Organic Nitrogen Compound Contains Isocyanate Group Patents (Class 523/415)
  • Patent number: 5360839
    Abstract: 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: Grant
    Filed: April 13, 1993
    Date of Patent: November 1, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Motoi Tanimoto, Tatsuo Yoshida, Kenshiro Tobinaga, Yuji Toyoda
  • Patent number: 5356959
    Abstract: 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: Grant
    Filed: July 27, 1993
    Date of Patent: October 18, 1994
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Klaus Huemke, Christian Sinn
  • Patent number: 5356960
    Abstract: 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: Grant
    Filed: August 11, 1993
    Date of Patent: October 18, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Allisa Gam
  • Patent number: 5352525
    Abstract: 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: Grant
    Filed: February 25, 1993
    Date of Patent: October 4, 1994
    Assignee: BASF Lacke + Farben AG
    Inventors: Klaus Huemke, Dieter Faul, Ulrich Heimann
  • Patent number: 5350636
    Abstract: 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: Grant
    Filed: November 20, 1992
    Date of Patent: September 27, 1994
    Assignee: BASF Lacke+Farben Aktiengesellschaft
    Inventors: Klaus Huemke, Dieter Faul, Gerhard Hoffmann
  • Patent number: 5336702
    Abstract: 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: Grant
    Filed: December 3, 1992
    Date of Patent: August 9, 1994
    Assignee: Kansai Paint Co., Ltd.
    Inventor: Koji Kamikado
  • Patent number: 5331026
    Abstract: 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: Grant
    Filed: June 11, 1993
    Date of Patent: July 19, 1994
    Assignee: BASF Corporation
    Inventors: James W. Benefiel, Peter D. Clark, Laura M. Lanni
  • Patent number: 5330839
    Abstract: 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: Grant
    Filed: April 9, 1992
    Date of Patent: July 19, 1994
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Yoshio Yasuoka, Masafumi Kume, Tadayoshi Hiraki, Kiyoshi Kato, Hidehiko Haneishi, Masato Yamamoto
  • Patent number: 5330627
    Abstract: 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: Grant
    Filed: September 9, 1993
    Date of Patent: July 19, 1994
    Assignee: Herberts G.m.b.H.
    Inventors: Roland Grutter, Reiner Bohmert, Rolf Reinecke
  • Patent number: 5322863
    Abstract: 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: Grant
    Filed: August 7, 1992
    Date of Patent: June 21, 1994
    Assignee: BASF Lacke + Farben Aktiengesellschaft
    Inventors: Hans-Jurgen Figge, Holger Dartmann
  • Patent number: 5320738
    Abstract: 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: Grant
    Filed: August 2, 1993
    Date of Patent: June 14, 1994
    Assignee: PPG Industries, Inc.
    Inventor: Marvin L. Kaufman
  • Patent number: 5314971
    Abstract: 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: Grant
    Filed: August 18, 1993
    Date of Patent: May 24, 1994
    Assignee: Witco GmbH
    Inventors: Bernd Neffgen, Wolfgang Scherzer
  • Patent number: 5314594
    Abstract: 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: Grant
    Filed: December 9, 1992
    Date of Patent: May 24, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Kenneth S. Kirshenbaum
  • Patent number: 5308914
    Abstract: 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: Grant
    Filed: November 9, 1992
    Date of Patent: May 3, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Alexander Wallon, Lothar Maempel, Gerhard Auchter, Horst Seibert
  • Patent number: 5298538
    Abstract: 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: Grant
    Filed: April 11, 1990
    Date of Patent: March 29, 1994
    Assignee: BASF Corporation
    Inventors: Klaus Cibura, Yali F. Hallock, John A. Gilbert, John D. McGee
  • Patent number: 5288770
    Abstract: 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: Grant
    Filed: January 22, 1991
    Date of Patent: February 22, 1994
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Teiji Katayama, Eisaku Nakatani, Haruo Nagaoka, Kenji Yamamoto, Reiziro Nishida
  • Patent number: 5283269
    Abstract: 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: Grant
    Filed: January 14, 1993
    Date of Patent: February 1, 1994
    Assignee: BASF Lacke + Farben Aktiengesellschaft
    Inventors: Klaus Huemke, Dirk Lawrenz, Ulrich Heimann
  • Patent number: 5281316
    Abstract: 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: Grant
    Filed: May 29, 1992
    Date of Patent: January 25, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Robert J. Sikora, John J. Vincent
  • Patent number: 5276072
    Abstract: 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: Grant
    Filed: December 4, 1992
    Date of Patent: January 4, 1994
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Toshiyuki Ishii, Mitsuo Yamada, Motoi Tanimoto, Kenshiro Tobinaga
  • Patent number: 5274012
    Abstract: 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: Grant
    Filed: November 6, 1992
    Date of Patent: December 28, 1993
    Assignee: Witco GmbH
    Inventors: Bernd Neffgen, Wolfgang Scherzer
  • Patent number: 5272189
    Abstract: 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: Grant
    Filed: October 19, 1992
    Date of Patent: December 21, 1993
    Assignee: PPG Industries, Inc.
    Inventor: Marvin L. Kaufman
  • Patent number: 5262465
    Abstract: 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: Grant
    Filed: December 11, 1991
    Date of Patent: November 16, 1993
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Gunther Ott, Ulrich Heimann, David J. Santure, Udo Reiter
  • Patent number: 5227414
    Abstract: 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: Grant
    Filed: April 29, 1992
    Date of Patent: July 13, 1993
    Assignee: Tennant Company
    Inventors: G. Dale Ernst, Joseph S. Keute, Alan R. Schuweiler
  • Patent number: 5225461
    Abstract: 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: Grant
    Filed: February 7, 1992
    Date of Patent: July 6, 1993
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Koji Kamikado, Haruo Nagaoka
  • Patent number: 5221701
    Abstract: 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: Grant
    Filed: February 12, 1992
    Date of Patent: June 22, 1993
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Helmut Honig
  • Patent number: 5212216
    Abstract: 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: Grant
    Filed: August 13, 1990
    Date of Patent: May 18, 1993
    Assignee: Nissan Motor Co., Ltd.
    Inventors: Tsutomu Hattori, Hirofumi Masui, Katsuo Iizuka, Satoru Nishigaki, Mitsuyoshi Kitano, Yasuyuki Hirata
  • Patent number: 5210154
    Abstract: 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: Grant
    Filed: December 10, 1990
    Date of Patent: May 11, 1993
    Assignee: BASF Lacke + Farben Aktiengesellschaft
    Inventors: Klaus Weidemeier, Winfried Schmidt, Hans-Dieter Hille, Bodo Muller
  • Patent number: 5187198
    Abstract: 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: Grant
    Filed: May 13, 1991
    Date of Patent: February 16, 1993
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Reiziro Nishida, Akira Tominaga
  • Patent number: 5185065
    Abstract: 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: Grant
    Filed: August 1, 1991
    Date of Patent: February 9, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Allisa Gam, Robert A. Tessmer
  • Patent number: 5177125
    Abstract: 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: Grant
    Filed: August 14, 1991
    Date of Patent: January 5, 1993
    Assignee: BASF Lacke & Farben Aktiengeselllschaft
    Inventors: Thomas Schwerzel, Hans Schupp, Klaus Huemke, Ulrich Heimann
  • Patent number: 5171764
    Abstract: 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, e
    Type: Grant
    Filed: February 19, 1991
    Date of Patent: December 15, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Teiji Katayama, Eisaku Nakatani, Haruo Nagaoka, Kenji Yamamoto, Reiziro Nishida
  • Patent number: 5171765
    Abstract: 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: Grant
    Filed: May 8, 1991
    Date of Patent: December 15, 1992
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Daozhang Wang, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian
  • Patent number: 5147905
    Abstract: 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: Grant
    Filed: May 1, 1991
    Date of Patent: September 15, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert A. Dubois, Duane S. Treybig, Allyson Malzman, Pong S. Sheih, Alan R. Whetten
  • Patent number: 5147906
    Abstract: 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: Grant
    Filed: July 25, 1991
    Date of Patent: September 15, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Reiziro Nishida, Akira Tominaga
  • Patent number: 5139631
    Abstract: 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: Grant
    Filed: December 9, 1991
    Date of Patent: August 18, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Reiziro Mishida, Akira Tominaga
  • Patent number: 5135969
    Abstract: 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: Grant
    Filed: January 23, 1990
    Date of Patent: August 4, 1992
    Assignee: Shinto Paint Co., Ltd.
    Inventors: Minoru Tooyama, Akitoshi Shirasaka
  • Patent number: 5135970
    Abstract: 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: Grant
    Filed: September 28, 1990
    Date of Patent: August 4, 1992
    Assignee: Hoechst AG
    Inventors: Michael Honel, Gerd Walz, Peter Ziegler, Uwe Kubillus
  • Patent number: 5132341
    Abstract: 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: Grant
    Filed: February 12, 1991
    Date of Patent: July 21, 1992
    Assignee: Vianova Kunstharz, A.G.
    Inventor: Willibald Paar
  • Patent number: 5130004
    Abstract: 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: Grant
    Filed: February 20, 1990
    Date of Patent: July 14, 1992
    Assignee: PPG Industries, Inc.
    Inventors: Mark W. Johnson, Gregory J. McCollum
  • Patent number: 5130350
    Abstract: 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: Grant
    Filed: April 8, 1991
    Date of Patent: July 14, 1992
    Assignee: BASF Lacke & Farben Aktiengesellschaft
    Inventors: Thomas Schwerzel, Hans Schupp, Dirk Lawrenz, Hans Oslowski, Ulrich Heimann
  • Patent number: 5128393
    Abstract: 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: Grant
    Filed: June 11, 1991
    Date of Patent: July 7, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Stephen C. Peng, Taddesse Gebregiorgis
  • Patent number: 5124447
    Abstract: 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: Grant
    Filed: July 27, 1990
    Date of Patent: June 23, 1992
    Assignee: Miles Inc.
    Inventors: Edward P. Squiller, Peter H. Markusch
  • Patent number: 5120774
    Abstract: 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: Grant
    Filed: December 21, 1990
    Date of Patent: June 9, 1992
    Assignee: BASF Lacke & Farben AG
    Inventors: Michael Geist, Gunther Ott, Georg Schon
  • Patent number: 5116914
    Abstract: 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: Grant
    Filed: December 18, 1990
    Date of Patent: May 26, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Tapan K. Debroy
  • Patent number: 5114552
    Abstract: 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: Grant
    Filed: February 25, 1986
    Date of Patent: May 19, 1992
    Assignee: PPG Industries, Inc.
    Inventors: Gregory J. McCollum, George W. Mauer
  • Patent number: 5108575
    Abstract: 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: Grant
    Filed: August 8, 1990
    Date of Patent: April 28, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ding Y. Chung, Tapan K. Debroy
  • Patent number: 5106469
    Abstract: 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: Grant
    Filed: November 6, 1989
    Date of Patent: April 21, 1992
    Assignee: PPG Industries, Inc.
    Inventor: Mark W. Johnson
  • Patent number: 5101000
    Abstract: 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: Grant
    Filed: August 21, 1990
    Date of Patent: March 31, 1992
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Helmut Honig, Georg Pampouchidis
  • Patent number: 5096555
    Abstract: 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: Grant
    Filed: January 25, 1990
    Date of Patent: March 17, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Schupp, Thomas Schwerzel, Klaus Huemke, Dieter Faul
  • Patent number: 5089101
    Abstract: A cationic electrodeposition coating composition comprising[A] a neutralization product or a quaternary ammonium salt of a comb-shaped copolymer obtained by copolymerizing (a) 3 to 90 parts by weight of an ethylenically unsaturated monomer having a hydrocarbon chain with at least 8 carbon atoms at the molecular ends, (b) 1 to 50 parts by weight of at least one cationic (meth)acrylic monomer selected from the group consisting of aminoalkyl (meth)acrylates, aminoalkyl (meth)acrylamides (meth)acrylates containing a quaternary ammonium salt group and (meth)acrylamides containing a quaternary ammonium salt group, (c) 1 to 60 parts by weight of an alpha,beta-ethylenically unsaturated monomer other than the monomer (b), and (d) 0 to 95 parts by weight of an alpha,beta-ethylenically unsaturated monomer other than the monomers (a), (b) and (c),[B] a cationic epoxy resin capable of being dissolved or dispersed in water, and[C] a pigment.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: February 18, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Hirokazu Hayashi, Tetsuo Aihara, Haruo Nagaoka, Koji Kamikado, Eisaku Nakatani