JPH0342315B2 - - Google Patents
Info
- Publication number
- JPH0342315B2 JPH0342315B2 JP13765983A JP13765983A JPH0342315B2 JP H0342315 B2 JPH0342315 B2 JP H0342315B2 JP 13765983 A JP13765983 A JP 13765983A JP 13765983 A JP13765983 A JP 13765983A JP H0342315 B2 JPH0342315 B2 JP H0342315B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- acid
- caprolactone
- hydroxyl group
- polyester polyol
- 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.)
- Expired
Links
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 238000000576 coating method Methods 0.000 claims description 27
- -1 acrylic ester Chemical class 0.000 claims description 26
- 239000011248 coating agent Substances 0.000 claims description 26
- 229920005906 polyester polyol Polymers 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 18
- 229920006163 vinyl copolymer Polymers 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 13
- 229920003180 amino resin Polymers 0.000 claims description 11
- 239000011342 resin composition Substances 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 15
- 229920005862 polyol Polymers 0.000 description 13
- 150000003077 polyols Chemical class 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- NIDNOXCRFUCAKQ-RNGGSSJXSA-N (1r,2r,3s,4s)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@@H]2C=C[C@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-RNGGSSJXSA-N 0.000 description 1
- UJIHVZPVGXBWJZ-AATRIKPKSA-N (E)-4-(6-hydroxyhexoxy)-4-oxobut-2-enoic acid Chemical compound OCCCCCCOC(=O)\C=C\C(O)=O UJIHVZPVGXBWJZ-AATRIKPKSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- 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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- KYIMHWNKQXQBDG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC Chemical compound N=C=O.N=C=O.CCCCCC KYIMHWNKQXQBDG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 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
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- OGVXYCDTRMDYOG-UHFFFAOYSA-N dibutyl 2-methylidenebutanedioate Chemical compound CCCCOC(=O)CC(=C)C(=O)OCCCC OGVXYCDTRMDYOG-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IIQWTZQWBGDRQG-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;isocyanic acid Chemical group N=C=O.CCOC(=O)C(C)=C IIQWTZQWBGDRQG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 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 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 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 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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The present invention relates to a resin composition for coating, and more particularly, it comprises a specific hydroxyl group-containing vinyl copolymer, an ε-caprolactone-modified polyester polyol, and further an isocyanate compound or an amino resin as essential components. The present invention relates to a composition. Recently, the range of coating base materials has gradually expanded from metal bases such as iron to flexible materials such as plastics and rubber, and as a result, coatings on the latter materials have become extremely common. Furthermore, there is a demand for flexible covering materials or coating materials used therein. In this way, in order to obtain a coating material or coating material that provides a flexible cured coating film, acrylic polyols with a low glass transition point, polyhydric alcohols and polyhydric carboxylic acids are used as coating film-forming resin components. Polyester polyols obtained from and the like are effective. However, although cured coatings obtained using such acrylic polyols with low glass transition points and isocyanate compounds or amino resins have flexibility, they do not have sufficient hardness and solvent resistance, and they are not compatible with polyester polyols. Cured coating films obtained using isocyanate compounds or amino resins do not have sufficient weather resistance or flexibility at low temperatures. As described above, it is unlikely that a cured coating film that satisfies all of weather resistance, solvent resistance, and flexibility can be obtained from coating resin compositions that have the above-mentioned combinations. However, the present inventors have obtained a coating resin composition that can provide a cured coating film with excellent weather resistance, solvent resistance, and flexibility on flexible substrates such as plastics or rubber. As a result of intensive studies, it was discovered that a resin composition consisting of a hydroxyl group-containing vinyl copolymer, an ε-caprolactone-modified polyester polyol, and an isocyanate compound or an amino resin meets these objectives, and the present invention has been completed. I reached it. That is, the present invention consists of 1 to 40% by weight of a hydroxyl group-containing monomer, 99 to 10% by weight of (meth)acrylic acid ester, and 0 to 50% by weight of other copolymerizable monomers. Hydroxyl group-containing vinyl copolymer (A)
50 to 90 parts by weight and 50 parts by weight of ε-caprolactone modified polyester polyol (B) with a hydroxyl value of 20 to 300.
