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