With Reactant Containing At Least One Cyclic Ether Group Patents (Class 528/365)
  • Patent number: 4942215
    Abstract: 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: Grant
    Filed: November 18, 1988
    Date of Patent: July 17, 1990
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Alberto Greco, Luigi Raisa
  • Patent number: 4933420
    Abstract: Epoxide compounds and phenolic compounds are reacted in the presence of phosphonium compounds represented by the formula .crclbar.Z'R.sup.1 R.sup.2 R.sup.3 P.sym.-Z-P.sym.R.sup.1 R.sup.2 R.sup.3 Z'.crclbar. wherein each R.sup.1, R.sup.2 and R.sup.3 is independently an aromatic group or an inertly substituted aromatic group; Z is --(C(R.sup.4).sub.2).sub.a --; each R.sup.4 is independently hydrogen or a hydrocarbyl group containing from 1 to about 20 carbon atoms; Z' is any suitable anion and a has a value of at least 4.
    Type: Grant
    Filed: September 23, 1988
    Date of Patent: June 12, 1990
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Loan A. Ho
  • Patent number: 4929650
    Abstract: 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: Grant
    Filed: July 25, 1988
    Date of Patent: May 29, 1990
    Assignees: Mitsui Sekiyu Kagaku Kogyo Kabushiki Kaisha, Shinko Kosen Kogyo Kabushiki Kaisha
    Inventors: Makoto Kurauchi, Michio Hashimoto, Kiyoshi Hayasaki, Toshikazu Minami, Mutsuhiko Ohnishi, Yohei Suzuki
  • Patent number: 4923911
    Abstract: Curable mixtures comprising(a) at least one epoxy resin containing on average more than one, 1,2-epoxy group per molecule,(b) at least one cyclic carboxylic anhydride,(c) an adduct of a zinc salt of a C.sub.6 -C.sub.18 carboxylic acid with a tertiary amine, and(d) optionally a filler and/or further conventional modifiers have a long pot life without impairment of the brief curing time at elevated temperatures.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: May 8, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Kurt Munk
  • Patent number: 4882399
    Abstract: A method for the preparation of insoluble, infusible epoxy resins containing reversible crosslinks comprising the steps of:(a) forming a reaction mixture of(i) an epoxy compound having two or more epoxy groups, and(ii) a crosslinking agent containing two or more epoxy-reactive groups and further containing a disulfide bond, said crosslinking agent being selected from compounds having the formulaQ--X--S--S--X--Qwhere Q is an epoxy-reactive functional group selected from ##STR1## and X is a divalent aromatic or aliphatic hydrocarbon radical of one to ten carbon atoms, and(b) curing said reaction mixture under conditions conductive to the formation of a crosslinked resin.The epoxy resin can be solubilized by cleavage of the disulfide bond by reduction in the presence of a solvent. The resultant thiol groups can be reoxidized to form the disulfide linkages or can be modified by other reactions.
    Type: Grant
    Filed: August 21, 1987
    Date of Patent: November 21, 1989
    Assignee: Polytechnic University
    Inventors: Giuliana C. Tesoro, Vinod R. Sastri
  • Patent number: 4859721
    Abstract: The invention relates to polymers of formula (I) ##STR1## in which R.sup.1 and R.sup.2 represent optionally substituted alkylene, cycloalkylene or phenylene radicals, A represents hydrogen or carboxyl groups, B represents hydrogen or groups derived from carboxylic acids or isocyanates. The invention also relates to aqueous epoxy resin dispersions containing one or more polymers of general formula (I) in addition to bases, acid, one or more emulsifiers and, optionally, other active substances and auxiliaries typically used in epoxy resin dispersions and also water.The invention also relates to a process for the production of such aqueous epoxy resin dispersions and to the use of such resins in processes for the autophoretic coating of metallic surfaces.
    Type: Grant
    Filed: August 17, 1988
    Date of Patent: August 22, 1989
    Assignee: Henkel Kommaditgesellschaft auf Aktien
    Inventors: Doris Oberkobusch, Roland Morlock, Karl-Heinz Stritzke, Ludwig Schieferstein
  • Patent number: 4855366
    Abstract: A low viscosity product is obtained when an adduct is prepared by reacting (A) at least one polyglycidyl ether of a compound containing an average of more than one phenolic hydroxy group per molecule and (B) at least one aliphatic monocarboxylic acid containing 7 to 15 carbon atoms per molecule; wherein components (A) and (B) are present in amounts which provide a ratio of carboxylic acid groups per epoxide group of from about 0.01:1 to about 0.2:1.
    Type: Grant
    Filed: June 22, 1988
    Date of Patent: August 8, 1989
    Assignee: The Dow Chemical Company
    Inventor: Michael B. Cavitt
  • Patent number: 4853456
    Abstract: The invention is an epoxy resin thermoset adhesive composition. The composition comprises the cured reaction product of:(A) an epoxy base resin, and(B) a curing amount of an admixture comprising:1. an amidoamine of the formula: ##STR1## wherein: P is an iso or para phenylene moiety, and R is the polyoxypropylene moiety of the formula:H.sub.2 NCH(CH.sub.3)CH.sub.2 --[OCH.sub.2 CH(CH.sub.3)].sub.x NH--wherein: x ranges from 2 to 40, and2. an aliphatic polyetheramine, aromatic amine or mixture thereof.The compositions cured at elevated temperature cross-link to form adhesives demonstrating high peel strength and high shear strength.
    Type: Grant
    Filed: February 19, 1988
    Date of Patent: August 1, 1989
    Assignee: Texaco Chemical Company
    Inventors: Kathy B. Sellstrom, Terry L. Renken
  • Patent number: 4851485
    Abstract: Non-fluorinated epoxy resins of a known type are cross-linked by means of polyfunctional fluoroalkanes containing groups which are reactive with the epoxy groups and/or with the hydroxy groups present in the starting resin. The cross-linked products so obtained, having a fluorine content not higher than 15% by weight, and preferably ranging from 1% to 5%, exhibit a complex of properties which are typical of the corresponding fluorinated resins having a much higher fluorine content; in particular, oil- and water-repellency, resistance to hydrolysis and to solvents, and minimum absorption of water.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: July 25, 1989
    Assignee: Ausimont S.p.A.
    Inventors: Alberto Re, Claudio Tonelli, Vito Tortelli
  • Patent number: 4841017
    Abstract: Disclosed as a polyether compound having ether groups and vinyl double bonds represented by formula (I) ##STR1## and an epoxy resin represented by formula (II) ##STR2## wherein R.sup.1 represents a residue group of an organic compound having l active hydrogen atoms, n1 through nl each represents 0 or an integer of from 1 to 100, the sum of integers represented by n1 through nl is from 1 to 100, and l represents an integer of from 1 to 100, and A represents from 1 to 100, and A represents ##STR3## or a mixture of ##STR4## wherein R.sup.2 represents a residue group of mono epoxy compound, and B represents ##STR5## or a mixture of ##STR6## wherein X represents a ##STR7## group, wherein R.sup.3 represents a hydrogen atom, an alkyl group, an alkyl carbonyl group, or an arylcarbonyl group, provided that the epoxy resin represented by formula (II) contains at least one ##STR8## group: In a further aspect, the invention relates to processes for production thereof.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: June 20, 1989
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Murai, Katsuhisa Sakai
  • Patent number: 4829141
    Abstract: A process is disclosed for preparing an advanced epoxy resin by reacting a relatively low molecular weight polyepoxide with a phenol, thiophenol, carboxylic acid or carboxylic acid anhydride in the presence of a catalytic amount of an alkyl substituted phosphonium salt such as tributyl phosphonium bromide. The process can be carried out under reaction conditions, such as the presence of water, which are deleterious to certain epoxy advancement catalysts.
    Type: Grant
    Filed: July 31, 1987
    Date of Patent: May 9, 1989
    Assignee: Shell Oil Company
    Inventor: Roy J. Jackson
  • Patent number: 4829105
    Abstract: An anodic electrodeposition composition containing a water-soluble or water-dispersible modified epoxy resin derived from an epoxy resin having two epoxide groups and at least one alcoholic hydroxy group at the terminals and the middle of the resin backbone, respectively. The modified epoxy resin has at least one polymeric side chain block bound to said alcoholic hydroxy group and at least one acid group derived from said terminal epoxide group.
    Type: Grant
    Filed: January 28, 1988
    Date of Patent: May 9, 1989
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kazunori Kanda, Shinsuke Shirakawa, Hirotoshi Umemoto, Ryuzo Mizuguchi
  • Patent number: 4816545
    Abstract: Non-fluorinated epoxy resins of known type are crosslinked by means of polyfunctional perfluoropolyethers containing groups which are reactive with the epoxy groups and/or with the hydroxy groups present in the starting resin. The so-obtained crosslinked products, with a fluorine content not higher than 20% by weight, preferably comprised within the range of from 5% to 15%, are endowed with a set of properties typical of the corresponding fluorinated resins with a much higher fluorine content, in particular, water- and oil-repellence, resistance to hydrolysis and to solvents, minimum water absorption.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: March 28, 1989
    Assignee: Ausimont S.p.A.
    Inventors: Alberto Re, Gianni Donati
  • Patent number: 4814391
    Abstract: Certain cobalt(II) complexes such as secondary amine adducts of cobalt(II) acetylacetonate have been found useful as latent catalysts for anhydride-epoxy blends.
    Type: Grant
    Filed: May 9, 1988
    Date of Patent: March 21, 1989
    Assignee: General Electric Company
    Inventor: Robert E. Colborn
  • Patent number: 4814415
    Abstract: The invention is an epoxy resin thermoset adhesive composition. The composition comprises the cured reaction product of:(A) an epoxy base resin, and(B) a curing amount of an admixture comprising:1. an oxamidoamine of the formula: ##STR1## wherein: R is the polyoxypropylene moiety of the formula:H.sub.2 NCH(CH.sub.3)CH.sub.2 --[OCH.sub.2 CH(CH.sub.3)].sub.x NH--wherein: x ranges from 2 to 40, and2. an aliphatic polyetheramine, aliphatic polyamine, aromatic amine or mixture thereof.The adhesives are cured at elevated temperature. They are noted for high peel strength and good shear strength.
    Type: Grant
    Filed: February 19, 1988
    Date of Patent: March 21, 1989
    Assignee: Texaco Chemical Company
    Inventors: Kathy B. Sellstrom, David C. Alexander
  • Patent number: 4795791
    Abstract: 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 conecntration at which the branching catlayst can be employed, the resulting branched epoxy resins can be prepared without visible turbidity.
    Type: Grant
    Filed: November 27, 1987
    Date of Patent: January 3, 1989
    Assignee: The Dow Chemical Company
    Inventors: Raymond A. Koenig, Gunter H. Haertel
  • Patent number: 4791154
    Abstract: A composition comprising an epoxy resin and an aromatic azopolyamine curing agent is described. The use of azopolyamine curing agents in reactive monomer-diluted systems results in a high-modulus cured epoxy system.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: December 13, 1988
    Assignee: Shell Oil Company
    Inventors: Larry S. Corley, Donald R. Gehring
  • Patent number: 4771087
    Abstract: The invention discloses crosslinking components for hydroxy and/or primary and/or secondary amine groups containing cationic resins which can be used as binders for stoving paints, particularly for cathodically depositable electrodeposition paints. The crosslinking components are obtained through partial transesterification of transamidation of oligomeric KNOEVENAGEL-reaction products of C-H-active esters and carbonyl compounds with polyols or amines. The products can also be obtained through partial transesterification or transamidation of the C-H-active esters and subsequent KNOEVENAGEL-reaction.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: September 13, 1988
    Assignee: Vianova Kunstharz A.G.
    Inventors: Rudolf Schipfer, Gerhard Schmolzer, Wolfgang Daimer
  • 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: 4755582
    Abstract: 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: Grant
    Filed: August 21, 1986
    Date of Patent: July 5, 1988
    Assignee: PPG Industries, Inc.
    Inventors: William P. Blackburn, Ronald R. Ambrose, Samuel Porter, Jr., Mary J. Burkholder
  • Patent number: 4755580
    Abstract: A coated article is made by: (1) admixing an epoxy resin, with a dual curing agent admixture of (a) an irradiated mixture of carboxylic acid anhydride and carbon containing cyclic compound and (b) a boron trihalide complex selected from at least one of boron trihalide:amine and boron trihalide:ether, (2) applying the mixed resin and concentrated dual curing agent to the surface of an article, and (3) curing the applied resin and curing agent.
