Reactant Contains At Least One Heterocyclic Ring Patents (Class 528/73)
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Patent number: 5883216Abstract: The present invention relates to polyisocyanates containingi) 0.5 to 10 wt. % of amide and/or imide structural units (calculated as --CO--N.dbd., MW=42),ii) 5 to 20 wt. % of isocyanate groups (calculated as --NCO, MW=42) blocked with blocking agents which are monofunctional in the context of the isocyanate addition reaction andiii) 0 to 30 wt. % of chemically incorporated urethane groups (calculated as --NH--CO--O--, MW=59) obtained from the reaction of isocyanate groups with the hydroxyl groups of organic polyhydroxyl compounds.The present invention also relates to a process for the production of these lacquer polyisocyanates, their use as a binder for stoving lacquers optionally in combination with organic polyhydroxyl compounds and to their use as a binder component containing free hydroxyl groups and optionally blocked isocyanate groups by reacting and/or blending the polyisocyanates with organic polyhydroxyl compounds having a molecular weight of 62 to 350.Type: GrantFiled: June 27, 1996Date of Patent: March 16, 1999Assignee: Bayer AktiengesellschaftInventors: Reinhard Halpaap, Hans Schlegel, Jan Mazanek, Hans-Ulrich Meier-Westhues
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Patent number: 5874173Abstract: Heat-curing, solvent-free one-component adhesives which are based on polyurethanes and which do not give off elimination products, and which are derived from A) a hardener component consisting of polyaddition products containing hydroxyl and uretdione groups, B) a binder component comprising 1,2-epoxide compounds having more than one 1,2-epoxide group and one or more hydroxyl groups in the molecule, C) catalysts for polymerizing epoxide groups, optionally D) further hydroxyl-containing compounds and optionally E) auxiliaries and additives known from adhesives technology; a process for preparing these compounds and to their use as heat-curing, one-component, solvent-free, thermally stable and solvent-resistant polyurethane (PU) adhesives which do not give off elimination products.Type: GrantFiled: July 11, 1997Date of Patent: February 23, 1999Assignee: Huels AktiengesllschaftInventor: Andreas Wenning
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Patent number: 5872203Abstract: A 100% solids polyurethane adhesive composition for bonding polymeric roofing materials to roof-deck substrates is provided which includes two components. The first component comprises a monomeric or polymeric diisocyanate, or a polyurethane prepolymer formed by the reaction of the monomeric or polymeric diisocyanate with a polyol. The second component comprises a polyol selected from the group consisting of a polyether or polyester polyol, an alkanolamine diol, a hydroxyl-terminated homopolymer of polybutadiene, and mixtures thereof. The first and second components are combined such that the ratio of isocyanate groups in the first component to the ratio of hydroxyl groups in the second component is from about 0.5:1 to 1.5:1.Type: GrantFiled: September 25, 1995Date of Patent: February 16, 1999Assignee: ADCO Products, Inc.Inventors: Wei-Jian Wen, Brian Jonathan Briddell, Kathleen Louise Lamb
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Patent number: 5866633Abstract: A biocidal material comprises an organic biocide immobilized on a polymeric support characterized in that the support is water-insoluble and the biocide is covalently bound to the support by a hydrolytically stable covalent linkage. The material can be used for inhibiting bacterial growth in an aqueous medium e.g. the wash water of a photoprocessing system. The material can be housed in a flow-through container.Type: GrantFiled: March 4, 1996Date of Patent: February 2, 1999Assignee: Eastman Kodak CompanyInventors: Gregory Nigel Batts, Karen Leeming, Christoper Peter Moore
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Patent number: 5863980Abstract: A process for preparing a polyurethane prepolymer containing carboxylic group(s), or both carboxylic group(s) and double bond(s), which comprises the steps of 1) preparing a diol or triol monomer having carboxylic group(s), or having both carboxylic group(s) and double bond(s) by performing an addition reaction of at least one acid anhydride(s) which may contain double bond(s), with at least one triol or tetraol derivative(s) containing three or four hydroxyl groups in a molar ratio from 0.5:1 to 2:1; and then 2) reacting the obtained diol or triol monomer, or their mixture with a polyol and a diisocyanate or a diisocyanate polymer to give polyurethane prepolymer having an NCO content of 0.1 to 30%, is disclosed. In addition, a process for preparing a water-stable aqueous polyurethane dispersion by neutralizing, dispersing, and chain extending the polyurethane prepolymer obtained above is provided.Type: GrantFiled: December 20, 1996Date of Patent: January 26, 1999Assignee: Hepce Chem Co., Ltd.Inventors: Keun-Bae Choi, Ki-Soo Kim, Hyoung-Sug Kim, Seog-Jae Lee
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Patent number: 5861470Abstract: The invention discloses two-component water-based laminating adhesives, comprising aqueous polyurethane dispersions and water dispersible polyisocyanates based on the isocyanurates of hexamethylene diisocyanate, having enhanced machining characteristics. The invention further discloses a method for the preparation of dry-bond laminates having enhanced properties including dry-bond clarity and water resistance.Type: GrantFiled: March 7, 1997Date of Patent: January 19, 1999Assignee: H. B. Fuller Licensing & Financing, Inc.Inventors: Peter A. Voss, Thomas E. Rolando
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Patent number: 5859167Abstract: Cured, thermoset plastic articles derived from scrap polyurethanes are disclosed. The polyurethane is converted to a liquified mixture containing digested polyurethane and cyclic, unsaturated anhydride. A Lewis acid then catalyzes insertion of the cyclic, unsaturated anhydride into the polyether backbone of the polyurethane to give a liquid, unsaturated resin. The unsaturated resin can cured with a vinyl monomer in the presence of a free-radical initiator to give a cured, thermoset plastic.Type: GrantFiled: July 6, 1993Date of Patent: January 12, 1999Assignee: ARCO Chemical Technology, L.P.Inventors: Lau S. Yang, Diane A. Kooker
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Patent number: 5852203Abstract: The present invention relates to hydroxy-functional polyhydantoin prepolymers corresponding to the formula ##STR1## wherein R represents the residue obtained by removing the isocyanate groups from an organic monomeric diisocyanate, a polyisocyanate adduct or an NCO prepolymer containing hydantoin groups, R.sub.2 represents an organic group which is inert towards isocyanate groups at a temperature of 100.degree. C. or less, R.sub.3 and R.sub.4 may be identical or different and represent hydrogen or organic groups which are inert towards isocyanate groups at a temperature of 100.degree. C. or less, R.sub.5 represents the hydrocarbon radical obtained by removing the amino and hydroxyl groups from an amino alcohol, n has a value of 1 to 3 and m has a value of 2 to 6. The present invention is also directed to compositions suitable for the production of coatings, adhesives or elastomers containing these polyhydantoin prepolymers in combination with optionally blocked polyisocyanates or aminoplast resins.Type: GrantFiled: March 11, 1997Date of Patent: December 22, 1998Assignee: Bayer CorporationInventors: E. Haakan Jonsson, Douglas A. Wicks, Philip E. Yeske, Lyuba K. Gindin
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Patent number: 5849855Abstract: Disclosed is a blocked polyisocyanate composition comprising: a blocked polyisocyanate obtained by blocking the terminal isocyanate groups of a two or more terminal isocyanate groups-containing polyisocyanate derived from at least one diisocyanate selected from an aliphatic diisocyanate and an alicyclic diisocyanate with a blocking agent comprising at least one active methylene compound selected from a malonic diester and an acetoacetic ester; and a salt of a basic compound with an acidic compound, or a mixture of the salt with the basic compound or the acidic compound, the composition having a pH value of from 1 to 8.5. The blocked polyisocyanate composition of the present invention not only exhibits high stability even under high temperature conditions, but also is capable of maintaining such high stability for a prolonged period of time.Type: GrantFiled: August 19, 1996Date of Patent: December 15, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Taketoshi Usui, Yoshiyuki Asahina
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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: 5847067Abstract: Urea- and uretdione-functional polyisocyanates having the following formula (I): ##STR1## where ##STR2## n is an integer of from 1 to 20; R.sup.1, R.sup.3 =not more than one linear or branched (cyclo)alkyl radical having 1-14 carbon atoms or H and at least one of the formula: ##STR3## R.sup.2 =R, linear or branched (cyclo)alkyl radical having 6 carbon atoms; R.sup.4, R.sup.5 =identical or different hydrocarbon radicals having 1 to 14 carbon atoms.Type: GrantFiled: September 11, 1997Date of Patent: December 8, 1998Assignee: Huels AktiengesellschaftInventor: Rainer Gras
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Patent number: 5840823Abstract: Aqueous polyurethane dispersions having latent crosslinking properties containI) a disperse phase (P.I), containingIa) a polyurethane (PUR.Ia) which, in addition to groups which impart water dispersibility to the polyurethane, carries groups which have a C--C double bond and in which the double bond is activated by a carbonyl group bonded directly therewith, orIb) a mixture ofa polyurethane (PUR.Ib) which carries groups which impart water dispersibility to the polyurethane but not groups which have a C--C double bond and in which the double bond is activated by a carbonyl group bonded directly therewith anda compound (V.I) which differs from the polyurethanes PUR.Ia and PUR.Ib, and which carries groups which have a C--C double bond and in which the double bond is activated by a carbonyl group bonded directly therewith andII) a disperse phase (P.II) containing a compound which differs from the compounds (PUR.Ia), (PUR.Ib) and (V.Type: GrantFiled: February 25, 1997Date of Patent: November 24, 1998Assignee: BASF AktiengesellschaftInventors: Ulrike Licht, Nicolas Kokel, Karl Haberle, Renate Wustefeld
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Patent number: 5837795Abstract: A heat-curing 1-component coating material having a viscosity at 60.degree.C. of 1000-50,000 mPas, containingA) 85-96% by weight of at least one isocyanate prepolymer containing isocyanurate groups and urethane groups,B) 4-12% by weight of finely divided melamine having a mean particle diameter of 1-30 .mu.m, andC) 0-3% by weight of auxiliaries.Type: GrantFiled: August 25, 1997Date of Patent: November 17, 1998Assignee: Huels AktiengesellschaftInventors: Rainer Lomoelder, Peter Speier
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Patent number: 5837796Abstract: The present invention relates to a process for preparing polyisocyanates containing isocyanurate groups by trimerizing a portion of the isocyanate groups of an organic polyisocyanate component containinga) one or more diisocyanates corresponding to formula (1) ##STR1## wherein R represents a saturated, straight-chain, aliphatic hydrocarbon group having 8 to 15 carbon atoms and optionallyb) up to 95 NCO equivalent-%, based on the total equivalents a) and b), of one or more organic polyisocyanates other than a),in the presence of trimerization catalysts and terminating the trimerization reaction at any desired degree of trimerization.The invention also relates to the polyisocyanates containing isocyanurate groups obtained by this process and to their use, optionally in excess starting polyisocyanates and optionally blocked with blocking agents for isocyanate groups, as an isocyanate component for preparing polyisocyanate addition products.Type: GrantFiled: June 25, 1997Date of Patent: November 17, 1998Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Bernhard Jansen, Rolf-Volker Meyer
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Patent number: 5837794Abstract: TDI residue-based urethane-filled isocyanate compositions are produced by reacting a TDI residue satisfying specified criteria with a monofunctional alcohol in amounts such that the equivalent ratio of isocyanate groups to hydroxyl groups is from about 0.9:1 to about 1:0.9. This reaction product is then dissolved in a diisocyanate or polyisocyanate before, during or after reaction of that product with an epoxide having an epoxide equivalent weight of from about 44 to about 400 at a temperature of up to 120.degree. C. These TDI residue-based urethane-filled isocyanate compositions are particularly useful in the production of polyurethanes.Type: GrantFiled: October 27, 1997Date of Patent: November 17, 1998Assignee: Bayer CorporationInventors: William E. Slack, Scott A. Kane, James W. Rosthauser
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Patent number: 5834579Abstract: Tertiary amines having carbonate and urethane groups and optionally hydroxyl groups are produced by reacting a) a polyhydric alcohol and b) a primary-tertiary diamine with c) a carbonic acid derivative selected from the group consisting of optionally cyclic carbonates, urea, phosgene and bis-chlorocarbonates of alcohols of the same type as those used as component a). This reaction may be carried out in one or two steps. The tertiary amines produced by this process are useful as catalysts, which may optionally be incorporated into an isocyanate-reactive material, in the isocyanate addition reaction for the production of polyurethane plastics. These tertiary amines are particularly useful for the production of foam backed plastic films.Type: GrantFiled: June 16, 1997Date of Patent: November 10, 1998Assignee: Bayer AktiengesellschaftInventors: Klaus Konig, Ulrich Liman, Josef Sanders
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Patent number: 5817732Abstract: A thermally dissociative blocked polyisocyanate, wherein an isocyanate group of the polyisocyanate is protected with a thermally dissociative blocking agent, which polyisocyanate is a urethane-modified isocyanurate polyisocyanate,(1) that is obtained by a cyclic-trimerization of at least one aliphatic or alicyclic diisocyanate either after its reaction with or in the presence of a polyhydric alcohol having a valence of at least 3,(2) of which the average number of isocyanate functional groups in said polyisocyanate is in the range of 4.5 to 10, and(3) the viscosity of which measured at 25.degree. C. substantially in the absence of the aliphatic or alicyclic diisocyanate monomer and a solvent thereof is in the range of 5,000 to 100,000 mPa.multidot.s;a thermosetting hardener composition; anda thermosetting one-pack coating composition comprising the blocked polyisocyanate.Type: GrantFiled: October 8, 1996Date of Patent: October 6, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Yoshiyuki Asahina, Taketoshi Usui
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Patent number: 5798431Abstract: A process for the production of polyisocyanates containing isocyanurate groups by the catalytic trimerization of a mixture of low molecular weight isocyanate components having aliphatically and aromatically bound isocyanate groups in the presence of aminosilyl compounds, the resulting polyisocyanates and their use in coating compositions.Type: GrantFiled: July 15, 1996Date of Patent: August 25, 1998Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Carl-gerd Dieris, Lutz Schmalstieg, Reinhard Halpaap
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Patent number: 5795950Abstract: The present invention provides straight-chain crystalline polyuretdione which has a structure represented by formula (1): ##STR1## wherein Y represents ##STR2## X represents ##STR3## or --NCO; R.sub.1 is R.sub.2 or ##STR4## R.sub.2 is a residual group other than diol; R.sub.3 is a residual group obtained by removing an active hydrogen from a compound having one active hydrogen; R.sub.4 is a residual group obtained by removing two NCO groups from diisocyanate; and n is 1 or more,in formula (1), Y being replaced with a triazine ring represented by ##STR5## in the range of 0 to 15%, the polyuretdione having a latent NCO group content of 12 to 21% by weight, a weight-average molecular weight of 2000 to 20000 and a melting point of 60.degree. to 140.degree. C., and being not blocked at 40.degree. C. or less. The straight-chain crystalline polyuretdione of the present invention can be used as a hardener for powder coatings and does not cause a bad smell due to a blocking agent during baking of coating.Type: GrantFiled: November 18, 1996Date of Patent: August 18, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Kenshi Sugimoto, Shinji Suzuki, Ichiro Ibuki
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Patent number: 5789519Abstract: The present invention is directed to a polyisocyanate mixture whichi) is prepared from a monomeric starting material containinga) 95 to 100% by weight, based on the weight of a) and b), of an aliphatic diisocyanate having 4 to 18 carbons in the hydrocarbon chain andb) 0 to 5% by weight, based on the weight of a) and b), of a diisocyanate other component a),ii) has an equivalent weight that is at least 30% greater than the average molecular weight of the monomeric starting material and a viscosity of greater than 10,000 to 100,000 mPa.s when determined at 25.degree. C. on a sample having a solids content of 100% and containing less than 2% by weight of unreacted diisocyanates a) and b), andiii) contains isocyanurate groups and allophanate groups in a molar ratio of 10:1 to 1:10, wherein the allophanate groups are derived from urethane groups that are the reaction product of starting material i) with 0.01 to 0.6 moles, per mole of starting material i), of a monoalcohol having a molecular weight of up to 2500.Type: GrantFiled: April 12, 1996Date of Patent: August 4, 1998Assignee: Bayer CorporationInventors: William E. Slack, Douglas A. Wicks
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Reactivity improvement of urethane prepolymers of allophanate-modified diphenylmethane diisocyanates
Patent number: 5783652Abstract: This invention relates to mixtures of urethane prepolymers of allophanate-modified diphenylmethane diisocyanates with epoxides. The addition of the epoxide increases the reactivity of these prepolymers. It is now possible to form polyurethanes from these mixtures based on prepolymers of diphenylmethane diisocyanates wherein less catalyst is necessary.Type: GrantFiled: November 4, 1997Date of Patent: July 21, 1998Assignee: Bayer CorporationInventors: James W. Rosthauser, William E. Slack -
Patent number: 5777040Abstract: Curable compositions containing new classes of 1,3,5-triazine compounds as crosslinkers are disclosed, which compounds are of the general formula ##STR1## wherein each of Y, Z and optionally X are independently selected from a group of the formula (II), (III) and/or (IV) ##STR2## and wherein A, D, Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are as defined herein.Type: GrantFiled: July 3, 1997Date of Patent: July 7, 1998Assignee: Cytec Technology Corp.Inventors: Subban Ramesh, Laurence Lyman Williams, Ram Baboo Gupta, Lon-Tang Wilson Lin
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Patent number: 5777061Abstract: The present invention is directed to a powder coating composition containing as binderA) a polyisocyanate component which contains blocked isocyanate groups, is present in powder form, is solid below 40.degree. C. and liquid above 150.degree. C., and contains one or more polyisocyanatesi) having a blocked NCO content (calculated as NCO, MW 42) of 5 to 25% by weight andii) containing fluorine (calculated as F, AW 19) in an amount of 0.01 to 20% by weight,wherein the preceding percentages are based on the solids content of the polyisocyanate mixture andB) a polyhydroxyl component containing one or more high molecular weight polyols.Type: GrantFiled: February 14, 1996Date of Patent: July 7, 1998Assignee: Bayer CorporationInventors: Kenneth P. Yonek, Lanny D. Venham, Philip E. Yeske, Edward P. Squiller
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Patent number: 5777024Abstract: An allophanate-modified urethane resin is formed by reacting an allophanate-modified isocyanurate with one or more hydroxy-functional olefinic compounds, such as hydroxy-functional acrylates, methacrylates, allyl ethers, or vinyl ethers. Such resins typically have relatively low viscosities and can be used to make coating compositions for surfaces such as wood, cement, vinyl, plastic, metal, and glass on such diverse products as flooring, vinyl tiles and sheets, fiber optics, and plastic. Such coating compositions are typically curable by thermal processes or by high-energy irradiation, including UV/visible light or electron beam irradiation.Type: GrantFiled: April 30, 1997Date of Patent: July 7, 1998Assignee: The Valspar CorporationInventors: T. Howard Killilea, Donald W. Boespflug, Paul H. Stenson
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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: 5770674Abstract: The present invention is directed to a method of forming a gasket around a substrate from a novel polyurethane/urea composition via the RIM process. Window gaskets may be produced by this method. These novel polyurethane/urea compositions comprise the reaction product of a (cyclo)aliphatic polyisocyanate having a viscosity of less than about 25,000 mPa.multidot.s at 25.degree. C. and a NCO functionality of 2.0 to 4.0 with an isocyanate-reactive component comprising b1) a relatively high molecular weight organic compound containing hydroxyl groups, amine groups, or mixtures thereof; and b2) a low molecular weight chain extender selected from the group consisting of diols, primary amines, secondary amines, aminoalcohols, and mixtures thereof; in the presence of a catalyst. The isocyanate and isocyanate-reactive components are selected such that the crosslinking density of the resultant polyurethane/urea composition is at least 0.3 moles/kg.Type: GrantFiled: November 5, 1996Date of Patent: June 23, 1998Assignee: Bayer CorporationInventors: Ronald A. Cageao, A. Donald Meltzer, Brian R. Suddaby
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Patent number: 5767220Abstract: The present invention relates to ethylenically unsaturated polyurethanes which are substantially free from isocyanate groups and havea) a total content of (meth)acryloyl groups (calculated as C=C, MW 24) of 1 to 20% by weight.b) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 20% by weight andc) an isocyanurate group content (calculated as N.sub.3,C.sub.3,O.sub.3, MW 126) of up to 18% by weight,in which the allophanate and isocyanurate groups are prepared from aliphatic polyisocyanates.The present invention also relates to a one-component coating composition containing these ethylenically unsaturated polyurethanes.Type: GrantFiled: August 25, 1997Date of Patent: June 16, 1998Assignee: Bayer CorporationInventors: Lanny D. Venham, Arthur W. Mason, Michael K. Jeffries, Michael J. Dvorchak
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Patent number: 5760107Abstract: An electrodepositable composition is provided comprising:(A) a non-gelled cationic resin which is derived from a polyepoxide and which contains in the resin molecule cationic salt groups and active hydrogen groups selected from aliphatic hydroxyl and primary and secondary amino; and present as a separate component(B) a fully capped polyisocyanate curing agent containing substantially no free isocyanate groups. The electrodepositable composition contains from about 0.02 to 1.0 milliequivalents phenolic hydroxyl groups per gram of resin solids, and from about 0.1 to 2.0 milliequivalents beta-hydroxy ester groups per gram of resin solids. The composition provides excellent corrosion resistance when electrodeposited over steel substrates, and does not require lead in the formulation nor the use of a conventional chrome rinse for the steel substrate pretreatment before electrodeposition.Type: GrantFiled: October 1, 1996Date of Patent: June 2, 1998Assignee: PPG Industries, Inc.Inventors: Joseph T. Valko, Philippe Faucher, Richard F. Karabin, Thomas C. Moriarity, V. Eswarakrishnan, Ellor J. Van Buskirk, Gregory J. McCollum, Raphael O. Kollah
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Patent number: 5760142Abstract: Epoxide-amine dendrimers synthesized by a repetitive and step-wise addition reaction of epoxides comprising functional moieties which are available for conversion into amino groups followed by a reaction of these groups to primary amino moieties. The amino terminated dendrimers are reacted with (2,3-epoxypropoxy) methacrylate, a monoepoxide and/or a monoisocyante. The methacrylate terminated dendrimers are polymerizable using redox initiators and/or photoinitiators. The resulting dendrimers show a very low volume shrinkage from that of the starting materials, on the order of less than about 5 percent by volume.Type: GrantFiled: December 4, 1996Date of Patent: June 2, 1998Assignee: Dentsply DeTrey G.m.b.H.Inventor: Joachim E. Klee
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Patent number: 5756557Abstract: A method for preparing a polyurethane foam which comprises reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, a cell stabilizer and a catalyst composition comprising a compound represented by the following formula I or II, or any blend of compounds I and II.Type: GrantFiled: May 6, 1997Date of Patent: May 26, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Michael John Kimock, Mark Leo Listemann
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Patent number: 5750727Abstract: A polyisocyanate composition, comprising:A) from 55 to 87% by weight of a polyisocyanate which contains uretdione groups;B) from 10 to 30% by weight of blocking agent,C) from 3 to 30% by weight of polyol having more than two hydroxyl groups and/or chain extender having more than two hydroxyl groups, wherein the polyisocyanate contains more than two terminal, partially or fully blocked isocyanate groups and has a molecular weight of from 1000 to 10,000.Type: GrantFiled: February 12, 1996Date of Patent: May 12, 1998Assignee: Huels AktiengesellschaftInventor: Rainer Gras
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Patent number: 5750257Abstract: An insulated electrical wire coated with a polyamide-imide insulating material which is a copolymer of anhydrotrimellitic acid, aliphatic and aromatic dicarboxylic acids and a diisocyanate, with a molar ratio of the acids to the diisocyanate of from about 0.9:1.0 to about 1.1:1.0 and optionally further containing from about 1 part wt. to about 30 parts wt. of an epoxy resin per each 100 parts of the copolymer. Optionally the aforementioned insulation can be an interior, first coating, coated by a second coating of a polyamide, polyamide-imide, and when the first coat does not contain an epoxy, then a polyimide.Type: GrantFiled: June 27, 1996Date of Patent: May 12, 1998Assignees: Optec Dai-Itchi Denko Co., Ltd., Dainichiseika Color & Chemicals Mfg. Co., Ltd.Inventors: Hideo Doshita, Masahiro Koyano, Akihiro Goto, Kazuhisa Ishimoto, Makoto Tai
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Patent number: 5750629Abstract: The present invention relates to a process for preparing pure bis(isocyanatoalkyl)monouretdiones corresponding to formula (I) ##STR1## wherein R represents identical or different, linear or branched alkyl groups having 4 to 9 carbon atoms,by oligomerizing at least a portion of the isocyanate groups of aliphatic diisocyanates in the presence of catalysts which accelerate the dimerization of isocyanate groups, terminating the reaction at the desired degree of oligomerization, removing unreacted excess diisocyanate by extraction or thin film distillation to obtain a distillation residue, subjecting the distillation residue to thin film distillation at a temperature of 160.degree. to 220.degree. C. and a pressure of 0.01 to 1.0 mbar and obtaining bis(isocyanato-alkyl)monouretdiones corresponding to formula (I) as the distillate.Type: GrantFiled: January 23, 1997Date of Patent: May 12, 1998Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Laas, Reinhard Halpaap, Josef Pedain, Klaus Konig
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Patent number: 5747627Abstract: A room temperature curing polyurethane composition comprises a polyisocyanate compound or polyurethane prepolymer (A), an oxazolidine compound (B) having at least one oxazolidine ring, a compound (C) for accelerating the opening of the oxazolidine ring, and optionally a modified carbodiimide (D). The inventive polyurethane composition excels in storage stability and freedom of foaming when curing.Type: GrantFiled: August 19, 1996Date of Patent: May 5, 1998Assignee: The Yokohama Rubber Co., Ltd.Inventors: Kazushi Kimura, Toshimitsu Takeda, Hiroyuki Hosoda, Kazunori Ishikawa, Hiroyuki Okuhira
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Patent number: 5744568Abstract: The present invention relates to a process for the production of a polyurethane lens, which comprisesthe step (a) of providing a polyisocyanate compound and two or more polythiol compounds which have different reaction rates with the polyisocyanate compound and adding an alkyltin halide compound to the above polyisocyanate compound, and, after the step (a),the step (b) of mixing the polyisocyanate compound and the two or more polythiol compounds together with the alkyltin halide compound of the general formula (I) to allow them to react, and obtaining a polyurethane lens.Type: GrantFiled: February 18, 1997Date of Patent: April 28, 1998Assignee: Hoya CorporationInventors: Masahisa Kosaka, Yukio Kageyama
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Patent number: 5744569Abstract: In one-component and two-component polyurethane coating compositions comprising at least one reactive component capable of reacting with polyisocyanates, the reactive component is a compound A) containing an isocyanate group, a urethane, thiourethane or urea group and two capped isocyanate-reactive groups.Type: GrantFiled: June 28, 1996Date of Patent: April 28, 1998Assignee: BASF AktiengesellschaftInventors: Bernd Bruchmann, Hans Renz, Gunter Mohrhardt
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Patent number: 5739251Abstract: The present invention relates to ethylenically unsaturated polyurethanes which are substantially free from isocyanate groups and havea) a content of .beta.,.gamma.-ethylenically unsaturated ether groups (calculated as C.dbd.C, MW 24) incorporated through allophanate groups of 0.5 to 10% by weight,b) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 20% by weight andc) a total content of ethylenically unsaturated groups of (calculated as C.dbd.C, MW 24) of 1 to 15% by weight.The present invention also relates to ethylenically unsaturated polyisocyanates which contain allophanate groups and havei) an NCO content of 5 to 25% by weight,ii) a content of .beta.,.gamma.-ethylenically unsaturated ether groups (calculated as C.dbd.C, MW 24) incorporated through allophanate groups of 0.5 to 15% by weight andiii) an allophanate group content (calculated as N.sub.2 C.sub.2 HO.sub.3, MW 101) of 1 to 30%.Type: GrantFiled: March 27, 1997Date of Patent: April 14, 1998Assignee: Bayer CorporationInventors: Lanny D. Venham, Arthur W. Mason, Michael K. Jeffries, Michael J. Dvorchak
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Patent number: 5736609Abstract: The present invention discloses a sulfur-containing urethane-based resin composition of the present invention is directed to a sulfur-containing urethane-based resin composition which comprises a polythiol compound represented by formula (1): ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 each is a hydrogen atom or a mercapto group; x, y and z each is an integer of 0 to 8; and in their combinations, formula (1) has at least two mercapto groups,a polyiso(thio)cyanate compound, and a compound having two or more reactive unsaturated groups in an amount of 30 to 70% by weight based on the total weight of the composition, or a sulfur-containing urethane-based resin composition which comprises the polythiol compound represented by formula (1), the polyiso(thio)cyanate compound, the compound having two or more reactive unsaturated groups in an amount of 10 to 70% by weight based on the total weight, and a photopolymerization catalyst.Type: GrantFiled: June 14, 1996Date of Patent: April 7, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yoshihiro Irizato, Shinichi Umeda, Yoshinobu Kanemura, Teruyuki Nagata
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Patent number: 5731398Abstract: A black colorant composition useful for coloring polyurethanes is provided having a red benzothiazole azo colorant which, when combined with a complementary blue and yellow colorant, exhibits low flairing.Type: GrantFiled: May 31, 1996Date of Patent: March 24, 1998Assignee: Milliken Research CorporationInventors: Mark Edward Ragsdale, David Jesse Moody, Eric B. Stephens
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Patent number: 5731397Abstract: Spray polyurea elastomer systems have improved adhesion to a substrate with the incorporation of a functional alkoxy silane and water. Such systems typically also include a quasi-prepolymer of an isocyanate and an active hydrogen-containing material, and at least one amine resin, and preferably an amine-terminated chain extender. The system may also benefit from the incorporation of a higher than usual proportion of 2,4'-isomer methylene diisocyanate (MDI). The viscosity of the various components, as well as various processing characteristics, may be improved by the addition of an alkylene carbonate. The spray polyurea elastomer systems of this invention also have improved abrasion and impact resistance.Type: GrantFiled: April 16, 1996Date of Patent: March 24, 1998Assignee: Huntman Petrochemical CorporationInventors: Dudley J. Primeaux, II, Kenneth C. Anglin
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Patent number: 5726274Abstract: Polyurethane polymers having pendant carbamate groups are disclosed. The polymers are prepared by:(a) reacting a mixture comprising a polyol having at least one pendant carbamate group and a polyisocyanate to form a polyurethane having pendant carbamate groups, and(b) optionally, capping the polyurethane from (b) with an active hydrogen-containing capping agent.Type: GrantFiled: October 24, 1995Date of Patent: March 10, 1998Assignee: BASF CorporationInventors: Gregory L. Menovcik, Walter H. Ohrbom
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Patent number: 5726273Abstract: The present invention relates to heat-curable, cyclic isocyanate addition productsi) which are the reaction products of a polyisocyanate having two or more isocyanate groups with a compound containing two or more isocyanate-reactive groups andii) in which at least 10% by weight of the reaction products are in the form of cyclic groups containing urea and/or urethane groups.The present invention also relates to a process for the preparation of these cyclic isocyanate addition products and to the products obtained by curing these compositions at elevated temperatures, e.g., coatings, adhesives, molded articles, elastomers and foams.Type: GrantFiled: June 5, 1996Date of Patent: March 10, 1998Assignee: Bayer CorporationInventors: Douglas A. Wicks, Robert J. Kumpf, Sze-Ming Lee, Duane B. Priddy, Jr., Philip E. Yeske
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Patent number: 5726285Abstract: Condensation and addition polymers which comprise as structural repeating unit N,N'-bridged bistetramethylpiperidyloxy groups of the formula I ##STR1## in which m is 2 or 3 are suitable as light stabilizers and other stabilizers for organic materialType: GrantFiled: August 2, 1996Date of Patent: March 10, 1998Assignee: BASF AktiengesellschaftInventors: Alexander Aumuller, Hubert Trauth
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Patent number: 5723564Abstract: A process for the preparation of isocyanurate group-containing polyisocyanates in solvents which are inert towards isocyanate groups by reacting 0.2 to 1.5% of the isocyanate groups of diisocyanatotoluene with an aliphatic monohydric alcohol having 6 to 22 carbon atoms and subsequently trimerizing at least a portion of the isocyanate groups of the urethanized diisocyanates in the form of 40 to 70 wt. % solutions in lacquer solvents which are inert towards isocyanate groups, and the use of these polyisocyanates in two-component polyurethane coating compositions.Type: GrantFiled: June 21, 1996Date of Patent: March 3, 1998Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Carl-Gerd Dieris, Wolfgang Kremer, Bernd Riberi
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Patent number: 5714564Abstract: The present invention is directed to a polyisocyanate containinga) polyisocyanates containing isocyanurate groups and corresponding to formula 1 ##STR1## wherein R represents the residue obtained by removing one of the isocyanate groups from 4-isocyanatomethyl-1,8-octamethylene diisocyanate,optionally in admixture withb) unreacted 4-isocyanatomethyl-1,8-octamethylene diisocyanate,c) higher homologs of the polyisocyanates set forth in formula 1 containing more than one isocyanurate group andd) a polyisocyanate containing allophanate groups.The present invention also relates to the use of these polyisocyanate mixtures, optionally in blocked form, as an isocyanate component in one- or two-component coating compositions.Type: GrantFiled: August 21, 1996Date of Patent: February 3, 1998Assignee: Bayer CorporationInventor: Myron W. Shaffer
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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
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Patent number: 5710191Abstract: A method for preparing a polyurethane foam which comprises reacting an organic polyisocyanate and a polyol in the presence of a blowing agent, a cell stabilizer and a catalyst composition comprising at least one compound of either of the following formulas IA and IB: ##STR1## where R is hydrogen, methyl or hydroxymethyl. The preferred catalysts comprise 3-hydroxymethyl quinuclidine, 3-methyl-3-hydroxymethyl quinuclidine and 4-hydroxymethyl quinuclidine.Type: GrantFiled: May 21, 1996Date of Patent: January 20, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Mark Leo Listemann, Kristen Elaine Minnich, Brian Eugene Farrell, Lisa Ann Mercando, Michael John Kimock, James Dudley Nichols
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Patent number: 5710240Abstract: The invention relates to compounds of the formula I ##STR1## in which n is a number in the range from 1 to 100; X is --R.sup.7 --, --CO--, --CO--CO--, --CO--R.sup.2 --CO--, --CO--NH--R.sup.5 --NH--CO--, --CO--O--R.sup.6 --O--CO-- or ##STR2## where p is a number in the range from 0 to 6, X' is O or a direct bond, E is C.sub.1 -C.sub.12 alkyl, phenyl, C.sub.7 -C.sub.12 phenylalkyl or C.sub.5 -C.sub.12 cycloalkyl, and E' is hydrogen or is as defined for E;Z, when X is R.sup.7, is O or NR.sup.1 ; Z, when X is ##STR3## is O; and Z, in all other cases, is O, NH or NR.sup.1 ;R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.8 alkanoyl, benzoyl or C.sub.1 -C.sub.4 alkyl-substituted benzoyl;R.sup.2 and R.sup.7 are C.sub.1 -C.sub.18 alkylene; C.sub.2 -C.sub.18 alkylene which is interrupted by O or S; phenylene; a mixed aromatic/aliphatic radical containing 7 to 12 carbon atoms; naphthylene; or an --R.sup.4 --D--R.sup.4 -- radical;R.sup.Type: GrantFiled: February 26, 1996Date of Patent: January 20, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Alfred Steinmann
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Patent number: 5705594Abstract: Liquid polyamine crosslinking agent formulations based on trimerized toluylene 2,4- and/or 2,6-diisocyanate, with formation of an isocyanurate structure and hydrolysis of the isocyanate groups to amine groups, are described. The novel crosslinking agent formulations have a content of 40 to 80% of the total weight of the solids content of the crosslinking agent formulation of 1,3,5-tris-(3-amino-4-methyl-phenyl,2-methyl-3-aminophenyl) isocyanurate (I) which is not further condensed, and a content of not more than 1.0% of the total weight of the crosslinking agent formulations of toluylene-2,4- and/or -2,6-diamine (III). For the preparation, toluylene diisocyanate is trimerized, to form the isocyanurate structure, until 10 to 25% of the NCO groups have been reacted.Type: GrantFiled: December 16, 1996Date of Patent: January 6, 1998Assignee: Bayer AktiengesellschaftInventors: Klaus Konig, Otto Neuner, Werner Rasshofer
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Patent number: 5691438Abstract: Polyisocyanates which have 1,2,4,-triazole-blocked isocyanate groups and a blocked isocyanate group content of 7 to 14 wt. % and which are reaction products ofA) a polyisocyanate component selected from (i) lacquer polyisocyanates based on (cyclo)aliphatic diisocyanates or (ii) mixtures of these lacquer polyisocyanates with cycloaliphatic diisocyanates of a maximum molecular weight of 300,B) 50 to 80 equivalent-%, based on the isocyanate groups of component A), of a monofunctional isocyanate group blocking agent containing at least 90 wt. % of 1,2,4-triazole,C) 10 to 30 equivalent-%, based on the isocyanate groups of component A), of a polyester component having an OH number of 56 to 250 andD) 0 to 20 equivalent-%, based on the isocyanate groups of component A), of selected hydrazine derivatives.The present invention is also directed to the use of these blocked polyisocyanates as crosslinking agents in one-component polyurethane stoving lacquers.Type: GrantFiled: April 17, 1996Date of Patent: November 25, 1997Assignee: Bayer AktiengesellschaftInventors: Eberhard Konig, Theodor Engbert