Contains Nitrogen Atom Patents (Class 525/526)
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Patent number: 5728439Abstract: Disclosed is a multilayer packaging material which is suitable for use as a container for malt beverages and which is tinted so as to block at least 90% of light with wavelengths of electromagnetic radiation ranging from 300 nm to 500 nm. The tinted multilayer packaging materials of the present invention includes: (a) at least one layer of a carbon dioxide (CO.sub.2)-permeable polymeric packaging material, and (b) at least one layer of a CO.sub.2 -treated gas barrier coating, which has an oxygen permeability constant not more than 0.05 cubic centimeter-mil/100 square inches/atmosphere/day. The CO.sub.2 -permeable packaging material can be any polymeric material through which CO.sub.2 can pass and which can be used as a packaging material for food or beverages. The gas barrier coating has an oxygen permeability constant, before CO.sub.2 treatment, of less than 0.3. This gas barrier coating includes the reaction product of a polyamine (A) and a polyepoxide (B).Type: GrantFiled: December 4, 1996Date of Patent: March 17, 1998Assignee: PPG Industries, Inc.Inventors: Leland H. Carlblom, Jerome A. Seiner, Ken W. Niederst
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Patent number: 5721052Abstract: Thermosetting powder coating compositions adapted to form a grainy textured finish on heat sensitive substrates, especially wood products, such as particle board, conductive particle board, and medium density fiber board, without damaging the substrates comprise an epoxy resin, particularly bisphenol A type epoxy resins having low viscosities, either a catalytic curing agent comprising an imidazole, a substituted imidazole, or adduct of an imidazole or substituted imidazole and an epoxy resin, or a curing agent comprising an adduct of a polyamine and an epoxy resin, or a combination of the catalytic curing agent and curing agent, a texturing agent, a flow control agent, optional extender, and optional pigment. The thermosetting powder coatings have a cure time/temperature ranging from about 30 seconds at about 350.degree. F. peak substrate temperature down to about 20 minutes at about 225.degree. F.Type: GrantFiled: November 5, 1996Date of Patent: February 24, 1998Assignee: Morton International, Inc.Inventors: Jeno Muthiah, Andrew T. Daly, Richard P. Haley, Paul R. Horinka, Joseph J. Kozlowski, Glenn D. Correll
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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: 5712331Abstract: A curable resin system in supercritical carbon dioxide as diluent includes an epoxy resin, a co-reactant selected from poly N-substituted aziridines, and a catalyst to promote cure at ambient temperature. The system is compatible with various epoxy resins such as bisphenol A epoxy, bisphenol F epoxy, novolac epoxy, cycloaliphatic epoxy, triglycidyl-aminophenol, and triglycidyl isocyanurate. The aziridine co-reactant may be selected from reaction products of NH aziridines with acrylates and methacrylates of trimethylolpropane, ethylene glycol, propylene glycol, bisphenol A, bisphenol F, pentaerythritol, glycerol, and their alkoxylated derivatives; reaction products of NH aziridines with epoxy compounds; and 1-aziridine ethanol and its reaction products with epoxy and isocyanate functional compounds. Suitable catalysts include acid salts and complexes, strong electron accepting compounds, combinations of silicon hydrides and metal complexes, and non-halogen containing boron derivatives.Type: GrantFiled: August 15, 1995Date of Patent: January 27, 1998Assignee: Rockwell International CorporationInventor: Hong-Son Ryang
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Patent number: 5698292Abstract: The use of an amine salt of trifluoromethanesulfonic acid as a catalyst for the curing of hydroxyl-functional resins provides a wrinkle finish. The hydroxy-function may be present in polyesters, epoxies, and acrylate or methacrylate resins, among others. The polyester resins which are able to provide such a finish have a hot plate melt flow of at least about 50 mm but if it is more than 150 mm, the gel time of the resin must not be more than about 280 seconds. The minimum gel time in the case of polyesters is about 30 seconds.Type: GrantFiled: December 20, 1996Date of Patent: December 16, 1997Assignee: Morton International, Inc.Inventors: Douglas S. Richart, Charles P. Tarnoski
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Patent number: 5695852Abstract: The use of an amine salt of trifluoromethanesulfonic acid as a catalyst for the curing of hydroxyl-functional resins provides a wrinkle finish. The hydroxy-function may be present in polyesters, epoxies, and acrylate or methacrylate resins, among others. The polyester resins which are able to provide such a finish have a hot plate melt flow of at least about 50 mm but if it is more than 150 mm, the gel time of the resin must not be more than about 280 seconds. The minimum gel time in the case of polyesters is about 30 seconds.Type: GrantFiled: December 20, 1996Date of Patent: December 9, 1997Assignee: Morton International, Inc.Inventors: Douglas S. Richart, Charles P. Tarnoski
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Patent number: 5688877Abstract: A method of preparing epoxy parts wherein the interval of low viscosity of an amine-hardened epoxy system can be extended without sacrifice of cure time. Suitable catalysts for the epoxy-amine hardener reaction are generated in situ. As an advantage, more epoxy articles may be prepared with a given mold capacity having improved wet-out of fiber reinforcement attributed to a larger interval of low viscosity.Type: GrantFiled: June 11, 1996Date of Patent: November 18, 1997Assignee: The Dow Chemical CompanyInventors: Raymond A. Koenig, Joseph Gan, Richard J. Hayman
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Patent number: 5686185Abstract: A thermosetting epoxy resin powder coating composition is provided that comprises an epoxy resin composed of a diglycidyl ether of bisphenol A, a curing agent composed of a bisphenol A encapped diglycidyl ether of bisphenol A, and a cure catalyst composed of an imidazole adducted to a diglycidyl ether of bisphenol A, in which the ratio of curing agent to epoxy resin is below 70% stoichiometry, and preferably between about 10% and 60% stoichiometry. The thermosetting epoxy resin powder coating composition not only exhibits the desired flexibility and fast cure speeds, but also exhibits superior adhesion and superior resistance to delamination and cathodic disbondment, preferably having cathodic disbondment values typically less than 4 mm radial disbondment, and preferably less than 2 mm radial disbondment. Such properties are highly advantageous for protective powder coatings used on rebars and pipelines.Type: GrantFiled: December 30, 1996Date of Patent: November 11, 1997Assignee: Morton International, Inc.Inventors: Glenn D. Correll, Roy M. Berstler
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Patent number: 5681907Abstract: A curable epoxy resin composition comprising a polyepoxide resin and an amine curative characterized in that the amine curative comprises the reaction product of excess monomethylamine (MMA) and a polyglycidyl ether. 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 4, 1996Date of Patent: October 28, 1997Assignee: Air Products and Chemicals, Inc.Inventors: William Edward Starner, John Anthony Marsella, Lloyd Gerald Easterday
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Patent number: 5637365Abstract: Polyepoxide-polyamine gas barrier coatings for use on packaging materials such as polymeric containers are provided with low permeability at relatively low amine to epoxy cure ratios by including substantial aryloxy or aryloate group content. The aryloxy or aryloate content may be provided, for example, by polyglycidyl ether of resorcinol or polyglycidyl ester of phthalic acid.Type: GrantFiled: March 22, 1996Date of Patent: June 10, 1997Assignee: PPG Industries, Inc.Inventor: Leland H. Carlblom
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Patent number: 5631332Abstract: A curing agent for epoxy resins, prepared by reacting 2,5- and 2,6-bis(aminomethyl)-bicyclo[2.2.1]heptanes (1 equivalent of the active hydrogen in the amino group) with an epoxy resin (a reaction product of bisphenols or a novolak resin with epichlorohydrin; an epoxy equivalent of 150-300 g/eq.; two or more epoxy groups per molecule; bisphenol-A diglycidyl ether or bisphenol-F diglycidyl ether in particular)(0.025-0.50 equivalents of the epoxy group). The reaction temperature is 40.degree.-120.degree. C. The amount of the curing agent is within the range of 20-75 parts by weight relative to 100 parts by weight of an epoxy resin to be cured. The curing agent has a high curing rate at a room temperature, and the epoxy resins cured by it have a good appearance as well as excellent adhesion, water resistance, and chemical resistance. Therefore, the curing agent is suitable for paints, civil engineering and construction materials, adhesives, casting resins, laminates, etc.Type: GrantFiled: January 11, 1996Date of Patent: May 20, 1997Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Minato Karasawa, Takuji Shimizu
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Patent number: 5629098Abstract: This invention relates to an adhesive composition, comprising: (A) at least one multifunctional epoxy; and (B) the composition derived from (B-1) at least one difunctional epoxy resin and (B-2) at least one compound represented by the formulaR--(G).sub.n (1)wherein in Formula (I): R is an aromatic, alicyclic or heterocyclic group; G is a functional group selected from the group consisting of COOH, OH, SH, NH.sub.2, NHR.sup.1, (NHC(.dbd.NH)).sub.m NH.sub.2, R.sup.2 COOH, R.sup.2 OH, R.sup.2 SH, R.sup.2 NH.sub.2 and R.sup.2 NHR.sup.1, wherein R.sup.1 is a hydrocarbon group, R.sup.2 is an alkylene or alkylidene group and m is a number in the range of 1 to about 4; and n is a number ranging from 3 up to the number of displaceable hydrogens on R; with the proviso that when at least one G is NH.sub.2 or R.sup.2 NH.sub.2, n is a number ranging from 2 up to the number of displaceable hydrogens on R, and when at least one G is (NHC(.dbd.NH)).sub.m NH.sub.Type: GrantFiled: October 27, 1995Date of Patent: May 13, 1997Assignee: Gould Electronics Inc.Inventors: Charles A. Poutasse, Katherine V. Sack, Andrea M. Kovacs, James R. Winchester
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Patent number: 5618893Abstract: Binders for cathodic electrodeposition coatings based on epoxy resin-amine adducts are obtained by incorporation of oxazolidone structures in combination with diamine bridges built up in a specific manner. The modified epoxy resin-amine adducts are used in electro-dipping coatings together with crosslinking components. The stoved coating films have excellent corrosion protection, especially at the edges of workpieces.Type: GrantFiled: March 22, 1991Date of Patent: April 8, 1997Assignee: Vianova Kunstharz, AGInventors: Rudolf Schipfer, Gerhard Schm olzer
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Patent number: 5610209Abstract: A newly-blended one part system heat-resistant epoxy resin composition which exhibits excellent stability at room temperature, quickly undergoes the curing reaction, molded within short periods of time, and, after cured, exhibits excellent Tg, resistance against the water, resistance against degradation by heat, and a variety of excellent properties in combination. The heat-resistant epoxy resin composition having excellent stability at room temperature comprises an epoxy compound having two or more epoxy groups, a curing agent which comprises a naphthalenedicarboxylic dihydrazide as a main component, and a ceramic whisker as a filler.Type: GrantFiled: June 2, 1995Date of Patent: March 11, 1997Assignee: Japan Hydrazine Co., Ltd.Inventor: Shigeo Kiyono
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Patent number: 5599628Abstract: Described herein are compositions containing (a) a cycloaliphatic epoxy resin, (b) an aromatic amine hardener, and (c) a particular cure accelerator. These compositions afford unreinforced castings with a high level of mechanical properties and improved heat deflection temperatures.Type: GrantFiled: March 1, 1984Date of Patent: February 4, 1997Assignee: Amoco CorporationInventor: Hugh C. Gardner
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Patent number: 5596050Abstract: Described herein are resinous compositions comprising a particular cycloaliphatic epoxy resin and the adduct of these epoxy resins with an aromatic active hydrogen-containing compound. These compositions afford unreinforced castings with higher heat deflection temperatures, faster cure rates, and reduced water uptake than similar compositions containing epoxy adducts made from aliphatic polyols.Type: GrantFiled: March 1, 1984Date of Patent: January 21, 1997Assignee: Amoco CorporationInventors: Hugh C. Gardner, Michael J. Michno, Jr., Robert J. Cotter
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Patent number: 5591814Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: January 7, 1997Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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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: 5585446Abstract: An epoxy resin composition is disclosed that contains compounds that contain at least two 1,2-epoxide groups. The epoxide group-containing compounds are reaction products of compounds (A1) that contain at least two 1,2-epoxide groups per molecule, compounds (A2) that are polyoxyalkylenemonoamines that have a molecular weight of from 130 to 900 and, if desired, polyoxyalkylenemonoamines (A3) that have a molecular weight of from 900 to 5000 and/or polycarboxylic acids (A4). The resin composition additionally contains at least one hardener (B) and, if desired, customary additives (C).Type: GrantFiled: December 12, 1994Date of Patent: December 17, 1996Assignee: Hoechst AktiengesellschaftInventors: Manfred Marten, Bernhard Wehner
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Patent number: 5567792Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: October 22, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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Patent number: 5567748Abstract: A water miscible or soluble amine terminated resin useful as a curing agent comprising the reaction product of: A) a polyamine component comprising one or more hydrophilic poly(oxyalkylene) amines, and optionally one or more hydrophobic polyamines; B) a polyepoxide component comprising one or more diglycidyl ethers of a polyalkylene glycol, one or more diglycidyl ethers of a cycloalkylene glycol and optionally one or more hydrophobic polyglycidyl ethers, wherein the mixture is optionally advanced by an amine extender; C) optionally, a reactive diluent which is capable of reacting with an epoxy resin, and D) optionally, a catalyst for the reaction of an amine with an epoxy resin; wherein Component A is employed in an equivalent excess with respect to Component B such that the terminal moieties of the reaction product are amine moieties capable of reacting with an epoxy resin; the composition has an amine hydrogen equivalent weight of from 140 to 240; and the composition is water soluble or water miscible.Type: GrantFiled: May 25, 1994Date of Patent: October 22, 1996Assignee: The Dow Chemical CompanyInventors: Dieter H. Klein, Hans J. Wessely
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Patent number: 5567782Abstract: An epoxy resin composition is disclosed that contains compounds that contain at least two 1,2-epoxide groups. The epoxide group-containing compounds are reaction products of compounds (A1) that contain at least two 1,2-epoxide groups per molecule, compounds (A2) that are polyoxyalkylenemonoamines that have a molecular weight of from 130 to 900 and, if desired, polyoxyalkylenemonoamines (A3) that have a molecular weight of from 900 to 5000 and/or polycarboxylic acids (A4). The resin composition additionally contains at least one hardener (B) and, if desired, customary additives (C).Type: GrantFiled: April 5, 1995Date of Patent: October 22, 1996Assignee: Hoechst AktiengesellschaftInventors: Manfred Marten, Bernhard Wehner
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Patent number: 5565505Abstract: 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: June 14, 1994Date of Patent: October 15, 1996Assignee: Henkel CorporationInventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5565506Abstract: A self-dispersing curable epoxy composition is prepared upon contacting (a) 1.0 reactive equivalents of an epoxy resin, (b) from about 0.65 to 0.95 reactive equivalents of a polyhydric phenol, and (c) between 0.005 and 0.5 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: August 25, 1994Date of Patent: October 15, 1996Assignee: Henkel CorporationInventors: John G. Papalos, Reuben H. Grinstein, Shailesh Shah, Joseph L. Mulvey, Brian G. Jewell
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Patent number: 5561204Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: October 1, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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Patent number: 5554672Abstract: A primer comprises a liquid epoxy resin, a hydrophobic polyamine compound, a thixotropic agent and a silane coupling agent. After coating the primer on a wet concrete surface of a structure, a reinforced fiber sheet or similar material could be attached to the surface with a high level of adhesive strength without being influenced by the water. The reinforced fiber sheet is impregnated with a matrix resin and cured to achieve a satisfactory reinforcement of the concrete structure.Type: GrantFiled: March 17, 1994Date of Patent: September 10, 1996Assignee: Tonen CorporationInventors: Makoto Saito, Yoshimasa Chiba, Hiroyuki Misaki
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Patent number: 5554714Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: September 10, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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Patent number: 5548026Abstract: This invention is a two-part induction-curable epoxy adhesive comprising a first part of a polyfunctional epoxy such as a sorbitol polyglycidyl ether, and a diepoxy compound such as a diepoxy bisphenol-A wherein a portion of the diepoxy compound may preferably comprise a glycol-based epoxy having an epoxy equivalent weight of at least about 250. The second part of the adhesive is a curing agent which preferably maybe a mixture of nitrogen-based compounds di(aminoalkyl)ether of diethylene glycol, and a toughening agent. The invention also comprises a method of adjoining two substrates by applying the adhesive composition of the invention and curing as well as the article resulting from this method.Type: GrantFiled: June 5, 1995Date of Patent: August 20, 1996Assignee: H. B. Fuller CompanyInventors: Steven A. Jorissen, Gregory A. Ferguson, Krystyna Imirowicz
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Patent number: 5548058Abstract: A curing agent for epoxy resins is prepared from an amine and an epoxy, as well as subsequent modification by a polyisocyanate compound, in such a manner that the curing agent is in the form of small spherical particles. The particles can be as small as 0.1 microns. This curing agent can be easily dispersed in curing agent masterbatches and curable compositions with minimal effect on their storage stability. The resulting curable compositions have a wide range of applications, including automobile and electronic adhesives.Type: GrantFiled: June 7, 1995Date of Patent: August 20, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Souichi Muroi, Hsi-Chuan Tsai
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Patent number: 5536775Abstract: Amine curable compositions containing a partially acrylated epoxy resin useful for forming protective and/or decorative coatings on a variety of substrates, particularly flooring substrates.Type: GrantFiled: November 4, 1994Date of Patent: July 16, 1996Assignee: Sandoz Ltd.Inventors: Benedict S. Curatolo, Frank V. Apicella, Jr., Thomas W. Richardson, Sr.
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Patent number: 5525433Abstract: This invention relates to an adhesive composition, comprising: (A) at least one multifunctional epoxy; and (B) the composition derived from (B-1) at least one difunetional epoxy resin and (B-2) at least one compound represented by the formulaR--(G).sub.n (I)wherein in Formula (I): R is an aromatic, alicyclic or heterocyclic group; G is a functional group selected from the group consisting of COOH, OH, SH, NH.sub.2, NHR.sup.1, (NHC(.dbd.NH)).sub.m NH.sub.2, R.sup.2 COOH, R.sup.2 OH, R.sup.2 SH, R.sup.2 NH.sub.2 and R.sup.2 NHR.sup.1, wherein R.sup.1 is a hydrocarbon group, R.sup.2 is an alkylene or alkylidene group and m is a number in the range of 1 to about 4; and n is a number ranging from 3 up to the number of displaceable hydrogens on R; with the proviso that when at least one G is NH.sub.2 or R.sup.2 NH.sub.2, n is a number ranging from 2 up to the number of displaceable hydrogens on R, and when at least one G is (NHC(.dbd.NH)).sub.m NH.sub.Type: GrantFiled: June 6, 1995Date of Patent: June 11, 1996Assignee: Gould Electronics Inc.Inventors: Charles A. Poutasse, Katherine V. Sack, Andrea M. Kovacs, James R. Winchester
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Patent number: 5523363Abstract: A resin composition for aqueous coating, comprising, as the main components, a resin having hydroxyl group(s) and cationic group(s) and a certain novolac-substituted phenol type epoxy resin. This composition has excellent bath stability and low-temperature curability and is useful in cationic electrocoatings, in particular.Type: GrantFiled: September 30, 1993Date of Patent: June 4, 1996Assignee: Kansai Paint Co., Ltd.Inventors: Toshio Fujibayashi, Haruo Nagaoka
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Patent number: 5510431Abstract: Curable compositions containing (A) one or more epoxy resins, one (B) or more curing agents and (C) one or more cure controlling catalysts wherein at least one of components (A) or (B) or both components (A) and (B) contain a mesogenic moiety are prepared. These curable compositions permit processing at higher temperatures and improved properties. They are useful in the preparation of coatings, castings, electrical or laminates or composites and the like.Type: GrantFiled: June 1, 1995Date of Patent: April 23, 1996Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., James L. Bertram, Louis L. Walker
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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: 5508324Abstract: An epoxy resin curing composition comprising the product of the reaction of (A) a polyamine containing primary amine functionality and (B) a polyepoxide having an EEW of from 130 to 450 in a ratio of moles of polyamine per equivalents of polyepoxide sufficient to provide intermediate (C) which comprises an adduct of about two moles of polyamine and one mole polyepoxide, intermediate (C) being then reacted with an amount of a polyepoxy resin (D) sufficient to react with about 10-40% of the primary amines in intermediate (C) to provide adduct (E), and adduct (E) being end capped with a monoepoxide composition comprising an aromatic glycidyl ether or an alkyl substituted aromatic glycidyl ether, or both. The composition may be salted with a volatile acid such as acetic acid and blended with water to afford an aqueous composition containing 20 to 65% nonvolatiles.Type: GrantFiled: August 14, 1995Date of Patent: April 16, 1996Assignee: Air Products and Chemicals, Inc.Inventor: Michael I. Cook
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Patent number: 5491204Abstract: Barrier materials for reducing the permeability of plastic packaging materials are provided, characterized as containing at least about seven percent by weight amine nitrogen, or a total of at least about 17 percent amine nitrogen plus hydroxyl groups. The barrier materials exhibit oxygen permeability of less than about 1.5 cc-mil/100 in.sup.2 -day-atmosphere and a carbon dioxide permeability of less than about 15 cc-mil/100 in.sup.2 -day-atmosphere at 23.degree. C. and zero percent relative humidity. The barrier material is formed from a polyepoxide, a polyamine and an alkanolamine. Optionally the polyamine may comprise prereacted polymeric resin formed from a polyepoxide and a polyamine. Multilayer packaging materials and multilayer containers including the polyamine-polyepoxide barrier material are part of the invention.Type: GrantFiled: April 27, 1995Date of Patent: February 13, 1996Assignee: PPG Industries, Inc.Inventors: Richard M. Nugent, Jr., Ken W. Niederst, Jerome A. Seiner
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Patent number: 5488085Abstract: Polymer polyols prepared by a semi-batch process using a small amount of a seed polymer polyol are disclosed. The final polymer polyol has a broader particle size distribution as compared to an identically prepared polymer polyol prepared in the absence of the seed polymer polyol. The polymer polyols are suitable for use in producing polyurethanes, particularly polyurethane foams.Type: GrantFiled: August 18, 1994Date of Patent: January 30, 1996Assignee: ARCO Chemical Technology, L.P.Inventors: John E. Hayes, Donald W. Simroth, Xinhua Zhou
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Patent number: 5484853Abstract: A two-part adhesive composition having superior adhesive strength at cryogenic temperatures contains a urethane resin composition part and a hardener part. The urethane resin composition part comprises 50 to 99% by weight of a modified polyurethane prepolymer having an epoxy group at each of its respective ends and 1 to 50% by weight of a modified urethane compound having substantially no ether cyanate (NCO) groups and at least two epoxy groups per molecule and a molecular weight of less than 800 daltons. The hardener part is a polyamine containing primary or secondary amine groups. The equivalent ratio of the amine groups of the polyamine to the epoxy groups of the urethane resin composition part is 0.5 to 2.0.Type: GrantFiled: July 28, 1993Date of Patent: January 16, 1996Assignee: China Technical Consultants, Inc.Inventors: Der-Shyang Chen, Hung-Chung Hsia, Chen-Chi M. Ma, Wang-Nang Wang
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Patent number: 5480958Abstract: This invention relates to improved one part polyepoxide resins which are tough and have enhanced flexible and elastic properties. The polyepoxide resins comprise a polyepoxide resin based on a polyglycidyl ether of a phenol, an oxazolidone toughener and a latent amine curative. The improvement in the polyepoxide resin formulation comprises incorporating an oxazolidone toughener represented by the formula: ##STR1## wherein R is the residue of an aliphatic glycol or aliphatic ether glycol having from 2 to 20 carbon atoms.Type: GrantFiled: September 21, 1994Date of Patent: January 2, 1996Assignee: Air Products and Chemicals, Inc.Inventors: William E. Starner, Richard S. Myers
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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: 5460860Abstract: Mesogen containing biaxially oriented films are prepared from curable mixtures containing an epoxy resin and a curing agent therefor. Certain of the mesogen containing biaxially oriented films possess unique properties, such as a metallic like, highly reflective appearance. These films are useful in adhesives, coatings, laminates or composites and the like.Type: GrantFiled: May 20, 1994Date of Patent: October 24, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls, Peter E. Pierini, David A. Waldman, Lalitha Reddy
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Patent number: 5458929Abstract: Laminates containing one or more plies of substrate material impregnated with a composition containing (A) one or more epoxy resins, (B) one or more curing agent and (C) about 0.00005 to about 0.1 mole per epoxide equivalent of cure controlling catalyst, wherein at least one of components (A) or (B) contain at least one mesogenic moiety, which, optionally, has been subjected to either (a) the application of an electric field, (b) the application of a magnetic field, (c) drawing or shear forces, or (d) any combination thereof, are prepared.Type: GrantFiled: February 15, 1994Date of Patent: October 17, 1995Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., James L. Bertram, Louis L. Walker, William A. Clay
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Patent number: 5439977Abstract: An acid anhydride-containing one package epoxy resin composition consisting indispensably of (1) an epoxy resin having two or more epoxy groups in one molecule, (2) an acid anhydride, (3) at least one of (a) a liquid latent curing accelerator, (b) a latent curing accelerator soluble in an epoxy resin having two or more epoxy groups in one molecule and (c) a latent curing accelerator soluble in an acid anhydride, and (4) a dispersible latent curing accelerator, wherein the ratio of (1) to (2) is from 0.8 to 1.2, defined as the number of acid anhydride equivalents/the number of epoxy equivalents, and the amounts of (3) and (4) each are from 0.1 to 10 parts by weight to 100 parts by weight of the epoxy resin. The composition has excellent infiltrability, storage stability and reactivity.Type: GrantFiled: April 15, 1994Date of Patent: August 8, 1995Assignee: Ajinomoto Co., Inc.Inventors: Tadahiko Yokota, Hiroyuki Sakata, Kiyomiki Hirai, Koji Takeuchi
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Patent number: 5438109Abstract: Barrier materials for reducing the permeability of plastic packaging materials are provided, characterized as containing at least about seven percent by weight amine nitrogen, or a total of at least about 17 percent amine nitrogen plus hydroxyl groups. The barrier materials exhibit oxygen permeability of less than about 1.5 cc-mil/100 in.sup.2 -day-atmosphere and a carbon dioxide permeability of less than about 15 cc-mil/100 in.sup.2 -day-atmosphere at 23.degree. C. and zero percent relative humidity. The barrier material can be formed from polyepoxide and polyamine. Optionally the polyamine may comprise prereacted polymeric resin formed from a polyepoxide and a polyamine. Multilayer packaging materials and multilayer containers including the polyamine-polyepoxide barrier material are part of the invention.Type: GrantFiled: December 17, 1993Date of Patent: August 1, 1995Assignee: PPG Industries, Inc.Inventors: Richard M. Nugent, Jr., Ken W. Niederst, Jerome A. Seiner
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Patent number: 5430112Abstract: Epoxy resin compositions which contain (1) an epoxy resin which has two or more epoxy groups in its molecule, (2) a polythiol compound which has two or more thiol groups in its molecule and (3) an accelerator which is (i) a solid dispersion-type amine adduct latent curing accelerator or (ii) the product of a reaction between a compound which contains one or more isocyanate groups in its molecule and a compound which has at least one primary and/or secondary amino group in its molecule, exhibit excellent curability at relatively low heating temperatures as well as a long working life.Type: GrantFiled: October 21, 1993Date of Patent: July 4, 1995Assignee: Ajinomoto Co., Inc.Inventors: Hiroyuki Sakata, Tadahiko Yokota, Kenichi Mori, Kiyomiki Hirai, Koji Takeuchi, Toshihiko Hatajima
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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: 5418263Abstract: A cathodic electrodeposition paint containing as a binder resin an amine-epoxy resin adduct and a blocked polyisocyanate crosslinker is disclosed. The binder resin and the crosslinker are emulsified in an aqueous medium containing a neutralizing agent with the aid of amine adduct of a monoepoxide compound having a hydrophobic group or block. Not only the amine-monoepoxide adduct functions as a surfactant but also it is deposited electrically and then cured with the crosslinker integrally with the binder resin.Type: GrantFiled: April 19, 1994Date of Patent: May 23, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Toshiaki Sakamoto, Yoshio Kojima, Kenshiro Tobinaga
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Patent number: 5416173Abstract: An amine reacted acrylated epoxy resin blend that is particularly suitable for impregnating a fiber material and at least initial curing by exposure to ionizing radiation. These epoxy resins are basically produced by combining epoxy resins, including esterified epoxy resins, with stoichiometric quantities of aliphatic or cyclo aliphatic polyamines. The resins can be used to impregnate fibers which are exposed to ionizing radiation such as an electron beam or ultraviolet light and immediately formed into a structure, such as by filament winding. A short exposure to the ionizing radiation produces a stress-free, self supporting structure that can be fully cured through simple heating without elaborate tooling, vacuum bagging, autoclaves or the like.Type: GrantFiled: July 15, 1994Date of Patent: May 16, 1995Assignee: Martin Marietta CorporationInventors: John Gagliani, Ronald K. Giesy
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Patent number: 5407978Abstract: An advanced thermosetting epoxy powder composition comprising from about 95 epoxide equivalent percent to about 99 epoxide equivalent percent of a diglycidyl ether of an aromatic bisphenol, from about 1 to about 5 epoxide equivalent percent of at least one trifunctional polyglycidyl ether of an aliphatic polyol, a curing agent selected from the group consisting of dihydric bisphenol such as bisphenol-A and mixtures of bisphenol-A and bisphenol A endcapped diglycidyl ether of bisphenol A, and a curing accelerator selected from the group consisting of imidazoles and imidazole adducts with polyglycidyl ether of aliphatic polyol.Type: GrantFiled: May 7, 1993Date of Patent: April 18, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Bymark, Allen L. Griggs, James S. McHattie, Taun L. McKenzie
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Patent number: 5405701Abstract: A resin composition for aqueous coating, comprising as main components(A) a resin having hydroxyl groups and cationic groups, and(B) a compound having, in the molecule, at least two glycidyl groups each in a glycidylamino group represented by the following formula ##STR1## (R is a group selected from a hydrogen atom and a glycidyl group) directly bonding to carbon atoms of the aromatic ring. This composition is excellent in storage stability, low-temperature curability, etc. and is useful in cationic electrocoatings, in particular.Type: GrantFiled: April 15, 1993Date of Patent: April 11, 1995Assignee: Kansai Paint Co., Ltd.Inventors: Toshio Fujibayashi, Haruo Nagaoka