TWI325883B - Low gloss, low temperature curing powder coating compositions - Google Patents
Low gloss, low temperature curing powder coating compositions Download PDFInfo
- Publication number
- TWI325883B TWI325883B TW92130912A TW92130912A TWI325883B TW I325883 B TWI325883 B TW I325883B TW 92130912 A TW92130912 A TW 92130912A TW 92130912 A TW92130912 A TW 92130912A TW I325883 B TWI325883 B TW I325883B
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- Taiwan
- Prior art keywords
- acrylate
- meth
- acid
- group
- carboxylic acid
- Prior art date
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- 239000000843 powder Substances 0.000 title claims abstract description 57
- 239000008199 coating composition Substances 0.000 title claims abstract description 28
- 238000013035 low temperature curing Methods 0.000 title description 2
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 66
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 229920000728 polyester Polymers 0.000 claims abstract description 60
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 43
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 41
- 238000000576 coating method Methods 0.000 claims abstract description 40
- 239000011248 coating agent Substances 0.000 claims abstract description 29
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 239000000758 substrate Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 75
- 239000002253 acid Substances 0.000 claims description 66
- 230000009477 glass transition Effects 0.000 claims description 56
- -1 glyceryl acryl Chemical group 0.000 claims description 49
- 229920001577 copolymer Polymers 0.000 claims description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 229910052797 bismuth Inorganic materials 0.000 claims description 17
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 15
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 229920005862 polyol Polymers 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
- 239000011976 maleic acid Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052712 strontium Inorganic materials 0.000 claims description 7
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 238000013007 heat curing Methods 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 5
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 5
- 150000007519 polyprotic acids Polymers 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
- 239000002023 wood Substances 0.000 claims description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000011094 fiberboard Substances 0.000 claims description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 238000001029 thermal curing Methods 0.000 claims description 3
- 239000004711 α-olefin Substances 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- LHXNVCCLDTYJGT-UHFFFAOYSA-N 1-(oxiran-2-ylmethoxy)propan-2-ol Chemical compound CC(O)COCC1CO1 LHXNVCCLDTYJGT-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 2
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 2
- 229940018557 citraconic acid Drugs 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- 239000011087 paperboard Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims 2
- 238000005227 gel permeation chromatography Methods 0.000 claims 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- CYQKECCDKADPPI-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl)methanone Chemical compound C1CC2OC2CC1C(=O)C1CC2OC2CC1 CYQKECCDKADPPI-UHFFFAOYSA-N 0.000 claims 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 claims 1
- 238000007872 degassing Methods 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
- 239000002320 enamel (paints) Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims 1
- 239000004611 light stabiliser Substances 0.000 claims 1
- 229910052755 nonmetal Inorganic materials 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims 1
- 229920000193 polymethacrylate Polymers 0.000 claims 1
- 150000003097 polyterpenes Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 229940124543 ultraviolet light absorber Drugs 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 29
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
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- 239000002904 solvent Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
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- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 8
- 150000003003 phosphines Chemical class 0.000 description 8
- 239000013557 residual solvent Substances 0.000 description 8
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
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- LVMCAEWDDHHMDZ-UHFFFAOYSA-K [butyl-di(octanoyloxy)stannyl] octanoate Chemical compound CCCC[Sn+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O LVMCAEWDDHHMDZ-UHFFFAOYSA-K 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
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- 239000004925 Acrylic resin Substances 0.000 description 4
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- 239000011230 binding agent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
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- 239000003292 glue Substances 0.000 description 3
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture 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
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Classifications
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/03—Powdery paints
- C09D5/032—Powdery paints characterised by a special effect of the produced film, e.g. wrinkle, pearlescence, matt finish
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
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)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicinal Preparation (AREA)
- Laminated Bodies (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02024806 | 2002-11-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200417585A TW200417585A (en) | 2004-09-16 |
| TWI325883B true TWI325883B (en) | 2010-06-11 |
Family
ID=32309315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW92130912A TWI325883B (en) | 2002-11-07 | 2003-11-05 | Low gloss, low temperature curing powder coating compositions |
Country Status (12)
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| EP (1) | EP1563017B1 (enExample) |
| JP (1) | JP2006505639A (enExample) |
| CN (1) | CN100369983C (enExample) |
| AT (1) | ATE419313T1 (enExample) |
| AU (1) | AU2003276200B2 (enExample) |
| CA (1) | CA2504696C (enExample) |
| DE (1) | DE60325636D1 (enExample) |
| ES (1) | ES2316868T3 (enExample) |
| NZ (1) | NZ539764A (enExample) |
| TW (1) | TWI325883B (enExample) |
| WO (1) | WO2004041943A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7529754B2 (en) * | 2003-03-14 | 2009-05-05 | Websense, Inc. | System and method of monitoring and controlling application files |
| US20070160849A1 (en) * | 2005-12-20 | 2007-07-12 | Frank Niggemann | Powder coating composition suitable for thermo-sensitive substrates |
| EP1978064A1 (en) * | 2007-04-04 | 2008-10-08 | DuPont Powder Coatings Ibérica, S.L. | Powder coating composition |
| EP2085440A1 (en) * | 2008-01-31 | 2009-08-05 | Cytec Italy, S.R.L. | Powder Compositions |
| EP2085441A1 (en) | 2008-01-31 | 2009-08-05 | Cytec Surface Specialties, S.A. | Powder Composition |
| US20100022712A1 (en) | 2008-07-25 | 2010-01-28 | Merritt William H | Coating Composition and Cured Film Formed Therefrom |
| US8158698B2 (en) * | 2009-07-24 | 2012-04-17 | E. I. Du Pont De Nemours And Company | Powder coating composition and process of manufacture |
| EP2630178B1 (en) * | 2010-10-14 | 2015-12-09 | Coatings Foreign IP Co. LLC | Low-bake powder coating composition |
| EP2441787A1 (en) * | 2010-10-14 | 2012-04-18 | E. I. du Pont de Nemours and Company | Low-bake powder coating composition |
| EP2441810A1 (en) * | 2010-10-14 | 2012-04-18 | E. I. Du Pont De Nemours And Company | Coating process with low-bake powder coating composition |
| JP6127441B2 (ja) * | 2011-11-07 | 2017-05-17 | 住友化学株式会社 | 硬化性樹脂組成物 |
| CN102766263B (zh) * | 2012-08-13 | 2013-10-30 | 佛山市高明同德化工有限公司 | 羟基丙烯酸树脂及其制备方法 |
| CN103613698B (zh) * | 2013-11-26 | 2016-08-10 | 阜阳市诗雅涤新材料科技有限公司 | 一种粉末涂料用热固性丙烯酸树脂及其合成方法和用途 |
| CN105273558B (zh) * | 2015-11-06 | 2018-04-06 | 广州擎天材料科技有限公司 | 一种低温固化型环氧基丙烯酸透明粉末涂料及其制备方法 |
| DE102016207548A1 (de) * | 2016-05-02 | 2017-11-02 | Tesa Se | Härtbare Klebemasse und darauf basierende Reaktivklebebänder |