    Type: Grant
    Filed: November 3, 1986
    Date of Patent: July 5, 1988
    Assignee: Westinghouse Electric Corp.
    Inventors: Howard E. Saunders, Rajender K. Sadhir, Richard D. Buckley
  • Patent number: 4739028
    Abstract: 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: Grant
    Filed: March 2, 1987
    Date of Patent: April 19, 1988
    Assignee: Canadian Patents & Development Limited
    Inventors: Paul D. McLean, Andrew Garton, Robert F. Scott
  • Patent number: 4732958
    Abstract: According to the invention, a relatively low molecular weight epoxy resin is reacted with a hydroxyl group-containing compound in the presence of a bis(trihydrocarbyl phosphine)iminium salt catalyst to produce a high molecular weight fusion reaction product. The process is particularly useful in reacting an epoxy resin having a molecular weight of less than about 500 with bisphenol-A in the presence of a bis(phosphine)iminium halide to produce a fusion reaction product having a molecular weight within the range of about 500 to 7000. The catalyst is relatively water-insensitive, and the reaction can therefore be carried out in the presence of water.
    Type: Grant
    Filed: December 30, 1986
    Date of Patent: March 22, 1988
    Assignee: Shell Oil Company
    Inventors: Roy J. Jackson, Larry S. Corley
  • Patent number: 4711936
    Abstract: A curing agent for an epoxy resin comprises a cyclodextrin clathrate compound of a compound which is reactive with an epoxy group, a curing agent for an epoxy resin comprising a mixture of a cyclodextrin clathrate compound of a compound which is reactive with an epoxy group with a trace amount of amylase, and methods for the preparation of these curing agents. The curing agents are stable at room temperature, and the curing reaction is initiated under remarkably simple conditions.
    Type: Grant
    Filed: November 13, 1985
    Date of Patent: December 8, 1987
    Assignee: Japan Liquid Crystal Co., Ltd.
    Inventors: Ichiro Shibanai, Kenji Nakamura
  • Patent number: 4707535
    Abstract: This invention is directed to adducts of a poly(active hydrogen) organic compound and a polyepoxide comprising the reaction product of a poly(active hydrogen) organic compound and a polyepoxide containing two or more epoxy groups per molecule, said poly(active hydrogen) organic compound being employed in an amount at least sufficient to effect substantially complete reaction of the epoxy groups of the polyepoxide. The adducts are useful in the formulation of high solids coating compositions, polyurethane elastomers, inks, sealants, adhesives and the like.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: November 17, 1987
    Assignee: Union Carbide Corporation
    Inventor: Joseph V. Koleske
  • Patent number: 4692504
    Abstract: A method is disclosed for deactivating a hydrocarbyl phosphonium salt catalyst of an epoxy resin fusion reaction. The method involves contacting the hydrocarbyl phosphonium salt catalyst with a sulfonic acid, such as p-toluenesulfonic acid or methane sulfonic acid. The method is particularly suited for deactivation of moisture-resistant phosphonium salts such as methylene bis(triphenyl phosphonium halide)s.
    Type: Grant
    Filed: April 30, 1986
    Date of Patent: September 8, 1987
    Assignee: Shell Oil Company
    Inventor: Harry Frank
  • Patent number: 4689388
    Abstract: A curable epoxy resin composition, comprising (1) an alicyclic epoxy resin having an average of more than one epoxy group per molecule, (2) a polybasic acid hydrazide, and (3) a latent curing agent for said epoxy resin which comprises an addition product obtained by reacting (a) a polyfunctional epoxy compound with (b) a compound having at least one functional group in the molecule selected from the group consisting of OH, SH, COOH and CONHNH.sub.2 together with a tertiary amino group, or by reacting said components (a) and (b) with (c) an organic compound which has more than two active hydrogen atoms in the molecule, said reactions occurring under conditions in which the ratio of (a) to (b) or (a) to (b) and (c) ranges from 0.8 to 2.5 equivalents of (a) per equivalent of the total active hydrogen atoms in component (b) and in components (b) and (c), the molar ratio of (c) to (b) being 0.2:1 to 1:1, and said addition product having a softening point of 60.degree. to 180.degree. C.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: August 25, 1987
    Assignee: Ajinomoto Co., Inc.
    Inventors: Kiyomiki Hirai, Koji Takeuchi, Hiroshi Sakamoto, Masahiro Abe
  • Patent number: 4689376
    Abstract: This invention relates to heat-hardenable epoxide resin mixtures of at least one 1,2-polyepoxide having more than one 1,2-epoxide group per molecule, at least one cyclic carboxylic acid anhydride and at least one ammonium phosphonate or ammonium phosphate as a hardening catalyst, as well as further optional auxiliaries.
    Type: Grant
    Filed: December 12, 1985
    Date of Patent: August 25, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dimitrios Kerimis, Hanns P. Muller, Walter Uerdingen, Heinrich Heine
  • Patent number: 4683284
    Abstract: 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: Grant
    Filed: June 23, 1986
    Date of Patent: July 28, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • 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: 4663072
    Abstract: This invention relates to a stable acid anhydride paste mixture useful as a crosslinking agent for epoxy resins and a dual catalyst system therefor. In particular, the anhydride mixture comprises high melting point acid anhydride, a liquid acid anhydride, and a low melting point acid anhydride. The dual catalyst system comprises tertiary amine catalysts with boron trihalide amine complex catalysts.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: May 5, 1987
    Assignee: Ford Motor Company
    Inventor: Mo-Fung Cheung
  • Patent number: 4661541
    Abstract: This application discloses a synthetic resin based on alcohol-modified polyepoxides. The synthetic resin can be prepared by reacting a diepoxide, or a mixture of diepoxides, having an epoxide equivalent weight of less than about 500, with compounds with a hydroxyl group, which is reactive towards epoxide groups, in a molar ratio from about 2:1 to about 7:6 at temperatures from about 100.degree. C. to about 180.degree. C. in an organic solvent free of hydroxyl groups. The synthetic resin has terminal epoxide groups and a mean molecular weight from about 400 to about 5000.
    Type: Grant
    Filed: March 14, 1985
    Date of Patent: April 28, 1987
    Assignee: BASF Farben & Fasern AG
    Inventors: Wolfgang Batzill, Arnold Dobbelstein, Michael Geist, Georg Schon, Gunther Ott
  • Patent number: 4661562
    Abstract: A process for the rapid formation of thermoset polymers by polymerizing a mixture of a polyepoxide with a polycarboxylic acid containing an alkali or alkaline earth metal cationic complex catalyst is disclosed.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: April 28, 1987
    Assignee: Ashland Oil, Inc.
    Inventor: Anil B. Goel
  • Patent number: 4658009
    Abstract: Disclosed is a 2-substituted-4,6-diamino-s-triazine/isocyanuric acid adduct represented by the following formula: ##STR1## wherein R stands for an alkyl group having 2 to 20 carbon atoms, an unsubstituted or cyano group-substituted aryl group, or a group of the formula R.sup.1 --CH.sub.2 CH.sub.2 -- in which R.sup.1 stands for an alkoxy group having up to 20 carbon atoms, an acyloxy group, an amino group, an N-substituted amino group, a benzotriazolyl group or a 2-alkylimidazolyl-(4)-dithiocarbonyl group, or by the following formula: ##STR2## wherein R.sup.2 stands for an alkylene group which may have an intervening imino or phenylene group.When this adduct is used for curing a polyepoxy resin, a cured product having good heat resistance, insulating property and adhesion and an excellent migration-preventing effect is formed.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: April 14, 1987
    Assignee: Shikoku Chemicals Corporation
    Inventors: Kazuo Kamagata, Toshiaki Yamada, Natsuo Sawa
  • Patent number: 4652605
    Abstract: A polymeric reaction product, a process for its preparation and a coating composition containing the reaction product as a binder are described. The polymeric reaction product is prepared by the vinyl addition polymerization of a vinyl monomer component of which at least 50 percent by weight is an active hydrogen-containing vinyl monomer in the presence of a polymeric diluent. The rate of polymerization is controlled such that the amount of unreacted vinyl monomer, on the average, does not exceed 10 percent by weight of the total weight of the reaction mixture.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: March 24, 1987
    Assignee: PPG Industries, Inc.
    Inventors: Wen-Hsuan Chang, Michael M. Chau, J. Alden Erikson, Robert J. Lipinski, David T. McKeough, Richard M. Nugent, Jr.
  • Patent number: 4645818
    Abstract: 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: Grant
    Filed: December 11, 1985
    Date of Patent: February 24, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Christopher M. Andrews
  • Patent number: 4644036
    Abstract: Michael addition products of monocarboxylic or dicarboxylic acid esters, capable of undergoing Michael addition, with compounds containing double bonds capable of undergoing Michael addition are suitable for use as a curing component for synthetic resins containing groups capable of amide formation and/or ester formation with carboxylic acids. In particular, the Michael addition products of acetoacetic esters or malonic esters with esters, amides or urea derivatives of .alpha., .beta.-unsaturated monocarboxylic or dicarboxylic acids are used. The structure and the functionality of the curing component can be varied in many ways. It can be attached directly to the synthetic resin molecule, so that self-curing synthetic resins are obtained.
    Type: Grant
    Filed: April 26, 1984
    Date of Patent: February 17, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerd Walz, Ernst-August Theiling
  • Patent number: 4612359
    Abstract: Thermosettable compositions are prepared which contain (A) from about 0.1 to 100 percent by weight of an esterified aromatic cyanate; (B) from zero to about 99.9 percent by weight of an aromatic polycyanate, an aromatic polycyanamide or mixture thereof and (C) from zero to about 99.9 percent by weight of an epoxy resin.
    Type: Grant
    Filed: October 16, 1985
    Date of Patent: September 16, 1986
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • 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: 4587311
    Abstract: There are described novel imidazolides (N-acylimidazoles) of the formula I ##STR1## wherein R.sub.1 is methyl, ethyl or isopropyl,R.sub.2, R.sub.3 and R.sub.4 independently of one another are each hydrogen, methyl, ethyl or isopropyl, with the proviso that R.sub.2 is hydrogen only when R.sub.1 is isopropyl,R.sub.5, R.sub.6 and R.sub.7 independently of one another are each hydrogen, methyl, ethyl or isopropyl, or phenyl which is unsubstituted or substituted by methyl or ethyl groups, with the proviso that at least one of the symbols R.sub.5, R.sub.6 and R.sub.7 is phenyl which is unsubstituted or substituted according to definition.The imidazolides (I) are suitable as curing agents for polyepoxide compounds.
    Type: Grant
    Filed: April 20, 1984
    Date of Patent: May 6, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Schmid, Helmut Zondler, Michael Fischer, Werner Stauffer
  • Patent number: 4579933
    Abstract: N-cyanoacylamide compounds are prepared by reacting 1 mol of an N-cyanocarboxylic acid amide salt with 1 mol of a halogen compound in a polar, aprotic solvent.The N-cyanoacylamide compounds can be used for hardening epoxide resins, for the preparation of isomelamine or for the preparation of linear polymers which can be crosslinked by heat.
    Type: Grant
    Filed: April 22, 1985
    Date of Patent: April 1, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Stockinger, Friedrich Lohse, Roland Moser
  • Patent number: 4565859
    Abstract: A polyether compound having ether groups and vinyl double bonds represented by formula (I) ##STR1## wherein R.sub.1 represents a residue of an organic compound having l active hydrogen atoms, n.sub.1 through n.sub.l each represents 0 or an integer of from 1 to 100, the sum of the integers represented by n.sub.1 through n.sub.l is from 1 to 100, andl represents an integer of from 1 to 100, and A represents ##STR2## and a process for production thereof; an epoxy resin represented by formula (II) ##STR3## wherein R.sub.1 and n.sub.1 through n.sub.l are defined above, and B is an oxycyclohexane unit having a substituent and is represented by formula (III) ##STR4## wherein X represents a ##STR5## --CH.dbd.CH.sub.2, or ##STR6## groups, wherein R.sub.
    Type: Grant
    Filed: January 29, 1985
    Date of Patent: January 21, 1986
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Takaaki Murai, Shoji Watanabe, Kimio Inoue, Toyokazu Yagii
  • Patent number: 4559398
    Abstract: A curable composition consisting ofA. 100 parts by weight of an epoxy resin,B. from 4 to 100 parts by weight of a conventional curing agent for epoxy resins, andC. from 0.1 to 5 parts by weight of an N-acylimidazole which possesses an aromatic acyl component which is substituted at the two positions ortho to the carbonyl groupcan be used to produce moldings, coatings, finishes, adhesives and composite fiber materials.
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: December 17, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Tesch, Andreas Henne, Manfred Heym, Herbert Stutz
  • Patent number: 4554341
    Abstract: Heat curable epoxy-styrene compositions exhibiting improved processability, low viscosity, long pot life, and fire retardancy 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: Grant
    Filed: February 27, 1985
    Date of Patent: November 19, 1985
    Assignee: Shell Oil Company
    Inventor: Robert C. Allen
  • Patent number: 4550154
    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, comprising the reaction product of diepoxide with diphenol, dicarboxylic acid and acid component comprising hydroxy functional acid and optionally further comprising fatty acid; 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: October 29, 1985
    Assignee: Ford Motor Company
    Inventor: Panagiotis I. Kordomenos
  • Patent number: 4549008
    Abstract: Novel tetraglycidyl ethers of the formula ##STR1## wherein X is a group ##STR2## R is hydrogen or methyl, and n is an integer from 2 to 4. The novel tetraglycidyl ethers can be used in curable mixtures, together with a curing agent for epoxide resins, in particular for the protection of surfaces.
    Type: Grant
    Filed: August 13, 1984
    Date of Patent: October 22, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Renner, Peter Grutter, Rolf Hugi
  • Patent number: 4542202
    Abstract: An addition product obtained by reacting (a) a polyfunctional epoxy compound and (b) a compound having at least one functional group of OH group, SH group, COOH group and CONHNH.sub.2 group together with a tertiary amino group in the molecule, and an addition product obtained (a), (b) and (c) an organic compound having two or more active hydrogen atoms in the molecule (excluding a compound having an epoxy group or tertiary amino group) are good curing agents for epxoy resin. The curing agents are useful in formulating novel storable one-package, heat-curable epoxy resin-based compositions.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: September 17, 1985
    Assignee: Ajinomoto Co., Inc.
    Inventors: Koji Takeuchi, Masahiro Abe, Nobuo Ito, Kiyomiki Hirai
  • Patent number: 4540769
    Abstract: Aromatic N-glycidylamines are prepared by treatment of an amine having at least one, and preferably two or more aromatic amino hydrogen atoms, with epichlorohydrin in the presence, as catalyst, of a di- or higher-valent metal salt of nitric or perchloric acid, or of a carboxylic or sulphonic acid substituted by fluorine, chlorine or bromine on the carbon atom alpha to the carboxylic or sulphonic acid group, and dehydrochlorinating the product. The presence of the metal salt gives a product having a higher glycidyl content and a lower viscosity than does the same reaction in the absence of such a salt.Suitable aromatic amines include aniline, phenylene diamines, phenylene diamines substituted on the aromatic ring and bis(4-aminophenyl)methane. The metal salt may be of, for example, magnesium, calcium, zinc, manganese, nickel, iron, lanthanum, vanadium, ytterbium or uranium.
    Type: Grant
    Filed: September 25, 1984
    Date of Patent: September 10, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Bryan Dobinson, Michael R. Thoseby
  • Patent number: RE32628
    Abstract: A solvent-free curable composition has a long shelf life and consists ofA 100 parts by weight of an epoxy resin andB from 10 to 100 parts by weight of .[.,.]. .Iadd.4,4-bis-(para-aminobenzoyl)-piperazine .Iaddend.as a curing agent for the epoxy resin, .[.an aromatic diamine containing ##STR1## groups,.]. with or without C from 0.01 to 5 parts by weight of an accelerator, the curing agent for the epoxy resin being finely dispersed in the latter and preferably having a particle size of less than 10 .mu.m. .[.The preferred epoxy resin curing agent is 4,4'-diaminodiphenyl ketone..]. The curable composition is used in particular for the preparation of fiber-reinforced materials.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: March 22, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Tesch, Manfred Heym, Walter Doerflinger, Herbert Stutz, Peter Neumann, Dietmar Nissen, Gerhard Schaefer