JP5165156B2 - Weather-resistant coating composition and method for forming coated article having weather-resistant coating film - Google Patents
Weather-resistant coating composition and method for forming coated article having weather-resistant coating film Download PDFInfo
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- JP5165156B2 JP5165156B2 JP2012518661A JP2012518661A JP5165156B2 JP 5165156 B2 JP5165156 B2 JP 5165156B2 JP 2012518661 A JP2012518661 A JP 2012518661A JP 2012518661 A JP2012518661 A JP 2012518661A JP 5165156 B2 JP5165156 B2 JP 5165156B2
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- JP
- Japan
- Prior art keywords
- meth
- hydrolyzable silyl
- silyl group
- group
- weather
- 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.)
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- 238000000576 coating method Methods 0.000 title claims description 119
- 239000011248 coating agent Substances 0.000 title claims description 107
- 239000008199 coating composition Substances 0.000 title claims description 75
- 238000000034 method Methods 0.000 title claims description 17
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 133
- 150000001875 compounds Chemical class 0.000 claims description 63
- 239000002904 solvent Substances 0.000 claims description 51
- 229920000178 Acrylic resin Polymers 0.000 claims description 45
- 239000004925 Acrylic resin Substances 0.000 claims description 45
- 239000007787 solid Substances 0.000 claims description 36
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- 229920002050 silicone resin Polymers 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 18
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 150000001336 alkenes Chemical class 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 95
- -1 silyl compound Chemical class 0.000 description 87
- 239000003973 paint Substances 0.000 description 37
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 19
- 229910052500 inorganic mineral Inorganic materials 0.000 description 19
- 239000011707 mineral Substances 0.000 description 19
- 229910000831 Steel Inorganic materials 0.000 description 16
- 239000010959 steel Substances 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 15
- 239000003822 epoxy resin Substances 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 229920000647 polyepoxide Polymers 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 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 14
- 238000012360 testing method Methods 0.000 description 14
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 238000001723 curing Methods 0.000 description 13
- 239000006087 Silane Coupling Agent Substances 0.000 description 11
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 10
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 10
- 239000000049 pigment Substances 0.000 description 10
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 9
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 7
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007774 longterm Effects 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 230000003449 preventive effect Effects 0.000 description 5
- 230000008439 repair process Effects 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 4
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 4
- 239000007888 film coating Substances 0.000 description 4
- 238000009501 film coating Methods 0.000 description 4
- 230000036541 health Effects 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 150000001282 organosilanes Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 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 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 3
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RMKZLFMHXZAGTM-UHFFFAOYSA-N [dimethoxy(propyl)silyl]oxymethyl prop-2-enoate Chemical compound CCC[Si](OC)(OC)OCOC(=O)C=C RMKZLFMHXZAGTM-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 description 3
- 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 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000011527 polyurethane coating Substances 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 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 3
- 239000000126 substance Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical compound CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 2
- MIMKRVLJPMYKID-UHFFFAOYSA-N 1-ethenoxynonane Chemical compound CCCCCCCCCOC=C MIMKRVLJPMYKID-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- PSLRXNFNXYNXEK-UHFFFAOYSA-N 2-triethoxysilylethyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCOC(=O)C=C PSLRXNFNXYNXEK-UHFFFAOYSA-N 0.000 description 2
- BUJVPKZRXOTBGA-UHFFFAOYSA-N 2-trimethoxysilylethyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCOC(=O)C=C BUJVPKZRXOTBGA-UHFFFAOYSA-N 0.000 description 2
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 2
- UDWIZRDPCQAYRF-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl prop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C=C UDWIZRDPCQAYRF-UHFFFAOYSA-N 0.000 description 2
- BFDBEDDUOYPWBW-UHFFFAOYSA-N 3-[diethyl(methoxy)silyl]propyl prop-2-enoate Chemical compound CC[Si](CC)(OC)CCCOC(=O)C=C BFDBEDDUOYPWBW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MYEFGHBUFAPKJO-UHFFFAOYSA-N 3-[methyl(dipropoxy)silyl]propyl prop-2-enoate Chemical compound CCCO[Si](C)(OCCC)CCCOC(=O)C=C MYEFGHBUFAPKJO-UHFFFAOYSA-N 0.000 description 2
- OJPSFJLSZZTSDF-UHFFFAOYSA-N 3-ethoxyprop-1-ene Chemical compound CCOCC=C OJPSFJLSZZTSDF-UHFFFAOYSA-N 0.000 description 2
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 2
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004566 building material Substances 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
- FFOWIEZZYLIBTD-UHFFFAOYSA-N butan-2-olate zirconium(4+) Chemical compound CCC(C)O[Zr](OC(C)CC)(OC(C)CC)OC(C)CC FFOWIEZZYLIBTD-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- DMZWVCJEOLBQCZ-UHFFFAOYSA-N chloro(ethenyl)silane Chemical class Cl[SiH2]C=C DMZWVCJEOLBQCZ-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- YOQPKXIRWPWFIE-UHFFFAOYSA-N ctk4c8335 Chemical compound CC(=C)C(=O)OCCOP(=O)=O YOQPKXIRWPWFIE-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- MAYIDWCWWMOISO-UHFFFAOYSA-N dichloro-bis(ethenyl)silane Chemical compound C=C[Si](Cl)(Cl)C=C MAYIDWCWWMOISO-UHFFFAOYSA-N 0.000 description 1
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 1
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-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
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- XYYQWMDBQFSCPB-UHFFFAOYSA-N dimethoxymethylsilane Chemical compound COC([SiH3])OC XYYQWMDBQFSCPB-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- AJPODVQGWMNSJT-UHFFFAOYSA-N hexan-2-olate zirconium(4+) Chemical compound [Zr+4].CCCCC(C)[O-].CCCCC(C)[O-].CCCCC(C)[O-].CCCCC(C)[O-] AJPODVQGWMNSJT-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- AMVXVPUHCLLJRE-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)hexane-1,6-diamine Chemical compound CO[Si](OC)(OC)CCCNCCCCCCN AMVXVPUHCLLJRE-UHFFFAOYSA-N 0.000 description 1
- XKLJRDXPVLBKKA-UHFFFAOYSA-N n'-[2-[dimethoxy(2-phenylethyl)silyl]oxyethyl]ethane-1,2-diamine Chemical compound NCCNCCO[Si](OC)(OC)CCC1=CC=CC=C1 XKLJRDXPVLBKKA-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- CUSBWBKXZPGKAS-UHFFFAOYSA-N n-[1-(hexylamino)-1-oxo-3-[4-(2-pyrrolidin-1-ylethoxy)phenyl]propan-2-yl]-4-methylbenzamide Chemical compound C=1C=C(C)C=CC=1C(=O)NC(C(=O)NCCCCCC)CC(C=C1)=CC=C1OCCN1CCCC1 CUSBWBKXZPGKAS-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000007591 painting process Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- LTEHWCSSIHAVOQ-UHFFFAOYSA-N tripropyl borate Chemical compound CCCOB(OCCC)OCCC LTEHWCSSIHAVOQ-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
- C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Description
本発明は、耐候性塗料組成物、及び耐候性塗膜を有する塗装物品の形成方法に関する。 The present invention relates to a weather-resistant coating composition and a method for forming a coated article having a weather-resistant coating film.
橋梁、プラント、タンク等の鋼製構造物、鋼板、鋼管等の金属製品等を外界の腐食環境から保護し、そして美観を維持する機能を付与するために防食塗装が施工されている。鋼製構造物の防食塗装には、例えば、ジンクリッチペイント、エポキシ樹脂系の下塗り塗料、中塗り塗料、及びポリウレタン樹脂系、フッ素樹脂系の上塗り塗料を組み合わせた少なくとも3回以上の塗装工程が行われることが一般的である。特に、既設の鋼製構造物に塗装を行う場合には、足場のない高所での作業となるうえに、人件費、足場代が塗装コストのうち8割以上を占めることも多く、塗装回数をできるだけ少なくし、塗装工程を短縮することが安全性、経済性等の点から強く求められていた。 Anti-corrosion coating is applied to protect steel structures such as bridges, plants and tanks, metal products such as steel plates and steel pipes from the corrosive environment of the outside world, and to provide a function of maintaining aesthetics. For anticorrosion coating of steel structures, for example, at least three or more coating processes combining zinc rich paint, epoxy resin-based undercoating, intermediate coating, and polyurethane resin-based or fluororesin-based overcoating are performed. It is common that In particular, when painting existing steel structures, work is done at high places without scaffolding, and labor costs and scaffolding costs often account for more than 80% of the painting cost. In view of safety and economy, there has been a strong demand for reducing the coating process and shortening the painting process.
例えば、特許文献1には、鋼製構造物の防食と美観維持のために、防食性と耐候性に優れた塗膜を常温でかつ1回の塗装工程でも形成しうる塗料組成物を提供することを目的とした、アクリル樹脂、1分子中に少なくとも2つのエポキシ基を有するエポキシ樹脂、アミノシランを含み得るアミン硬化剤、及び硬化触媒を含む塗料組成物が開示されている。 For example, Patent Document 1 provides a coating composition that can form a coating film excellent in corrosion resistance and weather resistance at room temperature and in a single coating process in order to prevent corrosion and maintain aesthetics of a steel structure. To this end, a coating composition is disclosed that includes an acrylic resin, an epoxy resin having at least two epoxy groups in a molecule, an amine curing agent that can include aminosilane, and a curing catalyst.
特許文献1に記載の塗料組成物により得られる硬化塗膜は、1回の塗装仕上げで形成され、そして優れた防食性及び耐候性を有するので、1回の塗装で長期間に渡り鋼製構造物等の美観を維持できる。 The cured coating film obtained by the coating composition described in Patent Document 1 is formed by a single coating finish, and has excellent corrosion resistance and weather resistance. You can maintain the beauty of things.
一方、近年、重防食塗装においても、長期のメンテナンスコスト削減を指向して、上塗り塗料としてフッ素樹脂系塗料が使用されるケースが増加している。
例えば、特許文献2には、防錆性及び耐候性を長期間保持し、任意の着色を可能にした、省工程の耐候性鋼の防食法を提供することを目的とした、加水分解性シリル基を有するフッ素樹脂等、オルガノシラン又はその部分加水分解縮合物、無公害防錆顔料、及び着色剤を含有する着色有機無機複合上塗り塗料と、当該上塗り塗料を用いた耐候性鋼の防食法が記載されている。On the other hand, in recent years, even in heavy anticorrosion coatings, there are increasing cases in which fluororesin-based paints are used as top coats in order to reduce long-term maintenance costs.
For example, Patent Document 2 discloses a hydrolyzable silyl compound that aims to provide an anticorrosion method for a weather-resistant steel with a reduced number of processes that retains rust resistance and weather resistance for a long period of time and enables arbitrary coloring. A colored organic-inorganic composite topcoat containing a fluororesin having a group, organosilane or a partially hydrolyzed condensate thereof, a pollution-free rust preventive pigment, and a colorant, and a corrosion-resistant method for weathering steel using the topcoat Have been described.
ところで、近年、環境調和、住民の健康等への配慮が強く求められ、また、安全問題としても、消防法、労働安全衛生法、PL法等に配慮し、危険性のより少ない塗料が求められている。
また、近年、新設される構造物が減少し、既設の構造物に対する塗り替え市場が拡がっており、塗り替え時の塗り重ね不良、例えば、チヂミが生じにくい塗料が求められている。従って、塗装環境が良好で且つ塗り重ね性に優れる、溶解性の高すぎない溶剤を含む塗料、いわゆる、弱溶剤系塗料の開発が活発に行われている。By the way, in recent years, there has been a strong demand for environmental harmony and the health of residents, and as a safety issue, paints with less danger are demanded in consideration of the Fire Service Law, Industrial Safety and Health Law, PL Law, etc. ing.
In recent years, the number of newly installed structures has decreased, and the market for repainting existing structures has expanded, and there is a need for paints that are less prone to coating defects during repainting, for example, blemishes. Therefore, development of paints containing a solvent having a good coating environment and excellent recognizability and not too high solubility, that is, so-called weak solvent paints, has been actively conducted.
例えば、特許文献3には、所定の水酸基含有フッ素樹脂、ポリイソシアネート、弱溶剤及び所定の水酸基含有アクリル樹脂を含み、塗料樹脂固形分における、フッ素原子含有量が2〜25質量%、水酸基価が20〜60mgKOH/gである弱溶剤型フッ素樹脂系塗料組成物が開示されている。 For example, Patent Document 3 includes a predetermined hydroxyl group-containing fluororesin, polyisocyanate, weak solvent, and a predetermined hydroxyl group-containing acrylic resin, and the fluorine atom content in the coating resin solid content is 2 to 25% by mass and the hydroxyl value is A weak solvent type fluororesin-based coating composition that is 20 to 60 mg KOH / g is disclosed.
しかし、特許文献2及び3に記載された塗料組成物は、鋼製構造物等の長期耐候性に影響を与えうる厚膜塗装性が不十分であった。
従って、本発明は、厚膜塗装性に優れ、そして長期耐候性に優れた塗膜を形成することができる耐候性塗料組成物を提供することを目的とする。However, the coating compositions described in Patent Documents 2 and 3 have insufficient thick film coatability that can affect long-term weather resistance of steel structures and the like.
Accordingly, an object of the present invention is to provide a weather-resistant coating composition that can form a coating film that is excellent in thick film paintability and excellent in long-term weather resistance.
本発明者らは、鋭意検討した結果、加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)を含む耐候性塗料組成物を見出した。 As a result of intensive studies, the inventors of the present invention have weather resistance including a hydrolyzable silyl group-containing fluororesin (A), a hydrolyzable silyl group-containing acrylic resin (B), and a hydrolyzable silyl group-containing silicone resin (C). A coating composition was found.
本発明の耐候性塗料組成物は、厚膜塗装性に優れ、そして長期耐候性に優れた塗膜を形成することができる。 The weather-resistant coating composition of the present invention can form a coating film excellent in thick film paintability and excellent in long-term weather resistance.
本発明の耐候性塗料組成物は、加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)を含んでなる。 The weather resistant coating composition of the present invention comprises a hydrolyzable silyl group-containing fluororesin (A), a hydrolyzable silyl group-containing acrylic resin (B), and a hydrolyzable silyl group-containing silicone resin (C).
≪加水分解性シリル基含有フッ素樹脂(A)≫
加水分解性シリル基含有フッ素樹脂(A)は、分子中に、加水分解性シリル基と、フッ素含有オレフィン単位とを有する樹脂である。加水分解性シリル基含有フッ素樹脂(A)は、加水分解性シリル基含有フッ素樹脂(A)の固形分質量に基づいて、フッ素含有オレフィン単位を、好ましくは約1質量%以上含み、より好ましくは約5質量%以上含み、さらに好ましくは約10質量%以上含み、そしてさらに好ましくは約15質量%以上含む。≪Hydrolyzable silyl group-containing fluororesin (A) ≫
The hydrolyzable silyl group-containing fluororesin (A) is a resin having a hydrolyzable silyl group and a fluorine-containing olefin unit in the molecule. The hydrolyzable silyl group-containing fluororesin (A) preferably contains about 1% by mass or more of fluorine-containing olefin units, more preferably, based on the solid content mass of the hydrolyzable silyl group-containing fluororesin (A). It contains about 5% by weight or more, more preferably about 10% by weight or more, and more preferably about 15% by weight or more.
本明細書において、「加水分解性シリル基」は、加水分解によりシラノール基を生成し、当該シラノール基が脱水縮合して、シロキサン結合を形成する基であり、ケイ素原子に直接結合した一価の加水分解性原子(水と反応することでシラノール基を生成する原子)及びケイ素原子に直接結合した一価の加水分解性基(水と反応することでシラノール基を生成する基)の両方又は一方を有するシリル基である限り特に限定されない。上記加水分解性シリル基の具体例としては、例えば、クロロシリル基、ブロモシリル基等のハロゲン化シリル基、メトキシシリル基、エトキシシリル基、プロポキシシリル基、ブトキシシリル基等のアルコキシシリル基等、並びにそれらの任意の組み合わせが挙げられる。 In the present specification, the “hydrolyzable silyl group” is a group that forms a silanol group by hydrolysis, which undergoes dehydration condensation to form a siloxane bond, and is a monovalent bond directly bonded to a silicon atom. Either or both of hydrolyzable atoms (atoms that generate silanol groups by reacting with water) and monovalent hydrolyzable groups directly bonded to silicon atoms (groups that generate silanol groups by reacting with water) As long as it is a silyl group having, there is no particular limitation. Specific examples of the hydrolyzable silyl group include, for example, halogenated silyl groups such as chlorosilyl group and bromosilyl group, alkoxysilyl groups such as methoxysilyl group, ethoxysilyl group, propoxysilyl group, butoxysilyl group, and the like. Any combination of these is mentioned.
