Carbon To Carbon Unsaturation Containing Patents (Class 568/685)
  • Patent number: 9024077
    Abstract: A fluorine-containing vinyl ether compound of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOCH?CH2 is produced by subjecting a fluorine-containing alcohol of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOH wherein n is an integer of 1 to 6, a is an integer of 1 to 4, b is an integer of 1 to 3, and c is an integer of 1 to 3, and 2-haloethyl vinyl ether of the formula: XCH2CH2OCH?CH2 to XCH2CH2OH-elimination reaction in the presence of a palladium-based catalyst and an aliphatic amine. The fluorine-containing vinyl ether compound contain a perfluoroalkyl group having 6 or less carbon atoms, which is said to have low bioaccumulation potential.
    Type: Grant
    Filed: August 24, 2011
    Date of Patent: May 5, 2015
    Assignee: Unimatec Co., Ltd.
    Inventors: Soichiro Murakami, Keisuke Kokin, Seiichiro Murata
  • Patent number: 8981162
    Abstract: Provided is a method for preparing fluorine-containing vinyl ether. The method comprises: carrying out hydrolytic neutralization on a small molecular weight byproduct which is produced in the process of preparing perfluoropolyether or a perfluorinated surfactant by photooxidation of fluorine-containing olefin; and obtaining fluorine-containing vinyl ether by drying and cracking. The byproduct produced in the process of preparing perfluoropolyether or the perfluorinated surfactant is utilized, thereby solving the emission problem of industrial wastes, reducing environment pollution, and generating available fluorine-containing vinyl ether.
    Type: Grant
    Filed: August 15, 2012
    Date of Patent: March 17, 2015
    Assignee: Zhonghao Chenguang Research Institute of Chemical Industry Company Limited
    Inventors: Ming Zhang, Xucang Yang, Xiaofeng Peng
  • Publication number: 20140330046
    Abstract: Provided is a method for preparing fluorine-containing vinyl ether. The method comprises: carrying out hydrolytic neutralization on a small molecular weight byproduct which is produced in the process of preparing perfluoropolyether or a perfluorinated surfactant by photooxidation of fluorine-containing olefin; and obtaining fluorine-containing vinyl ether by drying and cracking. The byproduct produced in the process of preparing perfluoropolyether or the perfluorinated surfactant is utilized, thereby solving the emission problem of industrial wastes, reducing environment pollution, and generating available fluorine-containing vinyl ether.
    Type: Application
    Filed: August 15, 2012
    Publication date: November 6, 2014
    Applicant: ZHONGHAO CHENGUANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY COMPANY LIMITED
    Inventors: Ming Zhang, Xucang Yang, Xiaofeng Peng
  • Publication number: 20140323672
    Abstract: Perfluoro-t-butoxyallyl ether and perfluoro-t-butoxypropargyl ether and methods for their synthesis are disclosed. Also disclosed are methods for making polymers from the perfluoro-t-butoxyallyl ether and perfluoro-t-butoxypropargyl ether.
    Type: Application
    Filed: April 24, 2014
    Publication date: October 30, 2014
    Inventors: Istvan T. HORVATH, K. C. Lau, Matthew Y. Lui, Edwin Law, Kwun Chung Paul Wong
  • Patent number: 8802899
    Abstract: A process for the manufacture of a perfluorovinylether by hydrodehalogenation of a halofluoroether (HFE) having general formula (I-A) or (I-B): wherein Rf represents a C1-C6 perfluoro(oxy)alkyl group; Rf?, Rf? and Rf??, equal to or different from each other, independently represent fluorine atoms or C1-C5 perfluoro(oxy)alkyl groups; X and X?, equal to or different from each other, are independently chosen among Cl, Br or I; Rf* and Rf*?, equal to or different from each other, independently represent fluorine atoms or C1-C3 perfluoro(oxy)alkyl groups; Y1 and Y2, equal to or different from each other, independently represent fluorine atoms or C1-C3 perfluoroalkyl groups. The process comprises contacting the halofluoroether (HFE) with hydrogen in the presence of a catalyst comprising at least one transition metal of group VIII B at a temperature of at most 340° C.
    Type: Grant
    Filed: June 4, 2009
    Date of Patent: August 12, 2014
    Assignee: Solvay Specialty Polymers Italy S.p.A.
    Inventors: Stefano Millefanti, Vito Tortelli, Giuseppe Marchionni
  • Publication number: 20130324769
    Abstract: The invention pertains to a process for the manufacture of a perfluorovinylether by hydrodehalogenation of a halofluoroether (HFE) having general formula (I-A) or (I-B): RfO—CRf?X—CRf?Rf??X???(I-A) wherein Rf represents a C1-C6 perfluoro(oxy)alkyl group; Rf?, Rf? and Rf??, equal or different from each other, independently represent fluorine atoms or C1-C5 perfluoro(oxy)alkyl groups; X and X?, equal or different from each other, are independently chosen among Cl, Br or I; wherein Rf* and Rf*?, equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoro(oxy)alkyl groups; Y1 and Y2, equal or different from each other, independently represent fluorine atoms or C1-C3 perfluoroalkyl groups; X and X? are as above defined; said process comprising contacting said halofluoroether (HFE) with hydrogen in the presence of a catalyst comprising palladium and at least one transition metal (M) selected from the group consisting of the metals of group VIIIB, other than palladium, and o
    Type: Application
    Filed: February 2, 2012
    Publication date: December 5, 2013
    Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Stefano Millefanti, Vito Tortelli, Giuseppe Marchionni, Stefania Albonetti, Manuel Gregori, Giuseppe Fornasari
  • Publication number: 20130178659
    Abstract: A fluorine-containing vinyl ether compound of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOCH?CH2 is produced by subjecting a fluorine-containing alcohol of the formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cOH wherein n is an integer of 1 to 6, a is an integer of 1 to 4, b is an integer of 1 to 3, and c is an integer of 1 to 3, and 2-haloethyl vinyl ether of the formula: XCH2CH2OCH?CH2 to XCH2CH2OH-elimination reaction in the presence of a palladium-based catalyst and an aliphatic amine. The fluorine-containing vinyl ether compound contain a perfluoroalkyl group having 6 or less carbon atoms, which is said to have low bioaccumulation potential.
    Type: Application
    Filed: August 24, 2011
    Publication date: July 11, 2013
    Applicant: Unimatec Co., Ltd.
    Inventors: Soichiro Murakami, Keisuke Kokin, Seiichiro Murata
  • Patent number: 8415439
    Abstract: The present invention provides an ETFE-type copolymer having a high melt tension and excellent blow moldability. An ethylene-tetrafluoroethylene copolymer which comprises ethylene units, tetrafluoroethylene units and units of a monomer (A) having at least two copolymerizable double bonds and which has a ratio (X/W) of its melt tension (XmN) to a load (Wkg) applied for the measurement of the melt tension being at least 0.8.
    Type: Grant
    Filed: April 13, 2010
    Date of Patent: April 9, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Shintaro Fukunaga, Atsushi Funaki
  • Publication number: 20110098512
    Abstract: A process for the manufacture of a perfluorovinylether by hydrodehalogenation of a halofluoroether (HFE) having general formula (I-A) or (I-B): wherein Rf represents a C1-C6 perfluoro(oxy)alkyl group; Rf?, Rf? and Rf??, equal to or different from each other, independently represent fluorine atoms or C1-C5 perfluoro(oxy)alkyl groups; X and X?, equal to or different from each other, are independently chosen among Cl, Br or I; Rf* and Rf*?, equal to or different from each other, independently represent fluorine atoms or C1-C3 perfluoro(oxy)alkyl groups; Y1 and Y2, equal to or different from each other, independently represent fluorine atoms or C1-C3 perfluoroalkyl groups. The process comprises contacting the halofluoroether (HFE) with hydrogen in the presence of a catalyst comprising at least one transition metal of group VIII B at a temperature of at most 340° C.
    Type: Application
    Filed: June 4, 2009
    Publication date: April 28, 2011
    Applicant: SOLVAY SOLEXIS S.P.A.
    Inventors: Stefano Millefanti, Vito Tortelli, Giuseppe Marchionni
  • Publication number: 20110082312
    Abstract: The present invention relates to a process for the preparation of compounds containing CF3O groups using compounds containing at least one group Y, in which Y=—Hal, —OSO2(CF2)zF, —OSO2CzH2z+1 (z=1-10), —OSO2F, —OSO2Cl, —OC(O)CF3— or —OSO2Ar, to a process for the preparation of compounds containing CF3O groups using KOCF3 and/or RbOCF3, and to novel compounds containing CF3O groups, and to the use thereof.
    Type: Application
    Filed: May 4, 2009
    Publication date: April 7, 2011
    Applicant: MERCK PATENT GESELLSCHAFT MIT DESCHRANKTER HAFTUNG
    Inventors: Nikolai (Mykola) Ignatyev, Wolfgang Hierse, Martin Seidel, Andreas Bathe, Jens Schroeter, Karsten Koppe, Thorsten Meier, Peter Barthen, Walter Frank
  • Publication number: 20110082313
    Abstract: Halogenated ?-fluoroethers (or bis-derivatives thereof) can be produced by reacting a halogenated hemiacetal (or bis-derivative thereof) with sulfuryl fluoride (S2F2) in the presence of an organic base. The reaction is conducted preferably in the presence of “a salt or complex of an organic base with hydrogen fluoride”, whereby the objective dehydroxyfluorination can proceed extremely favorably. It is still preferable to use as the starting substrate a halogenated hemiacetal prepared from fluoral or 3,3,3-trifluoropyruvic acid ester. Thus, industrially important halogenated ?-fluoroethers can be industrially produced with high selectivity and in high yield.
    Type: Application
    Filed: May 14, 2009
    Publication date: April 7, 2011
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Akihiro Ishii, Manabu Yasumoto
  • Publication number: 20100267995
    Abstract: A method for preparing a fluorinated vinyl ether compound comprising reacting a fluorinated ether substrate having (i) a hydrogen atom on a carbon atom that is alpha to an etheric oxygen and (ii) a fluorine atom on a carbon atom that is beta to the etheric oxygen, with an organolithium base to provide a reaction product comprising a fluorinated vinyl ether compound.
    Type: Application
    Filed: April 20, 2009
    Publication date: October 21, 2010
    Applicants: BAXTER INTERNATIONAL INC., BAXTER HEALTHCARE S.A.
    Inventors: Chialang Grand Huang, Linas V. Kudzma
  • Patent number: 7795477
    Abstract: A process for preparing perfluorovinylethers having general formula: RfO—CF?CF2??(IA) where Rf is a C1-C3 alkyl perfluorinated substituent, comprises the steps of: 1a) fluorinating olefins of formula: CY?Y?CY?Cl??(II) where Y, Y? and Y?, equal to or different from each other, are H, Cl, Br, and are not contemporaneously hydrogen; and obtaining fluorohalogencarbons of formula: FCY?Y—CY?ClF??(III) where Y, Y? and Y? are as above; 2a) dehalogenating or dehydrohalogenating fluorohalogencarbons (III) and obtaining fluorohalogenolefins of formula: FCYI?CYIIF??(IV) where YI and YII, equal to or different from each other, are H, Cl, Br and are not contemporaneously H; 3a) reacting a hypofluorite of formula RfOF and a fluorohalogenolefin (IV), and obtaining the fluorohalogenethers of formula: RfO—CFYI—CF2YII??(I) where YI, YII, equal to or different from each other, are Cl, Br, H and are not be contemporaneously H; and 4a) dehalogenating or dehydrohalogenating compounds (I) and obtaining perfluorov
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: September 14, 2010
    Assignee: Solvay Solexis S.p.A.
    Inventors: Vito Tortelli, Pierangelo Calini, Alberto Zompatori, Emanuela Antenucci
  • Publication number: 20100209600
    Abstract: Disclosed are compositions comprising a compound having the formula CF3(CF2)xCF?CFCF(OR)(CF2)yCF3, wherein R is CH3 or C2H5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=1, 2 or 3. Also disclosed are unsaturated fluoroethers selected from the group consisting of CF3(CF2)xCF?CFCF(OR)(CF2)yCF3, CF3(CF2)xC(OR)?CFCF2(CF2)yCF3, CF3CF?CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF?C(OR)CF2(CF2)yCF3, and mixtures thereof, wherein R can be either CH3, C2H5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=0, 1, 2 or 3. Also disclosed herein are novel methods of using a composition comprising at least one of the compounds described above as novel solvents, carrier fluids, dewatering agents, degreasing solvents or defluxing solvents.
    Type: Application
    Filed: February 8, 2010
    Publication date: August 19, 2010
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: JOAN ELLEN BARTELT, Robert D. Lousenberg
  • Publication number: 20100025619
    Abstract: Compounds of general formula (I) CxFy—O—CF?CFW wherein x is 1, 2, 3, 4, 5 or 6, y=2x+1, and wherein W is F, CF3, C2F5, C3F7, or formula (II), CxFy—O—CX?CYZ wherein x and y have the meaning given above, X stands for H or F, Y stands for H or F and Z stands for H, F. CF3 or C2F5 with the proviso that at least one of X, Y or Z are H and that not more than 2 hydrogen atoms are contained in the compound of general formula (II), are suitable as or part of refrigerants, solvents, blowing agents, fire extinguishants, ORC liquids, heat transformer liquids, heat pipe liquids or aerosol-producing gases. Preferred co-refrigerants are CF3I, HFC-134a or one or more pentafluoropropenes.
    Type: Application
    Filed: July 11, 2007
    Publication date: February 4, 2010
    Applicant: SOLVAY FLUOR GMBH
    Inventors: Marcello Riva, Christoph Meurer, Felix Flohr, Helge Rau
  • Patent number: 7612242
    Abstract: A process for preparing fluorovinylethers having general formula: RfO—CF?CF2??(IA) wherein Rf is a fluorinated or perfluorinated alkyl or cycloalkyl substituent; comprising the following reaction steps: 1) reaction of a hypofluorite; 2) dehalogenation or dehydrohalogenation of the fluorohalogenethers obtained in step 1) and obtainment of vinyl ethers; 3) fluorination with fluorine of the vinyl ethers and obtainment of fluorohalogenethers; and 4) dehydrohalogenation of the fluorohalogenethers and obtainment of the fluorovinylethers of formula (IV). The compounds of formula (IA) can be used, for example, in the preparation of various polymers, such as fluorinated elastomers and fluorinated thermoprocessable semicrystalline polymers.
    Type: Grant
    Filed: December 6, 2006
    Date of Patent: November 3, 2009
    Assignee: Solvay Solexis S.p.A.
    Inventors: Vito Tortelli, Pierangelo Calini, Alberto Zompatori, Emanuela Antenucci
  • Publication number: 20090124774
    Abstract: Disclosed herein are novel fluoroolefins of formula Rf-O—(CF2CF2)n(CH2CF2)m—CH?CH2, wherein n is 1 or 2, m is 0 or 1 and Rf is a C1-C8 fluoroalkyl or fluoroalkoxy group. The fluoroolefins may be oxidized to manufacture fluorinated carboxylic acids. Also disclosed are fluoropolymers comprising copolymerized units of the fluoroolefins of the invention and at least one other fluoromonomer.
    Type: Application
    Filed: October 14, 2008
    Publication date: May 14, 2009
    Inventors: Ming-Hong Hung, Sheng Peng
  • Patent number: 7531701
    Abstract: A process for the preparation of an allyloxytrifluoropropene derivative of the formula CF3CH?CR1(OCH2CR?CH2) wherein R1 is hydrogen, fluoro, or an allyloxy group represented by the formula —OCH2CR?CH2 wherein R is hydrogen or methyl including contacting (I) a compound represented by the formula CF3CH?CR2R3 wherein R2 is selected from the group consisting of hydrogen, chloro, and fluoro and wherein R3 is chloro or fluoro; and (ii) an allyl alcohol derivative of the formula HOCH2CR?CH2 wherein R is selected from the group consisting of: hydrogen and methyl; wherein the contacting is carried out in the presence of a base and optionally a solvent at a temperature and length of time sufficient to produce the allyloxytrifluoropropene derivative. A process for the preparation of polymers of the allyloxytrifluoropropene derivatives is also provided.
    Type: Grant
    Filed: September 10, 2007
    Date of Patent: May 12, 2009
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv R. Singh, Gregory J. Shafer
  • Patent number: 7465837
    Abstract: Fluorinated vinyl ethers are provided having the structure of formula (I) the structure of formula (I) wherein at least one of X and Y is a fluorine atom, and L, R1, R2, R3, R4 are as defined herein. Also provided are copolymers prepared by radical polymerization of (I) and a second monomer that may not be fluorinated. The polymers are useful in lithographic photoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, and are thus useful in DUV lithographic photoresist compositions. A method for using the composition to generate resist images on a substrate is also provided, i.e., in the manufacture of integrated circuits or the like.
    Type: Grant
    Filed: August 10, 2006
    Date of Patent: December 16, 2008
    Assignee: International Business Machines Corporation
    Inventors: Richard A. DiPietro, Hiroshi Ito
  • Patent number: 7319173
    Abstract: A process for preparing (per)fluorohalogenethers having general formula: wherein: A and A?, equal to our different from each other, are selected among Cl, Br, H; m=1, 2; n=0, 1; R1 is a fluorinated substituent, preferably perfluorinated, selected from the following groups: C1-C20 linear or branched alkylic; C3-C7 cycloalkylic; aromatic, C6-C10 arylalkyl; heterocyclic or C5-C10-alkylheterocyclic; preferably perfluoroalkyl; R? is as defined in the application; by reaction of carbonyl compounds having formula: wherein: R1 and n are as above; u=0, 1; R? is as defined in the application; in liquid phase, with elemental fluorine and with olefinic compounds of formula: CAF?CA?F2??(III) wherein A and A? are as above, at temperatures from ?120° C. to ?20° C., preferably from ?100° C. to ?40° C., optionally in the presence of an inert solvent under the reaction conditions.
    Type: Grant
    Filed: January 28, 2005
    Date of Patent: January 15, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Vito Tortelli, Stefano Millefanti, Pierangelo Calini
  • Publication number: 20070203368
    Abstract: A process for preparing perfluorovinylethers having general formula: RfO—CF?CF2 ??(IA) wherein Rf is a C1-C3 alkyl perfluorinated substituent; comprising the following steps: 1a) fluorination with fluorine of olefins of formula: CY?Y?CY?Cl ??(II) wherein Y, Y? and Y?, equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y? and Y? are not contemporaneously hydrogen; and obtainment of fluorohalogencarbons of formula: FCY?Y—CY?ClF ??(III) wherein Y, Y? and Y? are as above; 2a) dehalogenation or dehydrohalogenation of the fluorohalogencarbons (III) and obtainment of fluorohalogen olefins of formula: FCYI?CYIIF ??(IV) wherein YI and YII, equal to or different from each other, have the meaning of H, Cl, Br with the proviso that YI and YII are not both H; 3a) reaction between a hypofluorite of formula RfOF and a fluorohalogenolefin (IV), obtaining the fluorohalogenethers of formula: RfO—CFYI—CF2YII ??(I) wherein YI, YII, equal to or different from ea
    Type: Application
    Filed: December 11, 2006
    Publication date: August 30, 2007
    Inventors: Vito Tortelli, Pierangelo Calini, Alberto Zompatori, Emanuela Antenucci
  • Patent number: 7247757
    Abstract: A method of producing a fluorine-containing vinyl ether compound, which contains the step of: fluorinating a compound of formula (I-1) or (I-2): wherein R is a straight-chain, branched-chain or cyclic alkyl group that may have a substituent and/or an unsaturated bond; X11 is a halogen atom other than a fluorine atom; X12, X13, and X14 each independently are a halogen atom; X21 is a halogen atom other than a fluorine atom; and X22 and X23 each independently are a halogen atom.
    Type: Grant
    Filed: October 5, 2005
    Date of Patent: July 24, 2007
    Assignee: Fujifilm Corporation
    Inventors: Takayuki Ito, Yushi Kaneko
  • Publication number: 20070149827
    Abstract: A process for preparing fluorovinylethers having general formula: RfO—CF?CF2 ??(IA) wherein Rf is a fluorinated or perfluorinated alkyl or cycloalkyl substituent; comprising the following reaction steps: 1) reaction of a hypofluorite of formula RfOF, wherein Rf is as above, with an olefin of formula: CY?Y?CY?CI ??(II) wherein Y, Y? and Y?, equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y? and Y? are not contemporaneously hydrogen; 2) dehalogenation or dehydrohalogenation of the fluorohalogenethers obtained in step 1) and obtainment of vinyl ethers of formula: RfO—CYI?CYIIF ??(IV) wherein YI and YII, equal to or different from each other, have the meaning of H, Cl, Br with the proviso that YI and YII are not both H; 3) fluorination with fluorine of the vinyl ethers (IV) and obtainment of fluorohalogenethers of formula: RfO—CFYI—CF2YII ??(I) wherein YI, YII, equal to or different from each other, are Cl, Br, H with the proviso that YI and YII
    Type: Application
    Filed: December 6, 2006
    Publication date: June 28, 2007
    Inventors: Vito Tortelli, Pierangelo Calini, Alberto Zompatori, Emanuela Antenucci
  • 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: 7102031
    Abstract: It is an object to obtain from a mixture of a specific diene compound (1) and a compound (2) with the same molecular weight and molecular formula hard to separate by distillation, the diene compound (1) in high purity without using any special reagent or complicated technique. Namely, the present invention provides a method of inducing the Claisen rearrangement reaction of the compound (2) in a mixture containing CR1R2?CR3CFR4CR5R6OCR7?CR8R9 (1) and CFR1R2CR3?CR4CR5R6OCR7?CR8R9 (2), and separating the diene compound (1) from a Claisen rearrangement reaction product; or converting the Claisen rearrangement reaction product into a derivative and then separating the diene compound (1) from the derivative of the Claisen rearrangement reaction product. Wherein, R1 to R9 each represent a fluorine atom or the like.
    Type: Grant
    Filed: June 10, 2004
    Date of Patent: September 5, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Masao Iwaya, Hidekazu Okamoto, Kazuya Oharu
  • Patent number: 7053237
    Abstract: A process for producing a fluorinated ester through a small number of steps, is presented. The process for producing a fluorinated ester, comprises a transesterification step in which RAF—COOCF2—RAF and RA—CH2OH are subjected to a transesterification reaction to obtain RAF—COOCH2—RA, and a fluorination step in which the obtained compound is fluorinated to obtain a reaction product containing RAF—COOCF2—RAF. Here, in the formulae, RA is a monovalent organic group, and RAF is the same group as RA or a monovalent organic group obtained by fluorination of RA.
    Type: Grant
    Filed: July 16, 2003
    Date of Patent: May 30, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi, Masakuni Sato, Masahiro Ito, Koichi Yanase, Yasuhiro Suzuki
  • Patent number: 6849194
    Abstract: Highly fluorinated, saturated, and unsaturated fluoroethers are efficient, economical, non-ozone-depleting fire extinguishing agents used alone or in blends with other fire extinguishing agents in total flooding and portable systems. Methods for producing ethers, halogenated ether intermediates, and fluoroethers are disclosed. Novel fluoroether compositions are disclosed. Fluoroether extinguishing mixtures, methods, and systems are disclosed.
    Type: Grant
    Filed: May 12, 2003
    Date of Patent: February 1, 2005
    Assignee: PCBU Services, Inc.
    Inventors: Mark Robin, Thomas F. Rowland, John Chien, Janet Boggs, Mitchel Cohn, Vicki Hedrick, Stephan Brandstadter
  • Patent number: 6756458
    Abstract: A novel polymer useful as an optical resin material excellent in heat resistance, a novel monomer for obtaining the polymer, etc., are provided. A fluorinated diene represented by CF2═CF(CF2)nC(CF3)ROCF═CF2 (wherein R is a fluorine atom or a trifluoromethyl group, and n is an integer of from 1 to 3), and a polymer thereof.
    Type: Grant
    Filed: December 2, 2002
    Date of Patent: June 29, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Kimiaki Kashiwagi, Gen Ogawa, Masakuni Sato, Kazuya Oharu, Isamu Kaneko, Norihide Sugiyama, Shin Tatematsu
  • Patent number: 6670511
    Abstract: A fluorine-containing diene represented by the formula 1: CF2═CF(CF2)nCXYOCF═CF2  Formula 1 wherein each of X and Y which are independent of each other, is an atom selected from a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, provided that X and Y are not simultaneously hydrogen atoms or fluorine atoms, and n is an integer of from 1 to 3.
    Type: Grant
    Filed: May 15, 2002
    Date of Patent: December 30, 2003
    Assignee: Asahi Glass Company Limited
    Inventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
  • Patent number: 6653511
    Abstract: A perfluoropolyether and a composition comprising the perfluoropolyether are provided in which the perfluoropolyether comprises at least one bromine or iodine atom at the primary position of the perfluoropolyether. Also provided is a process for producing the composition in which the process comprises contacting a perfluoropolyether acid fluoride moiety with a metal bromide or metal iodide or a suitable polyether secondary iodide under a condition sufficient to effect the production of a perfluoropolyether comprising at least one bromine or iodine at the primary position.
    Type: Grant
    Filed: September 9, 2002
    Date of Patent: November 25, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Jon L. Howell, Erik W. Perez, Alfred Waterfeld, Chadron Mark Friesen, Joseph Stuart Thrasher, Ireneusz Nowak
  • Patent number: 6559268
    Abstract: A perfluoro group-containing compound are represented by the following formula (I): —Rf— is a perfluoro group; and —A represents —OH or a group: or —CyF2y+1 or —CzF2z−1 and a perfluoro group-containing polymerizable compound represented by the following formula (II): R1—O—CH2—CH(OH)—CH2—O—Rf—B  (II) In Formula (II), —Rf— is a perfluoro group; —B is —OH or —O—CH2—CH(OH)—CH2—O—R2, or —CyF2y+1 or —CzF2z−1; and R1 and R2 each is a dehydroxyl residue of a (meth)acryloyl group-containing compound or a vinyl group-containing compound. The hardened polymer from the compound has water-repellency, oil-repellency and adhering ability.
    Type: Grant
    Filed: March 17, 2000
    Date of Patent: May 6, 2003
    Assignee: Kyoeisha Chemcial Co., Ltd.
    Inventors: Junichi Ikeda, Hajimu Kawa
  • Patent number: 6448452
    Abstract: A polymer which contains monomer units formed by polymerization of a fluorine-containing diene of formula 1: CF2═CF(CF2)nCXYOCF═CF2 Wherein X and Y are hydrogen and chlorine, hydrogen and-bromine, hydrogen and iodine, fluorine and chlorine, fluorine and bromine, fluorine and iodine, chlorine and bromine, chlorine and iodine, bromine and bromine, bromine and iodine, or iodine and iodine and n is an integer from 1 to 3.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: September 10, 2002
    Assignee: Asahi Glass Company Limited
    Inventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
  • Patent number: 6300526
    Abstract: Hydro-2,2-difluoroalkylvinylethers having the formula CF2═CH—O—RA  (I) wherein RA is a radical containing fluorine, optionally containing halogens such as Cl, Br, I, hydrogen, functional groups CM, COOR′, CON(R′)2, SO2OR′, m wherein R′ is a C1-C5 alkyl, RA being selected from the following: a linear or branched, saturated or unsaturated C2-C20 fluoroalkyl, or a saturated or unsaturated C4-C6 fluorinated cyclic group wherein optionally from 1 to 2 carbon atoms are substituted with oxygen atoms, or a linear, branched saturated or unsaturated, C3-C15 fluorooxyalkyl group, containing one or Core oxygen atoms.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: October 9, 2001
    Assignee: Austmont S.p.A.
    Inventors: Walter Navarrini, Antonio Russo
  • Patent number: 6255535
    Abstract: The present invention describes a novel process for the preparation of perfluoro allyl ethers. The process involves providing a hydrogen-containing precursor comprising at least one 1,2-dichloro alkyl ether moiety, fluorinating the precursor to provide a perfluorinated intermediate, and dechlorinating the perfluorinated intermediate to the corresponding perfluorinated ether. A reaction product of a perfluorinated olefin and an allyl ether may also be used as a precursor. Such a reaction product is chlorinated before the fluorination step. Perfluoro vinyl or allyl ethers may be used in place of the perfluorinated olefin. Novel perfluoro alkoxy compounds are also described.
    Type: Grant
    Filed: December 22, 1999
    Date of Patent: July 3, 2001
    Assignees: Dyneon LLC, 3M Innovative Properties Company
    Inventors: Jay F. Schulz, George G. I. Moore, Werner Schwertfeger, Klaus Hintzer, Zai-Ming Qiu, Miguel A. Guerra, Erik D. Hare, Allan T. Worm
  • Patent number: 6255536
    Abstract: The present invention describes a novel process for the preparation of perfluorovinyl ethers. The process involves providing a hydrocarbon precursor that may be partially halogenated, fluorinating the precursor to provide a perfluorinated intermediate, and converting the perfluorinated intermediate to the desired perfluorinated ether. Novel perfluorovinyl ethers are also provided.
    Type: Grant
    Filed: December 22, 1999
    Date of Patent: July 3, 2001
    Assignees: Dyneon LLC, 3M Innovative Properties Company
    Inventors: Allan T. Worm, George G. I. Moore, Miguel A. Guerra, Werner Schwertfeger, Klaus Hintzer, Zai-Ming Qiu, Erik D. Hare
  • Patent number: 6245949
    Abstract: A method for fluoromethylating halogenated alcohols. The method includes the step of providing an alpha-halogenated alcohol of the formula R1C(CX3)2OH, wherein R1 is selected from the group consisting of hydrogen and alkyl groups. The alpha-halogenated alcohol is reacted with a first compound of the formula CH2(OR2)2 in the presence of an acid catalyst to form an acetal. The resulting acetal is then chlorinated with a chlorinating agent to form a chloride compound of the formula R1C(CX3)2OCH2Cl. The chloride compound is then converted to a fluoride compound of the formula R1C(CX3)2OCH2F using a fluorinating agent.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: June 12, 2001
    Assignee: Abbott Laboratories
    Inventors: Christopher Bieniarz, Kornepati V. Ramakrishna
  • Patent number: 6198009
    Abstract: Perfluoropropylvinylether (FPVE) purification process with C1-C10 alcohols or mixtures thereof.
    Type: Grant
    Filed: April 2, 1999
    Date of Patent: March 6, 2001
    Assignee: Ausimont S.p.A.
    Inventors: John W. Blanke, Julio A. Abusleme
  • 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: 6025521
    Abstract: This invention relates to carbon based initiators for polymerization and telomerization reactions. Polymers produced are useful as water repellants and materials with high temperature resistance. Telomers are useful as intermediates in the production of chemically inert and temperature resistant materials.
    Type: Grant
    Filed: May 9, 1997
    Date of Patent: February 15, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Carl George Krespan, Viacheslav Alexandrovich Petrov
  • Patent number: 6023002
    Abstract: Described is a reaction of a fluorinated alkoxide with an alkyl fluorovinylalkyl ether, the alkyl fluorovinylalkyl ether having alpha-beta carbon-carbon unsaturation relative to the ether oxygen, to produce a hydrofluoroether.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: February 8, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Frederick E. Behr, Yuri Cheburkov
  • Patent number: 5834612
    Abstract: A fluorine-containing organic compound of the following formula (1):R.sup.f CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2 ( 1)wherein R.sup.f is a C.sub.1-20 fluoroalkyl group.
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: November 10, 1998
    Assignees: Asahi Glass Company Ltd., OSI Specialties, Inc.
    Inventors: Yutaka Furukawa, Seisaku Kumai, Jeffery A. Cooke, Gerald J. Murphy, George A. Policello
  • Patent number: 5777179
    Abstract: A process for the production of perfluoromethyl perfluorovinyl ether (PMVE) and perfluoroethyl perfluorovinyl ether (PEVE) from hexafluoropropylene epoxide (HFPO) and a mixture comprising carbonyl fluoride (CF) and perfluoroacetyl fluoride (PAF) is disclosed. The process includes a step (a) involving the reaction of hexafluoropropylene epoxide (HFPO) with a mixture of carbonyl fluoride (CF) and perfluoroacetyl fluoride (PAF) to produce a mixture of 2,3,3,3-tetrafluoro-2-(trifluoromethoxy)propionic acid fluoride (PMPF) and 2,3,3,3-tetrafluoro-2-(pentafluoroethoxy)propionic acid fluoride (PEPF). In a second step, a mixture of PMPF and PEPF made in the step (a) is dehalocarbonylated to produce a mixture of PMVE and PEVE.
    Type: Grant
    Filed: May 24, 1996
    Date of Patent: July 7, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Baishen Liang, Ming-Hong Hung, Paul Raphael Resnick
  • Patent number: 5650544
    Abstract: The present invention provides a process for producing an unsaturated ether, which comprises subjecting a glycol ether to intramolecular dehydration in a gas phase in the presence of a catalyst to convert the glycol ether into an unsaturated ether directly in a one-step reaction. As the catalyst, an oxide containing, for example, silicon and an alkali metal is used. The process, which uses no auxiliary raw material, can produce an unsaturated ether (a vinyl ether and/or an allyl ether) simply and safely without generating any waste material derived from the auxiliary raw material.
    Type: Grant
    Filed: September 15, 1995
    Date of Patent: July 22, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kimio Ariyoshi, Yuuji Shimasaki
  • Patent number: 5648560
    Abstract: A process for preparing perhaloethers from perhaloolefins by reacting at least one fluorooxy compound R.sub.x --OF, wherein R.sub.x is a perhaloalkyl radical, with a perfluoroolefin in a liquid phase, optionally containing an organic solvent inert to the perfluoroolefin, while maintaining the temperature of the liquid phase in the range of -30.degree. to -120.degree. C. The process includes continuously feeding to the liquid phase a stream of an inert gas and a gaseous stream of the fluorooxy compound.
    Type: Grant
    Filed: December 9, 1994
    Date of Patent: July 15, 1997
    Assignee: Ausimont S.p.A.
    Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani, Walter Navarrini
  • Patent number: 5453549
    Abstract: An extremely reactive and highly copolymerizable hexafluoropropylene oxide oligoether derivative, to give bi- or ter-polymers with fluoroolefins and perfluoroalkyl vinyl ethers, which is represented by general formula: ##STR1## wherein X is a fluorine atom or trifluoromethyl group; and n is an integer of 2-5.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: September 26, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Noriyuki Koike, Kouichi Yamaguchi, Hiromasa Yamaguchi, Kouji Takano
  • Patent number: 5401886
    Abstract: Disclosed herein is a partially fluorinated polymer containing cyclic units. The polymer is particularly useful in for coatings and encapsulants. Also disclosed herein is the novel monomer from which the polymer is made, and a novel intermediate for that monomer.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: March 28, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Zhen-Yu Yang
  • Patent number: 5399779
    Abstract: Perfluoro-2-methyl-4-methoxypentane is prepared with high selectivity by reacting perfluoro-4-methyl-2-pentene with CF.sub.3 OF at a temperature ranging from -40.degree. to +50.degree.. The reaction is preferably carried out by continuously bubbling a gaseous CF.sub.3 OF flow into a liquid phase consisting of the abovesaid pentene optionally dissolved in a solvent.
    Type: Grant
    Filed: September 15, 1993
    Date of Patent: March 21, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Vito Tortelli, Claudio Tonelli, Walter Navarrini, Simonetta Fontana
  • Patent number: 5391796
    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: August 12, 1993
    Date of Patent: February 21, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5350497
    Abstract: Disclosed herein is a process for making perfluoro(alkyl vinyl ethers) by fluorination with elemental fluorine of selected novel partially fluorinated (di)chloroethyl ethers, followed by dehalogenation to the corresponding perfluoro(alkyl vinyl ether). The perfluoro(alkyl vinyl ethers) are useful as monomers for molding resins and elastomers.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: September 27, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Shlomo Rozen
  • Patent number: RE35568
    Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine .[.group.]. in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and .Iadd.halogenated .Iaddend.alkoxy-substituted .[.halogenated.]. aliphatic groups, wherein the method comprises the step of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: July 22, 1997
    Assignee: Ohmeda Pharmaceutical Products Division Inc.
    Inventors: Donald F. Halpern, Mark L. Robin