WO2017141527A1 - Composition de revêtement et article revêtu - Google Patents
Composition de revêtement et article revêtu Download PDFInfo
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- WO2017141527A1 WO2017141527A1 PCT/JP2016/086870 JP2016086870W WO2017141527A1 WO 2017141527 A1 WO2017141527 A1 WO 2017141527A1 JP 2016086870 W JP2016086870 W JP 2016086870W WO 2017141527 A1 WO2017141527 A1 WO 2017141527A1
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- 239000008199 coating composition Substances 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- -1 titanium alkoxide compound Chemical class 0.000 claims description 40
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 20
- 229960002479 isosorbide Drugs 0.000 claims description 17
- 239000010936 titanium Substances 0.000 claims description 9
- 229910052719 titanium Inorganic materials 0.000 claims description 9
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 229960000834 vinyl ether Drugs 0.000 claims description 3
- VPRMGOPLYBDBLB-WRWGMCAJSA-N (3s,3ar,6r,6ar)-3,6-bis(prop-2-enoxy)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound C=CCO[C@H]1CO[C@@H]2[C@H](OCC=C)CO[C@@H]21 VPRMGOPLYBDBLB-WRWGMCAJSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 abstract description 25
- 238000000576 coating method Methods 0.000 abstract description 22
- 230000000903 blocking effect Effects 0.000 abstract description 3
- 230000005540 biological transmission Effects 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 10
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KLDXJTOLSGUMSJ-UHFFFAOYSA-N OC(COC12)C1OCC2O Chemical compound OC(COC12)C1OCC2O KLDXJTOLSGUMSJ-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940052303 ethers for general anesthesia Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
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- 238000001179 sorption measurement Methods 0.000 description 2
- 238000000411 transmission spectrum Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- KLDXJTOLSGUMSJ-BXKVDMCESA-N (3s,3as,6s,6as)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@H]2[C@@H](O)CO[C@H]21 KLDXJTOLSGUMSJ-BXKVDMCESA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- SNOJPWLNAMAYSX-UHFFFAOYSA-N 2-methylpropan-1-ol;titanium Chemical compound [Ti].CC(C)CO.CC(C)CO.CC(C)CO.CC(C)CO SNOJPWLNAMAYSX-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- MCDBEBOBROAQSH-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl prop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C=C MCDBEBOBROAQSH-UHFFFAOYSA-N 0.000 description 1
- BIGOJJYDFLNSGB-UHFFFAOYSA-N 3-isocyanopropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCC[N+]#[C-] BIGOJJYDFLNSGB-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SAZOJNMYWMWJPP-UHFFFAOYSA-N CO[Si](CCCOC1=CC=C(C=C1)CCC)(OC)OC Chemical group CO[Si](CCCOC1=CC=C(C=C1)CCC)(OC)OC SAZOJNMYWMWJPP-UHFFFAOYSA-N 0.000 description 1
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- 229920000298 Cellophane Polymers 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- DUMWHCLFZJQIGA-UHFFFAOYSA-N [methoxy(dimethyl)silyl] trimethyl silicate Chemical compound CO[Si](C)(C)O[Si](OC)(OC)OC DUMWHCLFZJQIGA-UHFFFAOYSA-N 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
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- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
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- 239000000499 gel Substances 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- DPNUIZVZBWBCPB-UHFFFAOYSA-J titanium(4+);tetraphenoxide Chemical compound [Ti+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 DPNUIZVZBWBCPB-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DAHWFTWPSFSFMS-UHFFFAOYSA-N trihydroxysilane Chemical compound O[SiH](O)O DAHWFTWPSFSFMS-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
Definitions
- the present invention relates to a coating composition and a coated article. More specifically, the present invention relates to a coating composition comprising a silicone composition containing an alkoxysilane compound having a bicyclic ether structure, and a coating formed by coating with the composition. It relates to goods.
- ultraviolet rays have characteristics that are not found in visible light, they are used in various fields such as analytical equipment such as ultraviolet photography, bill authentication equipment, or photochemical reaction equipment.