加水分解性シリル基含有フッ素樹脂(A)は、加水分解性シリル基と、フッ素含有オレフィン単位とを有する限り、構造は特に限定されず、任意の方法により製造されたものが挙げられ、そして市販されている。 The structure of the hydrolyzable silyl group-containing fluororesin (A) is not particularly limited as long as it has a hydrolyzable silyl group and a fluorine-containing olefin unit, and examples thereof include those produced by any method, and are commercially available. Has been.
例えば、加水分解性シリル基含有フッ素樹脂(A)は、フッ素含有オレフィン(a1)、所望によるフッ素含有重合性不飽和化合物(a2)、加水分解性シリル基含有重合性不飽和化合物(a3)、及び所望によるその他の重合性不飽和化合物(a4)の単量体単位を含むができる。For example, the hydrolyzable silyl group-containing fluororesin (A) comprises a fluorine-containing olefin (a 1 ), an optional fluorine-containing polymerizable unsaturated compound (a 2 ), a hydrolyzable silyl group-containing polymerizable unsaturated compound (a 3 ), and optionally other monomeric units of the polymerizable unsaturated compound (a 4 ).
フッ素含有オレフィン(a1)としては、例えば、フッ化ビニリデン、トリフルオロエチレン、テトラフルオロエチレン、ブロモトリフルオロエチレン、クロロトリフルオロエチレン、ペンタフルオロプロピレン、ヘキサフルオロプロピレン等が挙げられる。Examples of the fluorine-containing olefin (a 1 ) include vinylidene fluoride, trifluoroethylene, tetrafluoroethylene, bromotrifluoroethylene, chlorotrifluoroethylene, pentafluoropropylene, and hexafluoropropylene.
所望によるフッ素含有重合性不飽和化合物(a2)としては、フルオロアルキルトリフルオロビニルエーテル、パーフルオロアルキルトリフルオロビニルエーテル等のフルオロビニルエーテル;ヘキサフルオロイソプロピル(メタ)アクリレート、パーフルオロオクチルメチル(メタ)アクリレート、パーフルオロオクチルエチル(メタ)アクリレート等のフルオロアルキル(メタ)アクリレート等;並びにこれらの任意の組み合わせが挙げられる。
なお、本明細書において、(メタ)アクリレートは、アクリレート及びメタクリレート、あるいはアクリレート又はメタクリレートを意味する。Examples of the fluorine-containing polymerizable unsaturated compound (a 2 ) optionally include fluoroalkyl ethers such as fluoroalkyl trifluorovinyl ether and perfluoroalkyl trifluorovinyl ether; hexafluoroisopropyl (meth) acrylate, perfluorooctylmethyl (meth) acrylate, And fluoroalkyl (meth) acrylates such as perfluorooctylethyl (meth) acrylate; and any combination thereof.
In the present specification, (meth) acrylate means acrylate and methacrylate, or acrylate or methacrylate.
加水分解性シリル基含有重合性不飽和化合物(a3)としては、例えば、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ジビニルジメトキシシラン、ジビニルジエトキシシラン、ビニルメチルジメトキシシラン、ビニルメチルジエトキシシラン、ビニルトリス(メトキシエトキシ)シラン等のビニルアルコキシシラン(a31);ビニルトリクロロシラン、ジビニルジクロロシラン、ビニルメチルジクロロシラン等のビニルクロロシラン;γ−(メタ)アクリロキシプロピルトリメトキシシラン、γ−(メタ)アクリロキシプロピルトリエトキシシラン、β−(メタ)アクリロキシエチルトリメトキシシラン、β−(メタ)アクリロキシエチルトリエトキシシラン、γ−(メタ)アクリロキシプロピルメチルジメトキシシラン、γ−(メタ)アクリロキシプロピルメチルジエトキシシラン、γ−(メタ)アクリロキシプロピルメチルジプロポキシシラン、γ−(メタ)アクリロキシブチルフェニルジメトキシシラン、γ−(メタ)アクリロキシプロピルジエチルメトキシシラン等の(メタ)アクリロキシアルコキシシラン等;並びにそれらの任意の組み合わせが挙げられる。
なお、本明細書において、(メタ)アクリロキシ基は、アクリロキシ基及びメタクリロキシ基、あるいはアクリロキシ基又はメタクリロキシ基を意味する。Examples of the hydrolyzable silyl group-containing polymerizable unsaturated compound (a 3 ) include vinyltrimethoxysilane, vinyltriethoxysilane, divinyldimethoxysilane, divinyldiethoxysilane, vinylmethyldimethoxysilane, vinylmethyldiethoxysilane, Vinylalkoxysilanes (a 31 ) such as vinyltris (methoxyethoxy) silane; Vinylchlorosilanes such as vinyltrichlorosilane, divinyldichlorosilane, vinylmethyldichlorosilane; γ- (meth) acryloxypropyltrimethoxysilane, γ- (meth) Acryloxypropyltriethoxysilane, β- (meth) acryloxyethyltrimethoxysilane, β- (meth) acryloxyethyltriethoxysilane, γ- (meth) acryloxypropylmethyldimethoxysilane, γ- (me (G) Acryloxypropylmethyldiethoxysilane, γ- (meth) acryloxypropylmethyldipropoxysilane, γ- (meth) acryloxybutylphenyldimethoxysilane, γ- (meth) acryloxypropyldiethylmethoxysilane, etc. ) Acryloxyalkoxysilane and the like; and any combination thereof.
In the present specification, the (meth) acryloxy group means an acryloxy group and a methacryloxy group, or an acryloxy group or a methacryloxy group.
加水分解性シリル基含有重合性不飽和化合物(a3)は、ビニルアルコキシシラン(a31)、すなわち、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ジビニルジメトキシシラン、ジビニルジエトキシシラン、ビニルメチルジメトキシシラン、ビニルメチルジエトキシシラン、ビニルトリス(メトキシエトキシ)シラン等、並びにそれらの組み合わせから成る群から選択されることが好ましい。The hydrolyzable silyl group-containing polymerizable unsaturated compound (a 3 ) is vinyl alkoxysilane (a 31 ), that is, vinyltrimethoxysilane, vinyltriethoxysilane, divinyldimethoxysilane, divinyldiethoxysilane, vinylmethyldimethoxysilane. , Vinylmethyldiethoxysilane, vinyltris (methoxyethoxy) silane, and the like, and combinations thereof.
また、所望によるその他の重合性不飽和化合物(a4)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、n−プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、tert−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、n−オクチル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、トリデシル(メタ)アクリレート等の直鎖状、分岐状又は環状アルキル基含有(メタ)アクリレート;N−メトキシメチル(メタ)アクリルアミド、N−ブトキシメチル(メタ)アクリルアミド、メトキシエチル(メタ)アクリレート、メトキシプロピル(メタ)アクリレート、エトキシエチル(メタ)アクリレート、エトキシプロピル(メタ)アクリレート等のアルコキシアルキル(メタ)アクリレート;ポリエチレングリコールモノメトキシ(メタ)アクリレート等のポリアルキレングリコールモノアルコキシ(メタ)アクリレート等のアルコキシ基含有(メタ)アクリレート;グリシジル(メタ)アクリレート、3,4−エポキシシクロヘキシルメチル(メタ)アクリレート等のエポキシ基含有(メタ)アクリレート;スチレン、ビニルトルエン等の芳香族ビニル化合物;アクリル酸、メタクリル酸、ヒドロキシアルキル(メタ)アクリレートと酸無水物とのハーフエステル化物等のカルボキシル基含有(メタ)アクリレート;2−アクリルアミド−2−メチルプロパンスルホン酸等のスルホン酸基含有(メタ)アクリレート;アシッドホスホオキシエチル(メタ)アクリレート、リン酸モノ−〔(2−ヒドロキシエチル)(メタ)アクリル酸〕エステル等のリン酸基含有(メタ)アクリレート;N,N−ジメチルアミノエチル(メタ)アクリレート、N,N−ジエチルアミノエチル(メタ)アクリレート、N,N−ジメチルアミノプロピル(メタ)アクリレート、N−t−ブチルアミノエチル(メタ)アクリレート、N,N−ジメチルアミノブチル(メタ)アクリレート等のアミノ基含有(メタ)アクリレート;(メタ)アクリロイルオキシエチルトリメチルアンモニウムクロライド、メタクリル酸ジメチルアミノエチルメチルクロライド等の第4級アンモニウム塩基含有(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、ヒドロキシプロピル(メタ)アクリレート、2,3−ジヒドロキシブチル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート等のヒドロキシアルキル(メタ)アクリレート、上記ヒドロキシアルキル(メタ)アクリレートにε−カプロラクトン等のラクトンを開環重合した化合物、及びポリエチレングリコールモノ(メタ)アクリレート等の多価アルコールとアクリル酸又はメタクリル酸とのモノエステル化物等の水酸基含有(メタ)アクリレート;シクロヘキシルビニルエーテル、ノニルビニルエーテル、2−エチルヘキシルビニルエーテル、ヘキシルビニルエーテル、エチルビニルエーテル、n−ブチルビニルエーテル、t−ブチルビニルエーテル等のビニルエーテル;エチルアリルエーテル、ヘキシルアリルエーテル等のアリルエーテル;「ベオバ−9」、「ベオバ−10」(いずれもシェル化学社製、商品名)等のカルボン酸ビニルエステル;エチレン、プロピレン、イソブチレン等のオレフィン等、並びにそれらの任意の組み合わせが挙げられる。Moreover, as other polymerizable unsaturated compound (a 4 ) as desired, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl ( (Meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) Linear, branched or cyclic alkyl group-containing (meth) acrylates such as acrylate, isobornyl (meth) acrylate, tridecyl (meth) acrylate; N-methoxymethyl (meth) acrylamide, N-butoxymethyl (meth) acrylic Alkoxyalkyl (meth) acrylates such as amide, methoxyethyl (meth) acrylate, methoxypropyl (meth) acrylate, ethoxyethyl (meth) acrylate, ethoxypropyl (meth) acrylate; polyalkylenes such as polyethylene glycol monomethoxy (meth) acrylate Alkoxy group-containing (meth) acrylates such as glycol monoalkoxy (meth) acrylate; Epoxy group-containing (meth) acrylates such as glycidyl (meth) acrylate and 3,4-epoxycyclohexylmethyl (meth) acrylate; Styrene, vinyltoluene and the like Aromatic vinyl compounds; carboxyl group-containing (meth) acrylates such as acrylic acid, methacrylic acid, half-esterified products of hydroxyalkyl (meth) acrylates and acid anhydrides Sulfonic acid group-containing (meth) acrylate such as 2-acrylamido-2-methylpropanesulfonic acid; acid phosphooxyethyl (meth) acrylate, mono-[(2-hydroxyethyl) (meth) acrylic acid] Phosphoric acid group-containing (meth) acrylates such as esters; N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N-dimethylaminopropyl (meth) acrylate, Nt -Amino group-containing (meth) acrylates such as butylaminoethyl (meth) acrylate and N, N-dimethylaminobutyl (meth) acrylate; (meth) acryloyloxyethyltrimethylammonium chloride, dimethylaminoethylmethyl methacrylate methacrylate and the like 4th grade Ammoni Um base-containing (meth) acrylate; hydroxyalkyl (meth) such as 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, 2,3-dihydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate Hydroxyl groups such as acrylates, compounds obtained by ring-opening polymerization of lactones such as ε-caprolactone to the above hydroxyalkyl (meth) acrylates, and monoesterified products of polyhydric alcohols such as polyethylene glycol mono (meth) acrylate and acrylic acid or methacrylic acid Containing (meth) acrylate; cyclohexyl vinyl ether, nonyl vinyl ether, 2-ethylhexyl vinyl ether, hexyl vinyl ether, ethyl vinyl ether, n-butyl vinyl ether, t-butyl vinyl Vinyl ethers such as ruether; allyl ethers such as ethyl allyl ether and hexyl allyl ether; carboxylic acid vinyl esters such as “Beova-9” and “Beova-10” (both manufactured by Shell Chemical Co., Ltd.); ethylene, propylene, Examples include olefins such as isobutylene, and any combination thereof.
その他の重合性不飽和化合物(a4)としては、(メタ)アクリロイル基含有化合物(a41)が好ましい。
なお、本明細書において、「(メタ)アクリロイル」基は、アクリロイル基及びメタクリロイル基、あるいはアクリロイル基又はメタクリロイル基を意味し、そして「(メタ)アクリル酸」は、アクリル酸及びメタクリル酸、あるいはアクリル酸又はメタクリル酸を意味する。As the other polymerizable unsaturated compound (a 4 ), a (meth) acryloyl group-containing compound (a 41 ) is preferable.
In the present specification, “(meth) acryloyl” group means acryloyl group and methacryloyl group, or acryloyl group or methacryloyl group, and “(meth) acrylic acid” means acrylic acid and methacrylic acid, or acrylic. It means acid or methacrylic acid.
(メタ)アクリロイル基含有化合物(a41)の例として、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、tert−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、n−オクチル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、トリデシル(メタ)アクリレート等の直鎖状、分岐状又は環状アルキル基含有(メタ)アクリレート;N−メトキシメチル(メタ)アクリルアミド、N−ブトキシメチル(メタ)アクリルアミド、メトキシエチル(メタ)アクリレート、メトキシプロピル(メタ)アクリレート、エトキシエチル(メタ)アクリレート、エトキシプロピル(メタ)アクリレート等のアルコキシアルキル(メタ)アクリレート;ポリエチレングリコールモノメトキシ(メタ)アクリレート等のポリアルキレングリコールモノアルコキシ(メタ)アクリレート等のアルコキシ基含有(メタ)アクリレート;グリシジル(メタ)アクリレート、3,4−エポキシシクロヘキシルメチル(メタ)アクリレート等のエポキシ基含有(メタ)アクリレート;アクリル酸、メタクリル酸、ヒドロキシアルキル(メタ)アクリレートと酸無水物とのハーフエステル化物等のカルボキシル基含有(メタ)アクリレート;2−アクリルアミド−2−メチルプロパンスルホン酸等のスルホン酸基含有(メタ)アクリレート;アシッドホスホオキシエチル(メタ)アクリレート、リン酸モノ−〔(2−ヒドロキシエチル)(メタ)アクリル酸〕エステル等のリン酸基含有(メタ)アクリレート;N,N−ジメチルアミノエチル(メタ)アクリレート、N,N−ジエチルアミノエチル(メタ)アクリレート、N,N−ジメチルアミノプロピル(メタ)アクリレート、N−t−ブチルアミノエチル(メタ)アクリレート、N,N−ジメチルアミノブチル(メタ)アクリレート等のアミノ基含有(メタ)アクリレート;(メタ)アクリロイルオキシエチルトリメチルアンモニウムクロライド、メタクリル酸ジメチルアミノエチルメチルクロライド等の第4級アンモニウム塩基含有(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、ヒドロキシプロピル(メタ)アクリレート、2,3−ジヒドロキシブチル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート等のヒドロキシアルキル(メタ)アクリレート、上記ヒドロキシアルキル(メタ)アクリレートにε−カプロラクトン等のラクトンを開環重合した化合物、及びポリエチレングリコールモノ(メタ)アクリレート等の多価アルコールとアクリル酸又はメタクリル酸とのモノエステル化物等の水酸基含有(メタ)アクリレート等;並びにそれらの組み合わせが挙げられる。Examples of the (meth) acryloyl group-containing compound (a 41 ) include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (Meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) ) Linear, branched or cyclic alkyl group-containing (meth) acrylates such as acrylate and tridecyl (meth) acrylate; N-methoxymethyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, and methoxy Alkoxyalkyl (meth) acrylates such as siethyl (meth) acrylate, methoxypropyl (meth) acrylate, ethoxyethyl (meth) acrylate, and ethoxypropyl (meth) acrylate; polyalkylene glycol monoalkoxy such as polyethylene glycol monomethoxy (meth) acrylate Alkoxy group-containing (meth) acrylates such as (meth) acrylate; Epoxy group-containing (meth) acrylates such as glycidyl (meth) acrylate and 3,4-epoxycyclohexylmethyl (meth) acrylate; acrylic acid, methacrylic acid, hydroxyalkyl ( Carboxyl group-containing (meth) acrylates such as half esterified products of (meth) acrylates and acid anhydrides; sulfos such as 2-acrylamido-2-methylpropanesulfonic acid Acid group-containing (meth) acrylate; Acid phosphooxyethyl (meth) acrylate, phosphoric acid group-containing (meth) acrylate such as mono-[(2-hydroxyethyl) (meth) acrylic acid] ester; N, N -Dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N-dimethylaminopropyl (meth) acrylate, Nt-butylaminoethyl (meth) acrylate, N, N-dimethylamino Amino group-containing (meth) acrylates such as butyl (meth) acrylate; (meth) acryloyloxyethyltrimethylammonium chloride, quaternary ammonium base-containing (meth) acrylates such as dimethylaminoethylmethyl chloride methacrylate; 2-hydroxyethyl ( Meta) Acrylate, hydroxypropyl (meth) acrylate, 2,3-dihydroxybutyl (meth) acrylate, hydroxyalkyl (meth) acrylate such as 4-hydroxybutyl (meth) acrylate, and the above hydroxyalkyl (meth) acrylate such as ε-caprolactone Examples thereof include a compound obtained by ring-opening polymerization of a lactone, a hydroxyl group-containing (meth) acrylate such as a monoesterified product of a polyhydric alcohol such as polyethylene glycol mono (meth) acrylate and acrylic acid or methacrylic acid; and combinations thereof.
