Fiber Or Elastomer Prepared From An Isocyanate Reactant Patents (Class 528/906)
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Patent number: 8765901Abstract: A spandex comprising a polyurethane or polyurethaneurea reaction product of at least one diisocyanate compound and a poly(tetramethylene-co-ethyleneether) glycol comprising constituent units derived by copolymerizing tetrahydrofuran and ethylene oxide wherein the percentage of ethylene ether moieties is from about 16 to about 70 mole percent with at least one chain extender selected from the group consisting of diamines and diols and at least one chain terminator wherein the spandex is spun at a speed in excess of about 750 meters per minute.Type: GrantFiled: May 8, 2006Date of Patent: July 1, 2014Assignee: Invista North America S.ár.l.Inventors: Charles F. Palmer, Jr., Gary A. Lodoen
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Patent number: 8759467Abstract: A process for producing a polyurethane, which comprises using a polyester polyol (a-1), a polyether polyol (b), an isocyanate compound (c) and a chain extender (d) as a raw material to produce a polyurethane, wherein the polyester polyol (a-1) is a polyester polyol (a-1) obtained by forming an ester bond between either a carboxyl group of a polycarboxylic acid (i-1) having a polysiloxane framework and a plurality of carboxyl groups or an ester group of a polycarboxylic acid ester (i-2) having a polysiloxane framework and a plurality of ester groups, and a hydroxyl group of a polyether polyol (ii).Type: GrantFiled: April 27, 2012Date of Patent: June 24, 2014Assignee: Mitsubishi Chemical CorporationInventors: Takanori Taniguchi, Haruhiko Kusaka, Youko Nakagawa, Daisuke Hirooka, Hisashi Nagahama
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Patent number: 8420765Abstract: A polyurethaneurea composition comprises a reaction product of at least one diisocyanate compound, a polymeric glycol, a poly(tetramethylene-co-ethyleneether) glycol comprising constituent units derived by copolymerizing tetrahydrofuran and ethylene oxide (EO) wherein the portion of the constituent units derived from ethylene oxide is present in the poly(tetramethylene-co-ethyleneether) glycol from greater than about 37 to about 70 mole percent, at least one diamine chain extender, and at least one chain terminator. The invention further relates to the use of blends of polymeric glycols and poly(tetramethylene-co-ethyleneether) glycols as the soft segment base in spandex compositions. The invention also relates to new polyurethane compositions comprising polymeric glycols and poly(tetramethylene-co-ethyleneether) glycols, and their use in spandex.Type: GrantFiled: May 8, 2006Date of Patent: April 16, 2013Assignee: Invista North America S.ár.l.Inventor: Charles F. Palmer, Jr.
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Patent number: 8242229Abstract: Polyurethane prepolymers are described which are prepared from 2,4?-diiso-cyanate diphenylmethane (2,4?-MDI), a polyol component and an aliphatic diisocyanate. These prepolymers can be cured with aliphatic, cycloaliphatic and/or aromatic amines to form a cured urethane elastomer. In comparison to cured urethane elastomers based on monomeric 2,4?-MDI, these prepolymers provide elastomers with extended pour life, i.e. they exhibit a slower rate of viscosity buildup after curative and prepolymer are mixed which results in a reduced propensity to crack during the curing process and gives the opportunity to cast larger parts. In comparison to polyurea/urethanes prepared from cured TDI-prepolymers and which optionally include H12-MDI, the prepolymers of the invention have better health and safety aspects.Type: GrantFiled: January 23, 2008Date of Patent: August 14, 2012Assignee: Bayer MaterialScience AGInventors: Jens Krause, James-Michael Barnes, Manfred Schmidt, Wieland Hovestadt
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Patent number: 7838617Abstract: Commercial spandex can be prepared with greater efficiency, improved consistency and at lower costs from a high-solids content polyurethaneurea polymer solution. The polyurethaneurea is prepared using a combination of 4,4?-MDI and 2,4?-MDI, and an amount of chain extenders and chain terminators such that the polymer solution, prior to spinning, is highly soluble and has an appropriate pre-spun IV and primary amine content. Such spandex fibers, and the fabrics and garments comprising them, have good dyeability and colorfastness, as well as other desirable characteristics.Type: GrantFiled: November 3, 2004Date of Patent: November 23, 2010Assignee: INVISTA North America s.àr.l.Inventors: Nathan E. Houser, Gordon W. Selling, Beverly Jean Selle, Steven Peter Pardini, Robert Dewhurst, Elizabeth Todd Singewald
