Organic Nh, =nh, Hnh Nitrogen Reactant Contains At Least One Halogen Atom Patents (Class 528/63)
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Patent number: 6127505Abstract: The present invention is an optically clear, high hardness, impact resistant polyurethane which provides exceptionally high heat distortion temperatures and excellent chemical resistance. The invention is particularly useful for transparency applications that require excellent impact resistance coupled with high heat distortion temperatures, such as architectural glazings vehicles, glazings, riot shields, aircraft canopies, face masks, visors, opthalmic and sun lenses, protective eyewear, and transparent armor.Type: GrantFiled: September 2, 1998Date of Patent: October 3, 2000Assignee: Simula Inc.Inventor: Edwin C. Slagel
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Patent number: 6077456Abstract: This invention is a liquid polyisocyanate prepolymer comprising the reaction product of an organic polyisocyanate blend and a polyoxyalkylene polyol, where polyisocyanate blend isA) a diphenylmethane diisocyanate comprising from 50 weight percent to 95 weight percent 4,4'-diphenylmethane diisocyanate, from 5 weight percent to 50 weight percent 2,4'-diphenylmethane diisocyanate, and less than 10 weight percent 2,2'-diphenylmethane diisocyanate, said weight percentages based on the total weight of the ingredients in A);B) a polymethylene polyphenyl polyisocyanate comprising from 30 weight percent to 70 weight percent diphenylmethane diisocyanate, the remainder comprising polymethylene polyphenyl polyisocyanates having functionalities greater than two, said weight percentages based on the total weight of the ingredients in B);C) and optionally a uretonimine-carbodiimide modified diisocyanate comprising from 10 weight percent to 35 weight percent uretonimine-carbodiimide species, the remainder comprising essentiaType: GrantFiled: June 20, 1994Date of Patent: June 20, 2000Assignee: BASF CorporationInventor: Thirumurti Narayan
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Patent number: 6046297Abstract: Polyurethane prepolymers are disclosed prepared with mononuclear aromatic diisocyanate such as toluene diisocyanate and an aliphatic diisocyanate such as H12MDI. These prepolymers can be cured with 4,4'-methylene-bis-(3-chloro-2,6-diethylaniline) to form a cured urethane elastomer with reduced propensity to crack during the curing process, extended pour life (a slower rate of viscosity buildup after curative and prepolymer are mixed), low hysteresis, and a low level of free toluene diisocyanates and/or other toxic or volatile substances to increase worker safety during processing. It has also been found that prepolymers made from toluene diisocyanate and cured with a blend of two aromatic diamine curatives yields urethane elastomers with the same reduced propensity to crack during the curing process.Type: GrantFiled: November 27, 1996Date of Patent: April 4, 2000Assignee: Uniroyal Chemical Company, Inc.Inventors: Ronald Owen Rosenberg, Ajaib Singh, Ronald Walter Fuest
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Patent number: 5994466Abstract: The present invention relates to polyurethane elastomer systems for industrial and paper mill rolls and more particularly to polyurethane covered rolls made from a new polyurethane composition of a polyurethane prepolymer cured with an aromatic diamine and a hydroxyl-terminated polybutadiene resin. Rolls made with this new polyurethane composition exhibit improved dynamics, hydrolytic stability, and reduced water vapor transmission over conventional polyurethane elastomer systems.Type: GrantFiled: June 11, 1997Date of Patent: November 30, 1999Assignee: Stowe Woodward CompanyInventor: Yan Yang
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Patent number: 5962617Abstract: The present invention is an optically clear impact resistant polyurethane which provides exceptionally high heat distortion temperatures and excellent chemical resistance. The invention is particularly useful for transparency applications that require excellent impact resistance coupled with high heat distortion temperatures, such as glazings for buildings, vehicles, riot shields, aircraft canopies, and face masks.Type: GrantFiled: February 1, 1996Date of Patent: October 5, 1999Assignee: Simula Inc.Inventor: Edwin C. Slagel
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Patent number: 5955559Abstract: Cast polyurethanes are preferably formed from a hydrogenated polydiene diol having from up to 2 terminal hydroxyl groups per molecule and a number average molecular weight between 1000 and 20,000, an isocyanate having two or more isocyanate groups per molecule. This composition is then reacted with an amine curing agent at 80 to 130.degree. C. to form a cast elastomer with excellent hydrolytic stability. The amine curing agent must be a hindered aromatic amine crosslinker with low polarity and a solubility parameter of less than 10.5.Type: GrantFiled: September 8, 1997Date of Patent: September 21, 1999Assignee: Shell Oil CompanyInventors: Dale Lee Handlin, Jr., Steven Soohyun Chin, Aisa Sendijarevic, Vahid Sendijarevic, Kurt C. Frisch
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Patent number: 5880252Abstract: Pyrrolidonyl-containing polyesters and polyamides I to III ##STR1## where R, X, A and Z are defined herein, are suitable as film formers and conditioners in hair-cosmetic formulations, for stabilizing hydrogen-peroxide in aqueous solution, for complexing iodine, as tablet binders and as a constituent of film coatings in pharmaceutical preparations, for enzyme and bleach stabilization in detergent formulations, as an auxiliary in the production and finishing of textiles, as a solubilizer and protective colloid in the preparation and stabilization of polymer dispersions, and as an adhesive raw material.Type: GrantFiled: March 22, 1996Date of Patent: March 9, 1999Assignee: BASF AktiengesellschaftInventors: Son Nguyen Kim, Jorg Breitenbach, Axel Sanner, Peter Hossel, Siegfried Lang
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Patent number: 5827919Abstract: Fluorourethane additives for water-dispersed coating compositions comprising the product of the reaction of 1) at least one diisocyanate, or polyisocyanate or a mixture of polyisocyanates containing at least three isocyanate groups per molecule, (2) at least one fluorochemical compound containing at least one Zerewitinoff hydrogen in an amount sufficient to react with 5% to 80% of the isocyanate groups in the diisocyanate or polyisocyanate, (3) at least one compound of the formula R.sub.10 --(R.sub.2).sub.k --YH in an amount sufficient to react with 5% to 80% of the isocyanate groups in the diisocyanate or polyisocyanate and wherein R.sub.10 is a C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 omega-alkenyl radical, or C.sub.1 -C.sub.18 omega-alkenoyl; R.sub.2 is --C.sub.n H.sub.2 n-- optionally end-capped with --?OCH.sub.2 C(R.sub.4)H!.sub.p --, --?OCH.sub.2 C(CH.sub.2 Cl)H!p--, or --C(R.sub.5) (R.sub.6) (OCH.sub.2 C?CH.sub.2 Cl!H).sub.p --, wherein R.sub.4, R.sub.5, and R.sub.Type: GrantFiled: August 7, 1996Date of Patent: October 27, 1998Assignee: E. I. du Pont de Nemours and CompanyInventor: Donald Douglas May
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Patent number: 5654390Abstract: A trimodal molecular weight toluene diisocyanate endcapped polyether polyol prepolymer is disclosed having free toluene diisocyanate below 0.5 weight percent where the three molecular weight polyols used are 300-800, 800 to 1500 and 1500-10000. Processes to make and use these prepolymers as polyurethane castable elastomers having exceptionally long flex fatigue lives using environmentally friendly materials essentially free of TDI are also disclosed.Type: GrantFiled: November 17, 1995Date of Patent: August 5, 1997Assignee: Uniroyal Chemical Company, Inc.Inventors: Vincent John Gajewski, Christopher James Maupin
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Patent number: 5648447Abstract: Polyurethane elastomers of improved elongation, tensile strength and other physical properties are prepared from a polyol component containing a crystallizable polyol and from 5 to 35 equivalent percent of a low monol polyoxypropylene polyol by one-shot, quasiprepolymer, and preferably, by prepolymer techniques involving chain extension with an aliphatic diol or aromatic amine.Type: GrantFiled: December 22, 1995Date of Patent: July 15, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Stephen D. Seneker, Nigel Barksby, Bruce D. Lawrey
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Patent number: 5545697Abstract: An epoxy resin composition characterized by comprising (A) an epoxy resin containing an oxazolidone ring, (B) a halogen-containing epoxy resin and (C) a curing agent as its ingredients, wherein the ratio by weight of ingredients (A) to (B) is 5-100:95-0, the hydrolizable chlorine content of ingredients (A) and (B) is no more than 500 ppm and the amount of .alpha.-glycol is no more than 100 m eq/kg has excellent properties and can be employed as the materials for electronic applications and as paints, adhesives, molding materials, composite materials, laminates and sealing materials.Type: GrantFiled: February 14, 1994Date of Patent: August 13, 1996Assignee: Ciba-Geigy CorporationInventor: Hiroshi Uchida
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Patent number: 5530061Abstract: A process for producing an impact-resistant polyacetal resin composition, which comprises a first step of mixing with shear a polyacetal resin (A), a thermoplastic polyurethane (B) and a polyhydric alcohol (C) having at least three hydroxyl groups in the molecule at a temperature of 180.degree. to 250.degree. C. and at a temperature at which said polyacetal resin (A) and said thermoplastic polyurethane (B) melt; and a second step of mixing with shear the resulting mixture obtained in the first step, in the presence of at least one compound (D) selected from the group consisting of a polyisocyanate (d.sub.1) and a compound (d.sub.2) which generates a polyisocyanate under heat, at a temperature of 180.degree. to 250.degree. C. and at a temperature at which said polyacetal resin (A) and said thermoplastic polyurethane (B) melt.Type: GrantFiled: November 14, 1994Date of Patent: June 25, 1996Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Daisuke Sanada, Masao Hasegawa, Satoshi Nagai, Hiroshi Mimura
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Patent number: 5410009Abstract: A polyurethaneurea elastomer obtained by reacting a polyisocyanate component obtained by reacting 1,5-naphthalene diisocyanate with a polyol, with an amine component consisting essentially of an amine compound of the formula (1): ##STR1## wherein R is a bivalent polyalkylene polyether or polyalkylene polyester having an average molecular weight of at least 200, which may contain unsaturated bonds in the polyalkylene.Type: GrantFiled: June 28, 1993Date of Patent: April 25, 1995Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Kaneyoshi Kato, Yoshijiro Oyaizu
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Patent number: 5340902Abstract: This invention relates to the production of spandex fibers made from segmented polyurethane(urea)s which are prepared from low unsaturation-containing polyols made by polymerizing alkylene oxides in the presence of a double metal cyanide complex catalyst. With the low unsaturation-containing polyols, spandex fibers can be prepared that have better physical properties than fibers prepared with PTMEG polyols.Type: GrantFiled: June 4, 1993Date of Patent: August 23, 1994Assignee: Olin CorporationInventors: Curtis P. Smith, James M. O'Connor
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Patent number: 5326846Abstract: A process for producing an impact-resistant polyacetal resin composition, which comprises mixing with shear a polyacetal resin (A), a thermoplastic polyurethane (B), a polyhydric alcohol (C) having at least three hydroxyl groups in the molecule and at least one compound (D) selected from the group consisting of a polyisocyanate (d.sub.1) and a compound (d.sub.2) which generates a polyisocyanate under heat, while at least two components (A) and (B) are melted. An injection-molded article from the impact-resistant polyacetal resin composition, provided by the above process, exhibits superior tensile strength and elongation at break at weld portions.Type: GrantFiled: April 1, 1993Date of Patent: July 5, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Satoshi Nagai, Masao Hasegawa, Hiroshi Mimura, Makoto Kobayashi
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Patent number: 5284888Abstract: A corrosion inhibiting, EMI/RFI shielding composition is provided comprising a polyurethane resin which comprises a hydroxy or amine functional first polymer and an isocyanate, or isocyanurate terminated second polymer, a stabilized conductive filler, and an azole. In one embodiment of the invention a composition is provided comprising a polyurethane which comprises a fluoroolefin vinyl ether and an isocyanurate, a stabilized copper powder, and a triazole selected from the group consisting of alkyl substituted aromatic triazoles and other azoles. The invention further provides a method of composition a substrate with a composition of the invention in order to provide EMI/RFI shielding and prevent corrosion, and a substrate thus coated.Type: GrantFiled: October 28, 1991Date of Patent: February 8, 1994Assignee: Chomerics, Inc.Inventor: Noredin H. Morgan
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Patent number: 5262448Abstract: The present invention relates to a process for the production of an optionally cellular elastomeric molded article having a compact surface and based on a polyurea elastomer containing urethane groups which is the reaction product ofa) a polyisocyanate component based on a polyisocyanate of the diphenylmethane series,b) a polyol component based on a polyether polyol, a polyester polyol or mixtures thereof andc) a polyamine component containing1) 50 to 95% by weight, based on the weight of component c), of at least one sterically hindered aromatic diamine and2) 5 to 50% by weight, based on the weight of component c), of at least one compound which has a molecular weight of about 1,000 to 12,000,by reacting component a) with at least 90% by weight of component b) at an NCO/OH equivalent ratio of at least 4:1 to form an NCO semi-prepolymer and subsequently reacting the NCO semi-prepolymer with component c) and the remainder of component b) by the reaction injection molding process to form the polyurea elastomerType: GrantFiled: April 27, 1990Date of Patent: November 16, 1993Assignee: Bayer AktiengesellschaftInventors: Andreas Ruckes, Hans-Joachim Meiners, Heinrich Boden, Manfred Schmidt