加水分解性シリル基含有フッ素樹脂(A)は、弱溶剤に溶解性を有することが好ましい。
「弱溶剤」は、当技術分野で周知な用語であり、一般的には溶解力の弱い溶剤を意味する。上記弱溶剤には、労働安全衛生法による有機溶剤の分類において、第3種有機溶剤と列挙されるものが含まれる。第3種有機溶剤の例として、ガソリン、灯油、コールタールナフサ(ソルベントナフサを含む)、石油エーテル、石油ナフサ、石油ベンジン、テレピン油、ミネラルスピリット(ミネラルシンナー、ペトロリウムスピリット、ホワイトスピリット及びミネラルターペンを含む)が挙げられる。The hydrolyzable silyl group-containing fluororesin (A) preferably has solubility in a weak solvent.
“Weak solvent” is a well-known term in the art, and generally means a solvent having a weak dissolving power. The weak solvents include those listed as the third type organic solvents in the classification of organic solvents according to the Industrial Safety and Health Act. Examples of Class 3 organic solvents include gasoline, kerosene, coal tar naphtha (including solvent naphtha), petroleum ether, petroleum naphtha, petroleum benzine, turpentine oil, mineral spirit (mineral thinner, petroleum spirit, white spirit and mineral turpentine Are included).
上記弱溶剤は市販品されており、上記弱溶剤の市販品として、例えば、「スワゾール1000」及び「スワゾール1500」(以上、丸善石油株式会社製)、「ソルベッソ150」、「ソルベッソ200」、「HAWS」及び「LAWS」(以上、シェルジャパン社製)、「エッソナフサNo.6」及び「エクソールD30」(商品名、エクソンモービル化学社製)、「ペガゾール3040」(商品名、エクソンモービル化学社製)、「Aソルベント」、「クレンゾル」及び「イプゾール100」(出光興産株式会社製)、「ミネラルスピリットA」、「ハイアロム2S」及び「ハイアロム2S」(以上、新日本石油化学株式会社製)、「リニアレン10」及び「リニアレン12」(以上、出光石油化学株式会社製)、「リカソルブ900」、「リカソルブ910B」及び「リカソルブ1000」(以上、新日本理化株式会社製)等が挙げられる。 The weak solvent is a commercially available product. For example, “Swazole 1000” and “Swazole 1500” (manufactured by Maruzen Petroleum Co., Ltd.), “Solvesso 150”, “Solvesso 200”, “ “HAWS” and “LAWS” (manufactured by Shell Japan Co., Ltd.), “Essonaphtha No. 6” and “Exor D30” (trade name, manufactured by ExxonMobil Chemical Co., Ltd.), “Pegasol 3040” (trade name, manufactured by ExxonMobil Chemical Co., Ltd.) ), “A Solvent”, “Clensol” and “Ipsol 100” (manufactured by Idemitsu Kosan Co., Ltd.), “Mineral Spirit A”, “High Alom 2S” and “High Alom 2S” (above, Shin Nippon Petrochemical Co., Ltd.), “Linearene 10” and “Linearene 12” (made by Idemitsu Petrochemical Co., Ltd.), “Ricasolve 900” "Rikasorubu 910B" and "Rikasorubu 1000" (or more, New Japan Chemical Co., Ltd.), and the like.
加水分解性シリル基含有フッ素樹脂(A)は、上記弱溶剤の存在下、又は上記弱溶剤及びそれ以外のその他の有機溶剤の存在下で、上述の単量体を重合することにより製造することができる。上記その他の有機溶剤としては、公知の溶剤、例えば、n−ブタン、n−ヘキサン、n−ヘプタン、n−オクタン、シクロペンタン、シクロヘキサン、シクロブタン等の炭化水素溶剤;トルエン、キシレン等の芳香族系溶剤;メチルイソブチルケトン等のケトン系溶剤;n−ブチルエーテル、ジオキサン、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコール等のエーテル系溶剤;酢酸エチル、酢酸n−ブチル、酢酸イソブチル、エチレングリコールモノメチルエーテルアセテート、ブチルカルビトールアセテート等のエステル系溶剤;メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン等のケトン系溶剤;エタノール、イソプロパノール、n−ブタノール、sec−ブタノール、イソブタノール等のアルコール系溶剤等;並びにそれらの組み合わせが挙げられる。 The hydrolyzable silyl group-containing fluororesin (A) is produced by polymerizing the above monomer in the presence of the weak solvent or in the presence of the weak solvent and other organic solvents other than the weak solvent. Can do. Examples of the other organic solvents include known solvents, for example, hydrocarbon solvents such as n-butane, n-hexane, n-heptane, n-octane, cyclopentane, cyclohexane, cyclobutane; and aromatic solvents such as toluene and xylene. Solvents; ketone solvents such as methyl isobutyl ketone; ether solvents such as n-butyl ether, dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol; ethyl acetate, acetic acid Esters such as n-butyl, isobutyl acetate, ethylene glycol monomethyl ether acetate, butyl carbitol acetate; methyl ethyl ketone, methyl isobutyl ketone, diisobutyl keto Ketone solvents and the like; ethanol, isopropanol, n- butanol, sec- butanol, alcohol solvents such as isobutanol; and combinations thereof.
加水分解性シリル基含有フッ素樹脂(A)の不揮発性成分の重量平均分子量は、特に制限されるものではないが、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)との相溶性、長期耐候性、並びに弱溶剤への溶解性の観点から、一般的に約2,000〜約200,000の範囲にあり、そして好ましくは約3,000〜約60,000の範囲にある。 Although the weight average molecular weight of the non-volatile component of the hydrolyzable silyl group-containing fluororesin (A) is not particularly limited, the hydrolyzable silyl group-containing acrylic resin (B) and the hydrolyzable silyl group-containing silicone resin From the viewpoint of compatibility with (C), long-term weather resistance, and solubility in weak solvents, it is generally in the range of about 2,000 to about 200,000, and preferably about 3,000 to about 60. In the range of 1,000.
なお、本明細書において、重量平均分子量は、ゲルパーミエーションクロマトグラフ(GPC)を用いて測定した保持時間(保持容量)を、同一条件で測定した分子量既知の標準ポリスチレンの保持時間(保持容量)によりポリスチレンの分子量に換算して求めた値である。 In this specification, the weight average molecular weight is the retention time (retention capacity) of a standard polystyrene having a known molecular weight measured under the same conditions as the retention time (retention capacity) measured using a gel permeation chromatograph (GPC). Is a value obtained by converting to a molecular weight of polystyrene.
上記重量平均分子量は、例えば、ゲルパーミエーションクロマトグラフ装置として、「HLC8120GPC」(商品名、東ソー社製)を使用し、カラムとして、「TSKgel G−4000HXL」、「TSKgel G−3000HXL」、「TSKgel G−2500HXL」及び「TSKgel G−2000HXL」(商品名、いずれも東ソー社製)の4本を使用し、検出器として、示差屈折率計を使用し、移動相:テトラヒドロフラン、測定温度:40℃、流速:1mL/minの条件下で測定することができる。 The weight average molecular weight is, for example, using “HLC8120GPC” (trade name, manufactured by Tosoh Corporation) as a gel permeation chromatograph apparatus, and “TSKgel G-4000HXL”, “TSKgel G-3000HXL”, “TSKgel” as columns. G-2500HXL ”and“ TSKgel G-2000HXL ”(trade names, both manufactured by Tosoh Corporation) were used, a differential refractometer was used as a detector, mobile phase: tetrahydrofuran, measurement temperature: 40 ° C. The flow rate can be measured under the condition of 1 mL / min.
≪加水分解性シリル基含有アクリル樹脂(B)≫
加水分解性シリル基含有アクリル樹脂(B)は、樹脂中に、加水分解性シリル基と、(メタ)アクリロイル基に由来する基とを有するアクリル系共重合体である。
なお、加水分解性シリル基含有アクリル樹脂(B)は、加水分解性シリル基含有アクリル樹脂(B)の固形分質量に基づいて、フッ素含有オレフィン単位を、好ましくは約15質量%以下含み、より好ましくは約10質量%以下含み、さらに好ましくは約5質量%以下含み、さらに好ましくは約1質量%以下含み、そしてさらに好ましくはフッ素含有オレフィン単位を含まない。≪Hydrolysable silyl group-containing acrylic resin (B) ≫
The hydrolyzable silyl group-containing acrylic resin (B) is an acrylic copolymer having a hydrolyzable silyl group and a group derived from a (meth) acryloyl group in the resin.
The hydrolyzable silyl group-containing acrylic resin (B) preferably contains about 15% by mass or less of fluorine-containing olefin units based on the solid content mass of the hydrolyzable silyl group-containing acrylic resin (B). Preferably, it contains about 10% by weight or less, more preferably about 5% by weight or less, more preferably about 1% by weight or less, and more preferably no fluorine-containing olefin units.
加水分解性シリル基含有アクリル樹脂(B)の例としては、加水分解性シリル基含有重合性不飽和化合物(b1)と、(メタ)アクリロイル基含有化合物(b2)との単量体単位を含むものが挙げられる。Examples of the hydrolyzable silyl group-containing acrylic resin (B) include monomer units of a hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) and a (meth) acryloyl group-containing compound (b 2 ). The thing containing is mentioned.
加水分解性シリル基含有アクリル樹脂(B)が加水分解性シリル基含有重合性不飽和化合物(b1)及び(メタ)アクリロイル基含有化合物(b2)の単量体単位を含む実施形態では、加水分解性シリル基含有アクリル樹脂(B)は、全単量体単位を基準として、加水分解性シリル基含有重合性不飽和化合物(b1)及び(メタ)アクリロイル基含有化合物(b2)を、単量体単位として、それぞれ、好ましくは約1〜約50質量%及び約50〜約99質量%、より好ましくは約2〜約30質量%及び約70〜約98質量%、さらに好ましくは約3〜約20質量%及び約80〜約97質量%含む。耐候性塗料組成物の貯蔵安定性、並びに形成される塗膜の硬化性及び塗膜物性の観点からである。In the embodiment in which the hydrolyzable silyl group-containing acrylic resin (B) includes monomer units of the hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) and the (meth) acryloyl group-containing compound (b 2 ), The hydrolyzable silyl group-containing acrylic resin (B) comprises a hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) and a (meth) acryloyl group-containing compound (b 2 ) on the basis of all monomer units. The monomer units are preferably about 1 to about 50% by weight and about 50 to about 99% by weight, more preferably about 2 to about 30% by weight and about 70 to about 98% by weight, respectively, more preferably about 3 to about 20% by weight and about 80 to about 97% by weight. This is from the viewpoint of the storage stability of the weather-resistant coating composition, the curability of the formed coating film and the physical properties of the coating film.
加水分解性シリル基含有アクリル樹脂(B)は、任意の公知の方法、例えば、アゾ化合物、過酸化物等を開始剤に用いたラジカル重合法等により製造することができ、また、市販されている。 The hydrolyzable silyl group-containing acrylic resin (B) can be produced by any known method, for example, a radical polymerization method using an azo compound, a peroxide, or the like as an initiator, and is commercially available. Yes.
加水分解性シリル基含有重合性不飽和化合物(b1)としては、「加水分解性シリル基含有フッ素樹脂(A)」における加水分解性シリル基含有重合性不飽和化合物(a3)に記載されるものが挙げられる。
(メタ)アクリロイル基含有化合物(b2)としては、「加水分解性シリル基含有フッ素樹脂(A)」における(メタ)アクリロイル基含有化合物(a41)と同一の化合物、及びヘキサフルオロイソプロピル(メタ)アクリレート、パーフルオロオクチルメチル(メタ)アクリレート、パーフルオロオクチルエチル(メタ)アクリレート等のフルオロアルキル(メタ)アクリレート等;並びにこれらの任意の組み合わせが挙げられる。The hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) is described in the hydrolyzable silyl group-containing polymerizable unsaturated compound (a 3 ) in the “hydrolyzable silyl group-containing fluororesin (A)”. Can be mentioned.
As the (meth) acryloyl group-containing compound (b 2 ), the same compound as the (meth) acryloyl group-containing compound (a 41 ) in “hydrolyzable silyl group-containing fluororesin (A)”, and hexafluoroisopropyl (meta ) Acrylate, perfluorooctylmethyl (meth) acrylate, fluoroalkyl (meth) acrylate such as perfluorooctylethyl (meth) acrylate, and the like; and any combination thereof.
なお、加水分解性シリル基含有アクリル樹脂(B)は、当然ながら、加水分解性シリル基含有重合性不飽和化合物(b1)の単量体単位として、加水分解性シリル基と、(メタ)アクリロイル基とを有する重合性不飽和化合物、例えば、(メタ)アクリロキシアルコキシシラン、例えば、γ−(メタ)アクリロキシプロピルトリメトキシシラン、γ−(メタ)アクリロキシプロピルトリエトキシシラン、β−(メタ)アクリロキシエチルトリメトキシシラン、β−(メタ)アクリロキシエチルトリエトキシシラン、γ−(メタ)アクリロキシプロピルメチルジメトキシシラン、γ−(メタ)アクリロキシプロピルメチルジエトキシシラン、γ−(メタ)アクリロキシプロピルメチルジプロポキシシラン、γ−(メタ)アクリロキシブチルフェニルジメトキシシラン、γ−(メタ)アクリロキシプロピルジエチルメトキシシラン等の単量体単位を含むことができる。The hydrolyzable silyl group-containing acrylic resin (B) is, as a matter of course, a hydrolyzable silyl group and (meth) as a monomer unit of the hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ). A polymerizable unsaturated compound having an acryloyl group, for example, (meth) acryloxyalkoxysilane, for example, γ- (meth) acryloxypropyltrimethoxysilane, γ- (meth) acryloxypropyltriethoxysilane, β- ( (Meth) acryloxyethyltrimethoxysilane, β- (meth) acryloxyethyltriethoxysilane, γ- (meth) acryloxypropylmethyldimethoxysilane, γ- (meth) acryloxypropylmethyldiethoxysilane, γ- (meth) ) Acryloxypropylmethyldipropoxysilane, γ- (meth) acryloxybutylphenyldi Monomer units such as methoxysilane and γ- (meth) acryloxypropyldiethylmethoxysilane can be included.
加水分解性シリル基含有アクリル樹脂(B)は、形成される塗膜の耐候性の観点から、(メタ)アクリロイル基含有化合物(b2)としてメタクリロイル基含有化合物(b21)を含むことが好ましい。
(メタ)アクリロイル基含有化合物(b2)がメタクリロイル基含有化合物(b21)である実施形態では、加水分解性シリル基含有アクリル樹脂(B)は、加水分解性シリル基含有アクリル樹脂(B)の固形分質量に基づいて、メタクリロイル基含有化合物(b21)の単位を、好ましくは約50質量%以上、そしてより好ましくは70質量%以上有することが、形成される塗膜の耐候性の観点から望ましい。The hydrolyzable silyl group-containing acrylic resin (B) preferably contains a methacryloyl group-containing compound (b 21 ) as the (meth) acryloyl group-containing compound (b 2 ) from the viewpoint of the weather resistance of the coating film to be formed. .
In an embodiment in which the (meth) acryloyl group-containing compound (b 2 ) is a methacryloyl group-containing compound (b 21 ), the hydrolyzable silyl group-containing acrylic resin (B) is a hydrolyzable silyl group-containing acrylic resin (B). From the viewpoint of the weather resistance of the coating film to be formed, the unit of the methacryloyl group-containing compound (b 21 ) is preferably about 50% by mass or more and more preferably 70% by mass or more based on the solid content mass of Is desirable.
メタクリロイル基含有化合物(b21)としては、加水分解性シリル基含有重合性不飽和化合物(b1)及び(メタ)アクリロイル基含有化合物(b2)で例示された化合物のうちメタクリロイル基を含有する化合物を挙げることができ、例えば、γ−メタクリロキシプロピルトリメトキシシラン、γ−メタクリロキシプロピルトリエトキシシラン、β−メタクリロキシエチルトリメトキシシラン、β−メタクリロキシエチルトリエトキシシラン、γ−メタクリロキシプロピルメチルジメトキシシラン、γ−メタクリロキシプロピルメチルジエトキシシラン、γ−メタクリロキシプロピルメチルジプロポキシシラン、γ−メタクリロキシブチルフェニルジメトキシシラン、γ−メタクリロキシプロピルジエチルメトキシシラン等のメタクリロキシアルコキシシラン;メチルメタクリレート、エチルメタクリレート、n−プロピルメタクリレート、イソプロピルメタクリレート、n−ブチルメタクリレート、イソブチルメタクリレート、tert−ブチルメタクリレート、2−エチルヘキシルメタクリレート、n−オクチルメタクリレート、ラウリルメタクリレート、ステアリルメタクリレート、シクロヘキシルメタクリレート、イソボルニルメタクリレート、トリデシルメタクリレート等の直鎖状、分岐状又は環状アルキル基含有メタクリレート;メトキシエチルメタクリレート、メトキシプロピルメタクリレート、エトキシエチルメタクリレート、エトキシプロピルメタクリレート等のアルコキシアルキルメタクリレート;2−ヒドロキシエチルメタクリレート、ヒドロキシプロピルメタクリレート、2,3−ジヒドロキシブチルメタクリレート、4−ヒドロキシブチルメタクリレート等のヒドロキシアルキルメタクリレート;アシッドホスホオキシエチルメタクリレート、リン酸モノ−[(2−ヒドロキシエチル)メタクリル酸]エステル等のリン酸基含有メタクリレート;メタクリル酸などのカルボキシル基含有メタクリレート;並びにそれらの組み合わせが挙げられる。The methacryloyl group-containing compound (b 21 ) contains a methacryloyl group among the compounds exemplified by the hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) and the (meth) acryloyl group-containing compound (b 2 ). For example, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropyltriethoxysilane, β-methacryloxyethyltrimethoxysilane, β-methacryloxyethyltriethoxysilane, γ-methacryloxypropyl Methacryloxy such as methyldimethoxysilane, γ-methacryloxypropylmethyldiethoxysilane, γ-methacryloxypropylmethyldipropoxysilane, γ-methacryloxybutylphenyldimethoxysilane, γ-methacryloxypropyldiethylmethoxysilane Coxysilane; methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, n-octyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, isobol Linear, branched or cyclic alkyl group-containing methacrylates such as nyl methacrylate and tridecyl methacrylate; alkoxyalkyl methacrylates such as methoxyethyl methacrylate, methoxypropyl methacrylate, ethoxyethyl methacrylate and ethoxypropyl methacrylate; 2-hydroxyethyl methacrylate and hydroxypropyl Meta Hydroxyalkyl methacrylates such as relate, 2,3-dihydroxybutyl methacrylate and 4-hydroxybutyl methacrylate; phosphate group-containing methacrylates such as acid phosphooxyethyl methacrylate and phosphoric acid mono-[(2-hydroxyethyl) methacrylic acid] ester; And carboxyl group-containing methacrylates such as methacrylic acid; and combinations thereof.
加水分解性シリル基含有アクリル樹脂(B)が加水分解性シリル基含有重合性不飽和化合物(b1)及び(メタ)アクリロイル基含有化合物(b2)の単量体単位を含む実施形態では、(メタ)アクリロイル基含有化合物(b2)が、(メタ)アクリル酸の、炭素数が約4〜18の直鎖状、分岐状又は環状アルキルエステル(b22)を含むことが好ましい。加水分解性シリル基含有アクリル樹脂(B)の弱溶剤に対する溶解性が向上し、加水分解性シリル基含有フッ素樹脂(A)及び加水分解性シリル基含有アクリル樹脂(B)との相溶性が向上し、そして形成される塗膜の耐候性が向上するためである。In the embodiment in which the hydrolyzable silyl group-containing acrylic resin (B) includes monomer units of the hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) and the (meth) acryloyl group-containing compound (b 2 ), The (meth) acryloyl group-containing compound (b 2 ) preferably contains a linear, branched or cyclic alkyl ester (b 22 ) of (meth) acrylic acid having about 4 to 18 carbon atoms. Improved solubility of hydrolyzable silyl group-containing acrylic resin (B) in weak solvents and improved compatibility with hydrolyzable silyl group-containing fluororesin (A) and hydrolyzable silyl group-containing acrylic resin (B) This is because the weather resistance of the formed coating film is improved.
(メタ)アクリル酸の、炭素数が約4〜18の直鎖状、分岐状又は環状アルキルエステル(b22)の例として、n−ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、tert−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、n−オクチル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、トリデシル(メタ)アクリレート等、並びにそれらの組み合わせが挙げられる。(Meth) acrylic acid, carbon atoms approximately 4-18 linear, examples of branched or cyclic alkyl ester (b 22), n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert- butyl (Meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tridecyl (meth) acrylate And combinations thereof.
また、(メタ)アクリロイル基含有化合物(b2)には、(メタ)アクリル酸のヒドロキシアルキルエステルが含まれる。上記(メタ)アクリル酸のヒドロキシアルキルエステルの例として、2−ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、2,3−ジヒドロキシブチル(メタ)アクリレート、4−ヒドロキシブチル(メタ)アクリレート等の(メタ)アクリル酸のヒドロキシアルキルエステル、当該ヒドロキシアルキルエステルにε−カプロラクトン等のラクトンを開環重合した化合物、及びポリエチレングリコールモノ(メタ)アクリレート等の多価アルコールと(メタ)アクリル酸とのモノエステル化物等、並びにそれらの組み合わせが挙げられ、2−ヒドロキシエチルメタクリレートが好ましい。2−ヒドロキシエチル(メタ)アクリレートは、形成される塗膜の光沢を高くする観点から好ましい。Further, the (meth) acryloyl group-containing compound (b 2 ) includes a hydroxyalkyl ester of (meth) acrylic acid. Examples of hydroxyalkyl esters of (meth) acrylic acid include 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, 2,3-dihydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and the like (Meth) acrylic acid hydroxyalkyl ester, a compound obtained by ring-opening polymerization of a lactone such as ε-caprolactone to the hydroxyalkyl ester, and a polyhydric alcohol such as polyethylene glycol mono (meth) acrylate and (meth) acrylic acid Examples thereof include monoesterified products and the like, and combinations thereof, and 2-hydroxyethyl methacrylate is preferable. 2-hydroxyethyl (meth) acrylate is preferable from the viewpoint of increasing the gloss of the coating film to be formed.
加水分解性シリル基含有アクリル樹脂(B)が(メタ)アクリル酸のヒドロキシアルキルエステルを含む実施形態では、加水分解性シリル基含有アクリル樹脂(B)が、全単量体単位を基準として、(メタ)アクリル酸のヒドロキシアルキルエステルを、好ましくは約0.1〜40質量%、そしてより好ましくは1〜20質量%含む。形成される塗膜の光沢と、弱溶剤への溶解性の観点からである。 In the embodiment in which the hydrolyzable silyl group-containing acrylic resin (B) includes a hydroxyalkyl ester of (meth) acrylic acid, the hydrolyzable silyl group-containing acrylic resin (B) is based on the total monomer unit ( The hydroxyalkyl ester of meth) acrylic acid is preferably contained in an amount of about 0.1 to 40% by weight, and more preferably 1 to 20% by weight. This is from the viewpoint of the gloss of the formed coating film and the solubility in a weak solvent.
本発明の別の実施形態に従う耐候性塗料組成物では、加水分解性シリル基含有アクリル樹脂(B)が、加水分解性シリル基含有重合性不飽和化合物(b1)と、(メタ)アクリロイル基含有化合物(b2)と、その他の重合性不飽和化合物(b3)との単量体単位を含む。In the weather resistant coating composition according to another embodiment of the present invention, the hydrolyzable silyl group-containing acrylic resin (B) comprises a hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) and a (meth) acryloyl group. It contains monomer units of the containing compound (b 2 ) and other polymerizable unsaturated compounds (b 3 ).
その他の重合性不飽和化合物(b3)としては、加水分解性シリル基含有フッ素樹脂(A)において、その他の重合性不飽和化合物(a4)として列挙したものから(メタ)アクリロイル基含有化合物(b2)を除いたもの、例えば、スチレン、ビニルトルエン等の芳香族ビニル化合物;シクロヘキシルビニルエーテル、ノニルビニルエーテル、2−エチルヘキシルビニルエーテル、ヘキシルビニルエーテル、エチルビニルエーテル、n−ブチルビニルエーテル、t−ブチルビニルエーテル等のビニルエーテル;エチルアリルエーテル、ヘキシルアリルエーテル等のアリルエーテル;「ベオバ−9」、「ベオバ−10」(いずれもシェル化学社製、商品名)等のカルボン酸ビニルエステル;エチレン、プロピレン、イソブチレン等のオレフィン等が挙げられる。As other polymerizable unsaturated compound (b 3 ), those listed as other polymerizable unsaturated compounds (a 4 ) in hydrolyzable silyl group-containing fluororesin (A), (meth) acryloyl group-containing compounds Excluding (b 2 ), for example, aromatic vinyl compounds such as styrene and vinyl toluene; cyclohexyl vinyl ether, nonyl vinyl ether, 2-ethylhexyl vinyl ether, hexyl vinyl ether, ethyl vinyl ether, n-butyl vinyl ether, t-butyl vinyl ether, etc. Vinyl ethers; allyl ethers such as ethyl allyl ether, hexyl allyl ether; carboxylic acid vinyl esters such as “Beova-9” and “Beova-10” (both manufactured by Shell Chemical Co., Ltd.); ethylene, propylene, isobutylene, etc. Olefi Etc. The.
また、その他の重合性不飽和化合物(b3)には、フルオロアルキルトリフルオロビニルエーテル、パーフルオロアルキルトリフルオロビニルエーテル等のフルオロビニルエーテルが含まれうる。In addition, the other polymerizable unsaturated compound (b 3 ) may include fluorovinyl ethers such as fluoroalkyl trifluorovinyl ether and perfluoroalkyl trifluorovinyl ether.
加水分解性シリル基含有アクリル樹脂(B)は、弱溶剤に溶解性を有することが好まし。加水分解性シリル基含有アクリル樹脂(B)は、上記弱溶剤の存在下、又は上記弱溶剤及びそれ以外のその他の有機溶剤の存在下で、上述の単量体を重合することにより製造することができる。 The hydrolyzable silyl group-containing acrylic resin (B) preferably has solubility in a weak solvent. The hydrolyzable silyl group-containing acrylic resin (B) is produced by polymerizing the above monomers in the presence of the weak solvent or in the presence of the weak solvent and other organic solvents. Can do.
加水分解性シリル基含有アクリル樹脂(B)の不揮発性成分の重量平均分子量は、特に限定されるものではないが、硬化性、耐候性及び厚膜塗装性の観点から、約1,000〜約100,000の範囲にあり、そして好ましくは約2,000〜約80,000の範囲にある。 Although the weight average molecular weight of the non-volatile component of the hydrolyzable silyl group-containing acrylic resin (B) is not particularly limited, from the viewpoint of curability, weather resistance and thick film coatability, about 1,000 to about 1,000 It is in the range of 100,000, and preferably in the range of about 2,000 to about 80,000.
≪加水分解性シリル基含有シリコーン樹脂(C)≫
加水分解性シリル基含有シリコーン樹脂(C)は、耐候性塗料組成物の厚膜塗装性の観点から配合される成分であり、樹脂中に、加水分解性シリル基を含有し且つポリシロキサン骨格を有する樹脂である。≪Hydrolysable silyl group-containing silicone resin (C) ≫
The hydrolyzable silyl group-containing silicone resin (C) is a component blended from the viewpoint of thick film coating properties of the weather-resistant coating composition, and contains a hydrolyzable silyl group and a polysiloxane skeleton in the resin. It is resin which has.
加水分解性シリル基含有シリコーン樹脂(C)は、例えば、次の式(1):
SiXnY4-n 式(1)
(式中、Xは、水酸基又はアルコキシ基を表わし、Yは、置換基を有していてもよい1価の炭化水素基を表わし、そしてnは、1〜4の整数を表わす。)
で表わされる、同一又は異なる2以上のオルガノシランが化学結合することにより生成した樹脂、例えば、オリゴマーである。The hydrolyzable silyl group-containing silicone resin (C) is, for example, the following formula (1):
SiX n Y 4-n formula (1)
(Wherein X represents a hydroxyl group or an alkoxy group, Y represents a monovalent hydrocarbon group which may have a substituent, and n represents an integer of 1 to 4)
A resin formed by chemical bonding of two or more of the same or different organosilanes, for example, an oligomer.
加水分解性シリル基含有シリコーン樹脂(C)において、式(1)で表されるオルガノシランが、直鎖状、又は分岐鎖状に結合されることができる。また、加水分解性シリル基含有シリコーン樹脂(C)は、ケイ素原子と直接結合する炭化水素基を有することが好ましい。 In the hydrolyzable silyl group-containing silicone resin (C), the organosilane represented by the formula (1) can be bonded linearly or branched. The hydrolyzable silyl group-containing silicone resin (C) preferably has a hydrocarbon group that is directly bonded to a silicon atom.
式(1)で表されるオルガノシランとしては、例えば、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリアセトキシシラン、γ−アミノプロピルトリメトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、γ−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、γ−(メタ)アクリロキシプロピルトリメトキシシラン、フェニルトリメトキシシラン、フェニルトリアセトキシシラン、γ−メルカプトプロピルトリメトキシシラン、γ−クロロプロピルトリメトキシシラン、β−シアノエチルトリエトキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリプロポキシシラン、メチルトリブトキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、テトラメトキシシラン、テトラエトキシシラン、テトラプロポキシシラン、テトラブトキシシラン、ジメチルジクロロシラン、ジフェニルジクロロシラン、メチルフェニルジメトキシシラン、トリメチルメトキシシラン、トリメチルエトキシシラン、γ−アシノプロピルトリエトキシシラン、4−アシノブチルトリエトキシシラン、p−アミノフェニルトリメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、アミノエチルアミノメチルフェネチルトリメトキシシラン、3−グリシドキシプロピルトリメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、4−アミノブチルトリエトキシシラン、N−(6−アミノヘキシル)アミノプロピルトリメトキシシラン、3−クロロプロピルトリメトキシシラン、3−クロロプロピルトリクロロシラン、(p−クロロメチル)フェニルトリメトキシシラン、4−クロロフェニルトリメトキシシラン、3−メタクリロキシプロピルトリメトキシシラン、3−メタクリロキシプロピルトリエトキシシラン、3−アクリロキシプロピルトリメトキシシラン、スチリルエチルトリメトキシシラン、3−メルカプトプロピルトリメトキシシラン、ビニルトリス(2−メトキシエトキシ)シラン、トリフルオロプロピルトリメトキシシラン等、並びにそれらの任意の組み合わせが挙げられる。 Examples of the organosilane represented by the formula (1) include dimethyldimethoxysilane, dimethyldiethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, γ- Aminopropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ- (3,4-epoxycyclohexyl) ) Ethyltriethoxysilane, γ- (meth) acryloxypropyltrimethoxysilane, phenyltrimethoxysilane, phenyltriacetoxysilane, γ-mercaptopropyltrimethoxysilane, γ-chloropropyltrimethoxy Sisilane, β-cyanoethyltriethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltributoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane , Tetrabutoxysilane, dimethyldichlorosilane, diphenyldichlorosilane, methylphenyldimethoxysilane, trimethylmethoxysilane, trimethylethoxysilane, γ-acinopropyltriethoxysilane, 4-acinobutyltriethoxysilane, p-aminophenyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, aminoethylaminomethylphenethyltrimethoxysilane, 3-glyci Doxypropyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 4-aminobutyltriethoxysilane, N- (6 -Aminohexyl) aminopropyltrimethoxysilane, 3-chloropropyltrimethoxysilane, 3-chloropropyltrichlorosilane, (p-chloromethyl) phenyltrimethoxysilane, 4-chlorophenyltrimethoxysilane, 3-methacryloxypropyltrimethoxy Silane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, styrylethyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, vinyltris (2-methoxy Ethoxy) silane, trifluoropropyl trimethoxy silane, as well as any combination thereof.
加水分解性シリル基含有シリコーン樹脂(C)は、加水分解性シリル基含有フッ素樹脂(A)及び加水分解性シリル基含有アクリル樹脂(B)との相溶性、耐候性塗料組成物の厚膜塗装性、及び形成される塗膜の耐屈曲性の観点から、ケイ素原子と直接結合するメチル基及び/又はフェニル基を有していることが好ましい。 The hydrolyzable silyl group-containing silicone resin (C) is compatible with the hydrolyzable silyl group-containing fluororesin (A) and the hydrolyzable silyl group-containing acrylic resin (B), and is a thick film coating of a weather-resistant coating composition. From the viewpoint of the property and the bending resistance of the formed coating film, it preferably has a methyl group and / or a phenyl group directly bonded to a silicon atom.
加水分解性シリル基含有シリコーン樹脂(C)の不揮発性成分の重量平均分子量は、特に制限されるものではないが、加水分解性シリル基含有フッ素樹脂(A)及び加水分解性シリル基含有アクリル樹脂(B)との相溶性、耐候性塗料のハイソリッド化、厚膜塗装性、並びに形成される塗膜の耐屈曲性の観点から、一般に約400〜約30,000、そして好ましくは約400〜約20,000の範囲にある。 Although the weight average molecular weight of the non-volatile component of the hydrolyzable silyl group-containing silicone resin (C) is not particularly limited, the hydrolyzable silyl group-containing fluororesin (A) and the hydrolyzable silyl group-containing acrylic resin From the viewpoint of compatibility with (B), high solidification of the weather-resistant paint, thick film coatability, and bending resistance of the formed coating film, it is generally about 400 to about 30,000, and preferably about 400 to It is in the range of about 20,000.
加水分解性シリル基含有シリコーン樹脂(C)の市販品としては、例えば、「SR2406」、「SR2410」、「SR2420」、「SR2416」、「SR2402」、「AY42−161」、「DC−3074」及び「DC−3037」(以上、東レ・ダウコーニング・シリコーン株式会社製)、「FZ−3704」及び「FZ−3511」(以上、日本ユニカー社製)、「KC−89S」、「KR−500」、「X−40−9225」、「X−40−9246」、「X−40−9250」、「KR−217」、「KR−9218」、「KR−213」、「KR−510」、「X−40−9227」、「X−40−9247」、「X−41−1053」、「X−41−1056」、「X−41−1805」、「X−41−1810」、「X−40−2651」、「X−40−2308」、「X−40−9238」、「X−40−2239」、「X−40−2327」、「KR−400」、「X−40−175」及び「X−40−9740」(以上、信越化学工業株式会社製)等が挙げられる。 Examples of commercially available hydrolyzable silyl group-containing silicone resins (C) include “SR2406”, “SR2410”, “SR2420”, “SR2416”, “SR2402”, “AY42-161”, and “DC-3074”. And “DC-3037” (manufactured by Toray Dow Corning Silicone Co., Ltd.), “FZ-3704” and “FZ-3511” (manufactured by Nihon Unicar), “KC-89S”, “KR-500”. ”,“ X-40-9225 ”,“ X-40-9246 ”,“ X-40-9250 ”,“ KR-217 ”,“ KR-9218 ”,“ KR-213 ”,“ KR-510 ”, “X-40-9227”, “X-40-9247”, “X-41-1053”, “X-41-1056”, “X-41-1805”, “X-41-1810” "X-40-2651", "X-40-2308", "X-40-9238", "X-40-2239", "X-40-2327", "KR-400", "X-40 -175 "and" X-40-9740 "(manufactured by Shin-Etsu Chemical Co., Ltd.).
≪耐候性塗料組成物≫
本発明の耐候性塗料組成物は、加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)を、それらの総固形分質量に基づいて、それぞれ、約1〜約90質量%、約3〜約94質量%、及び約3〜約50質量%、そして好ましくは約5〜約90質量%、約3〜約90質量%、及び約5〜約40質量%含む。耐候性塗料組成物のハイソリッド化、厚膜塗装性、形成される塗膜の仕上がり性(主に光沢)及び耐候性等の観点からである。≪Weather-resistant paint composition≫
The weather resistant coating composition of the present invention comprises a hydrolyzable silyl group-containing fluororesin (A), a hydrolyzable silyl group-containing acrylic resin (B) and a hydrolyzable silyl group-containing silicone resin (C). From about 1 to about 90%, from about 3 to about 94%, and from about 3 to about 50%, and preferably from about 5 to about 90%, from about 3 to about 90%, respectively, based on solids weight And about 5 to about 40% by weight. This is from the standpoints of high solidification of the weather-resistant coating composition, thick film coating properties, finish of the formed coating film (mainly gloss), weather resistance, and the like.
なお、本明細書において、「固形分」は、試料中の水、有機溶剤等の揮発成分を除いた不揮発性成分の比率を意味し、試料約2gを、105℃で3時間乾燥させ、乾燥前後の質量から求めることができる。また、本明細書において、「固形分質量」は、試料中の上記不揮発性成分の質量を意味する。 In this specification, “solid” means the ratio of non-volatile components excluding volatile components such as water and organic solvent in the sample, and about 2 g of the sample is dried at 105 ° C. for 3 hours and dried. It can be determined from the mass before and after. Moreover, in this specification, "solid content mass" means the mass of the said non-volatile component in a sample.
本発明の実施形態の1つに従う耐候性塗料組成物では、形成される塗膜に低汚染性を付与するために、オルガノシリケート(D)をさらに含む。
オルガノシリケート(D)は、加水分解性シリル基含有シリコーン樹脂(C)以外の化合物であり、例えば、ケイ素原子と直接結合する炭化水素基を有さない、次の式(2):
Si(−OR1)4 式(2)
(式中、R1は、アルキル基、アリール基及びアラルキル基から選択される、同一又は異なる1価の炭化水素基である)
で示される化合物、並びにその部分加水分解及び縮合物が挙げられる。
式(2)において、R1は、炭素数1〜4のアルキル基であることが好ましい。In the weather resistant coating composition according to one of the embodiments of the present invention, an organosilicate (D) is further included in order to impart low contamination to the formed coating film.
The organosilicate (D) is a compound other than the hydrolyzable silyl group-containing silicone resin (C), and has, for example, the following formula (2) having no hydrocarbon group directly bonded to a silicon atom:
Si (-OR 1 ) 4 formula (2)
(Wherein R 1 is the same or different monovalent hydrocarbon group selected from an alkyl group, an aryl group and an aralkyl group)
And the partial hydrolysis and condensate thereof.
In Formula (2), R 1 is preferably an alkyl group having 1 to 4 carbon atoms.
オルガノシリケート(D)の例としては、テトラメトキシシラン、テトラエトキシシラン、テトラ−n−プロポキシシラン、テトラ−イソプロポキシシラン、テトラ−n−ブトキシシラン、テトラ−イソブトキシシラン、テトラ−t−ブトキシシラン、及びそれらの任意の組み合わせ、並びにそれらの部分加水分解及び縮合物が挙げられる。 Examples of organosilicate (D) include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-isopropoxysilane, tetra-n-butoxysilane, tetra-isobutoxysilane, and tetra-t-butoxysilane. , And any combination thereof, and partial hydrolysis and condensates thereof.
オルガノシリケート(D)の市販品としては、例えば、「エチルシリケート45」、「エチルシリケート40」及び「エチルシリケート48」(以上、コルコート社製)、「シリケート45」及び「シリケート40」(以上、多摩化学工業社製)、「TES40WN」(以上、旭化成ワッカーシリコーン社製)等を挙げることができる。 Examples of the commercially available organosilicate (D) include, for example, “ethyl silicate 45”, “ethyl silicate 40” and “ethyl silicate 48” (manufactured by Colcoat Co.), “silicate 45” and “silicate 40” (and above, Tama Chemical Industry Co., Ltd.), “TES40WN” (above, manufactured by Asahi Kasei Wacker Silicone Co., Ltd.) and the like.
耐候性塗料組成物がオルガノシリケート(D)を含む実施形態では、耐候性塗料組成物は、オルガノシリケート(D)を、加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)の総固形分質量100質量部に基づいて、固形分質量で、好ましくは約1〜約30質量部、そしてより好ましくは約5〜約20質量部の範囲で含む。形成される塗膜の耐ワレ性の観点からである。 In the embodiment in which the weather-resistant coating composition contains an organosilicate (D), the weather-resistant coating composition comprises an organosilicate (D), a hydrolyzable silyl group-containing fluororesin (A), and a hydrolyzable silyl group-containing acrylic. Based on 100 parts by mass of the total solid content of the resin (B) and the hydrolyzable silyl group-containing silicone resin (C), the solid content is preferably about 1 to about 30 parts by mass, and more preferably about 5 to 5 parts by mass. It is included in the range of about 20 parts by mass. This is from the viewpoint of crack resistance of the formed coating film.
本発明の実施形態の1つに従う耐候性塗料組成物では、耐候性塗料組成物は、従来公知の顔料を含む。上記顔料としては、例えば、酸化チタン、ベンガラ、シアニン系着色顔料、カーボンブラック、ジルコン粉末等の着色顔料;シリカ、バリタ粉、沈降性硫酸バリウム、炭酸バリウム、炭酸カルシウム、石膏、クレー、ホワイトカーボン、珪藻土、タルク、炭酸マグネシウム、アルミナホワイト、グロスホワイト、タンカル等の体質顔料等、並びにそれらの組み合わせが挙げられる。 In the weather-resistant coating composition according to one of the embodiments of the present invention, the weather-resistant coating composition includes a conventionally known pigment. Examples of the pigment include coloring pigments such as titanium oxide, bengara, cyanine color pigments, carbon black and zircon powder; silica, barita powder, precipitated barium sulfate, barium carbonate, calcium carbonate, gypsum, clay, white carbon, Examples thereof include extender pigments such as diatomaceous earth, talc, magnesium carbonate, alumina white, gloss white, and tancal, and combinations thereof.
耐候性塗料組成物が顔料を含む実施形態では、耐候性塗料組成物は、顔料を、加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)の総固形分質量100質量部に基づいて、固形分質量で、好ましくは約50〜約100質量部、そしてより好ましくは約60〜約90質量部含む。形成される塗膜の厚膜塗装性、及び耐候性の観点からである。 In the embodiment in which the weather-resistant coating composition includes a pigment, the weather-resistant coating composition includes the pigment, hydrolyzable silyl group-containing fluororesin (A), hydrolyzable silyl group-containing acrylic resin (B), and hydrolyzable. Based on the total solid mass of 100 parts by mass of the silyl group-containing silicone resin (C), the solid content is preferably about 50 to about 100 parts by mass, and more preferably about 60 to about 90 parts by mass. This is from the viewpoint of thick film coatability and weather resistance of the formed coating film.
本発明の実施形態の1つに従う耐候性塗料組成物では、塗膜の常温硬化性を向上させ、早期に耐候性に優れた塗膜を形成させるために、耐候性塗料組成物が、加水分解性シリル基の重縮合を促進する触媒を含む。 In the weather-resistant coating composition according to one of the embodiments of the present invention, the weather-resistant coating composition is hydrolyzed in order to improve the room temperature curability of the coating and form a coating excellent in weather resistance at an early stage. The catalyst which accelerates | stimulates the polycondensation of a functional silyl group is included.
上記触媒としては、従来公知のものが挙げられ、そして上記触媒の例として、ジアセチル錫ジアセテート、ジブチル錫ジラウレート、ジブチル錫ジアセテート、ジオクチル錫ジラウレート、ジアセチル錫ジオクトエート、オクチル酸錫、ジブチル錫ジアセテート、ジブチル錫ジオクトエート等の有機錫化合物;アルミニウムトリメトキシド、アルミニウムトリス(アセチルアセトネート)、アルミニウムトリ−n−ブトキシド、アルミニウムトリス(アセトアセテートエチル)、アルミニウムジイソプロポキシ(アセトアセテートエチル)、アルミニウムアセチルアセトナート等の有機アルミニウム化合物;チタニウムテトラ(モノエチルエトキシド)、チタニウムテトラ(モノエチルエトキシド)、チタニウムテトラ(モノブチルエトキシド)、チタニウムテトラキス(アセチルアセトネート)、テトラノルマルブチルチタネート等の有機チタン化合物;ジルコニウムテトラ(モノメチルエトキシド)、ジルコニウムテトラ(モノエチルエトキシド)、ジルコニウムテトラ(モノブチルエトキシド)、ジルコニウムノルマルプロピレート、ジルコニウムノルマルブチレート、ジルコニウムテトラキス(アセチルアセトネート)等の有機ジルコニウム化合物;ナフテン酸亜鉛等の有機亜鉛化合物;オクチル酸コバルト、ナフテン酸コバルト等の有機コバルト化合物;トリメチルアミン、トリエチルアミン、2−(ジメチルアミノ)エチルメタクリレート、1,4−ジアザビシクロ[2.2.2]オクタン、1,8−ジアザビシクロ[5.4.0]−7−ウンデセン、1,5−ジアザビシクロ[4.3.0]−5−ノネン、1−メチルピペリジン、1−メチルピロリジン等の脂肪族アミン、ピリジン、4−ジメチルアミノピリジン、4−(1−ピペリジル)ピリジン、N−メチルイミダゾール、N,N−ジメチルアニリン等のアミン触媒;カルボン酸の鉛、スズ、亜鉛、及び鉄錯体;ホウ酸トリメチル、ホウ酸トリエチル、ホウ酸トリプロピル、ホウ酸トリブチル、ホウ酸トリフェニル、ホウ酸トリ(4−クロロフェニル)、ホウ酸トリヘキサフルオロイソプロピル等のホウ酸エステル等のホウ酸化合物等、並びにそれらの組み合わせが挙げられる。 Examples of the catalyst include those conventionally known, and examples of the catalyst include diacetyltin diacetate, dibutyltin dilaurate, dibutyltin diacetate, dioctyltin dilaurate, diacetyltin dioctoate, tin octylate, and dibutyltin diacetate. , Organotin compounds such as dibutyltin dioctoate; aluminum trimethoxide, aluminum tris (acetylacetonate), aluminum tri-n-butoxide, aluminum tris (acetoacetate ethyl), aluminum diisopropoxy (acetoacetate ethyl), aluminum acetyl Organoaluminum compounds such as acetonate; titanium tetra (monoethyl ethoxide), titanium tetra (monoethyl ethoxide), titanium tetra (monobutyl ethoxy) ), Organic titanium compounds such as titanium tetrakis (acetylacetonate) and tetranormal butyl titanate; zirconium tetra (monomethyl ethoxide), zirconium tetra (monoethyl ethoxide), zirconium tetra (monobutyl ethoxide), zirconium normal propylate Organic zirconium compounds such as zirconium normal butyrate and zirconium tetrakis (acetylacetonate); organic zinc compounds such as zinc naphthenate; organic cobalt compounds such as cobalt octylate and cobalt naphthenate; trimethylamine, triethylamine, 2- (dimethylamino) ) Ethyl methacrylate, 1,4-diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene, 1,5-diaza Aliphatic amines such as cyclo [4.3.0] -5-nonene, 1-methylpiperidine, 1-methylpyrrolidine, pyridine, 4-dimethylaminopyridine, 4- (1-piperidyl) pyridine, N-methylimidazole, Amine catalysts such as N, N-dimethylaniline; lead, tin, zinc, and iron complexes of carboxylic acids; trimethyl borate, triethyl borate, tripropyl borate, tributyl borate, triphenyl borate, triborate borate ( 4-chlorophenyl), boric acid compounds such as boric acid esters such as trihexafluoroisopropyl borate, and combinations thereof.
本発明の実施形態の1つに従う耐候性塗料組成物では、耐候性塗料組成物が1液型の塗料組成物であり、そして別の実施形態では、主剤及び硬化剤からなる2液型の塗料組成物である。 In the weather-resistant coating composition according to one of the embodiments of the present invention, the weather-resistant coating composition is a one-component paint composition, and in another embodiment, a two-component paint comprising a main agent and a curing agent It is a composition.
上記2液型の塗料組成物は、加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)を含む主剤と、触媒を含む硬化剤との2液型の塗料組成物であることが好ましい。塗装直前に主剤及び硬化剤を混合し、所望により溶剤で塗装粘度を調整した後に塗装することができるため、低温環境下でも、塗装後早期に厚膜で耐候性、仕上がり性等に優れた塗膜が得られる。また、貯蔵段階(封缶状態)での貯蔵安定性に優れる。 The two-component coating composition includes a hydrolyzable silyl group-containing fluororesin (A), a hydrolyzable silyl group-containing acrylic resin (B), and a hydrolyzable silyl group-containing silicone resin (C), A two-component coating composition with a curing agent containing a catalyst is preferable. Since the main agent and curing agent can be mixed immediately before coating and the coating viscosity can be adjusted with a solvent if desired, coating can be performed even in low-temperature environments, with a thick film and excellent weather resistance, finish, etc. early after coating. A membrane is obtained. Moreover, it is excellent in the storage stability in the storage stage (sealed can state).
本発明の実施形態の1つに従う耐候性塗料組成物では、耐候性塗料組成物がハイソリッド型である。当該実施形態では、貯蔵段階(封缶状態)における耐候性塗料組成物又は主剤の固形分が、例えば、約60〜約85質量%、特に約65〜約80質量%の範囲にある。 In the weather-resistant coating composition according to one of the embodiments of the present invention, the weather-resistant coating composition is a high solid type. In this embodiment, the solid content of the weather-resistant coating composition or main ingredient in the storage stage (sealed state) is, for example, in the range of about 60 to about 85% by mass, particularly about 65 to about 80% by mass.
また、本発明の実施形態の1つに従う耐候性塗料組成物では、耐候性塗料組成物が、弱溶剤型の塗料組成物である。当該実施形態では、貯蔵段階(封缶状態)における塗料又は主剤に含まれる弱溶剤の比率が、全有機溶剤量を基準として、約80質量%以上、特に約80〜約100質量%の範囲にあることが好ましい。耐候性塗料組成物が弱溶剤型の塗料組成物であることにより、耐候性塗料組成物を下地、例えば、古い塗膜の上に塗装した際のチヂミの発生等を抑制することができ、そして塗装作業性にも優れる。なお、弱溶剤としては、上述の第3種有機溶剤の群から選択される一又は複数の溶剤が挙げられる。 In the weather resistant coating composition according to one of the embodiments of the present invention, the weather resistant coating composition is a weak solvent type coating composition. In this embodiment, the ratio of the weak solvent contained in the paint or the main agent in the storage stage (sealed can state) is in the range of about 80% by mass or more, particularly about 80 to about 100% by mass, based on the total amount of organic solvent. Preferably there is. Since the weather-resistant coating composition is a weak solvent type coating composition, it is possible to suppress the occurrence of wrinkles and the like when the weather-resistant coating composition is applied onto a base, for example, an old coating film, and Excellent paint workability. In addition, as a weak solvent, the 1 or several solvent selected from the group of the above-mentioned 3rd type organic solvent is mentioned.
耐候性塗料組成物が弱溶剤型の塗料組成物である実施形態では、耐候性塗料組成物は、弱溶剤の他に、全有機溶剤量を基準として、労働安全衛生法における第1種有機溶剤及び第2種有機溶剤を、好ましくは約20質量%以下、そしてより好ましくは約5質量%以下含むことができる。 In an embodiment in which the weather-resistant coating composition is a weak solvent-type coating composition, the weather-resistant coating composition is a first organic solvent in the Industrial Safety and Health Act based on the total amount of organic solvents in addition to the weak solvent. And the second organic solvent may be contained in an amount of preferably about 20% by mass or less, and more preferably about 5% by mass or less.
なお、第1種有機溶剤としてとは、クロロホルム、四塩化炭素、1,2−ジクロルエタン、1,2−ジクロルエチレン、1,1,2,2−テトラクロルエタン、トリクロルエタン、二硫化炭素、及びそれらの任意の組み合わせ等が挙げられる。 Examples of the first type organic solvent include chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,2-dichloroethylene, 1,1,2,2-tetrachloroethane, trichloroethane, carbon disulfide, And any combination thereof.
第2種有機溶剤とは、いわゆる強溶剤と呼ばれるものであり、例えば、アセトン、イソブチルアルコール、イソプロピルアルコール、イソペンチルアルコール、エチルアルコール、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノ−n−ブチルエーテル、エチレングリコールモノメチルエーテル、オルト−ジクロロベンゼン、キシレン、クレゾール、クロルベンゼン、酢酸イソブチル、酢酸イソプロピル、酢酸イソペンチル、酢酸エチル、酢酸−n−ブチル、酢酸−n−プロピル、酢酸−n−ペンチル、酢酸メチル、シクロヘキサノール、シクロヘキサノン、1,4−ジオキサン、ジクロロメタン、N,N−ジメチルホルムアミド、スチレン、テトラクロロエチレン、テトラヒドロフラン、1,1,1−トリクロルエタン、トルエン、n−ヘキサン、1−ブタノール、2−ブタノール、メタノール、メチルイソブチルケトン、メチルエチルケトン、メチルシクロヘキサノール、メチルシクロヘキサノン、メチル−n−ブチルケトン等、並びにそれらの任意の組み合わせを挙げることができる。 The second type organic solvent is a so-called strong solvent, for example, acetone, isobutyl alcohol, isopropyl alcohol, isopentyl alcohol, ethyl alcohol, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol mono -N-butyl ether, ethylene glycol monomethyl ether, ortho-dichlorobenzene, xylene, cresol, chlorobenzene, isobutyl acetate, isopropyl acetate, isopentyl acetate, ethyl acetate, -n-butyl acetate, -n-propyl acetate, acetic acid -n- Pentyl, methyl acetate, cyclohexanol, cyclohexanone, 1,4-dioxane, dichloromethane, N, N-dimethylformamide, styrene, tetrachloroethylene, te Lahydrofuran, 1,1,1-trichloroethane, toluene, n-hexane, 1-butanol, 2-butanol, methanol, methyl isobutyl ketone, methyl ethyl ketone, methyl cyclohexanol, methyl cyclohexanone, methyl-n-butyl ketone, and the like Any combination can be mentioned.
本発明のいくつかの実施形態に従う耐候性塗料組成物では、耐候性塗料組成物が、シランカップリング剤;防錆顔料;硬化剤成分;アクリル樹脂、エポキシ樹脂、アルキド樹脂、ウレタン樹脂等の改質用樹脂;有機溶剤;反応性希釈剤;付着付与剤、沈降防止剤、分散剤、湿潤剤、脱水剤等の塗料用添加剤等を含む。 In the weather-resistant coating composition according to some embodiments of the present invention, the weather-resistant coating composition is a modified silane coupling agent; rust preventive pigment; curing agent component; acrylic resin, epoxy resin, alkyd resin, urethane resin, or the like. Resin for quality; Organic solvent; Reactive diluent; Additive for coating such as adhesion imparting agent, anti-settling agent, dispersant, wetting agent, dehydrating agent and the like.
上記シランカップリング剤としては、例えば、γ−(2−アミノエチル)アミノプロピルトリメトキシシラン、γ−アミノプロピルトリエトキシシラン、N−β(アミノエチル)γ−アミノプロピルトリメトキシシラン、N−β(アミノエチル)γ−アミノプロピルメチルジメトキシシラン等のアミノ基含有シランカップリング剤;γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルメチルジメトキシシラン等のグリシジル基含有シランカップリング剤;γ−メルカプトプロピルトリメトキシシラン等のメルカプト基含有シランカップリング剤;ビニルトリエトキシシラン、ビニルトリメトキシシラン、ビニルトリス(メトキシエトキシ)シラン等のビニル基含有シランカップリング剤;γ−(メタ)アクリロイルオキシプロピルトリメトキシシラン、γ−(メタ)アクリロイルオキシプロピルトリエトキシシラン、γ−(メタ)アクリロイルオキシプロピルジメトキシメチルシラン等の(メタ)アクリロイル基含有シランカップリング剤等が挙げられる。 Examples of the silane coupling agent include γ- (2-aminoethyl) aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β. (Aminoethyl) amino group-containing silane coupling agents such as γ-aminopropylmethyldimethoxysilane; glycidyl group-containing silane coupling agents such as γ-glycidoxypropyltrimethoxysilane and γ-glycidoxypropylmethyldimethoxysilane; Mercapto group-containing silane coupling agents such as γ-mercaptopropyltrimethoxysilane; Vinyl group-containing silane coupling agents such as vinyltriethoxysilane, vinyltrimethoxysilane and vinyltris (methoxyethoxy) silane; γ- (meth) acryloyloxy The Pills trimethoxysilane, .gamma. (meth) acryloyloxy propyl triethoxysilane, .gamma. (meth) acryloyloxy propyl, such as dimethoxymethyl silane (meth) acryloyl group-containing silane coupling agent and the like.
耐候性塗料組成物がシランカップリング剤を含む実施形態では、耐候性塗料組成物は、シランカップリング剤を、加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)の総固形分質量100質量部に基づいて、好ましくは約1.0〜約30質量部、そしてより好ましくは約1.5〜約20質量部の範囲で含む。付着性向上の観点からである。 In the embodiment in which the weather-resistant coating composition contains a silane coupling agent, the weather-resistant coating composition contains a silane coupling agent, a hydrolyzable silyl group-containing fluororesin (A), a hydrolyzable silyl group-containing acrylic resin ( Preferably from about 1.0 to about 30 parts by weight, and more preferably from about 1.5 to about 20 parts by weight, based on 100 parts by weight of the total solid content of B) and the hydrolyzable silyl group-containing silicone resin (C). Included in the range of parts. This is from the viewpoint of improving adhesion.
本発明の実施形態の1つに従う耐候性塗料組成物では、耐候性塗料組成物が常温硬化型であり、形成した硬化塗膜が優れた性能を発揮することができる。本発明の他の実施形態に従う耐候性塗料組成物では、耐候性塗料組成物が乾燥硬化型又は加熱硬化型である。
本発明の耐候性塗料組成物の用途としては、特に制限されるものではないが、橋梁、送電鉄塔、プラント、タンク等の鋼製構造物の重防食塗装の上塗り用途が挙げられる。In the weather resistant coating composition according to one of the embodiments of the present invention, the weather resistant coating composition is a room temperature curing type, and the formed cured coating film can exhibit excellent performance. In the weather resistant coating composition according to another embodiment of the present invention, the weather resistant coating composition is of a dry curing type or a heat curing type.
Although it does not restrict | limit especially as a use of the weather-resistant coating material composition of this invention, The top coating use of heavy anticorrosion coating of steel structures, such as a bridge, a power transmission tower, a plant, a tank, is mentioned.
≪耐候性塗膜を有する塗装物品の製造方法≫
耐候性塗料組成物を塗装すべき被塗物としては、所望により下地処理された金属素材、例えば、鋼板、亜鉛めっき、ステンレス、アルミニウム等、アルカリ性を有する基材、例えば、コンクリート、モルタル、スレート、スレート瓦等、窯業系建材、プラスチック等、並びにそれらの上に古い塗膜が形成されているものが挙げられる。≪Method for producing coated article having weather-resistant coating film≫
As an object to be coated with a weather-resistant coating composition, a metal material subjected to a ground treatment as desired, for example, a steel plate, galvanized, stainless steel, aluminum, etc., an alkaline substrate such as concrete, mortar, slate, Examples include slate roof tiles, ceramic building materials, plastics, etc., and those on which an old coating film is formed.
耐候性塗膜を有する塗装物品は、例えば、上記被塗物に、上記耐候性塗料組成物を塗装し、耐候性塗膜を形成することにより製造することができる。
上記耐候性塗料組成物は、例えば、スプレー塗り、ローラー塗り、刷毛塗り、流し塗り等の公知の手段で塗装することができる。A coated article having a weather-resistant coating film can be produced, for example, by applying the weather-resistant coating composition to the article to be coated to form a weather-resistant coating film.
The weather-resistant coating composition can be applied by known means such as spray coating, roller coating, brush coating, and flow coating.
また、本発明の実施形態の1つに従う耐候性塗膜を有する塗装物品の製造方法では、耐候性塗料組成物により耐候性塗膜を形成する前に、被塗物に下塗り塗料を塗装し、防食塗膜を形成する。 In the method for producing a coated article having a weather-resistant coating film according to one of the embodiments of the present invention, before forming the weather-resistant coating film with the weather-resistant coating composition, an undercoat paint is applied to the article to be coated, Form an anticorrosion coating.
上記下塗り塗料としては、当技術分野で公知の下塗り塗料が挙げられる。
上記下塗り塗料の例として、エポキシ樹脂塗料、変性エポキシ樹脂塗料、エポキシ樹脂系ガラスフレーク塗料、エポキシ樹脂被覆材料、超厚膜形エポキシ樹脂塗料、エポキシ樹脂ジンクリッチペイント、無機ジンクリッチペイント、塩化ゴム樹脂系塗料、フタル酸樹脂系塗料、エポキシエステル樹脂塗料等が挙げられる。Examples of the undercoat paint include undercoat paints known in the art.
Examples of the above-mentioned undercoat paints include epoxy resin paints, modified epoxy resin paints, epoxy resin glass flake paints, epoxy resin coating materials, ultra-thick film epoxy resin paints, epoxy resin zinc rich paints, inorganic zinc rich paints, and chlorinated rubber resins. Paints, phthalic acid resin paints, epoxy ester resin paints, and the like.
上記下塗り塗料は、1回塗り又は複数回塗りにより塗装され、その膜厚は、乾燥膜厚で、好ましくは約10〜約2,500μm、より好ましくは約30〜約600μm、そしてさらに好ましくは約60〜約120μmの範囲にある。 The undercoat paint is applied by one or more coatings, and the thickness thereof is a dry film thickness, preferably about 10 to about 2,500 μm, more preferably about 30 to about 600 μm, and more preferably about It is in the range of 60 to about 120 μm.
本発明の耐候性塗料組成物は厚膜塗装性を有しているため、中塗り塗装を省略し、中塗り及び上塗りを兼ねることができる。本発明の耐候性塗料組成物が中塗り及び上塗りを兼ねる場合には、上記耐候性塗料組成物は、1回塗り又は複数回塗りで塗装され、塗膜の膜厚は、乾燥膜厚で約50〜約150μm、特に約50〜約100μmの範囲であることができる。 Since the weather-resistant coating composition of the present invention has thick film coatability, the intermediate coating can be omitted, and the intermediate coating and the top coating can be combined. When the weather-resistant coating composition of the present invention also serves as an intermediate coating and a top coating, the weather-resistant coating composition is applied by a single coating or multiple coatings, and the film thickness of the coating film is about a dry film thickness. It can range from 50 to about 150 μm, in particular from about 50 to about 100 μm.
本発明のさらに別の実施形態に従う耐候性塗膜を有する塗装物品の製造方法では、耐候性塗料組成物を塗装する前に、下塗り塗料による防食塗膜の上に、中塗り塗料により中塗り塗膜を形成する。 In the method for producing a coated article having a weather-resistant coating film according to still another embodiment of the present invention, an intermediate coating is applied on the anticorrosion coating by the undercoat before applying the weather-resistant coating composition. A film is formed.
上記中塗り塗料の例として、エポキシ樹脂系塗料、ポリウレタン系塗料、エポキシ樹脂MIO塗料、フェノール樹脂系MIO塗料、塩化ゴム樹脂系塗料、フタル酸樹脂系塗料等が挙げられる。当該実施形態では、下塗り塗料を、乾燥膜厚が好ましくは約30〜約1,200μm、より好ましくは約30〜約600μm、さらに好ましくは約60〜約120μmとなるように塗装し、そして中塗り塗料を、乾燥膜厚が好ましくは約30〜約80μm、より好ましくは約30〜約60μmとなるように塗装し、そして耐候性塗料組成物を、乾燥膜厚が好ましくは約20〜約60μm、より好ましくは約20〜約50μmとなるように塗装することができる。
上記下塗り塗料、中塗り塗料及び耐候性塗料組成物は、それぞれ、1回又は複数回で塗装することができる。Examples of the intermediate coating include epoxy resin coatings, polyurethane coatings, epoxy resin MIO coatings, phenol resin MIO coatings, chlorinated rubber resin coatings, and phthalic acid resin coatings. In this embodiment, the primer coating is applied such that the dry film thickness is preferably about 30 to about 1,200 μm, more preferably about 30 to about 600 μm, and even more preferably about 60 to about 120 μm, and intermediate coating The paint is applied such that the dry film thickness is preferably about 30 to about 80 μm, more preferably about 30 to about 60 μm, and the weather resistant paint composition is preferably about 20 to about 60 μm in dry film thickness, More preferably, the coating can be performed so as to have a thickness of about 20 to about 50 μm.
Each of the undercoat paint, intermediate coat paint and weather resistant paint composition can be applied once or multiple times.
本発明のさらに別の実施形態に従う耐候性塗膜を有する塗装物品の製造方法では、フタル酸樹脂系、ウレタン樹脂系、アクリルシリコン樹脂系、ふっ素樹脂系の上塗り塗料、アルキド樹脂系、アクリル変性エポキシ樹脂系、シリコン変性エポキシ樹脂系の下塗りと上塗りとを兼ねる塗料のさらに上に、オーバートップコートとして、上記耐候性塗料組成物を塗装する。 In a method for producing a coated article having a weather-resistant coating film according to still another embodiment of the present invention, a phthalic acid resin-based, urethane resin-based, acrylic silicon resin-based, fluorine resin-based top coating, alkyd resin-based, acrylic-modified epoxy The above weather-resistant coating composition is applied as an overtop coat on a coating that serves both as a resin-based and silicon-modified epoxy resin-based undercoat and topcoat.
本発明の耐候性塗料組成物は、常温乾燥の条件でも容易に硬化することができ、防食塗装が施工されるような厳しい環境下においても長期に渡って耐候性に優れる塗膜を形成することができる。
また、本塗料の耐候性塗料組成物は、厚膜塗装性に優れるため、上塗り塗料としてだけでなく、中塗り塗料と上塗り塗料を兼ねる中上塗り塗料としても適用されうる。The weather-resistant coating composition of the present invention can be easily cured even under conditions of room temperature drying, and forms a coating film having excellent weather resistance over a long period of time even in a severe environment where anticorrosion coating is applied. Can do.
Further, since the weather-resistant coating composition of the present coating is excellent in thick film coating properties, it can be applied not only as a top coating but also as a middle top coating that serves as both an intermediate coating and a top coating.
さらに、本発明の耐候性塗料組成物は、長期耐候性を有する耐候性塗膜を形成することができるので、塗り替えまでの期間を長くすることができ、且つ塗装工程を省略することも可能であるために、鋼製構造物等の被塗物の塗装に関わるメンテナンスコストを大幅に抑えることができる。 Furthermore, since the weather-resistant coating composition of the present invention can form a weather-resistant coating film having long-term weather resistance, the period until repainting can be lengthened, and the coating process can be omitted. Therefore, the maintenance cost related to the coating of the object such as a steel structure can be greatly reduced.
以下、本発明を実施例によりさらに具体的に説明する。ただし、本発明はこれらの実施例のみに限定されるものではない。なお、下記例中の「部」及び「%」はそれぞれ「質量部」及び「質量%」を意味する。 Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to only these examples. In the following examples, “part” and “%” mean “part by mass” and “% by mass”, respectively.
≪塗料組成物の製造≫
[実施例1〜37及び比較例1〜3]
表1の組成に従って、容器に、各材料を添加し、そして攪拌することにより、固形分が約75%の塗料組成物No.1〜40を製造した。
なお、表1において、括弧内の数字、すなわち、加水分解性シリル基含有フッ素樹脂(A)及び加水分解性シリル基含有アクリル樹脂(B)の量は、固形分質量を意味し、そして括弧のない数字、すなわち、シリコーンオリゴマー、オルガノシリケート、触媒及びシランカップリング剤の量は、実際に添加した量を意味する。≪Manufacture of paint composition≫
[Examples 1-37 and Comparative Examples 1-3]
According to the composition of Table 1, each material was added to the container and stirred to obtain a coating composition No. having a solid content of about 75%. 1-40 were manufactured.
In Table 1, the numbers in parentheses, that is, the amounts of hydrolyzable silyl group-containing fluororesin (A) and hydrolyzable silyl group-containing acrylic resin (B) mean the solid content mass, and No numbers, i.e., amounts of silicone oligomer, organosilicate, catalyst and silane coupling agent, refer to the amount actually added.
≪試験塗板の作成≫
A.耐候性塗料組成物が上塗り塗料である例:
アセトンで脱脂した鋼板上に、弱溶剤可溶厚膜型変性エポキシ樹脂系錆止め塗料(「エスコNBセーフティ」(商品名、関西ペイント社製、主剤/アミン硬化剤=17/1)を、乾燥膜厚が60μmとなるようにスプレー塗装し、23℃で24時間乾燥させ、次いで中塗り塗料として弱溶剤可溶イソシアネート硬化ポリウレタン塗料(「セラテクトマイルド中塗り」(商品名、関西ペイント社製、主剤/イソシアネート硬化剤質量比10/1)を、乾燥膜厚が30μmとなるようにスプレー塗装し、23℃で24時間乾燥させ、次いで、塗料組成物No.1〜40を、乾燥膜厚が25μmとなるようにスプレー塗装し、23℃で168時間乾燥させることにより、試験板(A)No.1〜40を製造した。≪Creation of test coating board≫
A. Examples where the weather resistant coating composition is a top coat:
On a steel plate degreased with acetone, a weak solvent soluble thick film type modified epoxy resin-based rust preventive paint ("ESCO NB Safety" (trade name, manufactured by Kansai Paint Co., Ltd., main agent / amine curing agent = 17/1), dried film Spray-coated to a thickness of 60 μm, dried at 23 ° C. for 24 hours, and then weakly solvent-soluble isocyanate-cured polyurethane coating (“Serect Mild Intermediate Coating” (trade name, manufactured by Kansai Paint Co., Ltd. / Isocyanate curing agent mass ratio 10/1) is spray-coated so that the dry film thickness is 30 μm, dried at 23 ° C. for 24 hours, and then coating composition Nos. 1 to 40 are obtained with a dry film thickness of 25 μm. The test plate (A) Nos. 1 to 40 were manufactured by spray coating so as to be and dried at 23 ° C. for 168 hours.
B.耐候性塗料組成物が中塗り及び上塗りを兼ねる塗料である例
アセトンで脱脂した鋼板上に、弱溶剤可溶厚膜型変性エポキシ樹脂系錆止め塗料(「エスコNBマイルドH」(商品名、関西ペイント社製、主剤/アミン硬化剤=9/1)を、乾燥膜厚が120μmとなるようにスプレー塗装し、23℃で24時間乾燥させ、次いで、塗料組成物No.1〜40を、乾燥膜厚が55μmとなるようにスプレー塗装し、23℃で168時間乾燥させることにより、試験板(B)No.1〜40を製造した。B. An example of a weather-resistant coating composition that serves as an intermediate coat and top coat. On a steel plate degreased with acetone, a weak solvent soluble thick film type modified epoxy resin-based rust preventive paint ("ESCO NB Mild H" (trade name, Kansai Paint) Co., Ltd., main agent / amine curing agent = 9/1) was spray-coated so that the dry film thickness was 120 μm, dried at 23 ° C. for 24 hours, and then coating compositions No. 1 to 40 were dried films Test plates (B) No. 1 to 40 were produced by spray coating so that the thickness was 55 μm and drying at 23 ° C. for 168 hours.
≪性能評価≫
試験板(A)No.1〜40と、試験板(B)No.1〜40とを評価した。結果を下記表1に示す。≪Performance evaluation≫
Test plate (A) No. 1 to 40 and the test plate (B) No. 1 to 40 were evaluated. The results are shown in Table 1 below.
≪加水分解性シリル基含有フッ素樹脂(A)≫
[A1]
クロロトリフルオロエチレン/シクロヘキシルアクリレート/n−ブチルアクリレート/ビニルトリメトキシシラン=37/49/10/4の共重合体の溶液、重量平均分子量:30,000、固形分:64%、溶剤:ミネラルスピリット
[A2]
クロロトリフルオロエチレン/シクロヘキシルアクリレート/ビニルトリメトキシシラン=48/46/6の共重合体の溶液、重量平均分子量:40,000、固形分:64%、溶剤:ミネラルスピリット≪Hydrolyzable silyl group-containing fluororesin (A) ≫
[A1]
Chlorotrifluoroethylene / cyclohexyl acrylate / n-butyl acrylate / vinyl trimethoxysilane = 37/49/10/4 copolymer solution, weight average molecular weight: 30,000, solid content: 64%, solvent: mineral spirit [A2]
Solution of copolymer of chlorotrifluoroethylene / cyclohexyl acrylate / vinyltrimethoxysilane = 48/46/6, weight average molecular weight: 40,000, solid content: 64%, solvent: mineral spirit
[A3]
クロロトリフルオロエチレン/シクロヘキシルアクリレート/tert−ブチルアクリレート/ビニルトリメトキシシラン=28/39/28/5の共重合体の溶液、重量平均分子量:20,000、固形分:64%、溶剤:ミネラルスピリット[A3]
Solution of copolymer of chlorotrifluoroethylene / cyclohexyl acrylate / tert-butyl acrylate / vinyltrimethoxysilane = 28/39/28/5, weight average molecular weight: 20,000, solid content: 64%, solvent: mineral spirit
≪加水分解性シリル基含有アクリル樹脂(B)≫
[B1]
イソボルニルアクリレート/シクロヘキシルメタクリレート/イソブチルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=20/30/20/20/10の共重合体の溶液、重量平均分子量:20,000、固形分:60%、溶剤:ミネラルスピリット≪Hydrolysable silyl group-containing acrylic resin (B) ≫
[B1]
Solution of copolymer of isobornyl acrylate / cyclohexyl methacrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 20/30/20/20/10, weight average molecular weight: 20,000, solid Min: 60%, Solvent: Mineral Spirit
「B2]
イソボルニルアクリレート/シクロヘキシルメタクリレート/イソブチルメタクリレート/2−エチルへキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=5/40/20/30/5の共重合体の溶液、重量平均分子量:25,000、固形分:60%、溶剤:ミネラルスピリット“B2”
Solution of copolymer of isobornyl acrylate / cyclohexyl methacrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 5/40/20/30/5, weight average molecular weight: 25,000 , Solid content: 60%, Solvent: Mineral spirit
[B3]
イソボルニルアクリレート/シクロヘキシルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=30/50/10/10の共重合体の溶液、重量平均分子量:30,000、固形分:60%、溶剤:ミネラルスピリット[B3]
Solution of copolymer of isobornyl acrylate / cyclohexyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 30/50/10/10, weight average molecular weight: 30,000, solid content: 60%, Solvent: Mineral Spirit
[B4]
イソボルニルアクリレート/シクロヘキシルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=50/25/15/10の共重合体の溶液、重量平均分子量:28,000、固形分:60%、溶剤:ミネラルスピリット[B4]
Solution of copolymer of isobornyl acrylate / cyclohexyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 50/25/15/10, weight average molecular weight: 28,000, solid content: 60%, Solvent: Mineral Spirit
[B5]
イソボルニルアクリレート/シクロヘキシルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=10/55/20/15の共重合体の溶液、重量平均分子量:24,000、固形分:60%、溶剤:ミネラルスピリット[B5]
Solution of copolymer of isobornyl acrylate / cyclohexyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 10/55/20/15, weight average molecular weight: 24,000, solid content: 60%, Solvent: Mineral Spirit
[B6]
イソボルニルアクリレート/イソブチルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=20/35/35/10の共重合体の溶液、重量平均分子量:31,000、固形分:60%、溶剤:ミネラルスピリット[B6]
Solution of copolymer of isobornyl acrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 20/35/35/10, weight average molecular weight: 31,000, solid content: 60%, Solvent: Mineral Spirit
[B7]
イソボルニルアクリレート/2−ヒドロキシエチルメタクリレート/イソブチルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=20/5/30/35/10の共重合体の溶液、重量平均分子量:30,000、固形分:60%、溶剤:ミネラルスピリット[B7]
Solution of copolymer of isobornyl acrylate / 2-hydroxyethyl methacrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 20/5/30/35/10, weight average molecular weight: 30, 000, solid content: 60%, solvent: mineral spirit
[B8]
イソボルニルアクリレート/シクロヘキシルメタクリレート/2−ヒドロキシエチルメタクリレート/イソブチルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=20/20/10/5/35/10の共重合体の溶液、重量平均分子量:35,000、固形分:60%、溶剤:ミネラルスピリット[B8]
Solution of copolymer of isobornyl acrylate / cyclohexyl methacrylate / 2-hydroxyethyl methacrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 20/20/10/5/35/10, weight Average molecular weight: 35,000, solid content: 60%, solvent: mineral spirit
[B9]
イソボルニルアクリレート/メチルメタクリレート/2−ヒドロキシエチルメタクリレート/イソブチルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=20/10/15/15/35/5の共重合体の溶液、重量平均分子量:40,000、固形分:60%、溶剤:ミネラルスピリット[B9]
Isobornyl acrylate / methyl methacrylate / 2-hydroxyethyl methacrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 20/10/15/15/35/5 copolymer solution, weight Average molecular weight: 40,000, solid content: 60%, solvent: mineral spirit
[B10]
シクロヘキシルメタクリレート/t−ブチルメタクリレート/2−ヒドロキシエチルメタクリレート/イソブチルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=25/10/15/15/30/5の共重合体の溶液、重量平均分子量:22,000、固形分:60%、溶剤:ミネラルスピリット[B10]
Solution of cyclohexyl methacrylate / t-butyl methacrylate / 2-hydroxyethyl methacrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 25/10/15/15/30/5 copolymer, weight Average molecular weight: 22,000, solid content: 60%, solvent: mineral spirit
[B11]
シクロヘキシルメタクリレート/t−ブチルメタクリレート/イソブチルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=35/15/15/25/10の共重合体の溶液、重量平均分子量:33,000、固形分:60%、溶剤:ミネラルスピリット[B11]
Solution of copolymer of cyclohexyl methacrylate / t-butyl methacrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 35/15/15/25/10, weight average molecular weight: 33,000, solid Min: 60%, Solvent: Mineral Spirit
[B12]
シクロヘキシルメタクリレート/イソブチルメタクリレート/2−エチルヘキシルメタクリレート/γ−メタクリロキシプロピルトリメトキシシラン=45/15/30/10の共重合体の溶液、重量平均分子量:29,000、固形分:60%、溶剤:ミネラルスピリット[B12]
Solution of copolymer of cyclohexyl methacrylate / isobutyl methacrylate / 2-ethylhexyl methacrylate / γ-methacryloxypropyltrimethoxysilane = 45/15/30/10, weight average molecular weight: 29,000, solid content: 60%, solvent: Mineral spirits
≪加水分解性シリル基含有シリコーン樹脂(C)≫
[C1]
加水分解性シリル基含有フェニルメチルアルコキシシリコーンオリゴマー、重量平均分子量:1,200、固形分:100%
[C2]
加水分解性シリル基含有フェニルメチルアルコキシシリコーンオリゴマー、重量平均分子量:6,000、固形分:100%
[C3]
加水分解性シリル基含有ジメチルアルコキシシリコーンオリゴマー、重量平均分子量:2,500、固形分:100%≪Hydrolysable silyl group-containing silicone resin (C) ≫
[C1]
Hydrolyzable silyl group-containing phenylmethylalkoxysilicone oligomer, weight average molecular weight: 1,200, solid content: 100%
[C2]
Hydrolyzable silyl group-containing phenylmethylalkoxysilicone oligomer, weight average molecular weight: 6,000, solid content: 100%
[C3]
Hydrolyzable silyl group-containing dimethylalkoxysilicone oligomer, weight average molecular weight: 2,500, solid content: 100%
≪オルガノシリケート(D)≫
[D1]
「エチルシリケート48」、商品名、多摩化学社製、テトラエトキシシランの縮合物≪Organosilicate (D) ≫
[D1]
"Ethyl silicate 48", trade name, manufactured by Tama Chemicals, condensate of tetraethoxysilane
≪その他の成分≫
[E1]
二酸化チタン、「TRONOX CR−826」、商品名、TRONOX PIGMENTS社製
[E2]
増粘剤、「ディスパロン6820−10M」、商品名、楠本化成株式会社、アマイド
[E3]
触媒、「SCAT−8」、商品名、ジブチル錫アセテート
[E4]
シランカップリング剤、3−グリシドキシプロピルトリエトキシシラン≪Other ingredients≫
[E1]
Titanium dioxide, “TRONOX CR-826”, trade name, manufactured by TRONOX PIGMENTS [E2]
Thickener, “Disparon 6820-10M”, trade name, Enomoto Kasei Co., Ltd., Amide [E3]
Catalyst, “SCAT-8”, trade name, dibutyltin acetate [E4]
Silane coupling agent, 3-glycidoxypropyltriethoxysilane
[耐候性]
キセノンウェザーメーター試験機を用いて、試験板(A)及び試験版(B)の促進耐候性を評価した。5000時間経過後の塗膜の光沢を、促進耐候性試験を行っていない初期の塗膜の光沢と、下記の基準に従って比較した。
◎:光沢がほとんど低下しなかった
○:光沢が若干低下したが、製品として問題がない
△:光沢がやや低下した
×:光沢が著しく低下した[Weatherability]
The accelerated weather resistance of the test plate (A) and the test plate (B) was evaluated using a xenon weather meter tester. The gloss of the coating after 5000 hours was compared with the gloss of the initial coating without the accelerated weather resistance test, according to the following criteria.
◎: Gloss was hardly decreased. ○: Gloss was slightly decreased, but there was no problem as a product. △: Gloss was slightly decreased. X: Gloss was significantly decreased.
[耐屈曲性]
塗料組成物No.1〜40を、アセトンで脱脂した鋼板上に、乾燥膜厚が25μmとなるようにスプレー塗装し、23℃で168時間乾燥させることにより、試験板(C)No.1〜40を製造し、試験板(C)No.1〜40の耐屈曲性を評価した。
耐屈曲性は、JIS K 5600−5−1:1999の第5部:塗膜の機械的性質、第1節:耐屈曲性(円筒形マンドレル法)に従い、マンドレルの直径が10mmのタイプIの試験装置を用いて、下記基準に従って評価した。[Flexibility]
Coating composition No. 1 to 40 were spray-coated on a steel plate degreased with acetone so that the dry film thickness was 25 μm, and dried at 23 ° C. for 168 hours. 1 to 40 are manufactured and the test plate (C) No. 1 is manufactured. The bending resistance of 1 to 40 was evaluated.
According to JIS K 5600-5-1: 1999, part 5: mechanical properties of the coating film, section 1: bending resistance (cylindrical mandrel method), the mandrel diameter is 10 mm. Evaluation was performed according to the following criteria using a test apparatus.
◎:屈曲面の塗膜に変化が観察されなかった
○:屈曲面の塗膜にワレは観察されなかったが、塗膜に僅かに変化があった
△:屈曲部の塗膜の一部にワレが観察された
×:屈曲部の塗膜全体にワレが観察された◎: No change was observed in the coating film on the bent surface ○: No crack was observed in the coating film on the bent surface, but there was a slight change in the coating film △: Part of the coating film on the bent portion Cracks were observed x: Cracks were observed in the entire coating film at the bent portion
[防食性]
試験板(C)No.1〜40に、カッターナイフで、金属基材に達するように、幅1mmのX字型の傷を付け、500時間の塩水噴霧試験を実施し、塗膜の状態を下記基準に従って評価した。
○:カッターナイフで傷を付けた箇所に異常が観察されなかった
△:カッターナイフで傷を付けた箇所を中心にわずかに錆が観察された
×:カッターナイフで傷を付けた箇所を中心に著しい錆が観察された[Anti-corrosion]
Test plate (C) No. From 1 to 40, an X-shaped scratch having a width of 1 mm was applied with a cutter knife so as to reach the metal substrate, a 500 hour salt spray test was performed, and the state of the coating film was evaluated according to the following criteria.
○: No abnormality was observed at the place where the scratch was made with the cutter knife. △: Slight rust was observed around the place where the scratch was made with the cutter knife. X: Around the place where the damage was made with the cutter knife. Significant rust was observed
[厚膜塗装性]
垂直に立てたアセトンで脱脂した鋼板上に、塗料組成物No.11〜40を、JIS K 5400−6.4に示すサグテスターを用いて塗装し、23℃で24時間乾燥させた後、塗膜の流れていない部分の乾燥膜厚の上限を測定し、下記基準で評価した。
◎:上限が60μm以上であった
○:上限が55μm以上且つ60μm未満であった
△:上限が50μm以上且つ55μm未満であった
×:上限が50μm未満であった[Thick film paintability]
On the steel plate degreased vertically with acetone, the coating composition No. After coating 11-40 using a sag tester shown in JIS K 5400-6.4 and drying at 23 ° C. for 24 hours, the upper limit of the dry film thickness of the part where the coating film does not flow was measured, and the following criteria It was evaluated with.
◎: The upper limit was 60 μm or more ○: The upper limit was 55 μm or more and less than 60 μm △: The upper limit was 50 μm or more and less than 55 μm ×: The upper limit was less than 50 μm
[補修性]
アセトンで脱脂した鋼板上に、弱溶剤可溶厚膜型変性エポキシ樹脂系錆止め塗料(「エスコNBセーフティ」(商品名、関西ペイント社製、主剤/アミン硬化剤=17/1)を、乾燥膜厚が60μmとなるようにスプレー塗装し、23℃で24時間乾燥させ、その上に、弱溶剤可溶イソシアネート硬化ポリウレタン塗料(「セラテクトマイルド中塗り」(商品名、関西ペイント社製、主剤/イソシアネート硬化剤質量比10/1)を、乾燥膜厚が30μmとなるようにスプレー塗装し、23℃で24時間乾燥させ、そしてその上に、塗料組成物No.1〜40を、乾燥膜厚が25μmとなるようにスプレー塗装し、23℃で168時間乾燥させた。次いで、その上に、補修用上塗り塗膜として、同一の塗料組成物No.1〜40を、乾燥膜厚が25μmとなるようにスプレー塗装し、23℃で168時間乾燥させることにより、試験板(D)No.1〜40を製造した。試験板(D)No.1〜40を、水に168時間浸漬し、水から引き上げ直後に、JIS K5600の「第5部:塗膜の機械的性質」、「第6節:付着性(クロスカット法)」に従って付着性を試験し、下記基準に従って評価した。[Repairability]
On a steel plate degreased with acetone, a weak solvent soluble thick film type modified epoxy resin-based rust preventive paint ("ESCO NB Safety" (trade name, manufactured by Kansai Paint Co., Ltd., main agent / amine curing agent = 17/1), dried film Spray-coated to a thickness of 60 μm and dried at 23 ° C. for 24 hours. On top of this, a weak solvent-soluble isocyanate-cured polyurethane coating (“Serect Mild Intermediate Coating” (trade name, manufactured by Kansai Paint Co., Ltd., main agent / Isocyanate curing agent mass ratio 10/1) was spray-coated so that the dry film thickness was 30 μm, dried at 23 ° C. for 24 hours, and then, coating composition No. 1 to 40 was dried film thickness. Was spray-coated so as to be 25 μm, and dried for 168 hours at 23 ° C. Next, the same coating composition No. 1 to 40 was applied as a top coat film for repair onto the coating film. The test plate (D) No. 1 to 40 was produced by spray coating to 5 μm and drying at 23 ° C. for 168 hours.The test plate (D) No. 1 to 40 was immersed in water for 168 hours. Immediately after pulling up from the water, the adhesion was tested in accordance with JIS K5600 “Part 5: Mechanical properties of coating film” and “Section 6: Adhesion (cross-cut method)” and evaluated according to the following criteria.
◎:補修用上塗り塗膜が剥離しなかった
○:補修用上塗り塗膜が僅かに剥離した
△:補修用上塗り塗膜が一部剥離した
×:補修用上塗り塗膜が剥離した◎: Repair topcoat film did not peel ○: Repair topcoat film slightly peeled △: Repair topcoat film partially peeled ×: Repair topcoat film peeled
本発明は、以下のJ1〜J13に関する。
[J1]
加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)を含む耐候性塗料組成物。
[J2]
加水分解性シリル基含有フッ素樹脂(A)が、フッ素含有オレフィン(a1)と、加水分解性シリル基含有重合性不飽和化合物(a3)との単量体単位を含む、J1に記載の組成物。The present invention relates to the following J1 to J13.
[J1]
A weatherable coating composition comprising a hydrolyzable silyl group-containing fluororesin (A), a hydrolyzable silyl group-containing acrylic resin (B), and a hydrolyzable silyl group-containing silicone resin (C).
[J2]
The hydrolyzable silyl group-containing fluororesin (A) according to J1, comprising a monomer unit of a fluorine-containing olefin (a 1 ) and a hydrolyzable silyl group-containing polymerizable unsaturated compound (a 3 ). Composition.
[J3]
加水分解性シリル基含有フッ素樹脂(A)が、フッ素含有オレフィン(a1)と、ビニルアルコキシシラン(a31)と、(メタ)アクリロイル基含有化合物(a41)との単量体単位を含む、J1又はJ2に記載の組成物。
[J4]
加水分解性シリル基含有アクリル樹脂(B)が、加水分解性シリル基含有重合性不飽和化合物(b1)と、(メタ)アクリロイル基含有化合物(b2)との単量体単位を含む、J1〜J3のいずれか一項に記載の組成物。[J3]
The hydrolyzable silyl group-containing fluororesin (A) includes monomer units of a fluorine-containing olefin (a 1 ), a vinylalkoxysilane (a 31 ), and a (meth) acryloyl group-containing compound (a 41 ). , J1 or J2.
[J4]
The hydrolyzable silyl group-containing acrylic resin (B) includes monomer units of a hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) and a (meth) acryloyl group-containing compound (b 2 ). The composition as described in any one of J1-J3.
[J5]
加水分解性シリル基含有アクリル樹脂(B)が、全単量体単位を基準として、加水分解性シリル基含有重合性不飽和化合物(b1)及び(メタ)アクリロイル基含有化合物(b2)を、単量体単位として、それぞれ、1〜50質量%及び50〜99質量%含む、J1〜J4のいずれか一項に記載の組成物。[J5]
The hydrolyzable silyl group-containing acrylic resin (B) contains, based on all monomer units, a hydrolyzable silyl group-containing polymerizable unsaturated compound (b 1 ) and a (meth) acryloyl group-containing compound (b 2 ). The composition according to any one of J1 to J4, which contains 1 to 50% by mass and 50 to 99% by mass as monomer units, respectively.
[J6]
加水分解性シリル基含有アクリル樹脂(B)が、単量体単位として、(メタ)アクリル酸と、炭素数4〜18の直鎖状、分岐状又は環状アルコールとのエステル(b22)を含む、J1〜J5のいずれか一項に記載の組成物。
[J7]
加水分解性シリル基含有シリコーン樹脂(C)が、ケイ素原子に直接結合するメチル基及び/又はフェニル基を有するオリゴマーである、J1〜J6のいずれか一項に記載の組成物。[J6]
The hydrolyzable silyl group-containing acrylic resin (B) contains an ester (b 22 ) of (meth) acrylic acid and a linear, branched or cyclic alcohol having 4 to 18 carbon atoms as a monomer unit. , The composition according to any one of J1 to J5.
[J7]
The composition according to any one of J1 to J6, wherein the hydrolyzable silyl group-containing silicone resin (C) is an oligomer having a methyl group and / or a phenyl group directly bonded to a silicon atom.
[J8]
加水分解性シリル基含有フッ素樹脂(A)、加水分解性シリル基含有アクリル樹脂(B)及び加水分解性シリル基含有シリコーン樹脂(C)を、それらの総固形分質量に基づいて、それぞれ、1〜90質量%、3〜94質量%、及び3〜50質量%含む、J1〜J7のいずれか一項に記載の組成物。[J8]
The hydrolyzable silyl group-containing fluororesin (A), the hydrolyzable silyl group-containing acrylic resin (B) and the hydrolyzable silyl group-containing silicone resin (C) are each 1 based on their total solid mass. The composition as described in any one of J1-J7 containing -90 mass%, 3-94 mass%, and 3-50 mass%.
[J9]
加水分解性シリル基の重縮合を促進する触媒をさらに含む、J1〜J8のいずれか一項に記載の組成物。
[J10]
弱溶剤型の塗料組成物である、J1〜J9のいずれか一項に記載の組成物。[J9]
The composition according to any one of J1 to J8, further comprising a catalyst that promotes polycondensation of hydrolyzable silyl groups.
[J10]
The composition according to any one of J1 to J9, which is a weak solvent type coating composition.
[J11]
耐候性塗膜を有する塗装物品の製造方法であって、
被塗物に、J1〜10のいずれか一項に記載の組成物を塗装し、耐候性塗膜を形成するステップ、
を含む方法。[J11]
A method for producing a coated article having a weather resistant coating,
Applying the composition according to any one of J1 to 10 to an object to be coated to form a weather-resistant coating film;
Including methods.
[J12]
上記耐候性塗膜を形成するステップの前に、被塗物に下塗り塗料を塗装し、防食塗膜を形成するステップを含む、J11に記載の方法。
[J13]
上記防食塗膜を形成するステップの後且つ上記耐候性塗膜を形成するステップの前に、上記防食塗膜の上に中塗り塗料を塗装し、中塗り塗膜を形成するステップを含む、請求項12に記載の方法。[J12]
The method according to J11, comprising a step of applying an undercoating paint to an article to form an anticorrosion coating before the step of forming the weather resistant coating.
[J13]
After the step of forming the anticorrosion coating film and before the step of forming the weather resistant coating film, the method includes a step of applying an intermediate coating on the anticorrosion coating film to form an intermediate coating film. Item 13. The method according to Item 12.
Claims (13)
オルガノシリケート(D)が、次の式:
Si(−OR1)4
(式中、R1は、アルキル基、アリール基及びアラルキル基から選択される、同一又は異なる1価の炭化水素基である)
で示される化合物、及びその部分加水分解及び縮合物、並びにそれらの組み合わせから成る群から選択される、
前記耐候性塗料組成物。 A hydrolyzable silyl group-containing fluorocarbon resin (A), the hydrolyzable silyl group-containing acrylic resin (B), the hydrolyzable silyl group-containing silicone resin (C), a hydrolyzable silyl group-containing silicone resin (C) containing organosilicate (D) and a component other than, a weather resistant coating composition of weak solvent type,
Organosilicate (D) has the following formula:
Si (—OR 1 ) 4
(Wherein R 1 is the same or different monovalent hydrocarbon group selected from an alkyl group, an aryl group and an aralkyl group)
Selected from the group consisting of compounds represented by: and partial hydrolysis and condensates thereof, and combinations thereof,
The weather-resistant coating composition.
被塗物に、請求項1〜10のいずれか一項に記載の組成物を塗装し、耐候性塗膜を形成するステップ、
を含む方法。A method for producing a coated article having a weather resistant coating,
Applying the composition according to any one of claims 1 to 10 to an object to be coated to form a weather-resistant coating film;
Including methods.
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JP6497695B2 (en) * | 2014-11-25 | 2019-04-10 | 関西ペイント株式会社 | Room temperature curable weatherable paint composition |
CN104371472B (en) * | 2014-12-03 | 2016-01-06 | 温州泓呈祥科技有限公司 | A kind of weatherability coating and preparation method thereof |
CN104403507A (en) * | 2014-12-18 | 2015-03-11 | 无锡伊诺永利文化创意有限公司 | Paint special for outdoor advertisements |
JP6497697B2 (en) * | 2015-01-30 | 2019-04-10 | 関西ペイント株式会社 | Room temperature curable weatherable paint composition |
JP2017145355A (en) * | 2016-02-19 | 2017-08-24 | 大日本塗料株式会社 | Two-liquid aqueous undercoating composition, coated body, and method for producing the same |
JP2023052716A (en) * | 2020-03-16 | 2023-04-12 | Agc株式会社 | Paint and base material with coating film |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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LAPS | Cancellation because of no payment of annual fees |