Organic Nitrogen Compound Is Amine-aldehyde Condensation Product Patents (Class 523/416)
  • Patent number: 4719253
    Abstract: New aqueous dispersible cathodic electrocoat resin compositions containing both secondary amine and 1,3-benzoxazine functionality cure by oxazine self-additon and/or oxazine/amine reactions. Such compositions are prepared in a multi-stage process to give corrosion and chemical resistant coatings which exhibit good package (tank and feed) stability.
    Type: Grant
    Filed: August 1, 1986
    Date of Patent: January 12, 1988
    Assignee: The Glidden Company
    Inventors: Edward T. Turpin, David T. Thrane
  • Patent number: 4713406
    Abstract: Binders for cathodic electrocoating which are based on polyadducts/polycondensates which carry basic nitrogen groups and are rendered water-dilutable by protonation with an acid, and one or more crosslinking agents for these polyadducts/polycondensates, their use and electrocoating baths prepared from them.These binders essentially consist of a mixture of(A) from 50 to 90% by weight of a polyadduct/polycondensate which carries basic nitrogen groups and is obtainable by reacting(a) an essentially epoxide-free adduct of a secondary amine and polyepoxide compound with(b) a condensate of a diamine/polyepoxide adduct which is prepared in the presence of excess diamine and separated off from excess diamine after complete conversion of the epoxide groups, with one or more mono- and/or dicarboxylic acids of not less than 6 carbon atoms.(B) from 10 to 50% by weight of a crosslinking agent which does not react with component (A) at room temperature but reacts with the latter at elevated temperatures with crosslinking.
    Type: Grant
    Filed: November 25, 1986
    Date of Patent: December 15, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Schupp, Rolf Osterloh, Werner Loch, Klaas Ahlers
  • Patent number: 4710561
    Abstract: A resin coating composition comprising an epoxy resin derivative having an imidazoline ring functional group of the formula ##STR1## wherein R.sub.1 represents an alkylene group having 2 to 6 carbon atoms, each of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represents a hydrogen atom or a methyl group, and R.sub.6 represents a residue of a carboxylic acid,as a resin binder. This resin coating composition is useful for cationic electrodeposition coating.
    Type: Grant
    Filed: November 26, 1986
    Date of Patent: December 1, 1987
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Akira Tominaga, Reiziro Nishida
  • Patent number: 4699937
    Abstract: A synthetic resin carrying basic nitrogen groups, its preparation, coating materials prepared from this resin, and a process for cathodic electrocoating.This synthetic resin is obtained by reacting(A) an epoxy resin which(B) a diketimine of a diprimary amineand, if required,(C) with a secondary amine, which may additionally contain a tertiary amino group, with a ketimine of a primary monoamine and/or with a ketimine of a primary/tertiary diamine,a diketimine obtained from(B.sub.1) a ketone and(B.sub.2) a branched aliphatic diprimary diamine of 5 to 9 carbon atoms and/or(B.sub.3) one or more diaminodiamides which are obtained by condensation of 2 moles of diamine (B.sub.2) and 1 mole of a dicarboxylic acidbeing employed as component (B).After protonation with an acid, this synthetic resin is useful as a binder for cathodic electrocoating.
    Type: Grant
    Filed: December 12, 1985
    Date of Patent: October 13, 1987
    Assignee: BASF Farben+Fasern Aktiengesellschaft
    Inventors: Werner Loch, Eberhard Schupp, Rolf Osterloh, Klaas Ahlers
  • Patent number: 4698141
    Abstract: A method for preparing an advanced epoxy cationic resin from an epoxy-based resin containing oxirane groups by converting at least some of the oxirane groups to cationic groups, wherein the improvement is using as the epoxy-based resin an advanced epoxy resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of a polyetherpolyol, such as a condensation product of dipropylene glycol and epichlorohydrin having an epoxy equivalent weight of 185, (2) a diglycidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A and (3) a dihydric phenol such as bisphenol A and optionally a capping agent such as p-nonylphenol.Coating compositions suitable for electrodeposition are prepared from the product obtained by the process.