| DE102016207540A1 (de) | 2016-05-02 | 2017-11-02 | Tesa Se | Wasserdampfsperrende Klebemasse mit hochfunktionalisiertem Poly(meth)acrylat |
| KR102394180B1 (ko) * | 2017-04-07 | 2022-05-03 | 피피지 인더스트리즈 오하이오 인코포레이티드 | 코팅 조성물, 이로부터 형성된 유전체성 코팅, 및 유전체성 코팅의 제조 방법 |
| CN111978832A (zh) * | 2020-09-01 | 2020-11-24 | 常州崇高纳米材料有限公司 | 一种抗菌抗病毒粉末涂料及其制备方法 |
| CN112680074B (zh) * | 2020-12-29 | 2022-05-06 | 老虎表面技术新材料（苏州）有限公司 | 一种消光超低温固化粉末涂料组合物及其涂层 |
| JP2023151759A (ja) * | 2022-04-01 | 2023-10-16 | 関西ペイント株式会社 | 粉体塗料 |
| KR20250036128A (ko) * | 2022-07-13 | 2025-03-13 | 알넥스 유에스에이 인크. | 분말 코팅 조성물 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758632A (en) * | 1971-08-16 | 1973-09-11 | Ford Motor Co | Polymer and a flow control agent powdered coating composition of unsaturated glycidyl and anhydride co |
| JPS4941443A (enExample) * | 1972-08-30 | 1974-04-18 | ||
| JPS4947456A (enExample) * | 1972-09-08 | 1974-05-08 | ||
| JPS5117223A (en) * | 1974-08-05 | 1976-02-12 | Asahi Chemical Ind | Kairyosareta funmatsutoryoyososeibutsu |
| JPS53132033A (en) * | 1977-04-22 | 1978-11-17 | Nippon Paint Co Ltd | Coating powder composition |
| JPS5647457A (en) * | 1979-09-27 | 1981-04-30 | Hitachi Chem Co Ltd | Resin composition for powder coating material |
| JPS56136856A (en) * | 1980-03-31 | 1981-10-26 | Dainippon Ink & Chem Inc | Powder coating resin composition |
| JPS5934742B2 (ja) * | 1980-06-17 | 1984-08-24 | 大成化工株式会社 | 粉体塗料用樹脂組成物 |
| JPS57205458A (en) * | 1981-06-12 | 1982-12-16 | Dainippon Ink & Chem Inc | Resin composition for powdered paint |
| US5202382A (en) * | 1989-09-18 | 1993-04-13 | Ppg Industries, Inc. | Thermosetting powder coating composition containing a mixture of low Tg and high Tg polymers with acid functional groups |
| US5498783A (en) * | 1994-08-22 | 1996-03-12 | Basf Corporation | Powder coating composition resistant to overspray incompatibility defects |
| JP3243165B2 (ja) * | 1995-01-24 | 2002-01-07 | 日本ペイント株式会社 | 硬化性樹脂組成物、塗料組成物および塗膜形成方法 |
| JPH09221612A (ja) * | 1996-02-19 | 1997-08-26 | Kansai Paint Co Ltd | 熱硬化性ポリエステル粉体塗料 |
| DE19810220C2 (de) * | 1998-03-10 | 2001-04-19 | Herberts & Co Gmbh | Überzugsmittel und deren Verwendung zur Herstellung von Mehrschichtlackierungen |
| US6294610B1 (en) * | 1999-11-29 | 2001-09-25 | Rohm And Haas Company | Coating powders for heat-sensitive substrates |
| US6407181B1 (en) * | 2000-08-21 | 2002-06-18 | Rohm And Haas Company | Low temperature curing powder coating for producing reduced gloss, weatherable coatings |
| JP2003176447A (ja) * | 2001-12-12 | 2003-06-24 | Dainippon Toryo Co Ltd | 粉体塗料組成物 |
-
2003
- 2003-10-29 JP JP2004548802A patent/JP2006505639A/ja active Pending
- 2003-10-29 ES ES03810413T patent/ES2316868T3/es not_active Expired - Lifetime
- 2003-10-29 US US10/529,255 patent/US20060166001A1/en not_active Abandoned
- 2003-10-29 AU AU2003276200A patent/AU2003276200B2/en not_active Ceased
- 2003-10-29 AT AT03810413T patent/ATE419313T1/de not_active IP Right Cessation
- 2003-10-29 WO PCT/EP2003/011972 patent/WO2004041943A1/en not_active Ceased
- 2003-10-29 CN CNB2003801021787A patent/CN100369983C/zh not_active Expired - Fee Related
- 2003-10-29 CA CA2504696A patent/CA2504696C/en not_active Expired - Fee Related
- 2003-10-29 NZ NZ539764A patent/NZ539764A/en not_active IP Right Cessation
- 2003-10-29 EP EP20030810413 patent/EP1563017B1/en not_active Expired - Lifetime
- 2003-10-29 DE DE60325636T patent/DE60325636D1/de not_active Expired - Lifetime
- 2003-11-05 TW TW92130912A patent/TWI325883B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2504696A1 (en) | 2004-05-21 |
| ATE419313T1 (de) | 2009-01-15 |
| CA2504696C (en) | 2012-03-20 |
| CN100369983C (zh) | 2008-02-20 |
| EP1563017A1 (en) | 2005-08-17 |
| CN1708561A (zh) | 2005-12-14 |
| WO2004041943A1 (en) | 2004-05-21 |
| NZ539764A (en) | 2007-03-30 |
| DE60325636D1 (de) | 2009-02-12 |
| EP1563017B1 (en) | 2008-12-31 |
| US20060166001A1 (en) | 2006-07-27 |
| JP2006505639A (ja) | 2006-02-16 |
| ES2316868T3 (es) | 2009-04-16 |
| TW200417585A (en) | 2004-09-16 |
| AU2003276200A1 (en) | 2004-06-07 |
| AU2003276200B2 (en) | 2009-04-23 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |