JP6859874B2 - 活性エネルギー線硬化性樹脂組成物及び積層体 - Google Patents
活性エネルギー線硬化性樹脂組成物及び積層体 Download PDFInfo
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- JP6859874B2 JP6859874B2 JP2017128141A JP2017128141A JP6859874B2 JP 6859874 B2 JP6859874 B2 JP 6859874B2 JP 2017128141 A JP2017128141 A JP 2017128141A JP 2017128141 A JP2017128141 A JP 2017128141A JP 6859874 B2 JP6859874 B2 JP 6859874B2
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- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 1
- LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 description 1
- AQROEYPMNFCJCK-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-tert-butyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O AQROEYPMNFCJCK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JCGAFSOOJHZRCB-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methoxycarbonyl]hexanoic acid Chemical compound CCCCC(C(O)=O)C(=O)OCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JCGAFSOOJHZRCB-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
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical group OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- BSMGLVDZZMBWQB-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=CC=C1 BSMGLVDZZMBWQB-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 1
- DRXGKQPTFWTTJW-UHFFFAOYSA-N 5-butoxy-2-[4-(4-butoxy-2-hydroxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5-triazin-2-yl]phenol Chemical compound OC1=CC(OCCCC)=CC=C1C1=NC(C=2C(=CC(OCCCC)=CC=2)O)=NC(C=2C(=CC(OCCCC)=CC=2)OCCCC)=N1 DRXGKQPTFWTTJW-UHFFFAOYSA-N 0.000 description 1
- OCIFJWVZZUDMRL-UHFFFAOYSA-N 6-hydroxyhexyl prop-2-enoate Chemical compound OCCCCCCOC(=O)C=C OCIFJWVZZUDMRL-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- YRXGUZPUZBCGST-UHFFFAOYSA-N [2-(hydroxymethoxy)phenyl]-phenylmethanone Chemical compound OCOC1=CC=CC=C1C(=O)C1=CC=CC=C1 YRXGUZPUZBCGST-UHFFFAOYSA-N 0.000 description 1
