JPWO2019066029A1 - カチオン電着塗料組成物 - Google Patents
カチオン電着塗料組成物 Download PDFInfo
- Publication number
- JPWO2019066029A1 JPWO2019066029A1 JP2019545171A JP2019545171A JPWO2019066029A1 JP WO2019066029 A1 JPWO2019066029 A1 JP WO2019066029A1 JP 2019545171 A JP2019545171 A JP 2019545171A JP 2019545171 A JP2019545171 A JP 2019545171A JP WO2019066029 A1 JPWO2019066029 A1 JP WO2019066029A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- cationic
- electrodeposition coating
- resin
- coating composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000002091 cationic group Chemical group 0.000 title claims abstract description 99
- 238000004070 electrodeposition Methods 0.000 title claims abstract description 72
- 239000008199 coating composition Substances 0.000 title claims abstract description 53
- 229920005989 resin Polymers 0.000 claims abstract description 65
- 239000011347 resin Substances 0.000 claims abstract description 65
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 63
- 239000003822 epoxy resin Substances 0.000 claims abstract description 61
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 41
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 41
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 22
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 22
- 125000000962 organic group Chemical group 0.000 claims description 69
- 238000004519 manufacturing process Methods 0.000 claims description 56
- 238000000576 coating method Methods 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 239000011248 coating agent Substances 0.000 claims description 38
- 239000007787 solid Substances 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000003277 amino group Chemical group 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 abstract description 22
- -1 phenol compound Chemical class 0.000 description 143
- 239000002585 base Substances 0.000 description 62
- 239000000047 product Substances 0.000 description 44
- 125000000217 alkyl group Chemical group 0.000 description 37
- 125000003710 aryl alkyl group Chemical group 0.000 description 33
- 239000000049 pigment Substances 0.000 description 29
- 125000003118 aryl group Chemical group 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 150000002460 imidazoles Chemical class 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 201000006747 infectious mononucleosis Diseases 0.000 description 19
- 239000006185 dispersion Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- 125000003342 alkenyl group Chemical group 0.000 description 17
- 125000000304 alkynyl group Chemical group 0.000 description 17
- 239000000178 monomer Substances 0.000 description 17
- 229920000768 polyamine Polymers 0.000 description 17
- 125000000753 cycloalkyl group Chemical group 0.000 description 16
- 239000012948 isocyanate Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 125000005309 thioalkoxy group Chemical group 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 15
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002981 blocking agent Substances 0.000 description 9
- 239000003973 paint Substances 0.000 description 9
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 230000003746 surface roughness Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- GSURCHOJQKUXJB-UHFFFAOYSA-N C[N+]1=C(N(C=C1)CCCCCCCC)C(=O)[O-] Chemical compound C[N+]1=C(N(C=C1)CCCCCCCC)C(=O)[O-] GSURCHOJQKUXJB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- HESZXGSSISDCNI-UHFFFAOYSA-N 1,3-dimethylimidazol-1-ium-2-carboxylate Chemical compound CN1C=C[N+](C)=C1C([O-])=O HESZXGSSISDCNI-UHFFFAOYSA-N 0.000 description 3
- ISXOFOISGKIHMI-UHFFFAOYSA-M 1,3-dioctylimidazol-1-ium acetate Chemical compound C(C)(=O)[O-].C(CCCCCCC)[N+]1=CN(C=C1)CCCCCCCC ISXOFOISGKIHMI-UHFFFAOYSA-M 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 3
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 0 *C(*)(*)c1ccc(*)cc1 Chemical compound *C(*)(*)c1ccc(*)cc1 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- KLMZKZJCMDOKFE-UHFFFAOYSA-N 1-octylimidazole Chemical compound CCCCCCCCN1C=CN=C1 KLMZKZJCMDOKFE-UHFFFAOYSA-N 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
