CA1113630A - Revetements deposables par voie cathodique - Google Patents

Revetements deposables par voie cathodique

Info

Publication number: CA1113630A
Authority: CA; Canada
Prior art keywords: groups; coating composition; acid; basic; macromolecular
Prior art date: 1977-09-23
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA309,512A

Other languages

English (en)

Inventor

Gerhard Schmolzer

Heiner Verdino

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Allnex Austria GmbH

Original Assignee

Vianova Resins AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-09-23

Filing date

1978-08-17

Publication date

1981-12-01

1978-08-17 Application filed by Vianova Resins AG filed Critical Vianova Resins AG

1981-12-01 Application granted granted Critical

1981-12-01 Publication of CA1113630A publication Critical patent/CA1113630A/fr

Status Expired legal-status Critical Current

Links

239000008199 coating composition Substances 0.000 title claims abstract description 34
239000002253 acid Substances 0.000 claims abstract description 62
239000011230 binding agent Substances 0.000 claims abstract description 32
-1 cyclic lactam Chemical class 0.000 claims abstract description 25
150000001875 compounds Chemical class 0.000 claims abstract description 22
150000001412 amines Chemical class 0.000 claims abstract description 20
229920005989 resin Polymers 0.000 claims abstract description 18
239000011347 resin Substances 0.000 claims abstract description 18
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 11
239000007795 chemical reaction product Substances 0.000 claims abstract description 9
150000002148 esters Chemical class 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 5
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims abstract description 4
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims abstract description 4
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims abstract description 4
FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 claims abstract description 3
229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
229910001868 water Inorganic materials 0.000 claims description 24
150000008064 anhydrides Chemical group 0.000 claims description 14
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
229920001577 copolymer Polymers 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
239000003431 cross linking reagent Substances 0.000 claims description 6
239000000178 monomer Substances 0.000 claims description 6
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125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229920000728 polyester Polymers 0.000 claims description 4
235000020354 squash Nutrition 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
125000000524 functional group Chemical group 0.000 claims description 3
NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 claims description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
239000000306 component Substances 0.000 claims 17
OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims 1
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
230000036961 partial effect Effects 0.000 abstract description 14
238000005260 corrosion Methods 0.000 abstract description 6
125000000217 alkyl group Chemical group 0.000 abstract description 5
230000007797 corrosion Effects 0.000 abstract description 5
230000002378 acidificating effect Effects 0.000 abstract description 4
238000004132 cross linking Methods 0.000 abstract description 4
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238000006243 chemical reaction Methods 0.000 description 35
239000007787 solid Substances 0.000 description 15
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239000000243 solution Substances 0.000 description 13
150000007513 acids Chemical class 0.000 description 11
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 10
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 10
238000000151 deposition Methods 0.000 description 10
239000002904 solvent Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000000576 coating method Methods 0.000 description 9
230000008021 deposition Effects 0.000 description 9
229920001228 polyisocyanate Polymers 0.000 description 9
239000005056 polyisocyanate Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000003973 paint Substances 0.000 description 8
125000003700 epoxy group Chemical group 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
238000000034 method Methods 0.000 description 7
239000000049 pigment Substances 0.000 description 7
229910000831 Steel Inorganic materials 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
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 6
150000004985 diamines Chemical group 0.000 description 6
239000007788 liquid Substances 0.000 description 6
238000006386 neutralization reaction Methods 0.000 description 6
239000010959 steel Substances 0.000 description 6
150000001252 acrylic acid derivatives Chemical class 0.000 description 5
239000011248 coating agent Substances 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
229930185605 Bisphenol Natural products 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
150000001993 dienes Chemical class 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000002994 raw material Substances 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
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 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UXKQNCDDHDBAPD-UHFFFAOYSA-N 4-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UXKQNCDDHDBAPD-UHFFFAOYSA-N 0.000 description 3
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000004606 Fillers/Extenders Substances 0.000 description 3
239000005062 Polybutadiene Substances 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000010949 copper Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
229920001568 phenolic resin Polymers 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000758 substrate Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
229940086542 triethylamine Drugs 0.000 description 3
FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 2
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
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 2
238000007259 addition reaction Methods 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-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
239000003795 chemical substances by application Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
238000004070 electrodeposition Methods 0.000 description 2
239000003822 epoxy resin Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
229960004279 formaldehyde Drugs 0.000 description 2
235000019256 formaldehyde Nutrition 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
125000005462 imide group Chemical group 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
229920003986 novolac Polymers 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
150000002918 oxazolines Chemical class 0.000 description 2
239000004033 plastic Substances 0.000 description 2
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238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
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LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
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QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
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QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
239000013032 Hydrocarbon resin Substances 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
239000005058 Isophorone diisocyanate Substances 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
AEKNYBWUEYNWMJ-QWOOXDRHSA-N Pramiconazole Chemical group O=C1N(C(C)C)CCN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(CO3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 AEKNYBWUEYNWMJ-QWOOXDRHSA-N 0.000 description 1
229920000147 Styrene maleic anhydride Polymers 0.000 description 1
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125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 1
125000004018 acid anhydride group Chemical group 0.000 description 1
229920006243 acrylic copolymer Polymers 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
229940043232 butyl acetate Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
229940043276 diisopropanolamine Drugs 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
229940093858 ethyl acetoacetate Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229920006270 hydrocarbon resin Polymers 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
125000000879 imine group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000007373 indentation Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 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
150000004658 ketimines Chemical class 0.000 description 1
MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine powder Natural products NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000013849 propane Nutrition 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229920003987 resole Polymers 0.000 description 1
238000012552 review Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
NVKTUNLPFJHLCG-UHFFFAOYSA-N strontium chromate Chemical compound [Sr+2].[O-][Cr]([O-])(=O)=O NVKTUNLPFJHLCG-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
125000005628 tolylene group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
- C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
- C09D5/4465—Polyurethanes

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Paints Or Removers (AREA)
Polyurethanes Or Polyureas (AREA)
Epoxy Resins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA309,512A 1977-09-23 1978-08-17 Revetements deposables par voie cathodique Expired CA1113630A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ATA6816/77		1977-09-23
AT681677A AT353911B (de)	1977-09-23	1977-09-23	Kathodisch abscheidbares ueberzugsmittel

Publications (1)

Publication Number	Publication Date
CA1113630A true CA1113630A (fr)	1981-12-01

Family

ID=3590051

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA309,512A Expired CA1113630A (fr)	1977-09-23	1978-08-17	Revetements deposables par voie cathodique

Country Status (12)

Country	Link
JP (1)	JPS5447733A (fr)
AT (1)	AT353911B (fr)
BR (1)	BR7805272A (fr)
CA (1)	CA1113630A (fr)
DE (1)	DE2831382A1 (fr)
ES (1)	ES472330A2 (fr)
FR (1)	FR2404058A2 (fr)
GB (1)	GB1604070A (fr)
IT (1)	IT1159116B (fr)
SE (1)	SE7808186L (fr)
SU (1)	SU818491A3 (fr)
ZA (1)	ZA783924B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR860008244A (ko) *	1985-04-26	1986-11-14	스즈끼 마사오	수성 페인트 조성물
JPH0676567B2 (ja) *	1986-06-16	1994-09-28	関西ペイント株式会社	カチオン電着塗料用樹脂組成物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3799854A (en) *	1970-06-19	1974-03-26	Ppg Industries Inc	Method of electrodepositing cationic compositions
US3984299A (en) *	1970-06-19	1976-10-05	Ppg Industries, Inc.	Process for electrodepositing cationic compositions
JPS5318194B2 (fr) *	1973-07-10	1978-06-13
JPS538568B2 (fr) *	1974-09-20	1978-03-30

1977
- 1977-09-23 AT AT681677A patent/AT353911B/de not_active IP Right Cessation
1978
- 1978-05-31 GB GB26039/78A patent/GB1604070A/en not_active Expired
- 1978-07-17 DE DE19782831382 patent/DE2831382A1/de not_active Withdrawn
- 1978-07-17 ZA ZA00783924A patent/ZA783924B/xx unknown
- 1978-07-27 SE SE7808186A patent/SE7808186L/xx unknown
- 1978-08-03 ES ES472330A patent/ES472330A2/es not_active Expired
- 1978-08-16 SU SU782647709A patent/SU818491A3/ru active
- 1978-08-16 BR BR7805272A patent/BR7805272A/pt unknown
- 1978-08-17 CA CA309,512A patent/CA1113630A/fr not_active Expired
- 1978-08-17 FR FR7824058A patent/FR2404058A2/fr active Pending
- 1978-08-17 JP JP9959678A patent/JPS5447733A/ja active Pending
- 1978-09-22 IT IT28013/78A patent/IT1159116B/it active

Also Published As

Publication number	Publication date
JPS5447733A (en)	1979-04-14
IT7828013A0 (it)	1978-09-22
ATA681677A (de)	1979-05-15
SE7808186L (sv)	1979-03-24
GB1604070A (en)	1981-12-02
AT353911B (de)	1979-12-10
DE2831382A1 (de)	1979-04-05
FR2404058A2 (fr)	1979-04-20
ES472330A2 (es)	1979-12-16
ZA783924B (en)	1979-07-25
SU818491A3 (ru)	1981-03-30
IT1159116B (it)	1987-02-25
BR7805272A (pt)	1979-04-24

Legal Events

Date	Code	Title	Description
1998-12-01	MKEX	Expiry

Publication	Publication Date	Title
US5096556A (en)	1992-03-17	Cationic microgels and their use in electrodeposition
US3959106A (en)	1976-05-25	Method of electrodepositing quaternary sulfonium group-containing resins
US4857580A (en)	1989-08-15	Crosslinked coating resin
US4909915A (en)	1990-03-20	Non-autocross-linking binder combination, aqueous lacquer coating compounds containing the binder combination and a method for using the same
US4320220A (en)	1982-03-16	Cathodically depositable coating compositions and process for same
US5109040A (en)	1992-04-28	Aqueous cathodic electro-deposition lacquer coating compositions and method of using the same
PL136081B1 (en)	1986-01-31	Thermally hardenable cationic water soluble binder having protonophilic amino groups
CA1085530A (fr)	1980-09-09	Liants (iii) deposables a la cathode
AU601063B2 (en)	1990-08-30	Flexible aryl alkyl epoxy resins, their amine resin derivatives and their use in electrodeposition coatings
US4430462A (en)	1984-02-07	Cathodically depositable aqueous electro-dip lacquer coating composition
US4865705A (en)	1989-09-12	Non-auto crosslinking binder combination, aqueous coating compound containing the same and its use
US3658795A (en)	1972-04-25	Water-soluble coating compositions
EP0612818B1 (fr)	1997-05-07	Revêtement pour l'électrodéposition contenant des microparticules réticulées
AU691523B2 (en)	1998-05-21	Electro-dipcoating paint and process for dip-coating electroconductive substrates
US4197224A (en)	1980-04-08	Binders for cathodically depositable aqueous coating compositions employing an electrodeposition system
US7008998B2 (en)	2006-03-07	Method for making an aqueous dispersion
US4212779A (en)	1980-07-15	Cathodically depositable binders
US5008334A (en)	1991-04-16	Resins of epoxy/aromatic diol copolymer and block copolymer of epoxy/aromatic diol copolymer and a epoxy-capped polybutadiene (co)polymer
US7314900B2 (en)	2008-01-01	Aqueous dispersions and aqueous electrodepositable primers
CA1338690C (fr)	1996-11-05	Liants diluables dans l'eau et leur emploi pour substances de revetement, notamment dans la construction automobile
CA1094707A (fr)	1981-01-27	Traduction non-disponible
US4973613A (en)	1990-11-27	Lead-free cathodically depositable electrodeposition paints based on the reaction product of β-hydroxyalkylamines, titanium compounds, and formaldehyde
CA1113631A (fr)	1981-12-01	Liants cationiques pour produits de recouvrement durcissables a la chaleur et solubles dans l'eau
US4565852A (en)	1986-01-21	Crosslinkable composition comprising aminoepoxy resin-II
AU656438B2 (en)	1995-02-02	Cathodic electrodeposition coatings containing zinc hydroxyphosphite pigment