JP2022098704A - Active energy ray-curable resin composition, cured product and article - Google Patents
Active energy ray-curable resin composition, cured product and article Download PDFInfo
- Publication number
- JP2022098704A JP2022098704A JP2020212260A JP2020212260A JP2022098704A JP 2022098704 A JP2022098704 A JP 2022098704A JP 2020212260 A JP2020212260 A JP 2020212260A JP 2020212260 A JP2020212260 A JP 2020212260A JP 2022098704 A JP2022098704 A JP 2022098704A
- Authority
- JP
- Japan
- Prior art keywords
- active energy
- energy ray
- resin composition
- curable resin
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- -1 acrylate compound Chemical class 0.000 claims abstract description 43
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 42
- 150000007519 polyprotic acids Polymers 0.000 claims abstract description 38
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 12
- 150000002148 esters Chemical group 0.000 claims abstract description 12
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims description 22
- 239000011248 coating agent Substances 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000005299 abrasion Methods 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 description 48
- 229920000647 polyepoxide Polymers 0.000 description 48
- 239000004065 semiconductor Substances 0.000 description 18
- 239000011324 bead Substances 0.000 description 16
- 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 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000010419 fine particle Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002096 quantum dot Substances 0.000 description 5
- 239000012508 resin bead Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material 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
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- ZFEQSERZJMLTHK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)-2,3,5,6-tetramethylphenol Chemical compound CC1=C(O)C(C)=C(C)C(C=2C=CC(O)=CC=2)=C1C ZFEQSERZJMLTHK-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- YBNMDCCMCLUHBL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-pyren-1-ylbutanoate Chemical compound C=1C=C(C2=C34)C=CC3=CC=CC4=CC=C2C=1CCCC(=O)ON1C(=O)CCC1=O YBNMDCCMCLUHBL-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- JHGGYGMFCRSWIZ-UHFFFAOYSA-N 2,2-dichloro-1-(4-phenoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C(Cl)Cl)=CC=C1OC1=CC=CC=C1 JHGGYGMFCRSWIZ-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- CZAZXHQSSWRBHT-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-3,4,5,6-tetramethylphenol Chemical compound OC1=C(C)C(C)=C(C)C(C)=C1C1=CC=CC=C1O CZAZXHQSSWRBHT-UHFFFAOYSA-N 0.000 description 1
- JMVZGKVGQDHWOI-UHFFFAOYSA-N 2-(2-methylpropoxy)-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC(C)C)C(=O)C1=CC=CC=C1 JMVZGKVGQDHWOI-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- PSMYELRXRQIDAX-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(2-hydroxy-3-tridecoxypropoxy)phenol Chemical class OC1=CC(OCC(O)COCCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 PSMYELRXRQIDAX-UHFFFAOYSA-N 0.000 description 1
- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 1
- MIZUYZJRQGACDX-UHFFFAOYSA-N 2-[5-methyl-2-[(2-nitrophenyl)methoxy]phenyl]benzotriazole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C)=CC=C1OCC1=CC=CC=C1[N+]([O-])=O MIZUYZJRQGACDX-UHFFFAOYSA-N 0.000 description 1
- NXBXJOWBDCQIHF-UHFFFAOYSA-N 2-[hydroxy-[2-(2-methylprop-2-enoyloxy)ethoxy]phosphoryl]oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(=O)OCCOC(=O)C(C)=C NXBXJOWBDCQIHF-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
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-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
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 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
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 1
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 1
- HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical group C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 description 1
- BFPKYGRZERDWLA-UHFFFAOYSA-N 4-methylbicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1CC2C(C(O)=O)C(C(O)=O)C1(C)C2 BFPKYGRZERDWLA-UHFFFAOYSA-N 0.000 description 1
- JSBBGWWJLQNXNQ-UHFFFAOYSA-N 4-phenylbenzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC=C1 JSBBGWWJLQNXNQ-UHFFFAOYSA-N 0.000 description 1
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 229910017115 AlSb Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 1
- 229910004613 CdTe Inorganic materials 0.000 description 1
- 229910004611 CdZnTe Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910002601 GaN Inorganic materials 0.000 description 1
- 229910005540 GaP Inorganic materials 0.000 description 1
- 229910005542 GaSb Inorganic materials 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 229910004262 HgTe Inorganic materials 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 229910000673 Indium arsenide Inorganic materials 0.000 description 1
- GPXJNWSHGFTCBW-UHFFFAOYSA-N Indium phosphide Chemical compound [In]#P GPXJNWSHGFTCBW-UHFFFAOYSA-N 0.000 description 1
- 241000764773 Inna Species 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229910000661 Mercury cadmium telluride Inorganic materials 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910002665 PbTe Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- UAKWLVYMKBWHMX-UHFFFAOYSA-N SU4312 Chemical compound C1=CC(N(C)C)=CC=C1C=C1C2=CC=CC=C2NC1=O UAKWLVYMKBWHMX-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 1
- 229910005642 SnTe Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910007709 ZnTe Inorganic materials 0.000 description 1
- CBERLDHYJQHMCR-UHFFFAOYSA-N [4-dodecoxy-2-[(2-nitrophenyl)methoxy]phenyl]-phenylmethanone Chemical compound C=1C=CC=C([N+]([O-])=O)C=1COC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 CBERLDHYJQHMCR-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000005456 alcohol based solvent Substances 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
- 150000001412 amines Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 1
- MNUSMUGFHGAOIW-UHFFFAOYSA-N cyclohexane-1,1,2-tricarboxylic acid Chemical compound OC(=O)C1CCCCC1(C(O)=O)C(O)=O MNUSMUGFHGAOIW-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 229910021480 group 4 element Inorganic materials 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- WPYVAWXEWQSOGY-UHFFFAOYSA-N indium antimonide Chemical compound [Sb]#[In] WPYVAWXEWQSOGY-UHFFFAOYSA-N 0.000 description 1
- RPQDHPTXJYYUPQ-UHFFFAOYSA-N indium arsenide Chemical compound [In]#[As] RPQDHPTXJYYUPQ-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910003465 moissanite Inorganic materials 0.000 description 1
- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical compound FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- MZYHMUONCNKCHE-UHFFFAOYSA-N naphthalene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C21 MZYHMUONCNKCHE-UHFFFAOYSA-N 0.000 description 1
- KVQQRFDIKYXJTJ-UHFFFAOYSA-N naphthalene-1,2,3-tricarboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C(O)=O)C(C(=O)O)=CC2=C1 KVQQRFDIKYXJTJ-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- OCGWQDWYSQAFTO-UHFFFAOYSA-N tellanylidenelead Chemical compound [Pb]=[Te] OCGWQDWYSQAFTO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 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
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Epoxy Resins (AREA)
Abstract
Description
本発明は、高屈折率性能を有し、硬化物における優れた耐摩耗性を有する活性エネルギー線硬化性樹脂組成物、活性エネルギー線硬化性樹脂組成物の硬化物、及び物品に関する。 The present invention relates to an active energy ray-curable resin composition having high refractive index performance and excellent wear resistance in a cured product, a cured product of an active energy ray-curable resin composition, and an article.
近年、液晶表示装置等のディスプレイ技術の急速な発展に伴い、それに用いられるシート状又はフィルム状光学部材についても、新しい機能を有するものや、より高品質のものに対する需要が高まっている。このような光学部材としては、例えば、液晶表示装置のバックライトに用いられるプリズムシートやマイクロレンズシート等の輝度向上シートが挙げられる。これらの輝度向上シートは、通常、基材上に、表面に微細な凹凸構造を有する光学機能層が積層されてなるものであり、表面の微細な凹凸構造によって、バックライト光を屈折させることでディスプレイ正面の輝度を向上させることができる。該輝度向上シートには、少ない光量で高輝度を維持するために材料自身が高屈折率性能を有することが求められている。 In recent years, with the rapid development of display technology such as liquid crystal display devices, there is an increasing demand for sheet-shaped or film-shaped optical members used thereof having new functions and higher quality. Examples of such an optical member include a brightness improving sheet such as a prism sheet and a microlens sheet used for a backlight of a liquid crystal display device. These brightness improving sheets are usually formed by laminating an optical functional layer having a fine concavo-convex structure on the surface on a base material, and refracting the backlight light by the fine concavo-convex structure on the surface. The brightness of the front of the display can be improved. The luminance improving sheet is required to have a high refractive index performance by itself in order to maintain high luminance with a small amount of light.
従来知られている輝度向上シート用樹脂材料としては、金属酸化物ナノ粒子を含有した樹脂組成物であり、金属酸化物ナノ粒子がその粒度分布において、累積１０％粒子径が５～２５ｎｍ、累積５０％粒子径が７～３０ｎｍ、累積９０％粒子径が１５～５０ｎｍ、累積１００％粒子径が５０～２５０ｎｍの分布を持ち、樹脂成分として２つ以上のベンゼン骨格を有する化合物を含有することを特徴とする樹脂組成物が知られているが（例えば、特許文献１参照。）、このような無機微粒子配合型の樹脂材料は、高屈折率性能を有する一方で、硬化物における耐摩耗性が十分でない等の問題があった。 The conventionally known resin material for a brightness improving sheet is a resin composition containing metal oxide nanoparticles, and the metal oxide nanoparticles have a cumulative 10% particle size of 5 to 25 nm and a cumulative particle size distribution. It has a distribution of 50% particle size of 7 to 30 nm, cumulative 90% particle size of 15 to 50 nm, cumulative 100% particle size of 50 to 250 nm, and contains a compound having two or more benzene skeletons as a resin component. Although a characteristic resin composition is known (see, for example, Patent Document 1), such a resin material containing inorganic fine particles has high refractive index performance, but has wear resistance in a cured product. There were problems such as not enough.
そこで、高屈折率性能を有し、硬化物における優れた耐摩耗性を有する材料が求められていた。 Therefore, there has been a demand for a material having a high refractive index performance and excellent wear resistance in a cured product.
本発明が解決しようとする課題は、高屈折率性能を有し、硬化物における優れた耐摩耗性を有する活性エネルギー線硬化性樹脂組成物、硬化物及び物品を提供することである。 An object to be solved by the present invention is to provide an active energy ray-curable resin composition, a cured product and an article having high refractive index performance and excellent wear resistance in a cured product.
本発明者らは、上記課題を解決すべく鋭意検討した結果、一分子中に少なくとも２つの芳香環及び少なくとも１つのエポキシ基を有する化合物と、特定の多塩基酸無水物と、特定の（メタ）アクリレート化合物とを必須原料とする活性エネルギー線硬化性樹脂組成物を用いることによって、上記課題を解決できることを見出し、本発明を完成させた。 As a result of diligent studies to solve the above problems, the present inventors have found that a compound having at least two aromatic rings and at least one epoxy group in one molecule, a specific polybasic acid anhydride, and a specific (meth). ) The present invention has been completed by finding that the above problems can be solved by using an active energy ray-curable resin composition containing an acrylate compound as an essential raw material.
すなわち、本発明は、一分子中に少なくとも２つの芳香環及び少なくとも１つのエポキシ基を有する化合物（Ａ）と、多塩基酸無水物（Ｂ）と、アルキレンオキサイド鎖及び／又はエステル鎖を有する（メタ）アクリレート化合物（Ｃ）と、を必須原料とする活性エネルギー線硬化性樹脂組成物であって、前記多塩基酸無水物（Ｂ）が、脂環式多塩基酸無水物及び／又は芳香族多塩基酸無水物であり、前記化合物（Ｃ）が有するアルキレンオキサイド鎖の繰り返し単位数が、２～２０の範囲であり、エステル鎖の炭素原子数が、５以上であることを特徴とする活性エネルギー線硬化性樹脂組成物、前記活性エネルギー線硬化性樹脂組成物からなる硬化物、及び物品に関するものである。 That is, the present invention has a compound (A) having at least two aromatic rings and at least one epoxy group in one molecule, a polybasic acid anhydride (B), an alkylene oxide chain and / or an ester chain ( An active energy ray-curable resin composition containing a meta) acrylate compound (C) as an essential raw material, wherein the polybasic acid anhydride (B) is an alicyclic polybasic acid anhydride and / or an aromatic. It is a polybasic acid anhydride, and the number of repeating units of the alkylene oxide chain of the compound (C) is in the range of 2 to 20, and the number of carbon atoms of the ester chain is 5 or more. It relates to an energy ray-curable resin composition, a cured product made of the active energy ray-curable resin composition, and an article.
本発明の活性エネルギー線硬化性樹脂組成物は、高屈折率性能を有し、硬化物における優れた耐摩耗性を有することから、プリズムシート、マイクロレンズシート等の輝度向上シートなどの光学部材に好適に用いることができる。 Since the active energy ray-curable resin composition of the present invention has high refractive index performance and excellent wear resistance in the cured product, it can be used for optical members such as prism sheets, microlens sheets and other brightness-enhancing sheets. It can be suitably used.
本発明の活性エネルギー線硬化性樹脂組成物は、一分子中に少なくとも２つの芳香環及び少なくとも１つのエポキシ基を有する化合物（Ａ）と、多塩基酸無水物（Ｂ）と、アルキレンオキサイド鎖及び／又はエステル鎖を有する（メタ）アクリレート化合物（Ｃ）とを必須の原料とすることを特徴とする。 The active energy ray-curable resin composition of the present invention comprises a compound (A) having at least two aromatic rings and at least one epoxy group in one molecule, a polybasic acid anhydride (B), an alkylene oxide chain and an alkylene oxide chain. / Or a (meth) acrylate compound (C) having an ester chain is used as an essential raw material.
なお、本発明において、「（メタ）アクリレート」とは、アクリレート及び／又はメタクリレートを意味する。また、「（メタ）アクリロイル」とは、アクリロイル及び／又はメタクリロイルを意味する。さらに、「（メタ）アクリル」とは、アクリル及び／又はメタクリルを意味する。 In the present invention, "(meth) acrylate" means acrylate and / or methacrylate. Further, "(meth) acryloyl" means acryloyl and / or methacryloyl. Further, "(meth) acrylic" means acrylic and / or methacrylic.
前記化合物（Ａ）としては、一分子中に少なくとも２つの芳香環及び少なくとも１つのエポキシ基を有するものを用いる。例えば、ビスフェノール型エポキシ樹脂、フェニレンエーテル型エポキシ樹脂、ナフチレンエーテル型エポキシ樹脂、ビフェニル型エポキシ樹脂、トリフェニルメタン型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビスフェノールノボラック型エポキシ樹脂、ナフトールノボラック型エポキシ樹脂、ナフトール－フェノール共縮ノボラック型エポキシ樹脂、ナフトール－クレゾール共縮ノボラック型エポキシ樹脂、フェノールアラルキル型エポキシ樹脂、ナフトールアラルキル型エポキシ樹脂、ジシクロペンタジエン－フェノール付加反応型エポキシ樹脂、ビフェニルアラルキル型エポキシ樹脂、フルオレン型エポキシ樹脂、キサンテン型エポキシ樹脂、ジヒドロキシベンゼン型エポキシ樹脂、トリヒドロキシベンゼン型エポキシ樹脂、オキサゾリドン型エポキシ樹脂等が挙げられる。 As the compound (A), a compound having at least two aromatic rings and at least one epoxy group in one molecule is used. For example, bisphenol type epoxy resin, phenylene ether type epoxy resin, naphthylene ether type epoxy resin, biphenyl type epoxy resin, triphenylmethane type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol novolac type epoxy resin, Naftol novolak type epoxy resin, naphthol-phenol co-shrink novolak type epoxy resin, naphthol-cresol co-shrink novolak type epoxy resin, phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene-phenol addition reaction type epoxy resin, biphenyl Examples thereof include an aralkyl type epoxy resin, a fluorene type epoxy resin, a xanthene type epoxy resin, a dihydroxybenzene type epoxy resin, a trihydroxybenzene type epoxy resin, and an oxazolidone type epoxy resin.
前記ビスフェノール型エポキシ樹脂としては、例えば、ビスフェノールＡ型エポキシ樹脂、ビスフェノールＡＰ型エポキシ樹脂、ビスフェノールＢ型エポキシ樹脂、ビスフェノールＢＰ型エポキシ樹脂、ビスフェノールＥ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、ビスフェノールＳ型エポキシ樹脂等が挙げられる。 Examples of the bisphenol type epoxy resin include bisphenol A type epoxy resin, bisphenol AP type epoxy resin, bisphenol B type epoxy resin, bisphenol BP type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, and bisphenol S type epoxy. Examples include resin.
前記水添ビスフェノール型エポキシ樹脂としては、例えば、水添ビスフェノールＡ型エポキシ樹脂、水添ビスフェノールＢ型エポキシ樹脂、水添ビスフェノールＥ型エポキシ樹脂、水添ビスフェノールＦ型エポキシ樹脂、水添ビスフェノールＳ型エポキシ樹脂等が挙げられる。 Examples of the hydrogenated bisphenol type epoxy resin include hydrogenated bisphenol A type epoxy resin, hydrogenated bisphenol B type epoxy resin, hydrogenated bisphenol E type epoxy resin, hydrogenated bisphenol F type epoxy resin, and hydrogenated bisphenol S type epoxy. Examples include resin.
前記ビフェノール型エポキシ樹脂としては、例えば、４，４’－ビフェノール型エポキシ樹脂、２，２’－ビフェノール型エポキシ樹脂、テトラメチル－４，４’－ビフェノール型エポキシ樹脂、テトラメチル－２，２’－ビフェノール型エポキシ樹脂等が挙げられる。 Examples of the biphenol type epoxy resin include 4,4'-biphenol type epoxy resin, 2,2'-biphenol type epoxy resin, tetramethyl-4,4'-biphenol type epoxy resin, and tetramethyl-2,2'. -Biphenol type epoxy resin and the like can be mentioned.
前記水添ビフェノール型エポキシ樹脂としては、例えば、水添４，４’－ビフェノール型エポキシ樹脂、水添２，２’－ビフェノール型エポキシ樹脂、水添テトラメチル－４，４’－ビフェノール型エポキシ樹脂、水添テトラメチル－２，２’－ビフェノール型エポキシ樹脂等が挙げられる。 Examples of the hydrogenated biphenol type epoxy resin include hydrogenated 4,4'-biphenol type epoxy resin, hydrogenated 2,2'-biphenol type epoxy resin, and hydrogenated tetramethyl-4,4'-biphenol type epoxy resin. , Hydrophobic tetramethyl-2,2'-biphenol type epoxy resin and the like.
これらの化合物（Ａ）は、単独で用いることも２種以上を併用することもできる。また、これらの中でも、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能な活性エネルギー線硬化性樹脂組成物が得られることから、ビスフェノールＡ型エポキシ樹脂が好ましい。 These compounds (A) can be used alone or in combination of two or more. Further, among these, a bisphenol A type epoxy resin is preferable because an active energy ray-curable resin composition capable of forming a cured product having high refractive index performance and excellent wear resistance can be obtained.
前記多塩基酸無水物（Ｂ）としては、脂環式多塩基酸無水物及び／又は芳香族多塩基酸無水物を用いる。 As the polybasic acid anhydride (B), an alicyclic polybasic acid anhydride and / or an aromatic polybasic acid anhydride is used.
前記脂環式多塩基酸無水物としては、本発明では、酸無水物基が脂環構造に結合しているものを脂環式多塩基酸無水物とし、それ以外の構造部位における芳香環の有無は問わないものとする。前記脂環式多塩基酸無水物としては、例えば、テトラヒドロフタル酸、ヘキサヒドロフタル酸、メチルヘキサヒドロフタル酸、シクロヘキサントリカルボン酸、シクロヘキサンテトラカルボン酸、ビシクロ［２．２．１］ヘプタン－２，３－ジカルボン酸、メチルビシクロ［２．２．１］ヘプタン－２，３－ジカルボン酸、４－（２，５－ジオキソテトラヒドロフラン－３－イル）－１，２，３，４－テトラヒドロナフタレン－１，２－ジカルボン酸の酸無水物等が挙げられる。 As the alicyclic polybasic acid anhydride, in the present invention, an alicyclic polybasic acid anhydride having an acid anhydride group bonded to an alicyclic structure is used as an alicyclic polybasic acid anhydride, and the aromatic ring in other structural parts is used. It does not matter whether it is present or not. Examples of the alicyclic polybasic acid anhydride include tetrahydrophthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, cyclohexanetricarboxylic acid, cyclohexanetetracarboxylic acid, and bicyclo [2.2.1] heptane-2. 3-Dicarboxylic acid, methylbicyclo [2.2.1] heptane-2,3-dicarboxylic acid, 4- (2,5-dioxotetratetra-3-yl) -1,2,3,4-tetrahydronaphthalene- Examples thereof include acid anhydrides of 1,2-dicarboxylic acids.
前記芳香族多塩基酸無水物としては、例えば、フタル酸、トリメリット酸、ピロメリット酸、ナフタレンジカルボン酸、ナフタレントリカルボン酸、ナフタレンテトラカルボン酸、ビフェニルジカルボン酸、ビフェニルトリカルボン酸、ビフェニルテトラカルボン酸、ベンゾフェノンテトラカルボン酸の酸無水物等が挙げられる。 Examples of the aromatic polybasic acid anhydride include phthalic acid, trimellitic acid, pyromellitic acid, naphthalenedicarboxylic acid, naphthalenetricarboxylic acid, naphthalenetetracarboxylic acid, biphenyldicarboxylic acid, biphenyltricarboxylic acid and biphenyltetracarboxylic acid. Examples thereof include acid anhydrides of benzophenone tetracarboxylic acid.
これらの多塩基酸無水物（Ｂ）は、単独で用いることも２種以上を併用することもできる。 These polybasic acid anhydrides (B) can be used alone or in combination of two or more.
また、前記多塩基酸無水物（Ｂ）としては、必要に応じて、前記脂環式多塩基酸無水物及び前記芳香族多塩基酸無水物以外に脂肪族多塩基酸無水物を併用することもできる。 Further, as the polybasic acid anhydride (B), an aliphatic polybasic acid anhydride may be used in combination with the alicyclic polybasic acid anhydride and the aromatic polybasic acid anhydride, if necessary. You can also.
前記脂肪族多塩基酸無水物としては、例えば、シュウ酸、マロン酸、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、マレイン酸、フマル酸、シトラコン酸、イタコン酸、グルタコン酸、１，２，３，４－ブタンテトラカルボン酸の酸無水物等が挙げられる。また、前記脂肪族多塩基酸無水物としては、脂肪族炭化水素基は直鎖型及び分岐型のいずれでもよく、構造中に不飽和結合を有していてもよい。 Examples of the aliphatic polybasic acid anhydride include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelli acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, citraconic acid and itacone. Examples thereof include acid, glutaconic acid, and acid anhydrides of 1,2,3,4-butanetetracarboxylic acid. Further, as the aliphatic polybasic acid anhydride, the aliphatic hydrocarbon group may be either a linear type or a branched type, and may have an unsaturated bond in the structure.
前記多塩基酸無水物（Ｂ）としては、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能な活性エネルギー線硬化性樹脂組成物が得られることから、芳香族多塩基酸無水物を必須として用いることが好ましく、前記芳香族多塩基酸無水物の含有量が、前記多塩基酸無水物（Ｂ）中に３０～１００質量％の範囲が好ましく、１００質量％であることがより好ましい。 As the polybasic acid anhydride (B), an active energy ray-curable resin composition capable of forming a cured product having high refractive index performance and excellent wear resistance can be obtained. It is preferable to use the basic acid anhydride as an essential, and the content of the aromatic polybasic acid anhydride is preferably in the range of 30 to 100% by mass in the polybasic acid anhydride (B), preferably 100% by mass. It is more preferable to have.
また、前記多塩基酸無水物（Ｂ）の使用量は、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能な活性エネルギー線硬化性樹脂組成物が得られることから、前記化合物（Ａ）１００質量部に対して、３０～３００質量部の範囲が好ましく、５０～２００質量部の範囲がより好ましい。 Further, the amount of the polybasic acid anhydride (B) used is such that an active energy ray-curable resin composition capable of forming a cured product having high refractive index performance and excellent wear resistance can be obtained. The range of 30 to 300 parts by mass is preferable, and the range of 50 to 200 parts by mass is more preferable with respect to 100 parts by mass of the compound (A).
前記化合物（Ｃ）としては、アルキレンオキサイド鎖及び／又はエステル鎖を有する（メタ）アクリレート化合物を用いる。前記化合物（Ｃ）がアルキレンオキサイド鎖を有する場合、前記アルキレンオキサイド鎖の繰り返し単位は、２～２０の範囲であり、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能な活性エネルギー線硬化性樹脂組成物が得られることから、４～１５の範囲が好ましい。また、前記化合物（Ｃ）が、エステル鎖を有する場合、前記エステル鎖の炭素原子数は、５以上であり、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能な活性エネルギー線硬化性樹脂組成物が得られることから、５～２５の範囲が好ましい。 As the compound (C), a (meth) acrylate compound having an alkylene oxide chain and / or an ester chain is used. When the compound (C) has an alkylene oxide chain, the repeating unit of the alkylene oxide chain is in the range of 2 to 20, and it is possible to form a cured product having high refractive index performance and excellent wear resistance. The range of 4 to 15 is preferable because an active energy ray-curable resin composition can be obtained. When the compound (C) has an ester chain, the ester chain has 5 or more carbon atoms, has high refractive index performance, and can form a cured product having excellent wear resistance. The range of 5 to 25 is preferable because an active energy ray-curable resin composition can be obtained.
前記化合物（Ｃ）としては、例えば、ポリエチレングリコールモノ（メタ）アクリレート、ポリプロピレングリコールモノ（メタ）アクリレート、ポリエチレングリコール－プロピレングリコール－モノ（メタ）アクリレート、不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン付加物等が挙げられる。これらの化合物（Ｃ）は単独で用いることも２種以上を併用することもできる。また、これらの中でも、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能な活性エネルギー線硬化性樹脂組成物が得られることから、ポリエチレングリコールモノ（メタ）アクリレートが好ましい。 Examples of the compound (C) include polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, polyethylene glycol-propylene glycol-mono (meth) acrylate, and unsaturated fatty acid hydroxyalkyl ester-modified ε-caprolactone adduct. And so on. These compounds (C) can be used alone or in combination of two or more. Among these, polyethylene glycol mono (meth) acrylate is preferable because an active energy ray-curable resin composition capable of forming a cured product having high refractive index performance and excellent wear resistance can be obtained. ..
また、前記化合物（Ｃ）の使用量は、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能な活性エネルギー線硬化性樹脂組成物が得られることから、前記化合物（Ａ）１００質量部に対して、７０～６５０質量部の範囲が好ましく、９０～５００質量部の範囲がより好ましい。 Further, the amount of the compound (C) used is such that an active energy ray-curable resin composition capable of forming a cured product having high refractive index performance and excellent wear resistance can be obtained. A) The range of 70 to 650 parts by mass is preferable, and the range of 90 to 500 parts by mass is more preferable with respect to 100 parts by mass.
また、本発明の活性エネルギー線硬化性樹脂組成物は、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能なことから、下記一般式（１）、（２）、（３）又は（４）で表されるものであることが好ましい。 Further, since the active energy ray-curable resin composition of the present invention can form a cured product having high refractive index performance and excellent wear resistance, the following general formulas (1) and (2), It is preferably represented by (3) or (4).
［式（１）～（４）中、環Ａは、それぞれ独立して、芳香環又はシクロ環であり、Ｒ１は、それぞれ独立して水素原子又はメチル基であり、Ｒ２は、それぞれ独立して水素原子又はメチル基であり、Ｒ３は、それぞれ独立して水素原子又はメチル基である。Ｘは、－Ｏ－、－ＳＯ２－、下記構造式（５）で表される構造、又は下記構造式（６）で表される構造であり、ｍは、０又は１～１０の整数であり、ｎは、０又は１～１０の整数であり、ｍ＋ｎは、２～２０の整数である。また、ｒは、それぞれ独立して３～８の整数であり、ｓは、それぞれ独立して１～５の整数であり、ｔは、それぞれ独立して１～５の整数である。］ [In the formulas (1) to (4), ring A is independently an aromatic ring or a cyclo ring, R 1 is independently a hydrogen atom or a methyl group, and R 2 is independent. It is a hydrogen atom or a methyl group , and R3 is an independent hydrogen atom or a methyl group, respectively. X is -O-, -SO 2- , a structure represented by the following structural formula (5), or a structure represented by the following structural formula (6), and m is an integer of 0 or 1 to 10. Yes, n is an integer of 0 or 1 to 10, and m + n is an integer of 2 to 20. Further, r is an integer of 3 to 8 independently, s is an integer of 1 to 5 independently, and t is an integer of 1 to 5 independently. ]
本発明の活性エネルギー線硬化性樹脂組成物の製造方法としては、特に制限されず、適宜公知の方法により製造することができる。例えば、必須原料を含む原料の全てを一括で反応させる方法で製造してもよいし、原料を順次反応させる方法で製造してもよい。 The method for producing the active energy ray-curable resin composition of the present invention is not particularly limited, and the active energy ray-curable resin composition can be appropriately produced by a known method. For example, it may be produced by a method in which all the raw materials including the essential raw materials are reacted at once, or it may be produced by a method in which the raw materials are sequentially reacted.
前記原料を順次反応させる方法としては、例えば、先に多塩基酸無水物（Ｂ）と化合物（Ｃ）とを、トリフェニルホスフィン存在下、１００℃、１０時間で反応させ、反応生成物を得、次いで、得られた反応生成物と、化合物（Ａ）とをトリフェニルホスフィン存在下、１０５℃、１０時間で反応させて製造する方法が挙げられる。 As a method for sequentially reacting the raw materials, for example, the polybasic acid anhydride (B) and the compound (C) are first reacted at 100 ° C. for 10 hours in the presence of triphenylphosphine to obtain a reaction product. Then, a method of reacting the obtained reaction product with the compound (A) in the presence of triphenylphosphine at 105 ° C. for 10 hours can be mentioned.
これらの製造方法の中でも、高屈折率性能を有し、優れた耐摩耗性を有する硬化物を形成可能な活性エネルギー線硬化性樹脂組成物が得られることから、原料を順次反応させる方法が好ましい。 Among these production methods, an active energy ray-curable resin composition capable of forming a cured product having high refractive index performance and excellent wear resistance can be obtained, and therefore, a method in which raw materials are sequentially reacted is preferable. ..
また、本発明の活性エネルギー線硬化性樹脂組成物は、用いる活性エネルギー線の種類によっては、光重合開始剤を用いることが好ましい。前記光重合開始剤としては、例えば、１－ヒドロキシシクロヘキシルフェニルケトン、２－ヒドロキシ－２－メチル－１－フェニルプロパン－１－オン、１－〔４－（２－ヒドロキシエトキシ）フェニル〕－２－ヒドロキシ－２－メチル－１－プロパン－１－オン、チオキサントン及びチオキサントン誘導体、２，２’－ジメトキシ－１，２－ジフェニルエタン－１－オン、ジフェニル（２，４，６－トリメトキシベンゾイル）ホスフィンオキシド、２，４，６－トリメチルベンゾイルジフェニルホスフィンオキシド、ビス（２，４，６－トリメチルベンゾイル）フェニルホスフィンオキシド、２－メチル－１－（４－メチルチオフェニル）－２－モルフォリノプロパン－１－オン、２－ベンジル－２－ジメチルアミノ－１－（４－モルホリノフェニル）－１－ブタノン等の光ラジカル重合開始剤などが挙げられる。 Further, in the active energy ray-curable resin composition of the present invention, it is preferable to use a photopolymerization initiator depending on the type of active energy ray used. Examples of the photopolymerization initiator include 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- [4- (2-hydroxyethoxy) phenyl] -2-. Hydroxy-2-methyl-1-propane-1-one, thioxanthone and thioxanthone derivatives, 2,2'-dimethoxy-1,2-diphenylethan-1-one, diphenyl (2,4,6-trimethoxybenzoyl) phosphenyl Oxide, 2,4,6-trimethylbenzoyldiphenylphosphenyl oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphenyl oxide, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1- Examples thereof include photoradical polymerization initiators such as on, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone.
前記その他の光重合開始剤の市販品としては、例えば、「Ｏｍｎｉｒａｄ １１７３」、「Ｏｍｎｉｒａｄ １８４」、「Ｏｍｎｉｒａｄ １２７」、「Ｏｍｎｉｒａｄ ２９５９」、「Ｏｍｎｉｒａｄ ３６９」、「Ｏｍｎｉｒａｄ ３７９」、「Ｏｍｎｉｒａｄ ９０７」、「Ｏｍｎｉｒａｄ ４２６５」、「Ｏｍｎｉｒａｄ １０００」、「Ｏｍｎｉｒａｄ ６５１」、「Ｏｍｎｉｒａｄ ＴＰＯ」、「Ｏｍｎｉｒａｄ ８１９」、「Ｏｍｎｉｒａｄ ２０２２」、「Ｏｍｎｉｒａｄ ２１００」、「Ｏｍｎｉｒａｄ ７５４」、「Ｏｍｎｉｒａｄ ７８４」、「Ｏｍｎｉｒａｄ ５００」、「Ｏｍｎｉｒａｄ ８１」（ＩＧＭ Ｒｅｓｉｎｓ社製）；「ＫＡＹＡＣＵＲＥ ＤＥＴＸ」、「ＫＡＹＡＣＵＲＥ ＭＢＰ」、「ＫＡＹＡＣＵＲＥ ＤＭＢＩ」、「ＫＡＹＡＣＵＲＥ ＥＰＡ」、「ＫＡＹＡＣＵＲＥ ＯＡ」（日本化薬株式会社製）；「Ｖｉｃｕｒｅ １０」、「Ｖｉｃｕｒｅ ５５」（Ｓｔｏｆｆａ Ｃｈｅｍｉｃａｌ社製）；「Ｔｒｉｇｏｎａｌ Ｐ１」（Ａｋｚｏ Ｎｏｂｅｌ社製）、「ＳＡＮＤＯＲＡＹ １０００」（ＳＡＮＤＯＺ社製）；「ＤＥＡＰ」（Ｕｐｊｏｈｎ Ｃｈｅｍｉｃａｌ社製）、「Ｑｕａｎｔａｃｕｒｅ ＰＤＯ」、「Ｑｕａｎｔａｃｕｒｅ ＩＴＸ」、「Ｑｕａｎｔａｃｕｒｅ ＥＰＤ」（Ｗａｒｄ Ｂｌｅｎｋｉｎｓｏｐ社製）；「Ｒｕｎｔｅｃｕｒｅ １１０４」（Ｒｕｎｔｅｃ社製）等が挙げられる。これらの光重合開始剤は、単独で用いることも、２種以上を併用することもできる。 Examples of commercially available products of the other photopolymerization initiators include "Omnirad 1173", "Omnirad 184", "Omnirad 127", "Omnirad 2959", "Omnirad 369", "Omnirad 379", "Omnirad 90". "Omnirad 4265", "Omnirad 1000", "Omnirad 651", "Omnirad TPO", "Omnirad 819", "Omnirad 2022", "Omnirad 2100", "Omnirad 2100", "Omnirad 754", "Omnirad" "Omnirad 81" (manufactured by IGM Resins); "KAYACURE DETX", "KAYACURE MBP", "KAYACURE DMBI", "KAYACURE EPA", "KAYACURE OA" (manufactured by Nippon Kayaku Co., Ltd.); "Vicure 10" "Vicure 55" (manufactured by Stoffa Chemical); "Trigonal P1" (manufactured by Akzo Nobel), "SANDORAY 1000" (manufactured by SANDOZ); "DEAP" (manufactured by Upjon Chemical), "QuantuQua" , "Chemistry EPD" (manufactured by Ward Brenkinsop); "Runtecure 1104" (manufactured by Runtec) and the like. These photopolymerization initiators may be used alone or in combination of two or more.
また、前記光重合開始剤は、アミン化合物、尿素化合物、含硫黄化合物、含燐化合物、含塩素化合物、ニトリル化合物等の光増感剤を併用することもできる。 Further, as the photopolymerization initiator, a photosensitizer such as an amine compound, a urea compound, a sulfur-containing compound, a phosphorus-containing compound, a chlorine-containing compound, and a nitrile compound can also be used in combination.
前記光重合開始剤の使用量は、本発明の活性エネルギー線硬化性組成物の不揮発分１００質量部に対して０．０５～２０質量部の範囲で用いることが好ましく、０．１～１０質量部の範囲で用いることがより好ましい。 The amount of the photopolymerization initiator used is preferably in the range of 0.05 to 20 parts by mass with respect to 100 parts by mass of the non-volatile content of the active energy ray-curable composition of the present invention, and is 0.1 to 10 parts by mass. It is more preferable to use it in the range of parts.
本発明で用いる活性エネルギー線硬化性樹脂組成物は、更に必要に応じて、前記化合物（Ａ）、前記多塩基酸無水物（Ｂ）、及び前記化合物（Ｃ）以外のその他の成分を含有していてもよい。なお、前記活性エネルギー線硬化性樹脂組成物中の前記化合物（Ａ）、前記多塩基酸無水物（Ｂ）、及び前記化合物（Ｃ）の含有量は、前記活性エネルギー線硬化性樹脂組成物の不揮発分中に５０～１００質量％の範囲が好ましく、１００質量％であることがより好ましい。 The active energy ray-curable resin composition used in the present invention further contains the compound (A), the polybasic acid anhydride (B), and other components other than the compound (C), if necessary. May be. The content of the compound (A), the polybasic acid anhydride (B), and the compound (C) in the active energy ray-curable resin composition is the content of the active energy ray-curable resin composition. The non-volatile content is preferably in the range of 50 to 100% by mass, more preferably 100% by mass.
前記その他の成分は、例えば、無機微粒子、シランカップリング剤、リン酸エステル化合物、溶剤、紫外線吸収剤、酸化防止剤、シリコン系添加剤、フッ素系添加剤、帯電防止剤、有機ビーズ、量子ドット（ＱＤ）、レオロジーコントロール剤、脱泡剤、防曇剤、着色剤等が挙げられる。 The other components include, for example, inorganic fine particles, silane coupling agents, phosphoric acid ester compounds, solvents, ultraviolet absorbers, antioxidants, silicon-based additives, fluorine-based additives, antistatic agents, organic beads, and quantum dots. (QD), a rheology control agent, a defoaming agent, an antifogging agent, a coloring agent and the like can be mentioned.
前記無機微粒子は、活性エネルギー線硬化性樹脂組成物の硬化塗膜における硬度や屈折率等を調整する等の目的で添加されるものであり、公知慣用の種々の無機微粒子を用いることができる。前記無機微粒子としては、シリカ、アルミナ、ジルコニア、チタニア、チタン酸バリウム、三酸化アンチモン等が挙げられる。これらの無機微粒子は、単独で用いることも２種以上を併用することもできる。このうち特に汎用性が高いシリカ粒子は、フュームドシリカや、沈殿法シリカ、ゲルシリカ、ゾルゲルシリカ等と呼ばれる湿式シリカなど様々な種類があるが、いずれを用いてもよい。また、無機微粒子の表面はシランカップリング剤等で修飾されていてもよい。無機微粒子の粒子径は所望の塗膜性能等に応じて適宜調節されるが、動的光散乱法による測定値が１０～２５０ｎｍの範囲であることが好ましい。無機微粒子を用いる場合、その添加量は、活性エネルギー線硬化性樹脂組成物の不揮発分１００質量部に対して、０．１～６０質量部の範囲が好ましい。 The inorganic fine particles are added for the purpose of adjusting the hardness, refractive index, etc. of the cured coating film of the active energy ray-curable resin composition, and various known and commonly used inorganic fine particles can be used. Examples of the inorganic fine particles include silica, alumina, zirconia, titania, barium titanate, antimony trioxide and the like. These inorganic fine particles may be used alone or in combination of two or more. Among these, there are various types of silica particles having particularly high versatility, such as fumed silica, wet silica called precipitation method silica, gel silica, sol gel silica and the like, and any of them may be used. Further, the surface of the inorganic fine particles may be modified with a silane coupling agent or the like. The particle size of the inorganic fine particles is appropriately adjusted according to the desired coating film performance and the like, but the measured value by the dynamic light scattering method is preferably in the range of 10 to 250 nm. When the inorganic fine particles are used, the addition amount thereof is preferably in the range of 0.1 to 60 parts by mass with respect to 100 parts by mass of the non-volatile content of the active energy ray-curable resin composition.
前記シランカップリング剤としては、例えば、［（メタ）アクリロイルオキシアルキル］トリアルキルシラン、［（メタ）アクリロイルオキシアルキル］ジアルキルアルコキシシラン、［（メタ）アクリロイルオキシアルキル］アルキルジアルコキシシラン、［（メタ）アクリロイルオキシアルキル］トリアルコキシシラン等の（メタ）アクリロイルオキシ系シランカップリング剤；トリアルキルビニルシラン、ジアルキルアルコキシビニルシラン、アルキルジアルコキシビニルシラン、トリアルコキシビニルシラン、トリアルキルアリルシラン、ジアルキルアルコキシアリルシラン、アルキルジアルコキシアリルシラン、トリアルコキシアリルシラン等のビニル系シランカップリング剤；スチリルトリアルキル、スチリルジアルキルアルコキシシラン、スチリルアルキルジアルコキシシラン、スチリルトリアルコキシシラン等のスチレン系シランカップリング剤；（グリシジルオキシアルキル）トリアルキルシラン、（グリシジルオキシアルキル）ジアルキルアルコキシシラン、（グリシジルオキシアルキル）アルキルジアルコキシシラン、（グリシジルオキシアルキル）トリアルコキシシラン、［（３，４－エポキシシクロヘキシル）アルキル］トリメトキシシラン、［（３，４－エポキシシクロヘキシル）アルキル］トリアルキルシラン、［（３，４－エポキシシクロヘキシル）アルキル］ジアルキルアルコキシシラン、［（３，４－エポキシシクロヘキシル）アルキル］アルキルジアルコキシシラン、［（３，４－エポキシシクロヘキシル）アルキル］トリアルコキシシラン等のエポキシ系シランカップリング剤；（イソシアネートアルキル）トリアルキルシラン、（イソシアネートアルキル）ジアルキルアルコキシシラン、（イソシアネートアルキル）アルキルジアルコキシシラン、（イソシアネートアルキル）トリアルコキシシラン等のイソシアネート系シランカップリング剤などが挙げられる。これらのシランカップリング剤は、単独で用いることも２種以上を併用することもできる。 Examples of the silane coupling agent include [(meth) acryloyloxyalkyl] trialkylsilane, [(meth) acryloyloxyalkyl] dialkylalkoxysilane, [(meth) acryloyloxyalkyl] alkyldialkoxysilane, and [(meth) acryloyloxyalkyl]. ) Acryloyloxyalkyl] (meth) acryloyloxy-based silane coupling agents such as trialkoxysilane; trialkylvinylsilane, dialkylalkoxyvinylsilane, alkyldialkoxyvinylsilane, trialkoxyvinylsilane, trialkylallylsilane, dialkylalkoxyallylsilane, alkyldialkoxyallylsilane , Vinyl-based silane coupling agents such as styrene-allylsilane; styrene-based silane coupling agents such as styryltrialkyl, styryldialkylalkoxysilane, styrylalkyldialkoxysilane, and styryltrialkoxysilane; (glycidyloxyalkyl) trialkylsilane, (Glysidyloxyalkyl) Dialkylalkoxysilane, (Glysidyloxyalkyl) Alkyldialkoxysilane, (Glysidyloxyalkyl) Trialkoxysilane, [(3,4-Epoxycyclohexyl) Alkyl] Trimethoxysilane, [(3,4-Epoxy) [Cyclohexyl) alkyl] trialkylsilane, [(3,4-epoxycyclohexyl) alkyl] dialkylalkoxysilane, [(3,4-epoxycyclohexyl) alkyl] alkyldialkoxysilane, [(3,4-epoxycyclohexyl) alkyl] Epoxy-based silane coupling agents such as trialkoxysilanes; isocyanate-based silane cups such as (isocyanaylalkyl) trialkylsilanes, (isocyanaylalkyl) dialkylalkoxysilanes, (isocyanisalkyl) alkyldialkoxysilanes, and (isocyanoxidealkyl) trialkoxysilanes. Examples include ring agents. These silane coupling agents can be used alone or in combination of two or more.
前記リン酸エステル化合物としては、例えば、分子構造中に（メタ）アクリロイル基を有するリン酸エステル化合物である日本化薬株式会社製「カヤマーＰＭ－２」、「カヤマーＰＭ－２１」、共栄社化学株式会社製「ライトエステルＰ－１Ｍ」「ライトエステルＰ－２Ｍ」、「ライトアクリレートＰ－１Ａ（Ｎ）」、ＳＯＬＶＡＹ社製「ＳＩＰＯＭＥＲ ＰＡＭ １００」、「ＳＩＰＯＭＥＲ ＰＡＭ ２００」、「ＳＩＰＯＭＥＲ ＰＡＭ ３００」、「ＳＩＰＯＭＥＲ ＰＡＭ ４０００」、大阪有機化学工業社製「ビスコート＃３ＰＡ」、「ビスコート＃３ＰＭＡ」、第一工業製薬社製「ニューフロンティア Ｓ－２３Ａ」；分子構造中にアリルエーテル基を有するリン酸エステル化合物であるＳＯＬＶＡＹ社製「ＳＩＰＯＭＥＲ ＰＡＭ ５０００」等の市販品が挙げられる。 Examples of the phosphate ester compound include "Kayamer PM-2" and "Kayamer PM-21" manufactured by Nippon Kayaku Co., Ltd., which are phosphate ester compounds having a (meth) acryloyl group in the molecular structure, and Kyoeisha Chemical Co., Ltd. Company-made "Light Ester P-1M" "Light Ester P-2M", "Light Ester P-1A (N)", SOLVAY "Sipomer PAM 100", "Sipomer PAM 200", "Sipomer PAM 300", "Sipomer PAM 300" "SIPOMER PAM 4000", "Biscoat # 3PA" manufactured by Osaka Organic Chemical Industry Co., Ltd., "Biscoat # 3PMA", "New Frontier S-23A" manufactured by Daiichi Kogyo Seiyaku Co., Ltd .; Phosphoric acid ester compound having an allyl ether group in its molecular structure. Examples thereof include commercially available products such as "SIPOMER PAM 5000" manufactured by SOLVAY.
前記溶剤は、活性エネルギー線硬化性樹脂組成物の塗工粘度調節等の目的で添加されるものであり、その種類や添加量は、所望の性能に応じて適宜調整される。一般には、活性エネルギー線硬化性樹脂組成物の不揮発分が１０～９０質量％の範囲となるように用いられる。前記溶剤としては、例えば、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン溶剤；テトラヒドロフラン、ジオキソラン等の環状エーテル溶剤；酢酸メチル、酢酸エチル、酢酸ブチル等のエステル；トルエン、キシレン等の芳香族溶剤；シクロヘキサン、メチルシクロヘキサン等の脂環族溶剤；カルビトール、セロソルブ、メタノール、イソプロパノール、ブタノール、プロピレングリコールモノメチルエーテルなどのアルコール溶剤；エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノプロピルエーテル等のグリコールエーテル系溶剤などが挙げられる。これらの溶剤は単独で用いることも２種以上を併用することもできる。 The solvent is added for the purpose of adjusting the coating viscosity of the active energy ray-curable resin composition, and the type and amount thereof are appropriately adjusted according to the desired performance. Generally, it is used so that the non-volatile content of the active energy ray-curable resin composition is in the range of 10 to 90% by mass. Examples of the solvent include ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone; cyclic ether solvents such as tetrahydrofuran and dioxolan; esters such as methyl acetate, ethyl acetate and butyl acetate; aromatic solvents such as toluene and xylene; cyclohexane. , Alicyclic solvents such as methylcyclohexane; alcohol solvents such as carbitol, cellosolve, methanol, isopropanol, butanol, propylene glycol monomethyl ether; ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monopropyl Examples thereof include glycol ether solvents such as ether. These solvents can be used alone or in combination of two or more.
前記紫外線吸収剤は、例えば、２－［４－｛（２－ヒドロキシ－３－ドデシルオキシプロピル）オキシ｝－２－ヒドロキシフェニル］－４，６－ビス（２，４－ジメチルフェニル）－１，３，５－トリアジン、２－［４－｛（２－ヒドロキシ－３－トリデシルオキシプロピル）オキシ｝－２－ヒドロキシフェニル］－４，６－ビス（２，４－ジメチルフェニル）－１，３，５－トリアジン等のトリアジン誘導体、２－（２’－キサンテンカルボキシ－５’－メチルフェニル）ベンゾトリアゾール、２－（２’－ｏ－ニトロベンジロキシ－５’－メチルフェニル）ベンゾトリアゾール、２－キサンテンカルボキシ－４－ドデシロキシベンゾフェノン、２－ｏ－ニトロベンジロキシ－４－ドデシロキシベンゾフェノン等が挙げられる。これらの紫外線吸収剤は、単独で用いることも２種以上を併用することもできる。 The ultraviolet absorber is, for example, 2- [4-{(2-hydroxy-3-dodecyloxypropyl) oxy} -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1, 3,5-Triazine, 2- [4-{(2-Hydroxy-3-tridecyloxypropyl) oxy} -2-hydroxyphenyl] -4,6-bis (2,4-dimethylphenyl) -1,3 , 5-Triazine derivatives such as triazine, 2- (2'-xanthencarboxy-5'-methylphenyl) benzotriazole, 2- (2'-o-nitrobenzyloxy-5'-methylphenyl) benzotriazole, 2- Examples thereof include xanthencarboxy-4-dodecyloxybenzophenone, 2-o-nitrobenzyloxy-4-dodecyloxybenzophenone and the like. These UV absorbers can be used alone or in combination of two or more.
前記酸化防止剤としては、例えば、ヒンダードフェノール系酸化防止剤、ヒンダードアミン系酸化防止剤、有機硫黄系酸化防止剤、リン酸エステル系酸化防止剤等が挙げられる。これらの酸化防止剤は、単独で用いることも２種以上を併用することもできる。 Examples of the antioxidant include a hindered phenol-based antioxidant, a hindered amine-based antioxidant, an organic sulfur-based antioxidant, a phosphoric acid ester-based antioxidant, and the like. These antioxidants may be used alone or in combination of two or more.
前記シリコン系添加剤は、例えば、ジメチルポリシロキサン、メチルフェニルポリシロキサン、環状ジメチルポリシロキサン、メチルハイドロゲンポリシロキサン、ポリエーテル変性ジメチルポリシロキサン共重合体、ポリエステル変性ジメチルポリシロキサン共重合体、フッ素変性ジメチルポリシロキサン共重合体、アミノ変性ジメチルポリシロキサン共重合体など如きアルキル基やフェニル基を有するポリオルガノシロキサン、ポリエーテル変性アクリル基を有するポリジメチルシロキサン、ポリエステル変性アクリル基を有するポリジメチルシロキサン等が挙げられる。これらのシリコン添加剤は、単独で用いることも２種以上を併用することもできる。 The silicon-based additive includes, for example, dimethylpolysiloxane, methylphenylpolysiloxane, cyclic dimethylpolysiloxane, methylhydrogenpolysiloxane, polyether-modified dimethylpolysiloxane copolymer, polyester-modified dimethylpolysiloxane copolymer, and fluorine-modified dimethyl. Examples thereof include polyorganosiloxane having an alkyl group and a phenyl group such as a polysiloxane copolymer and an amino-modified dimethylpolysiloxane copolymer, polydimethylsiloxane having a polyether-modified acrylic group, and polydimethylsiloxane having a polyester-modified acrylic group. Be done. These silicon additives can be used alone or in combination of two or more.
前記フッ素系添加剤は、例えば、ＤＩＣ株式会社「メガフェース」シリーズ等が挙げられる。これらのフッ素系添加剤は、単独で用いることも２種以上を併用することもできる。 Examples of the fluorine-based additive include DIC Corporation's "Megaface" series. These fluorine-based additives can be used alone or in combination of two or more.
前記帯電防止剤は、例えば、ビス（トリフルオロメタンスルホニル）イミド又はビス（フルオロスルホニル）イミドのピリジニウム、イミダゾリウム、ホスホニウム、アンモニウム、又はリチウム塩が挙げられる。これらの帯電防止剤は、単独で用いることも２種以上を併用することもできる。 Examples of the antistatic agent include pyridinium, imidazolium, phosphonium, ammonium, or lithium salt of bis (trifluoromethanesulfonyl) imide or bis (fluorosulfonyl) imide. These antistatic agents may be used alone or in combination of two or more.
前記有機ビーズは、例えば、ポリメタクリル酸メチルビーズ、ポリカーボネートビーズ、ポリスチレンビーズ、ポリアクリルスチレンビーズ、シリコーンビ－ズ、ガラスビーズ、アクリルビーズ、ベンゾグアナミン系樹脂ビーズ、メラミン系樹脂ビーズ、ポリオレフィン系樹脂ビーズ、ポリエステル系樹脂ビーズ、ポリアミド樹脂ビーズ、ポリイミド系樹脂ビーズ、ポリフッ化エチレン樹脂ビーズ、ポリエチレン樹脂ビーズ等が挙げられる。これらの有機ビーズは、単独で用いることも２種以上を併用することもできる。これら有機ビーズの平均粒径は１～１０μｍの範囲であることが好ましい。 The organic beads include, for example, polymethyl methacrylate beads, polycarbonate beads, polystyrene beads, polyacrylic styrene beads, silicone beads, glass beads, acrylic beads, benzoguanamine resin beads, melamine resin beads, and polyolefin resin beads. Examples thereof include polyester resin beads, polyamide resin beads, polyimide resin beads, polyfluoroethylene resin beads, and polyethylene resin beads. These organic beads can be used alone or in combination of two or more. The average particle size of these organic beads is preferably in the range of 1 to 10 μm.
前記量子ドット（ＱＤ）としては、例えば、ＩＩ－Ｖ族半導体化合物、ＩＩ－ＶＩ族半導体化合物、ＩＩＩ－ＩＶ族半導体化合物、ＩＩＩ－Ｖ族半導体化合物、ＩＩＩ－ＶＩ族半導体化合物、ＩＶ－ＶＩ族半導体化合物、Ｉ－ＩＩＩ－ＶＩ族半導体化合物、ＩＩ－ＩＶ－ＶＩ族半導体化合物、ＩＩ－ＩＶ－Ｖ族半導体化合物、Ｉ－ＩＩ－ＩＶ－ＶＩ族半導体化合物、ＩＶ族元素又はこれを含む化合物等が挙げられる。前記ＩＩ－ＶＩ族半導体化合物としては、例えば、ＺｎＯ、ＺｎＳ、ＺｎＳｅ、ＺｎＴｅ、ＣｄＳ、ＣｄＳｅ、ＣｄＴｅ、ＨｇＳ、ＨｇＳｅ、ＨｇＴｅ等の二元化合物；ＺｎＳｅＳ、ＺｎＳｅＴｅ、ＺｎＳＴｅ、ＣｄＺｎＳ、ＣｄＺｎＳｅ、ＣｄＺｎＴｅ、ＣｄＳｅＳ、ＣｄＳｅＴｅ、ＣｄＳＴｅ、ＣｄＨｇＳ、ＣｄＨｇＳｅ、ＣｄＨｇＴｅ、ＨｇＳｅＳ、ＨｇＳｅＴｅ、ＨｇＳＴｅ、ＨｇＺｎＳ、ＨｇＺｎＳｅ、ＨｇＺｎＴｅ等の三元化合物；ＣｄＺｎＳｅＳ、ＣｄＺｎＳｅＴｅ、ＣｄＺｎＳＴｅ、ＣｄＨｇＳｅＳ、ＣｄＨｇＳｅＴｅ、ＣｄＨｇＳＴｅ、ＣｄＨｇＺｎＴｅ、ＨｇＺｎＳｅＳ、ＨｇＺｎＳｅＴｅ、ＨｇＺｎＳＴｅ等の四元化合物などが挙げられる。前記ＩＩＩ－ＩＶ族半導体化合物としては、例えば、Ｂ４Ｃ３、Ａｌ４Ｃ３、Ｇａ４Ｃ３等が挙げられる。前記ＩＩＩ－Ｖ族半導体化合物としては、例えば、ＢＰ、ＢＮ、ＡｌＮ、ＡｌＰ、ＡｌＡｓ、ＡｌＳｂ、ＧａＮ、ＧａＰ、ＧａＡｓ、ＧａＳｂ、ＩｎＮ、ＩｎＰ、ＩｎＡｓ、ＩｎＳｂ等の二元化合物；ＧａＮＰ、ＧａＮＡｓ、ＧａＮＳｂ、ＧａＰＡｓ、ＧａＰＳｂ、ＡｌＮＰ、ＡｌＮＡｓ、ＡｌＮＳｂ、ＡｌＰＡｓ、ＡｌＰＳｂ、ＩｎＮＰ、ＩｎＮＡｓ、ＩｎＮＳｂ、ＩｎＰＡｓ、ＩｎＰＳｂ、ＧａＡｌＮＰ等の三元化合物；ＧａＡｌＮＡｓ、ＧａＡｌＮＳｂ、ＧａＡｌＰＡｓ、ＧａＡｌＰＳｂ、ＧａＩｎＮＰ、ＧａＩｎＮＡｓ、ＧａＩｎＮＳｂ、ＧａＩｎＰＡｓ、ＧａＩｎＰＳｂ、ＩｎＡｌＮＰ、ＩｎＡｌＮＡｓ、ＩｎＡｌＮＳｂ、ＩｎＡｌＰＡｓ、ＩｎＡｌＰＳｂ等の四元化合物などが挙げられる。前記ＩＩＩ－ＶＩ族半導体化合物としては、例えば、Ａｌ２Ｓ３、Ａｌ２Ｓｅ３、Ａｌ２Ｔｅ３、Ｇａ２Ｓ３、Ｇａ２Ｓｅ３、Ｇａ２Ｔｅ３、ＧａＴｅ、Ｉｎ２Ｓ３、Ｉｎ２Ｓｅ３、Ｉｎ２Ｔｅ３、ＩｎＴｅ等が挙げられる。前記ＩＶ－ＶＩ族半導体化合物としては、例えば、ＳｎＳ、ＳｎＳｅ、ＳｎＴｅ、ＰｂＳ、ＰｂＳｅ、ＰｂＴｅ等の二元化合物；ＳｎＳｅＳ、ＳｎＳｅＴｅ、ＳｎＳＴｅ、ＰｂＳｅＳ、ＰｂＳｅＴｅ、ＰｂＳＴｅ、ＳｎＰｂＳ、ＳｎＰｂＳｅ、ＳｎＰｂＴｅ等の三元化合物；ＳｎＰｂＳＳｅ、ＳｎＰｂＳｅＴｅ、ＳｎＰｂＳＴｅ等の四元化合物などが挙げられる。前記Ｉ－ＩＩＩ－ＶＩ族半導体化合物としては、例えば、ＣｕＩｎＳ２、ＣｕＩｎＳｅ２、ＣｕＩｎＴｅ２、ＣｕＧａＳ２、ＣｕＧａＳｅ２、ＣｕＧａＳｅ２、ＡｇＩｎＳ２、ＡｇＩｎＳｅ２、ＡｇＩｎＴｅ２、ＡｇＧａＳｅ２、ＡｇＧａＳ２、ＡｇＧａＴｅ２等が挙げられる。前記ＩＶ族元素又はこれを含む化合物としては、例えば、Ｃ、Ｓｉ、Ｇｅ、ＳｉＣ、ＳｉＧｅ等が挙げられる。量子ドットは単一の半導体化合物からなっていてもよいし、複数の半導体化合物からなるコアシェル構造を有していてもよい。また、その表面を有機化合物にて修飾したものであってもよい。 Examples of the quantum dot (QD) include II-V group semiconductor compounds, II-VI group semiconductor compounds, III-IV group semiconductor compounds, III-V group semiconductor compounds, III-VI group semiconductor compounds, and IV-VI group. Semiconductor compounds, I-III-VI group semiconductor compounds, II-IV-VI group semiconductor compounds, II-IV-V group semiconductor compounds, I-II-IV-VI group semiconductor compounds, IV group elements or compounds containing them, etc. Can be mentioned. Examples of the II-VI group semiconductor compound include binary compounds such as ZnO, ZnS, ZnSe, ZnTe, CdS, CdSe, CdTe, HgS, HgSe, and HgTe; ZnSeS, ZnSeTe, ZnSTe, CdZnS, CdZnSe, CdZnTe, and CdSe. 、ＣｄＳｅＴｅ、ＣｄＳＴｅ、ＣｄＨｇＳ、ＣｄＨｇＳｅ、ＣｄＨｇＴｅ、ＨｇＳｅＳ、ＨｇＳｅＴｅ、ＨｇＳＴｅ、ＨｇＺｎＳ、ＨｇＺｎＳｅ、ＨｇＺｎＴｅ等の三元化合物；ＣｄＺｎＳｅＳ、ＣｄＺｎＳｅＴｅ、ＣｄＺｎＳＴｅ、ＣｄＨｇＳｅＳ、ＣｄＨｇＳｅＴｅ、ＣｄＨｇＳＴｅ、ＣｄＨｇＺｎＴｅ、ＨｇＺｎＳｅＳ、ＨｇＺｎＳｅＴｅ、ＨｇＺｎＳＴｅ等の四Examples include the original compound. Examples of the group III-IV semiconductor compound include B 4 C 3 , Al 4 C 3 , Ga 4 C 3 , and the like. Examples of the group III-V semiconductor compound include binary compounds such as BP, BN, AlN, AlP, AlAs, AlSb, GaN, GaP, GaAs, GaSb, InN, InP, InAs, and InSb; , GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InNP, InNAs, InNSb, InPAs, InPSb, GaAlNP and other ternary compounds; Examples thereof include quaternary compounds such as InAlNP, InAlNAs, InAlNSb, InAlPAs, and InAlPSb. Examples of the III-VI group semiconductor compound include Al 2 S 3 , Al 2 Se 3 , Al 2 Te 3 , Ga 2 S 3 , Ga 2 Se 3 , Ga 2 Te 3 , Ga Te, In 2 S 3 , and In. 2 Se 3 , In 2 Te 3 , InTe and the like can be mentioned. Examples of the IV-VI group semiconductor compound include binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, and PbTe; SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbS, etc. Compounds; Examples thereof include quaternary compounds such as SnPbSSe, SnPbSeTe, and SnPbSTe. Examples of the I-III-VI group semiconductor compound include CuInS 2 , CuInSe 2 , CuInTe 2 , CuGaS 2 , CuGaSe 2 , CuGaSe 2 , AgInS 2 , AgInSe 2 , AgInTe 2 , AgGaSe 2 , AgGaS 2 , etc. Can be mentioned. Examples of the Group IV element or a compound containing the same include C, Si, Ge, SiC, SiGe and the like. The quantum dots may be composed of a single semiconductor compound or may have a core-shell structure composed of a plurality of semiconductor compounds. Further, the surface thereof may be modified with an organic compound.
これら各種の添加剤は、所望の性能等に応じて任意の量添加することができるが、通常、活性エネルギー線硬化性樹脂組成物の不揮発分１００質量部に対して、０．０１～４０質量部の範囲で用いることが好ましい。 These various additives can be added in any amount depending on the desired performance and the like, but usually 0.01 to 40 mass by mass with respect to 100 parts by mass of the non-volatile content of the active energy ray-curable resin composition. It is preferable to use it in the range of parts.
本発明の活性エネルギー線硬化性樹脂組成物は、前記各配合成分を混合して製造される。混合方法は特に限定されず、ペイントシェイカー、ディスパー、ロールミル、ビーズミル、ボールミル、アトライター、サンドミル、ビーズミル等を用いることができる。 The active energy ray-curable resin composition of the present invention is produced by mixing the above-mentioned compounding components. The mixing method is not particularly limited, and a paint shaker, a disper, a roll mill, a bead mill, a ball mill, an attritor, a sand mill, a bead mill and the like can be used.
本発明の硬化物は、前記活性エネルギー線硬化性樹脂組成物に、活性エネルギー線を照射することで得ることができる。前記活性エネルギー線としては、例えば、紫外線、電子線、α線、β線、γ線等の電離放射線が挙げられる。また、前記活性エネルギー線として、紫外線を用いる場合、紫外線による硬化反応を効率よく行う上で、窒素ガス等の不活性ガス雰囲気下で照射してもよく、空気雰囲気下で照射してもよい。 The cured product of the present invention can be obtained by irradiating the active energy ray-curable resin composition with active energy rays. Examples of the active energy ray include ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. When ultraviolet rays are used as the active energy rays, they may be irradiated in an atmosphere of an inert gas such as nitrogen gas or in an air atmosphere in order to efficiently carry out the curing reaction by the ultraviolet rays.
紫外線発生源としては、実用性、経済性の面から紫外線ランプが一般的に用いられている。具体的には、低圧水銀ランプ、高圧水銀ランプ、超高圧水銀ランプ、キセノンランプ、ガリウムランプ、メタルハライドランプ、太陽光、ＬＥＤ等が挙げられる。 As an ultraviolet ray generation source, an ultraviolet lamp is generally used from the viewpoint of practicality and economy. Specific examples thereof include low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, gallium lamps, metal halide lamps, sunlight, and LEDs.
前記活性エネルギー線の積算光量は、特に制限されないが、０．１～５０ｋＪ／ｍ２であることが好ましく、０．５～１０ｋＪ／ｍ２であることがより好ましい。積算光量が上記範囲であると、未硬化部分の発生の防止又は抑制ができることから好ましい。 The integrated light amount of the active energy rays is not particularly limited, but is preferably 0.1 to 50 kJ / m 2 , and more preferably 0.5 to 10 kJ / m 2 . When the integrated light amount is in the above range, it is preferable because the generation of the uncured portion can be prevented or suppressed.
なお、前記活性エネルギー線の照射は、一段階で行ってもよいし、二段階以上に分けて行ってもよい。 The irradiation of the active energy rays may be performed in one step or may be divided into two or more steps.
本発明の物品としては、例えば、光学部材等が挙げられる。 Examples of the article of the present invention include optical members and the like.
前記光学部材としては、例えば、プラスチックレンズ、偏光フィルム、位相差フィルム、反射防止フィルム、輝度向上フィルム（プリズムシート、マイクロレンズシート等）、光拡散フィルム、ハードコートフィルム、フィルム型液晶素子、タッチパネル等が挙げられる。 Examples of the optical member include a plastic lens, a polarizing film, a retardation film, an antireflection film, a brightness improving film (prism sheet, microlens sheet, etc.), a light diffusing film, a hard coat film, a film-type liquid crystal element, a touch panel, and the like. Can be mentioned.
以下、実施例と比較例とにより、本発明を具体的に説明する。なお、本発明は、以下に挙げた実施例に限定されるものではない。 Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples. The present invention is not limited to the examples listed below.
（実施例１：活性エネルギー線硬化性樹脂組成物（１）の調製）
温度計、冷却管、撹拌器を取り付けたフラスコに、フタル酸無水物１４８質量部（１．００モル）と不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン２モル付加物（株式会社ダイセル製「プラクセルＦＡ２Ｄ」）３５３質量部（１．０２モル）と２，６－ジ－ｔｅｒｔ－ブチル－ｐ－クレゾール２質量部、４－メトキシフェノール０．２質量部を仕込み、系内を１００℃に制御して８時間撹拌した。次いで、温度を６０℃まで低下させた後、ビスフェノールＡ型エポキシ樹脂（ＤＩＣ株式会社製「エピクロン８５０－Ｓ」）１８６質量部（０．５０モル）を加えて、１０５℃で７時間撹拌を続け、得られた反応物をろ過回収することで、活性エネルギー線硬化性樹脂組成物（１）を得た。
(Example 1: Preparation of active energy ray-curable resin composition (1))
In a flask equipped with a thermometer, a cooling tube, and a stirrer, 148 parts by mass (1.00 mol) of phthalic acid anhydride and 2 mol of unsaturated fatty acid hydroxyalkyl ester-modified ε-caprolactone (Dycel Co., Ltd. “Plaxel FA2D”) ”) 353 parts by mass (1.02 mol), 2 parts by mass of 2,6-di-tert-butyl-p-cresol and 0.2 parts by mass of 4-methoxyphenol were charged, and the inside of the system was controlled to 100 ° C. The mixture was stirred for 8 hours. Next, after lowering the temperature to 60 ° C., 186 parts by mass (0.50 mol) of bisphenol A type epoxy resin (“Epiclon 850-S” manufactured by DIC Corporation) was added, and stirring was continued at 105 ° C. for 7 hours. The obtained reaction product was collected by filtration to obtain an active energy ray-curable resin composition (1).
（実施例２：活性エネルギー線硬化性樹脂組成物（２）の調製）
実施例１で用いた不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン２モル付加物（株式会社ダイセル製「プラクセルＦＡ２Ｄ」）３５３質量部を、不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン１モル付加物（株式会社ダイセル製「プラクセルＦＡ１ＤＤＭ」）２３１質量部に変更した以外は実施例１と同様にして、活性エネルギー線硬化性樹脂組成物（２）を得た。
(Example 2: Preparation of active energy ray-curable resin composition (2))
353 parts by mass of the unsaturated fatty acid hydroxyalkyl ester-modified ε-caprolactone 2 mol adduct (“Plaxel FA2D” manufactured by Daicel Co., Ltd.) used in Example 1 was added to 1 mol of unsaturated fatty acid hydroxyalkyl ester modified ε-caprolactone (1 mol adduct). An active energy ray-curable resin composition (2) was obtained in the same manner as in Example 1 except that the amount was changed to 231 parts by mass (“Praccel FA1DDM” manufactured by Daicel Co., Ltd.).
（実施例３：活性エネルギー線硬化性樹脂組成物（３）の調製）
実施例１で用いた不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン２モル付加物（株式会社ダイセル製「プラクセルＦＡ２Ｄ」）３５３質量部をポリエチレングリコールモノアクリレート（ＥＯ鎖４．５モル相当）（日油株式会社製「ブレンマーＡＥ－２００」）３５９質量部に変更した以外は実施例１と同様にして、活性エネルギー線硬化性樹脂組成物（３）を得た。
(Example 3: Preparation of active energy ray-curable resin composition (3))
2 mol of unsaturated fatty acid hydroxyalkyl ester-modified ε-caprolactone used in Example 1 (“Plaxel FA2D” manufactured by Daicel Co., Ltd.) 353 parts by mass of polyethylene glycol monoacrylate (equivalent to 4.5 mol of EO chain) (Japanese oil) An active energy ray-curable resin composition (3) was obtained in the same manner as in Example 1 except that the amount was changed to 359 parts by mass of "Blemmer AE-200" manufactured by Blemmer AE-200 Co., Ltd.
（実施例４：活性エネルギー線硬化性樹脂組成物（４）の調製）
実施例１で用いた不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン２モル付加物（株式会社ダイセル製「プラクセルＦＡ２Ｄ」）３５３質量部をポリエチレングリコールモノアクリレート（ＥＯ鎖１０モル相当）（日油株式会社製「ブレンマーＡＥ－４００」）５４０質量部に変更した以外は実施例１と同様にして、活性エネルギー線硬化性樹脂組成物（４）を得た。
(Example 4: Preparation of active energy ray-curable resin composition (4))
2 mol of unsaturated fatty acid hydroxyalkyl ester-modified ε-caprolactone used in Example 1 (“Plaxel FA2D” manufactured by Daicel Co., Ltd.) 353 parts by mass of polyethylene glycol monoacrylate (equivalent to 10 mol of EO chain) (Nippon Oil Co., Ltd.) The active energy ray-curable resin composition (4) was obtained in the same manner as in Example 1 except that the amount was changed to 540 parts by mass of "Blemmer AE-400" manufactured by Blemmer AE-400.
（実施例５：活性エネルギー線硬化性樹脂組成物（５）の調製）
実施例１で用いたフタル酸無水物１４８質量部をｃｉｓ－シクロヘキサン－１，２－ジカルボン酸無水物１５４質量部に変更し、かつ、実施例１で用いた不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン２モル付加物（株式会社ダイセル製「プラクセルＦＡ２Ｄ」）３５３質量部をポリエチレングリコールモノアクリレート（ＥＯ鎖１０モル相当）（日油株式会社製「「ブレンマーＡＥ－４００」）５４０質量部に変更した以外は実施例１と同様にして、活性エネルギー線硬化性樹脂組成物（５）を得た。
(Example 5: Preparation of active energy ray-curable resin composition (5))
The 148 parts by mass of the phthalic acid anhydride used in Example 1 was changed to 154 parts by mass of the cis-cyclohexane-1,2-dicarboxylic acid anhydride, and the unsaturated fatty acid hydroxyalkyl ester-modified ε- used in Example 1 was changed. 353 parts by mass of caprolactone 2 mol addition ("Plaxel FA2D" manufactured by Daicel Co., Ltd.) was changed to 540 parts by mass of polyethylene glycol monoacrylate (equivalent to 10 mol of EO chain) ("Blemmer AE-400" manufactured by Nikko Co., Ltd.). The active energy ray-curable resin composition (5) was obtained in the same manner as in Example 1 except for the above.
（実施例６：活性エネルギー線硬化性樹脂組成物（６）の調製）
実施例１で用いたビスフェノールＡ型エポキシ樹脂（ＤＩＣ株式会社製「エピクロン８５０－Ｓ」）１８６質量部をナフタレン型エポキシ樹脂（ＤＩＣ株式会社「ＨＰ－４０３２ＳＳ」）１３６質量部に変更し、かつ、実施例１で用いた不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン２モル付加物（株式会社ダイセル製「プラクセルＦＡ２Ｄ」）３５３質量部をポリエチレングリコールモノアクリレート（ＥＯ鎖４．５モル相当）（日油株式会社製「ブレンマーＡＥ－２００」）３５９質量部に変更した以外は実施例１と同様にして、活性エネルギー線硬化性樹脂組成物（６）を得た。
(Example 6: Preparation of active energy ray-curable resin composition (6))
The 186 parts by mass of the bisphenol A type epoxy resin (“Epiclon 850-S” manufactured by DIC Co., Ltd.) used in Example 1 was changed to 136 parts by mass of the naphthalene type epoxy resin (“HP-4032SS” manufactured by DIC Co., Ltd.). 2 mol of unsaturated fatty acid hydroxyalkyl ester-modified ε-caprolactone used in Example 1 (“Placcel FA2D” manufactured by Daicel Co., Ltd.) 353 parts by mass of polyethylene glycol monoacrylate (equivalent to 4.5 mol of EO chain) (Japanese oil) The active energy ray-curable resin composition (6) was obtained in the same manner as in Example 1 except that the amount was changed to 359 parts by mass of "Blemmer AE-200" manufactured by Blemmer AE-200 Co., Ltd.
（比較例１：活性エネルギー線硬化性樹脂組成物（Ｒ１）の調製）
温度計、冷却管、撹拌器を取り付けたフラスコに、フタル酸無水物１４８質量部（１．００モル）と不飽和脂肪酸ヒドロキシアルキルエステル修飾ε-カプロラクトン２モル付加物（株式会社ダイセル製「プラクセルＦＡ２Ｄ」）３５３質量部（１．０２モル）と２，６－ジ－ｔｅｒｔ－ブチル－ｐ－クレゾール２質量部、４－メトキシフェノール０．２質量部を仕込み、系内を１００℃に制御して８時間撹拌した。次いで、温度を６０℃まで低下させた後、ネオペンチルグリコールジグリシジルエーテルを主成分とするエポキシ樹脂（株式会社ＡＤＥＫＡ製「ＥＤ－５２３Ｔ」）１０８質量部を加えて、１０５℃で７時間撹拌を続け、得られた反応物をろ過回収することで、活性エネルギー線硬化性樹脂組成物（Ｒ１）を得た。
(Comparative Example 1: Preparation of active energy ray-curable resin composition (R1))
In a flask equipped with a thermometer, a cooling tube, and a stirrer, 148 parts by mass (1.00 mol) of phthalic acid anhydride and 2 mol of unsaturated fatty acid hydroxyalkyl ester-modified ε-caprolactone (Dycel Co., Ltd. “Plaxel FA2D”) ”) 353 parts by mass (1.02 mol), 2 parts by mass of 2,6-di-tert-butyl-p-cresol and 0.2 parts by mass of 4-methoxyphenol were charged, and the inside of the system was controlled to 100 ° C. The mixture was stirred for 8 hours. Next, after lowering the temperature to 60 ° C., 108 parts by mass of an epoxy resin (“ED-523T” manufactured by ADEKA Co., Ltd.) containing neopentyl glycol diglycidyl ether as a main component was added, and the mixture was stirred at 105 ° C. for 7 hours. Subsequently, the obtained reaction product was collected by filtration to obtain an active energy ray-curable resin composition (R1).
（比較例２：活性エネルギー線硬化性樹脂組成物（Ｒ２）の調製）
温度計、冷却管、撹拌器を取り付けたフラスコに、フタル酸無水物１４８質量部（１．００モル）とヒドロキシエチルアクリレート１１８質量部と２，６－ジ－ｔｅｒｔ－ブチル－ｐ－クレゾール２質量部、４－メトキシフェノール０．２質量部を仕込み、系内を１００℃に制御して８時間撹拌した。次いで、温度を６０℃まで低下させた後、ビスフェノールＡ型エポキシ樹脂（ＤＩＣ株式会社製「エピクロン８５０－Ｓ」）１８６質量部（０．５０モル）を加えて、１０５℃で７時間撹拌を続け、得られた反応物をろ過回収することで、活性エネルギー線硬化性樹脂組成物（Ｒ２）を得た。
(Comparative Example 2: Preparation of active energy ray-curable resin composition (R2))
In a flask equipped with a thermometer, a cooling tube, and a stirrer, 148 parts by mass (1.00 mol) of phthalic anhydride, 118 parts by mass of hydroxyethyl acrylate, and 2 parts by mass of 2,6-di-tert-butyl-p-cresol. 0.2 parts by mass of 4-methoxyphenol was charged, and the inside of the system was controlled to 100 ° C. and stirred for 8 hours. Next, after lowering the temperature to 60 ° C., 186 parts by mass (0.50 mol) of bisphenol A type epoxy resin (“Epiclon 850-S” manufactured by DIC Corporation) was added, and stirring was continued at 105 ° C. for 7 hours. The obtained reaction product was collected by filtration to obtain an active energy ray-curable resin composition (R2).
上記の実施例及び比較例で得られた活性エネルギー線硬化性樹脂組成物を用いて、下記の測定及び評価を行った。 The following measurements and evaluations were carried out using the active energy ray-curable resin compositions obtained in the above Examples and Comparative Examples.