- Ultraviolet rays are mainly classified into near ultraviolet rays (wavelength 380 to 200 nm; NUV), far ultraviolet rays (vacuum ultraviolet ray) (wavelength 200 to 10 nm; FUV / VUV), and extreme ultraviolet rays (wavelength 1 to 31 nm; EUV / XUV). Since the atmosphere containing oxygen absorbs ultraviolet rays having a wavelength of 200 nm or less and the lens material has a low transmittance with respect to wavelengths of 180 nm or less, near ultraviolet rays are usually targeted.
- UV-A 400 nm-315 nm
- UV-B 315 nm-280 nm
- UV-C 280 nm-200 nm
- health UV rays 400 nm-360 nm
- chemical UV rays depending on the wavelength
- germicidal UV rays 280 nm-200 nm
- ultraviolet rays in the wavelength region of UV-C and germicidal UV rays are extremely toxic because ozone is generated from oxygen in the air and this ozone reacts with the DNA of the organism to damage the gene. For this reason, in applications other than sterilization, it has been desired to block ultraviolet light having a wavelength of less than 280 nm as much as possible even when transmitting ultraviolet light having a wavelength of 280 nm or longer.
- soda-lime glass used as a general window material absorbs even ultraviolet rays with a wavelength of 350 nm or less, so that sufficient ultraviolet intensity cannot be obtained, while heavy metal doped quartz glass absorbs ultraviolet wavelengths. Since many heavy metals are contained, the illuminance of ultraviolet rays is greatly reduced during use, and there is a problem that the effect of ultraviolet rays is halved even when the lamp is lit. Furthermore, a technique for selectively transmitting ultraviolet rays by coating the surface of quartz glass that transmits the entire near ultraviolet region by vacuum deposition or sputtering is also known (Patent Document 3). It requires a simple coating device and is not an easy technique.
- thermosetting coating agent having a siloxane skeleton is known as a coating agent used for coating a substrate such as a resin such as plastic or film, or glass, and many technical proposals have been made on this siloxane-based coating agent.
- Patent Documents 4 and 5 disclose a coating composition comprising a trihydroxysilane partial condensate and colloidal silica
- Patent Documents 6 and 7 disclose a partial condensate of alkyltrialkoxysilane and tetraalkoxysilane.
- the coating composition which has as a main component is disclosed.
- Patent Documents 8 and 9 report a technique for improving curability by adding a titanium chelate compound or a partially hydrolyzed condensate thereof as a curing catalyst to a coating agent.
- the present invention has been made in view of the above circumstances, and transmits ultraviolet light having a wavelength of 280 nm or more as much as possible and blocks ultraviolet light having a wavelength of less than 280 nm without impairing the characteristics of the curable coating composition having a siloxane bond.
- An object of the present invention is to provide a siloxane-based coating composition having such selective UV-transmitting optical properties.
- the present inventors have used a coating composition containing an alkoxysilane containing an alkoxysilane compound having a polycyclic ether structure such as an isosorbide structure, so that a wavelength of 280 nm or more can be used.
- the inventors have found that a cured film that transmits ultraviolet rays and blocks ultraviolet rays having a wavelength of less than 280 nm can be efficiently obtained, and the present invention has been completed.
- the present invention 1.
- the coating composition according to 1, wherein the curing catalyst is a titanium alkoxide compound, 3.
- a coated article comprising a substrate and a cured film formed by curing any one of the coating compositions 1 to 3 formed thereon; 5).
- R 1 is an ethylene group or a trimethylene group, and n is 0.
- the coating composition of the present invention By using the coating composition of the present invention, it is possible to form a hard film having excellent selective ultraviolet light transmission optical characteristics of transmitting ultraviolet light having a wavelength of 280 nm or more and blocking ultraviolet light having a wavelength of less than 280 nm. .
- the inorganic organosiloxane compound has hard physical properties, and at the same time, the organic polymer film-forming properties, crack resistance, flexibility, glass adhesion properties, and the like. A film having the same can be formed.
- the coating composition of the present invention capable of providing a hard film having such characteristics and a coated article having the film is various, such as an analytical instrument such as ultraviolet photography, a bill authenticity determination instrument, or a photochemical reaction apparatus. Can be used in the field.
- the coating composition according to the present invention comprises (A) an alkoxysilane containing a compound having a polycyclic ether structure represented by the following formula (I), a hydrolyzate or a condensate thereof, and (B) a curing catalyst. Including.
