With Organic Nitrogen Or Organic Sulfur Reactant Patents (Class 523/404)
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Patent number: 5500461Abstract: A process for producing stable dispersions of epoxy resins is presented in which an epoxy resin is mixed with water in the presence of a reactive surfactant to form a predispersed resin. To this predispersed resin, a micronized dicyandiamide based curing agent is added to form a predispersed resinous mass. The mass is stirred for a time and at a temperature sufficient to convert the predispersed resinous mass to a stable epoxy resin dispersion where the water is the continuous phase and the resin is the dispersed phase. The dispersion is useful as a one-pack epoxy resin system in applications such as binders for non-wovens, papers, textiles, composites, and laminates and in many coating applications.Type: GrantFiled: April 19, 1995Date of Patent: March 19, 1996Assignee: Shell Oil CompanyInventor: Glenda C. Young
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Patent number: 5491183Abstract: A cathodic electrodeposition paint containing a cationically modified epoxy resin and a crosslinker dispersed in an acidic aqueous medium is disclosed which contains an auxiliary resin component which is capable of improving the surface smoothness of the cured paint films and which is a reaction product produced by reacting a t-alkylphenol novolac epoxy resin with an amount of an active hydrogen compound sufficient to open all epoxy rings. When the thus produced auxiliary resin has a hydroxyl group, reaction thereof with a lactone or alkylene oxide, to graft a soft segment to the auxiliary resin improves not only the surface smoothness but also the impact strength of the paint films.Type: GrantFiled: November 4, 1994Date of Patent: February 13, 1996Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Ichiro Kawakami, Hiroyuki Nojiri, Toshiyuki Ishii
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Patent number: 5489630Abstract: A new epoxy hardener composition is the product of the reaction of (A) a poly(alkylene oxide) monoamine or diamine with a molecular weight (Mn) of about 500 to 3000 and (B) a di- or polyepoxide, in a ratio of epoxide to active amine hydrogens of about 1.1:1 to 6:1 to yield an intermediate (C), which in a second step is reacted with (D) a di- or polyamine, in a ratio of active amine hydrogens to epoxide of greater than about 25 to 1, preferably greater than about 30 to 1. The compositions of the invention are excellent emulsifiers of liquid epoxy resins in aqueous medium without the addition of added surfactants or acidic compounds, and can be used to prepare water resistant water-borne coatings and related products from both liquid and solid epoxy resins, that possess long pot lives and contain relatively small amounts of volatile organic compounds.Type: GrantFiled: November 28, 1994Date of Patent: February 6, 1996Assignee: Air Products and Chemicals, Inc.Inventor: Frederick H. Walker
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Patent number: 5475039Abstract: A curing agent for aqueous epoxy resin emulsions comprising 10-80% by weight of at least one emulsifier, 1-80% by weight of at least one coemulsifier, and 5-80% by weight of at least one bis(diamine)-diepoxide adduct. Optionally, the curing agent contains 0-80% by weight of a diamine or a mixture of two or more diamines.Type: GrantFiled: October 17, 1994Date of Patent: December 12, 1995Assignee: Sika AG, vorm. Kaspar Winkler & Co.Inventor: Pierre-Andre Butikofer
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Patent number: 5472998Abstract: An improved aqueous cathodic electrocoating composition having a binder of an epoxy-amine adduct which is of an epoxy resin that has been reacted with an amine, and a blocked polyisocyanate crosslinking agent; wherein the improvement is the use of a water soluble electrically conductive polymeric additive of a polyepoxy hydroxy ether resin reacted with a ketimine and optionally up to 60% of the epoxy end groups of the resin reacted with another amine and the resin has an epoxy equivalent weight of about 500-900, a weight average molecular weight of about 1,000-5,000 and an electrical conductivity of about 4,000-8,000 microsiemens to provide an electrocoating composition having improved throw power.Type: GrantFiled: September 16, 1994Date of Patent: December 5, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert A. Tessmer, Peter W. Uhlianuk, Ding Y. Chung
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Patent number: 5464913Abstract: A self-curing cationically electrodepositable resin useful as a paint composition having in the molecule:(1) a primary hydroxyl group,(2) a cationic group, and(3) at least one epoxy group-containing functional group represented by the following structural formulas (I) and (II): ##STR1## The electrodepositable resin is obtained by the reaction of an epoxy resin with at least three epoxy group-containing functional groups of structural formulas (I) and (II), a cationizing agent such as amino compounds, and a compound having at least one phenolic hydroxyl group per molecule.Type: GrantFiled: February 15, 1995Date of Patent: November 7, 1995Assignee: Kansai Paint Co., Ltd.Inventors: Reiziro Nishida, Akira Tominaga
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Patent number: 5464887Abstract: An aqueous electrocoating composition useful in a method of electrodeposition contains an electrodepositable resin, optionally a curing agent and a microparticulate crosslinked unsaturated polyester flatting agent. The microparticulate flatting agent provides the desired flatting effect without compromising coating properties such as corrosion resistance and flexibility.Type: GrantFiled: April 8, 1994Date of Patent: November 7, 1995Assignee: PPG Industries, Inc.Inventors: Matthew S. Scott, Gregory J. McCollum, Chester J. Szymanski, Craig A. Wilson
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Patent number: 5461090Abstract: Aqueous primer compositions containing substantially no volatile organic solvents, suitable for promoting the bonding of a metal adherend to a second adherend, are prepared by dispersing one or more solid epoxy resins and a solid curing agent into water such that the particle sizes of the solids are less than 30 .mu.m. The primer compositions are environmentally superior to solvent based primers without loss of physical properties, are storage stable, and exhibit excellent solvent resistance.Type: GrantFiled: October 1, 1993Date of Patent: October 24, 1995Assignee: Cytec Technology Corp.Inventor: David E. Sweet
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Patent number: 5459180Abstract: Polyol/epoxy adducts obtained by reaction of(A) an aliphatic polyol having an average molecular weight (Mw) of 200 to 2000 and(B) an epoxy compound having at least two epoxy groups per molecule and an epoxy equivalent weight of 100 to 2000,the equivalent ratio of the OH groups to the epoxy groups being 1:3.51 to 1:10, preferably 1:4 to 1:9, particularly preferably 1:45 to 1:8, and the epoxy equivalent weight of the adduct being between 150 g/eq and at least 800 g/eq, preferably between 250 g/eq and 1000 g/eq which adducts serve as nonionic emulsifiers in water-dilutable epoxy liquid resins.Type: GrantFiled: October 12, 1994Date of Patent: October 17, 1995Assignee: Hoechst AGInventors: Armin Pfeil, Joerg-Peter Geisler, Claus Godau, Bernhard Stengel-Rutkowski, Matthias Meyer, Stefan Petri
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Patent number: 5451306Abstract: The present invention relates to a film forming method, in which a specified electrodeposition paint composed of at least an emulsion, a gel fine particle dispersion, and a pigment paste is applied by an electrodeposition coating method to an electronic part metal surface having a burr, followed by drying and baking to form an insulating film having an average thickness of 20 to 100 .mu.m.Type: GrantFiled: March 16, 1994Date of Patent: September 19, 1995Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Kazuya Nakamura, Shigenori Uda, Tsuguo Inazawa, Masaru Kikuya
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Patent number: 5451305Abstract: The invention relates to a cathodic electro-dipping process wherein the electro-dipping primer employed contains a crosslinking agent which can be obtained by reactinga) a diol and/or a triol or a mixture of diols and/or a mixture of triols,b) diphenylmethane 4,4'-diisocyanate the melting point of which has been depressed, by partial reaction with a monool and/or polyol or a mixture of monools and/or a mixture of polyols, so far that it is liquid at room temperature andc) a masking agent or a mixture of masking agentsto give a crosslinking agent which is free from isocyanate groups.Type: GrantFiled: February 9, 1994Date of Patent: September 19, 1995Assignee: BASF Lacke +Farben AGInventors: Gunther Ott, Udo Reiter, Walter Jouck
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Patent number: 5441995Abstract: The present invention provides a paint film with fewer craters and indentations, while maintaining performance as an electrodeposition paint. The electrodeposition paint composition contains an aqueous dispersing system containing an electrodepositable resin and a block polymer containing polysiloxane units and polyalkylene oxide units.Type: GrantFiled: June 6, 1994Date of Patent: August 15, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Atsushi Ohgaki, Hiroharu Ohsugi, Hisaki Tanabe, Kenshiro Tobinaga, Yoshio Kojima
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Patent number: 5431791Abstract: An electrodeposition method is described where a conductive substrate is immersed in an electrodeposition coating composition comprising, in an aqueous medium:A) a resin having a plurality of acid-salted primary amine groups, andB) a curing agent having a plurality of cyclic carbonate groups.Type: GrantFiled: February 7, 1995Date of Patent: July 11, 1995Assignee: BASF CorporationInventors: Timothy S. December, Paul J. Harris
