Fluorine Is Sole Halogen Patents (Class 570/136)
  • Patent number: 6329529
    Abstract: Disclosed are a fluorinating agent represented by the general 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 including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.
    Type: Grant
    Filed: July 31, 1998
    Date of Patent: December 11, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
  • Patent number: 6284715
    Abstract: Fluorinated solvents are used for the application of fluorinated waxes to skis without impairing the physico-mechanical characteristics of the ski sole. The fluorinated waxes are applied to skis in the form of a spray or an aerosol allowing for quick and effective application of high melting point fluorinated waxes onto ski soles. The fluorinated solvent may be one or more linear, branched, cross-linked, or cyclic perfluorinated compounds having a boiling temperature ranging between 30° C. and 150° C., and preferably between 50° C. and 100° C. Fluorinated waxes can be dissolved in such solvents, and the mixtures of fluorinated waxes and solvents are stored in spray cans and are sprayed onto the ski soles as aerosols or as sprays.
    Type: Grant
    Filed: February 10, 2000
    Date of Patent: September 4, 2001
    Assignee: Centeiro Trading LDA
    Inventor: Gian Paolo Gambaretto
  • Patent number: 6255543
    Abstract: Selected novel partially fluorinated &agr;,&ohgr;-dienes can be free radically (co)polymerized to form polymers in which cyclic structures are present. The polymers are useful for films, coatings and molded parts.
    Type: Grant
    Filed: December 5, 2000
    Date of Patent: July 3, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Zhen-Yu Yang
  • Patent number: 6248889
    Abstract: A process for preparing a fluoride from its corresponding alcohol comprises the steps of (a) forming a mixture comprising (i) at least one fluorinated, saturated aliphatic or alicyclic sulfonyl fluoride (for example, perfluorobutanesulfonyl fluoride) and (ii) at least one primary or secondary alcohol; and (b) adding a molar excess of at least one strong, aprotic, non-nucleophilic, hindered, double bond-containing, organic base (for example, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) to the mixture.
    Type: Grant
    Filed: November 20, 1998
    Date of Patent: June 19, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Patricia M. Savu, Daniel C. Snustad
  • Publication number: 20010003786
    Abstract: The invention relates to the synthesis of difluoromethane by gas-phase catalytic fluorination of methylene chloride.
    Type: Application
    Filed: January 18, 2001
    Publication date: June 14, 2001
    Applicant: ELF ATOCHEM S.A.
    Inventors: Benoit Requieme, Sylvain Perdrieux, Bernard Cheminal, Eric Lacroix, Andre Lantz
  • Patent number: 6096932
    Abstract: A process is disclosed for increasing the fluorine content of an olefinic compound of the formula C.sub.n H.sub.m F.sub.2n-m, where n is an integer from 2 to 6 and m is an integer from 1 to 2n. The process involves (a) contacting the olefinic compound with a metal fluoride composition of the formula (AgF)(MF.sub.2).sub.x where M is selected from the group consisting of Mn, Fe, Co, Ni, Cu, Zn and mixtures thereof and x is a number from 0 to 1, at a temperature above 200.degree. C. sufficient to transfer F from the metal fluoride composition to the olefinic compound, thereby producing a chemically reduced metal fluoride composition comprising metallic silver; (b) oxidizing the reduced metal fluoride composition from (a) in the presence of HF to regenerate the metal fluoride composition of the formula (AgF)(MF.sub.2).sub.x ; and (c) recycling regenerated metal fluoride composition of (b) to (a). Also disclosed are a novel composition of the formula Ag.sub.10 F.sub.8 C.sub.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: August 1, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Munirpallam A. Subramanian
  • Patent number: 6072088
    Abstract: A compound having the formula:CF.sub.3 CH.sub.2-w (H.sub.1-x CH.sub.2-y R.sub.m R'.sub.n CH.sub.1-z).sub.p H.sub.2-q CF.sub.3wherein w=0, 1 or 2; x=0 or 1; y=0, 1 or 2; m=0, 1 or 2; n=0 or 1; z=0 or 1; p=1 or 2; and q=0, 1 or 2; with the provisos that 1.ltoreq.w+x.ltoreq.2, 1.ltoreq.q+z.ltoreq.2, and p.multidot.y=p(m+2n)+(p-1)(x+z)+q+w+x+z-2; and wherein R includes the halogens having an atomic number greater than 9, and radicals having a valence of 1, and wherein R' is a group having a valence of 2, and a process for preparing the compound.
    Type: Grant
    Filed: August 10, 1999
    Date of Patent: June 6, 2000
    Assignee: Alliedsignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 6031141
    Abstract: This invention provides a process for the manufacture of a fluoroolefin of the formula (R.sup.1).sub.2 C.dbd.C(R.sup.1).sub.2 wherein each R.sup.1 is independently selected from the group consisting of --H, --F, --CF.sub.3, --CHF.sub.2, --CH.sub.2 F, --C.sub.2 F.sub.5, --C.sub.2 HF.sub.4 and --C.sub.2 H.sub.2 F.sub.3, provided that at least one R.sup.1 is not --H. The process comprises contacting a hydrofluorocarbon of the formula (R.sup.1).sub.2 CHCF(R.sup.1).sub.2 with a catalyst comprising cubic chromium trifluoride, i.e., a chromium trifluoride having an X-ray diffraction powder pattern shown in Table I, at a temperature of from about 200.degree. C. to about 500.degree. C.
    Type: Grant
    Filed: August 6, 1998
    Date of Patent: February 29, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rao V.N. Mallikarjuna, Munirpallam A. Subramanian
  • Patent number: 5994599
    Abstract: A process is disclosed for preparing an adduct of the formula R.sup.1 CF.sub.2 CH.sub.2 OCF.sub.3-a-m (C.sub.2 H.sub.n X.sub.4-n F).sub.m R.sup.2.sub.a wherein R.sup.1 is selected from the group consisting of --(CF.sub.2).sub.p H and --C.sub.p F.sub.2p+1 where p is 0 or an integer from 1 to 6; R.sup.2 is selected from the group consisting of --H, --CHF.sub.2, --CHFCF.sub.3, --CHFOCF.sub.3, --CHFO(CF.sub.2).sub.2 CF.sub.3, and --CHClF; each X is independently selected from the group consisting of Br, Cl and F; a is 0 or 1; m is 1 or 2, provided that when a is 1 and R.sup.2 is other than hydrogen, then m is 1; and n is 0, 1 or 2. The process involves reacting a fluorinated ether of the formula R.sup.1 CF.sub.2 CH.sub.2 OCF.sub.3-a R.sup.2.sub.a with an olefin of the formula C.sub.2 H.sub.n X.sub.4-n in the liquid phase in the presence of antimony pentafluoride catalyst. Also disclosed is a process for preparing unsaturated ethers of the formula R.sup.1 CF.sub.2 CH.sub.2 OCF.sub.3-a-m (C.sub.2 H.sub.n X.sub.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: November 30, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Viacheslav Alexandrovich Petrov
  • Patent number: 5965059
    Abstract: An optically active compound which itself generally exhibits no antiferroelectric liquid crystal phase, but which can be added to an antiferroelectric liquid crystal or composition thereof having a high threshold voltage to reduce the threshold voltage of the resulting composition. Also disclosed is an antiferroelectric liquid crystal composition containing the optically active compound, a process for reducing the threshold voltage of an antiferroelectric liquid crystal composition, a process for producing the optically active compound, and a process for producing an optically active carboxylic acid as an intermediate.
    Type: Grant
    Filed: March 19, 1998
    Date of Patent: October 12, 1999
    Assignee: Takasago International Corporation
    Inventors: Shinya Yamada, Yukiharu Iwaya, Mamoru Yamada, Akio Yamaguchi, Hitoshi Kondo, Toshimitsu Hagiwara
  • Patent number: 5914423
    Abstract: A process for the preparation of a compound of formula (I):HetSCH.sub.2 CH.sub.2 CH.dbd.CF.sub.2 (I)wherein Het is an optionally substituted 5- or 6-membered heterocyclic ring, which comprises reacting a compound of formula (II):HetSH (II)with a compound of formula (III):CF.sub.2 .dbd.CHCH.sub.2 CH.sub.2 L (III)wherein L is chlorine or bromine or a group --OSO2R.sup.a wherein R.sup.a is a C1-4 alkyl group or a phenyl group optionally substituted by a C1-4 alkyl group.
    Type: Grant
    Filed: November 24, 1997
    Date of Patent: June 22, 1999
    Assignee: Zeneca, Limited
    Inventors: Michael Drysdale Turnbull, Nigel James Willetts, Steven Fitzjohn, Prafula Govind Kholia, Harjindersingh Bansal, Alfred Glyn Williams
  • Patent number: 5750808
    Abstract: A process is disclosed for the dehydrohalogenation of partially halogenated ethanes of the formula C.sub.2 H.sub.a Cl.sub.b F.sub.c where a is an integer from 1 to 4, b is an integer from 0 to 3 and c is an integer form 1 to 5 to produce olefins selected from the group consisting of C.sub.2 H.sub.a-1 Cl.sub.b-1 F.sub.c and C.sub.2 H.sub.a-1 Cl.sub.b F.sub.c-1. The process involves contacting C.sub.2 H.sub.a Cl.sub.b F.sub.c with a zeolite selected from the group consisting of NaX and CsY. Selective reaction of one isomer from a mixture of two isomers is disclosed as a means for purification of the relatively unreactive isomer. Also disclosed is a process for producing perfluorocyclobutane which involves contacting CHF.sub.2 CClF.sub.2 with such zeolites.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: May 12, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Wendell Richard Cassel, David Richard Corbin, V.N. Mallikarjuna Rao
  • Patent number: 5728902
    Abstract: A method for manufacturing 1,1,1,3,3-pentafluoropropene comprises the steps of adding 2-trifluoromethyl-3,3,3-trifluoropropionic acid under the presence of metal carbonate and/or metal hydrogencarbonate in an aprotic solvent at reaction temperature particularly from 40.degree. C. to 80.degree. C., of refining resulting reaction products to obtain 1,1,1,3,3-pentafluoropropene, and further of coexisting a desiccating agent therein.According to the method, 1,1,1,3,3-pentafluoropropene can be manufactured through industrially efficient and cost-effective way using 2-trifluoromethyl-3,3,3-trifluoropropionic acid as a raw material.
    Type: Grant
    Filed: August 14, 1996
    Date of Patent: March 17, 1998
    Assignee: Daikin Industries Ltd.
    Inventors: Hirokazu Aoyama, Akinori Yamamoto, Noriaki Shibata
  • Patent number: 5714654
    Abstract: A method is proposed for producing 1,1,1,3,3-pentafluoropropane, in which 1,1,3,3,3-pentafluoropropene is reduced at a temperature between 40.degree. C. and 300.degree. C. by reacting it with hydrogen in a gas phase in the presence of a palladium catalyst. Further, a method is proposed for producing 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene, in which the raw material 2-chloro-1,1,3,3,3-pentafluoropropene is hydrogenated especially at a temperature between 30.degree. C. and 450.degree. C. in the presence of a catalyst composed of at least one metal selected from palladium, platinum and rhodium. Further, a method is proposed of producing 1,1,3,3,3-pentafluoropropene, in which 1,1,1,3,3-pentafluoro-2,3-dichloropropane is dechlorinated by using hydrogen in the presence of a metal oxide catalyst. Based on these production methods, 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene can thus be produced with high yield rates.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: February 3, 1998
    Assignee: Daikin Industries Ltd.
    Inventors: Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Tatsuo Nakada
  • Patent number: 5681902
    Abstract: Free radical reaction of unsaturated material, dissolved in a polar, water immiscible organic solvent, & perfluoroalkyl iodide in the presence of buffer or means for adjusting pH of aqueous phase.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: October 28, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Donald Douglas May
  • Patent number: 5510544
    Abstract: Fluorinated terpenes useful in a wide variety of general cleaning and degreasing applications are disclosed. These compounds have high solvencies but reduced flash points, and include derivatives of paracymene and myrcene, both of which, while relatively unreactive, are nonetheless miscible with a wide variety of hydrocarbon soils. The compounds exhibit flash points of 25.degree. F. or more above those of the unmodified terpenes.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: April 23, 1996
    Assignee: Environmental Solvents Corporation
    Inventor: Gene E. Keyser
  • 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: 5462810
    Abstract: A magnetic recording medium comprises a nonmagnetic substrate and at least one ferromagnetic metal layer applied thereon and a protective layer formed on this metal layer and consisting of a compound which consists of an unfluorinated or partially fluorinated alkyl radical and a disulfide, hydroxyl or keto group.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: October 31, 1995
    Assignee: BASF Magnetics GmbH
    Inventors: Harald Keller, Ulrich Jaeger, Helmut Steininger, Helmut Kopke, Klaus D. Schomann, Hans-Peter Schildberg
  • Patent number: 5432259
    Abstract: The pyrolysis of fluorine polymers leads to a high yield of pure fluorinated monomers if the finely divided polymer is introduced, with steam, into a fluidized bed reactor which contains an inert, granular material as the fluidized material, the steam functioning as the fluidizing gas.
    Type: Grant
    Filed: October 4, 1994
    Date of Patent: July 11, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Schottle, Klaus Hintzer, Hans J. Staudt, Herbert Weber
  • Patent number: 5347058
    Abstract: Fluorinated olefins are produced by thermolysis of a silyl ester of a fluorinated aliphatic carboxylic acid in the presence of a catalyst which provides fluoride ion, such as potassium fluoride. The fluorinated olefins are useful as monomers and chemical intermediates.
    Type: Grant
    Filed: December 7, 1993
    Date of Patent: September 13, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5344580
    Abstract: Oligomers of compounds of the formulaX--(CF.sub.2).sub.a --O.sub.b --(CH.sub.2).sub.c --CH=CH.sub.2( 1)and co-oligomers of compounds of the formula (1) together with compounds of the formulaX--(CX.sub.2).sub.d --O.sub.b --(CX.sub.2).sub.c --CX=CX.sub.2( 2)in which X is hydrogen or fluorine, a is a number from 2 to 16, b and c are, independently of one another, 0 or 1, and d is a number from 0 to 6, with a mean degree of oligomerization of 2 to 4, are obtained by heating a solution of the monomers in a hydrocarbon together with a free radical-forming catalyst to 135.degree. to 180.degree. C. The oligomers are lubricating agents and lubricants.
    Type: Grant
    Filed: December 1, 1992
    Date of Patent: September 6, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Konrad von Werner
  • Patent number: 5342985
    Abstract: The invention relates to a process for the metathesis of olefins which comprises reacting an olefin of the formula YCZ.dbd.CZ--(CX.sub.2).sub.n R.sup.2 (II) whereinn is an integer from 1 to 28,X represents H or F,Y represents H or alkyl having from 1 to 10 carbon atoms andZ represents H or a non-aromatic hydrocarbon group having from 1 to 6 carbon atoms and R.sup.2 represents H, alkyl, halogen, COOR.sup.3 or OR.sup.4, wherein R.sup.3 and R.sup.4 represent alkyl having from 1 to 15 carbon atoms or phenyl which is unsubstituted or contains from 1 to 3 substituents or wherein R.sup.4 is trialkylsilyl R.sup.5 Si, wherein R.sup.5 represents alkyl having from 1 to 5 carbon atoms, at a catalyst comprising an oxidic carrier charged with a rhenium compound as defined hereinbefore.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: August 30, 1994
    Assignee: Hoechst AG
    Inventors: Wolfgang A. Herrmann, Werner Wagner, Ursula Volkhardt
  • Patent number: 5276222
    Abstract: The partially fluorinated alkene 4,4,4-trifluoro-2-methyl-1-butene is produced by the selective dehydrochlorination of 3-chloro-1,1,1-trifluoro-3-methylbutane in the presence of a suitable base at elevated temperatures. The alkene is converted to 1,2-epoxy-4,4,4-trifluoro-2-methylbutane which is polymerizable in the presence of an aluminum coordination catalyst. A copolymer can be made with epichlorohydrin.
    Type: Grant
    Filed: June 12, 1991
    Date of Patent: January 4, 1994
    Assignee: The B. F. Goodrich Company
    Inventor: Paul P. Nicholas
  • Patent number: 5274189
    Abstract: This invention relates to a process for producing linear hydrofluorocarbons of the formula XCF.sub.2 (CF.sub.2).sub.n CH.sub.2 F, where X is H or F, and n is 1 to 7 when X is H, and n is 0 to 7 when X is F, by a vapor phase catalytic reaction of HF and phosgene or sulfuryl chloride with corresponding compounds of the formula XCF.sub.2 (CF.sub.2).sub.n CH.sub.2 OZ where Z is H or --C(O)OCH.sub.2 (CF.sub.2).sub.n CF.sub.2 X.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: December 28, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Mario J. Nappa, Allen C. Sievert
  • Patent number: 5254774
    Abstract: A process for the oligomerization of hexafluoropropene comprises contacting hexafluoropropene with a catalyst or a mixture of catalysts selected from the group consisting of the cyanide, cyanate, and thiocyanate salts of alkali metals, quaternary ammonium, and quaternary phosphonium, in the presence of polar, aprotic solvent, e.g., acetonitrile. The process of the invention is especially useful for selectively preparing hexafluoropropene dimers, e.g., perfluoro-2-methyl-2-pentene and perfluoro-2-methyl-3-pentene, in good yield by the proper choice of solvent and catalyst.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: October 19, 1993
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Robert A. Prokop
  • Patent number: 5162594
    Abstract: This invention concerns a process for the production of polyfluoroolefins by the catalytic addition of polyfluoroallylic fluorides to fluoroethylenes. 1:1 and 1:2 Adducts such as F-pentene-2 and F-heptene-3 can be formed selectively and reduced further to dihydro- or trihydropolyfluoroalkanes, which are useful as HFC cleaning agents.
    Type: Grant
    Filed: October 4, 1991
    Date of Patent: November 10, 1992
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 5146017
    Abstract: A process is described for the reaction of at least one partly fluorinated alkene with catalysts containing tungsten complex compounds, at 10.degree. to 200.degree. C., if appropriate in the presence of at least one inert solvent. A mixture of a partly fluorinated alkene with another partly fluorinated alkene or with a non-fluorinated alkene can also be employed for the reaction. Longer-chain partly fluorinated compounds are thereby obtained which contain at least one internal C.dbd.C double bond. Ethylene or a short-chain alkene is furthermore produced and is separated off from the reaction mixture. The longer-chain partly fluorinated compounds are valuable intermediates and can be hydrogenated to give, for example, highly heat-resistant special lubricants.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: September 8, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Konrad V. Werner, Karin Weiss
  • Patent number: 5087776
    Abstract: The present invention relates to branched perfluoroalkanes which, having bonds between a quaternary carbon atom and a tertiary carbon atom, easily undergo a homolytic scission of the C--C bond thereby releasing (non-persistent) radicals which may be used as initiators of polymerization of ethylenically unsaturated monomers.A further object of the present invention are new perfluoroalkanes having at least 9 carbon atoms belonging to the above described group.
    Type: Grant
    Filed: February 6, 1991
    Date of Patent: February 11, 1992
    Assignee: Ausimont, S.p.A.
    Inventors: Claudio Tonelli, Vito Tortelli
  • Patent number: 5087777
    Abstract: Novel partially fluorinated alkenes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkenyl or fluoroalkenyl group having 1 to 6 carbon atoms have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.
    Type: Grant
    Filed: December 4, 1990
    Date of Patent: February 11, 1992
    Assignee: Allied-Signal Inc.
    Inventors: Chien C. Li, Kane D. Cook, Rajat S. Basu
  • Patent number: 5068470
    Abstract: The present invention relates to the synthesis of new terminal olefins, perfluoro 2,4-dimethyl 3-ethylpentene and perfluoro 2-isopropyl 3,3-dimethylbutene, and to the subsequent fluorination thereof in order to obtain highly branched perfluoroalkanes, capable of providing perfluoroalkyl radicals, which are utilizable as initiators for the polymerization of ethylenically unsaturated monomers.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: November 26, 1991
    Assignee: Ausimont, S.r.l
    Inventors: Claudio Tonelli, Vito Tortelli
  • Patent number: 5064864
    Abstract: This invention relates to certain novel di- and tetra-fluoro analogs of squalene and to their methods of use in lowering plasma cholesterol and in inhibiting squalene epoxidase in patients in need thereof.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: November 12, 1991
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Esa T. Jarvi, Michael L. Edwards, James R. McCarthy
  • Patent number: 5043490
    Abstract: Novel 1,1,2-trifluorodienes, which have a minimum of seven carbon atoms and may contain in their molecule a phenylene or a methylphenylene moiety, are useful monomers, that can be polymerized in the presence of either free radical or coordination catalysts and can undergo selective reactions such, as for example, epoxidation of the vinyl (nonfluorinated) double bond. The resulting perfluorovinyl epoxy compounds also are useful monomers, which can undergo polymerization to useful materials.
    Type: Grant
    Filed: May 30, 1990
    Date of Patent: August 27, 1991
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Aaron C. Su, Wei-Yuan Huang, Yuanfa Zhang
  • Patent number: 5026928
    Abstract: The present invention relates to the synthesis of new terminal olefins, perfluoro 2,4-dimethyl 3-ethylpentene and perfluoro 2-isopropyl 3,3-dimethylbutene, and to the subsequent fluorination thereof in order to obtain highly branched perfluoroalkanes, capable of providing perfluoroalkyl radicals, which are utilizable as initiators for the polymerization of ethylenically unsaturated monomers.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: June 25, 1991
    Assignee: Ausimont S.r.l.
    Inventors: Claudio Tonelli, Vito Tortelli
  • Patent number: 5017718
    Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: May 21, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami
  • Patent number: 5011859
    Abstract: This invention relates to certain novel di- and tetra-fluoro analogs of squalene and to their methods of use in lowering plasma cholesterol and in inhibiting squalene epoxidase in patients in need thereof.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: April 30, 1991
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Esa T. Jarvi, Michael L. Edwards, James R. McCarthy
  • Patent number: 5001163
    Abstract: An organic polymeric material, which is preferably perfluorinated and which comprises a polymeric chain and at least one group pendant from the chain, in which the group pendant from the chain comprises a saturated cyclic group and at least one ion-exchange group or group convertible thereto, and in which the ion-exchange group or group convertible thereto is linked to the polymeric chain through the cyclic group. Also an ion-exchange membrane produced from the polymeric material, an electrolytic cell containing the membrane, vinyl monomers from which the organic polymeric material may be produced and intermediates useful in production of the monomers.
    Type: Grant
    Filed: March 1, 1989
    Date of Patent: March 19, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Harold C. Fielding, Philip H. Gamlen, Ian M. Shirley
  • Patent number: 4997855
    Abstract: Nematodes and insects are controlled by application of vinyl fluorides of the formula ##STR1## where R is CH.sub.2 X--, CHX.sub.2 --, CX.sub.3 --, XCH.dbd.CH--, CH.sub.2 .dbd.CX-- or straight chain alkyl(C.sub.2 -C.sub.8);R.sup.1 is hydrogen, fluoro, chloro, bromo, CH.sub.2 Z--, CHZ.sub.2 -- or CZ.sub.3 --;R.sup.2, X and Z independently are hydrogen, fluoro, chloro or bromo; Y.sup.1, Y.sup.2, Y.sup.3, and Y.sup.4 independently are CH.sub.3 or any value of R.sup.2, X and Z; a is 0-12; n is 7-13; and n is greater than a.Particular species controlled are the root-knot, stunt, lesion, cyst and free-living nematodes, and the southern corn rootworm. The vinyl fluorides also have anthelmintic utility.
    Type: Grant
    Filed: September 15, 1988
    Date of Patent: March 5, 1991
    Assignee: FMC Corporation
    Inventor: Clinton J. Peake
  • Patent number: 4968851
    Abstract: A method of combating arthropods and nematodes which comprises applying thereto, to a habitat thereof or to an area from which they are to be excluded an arthropodicidally or nematocidally effective amount of at least one long-chain halogenoolefine of the formula (I) ##STR1## in which R represents a straight-chain or branched alkyl radical with 8 to 25 carbon atoms in the straight chain, the alkyl radical optionally being interrupted once or several times by a --C.tbd.C-- and/or ##STR2## in which Z and Z.sup.1 are identical or different and represent hydrogen or methyl andR.sup.1 represents hydrogen, alkyl or halogen.Those compounds are new wherein R has at least 12 carbon atoms in the straight chain.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Naumann, Benedikt Becker, Wolfgang Behrenz, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4967022
    Abstract: Processes for the preparation of perfluoroalkyl substituted allenes and novel bis-allenyl substituted perfluoroalkanes are disclosed.
    Type: Grant
    Filed: November 29, 1989
    Date of Patent: October 30, 1990
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ming-Hong Hung
  • Patent number: 4900874
    Abstract: A method for producing a fluorine-containing olefin represented by formula (I):Ch.sub.2 .dbd.CFR.sub.f (I)wherein R.sub.f represents a perfluoroalkyl group or a fluoroalkyl group comprising the step of contacting, at a high temperature, hydrogen gas with a 1,1-dihydro-2,2-difluoro alcohol represented by formula (II):HOCH.sub.2 CF.sub.2 R.sub.f (II)wherein R.sub.f represents a perfluoroalkyl group or a fluoroalkyl group.
    Type: Grant
    Filed: February 13, 1989
    Date of Patent: February 13, 1990
    Assignee: Daikin Industries, Ltd.
    Inventors: Kiyohiko Ihara, Fumihiko Yamaguchi, Shinichi Yamane
  • Patent number: 4898645
    Abstract: A process is described for the production of pure tetrafluoroethylene from a gas formed in the pyrolysis of a fluorocarbon compound having 1 to 4 carbon atoms, which can contain a hydrogen atom and a chlorine atom. The pyrolysis gas, after hydrogen chloride or hydrogen fluoride and also if necessary steam have been separated off, is condensed under pressure and distilled in a plurality of columns, in the first column the low boilers being distilled off, preferably with a reflux ratio of 6 to 15 kg per kg of tetrafluoroethylene produced, and in the second column tetrafluoroethylene, preferably with a reflux ratio of 3 to 5 kg per kg of tetrafluoroethylene produced. Per kg of tetrafluoroethylene produced, from 0.6 to 2 kg of difluoromonochloromethane are fed into the second column as a distillation aid. The novel process makes it possible to produce pure tetrafluoroethylene at comparatively reduced energy and apparatus costs.
    Type: Grant
    Filed: August 30, 1988
    Date of Patent: February 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Voigt, Reinhold Freudenreich
  • Patent number: 4820883
    Abstract: A method for preparing an unsaturated fluorocarbon by defluorinating a perfluoroalkene employing activated carbon.
    Type: Grant
    Filed: November 24, 1987
    Date of Patent: April 11, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 4820884
    Abstract: A method for preparing an unsaturated fluorocarbon by defluorinating a perfluoroalkane employing activated carbon.
    Type: Grant
    Filed: November 24, 1987
    Date of Patent: April 11, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 4818513
    Abstract: A gaseous feed stream comprising hydrogen fluoride and 1,1-difluoroethane is contacted with liquid organic barrier material in a condensing zone to partially condense the feed stream. The gaseous phase remaining after the partial condensation comprises most of the 1,1-difluoroethane originally present in the feed stream while the liquid condensate comprises most of the hydrogen fluoride originally present in the feed stream. The gaseous phase and the liquid condensate are removed from the condensing zone as separate streams. Less than about 50 percent of the 1,1-difluoroethane originally present in the feed stream reacts with hydrogen fluoride to form 1,1,1-trifluoroethane during the partial condensation and the removal of the separate streams from the condensing zone. The preferred liquid organic barrier material is 1,1,-trifluoroethane.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: April 4, 1989
    Assignee: PPG Industries, Inc.
    Inventors: Fred C. Trager, J. Douglas Mansell, W. Eugene Wimer
  • Patent number: 4788352
    Abstract: C.sub.4 to C.sub.7 trifluoroalkene compounds and a method for their preparation by the contact of C.sub.3 or C.sub.4 trifluoroalkenes with C.sub.2 to C.sub.4 olefins in the presence of a homogeneous palladium (II) catalyst.
    Type: Grant
    Filed: October 20, 1987
    Date of Patent: November 29, 1988
    Assignee: Shell Oil Company
    Inventor: Edgar J. Smutny
  • Patent number: 4668710
    Abstract: Included are trihalovinyl polyol ethers. The compositions have pendant 1,2,2-trihaloethenyl moieties. The compositions may be low viscosity oils or highly polymeric such as incorporated with a urethane or other polymers. One of the uses of the compositions is as flame retardants which may have high thermal stability and scorch resistance.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: May 26, 1987
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, William J. Kruper, Jr.
  • Patent number: 4618734
    Abstract: A perfluoroalkylene .alpha.,.omega.-diacetylene compound having a fluorocarbon chain of from 5 to about 20 carbon atoms between two acetylene end groups, and a method of forming same by first reacting perfluoroalkylene diiodide having the formula I(CF.sub.2).sub.n I, wherein n is a whole number from 5 to about 20, inclusive with bis(trimethylsilyl)acetylene, and converting the reaction product to the diacetylene with KF. The diacetylene has the general formula HC.tbd.C(CF.sub.2).sub.n C.tbd.CH, wherein n is as set forth above, and it can be polymerized to produce a clear, hard, cross-linked resin suitable for use as a coating on bearings and in the manufacture of aircraft windshields. Monofunctional counterparts of the HC.tbd.C(CF.sub.2).sub.n C.tbd.CH compounds can be formed by substituting perfluoroalkyl primary iodides for the diiodides in the above-described reaction.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: October 21, 1986
    Assignee: Fluorochem Inc.
    Inventors: Kurt Baum, Ronald O. Hunadi, Clifford D. Bedford
  • Patent number: 4613708
    Abstract: This invention concerns new branched perfluoroalkylated ethenes, their preparation and their use, in the form of aqueous emulsions, as oxygen carriers, and in particular as blood substitutes or as perfusion agents for the preservation of organs before transplant.
    Type: Grant
    Filed: February 18, 1983
    Date of Patent: September 23, 1986
    Assignee: Produits Chemiques Ugine Kuhlmann
    Inventors: Jean Riess, Francois Jeanneaux, Maurice Le Blanc, Andre Lantz
  • Patent number: 4604480
    Abstract: A method for the preparation of a first sulfone compound of the formula: ##STR1## wherein R.sub.a is ##STR2## where R.sub.b is Br and R.sub.c is H except that R.sub.b and R.sub.c together may be an electron pair when R.sub.6 is a radical of the formula: ##STR3## wherein X.sub.1 is independently chlorine, bromine or iodine and R.sub.1 and R.sub.2 are independently at each occurrence hydrogen or, substituted or unsubstituted, phenyl or alkyl where the substituents are halogen or alkoxy or additional --SO.sub.2 Br groups; provided that, each carbon atom of R.sub.1 or R.sub.2 which contains --SO.sub.2 Br also contains an X.sub.1 group and wherein R.sub.3 through R.sub.9 are independently --OZ,--C.sub.6 M.sub.5,--Z,--SiZ.sub.3 or --X.sub.2, where Z is hydrogen or substituted or unsubstituted phenyl, alkyl, alkenyl or alkynyl; X.sub.2 is chlorine, bromine, iodine or fluorine; M is independently at each occurrence Z or X.sub.2 ; R.sub.3 and R.sub.4 may together be an electron pair; two or more of R.sub.3, R.sub.
    Type: Grant
    Filed: August 15, 1983
    Date of Patent: August 5, 1986
    Assignee: The Research Foundation of State University of New York
    Inventors: Eric Block, Mohammad Aslam
  • Patent number: 4496483
    Abstract: S-(2-Halo-2-propen-l-yl) N-(hexamethyleneimino)thiolcarbamates in which the halo is preferably bromo or chloro. The compounds have biological activity and may be used, for example, as selective pre-emergence herbicides.
    Type: Grant
    Filed: September 12, 1983
    Date of Patent: January 29, 1985
    Assignee: United States Borax & Chemical Corporation
    Inventor: Don L. Hunter