Fluorine Containing Patents (Class 562/605)
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Patent number: 6972094Abstract: Upon recovering a fluorochemical surfactant from a fluorochemical-containing aqueous solution, there is provided a method for recovering the fluorochemical surfactant from the aqueous solution containing the surfactant. In the method, the fluorochemical surfactant is recovered by subjecting the aqueous solution containing the fluorochemical surfactant to a filtration treatment step with a reverse osmosis membrane so as to obtain from the aqueous solution, a concentrated aqueous solution in which the concentration of the fluorochemical surfactant is increased.Type: GrantFiled: August 8, 2001Date of Patent: December 6, 2005Assignee: Daikin Industries, Ltd.Inventors: Takuya Ichida, Masahiro Kondo
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Patent number: 6891064Abstract: The present invention provides a process for producing a fluoroalkylcarboxylic acid of the formula RfCOOH wherein Rf is a C1-16 fluoroalkyl group, which comprises oxidizing a fluoroalkyl alcohol of the formula RfCH2OH wherein Rf is as defined above using nitric acid. The process according to the present invention produces a fluoroalkylcarboxylic acid with high selectivity at low costs.Type: GrantFiled: May 20, 1999Date of Patent: May 10, 2005Assignee: Daikin Industries, Ltd.Inventors: Kazuyoshi Ichihara, Hirokazu Aoyama
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Patent number: 6743929Abstract: Sulfonamide-containing hydroxyethylamine compounds are effecive as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: September 6, 2000Date of Patent: June 1, 2004Assignee: G. D. Searle & Co.Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel Getman, Gary A. DeCrescenzo, John N. Freskos
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Publication number: 20040097755Abstract: Ionic compounds with a freezing point of up to 100° C. are formed by the reaction of an one amine salt of formula (I) R1R2R3R4N+X−, such as choline chloride with an organic compound (II) capable of forming a hydrogen bond with X; such as urea, wherein the molar ration of I to II is from 1:1.5 to 1:2.5. R1, R2, R3 and R4 may be H, optionally substituted C1 to C5 alkyl, optionally substituted C6 to C10 cycloalkyl, optionally substituted C6 to C12 aryl, optionally substituted C7 to C12 alkaryl, or R1 and R2 taken together may represent a C4 to C10 optionally substituted alkylene group, thereby forming with the N atom of formula I a 5 to 11-membered heterocyclic ring and all of R1, R2, R3 and R4 are not identical, X− may be NO3−, F, Cl−, Br−, I−, BF4−, ClO4−, CN−, SO3CF3−, or COOCF3−. The ionic compounds are useful as solvents, and electrolytes for example in electroplating, electrowinning, and electropolishing, and as catalysts.Type: ApplicationFiled: July 7, 2003Publication date: May 20, 2004Inventors: Andrew P. Abbott, David L. Davies, Glen Capper, Raymond K. Rasheed, Vasuki Tambyrajah
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Patent number: 6706193Abstract: Fluorinated emulsifiers can be recovered from an aqueous phase containing small amounts of fluoropolymer particles by treating the aqueous phase with a small amount of a nonionic surface-active agent, bringing the aqueous phase adjusted in this way into contact with an anionic exchanger resin, and liberating the adsorbed emulsifier from the exchanger resin. The finely divided fluoropolymer can be precipitated quantitatively in the untreated aqueous phase or the eluate using flocculating agents.Type: GrantFiled: December 11, 2001Date of Patent: March 16, 2004Assignee: 3M Innovative Properties CompanyInventors: Georg Burkard, Klaus Hintzer, Gernot Löhr
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Publication number: 20040024243Abstract: The present invention relates to a fluorination method for the synthesis of halofluoroorganic compounds which can be used, inter alia, as precursors in the synthesis of 2,3-unsaturated fluoroorganic carbonyl compounds comprising a fluorine substituent in the 2 position.Type: ApplicationFiled: February 5, 2003Publication date: February 5, 2004Inventors: Veronique Mathieu, Francine Janssens, James Franklin
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Patent number: 6613941Abstract: Fluorinated emulsifier acids can be isolated from wastewater by firstly removing fine solids and/or material which can be converted into fine solids from the wastewater, preferably by precipitation, subsequently bringing the wastewater into contact with an anion-exchange resin and eluting the adsorbed emulsifier acids from the latter.Type: GrantFiled: November 16, 2000Date of Patent: September 2, 2003Assignee: 3M Innovative Properties CompanyInventors: Bernd Felix, Reinhard Sulzbach, Stephan Führer, Thomas Kaiser, Hagen Kniep, Armin Budesheim
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Patent number: 6518442Abstract: The invention relates to a method for removing fluorinated emulsifying agent acids from waste waters, characterized in that the finely dispersed solids in the waste water are stabilized with a nonionic or cationic surfactant or an analogous acting surface active substance, the fluorinated emulsifying agent acids are subsequently bonded on an anion exchange resin and the fluorinated emulsifying agent acids are eluted from the latter.Type: GrantFiled: November 16, 2000Date of Patent: February 11, 2003Assignees: Dyneon GmbH & Co., KG, Axiva GmbHInventors: Bernd Felix, Tilman Zipplies, Stephan Führer, Thomas Kaiser, Armin Budesheim
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Patent number: 6509495Abstract: The invention concerns a selective hydrodehalogenation method characterised in that it comprises a step which consists in contacting a substrate including a sp 3 hybridisation carbon atom bearing an electro-attracting group and at least a fluorine atom, and a halogen atom heavier than fluorine, with a reagent comprising: an aqueous phase, a base, a group VIII metal as hydrogenation catalyst, and hydrogen dissolved in the aqueous phase, at a concentration in equilibrium with a gas phase whereof the partial pressure in hydrogen is not less than 50 kPa, advantageously ranging between 50 kPa and 2.10 7 Pa. The invention is applicable to organic synthesis.Type: GrantFiled: July 19, 2001Date of Patent: January 21, 2003Assignee: Rhodia ChimieInventors: Georges Cordier, Roland Jacquot
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Publication number: 20020151748Abstract: Fluorinated carboxylic acid, used as a surfactant in fluoropolymerization in aqueous media, can be recovered by scrubbing from the exhaust gas of the dryer during polymer drying and, after concentration and treatment with alumina, directly reused in fluoropolymerization in aqueous media.Type: ApplicationFiled: January 30, 2002Publication date: October 17, 2002Inventors: Clay Woodward Jones, Ta-Wei Fu
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Patent number: 6464895Abstract: The invention relates to a nucleophilic reagent which is useful for grafting a substituted difluoromethyl group onto a compound containing at least one electrophilic function, or for the synthesis of oxysulphide-containing and fluorine-containing organic derivatives, wherein said reagent comprises: a) a fluorocarboxylic acid of formula Ew—CF2—COOH where Ew represents an electron-withdrawing atom or group, at least partially salified with an organic or inorganic cation, and b) a polar aprotic solvent; and in that the content of releasable protons carried by its various components, including their impurities, is at most equal to half the initial molar concentration of the said fluorocarboxylic acid. A synthetic process uses this reagent by heating in order to graft a substituted difluoromethyl group onto various compounds.Type: GrantFiled: December 1, 1998Date of Patent: October 15, 2002Assignee: Rhodia ChimieInventors: Gérard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
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Patent number: 6437177Abstract: The present invention provides a compound of formula I or pharmaceutical acceptable salts thereof wherein R1 is C4-12 alkyl, C4-12 alkenyl, C4-12 alkynyl, —(CH2)h—C3-8 cycloalkyl, substituted and unsubstituted —(CH2)h-aryl, substituted and unsubstituted —(CH2)h-het, R2 is substituted and unsubstituted C1-12 alkyl, substituted and unsubstituted C2-12 alkenyl, substituted and unsubstituted C2-12 alkynyl, substituted and unsubstituted —(CH2)h—C3-8 cycloalkyl, substituted and unsubstituted —(CH2)h—C3-8 cycloalkenyl, substituted and unsubstituted —(CH2)h-aryl, substituted and unsubstituted —(CH2)h-heterocyclic ring, substituted and unsubstituted —(CH2)i—X—R4 (X is —O—, —S(═O)j—, —NR7—, —S(═O)2NR8—, or —C(═O)—), and —(CH2)iCHR5R6. The compounds are inhibitors of matrix metalloproteinases involved in tissue degradation.Type: GrantFiled: November 20, 1998Date of Patent: August 20, 2002Inventors: Martha A. Warpehoski, Mark Allen Mitchell, Donald E. Harper, Linda Louise Maggiora
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Patent number: 6437159Abstract: A process that can be used for isolating a fluorinated alkanoic acid from an aqueous solution also containing inorganic fluorides is provided. This process comprises (A) acidifying an aqueous solution comprising an ammonium or metal salt of a fluorinated alkanoic acid to produce an acidified solution, (B) heating the acidified solution to produce an organic layer and an aqueous layer, (C) separating and recovering the organic layer from the aqueous layer, (D) optionally washing the organic layer with an acid solution, (E) optionally isolating the fluorinated alkanoic acid, and (F) further optionally converting the fluorinated alkanoic acid to its ammonium or alkali metal salt.Type: GrantFiled: July 31, 2001Date of Patent: August 20, 2002Assignee: E. I. du Pont de Nemours and CompanyInventor: James Arnold Schultz
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Patent number: 6376705Abstract: Esters and other carboxylic acid derivatives of 3,3,4,4-tetrahydroperfluoroalkylcarboxylic acids are made by the iron promoted reaction of an ester of bromodifluoroacetic acid or other carboxylic acid derivatives and a (perfluoroalkyl)ethylene. The resulting products may be converted to the corresponding alkali metal or ammonium carboxylate slits which are useful as surfactants in fluoroolefin polymerizations.Type: GrantFiled: May 22, 2000Date of Patent: April 23, 2002Assignee: E. I. du Pont de Nemours and CompanyInventor: Weiming Qiu
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Patent number: 6365769Abstract: Novel mixtures of perfluoroalkyl halides and derivatives thereof are described. These mixtures contain some compounds with a straight perfluoroalkyl group and some with a branched perfluoroalkyl group. Methods of preparation and use are also described.Type: GrantFiled: February 15, 2000Date of Patent: April 2, 2002Assignee: 3M Innovative Properties CompanyInventors: Frederick E. Behr, Rudolf J. Dams, Johan E. DeWitte, Donald F. Hagen
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Patent number: 6281374Abstract: A process that can be used for isolating a fluorinated alkanoic acid from an aqueous solution also containing inorganic fluorides is provided. This process comprises (A) acidifying an aqueous solution comprising an ammonium salt of a fluorinated alkanoic acid to produce an acidified solution, (B) heating the acidified solution to produce an organic layer and an aqueous layer, (C) separating and recovering the organic layer from the aqueous layer, (D) optionally washing the organic layer with an acid solution, (E) optionally isolating the fluorinated alkanoic acid, and (F) further optionally converting the fluorinated alkanoic acid to its ammonium salt.Type: GrantFiled: August 23, 2000Date of Patent: August 28, 2001Assignee: E. I. du Pont de Nemours and CompanyInventor: James Arnold Schultz
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Patent number: 6245923Abstract: The process for the recovery of highly fluorinated carboxylic acids from off-gas streams, in which the off-gas is brought into contact with an alkaline washing solution of density >1.15 g/cm3 so that the salt of the highly fluorinated carboxylic acid settles out as a separate phase, proceeds particularly advantageously when the alkaline washing solution is a potassium carbonate solution.Type: GrantFiled: January 5, 1999Date of Patent: June 12, 2001Assignees: Dyneon GmbH, E. I. DuPont de Nemours & Co.Inventors: Reinhard Albert Sulzbach, Rainer Grasberger, Rik A. Brandenburg
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Patent number: 6222046Abstract: The invention has disclosed a trifluoroacetoxylation agent and a preparation process of the agent, which is safe and ease to handle, very useful in industry, and represented by the formula (1); wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group and can be the same or different, R1 and R2 or R3 and R4 can bond to form a ring containing a nitrogen atom or a nitrogen atom and other hetero atoms, and R1 and R3 can bond to form a ring containing a nitrogen atom or a nitrogen atom and other hetero atoms.Type: GrantFiled: August 9, 1999Date of Patent: April 24, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Hidetoshi Hayashi, Hiroshi Sonoda, Kenichi Goto, Kouki Fukumura, Junko Naruse, Teruyuki Nagata
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Patent number: 6184415Abstract: It has been discovered that it is possible to produce enantioselectively, a chiral 2-haloalkanoic acid or salt thereof, by subjecting a 2-halo-&agr;,&bgr;-alkenoic acid or salt, e.g., a 2-haloacrylic acid or salt, to asymmetric hydrogenation in the presence of an enantiometrically-enriched (BINAP)Ru(II) catalyst. In contrast to asymmetric hydrogenation of olefinic compounds having an electron rich, electropositive substituent in the 2-position, the substituent in the 2-position is an electronegative, electron-withdrawing halide substituent. The reaction is accelerated by inclusion of an alkali metal halide or quaternary ammonium halide in the reaction mixture.Type: GrantFiled: November 1, 1999Date of Patent: February 6, 2001Assignee: Albemarle CorporationInventors: Edward G. Samsel, Christi R. Bedell
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Patent number: 6166252Abstract: Process for preparing dichlorofluoroacetylfluoride (CFCl.sub.2 COF) comprising the following steps:a) fluorination with hydrofluoric acid (HF) of the trichloroacetyl halide in a fixed or fluidized tubular bed reactor, filled with fluorination catalysts and having a temperature profile between the inlet of the reactants and the outlet of the reaction products, in the range from 175.degree. C. to 275.degree. C.b) distillation of the reaction products with trichloroacetylfluoride recycle and recovery of a mixture formed by HF and CFCl.sub.2 COF;c) separation of the HF/CFCl.sub.2 COF mixture components by cooling at temperatures lower than -10.degree. C., and optionally the HF recycle.Type: GrantFiled: January 7, 1999Date of Patent: December 26, 2000Assignee: Ausimont S.p.A.Inventors: Piero Gavezotti, Julio A. Abusleme, Vito Tortelli
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Patent number: 6049001Abstract: Novel fluorine-containing carboxylic acid compounds of formula (II) are provided that can be reacted together with a base to produce industrially useful 3-(2-chloro-2-fluorovinyl)-2,2-dimethyl cyclopropanecarboxylic acid compounds of formula (I). The fluorine-containing containing carboxylic acid compounds of formula (II), if so desired, can be produced by reacting together a carboxylic acid compound of formula (III) and trichlorofluoromethane. In each of the formulas (I), (II), and (III), R is a lower alkyl group or a hydrogen atom.Type: GrantFiled: July 28, 1999Date of Patent: April 11, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Ken Otaka, Noritada Matsuo
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Patent number: 6046292Abstract: Mesogens are provided based on substituted unsaturated carboxylic acids such as acrylic and methacrylic acid. Substitution of a variety of hydrophobic tails onto the carboxylic acid or acid derivative via the vinyl carbon proximal to the carbonyl of the carboxylic acid results in mesogens that are capable of forming thermotropic and single-phase lyotropic mesophases over a broad range of compositions. The mesophases can be polymerized to lock in the ordered phases.Type: GrantFiled: February 3, 1999Date of Patent: April 4, 2000Assignee: The Univeristy of Southern MississippiInventors: Robert Y Lochhead, Lon J Mathias
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Patent number: 5905127Abstract: Mesogens are provided based on substituted unsaturated carboxylic acids such as acrylic and methacrylic acid. Substitution of a variety of hydrophobic tails onto the carboxylic acid or acid derivative via the vinyl carbon proximal to the carbonyl of the carboxylic acid results in mesogens that are capable of forming thermotropic and single-phase lyotropic mesophases over a broad range of compositions. The mesophases can be polymerized to lock in the ordered phases.Type: GrantFiled: April 8, 1997Date of Patent: May 18, 1999Assignee: The University of Southern MississippiInventors: Robert Y Lochhead, Lon J Mathias
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Patent number: 5763552Abstract: A partially-fluorinated surfactant having internal methylene groups and having the formula R.sub.f --(CH.sub.2).sub.m --R'.sub.f --COOM wherein m is 1-3, R.sub.f is perfluoroalkyl or perfluoroalkoxy, containing 3-8 carbon atoms, R'.sub.f is linear or branched perfluoroalkylene containing 1-4 carbon atoms, and M is NH.sub.4, Li, Na, K, or H is useful in polymerization of fluorinated monomers. High molecular weight can be achieved in homopolymerization of tetrafluoroethylene.Type: GrantFiled: July 1, 1997Date of Patent: June 9, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Ming-Hong Hung, Jose M. Rodriguez-Parada, Roger J. Zipfel
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Patent number: 5756849Abstract: The invention relates to a process and a nucleophilic reagent which is useful for grafting a substituted difluoromethyl group onto a compound containing at least one electrophilic function, characterized in that it comprises:a) a fluorocarboxylic acid of formula Ew--CF.sub.2 --COOH where Ew represents an electron-withdrawing atom or group, at least partially salified with an organic or inorganic cation, andb) a polar aprotic solvent;and in that the content of releasable protons carried by its various components, including their impurities, is at most equal to half the initial molar concentration of the said fluorocarboxylic acid.Type: GrantFiled: March 22, 1996Date of Patent: May 26, 1998Assignee: Rhone-Poulenc ChimieInventors: Gerard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
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Patent number: 5753776Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: May 19, 1998Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5750778Abstract: Certain fluoroalkanoic acids and derivatives, including 2-fluoroisobutyric acid and 2-fluoroisobutyryl chloride, useful as intermediates for fungicides, and methods of preparing them.Type: GrantFiled: August 10, 1993Date of Patent: May 12, 1998Assignee: Zeneca LimitedInventors: Patrick Jelf Crowley, Kevin Robert Lawson, Douglas John Smith, Donn Warwick Moseley
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Patent number: 5710317Abstract: A method for preparing difluoroacetic acid fluoride, which comprises reacting a 1-alkoxy-1,1,2,2-tetrafluoroethane of the formula HCF.sub.2 CF.sub.2 OR.sup.1 wherein R.sup.1 is a C.sub.1-4 alkyl group in a gas phase in the presence of a metal oxide catalyst.Type: GrantFiled: July 26, 1995Date of Patent: January 20, 1998Assignee: Asahi Glass Company Ltd.Inventors: Kazuya Oharu, Seisaku Kumai
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Patent number: 5700840Abstract: Fluorinated alkene compounds useful for controlling nematodes, insects, and acarids that prey on agricultural crops, these compounds having the formula BrCF.sub.2 CFClCH.sub.2 CO--R where R is R.sub.1 or R.sub.2. R.sub.1 is --SR.sub.5, halogen, --NHOH or --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are independently H; an aliphatic or aromatic group; an aliphatic amine group; an aliphatic carboxylic acid group; or R.sub.5 and R.sub.6 when taken with the N of R.sub.1 are an amino acid or a cyclic group or R.sub.1 is --OR.sub.5, where R.sub.5 is an aliphatic or aromatic group; an aliphatic amine group; or an aliphatic carboxylic acid group. R.sub.2 is --SR.sub.5 or --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are independently H; an aliphatic, aromatic or heterocyclic group; an aliphatic amine group; an aliphatic carboxylic acid group; R.sub.5 and R.sub.6 when taken with the N of R.sub.2 are an amino acid or a cyclic group; R.sub.5 and R.sub.6 when taken with the N of R.sub.Type: GrantFiled: May 23, 1995Date of Patent: December 23, 1997Assignee: Monsanto CompanyInventors: Dennis Paul Phillion, Peter Gerrard Ruminski, Gopichand Yalamanchili
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Patent number: 5674949Abstract: This invention pertains to a method for liquid-phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: October 7, 1997Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5672298Abstract: An electro-sensitive composition comprising a fluorine compound having a predetermined structure, and an electrically insulating medium capable of dissolving this fluorine compound when a voltage is applied thereto, is disclosed. This electro-sensitive composition has a straight chain or cyclic fluorocarbon, and fluorine compound particles possessing dissociable polarity, dispersed in an electrically insulating medium; by means of the application of a voltage to this electro-sensitive composition, the transparency and viscosity thereof can be easily adjusted.Type: GrantFiled: January 29, 1996Date of Patent: September 30, 1997Assignee: Fujikura Kasei Co., Ltd.Inventors: Kazuya Edamura, Yasufumi Otsubo
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Patent number: 5669964Abstract: An object of the present invention is to provide a compound which imparts a sufficient water repellency and a suitable oil repellency to substrates such as a fiber, a paper, a wood material, a hide, a leather, a resin, a glass, a metal, etc.The compound of the present invention is a fluoroalkylcarboxylic acid of the general formula (I), and its derivative of the general formula (II) (e.g. fluoroalkyl alcohol, fluoroalkyl carboxylic acid chloride, fluoroalkylcarboxylic acid amide and fluoroalkylamine).Type: GrantFiled: February 16, 1996Date of Patent: September 23, 1997Assignee: Matsushita Electric Industrial Co., Ltd.Inventor: Yoshiaki Kai
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Patent number: 5591877Abstract: Fluorinated carboxylic acids can be recovered from materials which contain them by releasing, if necessary, the carboxylic acids with sufficiently strong acids, esterifying the released acids and distilling off the esters. The esters can be advantageously directly hydrolyzed with aqueous ammonia solution to give the corresponding ammonium salts.Type: GrantFiled: May 3, 1995Date of Patent: January 7, 1997Assignee: Hoechst AGInventors: Reinhold Obermeier, Gunter Stefaniak
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Patent number: 5563295Abstract: A process for the production of an optically active carboxylic acid (I), which comprises subjecting an olefinic carboxylic acid (II) to asymmetric hydrogenation using a complex as a catalyst consisting of an optically active phosphine (III) and a ruthenium compound.Complex of ##STR1## with a ruthenium compound ##STR2## According to the process of the present invention, optically active carboxylic acids can be produced with high yield.Type: GrantFiled: March 7, 1995Date of Patent: October 8, 1996Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Xiaoyong Zhang, Kazuhiko Matsumura, Noboru Sayo, Hidenori Kumobayashi
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Patent number: 5545298Abstract: A process for preparing compounds corresponding to the formula RCFXC(O)Cl, in which X is fluorine or chlorine and R is fluorine or a perfluorinated C1- C10-alkyl group, preferably chlorodifluoroacetyl chloride, by photochemical oxidation of R122 (CF.sub.2 ClCHCl.sub.2) and the preparation of trifluoroacetyl chloride by photochemical oxidation of R123 (CF.sub.3 CHCl.sub.2) with oxygen under irradiation. The reaction is preferably carried out without pressurization and without addition of elemental chlorine.Type: GrantFiled: August 10, 1994Date of Patent: August 13, 1996Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Werner Rudolph, Kerstin Eichholz
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Patent number: 5539059Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.Type: GrantFiled: June 6, 1995Date of Patent: July 23, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5534192Abstract: Antistatic agents and their use in processing textiles or formed plastic substrates. The antistatic agent comprises a compound having a fluorocarbon moiety and an ethoxylated quaternary ammonium moiety. The antistatic composition increases the electrolytic conductivity of textile or plastic materials treated therewith, thereby increasing the rate of electrostatic charge dissipation thereof. The coatings remain effective after exposure of the treated substrate to an aqueous environment.Type: GrantFiled: February 22, 1995Date of Patent: July 9, 1996Assignee: Henkel CorporationInventors: Michael J. Incorvia, Stephen A. Fischer
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Patent number: 5527954Abstract: Provided is a process for the production of 2-fluoroisobutyric acid or its ester, which comprises reacting 2-hydroxyisobutyric acid or its ester with thionyl chloride and a hydrogen fluoride source.Type: GrantFiled: January 26, 1995Date of Patent: June 18, 1996Assignee: Idemitsu Kosan Co., Ltd.Inventors: Ryoichi Adachi, Masahiro Nishii, Tadashi Kikukawa, Yasuhito Kotsuji
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Patent number: 5478486Abstract: Antistatic agents and their use in processing textiles or formed plastic substrates. The antistatic agent comprises a compound having a fluorocarbon moiety and an ethoxylated quaternary ammonium moiety. The antistatic composition increases the electrolytic conductivity of treated textile or plastic materials, thereby increasing the rate of electrostatic charge dissipation thereof. The antistatic agents remain effective after exposure of the treated substrate to an aqueous environment.Type: GrantFiled: November 18, 1993Date of Patent: December 26, 1995Assignee: Henkel CorporationInventor: Michael J. Incorvia
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Patent number: 5461117Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 13, 1994Date of Patent: October 24, 1995Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5332790Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: July 26, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322904Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322903Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: January 17, 1992Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5312935Abstract: Fluorinated carboxylic acids which do not have the required purity for use as emulsifier in the polymerization of fluorinated monomers can, if necessary after prior de-watering, be treated with oxidants, whereupon the isolation of the pure product is carried out by crystallisation or, preferably, by distillation.Type: GrantFiled: April 21, 1993Date of Patent: May 17, 1994Assignee: Hoechst AktiengesellschaftInventors: Ludwig Mayer, Gernot Lohr
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Patent number: 5258547Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.Type: GrantFiled: January 9, 1992Date of Patent: November 2, 1993Assignee: Imperial Chemical Industries plcInventor: Gary N. Sheldrake
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Patent number: 5240566Abstract: A process for separating acetone, dichloromethane and trifluoroacetic acid from a mixture of acetone, dichloromethane, and a trifluoroacetic acid/acetone azeotropeby (1) fractionally distilling the mixture of acetone, dichloromethane, and the trifluoroacetic acid/acetone azeotrope;(2) fractionally distilling the mixture of the trifluoroacetic acid/acetone azeotrope and free acetone;(3) adding at least about 16 parts of water to the trifluoroacetic acid/acetone azeotrope per 100 parts by volume of the trifluoroacetic acid/acetone azeotrope;(4) fractionally distilling the mixture of free acetone and the water/trifluoroacetic acid azeotrope;(5) adding at least about 10 parts of sulfuric acid to the water/trifluoroacetic acid azeotrope per 100 parts by volume of the water/trifluoroacetic acid azeotrope;(6) fractionally distilling the mixture of trifluoroacetic acid and the water/sulfuric acid complex.Type: GrantFiled: December 7, 1992Date of Patent: August 31, 1993Assignee: The Goodyear Tire & Rubber CompanyInventors: Bruce R. Hahn, Thomas R. Maier, Surendra K. Chawla
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Patent number: 5206422Abstract: A process for the preparation of fluorinated carbonyl compounds from a fluorinated methyl or ethyl ether using tin tetrachloride as a catalyst. The fluorinated ether is contacted with the tin tetrachloride catalyst at a temperature between 0.degree. C. and 250.degree. C.Type: GrantFiled: October 11, 1991Date of Patent: April 27, 1993Assignee: The Dow Chemical CompanyInventor: David A. Babb
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Patent number: 5200549Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or methyl; ##STR2## wherein R.sub.2 is lower alkyl; R.sub.3 is phenyl, or phenyl substituted by 1 to 3 substituents selected from the group consisting of halo, lower alkyl, and lower alkoxy; and R.sub.4 is hydrogen or methyl or the corresponding hydroxy acid of formula ##STR3## and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as described above; or a pharmaceutically acceptable salt of said acid, a C.sub.1-4 alkyl ester of said acid, an acetylamino-substituted-C.sub.1-4 alkyl ester of said acid, a phenyl-dimethylamino ester of said acid or a .alpha.-monoglyceride of said acid.The compounds of formulas I and II are useful as agents for the treatment of hyperproliferative skin diseases such as psoriasis.Type: GrantFiled: September 24, 1991Date of Patent: April 6, 1993Assignee: Hoffman-La Roche Inc.Inventors: Peter M. Wovkulich, Milan R. Uskokovic, Ann Goldstein, John A. McLane
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Patent number: 5182039Abstract: Flotation aids, for use in ore flotation and beneficiation processes, comprising polyamines in the presence of fluorosubstituted organic compounds, either mixed therewith or at least partially-neutralized thereby, such that the resulting compositions separate silicate impurities and the like while also modifying and/or suppressing the froth generated. The synergistic nature of such compositions, certain embodiments of which are structurally novel, provide a cost-effective route to higher yields and increased production rates.Type: GrantFiled: March 29, 1991Date of Patent: January 26, 1993Assignee: Exxon Chemical Patents, Inc.Inventors: John C. Miller, William E. Welch
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Patent number: 5175345Abstract: A 2-fluoroisobutyric acid ester can be obtained at a high yield in one pot by reacting a 2-hydroxyisobutyric acid ester with fluorosulfuric acid in the absence or presence of a hydrogen fluoride source, or by reacting a 2-hydroxyisobutyric acid ester with chlorosulfuric acid in the presence of a hydrogen fluoride source.Type: GrantFiled: March 23, 1992Date of Patent: December 29, 1992Assignee: Idemitsu Kosan Company LimitedInventors: Izumi Terada, Masahiro Nishii, Kazufumi Nakamura