-ray-polymerizable compound (A) is 5-30 mass %.
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