Two Or More Nitrogen-containing Reactants Patents (Class 528/120)
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Patent number: 6172143Abstract: A resin composition for use in a liquid sealant, which is composed mainly of an epoxy compound, an epoxy resin curing agent and a polycarbodiimide resin, the proportion of the polycarbodiimide resin being 0.1 to 10 parts by weight relative to 100 parts by weight of the epoxy compound, and which is liquid or fluid at ordinary temperature. The liquid sealant comprises a resin composition which is composed mainly of an epoxy compound and a polycarbodiimide resin, the proportion of the polycarbodiimide resin being 0.1 to 10 parts by weight relative to 100 parts by weight of the epoxy compound, an epoxy resin curing agent, an epoxy resin curing accelerator and an inorganic powder. The sealant is liquid or fluid at ordinary temperature.Type: GrantFiled: January 12, 1999Date of Patent: January 9, 2001Assignee: Nisshinbo Industries, Inc.Inventors: Satoshi Amano, Hideshi Tomita
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Patent number: 6136944Abstract: The present invention relates to a flexible industrial adhesive composition which effectively bonds thermoplastic polymer substrates and substrates having low stiffness such as fabric, rubbers and asphaltic materials, to materials selected from metals, fabrics, rubbers, engineered materials, and concrete, said flexible industrial adhesive composition comprising:(a) one or more epoxy resin(s) having an average of at least 1.5 epoxy groups per molecule;(b) a liquid amine terminated polyamide prepared by reacting at least one C.sub.18-50 dicarboxylic acid and an aminoalkylpiperazine in a ratio of moles of aminoalkylpiperazine to equivalents of carboxyl group in the acid of greater than 0.75:1;(c) one or more optional polyamine(s); and(d) one or more optional filler(s);wherein the tensile modulus of the flexible industrial adhesive composition is less than 500,000 psi and the tensile elongation of the flexible industrial adhesive composition is greater than 10%.Type: GrantFiled: November 29, 1999Date of Patent: October 24, 2000Assignee: Shell Oil CompanyInventors: Steven Lee Stewart, Derek Scott Kincaid
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Patent number: 6077929Abstract: The present invention pertains to coating compositions including a particular class of internally blocked polyamines as replacement for traditional blocked and unblocked polyamine crosslinkers. The use of these internally blocked polyamines results in better appearance characteristics and a lower VOC than are generally available with the traditional blocked varieties.Type: GrantFiled: April 7, 1998Date of Patent: June 20, 2000Assignee: Akzo Nobel N.V.Inventors: Johannes Adrianus Pardoen, Wincenty Lambertus Stanislaw Pilaszek, Jan Wilhelm Ernst Moos, Keimpe Jan Van Den Berg
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Patent number: 6077886Abstract: A curable epoxy resin composition comprising (A) an epoxy resin, (B) a thixotropic agent in an amount sufficient to induce thixotropic properties, and a hardener comprising (C) at least one polyethyleneimine and (D) at least one other amine having at least 2 amino hydrogen atoms, the combined amounts of (C) and (D) being sufficient to effect cure of the epoxy resin.Type: GrantFiled: October 9, 1997Date of Patent: June 20, 2000Assignee: Ciba Specialty Chemicals CorpationInventors: Barry James Hayes, Kevin Brian Hatton
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Patent number: 6063893Abstract: A curing agent having less odor and providing a cured resin which is excellent in appearance, mechanical properties, water resistance and chemical resistance, and a one-component type humidity-curing resin composition having excellent storage stability and providing a cured matter which is excellent in appearance and physical properties. Specifically, provided are polyaminoamide or ketimine obtained by dehydration of 2,5- and/or 2,6-bis(aminomethyl)-bicyclo[2.2.1]heptane with carboxylic acids or ketones, a curing agent for epoxy resins using the same and a one-component type humidity-curing epoxy resin or urethane prepolymer composition containing the curing agent.Type: GrantFiled: May 26, 1998Date of Patent: May 16, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Minato Karasawa, Takeya Abe, Takuji Shimizu, Takeshi Iwaki
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Patent number: 6046282Abstract: Reactive diluents comprise the amide and/or imidazoline reaction products of low molecular weight carboxylic acids, such as acetic acid, and polyalkyleneamines, such as 2-aminoethylpiperazine (AEP) and triethylenetetramine (TETA). The reactive diluents are prepared by condensation reaction of the carboxylic acid and the polyalkyleneamine at elevated temperature generating a mixture of unreacted polyalkyleneamine, amides and/or imidazolines. The reactive diluent reaction products are used to reduce the viscosity of high viscosity polyamidoamines prepared from fatty dimer acids and polyethyleneamines. Also disclosed is an epoxy composition comprising the epoxy curative composition of a polyamidoamine curing agent reduced in viscosity by the addition of the reactive diluent reaction product and an epoxy resin, such as the diglycidyl ether of bisphenol A.Type: GrantFiled: January 6, 1998Date of Patent: April 4, 2000Assignee: Air Products and Chemicals, Inc.Inventors: William Edward Starner, Richard Scott Myers, Andrea Karen Smith
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Patent number: 6020069Abstract: An improved aqueous cathodic electrocoating composition of an aqueous carrier having dispersed therein a film forming binder of (1) an epoxy-resin amine adduct and (2) a blocked polyisocyanate crosslinking agent; wherein the improvement is an epoxy resin amine adduct which is a reaction product of an epoxy resin and a polyhydric phenol which is chain extended with a primary amine to form a chain extended epoxy resin having epoxy end groups and an equivalent amine to epoxy ratio is 1-10 to 4-10 and wherein the epoxy end groups of the resin are reacted with a ketimine and/or a diamine and the resulting chain extended epoxy resin has an epoxy equivalent weight of about 700-2,000 and is neutralized with an organic or inorganic acid; wherein the electrocoating composition has improved throw power and forms coatings that have improved corrosion resistance in comparison to conventional electrocoating compositions formed from epoxy resins extended with conventional diamines or polyols.Type: GrantFiled: June 18, 1998Date of Patent: February 1, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Joseph A. Antonelli, Christopher Scopazzi
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Patent number: 5977286Abstract: Epoxy resin compositions containing polyepoxides having at least two 1,2-epoxide groups are disclosed. The polyepoxides can be obtained by reacting (i) di- or polyepoxides or mixtures thereof with monoepoxides, (ii) one or more amines chosen from sterically hindered amines, disecondary diamines and diprimary diamines to form an epoxide-amine adduct, and (iii) subsequently reacting the epoxide-amine adduct with polyfunctional isocyanates. The composition also contains curing agents for the polyepoxides and can optionally contain additional 1,2-epoxide compounds and additives. The compositions are useful as coatings for bridging cracks, as adhesives and as constituents of paints.Type: GrantFiled: July 11, 1997Date of Patent: November 2, 1999Assignee: Vianova Resins GmbHInventors: Manfred Marten, Claus Godau
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Patent number: 5961684Abstract: A glass yarn sizing composition consisting of a solution having a viscosity of at most 400 cP and including less than 5 wt. % of solvent and at least one basic heat-polymerisable system which includes at least 60 wt. % of components having a molecular weight of less than 750, and at least 60 wt. % of a mixture of one or more components having at least one epoxy reactive function, and one or more components having at least one (preferably primary or secondary) amine reactive function, wherein the amount of components having at least one amine reactive function represents at least 6 wt. % of the composition. A method using said composition, and the resulting yarns coated with said composition, are also disclosed.Type: GrantFiled: September 4, 1997Date of Patent: October 5, 1999Assignee: Vetrotex FranceInventors: Patrick Moireau, Christelle Pousse
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Patent number: 5889125Abstract: A curing component (A) containing amino groups available for reaction with epoxy resins (B), wherein the curing component (A) is a condensation product of di- or polyhydroxyaromatics (A1) with polyamines (A2) is disclosed. The curing component (A) is useful in preparing curing mixtures (C) which include the curing component (A) and at least one epoxy resin (B), whereby the curing mixtures are useful in the production of shaped articles and as coatings.Type: GrantFiled: August 13, 1997Date of Patent: March 30, 1999Assignee: Vianova Resins GmbHInventors: Uwe Neumann, Claus Godau
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Patent number: 5872160Abstract: Disclosed is a denture adhesive composition comprising at least one non-adhesive self-supporting layer; and a partial salt of a lower alkyl vinyl ether-maleic acid copolymer, the partial salt copolymer comprising carboxyl groups, of which from about 50% to about 95% are neutralized by one or more metal cations; wherein the partial salt copolymer is covalently crosslinked with an organic crosslinker and wherein the molar ratio of organic crosslinker to carboxyl groups, prior to neutralization by the metal cations, is from about 0.1% to about 30%.Type: GrantFiled: March 27, 1997Date of Patent: February 16, 1999Assignee: The Procter &Gamble CompanyInventors: Nong Liang, Jayanth Rajaiah, Kimberly Ann Gilday-Weber
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Patent number: 5855961Abstract: This invention relates to coating compositions including one or more resins having amino-reactive groups; one or more polyamine curing agents; and one or more aminourethanes. The aminourethanes can be reaction products of (i) oligomeric or polymeric compounds which contain at least one, preferably two or more terminal 2-oxo-1,3-dioxolane groups (cyclic carbonate groups), and (ii) amines containing at least one primary, preferably two or more primary and, if desired, also secondary and tertiary amino groups. The ratios of equivalents of C1):C2) typically is from 1:1 to 1:10, preferably from 1:1.05 to 1:5 and particularly preferably from 1:1.1 to 1:2, and the end product preferably contains one or more free primary amino groups. The composition further may contain, if desired, pigments, fillers, one or more organic solvents, water and conventional additives.Type: GrantFiled: May 12, 1997Date of Patent: January 5, 1999Assignee: Vianova Resins GmbHInventors: Michael Hoenel, Armin Pfeil, Thomas Budnick, Heiner Schwan
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Patent number: 5783644Abstract: A curable epoxy resin composition comprising (I) an epoxy resin having more than one epoxy groups per one molecule, and (II) a specific Mannich base as essential components, with the amount of the Mannich base (II) being 1 to 50 parts by weight per 100 parts by weight of the epoxy resin (I), is lowly odoriferous and therefore easy of handling, is excellent in low-temperature curing characteristics, and its cured product exhibits excellent resistances to water, chemicals and amine blushing, and excellent physical properties.Type: GrantFiled: April 15, 1997Date of Patent: July 21, 1998Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuhiko Ando, Hiroshi Suzuki
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Patent number: 5770657Abstract: Provided are epoxy curing agents comprising the reaction product of reactants consisting essentially of a mono-alkylene polyamine having less than about 12 carbon atoms, an alicyclic diamine in an amount of greater than about 10% of the amine equivalents of said amine component, an aromatic mono-glycidyl ether having less than about 18 carbon atoms, and a diglycidyl ether of an aromatic diol having an average degree of oligomerization of less than about 3.5, wherein the ratio of primary amine equivalents of said alkylene polyamine to the total epoxide equivalents of said aromatic glycidyl ether and said diglycidyl ether of an aromatic diol is are greater than one, and the ratio of epoxide equivalents of said aromatic mono-glycidyl ether to epoxide equivalents of said diglycidyl ether of an aromatic diol is greater than one.Type: GrantFiled: July 3, 1996Date of Patent: June 23, 1998Assignee: Henkel CorporationInventors: Jason L. Chou, Shailesh Shah, Brian G. Jewell, Robert M. Moon
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Patent number: 5760162Abstract: In a process for the preparation of poly-o-hydroxyamides and poly-o-mercaptoamides, a bis-o-aminophenol or a bis-o-aminothiophenol is reacted at a temperature of .ltoreq.0.degree. C. with a mixed dianhydride of a dicarboxylic acid and a sulfonic acid with the following structure:E--SO.sub.2 --O--CO--R*--CO--O--SO.sub.2 --Ewhere E is an (optionally substituted) methyl, phenyl, or naphthyl group and R* is the parent body of the dicarboxylic acid.Type: GrantFiled: August 27, 1996Date of Patent: June 2, 1998Assignee: Siemens AktiengesellschaftInventors: Recai Sezi, Hellmut Ahne, Roland Gestigkeit, Kurt Geibel
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Patent number: 5728797Abstract: A suspension of finally divided hardened aminoplast or phenoplast resin, particularly melamine-formaldehyde resin, is prepared by mixing an aqueous solution of the resin or its precursors with a water-insoluble stabilizing agent, particularly microcrystalline cellulose; sufficient water is provided to exceed the water tolerance level of the resin and thus form a uniform emulsion or suspension of resin particles in water. Cure of the resin is then advanced such as by heating to form partially or fully cured resin particles of relatively uniform particle size.Type: GrantFiled: August 18, 1995Date of Patent: March 17, 1998Assignee: International PaperInventors: Robin D. O'Dell, Jayesh Shah, Alice M. Simon
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Patent number: 5726279Abstract: In a process for the preparation of poly-o-hydroxyamides and poly-o-mercaptoamides, a bis-o-aminophenol or a bis-o-aminothiophenol is reacted with a dicarboxylic acid derivative of the following structure: ##STR1## with D=O, S, or NH and where R* is the parent body of the dicarboxylic acid and the groups R.sup.1 through R.sup.4 are H, F, CH.sub.3, or CF.sub.3 (with a maximum of two CH.sub.3 or CF.sub.3 groups).Type: GrantFiled: August 29, 1996Date of Patent: March 10, 1998Assignee: Siemens AktiengesellschaftInventors: Recai Sezi, Hellmut Ahne
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Patent number: 5693743Abstract: The invention relates to aminoplastics, which are created by reacting comnds that contain amide groups with glutaric dialdehyde, and to a process for their preparation and to their use. The aminoplastic according to the invention is free of formaldehyde and can be hardened without difficulty by acidic catalysis or thermal processes. The aminoplastic is prepared by polycondensation of compounds that contain amide groups with glutaric dialdehyde in aqueous solution.Type: GrantFiled: October 10, 1995Date of Patent: December 2, 1997Assignee: Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung e.V.Inventors: Rudolf Nastke, Gerald Rafler
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Patent number: 5688905Abstract: An amine hardener composition for curing epoxy resin based coatings and related products comprising (A) from 5 to 75% of a diamine which possesses a vapor pressure less than about 133 Pascals at 20.degree. C., contains both a primary and a tertiary amine and corresponds to either of the structures: ##STR1## where R.sub.1 and R.sub.2 are independently C.sub.1 -C.sub.8 alkyl; X is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 --, or --CH.sub.2 --O--CH.sub.2 --; and n is 2-6, (B) from 5 to 95% of a polyamide, amidoamine, Mannich base or cycloaliphatic amine curing agent; and (C) from 0 to 50% of other active hydrogen containing dismines or polyamines. Coatings based on the composition can be formulated at up to 100% solids, and have an excellent combination of pot life and dry speed.Type: GrantFiled: September 20, 1995Date of Patent: November 18, 1997Assignee: Air Products and Chemicals, Inc.Inventor: Frederick Herbert Walker
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Patent number: 5652318Abstract: A flexible epoxy resin system is prepared by incorporating a combination of hardeners (A) and (B) in an epoxy resin, wherein the amounts of the two hardeners are varied to adjust the flexibility of the epoxy resin.Type: GrantFiled: June 4, 1996Date of Patent: July 29, 1997Assignee: Huels AktiengesellschaftInventors: Richard Braunstein, Bernhard Schleimer, Felix Schmitt, Joern Volker Weiss, Elmar Wolf
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Patent number: 5618905Abstract: A curable epoxy resin composition comprising a polyepoxide resin and an amine curative characterized in that the amine curative comprises a partially methylated polyalkylene polyamine having at least three amine nitrogens and at least two active amine hydrogens.Type: GrantFiled: January 16, 1996Date of Patent: April 8, 1997Assignee: Air Products and Chemicals, Inc.Inventors: John A. Marsella, William E. Starner, Richard S. Myers
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Patent number: 5616658Abstract: A curing agent for a composition useful for the production of matt epoxy resin and hybrid powder coatings, comprising a mixture ofa) salts of phthalic acid, isophthalic acid and terephthalic acid with the following amines ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are identical or different aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon radicals having 1-20 carbon atoms and in which one or more CH.sub.2 groups in the carbon chain may be replaced by 0 atoms, by NR.sub.4 groups where R.sub.4 =C.sub.1-6 -alkyl, CH--OH groups, and/or one or more terminal methyl groups may be replaced by dialkyl-substituted amino groups having 1 to 6 carbon atoms, and R.sub.1 and R.sub.2 may form a joint ring in which one CH.sub.2 group may be replaced by an O atom or by an NR.sub.4 group, and R.sub.1 =R.sub.2 =R.sub.3 --CH.sub.2 --CH.sub.2 -- attached via a common nitrogen atom, and n=3-11, and 0.5-2 mol of amine A)-C) per mole of acid, andb) pyromellitic acid and/or trimellitic acid, 0.Type: GrantFiled: January 10, 1995Date of Patent: April 1, 1997Assignee: Huels AktiengesellschaftInventors: Rainer Gras, Elmar Wolf
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Patent number: 5599629Abstract: Described herein is a composition comprising an epoxy resin containing at least one glycidyl amine group wherein the resin contains three or more epoxide groups per molecule and a particular aromatic amine hardener. These compositions possess the necessary balance of properties required for making prepreg and afford unreinforced castings with high moduli and strength.Type: GrantFiled: March 1, 1984Date of Patent: February 4, 1997Assignee: Amoco CorporationInventors: Hugh C. Gardner, Shahid P. Qureshi
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Patent number: 5591812Abstract: A curable epoxy resin composition comprising a polyepoxide resin and an amine curative characterized in that the amine curative comprises (a) the reaction product of excess monomethylamine (MMA) and an aliphatic or cycloaliphatic polyglycidyl ether and (b) an amine curative. When a diglycidyl ether is used in the reaction the resulting product can be described by the following structure: ##STR1## where R is an aliphatic, cycloaliphatic or aromatic organic radical and m is 0-3.Type: GrantFiled: January 26, 1996Date of Patent: January 7, 1997Assignee: Air Products and Chemicals, Inc.Inventor: William E. Starner
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Patent number: 5563224Abstract: Novel aminoplast anchored UV stabilizers are provided. Compared to unanchored stabilizers, the anchored stabilizers disclosed herein have increased compatibility with coating resins and have reduced volatility due to higher molecular weights resulting from anchoring. A process for preparing the anchored stabilizers by the reaction of unanchored stabilizers with alkoxymethylated aminoplasts in a sulfuric acid medium is also provided. The unanchored stabilizers include 2-(2-hydroxyaryl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyaryl)-4,6-diaryl-1,3,5-triazines, salicylic acid derivatives, 2-hydroxyoxanilides, and blocked derivatives thereof as well as mixtures of two or more stabilizers. The aminoplasts include alkoxymethylated derivatives of glycolurils, melamines, and benzoguanamines.Type: GrantFiled: May 23, 1995Date of Patent: October 8, 1996Assignee: Cytec Technology Corp.Inventors: Jeno G. Szita, Paul S. Waterman
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Patent number: 5545678Abstract: Amino-containing polymer systems which are suitable for the preparation of binders for printing inks can be obtained by synthesizing a polymer or polymer mixture A from at least one compound from each of the groups(a) epoxides, carbonates, epoxide-carbonates,(b) amines and(c) phenols,at least partial neutralization of the resulting polymer or polymer mixture A, and transfer to water, and optionally, preparing a water-insoluble polymer B which can be prepared by polymerization of ethylenically unsaturated monomers in the presence of the polymer or polymer mixture A.Type: GrantFiled: November 2, 1994Date of Patent: August 13, 1996Assignee: Hoechst AktiengesellschaftInventors: Astrid Giencke, Uwe Neumann, Bernd Mergardt, Gerd Walz
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Patent number: 5512372Abstract: Hardenable or polymerizable epoxy resin-based composition, characterized in that its hardener system comprises a combination in synergic quantities of:(i) at least one imidazole which, alone, can cause the polymerization of the epoxy resin only at a temperature above about 75.degree. C.,(ii) at least one polyamine compound which, alone, leads to the polymerization of the epoxy resin at a temperature lower than about 75.degree. C. Such a resin is particularly suitable for the manufacture of composite structures, applicable in particular in ship- or boatbuilding.Type: GrantFiled: August 24, 1994Date of Patent: April 30, 1996Assignee: Brochier, S.A.Inventors: Isabelle Blanc, Fran.cedilla.oise Eyriey, Xavier Gambert
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Patent number: 5508373Abstract: A method of curing an epoxy resin comprising mixing an epoxy resin with a curing agent is provided. The curing agent is selected from the group consisting of (i) a mixture consisting essentially of 1,2-diaminocyclohexane and an aliphatic polyamine (preferably at a molar ratio of 1,2-diaminocyclohexane to aliphatic polyamine of from about 1:1 to about 16:1, preferably about 2.5:1 to about 6:1 and more preferably about 3:1 to about 5:1) and (ii) the reaction product of reactants consisting essentially of an amine component consisting essentially of 1,2-diaminocyclohexane and an aliphatic polyamine and an epoxide component. The epoxide component has an epoxy functionality greater than one and is preferably a diglycidyl ether of an aromatic diol having an average degree of oligomerization of less than about 3.5., preferably less than about 1.5, and preferably derived from an alkyl bis-phenol, e.g. bisphenol A.Type: GrantFiled: August 4, 1994Date of Patent: April 16, 1996Assignee: Henkel CorporationInventors: Shailesh Shah, Robert M. Moon
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Patent number: 5503936Abstract: N-Alkyl-N'-aryl-p-phenylenediamines, when added at 2.5 to 12.5% by weight, based on the total weight of the epoxy resin and hardener, cause the epoxy resin after curing to exhibit substantial increases in physical properties, such as strength, stiffness, toughness and hot/wet properties, compared to the properties of the cured, but unmodified epoxy resin.Type: GrantFiled: January 12, 1995Date of Patent: April 2, 1996Assignee: Ciba-Geigy CorporationInventor: Yefim Blyakhman
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Patent number: 5492998Abstract: Novel polymers of general formula: ##STR1## wherein R is an alkyl or aryl group that contains an active hydrogen atom (as determined by the Zerewitinoff test); A is a spacing group having at least one carbon atom; B is a spacing group having at least two carbon atoms; and R and R' are alkyl or aryl groups. The polymer is synthesized via the Mannich pathway, involving formation of an imine intermediate.Type: GrantFiled: January 20, 1995Date of Patent: February 20, 1996Assignees: Lifesource International, Ltd., Jojani Inc.Inventor: Nicholas M. Irving
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Patent number: 5475039Abstract: A curing agent for aqueous epoxy resin emulsions comprising 10-80% by weight of at least one emulsifier, 1-80% by weight of at least one coemulsifier, and 5-80% by weight of at least one bis(diamine)-diepoxide adduct. Optionally, the curing agent contains 0-80% by weight of a diamine or a mixture of two or more diamines.Type: GrantFiled: October 17, 1994Date of Patent: December 12, 1995Assignee: Sika AG, vorm. Kaspar Winkler & Co.Inventor: Pierre-Andre Butikofer
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Patent number: 5464924Abstract: Polyaminoethers prepared by reacting (1) a primary amine or bis(secondary) diamine with (2) a diglyeidyl ether and (3) an amine- or epoxy-functionalized poly(alkylene oxide) exhibit a combination of low glass transition temperature (Tg of 14.degree. C. to 73.degree. C.) and low oxygen transmission rate (OTR of 0.53 to 19.0 cc-mil/100-in.sup.2 -atm-day).Type: GrantFiled: January 7, 1994Date of Patent: November 7, 1995Assignee: The Dow Chemical CompanyInventors: H. Craig Silvis, Shari L. Kram
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Patent number: 5445854Abstract: The present invention discloses oriented optical epoxy compositions comprising a reaction product of arylhydrazones with a monomer copolymerizable therewith and to oriented crosslinked polymeric composition comprising the reaction product of an epoxy arylhydrazone or the epoxy composition of the invention with a curing agent. The present invention also discloses processes for making the said compositions.Type: GrantFiled: November 29, 1993Date of Patent: August 29, 1995Assignee: The Dow Chemical CompanyInventors: Mark D. Newsham, Muthiah N. Inbasekaran, Michael N. Mang
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Patent number: 5426157Abstract: This invention relates to improved polyepoxide resins having enhanced physical and elastic properties. The polyepoxide resins comprise a polyepoxide resin based on a polyglycidyl ether of a phenolic-type compound and an acrylate-terminated urethane prepolymer. The improvement in the polyepoxide resin formulation comprises incorporating a polymethylated amine curative having two secondary amine hydrogens represented by the formula: ##STR1## wherein R is alkylene or polyalkylene polyamine having from 2 to 20 carbon atoms. The presence of the aliphatic amine reactive component along with the acrylate-terminated urethane prepolymer results in an epoxy resin having enhanced properties.Type: GrantFiled: March 16, 1994Date of Patent: June 20, 1995Assignee: Air Products and Chemicals, Inc.Inventors: William E. Starner, John A. Marsella, Richard S. Myers
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Patent number: 5420172Abstract: Cross-linked epoxy resins having nonlinear optical properties may be used in nonlinear optical media. These cross-linked epoxy resins may have the following structure: ##STR1## Z.sup.1 and Z.sup.2 being NLO-chromophores.Type: GrantFiled: August 23, 1993Date of Patent: May 30, 1995Assignee: Siemens AktiengesellschaftInventors: Jens Nordmann, Rainer Puehl
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Patent number: 5414067Abstract: This invention relates to an improved method for curing polyepoxide resins at elevated temperature and particularly to a method for reducing the time required to effect cure of thermosetting resins at elevated temperature without sacrificing performance. In the basic process, an epoxide resin comprising a polyglycidyl ether of a polyhydric phenol is mixed with cycloaliphatic amine, e.g., di(4-aminocyclohexyl)methane, di(4-amino-3-methylcyclohexyl)methane, and isophoronediamine in an amount sufficient to effect cure of the polyepoxide resin at an initial temperature and then raised to a final cure temperature. The improvement for reducing the time necessary for cure comprises:effecting an initial and partial cure of the epoxy resin at a temperature between 60.degree. and 100.degree. C.Type: GrantFiled: May 25, 1994Date of Patent: May 9, 1995Assignee: Air Products and Chemicals, Inc.Inventors: Menas S. Vratsanos, Andrea K. Smith
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Patent number: 5385990Abstract: A structural adhesive composition containing an epoxy compound, an amine hardener and a hydroxy-substituted aromatic compound having a pKa ranging from about 5 to 9.7 and a boiling point greater than about 210.degree. C. The utilization of a hydroxy-substituted aromatic compound having a pKa and a boiling point within the stated ranges provides for an adhesive composition which develops significant green strength, undergoes minimal sinkage during the bonding and curing process, and is capable of withstanding high temperature conditions.Type: GrantFiled: November 2, 1992Date of Patent: January 31, 1995Assignee: Lord CorporationInventors: Kirk J. Abbey, Stephen E. Howe, Beth C. Munoz
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Patent number: 5360887Abstract: A flame-retarded thermosetting resin composition is provided by blending about 5 to 45 mole % of a phenylcyanate having at least one halogen substituent at the ortho or para position relative to the cyanato group, and about 55 to 95 mole % of a halogen-free bis-4-phenylcyanate. A flame retardancy of V-O grade of UL94 is achieved in the thermoset resin of the composition without compromising dielectric, heat resistance, moisture absorption and other properties.Type: GrantFiled: July 28, 1993Date of Patent: November 1, 1994Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hidenari Tsunemi, Toshinobu Nakata, Koyoyuki Namura
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Patent number: 5360877Abstract: Epoxy interpenetrating polymer networks having chemical bonds between the interpenetrating networks are prepared from a first and a second polymer network, at least one of which contains an EPRXE resin; a resin having two epoxide functionalities represented by E and a reactive pendant nonepoxide functionality X. The two resin networks are sequentially crosslinked followed by activation of the pendant functionality of the EPRXE resin to form internetwork chemical bonds between the two resin networks affording an epoxy resin with both increased strength and toughness. The invention is also directed to the process of making interpenetrating polymer networks.Type: GrantFiled: May 13, 1993Date of Patent: November 1, 1994Assignee: Exxon Research and Engineering CompanyInventors: Jyi-Faa Hwang, John P. Dismukes
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Patent number: 5344897Abstract: Liquid coating agent based on a polymer containing acetoacetate groups and a polyamine in the form of the corresponding aldimine or ketimine, the polymer containing acetoacetate groups being obtained by reaction of a polyepoxide with water, an amine or a hydroxycarboxylic acid and subsequent esterification or transesterification with acetoacetic acid. These liquid coating agents are particularly suitable as binders in two-component automobile repair fillers or as two-component primers.Type: GrantFiled: October 29, 1993Date of Patent: September 6, 1994Assignee: Hoechst AGInventors: Gerhard Brindoepke, Uwe Kubillus, Helmut Plum
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Patent number: 5342904Abstract: Polymer modified adducts are prepared by (A) reacting (1) an epoxy resin having an average of more than one vicinal epoxide group with (2) a compound containing an average of two or more hydrogen atoms reactive with an epoxide group; and (B) partially vinylizing reacting the product from step (A); and (C) polymerizing the partially vinylized product from step (B) with (3) a polymerizable ethylenically unsaturated monomer; with the proviso that at least one of the components (1), (2) or (3) contain one or more mesogenic or rodlike moieties. These adducts are useful as epoxy resin curing agents.Type: GrantFiled: April 7, 1993Date of Patent: August 30, 1994Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5338782Abstract: A composition comprising a 1,2-dialkylidenecyclobutane such as 1,2-dimethylenecyclobutane, a polyimide such as a bismaleimide, an epoxy resin and a curing agent for the epoxy resin can be thermally cured to a tough polymer blend having a high glass transition temperature.Type: GrantFiled: May 27, 1993Date of Patent: August 16, 1994Assignee: Shell Oil CompanyInventor: Larry S. Corley
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Patent number: 5332785Abstract: A liquid coating composition based on a polymer containing acetoacetate groups and a polyamine in the form of the corresponding aldimine or ketimine, the polymer containing acetoacetate groups being obtained by reacting a polyepoxide containing hydroxyl groups, or a polyepoxide which is partially or completely reacted with monocarboxylic acids, with acetoacetic acid derivatives. These liquid coating compositions are suitable in particular as binders in two-component fillers for automotive refinishing or as two-component primers.Type: GrantFiled: March 29, 1993Date of Patent: July 26, 1994Assignee: Hoechst AktiengesellschaftInventor: Gerhard Brindoepke
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Patent number: 5292831Abstract: Phenoxy resins containing rodlike mesogenic moieties are prepared from phenolic hydroxyl containing compounds which contain such moieties.Type: GrantFiled: July 27, 1992Date of Patent: March 8, 1994Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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Patent number: 5288802Abstract: Curable coating compositions are provided containing an amine group containing polyepoxide resin, an acetoacetate containing polyester having a weight average molecular weight of at least 1000, and a polyacrylate containing material. The amine group containing polyepoxide can be modified with a ketone and/or an aldehyde to form a ketimine and/or an aldimine containing polyepoxide. The compositions are useful as coatings, particularly as ambient or low temperature curable automotive refinish primer coatings having good corrosion resistance, adhesion to both substrate and other organic coatings, sandability and pot-life.Type: GrantFiled: January 25, 1993Date of Patent: February 22, 1994Assignee: PPG Industries, Inc.Inventors: David N. Walters, Cathy A. Kreutzer, Padmanabhan Sundararaman
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Patent number: 5288816Abstract: The present invention relates to nonlinear optical materials comprising aminoaryl hydrazones and to nonlinear optical polymeric compositions containing recurring covalently bonded moieties derived from the aminoaryl hydrazones of the invention. The polymeric compositions of the present invention have high glass transition temperatures and exhibit stable nonlinear optical activity at high temperatures over a period of time.Type: GrantFiled: August 10, 1992Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventors: Muthiah N. Inbasekaran, Mark D. Newsham, Michael N. Mang
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Patent number: 5280091Abstract: This invention pertains to epoxy resins having increased chemical resistance to solvents, and good cured mechanical properties which are prepared by curing the epoxy resins with a curing agent comprising a mixture of methylene bridged poly(cyclohexyl-aromatic)amines. The methylene bridged poly(cyclohexyl-aromatic)amine curing agents are the residue obtained from the distillation of a mixture of poly(cyclohexylaromatic)amines formed by the hydrogenation of crude methylenedianiline or crude di(4-amino-3-methylcyclohexyl)methane.Type: GrantFiled: February 7, 1992Date of Patent: January 18, 1994Assignee: Air Products and Chemicals, Inc.Inventors: David A. Dubowik, Peter A. Lucas, Andrea K. Smith
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Patent number: 5279870Abstract: The present invention is directed to a novel epoxy polymeric composition resulting from reacting (A) at least one compound containing an average of more than one epoxide group per molecule with (B) at least one curing agent for component (A). At least a portion of the curing agent (B) is at least a first curing agent compound which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron withdrawing group. The present invention also includes a process for preparing the above polymeric materials. The polymeric materials of the present invention also exhibit nonlinear optical capabilities when formed into an optically transparent medium with a noncentrosymmetric alignment of molecules. The nonlinear optical materials of the present invention are useful in electrooptic devices for use in communications and data-processing.Type: GrantFiled: March 2, 1992Date of Patent: January 18, 1994Assignee: The Dow Chemical CompanyInventor: John J. Kester
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Patent number: 5280068Abstract: Curable epoxy resins are toughened with statistical monofunctional carboxyl, amine or epoxy terminated reactive polymers and have low viscosities before cure thereby making them useful in a wide range of applications. The cured epoxy resin systems which are modified by the statistical monofunctional reactive polymers have physical properties, such as adhesion and elongation, generally equal to or better than those of cured epoxy resin systems modified with statistical difunctional reactive polymers. A process of preparation for the modified epoxy resin systems of the present invention includes admixing an epoxy resin with a statistical monofunctional carboxyl, amine, or epoxy-terminated reactive polymer in the presence of a curing agent and reaction therewith to form the toughened, cured epoxy resin system.Type: GrantFiled: May 26, 1992Date of Patent: January 18, 1994Assignee: The B.F. Goodrich CompanyInventors: Alan R. Siebert, Robert J. Bertsch
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Patent number: 5273792Abstract: The present invention is directed to a novel epoxy polymeric composition resulting from reacting (A) at least one compound containing an average of more than one epoxide group per molecule with (B) at least one curing agent for component (A). At least a portion of the curing agent (B) is at least a first curing agent compound which contains (a) an average of more than one active amine hydrogen atom per molecule and (b) an average of at least one aromatic ring which contains at least one pendant monovalent electron withdrawing group. The present invention also includes a process for preparing the above polymeric materials. The polymeric materials of the present invention also exhibit nonlinear optical capabilities when formed into an optically transparent medium with a noncentrosymmetric alignment of molecules. The nonlinear optical materials of the present invention are useful in electrooptic devices for use in communications and data-processing.Type: GrantFiled: March 13, 1992Date of Patent: December 28, 1993Assignee: The Dow Chemical CompanyInventor: John J. Kester