Halogen In Acid Moiety Patents (Class 560/184)
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Patent number: 10000444Abstract: A fluorine-containing ether monocarboxylic acid aminoalkyl ester represented by the general formula: CnF2n+1O[CF(CF3)CF2O]aCF(CF3)COO(CH2)bNR1R2 (wherein R1 is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group, or an aralkyl group, preferably an alkyl group having 1 to 6 carbon atoms or an aryl group; R2 is an alkyl group having 1 to 12 carbon atoms, an aryl group, or an aralkyl group, preferably an alkyl group having 1 to 6 carbon atoms or an aryl group; n is an integer of 1 to 3; a is an integer of 2 to 20, preferably an integer of 4 to 10; and b is an integer of 1 to 12, preferably an integer of 1 to 3). Such a fluorine-containing ether monocarboxylic acid ester having an amino group at the end of the ester group is produced by reacting a perfluoroether carboxylic acid fluoride compound CnF2n+1O[CF(CF3)CF2O]aCF(CF3)COF and a hydroxyalkyl amine compound HO(CH2)bNR1R2 in the presence of an alkali metal fluoride.Type: GrantFiled: February 3, 2015Date of Patent: June 19, 2018Assignee: Unimatec Co., Ltd.Inventor: Keisuke Kokin
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Patent number: 9758470Abstract: A bis(perfluoroether carboxylic acid alkyl)amino ester represented by the general formula: {CnF2n+1O[CF(CF3)CF2O]aCF(CF3)COO(CH2)b}2NR, wherein R is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group, or an aralkyl group; preferably an alkyl group having 1 to 6 carbon atoms or an aryl group; n is an integer of 1 to 3; a is an integer of 0 to 20, preferably an integer of 1 to 6; and b is an integer of 1 to 12, preferably an integer of 1 to 4. The bis(perfluoroether carboxylic acid alkyl)amino ester having an amino group at the end of the ester group is produced by reacting a perfluoroether carboxylic acid fluoride compound of the formula: CnF2n+1O[CF(CF3)CF2O]aCF(CF3)COF and a bis(hydroxyalkyl)amine compound of the formula: HO(CH2)bNR(CH2)bOH at a molar ratio of 2:1 in the presence of an alkali metal fluoride.Type: GrantFiled: July 16, 2014Date of Patent: September 12, 2017Assignee: Unimatec Co., Ltd.Inventor: Keisuke Kokin
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Patent number: 9394243Abstract: The invention relates to (per)fluoropolyether block copolymers comprising: A) a fluoropolyoxyalkylene segment (chain Ra) comprising one or more units of formula (CHXCF2CF2O)— in which X is hydrogen or fluorine; B) a (per)fluoropolyoxyalkylene segment (chain Rf), that is to say a segment comprising recurring units having at least one catenary ether bond and at least one fluorocarbon moiety, said (per)fluoropolyoxyalkylene segment being different from chain Ra and having a molecular weight higher than 400 g/mol. These copolymers are endowed with improves lubricant properties or with improved water and oil-repellence properties.Type: GrantFiled: June 20, 2012Date of Patent: July 19, 2016Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Claudio Adolfo Pietro Tonelli, Simonetta Antonella Fontana, Marco Galimberti, Piero Gavezotti
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Patent number: 9228052Abstract: Provided is an allyl group-modified fluorooxyalkylene group-containing polymer that is represented by the following general formula (1) and has a number average molecular weight of 1,000 to 50,000 in terms of polystyrene, where Rf represents a monovalent or divalent fluorooxyalkylene group-containing polymer residue; “m” represents 1 or 2; X represents F or CF3; “n” represents an integer of 0 to 10; and ? represents 1 or 2. The fluorooxyalkylene group-containing polymer is excellent in terms of thermal stability and chemical stability, in addition to water- and oil-repellency, releasability, chemical resistance, lubricity, durability, antifouling property, and fingerprint-wiping property.Type: GrantFiled: October 27, 2014Date of Patent: January 5, 2016Assignee: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Ryusuke Sakoh, Takashi Matsuda
