Organic Nitrogen Compound Is Amine-aldehyde Condensation Product Patents (Class 523/416)
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Patent number: 5272187Abstract: A water-dilutable coating comprising a binder obtained from an epoxide resin-modified polyester possessing free carboxyl groups prepared from the reaction of:A) a polyester polymerized from:a.sub.1) a polycarboxylic acid containing at least three carboxyl groups and/ora.sub.2) a polyol containing at least one carboxyl group anda.sub.3) a polycarboxylic acid containing two carboxyl groups anda.sub.4) a polyol, wherein the polyester contains (cyclo)aliphatic elements having at least six carbon atoms;B) from 0.3-1.5 equivalents per polyester molecule of a bisphenol epoxide resin or a reaction product thereof containing at least one epoxide group per molecule with a carboxylic acid; andC) a crosslinking agent.Type: GrantFiled: October 21, 1992Date of Patent: December 21, 1993Assignee: BASF Lacke & Farben AGInventors: Lutz-Werner Gross, Ulrich Poth, Dieter Hille, Klaus Weidemeier
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Patent number: 5266611Abstract: An aqueous structural adhesive bonding primer composition containing a water-dispersible, modified phenoxy resin, an amine-aldehyde resin and a catalyst for reaction between the resins. The primer may contain corrosion inhibitors, including a novel chromate-free inhibitor system.Type: GrantFiled: July 21, 1992Date of Patent: November 30, 1993Assignee: The Dexter CorporationInventor: Andrew F. Teschendorf
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Patent number: 5219914Abstract: A washout resistant roof mastic is disclosed in which an emulsion is applied and contacted with a second material that causes the emulsion to flocculate and set quickly. The emulsion can be applied for example through an applicator that simultaneously applies the emulsion and the flocculant.Type: GrantFiled: December 27, 1989Date of Patent: June 15, 1993Assignee: Rohm and Haas CompanyInventor: Charles E. Warburton, Jr.
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Patent number: 5183835Abstract: A water-dilutable coating comprising a binder obtained from an epoxide resin-modified polyester possessing free carboxyl groups prepared from the reaction of:A) a polyester polymerized from:a.sub.1) a polycarboxylic acid containing at least three carboxyl groups and/ora.sub.2) a polyol containing at least one carboxyl group anda.sub.3) a polycarboxylic acid containing two carboxyl groups anda.sub.4) a polyol; wherein the polyester contains (cyclo)aliphatic elements having at least six carbon atoms; andB) from 0.3-1.5 equivalents per polyester molecule of a bisphenol epoxide resin or a reaction product thereof containing at least one epoxide group per molecule with a carboxylic acid.Type: GrantFiled: November 21, 1990Date of Patent: February 2, 1993Assignee: BASF Lacke & Farben AGInventors: Lutz-Werner Gross, Ulrich Poth, Dieter Hille, Klaus Weidemeier
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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: 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: 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: 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: 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: 5093392Abstract: An epoxy-acrylic graft copolymer useful as a paint film is prepared by the in-situ copolymerization of ethylenically unsaturated monomers including between 1% and 25% by weight of alkylated alkylol acrylamide monomer in the presence of at least 3% by weight of peroxide initiator in the absence of water. The unsaturated monomer chains are grafted by carbon-to-carbon grafts to the epoxy resin backbone. The resulting epoxy-acrylic graft copolymer is dispersed into water by adding amine, and is blended with from 1 to 40 parts by weight of aminoplast per 100 parts by weight of copolymer.Type: GrantFiled: May 8, 1991Date of Patent: March 3, 1992Assignee: The Glidden CompanyInventors: James T. K. Woo, Richard M. Marcinko
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Patent number: 5086090Abstract: The invention relates to a process for the preparation of aqueous dispersions to be further processed to electrocoating paints with baking temperatures below 160.degree. C. and baking times.ltoreq.30 minutes, which dispersions contain modified epoxide-amine adducts as binders and polyisocyanates blocked by hydroxyl groups as cross-linking agents.In this process polyepoxides and compounds containing one or more, preferably 2, hydroxyl groups per molecule are reacted at elevated temperatures in the presence of catalysts to furnish epoxide-containing intermediates.A solvent or a mixture of solvents is then added with external cooling ahd the solution is boiled under reflux, if necessary in vacuo, until the temperature of the solution drops to 95.degree. C. to 20.degree. C.Type: GrantFiled: June 13, 1990Date of Patent: February 4, 1992Assignee: BASF Lacke & Farben AGInventors: Michael Geist, Klaus Cibura, Walter Jouck, Gunther Ott, Jurgen Sadlowski, Manfred Dangschaft, Manfred Reimann
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Patent number: 5086092Abstract: Heat-curable aqueous coating agents for cathodic electrocoating contain(A) an amino-containing polymerization, polycondensation or polyaddition product as a binder which becomes water-dilutable on protonation with an acid,(B) a crosslinking agent and(C) from 0.05 to 10% by weight, based on components (A) and (B), of a monomeric organic complexing agent.Type: GrantFiled: April 12, 1991Date of Patent: February 4, 1992Assignee: BASF Lacke+Farben AktiengesellschaftInventors: Hans Schupp, Thomas Schwerzel, Dirk Lawrenz, Hans-Josef Oslowski, Ulrich Heimann
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Patent number: 5086091Abstract: The invention relates to cathodic water-dilutable binders which contain primary amino groups neutralized with acids and introduced via ketimine groups. The binders have been prepared by reacting(A) a synthetic resin containing epoxy groups with(B) at least one compound which, in addition to a mercapto group which is reactive toward epoxy groups, also possesses at least one ketimine group, and, if required,(C) other modifying compounds, such as, for example, monocarboxylic acids and/or other primary and/or secondary amines,and have then been neutralized with an acid.Type: GrantFiled: November 20, 1989Date of Patent: February 4, 1992Assignee: BASF Lacke & Farben AGInventors: Michael Geist, Klaus Cibura, Helmut Fobbe, Gunther Ott
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Patent number: 5076900Abstract: A low cure cathodic electrodepositable resin is disclosed. The backbone of the resin is a polyepoxide amine adduct having primary or secondary hydroxyl groups which is crosslinked with aminoplast resins and catalyzed by metal catalysts. The resin is capable of curing in a basic environment at a temperature below 150.degree. C. The resin can be salted with an acid and can be dissolved or dispersed in water. The aqueous dispersions can then be formulated into electrocoat primer coatings for metal objects.Type: GrantFiled: May 31, 1990Date of Patent: December 31, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Willem B. van der Linde, Edward Chu
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Patent number: 5064880Abstract: 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 is improved by using as the epoxy-based resin a blend of (I) an epoxy-based resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which diol is essentially free of ether oxygen atoms, such as a condensation product of 1,4-butanediol and epichlorohydrin, optionally (2) a diglycidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A, (3) a dihydric phenol such as bisphenol A, and optionally (4) a capping agent such as p-nonylphenol and (II) a different cationic epoxy-based resin. Such resin blends can be utilized in cathodic electrodeposition coating systems.Type: GrantFiled: September 8, 1989Date of Patent: November 12, 1991Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 5057556Abstract: A non-gelled amine-epoxide reaction product and acid addition salts thereof where the product is obtained by co-reacting;a) a secondary amine NHR.sup.1 R.sup.2, wherein R.sup.1 and R.sup.2 the same or different are C.sub.2 or C.sub.3 hydroxyalkyl groups,b) a polyepoxide,c) optionally a polyoxyalkylene polyamine,d) a product of the reaction between an epoxide with at least two epoxy groups and which contains less than 40% by weight of aromatic groups, and an amine of formula (1):NR.sup.3 R.sup.4 (CH.sub.2)n NH.sub.2 (1)in which n is from 2 to 6, and where R.sup.3 and R.sup.4, the same or different are methyl or ethyl, and optionally,e) a monoepoxidethe components of product (D) being chosen so that the non-gelled amine epxoide reaction product is a liquid at temperature above -5.degree. C.Type: GrantFiled: October 23, 1989Date of Patent: October 15, 1991Assignee: Imperial Chemical Industries PLCInventor: Richard P. Redman
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Patent number: 5039721Abstract: 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: July 21, 1989Date of Patent: August 13, 1991Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Thomas Schwerzel, Hans Schupp, Dirk Lawrenz, Hans Oslowski, Ulrich Heimann
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Patent number: 5021470Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.Type: GrantFiled: March 23, 1989Date of Patent: June 4, 1991Assignee: BASF CorporationInventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
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Patent number: 5019606Abstract: Aqueous solutions of polyamidoamine-epichlorohydrin resins and preparation and use thereof.A stable aqueous resin solution having a pH of not more than 7 and containing as the resin a water-thinnable polyamidoamine-epichlorohydrin resin (A) obtained by reaction of a water-thinnable basic polyamidoamine (B) comprising an acid component (B.sub.1) and an amine component (B.sub.2) with epichlorohydrin (C), the level of organically bound chlorine in the resin (A) being not more than 4% by weight.The present invention further relates to a process for preparing these products and to the use thereof in particular for increasing the wet strength of paper.Type: GrantFiled: June 30, 1989Date of Patent: May 28, 1991Assignee: Hoechst AGInventors: Manfred Marten, Walter Kamutzki
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Patent number: 5008351Abstract: Self-crosslinking cationic paint binders based on ureide-modified epoxy resins; the preparation of these binders and their use, particularly in electrodeposition paints, is described. The modification is effected with carboxylic compounds carrying ureide groups, blocked isocyanate groups and, optionally, tertiary amino groups. The carboxylic compounds are obtained through reaction of dicarboxylic acid anhydrides or compounds carrying dicarboxylic acid anhydrides with a substituted urea or a substituted biuret. The products show excellent resistance and adhesion characteristics.Type: GrantFiled: May 15, 1989Date of Patent: April 16, 1991Assignee: Vianova Kunstharz, A.G.Inventor: Willibald Paar
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Patent number: 4980397Abstract: A method for preparing an advanced epoxy cationic resin from an opoxy-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 an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (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 electro-deposition are prepared from the product obtained by the process.Type: GrantFiled: July 6, 1989Date of Patent: December 25, 1990Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 4980429Abstract: A low cure cathodic electrodepositable resin is disclosed. The backbone of the resin is a polyepoxide amine adduct which is crosslinked with aminoplast resins and catalyzed by metal catalysts. The resin is capable of curing in a basic environment at a temperature below 150.degree. C. The resin can be salted with an acid and can be dissolved or dispersed in water. The aqueous dispersions can then be formulated into electrocoat primer coatings for metal objects.Type: GrantFiled: January 26, 1990Date of Patent: December 25, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Edward Chu
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Patent number: 4980399Abstract: 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: February 5, 1990Date of Patent: December 25, 1990Assignee: BASF Lacke & Farben AGInventors: Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4977202Abstract: 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 an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (2) a digylcidylether 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: GrantFiled: July 6, 1989Date of Patent: December 11, 1990Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 4943359Abstract: Aqueous, heat-curable coating material, containing as vehicle 85 to 40 weight percent of a mixture of a fatty acid-free, acidic epoxide resin phosphate ester with an acid number of 10 to 150, prepared from an epoxide group-containing polyglycidyl ether and/or a polyglycidyl methacrylate resin with more than 1.3 epoxide groups per molecule and an epoxide equivalent weight of 180 to 5,000 and a phenolic resin-modified, carboxyl group-containing, oil-free polyester with an acid number of 15 to 175 and an OH number of 15 to 175, 0 to 25 weight percent of an epoxide resin graft copolymer with an acid number of 30 to 200, prepared from an epoxide group-free reaction product of fatty acid-free polyglycidyl ethers with more than 1.3 epoxide groups per molecule and an epoxide equivalent weight of 1,000 to 5,000 with .alpha.,.beta.Type: GrantFiled: April 6, 1988Date of Patent: July 24, 1990Assignee: Herberts Gesellschaft mit beschrankter HaftungInventors: Hans-Peter Patzschke, Albrecht Luttenberg, Hans-Jurgen Schlinsog, Wolfgang Bogdan
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Patent number: 4933379Abstract: A process is disclosed for preparing an aqueous paint composition including the steps of(a) mixing a pigment powder having a particle size less than about 20 micrometers, a cross-linking agent and an epoxy resin to form a liquid, solvent-free paste;(b) reacting the resultant paste with a secondary amine to provide at least one N-H function per epoxy group of the epoxy resin; and(c) neutralizing the resulting suspension of particles coated with an epoxy-amine adduct and a cross-linking agent.Also provided is a coating process employing the invention aqueous paint composition containing a transesterification-promoting metal compound.Type: GrantFiled: September 15, 1988Date of Patent: June 12, 1990Assignee: Shell Oil CompanyInventors: Henricus P. H. Scholten, Tette J. Dijkstra, Roeland Van Iperen
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Patent number: 4931157Abstract: An ungelled reaction product of a polyepoxide and an active hydrogen-containing material containing at least two active hydrogens per molecule is disclosed. The active hydrogen-containing material being a hydroxyalkyl-substituted urethane in which the hydroxy group is in the beta position to the urethane group. The reaction product is useful as a precursor in making cationic resins for use in cationic electrodeposition.Type: GrantFiled: February 18, 1988Date of Patent: June 5, 1990Assignee: PPG Industries, Inc.Inventors: Joseph T. Valko, Joseph E. Plasynski, Robert D. Miller
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Patent number: 4920175Abstract: Promotors for a crosslinking reaction involved in the curing of a system comprising crosslinkable polymers are bound to polymeric microparticles having a diameter of about 0.01 to 6 microns prepared by polymerizing a mixture of ethylenically unsaturated monomers. The microparticles carrying the crosslinking reaction promotor may be incorporated to coating compositions, printing inks, sealants, adhesives and other polymeric products in place of conventional crosslinking reaction promotors.Type: GrantFiled: July 28, 1988Date of Patent: April 24, 1990Assignee: Nippon Paint Co., Ltd.Inventors: Kazunori Kanda, Shinichi Ishikura, Keizou Ishii, Akio Kashihara
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Patent number: 4883572Abstract: 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 is improved by using as the epoxy-based resin a blend of (I) an epoxy-based resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which diol is essentially free of ether oxygen atoms, such as a condensation product of 1,4-butanediol and epichlorohydrin, optionally (2) a diglycidylether of a diphenol, or example a diglycidyl ether of disphenol A, (3) a diphenol such as bisphenol A, and optionally (4) a capping agent such as p-nonylphenol and (II) a different cationic opoxy-based resin. Such resin blends can be utilized in cathodic electrodeposition coating systems.Type: GrantFiled: July 2, 1987Date of Patent: November 28, 1989Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 4868230Abstract: 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 an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (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: GrantFiled: July 2, 1987Date of Patent: September 19, 1989Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 4857567Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.Type: GrantFiled: July 24, 1987Date of Patent: August 15, 1989Assignee: BASF Corporation, Inmont DivisionInventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
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Patent number: 4851460Abstract: An aqueous coating composition is described, containing, as binder, a mixture of (A) 50 to 95% by weight of a reaction product of a carboxy functional polycondensate containing epoxy groups, at least one copolymerisable o,-olefinically unsaturated monomer and conventional auxiliary agents, and (B) 50 to 5% by weight of a polyurethane dispersion, optionally together with a grinding resin. The process for the preparation of the aqueous coating compound and its use for the formation of coatings are also described.Type: GrantFiled: August 18, 1987Date of Patent: July 25, 1989Assignee: Herberts Gesellschaft mit Beschrankter HaftungInventors: Dieter Stranghoner, Hans-Peter Patzschke, Christa Luhmann
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Patent number: 4851459Abstract: High performance polymer systems based on water dispersed polyurethanes obtained from the reaction of NCO terminated prepolymers with a peroxide compound containing at least one active hydrogen atom, methods of making such polymer systems and their use as hydrolytically stable flexible substrate bonding agents are disclosed. Flexible packages, e.g., retortable laminate pouches, are formed by bonding together sections of films, foils or like flexible substrates using such adhesives.Type: GrantFiled: October 17, 1988Date of Patent: July 25, 1989Assignee: Century Adhesives Corp.Inventor: Balasubramaniam Ramalingam
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Self-crosslinking cationic paint binders based on ureide-modified epoxy resins and their preparation
Patent number: 4851486Abstract: Self-crosslinking cationic paint binders based on ureide-modified epoxy resins; the preparation of these binders and their use, particularly in electrodeposition paints, is described. The modification is effected with carboxylic compounds carrying ureide groups, blocked isocyanate groups and, optionally, tertiary amino groups. The carboxylic compounds are obtained through reaction of dicarboxylic acid anhydrides or compounds carrying dicarboxylic acid anhydrides with a substituted urea or a substituted biuret. The products show excellent resistance and adhesion characteristics.Type: GrantFiled: May 18, 1988Date of Patent: July 25, 1989Assignee: Vianova Kunstharz, A.G.Inventor: Willibald Paar -
Patent number: 4847314Abstract: A process of producing a room temperature-stable solvent solution from a high molecular weight crystalline ethylene glycol terephthalate solid polyester is disclosed in which the polyester is incorporated into a hot melt of an hydroxy-functional linear polyester having an hydroxy number of at least about 20, an acid number of less than about 30 and a molecular weight in the range of 1,000 to 10,000. This forms a molten mixture containing from about 20% to about 55% of terephthalate polyester which is maintained as a hot melt until a sample of the melt forms a clear to slightly cloudy solution in a 50% mixture thereof with 2-ethoxy diethanol glycol acetate. The reacted hot melt is then mixed with an organic solvent to form a solution which is useful in thermosetting solvent solution coating compositions.Type: GrantFiled: May 11, 1988Date of Patent: July 11, 1989Assignee: DeSoto, Inc.Inventors: Anthony J. Tortorello, Helene Gong
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Patent number: 4829105Abstract: An anodic electrodeposition composition containing a water-soluble or water-dispersible modified epoxy resin derived from an epoxy resin having two epoxide groups and at least one alcoholic hydroxy group at the terminals and the middle of the resin backbone, respectively. The modified epoxy resin has at least one polymeric side chain block bound to said alcoholic hydroxy group and at least one acid group derived from said terminal epoxide group.Type: GrantFiled: January 28, 1988Date of Patent: May 9, 1989Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kazunori Kanda, Shinsuke Shirakawa, Hirotoshi Umemoto, Ryuzo Mizuguchi
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Patent number: 4824927Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.Type: GrantFiled: January 23, 1987Date of Patent: April 25, 1989Assignee: BASF Lacke & Farben AKTInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4816300Abstract: The invention provides a process for the preparation of water-reducible carboxylated amide binders comprising the steps of:(1) reacting:(a) a substantially epoxy-free compound of general formula ##STR1## wherein A is the organic residue of a ring opening reaction of a vicinal epoxy group of a polyepoxide with ammonia or amine having at least two amino hydrogens, R.sup.1, R.sup.3 and R.sup.4 each is hydrogen or a C.sub.1-6 alkyl group, with the proviso that at least one of R.sup.1, R.sup.3 and R.sup.4 is hydrogen, R.sup.2 is a C.sub.2-12 alkylene group, x is 0 or 1 and y is a number from 0 to 4, with(b) a carboxyl group-containing mono- or polyester compound derived from a di- or polycarboxylic acid and a polyhydric alcohol having at least one glycol group per molecule, with the proviso that only one carboxyl group per molecule or di- or polycarboxylic acid has been esterified and the or each ester group is a .beta.-hydroxyester group,at a temperature in the range of from 80.degree. to 160.degree. C.Type: GrantFiled: January 15, 1988Date of Patent: March 28, 1989Assignee: Shell Oil CompanyInventors: Petrus G. Kooijmans, Roeland Van Iperen, Arjan Sikking
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Patent number: 4812215Abstract: An aqueous, cationically electrodepositable coating composition contains a ternary sulfonium or quaternary phosphonium group containing resin, an aminoplast or phenoplast crosslinking agent and a catalytic amount of a non-ionic ester of a sulfonic acid as latent acid catalyst to catalyze the reaction between the sulfonium or phosphonium group containing resin and the aminoplast crosslinking agent.Type: GrantFiled: August 12, 1988Date of Patent: March 14, 1989Assignee: PPG Industries, Inc.Inventors: Richard F. Karabin, Ken W. Niederst, Michael G. Sandala, Edward R. Coleridge
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Patent number: 4812493Abstract: A two component water-based composition which cures in two stages, an initial rapid curing stage and a slower curing stage, comprising as the first component, a mixture of a polyaldehyde chosen from the group consisting of glyoxal glutaraldehyde and derivatives of glyoxal and gluteraldehyde, and a water dispersible component chosen from the group consisting of poxy resin emulsions which can be emulsified in water, synthetic latexes stable at about pH 7 or less, low molecular weight resin emulsions, epoxy ester emulsions, water emulsified alkyds, and cationic, anionic and non-ionic asphalt emulsions and, as the second component, the non-gel reaction product of N,N'-bis(methoxymethyl) uron and a polyamine chosen from a group consisting of primary and secondary amines and/or a monoamine.Type: GrantFiled: April 10, 1987Date of Patent: March 14, 1989Assignee: Adhesive Coatings Co.Inventor: Lowell O. Cummings
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Patent number: 4810535Abstract: Disclosed herein are glycidol-modified polyepoxide-polyoxyalkylene polyamine adducts for use as additives in coatings to provide improved coating appearance.Type: GrantFiled: February 1, 1988Date of Patent: March 7, 1989Assignee: PPG Industries, Inc.Inventors: Gregory J. McCollum, Robert R. Zwack
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Patent number: 4801628Abstract: A non-water dispersible, oxirane-defunctionalized, etherified, phosphoric acid ester of an epoxy resin is useful in enhancing the adhesion of aqueous thermosetting coating compositions useful as a varnish or white coating for drawn and ironed aluminum containers. The epoxy resin ester is prepared by reacting(a) an epoxy resin having an epoxy equivalent weight of at least about 190;(b) orthophosphoric acid in an amount of 0.2 to 0.45 equivalents per equivalent of epoxy resin;(c) at least about 0.65 equivalents, per equivalent of epoxy resin, of a reactive hydroxyl-functional compound having at least one hydroxyl group reactive with an oxirane group of said epoxy resin, said hydroxyl-functional compound being a solvent for said epoxy resin and for the non water-dispersible, defunctionalized, etherified, phsophoric acid epoxy resin ester reaction product; and(d) water in an amount of 0-20% of the weight of the orthophosphoric acid.Type: GrantFiled: November 20, 1987Date of Patent: January 31, 1989Assignee: BASF Corporation, Coatings and Inks DivisionInventors: Deanna Ashing, Stanley Hiltenbeitel, Youssef Moussa, Patrick F. Aluotto
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Patent number: 4789696Abstract: Cationic paint binders, particularly binders of the type used in cathodic electrodeposition coatings which crosslink through transesterification, transamidation, transurethanization, or through the reaction of chain end double bonds catalyzed with a condensation product of a dialkyltinoxide and a compound carrying at least one hydroxyl group are described. The hydroxyl compounds are the aliphatic alcohols, phenols, alkanolamines, or the reaction products of primary amines with monoepoxy compounds. The catalysts of the invention provide very good stability and good compatibility in aqueous cationic paint materials.Type: GrantFiled: September 21, 1987Date of Patent: December 6, 1988Assignee: Vianova Kunstharz, A.G.Inventors: Willibald Paar, Johann Gmoser
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Patent number: 4777225Abstract: A process for producing self-crosslinking paint binders, water-soluble on protonation, based on the reaction product of aminoalkylation product carrying blocked isocyanate groups, NH-functional compounds, particularly of adducts of primary amines to diepoxy resins, and formaldehyde is described. The products produced according to the process are particularly suited for the formulation of high quality electrodeposition paints.Type: GrantFiled: November 9, 1987Date of Patent: October 11, 1988Assignee: Vianova Kunstharz, A.G.Inventor: Willibald Paar
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Patent number: 4777213Abstract: Promoters for a crosslinking reaction involved in the curing of a system comprising crosslinkable polymers are bound to polymeric microparticles having a diameter of about 0.01 to 6 microns prepared by polymerizing a mixture of ethylenically unsaturated monomers. The microparticles carrying the crosslinking reaction promoter may be incorporated to coating compositions, printing inks, sealants, adhesives and other polymeric products in place of conventional crosslinking reaction promoters.Type: GrantFiled: March 2, 1987Date of Patent: October 11, 1988Assignee: Nippon Paint Co., Ltd.Inventors: Kazunori Kanda, Shinichi Ishikura, Keizou Ishii, Akio Kashihara
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Patent number: 4752631Abstract: 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 crosslinkng agents for these polyadducts/polycondensates, and their use.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 adduct of a secondary amine and a polyepoxide compound, the adduct still containing free epoxide groups, with(b) a condensate which contains primary amino groups and is obtained from a primary diamine of not less than 4 carbon atoms and one or more mono- and/or dicarboxylic acids, one or more primary amino groups of the condensate (b) being used per free epoxide group of the adduct (a), and(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: GrantFiled: November 25, 1986Date of Patent: June 21, 1988Assignee: BASF Aktiengesellschaft PatentabteilungInventors: Eberhard Schupp, Rolf Osterloh, Werner Loch, Klaas Ahlers
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Patent number: 4751257Abstract: A resin coating composition characterized by containing as its resin binder an epoxy resin derivative having an oxazolidine ring functional group of the formula ##STR1## where R.sub.1 is an alkylene group of 2 to 6 carbon atoms, R.sub.2 and R.sub.3 are each hydrogen or methyl, and R.sub.4 and R.sub.5 are each a residue of aldehyde or ketone.Type: GrantFiled: September 9, 1986Date of Patent: June 14, 1988Assignee: Kansai Paint Co., Ltd.Inventor: Akira Tominaga
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Patent number: 4732950Abstract: A cathodic electrodeposition coating composition which comprises:(A) 100 parts by weight of an amine-unsaturated carboxylic acid adduct of epoxidized polybutadiene having a number average molecular weight of from 500 to 10,000 and containing from 70 to 200 mmol of a tertiary amino group, from 20 to 200 mmol of an .alpha.,.beta.-unsaturated monocarboxylate group and from 200 to 2,000 mmol of a carbon-carbon double bond, per 100 g of the resin;(B) from 20 to 200 parts by weight of an addition reaction product of (a) 1 mol of an epoxy resin containing at least two epoxy groups per molecule, and (b) from 1.5 to 2.0 mol of an .alpha.,.beta.-unsaturated monocarboxylic acid;(C) from 5 to 50 parts by weight of an addition reaction product of (a) 1 mol of an epoxy resin containing at least two epoxy groups per molecule, and (b) a mixture of from 0.5 to 1.5 mol of an .alpha., .beta.-unsaturated monocarboxylic acid and from 0.5 to 1.Type: GrantFiled: February 9, 1987Date of Patent: March 22, 1988Assignee: Dai Nippon Toryo Co., Ltd.Inventors: Masanori Nagai, Kenji Hasui, Toshio Shinohara
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Patent number: 4730011Abstract: A synthetic resin which contains quaternary ammonium groups, and its preparation.The water-dilutable synthetic resin which contains quaternary ammonium groups and furthermore contains one or more basic secondary and/or tertiary amino groups per quaternary ammonium group is an adduct of(A) a quaternary ammonium salt which is obtained by reacting(a) an organic compound containing two or more basic amino groups per molecule, one of which is a primary group and is protected as a ketimine by prior reaction with a ketone, and the remaining groups are tertiary groups, with(b) an organic or inorganic acid and(c) a monoepoxide compound, and, if necessary, then eliminating the ketone hydrolytically,(B) a resin which contains on average from 1.5 to 3.0 epoxide groups per molecule, and, if required,(C) one or more monofunctional organic compounds whose functional group is capable of undergoing an addition reaction with an epoxide.Type: GrantFiled: August 15, 1985Date of Patent: March 8, 1988Assignee: BASF AktiengesellschaftInventors: Werner Loch, Rolf Osterloh, Eberhard Schupp, Klaas Ahlers