JP5290504B2 - 水性塗料組成物 - Google Patents
水性塗料組成物 Download PDFInfo
- Publication number
- JP5290504B2 JP5290504B2 JP2006243548A JP2006243548A JP5290504B2 JP 5290504 B2 JP5290504 B2 JP 5290504B2 JP 2006243548 A JP2006243548 A JP 2006243548A JP 2006243548 A JP2006243548 A JP 2006243548A JP 5290504 B2 JP5290504 B2 JP 5290504B2
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- JP
- Japan
- Prior art keywords
- acid
- water
- compound
- group
- epoxy
- 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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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 50
- 239000003973 paint Substances 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 15
- -1 amine compound Chemical class 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000005056 polyisocyanate Substances 0.000 claims description 51
- 229920001228 polyisocyanate Polymers 0.000 claims description 51
- 238000000576 coating method Methods 0.000 claims description 39
- 239000011248 coating agent Substances 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000008199 coating composition Substances 0.000 claims description 27
- 239000004593 Epoxy Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 229920005749 polyurethane resin Polymers 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000006185 dispersion Substances 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 7
- 229920000877 Melamine resin Polymers 0.000 claims description 6
- 239000004640 Melamine resin Substances 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 6
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 4
- 230000003449 preventive effect Effects 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 64
- 239000000194 fatty acid Substances 0.000 description 64
- 229930195729 fatty acid Natural products 0.000 description 64
- 150000004665 fatty acids Chemical class 0.000 description 49
- 229920000647 polyepoxide Polymers 0.000 description 35
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 33
- 239000003822 epoxy resin Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 31
- 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 20
- 238000012360 testing method Methods 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
- 230000007797 corrosion Effects 0.000 description 19
- 238000005260 corrosion Methods 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000001035 drying Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 125000005442 diisocyanate group Chemical group 0.000 description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 239000002981 blocking agent Substances 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 9
