With Organic Nitrogen Reactant Which Contains Two Nh, =nh, Or Hnh Groups Patents (Class 528/61)
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Patent number: 4868268Abstract: Novel polyurethanes are prepared by reacting(a) an organic diisocyanate of formula ##STR1## wherein M represents --CH.dbd.CH--; --N.dbd.N--; --CH.dbd.N--; ##STR2## or and where R.sub.1 through R.sub.4 may be the same or different and represent hydrogen, halogen, CN, CF.sub.3 or saturated aliphatic C.sub.1 -C.sub.12 alkyl residues which may be interrupted by ether hydrogen atoms with(b) compounds of molecular weights of from between 400 and 10,000 and which contain at least two active hydrogen atoms reactive toward isocyanate groups.Type: GrantFiled: November 3, 1988Date of Patent: September 19, 1989Assignee: Bayer AktiengesellschaftInventors: Hanns P. Muller, Roland Gipp
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Patent number: 4866103Abstract: A polyisocyanate composition, suitable for use in the production of elastomers by the RIM process, said composition being the product of reacting an alcohol and/or thiol having an average hydroxyl and/or thiol functionality of from about 1.5 to about 4 and an average hydroxyl and/or thiol equivalent weight of at least 500 with at least 2 equivalents, per hydroxyl and/or thiol equivalent, of an organic polyisocyanate under such conditions that at least about 20% of the initially formed urethane and/or thiourethane groups are converted to allophanate and/or thioallophanate groups.Type: GrantFiled: September 16, 1988Date of Patent: September 12, 1989Assignees: ICI Americas Inc., Imperial Chemical Industries PLCInventors: Edward F. Cassidy, Herbert R. Gillis, Jan W. Leenslag, Alain Parfondry
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Patent number: 4857561Abstract: The present invention is directed to a polyisocyanate comprising the reaction product of(a) an isocyanate selected from the group consisting of methylenebis(phenylisocyanate), polymethylenepoly(phenylisocyanate), and mixtures thereof, and(b) a polyester polyol having a hydroxyl functionality of from 2 to 3 and a molecular weight of from about 750 to about 3500, said polyester polyol prepared by reacting neopentyl glycol and adipic acid,the isocyanate group content of said reaction product from about 14% to about 28% by weight. The invention is also directed to a RIM process using such prepolymers.Type: GrantFiled: August 30, 1988Date of Patent: August 15, 1989Assignee: Mobay CorporationInventors: Robson Mafoti, Neil H. Nodelman
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Patent number: 4855394Abstract: Condensates based on substituted ureas, their reaction products with di- and/or polyisocyanates, derivatives of di- and/or polycarboxylic acids or p-substituted phenols and/or their methylol derivatives, their preparation and their use. These condensates each contain two or more cyclic urea units and can be prepared either by reacting primary di- or polyamines with ureas and reacting the product with predominantly CH-acidic aldehydes or by reacting primary amines with isocyanates and reacting the product with predominantly CH-acidic aldehydes in the presence of an acidic catalyst. The said condensates and their reaction products are useful for the preparation of heat-curable coating materials and of binders for cathodic electrocoating.Type: GrantFiled: January 25, 1989Date of Patent: August 8, 1989Assignee: BASF AktiengesellschaftInventors: Ulrich Goeckel, Harro Petersen, Rolf Osterloh, Eberhard Schupp, Werner Loch, Thomas Schwerzel
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Patent number: 4855384Abstract: An isocyanate-terminated sulfocompound is the reaction product of a polyisocyanate and a sulfopolyol or sulfopolyamine which is the reaction product of one mole of a sulfodicarboxylic acid and about two moles of an aliphatic polyol or polyamine having two or more hydroxyl or amino groups attached to a linear chain and having a molecular weight of up to 2000. The sulfocompound can be reacted with ethylenically-unsaturated alcohols, water, polyamines, or polyols, to give ethylenically-unsaturated sulfocompounds, sulfopolyureas or sulfopolyurethanes.Type: GrantFiled: February 12, 1988Date of Patent: August 8, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventor: Wayne K. Larson
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Patent number: 4849458Abstract: A hydrophilic, segmented polyether polyurethane-urea that exhibits an increase in tensile strength and elongation when wet with water and is capable of forming visually clear films permeable to water vapor is disclosed.Type: GrantFiled: June 17, 1988Date of Patent: July 18, 1989Assignee: Matrix Medica, Inc.Inventors: Andrew M. Reed, Ian N. Askill, Willis W. Weber
