Five Or More Fluorine Atoms Patents (Class 526/253)
  • Patent number: 9034997
    Abstract: Provided is a fluorine- and epoxy group-containing copolymer with excellent workability at room temperature, high water-repellency, and excellent characteristics as a water vapor barrier. Also provided is an efficient method for producing said copolymer. The fluorine and epoxy group-containing copolymer is characterized by containing at least a monomer unit represented by general formula (1): {Therein, R1-R10 each independently represent an alkyl group having 1-3 carbon atoms or a hydrogen atom, R11 is a hydrogen atom, methyl group, or phenyl group, and R5 or R6 can be linked with R7 or R8 to form a ring.} and a monomer unit represented by general formula (2): {Therein, R12 and R13 each independently represent a hydrogen atom or a fluorine atom; R14 represents a hydrogen atom, fluorine atom, methyl group or trifluoromethyl group, and R15 represents a flourine atom or perfluoro group having at most 12 carbon atoms}.
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: May 19, 2015
    Assignee: Showa Denko K.K.
    Inventors: Hiroshi Uchida, Masanao Hara
  • Patent number: 9029464
    Abstract: Perfluoroelastomeric gel having the following properties: appearance: transparent gelatinous solid; water content between 10% and 90% by weight; density between 1.1 and 2.1 g/cm3; said gel satisfies the following test: dried in a stove at 90° C. until a constant weight gives curable perfluoroelastomers.
    Type: Grant
    Filed: June 19, 2013
    Date of Patent: May 12, 2015
    Assignee: Solvay Solexis S.p.A.
    Inventors: Stefano Arrigoni, Marco Apostolo, Margherita Albano
  • Patent number: 9023963
    Abstract: A method of producing a fluoropolymer by which a melt-processable fluoropolymer (A) having a specific unstable terminal group or groups (P) is subjected to melt-kneading in a kneader having a stabilization treatment zone to thereby produce a fluoro-polymer (B) resulting from conversion of the specific unstable terminal group or groups (P) to —CF2H. The specific unstable terminal group or groups (P) include alkoxycarbonyl groups, fluoroalkoxycarbonyl groups and/or carboxyl group quaternary nitrogen compound salts, the melt-kneading is carried out in the absence or presence of an alkali metal element or alkaline earth metal element, the content of the alkali metal element or alkaline earth metal element is not greater than 2 ppm of the composition under melt-kneading, and the melt-kneading in the stabilization treatment zone is carried out in the presence of water. A fluoro-polymerized material is also disclosed.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: May 5, 2015
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshiyuki Takase, Kenji Ishii, Shouji Fukuoka
  • Publication number: 20150110984
    Abstract: An object of the present invention it to provide a novel fluororesin that has excellent mechanical strength and chemical resistance, and very low permeability at high temperature. The fluorine resin a copolymer that includes copolymerized units derived from tetrafluoroethylene, vinylidene fluoride, and an ethylenically unsaturated monomer other than tetrafluoroethylene and vinylidene fluoride. The fluororesin has a storage modulus E?, as measured at 170° C. by a dynamic viscoelasticity analysis, in the range of 60 to 400 MPa.
    Type: Application
    Filed: December 23, 2014
    Publication date: April 23, 2015
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Takahiro KITAHARA, Takuma KAWABE
  • Patent number: 8997797
    Abstract: An object of the present invention it to provide a novel fluororesin that has excellent mechanical strength and chemical resistance, and very low permeability at high temperature. The fluorine resin a copolymer that includes copolymerized units derived from tetrafluoroethylene, vinylidene fluoride, and an ethylenically unsaturated monomer other than tetrafluoroethylene and vinylidene fluoride. The fluororesin has a storage modulus E?, as measured at 170° C. by a dynamic viscoelasticity analysis, in the range of 60 to 400 MPa.
    Type: Grant
    Filed: March 16, 2010
    Date of Patent: April 7, 2015
    Assignee: Daikin Industries, Ltd.
    Inventors: Takahiro Kitahara, Takuma Kawabe
  • Patent number: 8906821
    Abstract: A catalyst composition comprising a cation and an anion of the formula Anq?Qpm+, wherein m, n, p, and q are positive integers, wherein m*p=n*q, wherein Qm+is an organo onium, and Aq?is an anion, provided that at least one Aq?is selected from the formula (I) wherein each R independently is H, halo, alkyl, aryl, aralkyl, or cycloalkyl, and which also may be halogenated, fluorinated, or perfluorinated, wherein two or more of R and R? groups may together form a ring, wherein each R group independently may contain one or more heteroatom(s), wherein R? can be the same as R, with the proviso that R? cannot be halo, and wherein the catalyst composition is essentially free of hydrocarbon containing alcohol. Also provided are a fluoropolymer composition including this curative, a method of making a fluoropolymer, and fluoropolymer articles containing curable or cured fluoropolymer compositions.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: December 9, 2014
    Assignee: 3M Innovative Properties Company
    Inventors: Werner M. A. Grootaert, Kim M. Vogel, Dennis E. Vogel
  • Publication number: 20140335634
    Abstract: A mold release film, which is adapted to be disposed on the cavity surface of a mold to form a resin-encapsulated portion by encapsulating a semiconductor element of a semiconductor device with a curable encapsulation resin, has a tensile modulus of elasticity of from 10 to 24 MPa at 132° C. as measured in accordance with JIS K 7127, and a peak peel resistance of at most 0.8 N/25 mm.
    Type: Application
    Filed: July 29, 2014
    Publication date: November 13, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Wataru KASAI, Yoshiaki HIGUCHI, Masakazu ATAKU, Daisuke TAGUCHI, Satoshi OTSUGU
  • Patent number: 8883313
    Abstract: The present invention provides a polytetrafluoroethylene powder having moldability/processability as well as electrical characteristics in microwave bands. The present invention is a modified polytetrafluoroethylene powder which has (1) a dielectric loss tangent at 12 GHz of not higher than 2.0×10?4 and (2) a cylinder extrusion pressure of not higher than 45 MPa at a reduction ratio of 1600.
    Type: Grant
    Filed: April 4, 2005
    Date of Patent: November 11, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshinori Nanba, Yasuhiko Sawada, Shunji Kasai, Shuji Tagashira, Makoto Ono, Takahiro Taira, Hiroyuki Yoshimoto
  • Patent number: 8877870
    Abstract: A fluorinated elastic copolymer which has iodine atoms, bromine atoms, or both iodine and bromine atoms, at its molecular terminals and which includes repeating units (a) based on tetrafluoroethylene, repeating units (b) based on a fluorinated monomer having one polymerizable unsaturated bond (provided that tetrafluoroethylene is excluded), and repeating units (c) based on a fluorinated monomer having at least two polymerizable unsaturated bonds, wherein the ratio (molar ratio) of the repeating units (a) to the repeating units (b) is (a)/(b)=40/60 to 90/10, and the proportion of the repeating units (c) based on the total amount of the repeating units (a) and the repeating units (b) is from 0.01 to 1 mol %.
    Type: Grant
    Filed: July 15, 2011
    Date of Patent: November 4, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Hiroshi Funaki, Kunio Watanabe, Keigo Matsuura, Ng Soon Yeng
  • Patent number: 8835094
    Abstract: Fluoroalcohol compounds of formula (1) are useful in producing polymers which are used as the base resin to formulate radiation-sensitive resist compositions having transparency to radiation having a wavelength of up to 500 nm and improved development characteristics. R1 is hydrogen or a monovalent C1-C20 hydrocarbon group in which any constituent —CH2— moiety may be replaced by —O— or —C(?O)—, Aa is a (k1+1)-valent C1-C20 hydrocarbon or fluorinated hydrocarbon group, and k1 is 1, 2 or 3.
    Type: Grant
    Filed: September 19, 2011
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Takeru Watanabe, Tomohiro Kobayashi, Takeshi Kinsho
  • Patent number: 8829132
    Abstract: To provide an ethylene/tetrafluoroethylene copolymer which is excellent in heat resistance and flexibility. An ethylene/tetrafluoroethylene copolymer comprising repeating units (A) based on tetrafluoroethylene and repeating units (B) based on ethylene in a ratio of repeating units (A)/repeating units (B)=66/34 to 75/25 (molar ratio) and as an optional component, repeating units (C) based on a monomer represented by CH2?CX(CF2)nY (wherein each of X and Y which are independent of each other is a hydrogen atom or a fluorine atom, and n is from 2 to 8) in an amount of from 0 to 1 mol % based on the total number of moles of the repeating units (A) based on tetrafluoroethylene and the repeating units (B) based on ethylene, and having a volume flow rate measured at 297° C. of from 4 to 1,000 mm3/sec and an elastic modulus of at most 500 MPa.
    Type: Grant
    Filed: January 11, 2012
    Date of Patent: September 9, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Daisuke Taguchi, Shigeru Aida
  • Patent number: 8829087
    Abstract: Embodiments in accordance with the present invention provide polymers for forming layers/films useful in the manufacture of a variety of types of optoelectronic displays. Such embodiments also provide compositions of such polymers for forming such layers/films where the formed layers/films have high transparency over the visible light spectrum.
    Type: Grant
    Filed: December 9, 2011
    Date of Patent: September 9, 2014
    Assignees: Promerus, LLC, Sumitomo Bakelite Co., Ltd.
    Inventors: Osamu Onishi, Larry F. Rhodes, Nobuo Tagashira
  • Patent number: 8815490
    Abstract: The radiation-sensitive resin composition includes a first polymer, a second polymer and a radiation sensitive acid generator. The first polymer includes a repeating unit represented by formula (1). The second polymer includes an acid labile group and is dissociated by an action of acid so that alkali solubility is given by dissociation of said acid labile group. R1 represents a hydrogen atom, a methyl group or a trifluoromethyl group. R2 represents a single bond or a divalent linear, branched or cyclic, saturated or unsaturated hydrocarbon group having 1-20 carbon atoms. X represents a fluorine atom-substituted methylene group or a linear or branched fluoroalkylene group having 2-20 carbon atoms. R3 represents a hydrogen atom or a monovalent organic group.
    Type: Grant
    Filed: December 2, 2011
    Date of Patent: August 26, 2014
    Assignee: JSR Corporation
    Inventors: Yasuhiko Matsuda, Tomohisa Fujisawa, Yukari Hama, Takanori Kawakami
  • Patent number: 8785580
    Abstract: The invention relates to a polyvinylidene fluoride polymer having an ultra-high molecular weight, and unexpected physical properties. The ultra-high molecular weight polymer is clear, has a lower melting point, reduced crystallinity, excellent impact resistance, and a high elongation at the yield point. The ultra-high molecular weight polyvinylidene fluoride can be alone, or blended with other polymers, in final applications and articles.
    Type: Grant
    Filed: June 26, 2007
    Date of Patent: July 22, 2014
    Assignee: Arkema Inc.
    Inventor: Ramin Amin-Sanayei
  • Patent number: 8722809
    Abstract: The present invention provides a preparation process for converting to a vinylidene fluoride elastomer having a group having sulfinic acid, sulfinic acid derivative, sulfonic acid or sulfonic acid derivative at one end or both ends of its trunk chain, and the preparation process provides a vinylidene fluoride elastomer having, at one end or both ends of its trunk chain, end groups represented by the formula: —CR1R2—CR3R4—SO2H, wherein R1 to R4 may be the same or different and each is hydrogen atom or fluorine atom, by allowing a vinylidene fluoride elastomer having, at one end or both ends of its trunk chain, end groups represented by the formula: —CR1R2—CR3R4—X1, wherein R1 to R4 are as defined above, X1 is bromine atom or iodine atom, to react with a sulfur compound represented by the formula: (M1)nH2-nS2O4, wherein M1 is a monovalent or divalent metal ion or ammonium ion, n is an integer of 0 to 2.
    Type: Grant
    Filed: January 20, 2009
    Date of Patent: May 13, 2014
    Assignees: The University of Tokyo, Daikin Industries, Ltd.
    Inventors: Yuzo Komatsu, Haruhiko Mohri, Hirokazu Aoyama, Takanori Fukushima, Takuzo Aida
  • Patent number: 8637144
    Abstract: A process for the polymerization of a true tetrafluoroethylene (TFE) copolymer of the fine powder type is provided, wherein the copolymer contains polymerized comonomer units of at least one comonomer other than TFE in concentrations of at least or exceeding 1.0 weight percent, and which can exceed 5.0 weight percent, wherein the copolymer is expandable, that is, the copolymer may be expanded to produce strong, useful, expanded TFE copolymeric articles having a microstructure of nodes interconnected by fibrils.
    Type: Grant
    Filed: October 4, 2007
    Date of Patent: January 28, 2014
    Assignee: W. L. Gore & Associates, Inc.
    Inventor: Lawrence A. Ford
  • Patent number: 8557939
    Abstract: To provide an antifouling composition which is a fluorine-type antifouling composition using a short chain perfluoroalkyl group and which is excellent in antifouling properties and water/oil repellency and presents good durability against washing. An antifouling composition comprising a fluorocopolymer which comprises from 30 to 65 mass % of polymerized units (a) having a C1-6 perfluoroalkyl group, from 1 to 67 mass % of polymerized units (b1) having —(C2H4O)— and from 3 to 34 mass % of polymerized units (b2) having —(C4H8O)—, wherein the content of —(C2H4O)— is from 20 to 65 mass %, and the content of —(C4H8O)— is from 2 to 13 mass %.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: October 15, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Hiroyuki Hara, Shuichiro Sugimoto, Takao Hirono, Takashige Maekawa
  • Publication number: 20130188293
    Abstract: Provided is a film for a film capacitor in which electrical insulation, and especially electrical properties at high temperatures are improved while a high dielectric constant of a vinylidene fluoride resin is maintained. The film for a film capacitor includes a tetrafluoroethylene resin (a1) that includes a vinylidene fluoride unit and a tetrafluoroethylene unit in the vinylidene fluoride unit/tetrafluoroethylene unit ratio (mol %) of 0/100 to 49/51 as a film-forming resin (A).
    Type: Application
    Filed: September 21, 2011
    Publication date: July 25, 2013
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Meiten Koh, Eri Mukai, Nobuyuki Komatsu, Kouji Yokotani, Mayuko Tatemichi, Kakeru Hanabusa, Takahiro Kitahara, Takuma Kawabe
  • Patent number: 8481661
    Abstract: A noncrystalline fluoroelastomer which is a copolymer consisting essentially of vinylidene fluoride and a fluoromonomer represented by the general formula (1): CH2?CFRf??(1) wherein Rf is a straight or branched fluoroalkyl group containing 1 to 12 carbon atoms, and has a vinylidene fluoride units/fluoromonomer units mol ratio of 78/22 to 22/78 and a glass transition temperature of not higher than 25° C.
    Type: Grant
    Filed: March 5, 2010
    Date of Patent: July 9, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Shigeru Morita, Masanori Kitaichi, Shouji Fukuoka, Daisuke Ota
  • Patent number: 8378063
    Abstract: A process for producing fluoropolymer particles includes preparing a solution/dispersion containing fluoropolymer dissolved/dispersed in a first solvent such that the swelling of fluoropolymer by the first solvent is from 50 to 1,200%, and mixing the solution/dispersion with a second solvent such that fluoropolymer forms particles and the swelling of fluoropolymer by the mixture of the first and second solvents is from 0 to 100%. WC/WB is in the range of from 1 to 5, WB represents mass of the first solvent, WC/ represents mass of the second solvent, WC/WB represents a ratio of the mass of the second solvent to the mass of the first solvent. SBC/SB is at most 0.5. SBC represents the swelling by the mixture of the first and second solvents, SB represents the swelling by the first solvent, and SBC/SB represents a ratio of the swelling by the mixture to the swelling by the first solvent.
    Type: Grant
    Filed: December 22, 2009
    Date of Patent: February 19, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Susumu Saito, Tetsuji Shimohira, Takashi Saeki, Junichi Tayanagi
  • Publication number: 20130035461
    Abstract: Provided is a fluorine- and epoxy group-containing copolymer with excellent workability at room temperature, high water-repellency, and excellent characteristics as a water vapor barrier. Also provided is an efficient method for producing said copolymer. The fluorine and epoxy group-containing copolymer is characterized by containing at least a monomer unit represented by general formula (1): {Therein, R1-R10 each independently represent an alkyl group having 1-3 carbon atoms or a hydrogen atom, R11 is a hydrogen atom, methyl group, or phenyl group, and R5 or R6 can be linked with R7 or R8 to form a ring.} and a monomer unit represented by general formula (2): {Therein, R12 and R13 each independently represent a hydrogen atom or a fluorine atom; R14 represents a hydrogen atom, fluorine atom, methyl group or trifluoromethyl group, and R15 represents a flourine atom or perfluoro group having at most 12 carbon atoms.
    Type: Application
    Filed: May 19, 2011
    Publication date: February 7, 2013
    Applicant: SHOWA DENKO K.K.
    Inventors: Hiroshi Uchida, Masanao Hara
  • Patent number: 8362167
    Abstract: The invention provides a compound and tautomeric forms thereof having the formula: wherein Rf1 is selected from the group consisting of hydrogen, a straight chain, branched secondary or branched tertiary C1-C20 perfluoroalkyl group optionally containing ether or thioether linkages and C1-C10 perfluoroalicyclic group optionally containing ether or thioether groups; Rf2 is a straight or branched C1-C20 perfluoroalkylene group optionally substituted with ether and thiother linkages; and X is selected from the group consisting of fluorine and The invention also provides perfluoroelastomeric compositions cured with the perfluoroimidoylamidines of the invention as well as combinations of perfluoroimidoylamidines and other curing agents.
    Type: Grant
    Filed: July 10, 2007
    Date of Patent: January 29, 2013
    Assignee: LODESTAR Inc.
    Inventors: Gubanov Viktor Andreevich, Kollar Alexander Nikolaevich, Volkova Margarita Alekseevna, Tsipkina Irina Mikhailovna
  • Patent number: 8263719
    Abstract: A polymerization process for producing a tetra-fluoroethylene copolymer, and the copolymer produced thereby, are provided. The copolymer is of the dispersion/fine powder type and contains polymerized tetrafluoroethylene monomer units and co-polymerized higher homologous comonomer units having the formula (CnF(2n+1))CH?CH2, wherein 6?n<10, in which the primary particles are believed to have a core and shell structure and the polymerized comonomer units are present in an amount from 0.01 mol % to 0.3 mol %, based upon total copolymer composition. The copolymer has a raw dispersion primary particle size (RDPS) of less than 0.210 microns coupled with a standard specific gravity (SSG) of less than 2.143. Preferably the copolymer has comonomer units present in an amount from 0.05 mol % and 0.25 mol % and the RDPS is within the range between 0.178 microns and 0.200 microns, coupled with a SSG of less than 2.140.
    Type: Grant
    Filed: February 17, 2009
    Date of Patent: September 11, 2012
    Assignee: Gore Enterprise Holdings, Inc.
    Inventors: Edward A. Sabol, Richard L. Baillie
  • Patent number: 8247505
    Abstract: The present invention provides a process for preparing a fluorine-containing elastomer in a high productivity comparable to that of non-iodine transfer polymerization process by carrying out an iodine transfer polymerization at high pressure. The present invention also provides a fluorine-containing elastomer prepared by this process, and fluorine-containing molded articles. The process is a batch copolymerization process conducted under conditions that the reduced temperature of the critical constant is at least 0.95 and the reduced pressure of the critical constant is at least 0.
    Type: Grant
    Filed: August 27, 2007
    Date of Patent: August 21, 2012
    Assignee: Daikin Industries, Ltd.
    Inventors: Yousuke Nishimura, Masaki Irie, Sadashige Irie, Manabu Fujisawa, Satoshi Tokuno, Mitsuru Kishine
  • Patent number: 8226876
    Abstract: Disclosed herein is a method to produce a semi-crystalline fluoro-polymer film. A semi-crystalline fluoro-polymer material is used. The material is compressed to produce the film. During compression, the material is maintained at a temperature below the melting point of the material. The compression step can be cycled to allow cooling of the material between compression stages. Alternative methods are provided for compressing the material with a co-extrusion substrate, extruding the material and utilizing mandrel expansion for the material.
    Type: Grant
    Filed: May 9, 2006
    Date of Patent: July 24, 2012
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: O. Richard Hughes, Alfred R. Austen
  • Publication number: 20120149815
    Abstract: Embodiments in accordance with the present invention provide polymers for forming layers/films useful in the manufacture of a variety of types of optoelectronic displays. Such embodiments also provide compositions of such polymers for forming such layers/films where the formed layers/films have high transparency over the visible light spectrum.
    Type: Application
    Filed: December 9, 2011
    Publication date: June 14, 2012
    Applicants: Promerus LLC, Sumitomo Bakelite Co., Ltd.
    Inventors: Osamu Onishi, Larry F. Rhodes, Nobuo Tagashira
  • Patent number: 8193276
    Abstract: A fluorocopolymer capable of exhibiting excellent water and oil resistance even with its perfluoroalkyl group being a short chain, and a water and oil proofing composition containing it, are provided. A water and oil proofing composition containing a fluorocopolymer (A) comprising from 40 to 98 mass % of polymerized units (a?) having a C1-6 perfluoroalkyl group, from 1 to 50 mass % of polymerized units (b?) having an alkylene oxide and from 1 to 10 mass % of polymerized units (c?) based on a monomer represented by CH2?C(COOH)-Q-COOH (wherein Q is a C1-4 alkylene group, etc.).
    Type: Grant
    Filed: January 28, 2010
    Date of Patent: June 5, 2012
    Assignee: Asahi Glass Company, Limited
    Inventors: Shuichiro Sugimoto, Takao Hirono, Eiji Morimoto
  • Patent number: 8163857
    Abstract: A mixture of polyfluoroalkadienes represented by the general formulae: CF3(CF2)nCF?CH(CF2)m+1CH?CH2 [Ia] and CF3(CF2)n+1CH?CF(CF2)mCH?CH2 [Ib], wherein n is an integer of 0 to 5, and m is an integer of 0 to 6, is obtained as a mixture fraction of products [Ia] and [Ib] by reacting a polyfluoroalkyl iodide represented by the general formula: CF3(CF2)n+1CH2(CF2)m+1(CH2CH2)I [II], with an organic basic compound. The polyfluoroalkadiene mixture is compounds having a perfluoroalkyl group in which the number of successive CF2 groups is 5 or less, and is effectively used as a copolymerizable monomer in the production of resinous or elastomeric fluorine-containing copolymers, which are used as active ingredients of surface-treating agents, such as water- and oil-repellents and mold-release agents.
    Type: Grant
    Filed: June 12, 2009
    Date of Patent: April 24, 2012
    Assignee: Unimatec Co., Ltd.
    Inventors: Katsuyuki Sato, Seiichiro Murata, Akihiko Ikeda, Daisuke Murai, Mitsuru Maeda
  • Patent number: 8163858
    Abstract: A polyvinylidene difluoride copolymer with a fluoroolefin selected from 2,3,3,3-tetrafluoropropene, 1,1,3,3,3-pentafluoropropene, 2-chloro-pentafluoropropene, hexafluoropropylene, trifluoroethylene, chlorotrifluoroethylene, 3,3,3-trifluoro-2-trifluoromethylpropene and a mixture thereof, wherein the stoichiometry of the co-monomers defines the barrier properties of the copolymer. Such polymers include moisture barrier copolymers and oxygen barrier copolymer. Processes for preparing such moisture barrier copolymers and oxygen barrier copolymers are also provided.
    Type: Grant
    Filed: December 20, 2007
    Date of Patent: April 24, 2012
    Assignee: Honeywell International Inc.
    Inventors: George J Samuels, Gregory J Shafer, Tao Li, Clinton A Threlfall, Nancy Iwamoto, Eric J Rainal
  • Patent number: 8124699
    Abstract: The present invention relates to a method for the polymerization of fluoromonomers using non-fluorinated alkyl phosphonate surfactants, and to the fluoropolymers formed thereby. Specifically, the method of the polymerization uses one or more alkyl phosphonic acids or salts thereof.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 28, 2012
    Assignee: Arkema Inc.
    Inventors: Mehdi Durali, Lotfi Hedhli, Roice Wille
  • Publication number: 20120046420
    Abstract: A polymer containing a recurring unit having an aliphatic polycyclic structure, wherein at least two atoms constituting the ring skeleton of the aliphatic polycyclic structure constitute the main chain of the polymer, and the recurring unit has an aliphatic ring containing a sulfonyl group as the constitutive group of the ring skeleton, has high refractivity, high Abbe's number, high-level heat resistance, high-level light transmittance and low water absorption.
    Type: Application
    Filed: August 19, 2011
    Publication date: February 23, 2012
    Applicant: FUJIFILM Corporation
    Inventors: Rie OKUTSU, Seiya SAKURAI, Tatsuhiko OBAYASHI, Hiroaki MOCHIZUKI
  • Patent number: 8092736
    Abstract: A composition and its use as a mold release composition are disclosed. The composition comprises a fluorotelomer, which comprises repeat units derived from a fluoroalkene, and optionally a comonomer, and has an endgroup derived from an alcohol, an alcohol derivative, or a combination thereof, and said fluorotelomer has or comprises a structure depicted as H(CX2)pBqDr or a mixture of structures depicted as H(CX2)pBq and H(CX2)pDr, wherein each X is independently H or F, provided at least one X is F, p is a number from about 16 to about 1500, B represents a unit derived from a hydrofluorocarbon, q is a number from 0.02 to 0.4, D represents an endgroup derived from said alcohol, alcohol derivative, or combination thereof, and r is a number 0.2 to 1.0.
    Type: Grant
    Filed: November 24, 2008
    Date of Patent: January 10, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Robert Harvey Moffett
  • Patent number: 8080195
    Abstract: A method of producing a fluoropolymer by which a melt-processable fluoropolymer (A) having a specific unstable terminal group or groups (P) is subjected to melt-kneading in a kneader having a stabilization treatment zone to thereby produce a fluoro-polymer (B) resulting from conversion of the specific unstable terminal group or groups (P) to —CF2H. The specific unstable terminal group or groups (P) include alkoxycarbonyl groups, fluoroalkoxycarbonyl groups and/or carboxyl group quaternary nitrogen compound salts, the melt-kneading is carried out in the absence or presence of an alkali metal element or alkaline earth metal element, the content of the alkali metal element or alkaline earth metal element is not greater than 2 ppm of the composition under melt-kneading, and the melt-kneading in the stabilization treatment zone is carried out in the presence of water. A fluoro-polymerised material is also disclosed.
    Type: Grant
    Filed: November 19, 2004
    Date of Patent: December 20, 2011
    Assignee: Daikin Industries, Ltd
    Inventors: Yoshiyuki Takase, Kenji Ishii, Shouji Fukuoka
  • Patent number: 8058352
    Abstract: A membrane humidifier assembly includes a first flow field plate adapted to facilitate flow of a first gas thereto and a second flow field plate adapted to facilitate flow of a second gas thereto. A polymeric membrane is disposed between the first and second flow fields and adapted to permit transfer of water from the first flow field plate to the second flow field plate. The polymeric membrane includes a polymer having perfluorocyclobutyl groups.
    Type: Grant
    Filed: August 28, 2009
    Date of Patent: November 15, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Sean M MacKinnon, Timothy J. Fuller, Annette M. Brenner
  • Patent number: 8053530
    Abstract: A polymer useful as an ion conductor in fuel cells includes a perfluorocyclobutyl moiety and pendant PFSA side groups. The polymer is made by a variation of the Ullmann reaction. Ion conducting membranes incorporating the polymer are provided.
    Type: Grant
    Filed: August 26, 2009
    Date of Patent: November 8, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Timothy J. Fuller, Sean M MacKinnon, Michael R. Schoeneweiss
  • Patent number: 8048963
    Abstract: An ion exchange membrane is prepared from a block copolymer comprising a hydrophobic polymer segment and a polar polymer segment. The ion exchange membrane is formed by placing a film layer in steam, water or an electric field at a temperature greater than about 40° C. for sufficient amount of time to develop a bicontinuous morphology. The ion exchange membrane is also formed from a film layer comprising a block copolymer and a solvent. The film layer is placed in an electric field at an elevated temperature and dried therein. The film layer is thereby converted into an ion exchange membrane with bicontinuous morphology. The ion exchange membrane prepared according to these processes exhibits improved mechanical and electrochemical properties.
    Type: Grant
    Filed: August 31, 2009
    Date of Patent: November 1, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Timothy J. Fuller, Sean M MacKinnon, Michael R. Schoeneweiss
  • Patent number: 8044146
    Abstract: A polymer useful as an ion conducting membrane for fuel cell applications includes both main chain and side chain protogenic groups. Methods for preparing the polymer include addition of the side chains both before and after addition of the protogenic groups.
    Type: Grant
    Filed: April 16, 2010
    Date of Patent: October 25, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Lijun Zou, Sean M. MacKinnon, Timothy J. Fuller
  • Patent number: 8030405
    Abstract: A blend composition comprises a fluorine-containing polymer electrolyte and a fluoro-rubber. An electrolyte membrane may be prepared from the blend composition. The electrolyte membrane may be used in electrochemical cells such as electrolyzers, batteries and fuel cells.
    Type: Grant
    Filed: May 4, 2009
    Date of Patent: October 4, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Sean M MacKinnon, Timothy J. Fuller, Michael R. Schoeneweiss
  • Patent number: 8008404
    Abstract: A composite membrane for fuel cell applications includes a support substrate with a predefined void volume. The void volume is at least partially filled with an ion conducting polymer composition. Characteristically, the ion conducting polymer composition includes a first polymer with a cyclobutyl moiety and a second polymer that is different than the first polymer.
    Type: Grant
    Filed: May 4, 2009
    Date of Patent: August 30, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Sean M MacKinnon, Timothy J. Fuller
  • Patent number: 8003732
    Abstract: An ion conducting polymeric structure suitable for fuel cell applications is provided. The polymeric structure comprises a non-homogenous polymeric layer. The non-homogeneous layer is a blend of a first polymer comprising cyclobutyl moiety; and a second polymer having a non-ionic polymer segment. The weight ratio of the first polymer to the second polymer varies as a function of position within the non-homogenous layer. The blend composition may be cast into an electrolyte membrane that can be used to prepare electrochemical cells such as batteries and fuel cells.
    Type: Grant
    Filed: August 25, 2008
    Date of Patent: August 23, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Sean M MacKinnon, Michael R. Schoeneweiss, Timothy J. Fuller, Craig S. Gittleman
  • Publication number: 20110198224
    Abstract: The subject invention provides a process for efficiently producing electret coarse powder useful as electrophoretic particles for a large-screen display. The process for producing electret coarse powder comprises irradiating a fluorine-containing resin sheet with an electron beam or a radial ray to convert the fluorine-containing resin sheet into an electret sheet, and pulverizing the electret sheet.
    Type: Application
    Filed: March 5, 2010
    Publication date: August 18, 2011
    Applicant: SAKURA COLOR PRODUCTS CORPORATION
    Inventors: Tomotika Yoshitsugi, Hiroshi Inoue
  • Patent number: 7989566
    Abstract: An emulsion polymerization process for the production of non-elastomeric fluoropolymers is disclosed wherein at least one fluorosurfactant is employed as dispersant, said fluorosurfactant being a fluoroalkylphosphoric acid ester of the formula X-Rf-(CH2)n—O—P(O)(OM)2, wherein n is 1 or 2, X?H or F, M=a univalent cation, and Rf is a C4-C6 fluoroalkyl or fluoroalkoxy group. Optionally, a second dispersing agent may be employed in the polymerization, said second agent being a perfluoropolyether having at least one endgroup selected from the group consisting of carboxylic acid, a salt thereof, sulfonic acid and a salt thereof, phosphoric acid and a salt thereof.
    Type: Grant
    Filed: January 15, 2009
    Date of Patent: August 2, 2011
    Assignee: DuPont Performance Elastomers LLC
    Inventors: Michael Cregg Coughlin, Ming-Hong Hung
  • Patent number: 7989512
    Abstract: A method of forming an ionomeric membrane includes a step of reacting a first polymer in chlorosulfonic acid to form a first precipitate. The first precipitate comprising a polymer including a polymer unit having at least one —SO2Cl moiety attached thereto and includes a step of dissolving the first precipitate in a polar aprotic solvent to form the first solution. A polymeric membrane is then formed from the first solution such that the membrane includes the polymer unit having at least one —SO2Cl. The polymer including a polymer unit a polymer unit having at least one —SO2Cl is then reacted with a nucleophilic compound to form the polymeric membrane.
    Type: Grant
    Filed: March 17, 2010
    Date of Patent: August 2, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Timothy J. Fuller, Sean M MacKinnon, Michael R. Schoeneweiss
  • Patent number: 7985805
    Abstract: A polymer blend useful as an ion conductor in fuel cells includes a first polymer having a cyclobutyl moiety and a second polymer include a sulfonic acid group.
    Type: Grant
    Filed: May 4, 2009
    Date of Patent: July 26, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Timothy J. Fuller, Sean M MacKinnon, Michael R. Schoeneweiss, Craig S. Gittleman
  • Patent number: 7977433
    Abstract: A fluororubber composition including a polyol-crosslinkable fluororubber; a cross-linking accelerator comprising a quaternary ammonium salt; and a polyol crosslinking agent; wherein the weight ratio X (quaternary ammonium salt/polyol crosslinking agent) between the cross-linking accelerator and the polyol crosslinking agent is in a range of 0.40 to 0.60; and a production method of a cross-linked fluororubber product, comprising the steps of: previously polyol-crosslinking, as required, the fluororubber composition; and subsequently heat treating the polyol-crosslinked composition, in a temperature range of 200° C. to 300° C. for 0.1 to 48 hours. The fluororubber composition has surface has a lower friction coefficient, and the surface roughness of the cross-linked fluororubber product can be increased without applying a treatment to a mold.
    Type: Grant
    Filed: October 16, 2006
    Date of Patent: July 12, 2011
    Assignee: Nok Corporation
    Inventor: Hiroyuki Sano
  • Patent number: 7972732
    Abstract: A membrane humidifier assembly includes a first flow field plate adapted to facilitate flow of a first gas thereto and a second flow field plate adapted to facilitate flow of a second gas thereto. A polymeric membrane is disposed between the first and second flow fields and adapted to permit transfer of water from the first flow field plate to the second flow field plate. The polymeric membrane includes a polymer having perfluorocyclobutyl groups and a pendant side chain having a protogenic group.
    Type: Grant
    Filed: August 28, 2009
    Date of Patent: July 5, 2011
    Assignee: GM Global Technology Operations LLC
    Inventors: Sean M MacKinnon, Timothy J. Fuller, Annette M. Brenner
  • Patent number: 7968662
    Abstract: A repellent agent composition including an aqueous continuous phase and a graft copolymer dispersed in the aqueous continuous phase. The graft copolymer has a water soluble polymer trunk having hydroxyl groups and branches having fluorinated groups bonded to the polymer trunk at a carbon atom substituted with a hydroxyl group. Also disclosed is a method of making the graft copolymer and a substrate treated with the repellent composition.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: June 28, 2011
    Assignee: Daikin Industries, Ltd.
    Inventors: Anthony A. Parker, Joseph J. Marcinko, Franklin A. Adamsky, Bradley H. Hartong, Takashi Enomoto
  • Patent number: 7947425
    Abstract: Copolymers prepared by copolymerization of at least one fluorinated vinyl ether are provided. In one embodiment, the at least one fluorinated vinyl ether comprises ethylene directly substituted at an olefinic carbon atom with a moiety —OR* and optionally substituted with one, two, or three additional nonhydrogen substituents, wherein R* comprises a fluorinated alkyl moiety substituted with a protected or unprotected hydroxyl group, and further wherein an atom within R* may be (i) taken together with one of the additional nonhydrogen substituents, if present, or (ii) directly bound to an olefinic carbon atom, to form a ring. The polymers are useful, for example, 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.
    Type: Grant
    Filed: August 7, 2006
    Date of Patent: May 24, 2011
    Assignee: International Business Machines Corporation
    Inventors: Richard A. DiPietro, Hiroshi Ito
  • Patent number: 7947791
    Abstract: The present invention provides a fluorinated polymer excellent in the crosslinking reactivity, crosslinked rubber physical properties and chemical resistance, and its crosslinked rubber. A fluorinated polymer comprising repeating units (a) based on at least one monomer selected from the group consisting of ethylenic unsaturated compounds each having a hydroxyphenyl group, repeating units (b) based on at least one fluoromonomer selected from the group consisting of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, 3,3,3-trifluoropropene, 1,3,3,3-tetrafluoropropene, 1,1,2-trifluoroethylene, vinyl fluoride, 1,2-difluoroethylene and CF2?CF—O—Rf (wherein Rf is a C1-8 saturated perfluoroalkyl group or a perfluoro(alkoxyalkyl) group) and, if necessary, repeating units (c) based on at least one hydrocarbon monomer selected from the group consisting of ethylene, propylene and CH2?CH—O—R1.
    Type: Grant
    Filed: March 19, 2009
    Date of Patent: May 24, 2011
    Assignee: Asahi Glass Company, Limited
    Inventors: Jumpei Nomura, Toshikazu Yoneda, Mitsuru Seki, Hiroki Kamiya, Hiroshi Funaki, Takehiro Kose
  • Patent number: 7897693
    Abstract: In one embodiment, a copolymer comprises a sulfonatable segment covalently linked to an un-sulfonatable segment through an organic linking group. The sulfonatable group segment may be sulfonated through direction sulfonation or sulfonation through a spacer molecule. In another embodiment, a copolymer comprises a sulfonated segment and an unsulfonated segment. A membrane electrode assembly and a fuel cell may be produced using the copolymer.
    Type: Grant
    Filed: August 25, 2008
    Date of Patent: March 1, 2011
    Assignee: GM Global Technology Operations, Inc.
    Inventors: Sean M MacKinnon, Timothy J. Fuller