    Type: Grant
    Filed: July 18, 1986
    Date of Patent: October 6, 1987
    Assignee: The Dow Chemical Company
    Inventors: Kenneth W. Anderson, Richard A. Hickner
  • Patent number: 4686248
    Abstract: The preparation of water-thinnable thermosetting resin binder compositions for coatings is described wherein a polyglycidyl ether prepared by reacting a multifunctional polyglycidyl ether with a monofunctional phenol is reacted with a dicarboxylic acid in the presence of an esterification catalyst.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: August 11, 1987
    Assignee: Shell Oil Company
    Inventors: Jurrianus Bekooij, Petrus G. Kooijmans, Werner T. Raudenbusch, Stephen A. Stachowiak
  • Patent number: 4661541
    Abstract: This application discloses a synthetic resin based on alcohol-modified polyepoxides. The synthetic resin can be prepared by reacting a diepoxide, or a mixture of diepoxides, having an epoxide equivalent weight of less than about 500, with compounds with a hydroxyl group, which is reactive towards epoxide groups, in a molar ratio from about 2:1 to about 7:6 at temperatures from about 100.degree. C. to about 180.degree. C. in an organic solvent free of hydroxyl groups. The synthetic resin has terminal epoxide groups and a mean molecular weight from about 400 to about 5000.
    Type: Grant
    Filed: March 14, 1985
    Date of Patent: April 28, 1987
    Assignee: BASF Farben & Fasern AG
    Inventors: Wolfgang Batzill, Arnold Dobbelstein, Michael Geist, Georg Schon, Gunther Ott
  • Patent number: 4647604
    Abstract: The heat-curable coating agent according to the invention contains a combination of a binder, which possesses basic nitrogen groups and is rendered water-dilutable by protonation with an acid, and a crosslinking agent and, if required, pigments, fillers, corrosion inhibitors, surface coating assistants and catalysts, and the binder used is a reaction product of a dicarboxylic acid or of a dicarboxylate or of a (meth)acrylate oligomer or polymer with an adduct of a di- or triglycidyl ether and a polyamine, the polyamine containing 2 or more amine nitrogen atoms per molecule and one or more alkylene chains of 3 or more carbon atoms between the amino groups, and has an NH amine number of from 50 to 150 mg of KOH/g and is combined with aminoplasts and/or phenoplasts as crosslinking agents.The novel coating agent is useful as a binder for the cathodic electrocoating of metal articles.
    Type: Grant
    Filed: June 13, 1985
    Date of Patent: March 3, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz E. Kempter, Harro Petersen, Eberhard Schupp, Gunther Sabelus, Horst Schmidt
  • Patent number: 4638020
    Abstract: Disclosed herein are aqueous compositions comprising a base-neutralized blend of non-gelled phosphated epoxy and a resin which is non-self dispersible with a base, in water. Coating compositions of these blends are stable and form hydrophobic films of enhanced film properties, particularly in the area of can coatings.
    Type: Grant
    Filed: November 23, 1984
    Date of Patent: January 20, 1987
    Assignee: PPG Industries, Inc.
    Inventors: Roger M. Christenson, Mary E. Rosenberger, Marvin T. Tetenbaum
  • Patent number: 4610769
    Abstract: Aminoplast curable cationic coating compositions are disclosed. The coating compositions contain an onium salt group-containing polymer and an aminoplast curing agent which has at least one group of the structure: ##STR1## wherein R.sub.1 is carbon derived from an aldehyde or a ketone.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: September 9, 1986
    Assignee: PPG Industries, Inc.
    Inventors: Joseph F. Bosso, William J. Geiger
  • Patent number: 4609446
    Abstract: The disclosed invention involves water-dispersible binding agents for cationic electrodeposition coatings and a method for making them, the binding agents are the reaction product of (A) epoxy resins having a molecular weight greater than about 350; (B) polyfunctional, alcohols, carboxylic acids and/or SH-compounds having a molecular weight between about 500-5000 and (C) aminoalcohols with at least one protected primary or tertiary nitrogen atom.
    Type: Grant
    Filed: January 6, 1984
    Date of Patent: September 2, 1986
    Inventors: Michael Geist, Gunther Ott, Georg Schon
  • Patent number: 4609691
    Abstract: The invention relates to water-dispersible binders for cationic electro-dip paints with a base of modified epoxy resins. The binders are produced by reaction of(A) epoxy resins having a molecular weight of at least 350 with(B) elasticized polyphenols having a molecular weight of over 350 with addition to the epoxide groups and further reaction of the reaction product of (A) and (B) with(C) primary and/or secondary amines or ammonium salts to obtain the required water-dispersibility.
