EP0652911A1 - Powder coating composition with hydroxyalkylamide crosslinker - Google Patents
Powder coating composition with hydroxyalkylamide crosslinkerInfo
- Publication number
- EP0652911A1 EP0652911A1 EP93918083A EP93918083A EP0652911A1 EP 0652911 A1 EP0652911 A1 EP 0652911A1 EP 93918083 A EP93918083 A EP 93918083A EP 93918083 A EP93918083 A EP 93918083A EP 0652911 A1 EP0652911 A1 EP 0652911A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- hydroxyalkylamide
- functionality
- powder coating
- crosslinker
- 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.)
- Withdrawn
Links
- 239000000843 powder Substances 0.000 title claims abstract description 38
- 239000004971 Cross linker Substances 0.000 title claims abstract description 17
- 239000008199 coating composition Substances 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 12
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 4
- 239000011230 binding agent Substances 0.000 claims abstract description 3
- 238000000576 coating method Methods 0.000 claims description 30
- 239000011248 coating agent Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 10
- 229920000728 polyester Polymers 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- -1 tetracontyl Chemical group 0.000 description 29
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 244000028419 Styrax benzoin Species 0.000 description 8
- 235000000126 Styrax benzoin Nutrition 0.000 description 8
- 235000008411 Sumatra benzointree Nutrition 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229960002130 benzoin Drugs 0.000 description 8
- 235000019382 gum benzoic Nutrition 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 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
- 238000000034 method Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-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
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- CSSWCWIUAZSBHV-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)acetamide Chemical compound OCCN(C(=O)C)CCO CSSWCWIUAZSBHV-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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000004408 titanium dioxide Substances 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
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FODYSPZTKHCWGW-UHFFFAOYSA-N 1,2,5,5,6,6-hexachlorocyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(Cl)C=CC(Cl)(Cl)C(Cl)(Cl)C1(Cl)C(O)=O FODYSPZTKHCWGW-UHFFFAOYSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-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
- FLKHCKPUJWBHCW-UHFFFAOYSA-N 3,6-dichlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1C(O)=O FLKHCKPUJWBHCW-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005080 alkoxycarbonylalkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000005019 carboxyalkenyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940072282 cardura Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 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
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 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
- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 230000005674 electromagnetic induction Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001802 myricyl 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])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic 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
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- 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
Definitions
- the invention relates to a powder coating compostion comprising as a binder a polymer with free carboxylic acid groups and as a crosslinker a compound containing ⁇ -hydroxyalkylamide groups.
- a powder coating comprising a co-reactable mixture of an amorphous carboxylic acid group containing polyester and a ⁇ -hydroxyalkylamide is known from EP-A- 322834.
- the composition described in this application is cured - after application to a substrate - by heating the powder to 160-200°C so that the powder melts, forming a smooth layer. At that temperature the coating is chemically crosslinked due to an esterification reaction between the acid groups of the polymer and the hydroxy groups of the compound containing ⁇ -hydroxyalkylamide groups.
- a de-gasifying agent benzoin (0.5 to 3% by wt. of the powder composition) may be added to the composition.
- a de-gasifying agent is needed to ensure that the air and/or water entrapped due to melting of the powder (during a curing cycle) are removed from the paint layer as a result of the reaction. Any gas bubbles that remain in the coating reduce the adhesion of the coating to the substrate and markedly adversely affect the protection obtainable with the coating.
- compositions are characterized in EP-A-322834 as having good physical properties, such compositions are unsuitable for preparing a white or crystal-clear coating because the powder coating exhibits some degree of browning after curing, as indicated in Mercurio, New Perspective on Hydroxyamide Crosslinkers, 16th International Conf. in Org. Sci. and Tech. 235-49 (Athens, Greece 1990).
- browning appears to intensify upon heating the cured powder coating at a temperature of 200°C for a prolonged period of time (for example between 30 and 60 minutes). This discolouration upon excessive curing (yellowing on overbake) increases with the amount of benzoin. A lower amount of benzoin, on the other hand, results in a lower blister limit, such as lower than 60 ⁇ m, which results in surface defects.
- the object of the invention is to provide a powder coating composition in which it is possible to use a small amount of benzoin, for example between 0.05 and 0.8 wt.%, to obtain the highest possible blister limit, for example higher than 120 ⁇ m.
- the powder coatings must also retain good mechanical properties, such as, for example, good gloss, toughness and impact resistance and chemical properties such as for example a good chemical resistance.
- the invention is characterized in that the crosslinker comprises a combination of at least two compounds containing ⁇ -hydroxyalkylamide groups and each compound having different ⁇ -hydroxylalkylamide functionalities, the first compound having a ⁇ -hydroxy ⁇ alkylamide functionality of . 3 and the second compound having a ⁇ -hydroxyalkylamide functionality of . 3.
