Nitrogen Reactant Having At Least One Amino-nitrogen Atom Contains At Least One Aryl Group Patents (Class 528/124)
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Patent number: 6346573Abstract: A method for the manufacture of a one-component epoxy resin system comprises mixing at 15-30° C. and reacting at room temperature over 2-14 days (A) an epoxy resin and (B) an amine solidifying system present in insufficient quantities to cause gelation to yield a product with a Kofler Heat Bank melting point of less than 55° C. and a melting point stability of at least six months at normal workshop temperatures in the presence of (C) a hardener for (A) and the reaction product of (A) and (B) which is different from (B) and remains unreacted with (A) and (B) during the their reaction, (E) an expanding agent and (D) additives other than the expanding agent, provided that the reaction between (A) and (B) does not generate enough heat to activate a reaction between the remaining epoxy groups and hardener (C) or expanding agent (E).Type: GrantFiled: May 18, 1998Date of Patent: February 12, 2002Assignee: Vantico Inc.Inventor: Peter Drummond Boys White
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Patent number: 6329473Abstract: Epoxy resin compositions comprising polyepoxides having at least two 1,2-epoxide groups, which can be obtained by reaction of diepoxides or polyepoxides or mixtures thereof with monoepoxides, and one or more amines sterically hindered amines, such as disecondary polyoxyalkylenediamines, and/or diprimary diamines, if desired with the addition of further 1,2-epoxide compounds and also hardeners, and use thereof as a coating for crack bridging, as an adhesive and in powder surface coatings.Type: GrantFiled: March 23, 1995Date of Patent: December 11, 2001Assignee: Solutia Germany GmbH & Co., KGInventors: Manfred Marten, Claus Godau
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Patent number: 6309757Abstract: Gas barrier coating compositions are provided which include a polyamine component, a polyepoxide component and a hydroxy-substituted aromatic compound that is present in an amount sufficient to provide a gas barrier coating having an oxygen permeability less than or equal to 75 percent of the oxygen permeability of the same composition without a hydroxy-substituted aromatic compound. Also provided is a multi-layer packaging material having at least one gas permeable packaging material layer and at least one gas barrier material layer formed from the gas barrier coating composition. Sealable containers are also provided.Type: GrantFiled: February 16, 2000Date of Patent: October 30, 2001Assignee: PPG Industries Ohio, inc.Inventors: Leland H. Carlblom, Cynthia Kutchko, Ken W. Niederst
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Patent number: 6294597Abstract: A curable polymeric composition which is a liquid at 20° C. and which comprises 25 to 60% by weight of a resin component which comprises an epoxy, 5 to 25% by weight of a curing agent which comprises two components, a first component which is a cycloaliphatic amine or an aromatic amine, and a second component which is a polyamide amine, and 20 to 65% by weight of an inert inorganic filler. The curable composition can be used in a method of protecting a substrate such as a pipe or a pipe joint from corrosion or mechanical damage. In the method, the curable composition is first applied to the substrate, a polymeric covering layer is applied over the curable composition with an innermost layer of a heat-activatable sealant in intimate contact with the curable composition, and the curable composition is then cured. During the curing process, the heat-activatable sealant, e.g. a hot melt adhesive, remains in contact with the curable composition and interacts therewith.Type: GrantFiled: August 4, 1997Date of Patent: September 25, 2001Inventors: James Rinde, George Pieslak, Leon C. Glover
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Patent number: 6291626Abstract: Flame-retardant advanced epoxy resins and cured epoxy resins contain a rigid phosphorus group emanating from a dihydric phenol or naphthol which provides thermal and flame retardant properties. The advanced epoxy resins are suitable for making a fiber-reinforced epoxy resin composite which is useful in the fabrication of printed circuit boards. The cured epoxy resins can be used in semiconductor encapsulation applications.Type: GrantFiled: March 3, 1999Date of Patent: September 18, 2001Assignee: National Science CouncilInventors: Chun-Shan Wang, Jeng-Yueh Shieh
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Thermosetting composition, uses thereof and a flexible deployable preform comprising the composition
Patent number: 6187443Abstract: A thermosetting composition with a glass transition temperature of at least 100° C. comprises at least one epoxy resin formed from at least one polyepoxide containing at least two epoxy groups in its molecule and at least one aromatic polyamine containing at least two primary amino groups in its molecule, at least one alkyl substituent containing 1 to 12 carbon atoms located in the position alpha to one of the amino groups. The molar ratio of the amine to the epoxide is such that each amine group corresponds to 1.6 to 2.6 epoxy groups. The composition also includes a flow regenerator. The composition can be used as a protective coating for any metallic or non metallic surface. The invention also concerns a flexible deployable preform comprising the composition.Type: GrantFiled: September 30, 1997Date of Patent: February 13, 2001Assignee: Institut Francais du PetroleInventors: Paul Mariaggi, Henri Delhomme, Dominique Audigier, Frédérique Jacquemin-Hauviller -
Patent number: 6054221Abstract: Curable epoxy resin compositions, preferably solvent-free, wherein a fluorene amine curative is partially melt dissolved and partially dispersed as a solid in at least one aromatic polyepoxide. The compositions provide prepregs which exhibit tack with surprisingly good shelf life properties. Cured composites comprising the prepregs are also provided. The cured composites exhibit little resin migration and glass transition temperatures that are comparable to those of cured neat resins.Type: GrantFiled: October 15, 1999Date of Patent: April 25, 2000Assignee: 3M Innovative Properties CompanyInventors: Mark D. Weigel, Steven C. Hackett, Timothy J. Clemens
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Patent number: 6020426Abstract: A charge transporting block and an insulating block are block copolymerized or graft copolymerized to form a charge transporting copolymer. The charge transporting polymers may be used in an electrophotographic photoreceptor and an electrophotographic device.Type: GrantFiled: November 3, 1997Date of Patent: February 1, 2000Assignee: Fuji Xerox Co., Ltd.Inventors: Yasuhiro Yamaguchi, Fumiaki Tambo, Taketoshi Hoshizaki, Yasuo Sakaguchi, Ryosaku Igarashi, Masakazu Iijima, Taketoshi Higashi
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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: 6007917Abstract: Curable epoxy resin compositions, preferably solvent-free, wherein a fluorene amine curative is partially melt dissolved and partially dispersed as a solid in at least one aromatic polyepoxide. The compositions provide prepregs which exhibit tack with surprisingly good shelf life properties. Cured composites comprising the prepregs are also provided. The cured composites exhibit little resin migration and glass transition temperatures that are comparable to those of cured neat resins.Type: GrantFiled: December 22, 1997Date of Patent: December 28, 1999Assignee: 3M Innovative Properties CompanyInventors: Mark D. Weigel, Steven C. Hackett, Timothy J. Clemens
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Patent number: 5971071Abstract: Thermosetting compositions with improved latency are obtained by addition of a molten aromatic polyamine type curing agent to a liquid epoxy resin followed by cooling the mixture, causing the curing agent to form a suspension of fine particles in the epoxy resin by recrystallisation thereof. The compositions obtained can be used for the manufacture of prepregs with high latency for their use in processes requiring intermediate steps at 80.degree. C. over several hours.Type: GrantFiled: July 16, 1998Date of Patent: October 26, 1999Assignee: Institut Francais du PetroleInventors: Paul Mariaggi, Frederique Jacquemin-Hauviller, Henri Delhomme, Dominique Augigier
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Patent number: 5962093Abstract: A laminate structure comprises one or more layers of an organic polymer and one or more layers of a hydroxy-functionalized polyetheramine, wherein the hydroxy-functionalized polyetheramine layer is adhered directly to a contiguous organic polymer layer without an adhesive layer therebetween. The hydroxy-functionalized polyetheramine is prepared by reacting (1) a difunctional amine with (2) a diglycidyl ether or a diepoxy-functionalized poly(alkylene oxide) under conditions sufficient to cause the amine moieties to react with the epoxy moieties to form a polymer backbone having amine linkages, ether linkages and pendant hydroxyl moieties and then treating the reaction product with a monofunctional nucleophile which is not a primary or secondary amine.Type: GrantFiled: October 22, 1997Date of Patent: October 5, 1999Assignee: The Dow Chemical CompanyInventors: Jerry E. White, Joe T. Sanford, Terry W. Glass
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Patent number: 5906864Abstract: Aqueous coating composition, containingI) one or more amine hardeners,II) one or more water-dilutable epoxy resins,III) one or more pigments and/or fillers andIV) water and optionally one or more solvents and/or conventional lacquer additives,wherein the composition of the coating composition is selected in such a way that a hardened free film formed from the coating composition with a coat thickness between 30 and 80 .mu.m has a storage modulus E' of 10.sup.8 Pa to 5.times.10.sup.9 Pa in a temperature range from -50.degree. C. to 150.degree. C.Type: GrantFiled: June 23, 1997Date of Patent: May 25, 1999Assignee: Herberts Gesellschaft mit Beschrankter HaftungInventors: Michael Osterhold, Werner Lenhard, Wilfried Collong, Willi Schlesing
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Patent number: 5902643Abstract: 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: November 24, 1997Date of Patent: May 11, 1999Assignee: PPG Industries Inc.Inventors: Leland H. Carlblom, Jerome A. Seiner, Ken W. Niederst
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Patent number: 5840825Abstract: Disclosed is a gas barrier coating and multilayer packaging materials made therefrom. The gas barrier coating includes a polyamine (A), a polyepoxide (B), and a filler (C). Polyamine (A) includes at least one of the following: (a) an initial polyamine, and (b) an ungelled polyamine adduct which is the reaction product of the initial polyamine and epichlorohydrin and/or a polyepoxide having a plurality of glycidyl groups linked to an aromatic member. Polyepoxide (B) includes a polyepoxide having a plurality of glycidyl groups linked to an aromatic member. Filler (C) includes a platelet-type filler with the following particle size distribution: (a) a number mean particle diameter in the range from about 5.5 to about 15 microns, and (b) a volume mean particle diameter in the range from about 8 to about 25 microns. In addition, the present invention provides glossy, multilayer packaging materials containing an oxygen barrier material layer having an oxygen permeability constant not more than 0.Type: GrantFiled: December 4, 1996Date of Patent: November 24, 1998Assignee: PPG Incustries, Inc.Inventors: Leland H. Carlblom, Jerome A. Seiner
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Patent number: 5817737Abstract: Thermosetting compositions with improved latency are obtained by addition of a molten aromatic polyamine type curing agent to a liquid epoxy resin followed by cooling the mixture, causing the curing agent to form a suspension of fine particles in the epoxy resin by recrystallisation thereof. The compositions obtained can be used for the manufacture of prepregs with high latency for their use in processes requiring intermediate steps at 80.degree. C. over several hours.Type: GrantFiled: May 8, 1997Date of Patent: October 6, 1998Assignee: Institut Francais du PetroleInventors: Paul Mariaggi, Frederique Jacquemin-Hauviller, Henri Delhomme, Dominique Audigier
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Patent number: 5747615Abstract: Heat-curable resin systems containing at least one liquid monomer and one solid component, and which have superior tack and drape, may be prepared by slurry mixing a slurry compatible solid into at least one liquid monomer such that the finished resin system contains the solid as a discontinuous phase having a particle size of less than about 20 .mu.m.Type: GrantFiled: June 2, 1995Date of Patent: May 5, 1998Assignee: Cytec Technology Corp.Inventor: Linas Norman Repecka
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Patent number: 5739209Abstract: Reductive alkylation of branched, short chain diamines, such as 2-methyl-1,5-pentanediamine, with certain aldehydes or ketones of moderate molecular weight, such as benzaldehyde or methyl isobutyl ketone, produces novel tri- and difunctional amines which are useful in curing epoxy resins to compositions having improved flexibility and enhanced resistance to moisture and chemicals. Particularly favorable results are achieved when this curative is combined in the epoxy formulation with low molecular weight acrylic copolymers added as flexibilizers. Further improvements are available by including in the recipe monofunctional epoxy or acrylic reactive diluents.Type: GrantFiled: February 7, 1997Date of Patent: April 14, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Kevin Rodney Lassila, Mark David Conner
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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: 5728755Abstract: Curable epoxy resin compositions, preferably solvent-free, wherein a fluorene amine curative is partially melt dissolved and partially dispersed as a solid in at least one aromatic polyepoxide. The compositions provide prepregs which exhibit tack with surprisingly good shelf life properties. Cured composites comprising the prepregs are also provided. The cured composites exhibit little resin migration and glass transition temperatures that are comparable to those of cured neat resins.Type: GrantFiled: September 22, 1995Date of Patent: March 17, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Mark D. Weigel, Steven C. Hackett, Timothy J. Clemens
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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: 5639848Abstract: An ungelled thermoplastic resin having gas barrier properties and containing at least 7 percent by weight of amine nitrogen is derived via the reaction of a polyamine devoid of oxyalkylene moieties and containing up to about two primary amino nitrogen groups per molecule and a polyepoxide in a molar ratio of polyamine to polyepoxide of from 1.4:1 to 0.83:1.Type: GrantFiled: April 12, 1996Date of Patent: June 17, 1997Assignee: PPG Industries, Inc.Inventors: Richard M. Nugent, Jr., Ken W. Niederst, Jerome A. Seiner
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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: 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: 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: 5585453Abstract: Polycyclic spiroorthoester which undergo expansion on polymerization to f resins, rather than shrinkage on polymerization, are employed in fabrication of composite, filament-reinforced, interceptor motor cases. The advantages which accrue to such use of the specified resins relate to the imparting of unique characteristics to the interceptor motor case such as increased structural strength, a reduction in the number of microcracks and voids, and improved bonding between resin and reinforcement. These unique characteristics impart benefits where needed since composite motor cases are fabricated from high strength filaments or tapes such as fiberglass, graphite, poly-p-phenyleneterephthalamide (Kevlar), in a polymeric matrix, and the primary mode of failure is due either to poor adhesion between the matrix and the filament or tapes or because of the development of microcracks or voids in the matrix.The spiroorthoester, 1,4,6-trioxaspiro [4.Type: GrantFiled: July 14, 1982Date of Patent: December 17, 1996Assignee: The United States of America as represented by the Secretary of the ArmyInventor: David C. Sayles
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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: 5510432Abstract: Isocyanate prepolymers based on an aromatic diisocyanate and a polyether polyol in which at least 95% of the isocyanate groups are blocked by blocking agents selected fromA) about 50 to about 97 equivalent % of a phenol or substituted phenol,B) about 30 to about 50 equivalent % of a pyrazole or a substituted pyrazole andC) 0 to about 10 equivalent % of a blocking agent different from A) and B).These blocked isocyanate prepolymers are particularly useful for the production of flexible epoxy resin systems.Type: GrantFiled: May 31, 1995Date of Patent: April 23, 1996Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Rainer Rettig, Eberhard Konig
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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: 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: 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: 5418313Abstract: 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 contacted with methylenedianiline or derivative thereof, e.g., methylenedianiline and di(3-methyl-4-aminophenyl)methane 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 90.degree. and 130.degree.Type: GrantFiled: May 25, 1994Date of Patent: May 23, 1995Assignee: Air Products and Chemicals, Inc.Inventors: Andrea K. Smith, Menas S. Vratsanos
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Patent number: 5414125Abstract: A diamino-alpha-alkylstilbene useful as an epoxy resin curing agent is represented by the following Formula I: ##STR1## wherein R is independently hydrogen, a C.sub.1 -C.sub.10 hydrocarbyl(oxy) group or a halogen, nitro, nitrile, phenyl or --CO--R.sup.1 group wherein R.sup.1 is independently hydrogen or a C.sub.1 -C.sub.3 hydrocarbyl group; each R.sup.4 is independently hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl group; and Y is a ##STR2## group wherein n=0 or 1.Type: GrantFiled: July 23, 1993Date of Patent: May 9, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5412044Abstract: Adducts containing terminating nitro (nitroso) groups and one or more mesogenic moieties are prepared by reacting (A) at least one compound containing an average of more than one vicinal epoxide group per molecule with (B) at least one compound containing one or more nitro (nitroso) groups and an average of one reactive hydrogen atom per molecule; with the proviso that at least one member of components (A) and (B) contains a mesogenic moiety. Reduction of these adducts provides amines which are useful as curing agents for epoxy resins.Type: GrantFiled: May 12, 1994Date of Patent: May 2, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5393806Abstract: An improved liquid matrix system for producing fibre-reinforced plastic components is disclosed. The system comprises (i) a liquid diglycidyl ether of a halogenated bisphenol or a mixture of liquid polyglycidyl ether bisphenols at least one of which being a polyglycidyl ether halogenated bisphenol; and (ii) a curing agent that is a sterically hindered aromatic diamine containing two primary amino groups attached to the carbon atoms in the aromatic nucleus, said carbon atoms not adjacent to each other, and at least one C.sub.1 to C.sub.6 linear or branched alkyl or thioalkyl substituent; the improvement comprising adding to said system a curing accelerator composition containing a mixture of a boron halide and an imidazole unsubstituted or substituted with at least one C.sub.1 to C.sub.6 linear or branched alkyl or C.sub.6 to C.sub.10 aryl.Type: GrantFiled: December 26, 1991Date of Patent: February 28, 1995Assignee: Albemarle CorporationInventor: Farah D. Azarnia
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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: 5310770Abstract: Water-reducible curing agents for epoxy resins are made from the diglycidyl ether of cyclohexane dimethanol and a diamine selected from the group consisting of meta-xylylene diamine, isophorone diamine, diaminocyclohexane and 1,3-bisaminomethyl cyclohexane.Type: GrantFiled: December 30, 1992Date of Patent: May 10, 1994Assignee: Hi-Tek Polymers, Inc.Inventors: William J. DeGooyer, George A. Roy, II
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Patent number: 5300618Abstract: A curable resorcinol-based epoxy resin is disclosed having the general structural formula (I) ##STR1## wherein at least one of R.sub.1, R.sub.2, or R.sub.3 is selected from the group consisting of (a) the general structural formula (II) ##STR2## wherein R.sub.4 is selected from the group consisting of hydrogen and an alkyl group having 1 to about 4 carbon atoms, and (b) an allyl group.Type: GrantFiled: January 15, 1993Date of Patent: April 5, 1994Assignee: Indspec Chemical CorporationInventor: Raj B. Durairaj
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Patent number: 5296570Abstract: Compositions comprising epoxy resins containing one or more rodlike mesogenic moieties per molecule are cured with polyamines containing one or more rodlike mesogenic moieties per molecule. These curable compositions can be oriented by the application of an electric field or magnetic field or drawing and/or shear flow prior to and/or during curing. The resultant cured products exhibit an improvement in one or more physical and/or mechanical and/or thermal properties as compared to a like epoxy resin system which does not contain any rodlike mesogenic moieties.Type: GrantFiled: June 1, 1993Date of Patent: March 22, 1994Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
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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: 5290824Abstract: A novel photocrosslinkable polymeric system has been developed for processing into films having stable second-order nonlinear optical properties. In the present system, polymers bearing photo-crosslinkable chromophores, such as polyvinylcinnamate and are reacted with appropriately designed nonlinear optical molecules with the cinnamate or other photocrosslinkable functionalities for photocrosslinking at one, two or more points. The system can be poled and photocrosslinked in the poled state to yield a material with stable optical nonlinearity and large electro-optic coefficients.Type: GrantFiled: May 12, 1992Date of Patent: March 1, 1994Assignee: University of LowellInventors: Braja K. Mandal, Sukant K. Tripathy, Jan-Chuan Huang, Jayant Kumar
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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: 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: 5275853Abstract: Polyetheramines having improved barrier to oxygen are thermoplastic polymers having aromatic ether/amine repeating units in their backbones and pendant hydroxyl moieties. Such polyetheramines are prepared by reacting diglycidyl ethers of dihydric aromatic compounds such as the diglycidyl ether of bisphenol-A, hydroquinone, or resorcinol with amines having no more than two amine hydrogens per molecule, such as piperazine or ethanolamine.Type: GrantFiled: April 7, 1992Date of Patent: January 4, 1994Assignee: The Dow Chemical CompanyInventors: H. Craig Silvis, Jerry E. White
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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
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Patent number: 5273793Abstract: The present invention is directed to epoxy-based polymeric nonlinear optical materials in which a nonlinear optical active moiety or functionality forms the crosslink between polymer chains and a process for making the nonlinear optical (NLO) epoxy polymer including heating an epoxy resin and a curing agent such as a bi- or tri-functional aromatic amine containing an electron-withdrawing group, for example, diamino diphenylsulfone and poling the mixture under high voltage at elevated temperature for a period of time to bring about orientation of the nonlinear optical moieties in the polymer. The polymers have enhanced stability over polymers in which only one end of an NLO active moiety is attached to the polymer chain.Type: GrantFiled: August 19, 1992Date of Patent: December 28, 1993Assignee: The Dow Chemical CompanyInventors: John J. Kester, Mark D. Newsham
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Patent number: 5270406Abstract: Advanced epoxy resin compositions are prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties. Curable compositions containing these advanced epoxy resin compositions are useful in adhesives, coatings, laminates castings and the like.Type: GrantFiled: September 15, 1992Date of Patent: December 14, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
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Patent number: 5266661Abstract: Curable compositions are disclosed which contain (I) an advanced resin composition prepared by reacting epoxy resins with active hydrogen-containing compounds which contain mesogenic moieties and (II) a suitable curing agent.Type: GrantFiled: September 15, 1992Date of Patent: November 30, 1993Assignee: The Dow Chemical CompanyInventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.