WO2008031589A2 - Composition de peinture en poudre - Google Patents
Composition de peinture en poudre Download PDFInfo
- Publication number
- WO2008031589A2 WO2008031589A2 PCT/EP2007/007973 EP2007007973W WO2008031589A2 WO 2008031589 A2 WO2008031589 A2 WO 2008031589A2 EP 2007007973 W EP2007007973 W EP 2007007973W WO 2008031589 A2 WO2008031589 A2 WO 2008031589A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyamide
- acid
- coating
- composition
- powder paint
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 239000000843 powder Substances 0.000 title claims abstract description 63
- 239000003973 paint Substances 0.000 title claims abstract description 45
- 239000004952 Polyamide Substances 0.000 claims abstract description 43
- 229920002647 polyamide Polymers 0.000 claims abstract description 43
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 27
- 229920000642 polymer Polymers 0.000 claims abstract description 22
- 239000004971 Cross linker Substances 0.000 claims abstract description 21
- 239000000758 substrate Substances 0.000 claims abstract description 17
- 239000011230 binding agent Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims description 36
- -1 carboxyl- Chemical group 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 19
- 229920000728 polyester Polymers 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229920001002 functional polymer Polymers 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 150000008064 anhydrides Chemical class 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 150000001991 dicarboxylic acids Chemical class 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229920006020 amorphous polyamide Polymers 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002023 wood Substances 0.000 description 4
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-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
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 2
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 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
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229920006038 crystalline resin Polymers 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer 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
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-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
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- YQPCHPBGAALCRT-UHFFFAOYSA-N 2-[1-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1(CC(O)=O)CCCCC1 YQPCHPBGAALCRT-UHFFFAOYSA-N 0.000 description 1
- PPZYHOQWRAUWAY-UHFFFAOYSA-N 2-[2-(carboxymethoxy)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC=C1OCC(O)=O PPZYHOQWRAUWAY-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- TUZMHNASXCXMBO-UHFFFAOYSA-N 3-methylpentane-2,2-diol Chemical compound CCC(C)C(C)(O)O TUZMHNASXCXMBO-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- UUAGPGQUHZVJBQ-UHFFFAOYSA-N Bisphenol A bis(2-hydroxyethyl)ether Chemical compound C=1C=C(OCCO)C=CC=1C(C)(C)C1=CC=C(OCCO)C=C1 UUAGPGQUHZVJBQ-UHFFFAOYSA-N 0.000 description 1
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- 229910001018 Cast iron Inorganic materials 0.000 description 1
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- 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
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- 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
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- 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
- ZNQRMJAOWFEDEQ-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylic acid;cyclohexane-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1.OC(=O)C1(C(O)=O)CCCCC1 ZNQRMJAOWFEDEQ-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 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
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009432 framing Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 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
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 239000001993 wax Substances 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
- 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
-
- 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
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on 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
- 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
-
- 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
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Definitions
- the present invention relates to a thermosetting powder paint binder composition comprising a polymer.
- the present invention further relates to a cross-linker and a powder coating with adjustable gloss levels based on said powder paint binder composition.
- the semi- and low gloss powder paints are an important segment of the powder coating market. Low gloss coatings reduce the light reflection from the coated surface and visibility of surface defects like pinholes. For the indoor segment semi- and low gloss coatings play a major role in the design and styling trends of household appliances and metal furniture. For the outdoor segment coatings with reduced gloss are desirable for use with building materials, architectural window framing, motor vehicles and other traffic applications.
- Reduction in gloss occurs when surface irregularities or imperfections, which are equal or larger in size compared to the incident wavelength decrease specular reflection and increase diffuse scattering.
- the intensity of reflection depends on the degree of surface-smoothness.
- Mirrors for example, are recognised as high gloss surfaces as they reflect light with high clarity.
- micro-rough, irregular or micro textured paint films scatter light, only a reduced amount of light is reflected. In general, the rougher the surface the lower degree of gloss.
- a reduced gloss powder-coated surface will result when incompatible or uniformly distributed matting additives have been introduced in the powder paint formulation.
- mineral matting additives such as silica and talc
- incompatible organic additives such as waxes and cellulose derivatives can lead to insufficient UV and yellowing resistance, loss of adhesion, and poor mar or scratch resistance.
- An alternative option for producing a reduced gloss coating is to use the dry blend technique. That is, mixing two powder coating paints with different reactivity's to each other.
- the disadvantages of dry blends include poor batch-to-batch reproducibility of gloss and appearance plus higher manufacturing costs.
- a further disadvantage is that the over-sprayed powder can only be re-used in combination with controlled, continuous dosing of virgin powder.
- the "one-shot matt” technique is able to achieve reproducible semi- or low gloss powder paint compositions.
- the components of the binder formulation are usually subjected to a single extrudate.
- the binders in a one-shot matt paint composition usually contain amorphous polyester and at least one other component that is at least partly incompatible with the amorphous polyester polymer.
- amorphous polyester usually contain (semi)-crystalline polyester, acrylic or methacrylic polymers, cross-linker or mixture of cross-linkers may be used.
- (semi)-crystalline resins can be expensive increasing the cost of the coating. Furthermore, (semi)-crystalline resins can have a low Tg and low melting viscosity and cause a sharp drop in gloss at phase separation point during the cure. The low melting viscosity of the (semi)crystalline component complicates the extrusion of the powder paint binder. A further disadvantage is that the relatively low Tg lowers the Tg of the paint composition and compromises the powder stability of the paint.
- Coating formulations with acrylic and methacrylic polymers can give acceptable low gloss coatings.
- One major disadvantage of these systems is that the incompatibility between the acrylics and the polyesters is so severe that the slightest contamination leads to cratering.
- the gloss levels of these systems are not really adjustable.
- Low gloss powder coatings can also have inadequate mechanical properties. This is especially the case when the gloss level is les than 40% at 60°. Even more so when the gloss level is less than 30% at 60°. It is the object of the present invention to provide a thermosetting paint binder composition which has reproducible, adjustable gloss levels and/or superior mechanical properties.
- the compositions of the present invention are particularly attractive because of their flexibility to allow the user to adjust the gloss level to suit the application.
- the present compositions are particularly useful for low or semi-gloss applications.
- thermosetting powder paint binder compositions comprising thermosetting polyamide, a second polymer that is at least partly incompatible with the polyamide, and crosslinker(s).
- thermosetting powder paint compositions comprising carboxyl or hydroxyl functional polymer, thermosetting polyamide, and crosslinker(s).
- thermosetting powder paint compositions comprising polyamide that have a gloss of less than 80%, preferably less than 60%, more preferably less than 40%, at 60° as measured by ASTM D 523/70.
- the polyamide is preferably a thermosetting polyamide.
- the carboxyl or hydroxyl functional polymer for use herein is preferably selected from polyesters and/or polyacrylates.
- the polymer is selected from polyesters, more preferably from carboxylic acid group-containing polyesters.
- suitable polyesters are those based on a condensation reaction of linear aliphatic, branched aliphatic and cyclo-aliphatic polyols with aliphatic, cyclo-aliphatic and/or aromatic poly carboxylic acids and anhydrides.
- the ratio of polyol and acids or anhydrides is such that there is an excess of acid or anhydride over alcohol (so as) to form a polyester which has free carboxylic groups.
- Polyesters for use herein can comprise units of, for example, isophthalic acid, terephthalic acid, 2,6-naphthalene dicarboxylic acid, 4,4'-oxybisbenzoic acid, 3,6-dichloro phthalic acid, tetrachloro phthalic acid, tetrahydro phthalic acid, trimellitic acid, pyromellitic acid, hexahydro terephthalic acid (cyclohexane dicarboxylic acid), hexachloro endomethylene tetrahydro phthalic acid, phthalic acid, azelaic acid, sebacic acid, decane dicarboxylic acid, adipic acid, succinic acid, maleic acid and fumaric acid.
- polyesters are based on at least one of isophthalic acid and/or terephthalic acid.
- Trifunctional or higher functional acids may be used also. Examples of suitable such acids include trimellitic acid or pyromellitic acid. These tri- or higher functional acids may be used as end groups or to obtain branched polyesters.
- Hydroxy carboxylic acids and/or optionally lactones can also be used, for example, 12-hydroxy stearic acid, hydroxy pivalic acid and ⁇ -caprolactone.
- Monocarboxylic acids may also be used if desired.
- these acids are benzoic acid, tert. -butyl benzoic acid, hexahydro benzoic acid and saturated aliphatic monocarboxylic acids.
- Useful polyalcohols, in particular diols, reactable with the carboxylic acids to obtain the polyester include aliphatic diols. Examples are ethylene glycol, propane-1 ,2-diol, propane-1 ,3-diol, butane-1 ,2-diol, butane-1 ,4-diol, butane-1 ,3-diol,
- Tri- or higher functional alcohols may be used in order to obtain branched polyesters.
- suitable such polyols include glycerol, hexanetriol, trimethylol ethane, trimethylol propane tris-(2-hydroxyethyl)- isocyanurate, penta erythritol and sorbitol.
- the polyester may be prepared according to conventional procedures by esterification or transesterification, optionally in the presence of customary esterification catalysts for example dibutyltin oxide or tetrabutyl titanate. Preparation conditions and the COOH/OH ratio can be selected so as to obtain end products that have a particular desired acid number and/or a hydroxyl number.
- esterification catalysts for example dibutyltin oxide or tetrabutyl titanate.
- Preparation conditions and the COOH/OH ratio can be selected so as to obtain end products that have a particular desired acid number and/or a hydroxyl number.
- the polymer has an acid value between 20 and 200 mg KOH/gram resin and more preferably between 20 and 120 mg KOH/gram resin.
- the number average molecular weight (Mn) of the polymer is preferably between about 1 ,000 and about 7,000, more preferably between about 1 ,400 and about 6,000.
- the polymer is an amorphous solid at room temperature.
- the polymer preferably has a viscosity lower than 200 Pa.s (measured at 16O 0 C, Rheometrics CP 5), more preferably lower than 150 Pa.s.
- the glass transition temperature, Tg, of the polymer is preferably in the range between 20 0 C and100°C, more preferably from about 35 0 C to about 85 0 C, even more preferably from about 4O 0 C to about 75 0 C.
- the polyamide herein may be any suitable polyamide or mixture of polyamides.
- it may be an amorphous or a (semi)crystalline polyamide.
- the polyamide is an amorphous polyamide.
- amorphous means that the amorphous polyamide does not show a sharply defined melting on crystallization peak on a second DSC scan at a rate of 5°C/min.
- an amorphous polymer and/or polymer composition is characterized by a high degree of transparency (clarity) and a lack of a sharply defined melting point. With amorphous is meant here that the amount of crystallinity calculated from the DSC-measurement is less than 10%, preferably less than 5% and more preferably less than 1 %.
- the polyamide preferably contains functional end groups such as for example carboxyl groups, epoxy groups, anhydride groups, hydroxyl groups, amino groups, acetoacetonate groups, phosphoric acid groups, phosphorous acid groups and/or thio groups.
- functional end groups such as for example carboxyl groups, epoxy groups, anhydride groups, hydroxyl groups, amino groups, acetoacetonate groups, phosphoric acid groups, phosphorous acid groups and/or thio groups.
- the polyamide is a carboxyl-, a hydroxyl- or an amine functional polyamide. More preferably, the polyamide contains functional carboxyl groups.
- the amorphous polyamide preferably comprises the polycondensation reaction product (or residue) of at least one diamine component and at least one dicarboxylic acid component. It will be clear to the man skilled in the art that instead of, or in combination with, the dicarboxylic acid its anhydride can be used. Unless otherwise specified herein reference to a dicarboxylic acid is also meant to include anhydride.
- the amorphous polyamides herein can be based on one type of amine and one type of carboxylic acid or can be based on one type of amine combined with more than one type of carboxylic acid or can be based on one type of carboxylic acid with more than one type of amine or can be based on a combination of more than one type of amine with more than one type of carboxylic acid. It is preferred that the polyamide is based on 2 to 4 diamines and 1 to 3 dicarboxylic acids.
- Suitable dicarboxylic acids include, for example, dicarboxylic acids having from 3 to about 40 carbon atoms, and more preferably dicarboxylic acids selected from aromatic dicarboxylic acids preferably having 8 to 14 carbon atoms, aliphatic dicarboxylic acids preferably having 4 to 12 carbon atoms, and/or cycloaliphatic dicarboxylic acids preferably having 8 to 12 carbon atoms.
- the dicarboxylic acids may be branched, nonlinear or linear.
- the dicarboxylic acids are branched or non-linear.
- dicarboxylic acids include, for example, phthalic acid, isophthalic acid, terephthalic acid, 1 ,4-cyclohexanedicarboxylic acid, naphthalene-2,6-dicarboxylic acid, cyclohexanediacetic acid, diphenyl-4,4'-dicarboxylic acid, phenylenedi (oxyacetic acid), sebacic acid, succinic acid, adipic acid, glutaric acid and/or azelaic acid.
- phthalic acid isophthalic acid, terephthalic acid, 1 ,4-cyclohexanedicarboxylic acid, naphthalene-2,6-dicarboxylic acid, cyclohexanediacetic acid, diphenyl-4,4'-dicarboxylic acid, phenylenedi (oxyacetic acid), sebacic acid, succinic acid, adipic acid, glutaric acid and/or azelaic
- the diamine can be any suitable diamine.
- it can be of an aliphatic, cycloaliphatic, aliphatic-aromatic, or aromatic nature.
- the diamine component may comprise an aliphatic diamine having for example 2 to 12 carbon atoms.
- the aliphatic diamines may also contain aromatic groups in the molecule. With aromatic amines the glass transition temperature of the polyamide can be very high. It is preferred to use aliphatic and aromatic-aliphatic amines.
- With aliphatic amine is meant a compound in which the amine-group is directly coupled to an aliphatic chain.
- aromatic amine is meant a compound in which the amine group is directly coupled to an aromatic ring structure.
- the aliphatic diamines also include cycloaliphatic diamines such as, for example, piperazine.
- suitable aliphatic diamines include, for example, isophorondiamine, 1 ,2-ethylenediamine, 1 ,3-propylenediamine, 1 ,6- hexamethylenediamine, 1 ,12-dodecylenediamine, 1 ,4 cyclohexanebismethylamine, piperazine, p-xylylenediamine and/or m-xylylenediamine.
- the amine component may also comprise branching components to obtain branched polyamides.
- Suitable examples include, for example, di-alkylene-triamines such as, for example, di-ethylene- triamine, di-alkylene-tetramines, di-alkylene- pentamines, di-hexamethylene-triamine, poly- functional acids such as, for example, 1 ,3,5-benzene tricarboxylic acid, trimellitic anhydride and pyromelitic anhydride and poly- functional amino acids such as, for example, aspartic acid and glutamic acid.
- di-alkylene-triamines such as, for example, di-ethylene- triamine, di-alkylene-tetramines, di-alkylene- pentamines, di-hexamethylene-triamine
- poly- functional acids such as, for example, 1 ,3,5-benzene tricarboxylic acid, trimellitic anhydride and pyromelitic anhydride
- poly- functional amino acids such as, for example, aspartic acid and glutamic acid.
- the polyamide may have, for example, a linear or nearly linear, branched, star or dendritic structure.
- the present invention is not directed to the use of a polyesteramide as the thermosetting amorphous polyamide.
- polyesteramide is meant here and hereinafter a polymer that contains both ester-bonds as well as amide-bonds, where the polyamide according to the invention does not contain ester-bonds.
- composition may also comprise branching components to obtain branched polymers.
- branching components include di-alkylene-triamines such as di-ethylene- triamine, di-alkylene-tetramines, di-alkylene- pentamines, di-hexamethylene-triamine, poly functional acids such as 1 ,3,5-benzene tricarboxylic acid, trimellitic anhydride and pyromelitic anhydride and poly functional amino acids such as aspartic acid and glutamic acid.
- the polyamide may have, for example, linear or nearly linear, branched, star or dendritic structure.
- the polyamide has an acid number between 20 and 200 mg of KOH/gram of resin (polymer).
- the glass transition temperature (T 9 ) of the polyamide is between 2O 0 C and 200°C. More preferably the glass transition temperature (T 9 ) is between 40°C and 12O 0 C.
- the polyamide preferably has a viscosity lower than 200 Pa. s (measured at 16O 0 C, Rheometrics CP 5), more preferably lower than 150 Pa. s.
- the molecular weight (Mn) of the polyamide ranges between 1000 and 10,000 g/mol, and more preferably between 1400 and 6000 g/mol.
- any suitable crosslinker(s) may be used herein.
- the cross-linkers are capable of reacting with carboxyl-functional polymers.
- Various types of crosslinkers or mixtures of crosslinkers may be used herein.
- suitable crosslinkers include triglycidylisocyanurate (TGIC), epoxy resin, a crosslinker containing hydroxylamide group for example PRIMID, aliphatic oxirane, isocyanate, diglycidyl phtalate containing crosslinker, hexamethoxy-methylmelamine (HMMM), glycoluril(derivative), benzoguanamine (derivative), amino resin, phenolic resin
- the reduced gloss powder binding compositions herein are obtained by mixing the carboxyl or hydroxyl functional polymer, thermosetting polyamide, and crosslinker(s) in a single extrusion. More preferably all the components of the powder paint binder composition are mixed in a single extrusion.
- the present invention provides reduced gloss powder coatings which can be obtained with adjustable gloss levels by selecting the ratio between the polymers and the cross- linker.
- the present invention also provides reduced gloss powder coatings which can be obtained with reproducible gloss levels.
- the present invention provides reduced gloss powder coatings having improved mechanical properties at low gloss levels, excellent appearance, good powder stability, solvent resistance, outdoor durability, and/or resistance to yellowing during curing.
- the weight ratio of polymer comprising the carboxyl functional polymer and the thermosetting polyamide to cross-linker ranges between 50:50 and 98:2. More preferably this ratio ranges between 75:25 and 95:5.
- thermosetting powder paint binder composition is generally defined as the resinous part of the powder paint composition consisting of polymer and crosslinker(s) and this composition generally contains more than 50 wt.% polymer and less than 50 wt.% crosslinker(s).
- compositions may comprise one or more additives such as, for example, pigment, filler, degassing agent, flow agent and/ or stabilizer.
- Suitable pigments include inorganic pigments such as titanium dioxide, zinc sulphide, iron oxide and chromium oxide, and also organic pigments such as azo compounds.
- Suitable fillers include for example metal oxides, silicates, carbonates and/or sulphates.
- Primary and/or secondary antioxidants, UV stabilizers such as quinones, (sterically hindered) phenolic compounds, phosphonites, phosphites, thioethers, HALS compounds (hindered amine light stabilizers) and aromatic amines, may for example be used as stabilizers.
- degassing agents examples include benzoin and cyclohexane dimethanol bisbenzoate.
- flow agents include polyalkylacrylates, fluorohydrocarbons and silicone fluids.
- suitable additives include, for example, additives for improving tribocharging, such as sterically hindered tertiary amines that are described in EP-B-371528.
- One preferred additive for use herein is copper halogenides, particularly in combination with at least one other halogenide.
- suitable other halogenides include potassium and sodium halogenide, preferably potassium halogenide is used.
- the invention further relates to a process for coating a substrate with a thermosetting powder paint composition according to the invention comprising at least the following steps: a. Optionally pre-treating and/or pre-heating the substrate, b. Applying a thermosetting powder paint composition comprising a binder composition as described hereinabove to the substrate, c. Heating the coated substrate from step b) to a temperature and for such a period that the coating is at least partially cured, d. Optionally applying a second cure step.
- step a) and/ or d The process according to the invention is preferably used without the use of step a) and/ or d).
- the process can be used in various temperature regimes.
- the man skilled in the art can readily determine which temperature regime is most suitable for his application.
- the process according to the invention can be used to coat all kinds of substrates.
- suitable substrates include metal, (galvanized) steel, cast iron, other alloys, glass, ceramic, bricks, plastic, paper, cardboard, cork, solid wood, veneer, chip wood, wood composite material, for example particle board, high, medium or low density fibre board, plywood and other substrates that contain a significant amount of wood.
- the present invention also relates to a substrate fully or partially coated with a composition according to the invention or obtained by a process according to the invention.
- Thermosetting coatings intended for industrial applications are described further in general in Powder Coatings, Chemistry and Technology, Misev, pages 141-173 (1991).
- Thermoplastic powder paint compositions comprising a polyamide are disclosed for example at pages 28-34 of Powder Coatings, Chemistry and Technology, Misev,
- thermoplastic powder paint compositions are different from the thermosetting powder paint composition according to the present invention because of, amongst others, the different crosslink mechanism, the different crystallinity and the different molecular weight.
- Thermoplastic compositions comprising polyamide generally result in coatings that have insufficient or at least decreased hardness.
- This invention also relates to the use of the present binder compositions in powder paint compositions, especially in reduced gloss paint compositions.
- Powder paints according to the invention can be applied to a suitable substrate in the usual manner, for example by electrostatically spraying the powder onto an earthed substrate and curing the powder paint to a powder coating by exposing the powder paint composition to heat at a suitable temperature for a sufficient length of time.
- the applied powder can for example be heated in a gas oven, an electric oven or with the aid of infrared radiation or UV-radiation.