- the functionality stands for the average number of ⁇ -hydroxyalkylamide groups per molecule.
- Suitable compounds containing ⁇ - hydroxyalkylamide groups and having a functionality of ⁇ 3 can be depicted structurally according to formula (I):
- R 1 represents hydrogen, an alkyl group with 1- 5 carbon atoms (for example methyl, ethyl, n-propyl, n-butyl, sec. butyl, tert. butyl and pentyl) or a hydroxy- alkyl group with 1-5 carbon atoms (for example 2-hydroxy- ethyl, 3-hydroxypropyl, 2-hydroxypropyl, 4-hydroxybutyl, 3-hydroxybutyl, 2-hydroxy-2-methylpropyl, or the hydroxy derivatives of the pentyl isomers);
- R 2 and R 3 are the same or different and each independently represents hydrogen or a straight or branched alkyl group with 1-5 carbon atoms, while one of the groups R 2 and one of the groups R 3 may also form, together with the adjacent carbon atoms, a cycloalkyl group, such as, for example, cyclopentyl and cyclohexyl; R 2 and R 3 may also be hydroxyalkyl groups, such as, for example, hydroxy (C 1 -C 5 )-alkyl groups, hydroxymethyl and 1-hydroxyethyl, being preferred among the latter and
- A is an alkyl group with (1-10) carbon atoms
- R 1 represents 2-hydroxyethyl or hydrogen
- R 2 and R 3 are independent of one another hydrogen or hydroxy ( Ci-Cj J-alkyl .
- the first compound having a ⁇ - hydroxyalkylamide functionality of ⁇ 3 is a compound according to formula (II):
- Very suitable compounds having a ⁇ -hydroxyalkyl ⁇ amide functionality of ⁇ 3 are compounds according to formula (I) having a ⁇ -hydroxyalkylamide functionality of . 3 or compounds according to formula (III):
- A is an alkyl group with (1-10) carbon atoms
- R 1 represents 2-hydroxyethyl or hydrogen
- R 2 and R 3 are independent of one another hydrogen or hydroxy (C 1 _C 2 )-alkyl.
- the second compound having a ⁇ - hydroxyalkylamide functionality of r. 3 is a compound according to formula (IV):
- the functionality of the second compound having a functionality of ⁇ 3 according to formula (I) is 2.
- Compounds according to formula (V) are also very suitable as compounds having a functionality of _ 3:
- the weight ratio in the crosslinker between is preferably between 90:10 and 10:90 and more preferably between 80:20 and 20:80. This ratio depends on the functionality of the polymer with free carboxylic groups.
- the average functionality of the polymer is between 1.7 and 4.5 and preferably between 2.3 and 3.5.
- the weight ratio of the crosslinker to the polymer is usually between 10:90 and 3:97, more preferably between 20:80 and 3:97.
- the acid number of the polymer containing carboxyl groups is preferably between about 15 and about 150 mg KOH/gram resin, in particular is between about 20 and about 70 mg KOH/gram resin.
- the glass transition temperature, Tg is preferably between about 30°C and about 80°C and in particular ranges between about 35°C and about 65°C.
- the polymer that contains carboxyl groups is a polyester and/or a polyacrylate.
- Examples of preferred monomers for polyacrylates that can be incorporated in the main chain of the polymer are unsaturated monocarboxylic acids, such as, for example, acrylic acid, methacrylic acid and crotonic acid, unsaturated dicarboxylic acids, such as, for example, maleic acid, 2-methyl maleic acid, itaconic acid, and ⁇ - ⁇ -methylene glutaric acid, unsaturated anhydrides, such as, for example, maleic anhydride, itaconic anhydride, acrylic anhydride and methacrylic anhydride.
- unsaturated monocarboxylic acids such as, for example, acrylic acid, methacrylic acid and crotonic acid
- unsaturated dicarboxylic acids such as, for example, maleic acid, 2-methyl maleic acid, itaconic acid, and ⁇ - ⁇ -methylene glutaric acid
- unsaturated anhydrides such as, for example, maleic anhydride, itaconic anhydride, acrylic anhydride and methacrylic anhydr
- the polymer usually also consists of copolymerized esters of (meth)acrylic acid, such as, for example, methyl methacrylate, butyl acrylate, 2-ethyl hexyl acrylate or acrylonitrile, styrene and other ethylenically unsaturated compounds.
- (meth)acrylic acid such as, for example, methyl methacrylate, butyl acrylate, 2-ethyl hexyl acrylate or acrylonitrile, styrene and other ethylenically unsaturated compounds.
- Suitable polyesters can be obtained via standard preparation methods from essentially aromatic poly- carboxylic acids, such as, for example, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, trimellitic acid, 3,6-dichloro phthalic acid, tetrachloro phthalic acid, or, if obtainable, the anhydrides, acid chlorides or lower alkyl esters thereof.
- carboxylic acid component is composed at least of 50% by weight, preferably at least 70 mol %, of isophthalic acid and/or terephthalic acid. Exemplary procedures are described in said reference of Misev at pages 144-162.
- the polycarboxylic acids used can also be cyclo- aliphatic and/or acyclic polycarboxylic acids such as, for example, tetrahydro phthalic acid, hexahydro-endomethylene terephthalic acid, hexachloro tetrahydrophthalic acid, azelaic acid, sebacic acid, decane dicarboxylic acid, dimer fatty acid, adipic acid, succinic acid and maleic acid, in amounts of up to not more than 30 mol%, preferably up to not more than 20 mol%, of the total of carboxylic acids.
- cyclo- aliphatic and/or acyclic polycarboxylic acids such as, for example, tetrahydro phthalic acid, hexahydro-endomethylene terephthalic acid, hexachloro tetrahydrophthalic acid, azelaic acid, sebacic acid, decane dicarboxylic acid,
- Hydroxy-carboxylic acids and/or, optionally, lactones such as, for example, 12-hydroxy- stearic acid, ⁇ -caprolactone and the hydroxypivalic acid ester of neopentyl glycol can also be used.
- monocarboxylic acids such as, for example, benzoic acid, tert-butylbenzoic acid, hexahydro benzoic acid and saturated aliphatic monocarboxylic acids can also be added during the polyester preparation.
- polyols such as
- Suitable compounds for reacting with polycarboxylic acids include monoepoxides such as, for example, ethylene oxide, propylene oxide, monocarboxylic acid glycidyl ester (for example Cardura E10TM; Shell) or phenyl glycidyl ether.
- monoepoxides such as, for example, ethylene oxide, propylene oxide, monocarboxylic acid glycidyl ester (for example Cardura E10TM; Shell) or phenyl glycidyl ether.
- polyesters are prepared, using methods known per se, by esterification or transesterification, optionally in the presence of customary catalysts such as, for example, dibutyl tin oxide or tetrabutyl titanate, a suitable choice of the preparation conditions and of the COOH/OH ratio yielding end products with an acid number between 15 and 150.
- customary catalysts such as, for example, dibutyl tin oxide or tetrabutyl titanate
- the preparation and testing of the powder coating can take place in a customary manner, for example as described in Misev, Powder Coatings; Chemistry and Technology (Wiley and Sons, 1991) pp. 225-226.
- the powder coating can also contain mixtures of polyesters and polyacrylates.
- other resins such as, for example, an epoxy resin, can also be included in the powder coating composition.
- Suitable pigments include, for example, inorganic pigments such as titanium dioxide, zinc sulphide, iron oxide and chromium oxide, and organic pigments such as azo compounds.
- Suitable fillers include, for example, metal oxides, silicates, carbonates and sulphates.
- compositions according to the invention can be used as coating agents for metal, wood and plastic substrates.
- Examples are general-purpose industrial top coats, top coats on machinery and equipment, in particular top coats on metal, for example for tins, domestic and other small equipment, cars and the like.
- the invention will be elucidated with the following, non-restrictive examples and comparative example.
- Example I was repeated, use being made of the listed ingredients in the following amounts by weight (Table I).
- Example 1 The procedure of Example 1 was repeated, to make powder coatings from the ingredients listed in the following table A in the indicated amounts by weight. No acetyl diethanol amine was added.
- Benzoin 2.5 The powder coatings according to Examples I, II and Comparative Example A were electrostatically applied to steel panels and cured, during 15 minutes, at 180°C.
- the blister limit was determined via electromagnetic induction (see the already cited Misev, Powder Coatings, pp. 295-296).
- the powder coating compositions according to the present invention having the specified combinations of ⁇ - hydroxyalkylamides at a constant amount of benzoin yielded coatings having a desirable higher blister limit.
- the coatings obtained using the powder coating compositions according to the present invention also retained the desired mechanical properties.
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE9200687 | 1992-07-29 | ||
| BE9200687A BE1006097A3 (nl) | 1992-07-29 | 1992-07-29 | Poederverf op basis van een polymeer met vrije carbonzuurgroepen als bindmiddel en een beta-hydroxyalkylamidegroepen bevattende verbinding als crosslinker. |
| PCT/NL1993/000155 WO1994003545A1 (en) | 1992-07-29 | 1993-07-21 | Powder coating composition with hydroxyalkylamide crosslinker |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0652911A1 true EP0652911A1 (en) | 1995-05-17 |
Family
ID=3886379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP93918083A Withdrawn EP0652911A1 (en) | 1992-07-29 | 1993-07-21 | Powder coating composition with hydroxyalkylamide crosslinker |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0652911A1 (enrdf_load_stackoverflow) |
| CN (1) | CN1086836A (enrdf_load_stackoverflow) |
| AU (1) | AU664482B2 (enrdf_load_stackoverflow) |
| BE (1) | BE1006097A3 (enrdf_load_stackoverflow) |
| TW (1) | TW248568B (enrdf_load_stackoverflow) |
| WO (1) | WO1994003545A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000055266A1 (en) * | 1999-03-12 | 2000-09-21 | Sir Industriale S.P.A. | MIXTURES OF β-HYDROXYALKYL AMIDES AND THEIR USE AS CROSS-LINKING AGENTS FOR THE PREPARATION OF POWDER PAINTS |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5401790A (en) * | 1994-03-31 | 1995-03-28 | Ppg Industries, Inc. | Waterborne coating compositions having improved smoothness |
| DE4430400A1 (de) * | 1994-08-26 | 1996-02-29 | Inventa Ag | Wärmehärtbares Beschichtungssystem aus mehreren Bindemittelharzen |
| TW385328B (en) * | 1995-06-14 | 2000-03-21 | Ciba Sc Holding Ag | Corrosion inhibitors in powder coatings |
| US5744531A (en) * | 1996-06-24 | 1998-04-28 | Ppg Industries, Inc. | Anionic electrocoating compositions containing hydroxyalkylamide curing agents |
| ATE193045T1 (de) * | 1996-10-30 | 2000-06-15 | Inventa Ag | Wärmehärtbare beschichtungsmassen |
| US5858549A (en) * | 1997-01-07 | 1999-01-12 | National Starch And Chemical Investment Holding Corporation | (Hydroxyalkyl)urea crosslinking agents |
| US5840822A (en) * | 1997-09-02 | 1998-11-24 | National Starch And Chemical Investment Holding Corporation | Mono(hydroxyalkyl)urea and oxazolidone crosslinking agents |
| NL1007186C2 (nl) * | 1997-10-01 | 1999-04-07 | Dsm Nv | ß-hydroxyalkylamide groepen bevattend condensatiepolymeer. |
| DE10004136C2 (de) | 2000-01-31 | 2001-11-29 | Ems Chemie Ag | Wärmehärtbare Beschichtungsmassen |
| ATE302231T1 (de) * | 2001-12-06 | 2005-09-15 | Huntsman Adv Mat Switzerland | Wärmehärtbare harzzusammensetzung |
| US7887982B2 (en) * | 2005-03-18 | 2011-02-15 | Battelle Memorial Institute | Bio-based toner |
| EP1743924A1 (en) | 2005-07-11 | 2007-01-17 | DSM IP Assets B.V. | Powder paint composition |
| WO2009090234A1 (en) * | 2008-01-17 | 2009-07-23 | Dsm Ip Assets B.V. | Heat curable powder coating composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4801680A (en) * | 1987-12-30 | 1989-01-31 | Ppg Industries, Inc. | Hydroxyalkylamide powder coating curing system |
| US5101073A (en) * | 1990-08-27 | 1992-03-31 | Rohm And Haas Company | Production of β-hydroxyalkylamides |
-
1992
- 1992-07-29 BE BE9200687A patent/BE1006097A3/nl not_active IP Right Cessation
-
1993
- 1993-07-21 EP EP93918083A patent/EP0652911A1/en not_active Withdrawn
- 1993-07-21 WO PCT/NL1993/000155 patent/WO1994003545A1/en not_active Application Discontinuation
- 1993-07-21 AU AU47631/93A patent/AU664482B2/en not_active Ceased
- 1993-07-27 TW TW82105974A patent/TW248568B/zh active
- 1993-07-28 CN CN 93116866 patent/CN1086836A/zh active Pending
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9403545A1 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000055266A1 (en) * | 1999-03-12 | 2000-09-21 | Sir Industriale S.P.A. | MIXTURES OF β-HYDROXYALKYL AMIDES AND THEIR USE AS CROSS-LINKING AGENTS FOR THE PREPARATION OF POWDER PAINTS |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4763193A (en) | 1994-03-03 |
| TW248568B (enrdf_load_stackoverflow) | 1995-06-01 |
| BE1006097A3 (nl) | 1994-05-10 |
| CN1086836A (zh) | 1994-05-18 |
| WO1994003545A1 (en) | 1994-02-17 |
| AU664482B2 (en) | 1995-11-16 |
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