Material Contains A Phosphorus Atom Patents (Class 528/89)
  • Patent number: 4382130
    Abstract: Certain aryloxyphosphonium salts have been found to be effective as curing agents for various cationically polymerizable organic materials, such as epoxy resins, when incorporated into such materials. The materials are found to be moisture curable coating compositions.
    Type: Grant
    Filed: October 14, 1981
    Date of Patent: May 3, 1983
    Assignee: General Electric Company
    Inventors: Robert H. Ellison, Martin A. Byrne
  • Patent number: 4379908
    Abstract: The present invention provides an curable composition comprising (1) at least one epoxy compound containing at least one vicinal-epoxy groups, (2) a miscible amount of at least one ethylenically unsaturated monomer and (3) a curing amount of at least one catalyst selected from lithium or Group II metal salts of a non-nucleophilic acid.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: April 12, 1983
    Assignee: Shell Oil Company
    Inventor: Thomas F. Brownscombe
  • Patent number: 4374963
    Abstract: This invention relates to a heat curable composition comprising(a) a liquid, ethylenically unsaturated monomer, oligomer or prepolymer of the formula: ##STR1## wherein R is H or CH.sub.3, R.sub.1 is an organic moiety and n is at least 2,(b) an epoxy resin containing at least two ##STR2## groups, and (c) a thermal initiator member of the group consisting of(1) a substituted or unsubstituted diaryliodonium salt in combination with a free radical initiator,(2) a BF.sub.3 adduct,(3) a BF.sub.3 adduct in combination with a free radical initiator, and(4) dicyandiamide in combination with a free radical initiator.The system is stable at ordinary temperatures, but on heating the thermal initiator catalyzes the curing of the acrylate and the epoxy resin.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: February 22, 1983
    Assignee: W. R. Grace & Co.
    Inventors: Charles R. Morgan, David R. Kyle
  • Patent number: 4373073
    Abstract: Glycidyl ethers of monohydric or polyhydric phenols of high purity are obtained if hydrogen halide is eliminated from halohydrin ethers of the phenols in aqueous alkalis in the presence of one or more onium compounds selected from quaternary ammonium compounds having at least one aliphatic C.sub.4-22 hydrocarbon radical, quaternary phosphonium compounds and tertiary sulphonium compounds as catalyst, or in the presence of those compounds which form in the reaction medium in situ, before the addition of the alkali, such onium compounds from the halohydrin ethers together with tertiary amines, tertiary phosphines or thioethers. In comparison with the known processes, the rate of dehydrohalogenation can thereby be significantly increased as a result of which an increase in production is achieved. Moreover, significantly purer reaction products are obtained by the avoidance of side reactions.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: February 8, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Bernhard Wojtech, Hans-Joachim Kiessling, Wilhelm Becker, Kurt Hermann
  • Patent number: 4370465
    Abstract: Epoxy resins having improved properties are prepared by reacting an epoxy resin with a dihydric phenol in the presence of a sufficient quantity of a phosphonium catalyst such that the product resulting from reacting a mixture of the catalyst, epoxy resin and dihydric phenol has a % epoxide difference from the theoretical percent epoxide of from about 0.5 to about 4.0.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: January 25, 1983
    Assignee: The Dow Chemical Co.
    Inventors: Ross C. Whiteside, Jr., Adolphus V. Gist, George A. Doorakian
  • Patent number: 4368314
    Abstract: A curable composition comprising:(A) at least one spiro-orthoester compound having at least one spiro-orthoester group represented by the formula: [I] ##STR1## wherein n is an integer of 3-5, (B) at least one curing agent selected from the group consisting of organic polybasic acids and their anhydrides,(C) optionally, an epoxy compound having at least one epoxy group, and(D) optionally a cationic polymerization catalyst when the composition comprises ingredient (C).Said composition is small in shrinkage on curing, and provides a cured product of high dimensional accuracy when used as a molding material.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: January 11, 1983
    Assignee: Toagoesi Chemical Industry Co., Ltd.
    Inventors: Takeshi Endo, Kiyokazu Mizutani, Takahisa Ogasawara
  • Patent number: 4366295
    Abstract: Compositions containing a relatively low equivalent weight epoxy resin and an advancement catalyst for reacting said epoxy resin with a polyhydric phenol are stable at high storage temperatures when the advancement catalyst is a phosphonium salt of phosphoric acid, phosphorous acid or polyphosphoric acid.
    Type: Grant
    Filed: June 1, 1981
    Date of Patent: December 28, 1982
    Assignee: The Dow Chemical Company
    Inventors: Manuel C. Tyler, Jr., Avis L. McCrary
  • Patent number: 4365052
    Abstract: The invention relates to a method for the manufacture of transparent casting resins. According to the invention, a liquid acid anhydride (b) is admixed to a premixture (a), which is liquid at room temperture, of zinc octoate, a low-molecular weight acid ester and, optionally, an organic phosphite, and this mixture of (a) and (b) is added, preferably at temperatures .ltoreq.50.degree. C., to liquid aromatic diglycidyl ethers. Diphenyldecyl phosphite is particularly well suited as an organic phosphite. The casting resins obtained are transparent and find use particularly for casting-in and encapsulating opto-electronic components such as light-emitting diodes (and diode displays), photo diodes and photo transistors.
    Type: Grant
    Filed: April 16, 1981
    Date of Patent: December 21, 1982
    Assignee: Siemens Aktiengesellschaft
    Inventors: Ulrike Reeh, Hans Denk
  • Patent number: 4358577
    Abstract: High molecular weight epoxy resins containing hydrolyzed epoxy groups are prepared by reacting (A) a low molecular weight epoxy resin, and (B) a hydroxyl-containing compound in the presence of (C) a catalyst therefor and (D) an excess quantity of water and thereafter removing the excess water.
    Type: Grant
    Filed: November 26, 1980
    Date of Patent: November 9, 1982
    Assignee: The Dow Chemical Company
    Inventors: Avis L. McCrary, Michael G. Stevens
  • Patent number: 4358578
    Abstract: The instant invention provide a process for increasing the molecular weight of an epoxy resin by reacting (1) a polyepoxide containing more than one vicinal epoxy group in the molecule, preferably a normally liquid polyether of a polyhydric phenol, (2) a polyhydric phenol, (3) a catalytic amount of an alkali metal or alkaline earth metal salt of a non-nucleophilic acid, especially fluoboric acid and perchloric acid, preferably in the presence of (4) a base such as pyridine.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: November 9, 1982
    Assignee: Shell Oil Company
    Inventor: Thomas F. Brownscombe
  • Patent number: 4354015
    Abstract: Tetrahydrocarbyl phosphonium bicarbonate salts are described which are unexpectedly effective as catalysts for promoting the reaction between (a) vicinal epoxides and (b) phenols. These catalysts are particularly useful in preparing high molecular weight epoxy resins by the advancement reaction of an epoxy resin with a polyhydric phenol.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: October 12, 1982
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette, James L. Bertram
  • Patent number: 4352918
    Abstract: Epoxy resins having improved properties are prepared by reacting an epoxy resin with a dihydric phenol in the presence of a sufficient quantity of a phosphonium catalyst such that the product resulting from reacting a mixture of the catalyst, epoxy resin and dihydric phenol has a % epoxide difference from the theoretical percent epoxide of from about 0.5 to about 4.0.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: October 5, 1982
    Assignee: The Dow Chemical Company
    Inventors: Ross C. Whiteside, Jr., Adolphus V. Gist, George A. Doorakian
  • Patent number: 4345059
    Abstract: Epoxy resins are rendered fire retardant by the addition thereto of a 3-hydroxyalkylphosphine oxide. Other halogen containing flame retardants may or may not be present in the composition. Mixtures containing a brominated epoxide and/or a halogenated phosphine oxide provide a high level of flame retardance at low levels of the additive. The epoxy resins may be heat cured in the presence of an acid anhydride or amine to form a polymer having the phosphine oxide incorporated in the polymer molecule.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: August 17, 1982
    Assignee: FMC Corporation
    Inventors: Edward R. Fretz, Jr., Joseph Green
  • Patent number: 4343928
    Abstract: A high heat resistant transparency of epoxy resins cured with adducts of trimethoxyboroxine and benzyl alcohol is disclosed to resist intense heat for these transparencies in their use on military and industrial hardware. Additionally, the transparency may include phosphite or phosphate compounds to improve heat resistance, with the phosphate compound in sufficient concentrations to delay gel times such that the phenyl substituted alkyl alcohol may be eliminated from the composition. This transparency may exist in a composite with other layers of transparent material known to those skilled in the art. The epoxy transparency layer is bound to the other transparent layers, in a variety of configurations, using an interlayer of mercaptan terminated resins. These resins greatly improve resistance to moisture permeability in and about the edges of the entire transparency.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: August 10, 1982
    Assignee: Goodyear Aerospace Corporation
    Inventor: John R. Uram, Jr.
  • Patent number: 4342673
    Abstract: Novel coating systems comprising high-solids content blends of epoxy prepolymers, a catalyst complex comprising a complex iodonium salt and a copper salt, and a conventional pigment. The compositions cure rapidly to highly chemically resistant, tough coatings.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: August 3, 1982
    Assignee: General Electric Company
    Inventor: Austin A. Wolfrey
  • Patent number: 4340713
    Abstract: High molecular weight epoxy resins containing hydrolyzed epoxy groups are prepared by reacting (A) a low molecular weight epoxy resin and (B) a hydroxyl-containing compound in the presence of (C) water (D) a hydrolysis catalyst and (E) a catalyst for effecting the reaction between (A) and (B).
    Type: Grant
    Filed: November 26, 1980
    Date of Patent: July 20, 1982
    Assignee: The Dow Chemical Company
    Inventors: Rhetta Q. Davis, Michael B. Cavitt
  • Patent number: 4339567
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of a sulphoxonium salt (II) of formula ##STR1## where P denotes zero or 1,R.sup.6 denotes an arylene or aralkylene group,R.sup.7 denotes --H or a group of formula ##STR2## R.sup.8 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group,R.sup.9 has the same meaning as R.sup.8 but may alternatively represent a dialkylamino group or, if R.sup.8 represents an alkyl group, R.sup.9 may represent an arylamino group,R.sup.10 and R.sup.11 each independently have the same meaning as R.sup.8 but may also each denote --H,r represents 1, 2, or 3,Z.sup.r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4336366
    Abstract: Cationically polymerizable compounds, for example cyclic ethers, can be thermally polymerised if an aromatic iodonium salt of the formula I[(Ar.sup.1)(Ar.sup.2)I].sup.+ [MX.sub.n ].sup.- (I)in which Ar.sup.1 Ar.sup.2, M, X and n are as defined in claim 1, is used as the catalyst and an agent which forms free radicals on heating and has the formula III or IV ##STR1## in which R.sup.2, R.sup.3, R.sup.5, R.sup.6, R.sup.8 and m are as defined in claim 1, for example a benzpinacol silyl ether, is used as the co-catalyst. The process is of particular importance for heat-curing epoxide resins as a one-component system.
    Type: Grant
    Filed: February 20, 1981
    Date of Patent: June 22, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Godwin Berner, Rudolf Kirchmayr
  • Patent number: 4335179
    Abstract: A resin impregnated spacer, useful for bracing electrical conductors, comprises a porous, flexible, heat resistant material impregnated with an epoxy resin containing Lewis acid curing agent and an effective amount of dibutylphosphite.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: June 15, 1982
    Assignee: Westinghouse Electric Corp.
    Inventors: Morris A. Mendelsohn, Francis W. Navish
  • Patent number: 4330644
    Abstract: The present invention is directed to a curable composition comprising (1) a solid epoxy composition prepared by reacting (a) a solid epoxy resin prepared by reacting a normally liquid epoxy resin with a polyhydric phenol in the presence of an etherification catalyst with (b) a small amount of tris(hydroxymethyl) aminomethane and (2) at least one epoxy curing agent.
    Type: Grant
    Filed: April 3, 1981
    Date of Patent: May 18, 1982
    Assignee: Shell Oil Company
    Inventor: Roy A. Allen
  • Patent number: 4328150
    Abstract: The invention provides a novel epoxy-based curable resin composition suitable for encapsulation of electronic devices such as transistors, ICs, LSIs and the like. The composition comprises an epoxy compound, a novolac-type phenolic resin as the curing agent, an organophosphine compound such as triphenylphosphine and trilaurylphosphine as a curing accelerator and an inorganic filler. The advantages obtained by the combined use of the novolac-type phenolic resin and the organophosphine compound are very specific and the resin composition is imparted with remarkable flowability in molding and stability in storage in addition to the excellent electric properties at high temperatures and anti-moisture resistance of the cured shaped articles molded therefrom.
    Type: Grant
    Filed: March 12, 1981
    Date of Patent: May 4, 1982
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Kiyohiro Kondow, Tetuo Yoshida, Yuki Tateyama
  • Patent number: 4319974
    Abstract: UV curable mixtures of C.sub.(8-28) .alpha.-olefin oxides and certain onium salt photoinitiators, for example, certain diaryliodonium salts, or triarylsulfonium salts, and optionally polyfunctional epoxy resin, have been found useful in paper release coating applications.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: March 16, 1982
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4320222
    Abstract: A precatalyzed, elevated temperature storage-stable epoxy composition is described wherein the catalyst composition is a mixture of a phosphonium halide and an alkali metal salt of a hydroxide or halide. The preparation of higher molecular weight fusion products wherein the precatalyzed epoxy composition is reacted with a polyhydric phenol is also described.
    Type: Grant
    Filed: April 10, 1980
    Date of Patent: March 16, 1982
    Assignee: Shell Oil Company
    Inventor: John A. Lopez
  • Patent number: 4316006
    Abstract: Phosphorus containing polymers are prepared by copolymerizing a cyclic phosphite and an epoxide in the presence of an acid catalyst. The resulting polymer can be incorporated within a thermoplastic or thermosettable resin to increase the flame resistivity thereof.
    Type: Grant
    Filed: February 27, 1980
    Date of Patent: February 16, 1982
    Assignee: The Dow Chemical Company
    Inventor: Gerald K. McEwen
  • Patent number: 4314917
    Abstract: Novel coating systems comprising high solids content blends of epoxy prepolymers and a catalyst complex comprising a complex iodonium salt, a copper salt, and a tin salt and a conventional pigment. The compositions cure rapidly to highly chemically resistant, tough coatings.
    Type: Grant
    Filed: February 12, 1980
    Date of Patent: February 9, 1982
    Assignee: General Electric Company
    Inventor: Austin A. Wolfrey
  • Patent number: 4302573
    Abstract: Novel carboxylic acid metal salt/amine complexes are prepared by reacting 1 mol of a carboxylic acid metal salt of the formula(A.sup..crclbar.).sub.2 ME.sup.2+in which A.sup..crclbar. is the anion of a carboxylic acid which contains polar substituents or radicals and in particular contains an amide or imide grouping, such as a halogenoacetic acid, nitrilo-, cyano- or ureido-acetic acid, monoamidosuccinic acid, succinimidyl- or maleimidyl-alkanecarboxylic acid, benzenesulphonic acid or pyrrolidone-5-carboxylic acid, and Me.sup.2+ is a divalent metal cation, with 1 mol of a diamine of the formulaR.sub.1 --NH--R--NH--R.sub.2in which R is an aliphatic radical having not more than 7 C atoms or is a cycloaliphatic radical and R.sub.1 and R.sub.2 are hydrogen, alkyl having 1 to 4 C atoms, cyclohexyl, benzyl, 2-aminoethyl or 3-aminopropyl, in a polar organic solvent and in the temperature range from 25.degree. to 200.degree. C., to give complex compounds.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: November 24, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Friedrich Stockinger, Sameer H. Eldin, Friedrich Lohse
  • Patent number: 4302574
    Abstract: 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: Grant
    Filed: May 12, 1980
    Date of Patent: November 24, 1981
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, James L. Bertram
  • Patent number: 4299938
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic irradiation or by heating in the presence of an aryloxysulfoxonium salt of formula ##STR1## where either R.sup.6 and R.sup.7 separately denote lower alkyl (optionally substituted by halogen and interrupted in the chain by --O-- or --SO.sub.2 --), or an aryl or aryloxy group, or R.sup.6 and R.sup.7 together denote a divalent group forming with the S atom a heterocyclic radical; R.sup.8 denotes an aryl group; M denotes an atom of a metal or metalloid; X denotes a halogen atom; and n is 4, 5, or 6, for instance,p-chlorophenoxy-p-tolyl-p-phenoxysulfoxonium hexafluorophosphate and 1-phenoxy-1-oxidotetrahydrothiophenium tetrafluorborate.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: November 10, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4299944
    Abstract: A process for producing an epihalohydrin copolymer rubber, which comprises copolymerizing an epihalohydrin with another epoxy compound using as a catalyst the reaction product of an organoaluminum compound, a phosphoric acid compound and 1,8-diaza-bicyclo(5,4,0)undecene-7 or its salt.
    Type: Grant
    Filed: June 25, 1980
    Date of Patent: November 10, 1981
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Akio Maeda, Tatuo Usui, Atsushi Yasuda
  • Patent number: 4294886
    Abstract: A highly heat resistant transparency of epoxy resins cured with adducts of trimethoxyboroxine and benzyl alcohol is disclosed. This transparency may exist in a composite with other layers of transparent material known to those skilled in the art. The epoxy resin having the trimethoxyboroxine and benzyl alcohol may also have triphenyl phosphite which further increases the resistance to intense heat for these transparencies in their use on military and industrial hardware.
    Type: Grant
    Filed: August 28, 1979
    Date of Patent: October 13, 1981
    Assignee: Goodyear Aerospace Corporation
    Inventor: John R. Uram, Jr.
  • Patent number: 4293675
    Abstract: The complex formed between a tri-or pentavalent antimony halide and an organic phosphate ester has been found to be an effective catalyst for cationic polymerization reactions.
    Type: Grant
    Filed: February 26, 1980
    Date of Patent: October 6, 1981
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Robert J. Blachunis, Stephen W. Bany
  • Patent number: 4291145
    Abstract: The complex formed between a pentavalent antimony halide and an organic phosphate ester has been found to be an effective catalyst for cationic polymerization reactions.
    Type: Grant
    Filed: February 26, 1980
    Date of Patent: September 22, 1981
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Robert J. Balchunis, Stephen W. Bany
  • Patent number: 4289595
    Abstract: Photopolymerizable epoxide compositions are provided which contain photoinitiators decomposable upon exposure to electromagnetic radiation to produce a Lewis acid and polymerizable epoxide compounds including an epoxide ether compound having the following general structural formula: ##STR1## wherein n equals 1-3 and wherein R is an aliphatic or cycloaliphatic group having 5-12 carbon atoms. Other epoxide compounds may be used in combination therewith to provide compositions which cure rapidly to a tack-free condition at ambient temperatures. Specific epoxide ethers disclosed are those in which n=1 and R is a group selected from the class of 2,2-dimethylpropane, 2-ethyl-1,3-hexane, 1,4-dimethylcyclohexane and 1,10-decane.
    Type: Grant
    Filed: November 26, 1979
    Date of Patent: September 15, 1981
    Assignee: American Can Company
    Inventor: Anthony J. Tortorello
  • Patent number: 4284753
    Abstract: 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: Grant
    Filed: April 14, 1980
    Date of Patent: August 18, 1981
    Assignee: Shell Oil Company
    Inventor: Ralph W. Hewitt, Jr.
  • Patent number: 4282345
    Abstract: A method for preparing a resinous condensation product of an allylated phenol and an ethoxyline resin comprising reacting an allylated phenol with an ethoxyline resin in the presence of an acid catalyst and a compound selected from certain ketones and esters.
    Type: Grant
    Filed: April 16, 1980
    Date of Patent: August 4, 1981
    Assignee: General Electric Company
    Inventor: John D. Nelson
  • Patent number: 4276406
    Abstract: Catalysts for reacting vicinal epoxides with an aromatic hydroxyl-containing material result from the treatment of a solid substrate containing a plurality of ion-exchangeable cations with a polymer containing a multiplicity of quaternary onium cations in association with a reactive anion such that after treatment, there remains a sufficient quantity of the quaternary onium cations in association with the reactive anion to catalyze the reaction. These catalysts reduce the quantity of side reactions.
    Type: Grant
    Filed: April 10, 1980
    Date of Patent: June 30, 1981
    Assignee: The Dow Chemical Company
    Inventors: Georgia A. Monnerat, George E. Ham, Thomas J. Hairston, Melvin J. Hatch
  • Patent number: 4275190
    Abstract: Epoxy resin compositions catalyzed with combinations of diaryliodonium salts of complex halogenides and copper salt catalyst activators are rendered stable at room temperature, but fully activatable at elevated temperatures by including an effective amount of a carboxyl terminated copolymer of butadiene and acrylonitrile, a hydroxy terminated copolymer of butadiene and acrylonitrile or a mixture thereof.
    Type: Grant
    Filed: January 8, 1980
    Date of Patent: June 23, 1981
    Assignee: General Electric Company
    Inventor: Charles D. Dudgeon
  • Patent number: 4273914
    Abstract: 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: Grant
    Filed: March 6, 1980
    Date of Patent: June 16, 1981
    Assignee: Westinghouse Electric Corp.
    Inventors: James D. B. Smith, Arthur W. Ott
  • Patent number: 4259454
    Abstract: Curable organic resin compositions, such as epoxy resins, are provided, based on the use of dialkyl hydroxy arylsulfonium salts in combination with certain orgainc oxidants such as iodosoaromatic esters, or the use of certain amines or transition metals in combination with organic peroxides. The curable compositions can provide flexible or rigid organic resin foam when used with a volatile organic solvent as a result of exothermic heat of cure.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: March 31, 1981
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4246298
    Abstract: A method for the high speed coating of various substrates utilizes an epoxy composition containing a radiation-sensitive catalyst precursor which will decompose upon exposure to electromagnetic radiation to provide a Lewis acid effective to induce cationic polymerization of the epoxy composition. The formulation does not require any special epoxy monomeric materials or accelerators and is stable until so exposed. Subsequent to applying the formulation to the substrate, the coating is exposed to electromagnetic radiation and a controlled temperature of 50.degree.-90.degree. C. is maintained in the coating for a limited period of time to effect polymerization of the formulation to a tack free surface condition within a period of less than 30 seconds. Maintenance at the elevated temperature following initiation of irradiation may be for a period of as little as 0.5 second.
    Type: Grant
    Filed: March 14, 1979
    Date of Patent: January 20, 1981
    Assignee: American Can Company
    Inventors: Joseph M. Guarnery, William R. Watt
  • Patent number: 4238573
    Abstract: The curing temperature of an otherwise substantially conventional methacrylate coating composition is lowered and the weather resistance of the cured composition is improved by incorporating therein a phosphated and amine-neutralized epoxy resin.
    Type: Grant
    Filed: February 12, 1979
    Date of Patent: December 9, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Louis W. Hamilton
  • Patent number: 4225460
    Abstract: Microcapsules with liquid fills containing Lewis acid catalysts, catalyst concentrates comprising slurries of the microcapsules in liquid media and a method for preparing the microcapsules and concentrates.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: September 30, 1980
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Richard G. Newell
  • Patent number: 4221890
    Abstract: An epoxy resin composition which is useful for repairing concrete surfaces having an epoxy resin combined with a curing agent comprised of polyamines and phenolic accelerators. In one embodiment, the epoxy resin is conditioned with a resin modifier comprised of glycidylethers and phenolic and phosphite accelerators prior to being combined with the curing agent. The method for making the curing agent includes a first stage in which an aliphatic polyamine is combined with Bisphenol A and heated to 125.degree. C. for one hour and allowed to cool to room temperature and a second stage in which a second polyamine and an accelerator is added to the product of the first stage. In one embodiment of the method for preparing the curing agent, phenol is added to the mixture of the first stage when the mixture has cooled to 65.degree. C.
    Type: Grant
    Filed: September 30, 1977
    Date of Patent: September 9, 1980
    Assignee: Thermal-Chem, Inc.
    Inventor: Floyd E. Dimmick
  • Patent number: 4215210
    Abstract: A novel resin composition which is composed of molecules having an epi-bis type main skeleton of the formula ##STR1## X.sub.1 -X.sub.4 : H, Cl or Br R: H, or CH.sub.3and has a Gardner-Holdt viscosity of C to Z.sub.8 determined at 25.degree. C. for a solution in butyl carbitol in a concentration of 40% by weight.At least 40% of the entire terminal groups of the molecules of the novel composition consists of .alpha.-glycol groups of the formula ##STR2## wherein R represents hydrogen or methyl. The composition is more rapidly curable at lower temperatures than known epoxy resins having an epi-bis type main chain skeleton, and is useful as a paint or adhesive and also as an adhesion improver for other resins.
    Type: Grant
    Filed: June 9, 1978
    Date of Patent: July 29, 1980
    Assignee: Mitsubishi Petrochemical Company Limited
    Inventors: Kiyoaki Okayama, Yojiro Yamamoto
  • Patent number: 4177173
    Abstract: More rapid curing of polyepoxide resins is achieved by use of a curing system composed of at least one polymercaptan, at least one catalyst which is a poly[(N,N-dimethylamino)alkyl]ether and/or organic non-quaternized salts thereof derived from organic compounds having at least one acidic group and having a pKa greater than about 3.5 and, optionally, organic sulfide, tertiary phosphine or a tertiary amine having no bridged atoms, having no ether oxygen and having at least one tertiary amine group.
    Type: Grant
    Filed: December 20, 1978
    Date of Patent: December 4, 1979
    Assignee: Diamond Shamrock Corporation
    Inventor: Brian J. Carr
  • Patent number: 4173551
    Abstract: Aromatic onium salts, such as diaryliodonium salts, have been found to be effective thermal initiators for the polymerization of a variety of cationically polymerizable materials including epoxides, cyclic ethers, phenol formaldehyde resins, etc., when used in combination with various cocatalysts such as organic acids and copper salts.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: November 6, 1979
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4171420
    Abstract: 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: Grant
    Filed: September 26, 1978
    Date of Patent: October 16, 1979
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette
  • Patent number: 4145369
    Abstract: Flame-retardant epoxy resin compositions comprising a polyepoxide, an acid anhydride curing agent, an imidazole curing accelerator, aluminum trihydrate powder and red phosphorus powder or red phosphorus powder coated by a thermo-setting resin have a lower viscosity and therefore show a longer pot life and better workability on casting as compared with prior art resin compositions. Also, a fly-back transformer coil produced by casting of said flame-retardant epoxy resin compositions is flame-retardant. Even if it burns slightly, no toxic gas is produced. Therefore, the coil has advantages in that a magnet wire is not corroded and voids are difficult to be formed and thereby partial discharge is difficult to occur, resulting in a long life and a stable output voltage.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: March 20, 1979
    Assignee: Hitachi, Ltd.
    Inventors: Yasuo Hira, Ryoichi Sudo, Issei Takemoto, Tokio Isogai
  • Patent number: 4132706
    Abstract: 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: Grant
    Filed: April 5, 1976
    Date of Patent: January 2, 1979
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Lawrence G. Duquette
  • Patent number: 4131633
    Abstract: Certain phosphorus-containing compounds are described herein which are novel latent catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Precatalyzed epoxy resins are easily prepared using such catalysts.
    Type: Grant
    Filed: April 11, 1977
    Date of Patent: December 26, 1978
    Assignee: The Dow Chemical Company
    Inventors: George A. Doorakian, Dennis L. Schmidt, Martin C. Cornell, III