Wherein Unsaturated Reactant Contains Only One Free Carboxyl Group Patents (Class 525/531)
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Patent number: 5164464Abstract: Thermosettable vinyl ester resin compositions are prepared from polyepoxide compounds, optionally, monoepoxide compounds, at least one of which contains a mesogenic or rigid rodlike moiety and a monounsaturated monocarboxylic acid. These vinyl ester resins can be mixed with polymerizable ethylenically unsaturated monomers which can, if desired, contain a mesogenic or rigid rodlike moiety.Type: GrantFiled: June 7, 1991Date of Patent: November 17, 1992Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 5162456Abstract: 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: GrantFiled: June 18, 1991Date of Patent: November 10, 1992Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hisao Furukawa, Naotami Ando, Yasushi Kato
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Patent number: 5159024Abstract: 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: GrantFiled: November 19, 1986Date of Patent: October 27, 1992Assignee: Hoechst AGInventors: Gerhard Brindopke, Gerd Walz
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Patent number: 5157078Abstract: 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: GrantFiled: May 25, 1990Date of Patent: October 20, 1992Assignee: The Glidden CompanyInventors: James T. K. Woo, Gary C. Pompignano, Kevan A. Packard
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Patent number: 5155182Abstract: 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: GrantFiled: August 2, 1990Date of Patent: October 13, 1992Assignee: Schering AGInventors: Christian Burba, Werner Mrotzek
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Patent number: 5153277Abstract: 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: GrantFiled: May 26, 1989Date of Patent: October 6, 1992Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Toshio Awaji, Takao Omi, Kenichi Ueda
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Patent number: 5151470Abstract: Specified aminocrotonates are described for use as hardeners for expoxide resins.Type: GrantFiled: January 10, 1992Date of Patent: September 29, 1992Assignee: Miles Inc.Inventors: Joseph Sanders, Robson Mafoti, Peter H. Markusch
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Patent number: 5145920Abstract: The invention relates to oligomer epoxy resins which are derived especially from diphenols or from diglycidyl ethers based on these phenols, oligomer epoxy resins containing oxazolidinone groups and based on the novel diglycidyl ethers and curable mixtures containing the novel oligomer epoxy resins, and the reaction products of the novel oligomer epoxy resins with unsaturated carboxylic acids, preferably in the presence of a vinyl monomer to give phenacrylate resins, and phenacrylate resins containing oxazolidinone groups and based on the novel diglycidyl ethers.Type: GrantFiled: December 10, 1990Date of Patent: September 8, 1992Assignee: Bayer AktiengesellschaftInventors: Bernhard Hess, Dieter Freitag, Karsten-Josef Idel
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Patent number: 5132341Abstract: 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: GrantFiled: February 12, 1991Date of Patent: July 21, 1992Assignee: Vianova Kunstharz, A.G.Inventor: Willibald Paar
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Patent number: 5124406Abstract: 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: GrantFiled: December 28, 1990Date of Patent: June 23, 1992Assignee: Cargill, IncorporatedInventors: Thomas E. Rolando, Roger A. Schmidt, K. A. Pai Panandiker
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Patent number: 5116888Abstract: 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: GrantFiled: October 4, 1990Date of Patent: May 26, 1992Assignee: The Glidden CompanyInventors: James T. K. Woo, Gary C. Pompignano
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Patent number: 5098973Abstract: 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: GrantFiled: May 23, 1990Date of Patent: March 24, 1992Assignees: Sumitomo Rubber Industries Ltd., Nippon Kayaku Kabushiki KaishaInventors: Soichiro Kozuka, Tetsuya Kojimoto, Minoru Yokoshima
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Patent number: 5096938Abstract: 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: GrantFiled: April 3, 1990Date of Patent: March 17, 1992Assignee: BASF AktiengesellschaftInventors: Erich Beck, Wolfram Weiss, Horst Schmidt
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Patent number: 5082881Abstract: 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: GrantFiled: October 24, 1990Date of Patent: January 21, 1992Assignee: Nippon Shokubai Kagaku Kogyo Co., LtdInventors: Koichiro Saeki, Koji Nagaoka, Ichimoto Akasaki
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Patent number: 5077324Abstract: 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: GrantFiled: February 14, 1989Date of Patent: December 31, 1991Assignee: UPAT GmbH & Co.Inventors: Herbert Kistner, Christian Weber
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Patent number: 5073601Abstract: 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: GrantFiled: July 25, 1989Date of Patent: December 17, 1991Assignee: Ciba-Geigy CorporationInventors: Rolf Mulhaupt, Werner Rufenacht
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Patent number: 5069581Abstract: 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: GrantFiled: August 27, 1990Date of Patent: December 3, 1991Assignee: UPAT GmbH & CompanyInventors: Herbert Kistner, Christian Weber
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Patent number: 5066690Abstract: 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: GrantFiled: July 3, 1990Date of Patent: November 19, 1991Assignee: Cargill, IncorporatedInventors: Roger A. Schmidt, Bryan R. Swenson
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Patent number: 5061770Abstract: 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: GrantFiled: April 14, 1989Date of Patent: October 29, 1991Assignee: Daikin Industries, Ltd.Inventors: Sinji Tamaru, Motonobu Kubo
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Patent number: 5055532Abstract: 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: GrantFiled: July 6, 1987Date of Patent: October 8, 1991Assignee: The Dow Chemical CompanyInventors: Dwight K. Hoffman, Virginia B. Messick, Michael G. Stevens
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Patent number: 5043387Abstract: 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: GrantFiled: April 4, 1989Date of Patent: August 27, 1991Assignees: Mitsui Petrochemical Industries, Ltd., Ricoh Company, Ltd.Inventors: Hideo Nakamura, Masaru Wakizaka, Yohzoh Yamamoto
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Patent number: 5026794Abstract: 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: GrantFiled: May 23, 1989Date of Patent: June 25, 1991Assignee: Polysar LimitedInventors: Kam W. Ho, Patrick W. Lam
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Patent number: 5024785Abstract: Epoxy resins and vinyl ester resins are prepared which contain a polymeric domain containing mesogenic or rigid rodlike moieties.Type: GrantFiled: January 17, 1989Date of Patent: June 18, 1991Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Deborah I. Haynes
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Patent number: 5015701Abstract: 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: GrantFiled: July 26, 1985Date of Patent: May 14, 1991Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Linda A. Domeier
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Patent number: 5002818Abstract: 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: GrantFiled: September 5, 1989Date of Patent: March 26, 1991Assignee: Hughes Aircraft CompanyInventors: James J. Licari, Gabriel G. Bakhit
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Patent number: 4996270Abstract: 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: GrantFiled: November 4, 1988Date of Patent: February 26, 1991Assignee: BASF AktiengesellschaftInventors: Bernhard Czauderna, Juergen Nieberle, Roland Peter, Dietmar Nissen
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Patent number: 4990577Abstract: 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: GrantFiled: February 10, 1989Date of Patent: February 5, 1991Assignee: Akzo N.V.Inventors: Arie Noomen, Paul M. Vandevoorde, Tamme Bartels, Gerardus J. W. M. Maters, Winsenty L. S. Pilaszek
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Patent number: 4973613Abstract: 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: GrantFiled: June 23, 1989Date of Patent: November 27, 1990Assignee: Vianova Kunstharz A.G.Inventor: Willibald Paar
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Patent number: 4962163Abstract: 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: GrantFiled: January 17, 1989Date of Patent: October 9, 1990Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Paul M. Puckett
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Patent number: 4956425Abstract: 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: GrantFiled: February 28, 1989Date of Patent: September 11, 1990Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Deborah I. Haynes
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Patent number: 4946875Abstract: 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: GrantFiled: January 9, 1989Date of Patent: August 7, 1990Assignee: Rohm and Haas CompanyInventors: Frederick J. Hirsekorn, William D. Emmons
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Patent number: 4931514Abstract: 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: GrantFiled: June 10, 1988Date of Patent: June 5, 1990Inventor: William D. Waters
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Patent number: 4876298Abstract: 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: GrantFiled: June 2, 1988Date of Patent: October 24, 1989Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Kunio Itoh, Toshio Shiobara
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Patent number: 4868252Abstract: 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: GrantFiled: May 27, 1987Date of Patent: September 19, 1989Assignee: Asahi Glass Company Ltd.Inventors: Takao Doi, Yutaka Yamada, Shigeyuki Kozawa
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Patent number: 4855366Abstract: 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: GrantFiled: June 22, 1988Date of Patent: August 8, 1989Assignee: The Dow Chemical CompanyInventor: Michael B. Cavitt
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Epoxy resins obtained from reaction of epoxyalkyl halides and aromatic hydroxyl-containing melamines
Patent number: 4855427Abstract: 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: GrantFiled: June 13, 1988Date of Patent: August 8, 1989Assignee: BASF AktiengesellschaftInventors: Roland Peter, Klaus Ebel, Thomas Allspach -
Patent number: 4855368Abstract: 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: GrantFiled: June 21, 1988Date of Patent: August 8, 1989Assignee: Ashland Oil, Inc.Inventors: Timothy A. Tufts, Dan Borgnaes, Billy M. Culbertson, Theodore C. Wilkinson
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Patent number: 4853279Abstract: 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: GrantFiled: March 27, 1987Date of Patent: August 1, 1989Assignee: Showa Highpolymer Co., Ltd.Inventors: Jouji Shibata, Kazuo Ohtani, Norio Shinohara, Toshiaki Hanyuda
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Patent number: 4847337Abstract: 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 bisphType: GrantFiled: October 14, 1986Date of Patent: July 11, 1989Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4845135Abstract: 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: GrantFiled: August 25, 1988Date of Patent: July 4, 1989Assignee: The Dow Chemical CompanyInventor: Michael B. Cavitt
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Patent number: 4837280Abstract: 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: GrantFiled: September 23, 1987Date of Patent: June 6, 1989Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Toshio Awaji, Kenichi Ueda, Daisuke Atobe
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Patent number: 4835228Abstract: 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: GrantFiled: November 30, 1987Date of Patent: May 30, 1989Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Deborah I. Haynes
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Patent number: 4835225Abstract: 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: GrantFiled: January 13, 1988Date of Patent: May 30, 1989Assignee: The Dow Chemical CompanyInventors: John L. Massingill, Jr., Raul A. Pabon, Jr.
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Patent number: 4832748Abstract: 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: GrantFiled: October 19, 1987Date of Patent: May 23, 1989Assignee: Toagosei Chemical Industry Co., Ltd.Inventors: Kunio Tawara, Toshiro Hirose
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Patent number: 4824500Abstract: 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: GrantFiled: November 3, 1987Date of Patent: April 25, 1989Assignee: The Dow Chemical CompanyInventors: Warren D. White, Paul M. Puckett, Larry T. Blankenship, Mary N. White
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Patent number: 4814398Abstract: 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: GrantFiled: December 28, 1987Date of Patent: March 21, 1989Assignee: Rohm and Haas Co.Inventors: Federick J. Hirsekorn, William D. Emmons
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Patent number: 4801653Abstract: 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: GrantFiled: December 21, 1987Date of Patent: January 31, 1989Assignee: PPG Industries, Inc.Inventors: Suryya K. Das, Rostyslaw Dowbenko, Samuel Porter
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Patent number: 4798877Abstract: 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: GrantFiled: April 8, 1985Date of Patent: January 17, 1989Assignee: The Dow Chemical CompanyInventors: Dwight K. Hoffman, Robert F. Harris, Richard A. Hickner
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Patent number: 4797432Abstract: 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: GrantFiled: November 19, 1987Date of Patent: January 10, 1989Assignee: The Dow Chemical CompanyInventor: Michael B. Cavitt
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Patent number: 4797456Abstract: 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: GrantFiled: December 9, 1982Date of Patent: January 10, 1989Assignee: The Dow Chemical CompanyInventors: Ritchie A. Wessling, Donald L. Schmidt, Kiyoshi I. Aikawa