Nitrogen-containing Alcohol, Inorganic Alcoholate, Or Ether Patents (Class 528/111)
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Patent number: 4959439Abstract: A piezoelectric polymer material comprising a cured product of a composition comprised of an epoxy resin having at least two epoxy groups in the molecules, a compound having a molecular weight not less than 1200 and containing defined numbers of amino groups, benzene rings, carbonyl groups and methylene groups, and a crosslinking agent. The cured product has dipolarly oriented micro crystals therein. A method for making such a piezoelectric polymer material is also described, in which the resin composition is thermally cured and contacted with an electric field at a high temperature to cause dipolar orientation in the product. The dipoles are frozen by cooling the product while applying the electric field.Type: GrantFiled: February 27, 1990Date of Patent: September 25, 1990Assignee: Toyokako Kabushiki KaishaInventors: Katsumi Tanino, Morihito Nakada
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Patent number: 4959398Abstract: A powdery adhesive comprised of spherical particles comprising 40 to 90 parts by weight of an epoxy resin component, 10 to 60 parts by weight of a rubber component and a latent curing agent contained inside the particles, the average particle size of the particles being from 0.1 to 500 .mu.m. The powdery adhesive may be prepared by a process comprising a step of preparing a compatible mixture comprising an epoxy resin component, a rubber component and a common organic solvent, a step of emulsifying or suspending the compatible mixture in an aqueous medium to form spherical particles, and a step of causing a phase separation of the epoxy resin component and the rubber component in the spherical particles.Type: GrantFiled: February 13, 1989Date of Patent: September 25, 1990Assignee: Toray Industries, Inc.Inventors: Koichiro Oka, Ikuo Hagiwara
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Patent number: 4956402Abstract: A synthetic resin which carries basic nitrogen groups and is water-dilutable by protonation with acid is obtainable by reacting(A) an epoxy resin having an average molecular weight M.sub.n of from 200 to 6,000 and on average from 1.5 to 3.0 epoxy groups per molecule with(B) a ketimine of a primary amine additionally containing one or more urethane groups and optionally also with(C) a diketimine of a diprimary amine containing no urethane groups and optionally also with(D) a secondary amine which may contain a tertiary amimo group also, a ketimine of a primary monoamine and/or a ketimine of a primary/tertiary diamine.Type: GrantFiled: June 23, 1988Date of Patent: September 11, 1990Assignee: BASF Lacke & Farben AktiengesellschaftInventors: Thomas Perner, Rolf Osterloh, Eberhard Schupp, Thomas Schwerzel, Klaas Ahlers
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Patent number: 4946911Abstract: Curable compositions comprising a curing agent and the product resulting from reacting (I) the product resulting from the free radical polymerization of (A) the composition resulting from (1) reacting (a) a compound containing an average of more than one vicinal epoxide group per molecule with (b) at least one unsaturated imide having a reactive hydrogen atom attached to the imide nitrogen atom in amounts which provide a ratio of moles of component (b) per epoxide group contained in component (a) of from about 0.01:1 to about 1.1:1; and (2) optionally, reacting the product of step (A) with (c) at least one of (i) at least one compound containing only one phenolic hydroxyl group, (ii) at least one secondary amine, or (iii) a combination of (i) and (ii) in amounts sufficient that the resulting product contains a percent epoxide value of not greater than about 1.Type: GrantFiled: May 22, 1989Date of Patent: August 7, 1990Assignee: The Dow Chemical CompanyInventor: Duane S. Treybig
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Patent number: 4946924Abstract: Secondary isopropylamine terminated polyoxyethylene and/or polyoxypropylene diamines or triamines are formed in a one-step reaction when a polyoxyethylene and/or polyoxypropylene primary diamine or triamine is hydrogenated with hydrogen in the presence of a hydrogenation catalyst, hydrogen and acetone. The secondary isopropylamine terminated polyoxyethylene and/or polyoxypropylene primary diamines or triamines are useful as curing agents for epoxy resins.Type: GrantFiled: October 31, 1988Date of Patent: August 7, 1990Assignee: Texaco Chemical CompanyInventors: George P. Speranza, Jiang-Jen Lin, James H. Templeton
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Patent number: 4940770Abstract: Disclosed are novel compositions useful in mixed epoxy material synthesis, poly(epoxy)-(urea) synthesis and cases where epoxy curing agents require flexibility which are essentially the reaction products of polyoxyalkylene polyamines and epoxides. Specifically the amine reactants comprise polyoxypropylene triamines, amine terminated alkylene glycols and polyoxypropylene diols, such as those represented by Texaco Chemical Company's JEFFAMINE.RTM. T-series, JEFFAMINE.RTM. EDR series and JEFFAMINE.RTM. D-series amines, respectively. The epoxide component prepolymers essentially comprise Bisphenol A diglycidyl ethers. The ratio of JEFFAMINE.RTM. amine to epoxide and the use of acetone are essential to prepare non-gelled products.Type: GrantFiled: November 14, 1988Date of Patent: July 10, 1990Assignee: Texaco Chemical Co.Inventors: George P. Speranza, Jiang-Jen Lin
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Patent number: 4921928Abstract: A piezoelectric polymer material comprising a cured product of a composition comprised of an epoxy resin having at least two epoxy groups in the molecules, a compound having a molecular weight not less than 1200 and containing defined numbers of amino groups, benzene rings, carbonyl groups and methylene groups, and a crosslinking agent. The cured product has dipolarly oriented micro crystals therein. A method for making such a piezoelectric polymer material is also described, in which the resin composition is thermally cured and contacted with an electric field at a high temperature to cause dipolar orientation in the product. The dipoles are frozen by cooling the product while applying the electric field.Type: GrantFiled: June 17, 1988Date of Patent: May 1, 1990Assignee: Toyokako Kabushiki KaishaInventors: Katsumi Tanino, Morihito Kakada
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Patent number: 4897435Abstract: A hydrophilic, substantially epoxy-free self-cross-linkable polymer contains hydroxyalkyl carbamate groups and one or more tertiary amine groups. The polymer suitably is made by reacting an epoxy resin having an average epoxy equivalent weight of from about 100 to about 700 with one or more amines having at least one secondary amine group and at least one hydroxyalkyl carbamate group or precursor thereof. A coating composition comprises an aqueous medium containing the polymer and, optionally, a cross-linking catalyst. A low temperature-curable coating is attained by utilization of the polymer with a suitable quaternary or ternary compound catalyst.Type: GrantFiled: February 17, 1984Date of Patent: January 30, 1990Assignee: American Cyanamid CompanyInventors: William Jacobs, III, Werner J. Blank
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Patent number: 4886867Abstract: Disclosed is a method for preparing a novel difunctional epoxy resin of the formula: ##STR1## where R is from a Bisphenol A diglycidyl ether and x=2 to .apprxeq.10, which comprises reacting an excess of a Bisphenol A diglycidyl ether with a secondary isopropyl amine derivative of a polyoxyalkylene primary diamine or triamine in the presence of acetone.A method for preparing a novel di- and trifunctional secondary amines of the formula: ##STR2## which comprises reacting a Bisphenol A diglycidyl ether with an excess of a secondary isopropyl amine derivative of a polyoxyalkylene primary diamine or triamine in the presence of acetone where R is from Bisphenol A diglycidyl ether and x=1, 2 or 3.Type: GrantFiled: November 14, 1988Date of Patent: December 12, 1989Assignee: Texaco Chemical CompanyInventors: Jiang-Jen Lin, George P. Speranza
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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: 4853442Abstract: Novel sulfur containing polyarylene polyether oligomers are disclosed. The oligomers are prepared through condensing salts of hydroxy and/or thio aromatic compounds, halobenzenoid compounds bearing two replaceable halogens and metal or ammonium sulfides following by end capping the resultant oligomer intermediate with a salt of a hydroxy and/or thio aromatic compound.Type: GrantFiled: April 3, 1987Date of Patent: August 1, 1989Assignee: Hercules IncorporatedInventor: Tuyen T. Nguyen
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Patent number: 4853456Abstract: The invention is an epoxy resin thermoset adhesive composition. The composition comprises the cured reaction product of:(A) an epoxy base resin, and(B) a curing amount of an admixture comprising:1. an amidoamine of the formula: ##STR1## wherein: P is an iso or para phenylene moiety, and R is the polyoxypropylene moiety of the formula:H.sub.2 NCH(CH.sub.3)CH.sub.2 --[OCH.sub.2 CH(CH.sub.3)].sub.x NH--wherein: x ranges from 2 to 40, and2. an aliphatic polyetheramine, aromatic amine or mixture thereof.The compositions cured at elevated temperature cross-link to form adhesives demonstrating high peel strength and high shear strength.Type: GrantFiled: February 19, 1988Date of Patent: August 1, 1989Assignee: Texaco Chemical CompanyInventors: Kathy B. Sellstrom, Terry L. Renken
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Patent number: 4847360Abstract: Adhesive active finish compositions for synthetic reinforcing members to bond the latter to vulcanizable rubber and reinforcing members for vulcanizable rubber. The adhesive composition comprises a water soluble epoxy compound, from about 20 to 100 parts by weight of a trialkanolamine having from 3 to about 15 carbon atoms and from about 0 to 80 parts by weight of a polyol co-curative having from 2 to about 15 carbon atoms and having at least 2 primary hydroxyls per molecule, wherein the stoichiometric ratio of hydroxyl groups to epoxy groups from the water soluble epoxy compound ranges from about 1:0.7 to 1:0.0003. A method of reinforcing articles of vulcanizable rubber with fibrous members includes the steps of applying to the fibrous member a first coating of the adhesive active finish; applying a second coating comprising resorcinol, formaldehyde and a rubber latex over the first coating; embedding the coated fibrous member in the vulcanizable rubber and, vulcanizing the rubber.Type: GrantFiled: June 21, 1988Date of Patent: July 11, 1989Assignee: The Firestone Tire & Rubber CompanyInventors: William L. Hergenrother, Mario N. DeTrano
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Patent number: 4837295Abstract: Epoxy resin adhesives in which polyoxyalkylene polyamines are used as curing agents possess significantly improved initial adhesion and thermal shock resistance when mono- or bis-unsaturated cyclic imides are present, e.g. maleimides, bis-maleimides, bicycloheptene discarboximides, and bis-bicyloheptene dicarboximides.Type: GrantFiled: March 4, 1988Date of Patent: June 6, 1989Assignee: Loctite CorporationInventors: Kieran F. Drain, Kris Kadziela
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Patent number: 4835241Abstract: The invention is an epoxy resin coating composition. The composition comprises:1. a bisphenol A resin, and2. an acrylate ester, reacted with a mixture of3. a polyether polyamine of the formula:a. NH.sub.2 CH(CH.sub.3)CH.sub.2 [OCH.sub.2 CH(CH.sub.3)].sub.x NH.sub.2wherein x ranges from 2 to 6, orb. ##STR1## wherein x+y+z ranges from 4 to 6; and 4. piperazine.The weather resistant formulations cure rapidly to form attractive blemish-free, blush-free coatings.Type: GrantFiled: September 3, 1987Date of Patent: May 30, 1989Assignee: Texaco Inc.Inventor: Harold G. Waddill
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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: 4828771Abstract: A method of producing a porous material having open pores comprises the steps of preparing an emulsion slurry by vigorously agitating a mixture comprising (i) a glycidyl type epoxy resin, (ii) a first hardener selected from the group consisting of modified polyamine hardeners each being prepared by modifying a polyamine hardener with a modifier, amine hardeners and mixtures thereof, (iii) a second hardener selected from the group consisting of polyamide hardeners, (iv) a filler and (v) water, casting said slurry in a water-impermeable mold, and hardening said slurry while it contains water. A large size molded product having a complicated contour and having open pores whose average pore diameter ranges from 0.2 to 10 microns can be produced with high dimensional accuracy.Type: GrantFiled: August 21, 1987Date of Patent: May 9, 1989Assignee: Toto Ltd.Inventors: Noboru Kishima, Akio Matsumoto
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Patent number: 4829142Abstract: Aminohydroxy fatty acid amides obtained by condensation from epoxidized fatty acid alkyl esters and polyfunctional aliphatic oligoamines may be employed as crosslinking agents for polyfunctional epoxide compounds used as adhesives and/or coating compositions.Type: GrantFiled: August 18, 1987Date of Patent: May 9, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Rene A. A. Gonzalez, Manfred Budnowski, Julius Herold, Horst Rutzen, Eberhard Schneider, Hans-Guenter Seltmann
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Patent number: 4828879Abstract: A polymer concrete system has been discovered which is useful in road overlay and repair. The binder for this aggregate-filled system consists of a liquid opoxy resin and triethyleneglycol diamine or tetraethylene glycol diamine curing agent. A piperazine accelerator ensures adequate strength development after short cure times at ambient temperatures.The binder-aggregate system is relatively flexible, has excellent compression and flexural strength and adheres well to the substrate. The system is distinguished by its fast cure to a compression strength of 3000 psi which will support automotive traffic.Type: GrantFiled: July 30, 1987Date of Patent: May 9, 1989Assignee: Texaco Inc.Inventors: Kathy B. Sellstrom, Harold G. Waddill
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Patent number: 4826930Abstract: Novel melamine-poly(oxyethylene or oxypropylene) diamine condensates are prepared which have the formula: ##STR1## Wherein: R represents H or--NH--CHR'--(CH.sub.2).sub.x --[--O--CH.sub.2 --CHR"--].sub.n --O--(CH.sub.2).sub.x --CHR'--NH.sub.2R' represents H or --CH.sub.3,R" represents H or -CH.sub.3 or CH.sub.2 CH.sub.3,x represents an integer having a value of 1 or 2, andn is a number having an average value of about 1 to about 2.The melamine-poly(oxyethylene or oxypropylene) diamine condensates have utility as curing agents for epoxy resins.Type: GrantFiled: April 22, 1988Date of Patent: May 2, 1989Assignee: Texaco Chemical CompanyInventors: Robert L. Zimmerman, Harold G. Waddill, George P. Speranza
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Patent number: 4826616Abstract: A piezoelectric pressure-sensitive element comprising a dispersion of a dipolarly oriented ferroelectric ceramic powder in a cured product of a composition comprised of an epoxy resin having at least two epoxy groups in the molecules, a compound having defined numbers of amino groups, benzene rings, carbonyl groups and methylene groups, and a crosslinking agent. A methd for making such a piezoelectric pressure-sensitive element is also described, in which the resin composition comprising a ferroelectric ceramic powder is thermally cured and applied with an electric field at a high temperature to cause dipolar orientation of at least the ceramic powder.Type: GrantFiled: June 17, 1988Date of Patent: May 2, 1989Assignee: Toyokako Kabushiki KaishaInventors: Katsumi Tanino, Morihito Nakada
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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: 4814415Abstract: The invention is an epoxy resin thermoset adhesive composition. The composition comprises the cured reaction product of:(A) an epoxy base resin, and(B) a curing amount of an admixture comprising:1. an oxamidoamine of the formula: ##STR1## wherein: R is the polyoxypropylene moiety of the formula:H.sub.2 NCH(CH.sub.3)CH.sub.2 --[OCH.sub.2 CH(CH.sub.3)].sub.x NH--wherein: x ranges from 2 to 40, and2. an aliphatic polyetheramine, aliphatic polyamine, aromatic amine or mixture thereof.The adhesives are cured at elevated temperature. They are noted for high peel strength and good shear strength.Type: GrantFiled: February 19, 1988Date of Patent: March 21, 1989Assignee: Texaco Chemical CompanyInventors: Kathy B. Sellstrom, David C. Alexander
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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: 4800215Abstract: Uncured compositions are prepared from dialkanolamines and polyglycidyl ethers of tris(hydroxyphenyl)alkanes. These compositions are water soluble or water miscible.Type: GrantFiled: March 18, 1988Date of Patent: January 24, 1989Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Willie L. Myles, Michael P. Kubisiak
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Patent number: 4789721Abstract: Carboxylic acid-polyetherpolyamine reaction products which contain as the principle reaction component, an amidoamine having the formula: ##STR1## where R=polyether segment as previously defined.Z=dicarboxylic acid of structure given in Examples 2 and obtained by reacting a polyoxypropylene and/or polyoxyethylene diamine with an aromatic dicarboxylic acid in molar proportions such that at least about 1.0 to 1.2 mole equivalents of amine are provided in the reaction mixture of each mole equivalent of carboxylic acid present in the reaction mixture. The amidoamines exhibit improved properties which allow for a rapid curing system even under ambient conditions and useful applications include coatings, adhesives, encapsulations, laminates and composite fabrications.Type: GrantFiled: July 27, 1987Date of Patent: December 6, 1988Assignee: Texaco Inc.Inventors: Harold G. Waddill, Jiang-Jen Lin, George P. Speranza
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Patent number: 4780524Abstract: The invention relates to a water-dilutable binder for cationic electrocoating finishes. For the preparation of the binders(A) a di-epoxide compound with an epoxide equivalent weight below 2,000 is reacted with(B) a phenol- or thiol-containing compound which reacts monofunctionally with epoxide groups, and with(C) primary and/or secondary amines or their salts and/or the salt of a tertiary amine, a sulfide/acid mixture or phosphine/acid mixture or a mixture of these compounds, as well as, if desired, with(D) a polyfunctional alcohol, a polycarboxylic acid, a polysulfide or a polyphenol.The components A and B are used in a molar ratio of from 10:1 to 1:1, preferably from 4:1 to 1.5:1 and the reaction of the component A with the component B is carried out at 100.degree. to 190.degree. C., if desired in the presence of a catalyst.Type: GrantFiled: January 23, 1987Date of Patent: October 25, 1988Assignee: BASF Lacke + Farben AGInventors: Arnold Dobbelstein, Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4769438Abstract: Diamines of the formula:H.sub.2 N(CH(CH.sub.3)CH.sub.2 O).sub.x nC.sub.4 H.sub.8 OCH.sub.2 CH(CH.sub.3)NH.sub.2are modified with 5 to 50 wt % of a diglycidyl ether of bisphenol A to form a prepolymer. When reacted with an epxoy resin, these modified diamines impart improved properties to the cured resin compared with the unmodified amine. Improved rate of cure and greater thermal shock resistance were achieved.The cured resin products are useful for coatings, adhesives, encapsulations, laminates and composite fabrications.Type: GrantFiled: June 29, 1987Date of Patent: September 6, 1988Assignee: Texaco Inc.Inventors: Robert L. Zimmerman, Harold G. Waddill, Kathy B. Sellstrom
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Patent number: 4766196Abstract: A rapid curing epoxy resin composition comprising a mixture of(A) A first component comprising a polyepoxide and(B) A second component comprising a mixture of the novel reaction product of(1) an ammonium salt of a non-nucleophilic acid with(2) the reaction product of(a) a bicyclic amide acetal with(b) an amine, and(3) an amine curing agent, is described.Type: GrantFiled: August 14, 1987Date of Patent: August 23, 1988Assignee: Ashland Oil, Inc.Inventors: Anil B. Goel, Teresa A. DeLong
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Patent number: 4751278Abstract: The adducts of monoepoxides with selected diamines, preferably m-xylylenediamine, are useful as curing agents for the curing of epoxy resin compositions at very low temperatures (25.degree.-50.degree. F., -4.degree. to 10.degree. C.).Type: GrantFiled: April 29, 1987Date of Patent: June 14, 1988Assignee: Ciba-Geigy CorporationInventor: Vincent Brytus
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Patent number: 4751257Abstract: A resin coating composition characterized by containing as its resin binder an epoxy resin derivative having an oxazolidine ring functional group of the formula ##STR1## where R.sub.1 is an alkylene group of 2 to 6 carbon atoms, R.sub.2 and R.sub.3 are each hydrogen or methyl, and R.sub.4 and R.sub.5 are each a residue of aldehyde or ketone.Type: GrantFiled: September 9, 1986Date of Patent: June 14, 1988Assignee: Kansai Paint Co., Ltd.Inventor: Akira Tominaga
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Patent number: 4739028Abstract: Epoxy resins have been found to be fortified (increased in strength and modulus yet not made brittle) by compounding:(a) a resin-forming polyepoxide(b) an amine curing agent for (a) and(c) a fortifier for (a)+(b) comprising the reaction product of(i) an aromatic polyhydroxy compound and(ii) a diepoxide with one epoxy group less reactive than the other:and heat curing the mixture. Strengths as high as 140 MPa and moduli as high as 4500 MPa have been attained with a ductile mode of failure.Type: GrantFiled: March 2, 1987Date of Patent: April 19, 1988Assignee: Canadian Patents & Development LimitedInventors: Paul D. McLean, Andrew Garton, Robert F. Scott
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Patent number: 4736011Abstract: Mannich condensates prepared from an imidazole, formaldehyde and a polyalkylene polyamine are useful as curing agents for epoxy resins.Preferably, a diamine is reacted with the imidazole and formaldehyde, as illustrated by the following formula: ##STR1## wherein: R represents hydrogen or a C.sub.1 -C.sub.Type: GrantFiled: October 2, 1986Date of Patent: April 5, 1988Assignee: Texaco Inc.Inventors: Harold G. Waddill, George P. Speranza
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Patent number: 4732961Abstract: A spherical particulate adhesive comprising particles of a partially amine cured epoxy resin as the main component and having an average particle size of 0.3 to 500 .mu.m, in which particles of the epoxy resin contain an at least partially compatible agent homogeneously in the interior thereof. This adhesive is a heat-curable adhesive and has a very high bonding force. After bonding, the adhesive is chemically stable and is especially preferably used for bonding in the field of electronic material, such as liquid crystal display devices, which are apt to be degraded by impurities and for which high-precision bonding is required.Type: GrantFiled: September 18, 1986Date of Patent: March 22, 1988Assignee: Toray Industries, Inc.Inventor: Koichiro Oka
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Patent number: 4724031Abstract: 2,6-Disubstituted 4-epoxypropyl glycidyl ethers of the formula ##STR1## wherein X is a group R' or X is a group of the formula ##STR2## and each of R and R' independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, a halogen atom or C.sub.6 -C.sub.10 aryl, can be used, together with customary epoxy resin hardeners, for the preparation of cured products, in particular for application in the electronics industry, or as adhesives. Compounds of the formula are also valuable reactive diluents for curable epoxy resin mixtures.Type: GrantFiled: June 4, 1986Date of Patent: February 9, 1988Assignee: Ciba-Geigy CorporationInventors: Charles E. Monnier, Sheik Abdul-Cader Zahir, Sameer H. Eldin
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Patent number: 4724254Abstract: The invention relates to water-dispersible binding agents for cationic electro-immersion varnishes on the basis of modified epoxy resins. The binding agents are reaction products of(A) low-molecular epoxy resins containing aromatic groups, with an equivalent epoxy weight of less than 375,(B) aliphatic and/or alicyclic polyfunctional alcohols and/or carboxylic acids with a molecular weight less than 350, where the intermediate product obtained from (A) and (B) has a content of aromatic groups of 10 to 45%, calculated as a phenylene group,(C) polyfunctional alcohols, carboxylic acids and/or SH-compounds with a molecular weight of 500 to 5000, and(D) amino alcohols with at least one concealed primary or a tertiary nitrogen atom.Type: GrantFiled: March 10, 1987Date of Patent: February 9, 1988Assignee: BASF Farben & Fasern AGInventors: Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4721770Abstract: N-Cyanocarboxylic acid amide derivatives which contain two or three ##STR1## groupings in the molecule are useful as hardeners for epoxide resins.Type: GrantFiled: June 24, 1986Date of Patent: January 26, 1988Assignee: Ciba-Geigy CorporationInventors: Friedrich Stockinger, Friedrich Lohse, Roland Moser
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Patent number: 4721742Abstract: Curable amide modified epoxy resins are prepared by polymerizing (I) the reaction product of (A) the reaction product of (1) an epoxy resin having an average of more than one 1,2-epoxy group per molecule and an average of from about 0 to about 30 aliphatic hydroxyl groups per molecule such as a diglycidyl ether of bisphenol A and (2) (a) a material having only one primary amine group per molecule such as monoethanolamine and (b) a material having only one secondary amine group per molecule such as diethanolamine wherein (a) and (b) are added sequentially with (a) being added first, or as a mixture with (B) an anhydride of an unsaturated dicarboxylic acid such as maleic anhydride with (II) a polymerizable ethylenically unsaturated monomer or mixture of monomers such as styrene and methacrylic acid. The resultant resin can be employed as is in the preparation of organic solvent borne coatings or it can be neutralized with a base so as to improve its stability in the preparation of aqueous coatings.Type: GrantFiled: November 7, 1986Date of Patent: January 26, 1988Assignee: The Dow Chemical CompanyInventors: James L. Bertram, Willie L. Myles
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Patent number: 4710561Abstract: A resin coating composition comprising an epoxy resin derivative having an imidazoline ring functional group of the formula ##STR1## wherein R.sub.1 represents an alkylene group having 2 to 6 carbon atoms, each of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represents a hydrogen atom or a methyl group, and R.sub.6 represents a residue of a carboxylic acid,as a resin binder. This resin coating composition is useful for cationic electrodeposition coating.Type: GrantFiled: November 26, 1986Date of Patent: December 1, 1987Assignee: Kansai Paint Co., Ltd.Inventors: Akira Tominaga, Reiziro Nishida
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Patent number: 4699937Abstract: A synthetic resin carrying basic nitrogen groups, its preparation, coating materials prepared from this resin, and a process for cathodic electrocoating.This synthetic resin is obtained by reacting(A) an epoxy resin which(B) a diketimine of a diprimary amineand, if required,(C) with a secondary amine, which may additionally contain a tertiary amino group, with a ketimine of a primary monoamine and/or with a ketimine of a primary/tertiary diamine,a diketimine obtained from(B.sub.1) a ketone and(B.sub.2) a branched aliphatic diprimary diamine of 5 to 9 carbon atoms and/or(B.sub.3) one or more diaminodiamides which are obtained by condensation of 2 moles of diamine (B.sub.2) and 1 mole of a dicarboxylic acidbeing employed as component (B).After protonation with an acid, this synthetic resin is useful as a binder for cathodic electrocoating.Type: GrantFiled: December 12, 1985Date of Patent: October 13, 1987Assignee: BASF Farben+Fasern AktiengesellschaftInventors: Werner Loch, Eberhard Schupp, Rolf Osterloh, Klaas Ahlers
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Patent number: 4695605Abstract: A structural adhesive which is particularly useful in vertical substrates is composed of a mixture of two components, the first component being an epoxy resin component comprising a poly epoxide and a polyisocyanate which has been allowed to react with less than an equivalent weight of a polyamine which is a primary or secondary polyamine and the second component being a hardener for the polyepoxide comprising a mixture of primary, secondary and tertiary amines, amido amines and phenolics.Type: GrantFiled: October 1, 1986Date of Patent: September 22, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4689388Abstract: A curable epoxy resin composition, comprising (1) an alicyclic epoxy resin having an average of more than one epoxy group per molecule, (2) a polybasic acid hydrazide, and (3) a latent curing agent for said epoxy resin which comprises an addition product obtained by reacting (a) a polyfunctional epoxy compound with (b) a compound having at least one functional group in the molecule selected from the group consisting of OH, SH, COOH and CONHNH.sub.2 together with a tertiary amino group, or by reacting said components (a) and (b) with (c) an organic compound which has more than two active hydrogen atoms in the molecule, said reactions occurring under conditions in which the ratio of (a) to (b) or (a) to (b) and (c) ranges from 0.8 to 2.5 equivalents of (a) per equivalent of the total active hydrogen atoms in component (b) and in components (b) and (c), the molar ratio of (c) to (b) being 0.2:1 to 1:1, and said addition product having a softening point of 60.degree. to 180.degree. C.Type: GrantFiled: January 23, 1986Date of Patent: August 25, 1987Assignee: Ajinomoto Co., Inc.Inventors: Kiyomiki Hirai, Koji Takeuchi, Hiroshi Sakamoto, Masahiro Abe
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Patent number: 4683283Abstract: An epoxide composition which is curable at a temperature in the range of from 25.degree. C. to 200.degree. C. which is composed of an epoxide resin, a phenol carbamate cure accelerator and an amine hardener is described.Type: GrantFiled: June 23, 1986Date of Patent: July 28, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4683281Abstract: A curable epoxide composition comprising an epoxide resin, a triaryl phosphite accelerator and a poly(alkylene oxide) polyamine or an amino alkyl piperazine hardener is disclosed.Type: GrantFiled: June 23, 1986Date of Patent: July 28, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4678712Abstract: A curable coating composition is prepared from two components; (1) a component having more than one epoxide group (an epoxy resin) and (2) a component having more than one group reactive with the epoxy groups of components (1) (i.e., a polyhydric phenol). Either component (1) or (2) is the reaction product of a compound containing at least one primary or secondary amino group and at least one aliphatic hydroxyl group with an epoxy resin and optionally a component reactive therewith. This reaction product contains terminal aliphatic hydroxyl groups and epoxy groups or groups reactive with epoxy groups. The components (1) and (2) are preferably normally solid materials and the coating composition is a powder coating composition.Type: GrantFiled: February 3, 1986Date of Patent: July 7, 1987Assignee: The Dow Chemical CompanyInventor: Brian W. Elliott
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Patent number: 4663190Abstract: A semiconductor element excellent in moisture resistance and thermal fatigue properties can be produced by forming a seal coating on at least part of the surface of semiconductor material, said seal coating being a cured resin obtained from an epoxy resin composition comprising (i) an epoxy resin, (ii) an organic dibasic acid dihydrazide and (iii) an imidazole.Type: GrantFiled: March 8, 1984Date of Patent: May 5, 1987Assignee: Hitachi Chemical Company, Ltd.Inventors: Koei Fujita, Yuji Aimono
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Patent number: 4658009Abstract: Disclosed is a 2-substituted-4,6-diamino-s-triazine/isocyanuric acid adduct represented by the following formula: ##STR1## wherein R stands for an alkyl group having 2 to 20 carbon atoms, an unsubstituted or cyano group-substituted aryl group, or a group of the formula R.sup.1 --CH.sub.2 CH.sub.2 -- in which R.sup.1 stands for an alkoxy group having up to 20 carbon atoms, an acyloxy group, an amino group, an N-substituted amino group, a benzotriazolyl group or a 2-alkylimidazolyl-(4)-dithiocarbonyl group, or by the following formula: ##STR2## wherein R.sup.2 stands for an alkylene group which may have an intervening imino or phenylene group.When this adduct is used for curing a polyepoxy resin, a cured product having good heat resistance, insulating property and adhesion and an excellent migration-preventing effect is formed.Type: GrantFiled: March 13, 1986Date of Patent: April 14, 1987Assignee: Shikoku Chemicals CorporationInventors: Kazuo Kamagata, Toshiaki Yamada, Natsuo Sawa
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Patent number: 4621025Abstract: Disclosed is a composition of an epoxy resin and about 0.1 to about 2 moles per epoxy equivalent weight of a .beta.-diketo amide having the general formula ##STR1## where R.sub.1 is selected from the group consisting of alkyl to C.sub.20, aliphatic, cycloaliphatic, and arylalkyl, R.sub.2 is selected from the group consisting of hydrogen and R.sub.1, and R.sub.3 is selected from the group consisting of aryl and R.sub.1. A .beta.-diketo modified epoxy resin is also disclosed which has the general formula ##STR2## The .beta.-diketo modified epoxy resin is used in resin compositions to increase their adherence to metals and to chelate with metal containing catalysts, forming self-catalyzed resins.Type: GrantFiled: September 23, 1985Date of Patent: November 4, 1986Assignee: Westinghouse Electric Corp.Inventor: James D. B. Smith
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Patent number: 4609685Abstract: Polyether polyols are modified by reaction with alkylene oxides and amino alcohol-epoxy resin adducts. The adducts are the reaction product of an epoxy resin and amino alcohol of the formula: ##STR1## wherein: x ranges from 1 to 4,y ranges from 1 to 40, andR is an alkyl of from 1 to 4 carbon atoms.These polyether polyols are used to prepare flexible polyurethane foams.Type: GrantFiled: May 6, 1985Date of Patent: September 2, 1986Assignee: Texaco Inc.Inventors: Michael Cuscurida, Harold G. Waddill
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Patent number: 4609446Abstract: The disclosed invention involves water-dispersible binding agents for cationic electrodeposition coatings and a method for making them, the binding agents are the reaction product of (A) epoxy resins having a molecular weight greater than about 350; (B) polyfunctional, alcohols, carboxylic acids and/or SH-compounds having a molecular weight between about 500-5000 and (C) aminoalcohols with at least one protected primary or tertiary nitrogen atom.Type: GrantFiled: January 6, 1984Date of Patent: September 2, 1986Inventors: Michael Geist, Gunther Ott, Georg Schon