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Patent number: 5427857Abstract: An improved aqueous cathodic electrocoating composition of an aqueous carrier having dispersed therein a film forming binder of (1) an epoxy resin-amine adduct and (2) a blocked polyisocyanate crosslinking agent; wherein the improvement is the use of a branched epoxy resin to form the adduct which is the reaction product of a polyhydric phenol and a branched epoxy macromonomer formed by the self condensation of an epoxy resin in the presence of a catalyst; the branched epoxy resin has an epoxy equivalent weight of about 700-2,000 and provides an electrocoating composition that has improved throw power and that forms coatings that have improved corrosion resistance in comparison to conventional electrocoating compositions formed from linear epoxy resins.Type: GrantFiled: June 28, 1994Date of Patent: June 27, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephen C. Peng
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Patent number: 5418263Abstract: A cathodic electrodeposition paint containing as a binder resin an amine-epoxy resin adduct and a blocked polyisocyanate crosslinker is disclosed. The binder resin and the crosslinker are emulsified in an aqueous medium containing a neutralizing agent with the aid of amine adduct of a monoepoxide compound having a hydrophobic group or block. Not only the amine-monoepoxide adduct functions as a surfactant but also it is deposited electrically and then cured with the crosslinker integrally with the binder resin.Type: GrantFiled: April 19, 1994Date of Patent: May 23, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Toshiaki Sakamoto, Yoshio Kojima, Kenshiro Tobinaga
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Patent number: 5409972Abstract: This invention relates to a process for the preparation of self-crosslinking cationic paint binders which can be diluted with water after protonation and are based on modified aminoalkylation products of phenols; to the binders prepared by this process and to their use for formulating water-dilutable paints, in particular electrodeposition paints which can be deposited cathodically. The process is characterized in that an aminoalkylation product of a phenol containing at least one secondary amino group is reacted with epoxide compounds, and after temperature treatment, the reaction product is reacted with partly blocked isocyanate compounds. The process permits the use of blocking agents which allow stoving temperatures in the range of 130 to 150.degree. C.Type: GrantFiled: May 7, 1992Date of Patent: April 25, 1995Assignee: Vianova Kunstharz, A.G.Inventors: Roland Feola, Willibald Paar, Georg Pampouchidis, Johann Gmoser, Helmut Honig
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Patent number: 5407748Abstract: A resin composition for aqueous paint contains, as main components, (A) a resin obtained by reacting a certain epoxy resin, an amine compound and a phenol compound and substantially containing neither primary or secondary amino group nor epoxy group; (B) a resin having phenolic hydroxyl groups and substantially containing neither primary nor secondary amino group, and (C) a resin compound having glycidyl groups or epoxy groups. The composition is excellent in dispersibility of each component and in storage stability. It has an extremely low heating loss of the coating film, and is excellent in smoothness, corrosion resistance, adhesion, etc.Type: GrantFiled: October 8, 1993Date of Patent: April 18, 1995Assignee: Kansai Paint Co., Ltd.Inventors: Toshio Fujibayahsi, Haruo Nagaoka
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Patent number: 5405701Abstract: A resin composition for aqueous coating, comprising as main components(A) a resin having hydroxyl groups and cationic groups, and(B) a compound having, in the molecule, at least two glycidyl groups each in a glycidylamino group represented by the following formula ##STR1## (R is a group selected from a hydrogen atom and a glycidyl group) directly bonding to carbon atoms of the aromatic ring. This composition is excellent in storage stability, low-temperature curability, etc. and is useful in cationic electrocoatings, in particular.Type: GrantFiled: April 15, 1993Date of Patent: April 11, 1995Assignee: Kansai Paint Co., Ltd.Inventors: Toshio Fujibayashi, Haruo Nagaoka
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Patent number: 5387625Abstract: A waterborne coating composition for metal containers, a method of coating a metal container, and a metal article useful as a food or beverage container are disclosed. The waterborne coating composition is a thermoplastic material and comprises: (a) a flexible, high molecular weight epoxy resin; (b) a medium molecular weight epoxy resin; (c) a resin having pendant carboxylic acid groups; (d) a fugitive base; and an aqueous carrier, wherein the waterborne coating composition includes about 0.5 to about 2.5 pounds volatile organic content per gallon of the composition, minus water.Type: GrantFiled: May 18, 1993Date of Patent: February 7, 1995Assignee: The Dexter CorporationInventors: Girish G. Parekh, Perumal T. Pillai, Devasia J. Ponmankal
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Patent number: 5382606Abstract: A curing agent for aqueous epoxy resin emulsions is described, which curing agent contains 10-80% by weight of at least one emulsifier, 1-80% by weight of at least one coemulsifier, and 5-80% by weight of at least one bis(diamine)-diepoxide adduct. Optionally, the curing agent furthermore contains 0-80% by weight of a diamine or a mixture of two or more diamines. Said curing agent has the ability of forming microemulsions when water is added, preferably non-ionic oil-in-water microemulsions. Said microemulsions have a good shelf life. They are useful as curing agent for any desired aqueous epoxy resin dispersions, and they can also be used as curing agent in compositions based on epoxy resin and cement mortar.Type: GrantFiled: April 28, 1993Date of Patent: January 17, 1995Assignee: Sika AG, vorm. Kaspar Winkler & Co.Inventor: Pierre-Andre Butikofer
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Patent number: 5380781Abstract: Cationically electrodepositable (gelled) fine particles using, as the base, an epoxy resin-amine adduct having hydrolysable alkoxysilane groups, and a cationic electrodeposition paint composition comprising said fine particles. Said fine particles give a paint film having excellent corrosion resistance and are useful as a rheology-controlling agent for cationic electrodeposition paint. Said electrodeposition paint composition has an excellent edge-covering property, and a paint film formed therewith on an article to be coated can give improved corrosion resistance to the edges of said article and has good surface smoothness.Type: GrantFiled: July 23, 1993Date of Patent: January 10, 1995Assignee: Kansai Paint Co., Ltd.Inventors: Kiyoshi Kato, Kenichi Yoneyama, Haruo Nagaoka, Kenji Yamamoto, Kazuyuki Morimoto, Masafumi Kume
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Patent number: 5364897Abstract: The invention provides polyisocyanate compositions having a uretonimine-modified isocyanate content of from 4% to 75% by weight, calculated on the whole composition, comprising a uretonimine-modified polyisocyanate and a non-ionic surface-active agent devoid of hydroxy, amino and carboxylic acid groups, and aqueous emulsions thereof having improved stability and pot-life.Type: GrantFiled: May 28, 1992Date of Patent: November 15, 1994Assignee: Imperial Chemical Industries PLCInventors: Ann E. Knight, Godelieve Bourbon
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Patent number: 5362772Abstract: A cationic finely divided polymeric microgel dispersed in an aqueous medium for use in cationic electrocoating compositions of a epoxy terminated polyepoxy hydroxy ether resin being end capped with a ketimine, a primary amine, secondary amine or mixtures thereof and amino siloxane to provide silanol groups and amino groups; the amino groups of the polymeric microgel being neutralized with an acid to form cationic groups for water dispersibility and the silanol groups being condensed with hydroxy groups of the resins and other silanol groups of the resin thereby forming a crosslinked microgel.Type: GrantFiled: July 9, 1993Date of Patent: November 8, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Peter W. Uhlianuk, Raymond S. Van Ham
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Patent number: 5360839Abstract: Cathodic electrodeposition paints are rendered hardly susceptible to oil droplet-induced craters by incorporating an amine-modified acrylic copolymer of t-butyl (meth)acrylate with a hydroxyl group-containing monomer and an oxirane ring-containing monomer in the form of an aqueous emulsion. The amine-modified acrylic copolymer may be an adduct with a half blocked organic diisocyanate. The paint gives a cured film substantially free from oil droplet-induced craters and having a good adhesion to an overcoating and a good surface smoothness.Type: GrantFiled: April 13, 1993Date of Patent: November 1, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Motoi Tanimoto, Tatsuo Yoshida, Kenshiro Tobinaga, Yuji Toyoda
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Patent number: 5360838Abstract: An advanced epoxy cationic resin useful as an electrodeposition coating and having a charge density of from 0.2 to 0.6 milliequivalent of cationic charge per gram of resin is prepared by reacting in the presence of a suitable catalyst (A) a composition comprising (1) at least one diglycidyl ether of (a) an oxyalkylated aromatic diol or (b) an oxyalkylated cycloaliphatic diol or (c) certain oxyalkylated aliphatic diols and (2) at least one diglycidyl ether of a dihydric phenol with (B) at least one dihydric phenol and optionally (C) a monofunctional capping agent.Components (A-1) and (A-2) are employed in quantities such that from 10 to 75 weight percent of the diglycidyl ethers contained in component (A) are contributed by component (A-1), and from 25 to 90 weight percent of such glycidyl ethers are contributed by component (A-2). Components (A) and (B) are employed in such quantities that the resultant epoxy resin has an average epoxide equivalent weight of from 350 to 10,000.Type: GrantFiled: June 14, 1993Date of Patent: November 1, 1994Assignee: The Dow Chemical CompanyInventors: Kenneth W. Anderson, Richard A. Hickner
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Patent number: 5356959Abstract: Epoxy resins obtainable by reactingA) a polyfunctional epoxide, which carries on average 1.5 to 2.5 epoxy groups per molecule and has an epoxide equivalent weight of from 100 to 2000, with based on 1 mol of epoxy groupsB) from 0.1 to 0.5 mol of an alkylphenol, the alkyl groups of which carry from 6 to 20 carbon atoms, andC) from 1 to 100 mmol of a polyoxyalkylenediol obtained from 1,2-propylene oxide, or of a copolymer obtained from 1,2-propylene oxide and other alkylene oxides, which has an average molecular weight of from 200 to 5000 and, on average, from 1 to 4 sulfonic acid groups bonded to methyl groups per molecule, and alsoD) from 0.2 to 0.3 mol of a diol, which isd1) a phenolic diol and/ord2) a polyoxyalkylenediol which has an average molecular weight of from 200 to 5000,with the proviso that the reaction product has an epoxide equivalent weight of from 1000 to 5000, can be converted to pigment resins suitable for electrodeposition coating and pigment pastes can then be prepared from said resins.Type: GrantFiled: July 27, 1993Date of Patent: October 18, 1994Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Klaus Huemke, Christian Sinn
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Patent number: 5356960Abstract: An improved aqueous electrocoating composition that contains an anticrater agent which is a reaction product of poly epoxy hydroxy ether resin, polyoxyalkylene diamine and an amino, glycidyl or isocyanate functional alkyl alkoxy silane having a number average molecular weight of about 1,000-6,000; electrodeposited finishes are formed that have a significant reduction in craters and are smooth and even finishes.Type: GrantFiled: August 11, 1993Date of Patent: October 18, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ding Y. Chung, Allisa Gam
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Patent number: 5350784Abstract: A two-component water-dispersible coating composition based on a blend of a water compatible polyamine-epoxy adduct and a resin compatible polyamine-epoxy adduct, and a polyepoxide resin. The water compatible polyamine-epoxy adduct is formed by reacting a polyamine having primary amine groups with a mixture of a monoepoxide and polyepoxide in which the amounts of monoepoxide and polyepoxide are such that the monoepoxide reacts with 10 to 50% of the primary amine groups and the polyepoxide reacts with 5 to 65% of the remaining primary amine groups. The resin compatible polyamine-epoxy adduct is formed by reacting a polyamine having primary amine groups with a monoepoxide or a polyepoxide in an amount which provides from about 0.4 to 1 equivalents epoxide per primary amine group. The amount of polyepoxide resin is such that there is from about 0.5 to 1.5 equivalents epoxide per active hydrogen equivalent.Type: GrantFiled: May 13, 1993Date of Patent: September 27, 1994Assignee: Air Products and Chemicals, Inc.Inventors: Stuart P. Darwen, David A. Cornforth
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Patent number: 5344856Abstract: The invention is a water dispersible epoxy resin composition comprising:(A) the reaction product of;(i) one or more polyepoxides;(ii) optionally, one or more poly(aromatic hydroxy) containing compounds,(iii) optionally, one or more chain terminators; and(iv) one or more nominally difunctional C.sub.12-36 fatty acids or a dimer of an unsaturated, fatty acid, andB) a sufficient amount of a surfactant to form a stable dispersion of the epoxy resin in water wherein the surfactant comprises an alkyl aryloxy poly(propyleneoxy) poly(ethyleneoxy) ethanol, a C.sub.12-36 hydrocarbyloxy poly(propyleneoxy) poly(ethyleneoxy) ethanol or a C.sub.12-36 hydrocarbylcarboxyloxy poly(propyleneoxy) poly(ethyleneoxy) ethanol. In another aspect the invention is a high solid aqueous emulsion of such epoxy resin reaction product and surfactant.Type: GrantFiled: May 17, 1993Date of Patent: September 6, 1994Assignee: The Dow Chemical CompanyInventor: Dieter H. Klein
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Patent number: 5336702Abstract: An aqueous resin dispersion containing as an aqueous resin component a polyurethane-modified epoxy-polyamine resin comprising a reaction product of an epoxy group-containing polyurethane compound obtained by the reaction of a polyhydroxy compound having a number average molecular weight of 50 to 8,000, a polyisocyanate compound, and a compound containing one hydroxyl group and at least one alicyclic epoxy group in a molecule; a bisphenol compound; a bisphenol diglycidyl ether compound; and an active hydrogen-containing amine compound. Said aqueous resin dispersion has excellent corrosion resistance and is suited especially for cathode electro-deposition coating.Type: GrantFiled: December 3, 1992Date of Patent: August 9, 1994Assignee: Kansai Paint Co., Ltd.Inventor: Koji Kamikado
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Patent number: 5336701Abstract: A process is provided for producing improved color acrylonitrile polymer gels involving compounding a composition of an acrylonitrile polymer with an electrophilic reagent to produce acrylonitrile polymer gels, and admixing water with the gels to reduce the yellowness thereof. Improved color, reduced gloss polycarbonate/graft polymer blends are provided by compounding the resultant gels with polycarbonate, a styrene-acrylonitrile copolymer and ABS graft polymer to form reduced gloss PC/ABS/SAN composition. The process provides acrylonitrile gels and reduced gloss compositions exhibiting improved levels of color. The blend compositions are useful as molding resins and the gelled acrylonitrile polymer is useful as a gloss reducing additive.Type: GrantFiled: September 28, 1992Date of Patent: August 9, 1994Assignee: General Electric CompanyInventors: Robert H. Wildi, Keith E. Cox, Jack A. Hill
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Patent number: 5330627Abstract: A thermosetting coating composition containingA) one or more binders convertible into liquid or dissolved form at least at the curing temperature and containing acidic groups, basic groups or ionic groups of similar charge,B) one or more binders convertible into liquid or dissolved form at least at the curing temperature and containing basic groups where (A) contains acidic groups, acidic groups where (A) contains basic groups or ionic groups of like charge opposite to the charge of the ionic groups of (A), binder (B) being noninterdiffusible under storage and application conditions, but interdiffusible with binder (A) under hardening conditions, andC) optionally standard solvents, pigments and/or typical paint auxiliaries and/or additives which do not lead to any interdiffusion of the binders A) and B) under storage and application conditions,and a process for the production of coatings by application of the coating composition and subsequent thermal curing.Type: GrantFiled: September 9, 1993Date of Patent: July 19, 1994Assignee: Herberts G.m.b.H.Inventors: Roland Grutter, Reiner Bohmert, Rolf Reinecke
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Patent number: 5324756Abstract: A pigment dispersant that is useful in a cathodic electrocoating composition is prepared by bringing into contact the following compounds: a cyclic alkylene urea amine, a polyepoxide and a dialkanol amine; this pigment dispersant has an advantage of allowing for the high pigment to binder ratios and minimizes the volatile organic content (VOC) in the electrocoating composition.Type: GrantFiled: May 5, 1993Date of Patent: June 28, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Taddesse Gebregiorgis
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Patent number: 5324404Abstract: In order to increase the stone chip resistance of automobile finishes aqueous electrocoating paints are used which are produced by the use of a pigment paste which contains as grinding resin an at least partially protonated epoxide-amine adduct which is obtainable by reacting(A) a glycidyl ether of a polyphenol which contains on statistical average at least one epoxide group in the molecule, or a mixture of such glycidyl ethers,(B) a polyglycidyl ether of a polyol which contains on statistical average more than 1.0 epoxide groups in the molecule, or a mixture of such polyglycidyl ethers, and(C) a compound which contains a primary amino group in the molecule or a mixture of such compoundswith each other in such a stoichiometric ratio that an epoxide-amine adduct is obtained in which on statistical average at least 2.Type: GrantFiled: July 28, 1992Date of Patent: June 28, 1994Assignee: BASF Lacke + Farben AktiengesellschaftInventors: Gunther Ott, Ulrich Heimann, Udo Reiter, David J. Santure, Thomas Brucken, Walter Jouck
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Patent number: 5324402Abstract: The invention relates to a cathodic electro-dipping process wherein the electro-dipping primer employed contains a crosslinking agent which can be obtained by(I) reacting, in a first stage,(a) diphenylmethane diisocyanate and(b) a monoalcohol or a mixture of monoalcohols to give an intermediate product (A) containing isocyanate groups, and(II) reacting this intermediate product (A) in a second stage with(c) a polyol or a mixture of polyols to give an intermediate product (B) containing hydroxyl groups which(III) is reacted in a third stage either with(d) a cycloaliphatic, aliphatic or araliphatic polyisocyanate or a mixture of such polyisocyanates and(e) a monofunctional masking agent or a mixture of such masking agents or with(f) a partially-masked polyisocyanate prepared from (d) and (e)to give a crosslinking agent which is free from isocyanate groups.Type: GrantFiled: February 4, 1993Date of Patent: June 28, 1994Assignee: BASF Lacke+Farben AktiengesellschaftInventors: Gunther Ott, Ulrich Heimann, Walter Jouck, Udo Reiter, David J. Santure
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Patent number: 5319004Abstract: Hardeners for epoxy resins, comprising reaction products of(A) polyamidoamines that were obtained by polycondensation of (a) dicarboxylic acids containing oxyalkylene groups, or their derivatives, with (b) polyamines containing at least two amino groups capable of undergoing condensation with (a),(B) polyamines containing at least two secondary amino groups, and(C) adducts of (c) polyepoxy compounds and (d) polyalkylene polyether polyols.Epoxy resins that have been cured with these hardeners exhibit in particular a very good water resistance.Type: GrantFiled: February 26, 1993Date of Patent: June 7, 1994Assignee: Hoechst AktiengesellschaftInventors: Manfred Marten, Bernhard Stengel-Rutkowski, Claus Godau
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Patent number: 5314971Abstract: Urethane-modified polyoxyalkylene epoxy resins useful in aqueous dispersions having the general formula ##STR1## where R and R.sup.1 are, independently of one another, ##STR2## wherein R.sup.3 is a C.sub.1-3 alkyl group,R.sup.4 is a C.sub.1-4 alkylenemoiety, ##STR3## each b is, independently of one another, an integer from 0 to 4, and c is 1 to 10;a is 1 to 20, andR.sub.2 is H and at least once the group ##STR4## R.sup.6 is a C.sub.1-5 alkyl group, R.sup.7 is H or CH.sub.3 --,d is 1 to 100,e is 0 or 1,f is 0 or 1, andR.sup.8 is an aliphatic, cyclic, alicyclic, aromatic or araliphatic hydrocarbon group.Type: GrantFiled: August 18, 1993Date of Patent: May 24, 1994Assignee: Witco GmbHInventors: Bernd Neffgen, Wolfgang Scherzer
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Patent number: 5312879Abstract: A method for preparing an advanced epoxy cationic resin from an epoxy 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 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 resin. Such resin blends can be utilized in cathodic electrodeposition coating systems.Type: GrantFiled: July 16, 1993Date of Patent: May 17, 1994Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 5310770Abstract: Water-reducible curing agents for epoxy resins are made from the diglycidyl ether of cyclohexane dimethanol and a diamine selected from the group consisting of meta-xylylene diamine, isophorone diamine, diaminocyclohexane and 1,3-bisaminomethyl cyclohexane.Type: GrantFiled: December 30, 1992Date of Patent: May 10, 1994Assignee: Hi-Tek Polymers, Inc.Inventors: William J. DeGooyer, George A. Roy, II
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Patent number: 5300541Abstract: Barrier materials for reducing the permeability of plastic packaging materials are provided, characterized as containing at least about seven percent by weight amine nitrogen, or a total of at least about 17 percent amine nitrogen plus hydroxyl groups. The barrier materials exhibit oxygen permeability of less than about 1.5 cc-mil/100 in.sup.2 -day-atmosphere and a carbon dioxide permeability of less than about 15 cc-mil/100 in.sup.2 -day-atmosphere at 23.degree. C. and zero percent relative humidity. The barrier material can be formed from polyepoxide and polyamine. Optionally the polyamine may comprise prereacted polymeric resin formed from a polyepoxide and a polyamine. Multilayer packaging materials and multilayer containers including the polyamine-polyepoxide barrier material are part of the invention.Type: GrantFiled: September 30, 1991Date of Patent: April 5, 1994Assignee: PPG Industries, Inc.Inventors: Richard M. Nugent, Jr., Ken W. Niederst, Jerome A. Seiner
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Patent number: 5298538Abstract: Plasticizing resins, aqueous dispersions of cationic resins, and methods of making the same for use in cathodic electrodeposition are disclosed. The resins are formed from reacting a polyoxyalkylenepolyamine, a phenol, and a formaldehyde. The reactants may further include a block building unit derived from a polyepoxide. When used in combination with other conventional electrodepositable resins, deposited films with improved mechanical properties and descreased tendency toward cratering are obtained.Type: GrantFiled: April 11, 1990Date of Patent: March 29, 1994Assignee: BASF CorporationInventors: Klaus Cibura, Yali F. Hallock, John A. Gilbert, John D. McGee
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Patent number: 5292832Abstract: Advanced epoxy cationic resins are prepared 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 oxyalkylated aromatic or cycloaliphatic diol, such as a condensation product of bisphenol A, ethylene oxide 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. Use of the diglycidylether of an oxyalkylated diol provides coating compositions with lower viscosity and produces deposition coatings of higher film build and better surface appearance than compositions without this component.Type: GrantFiled: January 5, 1993Date of Patent: March 8, 1994Assignee: The Dow Chemical CompanyInventor: Richard A. Hickner
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Patent number: 5288770Abstract: A resin composition for a cationically electrodepositable paint comprising(A) a resin having hydroxyl groups and cationic groups,(B) an epoxy resin having at least 2 epoxy functional groups each of which comprises an epoxy group directly bound to an alicyclic ring and/or bridged alicyclic ring on average per molecule, and(C) a finely divided gelled polymer as principal components, wherein said finely divided gelled polymer is obtained by emulsion polymerizing(C-1) a polymerizable monomer containing at least two radically polymerizable unsaturated groups in the molecule, and(C-2) a radically polymerizable unsaturated monomer other than the one mentioned in (C-1), abovein the presence of a reactive emulsifier containing an allyl group in the molecule.Type: GrantFiled: January 22, 1991Date of Patent: February 22, 1994Assignee: Kansai Paint Co., Ltd.Inventors: Teiji Katayama, Eisaku Nakatani, Haruo Nagaoka, Kenji Yamamoto, Reiziro Nishida
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Patent number: 5283124Abstract: A coating resin composition composed mainly of an epoxy resin derivative obtained by reacting an amine compound containing hydroxyl groups, one secondary amino group and an amide group in the molecule with an epoxy group of an epoxy resin. The resin composition can be used alone, or in combination with an epoxy resin containing, per molecule, on the average at least 2 epoxy functional groups each comprising an epoxy groups directly bound to an alicyclic ring and/or bridged alicyclic ring. The resin is useful in a cationically electrodepositable paint.Type: GrantFiled: March 1, 1991Date of Patent: February 1, 1994Assignee: Kansai Paint Co., Ltd.Inventors: Toshio Fujibayashi, Haruo Nagaoka
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Patent number: 5283269Abstract: Epoxy resins with urethane groups, containing on average per molecule from 0.5 to 5 groups of the formula I ##STR1## where the substituents R.sup.1 and R.sup.2 are C.sub.1 -C.sub.8 -alkyl groups, which may also be linked together to form five- or six-membered rings, which may contain an oxygen atom, or are each phenyl, are useful in electrocoating.Type: GrantFiled: January 14, 1993Date of Patent: February 1, 1994Assignee: BASF Lacke + Farben AktiengesellschaftInventors: Klaus Huemke, Dirk Lawrenz, Ulrich Heimann
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Patent number: 5276071Abstract: Cationic advanced resins are obtained by (I) reacting a composition comprising (A) an advanced epoxy resin composition comprising the product resulting from reacting a composition comprising (1) an aromatic hydroxyl-containing product resulting from reacting a composition comprising (a) at least one diglycidyl ether of (i) an oxyalkylated aromatic diol, or ii) at least one compound having two hydroxyl groups per molecule in which the hydroxyl groups are attached to an aliphatic or cycloaliphatic carbon atom and which compound is free of aromatic rings; or (iii) a combination of (i) and (ii); and (iv) optionally a diglycidyl ether compound different from (i) and (ii); and (b) at least one compound containing two aromatic hydroxyl groups per molecule; (2) at least one diglycidyl ether of a compound containing two aromatic groups per molecule; (3) optionally, one or more compounds containing two aromatic hydroxyl groups per molecule; and (4) optionally, a monofunctional capping agent; with (B) a nucleophilic comType: GrantFiled: February 9, 1993Date of Patent: January 4, 1994Assignee: The Dow Chemical CompanyInventors: Kenneth W. Anderson, Deborah L. Haynes, Ross C. Whiteside, Jr.
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Patent number: 5274012Abstract: The invention relates to modified polyoxyalkylene epoxy resins based on polyhydric phenols prepared by the addition of polyethers and/or polyether monourethanes containing isocyanate groups to higher-molecular-weight hydroxyl group-containing polyglycidyl compounds, and to the use of these reaction products in the preparation of stable aqueous dispersions.Type: GrantFiled: November 6, 1992Date of Patent: December 28, 1993Assignee: Witco GmbHInventors: Bernd Neffgen, Wolfgang Scherzer
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Patent number: 5270355Abstract: A paper coated resin has been provided which simultaneousy provides coated papers with improved ink receptivity, water resistance and blister resistance in a good balance. The resin is obtainable by introducing alicyclic amino and/or alicyclic epoxy compounds into a polyalkylenepolyamine-urea-aldehyde(epihalohydrin) resin or by introducing alicyclic amino and/or alicyclic epoxy compounds into a polyalkylenepolyamine-urea-aldehyde(epihalohydrin) resin and/or an amine-epihalohydrin resin and reacting or mixing these resins.Type: GrantFiled: January 13, 1992Date of Patent: December 14, 1993Assignee: DIC-Hercules Chemicals, Inc.Inventors: Hiroharu Kawano, Satoshi Takizawa, Hiroki Owaki, Haruka Hirayama
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Patent number: 5260355Abstract: 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: February 22, 1993Date of Patent: November 9, 1993Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 5248741Abstract: An advanced epoxy cationic resin useful as an electrodeposition coating having a charge density of from 0.2 to 0.6 milliequivalent of cationic charge per gram of resin is prepared by reacting in the presence of a suitable catalyst (A) a composition comprising (1) at least one diglycidyl ether of (a) an oxyalkylated aromatic diol or (b) an oxyalkylated cycloaliphatic diol or (c) certain oxyalkylated aliphatic diols and (2) at least one diglycidyl ether of a dihydric phenol with (B) at least one dihydric phenol and optionally (C) a monofunctional capping agent. Components (A-1) and (A-2) are employed in quantities such that from 10 to 75 weight percent of the diglycidyl ethers contained in component (A) are contributed by component (A-1), and from 25 to 90 weight percent of such glycidyl ethers are contributed by component (A-2). Components (A) and (B) are employed in such quantities that the resultant epoxy resin has an average epoxide equivalent weight of from 350 to 10,000.Type: GrantFiled: November 17, 1992Date of Patent: September 28, 1993Assignee: The Dow Chemical CompanyInventors: Kenneth W. Anderson, Richard A. Hickner