Organic Nh, =nh Or Hnh Nitrogen Reactant Contains A Carbocyclic Or Aromatic Ring Patents (Class 528/64)
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Patent number: 6762273Abstract: A curative blend for a thermosetting polyurethane material that allows for a polyurethane material with greater durability is disclosed herein. The curative blend is preferably composed of N,N″-dialkylamino-diphenyl-methane in an amount of 25 to 75 parts per one hundred parts of the curative blend and 4,4″-methylenebis-(2,6-diethyl)-aniline in an amount of 25 to 75 parts per one hundred parts of the curative blend. A preferred polyurethane prepolymer is polytetramethylene ether glycol terminated toluene diisocyanate prepolymer. The thermosetting polyurethane is preferably utilized as a cover for a golf ball. The cover is preferably formed over a core and boundary layer.Type: GrantFiled: May 31, 2002Date of Patent: July 13, 2004Assignee: Callaway Golf CompanyInventor: Pijush K. Dewanjee
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Patent number: 6747117Abstract: A polyurethane composition is disclosed that comprises an isocyanate-terminated polyurethane prepolymer, and a curative agent including a polyaspartic ester. Desirably, the curative agent includes a co-curative selected from the group consisting aromatic diamines and diols. This composition is useful for rotationally casting cylindrical parts. The invention includes the method for coating a cylindrical object.Type: GrantFiled: June 14, 2002Date of Patent: June 8, 2004Assignee: Crompton CorporationInventor: Vincent J. Gajewski
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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: 6734272Abstract: A polyurethane resin composition for casting is provided which for use as a molding material for optical lenses, resistance to discoloration and durability are excellent and the pot life is long enough take time for casting process. It comprises a polyisocyanate, a polyhydroxy compound and an aromatic polyamine. The aliphatic polyisocyanate is 4,4′-methylene-bis(cyclohexyl isocyanate) or isophorone diisocyanate, the polyhydroxy compound is a polyether diol or polyester diol having an average molecular weight of 700-1200 or their mixture, and the aromatic polyamine is 4,4′-methylene-bis(2-chloroaniline).Type: GrantFiled: October 12, 2001Date of Patent: May 11, 2004Assignee: Talex Optical Co., Ltd.Inventors: Kanichi Tamura, Shoichi Mitsuuchi
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Publication number: 20040049003Abstract: 1.Type: ApplicationFiled: May 27, 2003Publication date: March 11, 2004Inventors: Yoshiyuki Asahina, Kaoru Ueyanagi, Hironori Katagawa
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Patent number: 6689860Abstract: There is provided a solid golf ball comprising a multi-piece core and a cover made from polyurethane obtained by curing an isocyanate group-terminated urethane prepolymer including a residual polyisocyanate monomer content of not more than 0.1% by mass using an aromatic polyamine curing agent. The golf ball satisfies moldability of the polyurethane cover and durability, and exhibits excellent ball characteristic such as flight performance and shot feeling.Type: GrantFiled: November 29, 2001Date of Patent: February 10, 2004Assignee: Sumitomo Rubber Industries LimitedInventor: Satoshi Iwami
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Patent number: 6686436Abstract: There is provided a solid golf ball comprising a core and a cover made from polyurethane obtained by curing an isocyanate group-terminated urethane prepolymer including a residual polyisocyanate monomer content of not more than 0.1% by mass using an aromatic polyamine curing agent. The golf ball satisfies moldability of the polyurethane cover and durability, and exhibits excellent ball characteristic such as flight performance and shot feeling.Type: GrantFiled: November 27, 2001Date of Patent: February 3, 2004Assignee: Sumitomo Rubber Industries LimitedInventor: Satoshi Iwami
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Patent number: 6683152Abstract: An insert for a golf club, wherein the insert is formed of a polyurethane composition comprising a prepolymer comprised of a polyol and a polyisocyanate, and a curing agent; and wherein the polyisocyanate is selected from the group consisting of 4,4′-diphenylmethane diisocyanate, polymeric 4,4′-diphenylmethane diisocyanate, toluene diisocyanate, 3,3′-dimethyl-4,4′-biphenylene diisocyanate, p-phenylene diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, and isophorone diisocyanate.Type: GrantFiled: August 2, 2001Date of Patent: January 27, 2004Assignee: Acushnet CompanyInventors: Shenshen Wu, Murali Rajagopalan
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Patent number: 6683151Abstract: The invention relates to a compound comprising a reaction product of (A) an isocyanate functional compound of which at least 40 wt. %, relative to the total amount of (A), has a molecular weight of at least about 500, and (B) a nitrogen-containing compound capable of reacting with said isocyanate functional compound (A). The reaction product has a molecular weight of less then about 20,000 and comprises an effective amount of groups that are able to form reversible intermolecular physical interactions such that a resulting compound shows polymeric mechanical properties at a temperature below a transition temperature. The nitrogen-containing compound is, for instance, melamine, urea, acetoguanamine, benzoguanamine, cyanamide, dicyanamide, thiourea, isocytosine, pyrimidone or aminopyridine. The supramolecular compound comprising a suitable amount of the reaction products exhibits a relatively high elongation at break.Type: GrantFiled: February 24, 2000Date of Patent: January 27, 2004Assignee: DSM N.V.Inventors: Jacobus A. Loontjens, Johan E. G. A. Jansen, Bartholomeus J. M. Plum
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Patent number: 6649726Abstract: The two-component type polyurethane composition according to the present invention is obtained from a principal component containing a compound having an isocyanate group and a curing agent containing a compound having active hydrogen, and is characterized in that both the principal component and the curing agent contain substantially no thixotropic agent, the mixture of the principal component and the curing agent has a specific thixotropy-developing time and a specific slump, the active hydrogen compound has a specific flash point, and that the mass change of the two-component type polyurethane composition before/after boiling in boiling water under specific conditions is in a specific range.Type: GrantFiled: August 4, 2000Date of Patent: November 18, 2003Assignee: Mitsui Chemicals, Inc.Inventors: Hisashi Kawanabe, Hiroaki Sakaguchi, Kazuto Usaka, Takashi Abe
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Patent number: 6649706Abstract: A thixotroping agent comprising a reaction product of a isocyanto-containing compound and an amine. The isocyanto-containing compound comprises at least one of Ia) at least one isocyanate with at least one diisocyanate structural unit that has an unsaturated/aromatic or non-aromatic ring structure with 5-10 ring atoms and two isocyanate groups that are bound to the ring structure; Ib) at least one oligomer of the isocyanate Ia) with 2 to 10 isocyanate units; and Ic) at least one partially blocked isocyanate Ia) and/or at least one partially blocked oligomer Ib).Type: GrantFiled: November 14, 2001Date of Patent: November 18, 2003Assignee: BASF Coatings AGInventors: Ingrid Heid, Helmut Kleine Beckmann, Ulrike Röckrath, Hubert Baumgart
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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: 6635737Abstract: Low unsaturation, high molecular weight polyols having an unsaturation level below or equal to 0.006 milli-equivalents per gram, and preferably below 0.004 milli-equivalents per gram, and molecular weights of greater than or equal to about 2,000, and preferably between about 2,000 and 10,000, are converted into low unsaturation, high molecular-weight (LUSHMW) polyamines directly by amination reactions. The LUSHMW polyamines produce polymers having elongation, modulus, and tensile characteristics that are substantially better than those of conventional analogous polymers.Type: GrantFiled: May 25, 2001Date of Patent: October 21, 2003Assignee: Williamette Valley CompanyInventors: Donald A. Upson, Omar Tiba, Robert M. Loomis
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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: 6613864Abstract: A polyurethane composition useful for the manufacture of an elastomeric part is provided. The polyurethane composition comprises a polyisocyanate prepolymer and an active hydrogen containing compound, wherein from about 10 to about 60 percent by weight of the composition is a butylene oxide adduct and from about 70 to about 100 percent of the butylene oxide adduct is present in the polyisocyanate prepolymer. A method for preparing a polyurethane polymer from the polyurethane composition is also provided. Also, a method for preparing a polyurethane article from the polyurethane composition is provided.Type: GrantFiled: August 17, 2001Date of Patent: September 2, 2003Assignee: Dow Global Technologies Inc.Inventors: James R. Porter, Allan James, Kenneth B. Arnold
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Patent number: 6607795Abstract: Herein is disclosed an oxygen scavenging composition, comprising (i) an oxygen scavenging polymer comprising units having structure I: wherein R1 and R2 are independently selected from the group consisting of —O—, —NCO—, and —NR—, wherein R is selected from the group consisting of —H and —C1-C6 alkyls; (ii) a transition metal oxidation catalyst; and (iii) an energy-absorbing compound selected from the group consisting of microwave reactive materials and photoinitiators having a wavelength of maximum absorption of electromagnetic radiation from about 200 nm to about 750 nm. The oxygen scavenging composition can be used to form an oxygen scavenging packaging article.Type: GrantFiled: December 19, 2001Date of Patent: August 19, 2003Assignee: Chevron Phillips Chemical Company LPInventors: Hu Yang, Ta Yen Ching, Peter Kwan
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Patent number: 6607686Abstract: A prepolymer blend for a thermosetting polyurethane material that allows for control of the reaction time is disclosed herein. The prepolymer blend is preferably composed of a polyurethane prepolymer and dimethyl methylphosphonate. The thermosetting polyurethane is preferably utilized as a cover for a golf ball. The cover is preferably formed over a core and boundary layer.Type: GrantFiled: November 6, 2001Date of Patent: August 19, 2003Assignee: Callaway Golf CompanyInventor: Pijush K. Dewanjee
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Patent number: 6605684Abstract: This invention concerns a method for the preparation of polyurea elastomers, comprising: (a) reacting an amine chain extender with dialkyl maleate to form an aspartic ester, wherein the chain extender has a molar amount of amine groups that is greater than the moles of dialkyl maleate; (b) blending the aspartic ester with one or more polyoxyalkyleneamines to prepare a resin blend; (c) contacting the resin blend with an isocyanate under conditions effective to form a polyurea elastomer. This invention concerns a method for the preparation of polyurethane elastomers, comprising: (a) reacting an diamine chain extender with dialkyl maleate or fumarate, wherein the mole ratio of primary amine functionality in the diamine chain extender to dialkyl maleate or fumarate is more than 1:1; (b) coating a substrate with effective film forming amounts of the product of step (a), an isocyanate, and a polyhydroxyl compound under conditions effective to form a the polyurethane elastomer.Type: GrantFiled: January 14, 2002Date of Patent: August 12, 2003Assignee: Huntsman Petrochemical CorporationInventors: Dudley J. Primeaux, II, Robert L. Zimmerman, Kenneth M. Hillman
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Patent number: 6593443Abstract: A wound-core golf ball having a polyurethane cover is disclosed. The polyurethane cover is formed by curing a composition including an isocyanate group terminated polyurethane prepolymer containing a residual polyisocyanate monomer in an amount of not more than 0.1 mass %; and an aromatic polyamine compound. Use of this isocyanate group terminated polyurethane prepolymer enables the homogeneous curing reaction even at the low temperature, thus the golf ball which has the polyurethane cover exhibiting excellent performance is obtained.Type: GrantFiled: September 5, 2001Date of Patent: July 15, 2003Assignee: Sumitomo Rubber Industries, LimitedInventor: Satoshi Iwami
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Publication number: 20030120020Abstract: The invention is intended to provide a solid golf ball having a polyurethane cover having satisfactory formability and ball properties. The golf ball of the present invention provides the good shot feeling, the controllability, and the resilience by adjusting the hardness and the thickness of the polyurethane cover, and the hardness of the whole golf ball. Further, the formability of the polyurethane cover has been improved by controlling the amount of residual isocyanate monomer contained in the isocyanate group-terminated urethane prepolymer.Type: ApplicationFiled: November 25, 2002Publication date: June 26, 2003Inventors: Masatoshi Yokota, Kaname Yamada, Seigou Sakagami
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Patent number: 6562932Abstract: This invention relates to a process for the production of an optically clear, light-stable polyurethane-urea elastomer having an onset softening point of at least 130° C., processed at ambient temperature and casted in a mold at an isocyanate index of 95 to 120. This process comprises reacting: A) a liquid polyisocyanate or polyisocyanate prepolymer having an NCO group content of about 5 to about 50%, an average functionality of 2 to 3, a viscosity of less than 5,000 mPa.s at 25° C.; and B) an isocyanate-reactive component; in the presence of C) at least one organometallic catalyst. The present invention also relates to the optically clear, light-stable polyurethane-urea elastomers produced by this process.Type: GrantFiled: October 12, 2001Date of Patent: May 13, 2003Assignee: Bayer CorporationInventors: Peter H. Markusch, Robert L. Cline, Richard S. Pantone, Ralf Guether, Thomas L. Sekelik, Karl W. Haider
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Patent number: 6552155Abstract: The invention relates to polyaldimines of formula [1] and their use within moisture curable one part polyurea compositions. wherein j is an integer of 3 to 30 and R2 is unsubstituted homocyclic or heterocyclic aryl radical or alkyl, alkoxy, alkylthio or halogen substituted homocyclic or heterocyclic aryl radical.Type: GrantFiled: October 25, 2001Date of Patent: April 22, 2003Inventors: Arie Gutman, Gennadiy Nisnovich, Igor Zaltzman, Lev Judovich, Vladimir Kuznetsov
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Publication number: 20030065124Abstract: The invention is directed to polyurethane prepolymers having a reduced amount of unreacted monomeric diisocyanate, particularly diphenylmethane diisocyanate (MDI), prepared by distilling the prepolymer reaction product in the presence of at least one inert solvent whose boiling point is slightly below that of the monomeric diisocyanate; and to high performance cast polyurethane elastomers from the thus obtained prepolymers using diamine and/or diol chain extenders.Type: ApplicationFiled: August 2, 2001Publication date: April 3, 2003Inventors: Ronald O. Rosenberg, Rui Xie, Ajaib Singh
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Patent number: 6531076Abstract: Described are photochromic organic resin compositions and the impact resistant polymerizates and coating compositions made therefrom. The organic resin composition comprises the reaction product of at least one polyol having greater than 1.0 hydroxyl groups; at least one polyisocyanate having greater than 1.0 isocyanato groups; and at least one polyamine curing agent having greater than 1.0 amino groups. The polymerizates are made photochromic either by the addition of organic photochromic compounds to the reactants used to form the polymerizate or by methods that imbibe or transfer the photochromic compounds into the polymerizate. Optically clear photochromic and impact resistant articles such as ophthalmic lenses and articles having photochromic coatings prepared from the photochromic organic resin compositions are also described.Type: GrantFiled: January 19, 2001Date of Patent: March 11, 2003Assignee: PPG Industries Ohio, Inc.Inventors: John C. Crano, Carol L. Knox, Michael O. Okoroafor, Robert A. Smith, Rifat Tabakovic
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Patent number: 6530849Abstract: Disclosed herein is a golf ball comprising a core and a cover, said cover comprising a polyurethane elastomer comprising the reaction product of: A) at least one diisocyanate monomer; B) at least one polyol that is a homopolymer of propylene oxide having a molecular weight greater than 1000; and C) at least one hydroxy or amine functional chain extender; wherein the ratio of equivalents of chain extender plus polyol to equivalents of isocyanate is in the range of from about 0.6:1 to about 1.2:1, whereby said polyurethane elastomer possesses high shear resistance and good resilience.Type: GrantFiled: October 12, 2001Date of Patent: March 11, 2003Assignee: Uniroyal Chemical Company, Inc.Inventor: Thomas H. Peter
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Patent number: 6525131Abstract: Disclosed herein is a composition comprising an aromatic diamine that is a solid at room temperature and a stabilizing quantity of a hindered amine light stabilizer and its use as a polyurethane curing agent.Type: GrantFiled: September 18, 2001Date of Patent: February 25, 2003Assignee: Crompton CorporationInventor: Thomas H. Peter
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Patent number: 6509434Abstract: Mixtures of isomeric alkylthiated mononuclear aromatic amines comprising in the range of about 30 to about 70 mole percent of (i) at least one 3,5-di(alkyl-thio)-2,6-diamino-1-alkylbenzene and in the range of about 30 to about 70 mole percent of at least one 3,5-di(alkylthio)-2,4-diamino-1-alkylbenzene, such mixture containing at least about 90 mole percent of (i) and (ii), and optionally containing up to 10 mole percent of one or more isomers of (i) and/or (ii). An alkyl group may be present as a substituent in lieu of a hydrogen atom in the remaining ring position. These mixtures are useful as curatives or extenders in processes for making polyurethanes, polyurethane-ureas, and polyureas.Type: GrantFiled: March 20, 2000Date of Patent: January 21, 2003Assignee: Albemarle CorporationInventors: William R. Brown, John C. Prindle, Jr., Gregory H. Lambeth
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Publication number: 20030013835Abstract: A polyurea composition free from polyol linkages. A composition and process for producing a two component spray 100% polyurea elastomeric system wherein an A and a B component are mixed, wherein said A component is a prepolymer produced by an aromatic isocyanate and amine terminated materials and wherein said B component is 100% amine terminated reactive ingredients. The instant invention can be used as a spray system for lining and coating surfaces.Type: ApplicationFiled: April 25, 2001Publication date: January 16, 2003Inventors: Anastasios Zahariadis, Gerald Thermos
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Patent number: 6472487Abstract: Synthetic polymers having moieties capable of covalent or hydrogen bonding to cellulose and one or more amphiphilic moieties are disclosed. These polymers are capable of providing two distinct properties to paper products, such as tissues, which properties heretofore have been imparted through the use of at least two different molecules. The backbone of these synthetic polymers is based on modified vinyl polymers, such as polyvinyl alcohol, polyacrylamides and polyacrylic acids.Type: GrantFiled: May 14, 2001Date of Patent: October 29, 2002Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Wen Zyo Schroeder, Daniel Arthur Clarahan, Mike Thomas Goulet, Thomas Gerard Shannon
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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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Patent number: 6448364Abstract: This invention relates to a process for the production of a polyurethane elastomer by reacting a reaction mixture comprising (A) an isocyanate-reactive component having a molecular weight of 400 to 12,000, a functionality of about 2 to about 8 and being capped with 13 to 21% by weight of ethylene oxide, wherein the isocyanate-reactive groups are hydroxyl groups, amine groups or mixtures thereof; (B) an isocyanate-reactive component comprising (1) an isocyanate-reactive component containing at least two hydroxyl groups and having a molecular weight of from 62 to 399, and (2) an isocyanate-reactive component selected from the group consisting of (a) an isocyanate-reactive group containing tertiary amine polyether corresponding to a specific formula, (b) at least one organic amine compound containing at least two amine groups which are reactive with isocyanate groups; (C) potassium halide; (D) an internal mold release agent; (E) at least one catalyst, and (F) a polyisocyanate component.Type: GrantFiled: March 16, 2001Date of Patent: September 10, 2002Assignee: Bayer CorporationInventors: Jan L. R. Clatty, Michael T. Wellman, Stephen J. Harasin
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Patent number: 6433218Abstract: The pot life of an isocyanate formulation is controlled by including a chain extender having (a) at least two secondary amine groups, (b) no primary amine groups, and (c) a reactivity low enough that the chain extender will not react sufficiently with isocyanate groups present in the isocyanate formulation to increase the viscosity of the isocyanate formulation to more than 2000 mPa·s within 5 seconds in the isocyanate formulation.Type: GrantFiled: November 30, 1999Date of Patent: August 13, 2002Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack, Edward P. Squiller
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Patent number: 6429255Abstract: Adhesive compositions based on polyurethane and a polyamine suspension have a free isocyanate functional group content of between 2 and 9% by weight, with the polyamine being in the form of particles having a mean diameter of between 30 and 60 &mgr;m. A process for preparing the adhesive compositions involves reacting a polyol and a polyisocyanate to form a polyurethane prepolymer, wherein the prepolymer is mixed with the polyamine suspension. The adhesive compositions can be used for the adhesive bonding of materials, especially for motor vehicles.Type: GrantFiled: September 10, 1999Date of Patent: August 6, 2002Assignee: ATO Findley, S.A.Inventors: Michel Miskovic, Bruno Charriere, Jean-Yves Chenard, Gerard Guilpain
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Patent number: 6420445Abstract: Elastomers with improved physical properties, particularly hardness, resilience, tear strength, and compression set, may be prepared by the chain extension or moisture cure of isocyanate-terminated prepolymers prepared from a polyol component comprising a high molecular weight, low unsaturation polyoxypropylene diol and a low molecular weight diol. The elastomers are useful for applications such as rollers and other applications for which these physical properties are important.Type: GrantFiled: January 19, 2000Date of Patent: July 16, 2002Assignee: Bayer Antwerp N.V.Inventors: Nigel Barksby, Bruce D. Lawrey, Susan M. Clift
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Patent number: 6420509Abstract: The present invention relates to a polyurethane compound which has particular utility as a potting compound for fan exit guide vane assemblies of commercial gas turbine engines. The polyurethane compound comprises a formulation of polyurethane prepolymers mixed with an aromatic amine curing agent (hardener) in a volumetric mix ratio in the range of from about 0.9:1 to about 1:1. The polyurethane prepolymer consists of a blend of different polyethers based on diphenylmethane diisocyanate (MDI). The amine curing agent is a blend of oligomeric diamines with an aromatic diamine with a catalytic component. Both of the blends, in an uncured state, are liquid at room temperature.Type: GrantFiled: September 22, 2000Date of Patent: July 16, 2002Assignee: United Technologies CorporationInventors: John W. Putnam, Laurence E. Bernat, John P. Wesson, John H. Vontell
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Patent number: 6403752Abstract: Certain secondary aliphatic diamines are excellent chain extenders in the formation of polyurethanes, polyurea-polyurethane hybrids, and polyurea polymers, both elastomers and coatings, from both monomeric polyisocyanates and isocyanate-terminated prepolymers using the high-pressure impingement mixing reaction technique. These diamines include 1,4-di(alkylamino)cyclohexanes, 1-methyl-2,4-di(alkylamino)-3,5-dialkylcyclohexanes, N,N′-dialkyl isophoronediamine, 1,3-di(1′methyl-1′-alkylaminoethyl)benzene, and 1,6-di(alkylamino)hexane. These chain extenders may be used alone or in combination with other polyamines and with polyols. A broad spectrum of polymeric materials can be formed with a range of diverse properties.Type: GrantFiled: July 17, 2000Date of Patent: June 11, 2002Assignee: UOP LLCInventors: David W. House, Ray V. Scott, Jr.
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Patent number: 6399736Abstract: This invention concerns a method for the preparation of polyurea elastomers, comprising: (a) reacting an amine chain extender with dialkyl maleate to form an aspartic ester, wherein the chain extender has a molar amount of amine groups that is greater than the moles of dialkyl maleate; (b) blending the aspartic ester with one or more polyoxyalkyleneamines to prepare a resin blend; (c) contacting the resin blend with an isocyanate under conditions effective to form a polyurea elastomer. This invention concerns a method for the preparation of polyurethane elastomers, comprising: (a) reacting an diamine chain extender with dialkyl maleate or fumarate, wherein the mole ratio of primary amine functionality in the diamine chain extender to dialkyl maleate or fumarate is more than 1:1; (b) coating a substrate with effective film forming amounts of the product of step (a), an isocyanate, and a polyhydroxyl compound under conditions effective to form a the polyurethane elastomer.Type: GrantFiled: January 11, 2000Date of Patent: June 4, 2002Assignee: Huntsman Petrochemical CorporationInventors: Dudley J. Primeaux, II, Robert L. Zimmerman, Kenneth M. Hillman
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Patent number: 6353135Abstract: Aliphatic tetraketimine of the present invention are a novel class of compounds represented by the formula: wherein Et is ethyl, Me is methyl, and R is a residue of an aliphatic diisocyanate. The tetraketimine is made by condensing a novel ketimine with a diisocyanate. The ketimine has a free secondary amine after a polyamine selected from the group consisting of: H2N—C2H4—NH—C2H4—NH2, H2N—C2H4—NH—C2H4—NH—C2H4—NH2, H2N—(CH2)6—NH—(CH2)6—NH2, or tris(2-aminoethyl)amine is reacted with a ketone.Type: GrantFiled: August 31, 1999Date of Patent: March 5, 2002Assignee: The Boeing CompanyInventor: Larry K. Olli
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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: 6309313Abstract: Disclosed herein is a golf ball comprising a core and a cover, said cover comprising a polyurethane elastomer comprising the reaction product of: A) at least one diisocyanate monomer; B) at least one polyether polyol having a molecular weight greater than 1000 and selected from the group consisting of homopolymers of ethylene oxide, homopolymers of propylene oxide, and copolymers of ethylene oxide and propylene oxide; and C) at least one hydroxy or amine functional chain extender; wherein the ratio of equivalents of chain extender plus polyol to equivalents of isocyanate is in the range of from about 0.6:1 to about 1.2:1, whereby said polyurethane elastomer possesses high shear resistance and good resilience.Type: GrantFiled: March 6, 2000Date of Patent: October 30, 2001Assignee: Uniroyal Chemical Company, Inc.Inventor: Thomas H. Peter
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Patent number: 6294638Abstract: A soft, transparent and processable thermoplastic polyurethane resin suitable in optical application is disclosed. The resin is the product of reacting a diisocyanate, a chain extender, and a mixture of polyether polyols. The mixture of polyether polyols comprise (A) a C4 polyether polyol and (B) a C2-C3 polyether polyol where the weight ratio A/B is in the range of about 85/15 to 15/85.Type: GrantFiled: October 8, 1999Date of Patent: September 25, 2001Assignee: Bayer CorporationInventors: Steven C. Manning, Charles S. Gracik, Arthur W. Mason, Jack C. Chan
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Patent number: 6262217Abstract: Polyurethane compositions including the reaction product of a polyurethane prepolymer component including (a) at least one isocyanate-terminated polyalkadiene prepared by capping hydroxy-terminated polyalkadiene having a molecular weight from about 1500 to about 5000 grams per mol (g/mol) with isocyanate; and (b) at least one additional isocyanate-terminated polyalkadiene prepared by capping hydroxy-terminated polyalkadiene having a molecular weight from about 500 to about 1500 g/mol with isocyanate with a curative component. The compositions exhibit numerous useful properties, such as low glass transition temperature (Tg) high temperature stability, low viscosity at room and elevated temperatures, flexibility and flat dynamic mechanical properties versus temperature.Type: GrantFiled: December 15, 1997Date of Patent: July 17, 2001Assignee: Lord CorporationInventors: Jack N. Tallmadge, Ashish P. Diwanji, Mark A. Weih, Walter C. Wilhem
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Patent number: 6258917Abstract: An extrudable urea-extended thermoplastic polyurethane elastomer is formed from at least one aliphatic diisocyanate, at least one polyester glycol or polyether glycol, and at least one diamine curing agent. At least one second diamine curing agent and/or at least one extrusion processing aid may be included. The polyurethane has high-temperature-resistance and is thus extrudable at high temperatures. The polyurethane is also strong and durable. The polyurethane can be liquid-cast, transfer-molded, sprayed, and extruded without changing either the chemistry or stoichiometry of the polyurethane. The polyurethane may be used for making vehicle air bags or other any application for thermoplastic urethanes which requires increased thermal stability.Type: GrantFiled: September 21, 1998Date of Patent: July 10, 2001Assignee: Simula, Inc.Inventor: Edwin C. Slagel
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Patent number: 6221998Abstract: An isocyanate-based one-part moisture curable composition having excellent storage stability and high curing rate, and use of this composition enables production of a cured product of high flexibility without using any plasticizer. The composition comprises (A) an isocyanate compound having a structure wherein all of the isocyanate (NCO) groups in the molecule have secondary or tertiary carbon bonded thereto, and (B) a ketimine having ketimine (C═N) bond derived from a ketone or an aldehyde and an amine having a structure wherein &agr;-position of at least one of the carbon or the nitrogen of the ketimine bond has a branched carbon atom or a ring member carbon atom bonded thereto. A urethane prepolymer having such structure is preferable for use as the isocyanate compound (A).Type: GrantFiled: November 24, 1999Date of Patent: April 24, 2001Assignee: The Yokohama Rubber Co., Ltd.Inventors: Hiroyuki Okuhira, Naoya Adachi
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Patent number: 6207225Abstract: A solvent-free, two-component strip coating for metal surfaces is described which comprises the following components: A) 5 to 20% by weight of an optionally substituted aromatic diamine, 0.1 to 5% by weight of a dehydrator, 0.01 to 1% by weight of an accelerator based on tertiary amines, 0.01 to 1% by weight of an accelerator based on organic tin compounds, a polyether polyol based on poly(oxyalkylene) glycols as the remainder; B) 40 to 60% by weight of an aromatic diisocyanate based on a phenylene or toluylene diisocyanate, 40 to 60% by weight of a polyether polyol based (poly(oxyalkeylene) glycols. Despite its freedom from solvents, the strip coating according to the invention has rapid-hardening and rapid-drying properties, can be applied to a metal surface to be treated in a single spray operation and finally can be removed without problem and residue-free.Type: GrantFiled: December 10, 1998Date of Patent: March 27, 2001Assignee: Relius Coatings GmbH & Co.Inventors: Horst Lemke, Dieter Hohnholz
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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: 6174984Abstract: A polyurethane elastomer is disclosed that comprises the reaction product of: A) a prepolymer of at least one diisocyanate and at least one polyether polyol selected from the group consisting of a homopolymer of ethylene oxide, a homopolymer of propylene oxide, and a copolymer of ethylene oxide and propylene oxide, wherein free diisocyanate has been reduced to a level of less than 1% of the prepolymer; B) at least one alkylated8 aromatic diamine in a quantity sufficient to react with about 50% to about 105% of the available isocyanate content in the prepolymer; and C) at least one catalyst in a quantity sufficient to reduce the pot life to no more than two minutes; whereby said elastomer possesses high resilience and clarity and can be processed safely and at low cost.Type: GrantFiled: June 14, 1999Date of Patent: January 16, 2001Assignee: Uniroyal Chemical Company, Inc.Inventor: Thomas H. Peter
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Patent number: 6169141Abstract: The present invention relates to a coating composition containing: A) 25 to 50 wt. % of a polyisocyanate component, B) 5 to 20% wt. % of one or more polyaspartic acid esters C) 10 to 30 wt. % of one or more polyaldimines having a number average molecular weight of 112 to 600 D) 0.1 to 5.0 wt. % of an acetal corresponding to formula IV: E) 0.1 to 5.0 wt. % of castor oil. F) 0.1 to 10.0 wt. % of an organic solvent, G) 15 to 35 wt. % of a pigment and H) 0 to 10 wt. % of a coating additive other than D, F or G, wherein the sum of the percentages of components A to H is 100. The present invention also relates to the use of this coating composition as an anti-corrosive top coat.Type: GrantFiled: May 13, 1999Date of Patent: January 2, 2001Assignee: Bayer AktiengsellschaftInventors: Gerald Kurek, J{umlaut over (u)}rgen Schwindt, Peter Jahn
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Patent number: RE37386Abstract: A two component type polyurethane adhesive is provided for fiberglass reinforced plastics which requires no cleaning, preparation or treatment of the surface, and the like. The curative component is a nitrogen-free liquid polyether or polyester in an amount such that in association with a urethane prepolymer component containing free NCO groups, the ratio of the free NCO groups in the prepolymer component to the OH groups in said curative component is at least 1.2 and desirably at least 1.35. Such high NCO/OH ratios have unexpectedly been found to provide good adhesion and especially good humidity adhesion and peel strength adhesion to fiberglass reinforced plastics or metal surfaces which are free from any surface treatment.Type: GrantFiled: January 8, 1993Date of Patent: September 18, 2001Inventors: Earl G. Melby, H. William Cocain