JP2008019420A - 塗料用樹脂組成物および塗料 - Google Patents
塗料用樹脂組成物および塗料 Download PDFInfo
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- JP2008019420A JP2008019420A JP2007088334A JP2007088334A JP2008019420A JP 2008019420 A JP2008019420 A JP 2008019420A JP 2007088334 A JP2007088334 A JP 2007088334A JP 2007088334 A JP2007088334 A JP 2007088334A JP 2008019420 A JP2008019420 A JP 2008019420A
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- component
- resin composition
- resin
- coating
- amine
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- 238000000576 coating method Methods 0.000 title claims abstract description 67
- 239000011248 coating agent Substances 0.000 title claims abstract description 58
- 239000011342 resin composition Substances 0.000 title claims abstract description 41
- 239000003822 epoxy resin Substances 0.000 claims abstract description 24
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 24
- 239000004645 polyester resin Substances 0.000 claims abstract description 16
- 229920001225 polyester resin Polymers 0.000 claims abstract description 16
- 239000003973 paint Substances 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 125000002723 alicyclic group Chemical group 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 18
- 150000001735 carboxylic acids Chemical class 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 150000005846 sugar alcohols Polymers 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- -1 alicyclic diol Chemical class 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229920000877 Melamine resin Polymers 0.000 claims description 5
- 229920001228 polyisocyanate Polymers 0.000 claims description 5
- 239000005056 polyisocyanate Substances 0.000 claims description 5
- 239000004640 Melamine resin Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000007797 corrosion Effects 0.000 abstract description 13
- 238000005260 corrosion Methods 0.000 abstract description 13
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 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 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 4
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 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
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000007769 metal material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- WOZVHXUHUFLZGK-UHFFFAOYSA-N terephthalic acid dimethyl ester Natural products COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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- 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 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
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- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 1
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- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 238000010521 absorption reaction Methods 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 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
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical class NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 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
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
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Abstract
【解決手段】 アミン変性エポキシ樹脂(A)とポリエステル樹脂(B)を含有する塗料用樹脂組成物を用いる。
Description
攪拌機、冷却器、温度計および窒素ガス導入管を備えた反応容器に、ステアリルアミン38.3g、ジエタノールアミン7.7g、ビスフェノールA型エポキシ樹脂(商品名「エポトートYD−014」;東都化成(株)製:エポキシ基濃度950)350g、キシレン303gを仕込み、これらを窒素気流下で100℃において、5時間反応させることにより、(A1)成分を得た。この樹脂の物性値を表1に示す。
製造例1と同様の反応容器に、ステアリルアミン38.3g、ジエタノールアミン7.7g、ビスフェノールA型エポキシ樹脂(商品名「エポトートYD−014」;東都化成(株)製:エポキシ基濃度950)350g、キシレン303gを仕込み、これらを窒素気流下で100℃において、5時間反応させて、変性エポキシ樹脂を得た。次いで、同反応容器にイソホロンジイソシアネート8.3g、シクロヘキサノン303gを仕込み、これらを窒素気流下で100℃において5時間反応させることにより、(A2)成分を得た。この樹脂の物性値を表1に示す。
製造例2において、アミン成分の種類(括弧内は使用重量)を表1に示すように変えた他は製造例1と同様にして(A3)成分〜(A5)成分を得た。それぞれの物性値を表1に示す。
製造例1と同様の反応容器に、シクロヘキサンジメタノール68g、エチレングリコール54g、ネオペンチルグリコール68g、ヘキサヒドロ無水フタル酸52g、シクロヘキサン−1,4−ジカルボン酸231gを仕込み、攪拌下に反応系を加熱してこれらの原料を溶融させ、次いで170℃から220℃まで縮合反応で生成するメタノールと水を除去しながら3時間かけて徐々に昇温し、更に220℃で1時間保温した。次いで、反応系に三酸化アンチモンを0.10g仕込み、また反応容器に真空減圧装置をつないで、260℃、0.13kPaで2時間、減圧重縮合反応を行った。次いで、減圧状態を解除して反応系を150℃まで冷却し、反応系にソルベッソ#100(エクソン社製)を300部、ブチルセロソルブを300部加えて、(B1)成分を得た。この樹脂の物性値を表2に示す。
製造例6において、アルコール成分と酸成分の種類(括弧内は使用重量)を表2に示すように変えた以外は同様にして、(B2)成分を得た。この樹脂の物性値を表2に示す。
SA:ステアリルアミン
2−EHA:2−エチルヘキシルアミン
DEA:ジエタノールアミン
MEA:N−メチルエタノールアミン
YD014:「エポトートYD−014」
IPDI:イソホロンジイイソシアネート
CHDM:1,4−シクロヘキサンジメタノール
EG:エチレングリコール
NPG:ネオペンチルグリコール
1,4BG:1,4−ブタンジオール
HHPA:ヘキサヒドロ無水フタル酸
CHDA:シクロヘキサン−1,4−ジカルボン酸
DMT:テレフタル酸ジメチル
IPA:イソフタル酸
SBA:セバチン酸
Nv(%):固形分濃度
Mw:重量平均分子量
AV:アミン価
OHV:水酸基価
前記(A1)成分と前記(B1)成分をそれぞれ70mlずつサンプルビンに採取し、スパテラで十分に混合した後、泡が消失するまで放置した。次いで、(A1)成分と(B1)成分の合計固形分重量に対して20重量%となる量のメラミン樹脂(商品名「サイメル303」、日本サイテックインダストリーズ(株)製)を硬化剤として加え、同様に混合して放置した。得られた組成物を塗料として用いる。
実施例1と同様にして、表3に示す組み合わせによる塗料用樹脂組成物を得た。次いで、実施例1と同様にして架橋剤を加えて混合した。得られた組成物を塗料として用いる。
前記ビスフェノールA型エポキシ樹脂(エポトートYD−014)と前記(B1)成分を表3に示す割合量(固形分重量比)となるように混合し、比較用の塗料用樹脂組成物を得た。次いで、実施例1と同様にして架橋剤を加えて混合した。得られた組成物を塗料として用いる。前記(B2)成分についても同様にして、比較用の塗料用樹脂組成物を得、同様にして塗料とした。
前記(A1)成分〜(A5)成分、および(B1)成分〜(B2)成分をそれぞれ単独で塗料として用いた。
前記試験板を用いてJIS-K-5400に準じて塩水噴霧テストを行い、20日後、粘着テープ(約24mm幅)を用いて塗膜の剥離試験を行った。塗膜の剥離幅に応じて、耐食性の評価を以下の基準で評価をした。結果は表3に示す。
◎:2mm未満
○:2mm以上−3mm未満
△:3mm以上−6mm未満
×:6mm以上
前記試験板を用いて四片缶打ち抜き加工を行い、塗膜の剥離程度を以下の基準で目視評価した。結果は表3に示す。
◎:特に優秀(塗膜にワレやヒビが発生しない。)
○〜○△:優秀(塗膜のワレやヒビが1〜2箇所である。)
△〜△×:やや不良(塗膜のワレやヒビが3〜4箇所発生する。)
×:不良(塗膜にワレやヒビが5箇所以上発生する。)
実施例1〜14、比較例1〜2については、塗料用樹脂組成物の相溶性を以下の基準で目視評価した。結果は表3に示す。
○:クリア
△:やや濁り
×:白濁
なお、各評価間の状態は、例えば○△として表記する。
Claims (11)
- アミン変性エポキシ樹脂(A)とポリエステル樹脂(B)を含有する塗料用樹脂組成物。
- アミン変性エポキシ樹脂(A)が、アミン類(a1)およびビスフェノール型エポキシ樹脂(a2)を反応成分とするものである、請求項1に記載の塗料用樹脂組成物。
- アミン類(a1)が、分子内に炭素数3〜30のアルキル基を1つ以上有するアミン類であることを特徴とする、請求項1または2に記載の塗料用樹脂組成物。
- アミン変性エポキシ樹脂(A)が、更にポリイソシアネート類(a3)を反応成分とするものであることを特徴とする、請求項1〜3のいずれかに記載の塗料用樹脂組成物。
- ポリエステル樹脂(B)が、多価アルコール類(b1)および多価カルボン酸類(b2)を反応成分とするものである、請求項1〜4のいずれかに記載の塗料用樹脂組成物。
- ポリエステル樹脂(B)が、分子内に脂環構造を有するものであることを特徴とする、請求項1〜5のいずれかに記載の塗料用樹脂組成物。
- 多価アルコール類(b1)が脂環族ジオールであることを特徴とする、請求項1〜6のいずれかに記載の塗料用樹脂組成物。
- 多価カルボン酸類(b2)が脂環族ジカルボン酸であることを特徴とする、請求項1〜7のいずれかに記載の塗料用樹脂組成物。
- 請求項1〜8のいずれかに記載の塗料用樹脂組成物と硬化剤とを含有してなる塗料。
- 硬化剤がメラミン樹脂である、請求項9に記載の塗料。
- さらに溶剤を含有する請求項9または10に記載の塗料。
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JP2010235919A (ja) * | 2009-03-11 | 2010-10-21 | Arakawa Chem Ind Co Ltd | ラッカー型塗料用樹脂及び塗料 |
JP2019108443A (ja) * | 2017-12-18 | 2019-07-04 | 東洋インキScホールディングス株式会社 | 印刷インキ組成物 |
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JPH02212568A (ja) * | 1989-02-13 | 1990-08-23 | Arakawa Chem Ind Co Ltd | ラッカー型塗料用樹脂の製造方法 |
JPH0328858A (ja) * | 1989-06-27 | 1991-02-07 | Ricoh Co Ltd | 乾式電子写真用トナー |
JPH08501124A (ja) * | 1993-01-25 | 1996-02-06 | ピーピージー インダストリーズ,インコーポレイテッド | 自動車用再仕上げプライマーサーフェイサー |
JP2001009366A (ja) * | 1999-06-29 | 2001-01-16 | Nkk Corp | 成形加工性に優れた1コートプレコート鋼板及びその製造方法 |
JP2001139876A (ja) * | 1999-11-15 | 2001-05-22 | Toyobo Co Ltd | 塗料用樹脂組成物 |
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JPH02212568A (ja) * | 1989-02-13 | 1990-08-23 | Arakawa Chem Ind Co Ltd | ラッカー型塗料用樹脂の製造方法 |
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JP2019108443A (ja) * | 2017-12-18 | 2019-07-04 | 東洋インキScホールディングス株式会社 | 印刷インキ組成物 |
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