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- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 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
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Abstract
Description
項1.カチオン塩基含有樹脂(A)、ブロック化ポリイソシアネート化合物(B)、並びに下記式(1)で示されるイミダゾール変性物(C)を含有するカチオン電着塗料組成物。
項2.カチオン塩基含有樹脂(A)が、カチオン塩基含有エポキシ樹脂及び/又はカチオン塩基含有アクリル樹脂を含む項1に記載のカチオン電着塗料組成物。
項3.カチオン塩基含有樹脂(A)のカチオン塩基が、アミノ基、4級アンモニウム塩基、及びスルホニウム塩基からなる群より選ばれる少なくとも一種である項1に記載のカチオン電着塗料組成物。
項4.カチオン電着塗料組成物の樹脂固形分の総量を基準として、イミダゾール変性物(C)0.01〜10質量%含有する項1〜3のいずれか1項に記載のカチオン電着塗料組成物。
項5.項1〜4のいずれか1項に記載のカチオン電着塗料組成物からなる電着塗料浴に金属被塗物を浸漬し、電着塗装する塗装方法。
項6.項5に記載の塗装方法によって塗膜を形成する工程を含む、塗装物品の製造方法。
カチオン塩基含有樹脂(A)としては、カチオン塩基を含有する樹脂であれば、それ自体既知のものを特に制限なく用いることができる。なかでも、カチオン塩基含有エポキシ樹脂、カチオン塩基含有アクリル樹脂、またはその両方が好ましく、カチオン塩基含有エポキシ樹脂がより好ましい。
上記カチオン塩基含有エポキシ樹脂としては、例えば、アミノ基含有エポキシ樹脂、4級アンモニウム塩基含有エポキシ樹脂、及びスルホニウム塩基含有エポキシ樹脂などが挙げられ、いずれも好適に用いることができる。これらは1種を単独で又は2種以上を併用して用いることができる。
また、上記4級アンモニウム塩型エポキシ樹脂としては、アミン化合物に酸を付加して得られた塩をエポキシ樹脂に反応させて、またはエポキシ樹脂にアミン化合物を反応させ次いで酸を付加して、4級アンモニウム塩基を有するエポキシ樹脂を得ることができる。(例えば、特開2013−203966号公報参照)
上記カチオン塩基含有エポキシ樹脂の製造に使用されるエポキシ樹脂は、1分子中にエポキシ基を少なくとも1個、好ましくは2個以上有する化合物であり、その分子量は、少なくとも300、好ましくは400〜4000、さらに好ましくは800〜2500の範囲内の数平均分子量及び少なくとも160、好ましくは180〜2500、さらに好ましくは400〜1500の範囲内のエポキシ当量を有するものが適している。かかるエポキシ樹脂としては、例えば、ポリフェノール化合物とエピハロヒドリン(例えば、エピクロルヒドリン等)との反応によって得られるものを使用することができる。
ポリアルキレンオキシド鎖中のアルキレン基としては、炭素数が2〜8のアルキレン基が好ましく、エチレン基、プロピレン基またはブチレン基がより好ましく、プロピレン基が特に好ましい。
上記カチオン塩基含有アクリル樹脂としては、カチオン塩基含有アクリルモノマー及びその他のモノマーをラジカル共重合することによって製造することができる。
上記ブロック化ポリイソシアネート化合物(B)としては、ポリイソシアネート化合物(b−1)とブロック剤(b−2)との付加反応生成物である。また、必要に応じて、ブロック剤(b−2)以外の活性水素含有化合物を用い、ブロック剤(b−2)と共にポリイソシアネート化合物(b−1)と反応することができる。
上記イミダゾール変性物(C)は、下記式(1)で示される化合物である。
R1、R2、R3及び/又はR4が有機基である場合、当該有機基としては、例えば、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、シクロアルキルアルキル基、ヒドロキシアルキル基、アルコキシ基、チオアルコキシ基、アルコキシアルキル基、チオアルコキシアルキル基、アリール基、アリールアルキル基、アラルキル基、複素環基等の一価の有機基を挙げることができる。
R7及び/又はR8がアルキル基である場合、例えば、炭素数1〜10、好ましくは炭素数1〜6、より好ましくは炭素数1〜3、より好ましくは炭素数1〜2、より好ましくは炭素数1のアルキル基が挙げられる。R7及びR8は同一又は異なってもよいが、同一であることが好ましい。
は、同一でも異なっていてもよい。また、式(2)における上記部分は、パラ位置で窒素と結合すること、従って、下記構造を示すことが好ましい。
また、式(2)における
下記式(5)
で表される含窒素有機化合物(以下、含窒素有機化合物(5)という。)と下記式(6)
で表される炭酸ジアルキル(6)(以下、炭酸ジアルキル(6)という。)とを反応させて、式(7)
で表されるイミダゾール変性物(C1)を製造することができる。
下記式(8)
で表されるイソシアネート化合物(以下、イソシアネート化合物(8)という。)と前記イミダゾール変性物(C1)とを反応させて、式(9)
で表されるイミダゾール変性物(C2)を製造することができる。
で表されるイソシアネート化合物(以下、イソシアネート化合物(8’)という。)と前記イミダゾール変性物(C1)とを反応させる方法であって、当該反応の前、後及び/又はこれと同時に、さらに、イソシアネート基と反応するイミダゾール変性物(C1)以外の化合物(C3)(以下、化合物(C3)と示す)とを反応させて、下記式(9’)
で表されるイミダゾール化合物(C2’)を得る方法によっても製造することができる。
これらのイソシアネート化合物(8)としては、1種を単独で又は2種以上を併用して用いることができる。
本発明のカチオン電着塗料組成物におけるカチオン塩基含有樹脂(A)、及びブロック化ポリイソシアネート化合物(B)の配合割合としては、上記成分(A)及び(B)の樹脂固形分合計質量100部を基準にして、成分(A)の固形分を50〜90質量部、好ましくは55〜85質量部、成分(B)の固形分を10〜50質量部、好ましくは15〜45質量部の範囲内であることが、塗料安定性が良好で、仕上がり性、防食性に優れた塗装物品を得る為にも好ましい。また、イミダゾール変性物(C)の配合割合としては、例えば、カチオン電着塗料組成物の樹脂固形分の総量を基準として、0.01〜10質量%が好ましく、0.1〜8質量%がより好ましく、0.5〜6質量%がさらに好ましい。また、塗料中に含まれる樹脂全体のアミン価としては、樹脂固形分を基準として、アミン価が、通常20〜100mgKOH/gの範囲内であり、25〜90mgKOH/gの範囲内であることがより好ましい。
配合割合や樹脂全体のアミン価が上記範囲を外れると、上記の塗料特性及び塗膜性能のいずれかを損うことがあり好ましくない。
本発明は、前述のカチオン電着塗料組成物からなる電着浴に被塗物を浸漬する工程、及び被塗物を陰極として通電する工程を含む、カチオン電着塗膜の形成方法を提供する。また、本発明は、前述のカチオン電着塗料組成物からなる電着浴に被塗物を浸漬する工程、及び被塗物を通電して該被塗物に塗膜を形成する工程を含む、塗装物品の製造方法を提供する。
また、本発明は以下の構成を有することもできる。
[1]カチオン塩基含有樹脂(A)、ブロック化ポリイソシアネート化合物(B)、並びに下記式(1)で示されるイミダゾール変性物(C)を含有するカチオン電着塗料組成物。
[2]カチオン塩基含有樹脂(A)が、カチオン塩基含有エポキシ樹脂及び/又はカチオン塩基含有アクリル樹脂を含む[1]に記載のカチオン電着塗料組成物。
[3]カチオン塩基含有樹脂(A)のカチオン塩基が、アミノ基、4級アンモニウム塩基、及びスルホニウム塩基からなる群より選ばれる少なくとも一種である[1]に記載のカチオン電着塗料組成物。
[4]カチオン塩基含有樹脂(A)がアミノ基含有エポキシ樹脂、アミノ基含有エポキシ樹脂、またはその両方を含む[1]〜[3]のいずれか1項に記載のカチオン電着塗料組成物。
[5]R1、R2、R3、R4の有機基が、独立してアルキル基、アルケニル基、アルキニル基、シクロアルキル基、シクロアルキルアルキル基、ヒドロキシアルキル基、アルコキシ基、チオアルコキシ基、アルコキシアルキル基、チオアルコキシアルキル基、アリール基、アリールアルキル基、アラルキル基、又は複素環基である[1]〜[4]のいずれか1項に記載のカチオン電着塗料組成物。
[6]Xが酸素原子であり、R1及びR4が炭素数1〜5の有機基であり、R1の有機基及びR4の有機基は独立して、アルキル基、アルケニル基、アルキニル基、ヒドロキシアルキル基、アルコキシ基、チオアルコキシ基、アルコキシアルキル基、チオアルコキシアルキル基、アリール基、アリールアルキル基、アラルキル基、又は複素環基であり、R2及びR3は水素である[1]〜[5]のいずれか1項に記載のカチオン電着塗料組成物。
[7]Xが窒素原子であり、Yがアリール基又はアラルキル基である[1]〜[5]のいずれか1項に記載のカチオン電着塗料組成物。
[8]Yが式(2)で表される2価の基である[1]〜[5]のいずれか1項に記載のカチオン電着塗料組成物。
(式中、R7及びR8は同一又は異なって、水素又はアルキル基を示し、pは0以上の整数を示す。)
[9]Yが式(3)で表される2価の基である[1]〜[5]のいずれか1項に記載のカチオン電着塗料組成物。
(式中、R9、R10、及びR11は同一又は異なって、炭素数1以上の有機基であり、該有機基は酸素原子、窒素原子、硫黄原子及びハロゲン原子からなる群より選択される少なくとも一種を含んでもよく、s及びtは、0又は1であり、s及び/又はtが0の場合、
[10]Yが炭素数21以上の有機基である[7]〜[9]のいずれか1項に記載のカチオン電着塗料組成物。
[11]R1又はR4が炭素数6〜18(好ましくは6〜12)の有機基であり、有機基はアルキル基、アルケニル基、アルキニル基、シクロアルキル基、シクロアルキルアルキル基、ヒドロキシアルキル基、アルコキシ基、チオアルコキシ基、アルコキシアルキル基、チオアルコキシアルキル基、アリール基、アリールアルキル基、アラルキル基、又は複素環基である[7]〜[10]のいずれか1項に記載のカチオン電着塗料組成物。
[12]R1及びR4の一方が炭素数1〜5の有機基であり、R1及びR4の他方が炭素数6〜18(好ましくは6〜12)の有機基であり、R1の有機基及びR4の有機基は独立して、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、シクロアルキルアルキル基、ヒドロキシアルキル基、アルコキシ基、チオアルコキシ基、アルコキシアルキル基、チオアルコキシアルキル基、アリール基、アリールアルキル基、アラルキル基、又は複素環基である[7]〜[10]のいずれか1項に記載のカチオン電着塗料組成物。
[13]R1及びR4の一方が炭素数1〜5の有機基であり、R1及びR4の他方が炭素数6〜18(好ましくは6〜12)の有機基であり、R1の有機基及びR4の有機基は独立して、アルキル基、アルケニル基、アルキニル基、ヒドロキシアルキル基、アルコキシ基、チオアルコキシ基、アルコキシアルキル基、チオアルコキシアルキル基、アリール基、アリールアルキル基、アラルキル基、又は複素環基であり、R2及びR3は水素である[7]〜[10]のいずれか1項に記載のカチオン電着塗料組成物。
[14]R1及びR4が炭素数6〜18(好ましくは6〜12)の有機基であり、R1の有機基及びR4の有機基は独立して、アルキル基、アルケニル基、アルキニル基、シクロアルキル基、シクロアルキルアルキル基、ヒドロキシアルキル基、アルコキシ基、チオアルコキシ基、アルコキシアルキル基、チオアルコキシアルキル基、アリール基、アリールアルキル基、アラルキル基、又は複素環基である[7]〜[10]のいずれか1項に記載のカチオン電着塗料組成物。
[15]R2及びR3は水素である[7]〜[14]のいずれか1項に記載のカチオン電着塗料組成物。
[16]カチオン塩基含有樹脂(A)及びブロック化ポリイソシアネート化合物(B)の樹脂固形分合計質量100部を基準にして、カチオン塩基含有樹脂(A)の固形分を50〜90質量部、ブロック化ポリイソシアネート化合物(B)の固形分を10〜50質量部含む[1]〜[15]のいずれか1項に記載のカチオン電着塗料組成物。
[17]カチオン電着塗料組成物の樹脂固形分の総量を基準として、イミダゾール変性物(C)0.01〜10質量%含有する[1]〜[16]のいずれか1項に記載のカチオン電着塗料組成物。
[18][1]〜[17]のいずれか1項に記載のカチオン電着塗料組成物からなる電着塗料浴に金属被塗物を浸漬し、電着塗装する塗装方法。
[19][18]に記載の塗装方法によって塗膜を形成する工程を含む、塗装物品の製造方法。
各種樹脂の重合方法、塗料の製造方法、評価試験方法などは当該技術分野で従来公知の方法を用いている。
各例中の「部」は質量部、「%」は質量%を示す。
製造例1
攪拌機、温度計、窒素導入管および還流冷却器を取りつけたフラスコに、jER828EL(商品名、ジャパンエポキシレジン社製エポキシ樹脂、エポキシ当量190、数平均分子量350)1200部に、ビスフェノールA 500部及びジメチルベンジルアミン0.2部を加え、130℃でエポキシ当量850になるまで反応させた。
製造例2
攪拌機、温度計、窒素導入管および還流冷却器を取りつけたフラスコに、プロピレングリコールモノメチルエーテル200部を仕込み、窒素置換後、110℃に保った。この中に、以下に示す混合物を3時間かけて滴下した。
スチレン 300部
n−ブチルアクリレート 60部
メチルメタクリレート 60部
2−エチルヘキシルメタクリレート 240部
2−ヒドロキシエチルメタクリレート 240部
ジメチルアミノエチルメタクリレート 100部
2,2’−アゾビス(2−メチルブチロニトリル) 40部
滴下終了後から1時間経過後、この中に2,2’−アゾビス(2−メチルブチロニトリル)5部をプロピレングリコールモノメチルエーテル40部に溶かした溶液を1時間かけて滴下した。滴下終了後、これをさらに1時間110℃に保持したのち、メチルイソブチルケトンで調整し、固形分80%のアミノ基含有アクリル樹脂A−2溶液を得た。アミノ基含有アクリル樹脂A−2は、アミン価35mgKOH/g、水酸基価104mgKOH/g、数平均分子量10000であった。
製造例3
反応容器中に、コスモネートM−200(商品名、三井化学社製、クルードMDI、NCO基含有率 31.3%)270部、及びメチルイソブチルケトン127部を加え70℃に昇温した。この中にエチレングリコールモノブチルエーテル236部を1時間かけて滴下して加え、その後100℃に昇温し、この温度を保ちながら経時でサンプリングし、赤外線吸収スペクトル測定にて未反応のイソシアネート基の吸収がなくなったことを確認し、樹脂固形分80%のブロック化ポリイソシアネートB−1を得た。
製造例4
撹拌機、温度計、滴下ロートおよび還流冷却器を取り付けたフラスコに、jER828EL(商品名、ジャパンエポキシレジン社製エポキシ樹脂、エポキシ当量190、数平均分子量350)1010部に、ビスフェノールAを390部、プラクセル212(商品名、ポリカプロラクトンジオール、ダイセル化学工業株式会社、重量平均分子量約1250)240部及びジメチルベンジルアミン0.2部を加え、130℃でエポキシ当量が約1090になるまで反応させた。次に、ジメチルエタノールアミン134部及び濃度90%の乳酸水溶液150部を加え、90℃でエポキシ基が消失するまで反応させた。次いで、プロピレングリコールモノメチルエーテルを加えて固形分を調整し、固形分60%の4級アンモニウム塩基を含有する顔料分散用樹脂を得た。
イミダゾール変性物の製造例中、1H−NMRはブルカー株式会社製AV400を使用し、400MHzで測定した。IRは株式会社島津製作所製フーリエ変換赤外分光光度計IRAffinity−1、Smiths Detection株式会社製DuraSamplIRIIを使用し、全反射測定法で測定した。
1H−NMR(CD3OD)δ(ppm)=7.46(s,2H)、4.08(s,6H)。
1H−NMR(CD3OD)δ(ppm)=7.45(m,2H)、7.35−7.27(m,4H)、7.00(m,1H)、3.98(s,6H)。
1H−NMR(CD3OD)δ(ppm)=7.67(s,1H)、7.61(s,1H)、4.22(t,J=7.2Hz,2H)、3.94(s,3H)、1.91−1.84(m,2H)、1.32−1.26(m,10H)、0.85(t,J=7.2Hz,3H)
次いで、窒素置換した200mL試験管に1−オクチル−3−メチルイミダゾリウム−2−カルボキシレートのメタノール溶液4.0g(1−オクチル−3−メチルイミダゾリウム−2−カルボキシレート純分3.0g(13mmol))、フェニルイソシアネート1.5g(13mmol)及びトルエン100mLを仕込み、110℃で3時間撹拌した。得られた反応混合物を25℃に冷却後、減圧濃縮し、上記式(14)で表されるイミダゾール変性物Eを3.3g得た(収率84%)。イミダゾール変性物Eの1H−NMR分析結果を以下に示す。
1H−NMR(CD3OD)δ(ppm)=7.51(s,1H)、7.45―7.33(m,6H)、4.37(t,J=7.4Hz,2H)、3.97(s,3H)、1.91−1.86(m,2H)、1.35−1.27(m,10H)、0.88(t,J=6.8Hz,3H)。
製造例10 イミダゾール変性物Fの製造
1H−NMR(DMSO−d6)δ(ppm)=9.32(s,1H)、7.80(s,2H)、4.17(t,J=9.6Hz,4H)、1.78(m,4H)、1.63(s,3H)、1.23(m,20H)、0.85(t,J=6.4Hz,6H)
次いで、1,3−ジオクチルイミダゾリウム アセテート10.0g(0.03mol)、クロロベンゼン50.0g、モレキュラーシーブ4A3.0gを仕込み、窒素下で16時間静置した。その後、ろ過でモレキュラーシーブ4Aを除去し、得られた溶液を窒素置換した200mLの3つ口反応器に仕込み、N−フェニルカルバミン酸メチル15.4g(0.10mol)を加え、130℃で4時間攪拌した。撹拌後、得られた反応混合物を減圧濃縮し、褐色固体を24.0g得た。得られた褐色液体をアルミナカラムで単離し、上記式(15)で表される化合物イミダゾール変性物Fを得た。イミダゾール変性物Fの1H−NMR分析結果を以下に示す。
製造例11
製造例4で得た固形分60%の4級アンモニウム塩基を含有する顔料分散用樹脂8.3部(固形分5部)、酸化チタン14.5部、精製クレー7.0部、カーボンブラック0.3部、ジオクチル錫オキサイド(触媒)2部、及び脱イオン水20.3部を加え、ボールミルにて20時間分散し、固形分55%の顔料分散ペーストP−1を得た。
触媒の種類を下記表1記載のように変更した以外は製造例11と同様にして、固形分55%の顔料分散ペーストP−2〜5を得た(製造例12〜15)。触媒の種類及び配合量を下記表1に記載のように変更し、精製クレーを4部用いる以外、製造例11と同様にして、固形分55%の顔料分散ペーストP−6を得た(製造例16)。触媒の種類を下記表1に記載のように変更した以外は製造例11と同様にして、固形分55%の顔料分散ペーストP−7〜9を得た(製造例17〜19)。下記表1に記載のように触媒を用いず、精製クレーを9部用いる以外、製造例11と同様にして、固形分55%の顔料分散ペーストP−10を得た(製造例20)。
実施例1
製造例1で得られたアミノ基含有エポキシ樹脂A−1 87.5部(固形分70部)、製造例3で得られたブロック化ポリイソシアネートB−1 37.5部(固形分30部)を混合し、さらに10%酢酸13部を配合して均一に攪拌した後、脱イオン水を強く攪拌しながら約15分間を要して滴下して固形分34%のエマルションを得た。
次に、上記エマルション294部(固形分100部)、製造例12で得た顔料分散ペーストP−2 52.4部、脱イオン水350部を加え、固形分20%のカチオン電着塗料X−1を製造した。
アミノ基含有エポキシ樹脂A−1及び顔料分散ペーストP−2に代えて下記表2に記載された種類及び配合量のアミノ基含有樹脂及び顔料分散ペーストを用いる以外は実施例1と同様にして、カチオン電着塗料X−2〜12を製造した。
また、後述する評価試験(硬化性、仕上がり性)の結果を表中に記載した。ジオクチル錫オキサイドを含有する塗料に関しては、評価結果は合格レベルであるが環境面(有毒性)で不合格であるため比較例とした。
化成処理(商品名、パルボンド#3020、日本パーカライジング社製、リン酸亜鉛処理剤)を施した冷延鋼板(150mm(縦)×70mm(横)×0.8mm(厚))を被塗物として、実施例及び比較例で得た各々のカチオン電着塗料を用いて乾燥膜厚17μmとなるように電着塗装し、150℃と170℃で20分間焼付け乾燥して試験板(2枚)を得た。
試験板の塗面をサーフテスト301(商品名、株式会社ミツトヨ製、表面粗度計)を用いて、表面粗度値(Ra)をカットオフ0.8mmにて測定し、以下の基準で評価した。評価は、S〜Bが合格であり、Cが不合格である。
S:表面粗度値(Ra)が、0.2未満、
A:表面粗度値(Ra)が、0.2以上、かつ0.25未満、
B:表面粗度値(Ra)が、0.25以上、かつ0.3未満、
C:表面粗度値(Ra)が、0.3以上、を示す。
得られた試験板から、150℃及び170℃での硬化性(ゲル分率)を評価した。
評価は、A及びBが合格であり、Cが不合格である。
A:ゲル分率が、90%以上、
B:ゲル分率が、70%以上で、かつ90%未満、
C:ゲル分率が、70%未満、を示す。
(1)塗装前の試験板質量(X)を測定する。
(2)電着塗装及び焼付けをして、硬化塗膜の試験板質量(Y)を測定する。
(3)上記試験板をアセトンに浸漬し、加熱・還流させた状態で5時間処理する。
(4)処理後の試験板を乾燥させた試験板質量(Z)を測定する。
(5)下記式により、ゲル分率(%)を計算する。
ゲル分率(%)=〔Z−X〕/〔Y−X〕×100
Claims (6)
- カチオン塩基含有樹脂(A)、ブロック化ポリイソシアネート化合物(B)、並びに下記式(1)で示されるイミダゾール変性物(C)を含有するカチオン電着塗料組成物。
- カチオン塩基含有樹脂(A)が、カチオン塩基含有エポキシ樹脂及び/又はカチオン塩基含有アクリル樹脂を含む請求項1に記載のカチオン電着塗料組成物。
- カチオン塩基含有樹脂(A)のカチオン塩基が、アミノ基、4級アンモニウム塩基、及びスルホニウム塩基からなる群より選ばれる少なくとも一種である請求項1に記載のカチオン電着塗料組成物。
- カチオン電着塗料組成物の樹脂固形分の総量を基準として、イミダゾール変性物(C)0.01〜10質量%含有する請求項1〜3のいずれか1項に記載のカチオン電着塗料組成物。
- 請求項1〜4のいずれか1項に記載のカチオン電着塗料組成物からなる電着塗料浴に金属被塗物を浸漬し、電着塗装する塗装方法。
- 請求項5に記載の塗装方法によって塗膜を形成する工程を含む、塗装物品の製造方法。
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JP6995076B2 (ja) * | 2019-03-29 | 2022-01-14 | 関西ペイント株式会社 | カチオン電着塗料組成物 |
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