    Type: Grant
    Filed: August 31, 1984
    Date of Patent: September 2, 1986
    Assignee: BASF Farben & Fasern AG
    Inventors: Michael Geist, Gunther Ott, Georg Schon
  • Patent number: 4598109
    Abstract: A process of producing a water dispersible epoxy phosphate-solvent mixture is disclosed which comprises heating the solvent with orthophosphoric acid to reaction temperature together with additional water so that the total amount of water is sufficient to hydrolyze at least about 50% of the oxirane functionality in the polyepoxide which is used, slowly adding a resinous polyepoxide to this heated mixture so that reaction with phosphoric acid and hydrolysis of the oxirane groups will occur simultaneously to minimize the concentration of oxirane functionality in the reaction mixture as the reaction proceeds, thus minimizing epoxy-epoxy reactions which tend to increase the molecular weight of the epoxy phosphate which is formed, and then adding volatile amine to destroy any remaining oxirane functionality and to neutralize the epoxy phosphate to provide a water dispersible epoxy phosphate-solvent mixture.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: July 1, 1986
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4596843
    Abstract: A high solids coating composition which comprises 10-96 percent by weight resin solids of a low molecular weight epoxy oligomer, 2-35 percent by weight crosslinking glycoluril-formaldehyde resin and a primary sulfonic acid catalyst. The oligomer is condensed upon heating into a high molecular weight polymer film with simultaneous crosslinking with the crosslinking agent to provide the desired film properties.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: June 24, 1986
    Assignee: Insilco Corporation
    Inventor: Donald G. Wind
  • Patent number: 4594403
    Abstract: Amide-containing epoxy resin/amine adducts are prepared by a process in which an epoxy resin/amine adduct containing primary and/or secondary aminoalkyl groups is reacted with a carboxylic acid in the presence of esterification catalysts, particularly advantageously in the presence of an alcohol.The products prepared according to the invention are useful as binders for cathodic electrocoating.
    Type: Grant
    Filed: June 13, 1985
    Date of Patent: June 10, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz E. Kempter, Gunther Sabelus, Eberhard Schupp, Wolfram Weiss
  • Patent number: 4593078
    Abstract: The present invention is directed to polyglycidyl ethers having, on average, n epoxy groups per molecule, where 1<n.ltoreq.2, which comprise the reaction products of multifunctional polyglycidyl ethers having, on average, x epoxy groups per molecule, where x>2, with (x-n) mol of monofunctional phenols per mol of the multifunctional polyglycidyl ether and to a process for their preparation and their use in preparing thermosetting coating compositions, particularly for use in electrodeposition coating of articles.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: June 3, 1986
    Assignee: Shell Oil Company
    Inventors: Petrus G. Kooymans, Stephen A. Stachowiak, Jurrianus Bekooij, Werner T. Raudenbusch
  • Patent number: 4585814
    Abstract: There is disclosed solution copolymers of monoethylenically unsaturated monomers including a proportion of monoethylenically unsaturated carboxylic acid, with an oxirane-free epoxy acid ester phosphate having adducted onto the oxirane groups of a starting polyepoxide at least 10% thereof of ortho phosphoric acid as well as at least 0.5% by weight of a monoester of a saturated monohydric alcohol with a monoethylenically unsaturated dicarboxylic acid which resists homopolymerization, the remaining oxirane groups of the polyepoxide being esterified with monocarboxylic acid, etherified with monoalcohol or hydrolyzed with water. These copolymers can be neutralized with a volatile amine, especially ammonia and cured with aminoplast or phenoplast resins to provide coatings which cure to greater flexibility and better resistance to blushing on pasteurization exposure.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: April 29, 1986
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4575523
    Abstract: Cathodic electrodepositable resin compositions particularly adapted for use as film forming compositions in cathodic electrodeposition processes. The resin is the reaction product of a modified epoxy formed by reacting a polyepoxide with a water soluble or water miscible polyol, an excess of polyamine, and an aliphatic monoepoxide. The resin, when combined with a cross-linking agent and solubilized in an aqueous electrodeposition bath, is capable of depositing high build coatings in a short period of time with a low cross-linking temperature in a cathodic electrodeposition process. The resin compositions are salted with an acid and used as components of aqueous cathodic electrodeposition baths.