- carboxyl functional polvamide resin 2 488,30 grams of isophorone diamine, 615,10 grams of adipic acid and 200 grams of water were charged in a 2 liter reaction flask equipped with a stirrer, nitrogen sparge, a temperature control unit and distillation glassware. The reaction mixture was stirred until all the ingredients were dissolved. The mixture was heated slowly to 220 0 C, while the water was distilled off. After reaching the reaction temperature of 220 0 C the mixture was vacuum distilled for 30 minutes, the vacuum was set off and the resin discharged. The obtained resin was an amorphous, crystal clear polyamide having an acid value of 148 mg KOH/gram resin, a Tg of 76,0°C and a viscosity of 63,0 Pa. s at 160 0 C.
- powder paint compositions All components of the powder paint compositions were premixed in dry blender and extruded with Prism at 12O 0 C. The extrudate was cooled, ground and sieved. The sieve fraction smaller than 90 micrometers was used as powder paint.
- the powder paint was applied by Corona gun on to aluminium substrate A-36 and cured 10' at 200 0 C in electrical oven.
- Appearance -The coatings are viewed at in the reflection of a light source and are compare visually.
- Powder stability is determined via DIN 2409. Storage stability is determined via DIN 55990-7 at 40 0 C
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
Abstract
La présente invention concerne une composition de liant de peinture en poudre thermodurcissable comprenant du polyamide thermodurcissable, un autre polymère qui est au moins partiellement incompatible avec le polyamide et un ou plusieurs agents de réticulation. La présente invention concerne en outre des procédés de production de telles compositions, d'utilisation de telles compositions dans des compositions de peinture en poudre, ainsi que des substrats revêtus de telles compositions.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP06019233 | 2006-09-14 | ||
EP06019233.3 | 2006-09-14 |
Publications (2)
Publication Number | Publication Date |
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WO2008031589A2 true WO2008031589A2 (fr) | 2008-03-20 |
WO2008031589A3 WO2008031589A3 (fr) | 2008-05-22 |
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ID=37675063
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/007973 WO2008031589A2 (fr) | 2006-09-14 | 2007-09-13 | Composition de peinture en poudre |
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WO (1) | WO2008031589A2 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018009086A1 (fr) * | 2016-07-08 | 2018-01-11 | Cin Industrial Coatings, S.A. | Peinture en poudre thermodurcissable à propriétés antiadhérentes, procédés de fabrication et d'application respectifs et revêtement correspondant |
WO2018189166A1 (fr) * | 2017-04-11 | 2018-10-18 | Basf Coatings Gmbh | Agent de revêtement produisant des surfaces structurées |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4568606A (en) * | 1984-12-14 | 1986-02-04 | Morton Thiokol, Inc. | Powder coatable epoxy/polyester composition and electrical conductors coated therewith |
US4761336A (en) * | 1984-12-14 | 1988-08-02 | Morton Thiokol, Inc. | Powder coatable epoxy composition and post-tensioning cable coated therewith |
WO1997034708A1 (fr) * | 1996-03-19 | 1997-09-25 | Mar-Bal, Inc. | Pieces en plastique revetues de poudre et procede s'y rapportant |
AU2001288459A1 (en) * | 2000-08-29 | 2002-03-13 | Andrew W. Suman | Abradable dry powder coatings, methods for making and coating, and coated articles therefrom |
-
2007
- 2007-09-13 WO PCT/EP2007/007973 patent/WO2008031589A2/fr active Application Filing
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018009086A1 (fr) * | 2016-07-08 | 2018-01-11 | Cin Industrial Coatings, S.A. | Peinture en poudre thermodurcissable à propriétés antiadhérentes, procédés de fabrication et d'application respectifs et revêtement correspondant |
WO2018189166A1 (fr) * | 2017-04-11 | 2018-10-18 | Basf Coatings Gmbh | Agent de revêtement produisant des surfaces structurées |
CN110709480A (zh) * | 2017-04-11 | 2020-01-17 | 巴斯夫涂料有限公司 | 生产结构化表面的涂料 |
CN110709480B (zh) * | 2017-04-11 | 2022-07-12 | 巴斯夫涂料有限公司 | 生产结构化表面的涂料 |
US11427729B2 (en) | 2017-04-11 | 2022-08-30 | Basf Coatings Gmbh | Coating materials generating structured surfaces |
Also Published As
Publication number | Publication date |
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WO2008031589A3 (fr) | 2008-05-22 |
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