- GLLSGHWYBGERSE-UHFFFAOYSA-N [2-(hydroxymethoxy)phenyl]-phenylmethanone;sodium Chemical compound [Na].OCOC1=CC=CC=C1C(=O)C1=CC=CC=C1 GLLSGHWYBGERSE-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- DVQGYGDSAGBRSZ-UHFFFAOYSA-N bis(1-cyclohexylcyclohexa-2,4-dien-1-yl)methanone Chemical compound C1C=CC=CC1(C1CCCCC1)C(=O)C1(C2CCCCC2)CC=CC=C1 DVQGYGDSAGBRSZ-UHFFFAOYSA-N 0.000 description 1
- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- AEQPIBDYEXHEKN-UHFFFAOYSA-N butyl acetate;ethanol Chemical compound CCO.CCCCOC(C)=O AEQPIBDYEXHEKN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 150000002027 dodecanoic acid esters Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical compound O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000003003 phosphines 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
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007767 slide coating Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002023 wood Substances 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
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
分子中に不飽和二重結合を2つ有する化合物(B)10〜60重量%、
及び
平均一次粒子径が20〜80nmである金属酸化物微粒子(D)20〜60重量%
を含有する活性エネルギー線硬化性樹脂組成物。
エポキシ基、水酸基及びイソシアネート基からなる群より選ばれる少なくとも1種の官能基を有する単量体(a1)、並びにピペリジニル基を有する単量体(a2)を含む単量体成分の重合体(A1)と、
(A1)成分が有する官能基と反応し得る、官能基を有する単量体(a4)との反応生成物である、前項1の活性エネルギー線硬化性樹脂組成物。
二重結合当量は、以下の式1から算出した。
(式1)二重結合当量(g/eq)=[{(a1)〜(a4)成分の使用重量(g)}+{開始剤の使用重量(g)}]/(a4)成分の使用モル量(mol)
アミン当量は、以下の式2から算出した。
(式2)アミン当量(g/eq)=[{(a1)〜(a4)成分の使用重量(g)}+{開始剤の使用重量(g)}]/(a2)成分の使用モル量(mol)
撹拌装置、冷却管、滴下ロート及び窒素導入管を備えた反応容器に、グリシジルメタクリレート(以下、GMAという)を30部、1,2,2,6、6−ペンタメチル−4−ピペリジルメタクリレート(以下、HALS―1という)を20部、メチルメタクリレート(以下、MMAという)を50部、2,2´−アゾビスイソブチロニトリル(以下、AIBNという)を4部および酢酸ブチルを400部仕込んだ後、窒素気流下に約1時間かけて系内温度が約95℃になるまで昇温し、1時間保温した。次いで、あらかじめGMAを90部、HALS−1を60部、MMAを150部、およびAIBNを12部仕込んだ混合液を滴下ロートより、窒素気流下に約2時間を要して系内へ滴下し、同温度で3時間保温後、AIBNを1部仕込み、1時間保温した。その後、120℃に昇温し、2時間保温した。その後、反応系を冷却し、重合体(A1―1)の溶液を得た。
表1に示すような組成で、製造例1と同様の方法で製造し、重合体(A−2)〜(A−6)及び(F−1)をそれぞれ得た。
製造例1と同様の反応容器に、2−ヒドロキシエチルメタクリレート(以下、HEMAという)を30部、HALS−1を40部、MMAを30部、AIBNを4部および酢酸ブチルを400部仕込んだ後、窒素気流下に約1時間かけて系内温度が約95℃になるまで昇温し、1時間保温した。次いで、あらかじめHEMAを90部、HALS−1を120部、MMAを90部、およびAIBNを12部仕込んだ混合液を滴下ロートより、窒素気流下に約2時間を要して系内へ滴下し、同温度で3時間保温後、AIBNを1部仕込み、1時間保温した。その後、120℃に昇温し、2時間保温した。その後、反応系を冷却し、重合体(A7−1)の溶液を得た。
製造例1と同様の反応容器に、2−イソシアナトエチルメタクリレート(商品名:カレンズMOI、昭和電工(株)製、以下、MOIという)を30部、HALS−1を40部、MMAを30部、AIBNを4部および酢酸ブチルを400部仕込んだ後、窒素気流下に約1時間かけて系内温度が約95℃になるまで昇温し、1時間保温した。次いで、あらかじめMOIを90部、HALS−1を120部、MMAを90部、およびAIBNを12部仕込んだ混合液を滴下ロートより、窒素気流下に約2時間を要して系内へ滴下し、同温度で3時間保温後、AIBNを1部仕込み、1時間保温した。その後、120℃に昇温し、2時間保温した。その後、反応系を冷却し、重合体(A8−1)の溶液を得た。
(a1)成分
・GMA:グリシジルメタクリレート
・HEMA:2−ヒドロキシエチルメタクリレート
・MOI:2−イソシアナトエチルメタクリレート
(a2)成分
・HALS−1:1,2,2,6、6−ペンタメチル−4−ピペリジルメタクリレート
(a3)成分
・MMA:メチルメタクリレート
(a4)成分
・AA:アクリル酸
・AOI:2−イソシアナトエチルアクリレート
・HEA:2−ヒドロキシエチルアクリレート
重合体(A−1)40部(固形分重量:20部)、(B)成分として、ジメチロールトリシクロデカンジアクリレート(商品名:ライトアクリレートDCP−A、共栄社化学(株)製)20部、(C)成分として、ジメチロールプロパントリアクリレート(商品名:ビームセット730、荒川化学工業(株)製)10部、(D)成分としてプロピレングリコールモノメチルエーテル分散コロイダルシリカ(SiO2、平均一次粒子径:40〜60nm、固形分濃度:30%、商品名:PGM−AC4130Y、日産化学工業(株)製)167部(固形分重量:50部)、また光重合開始剤として1−ヒドロキシ−シクロヘキシル−フェニルケトン(商品名:イルガキュア184、チバ・ジャパン(株)製)を5部および、表面調整剤としてシリコーン表面調整剤であるBYK−310(ビックケミー社製)を0.2部加え、固形分濃度が33%となるようにプロピレングリコールモノメチルエーテル(以下、PMという)で希釈し、活性エネルギー線硬化性樹脂組成物を調製した。
表2に示す組成で、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をそれぞれ調製した。
厚さ2mmのポリカーボネート板の表面に、実施例1で得られた活性エネルギー線硬化性樹脂組成物をバーコーターで塗工層の厚さが10μmとなるように塗布し、80℃で2分乾燥させた。次いで、得られた塗工フィルムを大気中で、高圧水銀灯(積算光量:1000mJ/cm2、照射強度:200mW/cm2)の下を通過させて(搬送速度10m/分)、硬化させることにより、積層体を得た。また、実施例2〜13及び比較例1〜9の各樹脂組成物についても同様にして積層体をそれぞれ得た。
各積層体の表面につきJIS K 5400に従って、1mm間隔で基材まで達する切り込みを入れ、100マスの碁盤目セロハンテープ剥離試験を行い、初期密着性を評価した。
評価基準
○:剥がれがない ×:剥がれが発生
JIS K 7361−1に従って、各積層体のヘイズ値をヘイズメーターにて測定した。
評価基準
○:HAZE≦1.0% ×:HAZE>1.0%
ASTM−D−1044に従い、摩耗輪CS−10F、荷重500g、回転速度60rpm、摩耗回数500サイクルの条件で各積層体中の硬化被膜を摩耗させた後、JIS K 7361−1に従って、ヘイズメーターを用いて、ヘイズ値を測定し、変化量を算出した。耐摩耗性は下記の△HAZEで求め、値が小さいほど耐磨耗性に優れることを示す。
△HAZE(%)=(摩耗試験後のヘイズ値)−(摩耗試験前のヘイズ値)
評価基準
◎:△HAZE<5%
○:△HAZE<10%
×:△HAZE≧10%
55℃に設定した0.1Nの水酸化ナトリウム(NaOH)水溶液に、各積層体を4時間接触させた。その後、表面を純水で洗い流して乾燥させた後に、ATR法によるIR測定を行いシリカに由来するピークの変化を評価した。
評価基準
○:IRのピーク面積の変化量が20%以下
×:IRのピーク面積の変化量が20%を超える
温度140℃の熱風循環式乾燥器の中に、各積層体を入れて、200時間放置し、室温まで冷却した後、積層体の表面状態を目視で確認した。
○:変化なし
×:クラックがある
アイスーパーUVテスター(岩崎電気(株)製)を用いて、以下の試験条件で耐候性試験を実施した後、各積層体における硬化被膜の外観(クラック、剥離)を目視にて観察し、更にJIS K 7373に準拠して、色の変化を色差計(日本電色工業(株)製)を用いた透過法にて△YIを測定して、以下の基準で評価した。
(試験条件)
各積層体を80mW/cm2で照射、ブラックパネル温度63℃にて360時間試験を行い、6時間毎に硬化被膜の表面にイオン交換水を10秒間スプレーした。
評価基準
◎:目視変化なし、かつ△YIが2.0未満
○:目視変化なし、かつ△YIが2.0以上4.0未満
×:目視変化あり、または△YIが4.0以上
(B)成分
・B−1:ジメチロールトリシクロデカンジアクリレート(DCP−A)(商品名:ライトアクリレートDCP−A、共栄社化学(株)製)
・B−2:1,6−ヘキサンジオールジアクリレート(HDDA)(商品名:ライトアクリレート1.6HX−A、共栄社化学(株)製)
(C)成分
・C−1:ジメチロールプロパントリアクリレート(DMPTA)(商品名:ビームセット730、荒川化学工業(株)製)
・C−2:EO変性ジペンタエリスリトールヘキサアクリレート(DPH−12E)(商品名:NKエステルA−DPH−12E、新中村化学工(株)製)
金属酸化物微粒子
・D−1:プロピレングリコールモノメチルエーテル分散コロイダルシリカ(SiO2、平均一次粒子径:40〜50nm、固形分濃度:30%、商品名:PGM−AC4130Y、日産化学工業(株)製)
・D−2:プロピレングリコールモノメチルエーテルアセテート分散酸化ジルコニウム(ZrO2、平均一次粒子径:30〜40nm、固形分濃度:30%、商品名:TZP−108、大成化工(株)製)
・G−1:プロピレングリコールモノメチルエーテル分散コロイダルシリカ(SiO2、平均一次粒子径:10〜15nm、固形分濃度:40%、商品名:PGM−AC2140Y、日産化学工業(株)製)
・H−1:プロピレングリコールモノメチルエーテル分散コロイダルシリカ(SiO2、平均一次粒子径:100nm、固形分濃度:50%、商品名:アドマナノスラリーYA100C−LFG、(株)アドマテックス製)
厚さ2mmのポリアクリル板の表面に、実施例1の活性エネルギー線硬化性樹脂組成物をバーコーターで塗工層の厚さが10μmとなるように塗布し、80℃で2分乾燥させた。次いで、得られた塗工フィルムを大気中で、高圧水銀灯(積算光量:1000mJ/cm2、照射強度:200mW/cm2)の下を通過させて(搬送速度10m/分)、硬化させることにより、積層体を得た。前記積層体を用いて、同様の評価を行ったところ、いずれも良好な効果を示した。結果を表3に示す。
Claims (7)
- 一分子中に不飽和二重結合及びピペリジニル基を有する重合体(A)、
分子中に不飽和二重結合を2つ有する化合物(B)、
及び
平均一次粒子径が20〜80nmである金属酸化物微粒子(D)を含有する活性エネルギー線硬化性組成物であって、
前記活性エネルギー線硬化性樹脂組成物を100重量%として、
前記(A)成分10〜60重量%、前記(B)成分10〜60重量%、及び前記(D)成分20〜60重量%を含有し、
(A)成分が、
エポキシ基、水酸基及びイソシアネート基からなる群より選ばれる少なくとも1種の官能基を有する単量体(a1)、及びピペリジニル基を有する単量体(a2)を含む単量体成分の重合体(A1)と、
(A1)成分が有する官能基と反応し得る、官能基を有する単量体(a4)との反応生成物であり、
(a2)成分が、一般式(1)で表されるものである活性エネルギー線硬化性樹脂組成物。
- (A1)成分をなす単量体成分に、更に(a1)成分又は(a2)成分と共重合しうる単量体(a3)が含まれる、請求項1の活性エネルギー線硬化性樹脂組成物。
- (A)成分の二重結合当量が、250〜2000eq/gであり、かつアミン当量が400〜3000eq/gである、請求項1又は2の活性エネルギー線硬化性樹脂組成物。
- 更に、分子中に不飽和二重結合を3つ以上有する化合物(C)を含有する請求項1〜3のいずれかの活性エネルギー線硬化性樹脂組成物。
- (D)成分が、シリカ、ジルコニア及びアルミナからなる群より選ばれる1種以上である、請求項1〜4のいずれかの活性エネルギー線硬化性樹脂組成物。
- 請求項1〜5のいずれかの活性エネルギー線硬化性樹脂組成物の硬化被膜を基材の表面に有する積層体。
- 基材が、ポリカーボネート樹脂、ポリアクリル樹脂及びポリエチレンテレフタレートからなる群より選ばれる少なくとも1種である請求項6の積層体。
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