With Reactant Containing At Least One Cyclic Ether Group Patents (Class 528/365)
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Patent number: 4313859Abstract: The invention comprises a polymerizable liquid mixture of (a) a half ester characterized by the following empirical formula: ##STR1## wherein n is a number having an average value of about 1.5 to less than about 4, m is equal to the free valence of R less the average value of n, R is the hydroxyl-free residue of an organic polyol which contained from 2 to 4, inclusive, hydroxyl groups, OH, in formula (I) (b) maleic anhydride, (c) an epoxide containing two or more 1,2-epoxide radicals, (d) an ethylenically unsaturated monomer which forms a liquid homogeneous mixture with the half ester, maleic anhydride and epoxide, and (e) a basic compound.Type: GrantFiled: July 28, 1980Date of Patent: February 2, 1982Assignee: Union Carbide CorporationInventor: Hugh C. Gardner
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Patent number: 4310644Abstract: A vinyl ester resin composition having excellent physical, mechanical and handling properties is provided which comprises: a vinyl ester resin made by condensing an epoxy resin and an ethylenically unsaturated monocarboxylic acid; and a thixotropy imparting amount of a thixotropy imparting material selected from at least one condensation product of a sugar alcohol with an aromatic aldehyde.Type: GrantFiled: August 14, 1980Date of Patent: January 12, 1982Assignee: Milliken Research CorporationInventor: John W. Miley
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Patent number: 4308356Abstract: Resin-forming polyepoxides are mixed with polyoxazolidinyl compounds or polymers containing pendant oxazolidinyl groups in which the carbon atom in the 2-position of the heterocyclic ring is substituted with saturated hydrocarbon groups, such as dialkyl, or with an alkylene group forming a saturated ring with the carbon atom in the 2-position of the oxazolidinyl ring to form, in the absence of water, a stable composition which can be stored in closed containers for months without undergoing gelation. When such compositions are spread into films and the films exposed to moisture at ambient temperature, e.g., to ambient air having a relative humidity of at least 20% and temperature of about 15.degree. to 25.degree. C., the polymer serves to react with and cure the polyepoxide.Type: GrantFiled: January 30, 1980Date of Patent: December 29, 1981Assignee: Rohm and Haas CompanyInventors: William D. Emmons, Wayne E. Feely
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Patent number: 4302574Abstract: Certain tetrahydrocarbyl phosphonium phenoxide salts are described herein which are novel compounds and/or novel catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids or anhydrides. These catalysts are particularly useful in preparing high molecular weight epoxy resins by the advancement reaction of diglycidyl ether of bisphenol A with bisphenol A.Type: GrantFiled: May 12, 1980Date of Patent: November 24, 1981Assignee: The Dow Chemical CompanyInventors: George A. Doorakian, James L. Bertram
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Patent number: 4301261Abstract: The present invention provides an improved process for reducing the premature gelation during esterification of epoxy compounds containing tertiary, allylic or benzylic hydrogens (e.g., saturated epoxy resins) with ethylenically unsaturated monocarboxylic acids (e.g., acrylic acid) wherein the epoxy compound in pre-reacted with a trialkylphosphite (e.g., triethylphosphite) prior to the esterification.Type: GrantFiled: June 27, 1980Date of Patent: November 17, 1981Assignee: Shell Oil CompanyInventor: Roy J. Jackson
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Patent number: 4293672Abstract: The present invention provides an improved process for reducing the premature gelation during esterification of epoxy compounds containing tertiary, allylic or benzylic hydrogens, e.g., saturated epoxy resins, with ethylenically unsaturated monocarboxylic acids, e.g., acylic acid, which comprises prereacting the said epoxy compound with a hydroxylamine compound prior to the esterification step.Type: GrantFiled: June 27, 1980Date of Patent: October 6, 1981Assignee: Shell Oil CompanyInventor: Roy J. Jackson
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Patent number: 4293681Abstract: An anhydride blend of from 7 to 25 weight percent methyl endomethylenetetrahydrophathalic anhydride and from 75 to 93 weight percent hexahydrophthalic anhydride which is liquid at room temperature and imparts excellent properties to epoxy resins cured with the blend including unexpectedly high impact strength.Type: GrantFiled: February 21, 1980Date of Patent: October 6, 1981Assignee: Buffalo Color CorporationInventor: Edward P. Malik
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Patent number: 4284746Abstract: An epoxy resin composition which comprises (1) an epoxy resin having at least two epoxy groups per molecule and (2) an amine having at least one perfluoroalkyl group and at least one primary and/or secondary amino groups per molecule can be readily cured to afford a cured product, which shows excellent water resistance, oil resistance and stainproof property.Type: GrantFiled: October 12, 1979Date of Patent: August 18, 1981Assignee: Daikin Kogyo Co., Ltd.Inventor: Akira Ohmori
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Patent number: 4284753Abstract: Heat curable epoxy-styrene compositions exhibiting improved processability, low viscosity and long pot life, which when cured with a special acid anhydride/onium salt epoxy curing blend in combination with a free-radical catalyst, yield cured products exhibiting improved physical properties, such as increased heat deflection temperature, increased flexural strength and increased flexibility.Type: GrantFiled: April 14, 1980Date of Patent: August 18, 1981Assignee: Shell Oil CompanyInventor: Ralph W. Hewitt, Jr.