10 parts by weight of the isocyanate compound (C) and an appropriate amount of the isocyanate compound (C) as essential components. 90 parts by weight, 50 to 10 parts by weight of the above ε-caprolactone-modified polyester polyol (B), and an appropriate amount of an amino resin (D) as essential components. It is. Here, typical examples of the above-mentioned hydroxyl group-containing monomers include β-hydroxyethyl acrylate, β-hydroxyethyl methacrylate, β-hydroxypropyl acrylate, β-hydroxypropyl methacrylate,
-Hydroxybutyl acrylate or β-hydroxybutyl methacrylate, 3-chloro-2-
Hydroxypropyl (meth)acrylate, di-
2-hydroxyethyl fumarate, mono-2-hydroxyethyl-monobutyl fumarate, or mono(meth)acrylate of polyethylene glycol or polypropylene glycol,
"Plaxel FM or FA monomer" [Caprolactone addition monomers manufactured by Daicel Chemical Co., Ltd.]
Hydroxyalkyl esters of α,β-ethylenically unsaturated carboxylic acids such as, or adducts of these with ε-caprolactone: (meth)acrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid or citraconic acid unsaturated mono- or dicarboxylic acids such as, α,β-ethylenically unsaturated carboxylic acid hydroxyalkyl esters such as monoesters of these dicarboxylic acids and monohydric alcohols, and maleic acid, succinic acid, and phthalic acid. , hexahydrophthalic acid, tetrahydrophthalic acid, benzenetricarboxylic acid, benzenetetracarboxylic acid, "Himic acid" (product of Hitachi Chemical Co., Ltd.), anhydrides of polycarboxylic acids such as tetrachlorophthalic acid or dodecynylsuccinic acid. Various unsaturated carboxylic acids such as adducts of
"Cardilla E" (glycidyl esters of branched synthetic resin acids manufactured by Siel in the Netherlands), monoglycidyl esters of monovalent carboxylic acids such as coconut oil fatty acid glycidyl esters or glycidyl octylate esters or butyl glycidyl ether, ethylene oxide or adducts with monoepoxy compounds such as propylene oxide, or adducts with these and ε-caprolactone; (including degenerated types). In addition, typical examples of the above-mentioned (meth)acrylic esters include methyl (meth)acrylate, ethyl (meth)acrylate (meth)
n-butyl acrylate, i-(meth)acrylate
Butyl, 2-ethylhexyl (meth)acrylate,
Examples include lauryl (meth)acrylate and cyclohexyl (meth)acrylate. Furthermore, representative examples of the other copolymerizable monomers mentioned above include diesters of unsaturated dibasic acids such as styrene, dibutyl fumarate, dimethyl maleate, or dibutyl itaconate; Monomers containing acid groups, such as acrylic acid, fumaric acid or maleic acid, (meth)
Phosphorous atom-containing monomers such as acryloyloxyalkyl acid phosphates, silicon atom-containing monomers such as âKR-215â or âX-22-5002â [products of Shin-Etsu Chemical Co., Ltd.], or ( Acid amide monomers such as meth)acrylamide, etc.
Furthermore, there is no problem in using a portion of (meth)acrylonitrile or dimethylaminomethyl (meth)acrylate in combination. In order to prepare the above-mentioned hydroxyl group-containing vinyl copolymer (A) using the monomers listed above, aromatic systems such as toluene or xylene, ester systems such as ethyl acetate or butyl acetate, methyl ethyl ketone or methyl isobutyl Solution polymerization can be easily carried out using a ketone solvent such as ketone in the presence of a known and commonly used polymerization initiator that generates radical groups. On the other hand, in order to prepare the above-mentioned ε-caprolactone-modified polyester polyol (B), ε-
- This may be a method of adding caprolactone, or a method of adding ε-caprolactone to a polyhydric alcohol in advance and then esterifying a polyhydric carboxylic acid or even a monoepoxide or diepoxide. You can read it. Here, typical polyhydric alcohols include ethylene glycol, 1,4-butanediol, 1,6-hexanediol, glycerin, trimethylolpropane, and pentaerythritol, but of course, a mixture of these alcohols may be used. On the other hand, typical examples of the polycarboxylic acids mentioned above include succinic acid, adipic acid, azelaic acid, sebacic acid, decane-1,10-dicarboxylic acid, terephthalic acid, isophthalic acid, or phthalic acid (anhydride). Examples include acids, but these may of course be used in the form of a mixture. In addition to the compounds mentioned above, itaconic acid, fumaric acid, maleic acid, etc. can be used as the acid component, and oils and fats such as soybean oil, coconut oil, castor oil, tall oil, etc. can be used as acid components. Alternatively, there is no problem in using fatty acids obtained from the oil in combination with the above-mentioned compounds. Furthermore, typical monoepoxides or diepoxides mentioned above include "Carduura E" (glycidyl ester of Versateic acid manufactured by Schiel, Netherlands) and compounds commonly used as epoxy resins. The hydroxyl value of the thus obtained ε-caprolactone modified polyester polyol (B) is usually 20 to 300, but the isocyanate compound (C)
When used in combination with amino resin (D), the range is preferably from 25 to 200. On the other hand, when used in combination with amino resin (D), the range is preferably from 25 to 100. The polyester polyol (B) is used together with the hydroxyl group-containing vinyl copolymer (A) to constitute the "base polyol" component in the composition of the present invention. In other words, the hydroxyl group-containing vinyl copolymer (A) and this ε
-Caprolactone-modified polyester polyol (B)
The composition consisting of is cured with an isocyanate compound (C) or an amino resin (D), and the cured coating film thus obtained has excellent flexibility and solvent resistance. Here, the usage ratio (weight ratio) of the hydroxyl group-containing vinyl copolymer (A) and the ε-caprolactone modified polyester polyol (B): (A)/(B) = 50-90/50-10,
Preferably, (A)/(B)=60-80/40-20, and within this range, a coating film with good coating performance can be obtained. When the hydroxyl group-containing vinyl copolymer (A) is less than 50 parts by weight, the weather resistance is insufficient, and on the other hand, ε
-Caprolactone-modified polyester polyol (B)
If the amount is less than 10 parts by weight, it is not preferable because the flexibility of the coating film cannot be obtained. Next, in the present invention, typical isocyanate compounds (C) used as the curing agent (crosslinking agent) component include aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate; hexamethylene diisocyanate, trimethyl Aliphatic diisocyanates such as hexane diisocyanate; isophorone diisocyanate, methylcyclohexane-2,4
(or 2,6-) diisocyanate, 4,
Alicyclic diisocyanates such as 4'-methylenebis(cyclohexyl isocyanate) and 1,3-di(isocyanatomethyl)cyclohexane; or these diisocyanates and ethylene glycol, polyether polyols (polyethylene glycol, polypropylene glycol, polycaprolactone polyols, etc.). ), polyhydric alcohols such as trimethylolethane and trimethylolpropane, low molecular weight polyester resins (including oil-modified types) that have functional groups that can react with isocyanate groups, acrylic copolymers, water, etc. Adducts; or biuret bodies, copolymers of diisocyanates (including oligomers); furthermore, 2-hydroxypropyl (meth)acrylate-hexamethylene diisocyanate equimolar adducts, and isocyanate groups such as isocyanate ethyl methacrylate; Copolymers Known and commonly used so-called prepolymers with free isocyanate groups that are reactive with active hydrogen, such as copolymers that contain vinyl monomers as essential components and unsaturated double bonds. etc. can be used,
Commercially available compounds (C) include "Barnoc D-750, DN-950" (products of Dainippon Ink & Chemicals Co., Ltd.) and "Desmodyur N".
(product of Bayer, West Germany). On the other hand, typical examples of the crosslinking agent that is the amino resin (D) include methylolization of an amino group-containing compound such as melamine, urea, or guanamine with an aldehyde such as formalin, and then a lower aliphatic alcohol. There are products in which at least two of the methylol groups are etherified, and typical commercially available products include "Betsukamine P-138",
Examples include "Supervetsucomin J-820" (product of Dainippon Ink & Chemicals Co., Ltd.) and "Cymel 300" (product of American Cyanamid, Inc.). In obtaining the composition of the present invention, the blending ratio of the base polyol component consisting of the above-mentioned hydroxyl group-containing vinyl copolymer (A) and ε-caprolactone-modified polyester polyol (B) and the curing agent component is as follows: Although it varies depending on the type of the curing agent component, it is roughly as follows. That is, it is appropriate that the solid content weight ratio of the base polyol component and the amino resin (D) component is in the range of 90/10 to 60/40, while the solid content weight ratio of the base polyol component and the isocyanate compound (C) component is An appropriate solid content weight ratio is within a range where the ratio of the number of hydroxyl groups in the base polyol component to the number of isocyanate groups in the isocyanate compound (C) is 1/0.5 to 1/1.5. , weather resistance and solvent resistance can be ensured. Both curing agents or crosslinking agent components listed above and each of the above-mentioned hydroxyl group-containing vinyl copolymers
The cured coating film obtained using the coating resin composition of the present invention, which has a base resin (base polyol) component consisting of (A) and ε-caprolactone-modified polyester polyol (B) as essential components, is extremely flexible. The composition of the present invention can be applied to a wide range of substrates because it has excellent flexibility and impact resistance, especially at low temperatures, and also has excellent weather resistance and solvent resistance. For example, the composition of the present invention can be used not only as a coating agent for painting metals but also on flexible materials such as plastics or rubber, as well as on wood products or concrete products. Suitable for materials that require flexibility, such as for automobile bumpers. Next, the present invention will be specifically explained with reference to Reference Examples, Examples, and Comparative Examples. In the following, all parts and percentages are based on weight unless otherwise specified. Reference Example 1 [Preparation example of hydroxyl group-containing vinyl copolymer (A)] 250 g of toluene and 500 g of butyl acetate were supplied to a reactor equipped with a stirrer and a cooler, and the temperature inside the reactor was raised to 120°C. Heat and maintain at the same temperature, add 200 g of styrene, 400 g of n-butyl methacrylate,
Dissolve 5 g of azobisisobutyronitrile and 5 g of t-butyl peroxybenzoate in a monomer mixture consisting of 195 g of n-butyl acrylate, 200 g of β-hydroxyethyl methacrylate, and 5 g of acrylic acid, and 250 g of toluene. The dissolved material was added dropwise into the reactor over a period of 4 hours, and the temperature was kept at the same temperature for 10 hours. The nonvolatile content (NV) was 50.2%, and the hydroxyl value of the copolymer solution was 50.2%.