- 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 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 230000008961 swelling Effects 0.000 description 8
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 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 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 230000003472 neutralizing effect Effects 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- ZDGWGNDTQZGISB-UHFFFAOYSA-N acetic acid;perchloric acid Chemical compound CC(O)=O.OCl(=O)(=O)=O ZDGWGNDTQZGISB-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000007809 chemical reaction catalyst Substances 0.000 description 4
- 150000005676 cyclic carbonates Chemical group 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002253 Tannate Polymers 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000004566 building material Substances 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
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- 230000032050 esterification Effects 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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- 239000004094 surface-active agent Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
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- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 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 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 2
- PFUKECZPRROVOD-UHFFFAOYSA-N 1,3,5-triisocyanato-2-methylbenzene Chemical compound CC1=C(N=C=O)C=C(N=C=O)C=C1N=C=O PFUKECZPRROVOD-UHFFFAOYSA-N 0.000 description 2
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- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
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- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- 239000004970 Chain extender Substances 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WPKJBEXVSONQJM-UHFFFAOYSA-N N-butylbutan-1-amine 1,4-dioxane Chemical compound O1CCOCC1.C(CCC)NCCCC WPKJBEXVSONQJM-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-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
- 229910019142 PO4 Inorganic materials 0.000 description 2
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- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
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- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- 239000004246 zinc acetate Substances 0.000 description 1
- XSMMCTCMFDWXIX-UHFFFAOYSA-N zinc silicate Chemical compound [Zn+2].[O-][Si]([O-])=O XSMMCTCMFDWXIX-UHFFFAOYSA-N 0.000 description 1
- 235000019352 zinc silicate Nutrition 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- 150000003953 γ-lactams Chemical class 0.000 description 1
Landscapes
- Application Of Or Painting With Fluid Materials (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Description
ポリウレタン樹脂(A)の水性分散体
本発明においてエポキシプレポリマー(I)は、末端にアミノ基を有し、ポリエポキシ化合物(a)とアミン化合物(b)との反応によって得られるものである。
数平均分子量={M×m/(M−N)}+{N×n/(M−N)}
マー(II)との反応によって得られる。
架橋剤(B)としては、上記ポリウレタン樹脂(A)中の架橋性官能基と反応するものであれば特に限定なく使用できる。例えば、ブロックポリイソシアネート硬化剤(b1)、水分散性ポリイソシアネート硬化剤(b2)、水分散性ブロックポリイソシアネート硬化剤(b3)、メラミン樹脂(b4)、ポリイソシアネート硬化剤(b5)、ポリエポキシ化合物(b6)、フェノール樹脂、尿素樹脂、グアナミン樹脂等が好適に使用できる。
レットタイプ付加物、イソシアヌレート環付加物;水添MDI、及び水添MDIの誘導体;トリフェニルメタン−4,4’,4’’−トリイソシアネート、1,3,5−トリイソシアナトベンゼン、2,4,6−トリイソシアナトトルエン、4,4’−ジメチルジフェニルメタン−2,2’,5,5’−テトライソシアネートなどの1分子中に3個以上のイソシアネ−ト基を有するポリイソシアネート類;これらのポリイソシアネートのビューレットタイプ付加物、イソシアヌレート環付加物;エチレングリコール、プロピレングリコール、1,4−ブチレングリコール、ジメチロールプロピオン酸、ポリアルキレングリコール、トリメチロールプロパン、ヘキサントリオールなどのポリオールの水酸基にイソシアネート基が過剰量となる比率でポリイソシアネート化合物を反応させてなるウレタン化付加物;これらのウレタン化付加物のビューレットタイプ付加物、イソシアヌレート環付加物等が挙げられる。
本発明の水性塗料組成物は被塗物に、例えば、エアスプレー塗装、エアレススプレー塗装、静電塗装、ハケ塗装、ローラー塗装、リシンガン、万能ガン等により塗布することができる。塗装膜厚は、乾燥膜厚で1〜100μm、好ましくは5〜50μmの範囲が適当である。乾燥条件は、特に限定されるものではないが、好ましくは乾燥温度20〜220℃、乾燥時間1〜120分の範囲である。
本発明の塗装物品としては、上記塗膜形成方法により形成される塗装物品であれば特に制限されるものではなく、例えば、電気製品(電子レンジ、トースター、冷蔵庫、洗濯機など)の内外装、エアーコンディショナーの室内機、室外機、吹き出口およびダクト、空気清浄機、暖房機などのエアーコンディショナーの内外装、反射板などの照明器具、家具、機械部品、事務機器(机、本棚、ロッカー、書類棚など)の内外装、自動車(ホイール、ドアミラー、モール、ドアのノブ、ナンバープレート、ハンドル、インスツルメンタルパネルなど)、建設機械(ブルドーザ、油圧ショベル、クレーン、コンクリートポンプ車、ダンプトラックなど)、あるいは厨房器具類(レンジフード、流し台、調理台、ガスレンジ、換気扇など)の塗装用として、間仕切り、バスユニット、シャッター、ブラインド、カーテンレールなどの屋内塗装用として、外装用としては外壁、手摺り、門扉、シャッターなどの一般住宅外装、ビル外装など、窯業系サイジング材、発泡コンクリートパネル、コンクリートパネル、カーテンウォール、塩ビ鋼板やシートなどの建築用外装材、などが挙げられる。
エポキシプレポリマー(I−1)の作成
温度計、攪拌装置、還流冷却管を備えた4つ口フラスコを窒素置換させ、その中でエポキシ当量450g/eqのビスフェノールA型エポキシ樹脂(180g)を、プロピレングリコールモノプロピルエーテル(49.6g)に溶解し、これに2−アミノエタノール(18.3g)を加え、85℃で3時間保持し、アミノ基含有量(注1)が1.5〜1.55mmol/g程度となるまで反応させた。その後、メチルエチルケトン(148.7g)を加え、エポキシプレポリマー(I−1)溶液を得た。得られたエポキシプレポリマー(I−1)溶液の固形分濃度は50%、プレポリマーの数平均分子量は1983であった。
三角フラスコに試料(g)をはかりとり、これに40mlのメチルエチルケトンを加えて溶解する。溶解しにくい場合は50℃まで加熱して溶解する。次に、全量ピペットでCTAB(セチルトリメチルアンモニウムブロミド)溶液10mlを加えて均一にする。続いて、スクリーン指示薬0.2mlを正確に加えて、N/10過塩素酸−酢酸溶液で滴定し、最後の一滴で桃色が約30秒間続いたとき終点とする。アミノ基含有量は下記計算値から算出する。尚、CTAB溶液はCTAB20gに酢酸200mlを加えて溶解しさらにメチルエチルケトン200mlを加えて均一溶液に調整し、スクリーン指示薬は氷酢酸100mlにアルファズリン0.3gを溶解した溶液に、チモールブルー1.5gをメタノール500mlに溶解した溶液を混合して調整した。
計算式:E=(A-B)×0.1×F/S×0.01×W
ここでE:アミノ基含有量(mmol/g)
A:本試験のN/10過塩素酸-酢酸溶液の使用量(ml)
B:空試験のN/10過塩素酸-酢酸溶液の使用量(ml)
F:N/10過塩素酸-酢酸溶液のファクター
S:試料の加熱残分(%)
W:試料の量
温度計、攪拌装置、還流冷却管を備えた4つ口フラスコを窒素置換させ、その中で「ビスオール3PN」(注2)(212.3g)、「ビスオール6PN」(注3)(305.9g)、ジメチロールプロピオン酸(61.1g)をN−メチルピロリドン(154.2g)に溶解し、ヘキサメチレンジイソシアネート(191.7g)を30分かけて滴下し、60℃で1.5時間反応を行った。その後80℃に昇温し2時間反応を行って、イソホロンジイソシアネート(168.7g)を加え更に80℃で3時間、NCO価(注4)が25〜37程度となるまで反応させた。その後、メチルエチルケトン(418g)を加え、ウレタンプレポリマー(II−1)溶液を得た。得られたウレタンプレポリマー(II−1)溶液の固形分濃度は62.2%、プレポリマーの数平均分子量は2473、酸価は27.2mgKOH/gであった。