［屈折率の測定方法］
ガラス板上に実施例及び比較例で得られた活性エネルギー線硬化性樹脂組成物１００質量部に光重合開始剤（ＩＧＭ Ｒｅｓｉｎｓ社製「Ｏｍｎｉｒａｄ １８４」）３質量部を添加混合し、硬化時の膜厚が５０μｍになるようにアプリケーターを使用して塗布し、活性エネルギー線を照射して前記基材の表面に活性エネルギー線硬化性樹脂組成物の硬化塗膜を形成した。前記硬化塗膜をガラス基板より剥離し、その屈折率をアッべ屈折率計（株式会社アタゴ製「ＮＡＲ－３Ｔ」）を用いて測定した。
[Measurement method of refractive index]
To 100 parts by mass of the active energy ray-curable resin composition obtained in Examples and Comparative Examples, 3 parts by mass of a photopolymerization initiator (“Omnirad 184” manufactured by IGM Resins) was added and mixed on a glass plate, and when cured. The coating was applied using an applicator so that the film thickness was 50 μm, and the substrate was irradiated with active energy rays to form a cured coating film of the active energy ray-curable resin composition on the surface of the substrate. The cured coating film was peeled off from a glass substrate, and its refractive index was measured using an Abbe refractive index meter (“NAR-3T” manufactured by Atago Co., Ltd.).
［耐摩耗性の測定方法］
実施例及び比較例で得られた活性エネルギー線硬化性樹脂組成物１００質量部に光重合開始剤（ＩＧＭ Ｒｅｓｉｎｓ社製「Ｏｍｎｉｒａｄ １８４」）３質量部を添加混合し、適当なプラスチックフィルムに塗布した後、８０Ｗ高圧水銀ランプで紫外線照射することでフィルム上に硬化塗膜を有する積層体を得た。次いで、スチールウール（日本スチールウール株式会社製「ボンスター＃００００」）０．５ｇで直径２．４センチメートルの円盤状の圧子を包み、該圧子に５００ｇ重の荷重をかけて、該積層体の塗装表面を１０往復させる磨耗試験を行った。磨耗試験前後の積層フィルムのヘーズ値をスガ試験機株式会社製「ヘーズコンピュータＨＺ－２」を用いて測定し、それらの差の値（ｄＨ）を用いて、以下の基準に従い評価した。なお、差の値（ｄＨ）が小さいほど、耐摩耗性に優れる。
[Measurement method of wear resistance]
To 100 parts by mass of the active energy ray-curable resin composition obtained in Examples and Comparative Examples, 3 parts by mass of a photopolymerization initiator (“Omnirad 184” manufactured by IGM Resins) was added and mixed, and the mixture was applied to an appropriate plastic film. Then, by irradiating with ultraviolet rays with an 80 W high-pressure mercury lamp, a laminate having a cured coating film on the film was obtained. Next, 0.5 g of steel wool (“Bonster # 0000” manufactured by Nippon Steel Wool Co., Ltd.) wraps a disk-shaped indenter with a diameter of 2.4 cm, and a load of 500 g is applied to the indenter to apply a load of 500 g to the laminate. A wear test was performed in which the painted surface was reciprocated 10 times. The haze value of the laminated film before and after the wear test was measured using "Haze Computer HZ-2" manufactured by Suga Test Instruments Co., Ltd., and the difference value (dH) was used for evaluation according to the following criteria. The smaller the difference value (dH), the better the wear resistance.
Ａ：ｄＨが、２．０以下であった
Ｂ：ｄＨが、２．０超５．０以下であった。
Ｃ：ｄＨが、５．０超１０．０以下であった。
Ｄ：ｄＨが、１０．０超１５．０以下であった。
Ｅ：ｄＨが、１５．０超であった。
A: dH was 2.0 or less. B: dH was more than 2.0 and 5.0 or less.
C: dH was more than 5.0 and 10.0 or less.
D: dH was more than 10.0 and 15.0 or less.
E: dH was over 15.0.
表１に示した実施例１～６は、本発明の活性エネルギー線硬化性樹脂組成物を用いた例である。これらの活性エネルギー線硬化性樹脂組成物は、高い屈折率性能を有し、優れた耐摩耗性を有することが確認できた。 Examples 1 to 6 shown in Table 1 are examples using the active energy ray-curable resin composition of the present invention. It was confirmed that these active energy ray-curable resin compositions have high refractive index performance and excellent wear resistance.
一方、比較例１は、本発明で規定する一分子中に少なくとも２つの芳香環及び少なくとも１つのエポキシ基を有する化合物を有しない活性エネルギー線硬化性樹脂組成物を用いた例である。この活性エネルギー線硬化性樹脂組成物は、耐摩耗性には優れるものの、屈折率性能が不十分であることが確認できた。 On the other hand, Comparative Example 1 is an example using an active energy ray-curable resin composition having no compound having at least two aromatic rings and at least one epoxy group in one molecule defined in the present invention. It was confirmed that this active energy ray-curable resin composition has excellent wear resistance but insufficient refractive index performance.
比較例２は、本発明で規定するアルキレンオキサイド鎖及び／又はエステル鎖を有する（メタ）アクリレート化合物を有しない活性エネルギー線硬化性樹脂組成物を用いた例である。この活性エネルギー線硬化性樹脂組成物は、高い屈折率性能を有するものの、耐摩耗性が著しく不十分であることが確認できた。 Comparative Example 2 is an example using an active energy ray-curable resin composition having no (meth) acrylate compound having an alkylene oxide chain and / or an ester chain specified in the present invention. It was confirmed that this active energy ray-curable resin composition has high refractive index performance, but its wear resistance is remarkably insufficient.
Claims (7)
多塩基酸無水物（Ｂ）と、
アルキレンオキサイド鎖及び／又はエステル鎖を有する（メタ）アクリレート化合物（Ｃ）と、
を必須原料とする活性エネルギー線硬化性樹脂組成物であって、
前記多塩基酸無水物（Ｂ）が、脂環式多塩基酸無水物及び／又は芳香族多塩基酸無水物であり、
前記化合物（Ｃ）が有するアルキレンオキサイド鎖の繰り返し単位数が、２～２０の範囲であり、
エステル鎖の炭素原子数が、５以上であることを特徴とする活性エネルギー線硬化性樹脂組成物。 Compound (A) having at least two aromatic rings and at least one epoxy group in one molecule, and
Polybasic acid anhydride (B) and
With the (meth) acrylate compound (C) having an alkylene oxide chain and / or an ester chain,
An active energy ray-curable resin composition containing the above as an essential raw material.
The polybasic acid anhydride (B) is an alicyclic polybasic acid anhydride and / or an aromatic polybasic acid anhydride.
The number of repeating units of the alkylene oxide chain contained in the compound (C) is in the range of 2 to 20.
An active energy ray-curable resin composition characterized by having 5 or more carbon atoms in the ester chain.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020212260A JP2022098704A (en) | 2020-12-22 | 2020-12-22 | Active energy ray-curable resin composition, cured product and article |
| TW110146904A TW202239794A (en) | 2020-12-22 | 2021-12-15 | Active energy ray-curable resin composition, cured product, and article |
| CN202111571255.XA CN114656767A (en) | 2020-12-22 | 2021-12-21 | Active energy ray-curable resin composition, cured product, and article |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020212260A JP2022098704A (en) | 2020-12-22 | 2020-12-22 | Active energy ray-curable resin composition, cured product and article |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2022098704A true JP2022098704A (en) | 2022-07-04 |
Family
ID=82026100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020212260A Pending JP2022098704A (en) | 2020-12-22 | 2020-12-22 | Active energy ray-curable resin composition, cured product and article |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2022098704A (en) |
| CN (1) | CN114656767A (en) |
| TW (1) | TW202239794A (en) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101449325B (en) * | 2006-05-24 | 2011-02-16 | Dic株式会社 | Optical disk and ultraviolet-curable composition for optical disk |
| JPWO2010110407A1 (en) * | 2009-03-27 | 2012-10-04 | 昭和電工株式会社 | Transparent composite material |
| KR101581082B1 (en) * | 2009-10-16 | 2015-12-30 | 내셔널 프린팅 뷰로우 인코퍼레이티드 어드미니스트레이티브 에이전시 | Intaglio printing ink |
| CN101935494B (en) * | 2010-08-18 | 2013-11-13 | 梁鹏飞 | Ultraviolet-cured resin composition and preparation method thereof |
| TW201829615A (en) * | 2016-12-08 | 2018-08-16 | 日商迪愛生股份有限公司 | Active-energy-beam-curable resin composition, and laminate film |
| TW201946945A (en) * | 2018-05-15 | 2019-12-16 | 日商Ｄｉｃ股份有限公司 | Epoxy (meth) acrylate resin composition, curable resin composition, cured product, and article |
| WO2020209264A1 (en) * | 2019-04-10 | 2020-10-15 | Dic株式会社 | Actinic-ray-curable resin composition, cured object, layered product, and article |
-
2020
- 2020-12-22 JP JP2020212260A patent/JP2022098704A/en active Pending
-
2021
- 2021-12-15 TW TW110146904A patent/TW202239794A/en unknown
- 2021-12-21 CN CN202111571255.XA patent/CN114656767A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN114656767A (en) | 2022-06-24 |
| TW202239794A (en) | 2022-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111187379B (en) | Composition for forming quantum dot layer, quantum dot film, backlight unit, and liquid crystal display | |
| JP5989417B2 (en) | Ultraviolet curable silicone resin composition and image display device using the same | |
| EP3032294A1 (en) | Method for preparing quantum dot-polymer complex, quantum dot-polymer complex, light conversion film, backlight unit and display device having the same | |
| US10852584B2 (en) | Method for quantum dot-polymer composite, quantum dot-polymer composite, light conversion film comprising same, backlight unit, and display device | |
| JP6928596B2 (en) | A light conversion resin composition, a light conversion laminated base material containing the same, and an image display device using the same. | |
| WO2010067876A1 (en) | Curable composition comprising inorganic oxide microparticles that are surface-modified with maleimide groups | |
| KR102153733B1 (en) | Color filter and image display device using the same | |
| JP2017110137A (en) | Dual curable silicon composition and article using the same | |
| EP3177111A1 (en) | Organic el light-emitting device | |
| KR101773202B1 (en) | Adhesive, manufacturing method of display device using the same | |
| JP7131695B2 (en) | Active energy ray-curable resin composition, cured product, laminate and article | |
| JP2022098704A (en) | Active energy ray-curable resin composition, cured product and article | |
| JP2007171555A (en) | Hard coat film and optical functional film, optical lens and optical component | |
| AU2018270565B2 (en) | Optical transparent resin and electronic element formed using same | |
| WO2022244669A1 (en) | Ink composition, light conversion layer, color filter, and light conversion film | |
| JP5897341B2 (en) | Photosensitive resin composition | |
| CN110741025A (en) | Curable composition and laminated film | |
| TWI821441B (en) | Curable compositions, films, laminates and display devices | |
| KR20150078060A (en) | Composition for forming resin layer and flexible display substrate using the same | |
| JP7364098B2 (en) | Acrylic (meth)acrylate resin, active energy ray-curable resin composition, cured product and article | |
| KR102174182B1 (en) | A self-light emitting photosensitive resin composition, color filter and display device comprising the same | |
| JP2019174803A (en) | Light-converting resin composition, light-converting laminated substrate, and image display device using the same | |
| JP6919308B2 (en) | (Meta) Acryloyl group-containing resin and laminated film | |
| JP2020100686A (en) | Active energy ray curable resin composition, laminated film, producing method thereof, and producing method for decorative film | |
| JP7346817B2 (en) | Laminate and its uses |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20210415 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20231107 |