WO2008054353A2 - Compositions de revêtement pouvant être électrodéposées, et procédés apparentés - Google Patents
Compositions de revêtement pouvant être électrodéposées, et procédés apparentés Download PDFInfo
- Publication number
- WO2008054353A2 WO2008054353A2 PCT/US2006/031133 US2006031133W WO2008054353A2 WO 2008054353 A2 WO2008054353 A2 WO 2008054353A2 US 2006031133 W US2006031133 W US 2006031133W WO 2008054353 A2 WO2008054353 A2 WO 2008054353A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coating composition
- catalyst nanoparticles
- electrodepositable coating
- composition according
- resin
- Prior art date
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- 239000008199 coating composition Substances 0.000 title claims abstract description 70
- 238000000034 method Methods 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 140
- 239000003054 catalyst Substances 0.000 claims abstract description 96
- 239000002105 nanoparticle Substances 0.000 claims abstract description 79
- 229920005989 resin Polymers 0.000 claims abstract description 74
- 239000011347 resin Substances 0.000 claims abstract description 74
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000012736 aqueous medium Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical group 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims description 70
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 54
- 239000000463 material Substances 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000000758 substrate Substances 0.000 claims description 33
- 229920000647 polyepoxide Polymers 0.000 claims description 27
- 238000004070 electrodeposition Methods 0.000 claims description 26
- 239000000377 silicon dioxide Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 229910000416 bismuth oxide Inorganic materials 0.000 claims description 18
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 13
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 13
- 229910052750 molybdenum Inorganic materials 0.000 claims description 13
- 239000011733 molybdenum Substances 0.000 claims description 13
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052721 tungsten Inorganic materials 0.000 claims description 13
- 239000010937 tungsten Substances 0.000 claims description 13
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 11
- DQUIAMCJEJUUJC-UHFFFAOYSA-N dibismuth;dioxido(oxo)silane Chemical compound [Bi+3].[Bi+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O DQUIAMCJEJUUJC-UHFFFAOYSA-N 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 11
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 11
- 235000012239 silicon dioxide Nutrition 0.000 claims description 11
- 239000002981 blocking agent Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000011164 primary particle Substances 0.000 claims description 8
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 7
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910002115 bismuth titanate Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 6
- 239000011787 zinc oxide Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 238000000151 deposition Methods 0.000 claims description 4
- 230000008021 deposition Effects 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 description 73
- 238000010791 quenching Methods 0.000 description 41
- 238000001723 curing Methods 0.000 description 38
- 125000002091 cationic group Chemical group 0.000 description 34
- 239000000047 product Substances 0.000 description 34
- 239000007789 gas Substances 0.000 description 32
- 229920000728 polyester Polymers 0.000 description 30
- -1 for example Chemical class 0.000 description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- 239000002243 precursor Substances 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- 238000000576 coating method Methods 0.000 description 22
- 239000006185 dispersion Substances 0.000 description 22
- 239000005056 polyisocyanate Substances 0.000 description 18
- 229920001228 polyisocyanate Polymers 0.000 description 18
- 229920005862 polyol Polymers 0.000 description 18
- 239000000376 reactant Substances 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 17
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 150000003077 polyols Chemical class 0.000 description 12
- 229910001868 water Inorganic materials 0.000 description 12
- 150000002118 epoxides Chemical class 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000004814 polyurethane Substances 0.000 description 9
- 229920002635 polyurethane Polymers 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- 238000003917 TEM image Methods 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 229920000058 polyacrylate Polymers 0.000 description 7
- 150000003141 primary amines Chemical class 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000012159 carrier gas Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000001000 micrograph Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 6
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
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- 239000004615 ingredient Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 description 4
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000011144 upstream manufacturing Methods 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- DKWHHTWSTXZKDW-UHFFFAOYSA-N 1-[2-[2-[2-(2-butoxyethoxy)ethoxymethoxy]ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCOCCOCCOCCCC DKWHHTWSTXZKDW-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(III) oxide Inorganic materials O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000004658 ketimines Chemical class 0.000 description 3
- 230000033001 locomotion Effects 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
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- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 2
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
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- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012702 metal oxide precursor Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000007746 phosphate conversion coating Methods 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 229920006009 resin backbone Polymers 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910021487 silica fume Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 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
- 238000002076 thermal analysis method Methods 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical class CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4488—Cathodic paints
- C09D5/4496—Cathodic paints characterised by the nature of the curing agents
Definitions
- the present invention relates to cationic electrodepositable coating compositions comprising a resinous phase and certain catalyst nanoparticles dispersed in an aqueous medium, wherein the catalyst nanoparticles have a specified B.E.T. specific surface area to methods of preparing such compositions; and to methods for applying such compositions.
- Electrodeposition has gained prominence in the coating industry because, in comparison with non-electrophoretic coating methods, electrodeposition provides higher paint utilization, excellent corrosion resistance and low environmental contamination.
- Electrodeposition processes used anionic electrodeposition where the workpiece to be coated serves as the anode.
- cationic electrodeposition has become increasingly popular and today is the most prevalent method of electrodeposition.
- cationic electrodeposition compositions in use today are based on active hydrogen-containing resins derived from a polyepoxide and a capped or blocked polyisocyanate curing agent. Typically, these cationic electrodeposition compositions also contain organotin catalysts to lower the temperature at which the blocking agent is released from blocked polyisocyanate and to activate cure of the electrodeposition composition.
- organotin catalysts to lower the temperature at which the blocking agent is released from blocked polyisocyanate and to activate cure of the electrodeposition composition.
- Most of the common dialkyltin oxide catalysts are high melting, amorphous solid materials which must be introduced into the composition in the form of a catalyst paste prepared by dispersing the solid catalyst into a pigment wetting resin under extremely high shear conditions. Preparation of stable catalyst pastes can be very costly and time intensive.
- organotin catalysts can cause a multitude of surface defects in the cured electrodeposited coating composition.
- dibutyltin oxide dispersions can flocculate in the electrodeposition bath, resulting in oversized dibutyltin oxide agglomerates or particles which can settle in areas of the electrodeposition tank where agitation is poor.
- This flocculation phenomenon constitutes a loss of catalyst from the coating composition resulting in poor cure response.
- the flocculate particles can settle in the uncured electrodeposited coating causing localized "hot spots" or pinholes in the surface of the cured coating.
- electrodeposition bath stability can be adversely affected with the use of some organotin catalysts.
- Triorganotin compounds are known for use as catalysts in electrodepositable coating compositions comprised of an active hydrogen- containing resin and a blocked polyisocyanate curing agent. Such triorganotin compounds, however, have been observed to have poor cure response when used in conjunction with resinous components having phenolic hydroxyl groups. Moreover, some trialkyltin compounds, for example, tributyltin compounds, are known to be volatile at typical curing temperatures. Also, some trialkyltin compounds can be toxic. Further, many triorganotin compounds typically have the disadvantage of high cost.
- the present invention provides electrodepositable coating compositions comprising a resinous phase and catalyst nanoparticles dispersed in an aqueous medium, the resinous phase comprising: (a) a active hydrogen-containing, ionic salt group-containing resin; and (b) at least one curing agent; and catalyst nanoparticles for effecting cure between the resin (a) a curing agent (b), the catalyst nanoparticles being selected from the group consisting of bismuth oxide; bismuth silicate; bismuth titanate; molybdenum oxide; molybdenum silicate; molybdenum titanate; tungsten oxide; tungsten silicate; tungsten titanate; a combination of cerium - oxide, zinc oxide and silicon dioxide; a combination of cerium oxide and silicon dioxide; and combinations thereof, 1 wherein the catalyst nanoparticles have an average B. ET. specific surface area greater than 20 square meters per gram (m 2 /g).
- the present invention provides methods for electrocoating a conductive substrate serving as a cathode in an electrical circuit comprising the cathode and an anode, the cathode and anode being immersed in an aqueous electrocoating composition, the methods comprising passing electric current between the cathode and anode to cause deposition of the electrocoating composition onto the substrate as a substantially continuous film, the aqueous electrocoating composition comprising a resinous phase dispersed in an aqueous medium, the resinous phase comprising: (a) a active hydrogen group-containing, ionic group- containing electrodepositable resin; and (b) a curing agent, and catalyst nanoparticles for effecting cure between the resin (a) and the curing agent (b), the catalyst nanoparticles being selected from the group consisting of bismuth oxide; bismuth silicate; bismuth titanate; molybdenum oxide; molybdenum silicate; molybdenum titanate; tungsten
- Fig. 1 is a flow diagram of certain embodiments of suitable methods for making catalyst nanoparticles in accordance with the present invention
- FIG. 2 is a schematic diagram of an apparatus for producing catalyst nanoparticles in accordance with certain embodiments of the present invention
- FIG. 3 is a perspective view of a plurality of quench gas injection ports in accordance with certain embodiments of the present invention.
- Fig. 4 is a micrograph of a TEM image of a representative portion of the nanoparticles of Example 1 (10,000x magnification); and [0014] Fig. 5 is a micrograph of a TEM image of a representative portion of the nanoparticles of Example 2 (210,00Ox magnification).
- any numerical range recited herein is intended to include all sub-ranges subsumed therein.
- a range of "1 to 10" is intended to include all sub-ranges between and including the recited minimum value of 1 and the recited maximum value of 10, that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10.
- the present invention provides electrodepositable coating compositions comprising a resinous phase and catalyst nanoparticles dispersed in an aqueous medium, the resinous phase comprising: (a) at least one active hydrogen-containing, ionic salt group-containing resin; (b) at least one curing agent.
- the catalyst nanoparticles effect or facilitate cure between the resin (a) and the curing agent (b), as described in detail below.
- the catalyst nanoparticles are selected from the group consisting of bismuth oxide; bismuth silicate; bismuth titanate; molybdenum oxide; molybdenum silicate; molybdenum titanate; tungsten oxide; tungsten silicate; tungsten titanate; a combination of cerium oxide, zinc oxide and silicon dioxide; a combination of cerium oxide and silicon dioxide; and combinations thereof, such as composite particles of two or more of these compounds or combinations.
- the catalyst nanoparticles comprise bismuth oxide. In other embodiments, the catalyst particles comprise bismuth oxide and silica. In other embodiments, the catalyst particles comprise bismuth oxide and bismuth silicate. In other embodiments, the catalyst particles comprise bismuth oxide, bismuth silicate and silica. [0021] In some embodiments, the catalyst nanoparticles may be a complex metal oxide comprising a homogeneous mixture, or solid state solution of two or more (up to x) metal oxides, labeled MO1, MO 2 , . . . . MO x , [0022] The catalyst nanoparticles have an average B. ET.
- the BET specific surface area can be measured by any method well known to those skilled in the art, such as by nitrogen absorption according to ASTM D 3663-78 standard based upon the Brunauer, Emmett, and Teller method described in J. Am. Chem. Soc'y 60, 309 (1938).
- the BET specific surface area can be measured using a Gemini Model 2360 surface area analyzer (available from Micromeritics Instrument Corp. of Norcross, Georgia).
- the catalyst nanoparticles have a calculated equivalent spherical diameter of less than 500 nanometers, in other embodiments less than 100 nanometers and in still other embodiments less than 50 nanometers.
- a calculated equivalent spherical diameter can be determined from the B. ET. specific surface area according to the following equation:
- the catalyst nanoparticles can have an average primary particle size of less than 500 nanometers. In some embodiments, the catalyst nanoparticles can have an average primary particle size of less than 100 nanometers, and in other embodiments less than 50 nanometers. In some embodiments, the catalyst nanoparticles have an average primary particle size of less than 30 nanometers and in other embodiments less than 20 nanometers. The particles typically have an average primary particle size greater than 1 nm.
- the average primary particle size can be determined by visually examining an electron micrograph of a transmission electron microscopy ("TEM") image, measuring the diameter of the particles in the image, and calculating the average particle size ("APS") based on the magnification of the TEM image.
- TEM transmission electron microscopy
- APS average particle size
- the primary particle size of a particle refers to the smallest diameter sphere that will completely enclose the particle.
- the phrase "primary particle size" refers to the size of an individual particle as opposed to an agglomeration of two or more individual particles.
- compositions in accordance with the present invention can be incorporated into the compositions in accordance with the present invention to impart the desired properties and characteristics to the compositions.
- particles of varying particle sizes can be used in the compositions according to the present invention.
- the catalyst nanoparticles can be present in the coating composition in an amount sufficient to effect cure of the coating composition at or below a temperature of 360 0 F (182.2°C). In some embodiments, catalyst nanoparticles are present in the coating composition in an amount sufficient to effect cure of the coating composition at or below a temperature of 340°F (171.1 0 C). In other embodiments, catalyst nanoparticles are present in the coating composition in an amount sufficient to effect cure of the coating composition at or below a temperature of 320 0 F (160 0 C). In other embodiments, catalyst nanoparticles are present in the coating composition in an amount sufficient to effect cure of the coating composition at or below a temperature of 300 0 F (149°C).
- the cure temperature can vary based upon the amount and type of catalyst nanoparticles used.
- the particles When the film-forming composition of the present invention is in a liquid medium, the particles have an affinity for the medium of the composition sufficient to keep the particles suspended therein.
- the affinity of the particles for the medium is greater than the affinity of the particles for each other, thereby preventing agglomeration of the particles within the medium. This property is due to the nature of the particles themselves.
- the particles are also substantially free of any surface treatment.
- the particles used in the composition of the present invention may be added to the composition neat during the formulation thereof, and may be added at high loadings without appreciable viscosity increases, allowing for formulation of high solids coating compositions.
- the shape (or morphology) of the particles can vary depending upon the specific embodiment of the present invention and its intended application. For example, generally spherical morphologies can be used, as well as particles that are cubic, platy, or acicular (elongated or fibrous). In general, the particles are substantially spherical in shape.
- the catalyst nanoparticles may be prepared by various methods, including gas phase synthesis processes, such as, for example, flame pyrolysis, hot walled reactor, chemical vapor synthesis, among other methods. In certain embodiments, however, such particles are prepared by reacting together one or more organometallic and/or metal oxide precursors and any other ingredients in a fast quench plasma system.
- the particles may be formed in such a system by: (a) introducing materials into a plasma chamber; (b) rapidly heating the materials by means of a plasma to a selection temperature sufficient to yield a gaseous product stream; (c) passing the gaseous product stream through a restrictive convergent-divergent nozzle to effect rapid cooling and/or utilizing an alternative cooling method, such as a cool surface or quenching stream, and (d) condensing the gaseous product stream to yield ultrafine solid particles.
- an alternative cooling method such as a cool surface or quenching stream
- Materials suitable for use in the quench streams include, but are not limited to, hydrogen gas, carbon dioxide, air, water vapor, ammonia, mono, di and polybasic alcohols, silicon-containing materials (such as hexamethyldisilazane), carboxylic acids and/or hydrocarbons.
- the particular flow rates and injection angles of the various quench streams are not limited, so long as they impinge with each other within the gaseous product stream to result in the rapid cooling of the gaseous product stream to produce catalyst nanoparticles.
- the quench streams primarily cool the gaseous product stream through dilution, rather than adiabatic expansion, thereby causing a rapid quenching of the gaseous product stream and the formation of ultrafine solid particles prior to passing the particles into and through a converging member, such as a converging-diverging nozzle, as described below.
- a converging member such as a converging-diverging nozzle, as described below.
- the particles are, at step 500, passed through a converging member, wherein the plasma system is designed to minimize the fouling thereof.
- the converging member comprises a converging- diverging (De Laval) nozzle.
- the gas may be inert, such as argon, helium, or neon, reductive, such as hydrogen, methane, ammonia, and carbon monoxide, or oxidative, such as oxygen, nitrogen, and carbon dioxide.
- reductive such as hydrogen, methane, ammonia, and carbon monoxide
- oxidative such as oxygen, nitrogen, and carbon dioxide.
- Air, oxygen, and/or oxygen/argon gas mixtures are often used to produce ultrafine solid particles in accordance with the present invention.
- the plasma gas feed inlet is depicted at 31.
- Fig. 3 there is depicted a perspective view of a plurality of quench gas injection ports 40 in accordance with certain embodiments of the present invention.
- six (6) quench gas injection ports are depicted, wherein each port disposed at an angle " ⁇ " apart from each other along the circumference of the reactor chamber 20.
- " ⁇ " may have the same or a different value from port to port.
- at least four (4) quench gas injection ports 40 are provided, in some cases at least six (6) quench gas injection ports are present.
- each angle " ⁇ " has a value of no more than 90°.
- the plasma chamber walls may be internally heated by a combination of radiation, convection and conduction.
- cooling of the plasma chamber walls prevents unwanted melting and/or corrosion at their surfaces.
- the system used to control such cooling should maintain the walls at as high a temperature as can be permitted by the selected wall material, which often is inert to the materials within the plasma chamber at the expected wall temperatures. This is true also with regard to the nozzle walls, which may be subjected to heat by convection and conduction.
- the converging section of the nozzle has a high aspect ratio change in diameter that maintains smooth transitions to a first steep angle (such as > 45°) and then to lesser angles (such as ⁇ 45°degree.) leading into the nozzle throat.
- the purpose of the nozzle throat is often to compress the gases and achieve sonic velocities in the flow.
- the velocities achieved in the nozzle throat and in the downstream diverging section of the nozzle are controlled by the pressure differential between the plasma chamber and the section downstream of the diverging section of the nozzle. Negative pressure can be applied downstream or positive pressure applied upstream for this purpose.
- a converging-diverging nozzle of the type suitable for use in the present invention is described in United States Patent No.
- the catalyst is characterized in that the catalyst is substantially non-volatile at the curing temperature, that is, at temperatures at or below 360°F (182.2°C).
- substantially non- volatile is meant that the catalyst does not volatilize from the film into the curing oven environment at these temperatures during the curing process.
- the electrodepositable coating composition of the present invention comprises (a) one or more active hydrogen-containing, ionic salt group-containing resins, and (b) one or more curing agents.
- cyclic polyols can be used in preparing the polyglycidyl ethers of cyclic polyols.
- examples of other cyclic polyols include alicyclic polyols, particularly cycloaliphatic polyols such as 1 ,2-cyclohexane diol and 1 ,2- bis(hydroxymethyl)cyclohexane.
- the preferred polyepoxides have epoxide equivalent weights ranging from 180 to 2000, preferably from 186 to 1200.
- Epoxy group-containing acrylic polymers can also be used. These polymers typically have an epoxy equivalent weight ranging from 750 to 2000.
- the reaction product of the primary and/or secondary amine and the polyepoxide is made cationic and water dispersible by at least partial neutralization with an acid.
- Suitable acids include organic and inorganic acids.
- suitable organic acids include formic acid, acetic acid, methanesulfonic acid, and lactic acid.
- suitable inorganic acids include phosphoric acid and sulfamic acid.
- sulfamic acid is meant sulfamic acid itself or derivatives thereof; i.e., an acid of the formula:
- the extent of neutralization of the cationic electrodepositable composition varies with the particular reaction product involved. However, sufficient acid should be used to disperse the electrodepositable composition in water. Typically, the amount of acid used provides at least 20 percent of all of the total neutralization. Excess acid may also be used beyond the amount required for 100 percent total neutralization.
- the tertiary amine can be pre-reacted with the neutralizing acid to form the amine salt and then the amine salt reacted with the polyepoxide to form a quaternary salt group-containing resin. The reaction is conducted by mixing the amine salt with the polyepoxide in water. Typically, the water is present in an amount ranging from 1.75 to 20 percent by weight based on total reaction mixture solids.
- the reaction temperature can be varied from the lowest temperature at which the reaction will proceed, generally room temperature or slightly thereabove, to a maximum temperature of 100 °C (at atmospheric pressure). At higher pressures, higher reaction temperatures may be used. Preferably, the reaction temperature is in the range of 60 to 100 0 C. Solvents such as a sterically hindered ester, ether, or sterically hindered ketone may be used, but their use is not necessary.
- a portion of the amine that is reacted with the polyepoxide can be a ketimine of a polyamine, such as is described in U.S. Patent No. 4,104,147, column 6, line 23 to column 7, line 23.
- the ketimine groups decompose upon dispersing the amine-epoxy resin reaction product in water.
- Suitable active hydrogen-containing, cationic salt group- containing resins can include copolymers of one or more alkyl esters of acrylic acid or methacrylic acid optionally together with one or more other polymerizable ethylenically unsaturated monomers.
- Suitable alkyl esters of acrylic acid or methacrylic acid include methyl methacrylate, ethyl methacrylate, butyl methacrylate, ethyl acrylate, butyl acrylate, and 2-ethyl hexyl acrylate.
- Functional groups such as hydroxyl and amino groups can be incorporated into the acrylic polymer by using functional monomers such as hydroxyalkyl acrylates and methacrylates or aminoalkyi acrylates and methacrylates.
- Epoxide functional groups (for conversion to cationic salt groups) may be incorporated into the acrylic polymer by using functional monomers such as glycidyl acrylate and methacrylate, 3,4- epoxycyclohexylmethyl(meth)acrylate, 2-(3,4- epoxycyclohexyl)ethyl(meth)acrylate, or allyl glycidyl ether.
- epoxide functional groups may be incorporated into the acrylic polymer by reacting carboxyl groups on the acrylic polymer with an epihalohydrin or dihalohydrin such as epichlorohydrin or dichlorohydrin.
- the acrylic polymer can be prepared by traditional free radical initiated polymerization techniques, such as solution or emulsion polymerization, as known in the art, using suitable catalysts which include organic peroxides and azo type compounds and optionally chain transfer agents such as alpha-methyl styrene dimer and tertiary dodecyl mercaptan.
- Additional acrylic polymers which are suitable for forming the active hydrogen- containing, cationic resin (a) which can be used in the electrodepositable compositions of the present invention include those resins described in U.S. Patent Nos. 3,455,806 and 3,928,157.
- Polyurethanes can also be used as the polymer from which the active hydrogen-containing, cationic resin can be derived.
- the polyurethanes which can be used are polymeric polyols which are prepared by reacting polyester polyols or acrylic polyols such as those mentioned above with a polyisocyanate such that the OH/NCO equivalent ratio is greater than 1 :1 so that free hydroxyl groups are present in the product.
- Smaller polyhydric alcohols such as those disclosed above for use in the preparation of the polyester may also be used in place of or in combination with the polymeric polyols.
- polyurethane polymers suitable for forming the active hydrogen-containing, cationic resin (a) include the polyurethane, polyurea, and poly(urethane-urea) polymers prepared by reacting polyether polyols and/or polyether polyamines with polyisocyanates. Such polyurethane polymers are described in U.S. Patent No. 6,248,225.
- Epoxide functional groups may be incorporated into the polyurethane by methods well known in the art. For example, epoxide groups can be incorporated by reacting glycidol with free isocyanate groups. Alternatively, hydroxyl groups on the polyurethane can be reacted with an epihalohydrin or dihalohydrin such as epichlorohydrin or dichlorohydrin in the presence of alkali.
- Sulfonium group-containing polyurethanes can also be made by at least partial reaction of hydroxy-functional sulfide compounds, such as thiodiglycol and thiodipropanol, which results in incorporation of sulfur into the backbone of the polymer.
- the sulfur-containing polymer is then reacted with a monofunctional epoxy compound in the presence of acid to form the sulfonium group.
- Appropriate monofunctional epoxy compounds include ethylene oxide, propylene oxide, glycidol, phenylglycidyl ether, and CARDURA® E, available from Resolution Performance Products.
- the active hydrogen-containing, cationic salt group- containing polymer can be derived from a polyester.
- polyesters can be prepared in a known manner by condensation of polyhydric alcohols and polycarboxylic acids.
- Suitable polyhydric alcohols include, for example, ethylene glycol, propylene glycol, butylene glycol, 1 ,6-hexylene glycol, neopentyl glycol, diethylene glycol, glycerol, trimethylol propane, and pentaerythritol.
- polyesters examples include succinic acid, adipic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, and trimellitic acid.
- functional equivalents of the acids such as anhydrides where they exist or lower alkyl esters of the acids such as the methyl esters may be used.
- the polyesters contain a portion of free hydroxyl groups
- Sulfonium salt groups can be introduced by the reaction of an epoxy group-containing polymer of the types described above with a sulfide in the presence of an acid, as described in U.S. Patent Nos. 3,959,106 and 4,715,898. Sulfonium groups can be introduced onto the polyester backbones described using similar reaction conditions.
- the active hydrogens associated with the cationic resin include any active hydrogens which are reactive with isocyanates at temperatures sufficient to cure the electrodepositable composition as previously discussed, i.e., at temperatures at or below 360°F (182.2°C).
- the active hydrogens typically are derived from reactive hydroxyl groups, and primary and secondary amino, including mixed groups such as hydroxyl and primary amino.
- the active hydrogens are derived from hydroxyl groups comprising phenolic hydroxyl groups.
- the cationic resin can have an active hydrogen content of 1 to 4 milliequivalents, typically 2 to 3 milliequivalents of active hydrogen per gram of resin solids.
- the extent of cationic salt group formation should be such that when the resin is mixed with an aqueous medium and other ingredients, a stable dispersion of the electrodepositable composition will form.
- stable dispersion is meant one that does not settle or is easily redispersible if some settling occurs.
- non- gelled is meant that the resin is substantially free from crosslinking, and prior to cationic salt group formation, the resin has a measurable intrinsic viscosity when dissolved in a suitable solvent.
- a gelled resin having an essentially infinite molecular weight, would have an intrinsic viscosity too high to measure.
- the active hydrogen-containing, cationic salt group- containing resin (a) can be present in the electrodepositable composition of the present invention in an amount ranging from 40 to 95 weight percent, typically from 50 to 75 weight percent based on weight of total resin solids present in the composition.
- the electrodepositable composition of the present invention also comprises at least one curing agent, such as a polyisocyanate, polyester or carbonate.
- the polyisocyanate curing agent may be a fully blocked polyisocyanate with substantially no free isocyanate groups, or it may be partially blocked and reacted with the resin backbone as described in U.S. Patent 3,984,299.
- the polyisocyanate can be an aliphatic or an aromatic polyisocyanate or a mixture of the two. Diisocyanates are preferred, although higher polyisocyanates can be used in place of or in combination with diisocyanates.
- Suitable aliphatic diisocyanates are straight chain aliphatic diisocyanates such as 1 ,4-tetramethylene diisocyanate, norbornane diisocyanate, and 1 ,6-hexamethylene diisocyanate.
- cycloaliphatic diisocyanates can be employed. Examples include isophorone diisocyanate and 4,4'-methylene-bis-(cyclohexyl isocyanate).
- suitable aromatic diisocyanates are p-phenylene diisocyanate, diphenylmethane-4,4'-diisocyanate and 2,4- or 2,6-toluene diisocyanate.
- Isocyanate prepolymers for example, reaction products of polyisocyanates with polyols such as neopentyl glycol and trimethylol propane or with polymeric polyols such as polycaprolactone diols and triols (NCO/OH equivalent ratio greater than one) can also be used.
- a mixture of diphenylmethane-4,4'-diisocyanate and polymethylene polyphenyl isocyanate can be used.
- Any suitable alcohol or polyol can be used as a blocking agent for the polyisocyanate in the electrodepositable composition of the present invention provided that the agent will deblock at the curing temperature and provided a gelled product is not formed.
- Any suitable aliphatic, cycloaliphatic, or aromatic alkyl alcohol may be used as a blocking agent for the polyisocyanate including, for example, lower aliphatic monoalcohols such as methanol, ethanol, and n-butanol; cycloaliphatic alcohols such as cyclohexanol; aromatic-alkyl alcohols such as phenyl carbinol and methylphenyl carbinol.
- Glycol ethers may also be used as blocking agents. Suitable glycol ethers include ethylene glycol butyl ether, diethylene glycol butyl ether, ethylene glycol methyl ether and propylene glycol methyl ether.
- Suitable blocking agents include oximes such as methyl ethyl ketoxime, acetone oxime and cyclohexanone oxime and lactams such as epsilon-caprolactam.
- the curing agent comprises one or more polyester curing agents.
- Suitable polyester curing agents include materials having greater than one ester group per molecule.
- the ester groups are present in an amount sufficient to effect cross-linking at acceptable cure temperatures and cure times, for example at temperatures up to 250 0 C, and curing times of up to 90 minutes. It should be understood that acceptable cure temperatures and cure times will be dependent upon the substrates to be coated and their end uses.
- the polyester curing agent is substantially free of acid.
- substantially free of acid is meant having less than 0.2 meq/g acid.
- suitable polyester curing agents can include non-acidic polyesters prepared from a polycarboxylic acid anhydride, one or more glycols, alcohols, glycol mono-ethers, polyols, and/or monoepoxides.
- Non-acidic polyesters can be prepared, for example, by reacting, in one or more steps, trimellitic anhydride (TMA) with glycidyl esters of branched monocarboxylic acids in a molar ratio of 1 :1.5 to 1 :3, if desired with the aid of an esterification catalyst such as stannous octoate or benzyl dimethyl amine, at temperatures of 50-150 0 C. Additionally, trimellitic anhydride can be reacted with 3 molar equivalents of a monoalcohol such as 2-ethylhexanol.
- TMA trimellitic anhydride
- glycidyl esters of branched monocarboxylic acids in a molar ratio of 1 :1.5 to 1 :3, if desired with the aid of an esterification catalyst such as stannous octoate or benzyl dimethyl amine, at temperatures of 50-150 0 C.
- trimellitic anhydride can be reacted with
- trimellitic anhydride (1 mol.) can be reacted first with a glycol or a glycol monoalkyl ether, such as ethylene glycol monobutyl ether in a molar ratio of 1 :0.5 to 1 :1 , after which the product is allowed to react with 2 moles of glycidyl esters of branched monocarboxylic acids.
- a glycol or a glycol monoalkyl ether such as ethylene glycol monobutyl ether in a molar ratio of 1 :0.5 to 1 :1
- polycarboxylic acid anhydride i.e., those containing two or three carboxyl functions per molecule
- a mixture of polycarboxylic acid anhydrides can be reacted simultaneously with a glycol, such as 1 ,6- hexane diol and/or glycol mono-ether and monoepoxide, after which the product can be reacted with mono-epoxides, if desired.
- these non-acid polyesters can also be modified with polyamines such as diethylene triamine to form amide polyesters.
- polyamine-modified polyesters may be incorporated in the linear or branched amine adducts described above to form self-curing amine adduct esters.
- the catalyst nanoparticles can be incorporated into the electrodepositable composition of the present invention by any method or means provided that the stability of the composition is not compromised.
- the catalyst nanoparticles can be admixed with or dispersed in the reactants used to form the resin (a) during preparation of the resin (a).
- the catalyst nanoparticles can be admixed with or dispersed in one or more of the reactants used to form the resin (a) prior to resin preparation.
- the catalyst nanoparticles can be admixed with or dispersed in the resin (a) either prior to or subsequent to neutralization with an acid.
- the catalyst nanoparticles also can be added neat to the electrodepositable composition subsequent to dispersion in the aqueous medium. Additionally, if desired, the catalyst nanoparticles can be added online to the electrodeposition bath in the form of an additive material. It should be understood that the catalyst can be incorporated into the electrodepositable composition by one or more of the above described methods.
- the electrodepositable composition may optionally contain a coalescing solvent such as hydrocarbons, alcohols, esters, ethers and ketones.
- the electrodepositable composition of the present invention may further contain pigments and various other optional additives such as plasticizers, surfactants, wetting agents, defoamers, and anti- cratering agents, as well as adjuvant resinous materials different from the resin (a) and the curing agent (b).
- the present invention is directed to a method of coating a substrate further comprising a step of curing the composition after application to the substrate.
- the components used to form the compositions in these embodiments can be selected from the components discussed above, and additional components also can be selected from those recited above.
- [00128] Particles from solid precursors were prepared using a DC thermal plasma reactor system of the type described in United States Patent No. RE 37.853E.
- the main reactor system included a DC plasma torch (Model SG-100 Plasma Spray Gun commercially available from Praxair Technology, Inc., Danbury, Connecticut) operated with 60 standard liters per minute of argon carrier gas and 28 kilowatts of power delivered to the torch.
- Solid reactant feed compositions comprising the materials and amounts listed in Tables 1-5 were prepared and fed to the reactor at a rate of 2.5 grams per minute through a gas assistant powder feeder (Model 1264, commercially available from Praxair Technology, Inc., Danbury, Connecticut) located at the plasma torch outlet.
- Coating compositions were prepared using the components and weights (in grams) shown in Table 10. Coatings were prepared by adding components 1 to 3 to a suitable vessel under agitation with a tong press for 3 minutes.
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Abstract
L'invention concerne une composition de revêtement pouvant être électrodéposée comprenant une phase résineuse et des nanoparticules de catalyseur dispersées dans un milieu aqueux, la phase résineuse comprenant (a) au moins une résine contenant un groupe de sel ionique contenant de l'hydrogène actif ; et (b) au moins un agent de durcissement ; et les nanoparticules de catalyseur pour effectuer un durcissement entre la résine (a) et l'agent de durcissement (b). Les nanoparticules de catalyseur ont une surface spécifique BET moyenne supérieure à 20 mètres carrés par gramme (m2/g). Des procédés pour préparer et utiliser la composition sont également proposés.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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EP06851821A EP1948743A2 (fr) | 2005-08-26 | 2006-08-10 | Compositions de revêtement pouvant être électrodéposées, et procédés apparentés |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US11/213,174 | 2005-08-26 | ||
US11/213,174 US20070045116A1 (en) | 2005-08-26 | 2005-08-26 | Electrodepositable coating compositions and related methods |
Publications (3)
Publication Number | Publication Date |
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WO2008054353A2 true WO2008054353A2 (fr) | 2008-05-08 |
WO2008054353A3 WO2008054353A3 (fr) | 2008-08-14 |
WO2008054353A9 WO2008054353A9 (fr) | 2009-07-23 |
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PCT/US2006/031133 WO2008054353A2 (fr) | 2005-08-26 | 2006-08-10 | Compositions de revêtement pouvant être électrodéposées, et procédés apparentés |
Country Status (3)
Country | Link |
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US (1) | US20070045116A1 (fr) |
EP (1) | EP1948743A2 (fr) |
WO (1) | WO2008054353A2 (fr) |
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US20140150970A1 (en) | 2010-11-19 | 2014-06-05 | Ppg Industries Ohio, Inc. | Structural adhesive compositions |
US8796361B2 (en) | 2010-11-19 | 2014-08-05 | Ppg Industries Ohio, Inc. | Adhesive compositions containing graphenic carbon particles |
US10763490B2 (en) | 2011-09-30 | 2020-09-01 | Ppg Industries Ohio, Inc. | Methods of coating an electrically conductive substrate and related electrodepositable compositions including graphenic carbon particles |
US9832818B2 (en) | 2011-09-30 | 2017-11-28 | Ppg Industries Ohio, Inc. | Resistive heating coatings containing graphenic carbon particles |
US9761903B2 (en) | 2011-09-30 | 2017-09-12 | Ppg Industries Ohio, Inc. | Lithium ion battery electrodes including graphenic carbon particles |
US9475946B2 (en) | 2011-09-30 | 2016-10-25 | Ppg Industries Ohio, Inc. | Graphenic carbon particle co-dispersions and methods of making same |
US9988551B2 (en) | 2011-09-30 | 2018-06-05 | Ppg Industries Ohio, Inc. | Black pigments comprising graphenic carbon particles |
US10294375B2 (en) | 2011-09-30 | 2019-05-21 | Ppg Industries Ohio, Inc. | Electrically conductive coatings containing graphenic carbon particles |
US10240052B2 (en) | 2011-09-30 | 2019-03-26 | Ppg Industries Ohio, Inc. | Supercapacitor electrodes including graphenic carbon particles |
US8486363B2 (en) * | 2011-09-30 | 2013-07-16 | Ppg Industries Ohio, Inc. | Production of graphenic carbon particles utilizing hydrocarbon precursor materials |
US9938416B2 (en) | 2011-09-30 | 2018-04-10 | Ppg Industries Ohio, Inc. | Absorptive pigments comprising graphenic carbon particles |
US11430979B2 (en) | 2013-03-15 | 2022-08-30 | Ppg Industries Ohio, Inc. | Lithium ion battery anodes including graphenic carbon particles |
GB201410700D0 (en) * | 2014-06-16 | 2014-07-30 | Pq Silicas Uk Ltd | Curable liquid compositions |
US10377928B2 (en) | 2015-12-10 | 2019-08-13 | Ppg Industries Ohio, Inc. | Structural adhesive compositions |
US10351661B2 (en) | 2015-12-10 | 2019-07-16 | Ppg Industries Ohio, Inc. | Method for producing an aminimide |
CN106883760B (zh) * | 2017-03-07 | 2019-06-18 | 瑞娃科技(重庆)有限公司 | 一种高光水洗净纳米树脂及其制备方法 |
US11225441B2 (en) * | 2018-10-18 | 2022-01-18 | Praxair S.T. Technology, Inc. | Chromium-free silicate-based ceramic compositions with reduced curing temperature |
US11123715B2 (en) * | 2019-11-22 | 2021-09-21 | King Fahd University Of Petroleum And Minerals | Mesoporous composite catalysts containing bismuth silicate and transition metal oxide |
CN114846044A (zh) * | 2019-12-31 | 2022-08-02 | Ppg工业俄亥俄公司 | 可电沉积的涂层组合物 |
CN115551954A (zh) * | 2020-05-25 | 2022-12-30 | 巴斯夫涂料有限公司 | 具有改进催化活性的含铋电泳涂料 |
CA3199679A1 (fr) * | 2020-11-09 | 2022-05-12 | Huntsman Advanced Materials Americas Llc | Sechage par pulverisation de resines epoxy ou phenoxy solides |
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Also Published As
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US20070045116A1 (en) | 2007-03-01 |
WO2008054353A3 (fr) | 2008-08-14 |
EP1948743A2 (fr) | 2008-07-30 |
WO2008054353A9 (fr) | 2009-07-23 |
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