CA1179443A - Agents de liaisonnement dispersibles dans l'eau pour composes cationiques de revetement applicables par electrodeposition, et methode de realisation - Google Patents

Agents de liaisonnement dispersibles dans l'eau pour composes cationiques de revetement applicables par electrodeposition, et methode de realisation

Info

Publication number: CA1179443A
Authority: CA; Canada
Prior art keywords: component; acid; binding agent; weight; reaction
Prior art date: 1982-03-31
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

CA000400054A

Other languages

English (en)

Inventor

Horst Diefenbach

Arnold Dobbelstein

Michael Geist

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.)

BASF Farben und Fasern AG

Original Assignee

BASF Farben und Fasern 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.)

1982-03-31

Filing date

1982-03-31

Publication date

1984-12-11

1982-03-31 Application filed by BASF Farben und Fasern AG filed Critical BASF Farben und Fasern AG

1982-03-31 Priority to CA000400054A priority Critical patent/CA1179443A/fr

1984-12-11 Application granted granted Critical

1984-12-11 Publication of CA1179443A publication Critical patent/CA1179443A/fr

Status Expired legal-status Critical Current

Links

239000011230 binding agent Substances 0.000 title claims abstract description 79
238000000034 method Methods 0.000 title claims abstract description 75
125000002091 cationic group Chemical group 0.000 title claims abstract description 16
239000008199 coating composition Substances 0.000 title claims abstract description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 19
238000004519 manufacturing process Methods 0.000 title description 9
239000002253 acid Substances 0.000 claims abstract description 81
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 52
238000006243 chemical reaction Methods 0.000 claims abstract description 50
239000000203 mixture Substances 0.000 claims abstract description 37
229920000647 polyepoxide Polymers 0.000 claims abstract description 30
239000007795 chemical reaction product Substances 0.000 claims abstract description 27
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 27
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 25
238000000576 coating method Methods 0.000 claims abstract description 24
125000003118 aryl group Chemical group 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 20
150000001298 alcohols Chemical class 0.000 claims abstract description 19
125000001931 aliphatic group Chemical group 0.000 claims abstract description 19
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 18
239000000047 product Substances 0.000 claims abstract description 14
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150000003512 tertiary amines Chemical class 0.000 claims abstract description 11
125000002723 alicyclic group Chemical group 0.000 claims abstract description 9
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 claims abstract description 9
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239000003431 cross linking reagent Substances 0.000 claims description 24
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
OREAFAJWWJHCOT-UHFFFAOYSA-N dimethylmalonic acid Chemical group OC(=O)C(C)(C)C(O)=O OREAFAJWWJHCOT-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
229920002647 polyamide Polymers 0.000 claims description 4
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238000004070 electrodeposition Methods 0.000 abstract description 9
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239000006185 dispersion Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 9
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 8
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150000002334 glycols Chemical class 0.000 description 8
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NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
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125000004432 carbon atom Chemical group C* 0.000 description 7
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238000001816 cooling Methods 0.000 description 7
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235000011054 acetic acid Nutrition 0.000 description 6
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229920000642 polymer Polymers 0.000 description 6
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
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239000002981 blocking agent Substances 0.000 description 5
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JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
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KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
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YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 4
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235000010338 boric acid Nutrition 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
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XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
150000004658 ketimines Chemical class 0.000 description 4
238000002156 mixing Methods 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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238000000151 deposition Methods 0.000 description 1
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230000032050 esterification Effects 0.000 description 1
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230000001747 exhibiting effect Effects 0.000 description 1
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238000001914 filtration Methods 0.000 description 1
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239000001530 fumaric acid Substances 0.000 description 1
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GFMIDCCZJUXASS-UHFFFAOYSA-N hexane-1,1,6-triol Chemical compound OCCCCCC(O)O GFMIDCCZJUXASS-UHFFFAOYSA-N 0.000 description 1
OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-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
KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
IQOFOAJECLOAGR-UHFFFAOYSA-N nonane-4,5-diol Chemical compound CCCCC(O)C(O)CCC IQOFOAJECLOAGR-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
OSRKWUXYLYWDOH-UHFFFAOYSA-N phenyl(dipropyl)phosphane Chemical compound CCCP(CCC)C1=CC=CC=C1 OSRKWUXYLYWDOH-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical group 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
239000004632 polycaprolactone Substances 0.000 description 1
229940113115 polyethylene glycol 200 Drugs 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229940057847 polyethylene glycol 600 Drugs 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
229950006800 prenderol Drugs 0.000 description 1
230000037452 priming Effects 0.000 description 1
CZMAXQOXGAWNDO-UHFFFAOYSA-N propane-1,1,2-triol Chemical compound CC(O)C(O)O CZMAXQOXGAWNDO-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000036647 reaction Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920003987 resole Polymers 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
239000007787 solid 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
239000005720 sucrose Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 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
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

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CA000400054A 1982-03-31 1982-03-31 Agents de liaisonnement dispersibles dans l'eau pour composes cationiques de revetement applicables par electrodeposition, et methode de realisation Expired CA1179443A (fr)

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CA000400054A CA1179443A (fr)	1982-03-31	1982-03-31	Agents de liaisonnement dispersibles dans l'eau pour composes cationiques de revetement applicables par electrodeposition, et methode de realisation

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CA000400054A CA1179443A (fr)	1982-03-31	1982-03-31	Agents de liaisonnement dispersibles dans l'eau pour composes cationiques de revetement applicables par electrodeposition, et methode de realisation

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2012122098A1 (fr)	2011-03-06	2012-09-13	King Industries, Inc.	Compositions d'un complexe métal amidine et d'un second composé, compositions de revêtement les comprenant

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- 1982-03-31 CA CA000400054A patent/CA1179443A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2012122098A1 (fr)	2011-03-06	2012-09-13	King Industries, Inc.	Compositions d'un complexe métal amidine et d'un second composé, compositions de revêtement les comprenant

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Date	Code	Title	Description
2001-12-12	MKEC	Expiry (correction)
2002-03-31	MKEX	Expiry

Publication	Publication Date	Title
US4148772A (en)	1979-04-10	Amine acid salt-containing polymers for cationic electrodeposition
KR100211079B1 (ko)	1999-07-15	전착에 사용하기 적합한 양이온 수지 및 캡핑된 폴리이소시아네이트 경화제
CA1266546A (fr)	1990-03-06	Liants solubles a l'eau pour finis d'electrodeposition cationiques, et leur preparation
CA1268283A (fr)	1990-04-24	Bains d'electrodeposition cathodique a faible teneur en matieres organiques volatiles
US4436878A (en)	1984-03-13	Water-dispersible binders for cationic electropaints, and a process for their preparation
US4780524A (en)	1988-10-25	Water-dilutable binders for cationic electrocoating finishes and a process for the preparation thereof
CA1132282A (fr)	1982-09-21	Melanges resineux vulcanisables, par reaction d'addition de michael, utiles pour les revetements
EP0449962B1 (fr)	1996-02-28	Composition d'electrolaquage contenant un additif epoxy auto-condense de polyamine et revetements ainsi produits
EP0059895B1 (fr)	1985-04-17	Liants dispersibles dans l'eau pour électrodéposition cationique et procédé pour leur préparation
AU645277B2 (en)	1994-01-13	Flexible aryl alkyl epoxy resins, their amine resin derivatives and their use in electrodeposition coatings
US5070149A (en)	1991-12-03	Cationic resin composition with reduced emissions during baking
US4239878A (en)	1980-12-16	Process for preparing cationic electrodeposition-coating resin using monofunctional blocking agents and tertiary amines having at least two hydroxy groups
US4724254A (en)	1988-02-09	Water dispersible binders for cationic electra-coating and method for preparation
CA2058936C (fr)	1998-12-29	Procede d'emaillage par electrophorese cathodique; methode pour l'obtention d'un produit d'addition renfermant des groupes urethane
CA1179443A (fr)	1984-12-11	Agents de liaisonnement dispersibles dans l'eau pour composes cationiques de revetement applicables par electrodeposition, et methode de realisation
CA1217896A (fr)	1987-02-10	Agents d'enduction thermodurcissables, et leur emploi
US4624974A (en)	1986-11-25	Water-dispersible binders for cationic electro-dip paints, and method for their production
US5324402A (en)	1994-06-28	Process for coating electrically conductive substrates, water-based coatings and crosslinking agents containing masked NCO groups
US5416137A (en)	1995-05-16	Cathodic electrocoating compositions having improved throw power, containing multifunctional phenols
JP2001152088A (ja)	2001-06-05	カチオン電着塗料組成物
US6689459B1 (en)	2004-02-10	Clear cathodic electrocoating compositions
US5712349A (en)	1998-01-27	Water dispersible binders for cationic electrocoating finishes and a process for their preparation
CA1333438C (fr)	1994-12-06	Resines aminiques issues de resines souples de type arylalkylepoxy et leur utilisation dans les procedes de revetement par electrodeposition
JP4309976B2 (ja)	2009-08-05	電着塗料組成物
CA1335615C (fr)	1995-05-16	Liants dispersibles dans l'eau pour peintures cationiques pour electrolaquage, procede de fabrication et methode de mise en oeuvre sur supports electroconducteurs

CA1179443A - Agents de liaisonnement dispersibles dans l'eau pour composes cationiques de revetement applicables par electrodeposition, et methode de realisation - Google Patents

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