JP6108393B2 - 機能層を形成する方法 - Google Patents
機能層を形成する方法 Download PDFInfo
- Publication number
- JP6108393B2 JP6108393B2 JP2013150833A JP2013150833A JP6108393B2 JP 6108393 B2 JP6108393 B2 JP 6108393B2 JP 2013150833 A JP2013150833 A JP 2013150833A JP 2013150833 A JP2013150833 A JP 2013150833A JP 6108393 B2 JP6108393 B2 JP 6108393B2
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- Prior art keywords
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- meth
- compound
- acrylate
- parts
- Prior art date
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- -1 silane compound Chemical class 0.000 claims description 82
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- RCXMKFXRSOFCSI-UHFFFAOYSA-N dibutoxy-(3-isocyanatopropyl)-methylsilane Chemical compound CCCCO[Si](C)(OCCCC)CCCN=C=O RCXMKFXRSOFCSI-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- VNNPFQQFUFDPJM-UHFFFAOYSA-N diethoxy-(2-isocyanatoethyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CCN=C=O VNNPFQQFUFDPJM-UHFFFAOYSA-N 0.000 description 1
- PJIFJEUHCQYNHO-UHFFFAOYSA-N diethoxy-(3-isocyanatopropyl)-methylsilane Chemical compound CCO[Si](C)(OCC)CCCN=C=O PJIFJEUHCQYNHO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- SGOFQQOFFFUGGF-UHFFFAOYSA-N diphenylphosphoryl-(1,2,4-trimethylcyclohexa-2,4-dien-1-yl)methanone Chemical compound C1(=CC=CC=C1)P(C(C1(CC=C(C=C1C)C)C)=O)(C1=CC=CC=C1)=O SGOFQQOFFFUGGF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000001652 electrophoretic deposition Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011151 fibre-reinforced plastic Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- JTXAHXNXKFGXIT-UHFFFAOYSA-N propane;prop-1-ene Chemical group CCC.CC=C JTXAHXNXKFGXIT-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-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
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- FGKCGMMQJOWMFW-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;bromide Chemical compound [Br-].CC(=C)C(=O)OCC[N+](C)(C)C FGKCGMMQJOWMFW-UHFFFAOYSA-M 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Description
本発明においてガラス転移温度が80℃以上である硬化塗膜(I)は、基材面に前記範囲のガラス転移温度を有する硬化塗膜を形成し得る塗料組成物を塗装し硬化することによって得られるものである。
プラズマ処理は、具体的には、例えば、東芝メカニクス(株)社製のマイクロプラズマ処理装置TMP−7048A、TMW−7407、TMZ−9602−A、IPC社製の200S高周波プラズマ処理装置、及びヤマト科学(株)社製のPR−510、PDC210、及びウェッジ(株)社製のPS−1200AW等を用いて行うことができる。
コロナ放電処理は、市販のコロナ機、具体的には例えば、ピラー社製のソリッドステートコロナ処理機、SOFTAL社製のTreating Generator、及びVETAPHONE高周波インパルス表面処理機(例えば、T−2000、T−4000)等を用いて行うことができる。
活性エネルギー線処理の活性エネルギー線としては、紫外線、電子線、電磁波等を挙げることができる。紫外線処理は、具体的には例えば、エキシマーレーザー、高圧水銀灯、アーク灯等の光源を用いて行うことができる。
火炎処理は、バーナーなど火炎噴射装置を使用して火炎を基材表面に吹き付けることにより行うことができる。処理量としては、水酸基の生成量確保の観点から、硬化塗膜(I)面の水接触角が50°以下となる程度に行うことが好ましい。
本発明では、上記の通り水酸基を生成せしめ硬化塗膜(I)の処理面に、イソシアネート基含有不飽和化合物、イソシアネート基含有シラン化合物から選ばれる少なくとも1種を含有する組成物(A)を塗布し乾燥させてプライマー層(II)を形成する。
上記一般式(1)で表わされる化合物としては、具体的には、例えば、3−イソシアネートプロピルトリメトキシシラン、3−イソシアネートプロピルトリエトキシシラン、3−イソシアネートプロピルトリブトキシシラン、3−イソシアネートプロピルメチルジメトキシシラン、3−イソシアネートプロピルメチルジメトキシシラン、3−イソシアネートプロピルメチルジエトキシシラン、3−イソシアネートプロピルメチルジプロポキシシラン、3−イソシアネートプロピルメチルジブトキシシラン、2−イソシアネートエチルトリメトキシシラン、2−イソシアネートエチルトリエトキシシラン、2−イソシアネートエチルメチルジメトキシシラン、2−イソシアネートエチルメチルジエトキシシランなどが挙げられ、これらは単独で又は2種以上を併用して使用することができる。
本発明では、上記のとおり形成されたプライマー層と反応し得る反応性基を有する機能層(III)を形成する。反応性基としては、重合性不飽和基、アルコキシシリル基等が挙げられる。かかる機能層(III)の形成により、硬化塗膜(I)、プライマー層(II)及び機能層(III)が一体となって強固に結合した、表面が改質され新たに機能性が付与された塗装物品を得ることができる。
1)親水性を付与するための、親水性基、
2)撥水性/撥油性を付与するための、撥水性/撥油性基、
3)屈折率変動を付与するための、屈折率変動基、
4)紫外線吸収特性を付与するための、紫外線吸収性を有する官能基、
5)光安定性を付与するための、光安定性を有する官能基、
等を挙げることができる。
〔式中、R1は水素原子又はメチル基、R2は−CPH2P−、−C(CPH2P+1)H−、−CH2C(CPH2P+1)H−又は−CH2CH2O−、Rfは−CnF2n+1、−(CF2)nH、−CnF2n−CF3、−(CF2)pOCnF2nCjH2j+1、−(CF2)pOCmH2mCiH2iH、−N(CPH2P+1)COCnF2n+1、−N(CPH2P+1)SO2CnF2n+1である。但し、pは1〜10、nは1〜16、mは0〜10、jは0〜10、iは0〜16の整数である。〕
CF2=CFORg ・・・(II)
(式中Rgは炭素数1〜20のフルオロアルキル基を表わす。)
CH2=CHRg・・・(III)
(式中Rgは炭素数1〜20のフルオロアルキル基を表わす。)
CH2=CR3COOR5RjR6OCOCR4=CH2 ・・・(IV)
〔式中、R3、R4は水素原子又はメチル基、R5、R6は−CqH2q−、−C(CqH2q+1)H−、−CH2C(CqH2q+1)H−又は−CH2CH2O−、Rjは−CtF2tである。但し、qは1〜10、tは1〜16の整数である。〕
CH2=CHR7COOCH2(CH2Rk)CHOCOCR8=CH2・・・(V)
(式中、R7、R8は水素原子又はメチル基、Rkは−CyF2y+1である。但し、yは1〜16の整数である。)
上記のフッ素含有不飽和化合物としては、以下の具体例を挙げることができる。
R5Si(X)3 (2)
(但し、Xはアルコキシ基又はハロゲン原子を表し、R5が親水性基を表す)により表されるものが使用でき、親水性基は前述で列記の中から適宜選択される基を末端に有するものが挙げられ、例えば3−アミノプロピルトリエトキシシラン、スルホエチルトリメトキシシランなどが例示できる。
撹拌装置、温度計、冷却管、窒素ガス導入口を備えた四ツ口フラスコにエトキシエチルプロピオネート31部を仕込み、窒素ガス通気下で155℃に昇温した。155℃に達した後、窒素ガスの通気を止め、表1に示すモノマー及び重合開始剤の混合物を4時間かけて滴下した。155℃で窒素ガスを通気しながら2時間熟成させた後、100℃まで冷却し、酢酸ブチル32.5部で希釈することにより、固形分60%の各水酸基含有アクリル樹脂1〜5の溶液を得た。
上記製造例で得られた各水酸基含有アクリル樹脂及びポリイソシアネート化合物等を表2に示す配合にてディスパーを用いて攪拌混合して塗料化を行い、熱硬化性のクリヤ塗料1〜3を得た。
(注2)TINUVIN384:BASF社製、紫外線吸収剤
(注3)TINUVIN292:BASF社製、光安定剤
上記製造例で得られた水酸基含有アクリル樹脂4を固形分量で95部、水酸基含有アクリル樹脂5を固形分量で5部、「スミジュールN−3300」を54部、ジブチル錫ジラウレートを0.005部、トリエチルアミンを1.2部、オクチル酸を0.8部及びチタン白60部を均一に混合し、さらに酢酸ブチルでディスパーを用いて攪拌混合して塗料化を行い、熱硬化性の着色塗料1を得た。得られた着色塗料1による硬化塗膜のガラス転移温度は106℃であった。
「パルボンド#3020」(日本パーカライジング社製、りん酸亜鉛処理)を施した冷延鋼板(大きさ400×300×0.8mm)に、「エレクロンGT−10」(関西ペイント社製、熱硬化性エポキシ樹脂系カチオン電着塗料)を膜厚20μmとなるように電着塗装し、170℃で30分間加熱して硬化させ、該塗膜上に「TP−65」(関西ペイント社製、商品名、ポリエステル・メラミン樹脂系自動車中塗塗料)を乾燥膜厚35μmとなるようにエアスプレー塗装し、140℃で30分間加熱硬化させた。次いでその上に、水性ベースコート「WBC713T」(関西ペイント社製、商品名、アクリル・メラミン樹脂系自動車上塗ベースコート塗料、白塗色)を乾燥膜厚15μmとなるように塗装し、室温で5分間放置してから、80℃で10分間プレヒートを行なった後、未硬化の該塗膜上に、上記の通り製造したクリヤ塗料1を乾燥膜厚30μmとなるように塗装した後、140℃で30分間加熱硬化させることにより硬化塗膜面を有する試験板(I)を得た。
上記試験板(I)の作成において、水性ベースコート「WBC713T」を乾燥膜厚15μmとなるように塗装するまでは同様にして、ベースコート塗膜を140℃で30分間加熱硬化させた。その後、クリヤ塗料4(注4)を乾燥膜厚が20μmになるように塗装し、高圧水銀灯180W/cmにて線量700mJ/cm2となるよう照射して、クリヤ塗膜を硬化させることにより硬化塗膜面を有する試験板(IV)を得た。
表面を脱脂したABS板(大きさ100×150×3mm)に、上記の通り製造した着色塗料1を乾燥膜厚30μmとなるように塗装し、室温で5分間放置してから、80℃で20分間加熱硬化させることにより硬化塗膜面を有する試験板(V)を得た。
調製例1
イソシアネート基含有不飽和化合物(1)(注6)10部、「ネオスタンU−100」」(商品名、日東化成社製、ジブチル錫ジラウレート)0.05部及び酢酸ブチル90部を混合して溶液(A−1)を得た。
イソシアネート基含有不飽和化合物(1)10部及び酢酸ブチル90部を混合して溶液(A−2)を得た。
イソシアネート基含有不飽和化合物(1)10部、「ネオスタンU−100」 0.05部及びスワゾール1000(石油系炭化水素溶剤)90部を混合して溶液(A−3)を得た。
イソシアネート基含有不飽和化合物(1)10部、ヘキサエートカルシウム 0.05部及びスワゾール1000(石油系炭化水素溶剤)90部を混合して溶液(A−4)を得た。
イソシアネート基含有不飽和化合物(2)(注7)10部、「ネオスタンU−100 」0.05部及びスワゾール1000(石油系炭化水素溶剤)90部を混合して溶液(A−5)を得た。
イソシアネート基含有不飽和化合物(3)(注8)10部、「ネオスタンU−100」0.05部及びスワゾール1000(石油系炭化水素溶剤)90部を混合して溶液(A−6)を得た。
イソシアネート基含有シラン化合物(1)(注9)10部、「ネオスタンU−100」0.05部及び酢酸エチル90部を混合して溶液(A−7)を得た。
調製例8
「スミジュールN−3300」10部、「ネオスタンU−100」0.05部及び酢酸エチル90部を混合して溶液(A−8)を得た。
ペンタエリスリトールテトラアクリレート10部及び酢酸エチル90部を混合して溶液(A−9)を得た。
調製例10
メタクリロイルオキシエチル−N,N−ジメチルアンモニウム−α−メチルカルボキシベタイン10部、「IRGACURE184」(光重合開始剤、BASF社製)1部、エタノール80部及び脱イオン水10部を混合して組成物(B1−1)を得た。
メタクリロイルオキシエチル−N,N−ジメチル−N−(3−スルホプロピル)アンモニウムベタイン10部、「IRGACURE184」1部、エタノール80部及び脱イオン水10部を混合して組成物(B1−2)を得た。
ビニルスルホン酸10部、「IRGACURE184」1部、エタノール80部及び脱イオン水10部を混合して組成物(B1−3)を得た。
ビニルスルホン酸10部、水酸化ナトリウム3.7部及び脱イオン水10部を混合し、さらに「IRGACURE184」1部、エタノール80部を加えて混合して組成物(B1−4)を得た。
ビニルスルホン酸10部、ジメチルエタノールアミン8.2部及び脱イオン水10部を混合し、さらに「IRGACURE184」1部、エタノール80部を加えて混合して組成物(B1−5)を得た。
ビニルスルホン酸10部、28%アンモニア水5.6部及び脱イオン水6部を混合し、さらに「IRGACURE184」1部、エタノール80部を加えて混合して組成物(B1−6)を得た。
アリルスルホン酸ソーダ10部、「IRGACURE184」1部、エタノール80部及び脱イオン水10部を混合して組成物(B1−7)を得た。
「ファンクリルFA−400M」(メトキシポリエチレングリコールモノメタクリレート、日立化成工業社製)10部、「IRGACURE184」1部、エタノール80部及び脱イオン水10部を混合して組成物(B1−8)を得た。
「ノストラ H2」(親水基含有UV硬化コート剤、三井化学社製、固形分80%)12.5部、「IRGACURE184」 1部、エタノール77.5部及び脱イオン水10部を混合して組成物(B1−9)を得た。
「フルオレスター」(2,2,2−トリフルオロエチルメタクリレート、東ソーエフテック社製、固形分100%)10部、「IRGACURE184」1部及びスワゾール1000 90部を混合して組成物(B1−10)を得た。
「フルオレスター」8部、3−メチル−1,5−ペンタンジオールジアクリレート 2部、「IRGACURE184」1部及びスワゾール1000 90部を混合して組成物(B1−11)を得た。
「サイラプレーンFM−0711」(α−ブチル−ω−(3−メタクリロキシプロピル)ポリジメチルシロキサン、重量平均分子量1000、JNC社製、固形分100%)10部、「IRGACURE184」1部及びスワゾール1000 90部を混合して組成物(B1−12)を得た。
「LAMBIC−400EP」(親水基含有アルコキシシラン、10%エタノール溶液、大阪有機化学社製)を組成物(B2−1)として使用した。
「KBE−7803」(ヘプタデカフルオロデシルトリメトキシシラン、信越化学工業製)10部、イソプロパノール90部を混合して組成物(B2−2)を得た。
実施例1
コロナ処理(注10)を行った試験板(I)のクリヤ塗膜面に、溶液(A−1)を、マイクロワイプ(不織布)を用いて塗り伸ばした後、別の清浄なクロスでむらがなくなるまでふき取った後、赤外線ヒーターを用いて80℃で30分間加熱を行った。
試験板、プライマー層形成用溶液及び機能付与組成物として、表3に記載のものを使用し、試験板の処理及びプライマー層形成用溶液塗布後の加熱条件を、表3に記載のとおりに変更する以外は、実施例1と同様にして、各機能層形成試験板を得た。
コロナ装置(CG−102型コロナ放電発生装置、春日電機(株)社製)に試験板の塗膜面と放電管の距離を2mmに設定し、電流設定値3Aで放電させながら、試験板を1m/秒の速度で10パスさせた。水接触角が50°以下になっていることを確認してから各プライマー層形成用溶液を塗布した。
(注11)火炎処理:
ブタンガスのカートリッジがついたガスバーナーの火炎を試験板の塗膜面との距離を2cmに設定して、試験板上を速度5cm/秒で2パスさせた。水接触角が50°以下になっていることを確認してから各プライマー層形成用溶液を塗布した。
得られた機能層形成試験板の親水性及び撥水性を、水接触角を測定することにより評価した。水接触角の測定結果を表3に併せて示す。
上記L*値は、CIE等色関数に基づくL*値を測定することにより評価した。測定はBYKガードナー社製、カラーガイド45/0を用いて行なった。ΔL*値が小さい程、耐汚染性が良好であることを表わす。△L*値が1以下を○、1を超え〜3以下を△、3を超えるとき×とする。
Claims (5)
- 水酸基価80〜200mgKOH/gの水酸基含有樹脂及び硬化剤を含有する塗料組成物、またはラジカル重合性不飽和基含有化合物及び光重合開始剤を含有する塗料組成物から形成されるガラス転移温度が80℃以上である硬化塗膜(I)の表面に、酸化処理を行ない、次いで該処理面にイソシアネート基含有不飽和化合物及びイソシアネート基含有シラン化合物から選ばれる少なくとも1種を含有する組成物(A)を塗布し乾燥させてプライマー層(II)を形成した後、該プライマー層と反応し得る反応性基を有する機能層(III)を形成することを特徴とする機能層を形成する方法。
- 酸化処理が、プラズマ処理、コロナ放電、活性エネルギー線処理、及び火炎処理からなる群から選ばれた方法により行なわれる請求項1記載の方法。
- 機能層(III)が、機能性付与基含有不飽和化合物及び光重合開始剤を含有する組成物から形成されるものである請求項1または2に記載の方法。
- 機能層(III)が、機能性付与基含有シラン化合物を含有する組成物から形成されるものである請求項1ないし3のいずれか1項に記載の方法。
- 請求項1ないし4のいずれか1項に記載の方法により得られる機能層を有する塗装物品。
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