    Type: Grant
    Filed: January 29, 1985
    Date of Patent: March 11, 1986
    Assignee: Inmont Corporation
    Inventors: Terry L. Anderson, Tapan K. Deb Roy, Ding Y. Chung
  • Patent number: 4575524
    Abstract: Cathodic electrodepositable resin compositions particularly adapted for use as film forming compositions in cathodic electrodeposition processes. The resin is the reaction product of a modified epoxy formed by reacting a polyepoxide with a water soluble or water miscible polyol, an excess of polyamine, and a fatty acid. The resin, when combined with a cross-linking agent and solubilized in an aqueous electrodeposition bath, is capable of depositing high build coatings in a short period of time with a low cross-linking temperature in a cathodic electrodeposition process. The resin compositions are salted with an acid and used as components of aqueous cathodic electrodeposition baths.
    Type: Grant
    Filed: January 29, 1985
    Date of Patent: March 11, 1986
    Assignee: Inmont Corporation
    Inventors: Terry L. Anderson, Tapan K. Deb Roy, Ding Y. Chung
  • Patent number: 4568710
    Abstract: The invention relates to cathodically electrodepositable coating compositions comprising an aqueous dispersion of self-crosslinkable resin. The self-crosslinkable resin is amine and epoxide functional and prepared by reacting epoxide resin with fatty amidopolyamine at about room temperature so as to form a partially crosslinked resin, wherein at least about 50 percent of the amine groups have been neutralized with a water soluble acid. The partially crosslinked resin can be deposited from the bath onto a metal substrate and cured at elevated temperatures to form a coating offering excellent corrosion protection and having excellent adhesion to the substrate.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: February 4, 1986
    Assignee: Ford Motor Company
    Inventors: Robert A. Swider, Martha E. Horsch
  • Patent number: 4568709
    Abstract: Cathodically depositable electrodeposition paint binders comprising the reaction product of an epoxy resin with at least two epoxy groups with amines carrying primary amino groups and, optionally, with a carboxylic acid compound to provide an epoxy resin-amino adduct which is then reacted with a phenol and formaldehyde. The binders have excellent corrosion resistance and crosslink to provide coating films at relatively low stoving temperatures without splitting off of substances harmful to the environment.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: February 4, 1986
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Johann Gmoser, Helmut Honig, Wolfgang Daimer
  • Patent number: 4566963
    Abstract: This application discloses water-dispersible binders which are based on modified epoxide/amine adducts and are the reaction products ofA. polyepoxides having an epoxide equivalent greater than 1 and a mean molecular weight M.sub.n of 140 to 5,000 withB. diphenylolalkanoate esters andC. amines.
    Type: Grant
    Filed: February 25, 1985
    Date of Patent: January 28, 1986
    Assignee: BASF Farben + Fasern AG
    Inventors: Gunther Ott, Arnold Dobbelstein, Michael Geist, Georg Schon, Klaas Ahlers
  • Patent number: 4565838
    Abstract: Cathodically depositable electrodeposition paint binders comprising a mixture of (A) 95-50% by weight of the reaction product of an epoxy resin with at least two epoxy groups with amines carrying primary amino groups and, optionally, with a carboxylic acid compound to provide an epoxy resin-amino adduct which is then reacted with a phenol and formaldehyde; and (B) 5-50% by weight of an addition component which is substantially water-insoluble under the conditions of electrodeposition and being compatible with Component A. The presence of Component B in the binder provides increased resistance to corrosion, improvements in the surface quality of the stoved films, and enhanced crosslinking of the binder.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: January 21, 1986
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Wolfgang Daimer
  • Patent number: 4565852
    Abstract: A crosslinkable composition of matter is provided, which comprises first and second chain extended diepoxide resins, one or both of which are prepared using an excess of diepoxide reactant and modified by reaction with hydroxy functional secondary amine. The first resin, diene functional aminoepoxy resin, and the second resin, blocked dieneophile functional aminoepoxy resin, are co-reactive at elevated cure temperature. The diene functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional diene. The blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional blocked dieneophile chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional blocked dieneophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resins.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: January 21, 1986
    Assignee: Ford Motor Company
    Inventor: Saiyed B. A. Qaderi
  • Patent number: 4564648
    Abstract: Dispersion of an epoxy ester graft acrylic in water with a total of no more than 5% of organic volatiles and amines. These dispersions can be used in primer compositions for metal substrates having a minimum of organic solvent emissions and which can crosslink at temperatures from 110.degree.-200.degree. C., giving a good balance of hardness, flexibility, humidity, corrosion resistance and anti-chipping properties.