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Patent number: 4273914Abstract: A low temperature, fast curing epoxy insulating composition is made by low temperature mixing an epoxy resin with a carboxylic acid anhydride complex, the anhydride complex being the low temperature reaction product of a selected Lewis Acid catalyst and a carboxylic acid anhydride.Type: GrantFiled: March 6, 1980Date of Patent: June 16, 1981Assignee: Westinghouse Electric Corp.Inventors: James D. B. Smith, Arthur W. Ott
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Patent number: 4268656Abstract: A N-substituted piperazine or N-substituted homopiperazine adduct with a polyepoxide is used as a co-curing agent in epoxy resin systems containing a polyepoxide and a known curing agent such as dicyandiamide, a carboxylic acid anhydride, or a dihydrazide. The preferred adducts have a ratio of epoxy groups to secondary amino groups of between 1.2:1 and 3:1. The preferred polyepoxides are polyglycidyl ethers of 4,4'-isopropylidenediphenol (bisphenol A). Suitable adducts are prepared from N-methyl-, N-(2-hydroxyethyl)-, N-octyl-, N-phenyl- and N-benzyl piperazine and N-methyl homopiperazine.Type: GrantFiled: January 16, 1980Date of Patent: May 19, 1981Assignee: National Starch and Chemical CorporationInventors: Dilip K. Ray-Chaudhuri, Wen B. Chiao, Jules E. Schoenberg
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Patent number: 4252935Abstract: Esters of glycidyl polyethers of saturated phenols are especially useful in coating compositions having a low organic solvent content. The esters are the reaction products of from about 0.5 to about 1.5 equivalents of a saturated monocarboxylic acid with each epoxy group in a diglycidyl polyether of phenols where the aromatic rings of the phenols are saturated.Type: GrantFiled: July 31, 1979Date of Patent: February 24, 1981Assignee: PPG Industries, Inc.Inventors: Carl C. Anderson, William J. Birkmeyer, Roger M. Christenson, Rostyslaw Dowbenko, Ronald J. Lewarchik
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Patent number: 4250300Abstract: A fluorine-containing polyester which comprises essentially as the constituting units (a) a group of the formula: ##STR1## wherein Rf is a perfluoroalkyl group having 8 to 21 carbon atoms and n is an integer of 0 or 1 and (b) a group of the formula: ##STR2## wherein R is one of the groups represented by the formulas: ##STR3## wherein R.sub.1 to R.sub.6 is each a hydrogen atom or a lower alkyl group, R.sub.1 and R.sub.3 being optionally combined together at the terminal carbon atoms to form a cyclic ring, X is a halogen atom or a lower alkyl group and m is an integer of 0 to 4, and is useful as a water and oil-repelling agent or a non-sticking agent.Type: GrantFiled: March 12, 1979Date of Patent: February 10, 1981Assignee: Daikin Kogyo Co., Ltd.Inventors: Takeo Saegusa, Akira Yamada, Masaaki Iwase, Akitoshi Iwatani
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Patent number: 4248753Abstract: Resinous compositions which are the Michael adducts of primary and/or secondary amines and polymers containing alpha, beta-ethylenically unsaturated moieties in conjugation with carbonyl moieties are disclosed. The compositions are depositable on substrates to form films. The films are amenable to oxidative and aminoplast cures and cure with light color. The compositions are desirable for use in cationic electrodeposition.Type: GrantFiled: August 28, 1978Date of Patent: February 3, 1981Assignee: PPG Industries, Inc.Inventors: Stephen L. Buchwalter, Joseph F. Bosso, Roger M. Christenson
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Patent number: 4246161Abstract: A highly fluid, solventless, resinous, impregnating and coating composition, suitable as a high voltage insulation for electrical members, is made from an admixture containing: 100 parts of an epoxy resin, about 25 to 200 parts of an acid anhydride reactive with the epoxy resin, and about 0.002 to 1.00 part of a selected metal carbonyl, acting as a latent accelerator.Type: GrantFiled: August 8, 1979Date of Patent: January 20, 1981Assignee: Westinghouse Electric Corp.Inventors: James D. B. Smith, Robert N. Kauffman
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Patent number: 4240938Abstract: A water-soluble reactive binder, characterized by a combination of at least three of the components(a) at least one halogen-free polycarboxylic acid compound;(b) at least one salt-forming substance selected from the group consisting of alkali metal, alkaline earth metal and quaternary ammonium salts, organic bases and ammonia;(c) at least one component selected from the group consisting of(c1) a polymer containing OH groups; and(c2) an epoxide compound,wherein the components (a) to (c2) are present as such or at least partially in chemically bonded form, a process for its preparation, an article coated with said binder and an adhesive containing said binder.Type: GrantFiled: March 16, 1979Date of Patent: December 23, 1980Assignee: Hoechst AktiengesellschaftInventors: Kurt Kraft, Gerd Walz, Thaddaus Wirth, Ernst-August Theiling
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Patent number: 4202987Abstract: Novel bis-anthranilates are obtained by reacting 1 mol of a N,N'-bis-(hydroxyalkyl)-urea with 2 mols of isatoic anhydride. The novel bis-anthranilates are valuable chain extenders for polyurethanes and valuable crosslinking agents for polyurea and epoxide resins.Type: GrantFiled: December 4, 1978Date of Patent: May 13, 1980Assignee: Ciba-Geigy CorporationInventors: Jurgen Habermeier, Roland Moser, Wolfgang Seiz
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Patent number: 4197390Abstract: Chemically modified thickenable vinyl esters prepared by reacting an ethylenically unsaturated monocarboxylic acid with a polyepoxide in the presence of a small amount of a dicarboxylic acid. These resins are usually diluted with a copolymerizable monomer such as styrene, blended with a Group II metal oxide or hydroxide and other additives, and cured with a free-radical catalyst.Type: GrantFiled: February 22, 1979Date of Patent: April 8, 1980Assignee: Shell Oil CompanyInventor: Roy J. Jackson
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Patent number: 4192786Abstract: This invention relates to an epoxy resin composition suitable for impregnating coils of electrical apparatus such as motors, generators and the like. More particularly, this invention relates to an epoxy resin composition having excellent workability and a long pot life, which composition is prepared by adding the reaction product of the glycidyl ether of a monoalcohol and a metal carboxylate, which works as a reactive diluent and accelerator, to an epoxy resin having at least two epoxy groups per molecule and containing a curing agent.Type: GrantFiled: April 19, 1978Date of Patent: March 11, 1980Assignee: Mitsubishi Denki Kabushiki KaishaInventors: Kyoichi Shibayama, Kazuo Okahashi, Osamu Hayashi
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Patent number: 4191835Abstract: Bis-anthranilates of the formula I ##STR1## or mixtures thereof, in which, in the formula, m and n are each 0 or a number from 1 to 5, preferably a number from 1 to 3, and the sum of m and n must be at least 1, as novel chain extenders and crosslinking agents for the production of polyurethanes and polyurea resins. The compounds of the formula I are also suitable as curing agents for epoxide resins.Type: GrantFiled: December 4, 1978Date of Patent: March 4, 1980Assignee: Ciba-Geigy CorporationInventors: Jurgen Habermeier, Roland Moser
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Patent number: 4188474Abstract: A novel epoxy resin curing accelerator comprises oligomeric poly(ethylenepiperazine). The resins comprise a vicinal polyepoxide, a curing agent, and an amount of oligomeric poly(ethylenepiperazine) effective for accelerating the cure of the polyepoxide.Type: GrantFiled: September 11, 1978Date of Patent: February 12, 1980Assignee: Texaco Development CorporationInventors: Harold G. Waddill, Philip H. Moss
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Patent number: 4180607Abstract: Disclosed is an epoxy resin composition containing, as an essential curing component, 2,3,3',4'-biphenyltetracarboxylic dianhydride which is highly compatible with epoxy resins at a relatively low temperature and effective for producing cured epoxy resins having an excellent thermal resistance.Type: GrantFiled: August 31, 1978Date of Patent: December 25, 1979Assignee: Ube Industries, Ltd.Inventors: Ichiro Sasaki, Hiroshi Itatani, Mikito Kashima
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Patent number: 4178274Abstract: Casting resin compositions for sealing opto-electronic components on the basis of quick-setting casting resin compounds, consisting of at least one epoxy compound with a cycloaliphatic base with at least two oxiran rings in the molecule, at least one carbonic acid anhydride, a zinc octoate, a low-molecular polyol and/or a low-molecular acid ester and, optionally, an organic phosphorus compound and customary brighteners and light-scattering material in powder form and pigments. Especially suitable is a zinc octoate with a zinc content of 21 to 22% by weight. The compounds are used for covering and coating light-emitting diodes, photo transistors, photo diodes and light-emitting diode displays and as light guides for opto-electronic couplers.Type: GrantFiled: March 14, 1978Date of Patent: December 11, 1979Assignee: Siemens AktiengesellschaftInventors: Hans Denk, Ulrike Reeh
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Patent number: 4174455Abstract: Anthranilates of the formula ##STR1## wherein each R is hydrogen or ##STR2## each n is the number 2, 3 or 4, y is nought or 1 and X is an alkylene radical having 1 to 8 C atoms, meta- or para-phenylene or meta- or para-cyclohexylene, are obtained by reacting a hydroxyalkylated dicarboxylic acid diamide of the formula ##STR3## wherein each R is hydrogen or --CH.sub.2).sub.n OH and n, y and X are as defined above, with isatoic anhydride, preferably in the presence of an alkaline catalyst.The novel compounds are valuable chain extenders and crosslinking agents for the production of polyurethanes and polyurea resins and are also suitable as curing agents for epoxide resins.Type: GrantFiled: December 4, 1978Date of Patent: November 13, 1979Assignee: Ciba-Geigy CorporationInventors: Jurgen Habermeier, Roland Moser, Wolfgang Seiz
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Patent number: 4171420Abstract: The trisubstituted (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts and their hydrolyzed derivatives are novel latent catalysts for promoting reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.Type: GrantFiled: September 26, 1978Date of Patent: October 16, 1979Assignee: The Dow Chemical CompanyInventors: George A. Doorakian, Lawrence G. Duquette
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Patent number: 4158727Abstract: Metal-containing self-curing epoxy resin compositions are provided, which can advantageously be employed as adhesives, casting resins, paints and the like. The compositions comprise (i) a metal-containing compound represented by the general formula;HO--R.sub.1 --OOC--R--COOMOOC--R--COO--R.sub.1 --OH(ii) a dibasic acid anhydride, and (iii) an epoxy resin.Type: GrantFiled: November 4, 1977Date of Patent: June 19, 1979Assignee: Okura Kogyo Kabushiki KaishaInventor: Hideaki Matsuda
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Patent number: 4158090Abstract: A new composition capable of being cured to a solid resin highly resistant to boiling acetone which comprises: (a) a 1,2-epoxy resin containing on the average more than one 1,2-epoxy group per molecule; (b) a residue remaining from the process wherein cumene (C) is reacted with maleic anhydride (MA) in the presence of (that is, in contact with) zinc chloride to obtain a reaction product containing dimethylbenzyl succinic anhydride (DMBSA), 5-phenyl-5-methylhexane-1,2,3,4-tetracarboxylic acid dianhydride (PMTD) and addition products of C and MA containing more than two anhydride groups per molecule (AP) and wherein a sufficient amount of said DMBSA is removed from said reaction product to give a residue containing a maximum of 25 weight percent DMBSA; and (c) an accelerator.Type: GrantFiled: February 21, 1978Date of Patent: June 12, 1979Assignee: Gulf Research & Development CompanyInventors: Edward T. Sabourin, Walter P. Barie, Jr.
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Patent number: 4157428Abstract: New and useful blends of thermosetting resins with copolymers of certain amounts of ethylene with another monomer copolymerizable therewith to provide solid but flexible polymers, and a third monomer containing epoxy side groups, and optionally carbon monoxide, are provided. These blends result in performance unattainable with the thermosetting resin alone in terms of flexibility, toughness, and adhesion. Such blends may be used, for example, to produce flexible, semirigid or rigid films, coatings, fibers, foams or molded articles.Type: GrantFiled: March 4, 1977Date of Patent: June 5, 1979Assignee: E. I. Du Pont de Nemours and CompanyInventor: Clarence F. Hammer
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Patent number: 4147856Abstract: A new composition capable of being cured to a solid resin highly resistant to boiling acetone which comprises: (a) a 1,2-epoxy resin containing on the average more than one 1,2-epoxy group per molecule; (b) a residue remaining from the process wherein cumene (C) is reacted with maleic anhydride (MA) to obtain a reaction product containing dimethylbenzyl succinic anhydride (DMBSA), 5-phenyl-5-methylhexane-1,2,3,4-tetracarboxylic acid dianhydride (PMTD) and addition products of C and MA containing more than two anhydride groups per molecule (AP) and wherein a sufficient amount of said DMBSA is removed from said reaction product to give a residue containing a maximum of 25 weight percent DMBSA; and (c) an accelerator.Type: GrantFiled: February 21, 1978Date of Patent: April 3, 1979Assignee: Gulf Research & Development CompanyInventors: Edward T. Sabourin, Walter P. Barie, Jr.
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Patent number: 4146701Abstract: An epoxy resin having superior resistance to thermal shock comprises a vicinal polyepoxide, a curing amount of a certain bicyclic anhydride and an effective amount of an additive comprising a polyoxyalkylenepolyamine-maleic anhydride condensation product having thioureide, ureide or thioformamide or formamide end groups.Type: GrantFiled: March 27, 1978Date of Patent: March 27, 1979Assignee: Texaco Development Corp.Inventors: Harold G. Waddill, Heinz Schulze
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Patent number: 4140703Abstract: Novel phthalic acid derivatives, especially phthalic anhydrides, which are substituted by alkenylamino groups, and a process for their preparation are described. The novel phthalic acid derivatives are valuable intermediates for the preparation of corresponding esters, ester-amides or imides, which, in turn, are used in hot-curable mixtures which are stable on storage and have improved processing characteristics, in particular a prolonged pot life, for the production of mouldings of various types. Phthalic anhydrides substituted by alkenylamino groups, according to the invention, are also suitable as curing agents for epoxide resins. Products or materials cured therewith are distinguished by good mechanical and/or electrical properties.Type: GrantFiled: December 5, 1977Date of Patent: February 20, 1979Assignee: Ciba-Geigy CorporationInventors: Roland Darms, Hubert Meindl
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Patent number: 4137275Abstract: A highly fluid, solventless, resinous, impregnating and coating composition, suitable as a high voltage insulation for electrical members, is made from an admixture containing: 100 parts of an epoxy resin, about 25 to 200 parts of an acid anhydride reactive with the epoxy resin, and about 0.002 to 1.00 part of a selected metal acetylacetonate, acting as a latent accelerator.Type: GrantFiled: April 27, 1976Date of Patent: January 30, 1979Assignee: Westinghouse Electric Corp.Inventors: James D. B. Smith, Robert N. Kauffman
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Patent number: 4132706Abstract: The trisubstituted (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts and their hydrolyzed derivatives are novel latent catalysts for promoting reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.Type: GrantFiled: April 5, 1976Date of Patent: January 2, 1979Assignee: The Dow Chemical CompanyInventors: George A. Doorakian, Lawrence G. Duquette
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Patent number: 4116938Abstract: Resistance to thermal shock of certain anhydride cured epoxy resins is unexpectedly enhanced by addition of certain polyether diureide additives. This superior resistance does not appreciably compromise heat deflection properties. The resins comprise a vicinal polyepoxide, a curing amount of a certain bicyclic anhydride and an effective amount of a polyether diureide having terminal ureido groups and a molecular weight of from about 2,000 to about 3,000.Type: GrantFiled: November 22, 1976Date of Patent: September 26, 1978Assignee: Texaco Development Corp.Inventors: Heinz Schulze, Harold G. Waddill
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Patent number: 4113791Abstract: A resinous composition, suitable as a high voltage insulation for electrical members, is made from an admixture containing: 100 parts of an epoxy resin, about 25 to 200 parts of an acid anhydride reactive with the epoxy resin, about 0.01 to 2.0 parts of chromium or zirconium acetylacetonate, acting as a latent accelerator and about 0.3 to 30 parts of a selected organic carboxylic acid, acting as a co-accelerator.Type: GrantFiled: March 3, 1977Date of Patent: September 12, 1978Assignee: Westinghouse Electric Corp.Inventors: James D. B. Smith, Robert N. Kauffman
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Patent number: 4101459Abstract: To accelerate the curing of epoxide resins by aromatic, heterocyclic, or cycloaliphatic polyamines there are employed salts of trifluoromethanesulfonic acid.Type: GrantFiled: October 20, 1976Date of Patent: July 18, 1978Assignee: Ciba-Geigy CorporationInventor: Christopher Michael Andrews