Reactant Which Is Devoid Of A Heterocyclic Ring Containing Oxygen, Selenium Or Tellurium As Ring Atoms, Contains At Least One Nitrogen Atom Patents (Class 528/407)
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Patent number: 4983672Abstract: A method of improving epoxy resin compositions to provide a cured resin having improved glass transition temperature and toughness characteristics is provided. The method includes providing in an epoxy resin composition an effective amount of a 9,9-bis(hydroxphenyl)fluorene composition. The fluorene component acts as a chain extension agent and provides for increased glass transition temperature and less cross-link density. As a result, improved toughness occurs. In preferred applications a toughening agent is provided in the resin composition, to further enhance toughness. Preferred resin compositions, cured resins and methods of providing improved cured resins are also provided.Type: GrantFiled: December 23, 1987Date of Patent: January 8, 1991Assignee: Minnesota Mining and Manufacturing CompanyInventors: Carl J. Almer, William J. Schultz
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Patent number: 4968767Abstract: The invention relates to substituted 3-(N-imidazolyl)propionic hydrazides, to their use as curing agents in epoxy-resin compositions, and to curable epoxy-resin compositions containing them and comprised of (a) an epoxy resin, and (b) optionally of dicyandiamide, and (c) optionally of conventionally used nitrogen-containing heterocyclic amine compounds, for the production of molded articles.Type: GrantFiled: June 14, 1989Date of Patent: November 6, 1990Assignee: Schering AGInventors: Christian Burba, Werner Mrotzek
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Patent number: 4968732Abstract: This invention is directed to a compound of the formula ##STR1## wherein the substituents are defined hereinbelow. R is an aliphatic group, cycloaliphatic group, aryl group or araliphatic group andR.sup.1 and R.sup.2 are each independently hydrogen, lower alkyl or aryl,R.sup.3 is a chemical bond or ##STR2## Z and Z.sup.1 are independently O or NH, R.sup.5 is R,R.sup.4 is lower aliphatic, arylene, aryl lower alkylene or cycloaliphatic,wherein the aliphatic group contains up to 10 carbon atoms in the principal chain and up to a total of 15 carbon atoms;the cycloaliphatic group contains up to 10 ring carbon atoms and up to a total of 15 carbon atoms; andthe aryl group is an aromatic group containing from 6 to 10 ring carbon atoms and up to a total of 15 carbon atoms.These compounds are used as accelerators in epoxy resin compositions, comprising (a) an epoxy resin, (b) dicyandiamide and optionally (c) solvents, fillers, reinforcement materials or inert materials, pigments or aids, for the production of moldings.Type: GrantFiled: March 23, 1990Date of Patent: November 6, 1990Assignee: Schering AktiengesellschaftInventors: Christian Burba, Werner Mrotzek
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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: 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: 4933415Abstract: There are provided polyethers end-blocked with hydrolyzable silyl groups which have molecular weight from 500 to 50,000 and are represented by the formula: ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 individually represent a divalent hydrocarbon group, R.sup.5 represents a monovalent hydrocarbon group, R.sup.6 represents an alkyl group with 1 to 6 carbon atoms, A represents a substituted or non-substituted divalent aromatic group, a represents a number of 1 to 3, m represents a number of 10 to 500 and n represents a number of 1 or greater. The polyether is produced by reacting an epoxy end-blocked polyoxyalkylene, a mono-epoxy substituted hydrolyzable silane, and an aromatic diamine.Type: GrantFiled: August 26, 1988Date of Patent: June 12, 1990Assignee: Toshiba Silicone Co., Ltd.Inventors: Chiyuki Shimizu, Tamio Yoshida
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Patent number: 4933422Abstract: Accelerators for epoxide curing agents containing cyanamide are described which use an adduct and/or reaction product of (a) a specific imidazole derivative with (b) an organic acid having a pK.sub.A value of 0.5 to 5.0.The accelerators according to the invention impart to the epoxy resin-curing agent-accelerator system a longer shelf life compared with known accelerators.Type: GrantFiled: May 15, 1989Date of Patent: June 12, 1990Assignee: SKW Trostberg AktiengesellschaftInventor: Benedikt Hammer
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Patent number: 4931528Abstract: Disclosed is an epoxy resin curative exhibiting extended pot life, increased resistance to heat and chemicals, lower reactivity at ambient temperatures and increased reactivity at moderately elevated temperatures which comprises from 1 to 5 parts by weight of 1-isopropyl-2-methyl imidazole per 100 parts by weight epoxy resin. The latent reactive properties make the curative potentially useful in a variety of applications.Type: GrantFiled: May 8, 1989Date of Patent: June 5, 1990Assignee: Texaco Chemical CompanyInventors: Harold G. Waddill, George P. Speranza, Wei-Yang Su
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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: 4912190Abstract: An epoxy resin composition, including epoxy resin, cyanamide as a hardener, and 2-methylimidazole or 2,4-ethyl-methylimidazole as an accelerator in hardening the epoxy resin.Type: GrantFiled: May 6, 1988Date of Patent: March 27, 1990Assignee: AEG Isolier- Und Kunststoff GmbHInventor: Hans-Jurgen Schafer
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Patent number: 4910269Abstract: The invention is an epoxy resin coating composition. The composition comprises:1. a cycloaliphatic epoxy resin (hydrogenated bisphenol A resin), and2. a triacrylate ester, reacted with a mixture of3. a polyether polyamine of the formula:NH.sub.2 CH(CH.sub.3)CH.sub.2 [OCH.sub.2 CH(CH.sub.3)].sub.x NH.sub.2 a.wherein 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 blemish-free, attractive, high-gloss coatings.Type: GrantFiled: October 13, 1988Date of Patent: March 20, 1990Assignee: Texaco Chemical Co.Inventor: Harold G. Waddill
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Patent number: 4902777Abstract: N-(polyoxyalkyl)-N-(alkyl)amines are provided that are reactive with isocyanates to form polyurea and/or polyurethane urea polymers.Type: GrantFiled: March 31, 1988Date of Patent: February 20, 1990Assignee: Union Carbide Chemicals and Plastics Company, Inc.Inventors: Richard M. Gerkin, David J. Schreck, Danny E. Smith
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Patent number: 4902760Abstract: A cross-linked resin produced by heating a mixture of (a) a bis(2-oxazoline) compound, (b) an aromatic polyamine compound which has at least two amino groups in the molecule and (c) a polyepoxy compound which has at least two epoxy groups in the molecule at elevated temperatures, preferably in the presence of an oxazoline ring-opening polymerization catalyst. The resin shows a high mechanical strength and toughness, a very small water absorption and a very high resistance to heat.Type: GrantFiled: October 26, 1988Date of Patent: February 20, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kazuhiro Arita, Yasuo Sano
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Patent number: 4898923Abstract: A novel class of polymers comprises one or more dipyridinium units, having the formula ##STR1## contained within the main polymer backbone where Ar.sup.1, Ar.sup.2, and Ar.sup.3 are aromatic or heteroaromatic nuclei each of which can consist of one ring or two fused or catenated rings having 5 to 12 ring carbon and heteroatoms which can include 1 to 3 unitary heteroatoms selected from S, N, and O, R.sup.1 is any divalent organic bridging group, and Z.sup..crclbar. is a counterion.Type: GrantFiled: March 1, 1989Date of Patent: February 6, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Katritzky, Larry R. Krepski, Jerald K. Rasmussen, Steven M. Heilmann, Richard D. Tarr
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Patent number: 4894431Abstract: Curing systems for epoxy resins comprising an aliphatic or cycloaliphatic amine in combination with anhydrous methane sulfonic acid as an accelerator for the curing reaction.Type: GrantFiled: May 23, 1988Date of Patent: January 16, 1990Assignee: Ciba-Geigy CorporationInventors: Robert F. Armbruster, Rajan Eadara, William L. Miller
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Patent number: 4891408Abstract: Novel tetraglycidates have the formula ##STR1## wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl of 1 to 8 carbon atoms, perfluoroalkyl, or cycloalkylidene of 5 to 7 carbon atoms. 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: August 13, 1987Date of Patent: January 2, 1990Assignee: Amoco CorporationInventor: Richard H. Newman-Evans
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Patent number: 4889672Abstract: The process for producing a ceramic molding of the present invention comprises adding 0.1 to 20 parts by weight of an adduct of epoxidized polybutadiene with an organic amine to 100 parts by weight of a ceramic powder.Type: GrantFiled: February 2, 1988Date of Patent: December 26, 1989Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Mitsuo Akutsu, Keiji Tabata
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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: 4861810Abstract: The present invention relates to a new thermoplastic polymer composition having the processing characteristics of a thermosetting polymer along with an improved balance of properties including improved modulus/glass transition temperature/toughness balance. These new polymer compositions are prepared by reacting certain amine compounds with certain diepoxide compounds to form linear units which are lightly crosslinked. Also disclosed and claimed are processes for preparing such compositions, cured compositions and end-use applications.Type: GrantFiled: August 15, 1988Date of Patent: August 29, 1989Assignee: Shell Oil CompanyInventor: Kenneth C. Dewhirst
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Patent number: 4859761Abstract: Curable epoxy resin compositions containing cyanoguanidines of formula I ##STR1## wherein, for example, R.sup.1 and R.sup.2 are phenyl, as latent hardeners, have good properties and are especially suitable for use as laminating resins.Type: GrantFiled: August 30, 1988Date of Patent: August 22, 1989Assignee: Ciba-Geigy CorporationInventors: Peter Flury, Alex Alder
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Patent number: 4855386Abstract: A composition is provided comprising an epoxy resin and an aromatic amine curing agent, the latter which can be described by the formula ##STR1## in which each R is selected C.sub.2 -C.sub.7 alkyl and each R' is selected from C.sub.1 -C.sub.7 alkyl. The described composition has good physical properties for high-performance composite applications and has a relatively long working life.Type: GrantFiled: December 31, 1987Date of Patent: August 8, 1989Assignee: Shell Oil CompanyInventor: Ronald S. Bauer
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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: 4841021Abstract: A novel class of polymers comprises one or more dipyridinium units, having the formula ##STR1## contained within the main polymer backbone where Ar.sup.1, Ar.sup.2, and Ar.sup.3 are aromatic or heteroaromatic nuclei each of which can consist of one ring or two fused or catenated rings having 5 to 12 ring carbon and heteroatoms which can include 1 to 3 unitary heteroatoms selected from S, N and O, R.sup.1 is any divalent organic bridging group, and Z.sup..crclbar. is a counterion.Type: GrantFiled: November 30, 1987Date of Patent: June 20, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: Alan R. Katritzky, Larry R. Krepski, Jerald K. Rasmussen, Steven M. Heilmann, Richard D. Tarr
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Patent number: 4837302Abstract: A cross-linked resin as obtained by the reaction of a bis (2-oxazoline) compound with an aromatic compound having at least two amino groups shows low water-absorption, excellent in strength, and, in addition, tough and superior in heat-resistance.The resin composition comprising the cross-linked resin and reinforcements and/or fillers can be especially advantageously utilized for preparing a variety of molded articles practically usable in a broad application field, for example, space, aircraft, railway vehicles, automobiles, civil engineering, electrical and electronic appliances, cross-resistant equipment, sports and leisure equipment, medical equipment and industrial parts, as well as in the new application areas where conventional fiber-reinforced resins have hardly been utilized by the reason of insufficient strength, water-absorption, heat-resistance, etc.Type: GrantFiled: October 21, 1987Date of Patent: June 6, 1989Assignee: Takeda Chemical Industries, Ltd.Inventor: Yasuo Sano
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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: 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: 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: 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: 4804740Abstract: Urea compounds having a plurality of substituents selected from hydrogen, substituted hydrocarbyl radicals and unsubstituted hydrocarbyl radicals are good latent cure accelerators for thermosetting cyanate resin formulations. The resulting cyanate resin formulations are useful as coatings, adhesives and as impregnating resins, particularly in applications where extended storage at or near room temperature is desired.Type: GrantFiled: July 8, 1987Date of Patent: February 14, 1989Assignee: Amoco CorporationInventors: Hugh C. Gardner, Richard H. Newman-Evans
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Patent number: 4791154Abstract: A composition comprising an epoxy resin and an aromatic azopolyamine curing agent is described. The use of azopolyamine curing agents in reactive monomer-diluted systems results in a high-modulus cured epoxy system.Type: GrantFiled: November 30, 1987Date of Patent: December 13, 1988Assignee: Shell Oil CompanyInventors: Larry S. Corley, Donald R. Gehring
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Patent number: 4786667Abstract: Polyethers end-blocked with hydrolyzable silyl groups are manufactured by reacting an epoxy end-blocked linear polyoxyalkylene, a mono-epoxy substituted hydrolyzable silane and an aromatic diamine and compounded with filler to produce a room temperature curable elastomer.Type: GrantFiled: May 22, 1987Date of Patent: November 22, 1988Assignee: Toshiba Silicone Co., Ltd.Inventors: Chiyuki Shimizu, Tamio Yoshida
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Patent number: 4785046Abstract: This invention relates to novel polymers, i.e., poly(5-imidazolones) and a process for preparing same from the reaction of a diazlactone with a primary diamine and thereafter dehydrating the resultant polyamide product. The polymers have good thermal properties and can be used as a composite matrix with a refinforcing agent such as fiber glass.Type: GrantFiled: August 7, 1987Date of Patent: November 15, 1988Assignee: W. R. Grace & Co.-Conn.Inventor: Shiow C. Lin
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Patent number: 4783518Abstract: A rapid curing composition comprising a mixture of (A) a polyepoxide and an amine curing agent and (B) a novel thiocyanate salt of the reaction product of an alkylene polyamine, such as ethylene diamine, and a bicyclic amide acetal and a method for curing said composition are described.Type: GrantFiled: September 28, 1987Date of Patent: November 8, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4775734Abstract: A curable composition comprising a polyepoxide, an amine curing agent and a catalytic amount of a non-nucleophilic acid salt of an amine having the formula R(R')(R")NH.sup.+ X.sup.- wherein R, R' and R" independently represent an alkyl group having from 1 to 20 carbon atoms, an alkaryl group having from 7 to 20 carbon atoms or an oxyalkylene group having from 2 to 50 carbon atoms and wherein R' and R" independently also may represent hydrogen and R may also represent the formula [--Y--(R')(R")NH.sup.+ X.sup.- ].sub.n wherein R' and R" have the foregoing designations, Y represents an alkylene or alkylene ether group having from 2 to 50 carbon atoms and n represents an integer of from 1 to 5 is described.Type: GrantFiled: August 12, 1987Date of Patent: October 4, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4775735Abstract: A moisture curable composition comprising a mixture of(A) a polyepxoide(B) a polyimine curing agent and(C) an amine thiocyanate salt cure accelerator,and a process for curing said composition in an atmosphere having a relative humidity of from about 20% to about 90% at a temperature in the range of from about 15.degree. C. to about 150.degree. C. are described.Type: GrantFiled: October 7, 1987Date of Patent: October 4, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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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: 4762903Abstract: The invention relates to water-dilutable binders for cationic electrocoating finishes, the said binders containing latent primary amino groups. In order to prepare the binders, an epoxy resin is reacted with a polyamine, which in addition to a sterically hindered primary amino group also contains at least one primary amino group blocked by reaction with a ketone or aldehyde, and, if appropriate, further primary or secondary amines.Type: GrantFiled: January 23, 1987Date of Patent: August 9, 1988Assignee: BASF Lacke & Farben AGInventors: Michael Geist, Gunther Ott, Georg Schon
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Patent number: 4761466Abstract: An adhesive composition comprising a mixture of a polyepoxide, an amine curing agent and a thiocyanate salt of a compound having the formula ##STR1## wherein R represents an alkyl group having from 1 to 20 carbon atoms, an aryl group having from 6 to 20 carbon atoms or an alkaryl group having from 7 to 20 carbon atoms, R', R" and R'" independently represent hydrogen, an alkyl group having from 1 to 10 carbon atoms or an alkyl ether group having from 1 to carbon atoms and n represents 2 or 3 is described.Type: GrantFiled: August 12, 1987Date of Patent: August 2, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4757125Abstract: A process for accelerating the cure rate of a mixture comprising an epoxy resin and an amine hardener comprising including in the mixture from 0.5% to 15% by weight of a catalyst which is the reaction product of a bicyclic amide acetal and ammonium thiocyanate and curing the resulting mixture at a temperature of from about abient temperature to about 120.degree. C. is described.Type: GrantFiled: July 8, 1987Date of Patent: July 12, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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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: 4742148Abstract: A latent catalyst for epoxy resin systems is produced by the reaction between an aromatic dicyanate and imidazoles. The catalyst provides good curability, excellent mechanical properties, and remarkably extended shelf life. It also allows curing at room temperature.Type: GrantFiled: April 17, 1987Date of Patent: May 3, 1988Assignee: Hexcel CorporationInventors: Frank W. Lee, Kenneth S. Baron
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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: 4728555Abstract: Process for the preparation of .beta.-hydroxypolyamines by reaction of polyepoxide compounds with ammonia, in which at least one polyepoxide compound is treated in a first stage with liquid ammonia at temperatures below 50.degree. C., a homogeneous phase being formed, after which the reaction between the polyepoxide compound and ammonia is carried out in a second stage at 60.degree. to 130.degree. C., and when the reaction is complete, the excess ammonia is removed from the reaction mixture.The resulting .beta.-hydroxypolyamines are used as binders or--in protonated form--as binders which can be diluted with water, by themselves or in combination with suitable crosslinking agents.Type: GrantFiled: August 15, 1986Date of Patent: March 1, 1988Assignee: Hoechst AGInventors: Hans-Joachim Kiessling, Wilhelm Riemenschneider
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Patent number: 4711936Abstract: A curing agent for an epoxy resin comprises a cyclodextrin clathrate compound of a compound which is reactive with an epoxy group, a curing agent for an epoxy resin comprising a mixture of a cyclodextrin clathrate compound of a compound which is reactive with an epoxy group with a trace amount of amylase, and methods for the preparation of these curing agents. The curing agents are stable at room temperature, and the curing reaction is initiated under remarkably simple conditions.Type: GrantFiled: November 13, 1985Date of Patent: December 8, 1987Assignee: Japan Liquid Crystal Co., Ltd.Inventors: Ichiro Shibanai, Kenji Nakamura