Reactant Contains A Fluorine Atom Patents (Class 528/70)
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Patent number: 6486291Abstract: Coated porous materials that exhibit air permeability and repellency to liquids having a surface tension at least equal to or greater than 20 dynes/cm which are suitable for making ileostomy vent filters, transdermal drug substrates, agricultural and medical apparel, as well as paint and chemical protective garments. The coating for the porous material is applied as a curable composition containing fluorocarbon urethane precursors which are cross-linked in situ.Type: GrantFiled: November 30, 2000Date of Patent: November 26, 2002Assignee: Innovative Properties CompanyInventors: James S. Mrozinski, Malcolm B. Burleigh, Philip D. Radovanovic, Brian D. Johnson
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Patent number: 6479612Abstract: A polymer having at least one urea linkage derived by contacting (1) at least one polyisocyanate, or mixture of polyisocyanates, (2) at least one fluorocarbon alcohol, fluorocarbon thiol or fluorocarbon amine, (3) at least one straight or branched chain alcohol, amine or thiol, and (4) at least one alcohol containing a sulfonic acid group or its salt, and then (5) optionally at least one linking agent useful for imparting oil repellency and water repellency to substrates.Type: GrantFiled: June 19, 2000Date of Patent: November 12, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Thomas Wayne Del Pesco, Jack Kirchner, Andrew H. Liu
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Patent number: 6423809Abstract: The invention provides a polyurethane type polymeric material for coating optical fibers, based on a fluorinated diol with formula I: CnF2n+1—A—CH2OCH2—C (CH2OH)2—R where n is 2 to 20, and A signifies —CH═CH or —CH2CH2—, and R is an alkyl group containing 1 to 4 carbon atoms. The invention also provides a fiber coated with this polymer which has been light-cured, and a fiber drawing method comprising a step of coating the fiber with a material of the invention.Type: GrantFiled: February 12, 2001Date of Patent: July 23, 2002Assignee: AlcatelInventors: Sophie Vanpoulle, Gérard Orcel, Bob J. Overton, Marie-José Lina, Eric Lacroix
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Patent number: 6417314Abstract: The present invention provides, inter alia, novel fluorinated polyurethane elastomers (e.g., fluorinated thermoset polyurethane elastomers and fluorinated thermoplastic elastomers) prepared from polyether prepolymers formed from mono-substituted fluorinated oxetane monomers (FOX monomers). In addition, the present invention provides methods of making such fluorinated polyurethane elastomers.Type: GrantFiled: March 8, 2000Date of Patent: July 9, 2002Assignee: Aerojet-General CorporationInventors: Aslam A. Malik, Thomas G. Archibald
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Patent number: 6403760Abstract: Monofunctional polyfluorooxetane oligomers and polymers are prepared by the cationic polymerization of fluorooxetane monomers with a monoalcohol. The fluorooxetane oligomers or polymers can be copolymerized with generally cyclic ethers. Alternatively, the polyfluorooxetane oligomer or polymer having a single hydroxyl end group can be functionalized with a variety of compounds so as to yield a functional end group such as an acrylate, a methacrylate, an allylic, an amine, etc., with the functionalized oligomer or polymer being suitable for use in radiation curable or thermal curable coating compositions. These functionalized polymers can be copolymerized and cured to provide improvements in wetting and surface properties that have previously been provided by migratory chemicals such as waxes and oils.Type: GrantFiled: December 28, 1999Date of Patent: June 11, 2002Assignee: OMNOVA Solutions Inc.Inventors: Raymond J. Weinert, Guillermina C. Garcia, Aslam Malik, Roland Carlson, Robert E. Medsker
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Patent number: 6384174Abstract: Fluorine-containing diols represented by the following formula are provided: wherein Rf represents a perfluoroalkyl or perfluoroalkenyl group having 1 to 20 carbon atoms; X represents a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenylene group represented by —CH═CH—(CH2)n— in which n is from 1 to 10, or in which n is from 0 to 6; Y represents a direct bond, —O—, —NH—, or —R0—NH— in which R0 is an alkylene group having 1 to 6 carbon atoms; Z represents a direct bond or —N(R′)R— in which R is an alkylene group having 1 to 20 carbon atoms and R′ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R1 and R2 divalent organic groups; and R3 represents a residual group of diisocyanate. These diols are useful for polyurethanes.Type: GrantFiled: March 6, 2001Date of Patent: May 7, 2002Assignees: Dainichiseika Color & Chemicals Mfg. Co., Ltd., Ukima Colour & Chemicals Mfg. Co., Ltd.Inventors: Kazuyuki Hanada, Kazuya Kimura
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Patent number: 6376592Abstract: A water dispersion type water and oil repellent composition obtained by polymerizing the following polymerizable monomer mixture (b) in the presence of a compound (a) having a blocked isocyanate group and no polymerizable unsaturated group: (b) a mixture comprising a polymerizable monomer having a polyfluoroalkyl group and a polymerizable monomer having no polyfluoroalkyl group.Type: GrantFiled: August 12, 1999Date of Patent: April 23, 2002Assignee: Asahi Glass Company, Ltd.Inventors: Toyomichi Shimada, Takashige Maekawa
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Publication number: 20020045724Abstract: Water-soluble polyurethane according to the present invention is obtained from polyalkylene glycols, diisocyanates, and comb-shaped hydrophobic diols represented by the following general formula (3): 1Type: ApplicationFiled: December 12, 2000Publication date: April 18, 2002Inventors: Manabu Tsuruta, Masahiko Mitsuzuka, Yunzhi Wu
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Patent number: 6306958Abstract: Aqueous dispersions comprising as component A) a compound containing two or more blocked isocyanate groups in the molecule and as component B) a compound obtainable by reacting a diepoxy compound with a diamine or polyamine and subsequently reacting the resulting reaction product with an acid and possibly as component C) a dispersant are suited together with fluorine containing oligomers or polymers for the oil-, water- and soil-repellent finishing of fiber materials.Type: GrantFiled: December 16, 1999Date of Patent: October 23, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Franz Dirschl, Franz Mosch, Wilhelm Artner, Edeltraud Schidek, Heinz Gaugenrieder, Simpert Lüdemann, Erich Rössler
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Patent number: 6300633Abstract: An in-line spectrometric method for determining the distillation residue content in an opaque, dark-colored mixture containing an isocyanate and tar-like materials (residue) during the isocyanate production process. A probe capable of directing light at wavelengths of from 1050 to 2150 nm is inserted in a stream of the residue-containing mixture and light is transmitted through the stream. Light absorption data is collected and a near-infrared spectrum is generated. The residue content is then determined using a chemometric model. Knowledge of the residue content makes it possible to control and optimize the distillation process.Type: GrantFiled: July 6, 1998Date of Patent: October 9, 2001Assignee: Bayer CorporationInventors: Robert N. Hunt, Gary F. Allen, Julie A. Jackson, Peter Scharein, Peter J. Ryan, Donald Macnaughton, Jr., Klaus Sommer, Larry E. Philyaw
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Patent number: 6261695Abstract: A coating composition comprising a fluorine-containing compound of the following formula 1, a polyisocyanate, water and an organic solvent: Rf—Q—A 1 wherein R is a monovalent fluorine-containing organic group having from 2 to 20 carbon atoms, Q is a single bond or a bivalent linking group, and A is a group having a hydrogen atom reactive with an isocyanate group.Type: GrantFiled: December 17, 1998Date of Patent: July 17, 2001Assignee: Asahi Glass Company Ltd.Inventor: Kazusuke Kirimoto
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Patent number: 6242557Abstract: Use of crosslinked polymers for coil coating based on perfluoropolyethereal polymers, comprising as repeating units sequences of one or more oxyfluoroalkylenic units such as —CF2CF2O—, —CR4R5CF2CF2O— wherein R4 and R5 equal to or different from each other are chosen among H, Cl, F or perfluoroalkyl from 1 to 4 carbon atoms, —CF2CF(CF3)O—, —CFYO—, wherein Y is equal to F or CF3, having hydroxylic bifunctional termination, crosslinking being carried out with blocked polyisocyanates having at least 3 NCO groups.Type: GrantFiled: January 19, 2000Date of Patent: June 5, 2001Assignee: Ausimont S.p.A.Inventors: Tatiana Temtchenko, Massimo Malavasi
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Patent number: 6239247Abstract: The present invention provides a method for preparing a fluorochemical composition comprising a urethane by reacting: (A) fluorochemical oligomer of the formula (I): MfmMn—Q1—T1 wherein MfmMn represents a fluorochemical oligomer comprising m units derived from fluorinated monomer and n units derived from fluorine-free monomer and wherein the fluorinated monomers and fluorine-free monomers may be the same or different; m is a value of about 2 to 40; n is a value of about 0 to 20; T1 is an —OH or —NH2 moiety; Q1 and T1 together represent an organic residue obtained by removing a hydrogen atom from a chain transfer agent that is functionalized with T1; (B) monofunctional compound capable of reacting with an isocyanate and comprising a poly(oxyalkylene) group; (C) isocyanate blocking agent or a fluorine-free oligomer; and (D) isocyanate-reactive compound other than said fluorochemical oligomer, said isocyanate blocking agent, said fluorine-free oligomer and said monofunctional compound; wiType: GrantFiled: September 24, 1999Date of Patent: May 29, 2001Assignee: 3M Innovative Properties CompanyInventors: Kathy E. M. L. A. Allewaert, Rudolf J. Dams, Pierre J. Vander Elst
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Patent number: 6224782Abstract: The present invention provides a method for preparing a fluorochemical composition comprising polyurethane by reacting: (A) fluorochemical oligomer of formula (I): MfmMn—Q1—T1 wherein: MfmMn represents flurochemical oligomer comprising m units derived from fluorinated monomer and n units derived from fluorine-free monomer and wherein the fluorinated monomers and fluorine-free monomers may be the same or different; m represents a value of 2 to 40; n represents a value of 0 to 20; T1 is —OH or —NH2; Q1 and T1 together represent an organic residue obtained by removing a hydrogen atom from a chain transfer agent that is functionalized with T1; and (B) difunctional compound capable of reacting with an isocyanate and comprising a poly(oxyalkylene) group having 18 to 280 oxyalkylene moieties with (C) diisocyanate or triisocyanate.Type: GrantFiled: September 24, 1999Date of Patent: May 1, 2001Assignee: 3M Innovative Properties CompanyInventors: Kathy E. M. L. A. Allewaert, Frans A. Audenaert, Pierre J. Vander Elst
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Publication number: 20010000183Abstract: Coated porous materials that exhibit air permeability and repellency to liquids having a surface tension at least equal to or greater than 20 dynes/cm which are suitable for making ileostomy vent filters, transdermal drug substrates, agricultural and medical apparel, as well as paint and chemical protective garments. The coating for the porous material is applied as a curable composition containing fluorocarbon urethane precursors which are cross-linked in situ.Type: ApplicationFiled: November 30, 2000Publication date: April 5, 2001Applicant: 3M Innovative Properties CompanyInventors: James S. Mrozinski, Malcolm B. Burleigh, Philip D. Radovanovic, Brian D. Johnson
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Patent number: 6203872Abstract: Proposed is a process for sealing the seams of a water vapour permeable lining comprising a laminate of a textile material and a waterproof, but water vapour permeable film in which sections of said laminate with the textile sides facing one another are bonded together along the contours of the material to be lined, after which the lining is dipped in a solution of a hydrophilic polymer in an organic solvent which acts as a swelling agent for the waterproof film of the laminate, followed by evaporation of the solvent. The water vapour permeable film in the laminate preferably is made of a hydrophilic copolyetherester or copolyetheramide, while the hydrophilic polymer soluble in an organic solvent preferably is a copolyetherester.Type: GrantFiled: July 23, 1998Date of Patent: March 20, 2001Assignee: Akzo Nobel NVInventor: Dennis W Hannon
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Patent number: 6177531Abstract: A water and oil repellent composition containing, as an effective component, a copolymer comprising the following polymeric units (a), (b) and at least one member selected from (c) and (d): polymeric units (a): Polymeric units of a (meth)acrylate having a polyfluoroalkyl group; Polymeric units (b): Polymeric units of 2-isocyanate ethyl (meth)acrylate with the isocyanate group blocked; Polymeric units (c): Polymeric units of vinyl chloride; and Polymeric units (d): Polymeric units of an alkyl (meth)acrylate.Type: GrantFiled: July 23, 1998Date of Patent: January 23, 2001Assignee: Asahi Glass Company Ltd.Inventors: Toyomichi Shimada, Kyoichi Kaneko, Shuichiro Sugimoto, Takashige Maekawa
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Patent number: 6174956Abstract: A polyurethane polymer and method of preparing it is described. The process requires the combination of a soluble polyol with a di- or polyisocyanate under densified fluid conditions. The process to prepare a waterborne polyurethane involves the utilization of a polyol containing ionic or latent ionic groups which must undergo preneutralization before combining with the di- or polyisocyanate under densified fluid conditions. The resulting polyurethane is substantially free of an organic solvent.Type: GrantFiled: February 14, 1997Date of Patent: January 16, 2001Assignee: National Starch and Chemical Investment Holding CorporationInventors: Judith Lynne Kerschner, Sharon Harriott Jureller, John Socrates Thomaides, Robert William Humphreys, Carmine Phillip Iovine
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Patent number: 6160161Abstract: Per(poly)fluorinated polyoxyethylated carbamates of general formula (I) in which R.sub.F represents a perfluorinated group containing between 1 and 18 carbon atoms, W represents an oxo group or nothing, n is an integer from 1 to 10, m is from values 2 to 6, 80 or not defined, R is an alkyl group, R.sub.F W(CH.sub.2).sub.n+1 NHC(O)-- in which R.sub.F and W are as defined above, --(CHCH.sub.3 CH.sub.2 O).sub.30 (CH.sub.2 CH.sub.2).sub.80 C(O)NH(CH.sub.2).sub.n+1 R.sub.F in which R.sub.F is a perfluorinated group containing from 1 to 18 carbon atoms, R' is a hydrogen atom, an alkyl group containing between 1 and 18 carbon atoms which is optionally substituted, an optionally substituted aryl or aralkyl group, an allyl, methallyl or propargyl group or a perfluorinated chain having between 1 and 18 carbon atoms.Type: GrantFiled: December 23, 1998Date of Patent: December 12, 2000Assignee: F2 Chemicals LimitedInventors: Hedi Trabelsi, Wolfgang Roehlke, Peter Reuter, Massimo Napoli, Philippe Lucas, Kenneth Charles Lowe, Giampaolo Gambaretto, Ralf-Peter Franke, Carl Martin Edwards, Lino Conte, Aime Cambon
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Patent number: 6132931Abstract: A positive working photosensitive composition comprising a specific fluorine-containing copolymer. The positive working photosensitive composition has not only an ability to form a high contrast image but also an ability to inhibit halation, a satisfactory safe light tolerance and a wide development latitude, without lowering the sensitivity.Type: GrantFiled: October 29, 1999Date of Patent: October 17, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Koichi Kawamura, Noriaki Watanabe
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Patent number: 6111026Abstract: The invention relates to monomers derived from perhalogenated sultones, to a process for their preparation, to the polymers obtained from the said monomers and to their use for the production of ion-conductive materials.The monomers are compounds corresponding to the formula A--CFX--SO.sub.2 Z in which A denotes one groups [sic] R.sup.3 --O--CF.sub.2 -- or R.sup.3 -- or R.sup.1 R.sup.2 N--CO--; Z denotes F, Cl, --OSi(CH.sub.3).sub.3 or an ionic group, Z being other than F when A denotes R.sup.3 --O--CF.sub.2 -- or R.sup.3 --; X denotes F, Cl, H or R.sub.F, X being R.sub.F when A denotes R.sup.3 --; the radicals R.sup.1, R.sup.2 and R.sup.3 are chosen from polymerizable nonperfluorinated organic radicals; R.sub.F is chosen from perfluoroalkyl radicals and perfluoroaryl radicals.The polymers obtained from these monomers can be employed for the production of ion-conductive materials.Type: GrantFiled: November 10, 1997Date of Patent: August 29, 2000Assignees: Centre National de la Recherche Scientifique, Hydro-QuebecInventors: Michel Armand, Jean-Yves Sanchez, Salime Sylla
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Patent number: 6111050Abstract: A fluorine-containing curable composition comprises (A) a linear perfluoro compound having at least two secondary amino groups per molecule and a divalent perfluoroalkylene or divalent perfluoropolyether structure in the main chain, and (B) a crosslinkable fluorinated compound having at least three functional groups which are crosslinkable with the secondary amino groups of (A). This composition readily cures, with standing at room temperature or heating only, to a cured product having excellent solvent and chemical resistance.Type: GrantFiled: September 21, 1998Date of Patent: August 29, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Kouichi Yamaguchi, Noriyuki Koike, Masatoshi Arai, Hirofumi Kishita
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Patent number: 6080830Abstract: Products which are produced by reaction of diisocyanates with di- or polyhydric alcohols and/or with one or more mono- and/or diethers of such alcohols and subsequent reaction with organic amines containing two or more alcoholic hydroxyl groups and subsequent blocking of free isocyanate groups are suitable for the finishing of fiber materials, in particular in the form of aqueous dispersions as extenders for use in combination with polymers containing perfluoroalkyl groups for the oil-, water- and soil-repellent finishing of fiber materials.Type: GrantFiled: April 15, 1998Date of Patent: June 27, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Franz Dirschl, Franz Mosch, Theodor Angele, Wilhelm Artner, Edeltraud Schidek, Erich Rossler
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Patent number: 6071564Abstract: Use for protective coatings of compositions comprising (% by wt.): A) from 10 to 60% of a A1) (per)fluoropolyethereal prepolymer having a polyisocyanic functionality obtainable by reacting a bifunctional having hydroxylic functionality, said fluoropolyethers having --CH.sub.2 OH terminations directly linked to a perfluoroalkylic group CF.sub.2 or CF.sub.2 CFX (X.dbd.Cl, F) or CF(CF.sub.3), with a polyisocyanate containing isocyanurate rings, preferably obtained by cyclotrimerization of HDI, IPDI or other monomeric diisocyanates, by utilizing an excess of isocyanate groups comprised between 10 and 80% by moles; the above fluoropolyether prepolymer can be partially or totally replaced by A2) non fluorinated polyisocyanates containing isocyanurate rings and/or hydrogenated polyisocyanate prepolymers;B) from 0.1 to 50% of a (per)fluoropolyether having bifunctional hydroxylic functionality of the type --CF.sub.2 CH.sub.2 OH, --CF.sub.2 CFXCH.sub.2 OH (X.dbd.Cl, F) or --CF(CF.sub.3)CH.sub.Type: GrantFiled: June 10, 1997Date of Patent: June 6, 2000Assignee: Ausimont S.p.A.Inventors: Roberta Marchetti, Massimo Malavasi
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Patent number: 6040414Abstract: Use of crosslinked polymers for coil coating based on perfluoropolyethereal polymers, comprising as repeating units sequences of one or more oxyfluoroalkylenic units such as --CF.sub.2 CF.sub.2 O--, --CR.sub.4 R.sub.5 CF.sub.2 CF.sub.2 O-- wherein R.sub.4 and R.sub.5 equal to or different from each other are chosen among H, Cl, F or perfluoroalkyl from 1 to 4 carbon atoms, --CF.sub.2 CF(CF.sub.3)O--, --CFYO--, wherein Y is equal to F or CF.sub.3, having hydroxylic bifunctional termination, crosslinking being carried out with blocked polyisocyanates having at least 3 NCO groups.Type: GrantFiled: June 10, 1997Date of Patent: March 21, 2000Assignee: Ausimont S.p.A.Inventors: Tatiana Temtchenko, Massimo Malavasi
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Patent number: 6034207Abstract: A hexafluoropropene oxide polymer of formula (1) having a dispersity Mw/mn of up to 1.10 is useful as a raw material for liquid rubber. In formula (1), R is --COF, --I, --Br, --CH.sub.2 OH, --CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2, --COOR.sup.1 or --CONR.sup.2 R.sup.3 wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or monovalent C.sub.1-20 hydrocarbon groups which may contain N, O, Si or S, or R.sup.2 and R.sup.3 form a ring with the N atom, Rf is a C.sub.1-6 perfluoroalkylene group or a C.sub.2-10 perfluorooxyalkylene group, and x+y=30 to 400.Type: GrantFiled: April 1, 1999Date of Patent: March 7, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Noriyuki Koike, Takashi Matsuda, Shinichi Sato
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Patent number: 6001923Abstract: In accordance with the present invention, there are provided coating compositions for preparing crosslinked fluorinated polyurethane coatings and liners that exhibit high optical clarity and transparency, as well as resilience against adverse environmental effects. The present invention also provides methods for coating solid substrates with transparent, environmentally-resistant crosslinked, fluorinated polyurethane coatings, as well as the resulting coated articles.Type: GrantFiled: March 27, 1997Date of Patent: December 14, 1999Assignee: Pilkington Aerospace Inc.Inventors: Marlowe V. Moncur, Lin H. Hoo, E. John Houghton
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Patent number: 5989697Abstract: Claimed is a copolyether amide having a melting point in the range of 180.degree. to 260.degree. C., incorporating at least 10 wt. % and not more than 30 wt. % of ethylene oxide groups, and composed of 30 to 60 wt. % of polyamide segments and 70 to 40 wt. % of segments derived from a (cyclo)aliphatic or aromatic dicarboxylic acid or a dimeric fatty acid and a polyoxyalkylene diamine derived from a polyoxyalkylene group having a molecular weight of 600 to 6000 and an atomic ratio of carbon to oxygen of 2.0 to 4.3. Also claimed is a non-porous, waterproof film having a water vapor permeability of at least 1000 g/m.sup.2 day determined at 30.degree. C. and 50% RH in accordance with ASTM E96-66 which is based on a the use of these films in rainwear, shoes, tents, chairs, as mattress covers and underslating, for medical purpose garments, and for the manufacture of dressings.Type: GrantFiled: November 24, 1997Date of Patent: November 23, 1999Assignee: Akzo Nobel, NVInventor: Bert Gebben
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Patent number: 5959058Abstract: Use of fluorinated polymers based on fluoropolyethers for the preparation of crosslinkable high dry formulations comprising a fluorinated part R.sub.F and optionally an hydrogenated part R.sub.H, not containing groups capable of linking by means of hydrogen bonds to basic acceptors, an hydrogenated part Rh.sub.1 and Rh.sub.2, wherein Rh.sub.1 is equal to or different from Rh.sub.2, and Rh.sub.1 and/or Rh.sub.2 being linking bonds containing at least a functional group capable of linking by means of hydrogen bonds with basic acceptors, the bonds joining the fluorinated part to the hydrogenated part being of ether C--O simple type, the terminals T'.sub.a and T" being such as to render the structure mono-, bi- or polyfunctional, and subsequent crosslinking of the fluorinated polymer, the monofunctional products being always in admixture with a resin having even a higher functionality than the described type; the preferred fluorinated products have the formula:T"--(Rh.sub.2).sub.y (R.sub.H).sub.x --R.sub.F --(R.Type: GrantFiled: March 11, 1996Date of Patent: September 28, 1999Assignee: Ausimont S.p.A.Inventors: Claudio Tonelli, Massimo Scicchitano, Stefano Turri
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Patent number: 5914384Abstract: A coating composition that forms a finish that is soil resistant and easily cleaned having a binder of(A) an acrylic polymer of polymerized hydroxyl containing monomers of hydroxy alkyl (meth)acrylates having 1-4 carbon atoms in the alkyl groups and polymerized monomers from the group of alkyl (meth)acrylates having 1-18 carbon atoms in the alkyl groups, styrene or any mixtures of the above and the acrylic polymer has a weight average molecular weight of about 2,000-20,000 determined by gel permeation chromatography,(B) an acrylic polymeric additive of polymerized hydroxyl containing monomers of hydroxy alkyl (meth)acrylates having 1-4 carbon atoms in the alkyl groups, polymerized monomers from the group of alkyl (meth)acrylates having 1-18 carbon atoms in the alkyl groups, styrene or any mixtures of the above and polymerized fluoro alkyl containing monomer represented by the formula ##STR1## where R is selected from the group of hydrogen or an alkyl group having 1-2 carbon atoms, X is a divalent radical andType: GrantFiled: November 21, 1997Date of Patent: June 22, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Douglas Robert Anton, Michael J. Darmon, William Frank Graham, Richard Ronald Thomas
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Patent number: 5910557Abstract: The present invention relates to fluorochemical polyurethane compounds of the formula (I) according to claim 1, a method for their preparation and to compositions comprising that fluorochemical polyurethane compound. The compound and the composition comprising that compound are suitable to impart durable oil- and water-repellency and good laundry air-dry performance to substrates, such as fibers, woven or non-woven fabrics, carpets, leather and paper.Type: GrantFiled: May 12, 1997Date of Patent: June 8, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Frans A. Audenaert, Kathy E.M.L.A. Allewaert, Gert Hooftman, Makoto Nagase, Hugo R. Lens
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Patent number: 5849855Abstract: Disclosed is a blocked polyisocyanate composition comprising: a blocked polyisocyanate obtained by blocking the terminal isocyanate groups of a two or more terminal isocyanate groups-containing polyisocyanate derived from at least one diisocyanate selected from an aliphatic diisocyanate and an alicyclic diisocyanate with a blocking agent comprising at least one active methylene compound selected from a malonic diester and an acetoacetic ester; and a salt of a basic compound with an acidic compound, or a mixture of the salt with the basic compound or the acidic compound, the composition having a pH value of from 1 to 8.5. The blocked polyisocyanate composition of the present invention not only exhibits high stability even under high temperature conditions, but also is capable of maintaining such high stability for a prolonged period of time.Type: GrantFiled: August 19, 1996Date of Patent: December 15, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Taketoshi Usui, Yoshiyuki Asahina
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Patent number: 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: 5798409Abstract: The present invention relates to two-part reactive polyurethane compositons and the cured coatings prepared therefrom. The invention also relates to particular compositions and cured coatings therefrom that exhibit high damping character, excellent scratch-resistance, excellent mar-resistance, and self-healing characteristics. The invention also relates to a novel polyurethane prepolymer useful in some ofthe compositions. The invention also relates to method of making certain coatings of the invention.Type: GrantFiled: April 1, 1997Date of Patent: August 25, 1998Assignee: Minnesota Mining & Manufacturing CompanyInventor: Chia-Tie Ho
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Patent number: 5789513Abstract: A coating composition comprising an alkyd or urethane resin and a polyfluorourethane of Formula II(R.sub.f --X--O--CO--NH).sub.m --A--(NH--CO--O--R).sub.(p-m) IIwhereinR.sub.f is a C.sub.2 -C.sub.20 linear or branched fluorocarbon,X is --(CH.sub.2).sub.n --, --(CH.sub.2).sub.g SO.sub.z (CH.sub.2).sub.t --, or --SO.sub.2 N(R.sub.1)CH.sub.2 CH.sub.2 --wherein n is 1 to about 20; g and t are each independently 1 to about 3; z is 0, 1 or 2; and R.sub.1 is an alkyl of 1 to about 4 carbon atoms;A is an aliphatic, cycloaliphatic, aromatic, or heterocyclic radical;R is a C.sub.3 -C.sub.20 linear, branched, or cyclic aliphatic group containing at least one ethylenically unsaturated double bond and optionally at least one phenyl or phenyl substituted with C.sub.1 -C.sub.6 alkyl or halogen;p is 2 to 3; andm is from about 0.8 to about 1.25 when p is 2, and m is from about 1 to about (p-1) when p is greater than 2 is disclosed.Type: GrantFiled: February 26, 1997Date of Patent: August 4, 1998Assignee: E. I. du Pont de Nemours and CompanyInventor: Jack Robert Kirchner
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Patent number: 5777061Abstract: The present invention is directed to a powder coating composition containing as binderA) a polyisocyanate component which contains blocked isocyanate groups, is present in powder form, is solid below 40.degree. C. and liquid above 150.degree. C., and contains one or more polyisocyanatesi) having a blocked NCO content (calculated as NCO, MW 42) of 5 to 25% by weight andii) containing fluorine (calculated as F, AW 19) in an amount of 0.01 to 20% by weight,wherein the preceding percentages are based on the solids content of the polyisocyanate mixture andB) a polyhydroxyl component containing one or more high molecular weight polyols.Type: GrantFiled: February 14, 1996Date of Patent: July 7, 1998Assignee: Bayer CorporationInventors: Kenneth P. Yonek, Lanny D. Venham, Philip E. Yeske, Edward P. Squiller
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Patent number: 5773550Abstract: Isocyanurate- and uretdione-group-containing polyaddition product of an isophorone diisocyanate comprising the reaction product of:i) an isophorone diisocyanate which contains isocyanurate groups and uretdione groups; andii) a diol component selected from the group consisting of a diol, a disecondary diamine, a linear hydroxyl-containing polyester and a mixture thereof,wherein said isophorone diisocyanate comprises not more than 2% by weight of free isophorone diisocyanate and .gtoreq.5 wt. % of isophorone diisocyanate isocyanurate,wherein said isophorone diisocyanate is reacted with said diol component in an NCO/OH ratio of 1:0.5-1:0.95 and/or an NCO/NH ratio of 0.5:1 0.95:1.Type: GrantFiled: February 14, 1997Date of Patent: June 30, 1998Assignee: Huels AktiengesellschaftInventor: Elmar Wolf
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Patent number: 5747629Abstract: The present invention relates to polyisocyanate adducts containing allophanate groups, fluorine and optionally isocyanurate groups that are prepared by reacting compounds a) whichi) are substantially free of hydroxyl groups and isocyanate groups,ii) have an average of at least two urethane groups per molecule andiii) contain 0 to 50% by weight of fluorine, based on the weight of the polyisocyanate adducts,with an excess quantity, based on the equivalents of urethane groups, of polyisocyanates b), which optionally contain fluorine, to form polyisocyanate adducts and optionally removing at least a portion of the unreacted excess polyisocyanates b), provided that compounds a) and polyisocyanates b) contain a total of at least 0.001% by weight, of fluorine, based on the weight of the polyisocyanate adducts.Type: GrantFiled: December 16, 1996Date of Patent: May 5, 1998Assignee: Bayer CorporationInventors: Philip E. Yeske, William E. Slack, Edward P. Squiller
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Patent number: 5744549Abstract: The present invention is directed towards golf balls comprising a core, a cover and a coating composition layer, wherein the coating composition layer comprises a fluorinated polyurethane. The novel fluorinated polyurethane coating composition of the present invention enhance a variety of properties such as enhanced abrasion, impact and weathering resistance as compared to golf balls with conventional coating composition. Additionally, the presently claimed fluorinated polyurethane coatings also decrease the coefficient of friction of the surface of the golf ball, resulting in a modification of the spin rate when struck with a golf club and superior cleaning characteristics.Type: GrantFiled: June 3, 1996Date of Patent: April 28, 1998Assignee: Acushnet CompanyInventor: Mitchell E. Lutz
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Patent number: 5731399Abstract: Compounds are disclosed which correspond to general formula (I) ##STR1## wherein: R and R' each independently represent an alkyl chain of 1 to 10 carbon atoms, which may be branched, and which may be partially or fully fluorinated;n and n' each independently represent an integer of from 0 to 4, the R, respectively R' substituents may be the same or different when n, respectively n' is greater than 1;R.sub.1 and R.sub.2 independently represent hydrogen or an alkyl chain of 1 to 5 carbon atoms, which may be branched, and which may be partially or fully fluorinated, or R.sub.1 and R.sub.2 together represent an alkylene chain of 2 to 6 carbon atoms, which may be substituted by alkyl groups and which may be partially or fully fluorinated;and wherein the amino substituents are situated in ortho, meta or para position with regard to the oxy substituent;with the proviso that said compound does not correspond to bis-(2- and 3- and 4-aminophenoxy)methane.Type: GrantFiled: December 18, 1995Date of Patent: March 24, 1998Assignee: Imperial Chemical Industries PLCInventors: Steve Carter, Gonda Van Essche
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Patent number: 5725789Abstract: Oil and water repellent compositions for the treatment of fiber containing substrates such as fabric and the like, substrates treated with these compositions and methods for the treatment of substrates are described. The compositions of the invention comprise (a) a polyalkoxylated polyurethane and (b) a fluorochemical acrylate polymer comprising the polymerized reaction product of a fluorinated acrylate or methacrylate monomer, at least one alkyl acrylate or methacrylate monomer and a polymerizable cationic emulsifier comprising a quaternary amine surfactant. Additionally, (c) a polyalkylene glycol fluorochemical acrylate copolymer and (d) a fluorochemical adipate ester can also be included within the compositions. The above components are blended together within the composition at a weight ratios of (a):(b), or (a)+(c):(b), or (a)+(c)+(d):(b) of from 19:1 to 1:19 and preferably about 1:1.Type: GrantFiled: November 13, 1996Date of Patent: March 10, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Charles D. Huber, Michael A. Yandrasits
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Patent number: 5721328Abstract: The invention relates to monomers derived from perhalogenated sultones, to a process for their preparation, to the polymers obtained from the said monomers and to their use for the production of ion-conductive materials.The monomers are compounds corresponding to the formula A-CFX--SO.sub.2 Z in which A denotes one groups ?sic! R.sup.3 --O--CF.sub.2 -- or R.sup.3 - or R.sup.1 R.sup.2 N--CO--; Z denotes F, Cl, --OSi(CH.sub.3).sub.3 or an ionic group, Z being other than F when A denotes R.sup.3 --O--CF.sub.2 -- or R.sup.3 -; X denotes F, Cl, H or R.sub.F, X being R.sub.F when A denotes R.sup.3 -; the radicals R.sup.1, R.sup.2 and R.sup.3 are chosen from polymerizable nonperfluorinated organic radicals; R.sub.F is chosen from perfluoroalkyl radicals and perfluoroaryl radicals.The polymers obtained from these monomers can be employed for the production of ion-conductive materials.Type: GrantFiled: May 26, 1995Date of Patent: February 24, 1998Assignees: Centre National de la Recherche Scientifique, Hydro-QuebecInventors: Michel Armand, Jean-Yves Sanchez, Salime Sylla
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Patent number: 5708119Abstract: Bisperfluoroalkyl-substituted diols containing sulfide, sulfone or polysulfide linkages and a method for making them are described. These diols can react with isocyanates to form urethanes; diisocyanates to form polyturethanes; chloroformates to form carbonates; with carboxylic, sulfuric or phosphoric acids or derivatives to form carboxylate esters, sulfate esters, phosphate esters respectively. These diol compounds and their derivatives are useful for imparting oil and water repellency to substrates such as glass, wood, paper, leather, wool, cotton, polyester and other substrates.Type: GrantFiled: June 14, 1996Date of Patent: January 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Ted Deisenroth, Marlon Haniff
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Patent number: 5703194Abstract: This application is directed to novel fluorinated polymers and prepolymers derived from mono-substituted oxetane monomers having fluorinated alkoxymethylene side-chains and the method of making these compositions. The mono-substituted fluorinated oxetane monomers having fluorinated alkoxymethylene side-chains are prepared in high yield by the reaction of a fluorinated alkoxides with either 3-halomethyl-3-methyloxetane premonomers or aryl sulfonate derivative of 3-hydroxymethyl-3-methyloxetane premonomers. Preparation of a mono-substituted 3-bromomethyl-3-methyloxetane premonomer via a simple, high yield process amenable to commercial scaleup is also disclosed. The fluorinated oxetane monomers of this invention can be readily homo/co-polymerized in the presence of a Lewis acid and polyhydroxy compounds to obtain hydroxy-terminated polyether prepolymers having fluorinated alkoxymethylene side chains.Type: GrantFiled: June 7, 1995Date of Patent: December 30, 1997Assignee: Aerojet-General CorporationInventors: Aslam A. Malik, Thomas G. Archibald
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Patent number: 5693737Abstract: The invention relates to a blocked polyisocyanate having an NCO functionality of from 2.2 to 4.5 and an average molecular weight of 800 to 25,000 and containing (1) blocked isocyanate groups corresponding to an NCO content of 5 to 20 wt. % calculated as free NCO, relative to unblocked polyisocyanate, (2) 1 to 75 meq of ionic groups per 100 g of blocked polyisocyanate, and (3) 3 to 40 wt.Type: GrantFiled: January 19, 1996Date of Patent: December 2, 1997Assignee: Bayer AktiengesellschaftInventors: Helmut Reiff, Karl-Heinz Passon, Hans-Albert Ehlert, Peter Nussbaum
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Patent number: 5693747Abstract: Bisperfluoroalkyl-substituted diols containing sulfide, sulfone or polysulfide linkages and a method for making them are described. These diols can react with isocyanates to form urethanes; diisocyanates to form polyurethanes; chloroformates to form carbonates; with carboxylic, sulfuric or phosphoric acids or derivatives to form carboxylate esters, sulfate esters, phosphate esters respectively. These diol compounds and their derivatives are useful for imparting oil and water repellency to substrates such as glass, wood, paper, leather, wool, cotton, polyester and other substrates.Type: GrantFiled: July 3, 1996Date of Patent: December 2, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Ted Deisenroth, Marlon Haniff
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Patent number: 5679754Abstract: A water dispersible polymeric composition comprises at least one sulfo group containing segment, which group comprises at least one urethane or urea connecting group, said composition also comprising at least one hydrophobic segment, which segment comprises at least one urethane or urea connecting group. The composition when dried can provide a coating on a substrate or an article having low surface energy and preferably ink receptive properties. The article can provide release capabilities towards adhesives, particularly pressure sensitive adhesives.Type: GrantFiled: June 6, 1996Date of Patent: October 21, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Wayne K. Larson, Richard E. Bennett, Nicole L. Franchina
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Patent number: 5674951Abstract: Coating compositions are disclosed which use a polyoxetane polymer having CH.sub.2 --O---CH.sub.2 --R.sub.f side chains where R.sub.f is a highly fluorinated alkyl or polyether. The coating compositions use polyisocyanates to create isocyanate terminated polymers from the poly(oxetanes) and from various polyols from alkylene oxides or polyester polyols. These can be reacted together to form block copolymer structures or can be linked together when the coating is crosslinked. A preferred method is to use blocked isocyanate groups. Another preferred embodiment is to use the composition as a abrasion resistant coating for glass run channels.Type: GrantFiled: August 3, 1995Date of Patent: October 7, 1997Assignee: GenCorp Inc.Inventors: I. Glen Hargis, Charles M. Kausch, Russell A. Livigni, Aslam A. Malik, Earl G. Melby, Francis Jerome Vitus
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Patent number: 5674567Abstract: A primerless, one-part, heat curable, low volatile organic compound, polyurethane composition comprises a blocked polyurethane prepolymer made from a liquid hydroxyl terminated intermediate and an excess of a polyisocyanate, a curing agent, silicone and/or low friction polymer and optional fillers. Upon cure of the polyurethane composition, the silicone oil and/or low friction polymer generally imparts low friction and high abrasive resistant properties. A desired use is as a glass run channel coating.Type: GrantFiled: November 2, 1995Date of Patent: October 7, 1997Assignee: GenCorp Inc.Inventors: Charles M. Kausch, Earl G. Melby, Satish C. Sharma
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Patent number: 5672673Abstract: A method for the preparation of water-soluble polyaddition compounds containing perfluoroalkyl groups by the reaction of a polyisocyanate component A) with a fluorine-containing alcohol component B), hydrophilic monohydric polyether alcohols C), isocyanate-reactive tertiary amines D) and optionally other isocyanate-reactive components E) at an NCO index of 80 to 200, the resulting polyaddition compounds and their use as dispersants for incorporating solid substances into aqueous paints and coating compositions.Type: GrantFiled: June 17, 1996Date of Patent: September 30, 1997Assignee: Bayer AktiengesellschaftInventors: Stephan Kirchmeyer, Jan Mazanek, Karl-Heinz Kasler