Phenolic-aldehyde Or Phenolic-aldehyde-type Reaction Product Modified With 1,2-monoepoxide Prior To Mixing With Reactant Containing More Than One 1,2 Epoxy Group Per Mole Or Polymer Derived Therefrom Patents (Class 525/482)
  • 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: 5026789
    Abstract: A curable impact modified epoxy resin mixture suitable for producing high performance composites is composed ofA. an aromatic epoxy compound,B. an amine type curing agent,C. from 10 to 40% by weight of an aromatic thermoplastic oligomer which contains reactive groups, preferably a polyether sulfone, andD. from 0.1 to 10% by weight of a high molecular weight emulsifier, preferably a phenoxy resin, an epoxy resin or a thermoplastic copolymer, which is compatible not only with the epoxy compound A but also with oligomer C.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: June 25, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Weber, Walter Heckmann, Jurgen Mertes, Helmut Tesch, Volker Altstaedt, Wolfgang Eberle, Thomas Folda, Herbert Stutz, Hans-Gert Recker
  • Patent number: 5017674
    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-ether 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: June 27, 1990
    Date of Patent: May 21, 1991
    Inventors: Hisashi Tada, Yoshinobu Shiraishi, Shigetsuga Hayashi
  • Patent number: 5015675
    Abstract: A heat curable composition is provided which is useful for encapsulating microelectronic devices using a heat curable epoxy composition having a diaryliodonium hexafluoroantimonate salt as a catalyst in combination with an effective amount of a free radical generating aromatic compound as a cocatalyst.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: May 14, 1991
    Assignee: General Electric Company
    Inventors: Erik W. Walles, John H. Lupinski, James V. Crivello
  • Patent number: 5011904
    Abstract: Epoxy-containing compounds are prepared by dehydrohalogenating the reaction product of an epihalohydrin with the reaction product of a compound containing an average of more than one aromatic hydroxyl group per molecule with an alkylene oxide wherein the ratio of moles of epihalohydrin to hydroxyl groups is at least about 1.2:1. When these epoxy containing compounds are formulated into coatings, the resultant products have improved chemical resistance to acids.
    Type: Grant
    Filed: November 20, 1989
    Date of Patent: April 30, 1991
    Assignee: The Dow Chemical Company
    Inventors: Michael B. Cavitt, Dennis L. Steele, David J. Duncan
  • Patent number: 5010149
    Abstract: Disclosed is a can interior coating composition which contains (A) a modified bisphenol based epoxy resin formed by introducing at least one of a functional group represented by the following formula: ##STR1## where R is a bivalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, into a molecular terminal of a bisphenol based epoxy resin having an epoxy equivalent of 180 to 7,000 and a number average molecular weight of 350 to 10,000, and (B) a resol phenol resin obtained by reacting the modified bisphenol based epoxy resin (A) with formaldehydes in the presence of a basic catalyst.
    Type: Grant
    Filed: November 6, 1989
    Date of Patent: April 23, 1991
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Kaoru Morita, Atsushi Shioda
  • Patent number: 5009982
    Abstract: A photosetting liquid ink composition developable with a dilute alkaline aqueous solution and comprising (A) a resin curable with an activated energy ray, obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of a novolak type epoxy compound and an unsaturated monocarboxylic acid, (B) a photopolymerization initiator, and (C) a diluent can be used for the production of an etching resist or a solder resist in the manufacture of a printed circuit. This composition, when combined with a thermosetting component, produces a photosetting and thermosetting liquid ink composition.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: April 23, 1991
    Assignee: Taiyo Ink Manufacturing Co., Ltd.
    Inventors: Yuichi Kamayachi, Syoji Inagaki
  • Patent number: 5008350
    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: December 12, 1988
    Date of Patent: April 16, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriaki Saito, Shuichi Kanagawa, Hideshi Sakamoto
  • Patent number: 5006611
    Abstract: Heat-curable compositions of matter which are stable on storage and which contain(a) 10-70 parts by weight of an epoxy resin having a functionality of at least 3,(b) 90-30 parts by weight of an epoxy resin having a functionality of 2-2.5,(c) a diphenol, the amount of the diphenol being so chosen that 0.6-1.2 hydroxyl equivalents of the diphenol (c) are employed per epoxide equivalent of the epoxy resins (a) and (b), and(d) 10-150 parts by weight, relative to 100 parts by weight of the components (a) to (c), of a thermoplastic having phenolic end groups and having a glass transition temperature of at least 150.degree. C. which is compatible with the mixture of the components (a) to (c), are particularly suitable for the production of prepregs for fiber-reinforced composite materials or for the production of adhesive films. The cured shaped articles obtained therefrom are distinguished by a high heat distortion point and excellent mechanical strength properties.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: April 9, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Schmid, Sameer H. Eldin
  • Patent number: 5001174
    Abstract: An epoxy resin composition for semiconductor sealing which comprises, as essential components,(A) an epoxy resin comprising 50-100% by weight, based on total epoxy resin amount, of a polyfunctional epoxy resin represented by the formula (I) ##STR1## wherein n and m are each an integer of 0 or more, n+m=1-10, and R.sub.1, R.sub.2 and R.sub.3 which may be the same or different, are each selected from hydrogen atom, an alkyl group and a halogen atom, with the proviso that all of R.sub.1, R.sub.2 and R.sub.3 must not be hydrogen atom simultaneously,(B) a phenolic resin curing agent,(C) a silica filler, and(D) a curing accelerator.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: March 19, 1991
    Assignee: Sumitomo Bakelite Company Limited
    Inventors: Kenichi Yanagisawa, Naoki Mogi, Hironori Ohsuga, Hiroshi Shimawaki
  • Patent number: 4978712
    Abstract: A device fabrication method is disclosed in which a precursor polymeric or oligomeric material, capable of undergoing a curing reaction involving crosslinking and/or imidization, is at least partially cured and incorporated into the device being fabricated. Significantly, the at least partial curing is achieved by heating the material at generally increasing (although not necessarily continuously increasing) temperatures. In addition, the heat is supplied at a rate so that the temperature of the material is always maintained at or below the corresponding glass transition temperature of the material, which increases during the heating process.
    Type: Grant
    Filed: March 16, 1989
    Date of Patent: December 18, 1990
    Assignee: AT&T Bell Laboratories
    Inventors: Harvey E. Bair, Shiro Matsuoka
  • Patent number: 4975500
    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: November 22, 1989
    Date of Patent: December 4, 1990
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Abel Mendoza
  • Patent number: 4966928
    Abstract: An epoxy resin based powder coating composition is disclosed, comprising an epoxy resin, a reaction product of dicyclopentadiene and maleic anhydride, and a cure accelerator.The coating composition may further comprise an aromatic acid anhydride based curing agent, an impact modifier and a surface smoothing agent.The coating composition has stable powder characteristic and provides good heat resistance and electrical insulation.
    Type: Grant
    Filed: August 17, 1988
    Date of Patent: October 30, 1990
    Assignee: Somar Corporation
    Inventors: Katugi Kitagawa, Ichiro Akutagawa, Kazuya Ono
  • 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: 4957995
    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 fiberreinforced composite material containing as matrix a cured product of said epoxy resin composition and a fiber as reinforcing material.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: September 18, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuhisa Saito, Katsuya Watanabe, Kohichi Okuno, Kunimasa Kamio, Akira Morii
  • Patent number: 4933420
    Abstract: Epoxide compounds and phenolic compounds are reacted in the presence of phosphonium compounds represented by the formula .crclbar.Z'R.sup.1 R.sup.2 R.sup.3 P.sym.-Z-P.sym.R.sup.1 R.sup.2 R.sup.3 Z'.crclbar. wherein each R.sup.1, R.sup.2 and R.sup.3 is independently an aromatic group or an inertly substituted aromatic group; Z is --(C(R.sup.4).sub.2).sub.a --; each R.sup.4 is independently hydrogen or a hydrocarbyl group containing from 1 to about 20 carbon atoms; Z' is any suitable anion and a has a value of at least 4.
    Type: Grant
    Filed: September 23, 1988
    Date of Patent: June 12, 1990
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Loan A. Ho
  • Patent number: 4925901
    Abstract: Storage stable compositions are disclosed which comprise an epoxide containing compound, a phenolic hydroxyl containing compound, and a catalyst compound for catalyzing the reaction between epoxide groups and aromatic hydroxyl groups which catalyst comprises the product resulting from contacting an onium salt, amine, or amine salt with an acid or a salt of an acid having a weak nucleophilic anion.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: May 15, 1990
    Assignee: The Dow Chemical Company
    Inventors: James L. Bertram, Louis L. Walker, John W. Muskopf
  • Patent number: 4925773
    Abstract: A solder resist ink composition is disclosed which contains a photo-curable resin obtained by causing an unsaturated monocarboxylic acid to react with a cresolnovolak- or phenolnovolak-type epoxy resin, and causing a polybasic carboxylic anhydride to react with the resultant reaction product, a photo-curable resin obtained by causing an unsaturated monocarboxylic acid to react with a bisphenol A novolak- or cycloaliphatic oxirane novolak-type opoxy resin, and causing a polybasic carboxylic anhydride to react with the resultant reaction product, at least one photo-polymerizable compound selected from photo-polymerizable monomers, a photo-polymerization initiator, an organic solvent, and an inorganic filler. Also disclosed are two other solder resist ink compositions each having a different photo-curable component.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: May 15, 1990
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Masataka Miyamura, Yuusuke Wada, Kazuhiro Takeda, Yuji Nakaizumi, Teiji Kohara
  • Patent number: 4923912
    Abstract: An epoxy resin composition consisting essentially of(A) an epoxy resin,(B) a curing agent,(C) a curing promoter,(D) an organic silicon compound having at least one phenolic hydroxyl group per molecule, and(E) a filler.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: May 8, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yukio Sasaki, Takayuki Watanabe, Hiroshi Takamiya, Kazuo Watanabe, Yoko Yamazaki
  • 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: 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: 4876298
    Abstract: An epoxy resin composition which is adapted for use as an encapsulator of electronic or electric parts and which comprises an epoxy resin and a curing agent for the epoxy resin. A modified polymer obtained by reaction between an aromatic polymer and a fluorine-containing material is added to the epoxy resin, so that good characteristic properties are imparted to the resultant cured product.
    Type: Grant
    Filed: June 2, 1988
    Date of Patent: October 24, 1989
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Kunio Itoh, Toshio Shiobara
  • 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
  • Patent number: 4816496
    Abstract: Disclosed are photocurable compositions which comprise(A) a compound having at least one epoxy group and at least one photocurable unsaturated ethylenic double bond within the same molecule;(B) an organometallic compound and(C) a silicon compound capable of generating silanol group by irradiation of light, or comprise(A) a compound having at least one epoxy group and at least one photocurable unsaturated ethylenic double bond within the same molecule;(E) an epoxy compound;(F) an organic phosphorus compound; and(G) a photosensitizer.The compositions of the present invention have excellent film characteristics such as good adhesion property, light resistance, heat resistance and weathering resistance.
    Type: Grant
    Filed: May 30, 1985
    Date of Patent: March 28, 1989
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Moriyasu Wada, Shuichi Suzuki, Yuusuke Wada, Shuzi Hayase, Yukihiro Mikogami
  • Patent number: 4783363
    Abstract: An improvement in curable compositions which comprise a polyglycidyl ether such as the triglycidylether of tris(hydroxyphenyl)methane and a halogenated dihydric phenol such as tetrabromobisphenol A, the improvement being employing as the halogenated dihydric phenol one in which the halogen atoms are meta with respect to the hydroxyl groups such as 2,2',6,6'-tetrabromo-3 ,3',5,5'-tetramethyl-4,4'-biphenol. These compositions can be cured by heating in the presence or absence of a catalyst for reacting epoxy groups with phenolic hydroxyl groups such as 2-methyl imidazole. These compositions are particularly useful in the preparation of electrical laminates.
    Type: Grant
    Filed: March 11, 1987
    Date of Patent: November 8, 1988
    Assignee: The Dow Chemical Company
    Inventors: Jody R. Berman, Abel Mendoza
  • Patent number: 4774271
    Abstract: The invention relates to a process for the recovery of thermoplastic polymers from aqueous dispersions by spray-drying after treatment with carboxylic acid of formula I ##STR1## wherein X is a single bond, --CH.sub.2 -- or --C.sub.2 H.sub.
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: September 27, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Lindner, Pol Bamelis, Jurgen Hinz, Dieter Wittmann, Otto Koch, Burkhard Braun
  • Patent number: 4745024
    Abstract: A non-woven textiles comprising a web of organic fibers bonded together by a binder applied to the fibers as a powdered mixture of a non-heat reactive phenolic resin and at least one thermoreactive condensation resin selected from the group consisting of phenolic resins, epoxy resins and amino resins and then fused and a method of producing said textiles.
    Type: Grant
    Filed: July 20, 1987
    Date of Patent: May 17, 1988
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Karl Jellinek, Arno Gardziella, Karl-Heinz Schwieger, Peter Adolphs, Josef Suren
  • Patent number: 4727119
    Abstract: Halogenated aromatic epoxy resins are disclosed wherein the halogen atoms are in the meta position with respect to a glycidyl ether group attached to an aromatic ring.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: September 15, 1986
    Date of Patent: February 23, 1988
    Assignee: The Dow Chemical Company
    Inventors: Jody R. Berman, Chun S. Wang, Louis L. Walker, Abel Mendoza
  • Patent number: 4725653
    Abstract: This invention is directed to adducts of a polycaprolactone polyol and a polyepoxide comprising the reaction product of at least one polycaprolactone polyol and a polyepoxide containing two or more epoxy groups per molecule in a molar ratio of polycaprolactone polyol to polyepoxide of from about 2:1 to about 3:1, said adducts having an oxirane content of less than about 0.10 percent and a viscosity of less than about 3700 centistokes at 54.5.degree. C. The adducts are useful in the formulation of high solids coating compositions, polyurethane elastomers, inks, sealants, adhesives and the like.
    Type: Grant
    Filed: November 13, 1985
    Date of Patent: February 16, 1988
    Assignee: Union Carbide Corporation
    Inventor: Joseph V. Koleske
  • Patent number: 4701481
    Abstract: Curable compositions are prepared from reinforced epoxy resin compositions comprising (A) a filler material such as silica flour, (B) one or more epoxy resins at least one of which is a hydrocarbon novolac epoxy resin such as a phenol-dicyclopentadiene epoxy novolac resin and (C) one or more epoxy resin curing agents such as phenol-formaldehyde novolac resin. These compositions are particularly suitable for use in electrical applications such as the encapsulation and subsequent protection of electrical and micro-electronic devices and circuitry and in adhesive formulations.
    Type: Grant
    Filed: October 30, 1986
    Date of Patent: October 20, 1987
    Assignee: The Dow Chemical Company
    Inventors: Gary W. Bogan, Peter A. Lucas, Georgia A. Monnerat
  • Patent number: 4657992
    Abstract: The instant invention provides a method for making a cast epoxy resin body and the epoxy formulation therefor wherein the formulation includes a two part system. Component A of the system when mixed with Component B in a ratio of 10 to 40 parts of Component B to 100 parts of Component A undergoes a polymerization reaction to form the solid body. Component A consists essentially of from 40 to 70% by weight epoxy novolac polymer, from 30 to 50% by weight vinyl 3-cyclohexene diepoxide and from 0 to 20% by weight 3,4 epoxy cyclohexylmethyl-3,4-epoxy cyclohexane carboxylate. Component B of the system is a paste anhydride consisting essentially of a mixture of a partially hydrolyzed aryl tetracarboxylic acid dianhydride and an alicylic dicarboxylic anhydride.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: April 14, 1987
    Assignee: Coors Porcelain Company
    Inventors: Anthony Brennan, Edmee Files
  • Patent number: 4644023
    Abstract: A heat curable epoxy adhesive composition has been developed which is substantially insoluble in cold hydraulic fluid before it is cured and resistant to degradation in hot hydraulic fluid after it is heat cured. The adhesive comprises a diglycidyl ether of bisphenol-A, a lesser amount of an epoxy novolac resin and a catalytic amount of 2-ethyl-4-methyl imidazole curing agent. The adhesive is particularly adapted to automatically and permanently calibrate the relief pressure of check valves in hydraulic systems.
    Type: Grant
    Filed: May 9, 1985
    Date of Patent: February 17, 1987
    Assignee: General Motors Corporation
    Inventor: Richard K. Gray
  • Patent number: 4604308
    Abstract: The thermosetting powder lacquer is suited for covering the weld seams in metal containers for foodstuffs or beverages and comprises a mixture of at least two aromatic epoxide resins, a first component of which contains a maximum of two epoxide groups per molecule on the average and a second component of which contains more than two epoxide groups per molecule on the average, a hardener and a catalyst. As a hardener there is used a condensation product formed from the diglycidylether of bisphenol-A and bisphenol-A and as a catalyst dimethylaminophenol is used.
    Type: Grant
    Filed: August 7, 1985
    Date of Patent: August 5, 1986
    Assignee: Vernicolor AG
    Inventors: Hans R. Widmer, Christian Schmid
  • Patent number: 4604317
    Abstract: Curable compositions are disclosed which comprise a polyglycidyl ether such as the triglycidylether of tris(hydroxyphenyl)methane and a halogenated dihydric phenol such as tetrabromobisphenol A. These compositions can be cured by heating in the presence or absence of catalyst for reacting epoxy groups with phenolic hydroxyl groups such as 2-methyl imidazole. These compositions are particularly useful in the preparation of electrical laminates.
    Type: Grant
    Filed: May 24, 1985
    Date of Patent: August 5, 1986
    Assignee: The Dow Chemical Company
    Inventors: Jody R. Berman, Christine C. Berkefelt, Dale J. Aldrich
  • Patent number: 4552814
    Abstract: Epoxy resins are prepared by reacting a mixture of (A) a diglycidyl ether of a dihydric aliphatic material, (B) a polyglycidyl ether of a polyhydric phenol having an average of at least about 2.6 glycidyl ether groups per molecule and optionally (C) a diglycidyl ether of a dihydric phenol with a dihydric phenol in the presence of a catalyst.Coating compositions containing the aforementioned epoxy resins have improved chip resistance, chemical resistance or pencil hardness when cured.
    Type: Grant
    Filed: January 30, 1985
    Date of Patent: November 12, 1985
    Assignee: The Dow Chemical Company
    Inventors: Michael B. Cavitt, Neal L. Wassberg
  • Patent number: 4550128
    Abstract: A composition suitable for making circuitboards containing two different brominated epoxy polymeric components which are brominated diglycidyl ethers of bisphenol-A and epoxidized nonlinear novolak having at least about six terminal epoxy groups.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: October 29, 1985
    Assignee: International Business Machines Corporation
    Inventor: Leroy N. Chellis
  • Patent number: 4549000
    Abstract: The thermosetting powder lacquer is suited for covering the weld seams in metal containers for foodstuffs or beverages and comprises a mixture of at least two aromatic epoxide resins, a first component of which contains a maximum of two epoxide groups per molecule on the average and a second component of which contains more than two epoxide groups per molecule on the average, a hardener and a catalyst. As a hardener there is used a condensation product formed from the diglycidylether of bisphenol-A and bisphenol-A and as a catalyst dimethylaminophenol is used.
    Type: Grant
    Filed: March 5, 1984
    Date of Patent: October 22, 1985
    Assignee: Vernicolor AG
    Inventors: Hans R. Widmer, Christian Schmid
  • Patent number: 4544432
    Abstract: A method has been developed to use a structural epoxy adhesive to bond together surfaces of phosphated steel electrodeposited with an organic primer. The specially formulated epoxy adhesive contains a cross-linkable epoxy novolac resin, an epoxy reactive diluent, and an imidazole curing agent substituted in at least one position with an alkyl or a hydroxyalkyl group. The amount of the curing agent used in the formulation is much lower than that in a conventional two-part epoxy adhesive such that the adhesive will not attack or degrade the primer layer to weaken the bond strength. The reactive diluent used reduces the viscosity of the mixed adhesive system to facilitate dispersion and wetting of the adhesive on the coated steel surface. Bond strength achieved by this method is adequate for automotive structural applications and is capable of withstanding extended exposure to humidity, salt spray, and other hostile automotive environments without appreciable loss.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: October 1, 1985
    Assignee: General Motors Corporation
    Inventors: Robert T. Foister, Richard K. Gray
  • Patent number: 4532308
    Abstract: 1. An epoxy resin composition is described, comprising(1) a mixture of epoxides of Components (A), (B) and (C)Component (A):20 to 60 wt % of an epoxy compound having a spiroacetal ring represented by the formula: ##STR1## Component (B): 10 to 50 wt % of a brominated epoxy resinComponent (C):10 to 50 wt % of an epoxy resin selected from the group consisting of diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, novolac type epoxy resins and N,N,O-triglycidyl-aminophenol type epoxy resins, and(2) a hardening agent.
    Type: Grant
    Filed: July 24, 1984
    Date of Patent: July 30, 1985
    Assignees: Mitsubishi Petrochemical Co., Ltd., Mitsubishi Yuka Fine Chemicals Co., Ltd., Toray Industries, Inc.
    Inventors: Tadahide Sato, Kuniaki Tobukuro, Tosio Sugimoto, Kaoru Kanayama
  • Patent number: 4474929
    Abstract: Branched epoxy novolacs having from 5 to 10 (or more) glycidyl ether groups per molecule are prepared by the epoxidation of novolacs made by the reaction of mono- or dihydric phenols with mono- or dinuclear diphenols ring-substituted with 3- or 4-methylol and/or alkoxymethyl groups.
    Type: Grant
    Filed: September 30, 1983
    Date of Patent: October 2, 1984
    Assignee: The Dow Chemical Company
    Inventor: Paul G. Schrader
  • Patent number: 4440914
    Abstract: Solid epoxy resin systems comprising the reaction products of a polyepoxide compound with a functionality greater than two, a diglycidyl ether of a polyhydric phenol and a polyhydric phenol; said systems being applicable for use in a variety of applications and particularly in combination with phenolic novolac hardeners for molding applications.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: April 3, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: David Helfand, Ralph F. Sellers
  • Patent number: 4413105
    Abstract: This invention is directed to thermosettable ethylenically unsaturated epoxy ester resin compositions having improved storage stability and to a method for improving the storage stability of such compositions by adding an anaerobically effective polymerization inhibitor to the resin composition. The resin composition comprises the reaction product of a bisphenol-base epoxy resin, a novolac-base epoxy resin, or a mixture thereof with an ethylenically unsaturated monocarboxylic acid dissolved in a polymerizable monomer containing a >C.dbd.CH.sub.2 group. The polymerization inhibitors of this invention are 4-chloro-2-nitrophenol, 2,4-dichloro-6-nitrophenol, or mixtures thereof.
    Type: Grant
    Filed: May 12, 1982
    Date of Patent: November 1, 1983
    Assignee: The Dow Chemical Company
    Inventor: Raymond Koenig
  • Patent number: 4390664
    Abstract: A curable epoxy resin composition of substantially improved curing time and high temperature properties comprising a polyepoxide of the formula: ##STR1## wherein R is H or an alkyl of up to about 18 carbon atoms, X is H or halogen, Y is an alkyl of up to about 18 carbon atoms or methoxy, Z' is H or CH.sub.3, m is an integer of not less than 1, n is an integer of up to 2, and from about 25 to about 120 parts by weight, per 100 parts by weight of the polyepoxide, of an epoxy resin hardener.
    Type: Grant
    Filed: December 30, 1981
    Date of Patent: June 28, 1983
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventor: Kaoru Kanayama
  • Patent number: 4366295
    Abstract: Compositions containing a relatively low equivalent weight epoxy resin and an advancement catalyst for reacting said epoxy resin with a polyhydric phenol are stable at high storage temperatures when the advancement catalyst is a phosphonium salt of phosphoric acid, phosphorous acid or polyphosphoric acid.
    Type: Grant
    Filed: June 1, 1981
    Date of Patent: December 28, 1982
    Assignee: The Dow Chemical Company
    Inventors: Manuel C. Tyler, Jr., Avis L. McCrary
  • Patent number: 4339567
    Abstract: Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of a sulphoxonium salt (II) of formula ##STR1## where P denotes zero or 1,R.sup.6 denotes an arylene or aralkylene group,R.sup.7 denotes --H or a group of formula ##STR2## R.sup.8 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group,R.sup.9 has the same meaning as R.sup.8 but may alternatively represent a dialkylamino group or, if R.sup.8 represents an alkyl group, R.sup.9 may represent an arylamino group,R.sup.10 and R.sup.11 each independently have the same meaning as R.sup.8 but may also each denote --H,r represents 1, 2, or 3,Z.sup.r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: July 13, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: George E. Green, Edward Irving
  • Patent number: 4309473
    Abstract: A strand prepreg which comprises (i) a resin composition comprising 100 parts by weight of thermosetting resin having a softening point of 60.degree. C. or less and about 5 to 60 parts by weight of epoxy resin having a number average molecular weight of 5,000 or more and (ii) about 20 to 80% by volume strands of carbon fibers, glass fibers, aromatic polyamide fibers and the like, wherein the strands are impregnated with the resin composition.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: January 5, 1982
    Assignee: Toho Beslon Co., Ltd.
    Inventors: Tsuyoshi Minamisawa, Keitsugu Nohara
  • Patent number: 4200705
    Abstract: A curable vinyl ester composition is prepared by the process wherein an organic hydroxy compound is reacted with a stoichiometric excess of an ethylenically unsaturated carboxylic acid and, after substantial completion of that esterification, reacting an oxirane compound with the unesterified carboxyl groups.
    Type: Grant
    Filed: January 2, 1979
    Date of Patent: April 29, 1980
    Assignee: The Dow Chemical Company
    Inventor: Rhetta Q. Davis
  • Patent number: 4182732
    Abstract: A coating and adhesive composition that may be in finely divided powder form is provided comprising a solid phenolic resole (one-step) resin having a gel time of between 150 seconds to about 250 seconds at 150.degree. C., said resin being the reaction product of bisphenol-A and formaldehyde at a mole ratio between about 2.11 to 2.64 moles of formaldehyde per mole of bisphenol-A in the presence of a catalytic quantity of a condensation catalyst at a temperature of at least about 70.degree. C. that is acidified to a pH from about 3 up to 7 and dehydrated.
    Type: Grant
    Filed: September 28, 1977
    Date of Patent: January 8, 1980
    Assignee: Union Carbide Corporation
    Inventor: John S. Fry
  • Patent number: 4169187
    Abstract: A powder coating composition of a mixture of epoxy resins is obtained by blending two types of epoxy resins with a curing agent. One resin is of the epichlorohydrin-bisphenol-A type. The other resin is an epichlorohydrin-bisphenol-A epoxy modified with an epoxy-novolac. Cure is obtained by using a dicyandiamide crosslinking agent. The composition is useful as a coating for the interior of food and beverage containers. The composition is also useful as a lining in hot-water services when finely divided polyvinylidine fluoride powder is added for hydrophobicity.
    Type: Grant
    Filed: March 28, 1978
    Date of Patent: September 25, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Barbara L. Glazar