JPH1095937A - Resin molding having coating agent and cured coating - Google Patents
Resin molding having coating agent and cured coatingInfo
- Publication number
- JPH1095937A JPH1095937A JP8269145A JP26914596A JPH1095937A JP H1095937 A JPH1095937 A JP H1095937A JP 8269145 A JP8269145 A JP 8269145A JP 26914596 A JP26914596 A JP 26914596A JP H1095937 A JPH1095937 A JP H1095937A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- coating agent
- acid
- acrylate monomer
- 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.)
- Granted
Links
- 239000011248 coating agent Substances 0.000 title claims abstract description 88
- 238000000576 coating method Methods 0.000 title claims abstract description 42
- 239000011347 resin Substances 0.000 title claims abstract description 35
- 229920005989 resin Polymers 0.000 title claims abstract description 35
- 238000000465 moulding Methods 0.000 title abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 93
- -1 silane compound Chemical class 0.000 claims abstract description 55
- 239000010419 fine particle Substances 0.000 claims abstract description 37
- 239000000178 monomer Substances 0.000 claims abstract description 34
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 30
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 30
- 229910000077 silane Inorganic materials 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 239000011247 coating layer Substances 0.000 claims description 5
- 239000008119 colloidal silica Substances 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 abstract description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 38
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 239000004417 polycarbonate Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000005299 abrasion Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 10
- 235000011187 glycerol Nutrition 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000006482 condensation reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 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 5
- 239000003999 initiator Substances 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000001384 succinic acid Substances 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000001246 colloidal dispersion Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- CUYHZUQBWIJJCT-UHFFFAOYSA-N 1-[(1-cyanocyclopentyl)diazenyl]cyclopentane-1-carbonitrile Chemical compound C1CCCC1(C#N)N=NC1(C#N)CCCC1 CUYHZUQBWIJJCT-UHFFFAOYSA-N 0.000 description 1
- BRZFKNCKUAGWAB-UHFFFAOYSA-N 1-[diethoxy(ethyl)silyl]-3-sulfanylpropan-2-ol Chemical compound CCO[Si](CC)(OCC)CC(O)CS BRZFKNCKUAGWAB-UHFFFAOYSA-N 0.000 description 1
- QMHPZGKYXOBZCX-UHFFFAOYSA-N 1-[dimethoxy(methyl)silyl]-3-sulfanylpropan-2-ol Chemical compound CO[Si](C)(OC)CC(O)CS QMHPZGKYXOBZCX-UHFFFAOYSA-N 0.000 description 1
- KXYFSIKIDIULNX-UHFFFAOYSA-N 1-sulfanyl-3-triethoxysilylpropan-2-ol Chemical compound CCO[Si](OCC)(OCC)CC(O)CS KXYFSIKIDIULNX-UHFFFAOYSA-N 0.000 description 1
- ZJJGEJYFOROIHA-UHFFFAOYSA-N 1-sulfanyl-3-trimethoxysilylpropan-2-ol Chemical compound CO[Si](OC)(OC)CC(O)CS ZJJGEJYFOROIHA-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- SYENVBKSVVOOPS-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butyl prop-2-enoate Chemical compound CCC(CO)(CO)COC(=O)C=C SYENVBKSVVOOPS-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-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
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- XKBHBVFIWWDGQX-UHFFFAOYSA-N 2-bromo-3,3,4,4,5,5,5-heptafluoropent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(Br)=C XKBHBVFIWWDGQX-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- RBMWDBHKRZTOMB-UHFFFAOYSA-N 2-ethoxy-1-phenylethanone Chemical compound CCOCC(=O)C1=CC=CC=C1 RBMWDBHKRZTOMB-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
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- IQIWPLPOZHJNMX-UHFFFAOYSA-N 2-methyl-3-phenylpropanenitrile Chemical compound N#CC(C)CC1=CC=CC=C1 IQIWPLPOZHJNMX-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- DVNPFNZTPMWRAX-UHFFFAOYSA-N 2-triethoxysilylethanethiol Chemical compound CCO[Si](CCS)(OCC)OCC DVNPFNZTPMWRAX-UHFFFAOYSA-N 0.000 description 1
- LOSLJXKHQKRRFN-UHFFFAOYSA-N 2-trimethoxysilylethanethiol Chemical compound CO[Si](OC)(OC)CCS LOSLJXKHQKRRFN-UHFFFAOYSA-N 0.000 description 1
- RKCRTGUXAZZTIR-UHFFFAOYSA-N 3-[ethoxy(diethyl)silyl]propane-1-thiol Chemical compound CCO[Si](CC)(CC)CCCS RKCRTGUXAZZTIR-UHFFFAOYSA-N 0.000 description 1
- DQMRXALBJIVORP-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(C)CCCS DQMRXALBJIVORP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UGZVKSPNMDLPQH-UHFFFAOYSA-N 3-triaminosilylpropane-1-thiol Chemical compound N[Si](N)(N)CCCS UGZVKSPNMDLPQH-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LQMQMRDIAKCXNK-UHFFFAOYSA-N 4-[diethoxy(ethyl)silyl]butane-1-thiol Chemical compound CCO[Si](CC)(OCC)CCCCS LQMQMRDIAKCXNK-UHFFFAOYSA-N 0.000 description 1
- MAPRZJHECPREHW-UHFFFAOYSA-N 4-[diethoxy(methyl)silyl]butane-1-thiol Chemical compound CCO[Si](C)(OCC)CCCCS MAPRZJHECPREHW-UHFFFAOYSA-N 0.000 description 1
- ZDLNACVKVFFHBM-UHFFFAOYSA-N 4-[dimethoxy(methyl)silyl]butane-1-thiol Chemical compound CO[Si](C)(OC)CCCCS ZDLNACVKVFFHBM-UHFFFAOYSA-N 0.000 description 1
- XOPDLAXXEGMBJC-UHFFFAOYSA-N 4-[ethyl(dimethoxy)silyl]butane-1-thiol Chemical compound CC[Si](OC)(OC)CCCCS XOPDLAXXEGMBJC-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- ZWLDNGJSJBLBFK-UHFFFAOYSA-N 4-trimethoxysilylbutane-2-thiol Chemical compound CO[Si](OC)(OC)CCC(C)S ZWLDNGJSJBLBFK-UHFFFAOYSA-N 0.000 description 1
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229920006353 Acrylite® Polymers 0.000 description 1
- 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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- AHEOYAAZVWCUHW-UHFFFAOYSA-N SC(CCCO[Si](OC)(OC)C)C Chemical compound SC(CCCO[Si](OC)(OC)C)C AHEOYAAZVWCUHW-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- TZAMQIAPGYOUKF-UHFFFAOYSA-N diethoxyphosphoryl(phenyl)methanone Chemical compound CCOP(=O)(OCC)C(=O)C1=CC=CC=C1 TZAMQIAPGYOUKF-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- QKLCQKPAECHXCQ-UHFFFAOYSA-N ethyl phenylglyoxylate Chemical compound CCOC(=O)C(=O)C1=CC=CC=C1 QKLCQKPAECHXCQ-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 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
Landscapes
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Surface Treatment Of Optical Elements (AREA)
Abstract
(57)【要約】
【課題】 樹脂成形品に対し高い表面硬度を付与し、か
つ無溶剤化が可能なコーティング剤及び表面硬度の高い
硬化塗膜を有する樹脂成形品を提供する。
【解決手段】 （メタ）アクリレート単量体（ａ）と、
シラン化合物の加水分解物で微粒子表面が処理された金
属酸化物微粒子（ｂ）とを含むコーティング剤、及びそ
のコーティング剤の硬化塗膜を有する樹脂成形品。PROBLEM TO BE SOLVED: To provide a coating agent capable of imparting a high surface hardness to a resin molded product and eliminating solvent, and a resin molded product having a cured coating film having a high surface hardness. SOLUTION: A (meth) acrylate monomer (a),
A resin molding having a metal oxide fine particle (b) whose fine particle surface has been treated with a hydrolyzate of a silane compound, and a cured film of the coating agent.
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、コーティング剤及
び硬度の高い塗膜を有する樹脂成形品に関する。[0001] The present invention relates to a resin molded article having a coating agent and a coating film having high hardness.
【０００２】[0002]
【従来の技術】従来より、透明ガラス板の代替として、
耐破壊性の大きい透明樹脂材料が用いられることは広く
知られている。しかしながら、透明樹脂材料は、ガラス
に比較して表面が柔らかく、表面摩耗、引っかきにより
傷が付き易いという重大な欠点を有する。2. Description of the Related Art Conventionally, as an alternative to a transparent glass plate,
It is widely known that a transparent resin material having high resistance to destruction is used. However, the transparent resin material has a serious disadvantage that the surface is softer than glass and is easily damaged by surface wear and scratching.
【０００３】この樹脂材料の耐摩耗性を改良するための
試みは多数あり、最も一般的な方法は、例えば特開昭５
３−１０２９３６号公報、特開昭５３−１０４６３８号
公報、特開昭５４−９７６３３号公報等に記載されてい
るように、分子中に複数の（メタ）アクリロイルオキシ
基を有する化合物を樹脂成形品に塗布し、熱或いは紫外
線等の活性エネルギー線により硬化させ、耐摩耗性の優
れた樹脂成形品を得る方法である。しかしながら、かか
る方法は、硬化液も比較的安価で生産性にも優れるとい
う利点を有するが、硬化塗膜が有機物であることから、
硬化塗膜を有する樹脂成形品の耐摩耗性を得る上で限界
がある。There have been many attempts to improve the abrasion resistance of this resin material.
As described in JP-A-3-102936, JP-A-53-104638, JP-A-54-97633, etc., a compound having a plurality of (meth) acryloyloxy groups in a molecule is molded into a resin. This is a method of obtaining a resin molded product having excellent abrasion resistance by applying the composition on a substrate and curing the same with heat or active energy rays such as ultraviolet rays. However, such a method has the advantage that the curing liquid is also relatively inexpensive and excellent in productivity, but since the cured coating film is an organic substance,
There is a limit in obtaining abrasion resistance of a resin molded product having a cured coating film.
【０００４】一方、より高い表面硬度を樹脂成形品に付
与するため、例えば特開昭４８−２６８２２号公報、特
開昭５９−６４６７１号公報等に記載されているよう
に、アルコキシシラン化合物を樹脂成形品に塗布し、熱
により硬化させる方法、或いは特開昭５６−１０６９６
９号公報等に記載されているように、コロイダルシリカ
と樹脂の混合物を樹脂成形品に塗布し、熱により硬化さ
せる方法が知られている。On the other hand, in order to impart a higher surface hardness to a resin molded product, as described in, for example, JP-A-48-26822 and JP-A-59-64671, an alkoxysilane compound is used. A method in which the composition is applied to a molded article and cured by heat, or disclosed in JP-A-56-10696.
As described in, for example, Japanese Patent Application Laid-Open No. 9-205, a method is known in which a mixture of colloidal silica and a resin is applied to a resin molded product and cured by heat.
【０００５】しかしながら、これらの方法も、溶剤が用
いられるため乾燥工程を必要とし、また熱により硬化さ
せる必要があるため、エネルギー消費量が大きく、硬化
に長時間を要するため工業的に不利であり、さらに溶剤
を塗膜の硬化工程で揮散しなければならないことは、地
球環境保護の観点からも非常に好ましくないことであ
る。However, these methods also require a drying step because of the use of a solvent, and require curing by heat, which consumes a large amount of energy and requires a long time for curing, which is industrially disadvantageous. Further, the fact that the solvent must be volatilized in the curing step of the coating film is very undesirable from the viewpoint of protection of the global environment.
【０００６】[0006]
【発明が解決しようとする課題】本発明の目的は、樹脂
成形品に対し高い表面硬度を付与し、かつ無溶剤化が可
能なコーティング剤及び表面硬度の高い硬化塗膜を有す
る樹脂成形品を提供することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide a resin molded product having a coating agent capable of imparting a high surface hardness to a resin molded product and having no solvent and a cured coating film having a high surface hardness. To provide.
【０００７】[0007]
【課題を解決するための手段】本発明は、（メタ）アク
リレート単量体（ａ）若しくはその部分縮合物と、下記
一般式［１］で表されるシラン化合物の加水分解物で微
粒子の表面が処理された金属酸化物微粒子（ｂ）を含む
ことを特徴とするコーティング剤、Means for Solving the Problems The present invention relates to a method for preparing a fine particle surface comprising a (meth) acrylate monomer (a) or a partial condensate thereof and a hydrolyzate of a silane compound represented by the following general formula [1]: Wherein the coating agent comprises treated metal oxide fine particles (b).
【０００８】[0008]
【化２】 Embedded image
【０００９】及び、前記のコーティング剤を樹脂成形品
表面に塗布した塗布層をラジカル重合して得られる硬化
塗膜を有する樹脂成形品、にある。The present invention also provides a resin molded product having a cured coating film obtained by radical polymerization of a coating layer obtained by applying the coating agent on the surface of the resin molded product.
【００１０】[0010]
【発明の実施の形態】以下、本発明について説明する。
なお、本発明において、（メタ）アクリロイルオキシ基
はアクリロイルオキシ基及びまたはメタクリロイルオキ
シ基、（メタ）アクリル酸はアクリル酸及びまたはメタ
クリル酸、（メタ）アクリレートはアクリレート及びま
たはメタクリレートをそれぞれ意味する。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below.
In the present invention, (meth) acryloyloxy group means acryloyloxy group and / or methacryloyloxy group, (meth) acrylic acid means acrylic acid and / or methacrylic acid, and (meth) acrylate means acrylate and / or methacrylate.
【００１１】本発明のコーティング剤において、その一
方の構成成分である（メタ）アクリレート単量体（ａ）
は、硬化塗膜の硬度を付与する成分であり、その部分縮
合物であってもよい。（メタ）アクリレート単量体
（ａ）は、分子中に少なくとも２個の（メタ）アクリロ
イルオキシ基を有する多官能（メタ）アクリレート単量
体（ａ1）を主体とするものであり、多官能（メタ）ア
クリレート単量体（ａ1）は、その各（メタ）アクリロ
イルオキシ基を結合する残基が炭素水素またはその誘導
体であり、分子内にエーテル結合、チオエーテル結合、
エステル結合、アミド結合、ウレタン結合等を含むこと
ができる。In the coating agent of the present invention, (meth) acrylate monomer (a) which is one of the constituent components
Is a component for imparting the hardness of the cured coating film, and may be a partial condensate thereof. The (meth) acrylate monomer (a) is mainly composed of a polyfunctional (meth) acrylate monomer (a 1 ) having at least two (meth) acryloyloxy groups in the molecule. In the (meth) acrylate monomer (a 1 ), the residue for bonding each (meth) acryloyloxy group is carbon hydrogen or a derivative thereof, and an ether bond, a thioether bond,
It may contain an ester bond, an amide bond, a urethane bond and the like.
【００１２】多官能（メタ）アクリレート単量体
（ａ1）としては、例えば、多価アルコールと（メタ）
アクリル酸またはその誘導体から得られるエステル化
物、或いは多価アルコールと多価カルボン酸と（メタ）
アクリル酸またはその誘導体から得られる線状のエステ
ル化物が挙げられる。The polyfunctional (meth) acrylate monomer (a 1 ) includes, for example, polyhydric alcohol and (meth)
Esterified product obtained from acrylic acid or its derivative, or polyhydric alcohol, polycarboxylic acid and (meth)
A linear ester obtained from acrylic acid or a derivative thereof is exemplified.
【００１３】多価アルコールと（メタ）アクリル酸また
はその誘導体から得られるエステル化物の具体例として
は、ジエチレングリコールジ（メタ）アクリレート、ト
リエチレングリコールジ（メタ）アクリレート、テトラ
エチレングリコールジ（メタ）アクリレート等のポリエ
チレングリコールジ（メタ）アクリレート、１，４−ブ
タンジオールジ（メタ）アクリレート、１，６−ヘキサ
ンジオールジ（メタ）アクリレート、１，９−ノナンジ
オールジ（メタ）アクリレート、３−アクリロイルオキ
シ−２−ヒドロキシプロピル（メタ）アクリレート、ト
リメチロールプロパントリ（メタ）アクリレート、トリ
メチロールエタントリ（メタ）アクリレート、ペンタグ
リセロールトリ（メタ）アクリレート、ペンタエリスリ
トールトリ（メタ）アクリレート、ペンタエリスリトー
ルテトラ（メタ）アクリレート、グリセリントリ（メ
タ）アクリレート、次の一般式［３］で表される化合
物、Specific examples of an ester obtained from a polyhydric alcohol and (meth) acrylic acid or a derivative thereof include diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, and tetraethylene glycol di (meth) acrylate. Such as polyethylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 3-acryloyloxy -2-hydroxypropyl (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, pentaglycerol tri (meth) acrylate, pentaerythritol tri (meth) Acrylate, pentaerythritol tetra (meth) acrylate, glycerin tri (meth) acrylate, a compound represented by the following general formula [3],
【００１４】[0014]
【化３】 Embedded image
【００１５】例えばジペンタエリスリトールトリ（メ
タ）アクリレート、ジペンタエリスリトールテトラ（メ
タ）アクリレート、ジペンタエリスリトールペンタ（メ
タ）アクリレート、ジペンタエリスリトールヘキサ（メ
タ）アクリレート、トリペンタエリスリトールテトラ
（メタ）アクリレート、トリペンタエリスリトールペン
タ（メタ）アクリレート、トリペンタエリスリトールヘ
キサ（メタ）アクリレート、トリペンタエリスリトール
ヘプタ（メタ）アクリレート等が挙げられる。For example, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol tetra (meth) acrylate, tripentaerythritol Examples include pentaerythritol penta (meth) acrylate, tripentaerythritol hexa (meth) acrylate, and tripentaerythritol hepta (meth) acrylate.
【００１６】多価アルコールと多価カルボン酸と（メ
タ）アクリル酸またはその誘導体から得られる線状のエ
ステル化物としては、多価アルコールのヒドロキシル基
と、多価カルボン酸及び（メタ）アクリル酸またはその
誘導体の双方のカルボキシル基とが等量となるような混
合物を縮合反応させて得られる、飽和または不飽和ポリ
エステルポリ（メタ）アクリレートである。The linear ester obtained from a polyhydric alcohol, a polycarboxylic acid and (meth) acrylic acid or a derivative thereof includes a hydroxyl group of the polyhydric alcohol, a polycarboxylic acid and (meth) acrylic acid or A saturated or unsaturated polyester poly (meth) acrylate obtained by subjecting a mixture in which both carboxyl groups of the derivative and the carboxyl group have an equal amount to a condensation reaction.
【００１７】その好ましい組み合わせの具体例として
は、トリメチロールエタン／マロン酸／（メタ）アクリ
ル酸、トリメチロールプロパン／マロン酸／（メタ）ア
クリル酸、グリセリン／マロン酸／（メタ）アクリル
酸、ペンタエリスリトール／マロン酸／（メタ）アクリ
ル酸、トリメチロールエタン／コハク酸／（メタ）アク
リル酸、トリメチロールプロパン／コハク酸／（メタ）
アクリル酸、グリセリン／コハク酸／（メタ）アクリル
酸、ペンタエリスリトール／コハク酸／（メタ）アクリ
ル酸、Specific examples of preferred combinations include trimethylolethane / malonic acid / (meth) acrylic acid, trimethylolpropane / malonic acid / (meth) acrylic acid, glycerin / malonic acid / (meth) acrylic acid, Erythritol / malonic acid / (meth) acrylic acid, trimethylolethane / succinic acid / (meth) acrylic acid, trimethylolpropane / succinic acid / (meth)
Acrylic acid, glycerin / succinic acid / (meth) acrylic acid, pentaerythritol / succinic acid / (meth) acrylic acid,
【００１８】トリメチロールエタン／アジピン酸／（メ
タ）アクリル酸、トリメチロールプロパン／アジピン酸
／（メタ）アクリル酸、グリセリン／アジピン酸／（メ
タ）アクリル酸、ペンタエリスリトール／アジピン酸／
（メタ）アクリル酸、トリメチロールエタン／グルタル
酸／（メタ）アクリル酸、トリメチロールプロパン／グ
ルタル酸／（メタ）アクリル酸、グリセリン／グルタル
酸／（メタ）アクリル酸、ペンタエリスリトール／グル
タル酸／（メタ）アクリル酸、トリメチロールエタン／
セバシン酸／（メタ）アクリル酸、トリメチロールプロ
パン／セバシン酸／（メタ）アクリル酸、グリセリン／
セバシン酸／（メタ）アクリル酸、ペンタエリスリトー
ル／セバシン酸／（メタ）アクリル酸、Trimethylolethane / adipic acid / (meth) acrylic acid, trimethylolpropane / adipic acid / (meth) acrylic acid, glycerin / adipic acid / (meth) acrylic acid, pentaerythritol / adipic acid /
(Meth) acrylic acid, trimethylolethane / glutaric acid / (meth) acrylic acid, trimethylolpropane / glutaric acid / (meth) acrylic acid, glycerin / glutaric acid / (meth) acrylic acid, pentaerythritol / glutaric acid / ( (Meth) acrylic acid, trimethylolethane /
Sebacic acid / (meth) acrylic acid, trimethylolpropane / sebacic acid / (meth) acrylic acid, glycerin /
Sebacic acid / (meth) acrylic acid, pentaerythritol / sebacic acid / (meth) acrylic acid,
【００１９】トリメチロールエタン／フマル酸／（メ
タ）アクリル酸、トリメチロールプロパン／フマル酸／
（メタ）アクリル酸、グリセリン／フマル酸／（メタ）
アクリル酸、ペンタエリスリトール／フマル酸／（メ
タ）アクリル酸、トリメチロールエタン／イタコン酸／
（メタ）アクリル酸、トリメチロールプロパン／イタコ
ン酸／（メタ）アクリル酸、グリセリン／イタコン酸／
（メタ）アクリル酸、ペンタエリスリトール／イタコン
酸／（メタ）アクリル酸、トリメチロールエタン／無水
マレイン酸／（メタ）アクリル酸、トリメチロールプロ
パン／無水マレイン酸／（メタ）アクリル酸、グリセリ
ン／無水マレイン酸／（メタ）アクリル酸、ペンタエリ
スリトール／無水マレイン酸／（メタ）アクリル酸等が
挙げられる。Trimethylolethane / fumaric acid / (meth) acrylic acid, trimethylolpropane / fumaric acid /
(Meth) acrylic acid, glycerin / fumaric acid / (meth)
Acrylic acid, pentaerythritol / fumaric acid / (meth) acrylic acid, trimethylolethane / itaconic acid /
(Meth) acrylic acid, trimethylolpropane / itaconic acid / (meth) acrylic acid, glycerin / itaconic acid /
(Meth) acrylic acid, pentaerythritol / itaconic acid / (meth) acrylic acid, trimethylolethane / maleic anhydride / (meth) acrylic acid, trimethylolpropane / maleic anhydride / (meth) acrylic acid, glycerin / maleic anhydride Acid / (meth) acrylic acid, pentaerythritol / maleic anhydride / (meth) acrylic acid, and the like.
【００２０】多官能（メタ）アクリレート単量体
（ａ1）のその他の例としては、トリメチロールプロパ
ントルイレンジイソシアネート、或いはヘキサメチレン
ジイソシアネート、トリレンジイソシアネート、ジフェ
ニルメタンジイソシアネート、キシレンジイソシアネー
ト、４，４’−メチレンビス（シクロヘキシルイソシア
ネート）、イソホロンジイソシアネート、イソホロンジ
イソシアネート等のジイソシアネートとジオールとを反
応させて得た次の一般式［４］で表されるイソシアネー
トに、活性水素基含有（メタ）アクリレートをイソシア
ネート１分子当たり３モル以上を常法により反応させて
得られるウレタン（メタ）アクリレート、またはトリス
（２−ヒドロキシエチル）イソシアヌル酸のジ（メタ）
アクリレート、トリ（メタ）アクリレート等のポリ
［（メタ）アクリロイルオキシエチル］イソシアヌレー
ト等が挙げられ、さらには公知のエポキシポリ（メタ）
アクリレート、ウレタンポリ（メタ）アクリレート等が
挙げられる。Other examples of the polyfunctional (meth) acrylate monomer (a 1 ) include trimethylolpropane toluylene diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, xylene diisocyanate, and 4,4'- An isocyanate represented by the following general formula [4] obtained by reacting a diisocyanate such as methylene bis (cyclohexyl isocyanate), isophorone diisocyanate, or isophorone diisocyanate with a diol is added with an active hydrogen group-containing (meth) acrylate per isocyanate molecule. Urethane (meth) acrylate or tris (2-hydroxyethyl) isocyanuric acid di (meth) obtained by reacting 3 mol or more by a conventional method.
Poly [(meth) acryloyloxyethyl] isocyanurate such as acrylate and tri (meth) acrylate, and the like, and further known epoxy poly (meth)
Acrylate, urethane poly (meth) acrylate and the like can be mentioned.
【００２１】[0021]
【化４】 Embedded image
【００２２】前記のイソシアネートとの反応に用いる活
性水素を有する（メタ）アクリレートとしては、例えば
２−ヒドロキシエチル（メタ）アクリレート、２−ヒド
ロキシプロピル（メタ）アクリレート、２−ヒドロキシ
−３−メトキシプロピル（メタ）アクリレート、Ｎ−メ
チロール（メタ）アクリルアミド、Ｎ−ヒドロキシ（メ
タ）アクリルアミド、１，２，３−プロパントリオール
−１，３−ジ（メタ）アクリレート、３−（メタ）アク
リロイルオキシ−２−ヒドロキシプロピル（メタ）アク
リレート等が挙げられる。As the (meth) acrylate having an active hydrogen used in the reaction with the isocyanate, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-methoxypropyl ( (Meth) acrylate, N-methylol (meth) acrylamide, N-hydroxy (meth) acrylamide, 1,2,3-propanetriol-1,3-di (meth) acrylate, 3- (meth) acryloyloxy-2-hydroxy Propyl (meth) acrylate and the like.
【００２３】（メタ）アクリレート単量体（ａ）には、
分子中に少なくとも２個の（メタ）アクリロイルオキシ
基を有する多官能（メタ）アクリレート単量体（ａ1）
の他にに、希釈効果によるコーティング剤の粘度低減、
硬化塗膜層と基材との密着性向上、硬化塗膜の可撓性付
与の点から、多官能（メタ）アクリレート単量体
（ａ1）と共重合可能な単官能（メタ）アクリレート単
量体（ａ2）が混合されて含まれていてもよい。The (meth) acrylate monomer (a) includes:
Polyfunctional (meth) acrylate monomer having at least two (meth) acryloyloxy groups in the molecule (a 1 )
Besides, viscosity reduction of coating agent due to dilution effect,
From the viewpoint of improving the adhesion between the cured coating layer and the substrate and imparting flexibility to the cured coating film, a monofunctional (meth) acrylate monomer copolymerizable with the polyfunctional (meth) acrylate monomer (a 1 ) The monomer (a 2 ) may be contained as a mixture.
【００２４】共重合可能な単官能（メタ）アクリレート
単量体（ａ2）としては、例えば、メチル（メタ）アク
リレート、エチル（メタ）アクリレート、ブチル（メ
タ）アクリレート、ｉ−ブチル（メタ）アクリレート、
ｔ−ブチル（メタ）アクリレート、２−エチルヘキシル
（メタ）アクリレート、トリデシル（メタ）アクリレー
ト、シクロヘキシル（メタ）アクリレート、２−ヒドロ
キシエチル（メタ）アクリレート、２−ヒドロキシプロ
ピル（メタ）アクリレート、４−ヒドロキブチル（メ
タ）アクリレート、グリシジル（メタ）アクリレート、
テトラヒドロフルフリル（メタ）アクリレート、ベンジ
ル（メタ）アクリレート、エトキシエチル（メタ）アク
リレート、エチルカルビトール（メタ）アクリレート、
２−ヒドロキシ−３−クロロプロピル（メタ）アクリレ
ート、２，２，２−トリフルオロエチル（メタ）アクリ
レート、２，２，３，３−テトラフルオロプロピル（メ
タ）アクリレート、１Ｈ，１Ｈ，５Ｈ−オクタフルオロ
ペンチル（メタ）アクリレート、フェニル（メタ）アク
リレート、イソボルニル（メタ）アクリレート、ジシク
ロペンテニルオキシエチル（メタ）アクリレート、ジシ
クロペンテニル（メタ）アクリレート、シクロヘキシル
（メタ）アクリレート等が挙げられる。Examples of the copolymerizable monofunctional (meth) acrylate monomer (a 2 ) include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, i-butyl (meth) acrylate ,
t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, tridecyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (Meth) acrylate, glycidyl (meth) acrylate,
Tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, ethoxyethyl (meth) acrylate, ethyl carbitol (meth) acrylate,
2-hydroxy-3-chloropropyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H-octa Examples include fluoropentyl (meth) acrylate, phenyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and cyclohexyl (meth) acrylate.
【００２５】（メタ）アクリレート単量体（ａ）におけ
る多官能（メタ）アクリレート単量体（ａ1）と単官能
（メタ）アクリレート単量体（ａ2）との混合比率は、
硬化塗膜の硬度及びその基材との密着性の点から、多官
能（メタ）アクリレート単量体（ａ1）が５０〜１００
重量％、単官能（メタ）アクリレート単量体（ａ2）が
５０〜０重量％の比率からなる混合物であることが好ま
しい。混合物における多官能（メタ）アクリレート単量
体（ａ1）が５０重量％未満では、得られるコーティン
グ剤より得られる硬化後の塗膜に十分な硬度を付与する
ことができない。The mixing ratio of the polyfunctional (meth) acrylate monomer (a 1 ) and the monofunctional (meth) acrylate monomer (a 2 ) in the (meth) acrylate monomer (a) is as follows:
From the viewpoint of the hardness of the cured coating film and the adhesion to the substrate, the polyfunctional (meth) acrylate monomer (a 1 ) has a content of 50 to 100.
Wt%, it is preferable monofunctional (meth) acrylate monomer (a 2) is a mixture consisting of the ratio of 50 to 0% by weight. If the polyfunctional (meth) acrylate monomer (a 1 ) in the mixture is less than 50% by weight, it is not possible to impart sufficient hardness to a cured coating film obtained from the obtained coating agent.
【００２６】また、本発明のコーティング剤において、
他方の構成成分である前記一般式［１］で表されるシラ
ン化合物の加水分解物で微粒子の表面が処理された金属
酸化物微粒子（ｂ）は、前記一般式［１］で表されるシ
ラン化合物の加水分解物で、金属酸化物微粒子の表面が
修飾された無機微粒子である。本発明において「加水分
解物で表面が修飾された」とは、無機微粒子の表面の一
部または全部にシラン化合物の加水分解物が縮合反応に
より保持され或いはさらにその縮合物が保持された状態
に表面特性が改質されていることを意味する。なお、金
属酸化物微粒子（ｂ）には、シラン化合物の加水分解物
同士の縮合反応が進んだものが同一微粒子表面に保持さ
れている金属酸化物微粒子も含まれる。In the coating agent of the present invention,
The metal oxide fine particles (b) whose surfaces are treated with the hydrolyzate of the silane compound represented by the general formula [1], which is the other component, are silanes represented by the general formula [1]. These are inorganic fine particles in which the surface of metal oxide fine particles is modified with a hydrolyzate of a compound. In the present invention, "the surface is modified with a hydrolyzate" means that a hydrolyzate of a silane compound is retained by a condensation reaction on a part or all of the surface of the inorganic fine particles or a state in which the condensate is further retained. It means that the surface properties have been modified. In addition, the metal oxide fine particles (b) include metal oxide fine particles in which a condensation reaction between hydrolysates of a silane compound has progressed and which is held on the same fine particle surface.