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Patent number: 5231159Abstract: A molded elastomer having high and low temperature resistance in dynamic applications. The elastomer includes the reaction product of an amine or hydroxy terminated polyol having an unsaturated level of less than about 0.06 milliequivalents per gram polyol, an hydroxyl or amine terminated chain extender, and a polyisocyanate-containing prepolymer capable of rapid reaction times with said chain extender when admixed together in a mold.Type: GrantFiled: December 16, 1991Date of Patent: July 27, 1993Assignee: The Gates Rubber CompanyInventors: Philip M. Patterson, Richard L. Watkins
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Patent number: 5214121Abstract: Diols containing perfluoroalkyl radicals are produced by reacting compounds of the formulaR.sub.f --(E).sub.m --X'--H(R.sub.f =perfluoroalkyl radical, E is an alkylene group optionally interrupted by certain groups and/or substituted at the end, m=0 or 1, X'--H=--CONRH, --SO.sub.2 NRH or --SH) in a first step with diols containing at least 2 halogen atoms. Preferably the obtained products are reacted in a second reaction step with polyvalent isocyanates to prepolymers with free --NCO-- or free --OH--groups and these prepolymers are reacted in a third step with compounds containing isocyanate groups and/or hydroxyl groups. The first reaction step is carried out in an aprotic solvent which is insoluble in water, in the presence of an aqueous solution of an alkali metal carbonate. Intermediate products have not to be isolated.The obtained polyurethanes can be used in form of aqueous dispersions for the oil- and water repellent finishing of textiles.Type: GrantFiled: May 17, 1991Date of Patent: May 25, 1993Assignee: Ciba-Geigy CorporationInventors: Franz Mosch, LuSimpert, Michael Bernheim
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Patent number: 5204441Abstract: Branched-chain diols and a method of forming them by reacting 1,4-diiodoperfluorobutane and perfluoropropylene to obtain branched-chain diiodide adducts thereof, reacting the diiodide adducts with ethylene to obtain I--CH.sub.2 CH.sub.2 --R--CH.sub.2 CH.sub.2 --I, wherein R is a branched-chain perfluoroalkyl radical, and hydrolysing the iodo groups to alcohols to obtain HO--CH.sub.2 CH.sub.2 --R--CH.sub.2 CH.sub.2 --OH. These diols can be reacted with branched-chain diisocyanates to form polyurethanes of better processability and lower glass transition temperatures than polyurethanes prepared from linear fluorinated monomers.Type: GrantFiled: March 12, 1990Date of Patent: April 20, 1993Assignee: Fluorochem Inc.Inventors: Kurt Baum, Thomas G. Archibald, Aslam A. Malik
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Patent number: 5112933Abstract: An ether-based polyurethane article comprises a toluene diisocyanate-terminated polyether polyol prepolymer cured with a blended polyester polyol/diamine curative. The article may be made by mixing a toluene diisocyanate-terminated polyether polyol prepolymer with a blended polyester polyol/diamine curative to form a reaction mixture. A suitably shaped mold is preheated and filled with the reaction mixture with sufficient pressure to displace air in the mold. The reaction mixture is held in the preheated mold to cure the reaction mixture and form the article. The cast article is removed from the mold and post-cured to complete the chemical cross-linking reaction.Type: GrantFiled: April 16, 1991Date of Patent: May 12, 1992Assignee: Otis Elevator CompanyInventors: Hugh J. O'Donnell, Vincent J. Gajewski, Knizley James B., Richard L. Palinkas, Ronald O. Rosenberg
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Patent number: 5109034Abstract: This invention relates to a storage-stable solid isocyanate compositions that are substantially crystalline at room temperature comprising the reaction products of organic isocyanates with substoichiometric quantities of 2-methyl-1,3-propanediol.This invention further to a method of using the solid isocyanate compositions of the invention in the preparation of polyurethane products.Type: GrantFiled: June 3, 1991Date of Patent: April 28, 1992Assignee: Miles Inc.Inventor: Robson Mafoti
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Patent number: 5079329Abstract: This invention is directed to a latently reactive pasty molding material (masterbatch), which only becomes reactive above ambient temperature (about 25.degree. C.), for producing temperature-resistant, elasticized, molded, duromer components which is comprised of a mixture of a methylene-diphenyl diisocyanate and a diamine which is not reactive at ambient temperature, but is reactive above about 120.degree. C., which is selected from the group consisting of an alkali-halide salt complex, which is the reaction product of three moles at 4,4'-diphenylmethane diamine and of one mole halide salt, and alternatively a hexamethylene-6,6'-diamine carbamate; and about 1 to 625 parts by weight (per 100 parts methylene-diphenyl diisocyanate) of a low-molecular weight isocyanate-terminated polyesterpolyol-diisocyanate prepolymer, produced from polycaprolactone and a mixture of the toluylene diisocyanate isomers. The mixture has a NCO excess of up to 15% more than the sum of the free OH-- and NH.sup.2 -- constituents.Type: GrantFiled: May 1, 1990Date of Patent: January 7, 1992Assignee: Firma Carl FreudenbergInventors: Horst Muhlfeld, Gunter Schuhmacher
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Patent number: 5049638Abstract: A coating composition for forming a substantially non-porous moisture-permeable coating layer or film of a hydrophilic polyurethane resin, which comprises a polyol combination and a poloyisocyanate compound, or a prepolymer or polyurethane resin obtained by reacting them, said polyol combination comprising:(a) from about 50 to about 98% by weight of a polyoxyethylene polyol having an oxyethylene group content of from about 50 to about 90% by weight, a hydroxyl value of from about 15 to about 60 and at least 3 hydroxyl groups; and(b) from about 2 to about 50% by weight of a diol having a molecular weight of from about 62 to about 2,000 which may contain oxyethylene groups;provided that the molar equivalent ratio of the component (b) to the component (a) is from about 0.2 to about 5, and the total oxyethylene group content in the components (a) and (b) is at least about 70% by weight.Type: GrantFiled: June 29, 1989Date of Patent: September 17, 1991Assignee: Asahi Glass Company, Ltd.Inventors: Yukio Matsumoto, Nobuaki Kunii
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Patent number: 4945149Abstract: A coating composition for forming a substantially non-porous moisture-permeable coating layer or film of a hydrophilic polyurethane resin, which comprises a polyol combination and a polyisocyanate compound, or a prepolymer or polyurethane resin obtained by reacting them, said polyol combination comprising:(a) from about 50 to about 98% by weight of a polyoxyethylene polyol having an oxyethylene group content of from about 50 to about 90% by weight, a hydroxyl valve of from about 15 to about 60 and at least 3 hydroxyl groups; and(b) from about 2 to about 50% by weight of a diol having a molecular weight of from about 62 to about 2,000 which may contain oxyethylene groups;provided that the molar equivalent ratio of the component (b) to the component (a) is from about 0.2 to about 5, and the total oxyethylene group content in the components (a) and (b) is at least about 70% by weight.Type: GrantFiled: August 2, 1988Date of Patent: July 31, 1990Assignee: Asahi Glass Company Ltd.Inventors: Yukio Matsumoto, Nobuaki Kunii
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Patent number: 4931487Abstract: Polyurethanes are produced from compositions comprising at least one relatively high equivalent weight component and at least one chain extender selected from the group consisting of heterocyclic diamines, diaromatic disulfides, alkyl ethers of halogen-substituted aromatic diamines, polysubstituted alkyl diamines and alkyl acid esters of halogen-substituted diamino phenols of designated structures. Polyurethanes having high thermal stability, high tear strength and high modulus are produced.Type: GrantFiled: March 4, 1988Date of Patent: June 5, 1990Assignee: Dow Chemical CompanyInventors: Ralph D. Priester, Jr., Edwin J. Strojny, Debra H. Stutts
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Patent number: 4847307Abstract: The present invention is directed to a process for the production of optionally cellular, polyurethane elastomer moldings or optionally cellular, rigid structural polyurethanes by reacting a reaction mixture containing(i) a polyisocyanate,(ii) a high molecular weight polymer having at least two hydroxy groups and having a molecular weight of 400 to about 10,000,(iii) about 5 to 50% by weight, based on the weight of component (ii) of a chain-extender having at least two hydroxy groups and(iv) about 0.05 to 10 weight percent, based on the weight of components (ii) and (iii) of a salt based on a carboxy functional siloxane and an amidine group-containing compound of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: August 8, 1988Date of Patent: July 11, 1989Assignee: Mobay CorporationInventors: John E. Dewhurst, Stephen J. Harasin
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Patent number: 4837292Abstract: A shaped article of a polyurethane-urea spandex having a specific polycarbonate soft segments provides improved resistance to chlorine and mildew. The soft segment is derived from poly(pentane-1,5-carbonate)diol, poly(hexane-1,6-carbonate)diol, copolymers thereof, or mixtures thereof.Type: GrantFiled: December 17, 1987Date of Patent: June 6, 1989Assignee: E. I. DuPont De Nemours and CompanyInventor: Gary A. Lodoen
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Patent number: 4812487Abstract: There is disclosed polyurethane reaction mixtures containing a novel aromatic diamine as a curative. This invention is also concerned with cured polyurethanes prepared by reacting the aromatic diamine of this invention with a mixture of organic polyisocyanate and polymeric polyol containing an excess of said polyisocyanate or with a prepolymer of said polyisocyanate and a polymeric polyol. The use of the curative of this invention provides sufficient pot life for making castings as well as foams.Type: GrantFiled: March 15, 1988Date of Patent: March 14, 1989Assignee: The Goodyear Tire & Rubber CompanyInventor: Howard A. Colvin
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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: 4791187Abstract: The invention relates to essentially linear polyurethane elastomers, having improved properties, made from polyester or polyether diols, diisocyanates and chain extenders, the latter having liquid-crystalline properties; and also films and, in particular, fibres which are prepared on the basis of such liquid-crystalline polyurethane components and are shaped thermoplastically (via melting) or from solutions (by solution spinning processes). The invention furthermore relates to an appropriate process for the preparation of the polyurethane elastomers, particularly of PU elastomer fibres (Elasthan and Spandex fibres).Type: GrantFiled: August 7, 1987Date of Patent: December 13, 1988Assignee: Bayer AkteingesellschaftInventors: Carlhans Suling, Michael Kausch, Rudi Dauscher
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Patent number: 4789688Abstract: The present invention is directed to a process for the production of optionally cellular, polyurethane elastomer moldings or optionally cellular, rigid structural polyurethanes by reacting a reaction mixture containing(i) a polyisocyanate,(ii) a high molecular weight polymer having at least two hydroxy groups and having a molecular weight of 400 to about 10,000,(iii) about 5 to 50% by weight, based on the weight of component (ii) of a chain-extender having at least two hydroxy groups and(iv) about 0.05 to 10 weight percent, based on the weight of components (ii) and (iii) of a salt based on a carboxy functional siloxane and an amidine group-containing compound of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: January 20, 1988Date of Patent: December 6, 1988Assignee: Mobay CorporationInventors: John E. Dewhurst, Stephen J. Harasin
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Patent number: 4786703Abstract: This invention relates to a polyisocyanate prepolymer for polyurethane/urea elastomer synthesis and to the resulting elastomer. The prepolymer is formed by reacting toluenediisocyanate with a long chain polyol under conditions such that essentially a 2:1 adduct is formed. Excess toluenediisocyanate is removed prior to forming the elastomer.Type: GrantFiled: April 15, 1987Date of Patent: November 22, 1988Assignee: Air Products and Chemicals, Inc.Inventors: William E. Starner, Jeremiah P. Casey, Barton Milligan, Susan M. Clift
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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: 4774313Abstract: Improved crack growth resistance is obtained when glycerine is added to a non-cured urethane prepolymer system containing free NCO groups therein and cured with a metal halide salt complex of methylenedianiline. The prepolymer is made from a blend of a polyether polyol and a polyether intermediate having ethylene oxide end blocks thereon.Type: GrantFiled: November 18, 1987Date of Patent: September 27, 1988Assignee: The Firestone Tire & Rubber CompanyInventor: Joseph H. Tazewell
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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: 4618667Abstract: Urethane compositions generally free of phase separation patterns and flow lines are produced. One method includes the utilization of a nucleating compound which is generally added to a urethane prepolymer before any chain extension thereof. Examples of nucleating agents include urethanes, ureas and allophanates such as carboxylic acids, organic acid and anhydrides, amides, imides and the like. Another method includes adding a very small initial incremental amount of a curing agent to the prepolymer with an insoluble product being produced thereby and subsequently adding the remainder of the curing agent.Type: GrantFiled: April 18, 1985Date of Patent: October 21, 1986Assignee: The Firestone Tire & Rubber CompanyInventors: Edward L. Kay, Kenneth B. Roskos
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Patent number: 4587275Abstract: Polyurethane urea elastomers are produced by reacting polyisocyanates with compounds containing at least two isocyanate reactive hydrogen atoms having a molecular weight of 400 to 10,000 and mononuclear or dinuclear aromatic diamines. The aromatic diamines must have at least one sulfonamide group as a substituent on at least one of their aromatic rings. Known chain lengthening agents, activators, blowing agents, auxiliary agents and additives may also be included in the reaction mixture.Polyurethane elastomers produced by this process have excellent mechanical properties. In particular, such elastomers are soft yet have high tear propagation resistance.Type: GrantFiled: September 30, 1982Date of Patent: May 6, 1986Assignee: Bayer AktiengesellschaftInventors: Richard Kopp, Holger Meyborg, Gerhard Grogler, Jurgen Schwindt
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Patent number: 4581433Abstract: The present invention relates to coating compositions comprising (i) an isocyanate prepolymer based on bis(4-isocyanatocyclohexyl)methane and polyalkylene ether polyols having hydroxyl functionalities of 2 to 3 and (ii) at least one diprimary aromatic diamine having at least one alkyl substituent in an ortho-position to one amino group and two alkyl substituents in both ortho-positions to the other amino group.Type: GrantFiled: April 29, 1985Date of Patent: April 8, 1986Assignee: Mobay CorporationInventors: Terry A. Potter, Peter H. Markusch, David J. Prepelka
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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: 4556703Abstract: A prepolymer curable with a hydroxyl or amine functional curative to form a polyurethane elastomer composition having low heat buildup characteristics is disclosed. Specifically, the polyurethane prepolymer has terminally reactive isocyanate groups and is prepared by reaction of polymeric diol with a stoichiometric excess of a mixture of the 2,6- and 2,4-isomers of tolylene diisocyanate, said mixture containing from about 50 to about 90 wt % of the 2,6-isomer.The invention also relates to a polyurethane elastomer composition comprising the aforementioned prepolymer and a curingly effective amount of a curative selected from the group consisting of aromatic diamines, hydroxy functional compounds, and mixtures thereof, and optionally, from about 0.01 to 1 part of catalyst per hundred parts of prepolymer.Also disclosed are articles of manufacture produced from the above composition, as well as compositions wherein the mixture contains 40 to 100 wt % of the 2,6-isomer.Type: GrantFiled: May 14, 1984Date of Patent: December 3, 1985Assignee: American Cyanamid CompanyInventors: Ignazio S. Megna, Curtis A. Franz
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Patent number: 4532316Abstract: Reactive, 100 percent solids, segmented, phase-separating polyurethane prepolymers are provided, being the reaction products of:(i) a polyol (A) having a number average molecular weight of from about 600 to about 3500 and having a functionality of at least 2;(ii) an isocyanate (B) having a functionality of at least 2; and(iii) a low molecular weight chain extender (C) having a molecular weight in a range lower than about 500 and having a functionality of at least 2,characterized in that the above reactants are employed in such proportions as to satisfy the following equations: ##EQU1##Eq.sub.OH .gtoreq.Eq.sub.CE (b)Eq.sub.CE >O, (c)wherein Eq.sub.NCO is the equivalents of the isocyanate species employed, and Eq.sub.OH and Eq.sub.CE denote the equivalents, respectively, of the polyol and chain extender.Type: GrantFiled: May 29, 1984Date of Patent: July 30, 1985Assignee: W. L. Gore & Assoc., Inc.Inventor: Robert L. Henn
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Patent number: 4519432Abstract: This invention relates to reinforced tire utilizing polyurea or polyurethane formulations having low hysteresis. The polymer having low hysteresis is formed by reacting a prepolymer of an aromatic isocyanate and a high molecular weight difunctional polyol with a chain extender mix comprising an aromatic diamine and difunctional polyol. In these compositions the aromatic diisocyanate and aromatic diamine are selected so that there is substantial symmetry between the molecules. The reinforcement used is preferably an aromatic polyamide.Type: GrantFiled: February 8, 1984Date of Patent: May 28, 1985Assignee: Lim International S.A.Inventors: Andreas R. Schmidt, Herbert F. Strohmayer, Walter Sibral, Barton Milligan
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Patent number: 4507459Abstract: This invention pertains to the synthesis of polyurethane systems having low hysteresis. The systems are generated by reacting a prepolymer of a mononuclear diisocyanate and a polyol with a chain extender mix of a mononuclear aromatic diamine and a polyol. The prepolymer should have a free isocyanate content of from 2 to about 12% by weight and the chain extender mix should have an amine to polyol equivalent from about 0.5 to 5:1.Type: GrantFiled: February 8, 1984Date of Patent: March 26, 1985Assignee: Air Products and Chemicals, Inc.Inventors: Andreas R. Schmidt, Herbert F. Strohmayer, Walter Sibral, Barton Milligan
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Patent number: 4504648Abstract: A polyurethaneurea which comprises a polymer obtained by a polyaddition reaction of (a) a polyetherpolyol derivative and (b) an at least 2-valent polyisocyanate, the polyetherpolyol derivative having at least, on average, one terminal amino group in which at least, on average, one hydroxyl group is substituted by a residue of para-aminobenzoic acid ester, and having the general formula ##STR1## wherein n is an integer of 2 to 8, x is an average value and a positive number of 0.05 n to (n-1), A is an n-valent radical obtained by removal of hydroxyl groups from an n-valent polyoxyalkylenepolyol having a molecular weight of 400 to 10,000.Type: GrantFiled: November 7, 1983Date of Patent: March 12, 1985Assignee: Toyo Tire & Rubber Company, LimitedInventors: Kozo Otani, Yoshio Yamada, Hiroyuki Okumura
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Patent number: 4355119Abstract: Oligomeric formal diols are prepared by coupling segments of PTMEG, each having a molecular weight of 1000-3000, with formaldehyde. The formal diols are useful in preparing polyurethanes.Type: GrantFiled: November 6, 1981Date of Patent: October 19, 1982Assignee: E. I. DuPont de Nemours and CompanyInventor: Engelbert Pechhold
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Patent number: 4349656Abstract: A method for the preparation of a polyetherthioether copolymer glycol represented by the formula:H--OC.sub.2 H.sub.4 SC.sub.2 H.sub.4 --.sub.x --OC.sub.4 H.sub.8 --.sub.y OHwherein the mole ratio x/y is in the range of about 45:55 to 60:40, respectively. More specifically, a method for the preparation of a copolymer of thiodiethanol and 1,4-butanediol wherein the mole ratio x/y is about 50:50. Also, the copolymers produced thereby and polyurethane elastomers produced therefrom, particularly those produced from the 50:50 copolymer, and to their use in solid tires having improved dynamic mechanical properties.Type: GrantFiled: January 26, 1981Date of Patent: September 14, 1982Assignee: American Cyanamid CompanyInventors: Volker D. Arendt, Tsi T. Li
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Patent number: 4327204Abstract: A polyurethane elastomer is produced by mixing a hardener composition containing a polyamine, a long chain polyol having an average molecular weight of 300 to 4,000 and a catalyst with an isocyanate composition comprises a prepolymer having terminal isocyanate group and an average molecular weight of 500 to 5,000 and an organic diisocyanate monomer with or without a triisocyanate monomer and a ratio of isocyanate groups of said prepolymer to amino groups of said polyamine is in a range of 0.6:1 to 1.5:1 and a ratio of a total of isocyanate groups in said isocyanate composition to a sum of amino groups of said polyamine and hydroxyl group of said long chain polyol is in a range of 0.8:1 to 1.4:1.Type: GrantFiled: March 18, 1980Date of Patent: April 27, 1982Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshijiro Oyaizu, Wataro Koike, Chihiro Yazawa
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Patent number: 4324867Abstract: A process for preparing molded polyurethane-polyurea elastomers comprising reacting an organic polyisocyanate and a reactive polyol composition, said reactive polyol composition comprising(a) a polyol having an equivalent weight of from 700 to 4,000 and a functionality from 2 to 6; and(b) a reactive aromatic diamine which is soluble in said polyol at use temperatures and concentrations, has a pK.sub.b value greater than 10, and has the following structural formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 individually are radicals selected from the group consisting of hydrogen and alkyl radicals of 1 to 4 carbon atoms, and at least one of the alkyl radicals in each ring is a non-linear alkyl radical selected from the group consisting of isopropyl, isobutyl, and tertiary butyl radicals, and wherein R.sub.5 and R.sub.6 are radicals individually selected from the group consisting of hydrogen and alkyl radicals of 1 to 4 carbon atoms.Type: GrantFiled: October 6, 1980Date of Patent: April 13, 1982Assignee: BASF Wyandotte CorporationInventors: John T. Patton, Jr., John P. Rupert