Halogen Patents (Class 562/586)
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Patent number: 11274168Abstract: To provide a monomer composition in which the solubility of the polymerization inhibitor in the cyclic monomer is good, the stability of the cyclic monomer during storage is good, and the cyclic monomer and the polymerization inhibitor are easily separated by distillation; and a method for producing a high molecular weight fluorinated polymer from the monomer composition.Type: GrantFiled: February 22, 2019Date of Patent: March 15, 2022Assignee: AGC Inc.Inventors: Susumu Saito, Wakako Hashimoto
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Patent number: 10556874Abstract: N-(1,3,4-Oxadiazol-2-yl)arylcarboxamide derivatives of the general formula (I) are described as herbicides. In this formula (I), V, X and Z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. A represents an oxadiazole radical. W is CY or N.Type: GrantFiled: June 29, 2016Date of Patent: February 11, 2020Assignee: BAYER CROPSCIENCE AKTIENGESELLSCHAFTInventors: Arnim Koehn, Christian Waldraff, Hartmut Ahrens, Ines Heinemann, Ralf Braun, Hansjoerg Dietrich, Christopher Hugh Rosinger, Elmar Gatzweiler
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Patent number: 10548318Abstract: N-(Tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide derivatives of the general formula (I) are described as herbicides. In this formula (I), V, X and Z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. A represents a tetrazole or triazole radical. W is CY or N.Type: GrantFiled: June 29, 2016Date of Patent: February 4, 2020Assignee: BAYER CROPSCIENCE AKTIENGESELLSCHAFTInventors: Arnim Koehn, Christian Waldraff, Hartmut Ahrens, Ines Heinemann, Ralf Braun, Hansjoerg Dietrich, Christopher Hugh Rosinger, Elmar Gatzweiler
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Patent number: 9416251Abstract: There is provided an article prepared from a fluoroelastomer, the fluoroelastomer being derived from an emulsion, the emulsion comprising a fluorinated emulsifier represented by the formula F—(CF2)t—[O(CF2)n]m—O—(CHF)o—(CF2)p—X.Type: GrantFiled: September 20, 2013Date of Patent: August 16, 2016Assignee: 3M INNOVATIVE PROPERTIES COMPANYInventors: Klaus Hintzer, Kai H. Lochhaas, Michael Jürgens, Harald Kaspar, Tilman C. Zipplies, André Streiter
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Patent number: 9045411Abstract: To provide a method for recovering an anionic fluorinated emulsifier, whereby an anionic fluorinated emulsifier adsorbed on a basic ion exchange resin can be simply and efficiently recovered. A mixed liquid of an aqueous inorganic acid solution, a fluorinated medium and a non-fluorinated medium, is contacted to a basic ion exchange resin having an anionic fluorinated emulsifier adsorbed thereon, to recover a liquid phase containing the fluorinated medium, or an aqueous inorganic acid solution is contacted to a basic ion exchange resin having an anionic fluorinated emulsifier adsorbed thereon, then a mixed liquid of a fluorinated medium and a non-fluorinated medium is contacted thereto, and thereafter the basic ion exchange resin and a liquid phase are separated to recover the liquid phase, whereupon from each liquid phase, an acid of the anionic fluorinated emulsifier is recovered.Type: GrantFiled: March 7, 2014Date of Patent: June 2, 2015Assignee: Asahi Glass Company, LimitedInventors: Shigeru Aida, Mizuna Toyoda, Kazuo Hamazaki
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Publication number: 20150112095Abstract: The present invention is drawn to a compound of formula (1): wherein Rf is C1 to C6 linear or branched fluoroalkyl, X is F or Cl, and R1 is H, CH3, or CH2CH3. The compound can be used to form partially fluorinated alcohols, derivatives, and polymers. Thus, the present invention provides compounds having lower fluorine content, the process for making lower fluorine containing compounds, and derivatives made from lower fluorine containing alcohols.Type: ApplicationFiled: October 17, 2013Publication date: April 23, 2015Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: ROMAN B. LARICHEV
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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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Publication number: 20140350181Abstract: The invention pertains to certain hydro-fluorocompounds of the following formula (I): RfO—RH—O—(CH2)m-[CF(X)n]—COOXa wherein: —Xa is H, a monovalent metal (preferably an alkaline metal) or an ammonium group of formula —N(R?n)4, wherein each of R?n, equal to or different from each other, independently represents a hydrogen atom or a C1-6 hydrocarbon group (preferably an alkyl group); —Rf is a C1-C6 (per)fluoroalkyl optionally comprising one or more catenary oxygen atoms, preferably Rf is a group of formula Rf—CH2—, wherein R?f is a C1-C5 perfluorinated group, possibly comprising one or more ethereal oxygens, preferably a C1-C3 perfluorinated group, possibly comprising one or more ethereal oxygens; —RH is a fluorine-free hydrocarbon group optionally comprising one or more catenary oxygen atoms; —X is F or CF3, preferably X is F; -m is 0 or 1; -n is 1 to 3, to a process for the manufacture of said hydro-fluorocompounds, to a method of making fluoropolymers in the presence of said hydro-fluorocompounds, and to flType: ApplicationFiled: May 24, 2012Publication date: November 27, 2014Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Vito Tortelli, Ivan Wlassics, Cristiano Monzani, Bradley Lane Kent, Alessandro Veneroni
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Publication number: 20140329771Abstract: The present invention is related to variants of mycolactones of formula (I), processes for the preparation thereof, pharmaceutical compositions thereof and their use in modulating inflammation, immunity and pain. Y—O—W (I), wherein Y and W are as defined in claim 1.Type: ApplicationFiled: November 16, 2012Publication date: November 6, 2014Inventors: Caroline Demangel, Nicolas Blanchard, Georges Bismuth, Jacques Eustache, Virginie Casarotto, Anne-Caroline Chany, Laure Guenin-Mace
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Patent number: 8822716Abstract: Disclosed is a method for preparing 7-halo-2-oxoheptylate, an intermediate of cilastatin. The main steps are as follows: A. Addition reaction, in which 6-halo-hexanal is reacted with a cyanide to obtain 7-halo-?-hydroxyl-heptonitrile; B. Hydrolysis reaction, in which 7-halo-?-hydroxyl-heptonitrile is converted to 7-halo-?-hydroxyl-heptylic acid; C. Esterification reaction, in which 7-halo-?-hydroxyl-heptylic acid is converted to 7-halo-?-hydroxyl-heptylate; and D. Oxidation reaction, in which 7-halo-?-hydroxyl-heptylate is converted to 7-halo-2-oxoheptylate. 7-halo-?-hydroxyl-heptylic acid or ester thereof, which is a new intermediate for synthesizing 7-halo-2-oxoheptylate or cilastatin, and a method for synthesizing cilastatin are also disclosed. The methods of the invention are suitable for commercial production because of their simple process and mild reaction condition.Type: GrantFiled: February 8, 2010Date of Patent: September 2, 2014Assignee: Zhejiang Hisoar Pharmaceutical Co., LtdInventors: He Tang, Wenqiu Yuan, Jia Fu
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Publication number: 20140243547Abstract: The present invention relates to mono- or bi-functional (per)fluoropolyethers comprising a linear (per)fluoropolyether chain having two ends, wherein one or two ends contain —CF(CF3)COF groups, to a process for preparing them and to their use as precursors in the preparation of further functionalised (per)fluoropolyethers. The invention also relates to these further functionalised (per)fluoropolyethers.Type: ApplicationFiled: September 25, 2012Publication date: August 28, 2014Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Simonetta Antonella Fontana, Claudio Adolfo Pietro Tonelli, Piero Gavezotti
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Patent number: 8710257Abstract: A method for preparing highly fluorinated carboxylic acids and theirs salts and the precursors thereof.Type: GrantFiled: November 18, 2010Date of Patent: April 29, 2014Assignee: 3M Innovative Properties CompanyInventors: Klaus Hintzer, Tilman C. Zipplies, Oleg Shyshkov
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Publication number: 20140051024Abstract: A fluorinated ester monomer is provided having formula (1) wherein R1 is H, CH3 or CF3, R2 and R3 are H or a monovalent hydrocarbon group, or R2 and R3 forms a hydrocarbon ring, R4 is a monovalent hydrocarbon group, and k is 0 or 1. A polymer obtained from the monomer has transparency to radiation with a wavelength of up to 200 nm and appropriate alkaline hydrolysis, is constructed such that any of water repellency, water slip and surface segregation may be adjusted by a choice of its structure, and is useful in forming ArF immersion lithography materials.Type: ApplicationFiled: October 23, 2013Publication date: February 20, 2014Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Takeshi KINSHO, Yuuki SUKA, Yuji HARADA, Koji HASEGAWA, Takeshi SASAMI
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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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Patent number: 8513457Abstract: A fluorine-containing unsaturated carboxylic acid represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R3 represents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R3 and W are defined as above, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R4, R5 and R6 may be combined to form a ring. This polymer compound can provide a chemically amplified resist composition that is transparent to KrF or ArF excimer laser light and has a high resolution and is capable of forming a pattern having a rectangular section with no swelling.Type: GrantFiled: May 17, 2012Date of Patent: August 20, 2013Assignee: Central Glass Company, LimitedInventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiro Yamanaka
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Patent number: 8492585Abstract: To provide a method for recovering an anionic fluorinated emulsifier, capable of easily and efficiently recovering an anionic fluorinated emulsifier adsorbed on a basic ion exchange resin. A basic ion exchange resin is brought into contact with a mixture of an aqueous inorganic acid solution and a non-aqueous fluorinated medium, or the basic ion exchange resin is brought into contact with an aqueous inorganic acid solution and then brought into contact with a non-aqueous fluorinated medium, then a phase of the non-aqueous fluorinated medium is recovered, and an acid of the anionic fluorinated emulsifier is recovered from the phase of the non-aqueous fluorinated medium.Type: GrantFiled: July 2, 2012Date of Patent: July 23, 2013Assignee: Asahi Glass Company, LimitedInventors: Junko Haga, Yasuhiko Matsuoka
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Publication number: 20130131267Abstract: 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: ApplicationFiled: January 18, 2013Publication date: May 23, 2013Applicant: DAIKIN INDUSTRIES, LTD.Inventor: DAIKIN INDUSTRIES, LTD.
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Patent number: 8440858Abstract: A method for preparing saturated partially fluorinated alkoxy carboxylic acids or salts thereof by treating a compound: (II), where Rf represents a fluorinated, linear or branched alkyl residue interruptible by one or more oxygen atoms, n is 0 or 1, with a Z-anion in a reaction medium comprising water and an organic solvent, where the Z-anion is selected from CN—, SCN— and OCN— or combinations thereof. A method of making partially fluorinated ethers of the general formula (I) wherein Rf is defined as above, n is 0 or 1, and Z is nitrile (—CN), azide (—N3), thiocyanate (—SCN) or cyanate (—OCN) group, said method comprising treating a fluorinated olefin of the general formula (II) wherein the Z-anion is CN—, OCN—, SCN— or N3?. A compound of the general formula (I) as previously described where Z is selected from SCN, OCN and N3.Type: GrantFiled: November 24, 2009Date of Patent: May 14, 2013Assignee: 3M Innovative Properties CompanyInventors: Tilman Zipplies, Klaus Hintzer, Oleg Shyshkov
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Publication number: 20130092866Abstract: The invention generally encompasses phosphonium ionic liquids, salts, compositions and their use in many applications, including but not limited to: as electrolytes in electronic devices such as memory devices including static, permanent and dynamic random access memory, as electrolytes in energy storage devices such as batteries, electrochemical double layer capacitors (EDLCs) or supercapacitors or ultracapacitors, electrolytic capacitors, as electrolytes in dye-sensitized solar cells (DSSCs), as electrolytes in fuel cells, as a heat transfer medium, among other applications. In particular, the invention generally relates to phosphonium ionic liquids, salts, compositions, wherein the compositions exhibit superior combination of thermodynamic stability, low volatility, wide liquidus range, ionic conductivity, and electrochemical stability. The invention further encompasses methods of making such phosphonium ionic liquids, salts, compositions, operational devices and systems comprising the same.Type: ApplicationFiled: December 5, 2012Publication date: April 18, 2013Inventors: Benjamin L. Rupert, Levi J. Irwin, Leanne Beer, Shilpa A. Worlikar, Steven Z. Shi
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Publication number: 20130075364Abstract: Methods for forming a pattern in a lithography process for semiconductor wafer manufacturing are provided. In an example, a method includes forming a photoresist layer over a material layer; performing a first exposure process on the photoresist layer, thereby forming an exposed photoresist layer having soluble portions and unsoluble portions; treating the exposed photoresist layer, wherein the treating includes one of performing a second exposure process on the exposed photoresist layer and forming an adsorbing chemical layer over the exposed photoresist layer; and developing the exposed and treated photoresist layer to remove the soluble portions of the photoresist layer, wherein the unsoluble portions of the photoresist layer form a photoresist pattern that exposes portions of the material layer.Type: ApplicationFiled: September 22, 2011Publication date: March 28, 2013Applicant: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY, LTD.Inventors: Chien-Wei Wang, Ko-Bin Kao, Wei-Liang Lin, Jui-Ching Wu, Chia-Hsiang Lin, Ai-Jen Jung
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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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Publication number: 20130034813Abstract: A chemically amplified positive resist composition comprising (A) a sulfonium salt of 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropionic acid, (B) an acid generator, (C) a base resin, and (D) an organic solvent is suited for ArF immersion lithography. The carboxylic acid sulfonium salt is highly hydrophobic and little leached out in immersion water. By virtue of controlled acid diffusion, a pattern profile with high resolution can be constructed.Type: ApplicationFiled: July 26, 2012Publication date: February 7, 2013Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Youichi Ohsawa, Masayoshi Sagehashi, Koji Hasegawa, Takeshi Sasami
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Patent number: 8304576Abstract: Halogenated ?-fluoroethers (or bis-derivatives thereof) can be produced by reacting a halogenated hemiacetal (or bis-derivative thereof) with sulfuryl fluoride (SO2F2) in the presence of an organic base. The reaction is conducted preferably in the presence of “a salt or complex of an organic base with hydrogen fluoride”, whereby the objective dehydroxyfluorination can proceed extremely favorably. It is still preferable to use as the starting substrate a halogenated hemiacetal prepared from fluoral or 3,3,3-trifluoropyruvic acid ester. Thus, industrially important halogenated ?-fluoroethers can be industrially produced with high selectivity and in high yield.Type: GrantFiled: May 14, 2009Date of Patent: November 6, 2012Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Manabu Yasumoto
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Publication number: 20120219596Abstract: Compounds according to formula (I) are particularly suitable for the treatment and/or prevention of a medical condition involving hypoxic, anoxic and/or inflamed mammalian tissue. Furthermore, the invention relates to the use of said compounds for preparing a medicament and to pharmaceutical preparations comprising such compounds.Type: ApplicationFiled: July 27, 2010Publication date: August 30, 2012Applicants: ETH Zurich, University of ZurichInventors: Ludwig K. Limbach, Inge K. Herrmann, Beatrice Beck-Schimmer, Wendelin J. Stark, Martin Urner
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Patent number: 8198480Abstract: This invention provides a novel compound which can be properly used as a surfactant, a method of producing a fluoropolymer, surfactant and a fluoropolymer aqueous dispersions using the novel compound. This invention is a fluoroalkylcarboxylic acid derivative which is represented by the general formula (i): Rf1(OCH2CF2CF2)n1OCX1X2CF2(Rf2)n2COOM??(i) wherein Rf1 represents a straight or branched fluoroalkyl group containing 1 to 20 carbon atoms, which fluoroalkyl group may optionally contain 1 to 5 oxygen atoms in the principal chain thereof, Rf2 represents a straight or branched fluoroalkylene group containing 1 to 25 carbon atoms, said fluoroalkylene group may optionally contain 1 to 5 oxygen atoms in the principal chain thereof, n1 represents an integer of 0 to 3, n2 represents an integer of 0 or 1, X1 and X2 are the same or different and each represents hydrogen atom or fluorine atom, and M represents NH4 or a monovalent metal element.Type: GrantFiled: August 6, 2009Date of Patent: June 12, 2012Assignee: Daikin Industries, Ltd.Inventors: Shigeru Morita, Yoshiki Tanaka, Keiko Washino, Nobuhiko Tsuda, Mitsuru Kishine
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Publication number: 20120083580Abstract: A fluorinated ester monomer is provided having formula (1) wherein R1 is H, CH3 or CF3, R2 and R3 are H or a monovalent hydrocarbon group, or R2 and R3 forms a hydrocarbon ring, R4 is a monovalent hydrocarbon group, and k is 0 or 1. A polymer obtained from the monomer has transparency to radiation with a wavelength of up to 200 nm and appropriate alkaline hydrolysis, is constructed such that any of water repellency, water slip and surface segregation may be adjusted by a choice of its structure, and is useful in forming ArF immersion lithography materials.Type: ApplicationFiled: September 22, 2011Publication date: April 5, 2012Inventors: Takeshi KINSHO, Yuuki Suka, Yuji Harada, Koji Hasegawa, Takeshi Sasami
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Publication number: 20120004365Abstract: A composition comprising a mixture of fluoropolyether acids or salts having a number average value of about 800 to about 2500 g/mol. The amount of fluoropolyether acids or salt in the mixture having a molecular weight of not more than 500 g/mol is not more than 50 ppm by weight of the total amount of fluoropolyether acids or salts in the mixture. The amount of fluoropolyether acids or salts in the mixture having a molecular weight of 2500 g/mol or greater is not more than 40% by weight of the total amount of fluoropolyether acids or salts in the mixture. Preferably the fluoropolyether acids or salts comprise an anionic group selected from the group consisting of carboxylate, sulfonate, sulfonamide anion and phosphonate. Also disclosed is an aqueous dispersion polymerization process for fluoropolymer manufacture employing polymerization agent comprising the specified mixture of fluoropolyether acids or salts.Type: ApplicationFiled: September 13, 2011Publication date: January 5, 2012Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Paul Douglas Brothers, Subhash Vishnu Gangal, Gregory Allen Chapman, Jon Lee Howell, Adam Paul Smith
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Publication number: 20110245520Abstract: A method for preparing saturated partially fluorinated alkoxy carboxylic acids or salts thereof by treating a compound: (II), where Rf represents a fluorinated, linear or branched alkyl residue interruptible by one or more oxygen atoms, n is 0 or 1, with a Z-anion in a reaction medium comprising water and an organic solvent, where the Z-anion is selected from CN—, SCN— and OCN— or combinations thereof. A method of making partially fluorinated ethers of the general formula (I) wherein Rf is defined as above, n is 0 or 1, and Z is nitrile (—CN), azide (—N3), thiocyanate (—SCN) or cyanate (—OCN) group, said method comprising treating a fluorinated olefin of the general formula (II) wherein the Z-anion is CN—, OCN—, SCN— or N3?. A compound of the general formula (I) as previously described where Z is selected from SCN, OCN and N3.Type: ApplicationFiled: November 24, 2009Publication date: October 6, 2011Inventors: Tilman Zipplies, Klaus Hintzer, Oleg Shyshkov
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Publication number: 20110213182Abstract: A process for the manufacture of a perfluorooxycarboxylate of formula (I): RfO—CF2CF2—O—CF2—COOXa (I), wherein Rf is a perfluoro(oxy)alkyl group, and Xa is H, a monovalent metal or an ammonium group of formula NRN4, with RN, equal or different at each occurrence, being H or a C1-6 hydrocarbon group, said process comprising: (A) reacting a perfluorovinylether of formula Rf—O—CF?CF2 with an ethylene glycol derivative selected among ethylene glycol (HO—CH2CH2—OH), glycolic acid (HO—CH2—COOH), glycolaldehyde (HO—CH2—CHO) and protected derivatives thereof, so as to yield the corresponding addition product of formula Rf—O—CFH—CF2—O—CH2-E, and E being selected among —CH2OH, —COOH and —CHO; (B) optionally protecting functional group E with suitable chemistry; (C) fluorinating the (protected) addition product to yield the corresponding perfluorinated addition product; (D) optionally deprotecting the perfluorinated addition product to yield corresponding acyl fluoride of formula Rf—O—CF2—CF2—O—CF2—C(O)F; and (E) hydrolType: ApplicationFiled: July 7, 2009Publication date: September 1, 2011Applicant: SOLVAY SOLEXIS S.P.A.Inventors: Giuseppe Marchionni, Vito Tortelli
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Publication number: 20110207880Abstract: The present invention provides peroxidic fluoropolyether and a fluorin-containing dispersion obtained from polymerization of fluorin-containing monomers in the presence of peroxidic fluoropolyether as a surfactant. The peroxidic fluoropolyether can be used as surfactant for producing aqueous dispersion of fluorin-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: ApplicationFiled: August 15, 2008Publication date: August 25, 2011Applicant: Nova-Duet Technologies, Pty. Ltd.Inventors: Xueduan Xie, Jun Qu, Rong Bai, Jianxin Zhang, Xucang Yang, Bo Chen, Jingang Zhang, Ming Zhang, Xianquan Hu, Yu Cheng
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Patent number: 7985877Abstract: The present invention provides a process for producing 1,1,1,3,3,3-hexafluoro-2-methoxypropane, wherein a novel compound, 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof is decarboxylated, or wherein an olefin compound represented by chemical formula (4): CF2?C(CF3)(OCH3) is reacted with a fluorinating agent; and a process for producing 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof by reacting a hydroxycarboxylic ester with a methylating agent and then hydrolyzing the reaction product, or hydrolyzing the hydroxycarboxylic ester and then reacting the resulting product with a methylating agent. In accordance with the invention, 1,1,1,3,3,3-hexafluoro-2-methoxypropane, which is useful as a raw material for, for example, the anesthetic Sevoflurane, can be produced efficiently and at low cost.Type: GrantFiled: May 31, 2007Date of Patent: July 26, 2011Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto, Yoshichika Kuroki, Atsushi Suzuki, Akinari Sugiyama
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Publication number: 20110152567Abstract: To provide a method for producing a perfluoro compound having hydroxyl groups, whereby agglomeration of a reduction reaction intermediate tends not to occur during a reduction reaction, and a perfluoro compound having —C(?O)OH can be used as a starting material. Reducing (A-C(?O)=Q=)nRfn in the presence of a metal hydride and an inorganic salt of lithium in an alcohol solvent to obtain (B—CH(OH)-Q-)n-m,(A-C(?O)-Q-)mRfn, wherein A is a hydroxyl group, a C1-5 alkoxy group, a hydrogen atom, a C1-5 alkyl group or the like, Q is a perfluoroalkylene group or the like, n is an integer of at least 1, m is an integer at least 0 and less than n, Rfn is an n valent perfluoro saturated hydrocarbon group or the like, and B is a group depending on A wherein when A is a hydroxyl group, a C1-5 alkoxy group or the like, B is a hydrogen atom, and when A is a hydrogen atom, a C1-5 alkyl group or the like, B is the same group as A.Type: ApplicationFiled: March 2, 2011Publication date: June 23, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Daisuke SHIRAKAWA, Yoshiyuki Gozu, Yoshitomi Morisawa
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Publication number: 20110082312Abstract: The present invention relates to a process for the preparation of compounds containing CF3O groups using compounds containing at least one group Y, in which Y=—Hal, —OSO2(CF2)zF, —OSO2CzH2z+1 (z=1-10), —OSO2F, —OSO2Cl, —OC(O)CF3— or —OSO2Ar, to a process for the preparation of compounds containing CF3O groups using KOCF3 and/or RbOCF3, and to novel compounds containing CF3O groups, and to the use thereof.Type: ApplicationFiled: May 4, 2009Publication date: April 7, 2011Applicant: MERCK PATENT GESELLSCHAFT MIT DESCHRANKTER HAFTUNGInventors: Nikolai (Mykola) Ignatyev, Wolfgang Hierse, Martin Seidel, Andreas Bathe, Jens Schroeter, Karsten Koppe, Thorsten Meier, Peter Barthen, Walter Frank
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Publication number: 20110034604Abstract: The invention provides a fluorinated surfactant having the general formula: [Rf—(O)t—CHF—(CF2)n—COO—]iXi+??(I) wherein Rf represents a partially or fully fluorinated aliphatic group optionally interrupted with one or more oxygen atoms, t is 0 or 1 and n is 0 or 1, Xi+ represents a cation having a valence i and i is 1, 2 or 3. The surfactant can be used in emulsion polymerization of fluoromonomers to prepare fluoropolymers.Type: ApplicationFiled: October 19, 2010Publication date: February 10, 2011Inventors: Klaus Hintzer, Michael Jürgens, Harald Kaspar, Herbert Königsmann, Andreas R. Maurer, Werner Schwertfeger, Tilman C. Zipplies
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Patent number: 7838608Abstract: The invention provides a fluorinated surfactant having the general formula: [Rf—(O)t—CHF—(CF2)n—COO—]iXi+??(I) wherein Rf represents a partially or fully fluorinated aliphatic group optionally interrupted with one or more oxygen atoms, t is 0 or 1 and n is 0 or 1, Xi+ represents a cation having a valence i and i is 1, 2 or 3. The surfactant can be used in emulsion polymerization of fluoromonomers to prepare fluoropolymers.Type: GrantFiled: December 19, 2006Date of Patent: November 23, 2010Assignee: 3M Innovative Properties CompanyInventors: Klaus Hintzer, Michael Jürgens, Harald Kaspar, Herbert Königsmann, Andreas R Maurer, Werner Schwertfeger, Tilman C. Zipplies
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Patent number: 7820859Abstract: The present invention provides a commercially viable process for the preparation of highly pure and optically active L-(+)-lactic acid and S-(?)-methyl lactate, in high yield, obtained from esterification of aqueous crude lactic acid solution produced by sugar cane juice fermentation broth and methanol in continuous counter current trickle phase approach or in continuous counter current bubble column manner, using stabilizers and the methyl lactate so obtained is recovered and followed by purification of reasonably pure methyl lactate using reagent mixture such as sodium bi-carbonate, mono-ethanolamine or di-ethanolamine, urea or sodium-bicarbonate, mono-ethanolamine or di-ethanolamine, thiourea to reduce the impurity of dimethyl ester of dicarboxylic such as dimethyl oxalate or di-methyl succinate or methyl ester of mono-carboxylic acid such as methyl pyruvate present as an impurity, so as to get highly pure S-(?)-methyl lactate followed by hydrolyzing highly pure S-(?)-methyl lactate using highly pure lactiType: GrantFiled: December 30, 2005Date of Patent: October 26, 2010Assignee: Council of Scientific & Industrial ResearchInventors: Prashant Purushottam Barve, Bhaskar Dattatreya Kulkarni, Sanjay Narayan Nene, Ravindra William Shinde, Milind Yashwant Gupte, Chandrashekhar Narayan Joshi, Gandhali Arun Thite, Vilas Bhiku Chavan, Tushar Ramchandra Deshpande
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Publication number: 20100197963Abstract: Provided are fluorinated oxy-carboxylic acids, derivatives of oxy-carboxylic acids, and methods of preparing oxy-carboxylic acids and derivatives thereof.Type: ApplicationFiled: September 26, 2008Publication date: August 5, 2010Applicant: 3M Innovative Properties CompanyInventors: Werner Schwertfeger, Klaus Hintzer, Egon Obermaier
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Patent number: 7737299Abstract: In the production of 2,2,3,3-tetrafluorooxethane by reaction of tetrafluoroethylene with a compound of formaldehyde generation source in anhydrous hydrogen fluoride, the reaction is carried out in the presence of polyfluoroalkylcarboxylic acid or polyfluoroalkyl ester thereof, represented by the following general formula RfCOORf? (where Rf is a polyfluoroalkyl group having 1-5 carbon atoms, and Rf? is a hydrogen atom or a polyfluoroalkyl group having 1-5 carbon atoms), preferably CF3COOH, CF3COOCH2CF2CF3, or CF3COOCH2CF3, whereby a high reaction yield can be attained.Type: GrantFiled: February 10, 2005Date of Patent: June 15, 2010Assignee: Unimatec Co., Ltd.Inventors: Sunao Ikeda, Takehiro Sonoi
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Publication number: 20100099845Abstract: Disclosed are processes for preparing a protected trifluorothreonine, or salt thereof or carboxylate derivative thereof, the process comprising: dihydroxylation of an alkene to yield a dihydroxyl compound; conversion of the dihydroxyl compound to a monohydroxyl compound; protection of the monohydroxyl compound to yield an azide compound; transformation of the azide compound to yield an amino compound; protection of the amino compound to yield a protected amine compound; and oxidation of the protected amine compound to yield the protected trifluorothreonine. Also disclosed are compounds having the structure: or salt thereof or carboxylate derivative thereof, wherein P2 is a hydroxyl protecting group, and wherein P3 is an amine protecting group. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.Type: ApplicationFiled: September 14, 2007Publication date: April 22, 2010Applicant: University of Utah Research FoundationInventors: Bruce Yu, Zhong-Xing Jiang, Nu Xiao
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Publication number: 20100010255Abstract: The present invention provides a novel ?-fluoromethoxycarboxylic ester represented by Formula (1): (CF3)2C(OCH2F)COOR wherein R is a hydrocarbon group that may have a substituent; a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether, the process including hydrolyzing and decarboxylating the ?-fluoromethoxycarboxylic ester; and a process for producing an ?-fluoromethoxycarboxylic ester represented by Formula (1): (CF3)2C (OCH2F)COOR, the process including reacting an ?-hydroxycarboxylic ester represented by Formula (2): (CF3)2C(OH)COOR with a halofluoromethane in the presence of an alkaline compound. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as an anesthetic compound, can be efficiently produced at low cost.Type: ApplicationFiled: June 27, 2007Publication date: January 14, 2010Applicant: Daikin Industries LTdInventors: Tatsuya Ohtsuka, Yoshichika Kuroki, Atsukhi Suzuki
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Patent number: 7589234Abstract: This invention provides a novel compound which can be properly used as a surfactant, a method of producing a fluoropolymer, surfactant and a fluoropolymer aqueous dispersions using the novel compound. This invention is a fluoroalkylcarboxylic acid derivative which is represented by the general formula (i): Rf1(OCH2CF2CF2)n1OCX1X2CF2(Rf2)n2COOM??(i) wherein Rf1 represents a straight or branched fluoroalkyl group containing 1 to 20 carbon atoms, which fluoroalkyl group may optionally contain 1 to 5 oxygen atoms in the principal chain thereof, Rf2 represents a straight or branched fluoroalkylene group containing 1 to 25 carbon atoms, said fluoroalkylene group may optionally contain 1 to 5 oxygen atoms in the principal chain thereof, n1 represents an integer of 0 to 3, n2 represents an integer of 0 or 1, X1 and X2 are the same or different and each represents hydrogen atom or fluorine atom, and M represents NH4 or a monovalent metal element.Type: GrantFiled: July 2, 2004Date of Patent: September 15, 2009Assignee: Daikin Industries, Ltd.Inventors: Shigeru Morita, Yoshiki Tanaka, Keiko Washino, Nobuhiko Tsuda, Mitsuru Kishine
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Publication number: 20090163653Abstract: To provide a perfluorocarboxylic acid salt excellent in a surface tension reducing ability. A perfluorocarboxylic acid salt having an iron content of at most 10 ppm by mass and represented by the following formula (1): RF(OCF(X1)CF2)k-1OCF(X2)COO?M+??(1) wherein RF is a C1-10 monovalent perfluorinated organic group, each of X1 and X2 is independently a fluorine atom or a trifluoromethyl group, k is an integer of at least 1, and M+ is an ammonium ion or an alkyl-substituted ammonium ion.Type: ApplicationFiled: February 24, 2009Publication date: June 25, 2009Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Hirokazu TAKAGI, Ryuji Seki
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Publication number: 20090156861Abstract: The present invention provides a process for producing 1,1,1,3,3,3-hexafluoro-2-methoxypropane, wherein a novel compound, 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof is decarboxylated, or wherein an olefin compound represented by chemical formula (4): CF2?C(CF3)(OCH3) is reacted with a fluorinating agent; and a process for producing 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof by reacting a hydroxycarboxylic ester with a methylating agent and then hydrolyzing the reaction product, or hydrolyzing the hydroxycarboxylic ester and then reacting the resulting product with a methylating agent. In accordance with the invention, 1,1,1,3,3,3-hexafluoro-2-methoxypropane, which is useful as a raw material for, for example, the anesthetic Sevoflurane, can be produced efficiently and at low cost.Type: ApplicationFiled: May 31, 2007Publication date: June 18, 2009Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto, Yoshichika Kuroki, Atsushi Suzuki, Akinari Sugiyama
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Publication number: 20080159954Abstract: The invention relates to the subjects characterized in the patent claims, namely metal chelates having a perfluorinated PEG radical, processes for their preparation, and their use, processes for their preparation and their use in NMR and X-ray diagnosis, radiodiagnosis and radiotherapy, and in MRT lymphography.Type: ApplicationFiled: October 17, 2007Publication date: July 3, 2008Inventors: Johannes Platzek, Heiko Schirmer, Hanns-Joachim Weinmann, Bernd Misselwitz, Ludwig Zorn
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Patent number: 7339073Abstract: A method for obtaining a 5-bromolevulinic acid methyl ester or a 5-chlorolevulinic acid methyl ester from either a bromination mixture or a chlorination mixture, containing either a 5-bromo-levulinic acid methyl ester or a 5-chlorolevulinic acid methyl ester, respectively, produced by either brominating or chlorinating levulinic acid or a levulinic acid methyl ester, and further including the steps of dissolving the bromination or chlorination mixture in an organic solvent or solvent mixture and cooling the solution, preferably to ?20° C.–?40° C., with the 5-bromolevulinic acid methyl ester or 5-chlorolaevulinic acid methyl ester being crystallized out of the solution. The 5-bromolevulinic acid methyl ester or 5-chlorolevulinic acid is then isolated by draining off the solution with the remaining bromination mixture or chlorination mixture, as appropriate.Type: GrantFiled: November 22, 2002Date of Patent: March 4, 2008Inventor: Sven Aldenkortt
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Patent number: 7321059Abstract: Compounds of formula (I): or salts or solvate thereof, wherein: n and N independently represent an integer 2 to 12; m1 and m2 independently represent an integer 1 to 15; and R1 and R2 independently represent —(CO)xC1-9 alkyl or —(CO)xC1-9 fluoroalkyl, which fluoroalkyl moiety contains at least 1 fluorine atom and not more than 3 consecutive perfluorocarbon atoms wherein x represents 0 or 1, as well as pharmaceutical formulations containing such compounds and processes for the manufacture of such compounds are disclosed. Intermediates of such compounds and processes for the manufacture of such intermediates are also disclosed.Type: GrantFiled: October 17, 2002Date of Patent: January 22, 2008Assignee: Glaxo Group LimitedInventors: Brian Edgar Looker, Christopher James Lunniss, Alison Judith Redgrave
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Patent number: 7195752Abstract: A pharmaceutical aerosol formulation that includes a particulate medicament, one or more fluorocarbon or hydrogen-containing fluorocarbon propellants and a compound of the general formula (I) or a salt or solvate thereof is disclosed, wherein A represents a straight chain C1-16 alkylene substituted by n groups of formula B; n represents an integer 1 to 3; and B independently represents C1-4 fluoroalkylC0-6 alkylene-, C1-4 fluoroalkylC0-6 alkylene-O—, or C1-4 alkylC0-6 alkylene-O— wherein at least one substituent of formula B contains at least one fluorine atom and each C1-4 fluoroalkyl- moiety contains one or more fluorine atoms but not more than 3 consecutive perfluorinated carbon atoms. Compounds of formula (I) and uses of such compounds are also disclosed.Type: GrantFiled: August 2, 2002Date of Patent: March 27, 2007Assignee: Glaxo Group LimitedInventors: Istvan Kaldor, Brian Edgar Looker, Christopher James Lunniss, Alison Judith Redgrave
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Patent number: 7161030Abstract: Hydrofluoroethers of formula: T-CFX?—O—Rf—CFX-T???(II) wherein: T=CH3; X, X?, equal to or different from each other, are selected between F, CF3; T00?=F, Cl, H, C1–C3 perfluoroalkyl, CH3, CH2OH, COCl, CHO, CO2H; Rf is a perfluoroalkylene or a perfluoropolyoxyalkylene and respective preparation process by reduction with hydrogen in the presence of a platinum catalyst supported on metal fluorides of the corresponding compounds with at least one —COCl end group.Type: GrantFiled: July 31, 2003Date of Patent: January 9, 2007Assignee: Solvay Solexis S.p.A.Inventors: Rosaldo Picozzi, Antonella Di Meo, Claudio Tonelli
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Patent number: 6982286Abstract: The present invention is directed to carbocyclic hydrazino compounds that function as inhibitors of copper-containing amine oxidases commonly known as semicarbazide-sensitive amine oxidases (SSAO), including the human SSAO known as Vascular Adhesion Protein-I (VAP-1). These SSAO inhibitors have therapeutic utility as drugs to treat conditions and diseases including, but not limited to, a number of inflammatory conditions and diseases (in particular chronic inflammatory conditions such as chronic arthritis, inflammatory bowel diseases, and chronic skin dermatoses), diseases related to carbohydrate metabolism and to aberrations in adipocyte differentiation or function and smooth muscle cell function, and vascular diseases. The novel compounds have the general formula: or a pharmaceutically acceptable solvate, hydrate, or salt thereof wherein R1 to R11 are as defined herein.Type: GrantFiled: July 12, 2001Date of Patent: January 3, 2006Assignee: Biotie Therapies Corp.Inventors: David John Smith, Ferenc Fülöp, Marjo Pihlavisto, László Lázár, Sakari Alaranta, Petri Vainio, Zsolt Szakonyi
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Patent number: 6923921Abstract: Described are fluorinated polyether compounds having a molecular weight range between 750 g/mol and 4000 g/mol where such polyether compounds are intermediates used in fluorinated compositions for treating various substrates.Type: GrantFiled: December 30, 2002Date of Patent: August 2, 2005Assignee: 3M Innovative Properties CompanyInventors: Richard M. Flynn, Daniel R. Vitcak, Richard S. Buckanin, Cheryl L. S. Elsbernd