- each Y represents the same or different —R 1 —SiR 2 n (OR 3 ) 3-n group
- R 1 represents an alkylene group having 1 to 6 carbon atoms
- R 2 and R 3 represents an alkyl group having 1 to 5 carbon atoms, which may be the same or different.
- Specific examples of the alkylene group having 1 to 6 carbon atoms are not particularly limited, and examples include methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene groups, etc. To 3 alkylene groups are preferred, and ethylene groups and trimethylene groups are more preferred.
- the alkyl group having 1 to 5 carbon atoms may be linear, cyclic or branched, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, and s-butyl. , T-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl group, etc., among which an alkyl group having 1 to 3 carbon atoms is preferable, a methyl group and an ethyl group are more preferable, and a methyl group is most preferable.
- n is an integer of 0 to 2, preferably 0 or 1, and more preferably 0.
- the compound represented by the above formula (I) is obtained by reacting a compound having a bicyclic ether structure and two OH groups with a compound having a C—C double bond, thereby producing a compound having a C—C double bond.
- the obtained compound and an alkoxysilane having a Si—H group can be obtained by a hydrosilylation reaction in the presence of a catalyst.
- the compound having a polycyclic ether structure and two OH groups may be any of D-isosorbide (hereinafter simply abbreviated as isosorbide), L-isosorbide, and stereoisomers of isomannide, and a combination of two or more of these. It may be used.
- dihydric alcohols are preferably those using isosorbide as a raw material from the viewpoint of easy availability.
- Isosorbide is 1,4: 3,6-dianhydro-D-sorbitol produced from bio raw materials. For example, it is a compound obtained by hydrogenating D-glucose and then dehydrating with an acid catalyst.
- the dehydration catalyst include sulfuric acid, paratoluenesulfonic acid, methanesulfonic acid, hydrochloric acid, phosphoric acid and the like. These dehydration reactions can generally be performed efficiently in an organic solvent such as toluene or xylene.
- the compound having the C—C double bond examples include allyl compounds and vinyl compounds. These compounds are reacted with the OH group of the compound having the above-mentioned double-ring ether structure and two OH groups.
- a bicyclic ether compound having a bond having a C—C double bond that is, an isosorbide-diallyl ether compound or an isosorbide-divinyl ether compound
- an alkoxysilane having a hydro group is synthesized in the presence of a hydrosilylation catalyst.
- a compound represented by the above formula (I) can be obtained by a hydrosilylation reaction.
- the compound represented by the above formula (I) is a bissilane compound, and can be produced by an addition reaction between an isosorbide-unsaturated ether compound and a hydrosilane compound represented by the following formula (III).
- H-SiR 2 n (OR 3 ) 3-n (III) (Wherein R 2 , R 3 and n represent the same meaning as described above.)
- hydrosilane compound represented by the above formula (III) a hydrosilane compound having 1 to 3, preferably 2 or 3 methoxy, ethoxy, propoxy, butoxy, or pentoxy groups in one molecule is suitable.
- trimethoxysilane and triethoxysilane are more preferable.
- the addition reaction between the isosorbide-unsaturated ether compound and the hydrosilane compound represented by the above formula (III) can be carried out under known hydrosilylation reaction conditions, preferably using a platinum catalyst, for example, at room temperature to 150
- the reaction is performed in the range of 0 ° C., more preferably 25 to 100 ° C.
- trimethoxysilane is used, the reaction is completed in about 30 minutes to 2 hours by heating to about 80 ° C.
- the component (A) of the present invention further includes a silane compound represented by the following formula (II), a cohydrolyzate or a condensate of these silane compounds.
- a silane compound represented by the following formula (II) a cohydrolyzate or a condensate of these silane compounds.
- a 1 represents an alkyl group having 1 to 10 carbon atoms which may be the same or different
- a 2 represents an aryl group, a halogenated alkyl group or a halogenated aryl which may be the same or different.
- a 3 represents a group of at least species, and A 3 represents an alkoxy group having 1 to 10 carbon atoms, an alkenyloxy group having 2 to 10 carbon atoms, or an acyloxy group having 1 to 10 carbon atoms, which may be the same or different, and a And b is any integer from 0 to 2, and a + b satisfies any integer from 0 to 2.