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Patent number: 7232876Abstract: A phosphorus-containing urethane (meth)acrylate compound obtained by reacting (A) a polyol compound comprising (A1) a phosphorus-containing polyol having a phosphorus atom, with (B) a bifunctional or greater polyisocyanate and (C) a hydroxyl group-containing (meth)acrylate.Type: GrantFiled: January 21, 2003Date of Patent: June 19, 2007Assignee: Showa Denko K.K.Inventors: Kenji Tamura, Yoshio Miyajima, Motoyuki Hirata
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Patent number: 7202322Abstract: A thermoplastic polyether polyurethane having high moisture vapor transmission, high melting point and static dissipative properties is disclosed. The thermoplastic polyether polyurethane is prepared by reacting a hydroxyl terminated polyether intermediate, an aromatic chain extender glycol, and a polyisocyanate. The polymers formed are useful for melt-spun fibers, fabric coatings for breathable garments, house wrap, roofing membranes, and other applications requiring high vapor transmission and high melting points.Type: GrantFiled: October 27, 2003Date of Patent: April 10, 2007Assignee: Noveon, Inc.Inventors: Ravi Ram Vedula, Kimberly Lynn Young
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Patent number: 7015299Abstract: Melt spun thermoplastic polyurethane polymers useful as textile fibers and having good tenacity and recovery and substantially no gelation are disclosed. The polymers are prepared by a three-step polymerization process including: preparation of “hard” segment oligomer, preparation of “soft” segment oligomer and final reaction of “hard” segment with “soft” segment in a twin-screw reaction extruder to obtain a final polyurethane product having relatively uniform distances between the “hard” segments. The “soft” segment oligomer comprises blocks of polymeric glycol (poly) urethanes end capped with isocyanate groups. The “hard” segment oligomer comprises blocks of low molecular weight C2–C6 glycol (poly) urethanes.Type: GrantFiled: April 30, 2001Date of Patent: March 21, 2006Inventor: W. Kenneth Wilkinson
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Patent number: 7001976Abstract: This invention relates to a water-soluble fiber and a method of manufacturing the fiber. The water-soluble fiber of the invention is composed of a high molecular compound with a weight average molecular weight of not less than 10,000, which high molecular compound is obtainable by reacting a polyalkylene oxide compound, which is obtainable by addition polymerization of an ethylene oxide-containing alkylene oxide and an organic compound containing two active hydrogen atoms, with a polycarboxylic acid, an anhydride thereof, a lower alkyl ester thereof, or a diisocyanate and is manufactured by spinning the same high molecular compound. The water-soluble fiber of the invention is not only high in elongation and tensile strength but is readily soluble in water.Type: GrantFiled: April 24, 2003Date of Patent: February 21, 2006Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Takeshi Fujita, Chuzo Isoda, Sejin Pu
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Patent number: 6984708Abstract: The invention provides spandex having improved hysteresis and a method for making such spandex. The spandex of the invention comprises the polyurethaneurea reaction product of: (a) poly(tetramethylene ether) glycol (b) 1-isocyanato-4-[(4-isocyanatophenyl)methyl]benzene wherein the mole ratio of diisocyanate to glycol is from about 1.52 to about 2.04; and (c) a mixture of chain extenders comprising: from about 35 to about 55 mole percent ethylene diamine; and from about 45 to about 65 mole percent 1,2-propanediamine.Type: GrantFiled: October 4, 2002Date of Patent: January 10, 2006Assignee: Invista North America S.a.r.l.Inventors: Hong Liu, Gregory L. Yoder, Robert O. Waldbauer, Jr.
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Patent number: 6964626Abstract: The present invention relates to molded polyurethane/urea elastomers, and specifically to improved polyurethane/urea elastomers having high temperature stability to about 140–150° C. and low temperature flexibility at about ?35–(?40)° C., for use in dynamic applications. These elastomers are particularly useful for application in belts, specifically in automotive timing or synchronous belts, V-belts, multi V-ribbed or micro-ribbed belts, flat belting and the like. The polyurethane/urea elastomers of the present invention are prepared by reacting polyisocyanate prepolymers with symmetric primary diamine chain extenders, mixtures of symmetric primary diamine chain extenders and secondary diamine chain extenders, or mixtures of symmetric primary diamine chain extenders and non-oxidative polyols, which are all chosen to eliminate the need for catalysts via standard molding processes, and to improve phase separation.Type: GrantFiled: June 12, 1996Date of Patent: November 15, 2005Assignee: The Gates CorporationInventors: William W. L. Wu, James R. Stamp, W. Joe Brothers
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Patent number: 6956074Abstract: There is a provided a polyurethane composition, which exhibits an excellent property of preventing discoloring or coloring not only by oxidized nitrogen gases but also by heat, characterized in that (A) a hindered phenol antioxidant, and (B) an amide represented by the following general formula (I): R1—CONH2??(I) wherein R1 represents an alkyl group having 12 to 21 carbon atoms is compounded in the polyurethane.Type: GrantFiled: August 19, 1999Date of Patent: October 18, 2005Assignee: Sumitomo Chemical Company, Ltd.Inventors: Kenji Kimura, Kanako Fukuda, Mutsuko Higo, Kunihito Miyake
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Patent number: 6916896Abstract: Commercially acceptable spandex can be prepared with greater efficiency, improved consistency and at lower costs from a high-solids content polyurethaneurea polymer solution. The polyurethaneurea is prepared using a combination of 4,4?-MDI and 2,4?-MDI, and an amount of chain extenders and chain terminators such that the polymer solution, prior to spinning, is highly soluble and has an appropriate pre-spun IV and primary amine content.Type: GrantFiled: May 5, 2003Date of Patent: July 12, 2005Assignee: Invista North America S.a.r.l.Inventors: Gordon W. Selling, Nathan E. Houser
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Patent number: 6906163Abstract: Segmented polyurethane/ureas useful for the production of spandex, particularly spandex fibers, are made from isocyanate-terminated prepolymers formed by reacting excess isocyanate with an isocyanate-reactive component satisfying specified compositional requirements in the presence of a catalyst which promotes linear polymerization but does not cause degradation of the polymer. Suitable catalysts include metal salts of organic fatty acids and/or of naphthenic acid. The isocyanate-reactive component includes at least 10 equivalent percent of a polyoxypropylene diol having a number average molecular weight of at least about 1500 Da and an average unsaturation level less than or equal to 0.03 meq/g and up to 90 equivalent percent of a polytetramethylene glycol having a number average molecular weight of at least 200 Da.Type: GrantFiled: May 30, 2002Date of Patent: June 14, 2005Assignee: Bayer Materialscience LLCInventors: Bruce D. Lawrey, Thomas A. J. Gross, Rolf-Volker Meyer
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Patent number: 6903179Abstract: Segmented polyurethane/ureas useful in the production of spandex are produced by chain extending an isocyanate-terminated prepolymer in the presence of a solvent. The isocyanate-terminated prepolymer is formed by reacting a stoichiometric excess of an isocyanate with an isocyanate-reactive component that includes more than 50 equivalent percent of a high molecular weight polyoxyalkylene diol having an unsaturation level no greater than about 0.015 meq/g and up to about 50 equivalent percent of a polytetramethylene ether glycol.Type: GrantFiled: May 30, 2002Date of Patent: June 7, 2005Assignee: Bayer Materialscience LLCInventor: Bruce D. Lawrey
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Patent number: 6780958Abstract: The invention provides an improved spandex that is prepared from a polyurethane that is the reaction product of organic diisocyanates, polymeric glycols, and polyols that have an aromatic functionality, such as alkoxylated phenols. The spandex has improved resistance to high temperature dyeing with minimal loss of physical properties, such as elastic recovery.Type: GrantFiled: July 24, 2002Date of Patent: August 24, 2004Assignee: RadiciSpandex CorporationInventor: Andrea DeGuia
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Patent number: 6737497Abstract: Segmented polyurethane/ureas useful in the production of spandex are produced by chain extending an isocyanate-terminated prepolymer with a diamine chain extender that includes: (1) from about 7 to 25 equivalent percent of an asymmetric aliphatic and/or cycloaliphatic diamine and (2) a linear diamine such as ethylene diamine in the presence of a solvent. The isocyanate-terminated prepolymer is produced by reacting a stoichiometric excess of an isocyanate with an isocyanate-reactive component that includes: (1) from about 10 to about 70 equivalent percent of a polyoxypropylene diol having a molecular weight in excess of 1500 Da and an average unsaturation level no greater than about 0.03 meq/g and (2) from about 30 to about 90 equivalent percent of a polytetramethylene ether glycol having a molecular weight of at least 600 Da.Type: GrantFiled: May 30, 2002Date of Patent: May 18, 2004Assignee: Bayer Polymers LLCInventors: Bruce D. Lawrey, Thomas A. J. Gross, Rolf-Volker Meyer
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Patent number: 6720403Abstract: Spandex having good whiteness retention, high heat-set efficiency, and percent set is made from comprises amide soluble polyurethaneurea polymers prepared by reacting polyether which comprises the reaction product of a polymeric glycols with ortho-substituted diisocyanates and bulky diamine chain extenders.Type: GrantFiled: November 1, 2002Date of Patent: April 13, 2004Assignee: E.I. duPont de Nemours and Co.Inventor: Nathan E. Houser
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Publication number: 20040068080Abstract: The invention provides spandex having improved hysteresis and a method for making such spandex.Type: ApplicationFiled: October 4, 2002Publication date: April 8, 2004Inventors: Hong Liu, Gregory L. Yoder, Robert O. Waldbauer
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Patent number: 6660825Abstract: The present invention can provide a lactone polyester diol at least containing &egr;-caprolactone and a dibasic acid as constructing component units, and a polyurethane obtained using the diol and an organic diisocyanate can provide a spandex filament which is more excellent in a recovering ability of elasticity, strength, hydrolysis resistance, and heat resistance.Type: GrantFiled: July 15, 2002Date of Patent: December 9, 2003Assignee: Daicel Chemical Industries, LTDInventor: Toshio Endo
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Patent number: 6639041Abstract: A low set (at low temperatures) spandex, based on copoly(alkylene ethers), which are copolymers containing tetramethylene ether and either ethylene ether or 1,2-propylene ether moieties, is provided.Type: GrantFiled: May 31, 2002Date of Patent: October 28, 2003Assignee: DuPont-Toray Co. Ltd.Inventors: Hiroshi Nishikawa, Masao Umezawa
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Patent number: 6624281Abstract: Segmented polyurethane/ureas useful for the production of spandex are produced by chain extending, in the presence of a solvent, an isocyanate-terminated prepolymer prepared by reacting a stoichiometric excess of an isocyanate with an isocyanate-reactive component which includes: (1) from about 5 to about 30 equivalent percent of a polyoxy-propylene diol having a molecular weight of at least 1500 Da and an unsaturation level less than or equal to 0.03 meq/g; (2) from about 20 to about 60 equivalent percent of a polytetramethylene ether glycol having a molecular weight less than 1000 Da; and (3) from about 25 to about 65 equivalent percent of a polytetramethylene ether glycol having a molecular weight greater than or equal to 1000 Da.Type: GrantFiled: May 30, 2002Date of Patent: September 23, 2003Assignee: Bayer CorporationInventor: Bruce D. Lawrey
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Patent number: 6503996Abstract: The invention provides a highly uniform spandex fiber and a method for making it. The polyurethaneurea component of the spandex has both alkylurethane and monoalkylurea ends, with a ratio of monoalkylurea ends to alkylurethane ends of from 0.5:1 to 10:1.Type: GrantFiled: November 14, 2001Date of Patent: January 7, 2003Assignee: DuPont Dow Elastomers L.L.C.Inventors: Donald D. Bretches, Gary A. Lodoen
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Patent number: 6500911Abstract: The invention provides polyester dials suitable for preparation of polyurethanes, and provides polyurethanes derived therefrom. The invention also provides spandex filaments prepared from these polyurethanes, which exhibit improved elasticity, tensile strength, and resistance to hydrolysis. The present invention also provides dialkyl amino group-containing polyol additives having a high solubility in dimethylacetamide solvent, which when incorporated into a polyurethane protect the polyurethane and derived spandex filaments from deterioration or discoloration, and confer an improved modulus of elasticity. The polyurethanes and spandex filaments of the invention provide fabrics having a soft feeling, excellent hydrolysis resistance, wrinkle resistance, and adhesive properties, and which are particularly suitable for preparation of an artificial leather.Type: GrantFiled: March 8, 2001Date of Patent: December 31, 2002Assignee: Daicel Chemical Industries, Ltd.Inventors: Toshio Endo, Takuya Miho
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Patent number: 6485665Abstract: Polyurethane elastomer fibers with superior mechanical and heat distortion properties are obtained by a method in which (a) a segmented polyurethane polymer is produced on the basis of a macro-diol, an aliphatic diisocyanate, and a chain extender with at least two hydroxy and/or amino groups, where the polymer has a molar excess of isocyanate groups over the hydroxy and/or amino groups from the macro-diol and chain extender; (b) the polyurethane polymer is melt-extruded to form a fiber; and (c) The extruded fiber is subjected to a post-treatment. Steps (a) and (b) are carried out under temperature conditions and within a time interval where essentially no allophanate will be formed, while step (c) is performed under temperature conditions and within a time interval in which the polyurethane polymer is cross-linked through the formation of allophanate.Type: GrantFiled: July 19, 2000Date of Patent: November 26, 2002Assignee: Rhodianyl S.N.C.Inventors: Frank Hermanutz, Peter Hirt, Oliver Oess, Wilhelm Oppermann
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Publication number: 20020161137Abstract: Melt spun thermoplastic polyurethane polymers useful as textile fibers and having good tenacity and recovery and substantially no gelation are disclosed. The polymers are prepared by a three-step polymerization process including: preparation of “hard” segment oligomer, preparation of “soft” segment oligomer and final reaction of “hard” segment with “soft” segment in a twin-screw reaction extruder to obtain a final polyurethane product having relatively uniform distances between the “hard” segments. The “soft” segment oligomer comprises blocks of polymeric glycol (poly) urethanes end capped with isocyanate groups. The “hard” segment oligomer comprises blocks of low molecular weight C2-C6 glycol (poly) urethanes.Type: ApplicationFiled: April 30, 2001Publication date: October 31, 2002Inventor: W. Kenneth Wilkinson
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Patent number: 6472494Abstract: A high heat-set efficiency, high unload power spandex, based on a polyurethaneurea prepared from a polyether glycol, mixtures of 2,4′-MDI and 4,4′-MDI, and chain extenders, is provided.Type: GrantFiled: February 22, 2001Date of Patent: October 29, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Nathan E Houser, Gordon W Selling
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Patent number: 6458866Abstract: The invention concerns a polyurethane elastomer containing structural units of type (a), in which: the group —O—R1—O—is a macrodiol group with a molecular weight of approximately 500 to 10000, R2 is a bivalent aliphatic, cycloaliphatic and/or aliphatic-cycloaliphatic group; and X is a short-chain olefinically unsaturated group, Y is NH or O, n is an integer from 1 to 10 and m is an integer of at least 4. The invention also concerns a method of preparing this polyurethane elastomer which can be melt-spun to form fibres or melt-extruded to form foils. The fibres or foils can be exposed to energy-rich radiation such that crosslinking of the polyurethane occurs. Fibres according to the invention display superior properties in terms of textile-mechanical properties, in particular good tensile strength, elongation at tear, residual elongation and heat distortion temperature.Type: GrantFiled: May 15, 1998Date of Patent: October 1, 2002Assignee: Rhodia S.A.Inventors: Wilhelm Oppermann, Frank Hermanutz, Peter Hirt, Michael Schweizer, Oliver Oess
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Publication number: 20020107352Abstract: A continuous process for the production of thermoplastically processable polyurethane elastomer is disclosed. The process comprise adding acid H compounds in an amount calculated to control and render constant the melt viscosity of the product. The inventive elastomer has constant melt flow behavior and high thermal stability.Type: ApplicationFiled: December 3, 2001Publication date: August 8, 2002Inventors: Friedemann Muller, Wolfgang Brauer, Hans-Georg Hoppe, Hans-Georg Wussow, Hans Wagner
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Publication number: 20010044517Abstract: A high heat-set efficiency, high unload power spandex, based on a polyurethaneurea prepared from a polyether glycol, mixtures of 2,4′-MDI and 4,4′-MDI, and chain extenders, is provided.Type: ApplicationFiled: February 22, 2001Publication date: November 22, 2001Inventors: Nathan E. Houser, Gordon W. Selling
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Patent number: 6277942Abstract: Novel melt-spun elastomeric fibers and methods for their preparation. Embodiments are provided in which fibers are melt-spun from a melt-spinnable elastomeric polymer comprising a diisocyanate-capped polyol prepolymer which is chain-extended with an aromatic dihydroxy compound. Also provided are melt-spinnable elastomeric polymers and prepolymers therefor. The fibers may be knit or woven into textile articles including, inter alia, hosiery and pantyhose.Type: GrantFiled: May 19, 1998Date of Patent: August 21, 2001Assignee: Optimer, Inc.Inventor: Robert P. Foss
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Patent number: 6252031Abstract: A process for producing a polyurethane elastic material or polyurethane elastic yarn from a first polymer diol having a molecular weight of 600 or more, a second polymer diol having a molecular weight of 600 or more, a first low molecular weight diol having a molecular weight of 500 or less, a second low molecular weight diol, a first diisocyanate and a second diisocyanate as main starting materials, the total amount of the first diisocyanate and the second diisocyanate in the starting materials being 0.95 to 1.Type: GrantFiled: September 30, 1999Date of Patent: June 26, 2001Assignee: Nisshinbo Industries, Inc.Inventors: Nobuhisa Tsutsumi, Kenji Tamura, Mitsuhiko Yoshimoto
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Patent number: 6225435Abstract: A viscosity-stable solution of a polyurethaneurea, in the substantial absence of viscosity stabilizers, and spandex dry-spun therefrom, prepared from certain polyether glycols and aliphatic diisocyanates and ethylene diamine, are provided.Type: GrantFiled: September 1, 1999Date of Patent: May 1, 2001Assignee: DuPont Toray Co. Ltd.Inventors: Shingo Ito, Toshikazu Matsuda, Masao Umezawa
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Patent number: 6197915Abstract: The invention relates to thermoplastic polyurethanes obtainable by reacting a polyol composition (A) which consists essentially of a polyester-polyol (A-1) having a crystallization enthalpy of at most 70 J/g and a number-average molecular weight of from 1000 to 5000 and a polyether-polyol (A-2) having a number-average molecular weight of from 500 to 2500, and in which the average number, f, of the functional hydroxyl groups existing therein falls between 2.006 and 2.100, an organic diisocyanate (B), and a chain extender (C), at a ratio that satisfies the following formula: 1.00≦b/(a+c)≦1.10 wherein a indicates the number of moles of all polyols constituting the polyol composition (A), b indicates the number of moles of the organic diisocyanate (B), and c indicates the number of moles of the chain extender (C); to elastic fibers comprising them; and to a method for producing polyurethane elastic fibers by melt-spinning the thermoplastic polyurethane.Type: GrantFiled: June 23, 1999Date of Patent: March 6, 2001Assignee: Kuraray Co., Ltd.Inventors: Yoshihiro Yamana, Hiroyuki Ono
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Patent number: 6127506Abstract: A process for melt spinning spandex, utilizing a polyurethaneurea polymer prepared from a purified capped glycol, linear aliphatic diamines and a monoamine chain terminator, is provided.Type: GrantFiled: February 19, 1999Date of Patent: October 3, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: Robin N. Greene
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Patent number: 6100360Abstract: A polyurethane elastic fiber is prepared from a polyurethane prepolymer by reaction extruding the polyurethane prepolymer and a chain extender, preferably with twin-screw extruder, and melt spinning the resulting polyurethane elastomer from the extrusion. The polyurethane prepolymer is obtained by carrying out a pre-polymerization reaction of a polyester diol and a diisocyanate, wherein the polyester diol comprises two different types of polyol, the first type being poly(tetramethylene adipate) glycol or poly(.epsilon.-caprolactone) glycol and the second type being a reaction product of a diol and dicarboxylic acid having 36 carbon atoms.Type: GrantFiled: May 19, 1999Date of Patent: August 8, 2000Assignee: Acelon Chemicals & Fiber CorporationInventors: Yaw Kuo Twu, Jaw hsiung Tsai, Jing Xin Lin, Deng Hung Lee
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Patent number: 6093783Abstract: This invention relates to a water-soluble fiber and a method of manufacturing the fiber. The water-soluble fiber of the invention is composed of a high molecular compound with a weight average molecular weight of not less than 10,000, which high molecular compound is obtainable by reacting a polyalkylene oxide compound, which is obtainable by addition polymerization of an ethylene oxide-containing alkylene oxide and an organic compound containing two active hydrogen atoms, with a polycarboxylic acid, an anhydride thereof, a lower alkyl ester thereof, or a diisocyanate and is manufactured by spinning the same high molecular compound. The water-soluble fiber of the invention is not only high in elongation and tensile strength but is readily soluble in water.Type: GrantFiled: January 18, 1996Date of Patent: July 25, 2000Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Takeshi Fujita, Chuzo Isoda, Sejin Pu
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Patent number: 6063892Abstract: Polurethaneaureas prepared with 2,2-bis(4-isocyanatophenyl)propane or 1,4-bis(4-isocyanato-alpha,alpha-dimethylbenzyl)benzene, and spandex spun from such polyurethaneureas, are provided.Type: GrantFiled: October 5, 1999Date of Patent: May 16, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Nathan E. Houser, Chad J. Kolaskie
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Patent number: 5981686Abstract: A polyurethaneurea polymer and spandex spun therefrom, based on polymeric ester or ether glycols and MDI at certain capping ratios, and 1,3-diaminopentane chain extender, are provided.Type: GrantFiled: March 26, 1998Date of Patent: November 9, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: Robert Otto Waldbauer, Jr.
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Patent number: 5962619Abstract: A process for making clear elastomers is disclosed. First, a polyol having a narrow molecular weight distribution (Mw/Mn<1.5) reacts an aromatic diisocyanate at an NCO/OH ratio from about 1.3 to about 3.0 to give a non-viscous isocyanate-terminated prepolymer. A mixture that contains this prepolymer and an aliphatic diisocyanate is then reacted with an aromatic diamine to give a clear elastomer. The elastomers have excellent overall physical and mechanical properties, including resilience greater than 55%. The elastomers are valuable for in-line skates and other applications for which clarity is important.Type: GrantFiled: March 16, 1998Date of Patent: October 5, 1999Assignee: ARCO Chemical Technology, L.P.Inventors: Stephen D. Seneker, Chin-Chang Shen
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Patent number: 5959059Abstract: A thermoplastic polyether polyurethane having good rebound resilience and low hysteresis properties is prepared by the reaction of a diisocyanate with a hydroxyl terminated polyether having a weight average molecular weight of at least 1,400 and a glycol chain extender. The polyether contains alkylene oxide repeat units having from 2 to 6 carbon atoms and the chain extender glycol has from 2 to 16 carbon atoms. The amount of the chain extender glycol is from about 0.25 to about 2 moles per mole of the polyether.Type: GrantFiled: June 10, 1997Date of Patent: September 28, 1999Assignee: The B.F. Goodrich CompanyInventors: Ravi Ram Vedula, Stanley Raymond Goscewski
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Patent number: 5948875Abstract: New polyurethaneurea polymers and spandex made therefrom, based on certain glycols, MDI and a diamine chain extender mixture containing high proportions of 2-methyl-1,5-pentanediamine and prepared at selected capping ratios, are provided.Type: GrantFiled: March 26, 1998Date of Patent: September 7, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Hong Liu, Robert Otto Waldbauer, Jr.
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Patent number: 5879596Abstract: A process for making polyurethaneureas using cryogenic mixing is provided. Such polyurethaneureas are useful for making spandex and, ultimately, various types of clothing. The process involves cooling an isocyanate prepolymer or the like to a temperature of less than about -100.degree. C., forming a powder from the isocyanate prepolymer, adding at least one chain extender and/or chain terminator, and warming the powder to at least about room temperature to produce a polyurethaneurea. Such polyurethaneureas are useful for making spandex and, ultimately, various types of clothing.Type: GrantFiled: July 15, 1997Date of Patent: March 9, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: David H. Roach
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Patent number: 5843357Abstract: Spandex-type segmented polyurethane/urea elastomers having exceptional elongation, hysteresis, recovery, and other physical properties are prepared by the amine chain extension of an isocyanate-terminated prepolymer prepared by the reaction of a stoichiometric excess of isocyanate with a polyol blend comprising a low molecular weight diol having a molecular weight below 750 Da with a high molecular weight glycol which may be a 1500 Da to 20,000 Da molecular weight, ultra-low unsaturation polyoxypropylene glycol with an unsaturation of less than about 0.010 meq/g.Type: GrantFiled: September 8, 1997Date of Patent: December 1, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Stephen D. Seneker, Bruce D. Lawrey
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Patent number: 5723563Abstract: Spandex-type polyurethane/urea segmented elastomers with exceptional physical properties may be prepared by the aliphatic and/or cycloaliphatic diamine chain extension of a solution of isocyanate-terminated polyoxypropylene diol-derived prepolymer wherein the diol component comprises in major part an ultra-low unsaturation polyoxypropylene diol having an unsaturation of less than about 0.010 meq/g and a number average molecular weight greater than 2000 Da. The spandex polymers have commercially desirable percent set and are capable of exceeding the properties of the industry standard PTMEG elastomers in many respects, particularly in elongation and hysteresis.Type: GrantFiled: October 11, 1996Date of Patent: March 3, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Bruce D. Lawrey, Stephen D. Seneker
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Patent number: 5708118Abstract: Spandex-type segmented polyurethane/urea elastomers having exceptional elongation, hysteresis, recovery, and other physical properties are prepared by the amine chain extension of an isocyanate-terminated prepolymer prepared by the reaction of a stoichiometric excess of isocyanate with a polyol blend comprising a low molecular weight diol having a molecular weight below 750 Da with a high molecular weight glycol which may be a 1500 Da to 20,000 Da molecular weight, ultra-low unsaturation polyoxypropylene glycol with an unsaturation of less than about 0.010 meq/g.Type: GrantFiled: October 11, 1996Date of Patent: January 13, 1998Assignee: ARCO Chemical Technology, L.P.Inventors: Stephen D. Seneker, Bruce D. Lawrey
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Patent number: 5703158Abstract: Sulfonated polyester polyols and mixtures of sulfonated polyester polyols and hydroxy carboxylic acids are used to prepare improved aqueous anionic poly(urethane/urea) dispersions with a high crystallization rate, low heat activation temperature, high green strength, stability at low pH, which show good compatibility with other water based polymers and with crosslinkers. The aqueous anionic poly(urethane/urea) dispersions have high heat resistance after curing or blending with a crosslinker.Type: GrantFiled: November 22, 1994Date of Patent: December 30, 1997Assignee: H.B. Fuller Licensing & Financing, Inc.Inventors: Youlu Duan, Michael J. Dochniak, Sonja Stammler
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Patent number: 5691441Abstract: Substitution of from 5 to 50 equivalent percent of an ultra-low unsaturation polyoxypropylene diol for PTMEG in isocyanate-terminated prepolymers used in spandex production is found to lower considerably both prepolymer viscosity and hysteresis while substantially retaining other desirable physical properties. Such products may offer higher fiber production rates than are possible while employing an all PTMEG-derived polymer.Type: GrantFiled: October 11, 1996Date of Patent: November 25, 1997Assignee: Arco Chemical Technology, L.P.Inventors: Stephen D. Seneker, Bruce D. Lawrey
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Patent number: 5644015Abstract: The present invention relates to a process of producing a polymer suitable for manufacturing spandex filament having remarkable elastic recovery rate and heat-setting efficiency wherein the process comprises: stirring a mixture of a glycol and a diisocyante, where the molar ratio of diisocyanate to glycol is 1.5 to 1.64, in a homogenizer at about 40.degree. to about 50.degree. C. and reacting said mixture to give a first polymer containing less than 4 mole % of unreacted diisocyanate; then, reacting said polymer with a chain-extender mixture containing ethylenediamine, 1,2-diaminopropane, and diethylenetriamine, preferably, about 74 to about 80 mole % of ethylenediamine, about 19 to about 25 mole % of 1,2-diaminopropane and about 0.2 to about 0.8 mole % of diethylenetriamine. Elastic polyurethaneurea-based spandex filament is produced by dry-spinning the polymer.Type: GrantFiled: July 24, 1996Date of Patent: July 1, 1997Assignee: Hyosung T & C Co., Ltd.Inventors: Seung-Won Seo, Mun-Seon Kim
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Patent number: 5616676Abstract: A thermosetting polyurethane-urea elastic yarn having a thermosetting ratio of 45-65%, which is obtained by reacting a polyglycol which has a number average molecular weight of 600-6,000 and which has hydroxy at both terminals, with a molar excess of a diisocyanate compound to give an isocyanate-terminated polymeric intermediate, reacting the isocyanate-terminated polymeric intermediate with a diamine compound to give a segmented polyurethane-urea elastomer, and subjecting the obtained elastomer to a spinning step. The thermosetting polyurethane-urea elastic yarn of the present invention has superior mechanical properties and high thermosetting ratios. When applied to knit fabric, particularly to thin knit fabric for panty hose, superior appearance of the knit fabric can be achieved.Type: GrantFiled: October 18, 1995Date of Patent: April 1, 1997Assignee: Toyo Boseki Kabushiki KaishaInventor: Kenichi Katsuo