Material Contains A Transition Metal Atom Patents (Class 528/56)
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Patent number: 6906110Abstract: In a process for producing polyurethanes by reacting at least one polyisocyanate with at least one compound containing at least two hydrogen atoms which are reactive toward isocyanate groups, the compound having at least two active hydrogen atoms which is used is at least one polyether alcohol prepared by addition of alkylene oxides onto H-functional initiator substances by means of multimetal cyanide catalysis and the reaction is carried out in the presence of at least one metal salt.Type: GrantFiled: November 4, 2000Date of Patent: June 14, 2005Assignee: BASF AktiengesellschaftInventors: Reinhard Lorenz, Stephan Bauer, Dieter Junge, Eva Baum, Kathrin Harre, Jörg Erbes, Thomas Ostrowski, Georg Heinrich Grosch
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Patent number: 6888028Abstract: Using at least one compound selected from the group consisting of a zirconyl compound and a zirconium alcoholate as an allophanation catalyst, an allophanate group-containing polyisocyanate composition is produced from a starting material of at least one isocyanate compound selected from the group consisting of an aliphatic diisocyanate, an alicyclic diisocyanate and an isocyanate pre-polymer obtained therefrom, and another starting material of a hydroxyl group-containing compound.Type: GrantFiled: October 16, 2001Date of Patent: May 3, 2005Assignee: Asahi Kasei Kabushiki KaishaInventors: Shinichiro Watanabe, Kunio Naoi
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Patent number: 6881764Abstract: There is disclosed a polyurethane composition with a glass cullet filler. The composition comprises at least one polyol, an isocyanate, a catalyst and glass cullet. The glass cullet has an average particle size of not greater than 100 mesh and not less than 325 mesh. A method of producing a polyurethane composition with a glass cullet filler is also disclosed.Type: GrantFiled: December 4, 2001Date of Patent: April 19, 2005Assignee: Textile Rubber & Chemical Company, Inc.Inventors: Van I. Doesburg, Milton Bradley Giddens
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Patent number: 6835794Abstract: Golf equipment having improved cut and shear resistance that includes a polyurea composition, preferably saturated, formed of a polyurea prepolymer and a curing agent, wherein the polyurea prepolymer includes an isocyanate and a polyether amine, and wherein the curing agent includes a hydroxy-terminated curing agent, amine-terminated curing agent, or a mixture thereof.Type: GrantFiled: August 27, 2002Date of Patent: December 28, 2004Assignee: Acushnet CompanyInventors: Shenshen Wu, Craig A. Wilson, Murali Rajagopalan
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Patent number: 6815467Abstract: A method for producing a polyoxyalkylene polyol which comprises subjecting propylene oxide and ethylene oxide to ring-opening addition polymerization with an initiator in the presence of a catalyst, wherein the polyoxyalkylene polyol is a polyoxyalkylene polyol obtained by subjecting propylene oxide to ring-opening addition polymerization with an initiator in the presence of a double metal cyanide complex catalyst to form an oxypropylene block chain, subjecting ethylene oxide and propylene oxide to ring-opening addition polymerization randomly to form an oxyalkylene random chain, changing the catalyst and subjecting ethylene oxide to ring-opening addition polymerization in the presence of an alkali metal catalyst to form an oxyethylene block chain, and the polyoxyalkylene polyol is a polyoxyalkylene polyol having a hydroxyl value of from 5 to 56 mgKOH/g, a proportion of an initiator residue of at most 25 mass %, a proportion of the oxypropylene block chain of from 5 to 50 mass %, a total oxyethylene group cType: GrantFiled: July 18, 2002Date of Patent: November 9, 2004Assignee: Asahi Glass Company, LimitedInventors: Yoshinori Toyota, Akio Horie, Hiroshi Wada, Kayoko Sugiyama, Etsuko Akagi
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Publication number: 20040171785Abstract: Novel one-component polyurethane systems, to their preparation and use for preparing paints, inks and adhesives. The one-component polyurethane systems include one or more organic and/or inorganic compounds of molybdenum and/or of tungsten in which the molybdenum and/or tungsten has an oxidation state of at least +4.Type: ApplicationFiled: February 20, 2004Publication date: September 2, 2004Inventors: Christoph Gurtler, Jan Mazanek, Joachim Petzoldt, Heinz Schmidt, Stephan Nowak
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Publication number: 20040147706Abstract: A composition suitable for use as a catalyst for the reaction of an isocyanate compound or prepolymer thereof with an alcohol to form a polyurethane comprises a mixture of (a)an organometallic compound selected from: (i) a compound of formula M(RO)4, where M is titanium, zirconium, hafnium, aluminium, cobalt or iron or a mixture of these metals and OR is the residue of an alcohol ROH in which R comprises an (optionally substituted) C1-30 cyclic, branched or linear, alkyl, alkenyl, aryl or alkyl-aryl group or a mixture thereof, or; (ii) a complex of titanium, zirconium and/or hafnium and an acetoacetate ester and (b) a coordinating compound selected from a ketone, aldhehyde, carboxylic acid, sulphonic acid, nitride or an imine. An isocyanate composition containing a catalyst of the claimed composition is also described.Type: ApplicationFiled: December 1, 2003Publication date: July 29, 2004Inventor: Bruno Frederic Stengel
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Patent number: 6762314Abstract: An organometallic composition is described which comprises a complex of at least one orthoester of a metal having a formula M(ROAcAc)x(OR′)y in which M is selected from the group consisting of titanium, zirconium and hafnium; ROAcAc denotes an ester of an alochol ROH, in which R comprises an (optionally substituted) C1-30 cyclic, branched or linear, alkyl, alkenyl, aryl or alkyl-aryl group or a mixture thereof, with acetoacetic acid; OR′ is the residue of an alcohol R′OH in which R′ comprises an (optionally substituted) C7-30 cyclic, branched or linear, alkyl, alkenyl, aryl or alkyl-aryl group or a mixture thereof, and x and y are each in the range 1-3. The composition is useful as a curing agent for polyurethanes used in various applications.Type: GrantFiled: July 11, 2002Date of Patent: July 13, 2004Assignee: Imperial Chemical Industries PLCInventors: Martin G Partridge, Bruno F Stengel, John Ridland
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Patent number: 6756468Abstract: Cmpositions for coatings having a dry content higher than 80%, preferably of about 85-90% by weight, based on polyisocyanates and PFPEs, completely crosslinkable also in a range of temperatures between 5° C. and 20° C., comprising the following components: Component 1): mixture comprising: 1.a) Partially fluorinated prepolymers, having free NCO groups, obtained by reaction of (per)fluoropolyethers (PFPEs) diols having number average molecular weight Mn in the range 800-1,300 with the cyclic trimer of the isophorondiisocyanate, 1.b) non cyclic isocyanic trimer of hexamethylendiisocyanate, Component 2): (per) fluoropolyether (PFPE) diol with Mn in the range 350-700, preferably 500-650, component 3): inert organic solvent in crosslinking conditions, complement to 100% by weight of the composition.Type: GrantFiled: January 12, 2001Date of Patent: June 29, 2004Assignee: Ausimont S.p.A.Inventors: Stefano Turri, Carlo Pogliani
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Patent number: 6750310Abstract: Use of Titanium complex in a polyisocyanate composition comprising a titanium complex consisting of titanium and an acetoacetate ester in which the molar ratio of Ti to acetoacetate ester is in the range 1:2 and 1:8 and said acetoacetate ester is an ester of alcohol containing 1 to 4 carbon atoms for accelerating the binding of lignocellulosic materials.Type: GrantFiled: January 10, 2002Date of Patent: June 15, 2004Assignee: Huntsman International LLCInventor: Christopher J Skinner
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Patent number: 6743374Abstract: A self-emulsifiable polyisocyanate with high functionality, having the average number of functional groups in 4.3 or more and a viscosity of 8,000 mPa·s (at 25° C.) or less, which is obtained by subjecting a modified polyisocyanate containing allophanate bonds and a poly(oxyalkylene)glycol monoalkyl ether (e) having oxyethylene bonds in a total amount of 30 mole % or more in its molecule to a urethanization reaction, said modified polyisocyanate being obtained by reacting a polyol (a) having the average number of functional groups in an amount of 2 or more with an organic polyisocyanate (b) in the presence of an allophanate-forming catalyst (c) comprising a zirconium carboxylate; and a process for producing the same.Type: GrantFiled: July 31, 2002Date of Patent: June 1, 2004Assignee: Nippon Polyurethane Industry Co., Ltd.Inventors: Motomu Kita, Mitsushige Ikemoto, Toshiaki Sasahara
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Patent number: 6657036Abstract: The invention relates to polycondensation resins which are prepared by polycondensation of compounds having a low molecular weight and separation of small molecules in the presence of at least one hetergeneous catalyst. The invention also relates to polyaddition resins which are prepared by polyaddition in the presence of at least one heterogeneous catalyst. The invention further relates to the use of said polycondensation resins and polyaddition resins for the preparation of moulded parts, adhesives and coating materials.Type: GrantFiled: October 4, 2001Date of Patent: December 2, 2003Assignee: BASF Coatings AGInventors: Werner-Alfons Jung, Heinz-Peter Rink, Eberhard Fuchs, Wolfgang Straehle
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Patent number: 6646106Abstract: The invention concerns optically active polymers, obtainable by polymerizing chiral diphosphine having a C2 axis of symmetry, excluding all other symmetry element, with one or several polymerizable monomers, said chiral diphosphine consisting of a chiral body bearing two identical functional groups capable of reacting with said polymerizable monomers.Type: GrantFiled: December 11, 2001Date of Patent: November 11, 2003Assignees: Rhodia Chimie, Centre National de la Recherche Scientifique (CNRS)Inventors: Marc Lemaire, Rob Ter Halle, Emmanuelle Schulz, Benoît Colasson, Michel Spagnol, Christine Saluzzo, Thierry Lamouille
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Patent number: 6642342Abstract: The present invention relates to thermosetting two-component coating compositions containing A) at least one NCO prepolymer, B) at least one amine-free chain extender, C) at least one catalyst selected from metal 1,3-dicarbonylates and metal-oxo 1,3-dicarbonylates, wherein i) the metal 1,3-dicarbonylate contains as a neutral complex a metal cation with the electron configuration d0 of sub-group 3 or a lanthanide and ii) the metal-oxo 1,3-dicarbonylate contains a metal-oxo cation of sub-group 6 with the electron configuration d0. The present invention also relates to a process for preparing these coating compositions and to coated substrates prepared therefrom.Type: GrantFiled: June 26, 2002Date of Patent: November 4, 2003Assignee: Bayer AktiengesellschaftInventors: Michael Ludewig, Christoph Gürtler, Detlef-Ingo Schütze
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Patent number: 6613865Abstract: The invention relates to thermoplastic compositions that contain reactive isocyanate groups and that are suitable for use as desiccants for packaging moisture-sensitive goods, especially for polyurethane hotmelt adhesives that are cross-linked upon exposure to moisture. The compositions are formed by the reaction of hydroxy- or amino-containing polyols, including sugars, with an excess of polyisocyanates, and admixing the resulting product with polyurethane catalysts.Type: GrantFiled: April 26, 2002Date of Patent: September 2, 2003Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Robert Magunia, Gerald Petry, Michael Krebs
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Patent number: 6593444Abstract: Disclosed is a new class of TPUs with improved properties, based on poly(1,3-propanediol carbonate) diol, using 10 to 55% hard segment concentration, and cured with a diisocyanate. The composition provides a broader range of mechanical and thermal properties for TPU formulations, including improvements in hardness, higher elasticity modulus, and improved softening temperature and coefficient of thermal expansion, in addition to improved clarity.Type: GrantFiled: March 27, 2001Date of Patent: July 15, 2003Assignee: Shell Oil CompanyInventors: Thomas Clayton Forschner, Wyndham Henry Boon, Aisa Sendijarevic, Kurt Charles Frisch, David Eric Gwyn
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Patent number: 6590057Abstract: The invention provides polyurethane elastomers (PU elastomers), a process for their production using special catalyst mixtures and their use in particular for the manufacture of shoe soles.Type: GrantFiled: August 27, 2002Date of Patent: July 8, 2003Assignee: Bayer AktiengesellschaftInventors: Klaus Brecht, Wolfgang Grimm, Stephan Schleiermacher, Marc Schütze
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Patent number: 6548615Abstract: The invention relates to a reactive composition containing A) an isocyanate-containing compound, B) a polyol, C) an organic tin or bismuth compound, D) a thiol group-containing compound or a polyphenol which is able to react with an isocyanate group in the presence of a tertiary amine as activator and with adjacent hydroxyl groups and E) a hydrolyzable halogen compound, wherein the molar ratio SH and/or OH:metal is 2 to 500 and the molar ratio halogen/metal is 0.05 to 10.Type: GrantFiled: March 2, 2001Date of Patent: April 15, 2003Assignee: Bayer AktiengesellschaftInventors: Stefan Groth, Jan Mazanek, Rolf Langel, Detlef-Ingo Schütze, Jürgen Urban
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Patent number: 6512086Abstract: Process for the preparation of fluid organosilicon compounds usable in adhesive, coating and sealant formulations is described. The process includes the synthesis of organosilicon prepolymer compositions starting from unsaturated polyurethanes obtained in turn from unsaturated monoalcohol polyethers and diisocyanates with a controlled NCO/OH ratio, to which chlorosilanes are added in the presence of methyl or ethyl orthoformates.Type: GrantFiled: July 24, 2001Date of Patent: January 28, 2003Assignee: Mapei S.p.A.Inventors: Alberto Greco, Antonio Ausilio, Enrico Pozzi
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Publication number: 20020188047Abstract: An organometallic composition, suitable for use in curing polyisocyanate compositions, includes a complex of at least one metal selected from iron, cobalt and aluminum and at least one &bgr;-dicarbonyl compound wherein when the metal is iron (II) or cobalt (II) the molar ratio of &bgr;-dicarbonyl compound to metal is in the range from 2.1:1 to 10:1, and when the metal is aluminum (III), iron (III) or cobalt (III) the molar ratio of &bgr;-dicarbonyl compound to metal is in the range from 3.1:1 to 10:1. A polyisocyanate composition containing the organometallic composition and a process for binding lignocellulosic material is also described.Type: ApplicationFiled: February 1, 2002Publication date: December 12, 2002Applicant: Imperial Chemical Industries PLCInventors: Christopher J. Skinner, Martin G. Partridge
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Patent number: 6469121Abstract: A method for the preparation of a storage stable organic polyisocyanate having allophanate linkages prepared by reacting a urethane containing organic polyisocyanate with a reactive hydroxyl compound in the presence of a liquid organic titanium oxide, or zirconium oxide, or hafnium oxide catalyst that is fully miscible in the reactive hydroxyl compound is disclosed. After completion of the allophanate reaction, the catalyst is deactivated by the use of a strong inorganic acid, organic acid, organic chloroformate or acid chloride.Type: GrantFiled: December 29, 2000Date of Patent: October 22, 2002Assignee: BASF CorporationInventors: Jon Speier, Thirumurti Narayan, Nikolay Lebedinski
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Patent number: 6417315Abstract: A conductive quasi-solution useful for making a homogeneously conductive single-phase polyurethane, comprising a transition metal salt, a carrier solution, and a dispersing agent, wherein said conductive quasi-solution has a transition metal salt concentration between 10 and 30% by weight, and methods of making thermoset and thermoplastic polyurethane polymers therewith.Type: GrantFiled: January 16, 2001Date of Patent: July 9, 2002Assignee: Mearthane Products CorporationInventors: Albert C. Chiang, John A. Roderick
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Patent number: 6395861Abstract: A fast-curing polyurethane coating system for a game ball is described herein. The coating system comprises a mixture of a polyol, an isocyanate, a solvent and a surprisingly high level of catalyst which accelerates the curing process. The coating is a two-part polyurethane system which is preferably applied by spraying. The coating is particularly well-suited for use on golf balls, and also can be applied to other game balls such as softballs, baseballs, and cricket balls.Type: GrantFiled: March 1, 1996Date of Patent: May 28, 2002Assignee: Spalding Sports Worldside, Inc.Inventor: Thomas J. Kennedy, III
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Publication number: 20020052461Abstract: Disclosed is a new class of TPUs with improved properties, based on poly(1,3-propanediol carbonate) diol, using 10 to 550 hard segment concentration, and cured with a diisocyanate. The composition provides a broader range of mechanical and thermal properties for TPU formulations, including improvements in hardness, higher elasticity modulus, and improved softening temperature and coefficient of thermal expansion, in addition to improved clarity.Type: ApplicationFiled: March 27, 2001Publication date: May 2, 2002Inventors: Thomas Clayton Forschner, Wyndham Henry Boon, Aisa Sendijarevic, Kurt Charles Frisch, David Eric Gwyn, Sally S. Frisch
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Patent number: 6313060Abstract: A resilient polyurethane foam produced by using a polyether polyol produced by reacting alkylene oxides with a polyhydroxy compound having at least 2 hydroxyl groups as an initiator in the presence of the catalyst for alkylene oxide ring-opening polymerization of the present invention, which is excellent in foam physical properties, vibration characteristics and molding properties.Type: GrantFiled: March 8, 2000Date of Patent: November 6, 2001Assignee: Asahi Glass Company, LimitedInventors: Kayoko Sugiyama, Hiroki Fukuda, Akio Horie, Hiroshi Wada
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Patent number: 6300457Abstract: The present invention provides polyester/polyurethane/vinyl dioxolane based coating compositions containing no or essentially no volatile organic components. Oligomers for forming the coating compositions of the present invention are vinyl dioxolane end-capped polyesters and polyurethane oligomers.Type: GrantFiled: November 2, 1999Date of Patent: October 9, 2001Assignee: Foster Miller, Inc.Inventors: Leslie S. Rubin, Robert F. Kovar, Nese Orbey, Nelson Landrau, Paul Osenar
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Patent number: 6288200Abstract: Polyisocyanate composition comprising a Group IVB metal compound, preferably a titanium chelate, optionally in combination with a compatibilizing compound and/or conventional release agents and the use thereof in binding lignocellulosic material.Type: GrantFiled: October 30, 1996Date of Patent: September 11, 2001Assignee: Imperial Chemical Industries PLCInventors: Bruno Andrew Alphonse Jung, Jan Willem Leenslag, Hans Guido Godelieve Verbeke, Danny Anna Eduard Geukens
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Publication number: 20010007012Abstract: The invention provides a process for preparing an allophanate-containing compound in the presence of a metal catalyst and a tertiary amine. In a preferred process, the tertiary amine compound also has a hydroxyl group. The hydroxyl group can react with the isocyanate functionality. Also disclosed is a process in which an allophanate-containing compound is prepared with copper acetate monohydrate as a catalyst.Type: ApplicationFiled: February 7, 2001Publication date: July 5, 2001Inventor: Charles L. Tazzia
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Patent number: 6242555Abstract: A process for the production of micro-cellular or non-cellular, light-stable elastomeric, flexible or semi-flexible polyurethane moldings which are especially suited for window encapsulation applications from a reaction mixture by the reaction injection molding process, wherein: A) an isocyanate component containing an isophorone diisocyanate (IPDI) trimer/monomer mixture having an NCO content of from 24.Type: GrantFiled: May 13, 1998Date of Patent: June 5, 2001Assignee: RecticelInventors: Eddie Du Prez, Pierre Coppens
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Patent number: 6217984Abstract: An energy sensitive composition comprising a monomeric organometallic complex essentially free of nucleophilic groups and which, upon exposure to energy, bonds to basic reactive sites on a substrate via the metal center, leaving the polymerizable group of the complex unreacted and unrestricted; an energy sensitive composition at least one energy sensitive organometallic group is incorporated in or appended to the backbone of a polymer, such that the resulting coordinatively unsaturated organometallic group or groups bond to basic reactive sites on a substrate, thus forming permanent bonds, and further, the adherent compositions are useful in applications such as adhesion of polymers to substrates, protective coatings, printing plates, durable release coatings, primers, binders, and paints.Type: GrantFiled: May 21, 1992Date of Patent: April 17, 2001Assignee: 3M Innovative Properties CompanyInventors: Wesley J. Bruxvoort, Steven J. Keipert, Fred B. McCormick, Jerry W. Williams, Bradford B. Wright
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Patent number: 6184331Abstract: A conductive quasi-solution useful for making a homogeneously conductive single-phase polyurethane, comprising a transition metal salt, a carrier solution, and a dispersing agent, wherein said conductive quasi-solution has a transition metal salt concentration between 10 and 30% by weight, and methods of making thermoset and thermoplastic polyurethane polymers therewith.Type: GrantFiled: December 9, 1999Date of Patent: February 6, 2001Assignee: Mearthane Products CorporationInventors: Albert C. Chiang, John A. Roderick
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Patent number: 6177523Abstract: The present invention relates to functionalizable and crosslinkable polyurethanes formed of a polyurethane intermediate including one or more ester groups which react with an amine equivalent to form an amide unit. The polyurethane intermediate comprises the reaction product of alkyl ester of dihydroxypolyacid or dimethylolalkanoic acid, a polyoxyalkylene diol and an organic diisocyanate. The polyurethane is reacted with a solution of an amine equivalent and a solvent or an amine. An article of manufacture can be formed from the polyurethane.Type: GrantFiled: July 14, 1999Date of Patent: January 23, 2001Assignee: CardioTech International, Inc.Inventors: Murray H. Reich, John Teffenhart
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Patent number: 6133371Abstract: A sealant for forming a fluid seal between the faying surface of two metallic substrates that are compressively and mechanically joined together. The sealant is a liquid in its pre-cured condition and a dry solid in its cured condition. The transition of the sealant from its pre-cured condition to its cured condition occurs at room temperature. The sealant's curing time is not less than about 10 minutes and not more than about 16 hours. The cured sealant has a Shore A hardness between about 30 and 70. The cured sealant is impermeable and resistant to chemical attack by air, water, common solvents and petroleum fuels. Also, the cured sealant is resistant to compressive cold flow, however, the cured sealant is deformable to conform to an abutting surface or with a layer of similar sealant. The cured sealant is flexible and resistant to temperatures between about -65 degrees F. and about 250 degrees F.Type: GrantFiled: June 5, 1998Date of Patent: October 17, 2000Assignee: Hi-Shear CorporationInventor: Joseph Philipson
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Patent number: 6124380Abstract: The invention comprises a curable composition comprising: (i) a blocked reactive component wherein the blocked reactive component is a blocked isocyanate or a blocked isothiocyanate; (ii) a functional compound reactive with the blocked reactive component, the functional compound containing reactive hydrogen; (iii) a catalyst for promoting the reaction of the reactive component with the blocked functional compound, wherein said catalyst is based on the reaction product of manganese, cobalt, nickel, copper, zinc, germanium, antimony, or bismuth, or the oxides thereof with a mercaptan, or an organic acid, wherein said organic acid is hexanoic, oxalic, adipic, lactic, tartaric, salicylic, thioglycolic, succinic, or mercapto succinic acid, or the reaction product of copper or germanium, or the oxides thereof with a lower aliphatic acid.Type: GrantFiled: March 12, 1999Date of Patent: September 26, 2000Assignee: Elf Atochem North America, Inc.Inventors: Emily C. Bossert, Kevin Cannon, William D. Honnick, Wayne Ranbom
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Patent number: 6111051Abstract: A conductive quasi-solution useful for making a homogeneously conductive single-phase polyurethane, comprising a transition metal salt, a carrier solution, and a dispersing agent, wherein said conductive quasi-solution has a transition metal salt concentration between 10 and 30% by weight, and methods of making thermoset and thermoplastic polyurethane polymers therewith.Type: GrantFiled: August 7, 1998Date of Patent: August 29, 2000Assignee: Mearthane Products CorporationInventors: Albert C. Chiang, John A. Roderick
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Patent number: 6036879Abstract: Polyoxyalkylene polyols containing double metal cyanide complexes or residues thereof as are produced during the preparation of polyoxyalkylene polyols by the double metal cyanide complex catalyzed oxyalkylation of a suitably functional hydric initiator are stable without catalyst removal. Isocyanate-terminated prepolymers prepared from such polyols are surprisingly viscosity-stable relative to similar prepolymers prepared from polyols not containing double metal cyanide complexes or residues thereof.Type: GrantFiled: February 9, 1999Date of Patent: March 14, 2000Assignee: Arco Chemical Technology, L.P.Inventors: Bruce D. Lawrey, Stephen D. Seneker, Nigel Barksby
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Patent number: 6028128Abstract: The invention comprises a curable composition comprising: (i) a blocked reactive component wherein the blocked reactive component is a blocked isocyanate or a blocked isothiocyanate; (ii) a functional compound reactive with the blocked reactive component, the functional compound containing reactive hydrogen; (iii) a catalyst for promoting the reaction of the reactive component with the blocked functional compound, wherein said catalyst is based on the reaction product of manganese, cobalt, nickel, copper, zinc, germanium, antimony, or bismuth, or the oxides thereof with a mercaptan, or an organic acid, wherein said organic acid is hexanoic, oxalic, adipic, lactic, tartaric, salicylic, thioglycolic, succinic, or mercapto succinic acid, or the reaction product of copper or germanium, or the oxides thereof with a lower aliphatic acid.Type: GrantFiled: October 19, 1998Date of Patent: February 22, 2000Assignee: ELF Atochem North America, Inc.Inventors: Emily C. Bossert, Kevin Cannon, William D. Honnick, Wayne Ranbom
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Patent number: 5965686Abstract: The present invention is directed to novel metal organocomplexes as catalysts for the reaction of compounds with isocyanate and hydroxy functional groups to form urethane and/or polyurethane and the process employing such catalysts. More particularly, the present invention is directed to novel complexes of zirconium or hafnium with diketones or alkylacetoacetoates. These novel catalysts are useful for the production of urethanes and polyurethanes which are important in many industrial applications, such as: coatings, foams, adhesives, sealants, and reaction injection molding (RIM) plastics.Type: GrantFiled: August 24, 1998Date of Patent: October 12, 1999Assignee: King Industries, Inc.Inventors: Werner Blank, Zhiqiang Alex He, Marie Emmanuelle Picci, John James Florio
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Patent number: 5936034Abstract: The present invention provides a process for producing gel-coated, shaped articles wherein the total processing time is decreased compared to conventional processes and the physico-mechanical properties of the gel-coated, shaped articles produced therefrom are maintained.Type: GrantFiled: April 4, 1997Date of Patent: August 10, 1999Assignee: ECP Enichem Polimeri Netherlands B.V.Inventor: Stuart Smith
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Patent number: 5919888Abstract: Polyoxyalkylene polyols containing double metal cyanide complexes or residues thereof as are produced during the preparation of polyoxyalkylene polyols by the double metal cyanide complex catalyzed oxyalkylation of a suitably functional hydric initiator are stable without catalyst removal. Isocyanate-terminated prepolymers prepared from such polyols are surprisingly viscosity-stable relative to similar prepolymers prepared from polyols not containing double metal cyanide complexes or residues thereof.Type: GrantFiled: June 1, 1998Date of Patent: July 6, 1999Assignee: Arco Chemical Technology, L.P.Inventors: Bruce D. Lawrey, Stephen D. Seneker, Nigel Barksby
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Patent number: 5898057Abstract: A conductive quasi-solution useful for making a homogeneously conductive single-phase polyurethane, comprising a transition metal salt, a carrier solution, and a dispersing agent, wherein said conductive quasi-solution has a transition metal salt concentration between 10 and 30% by weight, and methods of making thermoset and thermoplastic polyurethane polymers therewith.Type: GrantFiled: May 27, 1997Date of Patent: April 27, 1999Assignee: Mearthane Products Corp.Inventors: Albert C. Chiang, John A. Roderick
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Patent number: 5859087Abstract: Provided is a radiation-curable primer coating composition, which is adapted to provide a printable primer coating on a polyolefin surface that is functionally resistant to delamination from the polyolefin surface over the temperature range from heat pasteurization temperatures to freezer storage temperatures. The primer composition being formulated from the following components:at least one monomer or oligomer having at least one functional group that polymerizes when exposed to radiation; andan effective amount of at least one zirconate or titanate, or a mixuture of a titanate and zirconate, to increase adhesion of the radiation-cured primer coating to said polyolefin surface.Type: GrantFiled: October 16, 1996Date of Patent: January 12, 1999Assignee: DSM NVInventor: Edward P. Zahora
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Patent number: 5849864Abstract: The present invention is addressed a formulation curable in the presence of an amine and containing one or more of a polyol or polymercapto resin, a polyisocyanate cross-linking agent, optionally a organic vehicle, and a tin catalyst complex. The present invention comprises the catalyst complex being formed from a metal catalyst and a complexing sulfonic acid in an equivalent ratio of complexing sulfonic acid to metal catalyst of greater than 2:1. Such curable formulation may be compounded into a coating, an adhesive (including a structural adhesive), a caulk, a foundry binder, or the like. Besides having excellent shelf life, long periods of open time are experienced with the novel catalyzed formulation. However, upon exposure to an amine, the catalyst complex becomes activated and then is effective to catalyze the NCO--OH reaction or the NCO--SH reaction to effect cure of the formulation.Type: GrantFiled: August 1, 1996Date of Patent: December 15, 1998Assignee: Ashland Chemical CompanyInventors: Gary M. Carlson, Laurence G. Dammann
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Patent number: 5847068Abstract: Cholesteric copolyisocyanates with repeating units of the formulae: ##STR1## and, where appropriate, of the formula ##STR2## where R.sup.1 is a chiral aliphatic or aromatic radical,R.sup.2 is a crosslinkable radical, andR.sup.3 is an achiral radical,and polymers obtainable by crosslinking the copolyisocyanates according to the invention with a polymerizable solvent, and pigments comprising the polymers according to the invention, are described.Type: GrantFiled: April 3, 1997Date of Patent: December 8, 1998Assignee: BASF AktiengesellschaftInventors: Georg Maxein, Bruce M. Novak, Rudolf Zentel, Harald Keller
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Patent number: 5821180Abstract: A laminate comprising a layer formed by melt molding a thermoplastic polyurethane and a fibrous base layer, a film or sheet melt molded from the thermoplastic polyurethane, and a thermoplastic polyurethane composition comprising the thermoplastic polyurethane and tin compound in an amount of 0.3 to 15 ppm (in terms of tin atom) based on the thermoplastic polyurethane; the thermoplastic polyurethane being a thermoplastic polyurethane obtained from a polymeric diol (a) having a number average molecular weight of 1,500 to 4,000, an organic diisocyanate (b) and a chain extender (c) and having an inherent viscosity of at least 0.9 dl/g and a retention of long-chain hard segments when heat melted of at least 80%, the polymeric diol (a) having a crystallization enthalpy (.DELTA.H) of not more than 70 J/g and having low molecular diol units comprising at least 30 mole % of 1,9-nonanediol units.Type: GrantFiled: August 13, 1997Date of Patent: October 13, 1998Assignee: Kuraray Co., Ltd.Inventors: Shizuo Iwata, Shinya Kato, Tetsuya Ashida, Hisao Yoneda, Koji Hirai
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Patent number: 5811505Abstract: An energy-polymerizable composition derived from ingredients comprising: a cyanate ester monomer or oligomer comprising an organic radical bonded through aromatic carbon atoms to at least two --OCN groups; a low molecular weight polyalkylene glycol; and an organometallic compound in which at least one carbon atom of an organic group is bonded to a metal atom. The composition can be cured by at least one of thermal energy, radiation, and accelerated particles, to produce a cured, homogeneous composition.Type: GrantFiled: December 17, 1997Date of Patent: September 22, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventor: Fred B. McCormick
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Patent number: 5770671Abstract: Isocyanates are polymerized in a simple manner by polymerizing aliphatic and/or aromatic isocyanates in the presence of metallocenes at temperatures from 20.degree. to 220.degree. C., optionally subject to increased or reduced pressure and optionally in the presence of an inert organic solvent, the metallocene being used in an amount of 5 to 50,000 ppm relative to the amount of isocyanates used.Type: GrantFiled: August 1, 1997Date of Patent: June 23, 1998Assignee: Bayer AktiengesellschaftInventors: Hartmut Nefzger, Bernd Quiring
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Patent number: 5741879Abstract: An energy-polymerizable composition derived from ingredients comprising: a cyanate ester monomer or oligomer comprising an organic radical bonded through aromatic carbon atoms to at least two --OCN groups; a low molecular weight polyalkylene glycol; and an organometallic compound in which at least one carbon atom of an organic group is bonded to a metal atom. The composition can be cured by at least one of thermal energy, radiation, and accelerated particles, to produce a cured, homogeneous composition.Type: GrantFiled: March 3, 1995Date of Patent: April 21, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventor: Fred B. McCormick
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Patent number: 5733945Abstract: Nickel acetyl acetonate catalysts used in the manufacture of polyurethanes and particularly polyurathane foam, is replaced with a more environmentally friendly organo-metallic catalyst, specifically other metal acetyl acetonates such as iron or copper. In accordance with an important feature of this invention, in addition to the metal acetyl acetonate, the catalyst system also includes acetyl acetone. The acetyl acetone acts as a delay mechanism to delay the catalytic action of the metal acetyl acetonate which is normally highly catalytic at relatively low temperatures. It will be appreciated that high catalytic activity at relatively low temperature will lead to deleterious premature cure. By adding acetyl acetone into the catalyst system, the acetyl acetone acts to delay and/or slow the catalytic action of the metal acetyl acetonate until the polyurethane is heated at which point the acetyl acetone is driven off and the metal acetyl acetonate then provides a relatively fast cure at the elevated temperature.Type: GrantFiled: December 4, 1995Date of Patent: March 31, 1998Assignee: Rogers CorporationInventor: Scott S. Simpson
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Patent number: 5714565Abstract: The present invention is directed to a heat resistant product prepared by reacting a) a mixture of i) an organic polyisocyanate, ii) an epoxide group containing compound, and iii), optionally, an organic compound containing an active methylene group and containing at least one electron withdrawing group adjacent to the methylene carbon, and b) at least one polyol which is free of any tertiary amine groups, with the reaction being conducted at an NCO:OH equivalent ratio of from 2:1 to 5:1. The reaction is conducted in the presence of a tertiary amine-free isocyanurate catalyst selected from the group consisting of oxides, alkoxides, hydroxides and carboxylates of alkali metals, alkaline earth metals, transition metals and quaternary ammonium.Type: GrantFiled: December 28, 1995Date of Patent: February 3, 1998Assignee: Bayer CorporationInventors: Neil H. Nodelman, David D. Steppan