Material Contains A Nitrogen Compound Patents (Class 528/93)
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Patent number: 5066735Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecules; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: April 12, 1990Date of Patent: November 19, 1991Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 5057557Abstract: Epoxy resins are modified by reaction with an acidified polytertiary amine-containing compound. These modified epoxy resins when cured result in products having improved properties.Type: GrantFiled: May 11, 1990Date of Patent: October 15, 1991Assignee: The Dow Chemical CompanyInventors: Duane S. Treybig, Pong S. Sheih, John M. McIntyre
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Patent number: 5057590Abstract: Bislactone curing agents are used to cure and copolymerize with epoxy-based esins. Preferably, the copolymerization is performed using a tertiary amine catalyst. During cure, the bislactone ring opens and expands. The use of bislactones as curing agents for epoxy-based resins avoids the shrinkage and accompanying stresses which occur when epoxy-based resins are cured conventionally. The novel bislactone cured epoxy-based polymers according the present invention are less prone to failure than are conventional epoxy-based polymers. In a further embodiment, the epoxy is copolymerized with a novel bislactone monomer having at least one trifluoromethyl group. The resulting fluorinated copolymer has a reduced surface energy.Type: GrantFiled: March 29, 1990Date of Patent: October 15, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventors: Allison M. Sikes, Robert F. Brady, Jr.
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Patent number: 5025077Abstract: A glue composition comprises a heat-hardenable resin, urea and possibly one or several glue additives, and is characterized by the presence of an additional gluing compound is polyol having a functionality of at least equal to three. This glue can be used for mineral fibers in the manufacture of insulation products having improved properties.Type: GrantFiled: July 28, 1988Date of Patent: June 18, 1991Assignee: Isover Saint-GobainInventors: Serge Tetart, Bernard Lericque
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Patent number: 5021537Abstract: A coating composition is provided comprising an epoxy resin, a polyacetoacetate, a curing agent for the epoxy resin, and an optional organic solvent. The presence of the polyacetoacetate permits the preparation of a fast-drying high-solids coating formulation.Type: GrantFiled: April 27, 1990Date of Patent: June 4, 1991Assignee: Shell Oil CompanyInventors: Charles J. Stark, Rita D. Pietruszka
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Patent number: 5017674Abstract: An epoxy resin composition is disclosed that can be cured at a temperature of 150.degree. C. or below, and can be used to provide a high performance carbon fiber composite material having a 0.degree. direction bending strength of 220 kg/mm.sup.2 or over, and an interlayer shear strength of 10 kg/mm.sup.2 or over.The composition is made up of:(A) an epoxy compound containing 10 to 100% by weight of m- or o-methyl-p-N,N-diglycidyl-aminophenyl-ether or its oligomer,(B) diaminodiphenylsulfone and/or diaminodiphenylmethane,(C) dicyandiamide, 2,6-xylenylbiguanide, o-tolylbiguanide, diphenylguanidine, adipil dihydrazide, azelayl dihydrazide, or isophthalic acid dihydrazide, and(D) a urea compound.Type: GrantFiled: June 27, 1990Date of Patent: May 21, 1991Inventors: Hisashi Tada, Yoshinobu Shiraishi, Shigetsuga Hayashi
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Patent number: 5003025Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.Type: GrantFiled: December 20, 1989Date of Patent: March 26, 1991Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4996284Abstract: A process for the preparation of a sulfonamide-based epoxy resinous composition, which includes the step of reacting a sulfonamide compound with a resinous composition containing a plurality of epoxide groups in the presence of a Lewis acid, is disclosed. The epoxy sulfonamide resins of the invention, which are being claimed, have applications in nail lacquer compositions and other cosmetics, adhesives, and in wood and paper coatings, as a plasticizer and as a modifier in injection molding applications for various resins.Type: GrantFiled: April 24, 1989Date of Patent: February 26, 1991Inventor: Leo X. Mallavarapu
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Patent number: 4981941Abstract: Fluoroepoxy resins for use in computer composite circuit boards. A "glass state" curing agent containing a fluorinated monoanhydride, a fluorinated dianhydride and a catalyst is compounded at a temperature of about 210.degree. C. The curing agent is blended with di- and tri-functional epoxy resins at 100.degree. C. or higher to give homogeneous fast-curing syrups. Fluoroepoxy resins inherently have low dielectric constants. This method produces a fluoroepoxy resin with higher crosslink densities and higher glass transition temperatures.Type: GrantFiled: March 27, 1989Date of Patent: January 1, 1991Assignee: The United States of America as represented by the Secretary of the NavyInventor: James R. Griffith
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Patent number: 4977214Abstract: Curable compositions comprise(A) a polyglycidyl ether of a polyhydric phenol,(B) a polyglycidyl ether of a polyhydric alcohol,(C) a nitrogen-containing latent hardener for epoxide resins and(D) as cure accelerator dispersed as a powder in the composition, a solid solution of a polymeric phenol with an aliphatic polyamine having two or more amine groups, each of the amine groups being tertiary and at least two of the amine groups being dimethylamino groups.The compositions are useful as adhesives, sealants, laminating resins and coatings.Type: GrantFiled: October 12, 1989Date of Patent: December 11, 1990Assignee: Ciba-Geigy CorporationInventor: Madan M. Bagga
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Patent number: 4959425Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resing having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: June 27, 1989Date of Patent: September 25, 1990Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4959398Abstract: A powdery adhesive comprised of spherical particles comprising 40 to 90 parts by weight of an epoxy resin component, 10 to 60 parts by weight of a rubber component and a latent curing agent contained inside the particles, the average particle size of the particles being from 0.1 to 500 .mu.m. The powdery adhesive may be prepared by a process comprising a step of preparing a compatible mixture comprising an epoxy resin component, a rubber component and a common organic solvent, a step of emulsifying or suspending the compatible mixture in an aqueous medium to form spherical particles, and a step of causing a phase separation of the epoxy resin component and the rubber component in the spherical particles.Type: GrantFiled: February 13, 1989Date of Patent: September 25, 1990Assignee: Toray Industries, Inc.Inventors: Koichiro Oka, Ikuo Hagiwara
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Patent number: 4956411Abstract: An epoxy resin composition is disclosed that can be cured at a temperature of 150.degree. C. or below, and can be used to provide a high performance carbon fiber composite material having a 0.degree. direction bending strength of 220 kg/mm.sup.2 or over, and an interlayer shear strength of 10 kg/mm.sup.2 or over.The composition is made up of:(A) an epoxy compound containing 10 to 100% by weight of m- or o-methyl-p-N,N-diglycidyl-aminophenyl-ester or its oligomer,(B) diaminodiphenylsulfone and/or diaminodiphenylmethane,(C) dicyandiamide, 2,6-xylenylbiguanide, o-tolylbiguanide, diphenylguanidine, adipil dihydrazide, azelayl dihydrazide, or isophthalic acid dihydrazide, and(D) a urea compound.Type: GrantFiled: January 30, 1989Date of Patent: September 11, 1990Assignee: Mitsubishi Rayon Company, Ltd.Inventors: Hisashi Tada, Yoshinobu Shiraishi, Shigetsugu Hayashi
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Patent number: 4954602Abstract: A liquid, epoxy resin composition suitable for use in fixation of a stator coil or a rotor coil is disclosed, which comprises (A) a mixture containing (a.sub.1) a Bisphenol A epoxy resin and (a.sub.2) an alicyclic epoxy resin; and (B) a curing agent including (b.sub.1) an acid anhydride, and (b.sub.2) a phenol compound of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 represent independently from each other a lower alkyl, R.sup.3 represents a lower alkylene and n is an integer of 1-5, the amount of the phenol compound (b.sub.2) being in the range of 2-8% based on the weight of the mixture (A).Type: GrantFiled: June 23, 1989Date of Patent: September 4, 1990Assignee: Somar CorporationInventors: Ichiro Akutagawa, Tsutomu Yamaguchi, Toshihiro Hanamori, Kunimitsu Matsuzaki, Shinobu Okamura
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Patent number: 4942215Abstract: A thermosetting liquid moulding composition comprising:(a) a polyepoxide containing at least two epoxide groups per molecule;(b) a tricarboxylic acid definable by the general formula: ##STR1## where: R.sup.1, R.sup.2 and R.sup.3 have the meaning given in the description; and(c) a diacarboxylic acid anhydride.This composition can be transformed by liquid moulding into manufactured articles particularly useful in the electrical sector.Type: GrantFiled: November 18, 1988Date of Patent: July 17, 1990Assignee: Enichem Synthesis S.p.A.Inventors: Alberto Greco, Luigi Raisa
