Organic Nitrogen Compound Contains Isocyanate Group Patents (Class 523/415)
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Patent number: 5362773Abstract: Aqueous radiation-curable binder dispersion essentially comprisingA) a radiation-curable binder containing (meth)acrylate groups andB) a radiation-curable emulsifier obtained by reaction of hydroxyalkyl (meth)acrylates, polyglycols, polyhydroxycarboxylic acids and polyisocyanates.Type: GrantFiled: August 26, 1993Date of Patent: November 8, 1994Assignee: Hoechst Aktiengesellschaaft AGInventors: Gerhard Brindoepke, Inge Kurth
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Patent number: 5360839Abstract: Cathodic electrodeposition paints are rendered hardly susceptible to oil droplet-induced craters by incorporating an amine-modified acrylic copolymer of t-butyl (meth)acrylate with a hydroxyl group-containing monomer and an oxirane ring-containing monomer in the form of an aqueous emulsion. The amine-modified acrylic copolymer may be an adduct with a half blocked organic diisocyanate. The paint gives a cured film substantially free from oil droplet-induced craters and having a good adhesion to an overcoating and a good surface smoothness.Type: GrantFiled: April 13, 1993Date of Patent: November 1, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Motoi Tanimoto, Tatsuo Yoshida, Kenshiro Tobinaga, Yuji Toyoda
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Patent number: 5356959Abstract: Epoxy resins obtainable by reactingA) a polyfunctional epoxide, which carries on average 1.5 to 2.5 epoxy groups per molecule and has an epoxide equivalent weight of from 100 to 2000, with based on 1 mol of epoxy groupsB) from 0.1 to 0.5 mol of an alkylphenol, the alkyl groups of which carry from 6 to 20 carbon atoms, andC) from 1 to 100 mmol of a polyoxyalkylenediol obtained from 1,2-propylene oxide, or of a copolymer obtained from 1,2-propylene oxide and other alkylene oxides, which has an average molecular weight of from 200 to 5000 and, on average, from 1 to 4 sulfonic acid groups bonded to methyl groups per molecule, and alsoD) from 0.2 to 0.3 mol of a diol, which isd1) a phenolic diol and/ord2) a polyoxyalkylenediol which has an average molecular weight of from 200 to 5000,with the proviso that the reaction product has an epoxide equivalent weight of from 1000 to 5000, can be converted to pigment resins suitable for electrodeposition coating and pigment pastes can then be prepared from said resins.Type: GrantFiled: July 27, 1993Date of Patent: October 18, 1994Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Klaus Huemke, Christian Sinn
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Patent number: 5356960Abstract: An improved aqueous electrocoating composition that contains an anticrater agent which is a reaction product of poly epoxy hydroxy ether resin, polyoxyalkylene diamine and an amino, glycidyl or isocyanate functional alkyl alkoxy silane having a number average molecular weight of about 1,000-6,000; electrodeposited finishes are formed that have a significant reduction in craters and are smooth and even finishes.Type: GrantFiled: August 11, 1993Date of Patent: October 18, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ding Y. Chung, Allisa Gam
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Patent number: 5352525Abstract: Water-thinnable coating compositions useful in electrocoating compriseA. a mixture ofA.sub.1. 50-95% by weight of one or more oligomeric or polymeric polyaddition or polycondensation compounds which have on average a molecular weight of from 200 to 20,000 and contain per molecule at least two hydroxyl groups and at least two primary and/or secondary amino groups, andA.sub.2. 5-50% by weight of a crosslinker that is reactive toward component A.sub.1, andB. a mixture ofB.sub.1. 90-99.9% by weight of one or more radical-polymerizable compounds which have an average molecular weight of from 100 to 10,000 and contain per molecule at least two olefinic double bonds, andB.sub.2. 0.1-10% by weight of a free radical initiator having a decomposition temperature within the range 50-150.degree. C.,the ratio of mixture A to mixture B being from 10:1 to 1:10 and mixture A being substantially chemically inert toward mixture B.Type: GrantFiled: February 25, 1993Date of Patent: October 4, 1994Assignee: BASF Lacke + Farben AGInventors: Klaus Huemke, Dieter Faul, Ulrich Heimann
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Patent number: 5350636Abstract: A synthetic resin contains, as essential components,A) a crosslinkable binder selected from the group consisting of the polymers, polyadducts or polycondensates having reactive centers in the form of hydroxyl, thio or primary or secondary amino groups andB) a crosslinking agent based on at least one polyoxyalkylene polyisocyanate andC) a crosslinking agent which differs from (B) and is based on.gamma..sub.1) a polyfunctional isocyanate which differs from (B) or.gamma..sub.2) an organic compound which reacts at elevated temperatures with free amino groups of component (A) with amide formation or.gamma..sub.3) an organic compound which reacts at elevated temperatures with hydroxyl groups of component (A) with transesterification or.gamma..sub.4) a phenolic Mannich base ora mixture of two or more crosslinking agents (.gamma..sub.1) to (.gamma..sub.4).Type: GrantFiled: November 20, 1992Date of Patent: September 27, 1994Assignee: BASF Lacke+Farben AktiengesellschaftInventors: Klaus Huemke, Dieter Faul, Gerhard Hoffmann
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Patent number: 5336702Abstract: An aqueous resin dispersion containing as an aqueous resin component a polyurethane-modified epoxy-polyamine resin comprising a reaction product of an epoxy group-containing polyurethane compound obtained by the reaction of a polyhydroxy compound having a number average molecular weight of 50 to 8,000, a polyisocyanate compound, and a compound containing one hydroxyl group and at least one alicyclic epoxy group in a molecule; a bisphenol compound; a bisphenol diglycidyl ether compound; and an active hydrogen-containing amine compound. Said aqueous resin dispersion has excellent corrosion resistance and is suited especially for cathode electro-deposition coating.Type: GrantFiled: December 3, 1992Date of Patent: August 9, 1994Assignee: Kansai Paint Co., Ltd.Inventor: Koji Kamikado
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Patent number: 5331026Abstract: The present invention is directed to a process for producing an aqueous cathodic electrocoating composition comprisingA) mixingi) a powder comprising a dispersion of a pigment in a solid resinii) a principal resiniii) a crosslinker and optionallyiv) an additive selected from the group consisting of organic solvents, catalysts, wetting agents, conditioning agents, thickeners, rheology control agents, antioxidants, surfactants, leveling agents and mixtures thereofB) salting with an acid andC) dispersing in deionized water.Type: GrantFiled: June 11, 1993Date of Patent: July 19, 1994Assignee: BASF CorporationInventors: James W. Benefiel, Peter D. Clark, Laura M. Lanni
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Patent number: 5330839Abstract: A blocked isocyanate group-containing electrocoating composition comprising at least one dialkyltin aromatic carboxylate and at least one bismuth or zirconium compound as a combined curing catalyst. This electrocoating composition gives an electrocoating film superior in corrosion resistance and low-temperature curability and has good bath stability over an extended period.Type: GrantFiled: April 9, 1992Date of Patent: July 19, 1994Assignee: Kansai Paint Co., Ltd.Inventors: Yoshio Yasuoka, Masafumi Kume, Tadayoshi Hiraki, Kiyoshi Kato, Hidehiko Haneishi, Masato Yamamoto
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Patent number: 5330627Abstract: A thermosetting coating composition containingA) one or more binders convertible into liquid or dissolved form at least at the curing temperature and containing acidic groups, basic groups or ionic groups of similar charge,B) one or more binders convertible into liquid or dissolved form at least at the curing temperature and containing basic groups where (A) contains acidic groups, acidic groups where (A) contains basic groups or ionic groups of like charge opposite to the charge of the ionic groups of (A), binder (B) being noninterdiffusible under storage and application conditions, but interdiffusible with binder (A) under hardening conditions, andC) optionally standard solvents, pigments and/or typical paint auxiliaries and/or additives which do not lead to any interdiffusion of the binders A) and B) under storage and application conditions,and a process for the production of coatings by application of the coating composition and subsequent thermal curing.Type: GrantFiled: September 9, 1993Date of Patent: July 19, 1994Assignee: Herberts G.m.b.H.Inventors: Roland Grutter, Reiner Bohmert, Rolf Reinecke
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Patent number: 5322863Abstract: The invention relates to a coating compound which comprises a binder solution containinga) 30 to 70% by weight of a binder,b) 2 to 30% by weight of a crosslinking agent,c) if appropriate, 1 to 7% by weight of neutralization agent,d) 20 to 60% by weight of solvent.Type: GrantFiled: August 7, 1992Date of Patent: June 21, 1994Assignee: BASF Lacke + Farben AktiengesellschaftInventors: Hans-Jurgen Figge, Holger Dartmann
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Patent number: 5320738Abstract: Electrodepositable coating compositions comprising an active hydrogen-containing ionic resin and a curing agent which contains blocked isocyanate groups and oxazolidone groups are disclosed. These coating compositions reduce the tendency of cured electrodeposited films to cause yellowing in subsequently applied topcoat systems. The use of these electrodepositable coating compositions in the process of electrodeposition is also disclosed.Type: GrantFiled: August 2, 1993Date of Patent: June 14, 1994Assignee: PPG Industries, Inc.Inventor: Marvin L. Kaufman
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Patent number: 5314971Abstract: Urethane-modified polyoxyalkylene epoxy resins useful in aqueous dispersions having the general formula ##STR1## where R and R.sup.1 are, independently of one another, ##STR2## wherein R.sup.3 is a C.sub.1-3 alkyl group,R.sup.4 is a C.sub.1-4 alkylenemoiety, ##STR3## each b is, independently of one another, an integer from 0 to 4, and c is 1 to 10;a is 1 to 20, andR.sub.2 is H and at least once the group ##STR4## R.sup.6 is a C.sub.1-5 alkyl group, R.sup.7 is H or CH.sub.3 --,d is 1 to 100,e is 0 or 1,f is 0 or 1, andR.sup.8 is an aliphatic, cyclic, alicyclic, aromatic or araliphatic hydrocarbon group.Type: GrantFiled: August 18, 1993Date of Patent: May 24, 1994Assignee: Witco GmbHInventors: Bernd Neffgen, Wolfgang Scherzer
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Patent number: 5314594Abstract: An improved aqueous electrocoating composition having a binder of an epoxy-amine adduct and a blocked polyisocyanate crosslinking agent; wherein the improvement is the use of an effective amount of an additive of an alkyl thioester or a polymeric product of an epoxy resin, polyalkylene glycol and a sugar to form an electrocoating composition that has significantly improved throwing power and provides a coating that has the necessary properties such as chip, solvent and corrosion resistance.Type: GrantFiled: December 9, 1992Date of Patent: May 24, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ding Y. Chung, Kenneth S. Kirshenbaum
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Patent number: 5308914Abstract: Aqueous dispersions containing a polyurethane and from 5 to 60% by weight, based on the polyurethane, of an adhesion-improving polymer, the polyurethane consisting essentially of(a) organic diisocyanates,(b) dihydroxy compounds which have a molecular weight of from more than 500 to 5,000 g/mol and contain no ionic groups or groups convertible into ionic groups,(c) compounds having one or two functional groups reactive toward isocyanate and at least one ionic group or group convertible into an ionic group and(d) compounds having at last 3 isocyante groups or at least 3 functional groups reactive toward isocyanate,(e) optionally compounds which differ from (c) and have two functional groups reactive toward isocyanate and a molecular weight of from 60 to 500 g/mol, the compounds (d) being used in amounts such that the functionality F of all components is from 2.01 to 2.5, and the polyurethane or a prepolymer thereof is prepared in a water-miscible solvent boiling below 100.degree. C.Type: GrantFiled: November 9, 1992Date of Patent: May 3, 1994Assignee: BASF AktiengesellschaftInventors: Alexander Wallon, Lothar Maempel, Gerhard Auchter, Horst Seibert
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Patent number: 5298538Abstract: Plasticizing resins, aqueous dispersions of cationic resins, and methods of making the same for use in cathodic electrodeposition are disclosed. The resins are formed from reacting a polyoxyalkylenepolyamine, a phenol, and a formaldehyde. The reactants may further include a block building unit derived from a polyepoxide. When used in combination with other conventional electrodepositable resins, deposited films with improved mechanical properties and descreased tendency toward cratering are obtained.Type: GrantFiled: April 11, 1990Date of Patent: March 29, 1994Assignee: BASF CorporationInventors: Klaus Cibura, Yali F. Hallock, John A. Gilbert, John D. McGee
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Patent number: 5288770Abstract: A resin composition for a cationically electrodepositable paint comprising(A) a resin having hydroxyl groups and cationic groups,(B) an epoxy resin having at least 2 epoxy functional groups each of which comprises an epoxy group directly bound to an alicyclic ring and/or bridged alicyclic ring on average per molecule, and(C) a finely divided gelled polymer as principal components, wherein said finely divided gelled polymer is obtained by emulsion polymerizing(C-1) a polymerizable monomer containing at least two radically polymerizable unsaturated groups in the molecule, and(C-2) a radically polymerizable unsaturated monomer other than the one mentioned in (C-1), abovein the presence of a reactive emulsifier containing an allyl group in the molecule.Type: GrantFiled: January 22, 1991Date of Patent: February 22, 1994Assignee: Kansai Paint Co., Ltd.Inventors: Teiji Katayama, Eisaku Nakatani, Haruo Nagaoka, Kenji Yamamoto, Reiziro Nishida
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Patent number: 5283269Abstract: Epoxy resins with urethane groups, containing on average per molecule from 0.5 to 5 groups of the formula I ##STR1## where the substituents R.sup.1 and R.sup.2 are C.sub.1 -C.sub.8 -alkyl groups, which may also be linked together to form five- or six-membered rings, which may contain an oxygen atom, or are each phenyl, are useful in electrocoating.Type: GrantFiled: January 14, 1993Date of Patent: February 1, 1994Assignee: BASF Lacke + Farben AktiengesellschaftInventors: Klaus Huemke, Dirk Lawrenz, Ulrich Heimann
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Patent number: 5281316Abstract: An improved aqueous electrocoating composition having a binder of an epoxy-amine adduct and a blocked polyisocyanate crosslinking agent; wherein the improvement is the use of an effective amount of a blend of a zinc containing compound and a lead pigment to form an electrocoating composition that has significantly improved throwing power and provides a coating that has the necessary properties such as chip, solvent and corrosion resistance.Type: GrantFiled: May 29, 1992Date of Patent: January 25, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ding Y. Chung, Robert J. Sikora, John J. Vincent
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Patent number: 5276072Abstract: Oxazolidone ring-containing epoxy resins (a) produced by the reaction between a diglycidyl ether or ester and an organic diisocyanate are reacted with (b) a first active hydrogen compound such as mono- or diols, mono- or dicarboxylic acids in less than a stoichiometric amount in terms of the active hydrogen atom relative to the epoxy group, and then with (c) a second active hydrogen compound such as amines or sulfide-acid mixtures or polycarboxylic acids in a stoichiometric amount relative to the remaining epoxy group. The resulting hydrophilic modified resin has an oxazolidone ring-containing backbone terminated with an ionizable group. A water-borne paints are formulated from the hydrophilic modified resin by dispersing in an aqueous medium containing a crosslinker and a neutralizing agent.Type: GrantFiled: December 4, 1992Date of Patent: January 4, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Toshiyuki Ishii, Mitsuo Yamada, Motoi Tanimoto, Kenshiro Tobinaga
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Patent number: 5274012Abstract: The invention relates to modified polyoxyalkylene epoxy resins based on polyhydric phenols prepared by the addition of polyethers and/or polyether monourethanes containing isocyanate groups to higher-molecular-weight hydroxyl group-containing polyglycidyl compounds, and to the use of these reaction products in the preparation of stable aqueous dispersions.Type: GrantFiled: November 6, 1992Date of Patent: December 28, 1993Assignee: Witco GmbHInventors: Bernd Neffgen, Wolfgang Scherzer
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Patent number: 5272189Abstract: Electrodepositable coating compositions comprising an active hydrogen-containing ionic resin and a curing agent which contains blocked isocyanate groups and oxazolidone groups are disclosed. These coating compositions reduce the tendency of cured electrodeposited films to cause yellowing in subsequently applied topcoat systems. The use of these electrodepositable coating compositions in the process of electrodeposition is also disclosed.Type: GrantFiled: October 19, 1992Date of Patent: December 21, 1993Assignee: PPG Industries, Inc.Inventor: Marvin L. Kaufman
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Patent number: 5262465Abstract: The invention relates to a cathodic electro-dipcoating process, wherein the electro-dipcoating composition used contains a cationic, amine-modified epoxy resin, which is obtainable by reacting(A) a polyepoxide,(B) an amine and(C) an adduct, which is obtainable by . . . (sic)(c1) a polyether- or polyester-polyol,(c2) a polyisocyanate and(c3) a compound which contains at least one hydrogen atom which is reactive towards isocyanate groups and at least one ketimine group in the molecule, and/or(D) a hydrolysis product of (C)with one another in a relative proportion such that 20 to 90% of the epoxy groups of component (A) are reacted with component (B) and the remaining epoxy groups are reacted with component (C) and/or (D), and--if still necessary--at least partially protonating the reaction product thus obtained.Type: GrantFiled: December 11, 1991Date of Patent: November 16, 1993Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Gunther Ott, Ulrich Heimann, David J. Santure, Udo Reiter
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Patent number: 5227414Abstract: An ambient temperature-curing aqueous urethane-epoxy emulsion coating composition is provided comprising an essentially organic solvent-free emulsion in water of:(a) a urethane oligomer, terminated with primary amine functional groups which are reactive with epoxides, said oligomer being the reaction product of an isocyanate-terminated polyurethane prepolymer and a mono- or polyketimine compound containing one other functional group bearing a single active hydrogen atom which reacts with the isocyanate groups to yield a ketimine-terminated urethane oligomer, said ketimine-terminated urethane oligomer being emulsified into the water by conversion of the ketimine groups into primary amine groups and formation of acid salt of 25-50% of the amine groups by a volatile organic acid; and(b) a polyepoxide in an amount sufficient to provide a ratio of total primary amino group hydrogen atoms to epoxide groups of about 0.9 to 2.Type: GrantFiled: April 29, 1992Date of Patent: July 13, 1993Assignee: Tennant CompanyInventors: G. Dale Ernst, Joseph S. Keute, Alan R. Schuweiler
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Patent number: 5225461Abstract: A coating resin composition comprising, as a main component, an amino group-containing, lactone-modified epoxy resin derivative obtained by subjecting a hydroxyl group-containing epoxy resin having epoxy equivalent of 200-400 and a cyclic ester compound represented by the general formula (I) ##STR1## (R is a hydrogen atom or a methyl group and n is 3-6) to an addition reaction to obtain an addition product and then reacting the addition product with a polyphenol compound and an amino group-containing compound. The resulting product is then reacted with a partially blocked polyisocyanate.Type: GrantFiled: February 7, 1992Date of Patent: July 6, 1993Assignee: Kansai Paint Co., Ltd.Inventors: Koji Kamikado, Haruo Nagaoka
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Patent number: 5221701Abstract: The invention relates to organotin compositions, to a process for their production, and to their use in catalyzing the crosslinking reactions of cationic paint binders crosslinkable by transesterification and/or transurethanization and/or by the reaction of terminal double bonds. The organotin compositions are prepared by dispersion of dibutyltin oxide in a dispersion medium comprising at least one substituted oxazolidine compound and, if appropriate, specially chosen water-tolerant organic solvents. Cationic paints, especially cathodically depositable electrocoating paints, catalyzed by the organotin compositions have very good sedimentation stability in dilute paint batches and show no surface defects in the stoved paint films.Type: GrantFiled: February 12, 1992Date of Patent: June 22, 1993Assignee: Vianova Kunstharz, A.G.Inventors: Willibald Paar, Helmut Honig
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Patent number: 5212216Abstract: A cationic electrodeposition paint composition suitable for a wheel of an automotive vehicle. The paint composition contains an amine-modified epoxy resin and a blocked isocyanate as main components. The paint composition further contains a nonionic emulsified and dispersed type acrylic resin within a range from 6 to 30% by weight in resinous solid content relative to the total resin content of the paint composition, a colloidal silica-containing gelled particulate within a range from 10 to 30 PHR in solid content in paint composition, and an alkyltin ester compound of an aliphatic carboxylic acid within a range from 0.1 to 10 PHR in solid content in the paint composition, thereby improving corrosion resistance of an edge portion of the wheel and a weatherability of a paint film coated on the surface of the steel plate of the wheel.Type: GrantFiled: August 13, 1990Date of Patent: May 18, 1993Assignee: Nissan Motor Co., Ltd.Inventors: Tsutomu Hattori, Hirofumi Masui, Katsuo Iizuka, Satoru Nishigaki, Mitsuyoshi Kitano, Yasuyuki Hirata
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Patent number: 5210154Abstract: The invention relates to water-thinnable baking paints, the use thereof as filler material and intermediate stone chip resistant coat as well as a process for painting motor vehicle bodies.The water-thinnable baking paints comprise as binders a combination of(I) 20 to 70% by weight of a water-thinnable polyurethane resin with an acid value of 15 to 35,(II) 20 to 70% by weight of an epoxy resin-modified water-thinnable polyester which can be prepared by reacting a polyester (A) with a molecular weight (number average) below 2000, an acid value of 35-240 and a hydroxyl value of 56-320, with 0.3 to 1.Type: GrantFiled: December 10, 1990Date of Patent: May 11, 1993Assignee: BASF Lacke + Farben AktiengesellschaftInventors: Klaus Weidemeier, Winfried Schmidt, Hans-Dieter Hille, Bodo Muller
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Patent number: 5187198Abstract: A resin composition for cationically electro-depositable paint comprising (A) a base resin containing a primary hydroxyl group and a cationic group and (B) a crosslinking agent, said crosslinking agent (B) being a product obtained by reacting (B-1) a compound containing in a molecule one hydroxyl group and at least one alicyclic epoxy group with (B-2) a polyisocyanate compound selected from aliphatic, alicyclic and aromatic-aliphatic polyisocyanates such that in principle, a free isocyanate group substantially does not remain.Type: GrantFiled: May 13, 1991Date of Patent: February 16, 1993Assignee: Kansai Paint Co., Ltd.Inventors: Reiziro Nishida, Akira Tominaga
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Patent number: 5185065Abstract: An electrocoating composition containing an epoxy amine adduct which is the reaction product of a polyepoxide resin and an amine, an acrylic amine resin and a blocked polyisocyanate crosslinking agent;wherein the composition is prepared by blending a first emulsion of the epoxy amine adduct and the blocked polyisocyanate crosslinking agent with a second emulsion of the acrylic amine resin and a blocked polyisocyanate crosslinking agent; where the first and second emulsions are each individually formed by blending the adduct or resin with the blocked crosslinking agent and then adding an organic acid to form a salt which forms a stable aqueous emulsion.Type: GrantFiled: August 1, 1991Date of Patent: February 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ding Y. Chung, Allisa Gam, Robert A. Tessmer
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Patent number: 5177125Abstract: A two-phase cathodic electrocoat is obtainable by coating an electrically conducting substrate with a mixture containingA) an aqueous cationic dispersion of a polycondensation or polyaddition product,B) an aqueous cationic dispersion of a polycondensation or polyaddition product having a glass transition temperature of from -80.degree. to 20.degree. C., the polymers of dispersions (A) and (B) being mutually incompatible, and C) optionally a crosslinking agent, a pigment paste, auxiliaries and/or additives, and then baking.Type: GrantFiled: August 14, 1991Date of Patent: January 5, 1993Assignee: BASF Lacke & Farben AktiengeselllschaftInventors: Thomas Schwerzel, Hans Schupp, Klaus Huemke, Ulrich Heimann
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Patent number: 5171765Abstract: This application describes a water dispersible polymeric vehicle comprising epoxy polymers having about 5 to 50 weight percent mesogens or a cross-linkable blend of an amine salt of a mesogenic carboxylic acid, cross-linker resin and an epoxy polymer, the mesogenic acid providing about 5 to 50 weight percent mesogenic groups to the blend.Type: GrantFiled: May 8, 1991Date of Patent: December 15, 1992Assignee: North Dakota State UniversityInventors: Frank N. Jones, Daozhang Wang, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian
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Patent number: 5171764Abstract: A resin composition for cationically electrodepositable paint comprising, as principal components, (A) a resin containing a hydroxyl group and a cationic group, (B) an epoxy resin containing, per molecule, on the average at least 2 epoxy group-containing functional groups with an epoxy group bound to an alicyclic skeleton and/or a bridged alicyclic skeleton, and (C) a finely divided gelled polymer, said finely divided gelled polymer (C) being obtained by, in the first step, emulsion polymerizing (I) a monomer component composed of(a) a polymerizable unsaturated vinylsilane monomer containing a vinylic double bond and a hydrolyzable alkoxysilane group,(b) a polymerizable monomer containing at least two radically polymerizable unsaturated groups in a molecule,(c) a polymerizable unsaturated monomer containing a vinylic double bond and a hydroxyl group, and(d) the other polymerizable unsaturated monomer using a cationic reactive emulsifying agent containing an allyl group in a molecule; and in the second step, eType: GrantFiled: February 19, 1991Date of Patent: December 15, 1992Assignee: Kansai Paint Co., Ltd.Inventors: Teiji Katayama, Eisaku Nakatani, Haruo Nagaoka, Kenji Yamamoto, Reiziro Nishida
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Patent number: 5147905Abstract: Advanced resins and unadvanced epoxy resins are disclosed wherein the unadvanced compound and at least a portion of the advanced epoxy resin contains at least one --O--R.sup.1 --O-- or --(O--CH.sub.2 --CHR.sup.2).sub.n --O-- group as a bridge between two groups selected independently from the group consisting of (1) a saturated or unsaturated cycloaliphatic group, (2) an aromatic group, (3) a group represented by the formula ##STR1## or (4) a group represented by the formula ##STR2## Also disclosed are nucleophilic derivatives thereof, as well as curable compositions and coating compositions containing the advanced or unadvanced epoxy resins or nucleophilic modified advanced or unadvanced epoxy resins. These advanced resins and unadvanced epoxy resins provide coatings with good flexibility or formability as exhibited by good flexural or formable properties determined by reverse impact, T-bend and wedge-bend tests, chip resistance, and with good corrosion resistance and throwpower.Type: GrantFiled: May 1, 1991Date of Patent: September 15, 1992Assignee: The Dow Chemical CompanyInventors: Robert A. Dubois, Duane S. Treybig, Allyson Malzman, Pong S. Sheih, Alan R. Whetten
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Patent number: 5147906Abstract: A cationically electrodepositable resin composition containing as main component primary hydroxyl group-containing cationic resin obtained by reacting epoxy resin (A) having at least three epoxy group-containing functional groups represented by the following structural formula (I) ##STR1## with primary or secondary amine compound (B) containing primary hydroxyl group and optionally, further phenol compound (C) having at least one phenolic hydroxyl group in one molecule, as well as a cationically electrodepositable paint composition containing as main components said cationic resin and curing agent.Type: GrantFiled: July 25, 1991Date of Patent: September 15, 1992Assignee: Kansai Paint Co., Ltd.Inventors: Reiziro Nishida, Akira Tominaga
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Patent number: 5139631Abstract: A cationic electrodeposition coating resin composition composed mainly of(A) a resin containing a primary hydroxyl group and a cationic group, and(B) an epoxy resin which is a copolymer comprising recurring units represented by formula (I) ##STR1## and recurring units represented by formula (II) ##STR2## wherein R denotes a C.sub.3 -C.sub.35 alkyl group, the proportion of the recurring units of formula being 1 to 75% by weight.Type: GrantFiled: December 9, 1991Date of Patent: August 18, 1992Assignee: Kansai Paint Co., Ltd.Inventors: Reiziro Mishida, Akira Tominaga
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Patent number: 5135969Abstract: A composition suitable for use as a coating composition depositable by cationic electrodeposition which has improved edge protection capability containing, in addition to the conventional ingredients used in compositions for cationic electrocoat, such as an aqueous cationic resin, micro-resin particles of a size sufficient to be water dispersible which particles comprise an internally crosslinked polymer of (A) an active hydrogen containing monomer and (B) a monomer containing at least two active double bonds, which polymer further contains a cationic group in sufficient proportion to allow the micro-resin particle to be water dispersed.Type: GrantFiled: January 23, 1990Date of Patent: August 4, 1992Assignee: Shinto Paint Co., Ltd.Inventors: Minoru Tooyama, Akitoshi Shirasaka
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Patent number: 5135970Abstract: The invention relates to the use of crosslinked polymer microparticles having an average particle size of at most 5 .mu.m and a glass transition temperature (Tg) of at least +30.degree. C. in aqueous paint preparations as filler and/or as partial substitute of white pigments, in particular of titanium dioxide.Among other things, the corresponding paints show increased spreading power, less tendency for sedimentation and reduced crater formation.Type: GrantFiled: September 28, 1990Date of Patent: August 4, 1992Assignee: Hoechst AGInventors: Michael Honel, Gerd Walz, Peter Ziegler, Uwe Kubillus
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Patent number: 5132341Abstract: A process for the production of cationic paint binders which are particularly suitable for formulating pigment pastes for cathodically depositable electrocoating paints is described. The paint binders produced according to the invention are modified epoxy resin-amine adducts which contain organically-chemically bonded titanium. The cured paint films provide excellent corrosion protection on non-pretreated sheet steel even in the absence of lead-containing compounds and/or lead pigments.Type: GrantFiled: February 12, 1991Date of Patent: July 21, 1992Assignee: Vianova Kunstharz, A.G.Inventor: Willibald Paar
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Patent number: 5130004Abstract: A pigment paste suitable for use in cationic electrodeposition is disclosed. The pigment paste comprises a cationic resinous grinding vehicle derived from an epoxy resin containing both quaternary ammonium and ternary sulfonium salt groups. Also disclosed are cationic electrodeposition paints containing the pigment paste and the use of these paints in the process of cationic electrodeposition. The paste improves the stability of lead-containing cationic electrodeposition paints.Type: GrantFiled: February 20, 1990Date of Patent: July 14, 1992Assignee: PPG Industries, Inc.Inventors: Mark W. Johnson, Gregory J. McCollum
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Patent number: 5130350Abstract: Cathodic electrocoating binders which are water-dilutable on protonation with an acid are obtainable by reactingA) an epoxy compound or a mixture of epoxy compounds having an epoxide equivalent weight of less than 2,000 withB) a compound which is monofunctional with respect to epoxides and contains aliphatic or phenolic OH groups andC) a secondary amine of 2 to 36 carbon atoms, with the proviso that the reaction product of A), B) and C) still contains free epoxy groups, andD) an amount of an amidoamine containing primary amino groups which is equivalent to or greater than the amount of these free epoxy groups, the said amidoamine being obtainable from a primary diamine and a mono- and/or dicarboxylic acid.Type: GrantFiled: April 8, 1991Date of Patent: July 14, 1992Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Thomas Schwerzel, Hans Schupp, Dirk Lawrenz, Hans Oslowski, Ulrich Heimann
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Patent number: 5128393Abstract: A pigment dispersant useful in cathodic electrocoat compositions is disclosed. The pigment dispersant is the reaction product of an organic monoepoxide or polyepoxide with a primary amine containing an imidazoline moiety. This pigment dispersant allows the maximazation of pigment to binder ratios and the minimization of volatile organic content (VOC) in electrocoat baths.Type: GrantFiled: June 11, 1991Date of Patent: July 7, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Stephen C. Peng, Taddesse Gebregiorgis
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Patent number: 5124447Abstract: The present invention is directed to a one-component polyurethane or polyurea composition which may be cured at either ambient or elevated temperature and is based ona) a liquid blocked polyisocyanate wherein the isocyanate groups have been blocked with a phenolic blocking agent.b) a solid polyamine salt which is insoluble in and dispersed throughout the liquid blocked polyisocyanate, the solid polyamine salt being based on the reaction product of a polyamine with an organic or inorganic acid.The present invention is also directed to a process for the preparation of a high molecular weight polymer by heating the one-component composition at elevated temperature or by adding a polar solvent to the above coating composition and allowing the composition to cure.Type: GrantFiled: July 27, 1990Date of Patent: June 23, 1992Assignee: Miles Inc.Inventors: Edward P. Squiller, Peter H. Markusch
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Patent number: 5120774Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes, the said binders containing latent primary amino groups. In order to prepare the binders, an epoxy resin is reacted with a polyamine, which in addition to a sterically hindered primary amino group also contains at least one primary amino group blocked by reaction with a ketone or aldehyde, and, if appropriate, further primary or secondary amines.Type: GrantFiled: December 21, 1990Date of Patent: June 9, 1992Assignee: BASF Lacke & Farben AGInventors: Michael Geist, Gunther Ott, Georg Schon
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Patent number: 5116914Abstract: An improved aqueous electrocoating composition that contains a catalyst for a curing the components of the electocoating composition of a blocked polyisocyanate and an epoxy amine adduct, wherein the catalyst is alkyl tin diacetyl acetonate, preferably, dibutol tin diacetyl acetonate.Type: GrantFiled: December 18, 1990Date of Patent: May 26, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ding Y. Chung, Tapan K. Debroy
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Patent number: 5114552Abstract: Curable electrocoating compositions and the use of these compositions in a method of electrodeposition are disclosed. The electrocoating compositions comprise an aqueous dispersion of an active hydrogen-containing ionic resin and a capped polyisocyanate in which the polyisocyanate comprises a mixture of a diphenyl-2,4'-diisocyanate, a diphenyl-4,4'-diisocyanate and optionally polyphenyl polyisocyanate in which the diphenyl-2,4'-diisocyanate comprises at least 5 percent by weight of a polyisocyanate mixture. The capped polyisocyanate mixture results in a more stable aqueous dispersion than comparable dispersions prepared with capped polyisocyanates derived from the more common diphenyl-4,4'-diisocyanate and mixtures of diphenyl-4,4'-diisocyanate with polyphenyl polyisocyanate.Type: GrantFiled: February 25, 1986Date of Patent: May 19, 1992Assignee: PPG Industries, Inc.Inventors: Gregory J. McCollum, George W. Mauer
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Patent number: 5108575Abstract: Disclosed herein is a cathodic electrodepositable resin containing polyamine enamine. It has been discovered that reacting epoxy resins with polyamine enamine is a viable method of introducing amine functionality to the epoxy resin. The polyamine enamine route results in the desired high pH and stable dispersion in the electrocoat bath.Type: GrantFiled: August 8, 1990Date of Patent: April 28, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ding Y. Chung, Tapan K. Debroy
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Patent number: 5106469Abstract: A cationic resin suitable for use as a pigment grinding vehicle is disclosed. The cationic resin is derived from an epoxy resin and contains ternary sulfonium groups and alkyl phenoxide groups. Pigment pastes derived from this cationic resin can be used in a method of cationic electrodeposition where they provide for films with high build and good appearance.Type: GrantFiled: November 6, 1989Date of Patent: April 21, 1992Assignee: PPG Industries, Inc.Inventor: Mark W. Johnson
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Patent number: 5101000Abstract: A process for the preparation of water-dilutable binders for cathodically depositable electrodeposition paints wherein 5 to 60 mol % of the epoxy groups of a resinous compound having at least two 1,2-epoxy groups per molecule are reacted with disecondary diamines obtained by the reaction of polypropylene glycol diglycidylethers or polypropylene glycol diacrylates with compounds containing a primary amino group is described. The binders prepared in accordance with the invention are suitable, in particular, for formulating electrodeposition paints, to provide films having a greater layer thickness under normal deposition conditions.Type: GrantFiled: August 21, 1990Date of Patent: March 31, 1992Assignee: Vianova Kunstharz, A.G.Inventors: Willibald Paar, Helmut Honig, Georg Pampouchidis
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Patent number: 5096555Abstract: A heat-curable, cathodically depositable aqueous electrocoating composition contains(A) from 50 to 95% by weight of a polymerization or polycondensation or polyaddition product which has an average molecular weight of from 200 to 20,000 and primary and/or secondary hydroxyl groups and primary, secondary and/or tertiary amino groups and is water-thinnable on protonation with an acid, and(B) from 5 to 50% by weight of a water-thinnable crosslinking agent having cationic groups or groups which are convertible into cationic groups by protonation with an acid.Type: GrantFiled: January 25, 1990Date of Patent: March 17, 1992Assignee: BASF AktiengesellschaftInventors: Hans Schupp, Thomas Schwerzel, Klaus Huemke, Dieter Faul