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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: 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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Patent number: 8791293Abstract: According to the present invention, there is provided a fluorine-containing sulfonate resin having a repeating unit of the following general formula (3). In order to prevent deficiency such as roughness after pattern formation or failure in pattern formation, the fluorine-containing sulfonate resin incorporates therein a photoacid generating function and serves as a resist resin in which “a moiety capable of changing its developer solubility by the action of an acid” and “a moiety having a photoacid generating function” are arranged with regularity.Type: GrantFiled: August 2, 2012Date of Patent: July 29, 2014Assignee: Central Glass Company, LimitedInventors: Kazunori Mori, Satoru Narizuka, Fumihiro Amemiya, Masaki Fujiwara
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Publication number: 20140162188Abstract: A positive resist composition is provided comprising a polymer comprising recurring styrene units having an ester group bonded to a CF3—C(OH)—R3 group (R3?H, CH3, or CF3) such as 1,1,1,3,3,3-hexafluoro-2-propanol and having a Mw of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.Type: ApplicationFiled: November 15, 2013Publication date: June 12, 2014Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Koji Hasegawa, Masaki Ohashi
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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: 20140024842Abstract: The invention discloses a method for the preparation of tert-butyl 6-chloro-3,5-dioxohexanoate from Meldrum's acid derivative and its use for the preparation of tert-butyl(4R,65)-(6-hydroxymethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetate (BHA), Rosuvastatin and Atorvastatin.Type: ApplicationFiled: March 29, 2012Publication date: January 23, 2014Applicant: LONZA LTDInventors: Christian Noti, Guixian Hu, Barry Jackson
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Patent number: 8592622Abstract: A polymerizable fluorine-containing compound represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R2 represents an acid-labile protecting 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 R2, 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 resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.Type: GrantFiled: January 4, 2011Date of Patent: November 26, 2013Assignee: Central Glass Company, LimitedInventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka
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Publication number: 20130267714Abstract: Compounds of the formula (I) in the form of a mixture of predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1??(I), wherein: Z1 is a C-bonded, secondary phosphine group of the formula —P(R)2, wherein R is a hydrocarbon radical or O-atom(s)-containing heterohydrocarbon radical having 1 to 18 carbon atoms and optionally substituted by C1-C6-alkyl, trifluoromethyl, C1-C6-alkoxy, trifluoromethoxy, (C1-C4-alkyl)2-amino, (C6H5)3Si, (C1-C12-alkyl)3Si or halogen; Q is selected from the group consisting of: (i) an optionally substituted achiral aromatic group, wherein the achiral aromatic group is bonded directly to Z1 through a carbon atom of the achiral aromatic group and bonded directly to P*R0R1 through a carbon atom of the achiral aromatic group, and (ii) an optionally substituted C1-C4-alkylene group; P* is a chiral phosphorus atom; R0 is methyl; and R1 is a C-bonded optically enriched or optically pure chiral, mono- or polycyclic, nonaromatic hydrocarbon ring; and preparType: ApplicationFiled: April 26, 2013Publication date: October 10, 2013Inventors: Benoit PUGIN, Matthias LOTZ, Heidi LANDERT, Adrian WYSS, Raphael AARDOOM, Bjorn GSCHWEND, Andreas PFALTZ, Felix SPINDLER
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Publication number: 20130165659Abstract: The present invention relates to a novel method for preparing a compound of formula (2) as the intermediate, which can be effectively used for preparation of a compound of formula (1) exhibiting good inhibitory activity against dipeptidyl peptidase IV enzyme.Type: ApplicationFiled: August 25, 2011Publication date: June 27, 2013Applicant: LG LIFE SCIENCES LTD.Inventors: Bong Chan Kim, Kyu Young Kim, Hee Bong Lee, Ji Eun An, Kyu Woong Lee
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Patent number: 8444857Abstract: A method for purifying a fluorinated carboxylic acid having an etheric oxygen atom and its derivative, with small decomposition and inclusion of impurities. A liquid containing at least one member selected from the group consisting of a fluorinated compound represented by application formulae (1) and (2) is held at a heating temperature of at most 150° C. and distilled. Further, the liquid is a liquid obtained from any of a waste liquid after an aqueous emulsion of a fluoropolymer is coagulated and the fluoropolymer is separated, an aqueous liquid obtained by cleaning an exhaust gas in a step of drying and/or a step of heat treatment of the separated fluoropolymer, and a liquid obtained by cleaning an anion exchange resin which has been brought into contact with the waste liquid or an aqueous dispersion obtained from the aqueous emulsion of the fluoropolymer, with an alkaline aqueous solution.Type: GrantFiled: December 9, 2010Date of Patent: May 21, 2013Assignee: Asahi Glass Company, LimitedInventors: Hirokazu Takagi, Ryuji Seki
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Publication number: 20120136151Abstract: The present invention relates to novel intermediate compounds used in preparing Rosuvastatin or the pharmaceutically acceptable salts thereof, to a method for preparing same, and to a method for preparing Rosuvastatin or the pharmaceutically acceptable salts thereof from the intermediates. The preparation method of the present invention has the effect of providing Rosuvastatin hemi-calcium salts with an excellent yield rate.Type: ApplicationFiled: April 8, 2010Publication date: May 31, 2012Inventors: Hongwoo Lee, Daejong Park, Choongleol Yoo, Donghyuk Nam, Hohyung Ryu, Dongjin Kim
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Publication number: 20120077121Abstract: Fluoroalcohol compounds of formula (1) are useful in producing polymers which are used as the base resin to formulate radiation-sensitive resist compositions having transparency to radiation having a wavelength of up to 500 nm and improved development characteristics. R1 is hydrogen or a monovalent C1-C20 hydrocarbon group in which any constituent —CH2— moiety may be replaced by —O— or —C(?O)—, Aa is a (k1+1)-valent C1-C20 hydrocarbon or fluorinated hydrocarbon group, and k1 is 1, 2 or 3.Type: ApplicationFiled: September 19, 2011Publication date: March 29, 2012Inventors: Koji HASEGAWA, Takeru Watanabe, Tomohiro Kobayashi, Takeshi Kinsho
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Publication number: 20120040189Abstract: To provide a surface treating agent and a composition for surface treatment capable of forming a coating film excellent in the water/oil repellency, the efficiency for removal of oil-and-fat stains, alkali resistance and heat resistance and having a low coefficient of friction; a method for treating the surface of an article by using the surface treating agent or the composition for surface treatment; an article having surface treatment applied; and a novel fluorinated ether compound useful as a surface treating agent. A surface treating agent comprising a compound represented by the following formula (A): RFO(CF2CF2O)aCF2C(O)N(H)b(-Q-OC(O)C(R)?CH2)2-b??(A) wherein RF is a C1-20 perfluoro monovalent saturated hydrocarbon group or the like; a is an integer of from 1 to 200; b is 0 or 1; Q is a C1-6 alkylene group or the like; and R is a hydrogen atom or a C1-3 alkyl group.Type: ApplicationFiled: October 21, 2011Publication date: February 16, 2012Applicant: Asahi Glass Company, LimitedInventors: Daisuke Shirakawa, Yoshiyuki Gozu, Taiki Hoshino
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Publication number: 20120016153Abstract: The invention relaters to a process for the production of an (S)- or (R)-4-halo-3-hydroxybutyrate, comprising reacting a 4-haloacetoacetate with hydrogen in the presence of a solvent, the solvent being a solvent mixture, which comprises a first solvent and a second solvent, wherein the first solvent is an aliphatic alcohol, preferably methanol, ethanol or propanol, and the second solvent is aprotic and comprises at least one oxygen atom; and a catalyst of the formula [RuXYZ]X, wherein X is halogen, preferably Cl or Br, or OAc, acetoacetate, allyl or ClO4, Y is a bidentate organic ligand having two phosphine groups, and Z is an arene, preferably cymene, benzene, xylene or toluene, or a polyene, preferably a diene, or an alkene.Type: ApplicationFiled: May 10, 2011Publication date: January 19, 2012Inventors: Dario Veghini, Markus Bicker, Miguel Angel Caraucán Dávila, Golo Heckmann, Thomas Ward, Christophe Malan, Julien Pierron, Antonio Zanotti-Gerosa, Hans Nedden, Laleh Jafarpour
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Publication number: 20110301378Abstract: Esters of 4-fluorosubstituted 3-oxo-alcanoic acids can be prepared by addition reaction of ketene with the respective acid chloride, subsequent esterification and hydrodechlorination. Preferred reaction products are esters of 4,4-difluoro-3-oxo-butanoic acid.Type: ApplicationFiled: August 14, 2008Publication date: December 8, 2011Applicant: SOLVAY (SOCIETE ANONYME)Inventor: Max Josef Braun
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Patent number: 8044235Abstract: A monomer is provided which is excellent in reactivity, can give high heat resistance and high refractive index, and has two or more polymerizable functional groups with different polymerization properties and an aromatic ring in the molecule. An industrial advantageous process for producing the monomer is also provided. The monomer is an aromatic isocyanate compound containing a (meth)acryloyl group, and is represented by Formula (I): wherein R1 is a single bond or a linear or branched alkylene group of 1 to 5 carbon atoms, R2 is a hydrogen atom or a methyl group, R3 is a single bond or a linear or branched alkylene group of 1 to 3 carbon atoms, X is independently a halogen atom or an electron-withdrawing group, m is an integer ranging from 0 to 4, n is an integer ranging from 1 to 3, and 1?m+n?5.Type: GrantFiled: March 15, 2006Date of Patent: October 25, 2011Assignee: Showa Denko K.K.Inventors: Kaneo Nozawa, Katsutoshi Ohno, Yotaro Hattori
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Patent number: 8026383Abstract: The invention relates to novel synthesis methods for the preparation of statin derivatives, which methods proceed by way of a key intermediate of formula I wherein X is halogen, acyloxy, activated hydrocarbyloxy, activated hydrocarbylthio or —N(CH3)OCH3, Ra is a hydroxy-protecting group and Rb is a carboxy-protecting group, and, as well as to the compound of formula I, to further new intermediates and methods for their preparation by Friedel-Crafts acylation.Type: GrantFiled: November 4, 2010Date of Patent: September 27, 2011Assignee: BASF SEInventors: Reinhold Öhrlein, Gabriele Baisch, Nicole End, Stephan Burkhardt, Martin Studer
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Patent number: 8022245Abstract: 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: GrantFiled: June 27, 2007Date of Patent: September 20, 2011Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Ohtsuka, Yoshichika Kuroki, Atsushi Suzuki
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Patent number: 8017786Abstract: The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form —OCH2O—, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.Type: GrantFiled: May 14, 2007Date of Patent: September 13, 2011Assignee: Northwest UniversityInventors: Xiaohui Zheng, Qunzheng Zhang, Shixiang Wang, Xinfeng Zhao
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Patent number: 8013182Abstract: The present invention provides a process for producing a novel compound, i.e., ?-chloromethoxycarboxylic acid ester represented by General Formula (1): (CF3)2C(OCH2Cl)COOR, wherein R is a hydrocarbon group which may be substituted with at least one atom selected from the group consisting of halogen, oxygen, nitrogen, and sulfur atoms, comprising reacting an ?-methoxycarboxylic acid ester represented by General Formula (2): (CF3)2C(OCH3)COOR, wherein R is as defined above, with molecular chlorine; and a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether represented by a chemical formula (CF3)2CH(OCH2F), comprising fluorinating and decarboxylating the ?-chloromethoxycarboxylic acid ester. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as a compound having an anesthetic property, can be produced efficiently and at a low cost.Type: GrantFiled: November 6, 2008Date of Patent: September 6, 2011Assignee: Daikin Industries, Ltd.Inventors: Yoshihiro Yamamoto, Tatsuya Ohtsuka
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Patent number: 8008523Abstract: A process for preparing monocarboxylic perfluoropolyethers of formula: A-O—(RF)z—(CFY)t—C(O)OX (I) wherein: X is H, C1-C10 alkyl, or an aryl group; Y=F, CF3; t=1, 2 or 3; A is a C1-C4 perfluoroalkyl end group; z=0 or 1; RF is a perfluorooxyalkylene chain; having a number average molecular weight in the range 180-8,000; comprising the following steps: a) one or more distillations of perfluoropolyethers (PFPE) of formula T-O—(RF)z-T? (II) wherein: z and RF are as above defined; T, T?, equal to or different from each other, are selected from acyl fluoride or carbonyl-containing functional end groups and non functional end groups to obtain one PFPE fraction of formula (II) wherein the difference between the minimum and the maximum molecular weight of the components is lower than or equal to 600; b) partial fluorination of the fraction obtained in a); c) esterification c1) and/or hydrolysis c2) of the mixture obtained in b); d) distillation of the product obtained in c2) or in c1).Type: GrantFiled: April 3, 2007Date of Patent: August 30, 2011Assignee: Solvay Solexis S.p.A.Inventors: Giuseppe Marchionni, Ugo De Patto, Pier Antonio Guarda
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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: 20110118482Abstract: Compounds of the formula (I), in the form of mixtures comprising predominantly one diastereomer or in the form of pure diastereomers, Z1-Q-P*R0R1 (I) in which Z1 is a C-bonded, secondary phosphine group —P(R)2; in which R is in each case independently hydrocarbon radicals or heterohydrocarbon radicals, or Z1 is the —P*R0R1 group; Q is a bivalent, achiral, aromatic base skeleton, a bivalent, achiral ferrocene base skeleton, an optionally substituted bivalent cycloalkane or heterocycloalkane skeleton, or a C1-C4-alkylene skeleton, and in which base skeletons a secondary phosphine group Z1 is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group, and in which base skeletons a P-chiral group —P*R0R1 is bonded directly to a carbon atom, or, in the case of cyclic base skeletons, directly to a carbon atom or via a C1-C4-alkylene group to a carbon atom such that the phosphorus atoms are linked via 1 to 7 atoms of a carbon chain optionally iType: ApplicationFiled: November 14, 2008Publication date: May 19, 2011Inventors: Benoît Pugin, Matthias Lotz, Heidi Landert, Adrian Wyss, Raphael Aardoom, Bjõrn Gschwend, Andreas Pfaltz, Felix Spindler
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Publication number: 20110098500Abstract: A polymerizable fluorine-containing compound represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R2 represents an acid-labile protecting 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 R2, 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 resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.Type: ApplicationFiled: January 4, 2011Publication date: April 28, 2011Applicant: Central Glass Company, LimitedInventors: Yoshimi ISONO, Jonathan Joachim Jodry, Satoru Narizuka
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Publication number: 20110082272Abstract: To provide a method for purifying a fluorinated carboxylic acid having an etheric oxygen atom and its derivative, with small decomposition and inclusion of impurities. A liquid containing at least one member selected from the group consisting of a fluorinated compound represented by the following formula (1) and a fluorinated compound represented by the following formula (2) is held at a heating temperature of at most 150° C. and distilled: RFOR1COOH??(1) RFOR1COOR2??(2) RF is a linear or branched monovalent fluoroorganic group which may have an etheric oxygen atom in its main chain, R1 is a linear or branched bivalent organic group, and R2 is a linear or branched monovalent organic group.Type: ApplicationFiled: December 9, 2010Publication date: April 7, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Hirokazu TAKAGI, Ryuji Seki
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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: 20110082313Abstract: Halogenated ?-fluoroethers (or bis-derivatives thereof) can be produced by reacting a halogenated hemiacetal (or bis-derivative thereof) with sulfuryl fluoride (S2F2) in the presence of an organic base. The reaction is conducted preferably in the presence of “a salt or complex of an organic base with hydrogen fluoride”, whereby the objective dehydroxyfluorination can proceed extremely favorably. It is still preferable to use as the starting substrate a halogenated hemiacetal prepared from fluoral or 3,3,3-trifluoropyruvic acid ester. Thus, industrially important halogenated ?-fluoroethers can be industrially produced with high selectivity and in high yield.Type: ApplicationFiled: May 14, 2009Publication date: April 7, 2011Applicant: CENTRAL GLASS COMPANY, LIMITEDInventors: Akihiro Ishii, Manabu Yasumoto
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Patent number: 7906676Abstract: The present invention relates to a novel process for the production of 3-amino-5-fluoro-4-dialkoxypentanoic acid ester used in the precursor of 3-amino-5-fluoro-4-oxopentanoic acid, represented by the following formula (I): wherein R1 and R2 are as defined in the Description.Type: GrantFiled: August 9, 2007Date of Patent: March 15, 2011Assignee: LG Life Sciences Ltd.Inventors: Hyun Ik Shin, Hyeong Wook Choi, Jae Hoon Lee, Kyu Woong Lee
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Publication number: 20110046411Abstract: The invention relates to novel synthesis methods for the preparation of statin derivatives, which methods proceed by way of a key intermediate of formula I wherein X is halogen, acyloxy, activated hydrocarbyloxy, activated hydrocarbylthio or —N(CH3)OCH3, Ra is a hydroxy-protecting group and Rb is a carboxy-protecting group, and, as well as to the compound of formula I, to further new intermediates and methods for their preparation by Friedel-Crafts acylation.Type: ApplicationFiled: November 4, 2010Publication date: February 24, 2011Inventors: REINHOLD ÖHRLEIN, Gabriele Baisch, Nicole End, Stephan Burkhardt, Martin Studer
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Patent number: 7855302Abstract: The invention relates to novel synthesis methods for the preparation of statin derivatives, which methods proceed by way of a key intermediate of formula I wherein X is halogen, acyloxy, activated hydrocarbyloxy, activated hydrocarbylthio or —N(CH3)OCH3, Ra is a hydroxy-protecting group and Rb is a carboxy-protecting group, and, as well as to the compound of formula I, to further new intermediates and methods for their preparation by Friedel-Crafts acylation.Type: GrantFiled: July 24, 2008Date of Patent: December 21, 2010Assignee: Ciba Specialty Chemicals Corp.Inventors: Reinhold Öhrlein, Gabriele Baisch, Nicole End, Stephan Burkhardt, Martin Studer
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Publication number: 20100256412Abstract: Provided are fluorinated polyethers and polyether oils and methods of preparation. The preparation involves a catalytic oxidation process of fluorinated vinyl ethers employing free oxygen.Type: ApplicationFiled: August 26, 2008Publication date: October 7, 2010Inventors: Werner Schwertfeger, Klaus Hintzer, Harald Kaspar, Egon Obermaier
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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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Publication number: 20090042996Abstract: A surfactant of formula 1 (Rf-A)a-Q-([B]k—R)b??Formula 1 wherein a and b are each independently 1 or 2; Rf is a linear or branched perfluoroalkyl radical having from 2 to about 20 carbon atoms, optionally interrupted with at least one oxygen; R is a C1 to C20 linear, branched or cyclic alkyl, or a C6 to C10 aryl; B is —(CH2CHR1O)x—, k is 0 or 1, x is 1 to about 20, A is —(CH2)m[(CHR1CH2O)]s—[(CH2)m(CH)tCHOH(CH2)m]e—, wherein each m is independently 0 to 3, s is 0 to about 30, t is 0 or 1, and e is 0 or 1, R1 is H or CH3, Q is: —OP(O)(O?M+)(O)—, —O—, —S—(CH2)m—C(O)—O—, —SO2—O— —CH2CH2O—C(O)CH2C(OH)(V)CH2C(O)O—; —(CH2CH2O)xCH2CH(OH)—(CH2CH2O)x—(CH2)m—Si[OSi(R2)3]2—, —SO2NR2—, —(CH2CH2O)zC(O)CH(SO3?M+)CH2C(O)(OCH2CH2)z— wherein z is 1 to about 15, or a bond when s is a positive integer, V is —C(O)OR3 and R3 is H, CH3 or Rf; R2 is C1 to C4 alkyl, and M+ is a Group 1 metal or an ammonium (NHxR2y)+ cation wherein x+y=4, and R2 is C1 to C4 alkyl, provided that when Q is —OP(O)(O?M+)(O)— or when Q is —(Type: ApplicationFiled: August 6, 2007Publication date: February 12, 2009Inventors: Charles Kenneth Taylor, Michael Joseph Michalczyk, Erick Jose Acosta
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Patent number: 7470808Abstract: A process for producing a fluorine-containing acrylic acid ester represented by CH2?C(Rf)(COOR) characterized in that 1-bromo-1-perfluoroalkylethene represented by CH2?CBr—Rf, or 1,2-dibromo-1-perfluoroalkylethane represented by CH2CBr—CHBr—Rf is allowed to react with an alcohol represented by ROH in the presence of a palladium catalyst, carbon monoxide, and two or more kinds of bases. The fluorine-containing acrylic acid ester is a useful compound having wide applications in materials for pharmaceuticals and functional polymers.Type: GrantFiled: March 24, 2004Date of Patent: December 30, 2008Assignees: Tosoh F-Tech, Inc., Sagami Chemical Research CenterInventors: Takamasa Fuchikami, Noriko Wakasa, Kenji Tokuhisa, Hideyuki Mimura, Shoji Arai
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Patent number: 7420078Abstract: The invention relates to synthesis methods for the preparation of statin derivatives, which methods proceed by way of a key intermediate of formula I wherein X is halogen, acyloxy, activated hydrocarbyloxy, activated hydrocarbylthio or N(CH3)OCH3, Ra is a hydroxy-protecting group, and Rb is a carboxy-protecting group, and, as well as to the compound of formula I, to further intermediates and methods for their preparation by Friedel-Crafts acylation.Type: GrantFiled: July 2, 2002Date of Patent: September 2, 2008Assignee: Ciba Specialty Chemicals Corp.Inventors: Reinhold Öhrlein, Gabriele Baisch, Nicole End, Stephan Burkhardt, Martin Studer
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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: 7271229Abstract: A fluorosulfonyl group-containing compound having a high polymerization reactivity, a process for its production, a sulfonyl group-containing polymerizable monomer led from the sulfonyl group-containing compound, and a polymer obtainable by polymerizing the sulfonyl group-containing polymerizable monomerType: GrantFiled: April 23, 2004Date of Patent: September 18, 2007Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Atsushi Watakabe, Masahiro Ito, Kunio Watanabe, Takeshi Eriguchi, Kimiaki Kashiwagi, Shu-zhong Wang
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Patent number: 7220878Abstract: The present invention concerns a method for purifying/separating a 2-fluoro-3-oxoalkylcarboxylic acid ester from a reaction mixture resulting from the fluorination of a 3-oxoalkylcarboxylic acid ester. The method involves depleting the reaction mixture of a hydrogen fluoride byproduct; and subsequently, separating the 2-fluoro-3-oxoalkylcarboxylic acid ester by distillation. The 2-fluoro-3-oxoalkylcarboxylic acid ester obtained by the method of the invention is highly pure and is thus suitable for use as an intermediate for the production of pharmacological products or agricultural chemicals.Type: GrantFiled: September 27, 2001Date of Patent: May 22, 2007Assignee: Tosoh F-Tech, Inc.Inventors: Norihisa Kondo, Hideyuki Mimura, Kosuke Kawada, Shoji Arai
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Patent number: 7019162Abstract: A process for producing a 2-fluoro-3-oxoalkylcarboxylic acid ester by fluorinating 3-oxoalkylcarboxylic acid ester with a fluorine gas is provided. The process is characterized in that the concentration of 3-oxoalkylcarboxylic acid ester in the reaction mixture for fluorination is maintained at 3 wt % or higher. Also provided is a process for purifying 2-fluoro-3-oxoalkylcarboxylic acid ester characterized in that 2-fluoro-3-oxoalkylcarboxylic acid ester is produced at high yield and with less impurities by washing fluorinated 3-oxoalkylcarboxylic acid ester with 3 or more times as much water as the amount of reaction mixture. According to the processes of the present invention, not only is the generation of unwanted by-products minimized, but fluorinated 3-oxoalkylcarboxylic acid ester can be purified in an efficient manner.Type: GrantFiled: December 25, 2001Date of Patent: March 28, 2006Assignee: Tosoh F-Tech, Inc.Inventors: Norihisa Kondo, Hideyuki Mimura, Kazunori Nukui, Kosuke Kawada, Shoji Arai
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Patent number: 6936722Abstract: (Per)haloethers having formula: X—(Rf)L—O—CF2CF2—O—CX1X2—CFX3X4??(I), process for obtaining them and hypofluorites usable in the synthesis of said (per)haloethers.Type: GrantFiled: February 4, 2003Date of Patent: August 30, 2005Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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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
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Patent number: 6894187Abstract: The present invention provides a method for obtaining a compound useful as a raw material for various fluororesins in high yield by a short process by using a starting material which is inexpensive and readily available.Type: GrantFiled: January 13, 2003Date of Patent: May 17, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Masahiro Ito, Daisuke Shirakawa, Masao Iwaya, Hidekazu Okamoto
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Publication number: 20040249190Abstract: The present invention concerns a method for purifying/separating a 2-fluoro-3-oxoalkylcarboxylic acid ester from a reaction mixture resulting from the fluorination of a 3-oxoalkylcarboxylic acid ester. The method involves depleting the reaction mixture of a hydrogen fluoride byproduct; and subsequently, separating the 2-fluoro-3-oxoalkylcarboxylic acid ester by distillation. The 2-fluoro-3-oxoalkylcarboxylic acid ester obtained by the method of the invention is highly pure and is thus suitable for use as an intermediate for the production of pharmacological products or agricultural chemicals.Type: ApplicationFiled: March 24, 2004Publication date: December 9, 2004Inventors: Norihisa Kondo, Hideyuki Mimura, Kosuke Kawada, Shoji Arai
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Patent number: 6815559Abstract: The invention relates to a process for producing 3,3,3-trifluoro-2-hydroxypropionic acid. This process includes the step of (a) bringing a 1,1-dihalogeno-3,3,3-trifluoroacetone into contact with a basic aqueous solution. The obtained 3,3,3-trifluoro-2-hydroxypropionic acid may be reacted with a C1-C6 lower alcohol under an acidic condition, thereby producing a 3,3,3-trifluoro-2-hydroxypropionate. This propionate may be reacted with a hydride reducing agent (e.g., sodium borohydride), thereby producing 3,3,3-trifluoro-2-hydroxypropanol. These products (i.e., 3,3,3-trifluoro-2-hydroxypropionic acid and its derivatives) are important intermediates for medicines and liquid crystals.Type: GrantFiled: June 19, 2003Date of Patent: November 9, 2004Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Masatomi Kanai, Yokusu Kuriyama, Manabu Yasumoto, Kenjin Inomiya
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Patent number: RE41184Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. Namely, the present invention provides a process which comprises reacting XSO2RA-E1 (1) with RB-E2 (2) to form XSO2RA-E-RB (3), then reacting (3) with fluorine in a liquid phase to form FSO2RAF-EF-RBF (4), and further, decomposing the compound to obtain FSO2RAF-EF1 (5), wherein RA is a bivalent organic group, E1 is a monovalent reactive group, RB is a monovalent organic group, E2 is a monovalent reactive group which is reactive with E1, E is a bivalent connecting group formed by the reaction of E1 with E2, RAF is a bivalent organic group formed by the fluorination of RA, etc., RBF is the same group as RB, etc., EF is a bivalent connecting group formed by the fluorination of E, etc.Type: GrantFiled: September 19, 2008Date of Patent: March 30, 2010Assignee: Asahi Glass Company, LimitedInventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa
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Patent number: RE41357Abstract: The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. Namely, the present invention provides a process which comprises reacting XSO2RA-E1 (1) with RB-E2 (2) to form XSO2RA-E-RB (3), then reacting (3) with fluorine in a liquid phase to form FSO2RAF-EF-RBF (4), and further, decomposing the compound to obtain FSO2RAF-EF1 (5), wherein RA is a bivalent organic group, E1 is a monovalent reactive group, RB is a monovalent organic group, E2 is a monovalent reactive group which is reactive with E1, E is a bivalent connecting group formed by the reaction of E1 with E2, RAF is a bivalent organic group formed by the fluorination of RA, etc., RBF is the same group as RB, etc., EF is a bivalent connecting group formed by the fluorination of E, etc.Type: GrantFiled: September 19, 2008Date of Patent: May 25, 2010Assignee: Asahi Glass Company, LimitedInventors: Masahiro Ito, Kunio Watanabe, Takashi Okazoe, Isamu Kaneko, Daisuke Shirakawa