(注2)ビスオール3PN:東邦化学工業株式会社製、プロピレンオキサイド変性ビスフェノールA(プロピレンオキサイド変性量=3モル)
(注3)ビスオール6PN:東邦化学工業株式会社製、プロピレンオキサイド変性ビスフェノールA(プロピレンオキサイド変性量=6モル)
(注4)NCO価:ウレタンプレポリマー1g中に含まれるイソシアネート基量(mg)で、下記測定方法にて追跡した。
三角フラスコに試料(g)を正しくはかりとり、ジオキサン10mlを加え、溶解した試料を50℃に加熱し、正しくはかりとったN/5ジブチルアミン−ジオキサン溶液10mlを加え、2分間かき混ぜて試料とジブチルアミンを反応させる。次に、ブロムフェノールブルー-エチルアルコール溶液を2〜3滴加えて、N/10塩酸溶液で滴定し、青色から黄緑色に変化したときを終点とする。
計算式N={0.1×42×(A-B)×f}/0.01×S×W}
ここでN:NCO価(試料1g中に含まれるNCOのmg数)
A:空試験のN/5ジブチルアミン-ジオキサン溶液を中和するのに使用したN/10塩酸溶液の量(ml)
B:試料の滴定に使用したN/10塩酸溶液の量(ml)
f:N/10塩酸溶液のファクター
S:試料の加熱残分(%)
W:試料の量(g)
42:NCOの分子量
上記と同様の装置を用い、62.6%ウレタンプレポリマー(II−1)溶液(1511g)を、攪拌状態で50℃に保持し、その中に50%エポキシプレポリマー(I−1)溶液(753.6g)を加え、1時間攪拌した。次いで40℃に冷却し、トリエチルアミン(36.8g)で中和し、脱イオン水(2392.6g)を加えて、分散した。その中に、脱イオン水(91.3g)で希釈したジエチレントリアミン(9.1g)を30分かけて滴下し、50℃で2時間保持した。その後、60℃でメチルエチルケトンを減圧留去することで、ポリウレタン樹脂の水性分散体(III−1)を得た。この水性分散体の固形分濃度は35.0%、ポリウレタン樹脂の酸価は19.4mgKOH/g、アミン価は8.1mgKOH/g、水酸基価は59.1mgKOH/gである。
エポキシプレポリマー(I−2)の作成
温度計、攪拌装置、還流冷却管を備えた4つ口フラスコを窒素置換させ、その中でエポキシ当量450g/eqのビスフェノールA型エポキシ樹脂(180.0g)を、プロピレングリコールモノプロピルエーテル(82.1g)に溶解し、これに3−アミノプロピルトリエトキシシラン(66.4g)を加え、85℃で3時間保持し、アミノ基含有量(注1)が1.21〜1.22mmol/g程度となるまで反応させた。その後、メチルエチルケトン(164.3g)を加え、エポキシプレポリマー(I−2)溶液を得た。得られたエポキシプレポリマー(I−2)溶液の固形分濃度は50%、プレポリマーの数平均分子量は2464、であった。
温度計、攪拌装置、還流冷却管を備えた4つ口フラスコを窒素置換させ、その中で「ビスオール3PN」(注2)(323.2g)、「ビスオール6PN」(注3)(465.8g)、ジメチロールプロピオン酸(104.5g)をN−メチルピロリドン(239.2g)に溶解し、ヘキサメチレンジイソシアネート(302.8g)を30分かけて滴下し、60℃で1.5時間反応を行った。その後80℃に昇温し2時間反応を行って、イソホロンジイソシアネート(266.4g)を加え更に80℃で3時間、NCO価(注4)が25〜37程度となるまで反応させた。その後、メチルエチルケトン(660g)を加え、ウレタンプレポリマー(II−2)溶液を得た。得られたウレタンプレポリマー(II−2)溶液の固形分濃度は61.9%、プレポリマーの数平均分子量は2438、酸価は29.9mgKOH/gであった。
上記と同様の装置を用い、61.9%ウレタンプレポリマー(II−2)溶液(236.2g)を、攪拌状態で50℃に保持し、その中に50%エポキシプレポリマー(I−2)溶液(147.9g)を加え、1時間攪拌した。次いで40℃に冷却し、トリエチルアミン(6.3g)で中和し、脱イオン水(408.2g)を加えて、分散した。その中に、脱イオン水(14.4g)で希釈したジエチレントリアミン(1.44g)を30分かけて滴下し、50℃で2時間保持した。その後、60℃でメチルエチルケトンを減圧留去することで、ポリウレタン樹脂の水性分散体(III−2)を得た。この水性分散体の固形分濃度は35.0%、ポリウレタン樹脂の酸価は19.9mgKOH/g、アミン価は7.6mgKOH/g、水酸基価は66.1mgKOH/gであった。
ポリウレタン樹脂水性分散体(III−3)の作成
温度計、攪拌装置、還流冷却管を備えた4つ口フラスコを窒素置換させ、その中で「ビスオール3PN」(注2)(446.9g)、「ビスオール6PN」(注3)(161g)、ジメチロールプロピオン酸(59.0g)をN−メチルピロリドン(133.6g)に溶解し、ヘキサメチレンジイソシアネート(241.9g)を30分かけて滴下し、60℃で1.5時間反応を行った。その後80℃に昇温し2時間反応を行って、イソホロンジイソシアネート(177.6g)を加え更に80℃で3時間、NCO価(注4)が25〜37程度となるまで反応させた。その後、メチルエチルケトン(332.4g)を加えた。ジメチルエタノールアミン(39.2g)で中和し、脱イオン水(2315.9g)を加えて、分散した。その中に、脱イオン水(285.6g)で希釈したヒドロキシエチルアミノエチルアミン(28.6g)を30分かけて滴下し、50℃で2時間保持した。その後、60℃でメチルエチルケトンを減圧留去することで、ポリウレタン樹脂の水性分散体(III−3)を得た。この水性分散体の固形分濃度は28.6%であった。
表1の配合に従い主剤をペイントシェーカーにて90分分散を行った後、架橋剤と混合・攪拌し、各水性塗料組成物を得た。各水性塗料組成物を下記性能試験に供した。結果を表1にあわせて示す。
(注6)サイメル325:サイテックインダストリー社製、メチル化メラミン樹脂、固形分80%
(注7)水分散性ポリイソシアネート硬化剤:数平均分子量550のメトキシポリエチレングリコール55gと「タケネートD170HN」(三井化学ポリウレタン株式会社製、ヘキサメチレンジイソシアネートのトリマー)504gを70℃の条件下でNCO価(注4)が218mg/gになるまで反応させ、固形分100%の水分散性ポリイソシアネートを得た。
(注8)ブロックポリイソシアネート硬化剤:デュラネートTPA−100(旭化成製、イソシアヌレート構造含有ポリイソシアネート、数平均分子量600、イソシアネート含有量23.1%)605g、および酢酸エチル120gを入れ100℃に加温し、窒素気流下でオキソコールC13(協和油化社製、トリデカノールの構造異性体)80gを加え100℃で2時間保持した。その後、マロン酸ジエチル345g、酢酸エチル60gを加えて60℃に保持した後、窒素気流下でナトリウムメトキシドの28%メタノール溶液を7.0g加え、60℃で12時間保持した。この反応生成物の605gに2−エチルヘキサノール488gを加え、90℃に昇温した。これを減圧条件下で系の温度を90〜110℃に保ちながら約1.5時間かけて溶剤を留出除去し、固形分100%のブロックポリイソシアネートを得た。
(1)耐水性試験:各組成物をリン酸亜鉛処理鋼板にアプリケーターにて乾燥膜厚が25μmとなるように塗装し、表1中に記載の乾燥条件で乾燥・加熱して、各試験板を作成した。得られた試験板を20℃の恒温水槽に7日間浸漬後、塗膜状態を目視で観察した。
◎:異常なし
○:若干フクレ、変色があるが、良好な状態
△:フクレ、変色があり、実用困難
×:フクレ、変色が著しい
(i)カット部の錆び・フクレ
◎:錆、フクレの最大幅がカット部より1mm未満(片側)
○:錆、フクレの最大幅がカット部より1mm以上、2mm未満(片側)
△:錆フクレの最大幅がカット部より2mm以上、3mm未満(片側)
×:錆、フクレの最大幅がカット部より3mm以上(片側)
(ii)一般部のブリスター
JIS K5600−8−2に準拠して評価
溶剤抽出残分(%)=(抽出した後の膜の重量/抽出前の膜の重量)×100(%)
本発明の水性塗料組成物からなる塗膜の上に上塗塗料を塗装して複層塗膜を形成させ、下記性能試験に供した。塗膜の作成条件及び性能試験結果を表2示す。
(4)耐水性試験:各水性塗料組成物をリン酸亜鉛処理鋼板にアプリケーターにて乾燥膜厚が25μmとなるように塗装し、表2中に記載の乾燥条件で乾燥・加熱して下塗塗膜を作成した。その塗膜上に表2記載の上塗塗料を乾燥膜厚が20μmとなるように塗装し表2中に記載の乾燥条件で乾燥・加熱して上塗塗膜を作成し、試験板を得た。得られた試験板を20℃の恒温水槽に7日間浸漬後、塗膜状態を目視で観察した。
◎:異常なし
○:若干フクレ、変色があるが、良好な状態
△:フクレ、変色があり、実用困難
×:フクレ、変色が著しい
(i)カット部の錆び・フクレ
◎:錆、フクレの最大幅がカット部より1mm未満(片側)
○:錆、フクレの最大幅がカット部より1mm以上、2mm未満(片側)
△:錆フクレの最大幅がカット部より2mm以上、3mm未満(片側)
×:錆、フクレの最大幅がカット部より3mm以上(片側)
(ii)一般部のブリスター
JIS K5600−8−2に準拠して評価
Claims (9)
- ポリエポキシ化合物(a)とアミノシランであるアミン化合物(b)との反応によって得られる末端にアミノ基を有するエポキシプレポリマー(I)と、カルボキシル基含有ジオール(c)を含む1分子中に水酸基を2つ以上含有する化合物(d)とポリイソシアネート化合物(e)との反応により得られる末端にイソシアネート基を有するウレタンプレポリマー(II)との反応によって得られるポリウレタン樹脂(A)の水性分散体、及びメラミン樹脂である架橋剤(B)を含有することを特徴とする水性塗料組成物。
- エポキシプレポリマー(I)が、ポリエポキシ化合物(a)中のエポキシ基とアミン化合物(b)中のアミノ基との当量比が1:0.5〜1:2となるように反応させて得られる請求項1記載の水性塗料組成物。
- エポキシプレポリマー(I)が、数平均分子量500〜10000の範囲内である請求項1又は2記載の水性塗料組成物。
- ウレタンプレポリマー(II)が、全成分中のイソシアネート基と水酸基との当量比が1:0.5〜1:0.9となるように反応させて得られる請求項1ないし3のいずれか1項に記載の水性塗料組成物。
- ウレタンプレポリマー(II)が、数平均分子量1000〜6000の範囲内である請求項1ないし4のいずれか1項に記載の水性塗料組成物。
- ポリウレタン樹脂(A)が、酸価10〜30mgKOH/g、アミン価0〜50mgKOH/g、及び水酸基価20〜200mgKOH/gである請求項1ないし5のいずれか1項に記載の水性塗料組成物。
- さらに防錆剤を含有する請求項1ないし6のいずれか1項に記載の水性塗料組成物。
- 被塗面に、請求項1ないし7のいずれか1項に記載の水性塗料組成物を塗装することを特徴とする塗膜形成方法。
- 請求項8に記載の方法により形成される塗装物品。
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JP2009281060A (ja) * | 2008-05-22 | 2009-12-03 | Shimizu Corp | 外装パネル |
JP5249061B2 (ja) * | 2009-01-13 | 2013-07-31 | 関西ペイント株式会社 | 水性塗料組成物及び塗装方法 |
EP3266578B1 (en) * | 2011-12-20 | 2020-07-15 | Cytec Industries Inc. | Dry fibrous material for subsequent resin infusion |
JP6458995B2 (ja) * | 2015-03-31 | 2019-01-30 | 大日本塗料株式会社 | コンクリートの断面修復及び剥落防止工法 |
KR101699953B1 (ko) * | 2015-05-27 | 2017-02-13 | 이영미 | 목재 가구용 방수제 |
CN112592455B (zh) * | 2020-12-09 | 2022-06-07 | 湖南林特科技有限公司 | 一种单组份水性环氧乳液的合成方法 |
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