Wherein Unsaturated Reactant Contains Only One Free Carboxyl Group Patents (Class 525/531)
  • Patent number: 4789712
    Abstract: Dispersions of polymers and optional dispersion stabilizers in a polyepoxide resin continuous phase is characterized in that the dispersion remains stable above 60.degree. C. The compositions are curable and are useful as coatings, in preparing laminates and reinforced plastics, and as adhesives. The compositions exhibit properties which are superior to compositions containing reactive liquid polymers.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: December 6, 1988
    Assignee: The Dow Chemical Company
    Inventors: Dwight K. Hoffman, Charles B. Arends
  • Patent number: 4775718
    Abstract: An elastomeric homopolymer or copolymer is reacted with or, in effect, grafted onto an unsaturated polyester and the reaction product or graft polymer may then be used in a thermosetting unsaturated polyester resin composition. The chemical linkage between the elastomeric polymer and the unsaturated polyester is a cyclic structure comprising 6 carbon atoms. The chemical bond is achieved by first treating the elastomeric polymer to incorporate a conjugated diolefin structure and then adding the conjugated diolefin group to an ethylenically unsaturated group in the polyester or a monomeric dienophile. When added to a monomeric dienophile, the polyester is then grafted onto the elastomeric polymer at the site of the monomeric dienophile. The chemical linkage or bonding occurs through a 4+2 Diels Alder addition.
    Type: Grant
    Filed: December 31, 1986
    Date of Patent: October 4, 1988
    Assignee: Shell Oil Company
    Inventor: Antonius A. Broekhuis
  • Patent number: 4766184
    Abstract: Vinyl ester resins are prepared by the reaction of one or more epoxy resins with polycarbonate resins or oligomers and the reaction of this product with polymerizable ethylenically monounsaturated monocarboxylic acids. The epoxy resins can be advanced with polyphenols during the reaction and/or further reacted with monoalcohols or monophenols. The modified epoxy resins used to make the vinyl ester resins have chain branching and/or crosslinking due to carbonate bonding to polycarbonate chain scission products. The vinyl ester resins are useful to make moldings, coatings, laminates and filaments.
    Type: Grant
    Filed: April 14, 1987
    Date of Patent: August 23, 1988
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4755570
    Abstract: This invention relates to polysulfide modified epoxy resins with enhanced physical and mechanical properties. The composition comprises the copolymerization product of epoxy resins and (vinylaryl)alkyl substituted polysulfides. Such compositions are useful in coating formulations and structural and electrical applications.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: July 5, 1988
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4755575
    Abstract: Described herein is an improved process for rapidly fabricating fiber reinforced thermoset resin articles comprising: (a) providing in a heatable matched metal die mold a bonded web of one or more fibers with a melting point or a glass transition temperature above about 130.degree. C., (b) providing in an accumulator zone a liquid body of a thermosettable organic material having a viscosity determined at 120.degree. C.
    Type: Grant
    Filed: July 25, 1986
    Date of Patent: July 5, 1988
    Assignee: Union Carbide Corporation
    Inventors: Linda A. Domeier, Richard G. Angell, Jr.
  • Patent number: 4755571
    Abstract: Curable compositions, especially suitable for use as adhesives, contain(A) an anaerobically polymerisable mixture which is stable in oxygen but polymerises when oxygen is excluded, comprising(i) a free radical polymerisable compound, such as an acrylate or methacrylate ester,(ii) an organic free radical initiator, such as a peroxide or hydroperoxide, and(iii) an organic accelerator of free radical polymerisation(B) an epoxide resin, and(C) a curing agent for epoxide resins that is a basic curing agent, a polymercaptan, or a polyhydric phenol.These compositions cure rapidly by an anaerobic curing mechanism and then develop high strength by cure of the epoxide resin.
    Type: Grant
    Filed: November 20, 1986
    Date of Patent: July 5, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Edward Irving, Terence J. Smith
  • Patent number: 4748211
    Abstract: A liquid, hydroxyl functional graft copolymer is prepared by the vinyl addition polymerization, in an inert organic medium, of a vinyl monomer component comprising at least a portion of a carboxyl functional vinyl monomer in the presence of a glycidyl ester containing acrylic polymer, the grafting occuring by the condensation reaction between the carboxyl groups of the vinyl monomer component and the epoxy groups of the glycidyl ester containing acrylic polymer. The graft copolymer is especially useful in formulating clear coating compositions which exhibit excellent sag resistance without the necessity for externally added rheology control agent.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: May 31, 1988
    Assignee: PPG Industries, Inc.
    Inventors: Suryya K. Das, Rostyslaw Dowbenko, Samuel Porter
  • Patent number: 4734469
    Abstract: A curable copolymer is provided wherein an unsaturated epoxy resin is prepared by reacting epoxy resin and acrylic and/or methacrylic acid, said unsaturated epoxy resin containing both a epoxy group and acryloyl and/or methacryloyl groups, with which a vinyl monomer is reacted in the presence of a radical catalyst to form an epoxy resin side chain. The resultant resin is finally reacted with acrylic and/or methacrylic acid to react with the remaining epoxy resin thereby resulting in terminal acryloyl and/or methacryloyl groups. This resin can be used as coating paint or molding resin or for a variety of other uses.
    Type: Grant
    Filed: May 12, 1986
    Date of Patent: March 29, 1988
    Assignee: Showa Highpower Co. Ltd.
    Inventors: Eiichiro Takiyama, Katsuhisa Morita
  • Patent number: 4732952
    Abstract: A B stageable thermosettable composition containing at least one polyepoxide and at least one linear anhydride monomer capable of forming a cyclopolymer in situ and processes for the formation of the B stage intermediate and final thermoset having a high service temperature is provided. The composition is useful in a two stage process; first to form a storage stable, flowable thermoplastic B stage intermediate by the free radical initiated vinyl polymerization of the linear anhydride in the liquid composition to a cyclic polymer and secondly to react the cyclic polymer with the poly epoxide to form a crosslinked high service temperature thermoset useful in the preparation of laminates, such as printed circuit boards, adhesives, and encapsulants.
    Type: Grant
    Filed: December 5, 1986
    Date of Patent: March 22, 1988
    Assignee: Rohm and Haas Company
    Inventors: Frederick J. Hirsekorn, William D. Emmons
  • Patent number: 4729696
    Abstract: A cartridge for use in fixing an anchor bolt that encludes a fluidtight constructed casing having therein a first fluidtight chamber and a second fluidtight chamber separated from the first chamber, the first chamber containing a resin composed mainly of an ester of an epoxy resin with an organic acid comprising acrylic acid, methacrylic acid or a mixture thereof, the second chamber containing a curing agent for the resin. By the use of such a cartridge in fixing an anchor bolt to a base, there can be attained a quick fixation of the anchor bolt to the base, a high adhesive strength between the anchor bolt and the base, and a high chemical resistance of the cured resin, with little or no lowering of the adhesive strength for an prolonged period of time.
    Type: Grant
    Filed: July 26, 1984
    Date of Patent: March 8, 1988
    Assignee: Asahi Kasei Kogyo
    Inventors: Koji Goto, Eiichi Suzuki
  • Patent number: 4725631
    Abstract: Acrylic diesters of bisphenol-alkyl-ether of formula: ##STR1## in which R.sub.1 and R.sub.2 may be a halogen or a C.sub.1 -C.sub.7 alkyl radical optionally halogen-substituted, and R.sub.3 may be hydrogen, halogen, or a C.sub.1 -C.sub.7 alkyl radical optionally halogen-substituted. Polymers obtained from the acrylic diesters of bisphenol-alkyl-ether of formula (1) and dental composites containing said acrylic diesters.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: February 16, 1988
    Assignee: Montedison S.p.A.
    Inventors: Catia Bastioli, Giancarlo Romano, Romano Mazzocchi
  • Patent number: 4719268
    Abstract: Polymer modified vinyl ester resin compositions are disclosed which comprise (I) a polymer modified epoxy resin which comprises (A) an epoxy resin wherein a portion of the epoxide groups have been reacted to provide groups containing polymerizable ethylenic unsaturation; (B) at least one vinyl terminated urethane oligomer and optionally (C) at least one polymerizable ethylenically unsaturated compound and (II) a monounsaturated monocarboxylic acid or mixture of such acids.
    Type: Grant
    Filed: March 31, 1986
    Date of Patent: January 12, 1988
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Virginia B. Messick
  • Patent number: 4708996
    Abstract: Dispersions of polymers and optional dispersion stabilizers in a polyepoxide resin continuous phase is characterized in that the dispersion remains stable above 60.degree. C. The compositions are curable and are useful as coatings, in preparing laminates and reinforced plastics, and as adhesives. The compositions exhibit properties which are superior to compositions containing reactive liquid polymers.
    Type: Grant
    Filed: October 25, 1984
    Date of Patent: November 24, 1987
    Assignee: The Dow Chemical Company
    Inventors: Dwight K. Hoffman, Charles B. Arends
  • Patent number: 4701474
    Abstract: Reduced reactivity polyols are provided as foam controllers in the production of polyurethane foams. When the foam controllers are incorporated into polyurethane foam formulations, foam rise time is increased without adverse effects on foam characteristics, such as load bearing capability, resiliency and porosity. The foam controllers are acid grafted polyethers, such as acrylic acid grafted poly(alkylene oxides), and can be employed in surprisingly low concentrations to control reactivity.
    Type: Grant
    Filed: April 9, 1986
    Date of Patent: October 20, 1987
    Assignee: Union Carbide Corporation
    Inventors: Frederick E. Bailey, Jr., Benny J. Argento
  • Patent number: 4692382
    Abstract: A coating composition has as its principal constituents(i) an isocyanate terminated urethane containing material; and(ii) a phosphatized polyepoxide essentially free of oxirane groups.The coating composition has excellent elongation and is particularly useful as a coating applied directly to metal. The coating composition is also useful as a primer in the preparation of multilayer coatings having good flexibility.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: September 8, 1987
    Assignee: PPG Industries, Inc.
    Inventors: Robert J. Schmitt, Leon A. Perez, Robert A. Montague, Marvin T. Tetenbaum, Ellor J. Van Buskirk
  • Patent number: 4692500
    Abstract: This invention relates to polysulfide modified epoxy resins with enhanced physical and mechanical properties. The composition comprises the copolymerization product of epoxy resins and (vinylaryl)alkyl substituted polysulfides. Such compositions are useful in coating formulations and structural and electrical applications.
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: September 8, 1987
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4692383
    Abstract: A coating composition is composed of a material or mixture of materials adapted to provide a source of:(i) carbonate moieties;(ii) isocyanate groups; and(iii) phosphatized polyepoxide essentially free of oxirane groups.The coating composition has excellent elongation and is particularly useful as a coating applied directly to metal. The coating composition is also useful as a primer in the preparation of multilayer coatings having good flexibility.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: September 8, 1987
    Assignee: PPG Industries, Inc.
    Inventors: Robert J. Schmitt, Leon A. Perez, Robert A. Montague, Marvin T. Tetenbaum
  • Patent number: 4690988
    Abstract: Vinylized epoxy resins, such as vinyl ester resins, comprise polymerizable ethylenic unsaturation and an in situ polymerized polymer, such as a polyalkyl acrylate. The vinylized epoxy resins can form stable dispersions and are useful in thermoset applications.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: September 1, 1987
    Assignee: The Dow Chemical Company
    Inventors: Dwight K. Hoffman, Michael G. Stevens, Virginia B. Messick
  • Patent number: 4668745
    Abstract: Novel compositions are prepared by reacting sulfur dioxide with the reaction product of a material having an average of more than one 1,2-epoxide group per molecule such as a diglycidyl ether of bisphenol A with a monoethylenically unsaturated monocarboxylic acid such as methacrylic acid in the presence of an oxidizing agent such as cumene hydroperoxide.
    Type: Grant
    Filed: June 4, 1986
    Date of Patent: May 26, 1987
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4661553
    Abstract: Vinyl ester resins are prepared by reacting a polyepoxide of a co-oligomerization product of a mixed cyanate of a polyphenol and a polymaleimide with a monounsaturated monocarboxylic acid.
    Type: Grant
    Filed: February 24, 1986
    Date of Patent: April 28, 1987
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4642321
    Abstract: A non-blocking, solid, adhesive composition comprising, (a) a film forming polymeric resin of average molecular weight between 10,000 and about 100,000 and having an epoxide, hydroxyl or unsaturated functionality greater than about 2, the polymeric resin being selected from the group consisting of polyesters, polyurethanes and epoxies; (b) at least one filler, or at least one polyfunctional compound of average molecular weight below about 7,000 and containing a polyaromatic backbone, or mixtures thereof, the weight ratio of (a) to (b) being between about 1.5:1 and about 9:1; and (c) a curing agent which is capable of cross-linking and curing the polymeric resin to a C-stage, the curing agent being present in an amount sufficient to C-stage the polymeric resin. The adhesive composition can be activated without becoming C-staged upon application of sufficient heat or ultrasonic energy for a time period less than one second.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: February 10, 1987
    Assignee: Kollmorgen Technologies Corporation
    Inventors: Andrew J. Schoenberg, Marju L. Friedrich
  • Patent number: 4640957
    Abstract: Polyimido-ester compounds having the formula RO-C(O)-R.sub.1 -C(O)-OR are disclosed wherein R is an alkylene N-dicarboximido radical containing cycloolefinic unsaturation and R.sub.1 is the divalent residue of an unsaturated polycarboxylic acid such as fumaric, itaconic, aconitic, mesaconic, or glutaconic acid. These compounds are blended with unsaturated resins such as unsaturated polyester resin or vinyl ester resin, and polymerizable unsaturated monomers such as styrene to provide thermosettable resin compositions which can be cured to provide castings or laminates with improved resistance to thermal aging.
    Type: Grant
    Filed: June 13, 1985
    Date of Patent: February 3, 1987
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Douglas L. Hunter
  • Patent number: 4618658
    Abstract: Polymer modified epoxy resin compositions are disclosed which comprise (A) an epoxy resin wherein a portion of the epoxide groups have been reacted to provide groups containing polymerizable ethylenic unsaturation; (B) at least one vinyl terminated urethane oligomer and optionally (C) at least one polymerizable ethylenically unsaturated compound. These compositions are useful as intermediates to novel polymer modified vinyl esters and thermoset (cured) products.
    Type: Grant
    Filed: May 16, 1985
    Date of Patent: October 21, 1986
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Virginia B. Messick
  • Patent number: 4616071
    Abstract: Novel thermosetting, solvent-based, crosslinkable and chain-extendable coating compositions are provided. The coating compositions are suitable to be formulated as high solids coating compositions and comprise bis-diene oligomers, bis-dieneophile oligomers, crosslinking agent, organic solvent and, preferably, catalyst. The composition cures at elevated temperature to provide a coating on a substrate, such as sheet steel or the like, which is highly resistant to corrosion, humidity and solvents and provides corrosion protection for the substrate.
    Type: Grant
    Filed: January 7, 1985
    Date of Patent: October 7, 1986
    Assignee: Ford Motor Company
    Inventor: Joseph W. Holubka
  • Patent number: 4612352
    Abstract: Water-soluble or water-dispersible graft polymers comprising at least 20% by weight, based on said graft polymer, of a hydrophilic graft constituent bonded to a carbon atom and at least one hydrophobic radical which is bonded to the graft constituent via a polyglycol ether chain, the polyglycol ether chain containing 2 to 200 ##STR1## groups. These graft polymers can be used individually, as mixtures or in combination with other active substances as, for example, antifoams, antistatic agents, builders, emulsifiers, padding assistants, wetting agents, paper deaerators, sludge dewatering assistants, textile assistants, greying inhibitors or detergents.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: September 16, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Paul Schafer, Heinz Abel, Christian Guth, Albert Stehlin
  • Patent number: 4603181
    Abstract: One-package type composition for in-mold coating is disclosed which contains (a) a urethane compound having at least two acryloyloxy or methacryloyloxy groups at the terminal and at least one 1-oxa-3,5-diazine-2,4,6-trione ring in the molecule, (b) an ester resin having at least one reactive double bond prepared by the reaction of an epoxy compound with an unsaturated carboxylic acid and (c) a vinyl monomer. The composition is useful for coating the molded product from fiberglass reinforced thermosetting polyester resin compounds within a mold. The composition, when coated, shows excellent adherence to the molded product and excellent water resistance.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: July 29, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Kenichi Nishino, Hiromu Miyashita, Tadao Fukui
  • Patent number: 4600754
    Abstract: Water dispersed phosphated epoxy-acrylic polymers are produced by first producing an epoxy phosphate followed by in-situ polymerization of ethylenically unsaturated monomers, including carboxyl monomers, in the presence of the epoxy phosphate and utilizing at least 3% peroxide catalyst based on the weight of monomers.
    Type: Grant
    Filed: May 10, 1984
    Date of Patent: July 15, 1986
    Assignee: SCM Corporation
    Inventor: Peter P. Winner
  • Patent number: 4595734
    Abstract: Epoxide-vinyl ester resins having significant amounts of epoxide and ethylenically unsaturated groups may be thickened by reaction thereof with polyfunctional amines. The resulting resinous products, when molded at elevated temperatures, exhibit increased viscosity and controlled flow.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: June 17, 1986
    Assignee: Interplastic Corporation
    Inventor: Thomas P. O'Hearn
  • Patent number: 4594398
    Abstract: Vinyl ester resins are prepared by reacting a polymerizable unsaturated carboxylic acid-containing compound with an epoxy resin prepared by dehydrohalogenating the reaction product of an epihalohydrin with the reaction product of an aromatic hydroxyl-containing compound and an unsaturated hydrocarbon.
    Type: Grant
    Filed: May 24, 1985
    Date of Patent: June 10, 1986
    Assignee: The Dow Chemical Company
    Inventors: Donald L. Nelson, Mary J. Lamont
  • Patent number: 4588788
    Abstract: Curable compositions are prepared from a blend of a polyepoxide, the esterification product of a mixture of carboxylic acids of the formula CH.sub.2 .dbd.CHCO.sub.2 (CH.sub.2 CH.sub.2 CO.sub.2).sub.n H (AOnPA herein), where the number average value of n is greater than about 0.1, and a mono- or polyhydric hydroxy-functional compound, and an aliphatic amine curing agent. Use of the esterification product as a reactive diluent for the polyepoxide gives coating and adhesive compositions with reduced toxicity.
    Type: Grant
    Filed: April 26, 1985
    Date of Patent: May 13, 1986
    Assignee: Rohm and Haas Company
    Inventors: William D. Emmons, Charles E. Warburton, Jr.
  • Patent number: 4587293
    Abstract: A composition is described which thermosets when admixed with a free radical generating catalyst which composition comprises (A) an unsaturated polyester resin or vinyl ester resin, (B) a reactive monomer prepared by reacting (1) an aromatic material containing, per molecule, one polymerizable ethylenically unsaturated group and one group containing an ether linked epoxide group; and (2) a material containing at least one oxyalkylene group and is terminated in a group having at least one hydrogen atom which is reactive with an ether linked epoxide group, and (C) a polymerizable ethylenically unsaturated non-resinous monomer different from Component (B).
    Type: Grant
    Filed: January 23, 1985
    Date of Patent: May 6, 1986
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4582880
    Abstract: A crosslinkable composition of matter is provided, which comprises certain diene functional aminoepoxy resin and certain functional aminoepoxy blocked dieneophile resin, which two resins are co-reactive at elevated cure temperature. The diene functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional diene. The blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional blocked dieneophile chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional blocked dieneophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resins. The crosslinkable composition of matter is useful in coating and other applications, especially solvent based primer coating compositions and cathodic electrocoating compositions.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 15, 1986
    Assignee: Ford Motor Company
    Inventor: Joseph W. Holubka
  • Patent number: 4568719
    Abstract: A resin composition comprising (I) at least one compound selected from the group consisting of hydroxyl-containing unsaturated polyesters, reaction products of polyepoxides and ethylenically unsaturated carboxylic acids and .beta.-polymers of diallyl phthalate (II) at least one monomer copolymerizable with said compound (I), which is selected from the group consisting of ethylenically unsaturated monomers and allylic unsaturated monomers, (III) a catalyst capable of polymerizing (I) and (II), (IV) at least one compound containing the oxirane ring, (V) a curing agent (excluding acid anhydrides, acids and amine compounds) capable of curing said compound (IV), and (VI) a catalyst capable of promoting the curing of (IV) by (V). A preferable composition further contains (VII) a polyisocyanate compound and (VIII) a promoter for the reaction between isocyanate group and hydroxyl group. The composition may contain fibrous reinforcing agents.
    Type: Grant
    Filed: May 30, 1984
    Date of Patent: February 4, 1986
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Hisashi Tada, Masahiro Saruta, Hideki Moriishi
  • Patent number: 4565852
    Abstract: A crosslinkable composition of matter is provided, which comprises first and second chain extended diepoxide resins, one or both of which are prepared using an excess of diepoxide reactant and modified by reaction with hydroxy functional secondary amine. The first resin, diene functional aminoepoxy resin, and the second resin, blocked dieneophile functional aminoepoxy resin, are co-reactive at elevated cure temperature. The diene functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional diene. The blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional blocked dieneophile chain extending reactant and, optionally, monofunctional end-capping reactant such as monohydroxy functional blocked dieneophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resins.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: January 21, 1986
    Assignee: Ford Motor Company
    Inventor: Saiyed B. A. Qaderi
  • Patent number: 4564646
    Abstract: A light- and thermosetting resin composition comprising (a) an unsaturated epoxy ester having a resin acid value of 5 or less, or a reaction product having a resin acid value of 5 or less obtained by reacting an unsaturated epoxy ester having a resin acid value of more than 5 with a monoepoxide, (b) one or more .alpha.,.beta.-unsaturated ethylenic monomers, and (c) one or more photosensitizers and peroxides can produce insulated electrical machinery and appliances improved in reliance and performance in a short treating time.
    Type: Grant
    Filed: February 16, 1984
    Date of Patent: January 14, 1986
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Hisashi Nishigaki, Yuji Aimono
  • Patent number: 4560713
    Abstract: A reinforced plastic molding having excellent heat resistance, toughness and adhesion property to a fibrous substrate is disclosed, comprising a fibrous substrate having impregnated and cured therein a curable composition comprising tri(meth)acrylate of trishydroxyalkyl isocyanurate, a modified phenol novolak-based epoxy resin and a polymerization initiator.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: December 24, 1985
    Assignee: Nitto Electric Industrial Co., Ltd.
    Inventors: Mitsuo Yoshihara, Yoshitada Morikawa, Yasuo Yamamoto, Mitsuharu Komada, Masaaki Hattori
  • Patent number: 4559393
    Abstract: A self-crosslinkable resin and composition of matter comprising same is provided, which resin comprises certain diene functional blocked dieneophile functional aminoepoxy resin, which resin is self-crosslinkable at elevated cure temperature. The diene functional blocked dieneophile functional aminoepoxy resin comprises the reaction product of diepoxide with amine functional diene chain extending reactant, mono-secondary amine functional blocked dieneophile and, optionally, monofunctional end-capping reactant such as mono-secondary amine functional diene and mono-secondary amine functional blocked dienophile. The composition may further comprise crosslinking agent reactive with hydroxy functionality of the resin. The crosslinkable composition of matter is useful in coating and other applications, especially solvent-based primer coating compositions and cathodic electrocoating compositions.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: December 17, 1985
    Assignee: Ford Motor Company
    Inventor: Joseph W. Holubka
  • Patent number: 4555554
    Abstract: Oligomeric vinyl esters are prepared by reacting (A) an epoxy resin prepared by co-oligomerizing (1) a mixed cyanate of a polyphenol and (2) an aromatic polyamine with (B) a monounsaturated monocarboxylic acid.These vinyl ester resins are (oligomeric vinyl ester and copolymerizable monomer blend) useful in the preparation of laminates, composites, castings, coatings and the like.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: November 26, 1985
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4555412
    Abstract: A process is provided for applying a coating to a substrate by bringing the substrate into contact with a liquid aqueous coating composition comprising a solid powdered epoxy group-containing compound having a number average molecular weight of at least 1,000, an epoxy equivalent weight of 450-7,500 and an average particle size of 0.5-35 .mu.m, dispersed in an aqueous medium containing an ionized polyamino compound having primary or secondary groups, the ratio of the number of reactive groups of the polyamino compound to the number of epoxy groups of the epoxy compound being at least 0.4. The coating composition is applied to the substrate at a temperature of 5.degree.-65.degree. C. and the resulting coating layer is cured at a temperature of 70.degree.-220.degree. C. This invention also relates to the liquid aqueous coating composition to be used in said process.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: November 26, 1985
    Assignee: Akzo nv
    Inventors: Gerhard Gunter, Hartmut Haeufler
  • Patent number: 4554346
    Abstract: A process for producing a curable resin which comprises reacting (a) at least one cyanate ester compound selected from the group consisting of polyfunctional cyanate esters having two or more cyanato groups per one molecule, prepolymers of the cyanate esters or mixtures thereof with (b) at least one compound having hydroxy group(s) and radical-polymerizable unsaturated double bond(s) in its molecule, the cyanate ester compound (a) and the compound (b) being used so that the ratio of the cyanato group to the hydroxy is in the range of from about 1:0.1 to about 1:2, in the presence of (c) a radical polymerization inhibitor at a temperature of about 80.degree.-about 140.degree. C.The curable resin produced according to the present invention is capable of giving cured products having excellent heat resistance and electrical properties.
    Type: Grant
    Filed: July 18, 1984
    Date of Patent: November 19, 1985
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Morio Gaku, Hidenori Kimbara, Jun Yokoi
  • Patent number: 4546129
    Abstract: New compositions of matter are disclosed which are allylated di and polycyclopentadiene diphenols. These new compositions are useful in thermoset resin compositions comprising styrene, a dicyclopentadiene-modified unsaturated polyesteramide and said allylated di and polycyclopentadiene diphenol(s).
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: October 8, 1985
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4540752
    Abstract: Solvent soluble epoxy-containing compositions prepared by polymerizing ethylenically unsaturated monomers such as alkyl acrylates in the presence of the reaction product of a liquid epoxy resin such as a diglycidyl ether of bisphenol A and acrylic acid and/or methacrylic acid. These compositions are useful in the preparation of coatings.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: September 10, 1985
    Assignee: The Dow Chemical Company
    Inventor: Russell T. McFadden
  • Patent number: 4532309
    Abstract: A stable water soluble epoxy resin suitable for use as a coating material is made by grafting an acid functional vinyl monomer onto unsaturated functional sites on an epoxy resin backbone.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: July 30, 1985
    Assignee: Parker Chemical Company
    Inventor: Andreas Lindert
  • Patent number: 4530978
    Abstract: Surface coating binders which contain tertiary amino groups, blocked isocyanate groups, hydroxyl groups and ether groups and are water-soluble or water-dispersible as a result of partial or complete salt formation with an acid are prepared by copolymerization of a mixture comprising(A) an olefinically unsaturated compound which contains a tertiary amino group,(B) an N-(1-alkenyl)-isocyanate which is blocked with a CH-, OH- or NH-acidic blocking agent and(C) an adduct of an epoxy resin based on bisphenol A and epichlorohydrin, and an olefinically unsaturated carboxylic acid of 3 to 20 carbon atoms, a secondary amine and, if required, a saturated monocarboxylic acid of 1 to 20 carbon atoms, with or without one or more copolymerizable, olefinically unsaturated compounds not mentioned under (A), (B) and (C).These surface coating binders are particularly useful as self-crosslinking or externally crosslinking binders for the cathodic electrocoating of metal articles.
    Type: Grant
    Filed: September 13, 1983
    Date of Patent: July 23, 1985
    Assignee: Basf Aktiengesellschaft
    Inventors: Juergen Gimpel, Volker Schwendemann, Erich Gulbins
  • Patent number: 4530962
    Abstract: An elastomer-modified unsaturated polymer comprises an unsaturated polyester or vinyl ester polymer modified by a low molecular weight elastomer. The elastomer has terminal groups provided by an epoxy resin which render it compatible with the unsaturated polymer. These elastomer-modified unsaturated polymers are useful for providing resin compositions which include a cross-linking agent for the unsaturated polymer. The elastomer is soluble in the resin composition, which is curable to provide an unsaturated resin matrix having particles of the modifying elastomer dispersed therein.
    Type: Grant
    Filed: November 9, 1982
    Date of Patent: July 23, 1985
    Assignee: Scott Bader Company Limited
    Inventor: Ian J. Alexander
  • Patent number: 4528334
    Abstract: Graft copolymers are obtained which are substantially free of insoluble homopolymers by grafting 3 to 15 percent by weight of acrylic acid onto poly(oxyalkylene) compounds.
    Type: Grant
    Filed: April 30, 1984
    Date of Patent: July 9, 1985
    Assignee: Union Carbide Corporation
    Inventors: Robert J. Knopf, Kenneth Drake
  • Patent number: 4525544
    Abstract: Vinyl ester resins are prepared from epoxy resins and an adduct of (1) alpha, beta ethylenically unsaturated acids or anhydrides containing 4 or 5 carbon atoms; (2) an unsaturated hydrocarbon selected from dimers, codimers, oligomers and cooligomers of dienes containing 4 to 6 carbon atoms; (3) if component (1) is an anhydride, water, and optionally; (4) isomerization catalysts or reactants that cause isomerization; (5) monofunctional acids selected from acrylic acid or methacrylic acid; and (6) alpha, beta ethylenically unsaturated anhydrides containing 4 or 5 carbon atoms.
    Type: Grant
    Filed: April 12, 1982
    Date of Patent: June 25, 1985
    Assignee: The Dow Chemical Company
    Inventors: Donald L. Nelson, Mary H. Lamont
  • Patent number: 4515934
    Abstract: Vinyl ester resin compositions containing triazine groups or both triazine and oxazoline groups are prepared by reacting (a) a polyepoxide containing triazine groups, or (b) a polyepoxide containing both triazine and oxazoline groups, or (c) a mixture of (a) and (b) above with (d) about 0.75 to about 1, preferably from about 0.9 to about 1, moles of a monounsaturated monocarboxylic acid or mixture of monounsaturated monocarboxylic acids per epoxide group in the presence of (e) a suitable quantity of a suitable catalyst.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: May 7, 1985
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4511710
    Abstract: Unwanted halogen values are removed from liquid resin, organic or hydrocarbon material by adding particulate crystalline lithium aluminate compounds to the liquid material to act as a halogen scavenger, then separating the crystalline aluminate compound from the liquid material.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: April 16, 1985
    Assignee: The Dow Chemical Company
    Inventors: Chun S. Wang, Kyle B. Benkendorfer, John L. Burba, III
  • Patent number: 4507432
    Abstract: In curing an unsaturated polyester resin in the presence of an organic peroxide added thereto, 4-methyl-2,4-diphenyl-pentene-1 is added to the mixture of the unsaturated polyester resin with the organic peroxide to enhance the curing properties.
    Type: Grant
    Filed: October 24, 1983
    Date of Patent: March 26, 1985
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Shigeki Banno, Takeshi Komai