CA2186008A1 - Curable resin composition, coating composition, coating method and coated article - Google Patents
Curable resin composition, coating composition, coating method and coated articleInfo
- Publication number
- CA2186008A1 CA2186008A1 CA002186008A CA2186008A CA2186008A1 CA 2186008 A1 CA2186008 A1 CA 2186008A1 CA 002186008 A CA002186008 A CA 002186008A CA 2186008 A CA2186008 A CA 2186008A CA 2186008 A1 CA2186008 A1 CA 2186008A1
- Authority
- CA
- Canada
- Prior art keywords
- weight
- group
- polymer
- coating
- epoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 59
- 238000000576 coating method Methods 0.000 title claims description 80
- 239000008199 coating composition Substances 0.000 title claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 85
- 229920000642 polymer Polymers 0.000 claims abstract description 81
- 239000002253 acid Substances 0.000 claims abstract description 59
- 239000004593 Epoxy Substances 0.000 claims abstract description 56
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 53
- 229920005573 silicon-containing polymer Polymers 0.000 claims abstract description 50
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 46
- 229920001225 polyester resin Polymers 0.000 claims abstract description 45
- 239000004645 polyester resin Substances 0.000 claims abstract description 45
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 41
- 239000011248 coating agent Substances 0.000 claims description 60
- 239000000178 monomer Substances 0.000 claims description 55
- 125000004018 acid anhydride group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 229920003180 amino resin Polymers 0.000 claims description 22
- 150000008065 acid anhydrides Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000005370 alkoxysilyl group Chemical class 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002015 acyclic group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000011247 coating layer Substances 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 238000003860 storage Methods 0.000 abstract description 13
- 239000000203 mixture Substances 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000008096 xylene Substances 0.000 description 20
- 229920000877 Melamine resin Polymers 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 239000004640 Melamine resin Substances 0.000 description 15
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 14
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 14
- 238000005516 engineering process Methods 0.000 description 12
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 238000013329 compounding Methods 0.000 description 10
- 239000003973 paint Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 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 9
- -1 2-ethylhexyl Chemical group 0.000 description 9
- 229920003270 Cymel® Polymers 0.000 description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 9
- 229940072282 cardura Drugs 0.000 description 8
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 8
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 230000005856 abnormality Effects 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 125000005011 alkyl ether group Chemical group 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 239000008247 solid mixture Substances 0.000 description 5
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- NPAIMXWXWPJRES-UHFFFAOYSA-N butyltin(3+) Chemical compound CCCC[Sn+3] NPAIMXWXWPJRES-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- DHQIYHHEPUYAAX-UHFFFAOYSA-N n-(4,6-diamino-1,3,5-triazin-2-yl)prop-2-enamide Chemical compound NC1=NC(N)=NC(NC(=O)C=C)=N1 DHQIYHHEPUYAAX-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 125000005372 silanol group Chemical group 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000009503 electrostatic coating Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 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 2
- 239000004566 building material Substances 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- VKNUORWMCINMRB-UHFFFAOYSA-N diethyl malate Chemical compound CCOC(=O)CC(O)C(=O)OCC VKNUORWMCINMRB-UHFFFAOYSA-N 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 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 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- RTSODCRZYKSCLO-UHFFFAOYSA-N malic acid monomethyl ester Natural products COC(=O)C(O)CC(O)=O RTSODCRZYKSCLO-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical class O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- SUQPHYAFSSXBNB-UHFFFAOYSA-N 16-methylheptadecyl dihydrogen phosphate Chemical compound CC(C)CCCCCCCCCCCCCCCOP(O)(O)=O SUQPHYAFSSXBNB-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
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- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6/104526 | 1994-04-19 | ||
| JP10452594 | 1994-04-19 | ||
| JP6/104525 | 1994-04-19 | ||
| JP10452694 | 1994-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2186008A1 true CA2186008A1 (en) | 1995-10-26 |
Family
ID=26444980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002186008A Abandoned CA2186008A1 (en) | 1994-04-19 | 1995-04-18 | Curable resin composition, coating composition, coating method and coated article |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5760137A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0756614B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP3148246B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100305452B1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2225095A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2186008A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69506854T2 (cg-RX-API-DMAC7.html) |
| TW (1) | TW319790B (cg-RX-API-DMAC7.html) |
| WO (1) | WO1995028452A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0805837B1 (en) | 1995-01-24 | 1998-12-23 | Nippon Paint Co., Ltd. | Curable resin composition, coating composition and method for forming coated film |
| JPH10130581A (ja) * | 1996-10-25 | 1998-05-19 | Nippon Paint Co Ltd | 外板用塗膜、塗料組成物、塗膜形成方法及び被塗物 |
| US6225434B1 (en) | 1997-08-01 | 2001-05-01 | Ppg Industries Ohio, Inc. | Film-forming compositions having improved scratch resistance |
| US5916992A (en) * | 1997-08-01 | 1999-06-29 | Ppg Industries Ohio, Inc. | Polysiloxane polyols |
| US5952443A (en) * | 1997-08-01 | 1999-09-14 | Ppg Industries Ohio, Inc. | Acetoacetate functional polysiloxanes |
| US5939491A (en) * | 1997-08-01 | 1999-08-17 | Ppg Industries Ohio, Inc. | Curable compositions based on functional polysiloxanes |
| WO1999033889A1 (en) | 1997-12-24 | 1999-07-08 | Shell Internationale Research Maatschappij B.V. | Copolymers of ethylenically unsaturated monomers to be used in powder coatings |
| EP1104790A4 (en) * | 1998-07-10 | 2004-03-24 | Otsuka Chemical Co Ltd | WEATHER RESISTANT COMPOSITION, COATING MATERIALS AND MOLDED ARTICLES |
| US6395835B1 (en) * | 1999-02-25 | 2002-05-28 | Kansai Paint Co., Ltd. | Thermocurable resin composition for coating |
| MX252994B (es) | 1999-07-30 | 2008-01-07 | Ppg Ind Ohio Inc | Composiciones de recubrimiento que tienen una mejor resistencia a las raspaduras, sustratos recubiertos, y metodos relacionados con los mismo. |
| US6610777B1 (en) | 1999-07-30 | 2003-08-26 | Ppg Industries Ohio, Inc. | Flexible coating compositions having improved scratch resistance, coated substrates and methods related thereto |
| CN1209427C (zh) | 1999-07-30 | 2005-07-06 | 匹兹堡玻璃板工业俄亥俄股份有限公司 | 具有改进抗刮性的涂料组合物、涂覆基材及其有关方法 |
| US6635341B1 (en) | 2000-07-31 | 2003-10-21 | Ppg Industries Ohio, Inc. | Coating compositions comprising silyl blocked components, coating, coated substrates and methods related thereto |
| JP2003089764A (ja) * | 2001-09-19 | 2003-03-28 | Nissan Motor Co Ltd | クリヤ塗料組成物及びそれを用いた複層塗膜 |
| AR040209A1 (es) * | 2002-06-14 | 2005-03-16 | Agrolinz Melamin Gmbh | Material de moldeo de amino resina para productos con flexibilidad mejorada y productos de amino resina con flexibilidad mejorada |
| US7288607B2 (en) * | 2004-10-12 | 2007-10-30 | E. I. Du Pont De Nemours & Co. | High solids primer composition based on epoxy ring opening curing reaction |
| JP4634131B2 (ja) * | 2004-12-16 | 2011-02-16 | 関西ペイント株式会社 | アミノ樹脂水分散体組成物及び熱硬化性水性塗料組成物 |
| JP5225058B2 (ja) * | 2008-12-24 | 2013-07-03 | 日産自動車株式会社 | 自動車車体の塗装方法及び塗膜を有する自動車車体 |
| JP5456381B2 (ja) * | 2009-06-11 | 2014-03-26 | Ｂａｓｆジャパン株式会社 | 塗料組成物、塗装仕上げ方法および塗装物品 |
| US9938429B2 (en) * | 2014-07-18 | 2018-04-10 | BASF Coating GmbH | Coatings with flexible hyperbranched polyols |
| JP6265860B2 (ja) * | 2014-07-28 | 2018-01-24 | 日本ペイント・オートモーティブコーティングス株式会社 | 複層塗膜の形成方法及び複層塗膜 |
| CN110408035A (zh) * | 2019-07-11 | 2019-11-05 | 华伦纳路新材料有限公司 | 一种高加工性改性有机硅树脂 |
| JP2024177918A (ja) * | 2023-06-12 | 2024-12-24 | 中国塗料株式会社 | １液型水性塗料組成物 |
| WO2025100337A1 (ja) * | 2023-11-08 | 2025-05-15 | 関西ペイント株式会社 | １液硬化型塗料組成物及び塗装方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA210573A (en) * | 1921-04-19 | Conley Ga? | Game | |
| DE2907997C2 (de) * | 1979-03-01 | 1982-04-15 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von härtbaren Copolymeren |
| JP2791438B2 (ja) * | 1988-09-09 | 1998-08-27 | 関西ペイント株式会社 | 樹脂組成物及びその硬化方法 |
| JPH0819315B2 (ja) * | 1990-04-05 | 1996-02-28 | 日本ペイント株式会社 | 熱硬化性樹脂組成物 |
| JP2852129B2 (ja) * | 1990-12-28 | 1999-01-27 | 日本ペイント株式会社 | 熱硬化性塗料組成物 |
| DE69301158T2 (de) * | 1992-01-17 | 1996-05-30 | Kanegafuchi Chemical Ind | Härtbare Lackzusammensetzung |
| AU663967B2 (en) * | 1992-09-09 | 1995-10-26 | Nippon Paint Co., Ltd. | A curable resin composition, a coating composition and a process for forming a coating film |
| JP2886007B2 (ja) * | 1992-10-23 | 1999-04-26 | 鐘淵化学工業株式会社 | 塗料用硬化性組成物 |
| US5376706A (en) * | 1992-11-17 | 1994-12-27 | E. I. Du Pont De Nemours And Company | Anhydride epoxy coating composition modified with a silane polymer |
| JP2816082B2 (ja) * | 1993-03-19 | 1998-10-27 | 信越化学工業株式会社 | 硬化性樹脂組成物 |
-
1995
- 1995-04-17 TW TW084103881A patent/TW319790B/zh active
- 1995-04-18 AU AU22250/95A patent/AU2225095A/en not_active Abandoned
- 1995-04-18 CA CA002186008A patent/CA2186008A1/en not_active Abandoned
- 1995-04-18 JP JP52687195A patent/JP3148246B2/ja not_active Expired - Lifetime
- 1995-04-18 DE DE69506854T patent/DE69506854T2/de not_active Expired - Fee Related
- 1995-04-18 US US08/727,464 patent/US5760137A/en not_active Expired - Lifetime
- 1995-04-18 EP EP95915342A patent/EP0756614B1/en not_active Expired - Lifetime
- 1995-04-18 WO PCT/JP1995/000757 patent/WO1995028452A1/en not_active Ceased
- 1995-04-18 KR KR1019960705853A patent/KR100305452B1/ko not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0756614B1 (en) | 1998-12-23 |
| KR100305452B1 (ko) | 2002-10-04 |
| JPH10503787A (ja) | 1998-04-07 |
| US5760137A (en) | 1998-06-02 |
| DE69506854D1 (de) | 1999-02-04 |
| AU2225095A (en) | 1995-11-10 |
| WO1995028452A1 (en) | 1995-10-26 |
| TW319790B (cg-RX-API-DMAC7.html) | 1997-11-11 |
| EP0756614A1 (en) | 1997-02-05 |
| KR970702334A (ko) | 1997-05-13 |
| DE69506854T2 (de) | 1999-06-17 |
| JP3148246B2 (ja) | 2001-03-19 |
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| Date | Code | Title | Description |
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