WO2010028144A1 - Thermal curable powder coating composition - Google Patents
Thermal curable powder coating composition Download PDFInfo
- Publication number
- WO2010028144A1 WO2010028144A1 PCT/US2009/055883 US2009055883W WO2010028144A1 WO 2010028144 A1 WO2010028144 A1 WO 2010028144A1 US 2009055883 W US2009055883 W US 2009055883W WO 2010028144 A1 WO2010028144 A1 WO 2010028144A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin binder
- powder coating
- coating composition
- poiyuretdione
- functional
- Prior art date
Links
- 239000000843 powder Substances 0.000 title claims abstract description 61
- 239000008199 coating composition Substances 0.000 title claims abstract description 51
- 239000011347 resin Substances 0.000 claims abstract description 57
- 229920005989 resin Polymers 0.000 claims abstract description 57
- 239000011230 binding agent Substances 0.000 claims abstract description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 43
- 238000002844 melting Methods 0.000 claims abstract description 18
- 230000008018 melting Effects 0.000 claims abstract description 18
- 238000000576 coating method Methods 0.000 claims description 26
- 239000000049 pigment Substances 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
- 239000011248 coating agent Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000002009 diols Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000011247 coating layer Substances 0.000 abstract description 4
- 239000010409 thin film Substances 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 238000001723 curing Methods 0.000 description 14
- 239000002245 particle Substances 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 150000002513 isocyanates Chemical class 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- -1 for example Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002987 primer (paints) Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 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
- 235000003625 Acrocomia mexicana Nutrition 0.000 description 1
- 244000202285 Acrocomia mexicana Species 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000010285 flame spraying Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-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
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase 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
- 150000002739 metals Chemical class 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000007751 thermal spraying Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- XREKCAGAPAEVFE-UHFFFAOYSA-J tri(hexadecanoyloxy)stannyl hexadecanoate Chemical compound [Sn+4].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O XREKCAGAPAEVFE-UHFFFAOYSA-J 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/097—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to urethdione groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3848—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing two nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2150/00—Compositions for coatings
- C08G2150/20—Compositions for powder coatings
Definitions
- the present invention is directed to a powder coating composition based on specific polyur ⁇ tdsone resins providing high flexibility in combination with excellent weather resistance of the coating layers an ⁇ high processability of the powder coating compositions.
- Epoxy, polyester and acryiic resm binders are well-known for the use in thermal curable powder coating compositions
- hydroxy! functional polyesters are curable with isocyanates to result in poSyurethane powder coatings, see D. Bates, The Science of Powder Coatings, Volume 1 , London. 1990, pages 56, 276-277, 282.
- Combinations of different resin binders and curing agents are investigated to receive specific desired properties of the coats ngs on different substrate surfaces.
- EP-A 1209182 EP-A 1323757 and WG 02/50147 refer to coating compositions based on specific urethane acrylates or a mixture of different polymers, for example, different ⁇ rethane acryiates, wherein the compositions are cured by ultra violet (UV) radiation to provide coatings with good mechanical properties and flexibility
- Thermal curable powder coating compositions based on urethane (meth) acryiates or specific polyester urethanes are disclosed in WO 01/25308.
- EP-A 410242 and WO 95/35332 and refer to good storage stability and increased weather resistance of the coatings,
- Uretdione based powder resins are used as curing agent (hardener) for hydroxyi-f ⁇ nctiona! polyester coating systems.
- Such ⁇ retdiooe based restns are amorphous, and they are produced from ssophorone diisocyanate.
- crystalline poiy ⁇ retdiones are disclosed used as hardener in powder coating compositions.
- the present invention provides a powder coating composition comprising at least one hydroxy! functional poiyuretdione resin binder, wherein the at least one hydroxyl functional poiyuretdione resin binder having a melting temperature of 60 to 180o C, in particular, 80 to 160oC,
- the powder coating composition according to the invention comprising the specific kind of the poiyuretdione resin binder makes it possible to provide desired technological properties, in particular, low curing temperatures, thin films and high flexibility in combination with an excellent weather resistance of the coating layers.
- the hydroxyl functional poiyuretdione resin binder of the invention can be used as self-curing binder resin. Additionally, the powder coating composition according to the invention comprising the hydroxyl functional poiyuretdione resin binder of the invention makes it possible to cure the resulting coatings without release of any blocking agents usually used in the isocyanate chemistry.
- the present invention refers to a powder coating composition
- a powder coating composition comprising 25 to 99 weight percent (wt%), preferably 40 to 95 wt%, of the at least one hydroxy! functional polyuretdsone resin binder, the wt% being based on the total weight of the powder coating composition.
- the at least one hydroxy! functional poiyuretdione resin binder of the invention has a melting temperature of 60 to 180oC, in particular 80 to 160oC.
- the melting temperatures are not in genera! sharp melting points, but instead the upper end of melting ranges with a breadth of, for example, 30 to 1 SOoC, depending from the kind of the resin binder.
- the melting ranges and thus the melting temperatures may be determined, for example, by DSC (differential scanning calorimetry) at heating rates of 10 K/mia determined according to DfN 53765 -8-10.
- upper end of melting ranges used in this description has the meaning of the range of Ts ⁇ determined according to DSN 53785 -B-1G.
- the at least one hydroxy! functional polyurefdione resin binder is very slightly, if at all, soluble in organic solvents conventional used in coatings and/or in water, the solubility amounting, for example, to less than 10, in particular less than 5 g per Sitre of butyl acetate or water at 2OoC.
- All the number-average molar mass data stated in the present description are number-average molar masses determined or to be determined by gel permeation chromatography (GPC; divinyibenzene- cross-linked polystyrene as the immobile phase, tetrahydrof ⁇ ran as the liquid phase, polystyrene standards), determined according to !SO 13885- 1 standard.
- the poly ⁇ retdione resin binders of the invention are hydroxy! functional resins and have hydroxy! values of, for example, 20 to 300 mg KOH/g.
- the hydroxy! value is defined as the number of mg of potassium hydroxide (KOH) which is equal to the number of mg acetic acid for acetalfzing of 1 g of the resin, determined according to DIN 53240.
- the hydroxy! functional poly ⁇ retdione resin may be produced in general by reacting isocyanate (NCO) functional uretdione(s) with alcohols in such a way that the ratio of free NCO groups to hydroxyl groups is in a range of 0.5 :1 to 0.5 : 3, preferably 0.5 ;1 to 0.5 ; 2.
- NCO isocyanate
- NCO f ⁇ nctionai uretdiones are uretdiones based on hexamethylene dtisocyanate (HDI). 1 ,4-cydoh ⁇ xandiisocyanate, biscyclohexylmethanditsocyanate, trimetyhlhexyldiisocyanate, isophorone dtisocyanate (IPDI), uretdiones based on aromatic structures known to those skilled in the art like dtphenylmethandiisocyanate (MDS).
- the uretdiones can contain other structures like isocyanurate structures besides the uretdione structure. Preferred are uretdiones based on aliphatic dhsocyanates.
- the alcohols can be linear and/or branched alcohols.
- Diofs and poiyois, such as triols. are particularly suitable, on its own, or in mixture.
- Diol(s) and poly ⁇ ls suitable for the production of the polyuretdione resins are not only diols and poiyois in the form of !ow moSar mass compounds defined by empirical and structural formula but also oligorneric or polymeric di ⁇ is or poiyois with number-average molar masses of, for example, up to 800, for example, corresponding hydroxyl-functionai poiyethers, polyesters or polycarbonates.
- Low molar mass poiyois defined by an empirical and structural formula are, however, preferred.
- Mono aicohois can be used particularly as chain stopper to terminate the polymer chain.
- mono alcohols are ethanol, propanol.
- linear and branched diois examples include ethylenglycol, isomeric propandioSs and butandiois, 1 ,2-propandi ⁇ i, 1 ,3-pro ⁇ andiol, 1,3-b ⁇ tandiol, 1 ,4-butandiol, 1 ,4-pentandioS, 1 ,5-pentandioi, 1 ,2-hexandiol, 1 ,5-hexandio!, 2,5-hexandiol, 1,8-hexandioi, 1 ,10-dekandioi, 1 ,12-dodekandiol, neopenylglykol, aiso (cyc!o)a!iphafic, aromatic or araliphatic diols with a molar mass in the range of, for example, 82 to 800 such as 1 ,4- cyclohexanedimetha ⁇ oi, hydrogenated bis
- ohexanediols the isomeric cyclohexa ⁇ edimetha ⁇ ols, tricyclodecanedimethanol, pentaerythritol.
- Preferred is the use of linear diols.
- (cyclo) aliphatic) used in this description and the claims encompasses cycIoaSiphatic, linear aliphatic, branched aliphatic and cycloaliphatic with aliphatic residues.
- the aromatic or araliphatic diols comprise diols with aromatically and/or aiiphaticaliy attached hydroxy ⁇ groups.
- polyois examples include glycerol, trimethylolethane, trimethylolpropane or pentaerythritoL
- monomers of isocyanates can be used for the preparation of the hydroxy! functional poiyuretdione resins of the invention.