    Type: Grant
    Filed: September 21, 1984
    Date of Patent: January 14, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Jozef T. Huybrechts, Victor R. Vleminckx
  • Patent number: 4563515
    Abstract: Cationic synthetic resin binders free of epoxy groups for the formulation of electrodeposition paints are described. The binders are the reaction product of an epoxy resin carrying at least two epoxy groups and having an epoxy equivalent of 190 to 1000, with from 0.1 to 1.0 amino groups per available epoxy group of a secondary amine carrying carboxylic acid amide groups. Upon being crosslinked on stoving with a suitable hardening component, the binders have improved water dilutability, permitting a reduction of the degree of neutralization necessary for electrodeposition application and improved intercoat adhesion to addition coats. These improved characteristics are significant with respect to an increase of current yield and in adhering additional coatings of a paint system.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: January 7, 1986
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Rudolf Schipfer, Wolfgang Daimer, Gerhard Schmolzer
  • Patent number: 4560717
    Abstract: Formaldehyde-containing cationic electrodepositable compositions to which are added a formaldehyde scavenger are disclosed. Also disclosed are the use of these compositions in a method of cationic electrodeposition. Free formaldehyde in cationic compositions can lower the pH of the compositions making them more corrosive to the metal parts such as ferrous metal tanks and attending piping and pumps in contact with such compositions. The presence of the formaldehyde scavenger in such compositions stabilizes the pH.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: December 24, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Roger M. Christenson, Joseph T. Valko, Joseph E. Plasynski, Roger L. Scriven
  • Patent number: 4559393
    Abstract: A self-crosslinkable resin and composition of matter comprising same is provided, which resin comprises certain diene functional blocked dieneophile functional aminoepoxy resin, which resin is self-crosslinkable at elevated cure temperature. The diene functional blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant, mono-secondary amine functional blocked dieneophile and, optionally, monofunctional end-capping reactant such as mono-secondary amine functional diene and mono-secondary amine functional blocked dienophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resin. The crosslinkable composition of matter is useful in coating and other applications, especially solvent-based primer coating compositions and cathodic electrocoating compositions.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: December 17, 1985
    Assignee: Ford Motor Company
    Inventor: Joseph W. Holubka
  • Patent number: 4557814
    Abstract: A synthetic resin which carries basic nitrogen groups and can be diluted with water as a result of protonation with an acid can be obtained by reacting an epoxy resin, having a mean molecular weight M.sub.n of from 300 to 6,000 and containing on average from 1.5 to 3.0 epoxide groups per molecule, with a diketimine of a primary diamine and, if appropriate, a secondary amine, which may additionally contain a tertiary amino group, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.These resins are useful as binders for coating agents, in particular for the cathodic electrocoating of electrically conductive substrates.
    Type: Grant
    Filed: July 11, 1984
    Date of Patent: December 10, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Schupp, Werner Loch, Rolf Osterloh, Klaas Ahlers
  • Patent number: 4539347
    Abstract: The instant invention is an epoxy resin curing agent based upon an epoxy novolac containing, on the average, between about 3 and about 7.5 epoxy groups per molecule, in which substantially all of the epoxide groups are reacted with a polyamine wherein each primary amine hydrogen in the resulting reaction product is further reacted with a monoepoxide or a monocarboxylic acid. The resulting epoxy resin curing agent may be used in a water based system for curing epoxide resins. The curing agent is rendered water soluble or water dispersible by salting with a conventional volatile monocarboxylic acid such as acetic, formic or propionic acid.
    Type: Grant
    Filed: September 20, 1984
    Date of Patent: September 3, 1985
    Assignee: Celanese Corporation
    Inventor: William J. DeGooyer
  • Patent number: 4535107
    Abstract: This invention is a method of treating polyester material for use in reinforcing rubber, the method being characterized by treating the polyester material with a treating liquid containing an epoxy compound and a melamine compound and subsequently heat treating the material at 100.degree.-250.degree. C.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: August 13, 1985
    Assignee: Unitika Limited
    Inventor: Shigemitsu Murase
  • Patent number: 4533682
    Abstract: Adducts of imidazolidine compounds, such as the reaction product of ethylene diamine with cyclohexanone, are provided with organic polyepoxides, especially with low molecular weight polyepoxides where the imidazolidine acts as a chain extender, and the adduct is reacted with an acid to protonate at least 50% of the amine groups in the adduct. These protonated adducts can be dispersed in water to form dispersion which cure with various curing agents. Aqueous electrocoating baths can be provided which electrodeposit at the cathode.
    Type: Grant
    Filed: April 29, 1983
    Date of Patent: August 6, 1985
    Assignee: DeSoto, Inc.
    Inventors: Anthony J. Tortorello, Nestor P. Hansen, Kathryn M. Jarocki
  • Patent number: 4515911
    Abstract: The invention relates to cathodically electrodepositable coating compositions comprising an aqueous dispersion of self-crosslinkable resin. The self-crosslinkable resin is amine and epoxide functional and prepared by reacting epoxide resin with polyamine at about room temperature, wherein at least 50 percent of the amine groups have been neutralized with water soluble acid. The polyamine contains at least one primary amine group and at least one tertiary amine group. The partially crosslinked resin product can be deposited on a metal substrate and cured at elevated temperatures to form a coating offering excellent corrosion protection and having excellent adhesion to the substrate.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: May 7, 1985
    Assignee: Ford Motor Company
    Inventors: Robert A. Swider, Martha E. Horsch
  • Patent number: 4501833
    Abstract: Aminoplast curable cationic coating compositions are disclosed. The coating compositions contain an onium salt group-containing polymer and an aminoplast curing agent which has at least one group of the structure: ##STR1## wherein R.sub.1 is carbon derived from an aldehyde or a ketone.
    Type: Grant
    Filed: May 16, 1983
    Date of Patent: February 26, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Joseph F. Bosso, William J. Geiger
  • Patent number: 4480083
    Abstract: Adducts of oxazolidine compounds, such as the reaction product of monoethanol amine with cyclohexanone, are adducted with an organic polyepoxide and the adduct is reacted with an acid to protonate at least 50% of the amine groups in the adduct. These protonated adducts can be dispersed in water to form dispersions which cure with various curing agents. When all the epoxy groups are consumed by reaction with the oxazolidine, aqueous electrocoating baths can be formulated which may contain aminoplast resin or phenoplast curing agents.
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: October 30, 1984
    Assignee: DeSoto, Inc.
    Inventors: Anthony J. Tortorello, Nestor P. Hansen
  • Patent number: 4476260
    Abstract: Zinc rich coatings with improved corrosion resistance are provided by a composition consisting essentially of zinc pigment, thermoplastic polyhydroxyether or thermosetting epoxy resin, an organosilane or its hydrolyzates and optionally aluminum trihydrate, and one or more dispersing agents.
    Type: Grant
    Filed: October 26, 1983
    Date of Patent: October 9, 1984
    Assignee: Union Carbide Corporation
    Inventor: George A. Salensky
  • Patent number: 4476262
    Abstract: A method for reducing extractable constituents of an undesirable monomer in compositions which comprise an ionic polymer and an addition polymer of the undesired monomer which comprises conducting an addition polymerization in the presence of the undesired monomer with another monomer which is copolymerizable therewith and which results in a less undesirable residue or a residue which is more easily removable, is disclosed.
    Type: Grant
    Filed: December 30, 1982
    Date of Patent: October 9, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Shaw C. Chu, Arthur T. Spencer
  • Patent number: 4435529
    Abstract: Novel compositions of matter comprising a reaction product of a tannin and epoxy material are hereby provided. The novel reaction products can be dispersed in an aqueous or solvent medium for use as a treating or coating composition which imparts excellent corrosion resistance to metals and exhibits excellent substrate and intercoat adhesion.
    Type: Grant
    Filed: February 11, 1982
    Date of Patent: March 6, 1984
    Assignee: PPG Industries, Inc.
    Inventors: Alan J. Kaylo, Nicholas T. Castellucci
  • Patent number: 4434256
    Abstract: Paint binders which are water soluble upon neutralization with bases comprising the reaction product of a polyepoxide containing reactive oxirane groups with phosphonic acids containing hydroxyl and/or vinyl groups. The paint binders when stoved at low temperatures have increased chemical resistance.
    Type: Grant
    Filed: August 10, 1982
    Date of Patent: February 28, 1984
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Gert Dworak, Werner Staritzbichler
  • Patent number: 4423166
    Abstract: Ungelled resins, aqueous dispersions of cationic resins, coating compositions, and electrodeposition using the resinous coating compositions are disclosed. The resins are formed from reacting polyepoxides with polyoxyalkylenepolyamines. The aqueous dispersions are prepared by at least partially neutralizing the resins to provide cationic groups and dispersing the cationic resins in aqueous medium. When added to cationic electrodepositable coating compositions, such as high throwpower compositions, the ungelled cationic resins provide better appearing, more flexible and water-resistant electrodeposited coatings.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: December 27, 1983
    Assignee: PPG Industries, Inc.
    Inventors: Thomas C. Moriarity, William J. Geiger
  • Patent number: 4420574
    Abstract: Ungelled resins, aqueous dispersions of cationic resins, coating compositions, and electrodeposition using the resinous coating compositions are disclosed. The resins are formed from reacting polyepoxides with polyoxyalkylenepolyamines. The aqueous dispersions are prepared by at least partially neutralizing the resins to provide cationic groups and dispersing the cationic resins in aqueous medium. When added to cationic electrode-positable coating compositions, such as high throwpower compositions, the ungelled cationic resins provide better appearing, more flexible and water-resistant electrodeposited coatings.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: December 13, 1983
    Assignee: PPG Industries, Inc.
    Inventors: Thomas C. Moriarity, William J. Geiger
  • Patent number: 4419467
    Abstract: An improved process for the preparation of cationic resins derived from polyepoxides is disclosed. Typically, the process comprises contacting the polyepoxide with particular polyether polyols and heating the two together to form a resin which may then be reacted with a cationic base group former such as an amine and acid. Aqueous dispersions of the cationic resins prepared by the improved process are useful for coating applications, particularly cationic electrodeposition. They exhibit good low temperature cure response and the cured coatings have good physical properties such as resistance to water, detergent and salt spray corrosion.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: December 6, 1983
    Assignee: PPG Industries, Inc.
    Inventors: Marco Wismer, Joseph F. Bosso
  • Patent number: 4410645
    Abstract: Sized glass fibers are provided that enables the production of sized glass fibers having improved filamentization. When these sized glass fibers are used for reinforcing polymeric materials the reinforced polymeric materials having good mechanical properties such as tensile strength and compaction without fuzz, fly or static properties of the strands. The reinforced polymeric materials and other improvements of the present invention eminate from the use of an interaction product of an epoxidized polar thermoplastic copolymer and an amino organo silane coupling agent in an aqueous sizing composition that also contains a predominant amount of a cross-linkable film former. The aqueous sizing composition has one or more cross-linkable film formers, one or more organo silane coupling agents and about 2 to about 12 weight percent of an interaction product of an unhydrolyzed or partially hydrolyzed amino organo silane coupling agent and an epoxidized polar thermoplastic copolymer.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: October 18, 1983
    Assignee: PPG Industries, Inc.
    Inventors: Balbhadra Das, L. Dow Moore
  • Patent number: 4397970
    Abstract: The invention is an improved process for preparing epoxy resin/phosphoric acid reaction products having high enough phosphomonoester contents to be water-dispersible (as base salts) and low enough free acid contents to yield water-resistant cured coatings. The phosphoric acid is provided as an acid source material deriveable by the reaction of a hydroxylic P--OH functionality-limiting agent (blocking agent) with phosphoric anhydride as such or as a reaction product thereof with less than six molecular proportions of water. A resin solvent, which may also function as the P--OH blocking agent but otherwise is inert and acceptable as part of the final coating resin formulation, is employed as the reaction medium. The epoxide/acid reaction is allowed to proceed, effectively in the absence of water, until the content in the reaction mixture of species indistinguishable from H.sub.3 PO.sub.4 by base-titration has dropped to a minimum.
    Type: Grant
    Filed: November 13, 1981
    Date of Patent: August 9, 1983
    Assignee: The Dow Chemical Company
    Inventors: Kent D. Campbell, Horst G. Langer, Patrick H. Martin
  • Patent number: 4396732
    Abstract: An amine resin soluble in water with the aid of an acid is produced by reacting a dihydric phenolic compound, such as a bisphenol, with a stoichiometric deficiency of preferably aromatic diepoxide, and then reacting the product containing less than -0.3 part of unreacted dihydric phenolic compound per part of reaction product with at least about 3.25 mol of formaldehyde per mol of said reaction product and with monosecondary amine to produce a Mannich base. This Mannich base is then reacted with additional diepoxide in an amount of from 0.5 to 2 epoxy equivalents per epoxy equivalent in the initially used diepoxide.
    Type: Grant
    Filed: July 13, 1981
    Date of Patent: August 2, 1983
    Assignee: DeSoto, Inc.
    Inventors: Kazys Sekmakas, Raj Shah
  • Patent number: 4396649
    Abstract: Tertiary nitrogen-containing chain-extended epoxy resins, capable of forming stable aqueous emulsions, may be produced by chain-extending an epoxy resin using a tertiary nitrogen containing ether or ester polyol for example, particularly, polycaprolactone which has been polymerization initiated by a tertiary amine polyol such as N-methyl diethanolamine. The corresponding amine salt is formed by treatment with an acid for example acetic acid and the resulting cationic polymer may be dispersed in water to form a cationic emulsion capable of being coated onto a substrate by electrodeposition. The chain extended resins, by virtue by their content of free epoxy groups are also usable for cross-linking and other uses.
    Type: Grant
    Filed: November 20, 1981
    Date of Patent: August 2, 1983
    Assignee: Interox Chemicals Limited
    Inventors: Brian E. Bailey, Joseph W. Lister
  • Patent number: 4379872
    Abstract: Amphoteric amino sulfonate derivatives of epoxy resins having at least one terminal group of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or methyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.20 alkyl or substituted alkyl, and R.sub.4 is C.sub.1 -C.sub.6 alkylene or substituted alkylene, which are reaction products of an epoxy resin having a plurality of terminal groups of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are as defined, with an amino sulfonate of the formula:R.sub.3 --NH--R.sub.4 --SO.sub.3 Mwherein R.sub.3 and R.sub.4 are as defined, and M is a cation.
    Type: Grant
    Filed: August 17, 1981
    Date of Patent: April 12, 1983
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Shin-Ichi Ishikura, Kazunori Kanda, Ryuzo Mizuguchi
  • Patent number: 4374965
    Abstract: Crosslinking compositions comprising (a) reaction product, optionally at least partially neutralized of certain di- or poly epoxy and hydroxy amines and (b) amino resin crosslinkers cure into alkaline resistant coatings that protect against corrosion even in absence of inhibiting pigments such as chromates. The crosslinking compositions may be formulated into a variety of primers including solvent and water base primers that cure within conventional schedules.
    Type: Grant
    Filed: April 10, 1980
    Date of Patent: February 22, 1983
    Assignee: Ford Motor Company
    Inventors: Ray A. Dickie, Joseph W. Holubka
  • Patent number: 4374213
    Abstract: Primers that are aqueous emulsions comprising (a) at least partially neutralized reaction product of di- or poly epoxy compounds and hydroxy amines made in water miscible solvents and (b) amino resin crosslinkers yield, upon curing, alkaline resistant coatings that provide corrosion protection even in absence of inhibiting pigments as chromates.
    Type: Grant
    Filed: April 10, 1980
    Date of Patent: February 15, 1983
    Assignee: Ford Motor Company
    Inventors: Ray A. Dickie, Joseph W. Holubka, S. Burhan A. Qaderi
  • Patent number: RE31616
    Abstract: Described herein is an organic coating composition particularly useful in cathodic electrodeposition comprising a dispersion, solution or suspension of a coating composition characterized by (a) a reaction product of a conjugated fatty acid ester and an acrylic containing monomer, preferably containing oxirane rings; and (b) Formula A within the molecule, being the reaction product of reacting an oxirane ring and an amine; wherein Formula A is:--CH.sub.2 --C(Z)--CH.sub.2 --N.dbd.wherein Z is hydrogen, hydroxyl, alkoxy of 1 to 6 carbon atoms; acyloxy of from 1 to 6 carbon atoms; (.dbd.O, as in a ketone),--OR'].sub.n H; --OR'].sub.n OH, and --OR'(CH.sub.2 OH)].sub.n OH,wherein R' is a saturated alkylene group of from 2 to 4 carbon atoms and n is a number from 1 to 6.Also described is a method of electrodepositing coating compositions containing said adducts onto a cathode.
    Type: Grant
    Filed: January 27, 1982
    Date of Patent: June 26, 1984
    Assignee: Wyandotte Paint Products
    Inventor: Ivan H. Tsou