Fluorine Containing Patents (Class 562/605)
  • Patent number: 6972094
    Abstract: 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: Grant
    Filed: August 8, 2001
    Date of Patent: December 6, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Takuya Ichida, Masahiro Kondo
  • Patent number: 6891064
    Abstract: 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: Grant
    Filed: May 20, 1999
    Date of Patent: May 10, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Kazuyoshi Ichihara, Hirokazu Aoyama
  • Patent number: 6743929
    Abstract: Sulfonamide-containing hydroxyethylamine compounds are effecive as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: September 6, 2000
    Date of Patent: June 1, 2004
    Assignee: G. D. Searle & Co.
    Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel Getman, Gary A. DeCrescenzo, John N. Freskos
  • Publication number: 20040097755
    Abstract: 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: Application
    Filed: July 7, 2003
    Publication date: May 20, 2004
    Inventors: Andrew P. Abbott, David L. Davies, Glen Capper, Raymond K. Rasheed, Vasuki Tambyrajah
  • Patent number: 6706193
    Abstract: 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: Grant
    Filed: December 11, 2001
    Date of Patent: March 16, 2004
    Assignee: 3M Innovative Properties Company
    Inventors: Georg Burkard, Klaus Hintzer, Gernot Löhr
  • Publication number: 20040024243
    Abstract: 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: Application
    Filed: February 5, 2003
    Publication date: February 5, 2004
    Inventors: Veronique Mathieu, Francine Janssens, James Franklin
  • Patent number: 6613941
    Abstract: 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: Grant
    Filed: November 16, 2000
    Date of Patent: September 2, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Bernd Felix, Reinhard Sulzbach, Stephan Führer, Thomas Kaiser, Hagen Kniep, Armin Budesheim
  • Patent number: 6518442
    Abstract: 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: Grant
    Filed: November 16, 2000
    Date of Patent: February 11, 2003
    Assignees: Dyneon GmbH & Co., KG, Axiva GmbH
    Inventors: Bernd Felix, Tilman Zipplies, Stephan Führer, Thomas Kaiser, Armin Budesheim
  • Patent number: 6509495
    Abstract: 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: Grant
    Filed: July 19, 2001
    Date of Patent: January 21, 2003
    Assignee: Rhodia Chimie
    Inventors: Georges Cordier, Roland Jacquot
  • Publication number: 20020151748
    Abstract: 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: Application
    Filed: January 30, 2002
    Publication date: October 17, 2002
    Inventors: Clay Woodward Jones, Ta-Wei Fu
  • Patent number: 6464895
    Abstract: 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: Grant
    Filed: December 1, 1998
    Date of Patent: October 15, 2002
    Assignee: Rhodia Chimie
    Inventors: Gérard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
  • Patent number: 6437177
    Abstract: 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: Grant
    Filed: November 20, 1998
    Date of Patent: August 20, 2002
    Inventors: Martha A. Warpehoski, Mark Allen Mitchell, Donald E. Harper, Linda Louise Maggiora
  • Patent number: 6437159
    Abstract: 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: Grant
    Filed: July 31, 2001
    Date of Patent: August 20, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: James Arnold Schultz
  • Patent number: 6376705
    Abstract: 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: Grant
    Filed: May 22, 2000
    Date of Patent: April 23, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Weiming Qiu
  • Patent number: 6365769
    Abstract: 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: Grant
    Filed: February 15, 2000
    Date of Patent: April 2, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Frederick E. Behr, Rudolf J. Dams, Johan E. DeWitte, Donald F. Hagen
  • Patent number: 6281374
    Abstract: 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: Grant
    Filed: August 23, 2000
    Date of Patent: August 28, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: James Arnold Schultz
  • Patent number: 6245923
    Abstract: 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: Grant
    Filed: January 5, 1999
    Date of Patent: June 12, 2001
    Assignees: Dyneon GmbH, E. I. DuPont de Nemours & Co.
    Inventors: Reinhard Albert Sulzbach, Rainer Grasberger, Rik A. Brandenburg
  • Patent number: 6222046
    Abstract: 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: Grant
    Filed: August 9, 1999
    Date of Patent: April 24, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hidetoshi Hayashi, Hiroshi Sonoda, Kenichi Goto, Kouki Fukumura, Junko Naruse, Teruyuki Nagata
  • Patent number: 6184415
    Abstract: 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: Grant
    Filed: November 1, 1999
    Date of Patent: February 6, 2001
    Assignee: Albemarle Corporation
    Inventors: Edward G. Samsel, Christi R. Bedell
  • Patent number: 6166252
    Abstract: 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: Grant
    Filed: January 7, 1999
    Date of Patent: December 26, 2000
    Assignee: Ausimont S.p.A.
    Inventors: Piero Gavezotti, Julio A. Abusleme, Vito Tortelli
  • Patent number: 6049001
    Abstract: 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: Grant
    Filed: July 28, 1999
    Date of Patent: April 11, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ken Otaka, Noritada Matsuo
  • Patent number: 6046292
    Abstract: 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: Grant
    Filed: February 3, 1999
    Date of Patent: April 4, 2000
    Assignee: The Univeristy of Southern Mississippi
    Inventors: Robert Y Lochhead, Lon J Mathias
  • Patent number: 5905127
    Abstract: 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: Grant
    Filed: April 8, 1997
    Date of Patent: May 18, 1999
    Assignee: The University of Southern Mississippi
    Inventors: Robert Y Lochhead, Lon J Mathias
  • Patent number: 5763552
    Abstract: 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: Grant
    Filed: July 1, 1997
    Date of Patent: June 9, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Andrew E. Feiring, Ming-Hong Hung, Jose M. Rodriguez-Parada, Roger J. Zipfel
  • Patent number: 5756849
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: May 26, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Gerard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
  • Patent number: 5753776
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 19, 1998
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5750778
    Abstract: Certain fluoroalkanoic acids and derivatives, including 2-fluoroisobutyric acid and 2-fluoroisobutyryl chloride, useful as intermediates for fungicides, and methods of preparing them.
    Type: Grant
    Filed: August 10, 1993
    Date of Patent: May 12, 1998
    Assignee: Zeneca Limited
    Inventors: Patrick Jelf Crowley, Kevin Robert Lawson, Douglas John Smith, Donn Warwick Moseley
  • Patent number: 5710317
    Abstract: 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: Grant
    Filed: July 26, 1995
    Date of Patent: January 20, 1998
    Assignee: Asahi Glass Company Ltd.
    Inventors: Kazuya Oharu, Seisaku Kumai
  • Patent number: 5700840
    Abstract: 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: Grant
    Filed: May 23, 1995
    Date of Patent: December 23, 1997
    Assignee: Monsanto Company
    Inventors: Dennis Paul Phillion, Peter Gerrard Ruminski, Gopichand Yalamanchili
  • Patent number: 5674949
    Abstract: This invention pertains to a method for liquid-phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 7, 1997
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5672298
    Abstract: 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: Grant
    Filed: January 29, 1996
    Date of Patent: September 30, 1997
    Assignee: Fujikura Kasei Co., Ltd.
    Inventors: Kazuya Edamura, Yasufumi Otsubo
  • Patent number: 5669964
    Abstract: 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: Grant
    Filed: February 16, 1996
    Date of Patent: September 23, 1997
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventor: Yoshiaki Kai
  • Patent number: 5591877
    Abstract: 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: Grant
    Filed: May 3, 1995
    Date of Patent: January 7, 1997
    Assignee: Hoechst AG
    Inventors: Reinhold Obermeier, Gunter Stefaniak
  • Patent number: 5563295
    Abstract: 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: Grant
    Filed: March 7, 1995
    Date of Patent: October 8, 1996
    Assignee: Takasago International Corporation
    Inventors: Hidemasa Takaya, Xiaoyong Zhang, Kazuhiko Matsumura, Noboru Sayo, Hidenori Kumobayashi
  • Patent number: 5545298
    Abstract: 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: Grant
    Filed: August 10, 1994
    Date of Patent: August 13, 1996
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Werner Rudolph, Kerstin Eichholz
  • Patent number: 5539059
    Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 23, 1996
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5534192
    Abstract: 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: Grant
    Filed: February 22, 1995
    Date of Patent: July 9, 1996
    Assignee: Henkel Corporation
    Inventors: Michael J. Incorvia, Stephen A. Fischer
  • Patent number: 5527954
    Abstract: 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: Grant
    Filed: January 26, 1995
    Date of Patent: June 18, 1996
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Ryoichi Adachi, Masahiro Nishii, Tadashi Kikukawa, Yasuhito Kotsuji
  • Patent number: 5478486
    Abstract: 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: Grant
    Filed: November 18, 1993
    Date of Patent: December 26, 1995
    Assignee: Henkel Corporation
    Inventor: Michael J. Incorvia
  • Patent number: 5461117
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: October 24, 1995
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5332790
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: July 26, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322904
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322903
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5312935
    Abstract: 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: Grant
    Filed: April 21, 1993
    Date of Patent: May 17, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Mayer, Gernot Lohr
  • Patent number: 5258547
    Abstract: 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: Grant
    Filed: January 9, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: Gary N. Sheldrake
  • Patent number: 5240566
    Abstract: 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: Grant
    Filed: December 7, 1992
    Date of Patent: August 31, 1993
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Bruce R. Hahn, Thomas R. Maier, Surendra K. Chawla
  • Patent number: 5206422
    Abstract: 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: Grant
    Filed: October 11, 1991
    Date of Patent: April 27, 1993
    Assignee: The Dow Chemical Company
    Inventor: David A. Babb
  • Patent number: 5200549
    Abstract: 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: Grant
    Filed: September 24, 1991
    Date of Patent: April 6, 1993
    Assignee: Hoffman-La Roche Inc.
    Inventors: Peter M. Wovkulich, Milan R. Uskokovic, Ann Goldstein, John A. McLane
  • Patent number: 5182039
    Abstract: 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: Grant
    Filed: March 29, 1991
    Date of Patent: January 26, 1993
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: John C. Miller, William E. Welch
  • Patent number: 5175345
    Abstract: 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: Grant
    Filed: March 23, 1992
    Date of Patent: December 29, 1992
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Izumi Terada, Masahiro Nishii, Kazufumi Nakamura