- the alkyl group having 1 to 10 carbon atoms may be linear, cyclic or branched, and specific examples thereof include n-hexyl in addition to the groups exemplified as the alkyl group having 1 to 5 carbon atoms. N-heptyl, n-octyl, n-nonyl, n-decyl, cyclohexyl group and the like.
- the carbon number of the alkenyl group is not particularly limited, but preferably 2 to 10 carbon atoms.
- halogenated alkyl group include a group in which at least one hydrogen atom of the group exemplified as the alkyl group having 1 to 10 carbon atoms is substituted with a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
- the number of carbon atoms of the aryl group is not particularly limited, but preferably 6 to 20 carbon atoms. Specific examples thereof include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9- Anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl group and the like can be mentioned.
- Specific examples of the halogenated aryl group include groups in which at least one hydrogen atom of the group exemplified as the aryl group is substituted with a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
- epoxyalkyl group examples include 3-glycidoxypropyl, 2- (3,4-epoxycyclohexyl) ethyl group and the like.
- (meth) acryloyloxyalkyl group examples include a 3- (meth) acryloyloxypropyl group.
- Specific examples of the mercaptoalkyl group include a 3-mercaptopropyl group.
- Specific examples of the aminoalkyl group include 3-aminopropyl, 2-aminoethyl group and the like.
- alkoxy group having 1 to 10 carbon atoms include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, n-hexoxy, and n-heptyloxy, n-octyloxy, n-nonyloxy, n-decyloxy groups and the like.
- alkenyloxy group having 2 to 10 carbon atoms include ethenyloxy, n-1-propenyloxy, n-2-propenyloxy, n-1-butenyloxy, n-2-butenyloxy, n-3-butenyloxy, n- Examples include 1-pentenyloxy and n-1-decenyloxy groups.
- Specific examples of the acyloxy group having 1 to 10 carbon atoms include formyloxy, acetoxy, propylonyloxy, butyryloxy, isobutyryloxy, pivaloyloxy, benzoyloxy group and the like.
- alkoxysilane represented by the formula (II) include tetramethoxysilane, tetraethoxysilane, tetra n-propoxysilane, tetraisopropoxysilane, tetra n-butoxysilane, tetraisobutoxysilane, and methyltrimethoxysilane.
- the compound represented by the above formula (I) used for the component (A) improves the hydrophilicity of the resulting cured film, decreases the water contact angle, or increases the refractive index. Since it is a component that exerts an action of increasing or reacting with a curing catalyst to absorb light of a specific wavelength, considering that these characteristics are sufficiently exhibited in the obtained cured film, (A)
- the ratio of the compound represented by the formula (I) in the component is such that the content of Si atoms derived from the compound represented by the formula (I) is 55 moles relative to the total number of Si atoms in the component (A). It is preferable to supply to the reaction system so as to be at least%.
- the obtained system is stabilized and various problems (whitening, foam, heterogeneity, etc.) at the time of coating film formation are prevented.
- the amount of water added is 1 to 10 mol with respect to a total of 1 mol of hydrolyzable groups represented by OR 3 and A 3 , respectively. More preferably, the amount is 1.5 to 5 mol.
- hydrolysis catalyst known catalysts can be used, and specific examples thereof include acidic hydrogen halide, carboxylic acid, sulfonic acid, acidic or weakly acidic oxide or inorganic salt, ion exchange resin and the like. Examples include solid acids.
- the amount of the hydrolysis catalyst used is preferably 0.001 to 10 mol% with respect to 1 mol of the hydrolyzable group (OR 3 and A 3 ).
- the hydrolysis reaction is preferably carried out under acidic conditions at a pH of 1 to 6, and more preferably carried out under a weakly acidic pH in the range of 4 to 6 from the viewpoint of the stability of the silanol groups produced.
- Hydrolysis and condensation conditions can be performed under known conditions, and may be performed in a solvent.
- Solvents include alcohols such as methanol, ethanol, propanol, isopropyl alcohol, n-butanol, isobutanol, t-butanol, diacetone alcohol; methyl propyl ketone, diethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol, etc.
- Ketones such as dipropyl ether, dibutyl ether, anisole, dioxane, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate; propyl acetate, butyl acetate, cyclohexyl acetate, etc.
- Examples include esters.
- the reaction temperature and time can be arbitrarily selected according to the azeotropic temperature of the system, and are not particularly limited, but are usually about 20 to 150 ° C. for about 30 minutes to 2 hours.
- a curing catalyst is added to the coating composition of the present invention.
- the curing catalyst it can be appropriately selected from conventionally known catalysts, but in the present invention, a titanium-based catalyst is particularly preferable, and is dissolved in the component (A) and a solvent used as necessary, or Those that are dispersed are preferred. Specific examples thereof include titanium alkoxide, titanium halide, alkyl titanium and the like, and titanium alkoxide is preferable.
- titanium alkoxide examples include titanium tetraisopropoxide, titanium tetra n-propoxide, titanium tetraisobutoxide, titanium tetra n-butoxide, titanium tetraphenoxide and the like, and titanium tetra n-butoxide is preferable.
- the blending amount of the component (B) is not particularly limited as long as it is an amount effective for curing the present composition, but a cured film having sufficient hardness can be produced and cracks in the cured film can be produced. And whitening, and appropriate use time of the composition, etc., the amount is preferably 0.001 to 10% by weight, preferably 0.01 to 5% by weight with respect to component (A). More preferred.
- the coating composition of the present invention may further contain (C) a solvent for the purpose of adjusting the concentration of the active ingredient.
- a polar organic solvent can be suitably used, and specific examples thereof include alcohols such as methanol, ethanol, propanol, isopropyl alcohol, n-butanol, isobutanol, t-butanol, diacetone alcohol; methyl propyl ketone, Ketones such as diethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol; dipropyl ether, dibutyl ether, anisole, dioxane, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc. And ethers such as propyl acetate, butyl acetate, and cyclohexyl acetate.
- composition of the coating composition of the present invention is appropriately designed in terms of the stability of the composition, transparency of the resulting cured film, hardness, adhesion, and crack resistance.
- the blending amount of component (A) with respect to the total amount of is preferably 50 to 99% by mass, more preferably 60 to 95% by mass.
- the above-described coating composition of the present invention is applied to at least one surface of a substrate directly or via one or more other layers and cured to form a film, thereby providing a coated article.
- the substrate is not particularly limited, and examples thereof include a resin molded body, ceramics or glass, and a transparent material is particularly preferable. Among these, a glass material is preferable, and quartz glass that can transmit ultraviolet rays is more preferable.
- Examples of the coating method include, from various known coating methods such as brush coating, spraying, dipping, flow coating, roll coating, curtain coating, spin coating, knife coating, and the like, and the shape of the substrate and the desired coating properties ( What is necessary is just to select suitably according to a film thickness etc.).
- the hydrolysis and condensation reaction of the component (A) in the coating film proceeds.
- any humidity of 10 to 100% RH may be used. In general, the higher the humidity, the faster the hydrolysis proceeds. Therefore, moisture may be added to the atmosphere as desired.
- the curing reaction temperature and time can be appropriately changed according to factors such as the substrate used, the moisture concentration, the catalyst concentration, and the type of hydrolyzable group. Usually, it is about 5 minutes to 5 hours within the range not exceeding the heat resistance temperature of the base material to be used, but it is preferable to heat within the range not exceeding the heat resistance temperature of the base material and cure for 10 minutes to 2 hours. Specifically, it is more preferable to cure at 30 to 150 ° C. for 30 minutes to 2 hours.
- the thickness of the cured film to be produced is not particularly limited, but it is 0 in consideration of hardness, imparting optical characteristics to the substrate, long-term stable adhesion, and no foaming or cracking. 5 to 60 ⁇ m is preferable, and 1 to 30 ⁇ m is more preferable. In order to obtain a desired thickness, the above-described series of coating and curing operations may be repeated to perform overcoating.
- the refractive index is a value at 25 ° C. measured with an Atago refractometer RX7000 ⁇
- the viscosity is a value measured at 25 ° C. with a rotational viscometer
- the weight average molecular weight is GPC ( It is a value (polystyrene conversion value) measured by a gel permeation chromatograph).
- 1 H-NMR was measured with Bruker AVANCE 400M.
- the reaction temperature during the dropping was controlled to be 65 ° C. or lower, and after completion of the dropping, the temperature of the system was maintained at 65 ° C. for 2 hours, and then the reaction mixture was cooled.
- 5 g of silica gel (Wakogel C-100, manufactured by Wako Pure Chemical Industries, Ltd.) was added to the reaction system, and the platinum catalyst was removed by adsorption filtration, followed by concentration under reduced pressure to remove toluene, and 460 g (0 .96 mol) was obtained.
- the refractive index was 1.4568 (589 nm).
- the 1 H-NMR spectrum of the obtained compound was measured and confirmed to be bis [(3-trimethoxysilyl) propoxy] isosorbide.
- Example 1 A 2 liter flask equipped with a nitrogen introduction tube, a stirrer, a condenser and a thermometer was charged with 95 g of the bis (trimethoxysilylsilylpropoxy) isosorbide obtained in Synthesis Example 1 and maintained at 20 ° C. with stirring. Here, 5 g of tetra-n-butoxy titanium was added as a curing catalyst to obtain a coating composition.
- Example 2 Example 1 was used except that bis [(2-trimethoxysilyl) ethoxy] isosorbide obtained in Synthesis Example 2 was used instead of bis [(3-trimethoxysilyl) propoxy] isosorbide obtained in Synthesis Example 1. In the same manner as in No. 1, a coating composition was obtained.
- ⁇ Completely transparent
- ⁇ Partially turbid
- Hardness The film surface was rubbed with a nail and measured whether it was scratched or not, and judged according to the following criteria.
- ⁇ Not scratched
- ⁇ Scratched
- Adhesiveness In accordance with JIS K5400, the test piece was cut with a razor blade in 6 vertical and horizontal intervals of 2 mm to make 25 grids, and was commercially available. After the cellophane adhesive tape (manufactured by Nichiban Co., Ltd.) was adhered closely, the number of squares (X) remaining without peeling off the coating was displayed as X / 25 when it was peeled off 90 ° toward the front.
- the cured films prepared from the coating compositions obtained in Examples 1 and 2 were excellent in transparency and adhesion in the visible light region, and also in the UV-A region ( It can be seen that the film shows selective ultraviolet transparency that satisfies both ultraviolet transparency at a wavelength of 315 nm or more) and ultraviolet shielding properties in the UV-C region (less than 280 nm).
- the cured film of Comparative Example 1 using a general methyl-based siloxane transmits ultraviolet light in a wide region from the UV-A region to the UV-C region, while being derived from bisphenol A instead of the isosorbide skeleton.
- Comparative Example 2 having a skeleton that shields not only the UV-C region but also the UV-A region. From the above results, by using the coating composition of the present invention, it is possible to form a hard film having a selective ultraviolet ray transmittance that satisfies both the ultraviolet ray transmittance in the UV-A region and the ultraviolet ray shielding property in the UV-C region. I found it possible.
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Abstract
L'invention concerne une composition de revêtement qui contient (A) un alcoxysilane contenant un composé représenté par la formule (I) ou un hydrolysat ou un condensat de celui-ci et (B) un catalyseur de durcissement, ladite composition de revêtement permettant d'obtenir un revêtement présentant des caractéristiques optiques sélectives de transmission du rayonnement ultraviolet, à savoir en transmettant un rayonnement ultraviolet ayant des longueurs d'onde supérieures ou égales à 280 nm dans toute la mesure du possible tout en bloquant complètement le rayonnement ultraviolet ayant des longueurs d'onde inférieures à 280 nm, sans perdre les avantages d'une composition de revêtement durcissable comprenant une liaison siloxane. (Dans la formule, les fractions Y peuvent être identiques ou différentes les unes des autres et représentent chacune un groupe représenté par -R1-SiR2
n(OR3)3-n, R1 représente un groupe alkylène comprenant de 1 à 6 atomes de carbone, et R2 et R3 peuvent être identiques ou différents l'un de l'autre et représentent chacun un groupe alkyle comprenant de 1 à 5 atomes de carbone. n représente un nombre entier entre 0 et 2).
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EP16890664.2A EP3418337A4 (fr) | 2016-02-19 | 2016-12-12 | Composition de revêtement et article revêtu |
US15/999,836 US20200071564A1 (en) | 2016-02-19 | 2016-12-12 | Coating composition and coated article |
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JP2016074020A JP6465061B2 (ja) | 2016-02-19 | 2016-04-01 | コーティング用組成物および被覆物品 |
JP2016-074020 | 2016-04-01 |
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