Fluorine-containing Monomer Patents (Class 524/805)
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Patent number: 10875940Abstract: 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: GrantFiled: February 5, 2019Date of Patent: December 29, 2020Assignee: AGC Inc.Inventor: Norihide Sugiyama
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Patent number: 10494554Abstract: 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: GrantFiled: June 7, 2013Date of Patent: December 3, 2019Assignees: 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
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Patent number: 9938403Abstract: 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: GrantFiled: January 11, 2016Date of Patent: April 10, 2018Assignee: 3M Innovative Properties CompanyInventors: Klaus Hintzer, Harald Kaspar, Herbert Koenigsmann, Helmut Traunspurger, Tilman C. Zipplies
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Patent number: 9714307Abstract: 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: GrantFiled: November 20, 2013Date of Patent: July 25, 2017Assignee: 3M Innovative Properties CompanyInventors: Klaus Hintzer, Harald Kaspar, Herbert Koenigsmann, Helmut Traunspurger, Tilman C. Zipplies
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Patent number: 9650479Abstract: 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: GrantFiled: December 19, 2014Date of Patent: May 16, 2017Assignees: W. L. Gore & Associates, Inc., W. L. Gore & Associates GmbHInventors: Lawrence A. Ford, Michael E. Kennedy, Shaofeng Ran, Todd S. Sayler, Gregory J. Shafer
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Patent number: 9644054Abstract: 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: GrantFiled: December 19, 2014Date of Patent: May 9, 2017Assignees: W. L. Gore & Associates, Inc., W. L. Gore & Associates GmbHInventors: Lawrence A. Ford, Michael E. Kennedy, Shaofeng Ran, Todd S. Sayler, Gregory J. Shafer
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Patent number: 9580590Abstract: 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: GrantFiled: August 27, 2012Date of Patent: February 28, 2017Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Takahiro Taira, Taku Yamanaka, Yoshinori Nanba, Atsuko Tanaka, Makoto Ono, Nobuhiko Tsuda, Taketo Kato
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Patent number: 9284690Abstract: 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 respectivType: GrantFiled: July 1, 2014Date of Patent: March 15, 2016Assignee: Taiwan Fluoro Technology Co., Ltd.Inventors: Jo-Yu Huang, Ren-Ren Chiou, Jih-Hsih Ho
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Patent number: 9260553Abstract: 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: GrantFiled: November 21, 2013Date of Patent: February 16, 2016Assignee: 3M INNOVATIVE PROPERTIES COMPANYInventors: Klaus Hintzer, Harald Kaspar, Herbert Koenigsmann, Helmut Traunspurger, Tilman C. Zipplies
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Publication number: 20150148482Abstract: 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: ApplicationFiled: May 22, 2013Publication date: May 28, 2015Inventors: Takashi Yoshimura, Kazuhiro Ohtsuka, Tadashi Ino, Noriyuki Shinoki, Masahiro Kondo
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Publication number: 20150148481Abstract: 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: ApplicationFiled: November 25, 2014Publication date: May 28, 2015Inventors: PAUL DOUGLAS BROTHERS, Subhash Vishnu Gangal, Dipti Dilip Khasnis
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Patent number: 9029471Abstract: 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: GrantFiled: September 30, 2008Date of Patent: May 12, 2015Assignee: E I du Pont du Nemours and CompanyInventors: Romain Severac, Agnes Ibos, Lamia Heuze, Renaud Laloux-Walther
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Patent number: 8969437Abstract: 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: GrantFiled: January 18, 2013Date of Patent: March 3, 2015Assignee: Daikin Industries, Ltd.Inventors: Nobuhiko Tsuda, Akinari Sugiyama
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Patent number: 8916643Abstract: 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: GrantFiled: April 18, 2011Date of Patent: December 23, 2014Assignee: Unimatec Co., Ltd.Inventors: Ji-Shan Jin, Satoshi Kurihara, Sumiko Mouri, Katsuyuki Sato
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Patent number: 8900412Abstract: 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: GrantFiled: October 31, 2011Date of Patent: December 2, 2014Assignee: Solenis Technologies Cayman, L.P.Inventors: Sachin Borkar, Marc C. Putnam
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Patent number: 8901264Abstract: 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: GrantFiled: September 9, 2010Date of Patent: December 2, 2014Assignee: Asahi Glass Company, LimitedInventors: Kazunori Sugiyama, Toyomichi Shimada, Nobuyuki Otozawa, Yuuichi Oomori, Minako Shimada
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Patent number: 8871882Abstract: 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: GrantFiled: February 14, 2012Date of Patent: October 28, 2014Assignee: Akron Polymer Systems, Inc.Inventors: Xiaoliang Zheng, Dong Zhang, Jiaokai Jing, Ted Calvin Germroth, Frank W. Harris, Thauming Kuo, Bin Wang, Douglas Stephens McWilliams
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Patent number: 8835551Abstract: 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: GrantFiled: September 11, 2008Date of Patent: September 16, 2014Assignee: 3M Innovative Properties CompanyInventors: 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
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Patent number: 8796368Abstract: 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: GrantFiled: August 8, 2008Date of Patent: August 5, 2014Assignee: Unimatec Co., Ltd.Inventors: Ji-Shan Jin, Sumiko Mouri, Katsuyuki Sato
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Publication number: 20140147745Abstract: 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: ApplicationFiled: January 29, 2014Publication date: May 29, 2014Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Mizuna TOYODA, Takehiro KOSE, Hiroki NAGAI
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Patent number: 8735520Abstract: 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: GrantFiled: October 19, 2011Date of Patent: May 27, 2014Assignee: E.I. du Pont de Nemours and CompanyInventor: Ronald Earl Uschold
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Patent number: 8735492Abstract: 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: GrantFiled: August 25, 2010Date of Patent: May 27, 2014Assignee: Daikin Industries, Ltd.Inventors: Katsuhiko Imoto, Shumi Nishii, Yoshinari Fukuhara
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Patent number: 8703998Abstract: 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: GrantFiled: June 20, 2011Date of Patent: April 22, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Sheng Peng, Phan Linh Tang
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Patent number: 8697822Abstract: 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: GrantFiled: June 26, 2006Date of Patent: April 15, 2014Assignee: Arkema Inc.Inventors: Mehdi Durali, Lotfi Hedhli, Ramin Amin-Sanayei
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Patent number: 8669034Abstract: Toner compositions, treated fluoropolymer particles, methods of making treated fluoropolymer particles, and the like, are disclosed.Type: GrantFiled: October 7, 2008Date of Patent: March 11, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Elliad Silcoff, Gili Assaf, Gil Bar-Haim, Albert Teishev
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Publication number: 20140005333Abstract: 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: ApplicationFiled: December 13, 2011Publication date: January 2, 2014Applicant: 3M INNOVATIVE PROPERTIES COMPANYInventors: Tatsuo Fukushi, Gregg D. Dahlke, Denis Duchesne, Werner M.A. Grootaert, Miguel A. Guerra, Larry A. Last, Peter J. Scott, Zai-Ming Qiu
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Publication number: 20130330621Abstract: 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: ApplicationFiled: August 19, 2013Publication date: December 12, 2013Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Mizuna NARUMI, Takehiro Kose, Hiroki Nagai
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Publication number: 20130331516Abstract: 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: ApplicationFiled: August 13, 2013Publication date: December 12, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: PAUL DOUGLAS BROTHERS, Subhash Vishnu Gangal
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Patent number: 8598290Abstract: 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: GrantFiled: June 29, 2007Date of Patent: December 3, 2013Assignee: Daikin Industries, Ltd.Inventors: Mitsuru Kishine, Masanori Kitaichi, Yousuke Nishimura, Manabu Fujisawa, Yoshiki Tanaka, Shintarou Ogata, Yutaka Ueta, Shigeru Morita
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Patent number: 8557938Abstract: 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: GrantFiled: November 10, 2005Date of Patent: October 15, 2013Assignee: Arkema Inc.Inventors: Lotfi Hedhli, Nafih Mekhilef
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Patent number: 8536269Abstract: 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: GrantFiled: August 15, 2008Date of Patent: September 17, 2013Assignee: Nova-Duct Technologies Pty LtdInventors: Xueduan Xie, Jun Qu, Rong Bai, Jianxin Zhang, Xucang Yang, Bo Chen, Jingang Zhang, Ming Zhang, Xianquan Hu, Yu Cheng
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Publication number: 20130225764Abstract: 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: ApplicationFiled: March 18, 2013Publication date: August 29, 2013Applicant: DAIKIN INDUSTRIES, LTD.Inventor: DAIKIN INDUSTRIES, LTD.
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Patent number: 8519072Abstract: 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: GrantFiled: June 23, 2011Date of Patent: August 27, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Paul Douglas Brothers, Subhash Vishnu Gangal
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Patent number: 8481660Abstract: 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: GrantFiled: January 20, 2009Date of Patent: July 9, 2013Assignee: Unimatec Co., Ltd.Inventors: Seiichiro Murata, Masayosi Horiuti, Katsuyuki Sato, Satoshi Kurihara
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Patent number: 8399703Abstract: 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: GrantFiled: July 24, 2008Date of Patent: March 19, 2013Assignee: Daikin Industries, Ltd.Inventors: Nobuhiko Tsuda, Akinari Sugiyama
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Patent number: 8394882Abstract: 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: GrantFiled: March 22, 2011Date of Patent: March 12, 2013Inventor: Zancy VonHooks
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Patent number: 8349954Abstract: 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: GrantFiled: April 2, 2009Date of Patent: January 8, 2013Assignee: Arkema Inc.Inventor: Lotfi Hedhli
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Patent number: 8338518Abstract: 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: GrantFiled: December 8, 2006Date of Patent: December 25, 2012Assignee: Arkema Inc.Inventors: Ramin Amin-Sanayei, Christyn Olmstead
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Publication number: 20120202946Abstract: 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: ApplicationFiled: October 22, 2010Publication date: August 9, 2012Applicant: Solvay Specialty Polymers Italy S.P.A.Inventors: Alessandro Veneroni, Claudio Oldani, Martina Corasaniti, Alessandro Ghielmi
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Publication number: 20120142858Abstract: 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: ApplicationFiled: November 16, 2011Publication date: June 7, 2012Applicant: Arkema Inc.Inventors: Ramin Amin-Sanayei, Mehdi Durali, Patrick Kappler, Greylan Burch
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Patent number: 8178612Abstract: 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: GrantFiled: January 19, 2005Date of Patent: May 15, 2012Assignee: E. I. du Pont de Nemours and CompanyInventor: Jurgen Hofmans
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Publication number: 20120116016Abstract: 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: ApplicationFiled: October 19, 2011Publication date: May 10, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventor: RONALD EARL USCHOLD
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Publication number: 20120116017Abstract: 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: ApplicationFiled: November 9, 2011Publication date: May 10, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Dipti Dilip Khasnis
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Publication number: 20120116015Abstract: 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: ApplicationFiled: November 9, 2011Publication date: May 10, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Dipti Dilip Khasnis
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Patent number: 8158734Abstract: 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: GrantFiled: March 22, 2007Date of Patent: April 17, 2012Assignee: Arkema Inc.Inventors: Ramin Amin-Sanayei, Christyn Olmstead
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Publication number: 20120004367Abstract: 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: ApplicationFiled: March 11, 2010Publication date: January 5, 2012Applicant: DAIKIN INDUSTRIES LTD.Inventors: Katsuhiko Imoto, Shumi Nishii, Yoshinari Fukuhara
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Patent number: 8013071Abstract: 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: GrantFiled: January 19, 2010Date of Patent: September 6, 2011Assignee: Asahi Glass Company, LimitedInventors: Naoko Sumi, Takashi Morizumi, Isao Kimura
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Patent number: 7999049Abstract: 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: GrantFiled: January 15, 2009Date of Patent: August 16, 2011Assignee: DuPont Performance Elastomers L.L.C.Inventors: Michael Cregg Coughlin, Ming-Hong Hung, Phan Linh Tang
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Patent number: 7989568Abstract: 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: GrantFiled: November 13, 2008Date of Patent: August 2, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Sheng Peng, Phan Linh Tang
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Patent number: 7985790Abstract: 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: GrantFiled: December 4, 2006Date of Patent: July 26, 2011Assignee: Solvay Solexis, S.p.A.Inventors: Fabio Polastri, Tiziana Poggio, Julio A. Abusleme