Mixed With Nitrogen-containing Chemical Treating Agent Patents (Class 525/504)
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Patent number: 5856382Abstract: A coating composition is described comprising, in an aqueous medium:A) a resin having a plurality of primary amine groups, andB) a curing agent having a plurality of cyclic carbonate groups.Type: GrantFiled: October 3, 1996Date of Patent: January 5, 1999Assignee: BASF CorporationInventors: Walter H. Ohrbom, Timothy S. December, Paul J. Harris
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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: 5846453Abstract: The preparation of alkoxylates of oligoamines or polyamines by a two-stage procedure where, in the first stage, one molecule of alkylene oxide per NH group is added onto the oligoamines or polyamines in the presence of water, alcohols or acids or a mixture thereof in the absence of a neutral or basic catalyst and, in the second stage, after removal of water and acids reaction with further alkylene oxide is carried out in the presence of a conventional neutral or basic catalyst, entails, before the second stage is carried out, an organic solvent or diluent or a mixture thereof from the group of(a) alcohols and phenols and their alkoxylates,(b) polyalcohols based on ethylene oxide, propylene oxide, butylene oxide or a mixture thereof,(c) N-substituted carboxamides,(d) alkanolmonoamines and alkanolpolyamines and their alkoxylates,(e) other alkoxylates of oligoamines or polyamines,(f) aromatic hydrocarbons,(g) aliphatic hydrocarbons,(h) ethers and(i) sulfones or sulfoxidesbeing added.Type: GrantFiled: April 7, 1997Date of Patent: December 8, 1998Assignee: BASF AktiengesellschaftInventors: Jurgen Mohr, Wolfgang Knauf, Wolf-Dieter Balzer, Knut Oppenlander, Wilhelmus Slotman
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Patent number: 5820987Abstract: An electrodepositable composition that has: (A) an active hydrogen-containing cationic resin, electrodepositable on a cathode, having: (1) a polyepoxide; (2) an oxygen-substituted diamine compound having the following formula: ##STR1## where n is an integer from 2 to 4; and where R.sup.1 or R.sup.2 are the same or different and either one or both contain at least one oxygen and are alkyl, cycloalkyl, substituted alkyl, or substituted cycloalkyl having from 1 to 6 carbon atoms, or R.sup.1 and R.sup.2 are alkanol groups having from 2 to 6 carbon atoms, or R.sup.1, R.sup.2, and the N atom form a cyclic group which is substituted or unsubstituted such as morpholine and 1-(3-aminopropyl) imidazole; and (B) at least partially blocked isocyanate or polyisocyanate curing agent. The diamine compound of Formula I can be used alone or in conjunction with one or more secondary amines, nonhydroxy group containing amines and/or amines with ring structures.Type: GrantFiled: August 21, 1996Date of Patent: October 13, 1998Assignee: PPG Industries, Inc.Inventors: Marvin L. Kaufman, Patrick O'Neill, Richard F. Karabin, Gregory J. McCollum
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Patent number: 5821317Abstract: The invention pertains to an adduct obtainable by condensation of a bisepoxy compound and a P-guanamine according to the formula ##STR1## wherein X is CR.sub.3 R.sub.4 --(CR.sub.1 R.sub.2).sub.n --CR.sub.5 R.sub.6 or o-phenylidene, n is 0 or 1, and R.sub.1 -R.sub.8 may be the same or different and represent H, methyl or ethyl, and the molar ratio P-guanamine: bisepoxide is 0.60 to 0.35. The adduct is used in the manufacture of synthetic materials, notably printed wiring boards (PWBs).Type: GrantFiled: August 13, 1997Date of Patent: October 13, 1998Assignee: Akzo Nobel NVInventors: Antonius Johannes Wilhelmus Buser, Jan Andre Jozef Schutyser
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Patent number: 5817736Abstract: Epoxy resin mixtures to produce prepregs and composites contain the following components:a phosphorus-modified epoxy resin with an epoxy value of 0.02 to 1 mol/100 g, made up of structural units derived from(a) polyepoxy compounds with at least two epoxy groups per molecule and(b) phosphinic acid anhydrides, phosphonic acid anhydrides or phosphonic acid half-esters;dicyandiamide and/or an aminobenzoic acid derivative as the hardener;an amino hardening accelerator.Type: GrantFiled: March 10, 1997Date of Patent: October 6, 1998Assignee: Siemens AktiengesellschaftInventors: Wolfgang von Gentzkow, Jurgen Huber
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Patent number: 5801218Abstract: The present invention provides a novel method for preparing a novel latent curing agent composition suitable for curing epoxy resin compositions. The present invention also provides the novel latent curing agent compositions.Type: GrantFiled: August 28, 1997Date of Patent: September 1, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Taun L. McKenzie, Allen L. Griggs
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Patent number: 5798399Abstract: The present invention provides a novel method for preparing a novel curing agent composition suitable for curing epoxy resin compositions. The present invention also provides the novel curing agent compositions.Type: GrantFiled: August 28, 1997Date of Patent: August 25, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Allen L. Griggs, Taun L. McKenzie
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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: 5780555Abstract: An amine curing agent composition for an epoxy resin is provided having low volatility and good processability containing a) a polyamine curing agent and b) an aliphatic alcohol-alkylene oxide adduct. An epoxy resin-polyamine curing agent system containing an aliphatic alcohol-alkylene oxide adduct is also provided.Type: GrantFiled: September 16, 1996Date of Patent: July 14, 1998Assignee: Shell Oil CompanyInventors: Larry Steven Corley, Kalyan Ghosh, Joseph Michael Hunter, Derek Scott Kincaid, Leo Meilus, Daniel James Weinmann
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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: 5770658Abstract: Modified epoxy resins are obtained by reaction of an epoxy resin with up to one mol equivalent per epoxy group of an alkyl or alkenyl substituted, hydroxy substituted aromatic acid, especially by reaction of a bisphenol A epoxy resin with an alkylated salicylic acid. Also are described a process for the production of such modified resins, curable compositions comprising the modified epoxy resin and products provided with the cured composition, especially in coating applications and civil engineering applications.Type: GrantFiled: June 14, 1996Date of Patent: June 23, 1998Assignee: Shell Oil CompanyInventors: Francoise Jacqueline Aline Baudoul, Seetha Maha Lakshmi Coleman-Kammula
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Patent number: 5763559Abstract: A guanidine-modified phenol-formaldehyde resole resin by reacting formaldehyde and phenol at a formaldehyde to phenol mole ratio above about 1.5:1 in the presence of an effective amount of an alkaline catalyst and in the presence of a catalytic amount of a guanidine salt. The resin is suitable for use in adhesives for high moisture content substrates.Type: GrantFiled: January 21, 1997Date of Patent: June 9, 1998Assignee: Georgia-Pacific Resins, Inc.Inventor: Eric Peter Black
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Patent number: 5763558Abstract: A process for hardening a composition and a hardenable composition, in wh there are used:at least one novolac resin;at least one hardener of the resin, selected from the group consisting of substituted melamines;at least one compound comprising at least one ##STR1## group, this compound being without methylol group and ether group corresponding to methylol, and/or at least one reagent capable of giving such a compound under the conditions of the hardening.The hardening of the resin is caused by the action of heat.Type: GrantFiled: June 11, 1996Date of Patent: June 9, 1998Assignee: Compagnie Generale Des Etablissements Michelin-Michelin & CieInventors: Brigitte Marie Chauvin, Olivier Durel
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Patent number: 5763506Abstract: A self-dispersing curable epoxy composition is prepared upon contacting (a) 1.0 reactive equivalents of an epoxy resin, (b) from about 0.01 to 1.0 reactive equivalents of a polyhydric phenol, and (c) between 0.005 and 0.025 reactive equivalents of an amine-epoxy adduct, wherein the amine-epoxy adduct is formed upon contacting 1.0 equivalents of an aliphatic polyepoxide and between 0.3 and 0.9 reactive equivalents of a polyoxyalkyleneamine. The self-dispersing curable epoxy resin forms an aqueous dispersion upon mixing with water. When cured, the dispersion is useful as a coating composition.Type: GrantFiled: September 26, 1996Date of Patent: June 9, 1998Assignee: Henkel CorporationInventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5760146Abstract: Epoxy resin mixtures for prepregs and compositesEpoxy resin mixtures for preparing prepregs and composites contain the following components:a phosphorus-modified epoxy resin with an epoxy value of 0.02 to 1 mol/100 g, made up of structural units derived from(a) polyepoxy compounds with at least two epoxy groups per molecule and(b) phosphinic acid anhydrides, phosphonic acid anhydrides, or phosphonic acid half-esters;a glycidyl group-free compound with phenolic OH groups in the form of bisphenol-A, bisphenol-F, or a high-molecular phenoxy resin obtained through the condensation of bisphenol-A or bisphenol-F with epichlorohydrin;an aromatic polyamine used as a hardening agent.Type: GrantFiled: March 10, 1997Date of Patent: June 2, 1998Assignee: Siemens AktiengesellschaftInventors: Wolfgang von Gentzkow, Jurgen Huber, Heinrich Kapitza, Wolfgang Rogler
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Patent number: 5759690Abstract: Epoxy resin mixtures for the production of prepregs and composites contain the following components:a phosphorus-modified epoxy resin with an epoxy value of 0.02 to 1 mol/100 g, made up of structural units derived from(a) polyepoxy compounds with at least two epoxy groups per molecule, and(b) phosphinic acid anhydrides, phosphonic acid anhydrides, or phosphonic acid half-esters;an amine-substituted aromatic sulfonic acid amide or hydrazide as a hardener;an amino hardening accelerator.Type: GrantFiled: March 10, 1997Date of Patent: June 2, 1998Assignee: Siemens AktiengesellschaftInventors: Wolfgang von Gentzkow, Jurgen Huber, Heinrich Kapitza, Wolfgang Rogler
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Patent number: 5760104Abstract: A binder solution of a phenolic novolak resin in solvent, preferably furfuryl alcohol containing at least one chemical agent such as amines containing one to five, preferably two to four, nitrogen atoms, glycerine or mixtures thereof. Preferably, the binder solution contains about 0.2 to about 1.5 weight percent water. The binder solution is for binding refractory objects, preferably those containing doloma (calcined dolomite) aggregate. Methods of mixing these ingredients and using the mixture are also disclosed. Bricks made from the doloma aggregate mixed with the binder solution show good ambient temperature green strength and enhanced modulus of rupture after curing and coking.Type: GrantFiled: July 9, 1997Date of Patent: June 2, 1998Assignee: Borden Chemical, Inc.Inventor: Arthur Harry Gerber
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Patent number: 5756596Abstract: An increase in the molecular weight of a polyamide or recycled polyamide, essentially without crosslinking, can be achieved by blending said polyamide with a polyfunctional epoxy resin and a sterically hindered hydroxyphenylalkylphosphonic acid ester or half-ester and heating the blend to above the melting point (or the glass transition temperature) of the polyamide, in the absence of a catalyst of the type used in the polymerization of polyamides.Type: GrantFiled: April 7, 1997Date of Patent: May 26, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Rudolf Pfaendner, Heinz Herbst, Kurt Hoffmann
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Patent number: 5756592Abstract: A continuous process for the production of a phenolic-based cyanate ester resin is provided and includes the steps of: feeding a phenolic organic compound, a trialkylamine and a cyanogen halide into a continuous, plug-flow type reactor; causing the reactants to flow through and react in the reactor over a period of time defined as a residence time; continuously reacting the phenolic organic compound, the triallckylamine and the cyanogen halide in the reactor; and maintaining a temperature in the reactor of between about -75.degree. C. to about 0.degree. C. The reactor has a length which is equal to or greater than ten times its internal diameter. The mol equivalent concentration of the cyanogen halide is greater than the mol equivalent concentration of the trialkylamine, and the mol equivalent of the trialkylamine is greater than the mol equivalent of the phenolic organic compound.Type: GrantFiled: November 15, 1996Date of Patent: May 26, 1998Assignee: AlliedSignal, Inc.Inventors: William B. Bedwell, Raymond J. Swedo, Bruce T. DeBona, George D. Green
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Patent number: 5756599Abstract: A process for producing a phenol-aldehyde (e.g., cresol-aldehyde) resin that is modified with a dihydroxybenzene compound. The resin may form a binder system when combined with a curing agent which includes an additional source of an aldehyde. The resin and adhesive are useful in the production of wood composite articles by a steam injection process.Type: GrantFiled: July 7, 1997Date of Patent: May 26, 1998Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5750595Abstract: There is disclosed a self-dispersing curable epoxy resin composition comprising the addition product of reactants comprising (a) 1.0 reactive equivalent of an epoxy resin, (b) from about 0.1 to 1.0. reactive equivalents of a polyhydric phenol, and (c) from about 0.005 to 0.5 reactive equivalents of an amine-epoxy adduct comprising the addition product of reactants comprising 1.0 reactive equivalent of a polyepoxide and from about 0.3 to 0.9 reactive equivalents of a compound having the structural formula:?R.sub.1 --O--!.sub.2-m --R.sub.2 --?--CH.sub.2 CH(R.sub.3)--X--R.sub.4 --NH.sub.2 !.sub.mwherein: R.sub.1 designates a monovalent organic radical selected from the group consisting of C.sub.1 to C.sub.12 aliphatic, alicyclic or aromatic hydrocarbons, and R.sub.2 represents a polyoxyalkylene chain having the structural formula:(CH.sub.2 --CH.sub.2 --O).sub.a --(CH.sub.2 --CH(R.sub.5)--O).sub.bwherein: R.sub.5 is a monovalent organic radical selected from the group consisting of C.sub.1 to C.sub.Type: GrantFiled: June 1, 1995Date of Patent: May 12, 1998Assignee: Henkel CorporationInventors: Kartar S. Arora, Michael S. Wiggins
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Patent number: 5739185Abstract: The present invention provides a cationic electrodepositable coating composition comprising:?I! a polyurethane-modified epoxy resin-amine adduct obtained by a reaction of:(A) a polyurethane compound having one terminal isocyanate group in the molecule, obtained by a reaction of (a) a polyhydroxy compound having a number-average molecular weight of 50-8,000, (b) a polyisocyanate compound, and (c) a compound having one active hydrogen atom in the molecule,(B) a bisphenol type epoxy resin having at least two epoxy groups in the molecule, and(C) an active-hydrogen-containing amine compound, and ?II! a nonionic film-forming resin.Type: GrantFiled: August 16, 1995Date of Patent: April 14, 1998Assignee: Kansai Paint Co., Ltd.Inventors: Hidehiko Haneishi, Masanobu Kudoh, Koji Kamikado
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Patent number: 5736196Abstract: A coating powder based on an epoxy resin is applied to a substrate and fused and cured thereon. Curing is effected by exposing the coating powder at the point of application to a fluid curative or cure catalyst, e.g., by exposing the fusing coating powder to an ammonia-containing atmosphere.Type: GrantFiled: October 2, 1996Date of Patent: April 7, 1998Assignee: Morton International, Inc.Inventors: Owen H. Decker, Dieter W. Jungclaus, Karl R. Wursthorn, Glenn D. Correll, David A. Mountz
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Patent number: 5733942Abstract: This invention relates to a granular phenolic resin forming material. Grains are obtained by pulverizing a hardened phenol resin or epoxy resin, particularly a waste, having aromatic rings. The grains are heated to react with a phenolic substance, to solubilize at least surfaces thereof, whereby the grains are made formable again. The pulverized, hardened grains and the phenolic substance, preferably a phenol, are mixed in the ratio of 100/10 to 100/90. An acid catalyst may be used, as necessary, in a quantity not exceeding 9 parts. A preferred reaction temperature is 80.degree. to 180.degree. C. at atmosphere pressure. The forming material of this invention may be formed with hexamine compounded therewith.Type: GrantFiled: September 25, 1996Date of Patent: March 31, 1998Assignee: Hisaji TanazawaInventors: Hisaji Tanazawa, Takeshi Hirohata, Ryutaro Nishimura
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Patent number: 5733954Abstract: The present invention provides a novel method for preparing a novel latent curing agent composition suitable for curing epoxy resin compositions. The present invention also provides the novel latent curing agent compositions.Type: GrantFiled: December 14, 1995Date of Patent: March 31, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Taun L. McKenzie, Allen L. Griggs
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Patent number: 5721323Abstract: A class of compounds which inhibits the reaction of a polyepoxide with a curing agent at low temperatures including an epoxy resin composition containinga) a polyepoxide;b) an amine or amide curing agent for the polyepoxide;c) at least about 15 meq (per equivalent of polyepoxide) of a catalyst for the reaction of the polyepoxide with the curing agent; andd) a cure inhibitor selected such that:(1) at about 171.degree. C. the composition has a gel time that is at least about 50 percent longer than a similar composition without the inhibitor, and(2) at about 175.degree. C. and higher the composition cures in no more than about 50 minutessuch that the composition cures rapidly with high cross-link density because it has a high catalyst loading, while the inhibitor lengthens the gel time to permit laminating and other processing.Type: GrantFiled: December 27, 1996Date of Patent: February 24, 1998Assignee: The Dow Chemical CompanyInventors: Craig E. Schultz, James L. Bertram, William A. Clay, Guang-Ming Xia, Joseph Gan
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Patent number: 5719239Abstract: A coated panel formed from a self-supporting cellulosic substrate and a top coating containing a thermoset resin having about 0.1-1.5 wt % free formaldehyde admixed with said resin; and (b) a thermoplastic polymer thoroughly admixed with said resin, wherein said thermoplastic polymer exhibits amine groups capable of reacting with at least some of the free formaldehyde under resin curing conditions. The coated panel can be embossed with decorative patterns such as wood grain without fracture of the coated surface or significant buildup on the press or embossing die surfaces.Type: GrantFiled: December 18, 1996Date of Patent: February 17, 1998Assignee: Georgia-Pacific Resins, Inc.Inventors: George E. Mirous, Bernard E. Sullivan
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Patent number: 5717011Abstract: The present invention provides a novel method for preparing a novel curing agent composition suitable for curing epoxy resin compositions. The present invention also provides the novel curing agent compositions.Type: GrantFiled: December 14, 1995Date of Patent: February 10, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Allen L. Griggs, Taun L. McKenzie
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Patent number: 5712039Abstract: The invention provides a curable, structural epoxy adhesive composition comprising: (a) an epoxy resin; (b) a curing agent for the epoxy resin; and (c) a compound of the formula I: ##STR1## in which R.sup.1 and R.sup.2, which may be the same or different, are selected from an alkyl group, a hydroxyalkyl group, a cycloalkyl group, an aryl group, an arylalkyl group, or a heterocyclic group in which the one to three non-carbon atoms in the ring are independently selected from S, N, and O.Type: GrantFiled: April 11, 1995Date of Patent: January 27, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Virginia C. Marhevka, Allen L. Griggs, Kent S. Tarbutton
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Patent number: 5709947Abstract: A method for the preparation of a diaminobisimide compound of the formula (I) substantially free of oligomers: ##STR1## wherein Ar.sup.1 is an optionally substituted aromatic residue which provides for good conjugation between the nitrogen containing groups; andAr is an optionally substituted aromatic residue characterized in that at least two molar proportions of an aromatic diamine of the formula (II)H.sub.2 N--Ar.sup.1 --NH.sub.2 (II)wherein Ar.sup.1 is as defined above,are heated with one molar proportion of an aromatic tetracarboxylic acid of the formula (III) or the corresponding dianhydride,(HOOC).sub.2 Ar(COOH).sub.2 (III)wherein Ar is as defined above,optionally in the presence of a polar solvent and optionally including 0.1 to 2 molar proportions of a tertiary amine.The compounds of formula (I) are useful curing agents in epoxy resin formulations.Type: GrantFiled: June 2, 1995Date of Patent: January 20, 1998Assignee: Commonwealth Scientific and Industrial Research OrganisationInventors: Jonathan Howard Hodgkin, Mervyn Benjamin Jackson, John West Loder
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Patent number: 5707741Abstract: 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: April 26, 1996Date of Patent: January 13, 1998Assignee: Hoechst AktiengesellschaftInventors: Michael Hoenel, Armin Pfeil, Thomas Budnick, Heiner Schwan
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Patent number: 5708120Abstract: The present invention relates to an epoxy composition that is isolated in the form of an infusible, gelled, heat curable, epoxy functional reaction product. The reaction product is formed by mixing together: (A) one or more epoxy resins or epoxy group containing compounds and (B) a hardener system which will react with (A) to give a gelled solid, but which does not cause complete curing of (A) under the reaction conditions chosen for reaction of (A) and (B) to give a gelled solid. The reaction product can be formed by including (C) an optional further hardener system for (A) and the reaction product of (A) and (B), which is different from (B), and which remains largely unreacted with (A) and (B) under said reaction conditions. The present invention further relates to a cured product of said epoxy composition.Type: GrantFiled: January 25, 1996Date of Patent: January 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Peter Drummond Boys White
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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: 5688876Abstract: 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: July 18, 1996Date of Patent: November 18, 1997Assignee: Asahi Denka Kogyo K.K.Inventors: Kazuhiko Ando, Hiroshi Suzuki
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Patent number: 5686506Abstract: A binder solution of a phenolic novolak resin in solvent, preferably furfuryl alcohol containing at least one chemical agent such as amines containing one to five, preferably two to four, nitrogen atoms, glycerine or mixtures thereof. Preferably, the binder solution contains about 0.2 to about 1.5 weight percent water. The binder solution is for binding refractory objects, preferably those containing doloma (calcined dolomite) aggregate. Methods of mixing these ingredients and using the mixture are also disclosed. Bricks made from the doloma aggregate mixed with the binder solution show good ambient temperature green strength and enhanced modulus of rupture after curing and coking.Type: GrantFiled: April 4, 1995Date of Patent: November 11, 1997Assignee: Borden Chemical, Inc.Inventor: Arthur Harry Gerber
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Patent number: 5686541Abstract: A modified epoxy resin is prepared by mixing an isocyanate terminated urethane prepolymer with an epoxy resin in reactive conditions. The modified epoxy resin has a low internal stress when it is cured due to the flexible backbone of the urethane prepolymer incorporated therein, and has a high glass transition temperature due to a rigid oxazolidone structure formed via the epoxy ring opening with the isocyanate groups, and thus is useful as an electronic encapsulant.Type: GrantFiled: November 14, 1995Date of Patent: November 11, 1997Assignee: National Science CouncilInventors: Chun-Shan Wang, Tsung-Han Ho
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Patent number: 5677006Abstract: 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: June 1, 1995Date of Patent: October 14, 1997Assignee: Hoechst AktiengesellschaftInventors: Michael Hoenel, Armin Pfeil, Thomas Budnick, Heiner Schwan
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Patent number: 5672432Abstract: Cathodic electrocoat compositions containing self-crosslinking polymers are described. The polymers of the invention are formed from an epoxide-functional prepolymer having polyepoxide and extender segments. Each extender segment has at least one pendant hydroxyalkyl carbamate group. The prepolymer is reacted with an amine compound having at least one blocked primary amine group and at least one epoxide-reactive group. The primary amine group is unblocked and the resultant polymer is dispersed in water with the aid of a neutralizing acid.Type: GrantFiled: November 16, 1995Date of Patent: September 30, 1997Assignee: BASF CorportionInventors: Paul J. Harris, Timothy S. December
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Patent number: 5670585Abstract: A process for preparing binder-coated fiber-glass products employs as a binder aqueous polymer systems comprising a nitrogenous formaldehyde resin such as a urea-extended alkaline phenol/formaldehyde resole together with an acidic polyacrylate which cocure to form a thermoset polymer while synergistically reducing ammonia emissions which normally occur during cure of the nitrogenous formaldehyde resin. The polymer system may be used in applications other than fiberglass where reduced emissions are desired.Type: GrantFiled: June 13, 1995Date of Patent: September 23, 1997Assignee: Schuller International, Inc.Inventors: Thomas J. Taylor, Paul Nedwick
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Patent number: 5667894Abstract: An improved aqueous cathodic electrocoating composition having a binder of an epoxy-amine adduct which is of an epoxy resin that has been reacted with an amine, and a blocked polyisocyanate crosslinking agent; wherein the improvement is the use of an alkane sulfonic acid as the neutralizing agent for the epoxy amine adduct to provide an electrocoating composition having improved throw power.Type: GrantFiled: June 5, 1996Date of Patent: September 16, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Joseph Albert Antonelli, Christopher Scopazzi, William Bertus Vanderlinde
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Patent number: 5662833Abstract: The present invention relates to electrically conducting thermoset compositions and methods for preparing them. In the compositions according to the invention, the conducting component is a polyaniline protonated with a protonic acid containing at least one hydroxyl group. The thermoset matrix can be, for instance, a phenol-formaldehyde resin, a melamine-formaldehyde resin, or a polyester resin.Type: GrantFiled: November 22, 1995Date of Patent: September 2, 1997Assignee: Neste OyInventors: Jukka Laakso, Jan-Erik Osterholm, Hannele Jarvinen
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Patent number: 5663247Abstract: A hyperbranched macromolecule of polyester type comprising a central monomeric or polymeric nucleus and at least one generation of a branching chain extender having at least three reactive sites of which at least one is a hydroxyl or hydroxyalkyl substituted hydroxyl group and at least one is a carboxyl or terminal epoxide group. The nucleus is an epoxide compound having at least one reactive epoxide group. Optionally, the macromolecule comprises at least one generation consisting of at least one spacing chain extender having two reactive sites of which one is a hydroxyl or hydroxyalkyl substituted hydroxyl group and one is a carboxyl or terminal epoxide group. The macromolecule may be terminated by means of at least one chain stopper.Type: GrantFiled: October 24, 1995Date of Patent: September 2, 1997Assignee: Perstorp ABInventors: Kent Sorensen, Bo Pettersson
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Patent number: 5652047Abstract: Preparation of binder resins having improved flow properties in the manufacture of curable fiber composites of natural or synthetic fiber materials, which are based on thermosetting novolaks which contain crosslinking agents and contain practically no free mononuclear phenols, by admixing polyglycols and/or polycarboxylic acids or anhydrides thereof and/or acid esters of polyglycols and polycarboxylic acids, preferably in amounts of in total up to 20% by weight, to the novolaks in the melt, pulverizing the mixture, after cooling to room temperature, and mixing it intimately with the required amount of pulverulent crosslinking agent.Type: GrantFiled: May 20, 1996Date of Patent: July 29, 1997Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hesse, Erhard Leicht, Richard Sattelmeyer, Ralph Schaefer
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Patent number: 5648171Abstract: Epoxy resin mixtures for producing prepregs and composites that are available at low cost and can be processed well yield flame-retardant molding materials even without the addition of flame retardants, and these molding materials have a high glass transition temperature and also have an improved interlaminar adhesion and adhesion to copper when they contain the following components:a phosphorus-modified epoxy resin with an epoxy value of 0.02 to 1 mol/100 g, composed of structural units derived from(A) polyepoxy compounds with at least two epoxy groups per molecule and(B) at least one compound from the group consisting of phosphinic acids, phosphonic acids, pyrophosphonic acids and phosphonic acid half-esters, andan aromatic polyamine as the hardener.Type: GrantFiled: September 14, 1995Date of Patent: July 15, 1997Assignee: Siemens AktiengesellschaftInventors: Wolfgang von Gentzkow, Jurgen Huber, Heinrich Kapitza, Wolfgang Rogler, Hans-Jerg Kleiner
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Patent number: 5648409Abstract: There is disclosed a self-disbursing curable epoxy resin composition comprising the addition product of reactants comprising (a) 1.0 reactive equivalent of an epoxy resin, (b) from about 0.40 to 0.95 reactive equivalents of a polyhydric phenol, and (c) from about 0.005 to 0.5 reactive equivalents of an amine-epoxy adduct comprising the addition product of reactants comprising 1.0 reactive equivalent of an aromatic polyepoxide and from about 0.3 to 0.9 reactive equivalents of a polyoxyalkyleneamine.Type: GrantFiled: December 29, 1994Date of Patent: July 15, 1997Assignee: Henkel CorporationInventors: Kartar S. Arora, David I. Devore, Reuben H. Grinstein, Grannis S. Johnson, John G. Papalos, Shailesh Shah
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Patent number: 5648435Abstract: A process of preparing multicyanate esters by: a) reacting an adduct of a tertiary amine and a phenol-formaldehyde oligomer or derivative thereof with cyanogen halide in a solvent reaction medium under conditions to form a reaction product stream containing at least one of the following compounds selected from the group consisting of tertiary amine-hydrohalide salt, solvent, and impurities, and, based upon the total weight of the reaction product stream excluding the weight of said tertiary amine-hydrohalide salt, from about 10 percent to about 40 percent of a multicyanate ester; b) recycling a portion of said reaction product stream into the mixture of step a; and c) separating and recovering said solvent and tertiary amine from said reaction product stream. The multicyanate ester products produced are useful as bonding agents in friction materials, molding materials, coatings, and adhesives.Type: GrantFiled: November 17, 1995Date of Patent: July 15, 1997Assignee: AlliedSignal Inc.Inventors: David W. H. Roth, Jr., Sajal Das
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Patent number: 5646199Abstract: A binder resin composition, a curing agent composition, a caking additive composition, a kit, a casting mold composition and a process for manufacturing a casting mold are disclosed, wherein a metallic compound containing a metallic element belonging to Group IB to VIII of the Periodic Table is utilized. The compositions are useful for the production of a sand mold for casting, having an excellent strength, from reclaimed sand, in a self-hardening or gas hardening mold process. The casting mold according to the present invention, which is manufactured in the presence of a metallic compound containing a metallic element belonging to Group IB to VIII of the Perioidic Table has excellent strength.Type: GrantFiled: July 21, 1992Date of Patent: July 8, 1997Assignee: Kao CorporationInventors: Akira Yoshida, Kazuhiko Kiuchi, Naoki Kyochika, Akio Mamba, Hitoshi Funada
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Patent number: 5643976Abstract: There is disclosed a self-dispersing curable epoxy resin composition comprising the addition product of reactants comprising (a) 1.0 reactive equivalent of an epoxy resin, (b) from about 0.40 to 0.95 reactive equivalents of a polyhydric phenol, and (c) from about 0.005 to 0.5 reactive equivalents of an amine-epoxy adduct comprising the addition product of reactants comprising 1.0 reactive equivalent of a polyepoxide and from about 0.3 to 0.9 reactive equivalents of a polyoxyalkyleneamine having the structural formula:R.sub.1 --O--R.sub.2 --CH.sub.2 CH(R.sub.3)--X--R.sub.4 --NH2wherein:R.sub.1 designates a monovalent organic radical selected from the group consisting of C.sub.1 to C.sub.12 aliphatic, alicyclic or aromatic hydrocarbons, andR.sub.2 represents a polyoxyalkylene chain having the structural formula:(CH.sub.2 --CH.sub.2 --O).sub.a --(CH.sub.2 --CH(R.sub.5)--O).sub.bwherein:R.sub.5 is a monovalent organic radical selected from the group consisting of C.sub.1 to C.sub.Type: GrantFiled: December 29, 1994Date of Patent: July 1, 1997Assignee: Henkel CorporationInventors: Kartar S. Arora, Michael S. Wiggins
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Patent number: 5641852Abstract: Disclosed is a thermosetting resin composition comprising cyanate resin, a compound containing at least one or more than one of a phenolic hydroxyl radical and an epoxy resin, wherein said resin has excellent adhesive and heat resistant properties while at the same time possessing a low hardening contraction rate and contributing to higher dimensional stability, and method of making the same.Type: GrantFiled: January 11, 1996Date of Patent: June 24, 1997Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hiroyuki Tsuji, Shoji Hara, Hirosaku Nagano