【００２７】本発明において、金属酸化物微粒子（ｂ）
を得る際に、金属酸化物微粒子の表面の処理に用いる、
加水分解物を生成させる前記一般式［１］で表されるシ
ラン化合物は、メルカプト基を有するシラン化合物と、
多官能（メタ）アクリレート単量体（ａ1）と同種の、
分子中に少なくとも２個の（メタ）アクリロイルオキシ
基を有する多官能（メタ）アクリレート単量体とを反応
させることにより調製することができる。この反応は、
マイケル型付加反応として知られており、室温で触媒な
しでも反応が進行するが、触媒によりその反応速度を増
大させることができる。この反応に用いられる触媒とし
ては、金属アルコキシド、ピペリジン、４級アンモニウ
ム塩、ターシャリホスフィン等が挙げられる、中でも触
媒活性の度合いや取扱い性の面からターシャリホスフィ
ン、特にトリフェニルホスフィンが好ましい。In the present invention, the metal oxide fine particles (b)
Used to treat the surface of the metal oxide fine particles when obtaining
The silane compound represented by the general formula [1] that generates a hydrolyzate includes a silane compound having a mercapto group,
The same type as the polyfunctional (meth) acrylate monomer (a 1 ),
It can be prepared by reacting a polyfunctional (meth) acrylate monomer having at least two (meth) acryloyloxy groups in the molecule. This reaction is
This reaction is known as a Michael-type addition reaction, and the reaction proceeds at room temperature without a catalyst, and the reaction speed can be increased by the catalyst. Examples of the catalyst used in this reaction include metal alkoxide, piperidine, quaternary ammonium salt, tertiary phosphine, etc. Among them, tertiary phosphine, particularly triphenyl phosphine, is preferable in view of the degree of catalytic activity and handleability.
【００２８】また、このメルカプト基を有するシラン化
合物と、多官能（メタ）アクリレート単量体との反応
は、溶媒中で行うことにより反応を促進することもでき
る、例えばアルコールのような極性の高い溶媒が好まし
いものとして挙げられ、さらには反応生成物からの溶媒
の除去の面からエタノール、イソプロパノール等の低沸
点のアルコールがより好ましい。The reaction between the silane compound having a mercapto group and the polyfunctional (meth) acrylate monomer can be accelerated by performing the reaction in a solvent. Solvents are preferred, and low-boiling alcohols such as ethanol and isopropanol are more preferred from the viewpoint of removing the solvent from the reaction product.
【００２９】メルカプト基を有するシラン化合物とし
て、好ましくは次の一般式［５］で表される化合物が挙
げられる。The silane compound having a mercapto group is preferably a compound represented by the following general formula [5].
【００３０】[0030]
【化５】 Embedded image
【００３１】一般式［５］におけるＲ1の具体例として
は、メチル、エチル、プロピル、ブチル、フェニル、オ
クタデシル、２−フェニルエチル、ビニル、３，３，３
−トリフルオロプロピル、２−（ペルフルオロエチル）
エチル、２−（ペルフルオロブチル）エチル等が挙げら
れ、Ｒ2の具体例としては、メチレン、エチレン、ブチ
レン、ヘキシレン、プロピレン、デシレン、−ＣＨ2Ｃ
Ｈ2ＣＨ（ＣＨ3）−、−ＣＨ2ＣＨ（ＣＨ3）−、−ＣＨ
2ＣＨ（ＣＨ3）ＣＨ2−等の未置換の２価の炭化水素
基、２−ヒドロキシプロピル等の置換基を有する２価の
炭化水素基が挙げられる。また、Ｘの具体例としては、
アルコキシ基、アミノ基、イソプロペノキシ基等が挙げ
られる。Specific examples of R 1 in the general formula [5] include methyl, ethyl, propyl, butyl, phenyl, octadecyl, 2-phenylethyl, vinyl, 3,3,3
-Trifluoropropyl, 2- (perfluoroethyl)
Ethyl, 2- (perfluorobutyl) ethyl and the like. Specific examples of R 2 include methylene, ethylene, butylene, hexylene, propylene, decylene, and —CH 2 C.
H 2 CH (CH 3) - , - CH 2 CH (CH 3) -, - CH
Examples thereof include an unsubstituted divalent hydrocarbon group such as 2 CH (CH 3 ) CH 2 — and a divalent hydrocarbon group having a substituent such as 2-hydroxypropyl. As a specific example of X,
Examples include an alkoxy group, an amino group, and an isopropenoxy group.
【００３２】メルカプト基を有するシラン化合物として
は、例えばγ−メルカプトピロピルトリメトキシシラ
ン、γ−メルカプトピロピルトリエトキシシラン、γ−
メルカプトピロピルジメトキシシラン、γ−メルカプト
ピロピルエチルジメトキシシラン、γ−メルカプトピロ
ピルメチルジエトキシシラン、γ−メルカプトピロピル
エチルジエトキシシラン、γ−メルカプトピロピルブチ
ルジメトキシシラン、δ−メルカプトブチルトリメトキ
シシラン、δ−メルカプトプロピルトリエトキシシラ
ン、δ−メルカプトブチルメチルジメトキシシラン、δ
−メルカプトブチルエチルジメトキシシラン、δ−メル
カプトブチルメチルジエトキシシラン、δ−メルカプト
ブチルエチルジエトキシシラン、γ−メルカプトイソブ
チルトリメトキシシラン、γ−メルカプトイソブチルメ
チルジメトキシシラン、γ−メルカプトブチルトリメト
キシシラン、γ−メルカプトブチルメチルトリメトキシ
シラン、γ−メルカプト−２−ヒドロキシプロピルトリ
メトキシシラン、γ−メルカプト−２−ヒドロキシプロ
ピルトリエトキシシラン、γ−メルカプト−２−ヒドロ
キシプロピルメチルジメトキシシラン、γ−メルカプト
−２−ヒドロキシプロピルエチルジエトキシシラン、γ
−メルカプトプロピルジメチルメトキシシラン、γ−メ
ルカプトプロピルジエチルエトキシシラン、β−メルカ
プトエチルトリメトキシシラン、β−メルカプトエチル
トリエトキシシラン、γ−メルカプトプロピルトリアミ
ノシラン等が挙げられる。Examples of the silane compound having a mercapto group include, for example, γ-mercaptopyropytritrimethoxysilane, γ-mercaptopyropytritriethoxysilane, γ-
Mercaptopyropyrdimethoxysilane, γ-mercaptopyropyrethyldimethoxysilane, γ-mercaptopyropylmethyldiethoxysilane, γ-mercaptopyropyrethyldiethoxysilane, γ-mercaptopyropyryldimethoxysilane, δ-mercaptobutyltrimethoxysilane Silane, δ-mercaptopropyltriethoxysilane, δ-mercaptobutylmethyldimethoxysilane, δ
-Mercaptobutylethyldimethoxysilane, δ-mercaptobutylmethyldiethoxysilane, δ-mercaptobutylethyldiethoxysilane, γ-mercaptoisobutyltrimethoxysilane, γ-mercaptoisobutylmethyldimethoxysilane, γ-mercaptobutyltrimethoxysilane, γ -Mercaptobutylmethyltrimethoxysilane, γ-mercapto-2-hydroxypropyltrimethoxysilane, γ-mercapto-2-hydroxypropyltriethoxysilane, γ-mercapto-2-hydroxypropylmethyldimethoxysilane, γ-mercapto-2- Hydroxypropylethyldiethoxysilane, γ
-Mercaptopropyldimethylmethoxysilane, γ-mercaptopropyldiethylethoxysilane, β-mercaptoethyltrimethoxysilane, β-mercaptoethyltriethoxysilane, γ-mercaptopropyltriaminosilane and the like.
【００３３】本発明において、前記一般式［１］で表さ
れるシラン化合物の加水分解物で表処理される金属酸化
物微粒子としては、ガラスファイバーチップ、ガラス
箔、シリカ、酸化チタン、アルミナ、タルク、マイカ、
クレー、水酸化アルミ等の微粒子或いはコロイド分散物
が挙げられ、中でも透明性の良好な硬化塗膜を得るため
には、シリカ、アルミナ等のコロイド分散物、特にコロ
イダルシリカが好ましく用いられる。In the present invention, the metal oxide fine particles treated with the hydrolyzate of the silane compound represented by the general formula [1] include glass fiber chips, glass foils, silica, titanium oxide, alumina, talc and the like. , Mica,
Fine particles or colloidal dispersions such as clay and aluminum hydroxide are mentioned. Among them, colloidal dispersions such as silica and alumina, particularly colloidal silica are preferably used in order to obtain a cured film having good transparency.
【００３４】また、金属酸化物微粒子の粒子径は、特に
限定はないが、好ましくは平均粒径が１ｎｍ〜１μｍの
もので、透明性の良好な硬化塗膜を得るためには、好ま
しくは平均粒径が１０〜５００ｎｍのものである。金属
酸化物微粒子として、コロイダルシリカを用いる場合に
は、その分散媒に特に限定はないが、分散媒としては、
水、メタノール、エタノール、イソプロピルアルコー
ル、ｎ−ブタノール等のアルコール類、セルソルブ類、
ジメチルアセトアミド、キシレン等が挙げられ、特にコ
ーティング剤の調製作業が簡便であることから、水、ア
ルコール類、セルソルブ類が好ましく用いられる。The particle diameter of the metal oxide fine particles is not particularly limited, but preferably has an average particle diameter of 1 nm to 1 μm, and is preferably an average particle diameter in order to obtain a cured coating film having good transparency. It has a particle size of 10 to 500 nm. When using colloidal silica as the metal oxide fine particles, there is no particular limitation on the dispersion medium, but as the dispersion medium,
Water, methanol, ethanol, isopropyl alcohol, alcohols such as n-butanol, cellosolves,
Examples thereof include dimethylacetamide and xylene. Water, alcohols, and cellosolves are preferably used because the preparation of the coating agent is particularly simple.
【００３５】金属酸化物微粒子（ｂ）を得るための、金
属酸化物微粒子の前記一般式［１］で表されるシラン化
合物の加水分解物による表面処理は、金属酸化物微粒子
の存在下にシラン化合物を加水分解する、或いは加水分
解した後、この加水分解物を縮合反応させることにより
容易に行うことができる。表面処理は、金属酸化物微粒
子１００重量部に対して前記一般式［１］で表されるシ
ラン化合物を好ましくは０．１〜５００重量部、より好
ましくは０．５〜２００重量部となる範囲で行えばよ
い。In order to obtain the metal oxide fine particles (b), the surface treatment of the metal oxide fine particles with the hydrolyzate of the silane compound represented by the general formula [1] is carried out in the presence of the metal oxide fine particles. After hydrolyzing the compound or hydrolyzing the compound, the hydrolyzate can be easily subjected to a condensation reaction. In the surface treatment, the silane compound represented by the general formula [1] is preferably 0.1 to 500 parts by weight, more preferably 0.5 to 200 parts by weight, based on 100 parts by weight of the metal oxide fine particles. It should be done in.
【００３６】このシラン化合物の量が０．５重量部より
少ない条件で得られる金属酸化物微粒子は、コーティン
グ剤中での分散安定性が不良となり、また、２００重量
部より条件で得られる金属酸化物微粒子を含むコーティ
ング剤は、粘度が高くなる傾向にあり、またコスト面で
高価なものとなる。The metal oxide fine particles obtained under the condition that the amount of the silane compound is less than 0.5 part by weight have poor dispersion stability in the coating agent, and the metal oxide fine particles obtained under the condition from 200 parts by weight. The coating agent containing fine particles tends to have a high viscosity and is expensive in terms of cost.
【００３７】また、このシラン化合物の加水分解を促進
する触媒として、無機酸または有機酸を用いることがで
きる。無機酸としては、例えば塩酸、フッ化水素酸、臭
化水素酸等のハロゲン化水素酸や、硫酸、硝酸、燐酸等
が挙げられ、また有機酸としては、例えば蟻酸、酢酸、
シュウ酸、（メタ）アクリル酸等が挙げられる。の有機
酸を用いることができる。As a catalyst for promoting the hydrolysis of the silane compound, an inorganic acid or an organic acid can be used. Examples of the inorganic acid include hydrochloric acid, hydrofluoric acid, hydrohalic acid such as hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like.Examples of the organic acid include formic acid, acetic acid, and the like.
Examples include oxalic acid and (meth) acrylic acid. Organic acids can be used.
【００３８】この金属酸化物微粒子（ｂ）を得る際のシ
ラン化合物を加水分解する反応系には、反応を温和かつ
均一に行うために、溶媒を用いることができる。用いら
れる溶媒としては、加水分解物であるシランアルコキシ
ド、水及び触媒と相溶性のあるものが望ましく、例えば
水、メタノール、エタノール、イソプロピルアルコール
等のアルコール類、アセトン、メチルイソブチルケトン
等のケトン類、テトラヒドロフラン、ジオキサン等のエ
ーテル類等が挙げられる。溶媒の使用量は、反応物の濃
度が希薄になりすぎると、反応速度が著しく遅くなる傾
向となるので、反応物を均一に溶解できる量であれば、
特に制限はない。In the reaction system for hydrolyzing the silane compound in obtaining the metal oxide fine particles (b), a solvent can be used in order to carry out the reaction mildly and uniformly. The solvent used is preferably a silane alkoxide that is a hydrolyzate, one that is compatible with water and a catalyst, for example, water, methanol, ethanol, alcohols such as isopropyl alcohol, acetone, ketones such as methyl isobutyl ketone, Ethers such as tetrahydrofuran and dioxane; The amount of the solvent used is such that if the concentration of the reactant is too low, the reaction rate tends to be extremely slow, so long as the reactant can be uniformly dissolved.
There is no particular limitation.
【００３９】金属酸化物微粒子の存在下での前記一般式
［１］で表されるシラン化合物の加水分解と縮合反応
は、溶媒の使用量にもよるが、２０〜１２０℃の温度で
３０分〜２４時間、好ましくは２０℃以上の沸点を有す
る溶媒を用い、その沸点温度条件下で１〜１０時間行え
ばよい。The hydrolysis and condensation reaction of the silane compound represented by the general formula [1] in the presence of the metal oxide fine particles may be carried out at a temperature of 20 to 120 ° C. for 30 minutes, depending on the amount of the solvent used. It is sufficient to use a solvent having a boiling point of 20 ° C. or higher for 1 to 10 hours under the conditions of the boiling point.
【００４０】本発明のコーティング剤において、（メ
タ）アクリレート単量体（ａ）と前記一般式［１］で表
されるシラン化合物の加水分解物で表面処理された金属
酸化物微粒子（ｂ）との混合比は、特に制限はないが、
好ましくは金属酸化物微粒子（ｂ）１００重量部に対し
て（メタ）アクリレート単量体（ａ）５〜２，０００重
量部の範囲であるが、本発明のコーティング剤を無溶剤
型として用いる場合には、コーティング剤の粘度を考慮
すると（メタ）アクリレート単量体（ａ）６０〜２，０
００重量部の範囲が好ましい。In the coating agent of the present invention, there are provided (meth) acrylate monomer (a) and metal oxide fine particles (b) surface-treated with a hydrolyzate of a silane compound represented by the above general formula [1]. Is not particularly limited,
Preferably, the amount of the (meth) acrylate monomer (a) is in the range of 5 to 2,000 parts by weight with respect to 100 parts by weight of the metal oxide fine particles (b). In consideration of the viscosity of the coating agent, (meth) acrylate monomer (a)
A range of 00 parts by weight is preferred.
【００４１】本発明のコーティング剤は、熱重合及びま
たは光重合により硬化させることができ、本発明のコー
ティング剤には、その硬化反応を促進させるために適宜
重合開始剤を添加することができる。重合開始剤として
は、熱重合開始剤として、例えばラウロイルパーオキサ
イド、ベンゾイルパーオキサイド、プロピオノイルパー
オキサイド、ｔ−ブチルパーオキシラウレート、ジクミ
ルパーオキサイド、ジ−ｔ−ブチルパーオキサイド、ク
メンハイドロパーオキサイド等の過酸化物系開始剤や、
２，２’−アゾビスイソブチロニトリル、１，１’−ア
ゾビス−１−シクロペンタノニトリル、ジメチル−２，
２’−アゾビスイソブチレート、１，１’−アゾビスシ
クロヘキサンカルボニトリル、４，４’−アゾビス−４
−シアノバレイックアシド、２，２’−アゾビス−２−
ベンジルプロピオニトリル等のアゾ系開始剤等が挙げら
れる。The coating agent of the present invention can be cured by thermal polymerization and / or photopolymerization, and a polymerization initiator can be appropriately added to the coating agent of the present invention in order to accelerate the curing reaction. Examples of the polymerization initiator include thermal polymerization initiators such as lauroyl peroxide, benzoyl peroxide, propionoyl peroxide, t-butylperoxylaurate, dicumyl peroxide, di-t-butyl peroxide, cumene hydro. Peroxide initiators such as peroxides,
2,2′-azobisisobutyronitrile, 1,1′-azobis-1-cyclopentanonitrile, dimethyl-2,
2'-azobisisobutyrate, 1,1'-azobiscyclohexanecarbonitrile, 4,4'-azobis-4
-Cyanovaleic acid, 2,2'-azobis-2-
An azo initiator such as benzylpropionitrile and the like can be mentioned.
【００４２】また、光重合開始剤として、例えばベンゾ
イン、ベンゾインメチルエーテル、ベンゾインエチルエ
ーテル、ベンゾインイソプロピルエーテル、ベンゾイン
イソブチルエーテル、アセトイン、ブチロイン、トルオ
イン、ベンジル、ベンゾフェノン、ｐ−メトキシベンゾ
フェノン、２，２−ジエトキシアセトフェノン、α，α
−ジメトキシ−α−フェニルアセトフェノン、メチルフ
ェニルグリオキシレート、エチルフェニルグリオキシレ
ート、４，４’−ビス（ジメチルアミノ）ベンゾフェノ
ン、２−ヒドロキシ−２−メチル−１−フェニルプロパ
ン−１−オン、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サイド、ベンゾイルジエトキシフ
ォスフィンオキサイド、チオキサントン、２−クロロチ
オキサントン、２，４−ジクロロチオキサントン、２−
メチルチオキサントン、２，４−ジメチルチオキサント
ン、２−イソプロピルチオキサントン、２，４−ジエチ
ルチオキサントン、２，４−ジイソプロピルチオキサン
トン等が挙げられ、特に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サイド、ベンゾイルジエ
トキシフォスフィンオキサイドが好ましいものとして挙
げられる。As the photopolymerization initiator, for example, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, acetoin, butyroin, toluoin, benzyl, benzophenone, p-methoxybenzophenone, 2,2-diene Ethoxyacetophenone, α, α
-Dimethoxy-α-phenylacetophenone, methylphenylglyoxylate, ethylphenylglyoxylate, 4,4′-bis (dimethylamino) benzophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, , 4,6-trimethylbenzoyldiphenylphosphine oxide, benzoyldiethoxyphosphine oxide, thioxanthone, 2-chlorothioxanthone, 2,4-dichlorothioxanthone, 2-
Methylthioxanthone, 2,4-dimethylthioxanthone, 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, etc., and particularly 2,4,6-trimethylbenzoyldiphenylphosphine oxide, benzoyldiethoxyphosphone Fin oxide is preferred.
【００４３】これらの熱重合開始剤や光重合開始剤は、
単独でまたは混合物として用いられる。コーティング剤
に添加される重合開始剤の量は、コーティング剤１００
重量部に対し０．０１〜１０重量部であることが好まし
い。重合開始剤の量が０．０１重量部より少ないと重合
開始剤としての効果が不足する傾向にあり、また、１０
重量部より多いと硬化塗膜の着色、耐候性の不良が起こ
る傾向にある。These thermal polymerization initiators and photopolymerization initiators are
Used alone or as a mixture. The amount of the polymerization initiator added to the coating agent is 100
It is preferably 0.01 to 10 parts by weight based on parts by weight. If the amount of the polymerization initiator is less than 0.01 part by weight, the effect as the polymerization initiator tends to be insufficient, and 10
If the amount is more than 10 parts by weight, coloring of the cured coating film and poor weather resistance tend to occur.
【００４４】本発明のコーティング剤には、必要に応
じ、さらに表面平滑剤、界面活性剤、紫外線吸収剤、光
安定剤、熱安定剤、貯蔵安定剤等の添加剤が添加されて
いてもよい。If necessary, additives such as a surface smoothing agent, a surfactant, an ultraviolet absorber, a light stabilizer, a heat stabilizer and a storage stabilizer may be added to the coating agent of the present invention. .
【００４５】本発明のコーティング剤は、無溶剤型とし
て使用できるが、必要であれば有機溶剤を含有させて使
用することも可能である。この有機溶剤としては、（メ
タ）アクリレート単量体（ａ）及び重合開始剤と均一に
混合することが可能で、かつ金属酸化物微粒子（ｂ）を
均一に分散させることが可能であれば特に限定されない
が、常圧での沸点が５０〜２００℃で、２５℃での粘度
が１０センチポイズ以下のものが適当である。The coating agent of the present invention can be used as a solventless type, but if necessary, may contain an organic solvent. As the organic solvent, particularly, it is possible to uniformly mix the (meth) acrylate monomer (a) and the polymerization initiator and to uniformly disperse the metal oxide fine particles (b). Although not limited, those having a boiling point at normal pressure of 50 to 200 ° C and a viscosity at 25 ° C of 10 centipoise or less are suitable.