- isocyanates are diisocyanates, for example, HDi, !PDI, hydrogenated MDI
- the hydroxy! functional poiyuretdione restn binders may be produced by reacting the monomers of isocyanates with the alcohof(s) in such a way that the content of free NCO groups to the content of hydroxy! groups is in a range of 0.5 :1 to 0.5 : 2, preferably 0.5 :1 to 0.5 ; 1.5.
- reaction conditions are selected in such a way that the ring opening of the uretdione ring can be avoided, that means, at reaction temperatures in the range of for example, 80 to 140X.
- the preparation of the hydroxy! functional poiyuretdione resin binders of the invention may be done in apparatus known for the preparation of polyur ⁇ thanes, in general, as known to a person ski ⁇ led in the art.
- the hydroxy! functional poiyuretdione resin binders of the invention may have a number-average molar mass in a range of 1000 to 10000, preferred 1000 to 5000.
- the resulted poiyuretdione resins of the invention do not require working up and may be used directly as hydroxy! functional poiyuretdione resin binder of the invention.
- the hydroxy! functional poiyuretdione resin binder of the invention can be used as self-curing binder resin in the powder coating composition according to the invention. This means, that it can be used without any use of further binder resins and curing agents usually used in powder coating compositions and as known to a person skilled in the art.
- the powder coating composition according to the invention comprising the hydroxyl functional poiyuretdione resin bmder of the invention makes it possible to cure the resulting coatings without release of any blocking agents usually used in the ssocyanate chemistry.
- the hydroxy! functional poiyuretdione resin binder of the invention can also be used as co-binder resin in the powder coating composition according to the invention together with further binder resins and optionally their curing agents usually used in powder coating compositions and as known to a person skilled in the art.
- Such further binder resins and curing agents may be crystalline, semi-crystalline and/or amorphous compounds. Examples for these different curing mechanisms are systems based on ⁇ poxy/acid addition, hydroxyl/blocked polyisocyanate, hydroxyi/esterification, UV-curing as known to those skilled in the art.
- binder resins polyester, polyurethane and (meth)acrylic copolymer resins and hybrid binders derived from these classes of binders, for example, with hydroxyl values of, for example. 60 to 300 mg of KOH/g and number-average molar masses of, for example, 500 to 10000.
- curing agents for these further resin binders are, for example, Vestagon BF 1540, Creian® EF 403, Cretan® LP LAS 3969.
- the coating composition according to the invention may contain the further binder ressns and their curing agents in amounts in a range up to 75 wt%, optionally, in a range of 1 to 75 wt%, the wt% being based on the total weight of the powder coating composition.
- the coating compositions of the present invention may further comprise one or more pigments, fillers and/or coating additives.
- Additives are selected from the group consisting of flow control agents, dispersants, thixotropic agents, adhesion promoters, antioxidants, light stabilizers, anticorrosson agents, inhibitors, catalysts, levelling agents, wetting agents, antieratering agents, and mixtures thereof.
- Catalysts, suitable for the self-curing hydroxy! functional polyuretciione resin binder can be used, for example, zinc hexadecanoat, tin hexadecanoat, zinc acetylacetonafe, or zinc acetate.
- the additives are used in conventional amounts known to the person skilled in the art, for example, 0,1 to 10 wt%, based on the totai wt% of the coating composition. in case of dua! cure coating compositions, usually used photoinstiators known to a person skilled in the art are contained therein.
- the coating compositions may also contain transparent pigments.
- coior-smparting and/or special effect-imparting pigments and/or fillers in amounts of. for example, 5 to 80 wt%. preferred 5 to 40 wt%, based on the total wt% of the coating composition.
- Suitable color-imparting pigments are any conventional coating pigments of an organic or inorganic nature. Examples of inorganic or organic color-imparting pigments are titanium dioxide, iron oxide pigments, carbon black, azo pigments, phthaiocyanine pigments, quinacndone pigments and pyrrolopyrrole pigments.
- special effect pigments are metal pigments, for example, of afuminum, copper or other metals, interference pigments, such as, for example, metal oxide-coated metal pigments, for example, iron oxide-coated aluminum, coated mica, such as, for example, titanium dioxide-coated mica, graphite effect-imparting pigments, iron oxide in flake form, liquid crystal pigments, coated aluminum oxide pigments, coated silicon dioxide pigments.
- fillers are silicon dioxide, aluminum silicate, barium sulfate, caioium carbonate and talc.
- powder coating compositions of the invention having a melt viscosity of below 50 Pas, particularly below 10 Pas, for example, 1 to 8 Pas.
- the present invention provides a powder coating composition comprising preferably (A) 25 to 99.9 wt% of at least one hydroxyl functional polyuretdione resin binder
- a powder coating composition comprising
- (B) 0 to 50 wt% and optionally, 1 to 50 wt% of at least one resin binder and optionally at least one curing agent, different from (A), and
- the components of the present invention are mixed, extruded and ground by conventional techniques employed in the powder coatings art familiar to a person of ordinary skill in the art. Typically, all of the components of the present powder coating formulation are added to a mixing container and mixed together. The blended mixture is then melt blended, for example, in a melt extruder. The extruded composition is then cooled and broken down and ground to a powder. The ground powder is subsequently screened to achieve the desired particle size, for example, an average particle size (mean particle diameter) of 20 to 200 ⁇ m, determined by means of laser diffraction.
- a predetermined amount of a component of the powder coating components be added, for example, to the pofyuretdi ⁇ ne resin (A) and further components of the composition according to the invention, and then premixed.
- the premix can then be extruded, cooled, and thereafter pulverized and classified.
- composition according to the invention may also be prepared by spraying from supercritical solutions, NAD "non-aqueous dispersion” processes or ultrasonic standing wave atomtzation process,
- specific components of the powder coating composition according to the invention for example, additives, pigments, fillers, may be processed with the finished powder coating particles after extrusion and grinding by a "bonding" process using an impact fusion.
- the specific components may be mixed with the powder coating particles.
- the individual powder coating particles are treated to softening their surface so that the components adhere to them and are homogeneously bonded with the surface of the powder coating particles.
- the softening of the powder particles' surface may be done by heat treating the particles to a temperature, e.g., 40 to 100oC, dependent from the melt behavior of the powder particles. After cooling, the mixture the desired particle size of the resulted particles may be proceed by a sieving process.
- the powder coating compositions of the present invention can be readily applied to metallic and non-metallic substrates.
- the compositions of the present invention can be used to coat metallic substrates including, but not limited to, steel, brass, aluminum, chrome, and mixtures thereof, and also to other substrates including, for example, heat-sen sits ve substrates, such as, substrates based on wood, plastics and paper, and other substrates based, for example, on glass and ceramics.
- the surface of the substrate may be subjected to a mecharticai treatment, such as, blasting followed by, in case of meta! substrates, acid rinsing, or cleaning followed by chemical treatment.
- a mecharticai treatment such as, blasting followed by, in case of meta! substrates, acid rinsing, or cleaning followed by chemical treatment.
- the powder coating composition of this invention may be applied by, e.g., electrostatic spraying, electrostatic brushing, thermal or flame spraying, fl ⁇ sdized bed coating methods, flocking, thbostatic spray application and the like, also coil coating techniques, ai! of which are known to those skilled in the art.
- the substrate Prior to applying the coating composition of the invention the substrate may be grounded but not pre-heated, so that the substrate is at an ambient temperature of about 25oC (77oF),
- the substrate to be coated may be preheated before the application of the powder composition according to the invention, and then either heated after the application of the powder composition or not.
- gas is commonly used for various heating steps, but other methods, e.g., microwaves, t ⁇ fra red (SR). near infra red (NIR) and/or ultra violet (UV) irradiation are also known.
- the preheating can be to a temperature ranging from 60 to 280oC (338 to 500oF) using means familiar to a person of ordinary skill in the art.
- the coating can be cured or post-cured by exposing by convective, gas and/or radiant heating, e.g., IR and/or NiR irradiation, as known in the art, to temperatures of, e.g., 100oC to 800oC (212 to 572oF), preferably, 14O"C to 2GGoC, object temperature in each case, for, e.g., 2 to 20 minutes in case of pre-heated substrates, and, for example, 4 to 30 minutes in case of non-pre-heafed substrates.
- the coated substrate is typically subjected to. for example, either air-cooling, or water quenching to lower the temperature to between, for example, 35 and 9OoC (95 and 194oF).
- the substrate is coated with an effective amount of the present powder coating composition so as to produce a dry film thickness that ranges, for example, from 10 to 300 ⁇ m, preferably 20 to 100 ⁇ m, particularly from 10 to 50 ⁇ m for very thin film coatings.
- the powder coating compositions according to the invention can be applied directly on the substrate surface as a primer coating or on a iayer of a primer which can be a liquid or a powder based primer.
