Fluorine-containing Monomer Patents (Class 524/805)
  • Patent number: 10875940
    Abstract: To provide a fluorinated polymer which can be heat-cured at low temperature (from room temperature to 150° C.). A fluorinated polymer containing units represented by the following formula (1): wherein X1 and X2 are each independently a hydrogen atom or a fluorine atom, Q1 is a single bond or an etheric oxygen atom, Rf1 is a fluoroalkylene group or a fluoroalkylene group having at least 2 carbon atoms and having an etheric oxygen atom between carbon atoms, Z1 is NR1—Y1, O—Y2 or S—Y3, R1 is a hydrogen atom, an alkyl group or an aryl group, and Y1, Y2 and Y3 are each independently a group having at least one hydrolyzable silyl group.
    Type: Grant
    Filed: February 5, 2019
    Date of Patent: December 29, 2020
    Assignee: AGC Inc.
    Inventor: Norihide Sugiyama
  • Patent number: 10494554
    Abstract: Provided is a coating film that can more reliably exhibit an excellent water repellency and an excellent oil repellency. This water- and oil-repellent coating film is a coating film formed on a surface of a material in order to impart water repellency and oil repellency, wherein (1) the coating film contains a metal oxide-containing composite particle; (2) the composite particle contains a) a metal oxide particle and b) a covering layer that contains a polyfluoroalkyl methacrylate resin and is formed on the surface of the metal oxide particle; and (3) a value obtained by dividing the fluorine content (weight %) of the composite particle by a surface area (m2/g) of the metal oxide particle is 0.025 to 0.180.
    Type: Grant
    Filed: June 7, 2013
    Date of Patent: December 3, 2019
    Assignees: TOYO ALUMINIUM KABUSHIKI KAISHA, NIPPON AEROSIL CO., LTD.
    Inventors: Kazunori Yamada, Tomonobu Sekiguchi, Hiroyuki Nishikawa, Hiroshi Oe, Yuya Terasawa, Masahiko Kamada, Toshio Morii, Yusuke Tosaki, Yukiya Yamashita
  • Patent number: 9938403
    Abstract: A method of making a highly fluorinated polymers and resulting aqueous mixtures. The method comprising polymerizing one or more perfluorinated monomers in an aqueous emulsion polymerization in the presence of a polymerizable fluorinated emulsifier to form a perfluorinated polymer. The polymerizable fluorinated emulsifier has the formula X2C?CX(CF2)m(CH2)n[O—(CX2)p]q—[O—(CX2)r]s?[O—(CX2—CX2)]t—[(O)w—(CX2)u]v—[CH2]z—Y. The method also provides for isolating the highly fluorinated polymer and post-fluorinating the isolated highly fluorinated polymer.
    Type: Grant
    Filed: January 11, 2016
    Date of Patent: April 10, 2018
    Assignee: 3M Innovative Properties Company
    Inventors: Klaus Hintzer, Harald Kaspar, Herbert Koenigsmann, Helmut Traunspurger, Tilman C. Zipplies
  • Patent number: 9714307
    Abstract: A method of making a partially fluorinated polymer dispersions and resulting aqueous mixtures. The method comprising polymerizing one or more fluorinated monomers in an aqueous emulsion polymerization in the presence of a polymerizable fluorinated emulsifier to form a fluorinated polymer. The polymerizable fluorinated emulsifier has the formula X2C?CX(CF2)m(CH2)n[O—(CX2)p]q-[O—(CX2)r]s—[O—(CX2—CX2)]t—[(O)w—(CX2)u]v-[CH2]z—Y.
    Type: Grant
    Filed: November 20, 2013
    Date of Patent: July 25, 2017
    Assignee: 3M Innovative Properties Company
    Inventors: Klaus Hintzer, Harald Kaspar, Herbert Koenigsmann, Helmut Traunspurger, Tilman C. Zipplies
  • Patent number: 9650479
    Abstract: A tetrafluoroethylene (TFE) copolymer film having a first endotherm between about 50° C. and about 300° C., a second endotherm between about 320° C. and about 350° C., and a third endotherm between about 350° C. and about 400° C. is provided. In exemplary embodiments, the third endotherm is approximately 380° C. In some embodiments, the second endotherm is between about 320° C. and about 330° C. or between about 330° C. and about 350° C. TFE copolymer films have a methane permeability less than about 20 ?g*micron/cm2/min. In addition, the dense articles have a void volume of less than about 20%. Methods for dense articles from core shell tetrafluoroethylene copolymers are also provided. The dense articles exhibit improved physical and mechanical properties such as adhesion and barrier properties.
    Type: Grant
    Filed: December 19, 2014
    Date of Patent: May 16, 2017
    Assignees: W. L. Gore & Associates, Inc., W. L. Gore & Associates GmbH
    Inventors: Lawrence A. Ford, Michael E. Kennedy, Shaofeng Ran, Todd S. Sayler, Gregory J. Shafer
  • Patent number: 9644054
    Abstract: A dense article that includes a dense TFE copolymer film is provided. The dense TFE copolymer film includes a first endotherm between about 50° C. and about 300° C., a second endotherm between about 320° C. and about 350° C., and a third endotherm between about 350° C. and about 400° C. To form the dense article, a core shell TFE copolymer is formed into a pellet, ram extruded into a tape, dried into a dried preform, and then stretched into a dense TFE copolymer film that exhibits improved physical and mechanical properties. The dense TFE copolymer film is produced directly from the dried preform at a deformation temperature less than about 335° C. and without increasing the porosity of the dried preform, as would conventionally be done in expansion processes. The dense TFE copolymer films have a methane permeability less than about 20 ?g*micron/cm2/min. The dense articles have a void volume less than about 20%.
    Type: Grant
    Filed: December 19, 2014
    Date of Patent: May 9, 2017
    Assignees: W. L. Gore & Associates, Inc., W. L. Gore & Associates GmbH
    Inventors: Lawrence A. Ford, Michael E. Kennedy, Shaofeng Ran, Todd S. Sayler, Gregory J. Shafer
  • Patent number: 9580590
    Abstract: The present invention aims to provide a novel method for producing an aqueous dispersion containing non-melt-processable polytetrafluoroethylene particles. The present invention relates to a method for producing an aqueous dispersion containing non-melt-processable polytetrafluoroethylene particles, the method including polymerizing tetrafluoroethylene in an aqueous medium in the presence of perfluoro hexanoic acid or its salt.
    Type: Grant
    Filed: August 27, 2012
    Date of Patent: February 28, 2017
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Takahiro Taira, Taku Yamanaka, Yoshinori Nanba, Atsuko Tanaka, Makoto Ono, Nobuhiko Tsuda, Taketo Kato
  • Patent number: 9284690
    Abstract: A water- and oil-repellent agent is produced by blending a fluorine-containing polymer and a fluorine-free polymer, wherein the fluorine-free polymer is 30-70% by weight of the total of the water- and oil-repellent agent, the fluorine-containing polymer is polymerized by a fluorine-containing monomer, a non-fluorinated branched monomer, a non-fluorinated crosslinking monomer, and an olefin monomer, and wherein the fluorine-containing monomer, the non-fluorinated branched monomer, the non-fluorinated crosslinking monomer, and the olefin monomer are 45-80%, 1-30%, 1-10%, and 10-50% by weight of the total of the fluorine-containing polymer respectively- and the fluorine-free polymer is polymerized by a non-fluorinated non-crosslinking monomer, a non-fluorinated crosslinking monomer, and an olefin monomer, wherein the non-fluorinated non-crosslinking monomer, the non-fluorinated crosslinking monomer, and the olefin monomer are 45-80%, 1-30%, and 10-50% by weight of the total of the fluorine-free polymer respectiv
    Type: Grant
    Filed: July 1, 2014
    Date of Patent: March 15, 2016
    Assignee: Taiwan Fluoro Technology Co., Ltd.
    Inventors: Jo-Yu Huang, Ren-Ren Chiou, Jih-Hsih Ho
  • Patent number: 9260553
    Abstract: A method of making a highly fluorinated polymers and resulting aqueous mixtures. The method comprising polymerizing one or more perfluorinated monomers in an aqueous emulsion polymerization in the presence of a polymerizable fluorinated emulsifier to form a perfluorinated polymer. The polymerizable fluorinated emulsifier has the formula X2C?CX(CF2)m(CH2)n[O—(CX2)p]q—[O—(CX2)r]s—[O—(CX2—CX2)]t—[(O)w—(CX2)u]v—[CH2]z—Y. The method also provides for isolating the highly fluorinated polymer and post-fluorinating the isolated highly fluorinated polymer.
    Type: Grant
    Filed: November 21, 2013
    Date of Patent: February 16, 2016
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Klaus Hintzer, Harald Kaspar, Herbert Koenigsmann, Helmut Traunspurger, Tilman C. Zipplies
  • Publication number: 20150148482
    Abstract: A method for preparing a fluoropolymer aqueous dispersion, including: step (A) of preparing a fluoropolymer aqueous dispersion comprising a fluoropolymer having at least one selected from the group consisting of —SO2Y and —COOR (wherein Y is a halogen, and R is a C1 to C4 alkyl) by emulsion polymerization; step (B) of heating the fluoropolymer aqueous dispersion to 50° C. or higher; and step (C) of contacting the fluoropolymer aqueous dispersion with an ion exchange resin for cation exchange after step (B), thereby providing a purified fluoropolymer aqueous dispersion, the fluoropolymer aqueous dispersion being adjusted to pH 7 or lower from the end of the polymerization in step (A) to the end of step (C).
    Type: Application
    Filed: May 22, 2013
    Publication date: May 28, 2015
    Inventors: Takashi Yoshimura, Kazuhiro Ohtsuka, Tadashi Ino, Noriyuki Shinoki, Masahiro Kondo
  • Publication number: 20150148481
    Abstract: Process for polymerizing fluoromonomer to form an aqueous dispersion of fluoropolymer particles including: (a) providing an aqueous medium in a polymerization reactor, (b) adding nucleating additive comprising polyalkylene oxide having a number average molecular weight of about 50 to about 2000 to the aqueous medium in an amount of about 0.1 ppm to about 50 ppm based on water in the aqueous medium, (c) exposing the nucleating additive to oxidizing agent to form a dispersion of oleophilic nucleation sites in the aqueous medium; (d) pressurizing the reactor by adding fluoromonomer, and (e) adding polymerization initiator to the aqueous medium to cause the polymerizing of the fluoromonomer to form fluoropolymer particles dispersed in the aqueous medium.
    Type: Application
    Filed: November 25, 2014
    Publication date: May 28, 2015
    Inventors: PAUL DOUGLAS BROTHERS, Subhash Vishnu Gangal, Dipti Dilip Khasnis
  • Patent number: 9029471
    Abstract: Various fluoropolymers have been proposed for imparting oil and water repellency to leather. Commonly, these fluoropolymers are amphiphilic; i.e., they are made from at least one monomer which is hydrophobic and at least one monomer which is hydrophilic. The present invention identifies and remedies disadvantages associated with the ability of amphiphilic fluoropolymers to impart oil and water repellency to leather. Contrary to conventional thinking, it has now been discovered that the incorporation of hydrophilic groups in a fluoropolymer undesirably reduces its ability to impart water resistance to leather. Correspondingly, it has also been discovered that a fluoropolymer incorporating fewer or no hydrophilic groups imparts superior oil and water repellency to leather when compared to fluoropolymers incorporating more hydrophilic groups. Therefore, this invention provides fluoropolymers which incorporate reduced levels of hydrophilic groups.
    Type: Grant
    Filed: September 30, 2008
    Date of Patent: May 12, 2015
    Assignee: E I du Pont du Nemours and Company
    Inventors: Romain Severac, Agnes Ibos, Lamia Heuze, Renaud Laloux-Walther
  • Patent number: 8969437
    Abstract: The invention provides a compound which is useful in production of a fluoropolymer and easy to be removed from the produced fluoropolymer, a method of producing the compound, and a method of producing a fluoropolymer using the compound. The invention provides a compound which is represented by Rf1—CH2O—CF2—CHF—Rf2—X, wherein Rf1 represents a fluoroalkyl group containing 1 to 5 carbon atoms, Rf2 represents a fluoroalkylene group containing 1 to 3 carbon atoms, X represents —COOM or —SO3M, and M represents one of H, K, Na, and NH4.
    Type: Grant
    Filed: January 18, 2013
    Date of Patent: March 3, 2015
    Assignee: Daikin Industries, Ltd.
    Inventors: Nobuhiko Tsuda, Akinari Sugiyama
  • Patent number: 8916643
    Abstract: A water- and oil-repellent includes, as an active ingredient, a fluorine-containing copolymer including as a copolymer unit (A) at least one of perfluoroalkylalkyl acrylates and corresponding methacrylates, (B) benzyl acrylate or benzyl methacrylate represented by the general formula: CnF2n+1CmH2mOCOCR?CH2 (wherein R represents a hydrogen atom or a methyl group; n represents 4, 5, or 6; and m represents 1, 2, 3, or 4), (C) a fluorine-free polymerizable monomer other than benzyl acrylate and benzyl methacrylate, and (D) a cross-linkable group-containing polymerizable monomer.
    Type: Grant
    Filed: April 18, 2011
    Date of Patent: December 23, 2014
    Assignee: Unimatec Co., Ltd.
    Inventors: Ji-Shan Jin, Satoshi Kurihara, Sumiko Mouri, Katsuyuki Sato
  • Patent number: 8900412
    Abstract: Stable, coating compositions are disclosed. The compositions comprise an aqueous solution of cationic polymer, starch, and a stabilizing agent. Method of using the coating composition to improve the dry strength of paper is also disclosed.
    Type: Grant
    Filed: October 31, 2011
    Date of Patent: December 2, 2014
    Assignee: Solenis Technologies Cayman, L.P.
    Inventors: Sachin Borkar, Marc C. Putnam
  • Patent number: 8901264
    Abstract: To provide a copolymer which can impart sufficient dynamic water repellency, after air-drying water repellency and friction durability to a surface of an article, and which has low impact on the environment, a method for producing the same, a water repellent composition and an article excellent in dynamic water repellency, after air-drying water repellency and friction durability.
    Type: Grant
    Filed: September 9, 2010
    Date of Patent: December 2, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Kazunori Sugiyama, Toyomichi Shimada, Nobuyuki Otozawa, Yuuichi Oomori, Minako Shimada
  • Patent number: 8871882
    Abstract: A method for the preparation of a fluoropolymer by means of emulsion polymerization of a reaction mixture in an aqueous medium is disclosed wherein the reaction mixture includes a fluoromonomer having the structure of wherein R1, R2, and R3 are each independently hydrogen atoms, alkyl groups, substituted alkyl groups, or halogens, wherein at least one of R1, R2, and R3 is a fluorine atom, and wherein R is each independently a substituent on the styrenic ring, n is an integer from 0 to 5 representing the number of the substituents on the styrenic ring; b) an emulsion stabilizer combination comprising: i) an anionic surfactant; and, ii) a cationic surfactant or a non-ionic surfactant; and, c) a free-radical initiator.
    Type: Grant
    Filed: February 14, 2012
    Date of Patent: October 28, 2014
    Assignee: Akron Polymer Systems, Inc.
    Inventors: Xiaoliang Zheng, Dong Zhang, Jiaokai Jing, Ted Calvin Germroth, Frank W. Harris, Thauming Kuo, Bin Wang, Douglas Stephens McWilliams
  • Patent number: 8835551
    Abstract: Iodine containing amorphous fluoropolymers having at least one fluoropolymer with a cure site, where the fluoropolymer has a Mooney viscosity of 2 or less (ML 1+10) at 100° C. according to ASTM D1646, and a peel strength to a roll mill of 10 dN/cm or less and methods for making such iodine containing amorphous fluoropolymers are described. Articles derived from the cured product of such iodine containing amorphous fluoropolymers are also described. Solutions, dispersions and coatings derived from such iodine containing amorphous fluoropolymers are also described.
    Type: Grant
    Filed: September 11, 2008
    Date of Patent: September 16, 2014
    Assignee: 3M Innovative Properties Company
    Inventors: Tatsuo Fukushi, Peter J. Scott, Cynthia N. Ferguson, Werner M. A. Grootaert, Denis Duchesne, Yeng Moua, Larry A. Last, Terri A. Shefelbine, Luke M. B. Rodgers
  • Patent number: 8796368
    Abstract: A water- and oil-repellent comprising an aqueous dispersion of a fluorine-containing copolymer including as a copolymerization unit (a) a perfluoroalkylalkyl (meth)acrylate represented by the general formula CnF2n+1CmH2mOCOCR?CH2 (wherein R represents hydrogen atom or methyl group; n represents 4, 5, or 6; and m represents 1, 2, 3, or 4), (b) benzyl (meth)acrylate, (c) a fluorine-free polymerizable monomer other than benzyl (meth)acrylate, and (d) a cross-linkable group-containing polymerizable monomer; and a blocked isocyanate added to the aqueous dispersion in a weight ratio of 0.05 to 3.0 to the weight of the solid content of the aqueous dispersion.
    Type: Grant
    Filed: August 8, 2008
    Date of Patent: August 5, 2014
    Assignee: Unimatec Co., Ltd.
    Inventors: Ji-Shan Jin, Sumiko Mouri, Katsuyuki Sato
  • Publication number: 20140147745
    Abstract: To provide a binder for a storage battery device, whereby good adhesion is obtainable, and it is possible to realize good charge and discharge characteristics in a secondary battery by well suppressing swelling of an electrode by an electrolytic solution. A binder for a storage battery device, which is made of a fluorinated copolymer comprising repeating units (a) derived from tetrafluoroethylene and repeating units (b) derived from propylene, wherein the molar ratio (a)/(b) is from 60/40 to 75/25, and the total of the repeating units (a) and (b) is at least 90 mol % in all repeating units.
    Type: Application
    Filed: January 29, 2014
    Publication date: May 29, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Mizuna TOYODA, Takehiro KOSE, Hiroki NAGAI
  • Patent number: 8735492
    Abstract: An object of the present invention is to provide a method for producing a fluoropolymer which produces a large number of particles with a small particle size using a specific non-fluorous compound having surfactant ability. The method for producing a fluoropolymer includes aqueous dispersion polymerization of a monomer including at least one fluoroolefin in the presence of a compound (1) represented by the formula: CH2?CR1—R2—O-(AO)p—X (in the formula, R1 is hydrogen or an alkyl group; R2 is an alkylene group having two or more carbon atoms; AO is a linear or branched oxyalkylene group having 2 to 4 carbon atoms; p is a positive integer; X is H or SO3Y wherein Y is NH4 or an alkaline metal; and AO may be the same or different and may form two or more blocks if there is more than one AO.
    Type: Grant
    Filed: August 25, 2010
    Date of Patent: May 27, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Katsuhiko Imoto, Shumi Nishii, Yoshinari Fukuhara
  • Patent number: 8735520
    Abstract: A process for producing vinyl fluoride polymer comprising polymerizing vinyl fluoride in an aqueous polymerization medium containing initiator and halogen-free surfactant with a critical micelle concentration of less than about 0.05 weight percent at 25° C. The halogen-free surfactant is present in the aqueous polymerization medium in an amount less than about 0.1 weight percent based on the weight of the aqueous polymerization medium. The aqueous polymerization medium is essentially free of halogen-containing surfactant. An aqueous dispersion comprising vinyl fluoride polymer particles present in a range of from about 5 to about 40 weight percent based on the weight of the aqueous phase, wherein said vinyl fluoride polymer particles have a Dv(50) of less than about 20 microns, and halogen-free surfactant, wherein said halogen-free surfactant is present in said aqueous dispersion in an amount less than 0.1 weight percent based on the weight of the aqueous phase.
    Type: Grant
    Filed: October 19, 2011
    Date of Patent: May 27, 2014
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Ronald Earl Uschold
  • Patent number: 8703998
    Abstract: A process comprising polymerizing in an aqueous medium at least one fluorinated olefin monomer other than vinylidene fluoride in the presence of a compound of formula (1): Rf(CH2CF2)m—(CH2)nSO3M??(1) wherein Rf is a C1 to C4 linear or branched perfluoroalkyl group, m is an integer of from 1 to 6, n is from 0 to 4, M is H, NH4, Li, Na or K, and a method of altering the surface behavior of a liquid comprising adding to the liquid the composition of a compound of formula (1).
    Type: Grant
    Filed: June 20, 2011
    Date of Patent: April 22, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Sheng Peng, Phan Linh Tang
  • Patent number: 8697822
    Abstract: The present invention relates to a method for the polymerization in an aqueous medium of monomers, and especially of fluoromonomers, using non-fluorinated surfactants; and the fluoropolymers formed therefrom. Specifically, the method of the polymerization uses one or more non-fluorinated surfactants selected from the group consisting of polyvinylphosphonic acid, polyacrylic acids, polyvinyl sulfonic acid, and salts thereof. Additionally, the use of polyvinylphosphonic acid, polyacrylic acids, polyvinyl sulfonic acid as surfactants in aqueous free radical polymerization is also novel.
    Type: Grant
    Filed: June 26, 2006
    Date of Patent: April 15, 2014
    Assignee: Arkema Inc.
    Inventors: Mehdi Durali, Lotfi Hedhli, Ramin Amin-Sanayei
  • Patent number: 8669034
    Abstract: Toner compositions, treated fluoropolymer particles, methods of making treated fluoropolymer particles, and the like, are disclosed.
    Type: Grant
    Filed: October 7, 2008
    Date of Patent: March 11, 2014
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: Elliad Silcoff, Gili Assaf, Gil Bar-Haim, Albert Teishev
  • Publication number: 20140005333
    Abstract: There are provided microemulsions derived from compositions containing oligomeric fluorosulfinic compounds and/or ethylenically unsaturated, polymerizable monomeric fluorosulfinic compounds and to their uses in (co)polymerization processes in aqueous emulsion of fluorinated monomers.
    Type: Application
    Filed: December 13, 2011
    Publication date: January 2, 2014
    Applicant: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Tatsuo Fukushi, Gregg D. Dahlke, Denis Duchesne, Werner M.A. Grootaert, Miguel A. Guerra, Larry A. Last, Peter J. Scott, Zai-Ming Qiu
  • Publication number: 20130330621
    Abstract: To produce a method for producing a fluorinated copolymer latex with a low content of metal components and with favorable stability of the latex even with a low content of an organic solvent. A method for producing a fluorinated copolymer latex, which comprises emulsion-polymerizing a monomer mixture containing tetrafluoroethylene and propylene in the presence of an aqueous medium, an anionic emulsifying agent and a thermally decomposable radical polymerization initiator at a polymerization temperature within a range of from 50° C. to 100° C., wherein the aqueous medium comprises water alone, or water and a water-soluble organic solvent, and the content of the water-soluble organic solvent is less than 1 part by mass per 100 parts by mass of water; and the amount of use of the anionic emulsifying agent is from 1.5 to 5.0 parts by mass per 100 parts by mass of the fluorinated copolymer to be formed.
    Type: Application
    Filed: August 19, 2013
    Publication date: December 12, 2013
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Mizuna NARUMI, Takehiro Kose, Hiroki Nagai
  • Publication number: 20130331516
    Abstract: A process comprising polymerizing at least one fluorinated monomer in an aqueous medium containing initiator and polymerization agent to form an aqueous dispersion of particles of fluoropolymer, the polymerization agent comprising: fluoropolyether acid or salt thereof having a number average molecular weight of at least about 800 g/mol; and fluorosurfactant having the formula: [R1—On-L-A?]Y+ wherein: R1 is a linear or branched partially or fully fluorinated aliphatic group which may contain ether linkages; n is 0 or 1; L is a linear or branched alkylene group which may be nonfluorinated, partially fluorinated or fully fluorinated and which may contain ether linkages; A? is an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion, and phosphonate; and Y+ is hydrogen, ammonium or alkali metal cation; with the proviso that the chain length of R1—On-L- is not greater than 6 atoms.
    Type: Application
    Filed: August 13, 2013
    Publication date: December 12, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: PAUL DOUGLAS BROTHERS, Subhash Vishnu Gangal
  • Patent number: 8598290
    Abstract: The present invention provides a method of producing a fluoroelastomer excellent in dispersion stability at low cost, at a high rate of polymerization and in high yields. The present invention is a method of producing a fluoroelastomer comprising an emulsion polymerization of a fluorinated monomer in the presence of a water-soluble radical polymerization initiator, wherein the emulsion polymerization is carried out in the presence of a compound (1) containing a functional group reactive in radical polymerization and a hydrophilic group and a fluorinated compound (2) containing a fluorocarbon group comprising 1 to 6 continuously united carbon atom with fluorine atom directly bound to each of them as well as a hydrophilic group.
    Type: Grant
    Filed: June 29, 2007
    Date of Patent: December 3, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Mitsuru Kishine, Masanori Kitaichi, Yousuke Nishimura, Manabu Fujisawa, Yoshiki Tanaka, Shintarou Ogata, Yutaka Ueta, Shigeru Morita
  • Patent number: 8557938
    Abstract: The invention relates to the preparation of branched fluoropolymers having long chain branches and little or no gels, by a process involving polymerization at high temperatures using persulfates and optionally multifunctional initiators. The invention also relates to gel-free, branched polymers with strain hardening produced by the process.
    Type: Grant
    Filed: November 10, 2005
    Date of Patent: October 15, 2013
    Assignee: Arkema Inc.
    Inventors: Lotfi Hedhli, Nafih Mekhilef
  • Patent number: 8536269
    Abstract: The present invention provides peroxidic fluoropolyether and a fluorine-containing dispersion obtained from polymerization of fluorine-containing monomers in the presence of peroxidic fluoropolyether as a surfactant. The peroxidic fluoropolyether can be used as surfactant for producing aqueous dispersion of fluorine-containing monomer in place of PFOA or the salts thereof. Thus the amount of PFOA or the salts thereof is reduced and the natural environment is protected. In addition, applying peroxidic fluoropolyether as surfactant and combining it with adjuvants, such as initiator, can induce the reaction moderate and can be beneficial to the polymerization control, thus reducing the amount of initiator or shortening the reaction time.
    Type: Grant
    Filed: August 15, 2008
    Date of Patent: September 17, 2013
    Assignee: Nova-Duct Technologies Pty Ltd
    Inventors: Xueduan Xie, Jun Qu, Rong Bai, Jianxin Zhang, Xucang Yang, Bo Chen, Jingang Zhang, Ming Zhang, Xianquan Hu, Yu Cheng
  • Publication number: 20130225764
    Abstract: A method for producing a fluoropolymer dispersion where a fine particle containing a fluoropolymer is dispersed in an aqueous dispersion medium, the fluoropolymer having a sulfonic acid group, and the method including a polymerization reaction step of emulsion polymerizing a fluorovinyl ether derivative and a fluorine-containing ethylenic monomer to give a fluoropolymer precursor, a hydrolysis step of hydrolyzing, in an aqueous medium, —SO2X1, where X1 represents a halogen atom, which the fluoropolymer precursor has thereby to give the fluoropolymer, the fluorovinyl ether derivative being represented by the following general formula (II): CF2?CF—O—(CF2CFY1—O)n—(CFY2)m-A1??(II) wherein Y1, n, Y1, m and A1 are as defined herein, the fluoropolymer precursor having a fluorovinyl ether derivative unit content of 5 to 40 mole percent, and the fluoropolymer dispersion being produced without drying the fluoropolymer precursor and the fluoropolymer.
    Type: Application
    Filed: March 18, 2013
    Publication date: August 29, 2013
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventor: DAIKIN INDUSTRIES, LTD.
  • Patent number: 8519072
    Abstract: A process comprising polymerizing at least one fluorinated monomer in an aqueous medium containing initiator and polymerization agent to form an aqueous dispersion of particles of fluoropolymer, the polymerization agent comprising: fluoropolyether acid or salt thereof having a number average molecular weight of at least about 800 g/mol; and fluorosurfactant having the formula: [R1—On-L-A?]Y+ wherein: R1 is a linear or branched partially or fully fluorinated aliphatic group which may contain ether linkages; n is 0 or 1; L is a linear or branched alkylene group which may be nonfluorinated, partially fluorinated or fully fluorinated and which may contain ether linkages; A? is an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion, and phosphonate; and Y+ is hydrogen, ammonium or alkali metal cation; with the proviso that the chain length of R1—On-L- is not greater than 6 atoms.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: August 27, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Paul Douglas Brothers, Subhash Vishnu Gangal
  • Patent number: 8481660
    Abstract: Disclosed is (1) a mixture of fluoroalkyl alcohol-unsaturated carboxylic acid derivatives represented by the general formulae: CF3(CF2)n(CH?CF)a(CF2CF2)b(CH2CH2)c OCOCR?CH2 and CF3(CF2)n?1(CF?CH)a CF2(CF2CF2)b(CH2CH2)cOCOCR?CH2, wherein R is a hydrogen atom or a methyl group, n is an integer of 1 to 5, a is an integer of 1 to 4, b is an integer of 0 to 3, and c is an integer of 1 to 3; (2) a fluorine-containing polymer containing the mixture as a polymerization unit; and (3) a water- and oil-repellent comprising the fluorine-containing polymer as an active ingredient. The fluoroalkyl alcohol-unsaturated carboxylic acid derivatives are produced by an esterification reaction of a mixture of fluoroalkyl alcohols represented by the general formulae: CF3(CF2)n(CH?CF)a(CF2CF2)b(CH2CH2)cOH and CF3(CF2)n?1(CF?CH)aCF2(CF2CF2)b, (CH2CH2)cOH, with acrylic acid or methacrylic acid.
    Type: Grant
    Filed: January 20, 2009
    Date of Patent: July 9, 2013
    Assignee: Unimatec Co., Ltd.
    Inventors: Seiichiro Murata, Masayosi Horiuti, Katsuyuki Sato, Satoshi Kurihara
  • Patent number: 8399703
    Abstract: The invention provides a compound which is useful in production of a fluoropolymer and easy to be removed from the produced fluoropolymer, a method of producing the compound, and a method of producing a fluoropolymer using the compound. The invention provides a compound which is represented by Rf1—CH2O—CF2—CHF—Rf2—X, wherein Rf1 represents a fluoroalkyl group containing 1 to 5 carbon atoms, Rf2 represents a fluoroalkylene group containing 1 to 3 carbon atoms, X represents —COOM or —SO3M, and M represents one of H, K, Na, and NH4.
    Type: Grant
    Filed: July 24, 2008
    Date of Patent: March 19, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Nobuhiko Tsuda, Akinari Sugiyama
  • Patent number: 8394882
    Abstract: An improved process for emulsion polymerization of fluoropolymers, such as polytetrafluoroethylene, employs reduced amounts of fluorinated emulsifiers. The addition of europium III chloride facilitates emulsion polymerization of fluoropolymers having comparable quality to those fluoropolymers made using conventional processes employing greater amounts of environmentally undesirable fluorinated emulsifiers.
    Type: Grant
    Filed: March 22, 2011
    Date of Patent: March 12, 2013
    Inventor: Zancy VonHooks
  • Patent number: 8349954
    Abstract: The present invention relates to a method for the polymerization of fluoromonomers using non-fluorinated polycaprolactone, and to the fluoropolymers formed thereby. Specifically, the method of the polymerization uses one or more polycaprolactone, or salts thereof.
    Type: Grant
    Filed: April 2, 2009
    Date of Patent: January 8, 2013
    Assignee: Arkema Inc.
    Inventor: Lotfi Hedhli
  • Patent number: 8338518
    Abstract: A novel aqueous polymerization process for making fluoropolymer dispersions is disclosed in which non-ionic non-fluorinated emulsifier is used to produce fluoropolymer emulsions. The emulsifiers used in the invention are those that contain segments of polyethylene glycol, polypropylene glycol, and/or polytetamethylene glycol with repeating units of 3 to 100. The process and fluoropolymer produced contain no fluorinated surfactant.
    Type: Grant
    Filed: December 8, 2006
    Date of Patent: December 25, 2012
    Assignee: Arkema Inc.
    Inventors: Ramin Amin-Sanayei, Christyn Olmstead
  • Publication number: 20120202946
    Abstract: The invention relates to a process for the isolation of (per)fluorinated polymers containing sulfonyl fluoride functional groups from a polymerization latex. The process comprises adding the polymerization latex to an aqueous electrolyte solution under high shear stirring at a temperature equal to or lower than the glass transition temperature of the polymer. The invention further relates to the (per)fluorinated polymers containing sulfonyl fluoride functional groups isolated by the process and characterised by a loss of weight at 200° C. lower than 1% as determined by thermogravimetric analysis.
    Type: Application
    Filed: October 22, 2010
    Publication date: August 9, 2012
    Applicant: Solvay Specialty Polymers Italy S.P.A.
    Inventors: Alessandro Veneroni, Claudio Oldani, Martina Corasaniti, Alessandro Ghielmi
  • Publication number: 20120142858
    Abstract: A novel aqueous polymerization process for making fluoropolymer dispersions is disclosed in which non-ionic non-fluorinated emulsifier is used to produce fluoropolymer emulsions. The emulsifiers contain blocks of polyethylene glycol, polypropylene glycol and/or polytetramethylene glycol. The process and fluoropolymer produced contain no fluorinated surfactant. The fluoropolymers have excellent resistance to discoloration.
    Type: Application
    Filed: November 16, 2011
    Publication date: June 7, 2012
    Applicant: Arkema Inc.
    Inventors: Ramin Amin-Sanayei, Mehdi Durali, Patrick Kappler, Greylan Burch
  • Patent number: 8178612
    Abstract: The present invention relates to an aqueous/oil emulsion containing fluoropolymer that is capable of forming thick coatings in a single pass, which coatings after drying and baking are free of cracks.
    Type: Grant
    Filed: January 19, 2005
    Date of Patent: May 15, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Jurgen Hofmans
  • Publication number: 20120116016
    Abstract: A process for producing vinyl fluoride polymer comprising polymerizing vinyl fluoride in an aqueous polymerization medium containing initiator and halogen-free surfactant with a critical micelle concentration of less than about 0.05 weight percent at 25° C. The halogen-free surfactant is present in the aqueous polymerization medium in an amount less than about 0.1 weight percent based on the weight of the aqueous polymerization medium. The aqueous polymerization medium is essentially free of halogen-containing surfactant. An aqueous dispersion comprising vinyl fluoride polymer particles present in a range of from about 5 to about 40 weight percent based on the weight of the aqueous phase, wherein said vinyl fluoride polymer particles have a Dv(50) of less than about 20 microns, and halogen-free surfactant, wherein said halogen-free surfactant is present in said aqueous dispersion in an amount less than 0.1 weight percent based on the weight of the aqueous phase.
    Type: Application
    Filed: October 19, 2011
    Publication date: May 10, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventor: RONALD EARL USCHOLD
  • Publication number: 20120116017
    Abstract: A process is provided for polymerizing fluoromonomer in an aqueous medium, wherein a dispersion of essentially surfactant-free hydrocarbon-containing oleophilic nucleation sites is first formed in the aqueous medium, and then polymerization is commenced to form a dispersion of fluoropolymer particles at the oleophilic nucleation sites, wherein the nucleation sites can be derived from hydrocarbon-containing compound. The surfactant used to stabilize the fluoropolymer dispersion can also be hydrocarbon-containing.
    Type: Application
    Filed: November 9, 2011
    Publication date: May 10, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Dipti Dilip Khasnis
  • Publication number: 20120116015
    Abstract: A polymerization process is provided, comprising polymerizing fluoromonomer in an aqueous medium to form a dispersion of fluoropolymer particles in the aqueous medium, said polymerizing being carried out in the presence of (i) polymerization initiator, and (ii) hydrocarbon-containing surfactant stabilizing the dispersion of fluoropolymer particles, the hydrocarbon-containing surfactant being passivated to reduce its the telogenic behavior.
    Type: Application
    Filed: November 9, 2011
    Publication date: May 10, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Dipti Dilip Khasnis
  • Patent number: 8158734
    Abstract: A novel aqueous polymerization process for making fluoropolymers is disclosed in which non-ionic non-fluorinated emulsifier is used to produce fluoropolymer emulsions. The emulsifiers used in the invention are those that contain segments of polyethylene glycol and/or polypropylene glycol with repeating units of 3 to 100.
    Type: Grant
    Filed: March 22, 2007
    Date of Patent: April 17, 2012
    Assignee: Arkema Inc.
    Inventors: Ramin Amin-Sanayei, Christyn Olmstead
  • Publication number: 20120004367
    Abstract: There is provided a method for producing an aqueous dispersion of fluorine-containing seed polymer (B) particles, comprising a step for preparing an aqueous dispersion of fluorine-containing polymer (A) particles by polymerizing monomer comprising at least one fluoroolefin in an aqueous dispersion in the presence of a compound (1) represented by the formula: CH2?CHCH2—O—R, wherein R is a hydrocarbon group which may have an oxygen atom, a nitrogen atom and/or a polar group, and (II) a step for seed-polymerizing ethylenically unsaturated monomer with the fluorine-containing polymer (A) particles in the aqueous dispersion of the fluorine-containing polymer (A) particles.
    Type: Application
    Filed: March 11, 2010
    Publication date: January 5, 2012
    Applicant: DAIKIN INDUSTRIES LTD.
    Inventors: Katsuhiko Imoto, Shumi Nishii, Yoshinari Fukuhara
  • Patent number: 8013071
    Abstract: A composition for aqueous coating material which has a low content of an organic solvent and presents little burden on the environment and which is excellent in storage stability. A composition for aqueous coating material, which comprises a synthetic resin containing a fluorinated copolymer (A) comprising from 40 to 60 mol % of a fluoroolefin unit, from 3 to 50 mol % of an alkyl vinyl ether or alkyl vinyl ester unit, from 4 to 30 mol % of a hydroxyl group-containing vinyl ether unit and 0.
    Type: Grant
    Filed: January 19, 2010
    Date of Patent: September 6, 2011
    Assignee: Asahi Glass Company, Limited
    Inventors: Naoko Sumi, Takashi Morizumi, Isao Kimura
  • Patent number: 7999049
    Abstract: An emulsion polymerization process for the production of fluoroelastomers 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=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 16, 2011
    Assignee: DuPont Performance Elastomers L.L.C.
    Inventors: Michael Cregg Coughlin, Ming-Hong Hung, Phan Linh Tang
  • Patent number: 7989568
    Abstract: A process comprising polymerizing in an aqueous medium at least one fluorinated olefin monomer other than vinylidene fluoride in the presence of a compound of formula (1): Rf(CH2CF2)m—(CH2)nSO3M??(1) wherein Rf is a C1 to C4 linear or branched perfluoroalkyl group, m is an integer of from 1 to 6, n is from 0 to 4, M is H, NH4, Li, Na or K, and a method of altering the surface behavior of a liquid comprising adding to the liquid the composition of a compound of formula (1).
    Type: Grant
    Filed: November 13, 2008
    Date of Patent: August 2, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Sheng Peng, Phan Linh Tang
  • Patent number: 7985790
    Abstract: A fluoropolymer composition comprising: at least one thermoplastic partially fluorinated fluoropolymer [polymer (F)]; water; less than 15% wt (based on total weight of composition) of a water-soluble solvent mixture [mixture (M)] comprising: at least one alcohol solvent [solvent (A)]; at least one glycol derivative solvent having a boiling point of at least 100° C. [solvent (GD)], wherein the solvent (GD) is a derivative of a compound comprising at least two hydroxyl groups, wherein at least one of the hydroxyl group has been derivatized to yield an ether or an ester bond.
    Type: Grant
    Filed: December 4, 2006
    Date of Patent: July 26, 2011
    Assignee: Solvay Solexis, S.p.A.
    Inventors: Fabio Polastri, Tiziana Poggio, Julio A. Abusleme