Nitrogen Reactant Having At Least One Amino-nitrogen Atom Contains At Least One Aryl Group Patents (Class 528/124)
  • Patent number: 6346573
    Abstract: 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: Grant
    Filed: May 18, 1998
    Date of Patent: February 12, 2002
    Assignee: Vantico Inc.
    Inventor: Peter Drummond Boys White
  • Patent number: 6329473
    Abstract: 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: Grant
    Filed: March 23, 1995
    Date of Patent: December 11, 2001
    Assignee: Solutia Germany GmbH & Co., KG
    Inventors: Manfred Marten, Claus Godau
  • Patent number: 6309757
    Abstract: 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: Grant
    Filed: February 16, 2000
    Date of Patent: October 30, 2001
    Assignee: PPG Industries Ohio, inc.
    Inventors: Leland H. Carlblom, Cynthia Kutchko, Ken W. Niederst
  • Patent number: 6294597
    Abstract: 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: Grant
    Filed: August 4, 1997
    Date of Patent: September 25, 2001
    Inventors: James Rinde, George Pieslak, Leon C. Glover
  • Patent number: 6291626
    Abstract: 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: Grant
    Filed: March 3, 1999
    Date of Patent: September 18, 2001
    Assignee: National Science Council
    Inventors: Chun-Shan Wang, Jeng-Yueh Shieh
  • Patent number: 6187443
    Abstract: 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: Grant
    Filed: September 30, 1997
    Date of Patent: February 13, 2001
    Assignee: Institut Francais du Petrole
    Inventors: Paul Mariaggi, Henri Delhomme, Dominique Audigier, Frédérique Jacquemin-Hauviller
  • Patent number: 6054221
    Abstract: 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: Grant
    Filed: October 15, 1999
    Date of Patent: April 25, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Mark D. Weigel, Steven C. Hackett, Timothy J. Clemens
  • Patent number: 6020426
    Abstract: 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: Grant
    Filed: November 3, 1997
    Date of Patent: February 1, 2000
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Yasuhiro Yamaguchi, Fumiaki Tambo, Taketoshi Hoshizaki, Yasuo Sakaguchi, Ryosaku Igarashi, Masakazu Iijima, Taketoshi Higashi
  • Patent number: 6020069
    Abstract: 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: Grant
    Filed: June 18, 1998
    Date of Patent: February 1, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Joseph A. Antonelli, Christopher Scopazzi
  • Patent number: 6007917
    Abstract: 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: Grant
    Filed: December 22, 1997
    Date of Patent: December 28, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Mark D. Weigel, Steven C. Hackett, Timothy J. Clemens
  • Patent number: 5971071
    Abstract: 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: Grant
    Filed: July 16, 1998
    Date of Patent: October 26, 1999
    Assignee: Institut Francais du Petrole
    Inventors: Paul Mariaggi, Frederique Jacquemin-Hauviller, Henri Delhomme, Dominique Augigier
  • Patent number: 5962093
    Abstract: 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: Grant
    Filed: October 22, 1997
    Date of Patent: October 5, 1999
    Assignee: The Dow Chemical Company
    Inventors: Jerry E. White, Joe T. Sanford, Terry W. Glass
  • Patent number: 5906864
    Abstract: 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: Grant
    Filed: June 23, 1997
    Date of Patent: May 25, 1999
    Assignee: Herberts Gesellschaft mit Beschrankter Haftung
    Inventors: Michael Osterhold, Werner Lenhard, Wilfried Collong, Willi Schlesing
  • Patent number: 5902643
    Abstract: 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: Grant
    Filed: November 24, 1997
    Date of Patent: May 11, 1999
    Assignee: PPG Industries Inc.
    Inventors: Leland H. Carlblom, Jerome A. Seiner, Ken W. Niederst
  • Patent number: 5840825
    Abstract: 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: Grant
    Filed: December 4, 1996
    Date of Patent: November 24, 1998
    Assignee: PPG Incustries, Inc.
    Inventors: Leland H. Carlblom, Jerome A. Seiner
  • Patent number: 5817737
    Abstract: 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: Grant
    Filed: May 8, 1997
    Date of Patent: October 6, 1998
    Assignee: Institut Francais du Petrole
    Inventors: Paul Mariaggi, Frederique Jacquemin-Hauviller, Henri Delhomme, Dominique Audigier
  • Patent number: 5747615
    Abstract: 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: Grant
    Filed: June 2, 1995
    Date of Patent: May 5, 1998
    Assignee: Cytec Technology Corp.
    Inventor: Linas Norman Repecka
  • Patent number: 5739209
    Abstract: 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: Grant
    Filed: February 7, 1997
    Date of Patent: April 14, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Kevin Rodney Lassila, Mark David Conner
  • Patent number: 5728439
    Abstract: 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: Grant
    Filed: December 4, 1996
    Date of Patent: March 17, 1998
    Assignee: PPG Industries, Inc.
    Inventors: Leland H. Carlblom, Jerome A. Seiner, Ken W. Niederst
  • Patent number: 5728755
    Abstract: 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: Grant
    Filed: September 22, 1995
    Date of Patent: March 17, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Mark D. Weigel, Steven C. Hackett, Timothy J. Clemens
  • Patent number: 5681907
    Abstract: 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: Grant
    Filed: January 4, 1996
    Date of Patent: October 28, 1997
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William Edward Starner, John Anthony Marsella, Lloyd Gerald Easterday
  • Patent number: 5639848
    Abstract: 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: Grant
    Filed: April 12, 1996
    Date of Patent: June 17, 1997
    Assignee: PPG Industries, Inc.
    Inventors: Richard M. Nugent, Jr., Ken W. Niederst, Jerome A. Seiner
  • Patent number: 5637365
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: June 10, 1997
    Assignee: PPG Industries, Inc.
    Inventor: Leland H. Carlblom
  • Patent number: 5616658
    Abstract: 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: Grant
    Filed: January 10, 1995
    Date of Patent: April 1, 1997
    Assignee: Huels Aktiengesellschaft
    Inventors: Rainer Gras, Elmar Wolf
  • Patent number: 5591812
    Abstract: 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: Grant
    Filed: January 26, 1996
    Date of Patent: January 7, 1997
    Assignee: Air Products and Chemicals, Inc.
    Inventor: William E. Starner
  • Patent number: 5585453
    Abstract: 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: Grant
    Filed: July 14, 1982
    Date of Patent: December 17, 1996
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: David C. Sayles
  • Patent number: 5554672
    Abstract: 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: Grant
    Filed: March 17, 1994
    Date of Patent: September 10, 1996
    Assignee: Tonen Corporation
    Inventors: Makoto Saito, Yoshimasa Chiba, Hiroyuki Misaki
  • Patent number: 5510432
    Abstract: 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: Grant
    Filed: May 31, 1995
    Date of Patent: April 23, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lutz Schmalstieg, Rainer Rettig, Eberhard Konig
  • Patent number: 5503936
    Abstract: 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: Grant
    Filed: January 12, 1995
    Date of Patent: April 2, 1996
    Assignee: Ciba-Geigy Corporation
    Inventor: Yefim Blyakhman
  • Patent number: 5492998
    Abstract: 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: Grant
    Filed: January 20, 1995
    Date of Patent: February 20, 1996
    Assignees: Lifesource International, Ltd., Jojani Inc.
    Inventor: Nicholas M. Irving
  • Patent number: 5445854
    Abstract: 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: Grant
    Filed: November 29, 1993
    Date of Patent: August 29, 1995
    Assignee: The Dow Chemical Company
    Inventors: Mark D. Newsham, Muthiah N. Inbasekaran, Michael N. Mang
  • Patent number: 5420172
    Abstract: 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: Grant
    Filed: August 23, 1993
    Date of Patent: May 30, 1995
    Assignee: Siemens Aktiengesellschaft
    Inventors: Jens Nordmann, Rainer Puehl
  • Patent number: 5418313
    Abstract: 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: Grant
    Filed: May 25, 1994
    Date of Patent: May 23, 1995
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Andrea K. Smith, Menas S. Vratsanos
  • Patent number: 5414125
    Abstract: 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: Grant
    Filed: July 23, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5412044
    Abstract: 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: Grant
    Filed: May 12, 1994
    Date of Patent: May 2, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5393806
    Abstract: 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: Grant
    Filed: December 26, 1991
    Date of Patent: February 28, 1995
    Assignee: Albemarle Corporation
    Inventor: Farah D. Azarnia
  • Patent number: 5360877
    Abstract: 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: Grant
    Filed: May 13, 1993
    Date of Patent: November 1, 1994
    Assignee: Exxon Research and Engineering Company
    Inventors: Jyi-Faa Hwang, John P. Dismukes
  • Patent number: 5310770
    Abstract: 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: Grant
    Filed: December 30, 1992
    Date of Patent: May 10, 1994
    Assignee: Hi-Tek Polymers, Inc.
    Inventors: William J. DeGooyer, George A. Roy, II
  • Patent number: 5300618
    Abstract: 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: Grant
    Filed: January 15, 1993
    Date of Patent: April 5, 1994
    Assignee: Indspec Chemical Corporation
    Inventor: Raj B. Durairaj
  • Patent number: 5296570
    Abstract: 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: Grant
    Filed: June 1, 1993
    Date of Patent: March 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5292831
    Abstract: Phenoxy resins containing rodlike mesogenic moieties are prepared from phenolic hydroxyl containing compounds which contain such moieties.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: March 8, 1994
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Robert E. Hefner, Jr., Paul M. Puckett
  • Patent number: 5290824
    Abstract: 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: Grant
    Filed: May 12, 1992
    Date of Patent: March 1, 1994
    Assignee: University of Lowell
    Inventors: Braja K. Mandal, Sukant K. Tripathy, Jan-Chuan Huang, Jayant Kumar
  • Patent number: 5288802
    Abstract: 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: Grant
    Filed: January 25, 1993
    Date of Patent: February 22, 1994
    Assignee: PPG Industries, Inc.
    Inventors: David N. Walters, Cathy A. Kreutzer, Padmanabhan Sundararaman
  • Patent number: 5288816
    Abstract: 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: Grant
    Filed: August 10, 1992
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: Muthiah N. Inbasekaran, Mark D. Newsham, Michael N. Mang
  • Patent number: 5279870
    Abstract: 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: Grant
    Filed: March 2, 1992
    Date of Patent: January 18, 1994
    Assignee: The Dow Chemical Company
    Inventor: John J. Kester
  • Patent number: 5275853
    Abstract: 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: Grant
    Filed: April 7, 1992
    Date of Patent: January 4, 1994
    Assignee: The Dow Chemical Company
    Inventors: H. Craig Silvis, Jerry E. White
  • Patent number: 5273792
    Abstract: 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: Grant
    Filed: March 13, 1992
    Date of Patent: December 28, 1993
    Assignee: The Dow Chemical Company
    Inventor: John J. Kester
  • Patent number: 5273793
    Abstract: 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: Grant
    Filed: August 19, 1992
    Date of Patent: December 28, 1993
    Assignee: The Dow Chemical Company
    Inventors: John J. Kester, Mark D. Newsham
  • Patent number: 5270406
    Abstract: 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: Grant
    Filed: September 15, 1992
    Date of Patent: December 14, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.
  • Patent number: 5266661
    Abstract: 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: Grant
    Filed: September 15, 1992
    Date of Patent: November 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Jimmy D. Earls, Paul M. Puckett, Robert E. Hefner, Jr.