- the powder coating compositions according to the invention can also be applied as a coating layer of a multilayer coating system based on liquid or powder coats, for example, as clear coat layer applied onto a color-imparting and/or special effect-imparting base coat layer or as pigmented one-layer coat applied onto a prior coating.
- Example 2 Preparation of .a ..powder coating .composition of the.invention
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09792232A EP2321362A1 (en) | 2008-09-04 | 2009-09-03 | Thermal curable powder coating composition |
CA2734162A CA2734162A1 (en) | 2008-09-04 | 2009-09-03 | Thermal curable powder coating composition |
CN2009801347793A CN102143982A (en) | 2008-09-04 | 2009-09-03 | Thermal curable powder coating composition |
US13/058,916 US20110136972A1 (en) | 2008-09-04 | 2009-09-03 | Thermal curable powder coating composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US19093808P | 2008-09-04 | 2008-09-04 | |
US61/190,938 | 2008-09-04 |
Publications (1)
Publication Number | Publication Date |
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WO2010028144A1 true WO2010028144A1 (en) | 2010-03-11 |
Family
ID=41297238
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2009/055883 WO2010028144A1 (en) | 2008-09-04 | 2009-09-03 | Thermal curable powder coating composition |
Country Status (6)
Country | Link |
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US (1) | US20110136972A1 (en) |
EP (1) | EP2321362A1 (en) |
CN (1) | CN102143982A (en) |
CA (1) | CA2734162A1 (en) |
RU (1) | RU2011112796A (en) |
WO (1) | WO2010028144A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20200002555A1 (en) * | 2017-03-13 | 2020-01-02 | Tiger Coatings Gmbh & Co. Kg | Curable coating material for non-impact printing |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US9206320B1 (en) * | 2013-07-18 | 2015-12-08 | Hentzen Coatings, Inc. | Matte-appearance powder coating compositions with chemical agent resistance |
CN109401580A (en) * | 2018-09-20 | 2019-03-01 | 中北大学 | A kind of non-isocyanate polyureas powdery paints |
US12031053B2 (en) * | 2019-10-17 | 2024-07-09 | Akzo Nobel Coatings International B.V. | Low gloss polyurethane coating compositions |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3923743A (en) * | 1973-03-13 | 1975-12-02 | Bayer Ag | Process for cross-linkable pulverulent coating compositions based on uretdione polyisocyanates |
US20020095019A1 (en) * | 1994-02-28 | 2002-07-18 | Huels Aktiengesellschaft | Polyaddition products containing hydroxyl and uretdione groups, process for their preparation, their use for the production of highly reactive polyurethane powder coatings which are free from elimination products, and the polyurethane powder coatings produced accordingly |
US20080182928A1 (en) * | 2006-09-23 | 2008-07-31 | Bayer Materialscience Ag | Polurethane powder lacquer |
-
2009
- 2009-09-03 RU RU2011112796/04A patent/RU2011112796A/en not_active Application Discontinuation
- 2009-09-03 US US13/058,916 patent/US20110136972A1/en not_active Abandoned
- 2009-09-03 EP EP09792232A patent/EP2321362A1/en not_active Withdrawn
- 2009-09-03 CA CA2734162A patent/CA2734162A1/en not_active Abandoned
- 2009-09-03 CN CN2009801347793A patent/CN102143982A/en active Pending
- 2009-09-03 WO PCT/US2009/055883 patent/WO2010028144A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3923743A (en) * | 1973-03-13 | 1975-12-02 | Bayer Ag | Process for cross-linkable pulverulent coating compositions based on uretdione polyisocyanates |
US20020095019A1 (en) * | 1994-02-28 | 2002-07-18 | Huels Aktiengesellschaft | Polyaddition products containing hydroxyl and uretdione groups, process for their preparation, their use for the production of highly reactive polyurethane powder coatings which are free from elimination products, and the polyurethane powder coatings produced accordingly |
US20080182928A1 (en) * | 2006-09-23 | 2008-07-31 | Bayer Materialscience Ag | Polurethane powder lacquer |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20200002555A1 (en) * | 2017-03-13 | 2020-01-02 | Tiger Coatings Gmbh & Co. Kg | Curable coating material for non-impact printing |
US11787960B2 (en) * | 2017-03-13 | 2023-10-17 | Tiger Coatings Gmbh & Co. Kg | Curable coating material for non-impact printing |
Also Published As
Publication number | Publication date |
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CA2734162A1 (en) | 2010-03-11 |
CN102143982A (en) | 2011-08-03 |
US20110136972A1 (en) | 2011-06-09 |
RU2011112796A (en) | 2012-10-10 |
EP2321362A1 (en) | 2011-05-18 |
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