Phenolic Reactant Contains At Least Three Distinct Aromatic Or Carbocyclic Rings Or Mixtures Thereof Patents (Class 528/98)
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Patent number: 5206074Abstract: 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: GrantFiled: February 20, 1991Date of Patent: April 27, 1993Assignee: International Business Machines CorporationInventors: Charles R. Davis, Ashit A. Mehta, Konstantinos Papathomas, Lee P. Springer, William J. Summa, David W. Wang
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Patent number: 5202407Abstract: 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: GrantFiled: January 24, 1992Date of Patent: April 13, 1993Assignee: The Dow Chemical CompanyInventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
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Patent number: 5200475Abstract: 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: GrantFiled: June 3, 1991Date of Patent: April 6, 1993Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 5191033Abstract: 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: GrantFiled: May 11, 1992Date of Patent: March 2, 1993Assignee: Texaco Chemical CompanyInventors: Michael Cuscurida, George P. Speranza, Kathy B. Sellstrom
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Patent number: 5185388Abstract: 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: GrantFiled: May 11, 1992Date of Patent: February 9, 1993Inventors: Yasuyuki Murata, Isako Konishi, Ryohei Tanaka, Yoshinori Nakanishi
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Patent number: 5182358Abstract: 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: GrantFiled: April 11, 1991Date of Patent: January 26, 1993Inventors: Allan S. Hay, Whan Gi Kim
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Patent number: 5179176Abstract: 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: GrantFiled: February 1, 1991Date of Patent: January 12, 1993Assignee: Shin-Etsu Chemical Company, Ltd.Inventors: Toshio Shiobara, Hisashi Shimizu, Takayuki Aoki
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Patent number: 5171765Abstract: 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: GrantFiled: May 8, 1991Date of Patent: December 15, 1992Assignee: North Dakota State UniversityInventors: Frank N. Jones, Daozhang Wang, Steven L. Kangas, Der-Shyang Chen, Adel F. Dimian
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Patent number: 5166184Abstract: 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: GrantFiled: April 24, 1992Date of Patent: November 24, 1992Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Michio Hashimoto, Taira Harada, Yoshihisa Kiso, Isao Kaneko, Gorou Suzuki
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Patent number: 5164464Abstract: 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: GrantFiled: June 7, 1991Date of Patent: November 17, 1992Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 5157165Abstract: 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: GrantFiled: November 22, 1991Date of Patent: October 20, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Naru Koike, Shigeru Iimuro, Mizuo Ito
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Patent number: 5149768Abstract: 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: GrantFiled: June 21, 1991Date of Patent: September 22, 1992Assignee: The Dow Chemical CompanyInventors: Jerry E. White, Anthony P. Haag, R. Garth Pews
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Patent number: 5145920Abstract: 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: GrantFiled: December 10, 1990Date of Patent: September 8, 1992Assignee: Bayer AktiengesellschaftInventors: Bernhard Hess, Dieter Freitag, Karsten-Josef Idel
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Patent number: 5134204Abstract: 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: GrantFiled: May 1, 1990Date of Patent: July 28, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Motoyuki Toriakai, Koutarou Asahina, Mikio Kitahara, Koichi Machida, Takayuki Kubo
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Patent number: 5115074Abstract: 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: GrantFiled: December 6, 1990Date of Patent: May 19, 1992Assignee: Teijin LimitedInventors: Hiroyuki Umetani, Shunichi Matsumura, Takeyoshi Yamada
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Patent number: 5102970Abstract: 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: GrantFiled: July 31, 1991Date of Patent: April 7, 1992Assignee: International Business Machines CorporationInventor: David W. Wang
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Patent number: 5098964Abstract: 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: GrantFiled: January 31, 1991Date of Patent: March 24, 1992Assignee: Shell Oil CompanyInventors: Ronald S. Bauer, Kailash C. B. Dangayach
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Patent number: 5098963Abstract: 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: GrantFiled: February 8, 1991Date of Patent: March 24, 1992Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Abel Mendoza
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Patent number: 5098965Abstract: 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: GrantFiled: January 31, 1991Date of Patent: March 24, 1992Assignee: Shell Oil CompanyInventors: Ronald S. Bauer, Kailash C. B. Dangayach
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Patent number: 5089588Abstract: 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: GrantFiled: February 26, 1991Date of Patent: February 18, 1992Assignee: The Dow Chemical CompanyInventors: Jerry E. White, David J. Brennan, Steven Pikulin
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Patent number: 5081206Abstract: 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: GrantFiled: May 29, 1990Date of Patent: January 14, 1992Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Kiyomi Yasuda, Terufumi Suzuki, Toshimasa Takata, Isao Kaneko
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Patent number: 5077375Abstract: 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: GrantFiled: January 22, 1991Date of Patent: December 31, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Noriaki Saito, Shuichi Kanagawa, Hideshi Sakamoto
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Patent number: 5075411Abstract: 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: GrantFiled: February 16, 1990Date of Patent: December 24, 1991Assignees: 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
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Patent number: 5070159Abstract: 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: GrantFiled: June 16, 1989Date of Patent: December 3, 1991Assignee: Hoechst AktiengesellschaftInventors: Erwin Dietz, Andreas Sommer, Adolf Kroh, Jurgen Hohn, Otmar Hafner, Wolfgang Rieper
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Patent number: 5068268Abstract: New epoxy polymers comprise lightly crosslinked linear molecules prepared from segments containing stiff units interconnected to form internally non-rotating, planar segments.Type: GrantFiled: September 12, 1989Date of Patent: November 26, 1991Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 5066735Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecules; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: April 12, 1990Date of Patent: November 19, 1991Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 5061779Abstract: 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: GrantFiled: March 14, 1989Date of Patent: October 29, 1991Assignee: International Business Machines CorporationInventor: David W. Wang
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Patent number: 5053475Abstract: 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: GrantFiled: June 22, 1990Date of Patent: October 1, 1991Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Hisashi Tada, Akira Agata, Masahiro Saruta, Takashi Murata, Takatoshi Kubo
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Patent number: 5039777Abstract: 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: GrantFiled: January 23, 1991Date of Patent: August 13, 1991Assignee: Bridgestone CorporationInventors: Toshihiro Yotsumoto, Koichi Morita, Takeshi Kinoshita
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Patent number: 5028668Abstract: 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: GrantFiled: July 6, 1990Date of Patent: July 2, 1991Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Abel Mendoza
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Patent number: 5025067Abstract: 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: GrantFiled: November 16, 1988Date of Patent: June 18, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Yohzoh Yamamoto, Goro Suzuki, Hideo Nakamura, Kiyomi Yasuda
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Patent number: 5021470Abstract: 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: GrantFiled: March 23, 1989Date of Patent: June 4, 1991Assignee: BASF CorporationInventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
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Patent number: 4996279Abstract: Dissymmetric new epoxy polymer materials have improved processability because they can be cured at lower temperatures.Type: GrantFiled: October 7, 1988Date of Patent: February 26, 1991Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 4994536Abstract: 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: GrantFiled: June 23, 1988Date of Patent: February 19, 1991Assignee: Rhone-Poulenc ChimieInventor: Rene Arpin
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Patent number: 4973649Abstract: 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: GrantFiled: March 3, 1989Date of Patent: November 27, 1990Assignee: Rhone-Poulenc ChimieInventor: Yves Camberlin
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Patent number: 4959438Abstract: 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: GrantFiled: January 27, 1989Date of Patent: September 25, 1990Assignee: Mitsubishi Rayon Company, Ltd.Inventors: Hisashi Tada, Akira Agata, Masahiro Saruta, Takashi Murata
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Patent number: 4959425Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resing having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: June 27, 1989Date of Patent: September 25, 1990Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4956440Abstract: Polymeric tertiary arylamine compounds of the phenoxy resin type which find utility especially in electrophotographic imaging.Type: GrantFiled: November 23, 1988Date of Patent: September 11, 1990Assignee: Xerox CorporationInventors: William W. Limburg, Dale S. Renfer, John F. Yanus, Leon A. Teuscher
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Patent number: 4956411Abstract: An epoxy resin composition is disclosed that can be cured at a temperature of 150.degree. C. or below, and can be used to provide a high performance carbon fiber composite material having a 0.degree. direction bending strength of 220 kg/mm.sup.2 or over, and an interlayer shear strength of 10 kg/mm.sup.2 or over.The composition is made up of:(A) an epoxy compound containing 10 to 100% by weight of m- or o-methyl-p-N,N-diglycidyl-aminophenyl-ester or its oligomer,(B) diaminodiphenylsulfone and/or diaminodiphenylmethane,(C) dicyandiamide, 2,6-xylenylbiguanide, o-tolylbiguanide, diphenylguanidine, adipil dihydrazide, azelayl dihydrazide, or isophthalic acid dihydrazide, and(D) a urea compound.Type: GrantFiled: January 30, 1989Date of Patent: September 11, 1990Assignee: Mitsubishi Rayon Company, Ltd.Inventors: Hisashi Tada, Yoshinobu Shiraishi, Shigetsugu Hayashi
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Patent number: 4954603Abstract: 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: GrantFiled: June 6, 1989Date of Patent: September 4, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Toshimasa Takata, Kenichi Mizuno
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Patent number: 4916202Abstract: 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: GrantFiled: September 17, 1987Date of Patent: April 10, 1990Assignee: University of DaytonInventors: John M. Butler, Richard P. Chartoff, James A. Harvey
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Patent number: 4916203Abstract: A curable resin composition comprises an epoxy compound and a propargyl aromatic ether.Type: GrantFiled: November 14, 1988Date of Patent: April 10, 1990Assignee: Shell Oil CompanyInventors: Anthony M. Pigneri, James Vick, III, deceased
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Patent number: 4910286Abstract: 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: GrantFiled: May 30, 1988Date of Patent: March 20, 1990Assignee: Eastman Kodak CompanyInventors: Alan W. White, Randy S. Beavers
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Patent number: 4908424Abstract: Certain bis-anthrols and bis-naphthols and their diglycidyl ethers are novel and useful in the preparation of new polyether thermoplastic compositions.Type: GrantFiled: February 6, 1989Date of Patent: March 13, 1990Assignee: Shell Oil CompanyInventors: Kenneth C. Dewhirst, Thomas G. Stewart, Jr.
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Patent number: 4900848Abstract: 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: GrantFiled: March 29, 1988Date of Patent: February 13, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhisa Saito, Katsuya Watanabe, Kohichi Okuno, Kunimasa Kamio, Akira Morii, Hiroshi Nakamura
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Patent number: 4895755Abstract: 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: GrantFiled: October 14, 1988Date of Patent: January 23, 1990Assignee: The Dow Chemical CompanyInventors: Jody R. Berman, Chun S. Wang, Louis L. Walker, Abel Mendoza
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Patent number: 4894431Abstract: 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: GrantFiled: May 23, 1988Date of Patent: January 16, 1990Assignee: Ciba-Geigy CorporationInventors: Robert F. Armbruster, Rajan Eadara, William L. Miller
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Patent number: 4891408Abstract: 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: GrantFiled: August 13, 1987Date of Patent: January 2, 1990Assignee: Amoco CorporationInventor: Richard H. Newman-Evans
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Patent number: 4874669Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a ketone solvent solution of a curable composition comprising (A) at least one aromatic based epoxy resin having an average number of epoxide groups per molecule of more than 2; (B) a mixture of (1) at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule; and (2) at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C), optionally, at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: August 15, 1988Date of Patent: October 17, 1989Assignee: The Dow Chemical CompanyInventors: Paul A. Larson, Dale J. Aldrich, Jody R. Berman
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Patent number: 4868059Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: November 16, 1987Date of Patent: September 19, 1989Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson