Two Or More 1,2-epoxy Reactants Patents (Class 528/103)
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Patent number: 5026743Abstract: Non-gelled amine-epoxide reaction products are obtained by co-reacting a secondary amine, a polyoxyalkylene polyamine, a polyepoxide and optionally a monoepoxide. The products are crosslinkable and are useful in aqueous coating compositions, particularly when applied to a substrate by cathodic electrodeposition.Type: GrantFiled: October 18, 1989Date of Patent: June 25, 1991Assignee: Imperial Chemical Industries PLCInventors: Michael P. Beresford, Richard P. Redman
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Patent number: 5021470Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.Type: GrantFiled: March 23, 1989Date of Patent: June 4, 1991Assignee: BASF CorporationInventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
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Patent number: 5011721Abstract: Chemorheologically viscosity tailored matrix resin formulation for use in forming prepregs and filament wound composite articles and having a specified viscosity profile comprising a curable matrix resin and an effective amount of a reactive resin curing agent reactive at room temperature and a latent resin curing agent substantially non-reactive at room temperature but activated upon heating or radiation such that the matrix resin formulation is adapted upon formulation to have a viscosity sufficiently low enough to enable the matrix resin to impregnate a filament or fiber at room temperature without the necessity for the application of heat or solvent and which, upon standing at room temperature after impregnation into the fiber or filament to form a prepreg composition, rises in viscosity to a viscosity level sufficiently high to prevent substantially any bleed of the matrix resin from winding tension upon spooling of the prepreg yet of sufficiently low enough viscosity to allow the prepreg to tack and draType: GrantFiled: October 16, 1989Date of Patent: April 30, 1991Assignee: Thiokol CorporationInventors: Owen H. Decker, Neal A. Mumford
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Patent number: 5011904Abstract: Epoxy-containing compounds are prepared by dehydrohalogenating the reaction product of an epihalohydrin with the reaction product of a compound containing an average of more than one aromatic hydroxyl group per molecule with an alkylene oxide wherein the ratio of moles of epihalohydrin to hydroxyl groups is at least about 1.2:1. When these epoxy containing compounds are formulated into coatings, the resultant products have improved chemical resistance to acids.Type: GrantFiled: November 20, 1989Date of Patent: April 30, 1991Assignee: The Dow Chemical CompanyInventors: Michael B. Cavitt, Dennis L. Steele, David J. Duncan
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Patent number: 5003025Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.Type: GrantFiled: December 20, 1989Date of Patent: March 26, 1991Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 5001175Abstract: The present invention is the reaction product of an aryl sulfonamide, at least one epoxy compounds comprising at least one diepoxy compound and optionally at least one monoepoxy compound. The diepoxy compound comprises two epoxy groups and the monoepoxy compound comprises one epoxy group. Preferably, the monoepoxy compound and the diepoxy compound have no hydroxyl groups or other functional groups. Specific embodiments include a reaction product derived from at least one monoepoxy compound and at least one diepoxy compound. The reaction product of the present invention has a relatively low molecular weight of from 450 to 2000, preferably 450 to 1000, and more preferably 450 to 800.Type: GrantFiled: April 11, 1989Date of Patent: March 19, 1991Assignee: Estron Chemical, Inc.Inventor: Stanislaw B. Skora
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Patent number: 4992525Abstract: Cationic resins based on epoxy resins which are modified through the introduction of phosphoric acid segments and the process of producing the resins are described. The reaction of the phosphoric acid is carried out in a multiple-step process whereby, in a first step, the diester is formed through reaction of ortho-phosphoric acid with 2 moles of a monoepoxy compound or through reaction of a polyphosphoric acid with n-1 moles of a monoalcohol and subsequent reaction with n+1 moles of a monoepoxy compound. The remaining acid group is reacted with a di- or polyepoxy resin. The products obtained can still contain unreacted epoxy groups. The protonable groups are introduced via the epoxy groups and/or via the hydroxy groups present or set free by opening of the oxirane ring. The binders can be combined with hardening components or may be formulated as self-crosslinking binders. The binders have excellent resistance to corrosion when stoved as electrodeposited coatings.Type: GrantFiled: April 28, 1988Date of Patent: February 12, 1991Assignee: Vianova Kunstharz, A.G.Inventors: Ingo Kriessmann, Willibald Paar
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Patent number: 4985530Abstract: A new thermosetting resin composition is disclosed which comprises a Bisphenol A-type epoxy resin having a number average molecular weight of smaller than 650 but not smaller than 450 and a ratio of the weight average molecular weight thereof to the number average molecular weight thereof of in the range of 1.3-3.0; and a curing agent capable of cross-linking the epoxy resin. The curing agent is preferably a compound represented by the following general formula: ##STR1## wherein X is --CR.sub.1 R.sub.2 --, --CO--, --COO--, --SO.sub.2 --, --SO--, --S--, --O--, --NR.sub.1 --, --SiR.sub.1 R.sub.2 -- or --POR.sub.1 -- where R.sub.1 and R.sub.2 each stands for hydrogen, a lower alkyl or a phenyl; Y and Y' each stands for hydrogen, a lower alkyl or an electron attractive group; R is a lower alkyl; and m and n each is an integer of 1-4, or a mixture thereof with a primary amine, a phenolic compound or an acid anhydride.Type: GrantFiled: July 27, 1989Date of Patent: January 15, 1991Assignee: Tonen CorporationInventors: Shinkichi Murakami, Osamu Watanabe, Sadahisa Wada, Hiroshi Inoue
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Patent number: 4980400Abstract: A trowelable, epoxy-based flooring material exhibits high impact strength, high chemical resistance and a closed exposed surface after curing, and has a hardener component including aliphatic amine and amino silane, a resin component including bisphenol formaldehyde epoxy and monoepoxide and an aggregate component, with the hardener and the resin being present in stoichiometric proportion.Type: GrantFiled: October 14, 1988Date of Patent: December 25, 1990Assignee: StonhardInventors: Frank C. Sessa, Carolyn E. Massey
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Patent number: 4980397Abstract: A method for preparing an advanced epoxy cationic resin from an opoxy-based resin containing oxirane groups by converting at least some of the oxirane groups to cationic groups, wherein the improvement is using as the epoxy-based resin an advanced epoxy resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (2) a diglycidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A and (3) a dihydric phenol such as bisphenol A and optionally a capping agent such as p-nonylphenol.Coating compositions suitable for electro-deposition are prepared from the product obtained by the process.Type: GrantFiled: July 6, 1989Date of Patent: December 25, 1990Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 4977214Abstract: Curable compositions comprise(A) a polyglycidyl ether of a polyhydric phenol,(B) a polyglycidyl ether of a polyhydric alcohol,(C) a nitrogen-containing latent hardener for epoxide resins and(D) as cure accelerator dispersed as a powder in the composition, a solid solution of a polymeric phenol with an aliphatic polyamine having two or more amine groups, each of the amine groups being tertiary and at least two of the amine groups being dimethylamino groups.The compositions are useful as adhesives, sealants, laminating resins and coatings.Type: GrantFiled: October 12, 1989Date of Patent: December 11, 1990Assignee: Ciba-Geigy CorporationInventor: Madan M. Bagga
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Patent number: 4977202Abstract: A method for preparing an advanced epoxy cationic resin from an epoxy-based resin containing oxirane groups by converting at least some of the oxirane groups to cationic groups, wherein the improvement is using as the epoxy-based resin an advanced epoxy resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (2) a digylcidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A and (3) a dihydric phenol such as bisphenol A and optionally a capping agent such as p-nonylphenol.Coating compositions suitable for electrodeposition are prepared from the product obtained by the process.Type: GrantFiled: July 6, 1989Date of Patent: December 11, 1990Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 4968730Abstract: Preparation of pigment paste resins for cathodically depositable coating compositions based on epoxy resin-amine adducts obtained from unmodified or modified epoxy resins, which by partial or complete reaction of secondary amino groups with formaldehyde contain oxazolidine structures; whose tertiary amino groups introduced via primary-tertiary diamines are quaternized to at least 20 mol % using an organic acid and a monoglycidyl compound and which in a solution adjusted with water to a correct application viscosity contain a total of 80 to 100 millimoles of acid per 100 g of solid resin are described. The pigment pastes possess, both in concentrated and dilute form, a stability which meets practical requirements and, because of their rheology, are readily processed to ensure formation of defect-free films both during deposition and crosslinking by stoving. The applied films have good properties.Type: GrantFiled: September 21, 1989Date of Patent: November 6, 1990Assignee: Vianova Kunstharz, A.G.Inventors: Helmut Honig, Georg Pampouchidis, Herbert Matzer
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Patent number: 4962179Abstract: A composition is disclosed containing an epoxidized fatty acid ester, an aromatic amine curing agent and an acid or metal salt accelerator. The composition can optionally contain a polyglycidyl ether of a polyhydric alcohol, an unsaturated monomer and a monoepoxy diluent. The composition has long pot life at room temperature and good flexibility and elongation.Type: GrantFiled: August 31, 1989Date of Patent: October 9, 1990Assignee: Shell Oil CompanyInventor: Larry S. Corley
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Patent number: 4959425Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resing having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: June 27, 1989Date of Patent: September 25, 1990Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4954602Abstract: A liquid, epoxy resin composition suitable for use in fixation of a stator coil or a rotor coil is disclosed, which comprises (A) a mixture containing (a.sub.1) a Bisphenol A epoxy resin and (a.sub.2) an alicyclic epoxy resin; and (B) a curing agent including (b.sub.1) an acid anhydride, and (b.sub.2) a phenol compound of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 represent independently from each other a lower alkyl, R.sup.3 represents a lower alkylene and n is an integer of 1-5, the amount of the phenol compound (b.sub.2) being in the range of 2-8% based on the weight of the mixture (A).Type: GrantFiled: June 23, 1989Date of Patent: September 4, 1990Assignee: Somar CorporationInventors: Ichiro Akutagawa, Tsutomu Yamaguchi, Toshihiro Hanamori, Kunimitsu Matsuzaki, Shinobu Okamura
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Patent number: 4940740Abstract: Heat curable epoxy resin systems are disclosed which may be cured to form monophasic matrix resins and adhesives which, when utilized as matrix resins in carbon fiber reinforced composites, are capable of forming quasiisotropic panels having CAI values greater than 275 MPa after an impact of 6.68 kJ/m, and which maintain their tack after extended storage at room temperature.Type: GrantFiled: April 21, 1989Date of Patent: July 10, 1990Assignee: BASF AktiengesellschaftInventors: Thomas Folda, Thomas Allspach
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Patent number: 4929650Abstract: A coating material for a tendon for prestressed concrete includes a curing composition, the curing time of which is so controlled that the composition is held in an uncured fluid state for a predetermined time after the concrete hardens. After the predetermined time passes, the composition cures. By coating a tendon for prestressed concrete with the coating material having such properties, an antirust effect of the tendon, an improved adhering force of the tendon to the concrete and a decreased cost of manufacturing prestressed concrete can be obtained.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignees: Mitsui Sekiyu Kagaku Kogyo Kabushiki Kaisha, Shinko Kosen Kogyo Kabushiki KaishaInventors: Makoto Kurauchi, Michio Hashimoto, Kiyoshi Hayasaki, Toshikazu Minami, Mutsuhiko Ohnishi, Yohei Suzuki
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Patent number: 4925886Abstract: A tough, durable, high temperature epoxy tooling composition for making cast-to-size forming tools. The composition comprises a bisphenol-A epoxy, a trifunctional aromatic epoxy, an anhydride catalyst, and an imidazole catalyst. The composition may optionally contain a filler system comprising filler particles having different diameters that are interstitially-matched.Type: GrantFiled: January 23, 1989Date of Patent: May 15, 1990Assignee: General Motors CorporationInventors: Richard P. Atkins, Chen-Shih Wang, Thomas J. Dearlove
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Patent number: 4914185Abstract: Adducts of metabrominated monophenols such as 3,5-dibromo-2,4,6-trimethylphenol and multifunctional epoxides such as cresol-formaldehyde epoxy novolac resins are disclosed to be useful in formulations for encapsulating electronic components.Type: GrantFiled: April 14, 1986Date of Patent: April 3, 1990Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Abel Mendoza
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Patent number: 4892925Abstract: 2,6-dibromo-3,5-dialkyl-4-hydroxybenzyl ethers, glycidyl ethers thereof and reaction products with phenolic hydroxyl-containing compounds, and glycidyl ethers of the resulting new phenolic hydroxyl-containing compounds.Type: GrantFiled: January 23, 1989Date of Patent: January 9, 1990Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Abel Mendoza, David B. Fritz
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Patent number: 4883830Abstract: A coating resin composition comprising mainly an epoxy-polyamine resin obtained by adding (d) an amine compound having active hydrogen to an epoxy resin, said epoxy resin being a reaction product of(a) a diepoxide compound represented by the following formula (I) ##STR1## wherein R represents a lower alkyl group or --CH.sub.2 OR' wherein R' represents a hydrocarbon group having 1 to 10 carbon atoms, and m+n is an integer of 1 to 6(b) a bisphenol, and(c) optionally, a bisphenol diglycidylether,(d) an amine compound having active hydrogen.Type: GrantFiled: November 3, 1988Date of Patent: November 28, 1989Assignee: Kansai Paint Co., Ltd.Inventors: Michiharu Kitabatake, Akira Tominaga
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Patent number: 4868059Abstract: Electrical laminates are prepared from prepreg materials prepared by impregnating a substrate with a laminating varnish comprising a solvent solution of a curable composition comprising (A) a mixture of at least one epoxy resin having an average of more than 1 but not more than 2 vicinal epoxy groups per molecule and at least one epoxy resin having an average of more than 2 vicinal epoxy groups per molecule; (B) a mixture of at least one phenolic hydroxyl-containing compound having an average of more than 1 but not more than 2 phenolic hydroxyl groups per molecule and at least one phenolic hydroxyl-containing compound having an average of more than 2 phenolic hydroxyl groups per molecule; and (C) at least one catalyst for effecting the reaction between (A) and (B).Type: GrantFiled: November 16, 1987Date of Patent: September 19, 1989Assignee: The Dow Chemical CompanyInventors: Louis L. Walker, Paul A. Larson
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Patent number: 4868230Abstract: A method for preparing an advanced epoxy cationic resin from an epoxy-based resin containing oxirane groups by converting at least some of the oxirane groups to cationic groups, wherein the improvement is using as the epoxy-based resin an advanced epoxy resin obtained by reacting in the presence of a suitable catalyst (1) a diglycidylether of an aliphatic diol which is essentially free of ether oxygen atoms, such as a diglycidyl ether of 1,4-butanediol, (2) a diglycidylether of a dihydric phenol, for example a diglycidyl ether of bisphenol A and (3) a dihydric phenol such as bisphenol A and optionally a capping agent such as p-nonylphenol.Coating compositions suitable for electrodeposition are prepared from the product obtained by the process.Type: GrantFiled: July 2, 1987Date of Patent: September 19, 1989Assignee: The Dow Chemical CompanyInventors: Nancy A. Rao, Richard A. Hickner
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Patent number: 4863575Abstract: An advanced epoxy cationic resin having a charge density of from 0.2 to 0.6 milliequivalent of cationic charge per gram of resin is prepared by reacting in the presence of a suitable catalyst (A) a composition comprising (1) at least one diglycidyl ether of (a) an oxyalkylated aromatic diol or (b) an oxyalkylated cycloaliphatic diol or (c) certain oxyalkyalted aliphatic diols and (2) at least one diglycidyl ether of a dihydric phenol with (B) at least one dihydric phenol and optionally (C) a monofunctional capping agent. Components (A-1) and (A-2) are employed in quantities such that from 10 to 75 weight percent of the diglycidyl ethers contained in component (A) are contributed by component (A-1), and from 25 to 90 weight percent of such glycidyl ethers are contributed by component (A-2). Components (A) and (B) are employed in such quantities that the resultant epoxy resin has an average epoxide equivalent weight of from 350 to 10,000.Type: GrantFiled: December 3, 1987Date of Patent: September 5, 1989Assignee: The Dow Chemical CompanyInventors: Kenneth W. Anderson, Richard A. Hickner
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Patent number: 4857567Abstract: A series of oligomeric adducts of diols and diepoxides are disclosed which are precursors of amine resins for use in electrodeposition coatings. The adducts are epoxide-alcohol addition products of a polyaromatic and/or a mono-aromatic diol and a polyaromatic bis-glycidyl ether, and/or a monoaromatic bis-glycidyl ether and/or an alkoxy arylene bis-glycidyl ether, thioether or amine. The coatings which include amine resin, cross linking agent, grind resin and pigment exhibit excellent corrosion resistance.Type: GrantFiled: July 24, 1987Date of Patent: August 15, 1989Assignee: BASF Corporation, Inmont DivisionInventors: James A. Laugal, Glenn E. Martin, Donald L. St. Aubin, Gerald G. Wold
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Patent number: 4857562Abstract: A fixing agent comprising Poly(alkylene oxide) moieties is used to fix a delayed cure of UV curable epoxy compositions exposed to UV radiation.Type: GrantFiled: March 7, 1988Date of Patent: August 15, 1989Assignee: General Electric CompanyInventors: Thomas P. Wacker, Raymond J. Zabinski
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Patent number: 4845172Abstract: Co-advanced epoxy resins prepared by the reaction of polyethers of polyhydric phenols, diglycidyl ethers of di-secondary alcohols and dihydric phenols, said co-advanced resins being heat curable with suitable curing agents to afford cured coating compositions exhibiting a variety of excellent physical properties and performance characteristics.The diglycidyl ethers have the following formula: ##STR1## as defined in the specification.Type: GrantFiled: April 26, 1988Date of Patent: July 4, 1989Assignee: Ciba-Geigy CorporationInventors: Vincent Brytus, Kenneth L. Payne
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Patent number: 4842910Abstract: The invention is a hollow fiber and tubesheet assembly which comprises(A) a non-random fiber bundle comprising water wet cellulose ester hollow fibers wherein the fiber is water wet when the assembly is fabricated, wherein any of said fibers processed using plasticizers have been leached to remove the plasticizer; and(B) a tubesheet which comprises the reaction product of:(i) an epoxy resin comprising about(a) between about 10 and 100 percent by weight of a diglycidyl ether of a dihydroxy benzene;(b) between about 0 and about 90 percent by weight of a polyglycidyl ether of a polyhydric phenol which is not a diglycidyl ether of dihydroxy benzene;(ii) a curing agent in sufficient amount to cure the epoxy resin composition;wherein a portion of the hollow fibers are embedded in the tubesheet.Type: GrantFiled: April 22, 1988Date of Patent: June 27, 1989Assignee: The Dow Chemical CompanyInventor: Terrence L. Caskey
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Patent number: 4840979Abstract: This invention provides a process for the preparation of cationic coating compositions, which comprises blending:(1) 5-35% w of a crosslinking compound, and(2) 65-95% w of a carboxylated amide group-containing amino binder being the reaction product of an amino group-containing resin binder and not more than about 0.1 mole of a cyclic anhydride per amino group equivalent of said amino group containing resin binder, which amino group-containing binder comprises the reaction product of(a) ammonia, and(b) a blend of(b.sub.1) a polyglycidyl ether having n epoxy groups per molecule, wherein 1<n<1.9, said polyglycidyl ether being the reaction product of a multifunctional polyglycidyl ether having x epoxy groups per molecule, wherein x>2, and (x-n) mol of a monofunctional phenol per mol of the multifunctional polyglycidyl ether, and(b.sub.Type: GrantFiled: June 10, 1988Date of Patent: June 20, 1989Assignee: Shell Oil CompanyInventors: Roeland Van Iperen, Johannes M. Van Der Mark, Petrus G. Kooijmans
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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: 4833227Abstract: Fluorinated polymers having epoxy resin structure, containing at least 10% by weight, preferably 20% by weight, of fluorine, prepared starting from epichlorohydrin and from one or more diols, at least one of which is a perfluoroalkylene diol, and by using conventional cross-linking agents for epoxy resins, such as anhydrides of dicarboxylic acids, di- or tri-isocyanates, polyfunctional amines.Type: GrantFiled: December 10, 1987Date of Patent: May 23, 1989Assignee: Ausimont S.p.A.Inventors: ALberto Re, Mario Alfieri
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Patent number: 4829105Abstract: An anodic electrodeposition composition containing a water-soluble or water-dispersible modified epoxy resin derived from an epoxy resin having two epoxide groups and at least one alcoholic hydroxy group at the terminals and the middle of the resin backbone, respectively. The modified epoxy resin has at least one polymeric side chain block bound to said alcoholic hydroxy group and at least one acid group derived from said terminal epoxide group.Type: GrantFiled: January 28, 1988Date of Patent: May 9, 1989Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kazunori Kanda, Shinsuke Shirakawa, Hirotoshi Umemoto, Ryuzo Mizuguchi
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Patent number: 4824927Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes. For the preparation of the binders, a di-epoxide compound, together with at least one mono-epoxide compound if desired, is converted by a polyaddition, carried out at 100.degree. to 195.degree. C. and initiated by a monofunctionally reacting initiator carrying either an alcoholic OH group, a phenolic OH group or an SH group, to form an epoxy resin which then subsequently is modified with(A) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or a phosphine/acid mixture and with, if desired,(B) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.Type: GrantFiled: January 23, 1987Date of Patent: April 25, 1989Assignee: BASF Lacke & Farben AKTInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4820797Abstract: Thermoset products are prepared by polymerizing (A) at least one thermosettable compound which contains both a maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and optionally (B) at least one of (1) at least one aromatic polycyanate such as bisphenol A dicyanate; (2) at least one polymaleimide such as N,N'-(methylenedi-p-phenylene)bismaleimide; (3) at least one material having an average of more than one vicinal epoxide group per molecule such as a diglycidyl ether of bisphenol A; (4) at least one polymerizable ethylenically unsaturated material such as styrene; or (5) a mixture of any two or more of components 1-4 in any combination.Type: GrantFiled: May 17, 1988Date of Patent: April 11, 1989Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4820784Abstract: Modified advanced epoxy resins are prepared by reacting (A) an 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 about 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 phosphorus-containing compound.Type: GrantFiled: January 13, 1988Date of Patent: April 11, 1989Assignee: The Dow Chemical CompanyInventors: John L. Massingill, Jr., Raul A. Pabon, Jr.
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Patent number: 4820798Abstract: Thermoset products are prepared by polymerizing (A) at least one thermosettable compound which contains both a maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and optionally (B) at least one of (1) at least one aromatic polycyanate such as bisphenol A dicyanate; (2) at least one polymaleimide such as N,N'-(methylenedi-p-phenylene)bismaleimide; (3) at least one material having an average of more than one vicinal epoxide group per molecule such as a diglycidyl ether of bisphenol A; (4) at least one polymerizable ethylenically unsaturated material such as styrene; or (5) a mixture of any two or more of components 1-4 in any combination.Type: GrantFiled: May 17, 1988Date of Patent: April 11, 1989Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4816300Abstract: The invention provides a process for the preparation of water-reducible carboxylated amide binders comprising the steps of:(1) reacting:(a) a substantially epoxy-free compound of general formula ##STR1## wherein A is the organic residue of a ring opening reaction of a vicinal epoxy group of a polyepoxide with ammonia or amine having at least two amino hydrogens, R.sup.1, R.sup.3 and R.sup.4 each is hydrogen or a C.sub.1-6 alkyl group, with the proviso that at least one of R.sup.1, R.sup.3 and R.sup.4 is hydrogen, R.sup.2 is a C.sub.2-12 alkylene group, x is 0 or 1 and y is a number from 0 to 4, with(b) a carboxyl group-containing mono- or polyester compound derived from a di- or polycarboxylic acid and a polyhydric alcohol having at least one glycol group per molecule, with the proviso that only one carboxyl group per molecule or di- or polycarboxylic acid has been esterified and the or each ester group is a .beta.-hydroxyester group,at a temperature in the range of from 80.degree. to 160.degree. C.Type: GrantFiled: January 15, 1988Date of Patent: March 28, 1989Assignee: Shell Oil CompanyInventors: Petrus G. Kooijmans, Roeland Van Iperen, Arjan Sikking
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Patent number: 4816546Abstract: Novel epoxy resins are prepared by dehydrohalogenating the reaction product of an epihalohydrin and a hydroxyalkyl containing polysulfide.Type: GrantFiled: June 23, 1987Date of Patent: March 28, 1989Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Paul L. Wykowski
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Patent number: 4816533Abstract: Epoxy resins have been found to be fortified (increased strength and modulus yet not brittle) by compounding(a) a resin-forming polyepoxide,(b) an amine curing agent for (a),(c) a fortifier for (a)+(b) comprising the reaction product of(i) an aromatic amine having an amine group attached to an aromatic ring; and(ii) non-symmetrical diepoxide;the reaction product optionally being further reacted with isocyanates or nitriles, in which case (ii) may be at least partly, a monoepoxide;and heat curing the mixture. Strengths as high as 130-150 MPa and modulus increases to as high as 5000 MPa have been attained along with a ductile mode of fracture.Type: GrantFiled: August 7, 1987Date of Patent: March 28, 1989Assignee: Canadian Patents and Development Ltd.Inventors: Paul D. McLean, Andrew Garton, Robert F. Scott
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Patent number: 4814414Abstract: Novel 3-ring tetraglycidates having the formula ##STR1## wherein ##STR2## Y=halogen, C.sub.1 -C.sub.4 alkyl; and n=0 to 4, are disclosed.Epoxy resin systems exhibiting good tensile properties and moisture sensitivity can be made by copolymerizing the tetraglycidates with a polyamine curing agent. Prepregs can be made by combining the epoxy resin systems with a fiber reinforcement. The epoxy resin system may include a co-epoxide.Type: GrantFiled: December 17, 1987Date of Patent: March 21, 1989Assignee: Amoco CorporationInventor: Richard H. Newman-Evans
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Patent number: 4810535Abstract: Disclosed herein are glycidol-modified polyepoxide-polyoxyalkylene polyamine adducts for use as additives in coatings to provide improved coating appearance.Type: GrantFiled: February 1, 1988Date of Patent: March 7, 1989Assignee: PPG Industries, Inc.Inventors: Gregory J. McCollum, Robert R. Zwack
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Patent number: 4797425Abstract: A method of producing a porous material having open pores comprises the steps of preparing an emulsion slurry by vigorously agitating a mixture comprising a main ingredient, a polyamide hardener, a filler and water, casting said emulsion slurry in a water-impermeable mold, hardening said slurry while it contains the water. The main ingredient is a bisphenol-type epoxy resin added with one or more reactive diluents each having one or more epoxy rings per molecule and added in an amount of 18 to 50 wt %, based on 100 wt % of said bisphenol-type epoxy resin. A large size molded product having a high wet bending strength and a complicated contour can be produced.Type: GrantFiled: September 3, 1987Date of Patent: January 10, 1989Assignee: Toto Ltd.Inventors: Noboru Kishima, Akio Matsumoto
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Patent number: 4777084Abstract: Viscous oligomeric epoxy resins can be quickly cured at temperatures of 100.degree. C. by incorporating a hardener that is a blend of (a) the oligomeric reaction product of bisphenol A and bisphenol A monoglycidyl ether and (b) an imidazole. The cured resins are tough and resistant to both moisture and high temperatures. Prepregs, in which glass, graphite or polymeric organic fiber sheets are saturated with these resins, are particularly useful in the repair of damaged aircraft and aerospace structures.Type: GrantFiled: October 8, 1987Date of Patent: October 11, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventor: Bruce A. Marteness
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Patent number: 4772645Abstract: Storage-stable, thermally-curable, one-part epoxy resin compositions comprising a curable opoxide resin; a curative amount of an aliphatic or non-aromatic cyclic polyol having about 2 to 18 carbon atoms, at least two hydroxy groups of said polyol being primary or secondary, and said polyol being free of strong acid groups, and free of electron-withdrawing substituents and large groups which cause steric hindrance in the .alpha.-position in relation to the carbon atoms attached to the methylol groups of the polyol; and a catalytic amount of an imidazole compound.Type: GrantFiled: December 11, 1987Date of Patent: September 20, 1988Assignee: Minnesota Mining and Manufacturing CompanyInventors: Kent S. Tarbutton, Janis Robins, John C. Tangen
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Patent number: 4769402Abstract: Aqueous solutions containing an epoxy resin in which epoxy groups have been replaced with a group M.sup.+ [--CH(OH)--CH.sub.2 --X--Ar--NH--C(O)--Q--C(O)--O].sup.- in which M is an alkali metal or onium ion, Q an organic bridging group having 2-3 carbon atoms in the bridge, Ar is arylene, X is S, O, NH, N-alkyl, SO.sub.2 NH or SO.sub.2 N-allyl, and preparation thereof by reacting an N-substituted imide with an epxoy resin and reacting the adduct thus formed with a base in the presence of water.Type: GrantFiled: May 11, 1987Date of Patent: September 6, 1988Assignee: Shell Oil CompanyInventors: Willem Karzijn, Petrus G. Kooijmans
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Patent number: 4764581Abstract: The invention relates to new, liquid-crystalline diglycidyle compounds of optionally ring-substituted 4-hydroxyphenyl 4-hydroxybenzoates, a synthesis of p-epoxypropoxy-phenyl p-epoxy-propoxybenzoate, furthermore epoxy resin mixtures containing the new diglycidyle compounds, and the use of the new diglycidyl compounds and the epoxy resin mixtures thereof in curable mixtures.Type: GrantFiled: June 22, 1987Date of Patent: August 16, 1988Assignee: Bayer AktiengesellschaftInventors: Hanns P. Muller, Roland Gipp, Heinrich Heine
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Patent number: 4764571Abstract: An epoxy resin having the formula: ##STR1## wherein R is a hydrogen atom or a methyl group, and n is an integer of from 0 to 15, and wherein said resin has an epoxy equivalent in the range of 260-345 g/eq.Type: GrantFiled: January 30, 1987Date of Patent: August 16, 1988Assignee: Sanyo-Kokusaku Pulp Company LimitedInventors: Hiroaki Namba, Minoru Hishinuma
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Patent number: 4758638Abstract: Advanced epoxy resins are prepared by reacting an epoxy resin composition containing a mixture of from 6% to less than 50% epoxide equivalents of an aliphatic diepoxide and from greater than 50% to 94% epoxide equivalents of an aromatic diepoxide with a dihydric phenol.Type: GrantFiled: September 9, 1987Date of Patent: July 19, 1988Assignee: The Dow Chemical CompanyInventors: Richard A. Hickner, Gwendolyn M. Grays, Kevin A. Owens
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Patent number: 4758636Abstract: A polyester composition comprises (1) a polyester being incapable of further substantial propagation of the chains by heating, being capable of forming the anisotropic phase in the molten state, being capable of the melt-processing and (2) an epoxy compound and is improved in heat resistance.Type: GrantFiled: November 21, 1986Date of Patent: July 19, 1988Assignee: Polyplastics Company, Ltd.Inventors: Kenji Hijikata, Toshio Kanoe