A solution of the hydroxyl group-containing vinyl copolymer (A) No. 43 was obtained. Hereinafter, this will be abbreviated as copolymer (A-1). Reference example 2 (same as above) 250 g of toluene was placed in the same reaction vessel as in reference example 1.
and 500g of butyl acetate, and the temperature inside the container was
Raise the temperature to 120â, and at the same temperature, add 150g of styrene, 400g of n-butyl methacrylate, and 195g of n-butyl acrylate.
g, β-hydroxyethyl methacrylate 250g,
A monomer mixture consisting of 5 g of acrylic acid and 5 g of azobisisobutyronitrile in 250 g of toluene.
and 5 g of t-butyl peroxybenzoate
NV was added dropwise over 4 hours and kept at the same temperature for 10 hours.
A solution of the hydroxyl group-containing vinyl copolymer (A) having a hydroxyl value of 50.5% and a hydroxyl value of 54 was obtained. Hereinafter, this will be abbreviated as copolymer (A-2). Reference Example 3 [Preparation example of ε-caprolactone modified polyester polyol (B)] 398.6 g of adipic acid, trimethylolpropane
153.9g, 404g of 1,6-hexanediol and 180g of isophthalic acid.
Next, 428.6 g of ε-caprolactone was added to this for an addition reaction, and the hydroxyl value of the solid content was 105.
An ε-caprolactone modified polyester polyol was obtained. Afterwards, this polyester polyol
A solution of ε-caprolactone-modified polyester polyol (B) having an NV of 60.5% and a hydroxyl value of 63 was obtained by dissolving it in 666.6 g of xylene and 285.7 g of methyl isobutyl ketone. Hereinafter, this will be abbreviated as polyol (B-1). Reference Example 4 (Same as above) An esterification reaction was carried out using 369.6 g of phthalic anhydride, 157.6 g of trimethylolpropane, and 517 g of "Carduura E", and then an addition reaction was carried out by adding 259.2 g of ε-caprolactone. An ε-caprolactone modified polyester polyol having a hydroxyl value of 123.5 was obtained. Afterwards, this polyester polyol
A solution of ε-caprolactone modified polyester polyol (B) having an NV of 60.1% and a hydroxyl value of 74 was obtained by dissolving it in 604 g of xylene and 259 g of methyl isobutyl ketone. Hereinafter, this will be abbreviated as polyol (B-2). Example 1 100% of the copolymer (A-1) obtained in Reference Example 1
of the polyol (B-1) obtained in Part and Reference Example 3.
35.7 parts and then "Taipeke R-820"
After mixing 47.6 parts of methyl-type titanium oxide manufactured by Ishihara Sangyo Co., Ltd. and dispersing it with a sand mill, the mixture was further mixed with ``Barnok DN-950'' [Dainippon Ink Chemical Industry Co., Ltd.].
After adding 39.2 parts of Isocyanate Compound (manufactured by Co., Ltd.) and diluting with thinner to adjust the viscosity of the paint, it was spray-painted on a mild steel plate and force-dried at 80°C for 30 minutes. Physical property tests were conducted on the cured coating film obtained here, and the results shown in Table 1 were obtained. Examples 2 to 4 and Comparative Example 1 Coating resin compositions were obtained at the blending ratios shown in Table 1, and then cured coating films were obtained using the respective coating resin compositions. Physical property tests on the membrane were conducted in the same manner as in Example 1. The results are summarized in the same table, and the evaluation criteria are as follows. â...Excellentã...Good Ã...Unsatisfactory
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ããã«ãã¹ãŒããŒããã«ãã³ïŒ¬â117â60ãã倧æ¥
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ÃâŠâŠäžå¯[Table] Examples 5 to 8 and Comparative Example 2 First, the hydroxyl group-containing vinyl copolymer (A) and the ε-caprolactone-modified polyester polyol (B) were mixed at the blending ratios shown in Table 2, and then the ε-caprolactone modified polyester polyol (B) was mixed. Disperse "Tiepeke R-820" with a sand mill,
Furthermore, after adding "Super Betsukamine L-117-60" [melamine resin manufactured by Dainippon Ink & Chemicals Co., Ltd.], dilute it with thinner to adjust the viscosity of the paint, and then apply each of the resulting paints. It was spray painted on a mild steel plate and then baked at 150°C for 20 minutes. Physical property tests were conducted on each of the cured coating films thus obtained, and the results shown in the table were obtained. The evaluation criteria for each physical property are as follows. â...Excellentã...Good Ã...Unsatisfactory
Claims (1)
ã¢ã¯ãªã«é žãšã¹ãã«ã®99ã10ééïŒ ãšããã®ä»ã®
å ±éåå¯èœãªåéäœã®ïŒã50ééïŒ ãšãããªãæ°Ž
é žåºå«æããã«å ±éåäœ(A)ã®50ã90éééšãšãæ°Ž
é žåºäŸ¡ã20ã300ãªãεâã«ããã©ã¯ãã³å€æ§ã
ãªãšã¹ãã«ããªãªãŒã«(B)ã®50ã10éééšãšãã€ãœ
ã·ã¢ããŒãååç©(C)ãšãå¿ é ã®æåãšããŠå«æã
ãããšãç¹åŸŽãšããã被èŠçšæš¹èçµæç©ã ïŒ æ°Žé žåºå«æåéäœã®ïŒã40ééïŒ ãšãïŒã¡ã¿ïŒ
ã¢ã¯ãªã«é žãšã¹ãã«ã®99ã10ééïŒ ãšããã®ä»ã®
å ±éåå¯èœãªåéäœã®ïŒã50ééïŒ ãšãããªãæ°Ž
é žåºå«æããã«å ±éåäœ(A)ã®50ã90éééšãšãæ°Ž
é žåºäŸ¡ã20ã300ãªãεâã«ããã©ã¯ãã³å€æ§ã
ãªãšã¹ãã«ããªãªãŒã«(B)ã®50ã10éééšãšãã¢ã
ãæš¹è(D)ãšãå¿ é ã®æåãšããŠå«æããããšãç¹
城ãšããã被èŠçšæš¹èçµæç©ã[Scope of Claims] 1 1 to 40% by weight of a hydroxyl group-containing monomer, and (meth)
50 to 90 parts by weight of a hydroxyl group-containing vinyl copolymer (A) consisting of 99 to 10% by weight of acrylic ester and 0 to 50% by weight of other copolymerizable monomers, and a hydroxyl value of 20 A resin composition for coating, characterized in that it contains 50 to 10 parts by weight of an ε-caprolactone-modified polyester polyol (B) of ~300 and an isocyanate compound (C) as essential components. 2 1 to 40% by weight of hydroxyl group-containing monomer and (meth)
50 to 90 parts by weight of a hydroxyl group-containing vinyl copolymer (A) consisting of 99 to 10% by weight of acrylic ester and 0 to 50% by weight of other copolymerizable monomers, and a hydroxyl value of 20 A resin composition for coating, characterized in that it contains 50 to 10 parts by weight of an ε-caprolactone-modified polyester polyol (B) of ~300 and an amino resin (D) as essential components.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13765983A JPS6031579A (en) | 1983-07-29 | 1983-07-29 | Coating resin composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP13765983A JPS6031579A (en) | 1983-07-29 | 1983-07-29 | Coating resin composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6031579A JPS6031579A (en) | 1985-02-18 |
JPH0342315B2 true JPH0342315B2 (en) | 1991-06-26 |
Family
ID=15203808
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP13765983A Granted JPS6031579A (en) | 1983-07-29 | 1983-07-29 | Coating resin composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6031579A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6420040B1 (en) * | 1999-04-30 | 2002-07-16 | The Valspar Corporation | Coating composition for metal substrates |
JP4872247B2 (en) | 2005-06-16 | 2012-02-08 | ïœïœïœã³ãŒãã£ã³ã°ã¹ãžã£ãã³æ ªåŒäŒç€Ÿ | Thermosetting coating composition |
-
1983
- 1983-07-29 JP JP13765983A patent/JPS6031579A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6031579A (en) | 1985-02-18 |
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