【００４６】用いられる有機溶剤としては、例えばエタ
ノール、イソプロピルアルコール、ノルマルプロピルア
ルコール、ノルマルブチルアルコール等のアルコール
類、ベンゼン、トルエン等の芳香族炭化水素類、アセト
ン、メチルエチルケトン等のケトン類、ジオキサン等の
エーテル類、酢酸エチル、酢酸ブチル等のエステル類、
Ｎ，Ｎ−ジメチルホルムアミド等が挙げられる。これら
の溶剤は、単独でまたは２種以上混合して用いられる。Examples of the organic solvent used include alcohols such as ethanol, isopropyl alcohol, normal propyl alcohol and normal butyl alcohol, aromatic hydrocarbons such as benzene and toluene, ketones such as acetone and methyl ethyl ketone, and dioxane. Ethers, esters such as ethyl acetate and butyl acetate,
N, N-dimethylformamide and the like. These solvents are used alone or in combination of two or more.
【００４７】本発明のコーティング剤は、樹脂成形品表
面に塗布し、この塗布層をラジカル重合により硬化させ
るときは、高い表面硬度を有する硬化塗膜を形成させる
ことができる。従って、本発明の他の発明は、コーティ
ング剤を樹脂成形品表面に塗布した塗布層をラジカル重
合して得られる硬化塗膜を有する樹脂成形品にある。When the coating agent of the present invention is applied to the surface of a resin molded product and this coating layer is cured by radical polymerization, a cured coating film having a high surface hardness can be formed. Accordingly, another aspect of the present invention is a resin molded product having a cured coating film obtained by radical polymerization of a coating layer obtained by applying a coating agent to the surface of the resin molded product.
【００４８】本発明の硬化塗膜を有する樹脂成形品にお
ける硬化塗膜、下記一般式［６］で表される構造を介し
て、前記（メタ）アクリレート単量体（ａ）からなる重
合体と金属酸化物微粒子（ｂ）とが結合している硬化塗
膜である。かかる一般式［６］で表される構造で結合し
ている硬化塗膜は、表面硬度が非常に高いという性能を
有するだけでなく、加熱成形性が良好であるため、本発
明の硬化塗膜を有する樹脂成形品を加熱成形した後も、
加熱成形前と同等の高い表面硬度を保持するもである。The cured coating film in the resin molded article having the cured coating film of the present invention, via a structure represented by the following general formula [6], a polymer comprising the (meth) acrylate monomer (a) The cured coating film is bonded to the metal oxide fine particles (b). The cured coating film bonded by the structure represented by the general formula [6] not only has a performance of very high surface hardness, but also has good heat moldability. Even after heat molding a resin molded product having
It maintains the same high surface hardness as before heat molding.
【００４９】[0049]
【化６】 Embedded image
【００５０】前記一般式［６］で表される構造は、金属
酸化物微粒子の表面にメルカプト基を有するシランカッ
プリング剤を付加した金属酸化物微粒子（ｂ）と、（メ
タ）アクリレート単量体（ａ）を混合してラジカル重合
を行うことにより、連鎖移動反応によりシランカップリ
ング剤のメルカプト基を（メタ）アクリレート重合体の
（メタ）アクリレート基と反応させて得ることができ
る。The structure represented by the general formula [6] has a metal oxide fine particle (b) obtained by adding a silane coupling agent having a mercapto group to the surface of the metal oxide fine particle, and a (meth) acrylate monomer By mixing (a) and performing radical polymerization, it can be obtained by reacting the mercapto group of the silane coupling agent with the (meth) acrylate group of the (meth) acrylate polymer by a chain transfer reaction.
【００５１】具体的には、本発明の硬化塗膜を有する樹
脂成形品は、例えば次のような方法で得ることができ
る。まず、（メタ）アクリレート単量体（ａ）またはそ
の部分縮合物中に、金属酸化物微粒子の表面を前記一般
式［１］で表されるシラン化合物の加水分解物で修飾し
た金属酸化物微粒子（ｂ）を添加して調合液（コーティ
ング剤）を得る、この調合液を樹脂成形品に塗布した
後、熱及びまたは光で硬化させると、前記一般式［６］
で表される構造を介して、（メタ）アクリレート重合体
と金属酸化物微粒子（ｂ）とが結合している硬化塗膜を
有する樹脂成形品が得られる。Specifically, the resin molded article having the cured coating film of the present invention can be obtained, for example, by the following method. First, in the (meth) acrylate monomer (a) or a partial condensate thereof, metal oxide fine particles in which the surface of the metal oxide fine particles is modified with a hydrolyzate of a silane compound represented by the above general formula [1] (B) is added to obtain a preparation liquid (coating agent). When this preparation liquid is applied to a resin molded product and cured by heat and / or light, the above-mentioned general formula [6]
A resin molded article having a cured coating film in which the (meth) acrylate polymer and the metal oxide fine particles (b) are bonded via the structure represented by
【００５２】本発明のコーティング剤により硬化塗膜が
形成される樹脂成形品としては、特にその種類に限定は
なく、アクリル樹脂、ポリカーボネート樹脂等公知の樹
脂の成形品が挙げられる。特に本発明のコーティング剤
を硬化して得られる硬化塗膜は、透明性、耐擦傷性及び
耐摩耗性に優れているため、本発明のコーティング剤に
より硬化塗膜が形成された樹脂成形品は、透明性、耐擦
傷性及び耐摩耗性が必要な光学部品材に好適なるもので
ある。The resin molded article on which the cured coating film is formed by the coating agent of the present invention is not particularly limited, and examples thereof include a molded article of a known resin such as an acrylic resin and a polycarbonate resin. In particular, the cured coating film obtained by curing the coating agent of the present invention is excellent in transparency, scratch resistance, and abrasion resistance. It is suitable for an optical component material requiring transparency, scratch resistance and abrasion resistance.
【００５３】また、本発明の硬化塗膜を有する樹脂成形
品は、曲げ加工等の加熱成形後でも、硬化塗膜の透明
性、耐擦傷性及び耐摩耗性が良好であるため、自動車用
ヘッドランプケース、オートバイ用ヘルメットシール
ド、車輛用窓材、冷蔵または冷凍用ショーケース用窓
材、樹脂製建材等の用途に用いることが可能である。Further, the resin molded article having the cured coating film of the present invention has good transparency, scratch resistance and abrasion resistance even after heat molding such as bending, so that the head for automobiles can be obtained. It can be used for applications such as lamp cases, motorcycle helmet shields, vehicle window materials, refrigerated or frozen showcase window materials, and resin building materials.
【００５４】[0054]
【実施例】以下、本発明を実施例により具体的に説明す
る。なお、実施例中の各物性の測定及び評価は以下に示
す方法に拠った。The present invention will be described below in more detail with reference to examples. In addition, the measurement and evaluation of each physical property in the examples were based on the following methods.
【００５５】〈全光線透過率〉ＪＩＳ Ｋ７１０５に準
拠し、全光線透過率を反射透過率計（村上色彩技術研究
所製、品番ＨＲ−１００型）を用いて測定した。<Total Light Transmittance> According to JIS K7105, the total light transmittance was measured using a reflection transmittance meter (manufactured by Murakami Color Research Laboratory, product number HR-100).
【００５６】〈密着性〉試料の硬化塗膜面にカミソリの
刃で１ｍｍ間隔に縦横に各１１本の切れ目を入れて１０
０個の目を作り、この目の面にセロテープ（ニチバン
（株）製粘着テープ）を貼り付けた後、９０゜の方向に
一気に引き剥し、硬化塗膜が基材から剥離せずに残った
目の数（ｎ）をｎ／１００で示した。<Adhesion> 11 cuts were made on the cured coating surface of the sample at 1 mm intervals vertically and horizontally with a razor blade.
After making zero eyes and attaching cellophane tape (adhesive tape manufactured by Nichiban Co., Ltd.) to the surface of the eyes, it was peeled off at a stretch in the direction of 90 °, leaving the cured coating film without peeling from the substrate. The number of eyes (n) is indicated by n / 100.
【００５７】〈ヘーズ値及び耐擦傷性〉＃０００番スチ
ールウールを径２５ｍｍの円形パッド面に装着し、往復
式摩擦試験機台上に、硬化塗膜面を上にして試料片を固
定し、この硬化塗膜面にスチールウール面が当接するよ
う円形パッドを置き、荷重１０００ｇ下で試験機を１０
０往復させ、試料片の硬化塗膜のスチールウールテスト
を行った。スチールウールテストを終了した試料片を洗
浄乾燥した後、試料片の硬化塗膜のヘーズ値をヘーズメ
ーターにより曇価として測定した、また、次式による値
を耐擦傷性とした。 耐擦傷性（％）＝スチールウールテスト後の試験片の曇
価（％）−スチールウールテスト前の試験片の曇価
（％）<Haze Value and Scratch Resistance> A # 000 steel wool was mounted on a circular pad surface having a diameter of 25 mm, and a sample piece was fixed on a reciprocating friction tester table with the cured coating surface facing up. A circular pad was placed so that the steel wool surface was in contact with the cured coating surface, and the test machine was operated under a load of 1000 g under a load of 1000 g.
Zero reciprocation was performed, and a steel wool test of the cured coating film of the sample piece was performed. After the steel wool test was completed, the sample piece was washed and dried, and then the haze value of the cured coating film of the sample piece was measured as a haze value using a haze meter. Scratch resistance (%) = Haze value (%) of test piece after steel wool test-Haze value (%) of test piece before steel wool test
【００５８】〈耐摩耗性〉試料片の硬化塗膜について、
テーバー摩耗試験法により、ＣＳ−１０Ｆ摩耗輪を用
い、片輪５００ｇの荷重で１００回転及び５００回転の
摩耗試験を行い、試料片の摩耗部の曇価をヘーズメータ
ーにより測定し、次式による値を耐擦傷性とした。な
お、曇価の測定は、摩耗サイクルの軌道の４箇所で行
い、その平均値とした。 耐摩耗性（％）＝テーバー摩耗試験後の試験片の曇価
（％）−テーバー摩耗試験前の試験片の曇価（％）<Abrasion resistance> Regarding the cured coating film of the sample piece,
Using the Taber abrasion test method, using a CS-10F wear wheel, a wear test was performed at 100 rotations and 500 rotations with a load of 500 g per wheel, and the haze value of the wear portion of the sample piece was measured with a haze meter, and the value was calculated by the following equation. Was determined to have scratch resistance. The haze was measured at four points on the trajectory of the wear cycle, and the average value was obtained. Abrasion resistance (%) = Haze value (%) of test piece after Taber abrasion test-Haze value (%) of test piece before Taber abrasion test
【００５９】（実施例１）イソプロパノール１３３重量
部、１，６−ヘキサンジオールジアクリレート（大阪有
機化学工業（株）製、以下、Ｃ６ＤＡという）１０４重
量部、γ−メルカプトピロピルトリメトキシシラン（信
越シリコーン（株）製、ＫＢＭ−８０３）３０重量部、
トリフェニルホスフィン（以下、ＴＰＰという）０．６
重量部からなる混合物を室温で７２時間攪拌し、シラン
化合物含有混合物（Ａ）を調製した。(Example 1) 133 parts by weight of isopropanol, 104 parts by weight of 1,6-hexanediol diacrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd .; hereinafter, referred to as C6DA), γ-mercaptopyropyrpropyltrimethoxysilane (Shinetsu Silicone) Manufactured by KBM-803) 30 parts by weight,
Triphenylphosphine (hereinafter referred to as TPP) 0.6
The mixture consisting of parts by weight was stirred at room temperature for 72 hours to prepare a silane compound-containing mixture (A).
【００６０】イソプロパノール分散コロイダルシリカ
（日産化学工業（株）製、ＩＰＡ−ＳＴ、固形分３０重
量％）１２５重量部の攪拌下に、前記のシラン化合物含
有混合物（Ａ）１００重量部及び０．０１規定の塩酸
４．５重量部を加え、４０℃で１時間攪拌してシラン化
合物含有混合物（Ａ）中のシラン化合物を加水分解する
とともに、この加水分解物とシリカの縮合反応を行い、
表面修飾したシリカを得た。その後、Ｃ６ＤＡ２１．９
重量部、トリメチロールエタン／コハク酸／アクリル酸
（モル比２：１：４）の縮合反応により得られたポリエ
ステルアクリレート（以下、ＴＡＳという）４０．５重
量部を加え、均一に攪拌した後、減圧して揮発分を除去
し、分散液（Ｂ）を得た。While stirring 125 parts by weight of isopropanol-dispersed colloidal silica (manufactured by Nissan Chemical Industries, Ltd., IPA-ST, solid content: 30% by weight), 100 parts by weight of the silane compound-containing mixture (A) and 0.01 part by weight were mixed. 4.5 parts by weight of a specified hydrochloric acid was added, and the mixture was stirred at 40 ° C. for 1 hour to hydrolyze the silane compound in the silane compound-containing mixture (A), and a condensation reaction between the hydrolyzate and silica was performed.
A surface-modified silica was obtained. Then, C6DA21.9
4 parts by weight of a polyester acrylate (hereinafter referred to as TAS) obtained by a condensation reaction of trimethylolethane / succinic acid / acrylic acid (molar ratio 2: 1: 4) were added, and the mixture was stirred uniformly. The pressure was reduced to remove volatile components, to obtain a dispersion (B).
【００６１】得られた分散液（Ｂ）１００重量部に、光
重合開始剤として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サイド（ＢＡＳＦ社製、Ｌｕｃ
ｉｒｉｎ ＴＰＯ、以下、ＴＰＯという）２．８重量部
及びベンゾフェノン（和光純薬（株）製）１重量部を加
えて攪拌溶解し、コーティング剤を得た。To 100 parts by weight of the obtained dispersion (B), 2,4,6-trimethylbenzoyldiphenylphosphine oxide (Luc, manufactured by BASF, Inc.) was used as a photopolymerization initiator.
2.8 parts by weight of irin TPO (hereinafter, referred to as TPO) and 1 part by weight of benzophenone (manufactured by Wako Pure Chemical Industries, Ltd.) were added and dissolved by stirring to obtain a coating agent.
【００６２】得られたコーティング剤を厚さ２ｍｍのポ
リカーボネート板（三菱レイヨン（株）製、ダイヤライ
トＰ、以下、ＰＣ板という）に塗布し、塗布面に厚さ５
０μｍのポリエチレンテレフタレートの２軸延伸フィル
ムを被せて積層し、ゴムロールで膜厚８μｍに設定し
た。次いで、７０℃の雰囲気下で４０分間保持した後、
フィルム面を上にして出力１２０Ｗ／ｃｍのメタルハラ
イドランプの下（距離２１０ｍｍ）を１．６ｍ／分の速
度で通過させ１段目の硬化を行い、フィルムを剥離した
後、塗膜面を上にして出力１２０Ｗ／ｃｍの高圧水銀灯
の下（距離２１０ｍｍ）を１．６ｍ／分の速度で通過さ
せ２段目の硬化を行った。得られた表面硬化ＰＣ板の評
価結果を表１に示した。The obtained coating agent is applied to a 2 mm-thick polycarbonate plate (Dialite P, manufactured by Mitsubishi Rayon Co., Ltd .; hereinafter, referred to as a PC plate), and a thickness of 5 mm is applied to the coated surface.
A biaxially stretched film of polyethylene terephthalate having a thickness of 0 μm was covered and laminated, and the thickness was set to 8 μm with a rubber roll. Then, after holding in an atmosphere of 70 ° C. for 40 minutes,
After passing through a 120 W / cm metal halide lamp (distance 210 mm) at a speed of 1.6 m / min with the film surface facing upward at a speed of 1.6 m / min, the first stage of curing is performed, and after the film is peeled off, the coating surface is oriented upward. Then, it passed under a high-pressure mercury lamp with an output of 120 W / cm (distance 210 mm) at a speed of 1.6 m / min to perform the second-stage curing. Table 1 shows the evaluation results of the obtained surface-hardened PC boards.
【００６３】（実施例２）実施例１において、ＴＡＳを
ジペンタエリスリトールヘキサアクリレート（日本化薬
（株）製、ＫＡＹＡＲＡＤ ＤＰＨＡ）に代えた以外
は、実施例１と同様にしてコーティング剤を得た。さら
にこのコーティング剤を用い、実施例１と同様にして硬
化塗膜を形成したＰＣ板を得た。得られた表面硬化ＰＣ
板の評価結果を表１に示した。Example 2 A coating agent was obtained in the same manner as in Example 1 except that TAS was changed to dipentaerythritol hexaacrylate (KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd.). . Using this coating agent, a PC board having a cured coating film formed thereon was obtained in the same manner as in Example 1. Obtained surface-hardened PC
Table 1 shows the evaluation results of the plates.
【００６４】（実施例３）実施例１において、ＴＡＳを
トリメチロールプロパンアクリレート（大阪有機化学工
業（株）製、ＴＭＰＴＡ）に代えた以外は、実施例１と
同様にしてコーティング剤を得た。さらにこのコーティ
ング剤を用い、実施例１と同様にして硬化塗膜を形成し
たＰＣ板を得た。得られた表面硬化ＰＣ板の評価結果を
表１に示した。Example 3 A coating agent was obtained in the same manner as in Example 1 except that TAS was changed to trimethylolpropane acrylate (TMPTA, manufactured by Osaka Organic Chemical Industry Co., Ltd.). Using this coating agent, a PC board having a cured coating film formed thereon was obtained in the same manner as in Example 1. Table 1 shows the evaluation results of the obtained surface-hardened PC boards.
【００６５】（実施例４）実施例１において、ＴＡＳを
トリトリス（２−ヒドロキシエチル）イソシアヌレート
のジアクリレート（東亜合成化学工業（株）製、アロニ
ックスＭ−２１５）に代えた以外は、実施例１と同様に
してコーティング剤を得た。さらにこのコーティング剤
を用い、実施例１と同様にして硬化塗膜を形成したＰＣ
板を得た。得られた表面硬化ＰＣ板の評価結果を表１に
示した。Example 4 The procedure of Example 1 was repeated, except that the TAS was replaced by tritris (2-hydroxyethyl) isocyanurate diacrylate (Aronix M-215, manufactured by Toa Gosei Chemical Industry Co., Ltd.). In the same manner as in Example 1, a coating agent was obtained. Further, a PC having a cured coating film formed using this coating agent in the same manner as in Example 1
I got a board. Table 1 shows the evaluation results of the obtained surface-hardened PC boards.
【００６６】（実施例５）実施例１において得られたコ
ーティング剤を、厚さ３ｍｍのポリメチルメタクリレー
ト板（三菱レイヨン（株）製、アクリライトＬ、以下、
ＰＭＭＡ板という）に塗布し、塗布面に厚さ５０μｍの
ポリエチレンテレフタレートの２軸延伸フィルムを被せ
て積層し、ゴムロールで膜厚８μｍに設定した。次い
で、７０℃の雰囲気下で４０分保持した後、フィルム面
を上にして出力１２０Ｗ／ｃｍのメタルハライドランプ
の下（距離２１０ｍｍ）を１．６ｍ／分の速度で通過さ
せ１段目の硬化を行い、フィルムを剥離した後、塗膜面
を上にして出力１２０Ｗ／ｃｍの高圧水銀灯の下（距離
２１０ｍｍ）を１．６ｍ／分の速度で通過させ２段目の
硬化を行った。得られた表面硬化ＰＭＭＡ板の評価結果
を表１に示した。Example 5 A 3 mm thick polymethyl methacrylate plate (Acrylite L, manufactured by Mitsubishi Rayon Co., Ltd .;
PMMA plate), a 50 μm-thick biaxially stretched film of polyethylene terephthalate was put on the coated surface and laminated, and the film thickness was set to 8 μm with a rubber roll. Next, after holding for 40 minutes in an atmosphere of 70 ° C., the film was passed under a metal halide lamp having an output of 120 W / cm (distance 210 mm) at a speed of 1.6 m / min with the film surface facing upward to cure the first stage. After the film was peeled off, the film was passed under a high-pressure mercury lamp with an output of 120 W / cm (distance 210 mm) at a speed of 1.6 m / min with the coating surface facing upward to perform second-stage curing. Table 1 shows the evaluation results of the obtained surface-hardened PMMA plates.
【００６７】（実施例６）実施例２で得たコーティング
剤を用い、実施例５と同様にして硬化塗膜を形成したＰ
ＭＭＡ板を得た。得られた表面硬化ＰＭＭＡ板の評価結
果を表１に示した。(Example 6) Using the coating agent obtained in Example 2 and forming a cured coating film in the same manner as in Example 5,
An MMA plate was obtained. Table 1 shows the evaluation results of the obtained surface-hardened PMMA plates.