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Patent number: 4929650Abstract: A coating material for a tendon for prestressed concrete includes a curing composition, the curing time of which is so controlled that the composition is held in an uncured fluid state for a predetermined time after the concrete hardens. After the predetermined time passes, the composition cures. By coating a tendon for prestressed concrete with the coating material having such properties, an antirust effect of the tendon, an improved adhering force of the tendon to the concrete and a decreased cost of manufacturing prestressed concrete can be obtained.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignees: Mitsui Sekiyu Kagaku Kogyo Kabushiki Kaisha, Shinko Kosen Kogyo Kabushiki KaishaInventors: Makoto Kurauchi, Michio Hashimoto, Kiyoshi Hayasaki, Toshikazu Minami, Mutsuhiko Ohnishi, Yohei Suzuki
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Patent number: 4925901Abstract: Storage stable compositions are disclosed which comprise an epoxide containing compound, a phenolic hydroxyl containing compound, and a catalyst compound for catalyzing the reaction between epoxide groups and aromatic hydroxyl groups which catalyst comprises the product resulting from contacting an onium salt, amine, or amine salt with an acid or a salt of an acid having a weak nucleophilic anion.Type: GrantFiled: November 18, 1988Date of Patent: May 15, 1990Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, John W. Muskopf
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Patent number: 4897460Abstract: The present invention relates to an one-packed type epoxy resin composition. An object of the present invention is to provide epoxy resin composition which have good compatibility with epoxy resin, exhibit excellent stability during storage and heat stability, can be used at about room temperature over a long period of time and can be rapidly cured at a relatively low temperature upon heating.Type: GrantFiled: January 28, 1987Date of Patent: January 30, 1990Assignee: Ajinomoto Co., Inc.Inventors: Hiroshi Sakamoto, Koji Takeuchi
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Patent number: 4882216Abstract: A film comprising a metal foil and a flexible epoxy resin layer covered therewith, wherein the flexible epoxy resin layer is formed from a flexible epoxy resin composition containing one or more polythiol compounds as a hardener, and a flexible printed wiring board produced therefrom.Type: GrantFiled: August 9, 1988Date of Patent: November 21, 1989Assignee: Kashima Industries Co.Inventors: Hideo Takimoto, Katsuji Tokuda, Koji Yamamoto
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Patent number: 4874669Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a ketone solvent solution of a curable composition comprising (A) at least one aromatic based epoxy resin having an average number of epoxide groups per molecule of more than 2; (B) a mixture of (1) at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule; and (2) at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C), optionally, at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: August 15, 1988Date of Patent: October 17, 1989Assignee: The Dow Chemical CompanyInventors: Paul A. Larson, Dale J. Aldrich, Jody R. Berman
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Patent number: 4868059Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: November 16, 1987Date of Patent: September 19, 1989Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4840980Abstract: A method of rheologically stabilizing polyamide-epoxy coatings comprises the addition of an ethoxylated quaternary ammonium chloride compound to the polyamide-epoxy coating to impart post catalyzed sag resistance stability to the coating particularly when the coating is applied to upright or vertical surfaces.Type: GrantFiled: February 29, 1988Date of Patent: June 20, 1989Assignee: The Glidden CompanyInventor: Alan J. Pekarik
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Patent number: 4824927Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.Type: GrantFiled: January 23, 1987Date of Patent: April 25, 1989Assignee: BASF Lacke & Farben AKTInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4808639Abstract: A liquid or viscous curable adhesive composition having a prolonged pot life which is composed of a liquid or viscous curable resin which has, preferably evenly and randomly dispersed therethroughout, a multiplicity of rupturable microcapsules containing a curing agent in an amount sufficient to cure the resin. The microcapsules are rupturable upon the application thereto of external pressure, or other mechanical manipulation. Upon rupture, the curing agent is released into coacting relationship with the curable resin and forms therewith an activated adhesive composition.Type: GrantFiled: July 22, 1987Date of Patent: February 28, 1989Assignee: Production Previews, Inc.Inventor: Milton Chernack
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Patent number: 4804740Abstract: Urea compounds having a plurality of substituents selected from hydrogen, substituted hydrocarbyl radicals and unsubstituted hydrocarbyl radicals are good latent cure accelerators for thermosetting cyanate resin formulations. The resulting cyanate resin formulations are useful as coatings, adhesives and as impregnating resins, particularly in applications where extended storage at or near room temperature is desired.Type: GrantFiled: July 8, 1987Date of Patent: February 14, 1989Assignee: Amoco CorporationInventors: Hugh C. Gardner, Richard H. Newman-Evans
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Patent number: 4780360Abstract: Electrically insulating composite materials formed from (1) epoxy resins and (2) polymeric fiber reinforcement which have high strength are formed if the cross-linking of the epoxy resin is accomplished by anionic polymerization using tertiary amines of the formula ##STR1## as catalyst.Type: GrantFiled: August 20, 1986Date of Patent: October 25, 1988Assignee: Siemens AktiengesellschaftInventors: Wolfgang Kleeberg, Klaus-Robert Hauschildt, Heinz Hacker
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Patent number: 4778863Abstract: Glycidyl derivatives of compounds containing --OH, --NH.sub.2 and/or --COOH groups are prepared by reacting in the presence of a mixture of solvents, at least one of which is a polar aprotic solvent, an excess of an epihalohydrin with a compound containing --OH, --NH.sub.2 and/or --COOH groups while continuously or incrementally adding an alkali metal hydroxide to the mixture and removing water from the reaction by codistillation with epihalohydrin and the solvents.Type: GrantFiled: August 13, 1987Date of Patent: October 18, 1988Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Zeng-kun Liao
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Patent number: 4775734Abstract: A curable composition comprising a polyepoxide, an amine curing agent and a catalytic amount of a non-nucleophilic acid salt of an amine having the formula R(R')(R")NH.sup.+ X.sup.- wherein R, R' and R" independently represent an alkyl group having from 1 to 20 carbon atoms, an alkaryl group having from 7 to 20 carbon atoms or an oxyalkylene group having from 2 to 50 carbon atoms and wherein R' and R" independently also may represent hydrogen and R may also represent the formula [--Y--(R')(R")NH.sup.+ X.sup.- ].sub.n wherein R' and R" have the foregoing designations, Y represents an alkylene or alkylene ether group having from 2 to 50 carbon atoms and n represents an integer of from 1 to 5 is described.Type: GrantFiled: August 12, 1987Date of Patent: October 4, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4771088Abstract: A method of stabilizing polyamide coatings comprises the addition of an ethoxylated quaternary ammonium chloride compound to the polyamide coating to impart sag resistance to the coating particularly when the coating is applied to upright or vertical surfaces.Type: GrantFiled: January 15, 1987Date of Patent: September 13, 1988Assignee: The Glidden CompanyInventor: Alan J. Pekarik
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Patent number: 4762585Abstract: A Process is described for lining the inner surfaces of pipes or pipe sections using the Insituform method by pressing a tubular flexible laminate made up of an essentially liquid-impermeable membrane and a fibrous layer which has been impregnated with a binder which is not as yet fully cured with the face with the binder against the inner surface of the pipe by means of liquid pressure in such a way that the laminate takes on the shape of the inner surface of the pipe and the binder becomes fully cured in the state, forming a firmly adhering internal lining. The binder used according to the invention in this process contains(a) a curing agent which is a salt of one or more (poly)amines having at least one tertiary nitrogen atom and one or more aromtic polyols or one or more aliphatically substituted phenols, the aliphatic radical having at least 9 carbon atoms, and(b) a liquid epoxy resin or a liquid mixture of epoxy resins and can, if desired, also contain(c) further additives.Type: GrantFiled: June 30, 1986Date of Patent: August 9, 1988Assignee: Ciba-Geigy CorporationInventors: Wolfgang Schneider, Kurt Amsler
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Patent number: 4756787Abstract: A co-curable composition, having utility as a first part of a two-part cationically curable composition and containing a latent curing component which is reactive with a latent curing component in a second part of the two-part composition to form curingly effective cations for the two-part composition, such co-curable composition comprising: (i) a cationically polymerizable material, and (ii) a dioxane-complexed metal salt of a non-nucleophilic anion. Also disclosed is a two-part composition curable by contact of respective parts with one another, comprising first and second parts of the aforementioned types. A preferred class of cation species comprises carbenium ions derived from reaction of an organic halide compound, as the first component, with a metal salt of a non-nucleophilic anion such as SbCl.sub.6.sup.-, SbCl.sub.3.sup.-, SbF.sub.6.sup.-, AsF.sub.6.sup.-, SnCl.sub.5.sup.-, PF.sub.6.sup.-, BF.sub.4.sup.-, CF.sub.3 SO.sub.3.sup.-, and ClO.sub.4.sup.-, as the second component.Type: GrantFiled: November 6, 1987Date of Patent: July 12, 1988Assignee: Loctite CorporationInventors: Kieran F. Drain, David J. Dunn
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Patent number: 4755582Abstract: Disclosed herein are high solids thermosetting coating compositions comprising hydroxy-functional polyepoxides and anhydrides as effective curing agents thereof. Films of these coating compositions are of remarkable appearance and are attended by remarkably low volatile organic content (VOC).Type: GrantFiled: August 21, 1986Date of Patent: July 5, 1988Assignee: PPG Industries, Inc.Inventors: William P. Blackburn, Ronald R. Ambrose, Samuel Porter, Jr., Mary J. Burkholder
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Patent number: 4755581Abstract: Disclosed herein are high solids thermosetting coating compositions comprising polyepoxides and anhydrides as effective curing agents therefor. Films from these coating compositions are of remarkable appearance and are attended by remarkably low volatile organic content (VOC).Type: GrantFiled: August 21, 1986Date of Patent: July 5, 1988Assignee: PPG Industries, Inc.Inventors: William P. Blackburn, Ronald R. Ambrose, Samuel Porter, Jr., Mary Jo Burkholder
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Patent number: 4751278Abstract: The adducts of monoepoxides with selected diamines, preferably m-xylylenediamine, are useful as curing agents for the curing of epoxy resin compositions at very low temperatures (25.degree.-50.degree. F., -4.degree. to 10.degree. C.).Type: GrantFiled: April 29, 1987Date of Patent: June 14, 1988Assignee: Ciba-Geigy CorporationInventor: Vincent Brytus
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Patent number: 4749728Abstract: A new transesterification catalyst comprises an epoxide and a non-acidic nucleophilic onium salt.Coating compositions having hydroxyl functional resin components and carboxylic ester components adapted for curing by transesterification following application to a substrate are formulated with in-situ formed cure catalyst comprising a non-acidic nucleophile and an epoxide-to-product coatings that readily cure by transesterification. Such coatings including polyesters, polyepoxides, and polyacrylates are useful in formulating high solids coatings and powder coatings having exceptional physical properties.Extremely low-temperature cure coatings were obtained by transesterifying mixtures of polyols and polymeric esters having multiple activated ester linkages having the structure ##STR1## wherein R' is lower alkyl and Y is --OH and O-alkyl radicals. These coatings provide low-temperature cure coatings for paper, plastic, and wood in addition to metal substrates.Type: GrantFiled: June 6, 1986Date of Patent: June 7, 1988Assignee: The Glidden CompanyInventors: Gary P. Craun, Kirk J. Abbey
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Patent number: 4742096Abstract: Improved powder coating compositions comprise a hydroxyl functional binder having carboxylic ester functionality and a transesterification cure catalyst comprising an epoxide and a non-acidic nucleophile, preferably onium salts. Resins such as hydroxyl functional acrylic, hydroxyl functional polyester, ester functional polyesters, and methyl succinate esters of bisphenol epoxides transesterify in the presence of an epoxide and phosphonium salts such as tetrabutylphosphonium acetate and yield coatings having exceptional hardness, impact resistance and solvent resistance at bake temperatures of about 300.degree. F.Type: GrantFiled: August 1, 1986Date of Patent: May 3, 1988Assignee: The Glidden CompanyInventor: Gary P. Craun
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Patent number: 4739028Abstract: Epoxy resins have been found to be fortified (increased in strength and modulus yet not made brittle) by compounding:(a) a resin-forming polyepoxide(b) an amine curing agent for (a) and(c) a fortifier for (a)+(b) comprising the reaction product of(i) an aromatic polyhydroxy compound and(ii) a diepoxide with one epoxy group less reactive than the other:and heat curing the mixture. Strengths as high as 140 MPa and moduli as high as 4500 MPa have been attained with a ductile mode of failure.Type: GrantFiled: March 2, 1987Date of Patent: April 19, 1988Assignee: Canadian Patents & Development LimitedInventors: Paul D. McLean, Andrew Garton, Robert F. Scott
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Patent number: 4737565Abstract: A composition comprising a mixture of a polyepoxide, an isocyanate and a salt of a polyamine and a polyhydric phenol and a process for curing said composition by heating it to a temperature in the range of from about 80.degree. C. to about 150.degree. C. are described.Type: GrantFiled: April 9, 1987Date of Patent: April 12, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4725652Abstract: Latent catalysts for epoxy reactions are prepared by reacting a tetrasubstituted onium compound such as tetrabutylphosphonium acetate.acetic acid complex or an amine compound with an acid having a weak-nucleophilic anion such as fluoboric acid. These catalysts provide stable latent catalysts for epoxy resins for advancement or curing reactions.Type: GrantFiled: March 4, 1987Date of Patent: February 16, 1988Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Louis L. Walker, Van I. W. Stuart
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Patent number: 4724031Abstract: 2,6-Disubstituted 4-epoxypropyl glycidyl ethers of the formula ##STR1## wherein X is a group R' or X is a group of the formula ##STR2## and each of R and R' independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, a halogen atom or C.sub.6 -C.sub.10 aryl, can be used, together with customary epoxy resin hardeners, for the preparation of cured products, in particular for application in the electronics industry, or as adhesives. Compounds of the formula are also valuable reactive diluents for curable epoxy resin mixtures.Type: GrantFiled: June 4, 1986Date of Patent: February 9, 1988Assignee: Ciba-Geigy CorporationInventors: Charles E. Monnier, Sheik Abdul-Cader Zahir, Sameer H. Eldin
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Patent number: 4722983Abstract: A process for the preparation of glycidyl compounds by reacting a compound containing at least one phenolic group with at least the equivalent amount, based on the phenolic group, of a halohydrin in a substantially anhydrous, aprotonic solvent in the presence of a solid, substantially anhydrous catalyst, is described, which process comprises carrying out the reaction at a temperature in the range from 40.degree. to 80.degree. C. in the presence of an alkali metal carbonate, an aprotonic dipolar solvent with a static relative dielectric constant of more than 25 (at 25.degree. C.) and a permanent electric dipole moment of more than 2.5 D being used, an additional feature of said solvent being that the transition energy of the solvatochromic absorption band of the dissolved N-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridinium perchlorate is in the range from 168 to 197.4 kJ/mole (at 25.degree. C.), or which process comprises carrying out the reaction at a temperature in the range from 60.degree. to 80.Type: GrantFiled: December 8, 1986Date of Patent: February 2, 1988Assignee: Ciba-Geigy CorporationInventors: Charles E. Monnier, Friedrich Stockinger
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Patent number: 4722990Abstract: Epoxy resins of increased functionality are prepared by branching the epoxy resin in the presence of a lithium or cesium compound as a branching catalyst until the desired functionality is obtained and thereafter terminating the branching reaction. Since the lithium and cesium compounds are not deactivated by the aliphatic chloride typically found in an epoxy resin, the branching reaction can effectively be conducted even at low concentrations of the lithium or cesium compound. Termination of the branching reaction is conducted by cooling the branching reaction mixture or by the addition of a deactivating agent which stops or effectively reduces the rate of the branching reaction. Due to the low concentration at which the branching catalyst can be employed, the resulting branched epoxy resins can be prepared without visible turbidity.Type: GrantFiled: August 15, 1985Date of Patent: February 2, 1988Assignee: The Dow Chemical CompanyInventors: Raymond A. Koenig, Guenter H. Haertel
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Patent number: 4717440Abstract: A two-part composition curable by contact of respective parts with one another, comprising: a first part comprising a cationically polymerizable material and a first latent curing component; and a second part comprising a cationically polymerizable material and a second latent curing component which is reactive with the first component to form cations which are curingly effective for the resin. A preferred class of cation species comprises carbenium ions derived from reaction of organic halide compounds, as the first component, with silver salts of non-nucleophilic anions, e.g., SbCl.sub.6.sup.-, SbCl.sub.3.sup.-, SbF.sub.6.sup.-, AsF.sub.6.sup.-, SnCl.sub.5.sup.-, PF.sub.6.sup.-, BF.sub.4.sup.-, CF.sub.3 SO.sub.3.sup.- and ClO.sub.4.sup.-, as the second component, The respective parts of the two-part composition may be applied to matable surfaces which then are contacted to effect rapid bonding cure of the composition.Type: GrantFiled: January 22, 1986Date of Patent: January 5, 1988Assignee: Loctite CorporationInventors: Kieran F. Drain, David J. Dunn
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Patent number: 4701513Abstract: This invention relates to the use of compositions of the formula: ##STR1## wherein n is 2 to 4 and X is --O--, --S-- or ##STR2## wherein R.sub.1 is an aliphatic or aromatic moiety as a curing agent for epoxy resins to form a thermoset material which has a reduced shrinkage.Type: GrantFiled: December 15, 1986Date of Patent: October 20, 1987Assignee: W. R. Grace & Co.Inventor: Shiow C. Lin
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Patent number: 4689375Abstract: The invention relates to curable mixtures comprising(a) at least one epoxy resin containing on average more than one epoxy group in the molecule,(b) at least one diethylphenyl-biguanide of formula I ##STR1## or a combination of a biguanide of formula I and a ketone resin, a ketone/formaledhyde resin or a phenoxy resin, as curing agent, and(c) optionally a curing accelerator.These mixtures are suitable for example as casting resins, laminating resins and, in particular, as powder coating compositions.Type: GrantFiled: September 19, 1985Date of Patent: August 25, 1987Assignee: Ciba-Geigy CorporationInventor: Horst Lauterbach
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Patent number: 4683284Abstract: A mixture of an adhesive composition comprising (A) an epoxy resin and an oxime carbamate and (B) an amine hardener containing primary, secondary or tertiary amino or amido-amine groups and its process for curing said adhesive are described.Type: GrantFiled: June 23, 1986Date of Patent: July 28, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4683283Abstract: An epoxide composition which is curable at a temperature in the range of from 25.degree. C. to 200.degree. C. which is composed of an epoxide resin, a phenol carbamate cure accelerator and an amine hardener is described.Type: GrantFiled: June 23, 1986Date of Patent: July 28, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4656207Abstract: Disclosed is a stiff, tough thermoset composite, the composite comprising a crosslinked epoxy resin matrix and high strength filaments. The resin matrix comprises a glassy discontinuous phase dispersed in a glassy continuous phase that continues throughout the resin matrix. Volume fractions of the discontinuous phase are at least about 35% of the total volume of the continuous and discontinuous phases combined in exceptionally tough composites.Also disclosed are novel resin compositions suitable for making these thermosets.Type: GrantFiled: February 19, 1985Date of Patent: April 7, 1987Assignee: Hercules IncorporatedInventors: Harold Jabloner, Brian J. Swetlin, Sung G. Chu
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Patent number: 4656208Abstract: Described are novel thermosetting epoxy resin compositions suitable for making cured resins, prepregs and stiff, tough thermoset composites. The thermosetting compositions comprise a polyepoxide component, an amine hardener and a specified amount of certain aromatic oligomers containing functional groups which are reactive with the polyepoxide and/or hardener under curing conditions for the composition. The cured resins have a multiphase morphology which comprises at least one glassy continuous phase and at least one glassy discontinuous phase and have a fracture toughness, K.sub.IC, of at least 1.0 MPam.sup.1/2.Type: GrantFiled: April 17, 1985Date of Patent: April 7, 1987Assignee: Hercules IncorporatedInventors: Sung G. Chu, Harold Jabloner, Brian J. Swetlin
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Patent number: 4645818Abstract: Heat-curable compositions are described, comprising(a) an epoxide resin and(b) an effective amount of a urea of formulaAr--NHCON(R.sup.3)R.sup.4whereAr represents an aromatic group linked through an aromatic carbon atom to the indicated nitrogen atom and which is substituted by an amido group, andR.sup.3 and R.sup.4 each represent an aliphatic, cycloaliphatic, or araliphatic hydrocarbyl group, optionally substituted by a halogen atom or a hydroxyl group, or R.sup.3 may further represent a hydrogen atom, or R.sup.3 nd R.sup.4, together with the indicated nitrogen atom, may represent a heterocyclic ring of 3 to 5 carbon atoms which may also have one oxygen atom in the ring.Such amidoarylureas may be used alone with the epoxide resin, or in combination with an accelerator for the heat-curing reaction, selected from dicyandiamide, carboxylic acid hydrazides, succinimide, cyanoacetamide, 1-cyano-3-(lower alkyl)guanidines, imidazoles, and carboxylic acid-tertiary amine salts.Type: GrantFiled: December 11, 1985Date of Patent: February 24, 1987Assignee: Ciba-Geigy CorporationInventor: Christopher M. Andrews