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Patent number: 4847321Abstract: The present invention relates to a process for the production of storable thermosetting polyurethane-polyurea compositions wherein a storable isocyanate component stabilized by a surface coating and a polyol and/or polyamine component are separately prepared. A one-component polyurethane-polyurea reactive mixture is formed by mixing just before the intended use the separate components under mild shear forces at a temperature below the thickening temperature of the final reactive mixture.Type: GrantFiled: August 8, 1988Date of Patent: July 11, 1989Assignee: Bayer AktiengesellschaftInventors: Heinrich Hess, Gerhard Grogler, Richard Kopp, Manfred Bock, Werner Clarenz
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Patent number: 4841007Abstract: Non-blocking, hemocompatible, thermoplastic, fluorinated polyetherurethanes and a method for their preparation from fluorinated polyether glycols, isocyanates, chain extenders and a non-fluorinated polyol. The method includes two steps in which the fluorinated glycol is reacted initially with the diisocyanate to give a prepolymer having terminal isocyanate groups, and the prepolymer is then reacted with the extender and non-fluorinated polyol. Medical devices are fabricated from the fluorinated polyetherurethane.Type: GrantFiled: March 28, 1988Date of Patent: June 20, 1989Assignee: Becton Dickinson and CompanyInventors: Richard J. Zdrahala, Marc A. Strand
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Patent number: 4831098Abstract: An antistatic agent containing a cationic and/or amphoteric, water-soluble or water-dispersible and heat-reactive blocked urethane prepolymer as an essential component, said prepolymer having at least one cationic group and/or at least one amphoteric group in its molecule and having isocyanate groups blocked with a thermally dissociable blocking agent. The antistatic agent is applicable to various materials and can give the antistatic property with the water repellency, which can be kept for a long term, to the materials.Type: GrantFiled: June 10, 1987Date of Patent: May 16, 1989Assignee: Dai-ichi Kogyo Seiyaku Co., Ltd.Inventors: Akio Watanabe, Toshiaki Doyama
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Patent number: 4816529Abstract: Ester-modified poly(alkylene carbonate) polyahls comprising the residues of at least one polyahl, polyalkyleneoxy moieties, poly(alkylene carbonate) moieties, the residues of at least one ester of a carboxylic acid, and a plurality of active hydrogen end group are disclosed. The ester-modified poly(alkylene carbonate) polyahl has a number average molecular weight higher than the number average molecular weight of any known poly(alkylene carbonate) polyahl comprising the same monomeric components. Also disclosed are isocyanate-functional prepolymers of these ester-modified poly(alkylene carbonate) polyahls formed by reactions of the ester-modified poly(alkylene carbonate) polyahls of this invention with excess organic polyisocyanates. Urethane/urea polymers formed by the reactions of the isocyanate-functional prepolymers with polyahls are also disclosed.Type: GrantFiled: November 17, 1986Date of Patent: March 28, 1989Assignee: The Dow Chemical CompanyInventor: Robert F. Harris
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Patent number: 4812524Abstract: Novel polyurea/polyurethane two-component adhesive compositions are disclosed which comprise the reaction product of (a) a blend of an amine terminated polybutadiene and a polyhydroxybutadiene with (b) an aliphatic or aromatic di- or polyisocyanate and optionally chain extenders, tackifiers, coupling agents fillers and curingly effective amounts of catalyst.Type: GrantFiled: May 8, 1986Date of Patent: March 14, 1989Assignee: Pony Industries, Inc.Inventor: Jamil Baghdachi
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Patent number: 4803257Abstract: A polyurethane adhesive composition which comprises a mixture of a polyisocyanate blocked with a phenolic blocking agent and a polyamine curing agent and optionally may contain a polyepoxide is described.Type: GrantFiled: April 24, 1987Date of Patent: February 7, 1989Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4798879Abstract: A polyurethane sealant composition is made from a polyurethane prepolymer having blocked isocyanate groups. A 1,8-diaza bicyclo(5:4:0)undecene-7 (DBU) catalyst or a derivative thereof is utilized in association with an amine curing agent having at least two primary amine groups to achieve a relatively fast cure time. The catalyst is a true catalyst in that it merely aids in unblocking the isocyanate groups whereby the curing agent can react therewith.Type: GrantFiled: March 25, 1987Date of Patent: January 17, 1989Assignee: The B.F. Goodrich CompanyInventors: Steven L. Hannah, Maureen R. Williams, Thomas W. Greenlee
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Patent number: 4798880Abstract: A shaped article of a polyurethane-urea spandex formed from polyalkaneether glycol that was capped with tertiary aralkyl diisocyanate and then chain extended with a specific tricomponent diamine mixture has unexpectedly good heat settability. The diamine mixture comprises 25 to 80% of hydrogenated m-phenylenediamine, 10 to 50% of hydrogenated p-phenylendiamine and 10 to 30% of tetrachloro-p-xylylenediamine.Type: GrantFiled: December 30, 1987Date of Patent: January 17, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gary A. Lodoen
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Patent number: 4778845Abstract: A one-component adhesive and/or sealing mass which is stable and pumpable at temperatures up to 30.degree. C. containsat least one prepolymer on the basis of a polyurethane, which contains from 0.1 to 15 percent by weight, referred to the prepolymer, of free, reactive isocyanate groups, andat least one with heat activatable hardener.Thereby the stoichiometric ratio between said prepolymer and said hardener is chosen in such a way that only a partial cross-linkage is possible during heating said mass to temperatures from 60.degree. C. to 180.degree. C., and that a product is obtained having from high viscous to plastic characteristics.The inventive masses may be used for bonding and/or sealing of one or more materials of the same or different origin to a composite.Type: GrantFiled: June 4, 1987Date of Patent: October 18, 1988Assignee: Sika AG, vorm. Kaspar Winkler & Co.Inventors: Hans-Peter Tschan, Lutz-Dieter Zabel, Ueli Pfenninger
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Patent number: 4777220Abstract: The present invention is directed to a process for the production of prepolymers containing free tertiary isocyanate groups by reacting(a) an organic diisocyanate containing one isocyanate group attached to a primary aliphatic carbon atom and an isocyanate group attached to a tertiary aliphatic or cycloaliphatic carbon atom with(b) a polyester polyol having a molecular weight of 800 to 12,000 and a hydroxyl functionality of 2 to 6 at an NCO/OH equivalent ratio of 1.6:1 to 2:1 to provide prepolymers having a molecular weight of about 1000 to 3000 and an NCO content of about 4 to 12%.The present invention is also directed to the prepolymers containing free isocyanate groups obtained by this process and to their use for the production of polyurethane lacquers and coatings.Type: GrantFiled: February 3, 1988Date of Patent: October 11, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhard Halpaap, Manfred Bock, Josef Pedain, Gerhard Klein, Dieter Arlt
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Patent number: 4772677Abstract: This invention relates to highly stretchable elasthane fibres (Spandex fibres) based on segmented polyurethane(urea)s with improved elastic properties and high resistance to microbial degradation, characterized in that the polyurethane(urea)s used for the synthesis of the elasthanes are prepared from mixtures of relatively high molecular weight copolyester diols in the molecular weight range of from 2,500 to 4,000 and relatively high molecular polytetrahydrofurandiols in the molecular weight range of from 1,500 to 3,000.Type: GrantFiled: November 23, 1987Date of Patent: September 20, 1988Assignee: Bayer AktiengesellschaftInventors: Michael Kausch, Carlhans Suling, Hans Schroer, Karlheinz Wolf, Rudi Dauscher
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Patent number: 4772643Abstract: A crosslinked and chain extended urethane-epoxy copolymer coating with high performance properties typical of two part urethane solution coatings results from cure at ambient temperatures (e.g. 70.degree. F.) when the two aqueous systems are merely mixed, stirred and spread at the site. One aqueous system is a dispersion of polyepoxides. The other aqueous system is a primary amine-terminated urethane oligomer in which no less than about 25% and no more than about 40% of the amine functionality is substituted by a salt of a volatile acid which aids dispersion of the oligomer. Minimal organic solvent is present, and as the acid evaporates, the primary amine is restored for linking with the epoxy groups.Type: GrantFiled: December 11, 1987Date of Patent: September 20, 1988Assignee: Tennant CompanyInventors: G. Dale Ernst, Alan R. Schuweiler
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Patent number: 4769435Abstract: The invention concerns a process for the manufacture of thermoplastic polyurethanes wherein an organic polyisocyanate is made to polymerize with a polyol (reactive with same isocyanate) in the presence of a chain extending agent having a molecular weight lower than 400, under continuous stirring, at a temperature higher than 150.degree. C. and for a time sufficient to obtain a product having a melt flow index lower than 25 g/10'.Type: GrantFiled: July 16, 1987Date of Patent: September 6, 1988Assignee: Ausimont S.p.A.Inventors: Gianflavio Lunardon, Lino Credali, Ermanno Benetti, Carlo Mulas
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Patent number: 4767796Abstract: Disclosed are novel storage stable liquid compositions derived from heating a liquefied methylenebis(phenyl isocyanate) with a minor proportion of a cycloalkane diol.The molded polyurethanes produced using the above liquid isocyanates are characterized by excellent resistance to elevated temperatures. In fact, their heat resistance is superior to similarly constituted prior art materials.Type: GrantFiled: December 17, 1987Date of Patent: August 30, 1988Assignee: The Dow Chemical CompanyInventors: Dolunay I. Cortelek, James R. Pritchard
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Patent number: 4767836Abstract: A storage stable polyurethane coating composition which may be heat cured under relatively mild conditions comprising an isocyanate which has been chemically blocked and a curing agent comprising a partially alkoxylated polyoxyalkylene amine is described.Type: GrantFiled: May 18, 1987Date of Patent: August 30, 1988Assignee: Texaco Inc.Inventor: Michael Cuscurida
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Patent number: 4758604Abstract: This invention is an active hydrogen-containing composition comprising(A) a relatively high equivalent weight liquid active hydrogen-containing material or mixture thereof having at least 50% of its active hydrogen containing groups in the form of primary and/or secondary amine groups;(B) a chain extender having an equivalent weight of about 31 to about 250 and about 2 active hydrogen-containing groups per molecule; and(C) from about 1 to about 30 parts, per 100 parts by weight of the composition, of an amide formed by the reaction of a C.sub.2 -C.sub.30 monocarboxylic acid with a relatively high equivalent weight amine-terminated polyether.Type: GrantFiled: April 7, 1987Date of Patent: July 19, 1988Assignee: The Dow Chemical CompanyInventor: Benny G. Barron
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Patent number: 4745170Abstract: This invention is a polyurethane and/or polyurea elastomer prepared in the reaction of:(a) an organic polyisocyanate;(b) a chain extender and(c) a polyether having a molecular weight from about 500 to about 10,000, which polyether is a block copolymer of ethylene oxide and butylene oxide comprising an internal poly(EO) block bonded on each side to a poly(BO) block, wherein oxybutylene moieties comprise from about 10 to about 90 percent of the total weight of the polyether.Type: GrantFiled: July 25, 1985Date of Patent: May 17, 1988Assignee: The Dow Chemical CompanyInventors: Kimbley A. Bushman, Michael K. Laughner
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Patent number: 4743632Abstract: Purified diisocyanate polyetherurethane prepolymers and process therefor. Polyetherurethane urea polymers prepared by mixing said prepolymers with an aqueous solution of an amino, ureido or hydroxy substituted amine or a like-substituted alpha-amino acid, and a method of using same as a space filling adhesive sealant in surgery.Type: GrantFiled: February 25, 1987Date of Patent: May 10, 1988Assignee: Pfizer Hospital Products Group, Inc.Inventor: N. Nash Marinovic
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Patent number: 4743672Abstract: A sag resistant two component polyurethane adhesive comprising a first polyisocyanate component and a second component comprising a polyol, a poly(alkylene oxide) polyamine and a polyurethane catalyst is described.Type: GrantFiled: February 26, 1987Date of Patent: May 10, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4740539Abstract: A two component structural adhesive which is composed of a mixture of an epoxy component which comprises a polyepoxide and a polyisocyanate and a hardener component which comprises a long chain, flexible polyamine and an epoxy resin homopolymerization catalyst is described.Type: GrantFiled: April 21, 1986Date of Patent: April 26, 1988Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4732919Abstract: This invention relates to a reaction injection molded elastomer made by reacting ingredients comprising a high molecular weight polyol or polyoxyalkylene polyamine, a chain extender and a quasi-prepolymer of a polyoxyalkylene polyamine and an aromatic isocyanate.Type: GrantFiled: November 6, 1986Date of Patent: March 22, 1988Assignee: Texaco Inc.Inventors: Robert A. Grigsby, Jr., Richard J. G. Dominguez, Wheeler C. Crawford
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Patent number: 4722966Abstract: A storage-stabile, radiation-hardenable, NCO-free aqueous emulsions based on ionic urethane-urea acrylates is disclosed. The emulsions are made up of partially acrylated cycloaliphatic polyisocyanates which have been acrylated by a hydroxyalkyl acrylate (to the extent of 10-60 equivalent-% NCO). These products are then reacted with polyhydroxy compounds (to the extent of 20-75 equivalent-% NCO), and then with sodium salts of aminocarboxylic acids (to the extent of 5-15 equivalent-% NCO), and finally they are reacted with water and/or aliphatic diamines (said aliphatic diamines in amounts corresponding to 1-5 equivalent-% NCO).Type: GrantFiled: July 18, 1986Date of Patent: February 2, 1988Assignee: Huls AktiengesellschaftInventor: Werner Flakus
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Patent number: 4721754Abstract: Compositions comprising blends of polyhydroxybutadiene homopolymers and amine terminated polybutadienes useful for the preparation of polyurea and/or polyurethane elastomers, sealants, coatings and binders are disclosed as well as a process for the preparation of the polyurea/polyurethanes.Type: GrantFiled: July 23, 1986Date of Patent: January 26, 1988Inventor: Jamil Baghdadchi
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Patent number: 4716209Abstract: An essentially isocyanate-free polyurethane polyurea polyethylenic oligomer is disclosed which is unusually strong and elastic. This oligomer is the reaction product of: (1) organic diisocyanate; (2) a stoichiometric deficiency of difunctional materials reactive therewith and consisting essentially of: (A) diol component selected from polycarbonate diol and polyoxyalkylene glycol, this diol component having a molecular weight of from 200 to 2000; (B) dihydric bisphenol-based alkylene oxide adduct containing from 2-10 alkylene groups per molecule; and (C) a diprimary diamine component selected from alkylene diamine and polyoxyalkylene diamine, this diamine component having a molecular weight of from about 70 to 800. Components (A) and (B) are present in a weight ratio of from 1:4 to 9:1 and component (C) is present to supply from 30 to 60 equivalent percent of the total equivalents of component (2).Type: GrantFiled: January 23, 1986Date of Patent: December 29, 1987Assignee: DeSoto, Inc.Inventors: Steven R. Schmid, Robert E. Ansel, Kevin P. Murray
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Patent number: 4705814Abstract: This invention relates to a reaction product of polyoxyalkylene polyamine and an isocyanate wherein the polyoxyalkylene polyamine is present in less than the stoichiometric amount.Type: GrantFiled: November 6, 1986Date of Patent: November 10, 1987Assignee: Texaco Inc.Inventors: Robert A. Grigsby, Jr., Richard J. G. Dominguez, George P. Speranza
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Patent number: 4701476Abstract: This invention is an improvement in a process for preparing polyurethane and/or polyurea polymers wherein an isocyanate terminated quasi-prepolymer is reacted with an active hydrogen-containing composition to form a polyurethane and/or polyurea polymer, the improvement comprising employing as the quasi-prepolymer a solution of an isocyanate terminated prepolymer in a monomeric polyisocyanate, wherein said isocyanate-terminated prepolymer is the reaction product of a polyisocyanate and a relatively high equivalent weight isocyanate-reactive material, and said isocyanate-terminated prepolymer has an average molecular weight of at least twice that of said relatively high equivalent weight isocyanate-reactive material.Type: GrantFiled: December 27, 1985Date of Patent: October 20, 1987Assignee: The Dow Chemical CompanyInventors: Donald J. Burchell, Jr., Richard D. Peffley
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Patent number: 4699968Abstract: Urethane elastomers are produced by reacting a prepolymer with a chain extender or cure agent in the presence of limited amounts of water without adverse effects on the physical properties of the cured polyurethane.Type: GrantFiled: April 18, 1986Date of Patent: October 13, 1987Assignee: The Firestone Tire & Rubber CompanyInventors: Edward L. Kay, Kenneth B. Roskos
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Patent number: 4695605Abstract: A structural adhesive which is particularly useful in vertical substrates is composed of a mixture of two components, the first component being an epoxy resin component comprising a poly epoxide and a polyisocyanate which has been allowed to react with less than an equivalent weight of a polyamine which is a primary or secondary polyamine and the second component being a hardener for the polyepoxide comprising a mixture of primary, secondary and tertiary amines, amido amines and phenolics.Type: GrantFiled: October 1, 1986Date of Patent: September 22, 1987Assignee: Ashland Oil, Inc.Inventor: Anil B. Goel
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Patent number: 4695618Abstract: A method for preparing polyurethane by spraying solventless, equal volume mixtures of:(a) a liquid polyisocyanate; polyisocyanurate or isocyanate terminated quasi-prepolymer; and(b) a curing agent comprised of a blend of from about 0 to 15% of a polyamine having an equivalent weight from about 30 to about 200, about 10 to 20% of a low molecular weight glycol having an equivalent weight of from about 30 to 200, about 40 to 80% of a relatively high molecular weight polyol or polyamine having an equivalent weight of about 350 to 2000, and about 1 to 20% of a synthetic zeolite molecular sieve, wherein the average equivalent weight of (b) is from about 150 to 500.Type: GrantFiled: May 23, 1986Date of Patent: September 22, 1987Assignee: Ameron, Inc.Inventor: Norman R. Mowrer
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Patent number: 4689356Abstract: This invention is a process for preparing polyurethane and/or polyurea elastomer comprising reacting a liquid, preformed isocyanate-terminated prepolymer, which prepolymer is the reaction product of a stoichiometric excess of a polyisocyanate and a relatively high equivalent weight isocyanate-reactive compound, with a chain extender mixture, which chain extender mixture comprises(a) a mixture comprising a hydroxyl-terminated chain extender and an aromatic amine terminated chain extender, and/or an aliphatic amine-terminated compound, or(b) a mixture comprising an aromatic amine-terminated chain extender and an aliphatic amine-terminated compound, wherein the isocyanate index is from about 70 to about 200.In this process, it is possible to prepare elastomers having excellent properties, particularly excellent flexural and thermal properties, which properties are difficult to obtain in a one-step process.Type: GrantFiled: December 10, 1985Date of Patent: August 25, 1987Assignee: The Dow Chemical CompanyInventors: Richard D. Peffley, John H. Spells, James A. Vanderhider
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Patent number: 4673722Abstract: A method of forming a high impact strength article of nylon/polyurea copolymer by reaction injection molding precursors of a polyurea prepolymer and a caprolactam together including the steps of prereacting a diisocyanate, a diamine and caprolactam to form a polyurea prepolymer having carbamyl caprolactam terminated end groups and then rapidly mixing the prepolymer with suitable amounts of caprolactam and a caprolactam alkali metal salt initiator and adding the mixture to a heated mold to polymerize the mixture and form the article.Type: GrantFiled: December 23, 1985Date of Patent: June 16, 1987Assignee: General Motors CorporationInventors: Zachariah G. Gardlund, MaryAnn Bator
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Patent number: 4671838Abstract: Preformed, energy-absorbing, scratch resistant, optical, flexible, and self-healing polyurethane sheets, which are adhesive under the influence of heat and pressure; bilayer glazing laminates and bilayer safety windshields including said sheets; wherein said polyurethane sheet is prepared preferably by reactive-casting on a horizontal support and formed preferably from a polyisocyanate monomer including about 2 to about 10 wt. % of urea groups.Type: GrantFiled: August 25, 1986Date of Patent: June 9, 1987Assignee: Saint-Gobain VitrageInventors: Jean L. Bravet, Daniel Colmon, Gerard Daude, Michel J. Moncheaux
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Patent number: 4663415Abstract: This invention relates to a process for the production of solid polyamines stabilized by a polyadduct covering and showing retarded reactivity comprising reacting(1) one or more solid organic polyamines in particulate form, said polyamines containing at least two primary and/or secondary amino groups and having melting points above 50.degree. C., and(2) from 0.1 to 25 equivalent % of isocyanate per amine equivalent of a water insoluble, difunctional and/or higher functional polyisocyanate,said reaction being conducted at a temperature below the melting point of said solid polyamine, and being conducted in the presence of(3) a liquid medium selected from the group consisting of(a) organic compounds containing two or more hydroxy groups and having molecular weights of from 62 to 10,000,(b) plasticizers,(c) water, and(d) mixtures thereofto form a suspension of polyadduct-covered stabilized polyamines in the liquid medium.Type: GrantFiled: July 29, 1985Date of Patent: May 5, 1987Assignee: Bayer AktiengesellschaftInventors: Gerhard Grogler, Richard Kopp, Heinrich Hess, Werner Rasshofer
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Patent number: 4647647Abstract: Addition compounds suitable as dispersing agents, obtainable by the reaction of polyisocyanates having an average functionality of from 2.5 to 6 with monohydroxyl compounds, reaction of the resulting reaction product with compounds of the formula IIG--(E).sub.n IIwherein E stands for --OH, --NH.sub.2 and/or --NHR (wherein R represents an alkyl group with 1 to 4 carbon atoms) and n stands for 2 or 3, and G represents an aliphatic, cycloaliphatic and/or aromatic group, and further reaction of the reaction product thus obtained with compounds of the formula IIIZ--Q IIIwherein Q stands for --OH, --NH.sub.2, --NHR (wherein R stands for an alkyl group having 1 to 4 carbon atoms) or --SH, and Z denotes a group having at least one basic group containing nitrogen. The invention also relates to processes for the preparation of these addition compounds, their use, and pulverulent or fibrous solids which are coated with these dispersing agents and are to be incorporated in liquid systems.Type: GrantFiled: December 24, 1984Date of Patent: March 3, 1987Assignee: BYK-Chemie GmbHInventors: Karlheinz Haubennestel, Peter Kramp
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Patent number: 4631329Abstract: The reduction in tensile strength exhibited in high humidity environments by "soft" polyurethanes prepared from aliphatic or cycloaliphatic diisocyanates can be substantially reduced if the molar ratio of diisocyanate and chain extender to isocyanate-reactive species other than said chain extender in the reaction mixtures from which said polyurethanes are prepared is at least 4.Type: GrantFiled: November 29, 1985Date of Patent: December 23, 1986Assignee: Dow Corning CorporationInventors: Gerald A. Gornowicz, Chi-Long Lee
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Patent number: 4607068Abstract: Radiation curable coating compositions, and especially electron beam-curable coating compositions, are disclosed in which magnetizable particles are dispersed in a liquid vehicle comprising a polyethylenically unsaturated polyurethane oligomer which includes a polycarbonate diol, and from 5% to 50%, based on the total weight of unsaturated material, of a polyethylenically unsaturated isocyanurate, such as a triacrylate of tris(2-hydroxyethyl) isocyanurate.Type: GrantFiled: June 3, 1985Date of Patent: August 19, 1986Assignee: DeSoto, Inc.Inventor: Robert E. Ansel
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Patent number: 4598121Abstract: A method for preparing an aqueous polyurethane dispersion, comprising (a) preparing a prepolymer with free NCO groups by reacting an aliphatic or cycloaliphatic polyisocyanate with a polyol, and an anionic compound; (b) dispersing said prepolymer in water; (c) reacting said water-dispersed prepolymer with a diamino hydrazide of the formula: ##STR1## wherein R is an alkylene group of 2 to 15 carbon atoms or a cycloalkylene or arylene group of 6 to 15 carbon atoms as a chain lengthening agent; (d) reacting the prepolymer of step (c) in said dispersion with formaldehyde to effect crosslinking.Type: GrantFiled: June 5, 1985Date of Patent: July 1, 1986Assignee: Chemische Werke Huls AGInventors: Josef Disteldorf, Hans-Jurgen Haage, Horst Schnurbusch
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Patent number: 4590254Abstract: Disclosed herein is a poly(urethane-urea) which is prepared by reverse-addition of an isocyanate-terminated prepolymer to an organic medium containing an alcoholic solvent and a chain extender comprising at least two isocyanate-reactive active hydrogen groups consisting essentially of amino groups.Type: GrantFiled: April 29, 1985Date of Patent: May 20, 1986Assignee: PPG Industries, Inc.Inventors: Wen-Hsuan Chang, David T. McKeough, Michael M. Chau
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Patent number: 4587322Abstract: Urethane-modified polyisocyanate compositions are made by reacting (a) an organic polyisocyanate or mixture of polyisocyanates having an NCO-content of from 5 to 45 wt % with (b) a hydantoin having an OH number of from 56 to 596 and containing two alcoholic hydroxyl groups. These reactants are used in quantities such that the NCO:OH equivalent ratio is from 2:1 to 50:1. The preferred polyisocyanates are 4,4'-diisocyanatodiphenylmethane and isomer mixtures thereof. The most preferred hydantoin is 5,5-dimethyl hydantoin. These urethane-modified polyisocyanates are particularly useful in the production of polyisocyanate addition products such as polyurethanes and polyisocyanurates.Type: GrantFiled: February 4, 1985Date of Patent: May 6, 1986Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Reiner Paul
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Patent number: 4579928Abstract: Urethane elastomers are produced by initially adding at least one incremental amount of a curing agent to a urethane prepolymer, having free polyisocyanate therein. Generally, free polyisocyanate-curing agent adducts are precipitated. Subsequently, the remaining amount of curing agent is added. Chain extension, accordingly, is favored which produces hard segment domains more evenly distributed in the polymer chain and imparts improved physical properties such as hardness, tear strength and high-low strain modulus.Type: GrantFiled: April 18, 1985Date of Patent: April 1, 1986Assignee: The Firestone Tire & Rubber CompanyInventors: Edward L. Kay, Kenneth B. Roskos
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Patent number: 4565645Abstract: Polyamines containing from 0.19 to 20.3 wt % primary amino groups are produced by hydrolyzing in a single stage an isocyanate with an excess of water, a relatively weak basic compound and a water-miscible polar solvent at a temperature from 50.degree. to 165.degree. C. The hydrolysis is conducted in a manner such that the reactants are substantially homogeneous during the reaction. The isocyanate should have an NCO-content of from 0.5 to 40 wt %. The weakly basic compound may be a carbonate or hydrogen carbonate of an alkali metal or an alkali or alkaline earth salt of a monocarboxylic or polycarboxylic acid or mixtures of such materials. The polyamines produced by this process are particularly useful in the production of polyurethanes.Type: GrantFiled: June 21, 1983Date of Patent: January 21, 1986Assignee: Bayer AktiengesellschaftInventors: Werner Rasshofer, Dieter Dieterich
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Patent number: 4562239Abstract: A tertiary nitrogen atom-containing urethane polymer which comprises units of the following formulas (I) and (II) as the essential components and units of the following formulas (III), (IV) and (V) as the optional components, the content of the unit of the formula (I) being not less than 10 milliequivalents in terms of the tertiary nitrogen atom per kilogram of the urethane polymer, and has a molecular weight of not less than 500: ##STR1## wherein R.sub.1 and R.sub.2 are each a C.sub.1 -C.sub.4 alkyl group and, when taken together with the adjacent nitrogen atom to which they are attached, represent a nitrogen-containing heterocyclic group, R.sub.3 is a C.sub.1 -C.sub.4 alkyl group, R.sub.4 is an optionally branched C.sub.1 -C.sub.8 alkylene group, m is a positive integer and n is zero or a positive integer but m+n is a number which can provide the unit of the formula (I) with a molecular weight of 131 to 6998 and the bondings in the unit of the formula (I) may be in random and/or block, R.sub.Type: GrantFiled: August 6, 1984Date of Patent: December 31, 1985Assignee: Toyo Boseki Kabushiki KaishaInventors: Noriomi Yamane, Yoshikazu Arimatsu, Kenichi Katsuo, Minoru Saitoh, Katsya Tani, Hideyuki Mitamura, Kamatani Hiroyoshi
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Patent number: 4554300Abstract: A method for preparing a polyurethane suitable for lining fuel tanks, said polyurethane having good, fuel resistance and improved hydrolysis resistance by using a ketimine of an aliphatic diamine as a curing agent in a three-component system composed of a prepolymer solution, a cement solution and a curing agent solution.Type: GrantFiled: April 12, 1985Date of Patent: November 19, 1985Assignee: Goodyear Aerospace CorporationInventors: Paul E. Liggett, Daniel A. Chung
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Patent number: 4554299Abstract: A method for preparing a polyurethane which has good long term flexibility, solvent resistance and resistance to hydrolysis, said method comprising mixing three components just prior to curing said components comprising a prepolymer solution, a cement solution and a crosslinking solution, said crosslinking solution comprising a solvent, an aromatic diamine and the ketimine of an aliphatic diamine.Type: GrantFiled: April 12, 1985Date of Patent: November 19, 1985Assignee: Goodyear Aerospace CorporationInventor: Paul E. Liggett