【００６８】（比較例１）ＴＡＳ ４０重量部、Ｃ６Ｄ
Ａ ６０重量部、ＴＰＯ ２．８重量部、ベンゾフェノ
ン１重量部を混合後、攪拌溶解してコーティング剤を得
た。得られたコーティング剤を、厚さ２ｍｍのＰＣ板に
塗布し、塗布面に厚さ５０μｍのポリエチレンテレフタ
レートの２軸延伸フィルムを被せ、ゴムロールで膜厚８
μｍに設定した。次いで、フィルム面を上にして出力１
２０Ｗ／ｃｍのメタルハライドランプの下（距離２１０
ｍｍ）を１．６ｍ／分の速度で通過させ１段目の硬化を
行い、フィルムを剥離し、塗膜面上にして出力１２０Ｗ
／ｃｍの高圧水銀灯の下（距離２１０ｍｍ）を１．６ｍ
／分の速度で通過させ２段目の硬化を行った。得られた
表面硬化ＰＣ板の評価結果を表１に示した。(Comparative Example 1) TAS 40 parts by weight, C6D
A 60 parts by weight, 2.8 parts by weight of TPO, and 1 part by weight of benzophenone were mixed and dissolved by stirring to obtain a coating agent. The obtained coating agent is applied to a PC board having a thickness of 2 mm, a biaxially stretched film of polyethylene terephthalate having a thickness of 50 μm is put on the application surface, and a film thickness of 8 is applied with a rubber roll.
It was set to μm. Then, output 1 with the film side up
Under a 20 W / cm metal halide lamp (distance 210
mm) at a speed of 1.6 m / min to cure the first stage, peel off the film, put it on the coating surface and output 120 W
/ M under a high pressure mercury lamp (distance 210 mm) is 1.6 m
/ Min and a second stage of curing was performed. Table 1 shows the evaluation results of the obtained surface-hardened PC boards.
【００６９】（比較例２）比較例１において、ＴＡＳを
ジペンタエリスリトールヘキサアクリレートに代えた以
外は、比較例１と同様にしてコーティング剤を得た。さ
らにこのコーティング剤を用い、比較例１と同様にして
硬化塗膜を形成したＰＣ板を得た。得られた表面硬化Ｐ
Ｃ板の評価結果を表１に示した。Comparative Example 2 A coating agent was obtained in the same manner as in Comparative Example 1, except that TAS was changed to dipentaerythritol hexaacrylate. Further, a PC board having a cured coating film formed thereon was obtained in the same manner as in Comparative Example 1 using this coating agent. Obtained surface hardening P
Table 1 shows the evaluation results of the C plate.
【００７０】（参考例１〜２）未処理のＰＣ板及びＰＭ
ＭＡ板の評価結果も併せ表１に示した。(Reference Examples 1 and 2) Untreated PC board and PM
Table 1 also shows the evaluation results of the MA plate.
【００７１】[0071]
【表１】 [Table 1]
【００７２】[0072]
【発明の効果】本発明のコーティング剤は、樹脂成形品
に対し高い表面硬度を付与し、かつ無溶剤化が可能なコ
ーティング剤である。そして、本発明のコーティング剤
による硬化塗膜を有する樹脂成形品は、表面硬度が高
く、特に透明な樹脂成形品として好適なるものである。The coating agent of the present invention is a coating agent which can impart high surface hardness to a resin molded product and can be made solvent-free. The resin molded article having the cured coating film of the coating agent of the present invention has a high surface hardness and is particularly suitable as a transparent resin molded article.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０９Ｄ 183/08 Ｇ０２Ｂ 1/10 Ｚ ──────────────────────────────────────────────────の Continued on front page (51) Int.Cl. 6 Identification code FI C09D 183/08 G02B 1/10 Z
Claims (4)
くはその部分縮合物と、下記一般式［１］で表されるシ
ラン化合物の加水分解物で微粒子の表面が処理された金
属酸化物微粒子（ｂ）を含むことを特徴とするコーティ
ング剤。 【化１】 1. Metal oxide fine particles whose surfaces are treated with a (meth) acrylate monomer (a) or a partial condensate thereof and a hydrolyzate of a silane compound represented by the following general formula [1]: A coating agent comprising (b). Embedded image
分子中に少なくとも２個の（メタ）アクリロイルオキシ
基を有する多官能（メタ）アクリレート単量体（ａ1）
５０〜１００重量％とそれと共重合可能な単官能（メ
タ）アクリレート単量体（ａ2）５０〜０重量％からな
る混合物である請求項１記載のコーティング剤。2. The method according to claim 1, wherein the (meth) acrylate monomer (a) is
Polyfunctional (meth) acrylate monomer having at least two (meth) acryloyloxy groups in the molecule (a 1 )
50-100% by weight and copolymerizable therewith monofunctional (meth) acrylate monomer (a 2) a coating agent according to claim 1 which is a mixture consisting of 50 to 0% by weight.
である請求項１または請求項２記載のコーティング剤。3. The coating agent according to claim 1, wherein the metal oxide fine particles are colloidal silica.
のコーティング剤を樹脂成形品表面に塗布した塗布層を
ラジカル重合して得られる硬化塗膜を有する樹脂成形
品。4. A resin molded article having a cured coating film obtained by radical polymerization of a coating layer obtained by applying the coating agent according to claim 1, 2 or 3 on the surface of the resin molded article.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26914596A JP3718563B2 (en) | 1996-09-20 | 1996-09-20 | Resin molded product having coating agent and cured coating film |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26914596A JP3718563B2 (en) | 1996-09-20 | 1996-09-20 | Resin molded product having coating agent and cured coating film |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1095937A true JPH1095937A (en) | 1998-04-14 |
| JP3718563B2 JP3718563B2 (en) | 2005-11-24 |
Family
ID=17468319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26914596A Expired - Lifetime JP3718563B2 (en) | 1996-09-20 | 1996-09-20 | Resin molded product having coating agent and cured coating film |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3718563B2 (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001055443A (en) * | 1999-08-19 | 2001-02-27 | Kansai Paint Co Ltd | Active energy light-curable composition and method for forming coating film thereof |
| JP2002187921A (en) * | 2000-10-11 | 2002-07-05 | Jsr Corp | Curable composition and cured product thereof |
| WO2004041888A1 (en) * | 2002-11-08 | 2004-05-21 | Mitsubishi Chemical Corporation | Radiation curing resin composition and cured product thereof |
| JP2006182880A (en) * | 2004-12-27 | 2006-07-13 | Mitsubishi Rayon Co Ltd | Curable composition |
| JP2015196685A (en) * | 2014-03-31 | 2015-11-09 | 株式会社松風 | Novel sulfur-containing silane coupling agent and dental composition containing the same |
| WO2019221268A1 (en) * | 2018-05-18 | 2019-11-21 | 三井化学株式会社 | Anti-fogging laminate and method for producing same |
| JPWO2024019139A1 (en) * | 2022-07-22 | 2024-01-25 | ||
| US12521932B2 (en) | 2019-10-09 | 2026-01-13 | Teijin Limited | Method of producing curved member and polycarbonate resin laminate with hard coat layer for heat bending |
-
1996
- 1996-09-20 JP JP26914596A patent/JP3718563B2/en not_active Expired - Lifetime
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001055443A (en) * | 1999-08-19 | 2001-02-27 | Kansai Paint Co Ltd | Active energy light-curable composition and method for forming coating film thereof |
| JP2002187921A (en) * | 2000-10-11 | 2002-07-05 | Jsr Corp | Curable composition and cured product thereof |
| WO2004041888A1 (en) * | 2002-11-08 | 2004-05-21 | Mitsubishi Chemical Corporation | Radiation curing resin composition and cured product thereof |
| US7569619B2 (en) | 2002-11-08 | 2009-08-04 | Mitsubishi Chemical Corporation | Radiation-curable resin composition and cured product thereof |
| JP2006182880A (en) * | 2004-12-27 | 2006-07-13 | Mitsubishi Rayon Co Ltd | Curable composition |
| JP2015196685A (en) * | 2014-03-31 | 2015-11-09 | 株式会社松風 | Novel sulfur-containing silane coupling agent and dental composition containing the same |
| WO2019221268A1 (en) * | 2018-05-18 | 2019-11-21 | 三井化学株式会社 | Anti-fogging laminate and method for producing same |
| JPWO2019221268A1 (en) * | 2018-05-18 | 2021-05-13 | 三井化学株式会社 | Anti-fog laminate and its manufacturing method |
| US12521932B2 (en) | 2019-10-09 | 2026-01-13 | Teijin Limited | Method of producing curved member and polycarbonate resin laminate with hard coat layer for heat bending |
| JPWO2024019139A1 (en) * | 2022-07-22 | 2024-01-25 | ||
| WO2024019139A1 (en) * | 2022-07-22 | 2024-01-25 | 株式会社日本触媒 | Composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3718563B2 (en) | 2005-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5695851A (en) | Coating composition and molded articles having a surface coated therewith | |
| CN109312038B (en) | Active energy ray-curable resin composition, resin molded product, and method for producing resin molded product | |
| JPWO1997011129A1 (en) | Abrasion-resistant film-forming coating composition and article coated with the film | |
| EP0869154A1 (en) | Coating composition forming wear-resistant coat and article covered with the coat | |
| WO2009119436A1 (en) | Composition for coating a plastic substrate, coating film formed therefrom, and formed body | |
| JP4363077B2 (en) | Active energy ray-curable composition and hard coat film | |
| JPH0314879A (en) | Coating composition | |
| JP4372268B2 (en) | Resin molded product having coating agent and coating layer | |
| WO2000006654A1 (en) | Coating material and molded resin with coating layer | |
| JP2004346228A (en) | Active energy ray-curable composition and hard coat film | |
| JP3718563B2 (en) | Resin molded product having coating agent and cured coating film | |
| JPH0314880A (en) | Coating composition | |
| JP3436492B2 (en) | Thin article having a wear-resistant thin film and optical disc | |
| JP3218132B2 (en) | Forming method of surface hardened film | |
| JP3442255B2 (en) | UV curable composition and material having functional surface | |
| JP3035468B2 (en) | Coating composition, surface-coated molded article using the same | |
| JP3819245B2 (en) | Curable composition for coating, coated article, and outer skin for automobile | |
| JP3072193B2 (en) | Coating composition and surface-coated article | |
| JP3088511B2 (en) | Coating composition and surface-coated article | |
| JP3025587B2 (en) | Coating composition and surface-coated molding | |
| JP3984424B2 (en) | Method for forming top coat film, coated article, and outer plate for automobile | |
| JP3782670B2 (en) | Curable composition for coating, coated article, outer plate for automobile, and active energy ray-curable composition | |
| JP2005162781A (en) | Curable composition and article | |
| JPH11157014A (en) | Resin molded article having coating layer and method for producing the same | |
| JP2005144872A (en) | Laminated plate, glazing material for window, and manufacturing method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20050527 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20050607 |
|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050728 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20050830 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20050905 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080909 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090909 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100909 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110909 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110909 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110909 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120909 Year of fee payment: 7 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120909 Year of fee payment: 7 |
|
| S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120909 Year of fee payment: 7 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130909 Year of fee payment: 8 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |