Chalcogen Double Bonded Directly To The Sulfur (e.g., Sulfonyl Fluorides, Etc.) Patents (Class 562/825)
  • Patent number: 9842993
    Abstract: A film-forming composition according to the present invention include fluororesin having a repeating unit of the general formula (1); and a fluorine-containing solvent. In the general formula (1), R1 each independently represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; and R2 each independently represents C1-C15 straight, C3-C15 branched or C3-C15cyclic fluorine-containing hydrocarbon gr which any hydrogen atom may be replaced by a fluorine atom with the proviso that the repeating unit contains at least one fluorine atom. This film-forming composition is suitably usable for the manufacturing of an organic semiconductor element because the composition can form a film on an organic semiconductor film; and the formed film has resistance to an etching solvent during the fine pattern processing of the organic semiconductor film by photolithography etc.
    Type: Grant
    Filed: July 14, 2014
    Date of Patent: December 12, 2017
    Assignee: Central Glass Company, Limited
    Inventors: Yoshiharu Terui, Haruhiko Komoriya, Fumito Kobayashi, Yukari Hara, Ikunari Hara
  • Patent number: 9765021
    Abstract: The preparation is described of a compound of formula (I) comprising an —SO2F function by reacting a compound of formula (II) with a fluorinating agent selected from hydrofluoric acid and an ionic fluoride of a monovalent or divalent cation: R—SO2F??(I) R?—SO2X??(II) where R is selected from the groups R1, R2 and R3: R1=—CnHaFb with n=1-10, a+b=2n+1, b?1; R2=—CxHyFz—SO2F with x=1-10, y+z=2x and z?1; R3=?-CcHhFf with c=1-10; h+f=2c and f?1; where R? is selected from the following groups R?1, R?2 and R?3: R?1=—CnHaXb with n=1-10, a+b=2n+1, b?1; R?2=—CxHyXz—SO2X with x=1-10, y+z=2x and z?1; R?3=?-CcHhXf with c=1-10; h+f=2c and f?1; ? denoting a phenyl group; X?Cl, Br.
    Type: Grant
    Filed: July 3, 2014
    Date of Patent: September 19, 2017
    Assignee: RHODIA OPERATIONS
    Inventor: François Metz
  • Publication number: 20140339096
    Abstract: In this method, RH2ORH1SO2F is added to hydrofluoric acid so as to form a thick solution (hydrogen bonded complex), and the solution is directly supplied to a liquid phase reaction system, in which an F2 gas is used. Alternatively, RH2ORH1SO2Cl is added to hydrofluoric acid so as no be converted into RH1ORH2SO2F by disc barging HCl, and the RH1ORH2SO2F is directly supplied to a liquid phase reaction system in which an F2 gas is used. Consequently, fluorination can be carried out safely and a compound having an objective structure can be produced at low cost without causing isomerization or the like.
    Type: Application
    Filed: August 4, 2014
    Publication date: November 20, 2014
    Inventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
  • Publication number: 20140093823
    Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography.
    Type: Application
    Filed: September 27, 2013
    Publication date: April 3, 2014
    Inventors: Robert L. BRAINARD, Shinya AKIBA, Ryo NADANO, Kenji HOSOI, Brian CARDINEAU
  • Publication number: 20120184763
    Abstract: In this method, RH2ORH1SO2F is added to hydrofluoric acid so as to form a thick solution (hydrogen bonded complex), and the solution is directly supplied to a liquid phase reaction system in which an F2 gas is used. Alternatively, RH2ORH1SO2Cl is added to hydrofluoric acid so as to be converted into RH1ORH2SO2F by discharging HCl, and the RH1ORH2SO2F is directly supplied to a liquid phase reaction system in which an F2 gas is used. Consequently, fluorination can be carried out safely and a compound having an objective structure can be produced at low cost without causing isomerization or the like.
    Type: Application
    Filed: September 29, 2010
    Publication date: July 19, 2012
    Applicants: Mitsubishi Materials Electronic Chemicals Co., Ltd, MITSUBISHI MATERIALS CORPORATION
    Inventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
  • Patent number: 8067585
    Abstract: The present invention relates to producing a disulfonyl fluoride compound easily and efficiently by utilizing coupling reaction where a compound (2) is obtained by subjecting a compound (1) wherein Y is a fluorine atom to photocoupling reaction, or subjecting a compound (1) wherein Y is a hydroxyl group, —OMa wherein Ma is an alkali metal atom, or —O(Mb)1/2 wherein Mb is an alkaline earth metal atom to electrolytic coupling reaction, and derivatives such as the following compound (7A) are obtained from the compound (2): FSO2-E-CX2—COY??(1) FSO2-E-CX2—CX2-E-SO2F??(2) wherein E is a single bond, —O—, a C1-20 alkylene group which may contain an etheric oxygen atom, or the like, X is a fluorine atom or the like, and Y is a fluorine atom, a hydroxyl group, or the like.
    Type: Grant
    Filed: October 1, 2007
    Date of Patent: November 29, 2011
    Assignee: Asahi Glass Company, Limited
    Inventors: Masao Iwaya, Kazuya Oharu, Hidekazu Okamoto
  • Patent number: 7781612
    Abstract: The present invention provides a process for producing a fluorinated sulfonyl fluoride useful as e.g. a material for an ion exchange resin, and a novel chemical substance useful as an intermediate in the production process.
    Type: Grant
    Filed: December 28, 2005
    Date of Patent: August 24, 2010
    Assignee: Asahi Glass Company, Limited
    Inventors: Koichi Murata, Takashi Okazoe, Eisuke Murotani
  • Publication number: 20090187044
    Abstract: A compound containing two fluorosulfonyl groups which are groups convertible to sulfonic acid groups, an intermediate therefor, and methods for their production with high productivity, are provided. Also provided are a fluorosulfonyl group-containing polymer obtained by polymerizing such a compound, and a sulfonic acid group-containing polymer obtained from such a polymer.
    Type: Application
    Filed: March 25, 2009
    Publication date: July 23, 2009
    Applicant: Asahi Glass Company, Limited
    Inventors: Isamu Kaneko, Atsushi Watakabe, Jyunichi Tayanagi, Susumu Saito
  • Patent number: 7531610
    Abstract: A compound containing two fluorosulfonyl groups which are groups convertible to sulfonic acid groups, an intermediate therefor, and methods for their production with high productivity, are provided. Also provided are a fluorosulfonyl group-containing polymer obtained by polymerizing such a compound, and a sulfonic acid group-containing polymer obtained from such a polymer.
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: May 12, 2009
    Assignee: Asahi Glass Company, Limited
    Inventors: Isamu Kaneko, Atsushi Watakabe, Jyunichi Tayanagi, Susumu Saito
  • Publication number: 20080146841
    Abstract: A compound containing two fluorosulfonyl groups which are groups convertible to sulfonic acid groups, an intermediate therefor, and methods for their production with high productivity, are provided. Also provided are a fluorosulfonyl group-containing polymer obtained by polymerizing such a compound, and a sulfonic acid group-containing polymer obtained from such a polymer.
    Type: Application
    Filed: January 28, 2008
    Publication date: June 19, 2008
    Applicant: Asahi Glass Company, Limited
    Inventors: Isamu Kaneko, Atsushi Watakabe, Jyunichi Tayanagi, Susumu Saito
  • Patent number: 7297815
    Abstract: It is an object of the present invention to solve difficulty in production and to provide a process to obtain fluorinated sulfonyl fluoride compound having various molecular structures efficiently at a low cost. That is, the present invention provides a process which comprises reacting (FSO2—)nRA(-E-RB)m (1F) with fluorine in a liquid phase to form (FSO2—)nRAF(-EF-RBF)m (2), and decomposing this compound to obtain (FSO2—)nRAF(-EF1)m (3), provided that RA is a (n+m) valent organic group having at least two carbon atoms, RAF is a group having RA fluorinated, or the like, each of RB and RBF is a fluorinated monovalent organic group, or the like, E is —COOCH2— or the like, EF is —COOCF2— or the like, EF1 is —COF or the like, n is an integer of at least 2, and m is an integer of at least 1.
    Type: Grant
    Filed: January 3, 2006
    Date of Patent: November 20, 2007
    Assignee: Asahi Glass Company, Limited
    Inventors: Koichi Murata, Takashi Okazoe, Eisuke Murotani
  • Patent number: 7176331
    Abstract: The present application provides a process to produce fluorinated vinyl ether by reacting a 2-alkoxypropionyl fluoride with a metal carbonate under anhydrous conditions in a stirred bed reactor at a temperature above the decarboxylation temperature of an intermediate carboxylate to produce a fluorinated vinyl ether. The process is carried out in the absence of solvent. With the process described, fluorinated vinyl ether of a high purity can be obtained in a high throughput manner.
    Type: Grant
    Filed: June 30, 2005
    Date of Patent: February 13, 2007
    Assignee: 3M Innovative Properties Company
    Inventor: Miguel Antonio Guerra
  • Patent number: 7157600
    Abstract: A process for preparing (per)fluorohalogenethers containing the —SO2F group, having general formula (I): FSO2—R—CF2OCAF—CA?F2??(I) wherein: A and A?, equal to or different from each other, are Cl or Br; R has the following meanings: a (per)fluorinated, preferably perfluorinated, substituent, optionally containing one or more oxygen atoms; by reaction of carbonyl compounds having formula (II): FSO2—R—COF??(II) wherein R is as above; in liquid phase with elemental fluorine and with olefinic compounds having formula (III): CAF?CA?F??(III) wherein A and A? are as above, operating at temperatures from ?120° C. to ?20° C., optionally in the presence of a solvent inert under the reaction conditions.
    Type: Grant
    Filed: March 10, 2004
    Date of Patent: January 2, 2007
    Assignee: Solvay Solexis S.p.A.
    Inventors: Vito Tortelli, Pierangelo Calini, Stefano Millefanti
  • Patent number: 7105697
    Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. Namely, the present invention provides a process which comprises reacting XSO2RA-E1 (1) with RB-E2 (2) to form XSO2RA-E-RB (3), then reacting (3) with fluorine in a liquid phase to form FSO2RAF-EF-RBF (4), and further, decomposing the compound to obtain FSO2RAF-EF1 (5), wherein RA is a bivalent organic group, E1 is a monovalent reactive group, RB is a monovalent organic group, E2 is a monovalent reactive group which is reactive with E1, E is a bivalent connecting group formed by the reaction of E1 with E2, RAF is a bivalent organic group formed by the fluorination of RA, etc., RBF is the same group as RB, etc., EF is a bivalent connecting group formed by the fluorination of E, etc.
    Type: Grant
    Filed: March 25, 2004
    Date of Patent: September 12, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa
  • Patent number: 7005545
    Abstract: The present invention provides a process for producing a fluorinated fluorosulfonylalkyl vinyl ether represented by general formula (2): CF2?CFO(CF2CF(CF3)O)nCF2CF2SO2F??(2) wherein n is an integer from 0 to 10, comprising fluorinating a perfluorovinylether sulfonate with SF4 and HF, the perfluorovinylether sulfonate being represented by general formula (1): CF2?CFO(CF2CF(CF3)O)nCF2CF2SO3M??(1) wherein M is Ma or Mb1/2, provided that Ma is an alkali metal and Mb is an alkaline earth metal; and n is as defined above. According to the process of the invention, the fluorinated fluorosulfonylalkyl vinyl ether can be produced in high yield in an industrially advantageous manner.
    Type: Grant
    Filed: May 23, 2003
    Date of Patent: February 28, 2006
    Assignee: Daikin Industries, Ltd.
    Inventors: Akinari Sugiyama, Tatsuya Ohtsuka, Kazuyoshi Ichihara, Toshiya Mantani
  • Publication number: 20040199009
    Abstract: A process for preparing (per)fluorohalogenethers containing the —SO2F group, having general formula (I):
    Type: Application
    Filed: March 10, 2004
    Publication date: October 7, 2004
    Applicant: SOLVAY SOLEXIS S.p.A.
    Inventors: Vito Tortelli, Pierangelo Calini, Stefano Millefanti
  • Patent number: 6790982
    Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. The present invention is also directed to a compound of the following formula (I) or a compound of the following formula (II): FSO2CH2CH2OCH2OCOCF(CF3)OCF2CF2CF3  (I) FSO2CF2CF2OCF2CF2OCOCF(CF3)OCF2CF2CF3  (II).
    Type: Grant
    Filed: May 21, 2003
    Date of Patent: September 14, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa
  • Publication number: 20040176636
    Abstract: There is provided a process for producing a fluorinated vinyl ether from a fluorinated acid fluoride compound having an ester group as a precursor of a carboxylic acid group, or a SO2F group as a precursor of a sulfonic acid group, in high yield by simple operations.
    Type: Application
    Filed: December 29, 2003
    Publication date: September 9, 2004
    Inventors: Nobuto Hoshi, Nobuyuki Uematsu, Masanori Ikeda
  • Publication number: 20040158099
    Abstract: Compounds of formula CH2Y—CH(COOR1)—O—CF2CF2—SO2F, usable in the synthesis of the fluorosulphonic vinylether —CF2═CF—O—CF2CF2—SO2F.
    Type: Application
    Filed: February 5, 2004
    Publication date: August 12, 2004
    Applicant: Ausimont S.P.A.
    Inventors: Vito Tortelli, Sara Maculan
  • Publication number: 20040116742
    Abstract: A method is provided for reacting hexafluoropropylene oxide (HFPO) with a perfluoroacyl fluorides according to the formula X—Rf—COF (II) to selectively produce a monoaddition product according to the formula X—Rf—CF2—O—CF(CF3)COF (I), wherein selectivity for the monoaddition product over the biaddition product is 90% or greater or more typically 95% or greater. A continuous or repeated-batch process is provided comprising the steps of: a) providing a mixture of X—Rf—COF (II), a fluoride salt, and a polar solvent; b) adding hexafluoropropylene oxide (HFPO) in an amount such that X—Rf—COF remains in molar excess of HFPO by at least 10% and reacting X—Rf—COF with HFPO; c) separating unreacted X—Rf—COF from a mixture of addition products of hexafluoropropylene oxide (HFPO) and X—Rf—COF; and d) repeating step a) using unreacted X—Rf—COF separated in step c).
    Type: Application
    Filed: December 17, 2002
    Publication date: June 17, 2004
    Applicant: 3M Innovative Properties Company
    Inventor: Miguel Antonio Guerra
  • Publication number: 20040097757
    Abstract: The invention relates to a fluorination process for producing fluorinated compounds.
    Type: Application
    Filed: December 3, 2003
    Publication date: May 20, 2004
    Inventors: Milos Cernik, Antonin Ruzicka, Zdirad Zak, Virginie Pevere, Christophe Michot
  • Publication number: 20040039201
    Abstract: The present invention relates to improved covalent coupling of two or more entities such as biomolecules, polymer compositions, organic/inorganic molecules/materials, and the like, including their combinations, through one or more novel reactive groups attached to linker groups of 2-1000 atoms length. The present invention also contemplates the use of bifunctional bridge molecules to link two or more entities, wherein the functional groups of the bridge molecules are the novel reactive groups of the present invention.
    Type: Application
    Filed: November 14, 2002
    Publication date: February 26, 2004
    Inventors: Ananda G. Lugade, Kurt D. Hoffacker, Adam J. Jenkins, Karri L. Michael-Ballard, Leonid Patsenker, Ewald Terpetchnixg
  • Publication number: 20030212297
    Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production.
    Type: Application
    Filed: May 21, 2003
    Publication date: November 13, 2003
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa
  • Patent number: 6624328
    Abstract: A method is provided for making a perfluorinated vinyl ether having a sulfonyl fluoride end-group according to the formula FSO2—(CF2)n—O—CF═CF2, where n is 2-5, comprising the steps of: a) fluorination of: to produce FSO2—(CF2)(n−1)—COF; b) reaction of FSO2—(CF2)(n−1)—COF with hexafluoropropylene oxide (HFPO) to produce FSO2—(CF2)(n)—O—CF(CF3)—COF; c) reaction of FSO2—(CF2)(n)—O—CF(CF3)—COF with a salt of a metal cation M+P, where p is the valence of M, to produce (FSO2—(CF2)(n)—O—CF(CF3)—COO−)pM+P; and d) thermal cracking of FSO2—(CF2)(n)—O—CF(CF3)—COO−)pM+P to produce FSO2—(CF2)(n)—O—CF═CF2.
    Type: Grant
    Filed: December 17, 2002
    Date of Patent: September 23, 2003
    Assignee: 3M Innovative Properties Company
    Inventor: Miguel Antonio Guerra
  • Publication number: 20030125582
    Abstract: Compounds of formula CH2Y—CH(COOR1)—O—CF2CF2—SO2F, usable in the synthesis of the fluorosulphonic vinylether —CF2═CF—O——CF2CF2—SO2F.
    Type: Application
    Filed: December 27, 2002
    Publication date: July 3, 2003
    Applicant: Ausimont S.p.A.
    Inventors: Vito Tortelli, Sara MacUlan
  • Patent number: 6580006
    Abstract: The present invention provides a catalytic process for preparing perfluoroethanesulfonyl fluoride and/or perfluorodiethylsulfone using a two-part catalytic process comprising a metal fluoride and a crown ether.
    Type: Grant
    Filed: May 2, 2002
    Date of Patent: June 17, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: William M. Lamanna, Michael D. Barrera, Gerald L. Bauer, Yuri Cheburkov
  • Publication number: 20020007083
    Abstract: The present invention provides a monomer having the formula A-B, wherein A is represented by Formula I: 1
    Type: Application
    Filed: April 6, 2001
    Publication date: January 17, 2002
    Applicant: 3M Innovative Properties Company
    Inventors: Darryl D. DesMarteau, Charles W. Martin, Lawrence A. Ford, Yuan Xie
  • Patent number: 6303814
    Abstract: N-(Triazoloazinyl)arylsulfonamide compounds, such as 2,6-dimethoxy-N-(8-chloro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide, 2-methoxy-4-(trifluoromethyl)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyridine-3-sulfonamide, and 2-methoxy-6-methoxycarbonyl-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzenesulfonamide were prepared from appropriately substituted 2-amino[1,2,4]triazolo [1,5-c]pyrimidine and 2-amino[1,2,4]triazolo[1,5-a]pyridine compounds and appropriately substituted benzene sulfonyl chloride and pyridine-3-sulfonyl chloride compounds. The compounds were found to be useful as herbicides.
    Type: Grant
    Filed: March 16, 2000
    Date of Patent: October 16, 2001
    Assignee: Dow AgroSciences LLC
    Inventors: Timothy C. Johnson, Robert J. Ehr, Mark A. Pobanz, Richard K. Mann, Timothy P. Martin, John C. Van Heertum
  • Patent number: 6274632
    Abstract: The invention relates to compounds of the formula (I): CF2═CX—CH2—CH2—S(O)—R wherein X represents hydrogen, halogen or lower alkyl, and R represents a group OR1 or NR2R3 wherein R1, R2 and R3 are as defined in the description. The compounds are useful for controlling insect and like pests of agriculture.
    Type: Grant
    Filed: September 10, 1999
    Date of Patent: August 14, 2001
    Assignee: Zeneca Limited
    Inventor: Roger Salmon
  • Patent number: 5684192
    Abstract: Sulfonyl fluoride substituted .alpha.,.beta.,.beta.-trifluorostyrene monomers are disclosed. The monomers are incorporated into polymeric compositions which are conveniently hydrolyzed to produce polymeric compositions which include ion-exchange moieties. The resulting compositions which include ion-exchange moieties are particularly suitable for use as solid polymer electrolytes in electrochemical applications, such as, for example, electrochemical fuel cells.
    Type: Grant
    Filed: December 20, 1995
    Date of Patent: November 4, 1997
    Assignee: Ballard Power Systems, Inc.
    Inventors: Charles Stone, Alfred E. Steck, Robert D. Lousenberg
  • Patent number: 5627292
    Abstract: The invention relates to monomers derived from perhalogenated sultones, to a process for their preparation, to the polymers obtained from the said monomers and to their use for the production of ion-conductive materials.The monomers are compounds corresponding to the formula A--CFX--SO.sub.2 Z in which A denotes one groups [sic] R.sup.3 --O--CF.sub.2 -- or R.sup.3 -- or R.sup.1 R.sup.2 N--CO--; Z denotes F, Cl, --OSi(CH.sub.3).sub.3 or an ionic group, Z being other than F when A denotes R.sup.3 --O--CF.sub.2 -- or R.sup.3 --; X denotes F, Cl, H or R.sub.F, X being R.sub.F when A denotes R.sup.3 --; the radicals R.sup.1, R.sup.2 and R.sup.3 are chosen from polymerizable nonperfluorinated organic radicals; R.sub.F is chosen from perfluoroalkyl radicals and perfluoroaryl radicals.The polymers obtained from these monomers can be employed for the production of ion-conductive materials.
    Type: Grant
    Filed: March 9, 1994
    Date of Patent: May 6, 1997
    Assignees: Centre National de la Recherche Scientifique, Hydro-Quebec
    Inventors: Michel Armand, Jean-Yves Sanchez, Salime Sylla
  • 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: 5318674
    Abstract: A process for preparing perfluoroalkanesulfonyl fluorides, e.g., perfluoromethanesulfonyl fluoride, comprises electrochemically fluorinating in the presence of anhydrous hydrogen fluoride at least one precursor compound selected from the group consisting of .alpha.,.beta.-difluoroalkane-.beta.-sultones, e.g., 1,1,2,2-tetrafluoroethane sultone, and the corresponding .alpha.-halocarbonylfluoroalkanesulfonyl halides, e.g., fluorocarbonyldifluoromethanesulfonyl fluoride. The process can be used to prepare perfluoroalkanesulfonyl fluorides in good yield and can be, for example, both more electrically-efficient and more fluorine-efficient than the conventional preparative method involving the electrochemical fluorination of hydrocarbon alkanesulfonyl halides.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: June 7, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Fredrick E. Behr, Yuri Cheburkov, John C. Hansen
  • Patent number: 5268511
    Abstract: A two step process, each of the steps being novel, for the production of trifluorovinyl ethers by reaction of a siloxane with selected acyl fluorides or carboxylic anhydrides, is disclosed. Also disclosed is a novel silyl ester intermediate.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: December 7, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5241110
    Abstract: This invention relates to a process for preparing perfluoroalkoxysulphonic compounds having formula: ##STR1## wherein R.sub.f represents a perfluoroalkyl or perfluoroethereal group, X represents F, OH or OM, in which M is an alkaline cation, an alkaline-earth cation, or X represents NR.sub.1 R.sub.2, in which R.sub.1 and R.sub.2, independently of each other, represent H or an alkyl group containing from 1 to 5 carbon atoms and p is a number selected from 1 to 2, characterized in that the perfluoro vinyl sulphonyl fluoride of formula (II) CF.sub.2 =CF--SO.sub.2 F is reacted with a hypofluorite of formula (III):R.sub.f (OF).sub.r (III)wherein R.sub.f is the same as defined above, and r represents 1 or 2, optionally in an inert solvent, at a temperature approximately ranging from -140.degree. C. to +40.degree. C.
    Type: Grant
    Filed: July 10, 1991
    Date of Patent: August 31, 1993
    Assignee: Ausimont S.p.A.
    Inventors: Walter Navarrini, Vittorio Montanari, Anna M. Staccione
  • Patent number: 5159105
    Abstract: Pentafluorosulfanyl fluoroaliphatic carbonyl and sulfonyl fluorides, derivatives of the acid fluorides and the preparation and use of the acid fluorides and derivatives. The fluoroaliphatic moiety of said acid fluorides comprise at least three fully-fluorinated carbon atoms. The derivatives of the acid fluorides are useful as surface-active agents and surface-treating agents.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: October 27, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: John C. Hansen, Patricia M. Savu
  • Patent number: 5117055
    Abstract: A perfluoroalkyl halogenide represented by the formula: ##STR1## wherein X stands for one element selected from the group consisting of iodine and bromine, R.sub.f for a perfluorohydrocarbon group, n for an integer in the range of 1 to 3, and m for an integer in the range of 1 to 3, provided that n and m satisfy the relationship, n.gtoreq.m, is produced by a method which consists essentially in subjecting a perfluorocarboxylic acid fluoride represented by the formula, ##STR2## wherein R.sub.f and n have the same meanings as defined above, to a thermal reaction with a lithium halogenide represented by XI, wherein X has the same meaning as defined above.
    Type: Grant
    Filed: February 22, 1990
    Date of Patent: May 26, 1992
    Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
  • Patent number: 5103049
    Abstract: Process for the synthesis of perfluoroalkenyl-sulfonyl fluorides of formula:R.sub.f --CF.dbd.CF--SO.sub.2 Fwherein:R.sub.f is F or a perfluoroalkyl of from 1 to 9 carbon atoms, consisting in bringing a perfluoroalkyl-(sulfonyl fluoride) monofluoroacetyl-fluride of formula R.sub.f --CF.sub.2 --CF(COF)SO.sub.2 F into contact with a reactant constituted by a carbonate of a metal belonging to Groups IA, IIA and IIB of the Periodical Table of the Elements at a temperature comprised within the range of from 150.degree. to 400.degree. C., and then recovering the desired product.The process is run in continuous.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: April 7, 1992
    Assignee: Ausimont S.r.l.
    Inventors: Walter Navarrini, Darryl D. DesMarteau
  • Patent number: 5103051
    Abstract: A continuous process for preparing perfluoroalkenyl sulfonyl fluorides (I)R.sub.f --CF.dbd.CF--SO.sub.2 F (I)wherein R.sub.f is selected from the group consisting of F and a perfluoroalkyl of from 1 to 9 carbon atoms is disclosed, in which a perfluoroalkyl (sulfonyl fluoride) monofluoroacetyl fluoride of formulaR.sub.f --CF.sub.2 --CF(COF)SO.sub.2 F (II)is used as the starting product.The starting product is contacted with a reactant selected from the group consisting of the oxides of an element of the Groups IA, IIA, IIB, IIIA and IVA of the Periodic Table of the Elements, and of their mixtures, at a temperature comprised within the range of from 150.degree. to 450.degree. C., and the compound (I) is recovered from the reaction effluent.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: April 7, 1992
    Assignee: Ausimont S.r.l.
    Inventors: Walter Navarrini, Silvana Modena
  • Patent number: 5103050
    Abstract: A continuous process for preparing perfluoroalkenyl sulfonyl fluorides (I)R.sub.f --CF.dbd.CF--SO.sub.2 F (I)wherein: R.sub.f is selected from the group consisting of F and a perfluoroalkyl radical of from 1 to 9 carbon atoms is disclosed, in which as the starting compound a sultone (II) ##STR1## is used. The starting compound is placed into contact with a reactant selected from the group consisting of oxides and carbonates of an element of the Groups IA, IIA and IIB, and of the oxides of an element of the Groups IIIA and IVA of the Periodic Table of the Elements, and their mixtures, at a temperature comprised within the range of from 150.degree. to 450.degree. C., and the compound (I) is recovered from the reaction effluent. and the compound (I) is recovered from the reaction effluent.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: April 7, 1992
    Assignee: Ausimont S.r.l.
    Inventors: Walter Navarrini, Silvana Modena
  • Patent number: 4983747
    Abstract: Disclosed is a process for the preparation of a perfluoroorganic compound, which comprises fluorinating a partially fluorinated or unfluorinated organic compound having carbon-to-fluorine bonds under mild conditions and then, contacting the resulting reaction mixture with a fluorine gas at a temperature of 110.degree. to 180.degree. C.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: January 8, 1991
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
  • Patent number: 4962282
    Abstract: Preparation of fluorooxy-fluorosulfonyl-fluorocompounds by means of the direct fluorination with elemental fluorine of various .beta.-sultones according to the following reaction scheme: ##STR1## wherein R.sub.1 and R.sub.2, which can be either equal to, or different from, each other, represent a fluorine or chlorine atom, or an alkyl radical partially or totally halogenated with fluorine and/or chlorine.The reaction takes place in continuous in the presence of a fluorination catalyst, preferably constituted by an alkali-metal fluoride preferably supported on a metal material, at temperatures comprised within the range of from -30.degree. C. to +100.degree. C., and under the pressure comprised within the range of from 50 to 800 kPa; said catalyst is a fixed-bed catalyst, or is suspended in a reaction medium inert under the operating conditions.
    Type: Grant
    Filed: February 13, 1990
    Date of Patent: October 9, 1990
    Assignee: Ausimont S.r.l.
    Inventors: Antonio Marraccini, Gabriele Perego
  • Patent number: RE41184
    Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. Namely, the present invention provides a process which comprises reacting XSO2RA-E1 (1) with RB-E2 (2) to form XSO2RA-E-RB (3), then reacting (3) with fluorine in a liquid phase to form FSO2RAF-EF-RBF (4), and further, decomposing the compound to obtain FSO2RAF-EF1 (5), wherein RA is a bivalent organic group, E1 is a monovalent reactive group, RB is a monovalent organic group, E2 is a monovalent reactive group which is reactive with E1, E is a bivalent connecting group formed by the reaction of E1 with E2, RAF is a bivalent organic group formed by the fluorination of RA, etc., RBF is the same group as RB, etc., EF is a bivalent connecting group formed by the fluorination of E, etc.
    Type: Grant
    Filed: September 19, 2008
    Date of Patent: March 30, 2010
    Assignee: Asahi Glass Company, Limited
    Inventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa
  • Patent number: RE41357
    Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. Namely, the present invention provides a process which comprises reacting XSO2RA-E1 (1) with RB-E2 (2) to form XSO2RA-E-RB (3), then reacting (3) with fluorine in a liquid phase to form FSO2RAF-EF-RBF (4), and further, decomposing the compound to obtain FSO2RAF-EF1 (5), wherein RA is a bivalent organic group, E1 is a monovalent reactive group, RB is a monovalent organic group, E2 is a monovalent reactive group which is reactive with E1, E is a bivalent connecting group formed by the reaction of E1 with E2, RAF is a bivalent organic group formed by the fluorination of RA, etc., RBF is the same group as RB, etc., EF is a bivalent connecting group formed by the fluorination of E, etc.
    Type: Grant
    Filed: September 19, 2008
    Date of Patent: May 25, 2010
    Assignee: Asahi Glass Company, Limited
    Inventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa
  • Patent number: RE41806
    Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. Namely, the present invention provides a process which comprises reacting XSO2RA-E1 (1) with RB-E2 (2) to form XSO2R4-E-RB (3), then reacting (3) with fluorine in a liquid phase to form FSO2RAF-EF-RBF (4), and further, decomposing the compound to obtain FSO2RAF-EFl (5), wherein RA is a bivalent organic group, E1 is a monovalent reactive group, RB is a monovalent organic group, E2 is a monovalent reactive group which is reactive with E1, E is a bivalent connecting group formed by the reaction of E1 with E2, RAF is a bivalent organic group formed by the fluorination of RA, etc., RBF is the same group as RB, etc., EF1 is a bivalent connecting group formed by the fluorination of E, etc.
    Type: Grant
    Filed: June 19, 2007
    Date of Patent: October 5, 2010
    Assignee: Asahi Glass Company, Limited
    Inventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa