With Nitrogen-containing Reactant Patents (Class 528/113)
  • Patent number: 4780524
    Abstract: 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: Grant
    Filed: January 23, 1987
    Date of Patent: October 25, 1988
    Assignee: BASF Lacke + Farben AG
    Inventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
  • Patent number: 4769420
    Abstract: 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: Grant
    Filed: November 25, 1986
    Date of Patent: September 6, 1988
    Assignee: BASF Lacke + Farben Aktiengesellschaft
    Inventors: Thomas Schwerzel, Rolf Osterloh, Eberhard Schupp, Klaas Ahlers
  • Patent number: 4761460
    Abstract: 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: Grant
    Filed: March 4, 1987
    Date of Patent: August 2, 1988
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Masahiko Otsuka, Hidekazu Ishimura
  • Patent number: 4749743
    Abstract: Disclosed herein is a low molecular weight epoxy-functional polyurethane and high solids thermosetting coating compositions prepared therewith.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: June 7, 1988
    Assignee: PPG Industries, Inc.
    Inventors: Ronald R. Ambrose, Samuel Porter, Jr.
  • Patent number: 4736010
    Abstract: 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: Grant
    Filed: April 6, 1987
    Date of Patent: April 5, 1988
    Assignees: Asahi Denka Kogyo K.K., A.C.R. Co., Ltd.
    Inventors: Hiroshi Suzuki, Yutaka Asakawa
  • Patent number: 4721742
    Abstract: 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: Grant
    Filed: November 7, 1986
    Date of Patent: January 26, 1988
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Willie L. Myles
  • Patent number: 4713406
    Abstract: Binders for cathodic electrocoating which are based on polyadducts/polycondensates which carry basic nitrogen groups and are rendered water-dilutable by protonation with an acid, and one or more crosslinking agents for these polyadducts/polycondensates, their use and electrocoating baths prepared from them.These binders essentially consist of a mixture of(A) from 50 to 90% by weight of a polyadduct/polycondensate which carries basic nitrogen groups and is obtainable by reacting(a) an essentially epoxide-free adduct of a secondary amine and polyepoxide compound with(b) a condensate of a diamine/polyepoxide adduct which is prepared in the presence of excess diamine and separated off from excess diamine after complete conversion of the epoxide groups, with one or more mono- and/or dicarboxylic acids of not less than 6 carbon atoms.(B) from 10 to 50% by weight of a crosslinking agent which does not react with component (A) at room temperature but reacts with the latter at elevated temperatures with crosslinking.
    Type: Grant
    Filed: November 25, 1986
    Date of Patent: December 15, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Schupp, Rolf Osterloh, Werner Loch, Klaas Ahlers
  • Patent number: 4705833
    Abstract: 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: Grant
    Filed: December 24, 1985
    Date of Patent: November 10, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuhisa Saito, Hisao Takagishi, Katsuya Watanabe, Kohichi Okuno, Junichi Kenmei, Kunimasa Kamio
  • Patent number: 4683285
    Abstract: 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: Grant
    Filed: October 22, 1985
    Date of Patent: July 28, 1987
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Helmut Honig
  • Patent number: 4673723
    Abstract: 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: Grant
    Filed: August 22, 1985
    Date of Patent: June 16, 1987
    Assignee: ATOCHEM
    Inventor: Daniel Cuzin
  • Patent number: 4668757
    Abstract: 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: Grant
    Filed: March 26, 1984
    Date of Patent: May 26, 1987
    Inventor: Gus Nichols
  • Patent number: 4634644
    Abstract: 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: Grant
    Filed: December 10, 1984
    Date of Patent: January 6, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Edward Irving, Terence J. Smith
  • Patent number: 4600763
    Abstract: 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: Grant
    Filed: September 5, 1985
    Date of Patent: July 15, 1986
    Assignee: Ashland Oil, Inc.
    Inventor: Anil Goel
  • Patent number: 4594403
    Abstract: Amide-containing epoxy resin/amine adducts are prepared by a process in which an epoxy resin/amine adduct containing primary and/or secondary aminoalkyl groups is reacted with a carboxylic acid in the presence of esterification catalysts, particularly advantageously in the presence of an alcohol.The products prepared according to the invention are useful as binders for cathodic electrocoating.
    Type: Grant
    Filed: June 13, 1985
    Date of Patent: June 10, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz E. Kempter, Gunther Sabelus, Eberhard Schupp, Wolfram Weiss
  • Patent number: 4594291
    Abstract: 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: Grant
    Filed: March 25, 1985
    Date of Patent: June 10, 1986
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, Jody R. Berman, James A. Clarke
  • Patent number: 4579932
    Abstract: 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: Grant
    Filed: November 7, 1983
    Date of Patent: April 1, 1986
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Helmut Honig
  • Patent number: 4568727
    Abstract: 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: Grant
    Filed: March 12, 1985
    Date of Patent: February 4, 1986
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Rolf Herzog, Dietrich Tichy, Harald Heerdegen, Rolf Kraas, Ulrich Grundke
  • Patent number: 4565852
    Abstract: A crosslinkable composition of matter is provided, which comprises first and second chain extended diepoxide resins, one or both of which are prepared using an excess of diepoxide reactant and modified by reaction with hydroxy functional secondary amine. The first resin, diene functional aminoepoxy resin, and the second resin, blocked dieneophile functional aminoepoxy resin, are co-reactive at elevated cure temperature. The diene functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional diene. The blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional blocked dieneophile chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional blocked dieneophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resins.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: January 21, 1986
    Assignee: Ford Motor Company
    Inventor: Saiyed B. A. Qaderi
  • Patent number: 4564648
    Abstract: Dispersion of an epoxy ester graft acrylic in water with a total of no more than 5% of organic volatiles and amines. These dispersions can be used in primer compositions for metal substrates having a minimum of organic solvent emissions and which can crosslink at temperatures from 110.degree.-200.degree. C., giving a good balance of hardness, flexibility, humidity, corrosion resistance and anti-chipping properties.
    Type: Grant
    Filed: September 21, 1984
    Date of Patent: January 14, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Jozef T. Huybrechts, Victor R. Vleminckx
  • Patent number: 4559393
    Abstract: A self-crosslinkable resin and composition of matter comprising same is provided, which resin comprises certain diene functional blocked dieneophile functional aminoepoxy resin, which resin is self-crosslinkable at elevated cure temperature. The diene functional blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant, mono-secondary amine functional blocked dieneophile and, optionally, monofunctional end-capping reactant such as mono-secondary amine functional diene and mono-secondary amine functional blocked dienophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resin. The crosslinkable composition of matter is useful in coating and other applications, especially solvent-based primer coating compositions and cathodic electrocoating compositions.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: December 17, 1985
    Assignee: Ford Motor Company
    Inventor: Joseph W. Holubka
  • Patent number: 4554332
    Abstract: 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: Grant
    Filed: July 5, 1983
    Date of Patent: November 19, 1985
    Assignee: Ford Motor Company
    Inventors: Panagiotis I. Kordomenos, Andrew H. Dervan, Dennis J. Grebur
  • Patent number: 4550146
    Abstract: 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: Grant
    Filed: December 19, 1984
    Date of Patent: October 29, 1985
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Willibald Paar, Helmut Honig
  • Patent number: 4547409
    Abstract: 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: Grant
    Filed: October 2, 1984
    Date of Patent: October 15, 1985
    Assignee: BASF Farben & Fasenn A.G.
    Inventors: Michael Geist, Horst Diefenbach
  • Patent number: 4546155
    Abstract: 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: Grant
    Filed: September 26, 1984
    Date of Patent: October 8, 1985
    Assignee: Ajinomoto Co., Inc.
    Inventors: Takeshi Hirose, Nobuo Ito, Kiyomiki Hirai, Koji Takeuchi
  • Patent number: 4543406
    Abstract: 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: Grant
    Filed: October 15, 1984
    Date of Patent: September 24, 1985
    Assignees: Nippon Paint Co., Ltd., Nippon Oil Company, Ltd.
    Inventors: Yutaka Otsuki, Hiroyoshi Omika, Akio Oshima, Yoshihiko Araki, Yasuyuki Tsuchiya
  • Patent number: 4537834
    Abstract: 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: Grant
    Filed: April 11, 1984
    Date of Patent: August 27, 1985
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Bappalige N. Achar, George M. Fohlen, John A. Parker
  • Patent number: 4533682
    Abstract: Adducts of imidazolidine compounds, such as the reaction product of ethylene diamine with cyclohexanone, are provided with organic polyepoxides, especially with low molecular weight polyepoxides where the imidazolidine acts as a chain extender, and the adduct is reacted with an acid to protonate at least 50% of the amine groups in the adduct. These protonated adducts can be dispersed in water to form dispersion which cure with various curing agents. Aqueous electrocoating baths can be provided which electrodeposit at the cathode.
    Type: Grant
    Filed: April 29, 1983
    Date of Patent: August 6, 1985
    Assignee: DeSoto, Inc.
    Inventors: Anthony J. Tortorello, Nestor P. Hansen, Kathryn M. Jarocki
  • Patent number: 4528127
    Abstract: 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: Grant
    Filed: August 10, 1984
    Date of Patent: July 9, 1985
    Assignee: The Dow Chemical Company
    Inventors: Rolf Holderegger, Josef H. Jilek
  • Patent number: 4507441
    Abstract: 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: Grant
    Filed: May 9, 1984
    Date of Patent: March 26, 1985
    Assignee: Scott Bader Company Limited
    Inventor: John O. Goring
  • Patent number: 4497938
    Abstract: 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: Grant
    Filed: December 27, 1983
    Date of Patent: February 5, 1985
    Assignee: Ford Motor Company
    Inventor: Panagiotis I. Kordomenos
  • Patent number: 4495335
    Abstract: 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: Grant
    Filed: March 7, 1983
    Date of Patent: January 22, 1985
    Assignee: BASF Farben & Fasern AG
    Inventors: Michael Geist, Horst Diefenbach
  • Patent number: 4480084
    Abstract: 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: Grant
    Filed: October 13, 1983
    Date of Patent: October 30, 1984
    Assignee: Ford Motor Company
    Inventors: Panagiotis I. Kordomenos, Delores J. Alexander, David M. Thomson
  • Patent number: 4477642
    Abstract: 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: Grant
    Filed: August 24, 1983
    Date of Patent: October 16, 1984
    Assignee: BASF Farben & Fasern AG
    Inventors: Michael Geist, Horst Diefenbach
  • Patent number: 4447594
    Abstract: 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: Grant
    Filed: December 21, 1981
    Date of Patent: May 8, 1984
    Assignee: Monsanto Company
    Inventors: Saul M. Cohen, John R. LeBlanc
  • Patent number: 4431781
    Abstract: 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: Grant
    Filed: October 12, 1982
    Date of Patent: February 14, 1984
    Assignee: Vianova Kunstharz, A.G.
    Inventor: Willibald Paar
  • Patent number: 4424336
    Abstract: 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: Grant
    Filed: September 16, 1982
    Date of Patent: January 3, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Theobald Haug
  • Patent number: 4423168
    Abstract: 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: Grant
    Filed: July 29, 1981
    Date of Patent: December 27, 1983
    Assignee: PPG Industries, Inc.
    Inventor: Joseph T. Valko
  • Patent number: 4410664
    Abstract: 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: Grant
    Filed: September 20, 1982
    Date of Patent: October 18, 1983
    Assignee: Plastics Engineering Company
    Inventor: Chung J. Lee
  • Patent number: 4398009
    Abstract: 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: Grant
    Filed: August 19, 1980
    Date of Patent: August 9, 1983
    Assignee: Siemens Aktiengesellschaft
    Inventors: Hellmut Ahne, Eberhard Kuhn, Roland Rubner
  • Patent number: 4379909
    Abstract: 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: Grant
    Filed: October 26, 1981
    Date of Patent: April 12, 1983
    Assignees: Hermann Wiederhold GmbH Corp., Imperial Chemical Industries PLC
    Inventors: Hans R. Falkenburg, Siegfried Krause, Robert C. McGuiness
  • Patent number: 4371665
    Abstract: 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: Grant
    Filed: December 22, 1981
    Date of Patent: February 1, 1983
    Assignees: Sumitomo Chemical Company, Limited, Tohto Kasei Co., Ltd.
    Inventors: Minoru Hino, Takao Oshima
  • Patent number: 4368317
    Abstract: 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: Grant
    Filed: May 11, 1981
    Date of Patent: January 11, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Lohse, Dieter Trachsler
  • Patent number: 4367319
    Abstract: 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: Grant
    Filed: December 15, 1980
    Date of Patent: January 4, 1983
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Georg Pampouchidis, Helmut Honig
  • Patent number: 4366274
    Abstract: 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: Grant
    Filed: December 15, 1980
    Date of Patent: December 28, 1982
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Georg Pampouchidis, Helmut Honig
  • Patent number: 4360655
    Abstract: 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: Grant
    Filed: June 1, 1981
    Date of Patent: November 23, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Theobald Haug
  • Patent number: 4338225
    Abstract: 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: Grant
    Filed: August 4, 1980
    Date of Patent: July 6, 1982
    Assignee: The Boeing Company
    Inventor: Clyde H. Sheppard
  • Patent number: 4332928
    Abstract: 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: Grant
    Filed: March 3, 1981
    Date of Patent: June 1, 1982
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, Calvin D. Welch
  • Patent number: 4324713
    Abstract: 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: Grant
    Filed: February 4, 1980
    Date of Patent: April 13, 1982
    Assignees: Nippon Zeon Co. Ltd., Nisson Motor Co. Ltd.
    Inventors: Ryuji Kita, Hisataka Komai, Makoto Wakabayashi, Haruyoshi Takagishi
  • Patent number: 4308188
    Abstract: 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: Grant
    Filed: June 2, 1980
    Date of Patent: December 29, 1981
    Assignee: International Minerals & Chemical Corp.
    Inventors: Zeno W. Wicks, Milton E. Woods, Chiew-Wah Koay
  • Patent number: 4301186
    Abstract: 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: Grant
    Filed: June 28, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder