Phenolic Reactant Contains At Least Three Distinct Aromatic Or Carbocyclic Rings Or Mixtures Thereof Patents (Class 528/98)
  • Patent number: 5206074
    Abstract: Disclosed is a polymeric product of diglycidyl bis phenol p-dialkyl benzene, and dicyanate diphenyl hexafluoro isopropane. Also disclosed is an organic polymeric dielectric composite of organic polymeric films, as polyimide films, dispersed in and reinforcing the organic polymeric adhesive reaction product of diglycidyl bis phenol p-dialkyl benzene, and dicyanate diphenyl hexafluoro isopropane. Further disclosed is an electronic circuit package that is adapted to receive at least one microelectronic circuit chip, with at least one layer having a substrate of an organic polymeric dielectric composite of organic polymeric films and the organic polymeric adhesive reaction product of diglycidyl bis phenol p-dialkyl benzene, and dicyanate diphenyl hexafluoro isopropane.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: April 27, 1993
    Assignee: International Business Machines Corporation
    Inventors: Charles R. Davis, Ashit A. Mehta, Konstantinos Papathomas, Lee P. Springer, William J. Summa, David W. Wang
  • Patent number: 5202407
    Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorus atom per molecule.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: April 13, 1993
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
  • Patent number: 5200475
    Abstract: A lightly-crosslinked thermosettable formulation comprises (a) a diepoxy resin, (b) an aromatic diamine of the structural formula ##STR1## in which each R is a divalent linking moiety selected from C.sub.1-6 alkylene, --S-- and --O--, and R' is ethyl, (c) an amine or phenolic crosslinking agent, and (d) 2,6-dialkyl aniline. The formulation exhibits relatively long outlife and can be used as the matrix resin in aerospace composites applications.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: April 6, 1993
    Assignee: Shell Oil Company
    Inventor: Kenneth C. Dewhirst
  • Patent number: 5191033
    Abstract: The invention is an epoxy resin composition. Diol initiators are reacted with alkylene oxide and 1 to 5 wt % epoxy resin. The epoxy resin is added internally, along the length of the diol chain to yield a modified polyol of molecular weight 2000 to 5000. The modified polyol is subjected to reductive amination to yield a polyamine. This polyamine is mixed with an epoxy base resin and cured to product epoxy resins demonstrating improved strength and adhesion.
    Type: Grant
    Filed: May 11, 1992
    Date of Patent: March 2, 1993
    Assignee: Texaco Chemical Company
    Inventors: Michael Cuscurida, George P. Speranza, Kathy B. Sellstrom
  • Patent number: 5185388
    Abstract: An electrical encapsulation composition is disclosed comprising (a) an epoxy resin which is the product of glycidating a polyphenolic compound which is the condensation product of (i) a substituted phenol which can be represented by the formula ##STR1## in which each R is selected independently from hydrogen, C.sub.1-5 alkyl and phenyl, with the provisos that at least two R groups are not hydrogen and that the R groups may be bonded in a ring structure, and (ii) an aromatic aldehyde or aromatic ketone having a phenolic hydroxyl group as represented by the general formula ##STR2## in which R' is selected from hydrogen, C.sub.1-5 alkyl and phenyl, R" is selected from C.sub.1-5 alkyl, phenyl, methoxy and halogen, and n is an integer from 0 to 4; (b) a curing agent for the epoxy resin; and (c) an inorganic filler.
    Type: Grant
    Filed: May 11, 1992
    Date of Patent: February 9, 1993
    Inventors: Yasuyuki Murata, Isako Konishi, Ryohei Tanaka, Yoshinori Nakanishi
  • Patent number: 5182358
    Abstract: Polymers and copolymers having high glass transition temperature and which are soluble in organic solvents are produced from highly hindered biphenols, in particular polyetherketones, polyethersulfones, polyesters and polyetherimides, as well as copolymers based on these polymers may be produced for a variety of applications.
    Type: Grant
    Filed: April 11, 1991
    Date of Patent: January 26, 1993
    Inventors: Allan S. Hay, Whan Gi Kim
  • Patent number: 5179176
    Abstract: An epoxy resin having a propenyl group conjugated with an aromatic ring is heat resistant and is easily molded and cured into products having high strength and Tg. It is thus useful as a resin component or modifier.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: January 12, 1993
    Assignee: Shin-Etsu Chemical Company, Ltd.
    Inventors: Toshio Shiobara, Hisashi Shimizu, Takayuki Aoki
  • Patent number: 5171765
    Abstract: This application describes a water dispersible polymeric vehicle comprising epoxy polymers having about 5 to 50 weight percent mesogens or a cross-linkable blend of an amine salt of a mesogenic carboxylic acid, cross-linker resin and an epoxy polymer, the mesogenic acid providing about 5 to 50 weight percent mesogenic groups to the blend.
    Type: Grant
    Filed: May 8, 1991
    Date of Patent: December 15, 1992
    Assignee: North Dakota State University
    Inventors: Frank N. Jones, Daozhang Wang, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian
  • Patent number: 5166184
    Abstract: A normally liquid epoxy resin obtainable by reaction of a bisphenol based oligocarbonate having terminal phenolic hydroxyl groups with an epihalohydrin, followed by dehydrohalogenation. The epoxy resin is capable of forming a tough cured product having improved flexural strength and flexural modulus. A process for the production of an epoxy resin foam in which a polyepoxy compound is crosslinked and simultaneously foamed by the aid of carbonate oligomers having terminal phenolic hydroxyl groups. The product is highly flexible against compression, bending and warp.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: November 24, 1992
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Michio Hashimoto, Taira Harada, Yoshihisa Kiso, Isao Kaneko, Gorou Suzuki
  • Patent number: 5164464
    Abstract: Thermosettable vinyl ester resin compositions are prepared from polyepoxide compounds, optionally, monoepoxide compounds, at least one of which contains a mesogenic or rigid rodlike moiety and a monounsaturated monocarboxylic acid. These vinyl ester resins can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: November 17, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5157165
    Abstract: Herein provided are a method for preparing 1,1,2,2-tetrakis(4-hydroxy-3,5-dimethylphenyl)ethane (TKXE) comprising subjecting two molecules of bis(3,5-dimethyl-4-hydroxyphenyl) methane to dehydration-condensation under oxidizing conditions, an epoxy resin prepared by epoxidating TKXE obtained by the method and an epoxy resin composition comprising TKXE obtained by the method as a hardener and an epoxy resin as well as methods for preparing the resin and composition. The method makes it possible to prepare highly pure TKXE in the form of crystals. Moreover, the epoxy resin and the epoxy resin composition can provide hardened products excellent in physical properties such as heat resistance and mechanical strength.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: October 20, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Naru Koike, Shigeru Iimuro, Mizuo Ito
  • Patent number: 5149768
    Abstract: Hydroxy-functional poly(ether sulfonamides) prepared by polymerizing an N,N'-dialkyl or N,N'-diaryldisulfonamide with a diepoxide in the presence of a suitable catalyst exhibit high barrier properties. These are suitable for use in the manufacture of articles such as rigid containers and flexible films exhibiting high barrier to oxygen.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: September 22, 1992
    Assignee: The Dow Chemical Company
    Inventors: Jerry E. White, Anthony P. Haag, R. Garth Pews
  • Patent number: 5145920
    Abstract: The invention relates to oligomer epoxy resins which are derived especially from diphenols or from diglycidyl ethers based on these phenols, oligomer epoxy resins containing oxazolidinone groups and based on the novel diglycidyl ethers and curable mixtures containing the novel oligomer epoxy resins, and the reaction products of the novel oligomer epoxy resins with unsaturated carboxylic acids, preferably in the presence of a vinyl monomer to give phenacrylate resins, and phenacrylate resins containing oxazolidinone groups and based on the novel diglycidyl ethers.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: September 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernhard Hess, Dieter Freitag, Karsten-Josef Idel
  • Patent number: 5134204
    Abstract: A resin composition for sealing semiconductors which shows high heat resistance and is suitable for sealing semiconductor devices, etc., and which comprises an organic component containing a polymaleimide compound represented by the general formula: ##STR1## where R.sub.1 is a m-valent organic group having at least 2 carbon atoms and m is a positive integer of 2 or more, epoxy compounds mainly consisting of an epoxy compound represented by the general formula: ##STR2## where n is a positive integer of 3-16 and a compound having two or more phenolic hydroxyl groups, and an inorganic filler.
    Type: Grant
    Filed: May 1, 1990
    Date of Patent: July 28, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Motoyuki Toriakai, Koutarou Asahina, Mikio Kitahara, Koichi Machida, Takayuki Kubo
  • Patent number: 5115074
    Abstract: There is provided a novolak-type hydroxycarboxylic acid or an ester thereof, an epoxy compound produced therefrom, a composite material comprising a matrix resin of the cured product and a reinforcing material, and a process for the production of the epoxy compound. The epoxy compound produces a cured product having excellent water resistance, heat resistance, chemical resistance, mechanical properties, dimensional stability and electrical properties.
    Type: Grant
    Filed: December 6, 1990
    Date of Patent: May 19, 1992
    Assignee: Teijin Limited
    Inventors: Hiroyuki Umetani, Shunichi Matsumura, Takeyoshi Yamada
  • Patent number: 5102970
    Abstract: A liquid expoxy composition containing a diglycidyl ether of a dihydric phenol and/or a diglycidyl ether of a tetrabrominated dihydric phenol, an epoxy with a functionality from 2.2 to 4, cycloaliphatic diamine curing agent, and thixotropic agent; and use thereof to fill drilled through-holes in circuit boards and cards and as isolation border around the edges of a board or card.
    Type: Grant
    Filed: July 31, 1991
    Date of Patent: April 7, 1992
    Assignee: International Business Machines Corporation
    Inventor: David W. Wang
  • Patent number: 5098964
    Abstract: A process is disclosed for preparing a low-chlorine tetrafunctional epoxy resin which employs crystallization of the epoxy resin from solution in a finishing step of the preparation process. The process involves (a) contacting, in a basic reaction medium, epichlorohydrin and a tetraphenol of ethane to produce a reaction product mixture containing a polyglycidyl ether of the tetraphenol of ethane; (b) dissolving the polyglycidyl ether in an organic solvent and, optionally, contacting the polyglycidyl ether with a dehydrochlorination agent; and (c) reducing the temperature of the organic solvent so as to effect crystallization of a low-chlorine fraction of the polyglycidyl ether.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: March 24, 1992
    Assignee: Shell Oil Company
    Inventors: Ronald S. Bauer, Kailash C. B. Dangayach
  • Patent number: 5098963
    Abstract: Adducts of metabrominated monophenols such as 3,5-dibromo-2,4,6-trimethylphenol and multifunctional epoxides such as cresol-formaldehyde epoxy novolac resins are disclosed to be useful in formulations for encapsulating electronic components.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: March 24, 1992
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Abel Mendoza
  • Patent number: 5098965
    Abstract: A process is disclosed for preparing a low-chlorine epoxy resin which employs crystallization of the epoxy from solution in a finishing step of the preparation process. The process involves (a) contacting, in a basic reaction medium, epichlorohydrin and a biphenol to produce a reaction product mixture containing a diglycidyl ether of the biphenol; (b) dissolving the diglycidyl ether in an organic solvent and, optionally, contacting the diglycidyl ether with a dehydrochlorination agent; and (c) reducing the temperature of the organic solvent so as to effect crystallization of a low-chlorine fraction of the diglycidyl ether.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: March 24, 1992
    Assignee: Shell Oil Company
    Inventors: Ronald S. Bauer, Kailash C. B. Dangayach
  • Patent number: 5089588
    Abstract: Hydroxy-functional poly(amide-ethers) are fabricated into articles such as rigid containers and flexible films exhibiting high barrier to oxygen transmission in both dry and moist environments. For example, a polymer prepared by reacting the diglycidyl ether of 4,4'-biphenol with N,N'-bis(m-hydroxyphenyl)-adipamide exhibits especially high barrier.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: February 18, 1992
    Assignee: The Dow Chemical Company
    Inventors: Jerry E. White, David J. Brennan, Steven Pikulin
  • Patent number: 5081206
    Abstract: A heat-resistant, flame-retardant epoxy resin composition is provided by combining or reating members selected from a polyfunctional epoxy resin, a bisphenol type epoxy resin, a highly halogenated bisphenol type epoxy resin, a low halogenated bisphenol type epoxy resin, and a halogenated bisphenol. The composition is suitable as a laminate useful for printed circuit boards.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: January 14, 1992
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Kiyomi Yasuda, Terufumi Suzuki, Toshimasa Takata, Isao Kaneko
  • Patent number: 5077375
    Abstract: A glycidyl ether of a phenolic compound of the formula: ##STR1## wherein each of R.sup.1 through R.sup.6 represents an alkyl group of from 1 to 6 carbon atoms; each of R.sup.7 to R.sup.12 represents a hydrogen atom, an alkyl group of from 1 to 4 carbon atoms, or an alkoxy group of from 1 to 4 carbon atoms; X represents a chlorine or bromine atom; GE represents a glycidyl ether group; a, b, c, d, and e are 0 or 1; and n is an average number of from 0.5 to 5. The high purity glycidyl ether of the phenolic compound can be produced by reacting the corresponding phenolic compound with an epichlorohydrin in an aprotic polar solvent in the presence of an alkali metal hydroxide and then treating the resulting crude glycidyl ether compound with an alkaline material in an organic solvent.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: December 31, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriaki Saito, Shuichi Kanagawa, Hideshi Sakamoto
  • Patent number: 5075411
    Abstract: A curable epoxy resin composition comprises (I) an epoxy resin and (II) a curing agent. It may comprise (III) another curing agent. It is preferable for it to comprise 25 to 95 wt.% of (I) and 5 to 45 wt.% of (II).1 an epoxy resin (I) represented by the general formula: ##STR1## wherein Z represents a group selected from among a hydrogen atom, a methyl group and an ethyl group, R represents a group selected from among a hydrogen atom and alkyl groups, and n represents a number of 0 to 1.6, and2 a curing agent comprising a polyamine reaction composition (II) obtained by reacting 1 mol of a phenol (II-1) having at least one unsubstituted reactive site in the aromatic nucleus with at least 1 mol of an aliphatic polyamine (II-2) and at least 1 mol of a carbonyl compound (II-3) having at least one carbonyl group in the molecule.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: December 24, 1991
    Assignees: Nissan Motor Co., Tsuchiya Mfg. Co., Ltd., Asahi Denka Kogyo K.K., A.C.R. Co., Ltd.
    Inventors: Akio Ogawa, Yukio Ohsaki, Takeichiro Takehara, Tadashi Ashida, Seiichiro Hashimoto
  • Patent number: 5070159
    Abstract: Addition compounds which are suitable as dispersants for solids in organic media are obtained from polyepoxides based on novolaks having 3 to 11 nuclei and a mixture of aliphatic, aromatic and/or heterocyclic amines.
    Type: Grant
    Filed: June 16, 1989
    Date of Patent: December 3, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Andreas Sommer, Adolf Kroh, Jurgen Hohn, Otmar Hafner, Wolfgang Rieper
  • Patent number: 5068268
    Abstract: New epoxy polymers comprise lightly crosslinked linear molecules prepared from segments containing stiff units interconnected to form internally non-rotating, planar segments.
    Type: Grant
    Filed: September 12, 1989
    Date of Patent: November 26, 1991
    Assignee: Shell Oil Company
    Inventor: Kenneth C. Dewhirst
  • Patent number: 5066735
    Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecules; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: November 19, 1991
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Paul A. Larson
  • Patent number: 5061779
    Abstract: A liquid epoxy composition containing a diglycidyl ether of a dihydric phenol and/or a diglycidyl ether of a tetrabrominated dihydric phenol, an epoxy with a functionality from 2.2 to 4, cycloaliphatic diamine curing agent, and thixotropic agent; and use thereof to fill drilled through-holes in circuit boards and cards and as isolation border around the edges of a board or card.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: October 29, 1991
    Assignee: International Business Machines Corporation
    Inventor: David W. Wang
  • Patent number: 5053475
    Abstract: An epoxy resin composition characterized by comprising, as essential components,(A) a bifunctional epoxy resin,(B) a trifunctional epoxy resin,(C) a phenol compound represented by the following formula ##STR1## (X.sub.1 to X.sub.8 each represent Br, Cl or H and at least four of X.sub.1 to X.sub.8 each represent Br or Cl; R.sub.1 and R.sub.2 each represent H or CH.sub.3), and(D) 4,4'-diaminodiphenyl sulfone or 3,3'-diaminodiphenyl sulfone.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: October 1, 1991
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Hisashi Tada, Akira Agata, Masahiro Saruta, Takashi Murata, Takatoshi Kubo
  • Patent number: 5039777
    Abstract: An aniline-resorcin-formaldehyde copolycondensation product having a particular mol ratio of aniline to resorcin is used in an adhesive composition for well adhering fibrous material to rubber.
    Type: Grant
    Filed: January 23, 1991
    Date of Patent: August 13, 1991
    Assignee: Bridgestone Corporation
    Inventors: Toshihiro Yotsumoto, Koichi Morita, Takeshi Kinoshita
  • Patent number: 5028668
    Abstract: Adducts of metabrominated monophenols such as 3,5-dibromo-2,4,6-trimethylphenol and multifunctional epoxides such as cresol-formaldehyde epoxy novolac resins are disclosed to be useful in formulations for encapsulating electronic components.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: July 2, 1991
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Abel Mendoza
  • Patent number: 5025067
    Abstract: An epoxy resin comprising an active hydrogen compound having at least three active hydrogen atoms capable of reacting with an epoxy group in its molecule or butadine or isoprene as a main monomer is modified with an oligomer having on average at least 1.5 equivalents of active hydrogen capable of reacting with an epoxy group in its molecule. An epoxy resin modified with a bisphenol and a compound having active hydrogen or acid anhydride groups capable of reacting with an epoxy group is also provided. A toner containing the epoxy resin as a binder is useful in electrostatography.
    Type: Grant
    Filed: November 16, 1988
    Date of Patent: June 18, 1991
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Yohzoh Yamamoto, Goro Suzuki, Hideo Nakamura, Kiyomi Yasuda
  • Patent number: 5021470
    Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: June 4, 1991
    Assignee: BASF Corporation
    Inventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
  • Patent number: 4996279
    Abstract: Dissymmetric new epoxy polymer materials have improved processability because they can be cured at lower temperatures.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: February 26, 1991
    Assignee: Shell Oil Company
    Inventor: Kenneth C. Dewhirst
  • Patent number: 4994536
    Abstract: Thermally stable bisimido polymers, devoid of diamine component and well adapted for the production of laminates, are prepared by copolymerizing (a) an N,N'-bismaleimide with (b) an acrylate comonomer, e.g., a novolak epoxy (meth)acrylate, in the presence of a catalytically effective amount of (c) an imidazole compound, and, optionally, (d) a chlorinated or brominated epoxy resin, or admixture thereof with a non-chlorinated or non-brominated epoxy resin.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: February 19, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventor: Rene Arpin
  • Patent number: 4973649
    Abstract: Novel thermosetting imido prepolymers having low melt viscosity, well adapted for the production, e.g., of preimpregnated shaped articles, are copolymerizates of at least one N,N'-bismaleimide; at least one hindered diprimary diamine, e.g., 4,4'-diamino-3,3',5,5'-tetraalkyl-diphenyl-methane or 1,3-diamino- or 1,4-diaminotrialkylbenzene; at least one comonomeric heterocycle, e.g., a vinylpyridine, N-vinyl-2-pyrrolidone, allyl isocyanurate, vinyltetrahydrofuran, and/or an imidazole compound; and at least one comonomeric (meth)acrylate.
    Type: Grant
    Filed: March 3, 1989
    Date of Patent: November 27, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventor: Yves Camberlin
  • Patent number: 4959438
    Abstract: An epoxy resin composition is disclosed, which comprises the following elements:(A) a bifunctional epoxy resin;(B) a trifunctional epoxy resin;(C) a phenolic compound represented by the following general formula: ##STR1## wherein X.sub.1, X.sub.2, X.sub.3, X.sub.4, X.sub.5, X.sub.6, X.sub.7, X.sub.8, X.sub.9, X.sub.10, X.sub.11, X.sub.12, R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom or a methyl group; and(D) 4,4'-diaminodiphenyl sulfone or 3,3'-diaminodiphenyl sulfone, wherein the molar ratio of epoxy groups in element (A) to those in element (B) is in the range of from 1/4.0 to 1/0.1, element (C) is used in an amount that satisfies the condition:1/0.9.ltoreq.(A+B)/C.ltoreq.1/0.1and element (D) is used in an amount that satisfies the condition:1/1.3.ltoreq.(A+B-C)/D.ltoreq.1/0.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: September 25, 1990
    Assignee: Mitsubishi Rayon Company, Ltd.
    Inventors: Hisashi Tada, Akira Agata, Masahiro Saruta, Takashi Murata
  • Patent number: 4959425
    Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resing having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: September 25, 1990
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Paul A. Larson
  • Patent number: 4956440
    Abstract: Polymeric tertiary arylamine compounds of the phenoxy resin type which find utility especially in electrophotographic imaging.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: September 11, 1990
    Assignee: Xerox Corporation
    Inventors: William W. Limburg, Dale S. Renfer, John F. Yanus, Leon A. Teuscher
  • Patent number: 4956411
    Abstract: An epoxy resin composition is disclosed that can be cured at a temperature of 150.degree. C. or below, and can be used to provide a high performance carbon fiber composite material having a 0.degree. direction bending strength of 220 kg/mm.sup.2 or over, and an interlayer shear strength of 10 kg/mm.sup.2 or over.The composition is made up of:(A) an epoxy compound containing 10 to 100% by weight of m- or o-methyl-p-N,N-diglycidyl-aminophenyl-ester or its oligomer,(B) diaminodiphenylsulfone and/or diaminodiphenylmethane,(C) dicyandiamide, 2,6-xylenylbiguanide, o-tolylbiguanide, diphenylguanidine, adipil dihydrazide, azelayl dihydrazide, or isophthalic acid dihydrazide, and(D) a urea compound.
    Type: Grant
    Filed: January 30, 1989
    Date of Patent: September 11, 1990
    Assignee: Mitsubishi Rayon Company, Ltd.
    Inventors: Hisashi Tada, Yoshinobu Shiraishi, Shigetsugu Hayashi
  • Patent number: 4954603
    Abstract: Disclosed is a heat-resistant flame-retardant epoxy resin composition comprising a halogen-containing epoxy resin obtained by reacting a trifunctional epoxy compound having a specific structure with a halogenated bisphenol in the presence of a catalyst. Furthermore, a novel specific trifunctional epoxy compound is disclosed, which is valuably used for the production of the above-mentioned halogen-containing epoxy resin.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: September 4, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Toshimasa Takata, Kenichi Mizuno
  • Patent number: 4916202
    Abstract: The present invention provides an epoxy resin of the formula ##STR1## where A is selected from the group consisting of --C(CH.sub.3).sub.2 --, --C(CF.sub.3).sub.2 --, --S--, --SO.sub.2 --, --CH.sub.2 --, --CO--, --O--, and --C.sub.3 H.sub.6 --, and each B.sub.1, B.sub.2, B.sub.3, and B.sub.4 is independently selected from the group consisting of --H, --F, --Cl, --Br, --I, --CH.sub.2 CH.dbd.CH.sub.2, --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7, and --C.sub.4 H.sub.9.The present invention also provides a curable composition comprising an epoxy resin of the foregoing formula (I) and an effective curing amount of a hardener for an epoxy resin. The moisture sensitivity of the cured castings and/or composites based on the epoxy resins is lower than known epoxy resin castings and/or composites that have comparable thermal stability, modulus, strength, processability, and toughness.
    Type: Grant
    Filed: September 17, 1987
    Date of Patent: April 10, 1990
    Assignee: University of Dayton
    Inventors: John M. Butler, Richard P. Chartoff, James A. Harvey
  • Patent number: 4916203
    Abstract: A curable resin composition comprises an epoxy compound and a propargyl aromatic ether.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: April 10, 1990
    Assignee: Shell Oil Company
    Inventors: Anthony M. Pigneri, James Vick, III, deceased
  • Patent number: 4910286
    Abstract: Disclosed are reactive phenolic compounds having the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are certain substituents. Also disclosed are certain polyesters normally susceptible to oxidative degradation having copolymerized therein at least one residue of one of the phenolic compounds.
    Type: Grant
    Filed: May 30, 1988
    Date of Patent: March 20, 1990
    Assignee: Eastman Kodak Company
    Inventors: Alan W. White, Randy S. Beavers
  • Patent number: 4908424
    Abstract: Certain bis-anthrols and bis-naphthols and their diglycidyl ethers are novel and useful in the preparation of new polyether thermoplastic compositions.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: March 13, 1990
    Assignee: Shell Oil Company
    Inventors: Kenneth C. Dewhirst, Thomas G. Stewart, Jr.
  • Patent number: 4900848
    Abstract: A low viscosity epoxy resin, i.e., a low viscosity polyglycidyl derivative, of an aminophenol having at least one alkyl group on its aromatic ring of which viscosity is 15 poises or below as measured at 25.degree. C., a resin composition containing said resin, and a fiber-reinforced composite material containing as matrix a cured product of said epoxy resin composition and a fiber as reinforcing material.
    Type: Grant
    Filed: March 29, 1988
    Date of Patent: February 13, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuhisa Saito, Katsuya Watanabe, Kohichi Okuno, Kunimasa Kamio, Akira Morii, Hiroshi Nakamura
  • Patent number: 4895755
    Abstract: Advanced epoxy resins are disclosed which result from the reaction of a relatively low molecular weight epoxy resin and a polyhydric phenol wherein at least one of the reactants contains at least one halogen atom which is meta with respect to a glycidyl ether group or a hydroxyl group attached to an aromatic ring. These advanced epoxy resins, when cured with a suitable curing agent, possess an improvement as compared to an advanced epoxy resin containing halogen atoms which are ortho with respect to a glycidyl ether group in at least one of thermal stability, glass transition temperature, relationship of viscosity to molecular weight and resistance to forming hydrolyzed halides in the presence of a refluxing solution of an alkali metal hydroxide.
    Type: Grant
    Filed: October 14, 1988
    Date of Patent: January 23, 1990
    Assignee: The Dow Chemical Company
    Inventors: Jody R. Berman, Chun S. Wang, Louis L. Walker, Abel Mendoza
  • Patent number: 4894431
    Abstract: Curing systems for epoxy resins comprising an aliphatic or cycloaliphatic amine in combination with anhydrous methane sulfonic acid as an accelerator for the curing reaction.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: January 16, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert F. Armbruster, Rajan Eadara, William L. Miller
  • Patent number: 4891408
    Abstract: Novel tetraglycidates have the formula ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl of 1 to 8 carbon atoms, perfluoroalkyl, or cycloalkylidene of 5 to 7 carbon atoms. Epoxy resin systems exhibiting good tensile properties and moisture sensitivity can be made by copolymerizing the tetraglycidates with a polyamine curing agent. Prepregs can be made by combining the epoxy resin systems with a fiber reinforcement. The epoxy resin system may include a co-epoxide.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: January 2, 1990
    Assignee: Amoco Corporation
    Inventor: Richard H. Newman-Evans
  • Patent number: 4874669
    Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a ketone solvent solution of a curable composition comprising (A) at least one aromatic based epoxy resin having an average number of epoxide groups per molecule of more than 2; (B) a mixture of (1) at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule; and (2) at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C), optionally, at least one catalyst for effecting the reaction between (A) and (B).
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: October 17, 1989
    Assignee: The Dow Chemical Company
    Inventors: Paul A. Larson, Dale J. Aldrich, Jody R. Berman
  • Patent number: 4868059
    Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: September 19, 1989
    Assignee: The Dow Chemical Company
    Inventors: Louis L. Walker, Paul A. Larson