JP5741142B2 - カチオン性ウレタン樹脂組成物及び金属コーティング剤 - Google Patents
カチオン性ウレタン樹脂組成物及び金属コーティング剤 Download PDFInfo
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- JP5741142B2 JP5741142B2 JP2011078623A JP2011078623A JP5741142B2 JP 5741142 B2 JP5741142 B2 JP 5741142B2 JP 2011078623 A JP2011078623 A JP 2011078623A JP 2011078623 A JP2011078623 A JP 2011078623A JP 5741142 B2 JP5741142 B2 JP 5741142B2
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- Prior art keywords
- urethane resin
- cationic urethane
- cyclic structure
- mass
- aliphatic cyclic
- Prior art date
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- 125000002091 cationic group Chemical group 0.000 title claims description 160
- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims description 148
- 239000011248 coating agent Substances 0.000 title claims description 103
- 239000011342 resin composition Substances 0.000 title claims description 61
- 229910052751 metal Inorganic materials 0.000 title claims description 15
- 239000002184 metal Substances 0.000 title claims description 15
- 150000003077 polyols Chemical class 0.000 claims description 148
- 229920005862 polyol Polymers 0.000 claims description 118
- 125000001302 tertiary amino group Chemical group 0.000 claims description 36
- 229920005906 polyester polyol Polymers 0.000 claims description 35
- 239000005056 polyisocyanate Substances 0.000 claims description 33
- 229920001228 polyisocyanate Polymers 0.000 claims description 33
- 239000004417 polycarbonate Substances 0.000 claims description 29
- 229920000515 polycarbonate Polymers 0.000 claims description 27
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 23
- 239000012736 aqueous medium Substances 0.000 claims description 19
- 125000001931 aliphatic group Chemical group 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 12
- 125000005372 silanol group Chemical group 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000005956 quaternization reaction Methods 0.000 claims description 3
- 238000000576 coating method Methods 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
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- -1 aluminum compound Chemical class 0.000 description 43
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- 239000002585 base Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000000203 mixture Substances 0.000 description 27
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- 239000000243 solution Substances 0.000 description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 22
- 239000000126 substance Substances 0.000 description 22
- 230000018044 dehydration Effects 0.000 description 21
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 16
- 238000002156 mixing Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 15
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 11
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 11
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- 239000001361 adipic acid Substances 0.000 description 10
- 235000011037 adipic acid Nutrition 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 9
- 229920001155 polypropylene Polymers 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 8
- 239000004970 Chain extender Substances 0.000 description 7
- 229910001335 Galvanized steel Inorganic materials 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 239000008397 galvanized steel Substances 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 230000003449 preventive effect Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 229920005749 polyurethane resin Polymers 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 241001163841 Albugo ipomoeae-panduratae Species 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
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- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
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- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 3
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- UYDJAHJCGZTTHB-UHFFFAOYSA-N cyclopentane-1,1-diol Chemical compound OC1(O)CCCC1 UYDJAHJCGZTTHB-UHFFFAOYSA-N 0.000 description 1
- LNGJOYPCXLOTKL-UHFFFAOYSA-N cyclopentane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C1 LNGJOYPCXLOTKL-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- ASGKDLGXPOIMTM-UHFFFAOYSA-N diethoxy-methyl-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](C)(OCC)OCC)CCC2OC21 ASGKDLGXPOIMTM-UHFFFAOYSA-N 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 229940043279 diisopropylamine Drugs 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
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004649 discoloration prevention Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- CPSYWNLKRDURMG-UHFFFAOYSA-L hydron;manganese(2+);phosphate Chemical compound [Mn+2].OP([O-])([O-])=O CPSYWNLKRDURMG-UHFFFAOYSA-L 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011656 manganese carbonate Substances 0.000 description 1
- 235000006748 manganese carbonate Nutrition 0.000 description 1
- 229940093474 manganese carbonate Drugs 0.000 description 1
- 229940077478 manganese phosphate Drugs 0.000 description 1
- 229940099596 manganese sulfate Drugs 0.000 description 1
- 239000011702 manganese sulphate Substances 0.000 description 1
- 235000007079 manganese sulphate Nutrition 0.000 description 1
- MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 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
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-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
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- CPTXPDMOZQHSFO-UHFFFAOYSA-N n-icosylicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCCCC CPTXPDMOZQHSFO-UHFFFAOYSA-N 0.000 description 1
- UQLQVWLBTRWAIP-UHFFFAOYSA-N n-nonadecylnonadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCCC UQLQVWLBTRWAIP-UHFFFAOYSA-N 0.000 description 1
- MFHKEJIIHDNPQE-UHFFFAOYSA-N n-nonylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCCC MFHKEJIIHDNPQE-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- YDFFPEXFCAUTSL-UHFFFAOYSA-N n-pentadecylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNCCCCCCCCCCCCCCC YDFFPEXFCAUTSL-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910000159 nickel phosphate Inorganic materials 0.000 description 1
- JOCJYBPHESYFOK-UHFFFAOYSA-K nickel(3+);phosphate Chemical compound [Ni+3].[O-]P([O-])([O-])=O JOCJYBPHESYFOK-UHFFFAOYSA-K 0.000 description 1
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
- BFDHFSHZJLFAMC-UHFFFAOYSA-L nickel(ii) hydroxide Chemical compound [OH-].[OH-].[Ni+2] BFDHFSHZJLFAMC-UHFFFAOYSA-L 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000765 poly(2-oxazolines) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000011780 sodium chloride 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
- 239000007787 solid Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- LUHFNMZIUWHSET-UHFFFAOYSA-N spiro[3.4]octane-3,3-diol Chemical compound OC1(O)CCC11CCCC1 LUHFNMZIUWHSET-UHFFFAOYSA-N 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide 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
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
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- 229960001763 zinc sulfate Drugs 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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、ポリプロピレングリコール−ジグリシジルエーテル(エポキシ当量201g/当量)590質量部を仕込んだ後、フラスコ内を窒素置換した。次いで、前記フラスコ内の温度が70℃になるまでオイルバスを用いて加熱した後、滴下装置を使用してジ−n−ブチルアミン380質量部を30分間で滴下し、滴下終了後、90℃で10時間反応させた。反応終了後、赤外分光光度計(FT/IR−460Plus、日本分光株式会社製)を用いて、反応生成物のエポキシ基に起因する842cm−1付近の吸収ピークが消失していることを確認し、3級アミノ基含有ポリオール(c3−1)(アミン当量339g/当量、水酸基当量339g/当量)を調製した。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、1,4−シクロヘキサンジメタノール617質量部とネオペンチルグリコール1010質量部とアジピン酸1823質量部とを反応させて得られた脂肪族環式構造含有ポリエステルポリオール(数平均分子量2000、脂肪族環式構造量1425mmol/kg)を1070質量部加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、1,4−シクロヘキサンジメタノール617質量部とネオペンチルグリコール1010質量部とアジピン酸1823質量部とを反応させて得られた脂肪族環式構造含有ポリエステルポリオール(数平均分子量2000、脂肪族環式構造量1425mmol/kg)を1070質量部加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、1,6−ヘキサンジオールとヘキサヒドロ無水フタル酸とを反応させて得られた脂肪族環式構造含有ポリエステルポリオール(数平均分子量2000、脂肪族環式構造量3700mmol/kg)を1070質量部加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、1,6−ヘキサンジオールとヘキサヒドロ無水フタル酸とを反応させて得られた脂肪族環式構造含有ポリエステルポリオール(数平均分子量2000、脂肪族環式構造量3700mmol/kg)を1070質量部加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、1,6−ヘキサンジオールとヘキサヒドロ無水フタル酸とを反応させて得られた脂肪族環式構造含有ポリエステルポリオール(数平均分子量2000、脂肪族環式構造量3700mmol/kg)を1070質量部加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、1,4−シクロヘキサンジメタノールと炭酸エステルとを反応させて得られた脂肪族環式構造含有ポリカーボネートポリオール(数平均分子量1000、脂肪族環式構造量6028mmol/kg)を474質量部、及び、ポリオキシテトラメチレングリコール(数平均分子量2000)123質量部を加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、ネオペンチルグリコールと1,4−ブタンジオールとテレフタル酸とアジピン酸とを反応させて得られたポリエステルポリオール(数平均分子量1900、脂肪族環式構造量0mmol/kg)を554質量部、及び、1,6−ヘキサンジオールと炭酸エステルとを反応させて得られた脂肪族ポリカーボネートポリオール(数平均分子量1000、脂肪族環式構造量0mmol/kg)947質量部を加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、ネオペンチルグリコールと1,4−ブタンジオールとテレフタル酸とアジピン酸とを反応させて得られたポリエステルポリオール(数平均分子量1900、脂肪族環式構造量0mmol/kg)を554質量部、及び、1,6−ヘキサンジオールと炭酸エステルとを反応させて得られた脂肪族ポリカーボネートポリオール(数平均分子量1000、脂肪族環式構造量0mmol/kg)947質量部を加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、ネオペンチルグリコールと1,4−ブタンジオールとテレフタル酸とアジピン酸とを反応させて得られたポリエステルポリオール(数平均分子量1900、脂肪族環式構造量0mmol/kg)を554質量部、及び、1,4−シクロヘキサンジメタノール86質量部を加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、1,4−シクロヘキサンジメタノール617質量部とネオペンチルグリコール1010質量部とアジピン酸1823質量部とを反応させて得られた脂肪族環式構造含有ポリエステルポリオール(数平均分子量2000、脂肪族環式構造量1425mmol/kg)を1070質量部を加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
温度計、撹拌装置、還流冷却管及び滴下装置を備えた4ツ口フラスコに、1,4−シクロヘキサンジメタノールと炭酸エステルとを反応させて得られた脂肪族環式構造含有ポリカーボネートポリオール(数平均分子量1000、脂肪族環式構造量6028mmol/kg)536質量部を加え、減圧度0.095MPaにて120〜130℃で脱水を行った。
A4サイズのガラス板に、高さ1mmの外枠を有するポリプロピレンフィルムを貼付し、該ポリプロピレンフィルム上に、実施例及び比較例で得られたカチオン性ウレタン樹脂組成物を6g/100cm2となるように塗布し、25℃で1日乾燥させることにより、厚さ約150μmからなる塗膜を作製した。
亜鉛メッキ鋼板の表面に、製造直後の前記カチオン性ウレタン樹脂組成物を0.4g/100cm2の塗布量になるように、フィルムアプリケーターを用いてそれぞれ塗布し、100℃で1分間乾燥することにより試験片を作製した。
前記試験片の塗膜表面に40質量%リン酸水溶液を0.5mL滴下し1時間放置した。
また、前記試験片の塗膜表面(2)に10質量%水酸化ナトリウム水溶液を0.5mL滴下し1時間放置した。
フィルムアプリケーターを用いて、亜鉛メッキ鋼板に製造直後の各種カチオン性ウレタン樹脂組成物を0.4g/100cm2の塗布量になるようにそれぞれ塗布し、100℃で1分間乾燥することにより試験片を作製した。
A4サイズのガラス板に、高さ1mmの外枠を有するポリプロピレンフィルムを貼付し、該ポリプロピレンフィルム上に、実施例及び比較例で得られたカチオン性ウレタン樹脂組成物を6g/100cm2となるように塗布し、25℃で1日乾燥させることにより、厚さ約150μmからなる塗膜を作製した。
ガルバニウム鋼板及び亜鉛メッキ鋼板の表面に、製造直後の前記カチオン性ウレタン樹脂組成物を0.4g/100cm2の塗布量になるように、フィルムアプリケーターを用いてそれぞれ塗布し、100℃で1分間乾燥することにより2種の試験片を作製した。
Claims (8)
- 3級アミノ基または4級アンモニウム塩基と、脂肪族環式構造とを有するカチオン性ウレタン樹脂(A)及び水性媒体(B)を含有するカチオン性ウレタン樹脂組成物であって、前記カチオン性ウレタン樹脂(A)が、下記一般式〔I〕で示される構造を有し、かつ、脂肪族環式構造含有ポリエステルポリオール(c1)及び脂肪族環式構造含有ポリカーボネートポリオール(c2)からなる群より選ばれる1種以上と、3級アミノ基または4級アンモニウム塩基含有ポリオール(c3)とを含むポリオール(C)、ならびに、ポリイソシアネート(D)を反応させて得られるものであり、前記カチオン性ウレタン樹脂(A)中に含まれる脂肪族環式構造の含有量が、前記カチオン性ウレタン樹脂(A)の全量に対して2000mmol/kg〜5500mmol/kgであることを特徴とするカチオン性ウレタン樹脂組成物。
- 前記カチオン性ウレタン樹脂(A)が、前記脂肪族環式構造含有ポリエステルポリオール(c1)由来の脂肪族環式構造を、前記カチオン性ウレタン樹脂(A)中に含まれる脂肪族環式構造の全量に対して30質量%〜100質量%の範囲で含むものである、請求項1に記載のカチオン性ウレタン樹脂組成物。
- 前記カチオン性ウレタン樹脂(A)が、3級アミノ基及び4級アンモニウム塩基からなる群より選ばれる1種以上を、前記カチオン性ウレタン樹脂(A)の全量に対して合計30mmol/kg〜450mmol/kgの範囲で含有するものである、請求項1に記載のカチオン性ウレタン樹脂組成物。
- 前記脂肪族環式構造含有ポリエステルポリオール(c1)が、前記脂肪族環式構造含有ポリエステルポリオール(c1)全体に対して脂肪族環式構造を1000mmol/kg〜5000mmol/kgの範囲で含有するものである、請求項1に記載のカチオン性ウレタン樹脂組成物。
- 前記3級アミノ基または4級アンモニウム塩基含有ポリオール(c3)がN−メチルジエタノールアミンである、請求項1に記載のカチオン性ウレタン樹脂組成物。
- 前記カチオン性ウレタン樹脂(A)が加水分解性シリル基またはシラノール基を有するものである、請求項1に記載のカチオン性ウレタン樹脂組成物。
- 前記カチオン性ウレタン樹脂(A)が、前記カチオン性ウレタン樹脂(A)全量に対して、前記加水分解性シリル基及びシラノール基からなる群より選ばれる1種以上を、合計100mmol/kg〜250mmol/kg含有するものである、請求項6に記載のカチオン性ウレタン樹脂組成物。
- 請求項1〜7のいずれか1項に記載のカチオン性ウレタン樹脂組成物からなる金属用コーティング剤。
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