With Nitrogen-containing Reactant Patents (Class 528/113)
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Patent number: 4780524Abstract: The invention relates to a water-dilutable binder for cationic electrocoating finishes. For the preparation of the binders(A) a di-epoxide compound with an epoxide equivalent weight below 2,000 is reacted with(B) a phenol- or thiol-containing compound which reacts monofunctionally with epoxide groups, and with(C) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or phosphine/acid mixture or a mixture of these compounds, as well as, if desired, with(D) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.The components A and B are used in a molar ratio of from 10:1 to 1:1, preferably from 4:1 to 1.5:1 and the reaction of the component A with the component B is carried out at 100.degree. to 190.degree. C., if desired in the presence of a catalyst.Type: GrantFiled: January 23, 1987Date of Patent: October 25, 1988Assignee: BASF Lacke + Farben AGInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4769420Abstract: Binders which are rendered water-dilutable by protonation with an acid, a process for their preparation and their use.These binders are obtainable by reacting a(A) Reaction product of a(a) carboxyl-containing component, consisting of a(a1) carboxyl-containing butadiene/acrylonitrile copolymer having a molecular weight of from 500 to 8,000, if necessary as a mixture with(a2) a dicarboxylic acid which differs from (a1) and, if appropriate,(a3) a monocarboxylic acid and(b) a diprimary and/or primary/secondary amine, with the proviso that from 0.7 to 5 moles of the said amine are used per mole of carboxyl groups of component (a),with one or more(B) epoxy resins having a mean molecular weight from 300 to 6,000 and containing on average from 1.5 to 3.0 epoxide groups per molecule and, if required,(C) an aliphatic or cycloaliphatic secondary amine.In combination with a crosslinking agent, they are useful as coating materials, in particular for cathodic electrocoating.Type: GrantFiled: November 25, 1986Date of Patent: September 6, 1988Assignee: BASF Lacke + Farben AktiengesellschaftInventors: Thomas Schwerzel, Rolf Osterloh, Eberhard Schupp, Klaas Ahlers
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Patent number: 4761460Abstract: There is provided a novel polymaleimide compound represent by the formula (a) ##STR1## The present polymaleimide compound has a curability comparable to that of an epoxy resin. In addition, it is noted that a cured product prepared from the present polymaleimide compound is excellent in heat resistance and adhesion property and has a low linear expansion coefficient as compared with an epoxy resin. The above-mentioned excellent characteristics of the present polymaleimide compound are never observed with respect to conventional maleimide resins. There is also provided specific compositions containing the present polymaleimide compound for exerting the excellent effects of the present polymaleimide compound most effectively.Type: GrantFiled: March 4, 1987Date of Patent: August 2, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Masahiko Otsuka, Hidekazu Ishimura
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Patent number: 4749743Abstract: Disclosed herein is a low molecular weight epoxy-functional polyurethane and high solids thermosetting coating compositions prepared therewith.Type: GrantFiled: October 6, 1986Date of Patent: June 7, 1988Assignee: PPG Industries, Inc.Inventors: Ronald R. Ambrose, Samuel Porter, Jr.
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Patent number: 4736010Abstract: An epoxy resin curing composition comprising a novel curing agent which is obtained by the amidation with elimination of alcohol between an adduct of a carboxyl-containing acrylonitrile-butadiene copolymer with an epoxidized fatty acid ester and an amide-forming nitrogenous compound. This composition exhibits improved adhesion involving peel strength to plastics, rubbers or flexible vinyl chloride resins and is excellent in mechanical strength and resistance to water and alkali and particularly to acid.Type: GrantFiled: April 6, 1987Date of Patent: April 5, 1988Assignees: Asahi Denka Kogyo K.K., A.C.R. Co., Ltd.Inventors: Hiroshi Suzuki, Yutaka Asakawa
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Patent number: 4721742Abstract: Curable amide modified epoxy resins are prepared by polymerizing (I) the reaction product of (A) the reaction product of (1) an epoxy resin having an average of more than one 1,2-epoxy group per molecule and an average of from about 0 to about 30 aliphatic hydroxyl groups per molecule such as a diglycidyl ether of bisphenol A and (2) (a) a material having only one primary amine group per molecule such as monoethanolamine and (b) a material having only one secondary amine group per molecule such as diethanolamine wherein (a) and (b) are added sequentially with (a) being added first, or as a mixture with (B) an anhydride of an unsaturated dicarboxylic acid such as maleic anhydride with (II) a polymerizable ethylenically unsaturated monomer or mixture of monomers such as styrene and methacrylic acid. The resultant resin can be employed as is in the preparation of organic solvent borne coatings or it can be neutralized with a base so as to improve its stability in the preparation of aqueous coatings.Type: GrantFiled: November 7, 1986Date of Patent: January 26, 1988Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Willie L. Myles
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Patent number: 4713406Abstract: 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: GrantFiled: November 25, 1986Date of Patent: December 15, 1987Assignee: BASF AktiengesellschaftInventors: Eberhard Schupp, Rolf Osterloh, Werner Loch, Klaas Ahlers
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Patent number: 4705833Abstract: A thermosettable heat-resistant resin composition containing (A) an amino group-terminated imide compound produced by imidating an aromatic diamine with an aromatic tetracarboxylic anhydride at a diamine:anhydride molar ratio of from 1.2:1 to 4:1, and (B) an epoxy resin having at least two epoxy groups, the molar ratio of the amino group of the imide compound to the epoxy group of the epoxy resin being 1:1.6 to 1:2.6.Type: GrantFiled: December 24, 1985Date of Patent: November 10, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhisa Saito, Hisao Takagishi, Katsuya Watanabe, Kohichi Okuno, Junichi Kenmei, Kunimasa Kamio
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Patent number: 4683285Abstract: The invention is directed to a process for the production of cationic binders for pigment pastes for water-dilutable paints, particularly for cathodic electrodeposition based on low molecular oxazolidine group carrying modified epoxy compounds, and to the pastes obtained. The process is characterized in that preferably aliphatic di- or polyepoxy compounds are reacted with primary mono- and/or diamines and optionally monocarboxy compounds and that oxazolidine groups are introduced into the molecule by reaction with carbonyl compounds. The products show extremely high pigment loading capacity and an excellent performance in cathodically depositable electrodeposition paints. The products permit formation of low solvent paint systems.Type: GrantFiled: October 22, 1985Date of Patent: July 28, 1987Assignee: Vianova Kunstharz, A.G.Inventors: Willibald Paar, Helmut Honig
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Patent number: 4673723Abstract: Compositions for the preparation of thermosetting or thermoplastic polymers, which compositions comprise a mixture of at least one polyepoxide and at least one polyamide oligomer, wherein the oligomer is a primary monoamine, an alpha,omega-primary or -secondary diamine, an alpha,omega-diacid or an alpha-primary amine,omega-acid, together with processes for preparing polymers and the uses of such materials for molding and for adhesives.Type: GrantFiled: August 22, 1985Date of Patent: June 16, 1987Assignee: ATOCHEMInventor: Daniel Cuzin
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Patent number: 4668757Abstract: Aromatic amines and their alkyl, amide, imide or amide-imide substituted derivatives in the presence of catalytic quantities of phenols, cresols, xylenols, bisphenols, and their like cause epoxide resins to thermoset at ambient temperatures. The resulting crosslinked polymers are useful for two component solution systems which provide corrosion and temperature resistant clear coatings or paints, and can also be used as solventless, liquid, two component systems for casting clear, pigmented or filled parts.Type: GrantFiled: March 26, 1984Date of Patent: May 26, 1987Inventor: Gus Nichols
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Patent number: 4634644Abstract: A layer of a liquid composition containing a residue that is polymerizable on contact with a gaseous polymerizing agent and a photocurable residue, which residues may be on the same or different molecules, is contained with a gaseous polymerizing agent so that the layer solidifies but remains photocurable. Subsequently the solidified layer is exposed to actinic radiation in a predetermined pattern and those parts of the layer that are not photocured are removed by treatment with a suitable solvent.Typical polymerizable residues include cyanoacrylates that polymerize on exposure to water vapor, ammonia, or an amine. Typical photocurable residues include acrylates, and methacrylates.The process is suitable for the manufacture of printing plates and printed circuits.Type: GrantFiled: December 10, 1984Date of Patent: January 6, 1987Assignee: Ciba-Geigy CorporationInventors: Edward Irving, Terence J. Smith
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Patent number: 4600763Abstract: A process for the production of novel polymers by the interpolymerization of a bicyclic amide acetal, a dicarboxylic acid anhydride and a polyepoxide at a temperature in the range of from 80.degree. C. to about 200.degree. C. and at a pressure in the range of from about ambient to about 50 atmospheres is described.Type: GrantFiled: September 5, 1985Date of Patent: July 15, 1986Assignee: Ashland Oil, Inc.Inventor: Anil Goel
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Patent number: 4594403Abstract: 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: GrantFiled: June 13, 1985Date of Patent: June 10, 1986Assignee: BASF AktiengesellschaftInventors: Fritz E. Kempter, Gunther Sabelus, Eberhard Schupp, Wolfram Weiss
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Patent number: 4594291Abstract: Relatively high molecular weight epoxy resins cured with conventional curing agents are disclosed wherein the relatively high molecular weight epoxy resin is prepared in the presence of the curing agents. The resultant cured epoxy resin has an improvement in Tg or toughness and the mixture prior to reaction and curing is much easier to apply as a coating or in the preparation of castings, laminates and the like as compared to applications of mixtures of relatively high molecular weight epoxy resins and the curing agents.Type: GrantFiled: March 25, 1985Date of Patent: June 10, 1986Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Jody R. Berman, James A. Clarke
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Patent number: 4579932Abstract: Cationic epoxy resin esters suitable as binders for stoving coating compositions, particularly for application by electrodeposition, and as mill base resins for grinding pigments and extenders; and a process for producing same is described. The resin esters are produced through reaction of a resinous compound carrying at least two 1,2-epoxy groups with carboxylic acids and, optionally, with primary and/or secondary alkyl- and/or alkanolamines. The carboxylic acid employed, totally or partially, is the reaction product of a dicarboxylic acid anhydride and a tertiary amine which has the structure - ##STR1## wherein R and R.sub.x are a hydrogen atom or an alkyl radical or an aryl radical which may be substituted, R.sub.Type: GrantFiled: November 7, 1983Date of Patent: April 1, 1986Assignee: Vianova Kunstharz, A.G.Inventors: Willibald Paar, Helmut Honig
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Patent number: 4568727Abstract: Storage stable, heat curable mixtures obtained from epoxy resins as a binder system containing latent hardening agents as well as fillers and additive materials which have outstanding mechanical and electrical properties and which are obtained as epoxy resin components of an adduct of a high molecular solid epoxy resin and 4,4'-diaminodiarylalkane in a molecular ratio of 1:0.01 to 0.05. The preferred economical curing agent is a phenol formaldehyde condensation product.Type: GrantFiled: March 12, 1985Date of Patent: February 4, 1986Assignee: Rutgerswerke AktiengesellschaftInventors: Rolf Herzog, Dietrich Tichy, Harald Heerdegen, Rolf Kraas, Ulrich Grundke
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Patent number: 4565852Abstract: 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: GrantFiled: December 27, 1983Date of Patent: January 21, 1986Assignee: Ford Motor CompanyInventor: Saiyed B. A. Qaderi
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Patent number: 4564648Abstract: 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: GrantFiled: September 21, 1984Date of Patent: January 14, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventors: Jozef T. Huybrechts, Victor R. Vleminckx
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Patent number: 4559393Abstract: 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: GrantFiled: December 27, 1983Date of Patent: December 17, 1985Assignee: Ford Motor CompanyInventor: Joseph W. Holubka
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Patent number: 4554332Abstract: Novel epoxy-polyester graft copolymer and novel, solvent-based thermosetting coating composition comprising said copolymer and blocked polyisocyanate crosslinking agent. Coating composition may be formulated as hot sprayable, high solids coating composition suitable for use as a chip resistant automotive vehicle primer adapted for use on body panel areas subject to chipping by stones, gravel and other road debris. Alternatively, composition may be formulated as a high solids composition sprayable with conventional spraying equipment. Epoxy-polyester monomers in presence of hydroxy functional epoxy ester resin precursor. Precursor resin is formed by reaction of diepoxide, chain extended with diphenol and dicarboxylic acid, with hydroxy functional secondary amine in chain terminating reaction.Type: GrantFiled: July 5, 1983Date of Patent: November 19, 1985Assignee: Ford Motor CompanyInventors: Panagiotis I. Kordomenos, Andrew H. Dervan, Dennis J. Grebur
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Patent number: 4550146Abstract: Process for producing cationic epoxy resins carrying oxazolidine groups suitable as paint binders, and particularly paint binders for the formulation of cathodically depositable paints, wherein the epoxy resin is reacted with a hydroxy functional oxazolidine compound or with an oxazolidine compound carrying in the ring the structure ##STR1## in the presence of a monocarboxy compound. The presence of the monocarboxy compound permits the direct reaction or linkage of the epoxy resin with the oxazolidine compound without gelation; and, additionally, the monocarboxy compound favorably influences the film-forming characteristics of the binders.Type: GrantFiled: December 19, 1984Date of Patent: October 29, 1985Assignee: Vianova Kunstharz, A.G.Inventors: Willibald Paar, Helmut Honig
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Patent number: 4547409Abstract: The invention relates to a self-crosslinking heat-curable binder, in particular for electropaints, which is based on an organic synthetic resin which contains primary and/or secondary and, if desired, also tertiary amino groups and esterified carboxyl groups and is water-dilutable due to partial or complete neutralization with acids. The esterified carboxyl groups are activated in the alcohol component by a substituent which induces a negative inductive effect.Type: GrantFiled: October 2, 1984Date of Patent: October 15, 1985Assignee: BASF Farben & Fasenn A.G.Inventors: Michael Geist, Horst Diefenbach
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Patent number: 4546155Abstract: A latent curing agent for epoxy resin, characterized in that the latent curing agent is an adduct obtained by reacting (a) a polyfunctional epoxy compound, (b) a compound having at least one OH, NH.sub.2, NH or SH group together with a tertiary amino group in the molecule and (c) a carboxylic acid anhydride is a good curing agent for epoxy resins. The present curing agent is useful in formulating storable, one-package, heat-curable epoxy resin-based compositions.Type: GrantFiled: September 26, 1984Date of Patent: October 8, 1985Assignee: Ajinomoto Co., Inc.Inventors: Takeshi Hirose, Nobuo Ito, Kiyomiki Hirai, Koji Takeuchi
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Patent number: 4543406Abstract: A cathode-precipitating electrodeposition coating having excellent low-temperature curability, said composition consisting essentially of(A) 100 parts by weight of a high molecular compound having a molecular weight of 500 to 10,000 and containing carbon-carbon double bonds with an iodine value of 50 to 500 and 30 to 300 millimoles of amino groups per 100 g,(B) 10 to 200 parts by weight of a product of reaction of a diglycidyl compound represented by the general formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: October 15, 1984Date of Patent: September 24, 1985Assignees: Nippon Paint Co., Ltd., Nippon Oil Company, Ltd.Inventors: Yutaka Otsuki, Hiroyoshi Omika, Akio Oshima, Yoshihiko Araki, Yasuyuki Tsuchiya
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Patent number: 4537834Abstract: Metal, preferably divalent copper, cobalt or nickel, phthalocyanine tetraamines are used as curing agents for epoxides. The resulting copolymers have high thermal and chemical resistance and are homogeneous. They are useful as binders for laminates, e.g. graphite cloth laminate.Type: GrantFiled: April 11, 1984Date of Patent: August 27, 1985Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Bappalige N. Achar, George M. Fohlen, John A. Parker
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Patent number: 4533682Abstract: 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: GrantFiled: April 29, 1983Date of Patent: August 6, 1985Assignee: DeSoto, Inc.Inventors: Anthony J. Tortorello, Nestor P. Hansen, Kathryn M. Jarocki
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Patent number: 4528127Abstract: This invention is directed to a composition for coating a substrate with a powder coating and to a method of making matt finishes. The composition comprises a solid polyepoxide resin, a solid curing agent in which at least 50 weight percent of the curing agent is a 1:1 mole ratio adduct of rosin and maleic anhydride, a catalyst for promoting the reaction between the polyepoxide and the curing agent, and a pigment. The method of making matt finishes comprises (1) applying to a surface the above-described composition and (2) curing the mixture at a temperature from 140.degree. to 250.degree. C.Type: GrantFiled: August 10, 1984Date of Patent: July 9, 1985Assignee: The Dow Chemical CompanyInventors: Rolf Holderegger, Josef H. Jilek
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Patent number: 4507441Abstract: A compound containing an epoxy group, is reacted with a carboxyl compound by heating a mixture of these compounds in the presence of a benzotriazole such as unsubstituted benzotriazole or tolyltriazole as accelerator. The accelerator is particularly effective in the reaction of a carboxyl compound which is a polyester containing free carboxylic acid groups with an epoxy compound which is triglycidyl cyanurate or an epoxy resin based on bisphenol A.Type: GrantFiled: May 9, 1984Date of Patent: March 26, 1985Assignee: Scott Bader Company LimitedInventor: John O. Goring
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Patent number: 4497938Abstract: Novel solvent-based thermosetting composition comprising (a) hydroxy functional epoxy ester resin of number average molecular weight (Mn) between about 1,000 and about 5,000, being formed by reaction of diepoxide, which has been chain extended with dicarboxylic acid, with hydroxy functional secondary amine in chain terminating reaction, in approximately 1:1 molar equivalent ratio; and (b) polyfunctional, hydroxy-reactive crosslinking agent, for example, aminoplast crosslinking agent or blocked polyisocyanate crosslinking agent comprising isocyanate groups blocked by reaction with an active hydrogen bearing blocking agent. Coating composition may be formulated as primer sprayable with conventional spraying equipment.Type: GrantFiled: December 27, 1983Date of Patent: February 5, 1985Assignee: Ford Motor CompanyInventor: Panagiotis I. Kordomenos
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Patent number: 4495335Abstract: The invention relates to a self-crosslinking heatcurable binder, in particular for electropaints, which is based on an organic synthetic resin which contains primary and/or secondary and, if desired, also tertiary amino groups and esterified carboxyl groups and is water-dilutable due to partial or complete neutralization with acids. The esterified carboxyl groups are activated in the alcohol component by a substituent which induces a negative inductive effect.Type: GrantFiled: March 7, 1983Date of Patent: January 22, 1985Assignee: BASF Farben & Fasern AGInventors: Michael Geist, Horst Diefenbach
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Patent number: 4480084Abstract: This invention is directed to polymeric compounds which contain the polyalkylpiperidine radical and at least two primary hydroxyl groups. These compounds are useful as light stabilizers for plastics and coatings. More particularly, the polymeric stabilizers is formed by chain extending polyalkylpiperidine with an excess of epoxy resin to form a diepoxide functional polymer which is then capped with hydroxy functional monomer.Type: GrantFiled: October 13, 1983Date of Patent: October 30, 1984Assignee: Ford Motor CompanyInventors: Panagiotis I. Kordomenos, Delores J. Alexander, David M. Thomson
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Patent number: 4477642Abstract: The invention relates to a selfcrosslinking heat-hardenable binder, in particular for electropaints, which is based on an organic synthetic resin which contains hydroxyl groups and esterified carboxyl groups in the form of carbalkoxymethyl ester groups and is water-dilutable by partial or complete acid-neutralization of amino groups present in the resin.Type: GrantFiled: August 24, 1983Date of Patent: October 16, 1984Assignee: BASF Farben & Fasern AGInventors: Michael Geist, Horst Diefenbach
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Patent number: 4447594Abstract: Heat-curable compositions comprising an ester of an ethylenically unsaturated acid and a polyhydric alcohol, an oxopropyl isocyanurate formed by the addition of from 2 to 3 moles of acrolein to 1 mole of isocyanuric acid and a free radical or ionic initiator. The compositions are useful as coatings, adhesives and the like.Type: GrantFiled: December 21, 1981Date of Patent: May 8, 1984Assignee: Monsanto CompanyInventors: Saul M. Cohen, John R. LeBlanc
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Patent number: 4431781Abstract: Paint binders and process of producing same water-soluble upon total or partial neutralization with inorganic or organic acids comprising the reaction product of an epoxy compound having at least two 1,2-epoxy groups with secondary oxazolidine amines and saturated or unsaturated carboxylic acids; said binders having a theoretical amine value of at least 35 mg KOH/g. The paint binders are particularly useful in paints formulated for cathodic deposition. Paints formulated with said binders exhibit good applicational characteristics including throwing power, and the cured films have good mechanical and chemical resistance.Type: GrantFiled: October 12, 1982Date of Patent: February 14, 1984Assignee: Vianova Kunstharz, A.G.Inventor: Willibald Paar
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Patent number: 4424336Abstract: Heat-curable mixtures of one or more epoxide compounds, which, on average, have more than one epoxide group in the molecule, and one or more .beta.-aminocrotonic acid derivatives, such as .beta.-aminocrotononitrile, .beta.-aminocrotonamide or .beta.-aminocrotonic acid esters, and also, if desired, a polyamine or polycarboxylic acid anhydride or a malenimide. The novel curable mixtures are distinguished by outstanding stability on storage, can be processed easily and give moulded materials with good mechanical properties.Type: GrantFiled: September 16, 1982Date of Patent: January 3, 1984Assignee: Ciba-Geigy CorporationInventor: Theobald Haug
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Patent number: 4423168Abstract: Coating compositions comprising a polymeric polyol with a polyester crosslinking agent having at least two beta-amido ester groups per molecule are disclosed. The compositions, when applied to a substrate and cured in the presence of a transesterification catalyst, give solvent-resistant coatings.Type: GrantFiled: July 29, 1981Date of Patent: December 27, 1983Assignee: PPG Industries, Inc.Inventor: Joseph T. Valko
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Patent number: 4410664Abstract: The resins described herein are polyimide-epoxy thermoset resins prepared by reacting a polyepoxide with a solution of an admixture of a polyimide dianhydride with another polyimide component, either a polyimide dianhydride or a polyimide diamine, at least one of which polyimide components is insoluble in the particular solvent in the absence of the other polyimide component or components. "Polyimide dianhydride" is an anhydride-terminated polyimide and "polyimide diamine" is an amine-terminated polyimide as represented by the respective formulas: ##STR1## wherein Ar', Ar and n are as defined hereinafter. For use in the present compositions, the polyimide dianhydride has an anhydride activity of at least 0.17 as defined herein, and the ratio of epoxy equivalent to anhydride plus amine equivalents is at least 1/1.Type: GrantFiled: September 20, 1982Date of Patent: October 18, 1983Assignee: Plastics Engineering CompanyInventor: Chung J. Lee
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Patent number: 4398009Abstract: The invention relates to oligomeric and/or polymeric precursor stages of polyoxazoles, as well as to a method for the preparation of these precursor stages. New radiation-reactive polymer precursor stages are provided comprised of addition products of olefinically unsaturated monoepoxides on hydroxyl group-containing polycondensation products of aromatic and/or heterocyclic dihydroxy diamino compounds with dicarboxylic-acid chlorides or esters. The radiation-reactive precursor stages according to the invention are suitable, for example, for the preparation of highly heat-resistant relief structures and as coatings for the optical fibers of light waveguides.Type: GrantFiled: August 19, 1980Date of Patent: August 9, 1983Assignee: Siemens AktiengesellschaftInventors: Hellmut Ahne, Eberhard Kuhn, Roland Rubner
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Patent number: 4379909Abstract: Coating lacquers, particularly useful for coating cans, comprise an epoxide resin, a polycarboxylic acid anhydride curing agent, an organic solvent and an accelerator derived from melamine, benzoguanamine or glycoluril. Particularly useful accelerators are the formaldehyde condensates of these materials and their ethers. The coatings are non-toxic and are cured at temperatures lower than conventional.Type: GrantFiled: October 26, 1981Date of Patent: April 12, 1983Assignees: Hermann Wiederhold GmbH Corp., Imperial Chemical Industries PLCInventors: Hans R. Falkenburg, Siegfried Krause, Robert C. McGuiness
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Patent number: 4371665Abstract: Modified epoxy resin composition having excellent flexibility and excellent compatibility with conventional epoxy resins as well as the original properties of the epoxy resin before modified such as mechanical strength, adhesion, heat resistance and chemical resistance, which is obtained by treating an epoxy resin with at least one modified adduct [D] of a conjugated diene polymer or copolymer which has an imido bond and/or amido bond and a semi-ester structure and has an acid value owing to a free carboxyl group of 5 to 100, said modified adduct being obtained by reacting an adduct [A] of a polymer of a conjugated diene having a number average molecular weight of 300 to 20,000 or a copolymer of the conjugated diene and a vinyl monomer with an .alpha.,.beta.-unsaturated dicarboxylic acid or its anhydride, with a compound [B] of the formula: ##STR1## and a compound [C] of the formula:R.sub.3 --CH.sub.2).sub.m OH [II].Type: GrantFiled: December 22, 1981Date of Patent: February 1, 1983Assignees: Sumitomo Chemical Company, Limited, Tohto Kasei Co., Ltd.Inventors: Minoru Hino, Takao Oshima
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Patent number: 4368317Abstract: A mixture for the preparation of novel cross-linked nitrogen-containing polyadducts, which contains(a) a N-cyanolactam of the formula I or II ##STR1## and (b) a monomeric or oligomeric organic compound having not less than 2 C atoms and not less than 2 hydroxyl groups.The mixture, with or without addition of a monohydroxy compound, can be used as a casting resin or adhesive, or for the production of foams or coatings.The symbols in the formula are all as defined in claim 1.Type: GrantFiled: May 11, 1981Date of Patent: January 11, 1983Assignee: Ciba-Geigy CorporationInventors: Friedrich Lohse, Dieter Trachsler
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Patent number: 4367319Abstract: Auto-crosslinking, cathodically depositable binders which are water-dilutable upon neutralization comprising the reaction product of:(A) 2 moles of a polyepoxy compound with from 2 to 10 epoxy groups per molecule and an epoxy equivalent of from 100 to 1000;(B) 0.1 to 2.0 moles of a diamine, the nitrogen atoms being secondary-secondary or primary-tertiary;(C) from 1 to 10 moles of an alpha,beta-unsaturated monocarboxylic acid; and(D) from 0.5 to 10 moles of dialkanol amine and/or of a monoalkanol monoalkyl amine,whereby the weight ratios of the components are chosen in order that the sum of the epoxy-reactive hydrogen atoms of components (B) through (D) substantially correspond to the number of epoxy groups of component (A), and the binder contains from 0.5 to 2.5 basic nitrogen atoms and from 0.5 to 2.5 polymerizable double bonds per 1000 molecular weight units.Type: GrantFiled: December 15, 1980Date of Patent: January 4, 1983Assignee: Vianova Kunstharz, A.G.Inventors: Georg Pampouchidis, Helmut Honig
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Patent number: 4366274Abstract: Auto-crosslinkable, cathodically depositable aqueous coating compositions which are the reaction product of 2 moles of a diepoxide, 1 mole of a secondary-secondary or primary-tertiary diamine, 0-1 moles of a saturated and/or unsaturated monocarboxylic acid, and 2-1 moles of a secondary amine with optional subsequent partial or total reaction of the hydroxy groups of the reaction product with an alpha,beta-unsaturated monoisocyanate. The binders are rendered water-soluble by neutralization with inorganic and/or organic acids. The binders are capable of being neutralized with low levels of neutralizing acids to provide a component of a coating composition which will cure at low temperatures to give films having excellent surface qualities.Type: GrantFiled: December 15, 1980Date of Patent: December 28, 1982Assignee: Vianova Kunstharz, A.G.Inventors: Georg Pampouchidis, Helmut Honig
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Patent number: 4360655Abstract: Heat-curable mixtures of one or more epoxide compounds, which, on average, have more than one epoxide group in the molecule, and one or more .beta.-aminocrotonic acid derivatives, such as .beta.-aminocrotononitrile, .beta.-aminocrotonamide or .beta.-aminocrotonic acid esters, and also, if desired, a polyamine or polycarboxylic acid anhydride or a maleimide. The novel curable mixtures are distinguished by outstanding stability on storage, can be processed easily and give moulded materials with good mechanical properties.Type: GrantFiled: June 1, 1981Date of Patent: November 23, 1982Assignee: Ciba-Geigy CorporationInventor: Theobald Haug
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Patent number: 4338225Abstract: A functionally terminated polybutadiene polymer is reacted with an epoxide to produce an epoxide terminated polybutadiene. A toughening agent and a peroxide free radical initiator are mixed with the epoxy terminated polybutadiene, and upon reaction a tough thermoset resin is produced having advanced chemical, electrical, and thermomechanical properties. Particular improvements are in the resistant-to-moisture and the tensile strain-to-failure properties.Type: GrantFiled: August 4, 1980Date of Patent: July 6, 1982Assignee: The Boeing CompanyInventor: Clyde H. Sheppard
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Patent number: 4332928Abstract: Polyaminopolyamide compounds are provided which comprise the reaction product of at least one carboxylic acid anhydride selected from mono-, di-, and poly-anhydrides with at least one polyamine of the formula:H.sub.2 N--R--(NH.sub.2).sub.xin an amount of at least about 2 moles per mole of carboxylic acid anhydride group wherein R is selected from an aromatic group containing from about 13 to about 34 carbon atoms; a cycloalkyl group containing from about 13 to about 34 carbon atoms; and an alkyl group containing from about 9 to about 25 carbon atoms, which may further contain at least one heteroatom selected from oxygen, nitrogen, and sulfur; and x is an integer of from about 2 to about 9, preferably from about 2 to about 5.Type: GrantFiled: March 3, 1981Date of Patent: June 1, 1982Assignee: Milliken Research CorporationInventors: Edward W. Kluger, Calvin D. Welch
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Patent number: 4324713Abstract: A two-package solventless rust preventive material comprises (A) a sprayable component essentially containing a liquid epoxy resin and a liquid polycarboxylic acid anhydride and (B) a sprayable component essentially containing a liquid primary or secondary amino compound and a curing accelerator, at least one of said components (A) and (B) essentially comprising a non-reactive epoxy resin diluent having a molecular weight of 300 to 4,000 and an electrically conductive powder.Type: GrantFiled: February 4, 1980Date of Patent: April 13, 1982Assignees: Nippon Zeon Co. Ltd., Nisson Motor Co. Ltd.Inventors: Ryuji Kita, Hisataka Komai, Makoto Wakabayashi, Haruyoshi Takagishi
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Patent number: 4308188Abstract: A water-dilutable polymer for use in water-borne coatings comprising the half ester zwitterion reaction product of a polymer containing cyclic acid anhydride groups with an alkanolamine of the formula ##STR1## where R is hydrogen or hydroxy, R.sup.1 is hydrogen, hydroxy or methyl and can be the same or different, and R.sup.2 is hydrogen or an aliphatic hydrocarbon group of from 1 to 3 carbon atoms.Type: GrantFiled: June 2, 1980Date of Patent: December 29, 1981Assignee: International Minerals & Chemical Corp.Inventors: Zeno W. Wicks, Milton E. Woods, Chiew-Wah Koay
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Patent number: 4301186Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.Type: GrantFiled: June 28, 1979Date of Patent: November 17, 1981Assignee: Bayer AktiengesellschaftInventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder