Wherein Unsaturated Reactant Contains Only One Free Carboxyl Group Patents (Class 525/531)
  • Patent number: 5164464
    Abstract: Thermosettable vinyl ester resin compositions are prepared from polyepoxide compounds, optionally, monoepoxide compounds, at least one of which contains a mesogenic or rigid rodlike moiety and a monounsaturated monocarboxylic acid. These vinyl ester resins can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.
    Type: Grant
    Filed: June 7, 1991
    Date of Patent: November 17, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 5162456
    Abstract: A curable resin comprising units of at least one prepolymer selected from the group consisting of a prepolymer (C) and a prepolymer (F); the prepolymer (C) having the formula (I): ##STR1## and the prepolymer (F) having the formula (III): ##STR2## The curable resin has the excellent flexibility, solvent resistance and adhesion to organic materials and the properties thereof can be controlled accordingly to desire, in addition to the excellent curability at ordinary temperature, adhesion to inorganic materials and weatherability.
    Type: Grant
    Filed: June 18, 1991
    Date of Patent: November 10, 1992
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hisao Furukawa, Naotami Ando, Yasushi Kato
  • Patent number: 5159024
    Abstract: Curing product based onA) compounds having at least two R.sup.1 R.sup.2 C.dbd.CR.sup.3 --X groups (I) andB) compounds having methanetricarboxamide units of the formula ##STR1## these compounds B) containing at least two groups having active H atoms of the type ##STR2## In order to prepare this curing product, the compounds A) and B) of an oligomeric and/or polymeric reaction product are reacted in the presence of at least one catalyst. The mixtures of A) and B) can be used as two-component lacquers on their own or together with customary additives.
    Type: Grant
    Filed: November 19, 1986
    Date of Patent: October 27, 1992
    Assignee: Hoechst AG
    Inventors: Gerhard Brindopke, Gerd Walz
  • Patent number: 5157078
    Abstract: A protective paint coating containing a polymeric binder having both hydrophobic and hydrophilic moieties in the polymeric structure comprises an acrylic-graft terpolymer. The terpolymer comprises aliphatic-modified glycidyl acrylate and epoxy resin coreacted with diphenol to form the terpolymer. Ethylenically unsaturated monomers, including carboxyl monomers, are in-situ copolymerized in the presence of the terpolymer to produce the acrylic-graft terpolymer. The aliphatic-modified glycidyl acrylate component of the terpolymer comprise the reaction product of a glycidyl acrylate and a branched aliphatic ethylenic monomer having a branched chain of 2 to 20 carbon atoms. The branched aliphatic chain and the carboxyl functionality provide the self-contained wetting agent properties to the polymeric binder structure.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: October 20, 1992
    Assignee: The Glidden Company
    Inventors: James T. K. Woo, Gary C. Pompignano, Kevan A. Packard
  • Patent number: 5155182
    Abstract: The invention relates to new imidazolyl derivatives, their use as curing agents in epoxy-resin compositions, and curable epoxy-resin compositions containing them and composed of an epoxy resin and compounds of the general formula ##STR1## where R is the group of the alcohol component used to produce the glycidyl ethers, R.sup.1 and R.sup.2 are, independently of each other, hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5, n is 2 or 3, R.sup.3 is COOH, --CH, --COHN--N.sub.H2, --COOCH.sub.2 --CH.sub.2 --OH or COOR.sup.4, R.sup.4 being an aliphatic hydrocarbon group having from 1 to 4 carbon atoms, and m is equal to the valence of R.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: October 13, 1992
    Assignee: Schering AG
    Inventors: Christian Burba, Werner Mrotzek
  • Patent number: 5153277
    Abstract: A resin composition useful as a matrix resin for a composite material comprises (A) from 30-80% by weight of an amino group-containing unsaturated ester compound obtained by ring-opening addition reacting an epoxy group-containing unsaturated compound (c) with an aromatic polyamine (a) or diamine (b) in an equivalent weight ratio of compound (c) to amino hydrogen atom of polyamine (a) or diamine (b) of from 0.25-0.9:1, (B) from 10-60% by weight of a polyepoxy compound, and (C) from 5-60% by weight of a radically polymerizable cross-linking agent such as p-methyl styrene.
    Type: Grant
    Filed: May 26, 1989
    Date of Patent: October 6, 1992
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Toshio Awaji, Takao Omi, Kenichi Ueda
  • Patent number: 5151470
    Abstract: Specified aminocrotonates are described for use as hardeners for expoxide resins.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: September 29, 1992
    Assignee: Miles Inc.
    Inventors: Joseph Sanders, Robson Mafoti, Peter H. Markusch
  • Patent number: 5145920
    Abstract: The invention relates to oligomer epoxy resins which are derived especially from diphenols or from diglycidyl ethers based on these phenols, oligomer epoxy resins containing oxazolidinone groups and based on the novel diglycidyl ethers and curable mixtures containing the novel oligomer epoxy resins, and the reaction products of the novel oligomer epoxy resins with unsaturated carboxylic acids, preferably in the presence of a vinyl monomer to give phenacrylate resins, and phenacrylate resins containing oxazolidinone groups and based on the novel diglycidyl ethers.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: September 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernhard Hess, Dieter Freitag, Karsten-Josef Idel
  • Patent number: 5132341
    Abstract: A process for the production of cationic paint binders which are particularly suitable for formulating pigment pastes for cathodically depositable electrocoating paints is described. The paint binders produced according to the invention are modified epoxy resin-amine adducts which contain organically-chemically bonded titanium. The cured paint films provide excellent corrosion protection on non-pretreated sheet steel even in the absence of lead-containing compounds and/or lead pigments.
    Type: Grant
    Filed: February 12, 1991
    Date of Patent: July 21, 1992
    Assignee: Vianova Kunstharz, A.G.
    Inventor: Willibald Paar
  • Patent number: 5124406
    Abstract: The present invention relates to an epoxy ester coating copolymer resin which is useful in the preparation of an air curable, high solids coating, which resin is the reaction product of components (I), (II) and (III); wherein (I) is a polymerizable base of (a) a fatty acid having free radical polymerizable double bonds and (b) a vinyl monomer selected from the group consisting of styrenes, vinyl toluene and mixtures thereof; (II) is an epoxy resin and (III) is a monobasic acid. The epoxy ester copolymer resin of the invention is prepared by the reaction of (I), (II) and (III) at an elevated temperature to an acid number below 10.
    Type: Grant
    Filed: December 28, 1990
    Date of Patent: June 23, 1992
    Assignee: Cargill, Incorporated
    Inventors: Thomas E. Rolando, Roger A. Schmidt, K. A. Pai Panandiker
  • Patent number: 5116888
    Abstract: A process for non-aqueous copolymerization of ethylenically unsaturated monomers including carboxyl functional monomers in the presence of epoxy resin by in-situ copolymerization is improved by utilizing a catalyst (initiator) combination of less than 2% peroxide and between 0.05% and 0.1% phosphonium catalyst. The carboxyl functional polymer can be aminated and dispersed into water to produce a protective coating composition useful for interior surfaces of beer and beverage cans.
    Type: Grant
    Filed: October 4, 1990
    Date of Patent: May 26, 1992
    Assignee: The Glidden Company
    Inventors: James T. K. Woo, Gary C. Pompignano
  • Patent number: 5098973
    Abstract: The invention relates to a hardening resin composition including a monomer represented by the formulas (1) or (2), a monomer represented by the formula (3), and epoxyacrylate or epoxymethacrylate. This composition is easily hardened at low temperature, weak in odor, small in shrinkage in hardening, excellent during durability against water and hot water, and thus suitable as the flooring material for a food processing factory, refrigerated warehouse, and cold storage. ##STR1## where R.sup.1 to R.sup.6, p and r are as defined.
    Type: Grant
    Filed: May 23, 1990
    Date of Patent: March 24, 1992
    Assignees: Sumitomo Rubber Industries Ltd., Nippon Kayaku Kabushiki Kaisha
    Inventors: Soichiro Kozuka, Tetsuya Kojimoto, Minoru Yokoshima
  • Patent number: 5096938
    Abstract: Radiation-curable catalysts are obtainable by reactingA) 1 equivalent of a dihydric to hexahydric oxyalkylated C.sub.2 -C.sub.10 -alcohol withB) from 0.05 to 1 equivalent of a dibasic to tetrabasic C.sub.3 -C.sub.36 -carboxylic acid or its anhydride andC) from 0.1 to 1.5 equivalents of acrylic acid and/or methacrylic acidand reacting the excess carboxyl groups with an equivalent amount of epoxide compound, and are used in radiation-curable coating materials.
    Type: Grant
    Filed: April 3, 1990
    Date of Patent: March 17, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Erich Beck, Wolfram Weiss, Horst Schmidt
  • Patent number: 5082881
    Abstract: A two-component type adhesive agent, comprising a polyvalentepoxy compound and an aqueous liquid of an amino group-containing polymer obtained by modifying a carboxyl group-containing polymer with an alkylene imine and possessed of an activated hydrogen atom.
    Type: Grant
    Filed: October 24, 1990
    Date of Patent: January 21, 1992
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd
    Inventors: Koichiro Saeki, Koji Nagaoka, Ichimoto Akasaki
  • Patent number: 5077324
    Abstract: A reactive composition for preparing synthetic resin bodies used in destructible multible-chamber cartridges and a process for anchoring a fastening element to the fastening base by introducing the destruction multiple-chamber cartridges containing the components of a curable adhesive in a drilling in the fastening base. When the fastening element is driven into the hole, the cartridge is destroyed, the synthetic resin components are mixed and harden forming a synthetic resin body. The reactive compound contains between 18 and 25 parts by weight of a pre-activated resin component composed of (A) between 3 and 60 parts by weight of a vinylester epoxy resin, (B) between 28 and 45 parts by weight of one or several ethylenically unsaturated monomeric compounds and (C) between 63 and 3 parts by weight of an unsaturated polyester and if necessary (D) between 10 and 0.1 part by weight of epoxy resin, between 0.4 and 1.2 parts by weight of hardeners and between 40 and 55 parts by weight of fillers.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: December 31, 1991
    Assignee: UPAT GmbH & Co.
    Inventors: Herbert Kistner, Christian Weber
  • Patent number: 5073601
    Abstract: The invention relates to compositions containing A) a liquid copolymer based on butadiene and at least one polar, ethylenically unsaturated comonomer, and B) a polyether prepolymer capped with hydroxyarylcarboxylic or hydroxyaralkylcarboxylic acids, or a capped polyester, polythioester or polyamide containing polyether segments. The phenolic hydroxyl group in component B) can also be etherified with epichlorohydrin and this product can be converted to an episulfide, if desired, or the phenolic hydroxyl group can be reacted with cyanogen halide to form a cyanate group.The stock compositions can be used in combination with epoxy resins to manufacture structural adhesives or sealing compounds.
    Type: Grant
    Filed: July 25, 1989
    Date of Patent: December 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Mulhaupt, Werner Rufenacht
  • Patent number: 5069581
    Abstract: A process for anchoring a fastener in a base comprising introducing a bore hole in the base a destructible multiple chamber cartridge containing a reactive set for producing a synthetic resin body. The reactive set contains 3-60 parts by weight of a vinyl ester epoxy resin, 28-45 parts by weight of styrene and/or methyl methacrylate, 63-3 parts by weight of an unsaturated polyester resin which is not an ester of a polyepoxide with an ethylenically unsaturated monocarboxylic acid, 10-0.1 parts by weight of an epoxy resin which is not an ester of a polyepoxide with an ethylenically unsaturated monocarboxylic acid, 0.4-1.2 parts by weight of an organic peroxide hardener component, 40-55 parts by weight filler, accelerators, and polymerization inhibitors. The organic peroxide and resin components are in separate chambers. The cartridge is driven into the borehole so that the cartridge is destroyed and the organic peroxide is mixed with the resin components whereby the resin is cured.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: December 3, 1991
    Assignee: UPAT GmbH & Company
    Inventors: Herbert Kistner, Christian Weber
  • Patent number: 5066690
    Abstract: Epoxy polyol resins which are copolymerized with a blend of monomers having polymerizable double bonds are described as suitable water dispersible polymeric vehicles for coating compositions.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: November 19, 1991
    Assignee: Cargill, Incorporated
    Inventors: Roger A. Schmidt, Bryan R. Swenson
  • Patent number: 5061770
    Abstract: A diallyl aromatic dicarboxylate derivative of the formula ##STR1## wherein Y is hydrogen atom or perfluoroalkenyl group having 6 to 14 carbon atoms, is a novel compound. The compound (1) is a starting material for a prepolymer containing a repeating unit derived from diallyl aromatic fluorine-containing dicarboxylate and represented by the formula ##STR2## wherein X is prefluoroalkenyl group having 6 to 14 carbon atoms.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: October 29, 1991
    Assignee: Daikin Industries, Ltd.
    Inventors: Sinji Tamaru, Motonobu Kubo
  • Patent number: 5055532
    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: July 6, 1987
    Date of Patent: October 8, 1991
    Assignee: The Dow Chemical Company
    Inventors: Dwight K. Hoffman, Virginia B. Messick, Michael G. Stevens
  • Patent number: 5043387
    Abstract: There is provided a process for preparing a novel polyol resin which does not substantially contain epoxy group wherein a bisphenol type epoxy resin (a) is subjected to the following steps (i), (ii) or (i), (iii) and (ii) in an optional sequence:(i) the step wherein epoxy group is reacted with a compound having one active hydrogen in its molecule (c), and(ii) the step wherein secondary hydroxyl group is at least partly esterified.(iii) the step wherein epoxy group is reacted with primary amine (b).
    Type: Grant
    Filed: April 4, 1989
    Date of Patent: August 27, 1991
    Assignees: Mitsui Petrochemical Industries, Ltd., Ricoh Company, Ltd.
    Inventors: Hideo Nakamura, Masaru Wakizaka, Yohzoh Yamamoto
  • Patent number: 5026794
    Abstract: This invention provides an adduct of an epoxy resin and a hydroxy free acrylate resin. The novel adduct contains vinyl unsaturation and hence may be copolymerized with an ethylenically unsaturated monomer to provide a tough thermoset resin.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: June 25, 1991
    Assignee: Polysar Limited
    Inventors: Kam W. Ho, Patrick W. Lam
  • Patent number: 5024785
    Abstract: Epoxy resins and vinyl ester resins are prepared which contain a polymeric domain containing mesogenic or rigid rodlike moieties.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: June 18, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Deborah I. Haynes
  • Patent number: 5015701
    Abstract: Described herein are curable molding compositions comprising a mixture of:(a) a vinyl ester produced by the addition of an unsaturated monocarboxylic acid to a polyepoxide and having a molecular weight greater than 300;(b) acrylic or methacrylic acid or a functionalized derivative thereof having a molecular weight of less than 300;(c) an ethylenically unsaturated monomer which is soluble in and copolymerizable with (a) and (b) and which is different from (b).The compositions can also contain one or more fibers with a melting point or a glass transition temperature above about 130.degree. C.
    Type: Grant
    Filed: July 26, 1985
    Date of Patent: May 14, 1991
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Linda A. Domeier
  • Patent number: 5002818
    Abstract: An adhesive mixture reworkably adheres electronic integrated circuit dies to hybrid microcircuit substrates, and includes a thermosetting epoxy resin. A thermoplastic resin additive allows the mixture to retain the high adhesive strength of the epoxy resin up to approximately 150.degree. C., or the upper limit of the operating and testing temperature range of the dies, and then soften sufficiently to enable defective dies to be removed at a temperature of preferably between 150.degree. C. and 200.degree. C. without damage to the substrate or adjacent dies.
    Type: Grant
    Filed: September 5, 1989
    Date of Patent: March 26, 1991
    Assignee: Hughes Aircraft Company
    Inventors: James J. Licari, Gabriel G. Bakhit
  • Patent number: 4996270
    Abstract: Vinyl ester resins possess unsaturated terminal groups and are based on polyphenols of the formulaC(ArOH).sub.m (R').sub.p --(CR.sub.2).sub.n --C(ArOH).sub.m (R").sub.p (I)or(ArOH)--CH.sub.2 --Ar--CH.sub.2 --[(ArOH)--CH.sub.2 --Ar--CH.sub.2 ].sub.n --(ArOH) (II)wherein R, R' and R" may be identical or different and are each H or CH.sub.3, Ar is phenylene which is unsubstituted or substituted by methyl or methoxy, n is 0, 1 or 2, m is 1 or 2 and p is 3-m.
    Type: Grant
    Filed: November 4, 1988
    Date of Patent: February 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Czauderna, Juergen Nieberle, Roland Peter, Dietmar Nissen
  • Patent number: 4990577
    Abstract: The invention provides a liquid coating composition curable at ambient temperature comprising a compound having at least 2 acryloyl groups or methacryloyl groups and an amino compound having a primary amino group which is blocked with an aldehyde or ketone, said amino compound being an aliphatic or cycloaliphatic amine containing 2-24 carbon atoms or an adduct of a molecular weight of 300-1500 of an epoxy compound or isocyanate compound or .alpha.,.beta.-ethylenically unsaturated carbonyl compound and a primary amine having a group reacting with said epoxy compound or isocyanate compound or .alpha., .beta.-ethylenically unsaturated carbonyl compound. A process for coating a substrate with such composition is also provided.
    Type: Grant
    Filed: February 10, 1989
    Date of Patent: February 5, 1991
    Assignee: Akzo N.V.
    Inventors: Arie Noomen, Paul M. Vandevoorde, Tamme Bartels, Gerardus J. W. M. Maters, Winsenty L. S. Pilaszek
  • Patent number: 4973613
    Abstract: Cathodically depositable electrodeposition paints contain binder combinations of cationic film-forming resins with organic titanium compounds which are obtained by reacting tetraalkyl orthotitanates or titanium acetyl acetonates with NH-functional .beta.-hydroxyalkylamine compounds, subsequently reacting with formaldehyde and with removal of the alcohol and/or acetyl acetone formed. The stoved paint films exhibit an excellent anti-corrosion effect on non-pretreated sheet steel.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: November 27, 1990
    Assignee: Vianova Kunstharz A.G.
    Inventor: Willibald Paar
  • Patent number: 4962163
    Abstract: Thermosettable vinyl ester compositions are prepared from an advanced epoxy resin containing a mesogenic or rodlike moiety and a monounsaturated monocarboxylic acid and, optionally, a monoepoxide compound. These vinyl ester compounds can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: October 9, 1990
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
  • Patent number: 4956425
    Abstract: Novel advanced epoxy resins are disclosed which are the product resulting from (I) polymerizing in the presence of a catalytic quantity of a suitable polymerization catalyst (A) the reaction product of (1) a mixture consisting of (a) a diglycidyl ether of a dihydric phenol or a diglycidyl ether of a dihydric cyclohexanol and (b) a diglycidyl ether of a mono-, di-or polyetherdiol with (2) a compound containing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group; with (B) a monomer mixture containing (1) at least one vinyl aromatic monomer, (2) a compound containing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group and optionally (3) a hydroxyalkyl acrylate or methacrylate or an alkyl acrylate or methacrylate; and (II) advancing in the presence of a catalytic quantity of a suitable advancement catalyst, the product from (I) with (C) a dihydric phenol.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: September 11, 1990
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Deborah I. Haynes
  • Patent number: 4946875
    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 theremoset useful in the preparation of laminates, such as printed circuit boards, adhesives, and encapsulants.
    Type: Grant
    Filed: January 9, 1989
    Date of Patent: August 7, 1990
    Assignee: Rohm and Haas Company
    Inventors: Frederick J. Hirsekorn, William D. Emmons
  • Patent number: 4931514
    Abstract: A method of accelerating the curing of a vinyl ester resin (e.g., vinyl ester adhesives) and related compositions comprising: a vinyl ester resin (e.g., bisphenol/epichlorohydrin condensation polymer end capped with methacrylic or ethylacrylic acid); a vinyl monomer (e.g., styrene or the like); a free radical initiator (e.g., MEKP); a free radical promoter (e.g., polyvalent metal naphthenates, polyvalent metal octoates or the like); and an accelerator selected from the group consisting of methyl acetoacetate and ethyl acetoacetate, such compositions are characterized by gel times under ten minutes and physical properties approaching fully cured values within one hour.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: June 5, 1990
    Inventor: William D. Waters
  • 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: 4868252
    Abstract: An epoxy resin composition comprising an epoxy resin and a polyfluoroalkyl group-containing polymer uniformly dispersed therein, said polymer having been formed by polymerizing a polyfluoroalkyl group-containing polymerizable compound in said epoxy resin.
    Type: Grant
    Filed: May 27, 1987
    Date of Patent: September 19, 1989
    Assignee: Asahi Glass Company Ltd.
    Inventors: Takao Doi, Yutaka Yamada, Shigeyuki Kozawa
  • Patent number: 4855366
    Abstract: A low viscosity product is obtained when an adduct is prepared by reacting (A) at least one polyglycidyl ether of a compound containing an average of more than one phenolic hydroxy group per molecule and (B) at least one aliphatic monocarboxylic acid containing 7 to 15 carbon atoms per molecule; wherein components (A) and (B) are present in amounts which provide a ratio of carboxylic acid groups per epoxide group of from about 0.01:1 to about 0.2:1.
    Type: Grant
    Filed: June 22, 1988
    Date of Patent: August 8, 1989
    Assignee: The Dow Chemical Company
    Inventor: Michael B. Cavitt
  • Patent number: 4855427
    Abstract: Epoxy resins obtained from an epoxyalkyl halide and an aromatic hydroxyl-containing melamine derivative, and vinyl ester resins based on a reaction product of the epoxy resin with an unsaturated monocarboxylic acid can be cured to give molded materials having high heat distortion resistance.
    Type: Grant
    Filed: June 13, 1988
    Date of Patent: August 8, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Roland Peter, Klaus Ebel, Thomas Allspach
  • Patent number: 4855368
    Abstract: Thermoset resinous molding compositions are provided by essentially instantaneously combining and reacting three basic resin forming components. The latter include an oligomeric ester or polyester containing polymerizable unsaturation and free hydroxyl group(s); a polyisocyanate; and an aromatic polyamine. The indicated thermosetting resin systems are especially adapted for use in a reaction injection molding (RIM) operation.
    Type: Grant
    Filed: June 21, 1988
    Date of Patent: August 8, 1989
    Assignee: Ashland Oil, Inc.
    Inventors: Timothy A. Tufts, Dan Borgnaes, Billy M. Culbertson, Theodore C. Wilkinson
  • Patent number: 4853279
    Abstract: A curable composition for a fiber-reinforced resin, comprises (A) 60-90 weight % of an epoxy-containing (meth)acrylate resin which contains an epoxy group and an unsaturated-monobasic acid ester group in its molecules and which is formed by the reaction of an epoxy resin containing at least two epoxy groups per molecule and having an epoxy equivalent of 100-1000 with an unsaturated-monobasic acid in an amount such that there are 0.2-0.7 equivalents of carboxyl groups per 1 equivalent of epoxy groups, (B) 40-10 weight % of a radical polymerizable monomer, (C) an organic peroxide, (D) a curing agent for the epoxy resin, and (E) one or more reinforcing materials selected from continuous fiber and fiber cloth.
    Type: Grant
    Filed: March 27, 1987
    Date of Patent: August 1, 1989
    Assignee: Showa Highpolymer Co., Ltd.
    Inventors: Jouji Shibata, Kazuo Ohtani, Norio Shinohara, Toshiaki Hanyuda
  • Patent number: 4847337
    Abstract: Advanced epoxy resin and polyester blends suitable for use in powder coatings are prepared by (I) polymerizing, in the presence of a suitable catalyst such as tertiary butyl perbenzoate, (A) the reaction product of (1) a diglycidyl ether of a dihydric phenol such as the diglycidyl ether of bisphenol A and with (2) a compound containing a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group such as methacrylic acid; with (B) a monomer feed containing (1) at least one vinyl aromatic monomer such as styrene; (2) a compound containing a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group such as methacrylic acid; and optionally (3) a hydroxyalkyl acrylate or methacrylate or an alkyl acrylate or methacrylate such as hydroxyethylacrylate; and (II) advancing, in the presence of a suitable advancement catalyst such as ethyltriphenylphosphonium acetate acetic acid complex, the resultant polymerized product with (C) a dihydric phenol such as bisph
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: July 11, 1989
    Assignee: The Dow Chemical Company
    Inventor: Robert E. Hefner, Jr.
  • Patent number: 4845135
    Abstract: Thermoplastic epoxy resins are prepared by (A) reacting an advanced epoxy resin prepared by reacting a mixture of (1) a relatively low equivalent weight aromatic based epoxy resin and (2) a (meth)acrylate polymer with (3) a dihydric phenol with (4) a monofunctional compound reactive with vicinal epoxide groups; and (B) mixing the product form (A) with the reaction product of (5) a relatively low equivalent weight epoxy resin and (6) a monofunctional compound reactive with vicinal epoxide groups. The resultant product is substantially free of residual epoxide groups. These resins are particularly useful in formulating pavement marking paints.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: July 4, 1989
    Assignee: The Dow Chemical Company
    Inventor: Michael B. Cavitt
  • Patent number: 4837280
    Abstract: A thermosetting resin composition of highly satisfactory storage stability comprises 100 parts by weight of a thermosetting resin composition, 0.0001 to 2.0 parts by weight of a thiuram compound possessing at least one atomic group represented by the following formula: ##STR1## wherein p stands for an integer in the range of 1 to 8, and 0.00001 to 0.1 part by weight (as copper metal) of a copper-containing compound.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: June 6, 1989
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Toshio Awaji, Kenichi Ueda, Daisuke Atobe
  • Patent number: 4835228
    Abstract: Novel advanced epoxy resins are disclosed which are the product resulting from (I) polymerizing in the presence of a catalytic quantity of a suitable polymerization catalyst (A) the reaction product of (1) a mixture consisting of (a) a diglycidyl ether of a dihydric phenol or a diglycidyl ether of a dihydric cyclohexanol and (b) a diglycidyl ether of a mono-, di- or polyetherdiol with (2) a compound containing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group; with (B) a monomer mixture containing (1) at least one vinyl aromatic monomer, (2) a compound containing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group and optionally (3) a hydroxyalkyl acrylate or methacrylate or an alkyl acrylate or methacrylate; and (II) advancing in the presence of a catalytic quantity of a suitable advancement catalyst, the product from (I) with (C) a dihydric phenol.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: May 30, 1989
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Deborah I. Haynes
  • Patent number: 4835225
    Abstract: Modified advanced epoxy resins are prepared by reacting (A) and advanced epoxy resin prepared by reacting (1) an epoxy resin having at least one aromatic ring, an average of more than one, but not more than abotu 2 vicinal epoxy groups per molecule and which contains at least one oxyalkylene or substituted oxyalkylene group per molecule; with (2) a dihydric phenol; with (B) a monoamine.
    Type: Grant
    Filed: January 13, 1988
    Date of Patent: May 30, 1989
    Assignee: The Dow Chemical Company
    Inventors: John L. Massingill, Jr., Raul A. Pabon, Jr.
  • Patent number: 4832748
    Abstract: A coating composition comprising (a) an imine obtained by reaction of an organic silicon compound having an aminoalkyl group and at least one alkoxy group with an organic carbonyl compound, (b) a compound having at least one oxirane ring, and optionally (c) a compound having at least one acryloyl or methacryloyl group.
    Type: Grant
    Filed: October 19, 1987
    Date of Patent: May 23, 1989
    Assignee: Toagosei Chemical Industry Co., Ltd.
    Inventors: Kunio Tawara, Toshiro Hirose
  • Patent number: 4824500
    Abstract: Damaged composites are repaired by use of a rubber modified vinyl ester resin composition as either an adhesive for bonding metal or cured composite to the area surrounding the damaged area or by placing an uncured reinforcing material saturated with a rubber modified vinyl ester resin composition over the prepared damaged zone and curing in place.
    Type: Grant
    Filed: November 3, 1987
    Date of Patent: April 25, 1989
    Assignee: The Dow Chemical Company
    Inventors: Warren D. White, Paul M. Puckett, Larry T. Blankenship, Mary N. White
  • Patent number: 4814398
    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 28, 1987
    Date of Patent: March 21, 1989
    Assignee: Rohm and Haas Co.
    Inventors: Federick J. Hirsekorn, William D. Emmons
  • Patent number: 4801653
    Abstract: A coating composition which exhibits excellent sag resistance without the necessity for externally added rheology control agent is prepared from a curing agent and an ungelled hydroxyl functional graft copolymer. The graft copolymer is prepared by the vinyl addition polymerization, in an inert organic solvent, of a vinyl monomer component containing at least a portion of a carboxyl functional vinyl monomer in the presence of a glycidyl ester containing acrylic polymer. The grafting occurs by the condensation reaction between the carboxyl groups of the vinyl monomer component and the epoxy groups of the glycidyl ester containing acrylic polymer.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: January 31, 1989
    Assignee: PPG Industries, Inc.
    Inventors: Suryya K. Das, Rostyslaw Dowbenko, Samuel Porter
  • Patent number: 4798877
    Abstract: Novel radiation-curable, water-compatible, resinous compositions result from (1) terminally unsaturated molecules which are the esters of an epoxy compound and (2) the reaction product of a glycidyl ether and an unsaturated acid having at least one glycidyl group per molecule converted to an onium salt of a quaternary ammonium or amine salt, with the anion of an inorganic or organic acid.
    Type: Grant
    Filed: April 8, 1985
    Date of Patent: January 17, 1989
    Assignee: The Dow Chemical Company
    Inventors: Dwight K. Hoffman, Robert F. Harris, Richard A. Hickner
  • Patent number: 4797432
    Abstract: Thermoplastic epoxy resins are prepared by (A) reacting an advanced epoxy resin prepared by reacting a mixture of (1) a relatively low equivalent weight aromatic based epoxy resin and (2) a (meth)acrylate polymer with (3) a dihydric phenol with (4) a monofunctional compound reactive with vicinal epoxide groups; and (B) mixing the product from (A) with the reaction product of (5) a relatively low equivalent weight epoxy resin and (6) a monofunctional compound reactive with vicinal epoxide groups. The resultant product is substantially free of residual epoxide groups. These resins are particularly useful in formulating pavement marking paints.
    Type: Grant
    Filed: November 19, 1987
    Date of Patent: January 10, 1989
    Assignee: The Dow Chemical Company
    Inventor: Michael B. Cavitt
  • Patent number: 4797456
    Abstract: Water-soluble sulfonium salts are converted, without the elimination of odorous volatile by-products, to water-insoluble products useful as binders in coating formulations by heating a water-soluble cyclic sulfonium salt in which the sulfonium sulfur is bonded only to aliphatic carbons.
    Type: Grant
    Filed: December 9, 1982
    Date of Patent: January 10, 1989
    Assignee: The Dow Chemical Company
    Inventors: Ritchie A. Wessling, Donald L. Schmidt, Kiyoshi I. Aikawa