Plural Carbons Bonded Directly To The Chalcogen (e.g., Ethers, Etc.) Patents (Class 562/111)
  • Patent number: 11155661
    Abstract: A method of making a copolymer is disclosed. The method includes copolymerizing components including tetrafluoroethylene and a compound represented by formula CF2?CF—O—(CF2)a—SO2X, wherein “a” is a number from 1 to 4, and X is —NZH, —NZ—SO2—(CF2)1-6—SO2X?, or —OZ, wherein Z is independently a hydrogen, an alkali metal cation, or a quaternary ammonium cation, and wherein X? is independently —NZH or —OZ. The components include at least 60 mole % of tetrafluoroethylene based on the total amount of components. A copolymer prepared by the method is also provided. A method of making a membrane using the copolymer is also provided. The present disclosure also provides a polymer electrolyte membrane that includes a copolymer made by the method and a membrane electrode assembly that includes such a polymer electrolyte membrane.
    Type: Grant
    Filed: September 22, 2016
    Date of Patent: October 26, 2021
    Assignee: 3M Innovative Properties Company
    Inventors: Gregg D. Dahlke, Denis Duchesne, Klaus Hintzer, Markus E. Hirschberg, Kai H. Lochhaas, Arne Thaler, Tilman C. Zipplies
  • Patent number: 9843074
    Abstract: The invention relates to lithium 1-trifluoromethoxy-1,2,2,2-tetra-fluoroethanesulphonate, the use of lithium 1-trifluoromethoxy-1,2,2,2-tetra-fluoroethanesulphonate as electrolyte salt in lithium-based energy stores and also ionic liquids comprising 1-trifluoro-methoxy-1,2,2,2-tetrafluoro-ethanesulphonate as anion.
    Type: Grant
    Filed: February 27, 2013
    Date of Patent: December 12, 2017
    Assignee: WESTFÄLISCHE WILHELMS-UNIVERSITÄT MÜNSTER
    Inventors: Gerd-Volker Röschenthaler, Martin Winter, Stefano Passerini, Katja Vlasov, Nataliya Kalinovich, Christian Schreiner Schreiner, Raphael Wilhelm Schmitz, Ansgar Romek Müller, Rene Schmitz, Tanja Schedlbauer, Alexandra Lex-Balducci, Miriam Kunze
  • Patent number: 9315404
    Abstract: A process comprising contacting deionized water with one or more Strecker sulfonation reaction products of one or more halogenated alkyl ethers in the presence of sulfite, wherein the one or more Strecker sulfonation reaction products each comprise one or more inorganic salts on a dry basis and one or more surfactant components, form a filtration mixture; loading the filtration mixture into a high pressure filtration system containing a membrane having a membrane molecular weight cutoff allowing preferential passage of the inorganic salts, for example, of greater than or equal to 200 Daltons; wherein the high pressure filtration system is operated at a pressure greater than ambient pressure and is configured to cause crossflow of the filtration mixture along a surface of the membrane resulting in a permeate solution which substantially passes through the membrane and a retentate solution which substantially does not pass through the membrane; wherein the permeate comprises less than or equal to 15 weight perc
    Type: Grant
    Filed: December 5, 2011
    Date of Patent: April 19, 2016
    Assignee: Dow Global Technologies LLC
    Inventors: Mark R. Smit, Edward D. Daugs, Raymond M. Collins
  • Patent number: 9035089
    Abstract: A method of making modified carbon materials for use in fabricating fuel cell components. The modified carbon may comprise pendant fluorocarbon groups bonded covalently bonded thereto. In one embodiment, a mixture is formed and comprises carbon material suitable for use in a fuel cell component, an organic solvent, a compound having the general formula I—R wherein R is a fluorocarbon, and a reductant.
    Type: Grant
    Filed: September 12, 2011
    Date of Patent: May 19, 2015
    Assignee: GM Global Technology Operations LLC
    Inventor: Ping Liu
  • Patent number: 8993210
    Abstract: A salt represented by the formula (I): wherein R1 and R2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group which can have one or more fluorine atoms and in which one or more —CH2— can be replaced by —O— or —CO—, R3 represents a group having a cyclic ether structure, and Z1+ represents an organic cation.
    Type: Grant
    Filed: February 15, 2011
    Date of Patent: March 31, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto
  • Patent number: 8969437
    Abstract: The invention provides a compound which is useful in production of a fluoropolymer and easy to be removed from the produced fluoropolymer, a method of producing the compound, and a method of producing a fluoropolymer using the compound. The invention provides a compound which is represented by Rf1—CH2O—CF2—CHF—Rf2—X, wherein Rf1 represents a fluoroalkyl group containing 1 to 5 carbon atoms, Rf2 represents a fluoroalkylene group containing 1 to 3 carbon atoms, X represents —COOM or —SO3M, and M represents one of H, K, Na, and NH4.
    Type: Grant
    Filed: January 18, 2013
    Date of Patent: March 3, 2015
    Assignee: Daikin Industries, Ltd.
    Inventors: Nobuhiko Tsuda, Akinari Sugiyama
  • Patent number: 8956799
    Abstract: A photoacid generator includes those of formula (I): wherein each Ra in formula 1 is independently H, F, a C1-10 nonfluorinated organic group, C1-10 fluorinated organic group, or a combination comprising at least one of the foregoing, provided at least one Ra is F or a C1-10 fluorinated organic group, the C1-10 fluorinated and nonfluorinated organic groups each optionally comprising O, S, N, or a combination comprising at least one of the foregoing heteroatoms; L1 is a linking group comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing; G+ is an onium salt of the formula (II): wherein in formula (II), X is S or I, each R0 is independently C1-30 alkyl group; a polycyclic or monocyclic C3-30 cycloalkyl group; a polycyclic or monocyclic C4-30 aryl group; or a combination comprising at least one of the foregoing, provided at least one R0 is substituted where each R0 is a C6 monocyclic aryl group, and wherein when X is I, a is 2, and where X is S, a is 3,
    Type: Grant
    Filed: December 12, 2012
    Date of Patent: February 17, 2015
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, William Williams, III
  • Publication number: 20150044509
    Abstract: Compounds of the formula (I), (Ia) or (Ib) wherein A1, and A? is for example (II) is 1 or 2; X is C1-C4 alkylene or CO; Y is for example O, O(CO), O(CO)O, R1 is for example hydrogen, d-dsalkyl, C3-C30cycloalkyl, phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or C3-C20heteroaryl, all of which optionally are substituted; R2 and R3 for example are C1-C10haloalkylene which is optionally substituted, or R2 and R3 are phenylene, which optionally is substituted; R4 is a group (A) or a group (B); R5 and R6 for example are C1-C20alkyl; or R4 and R5 or R4 and R6 together form a straight-chain C2-C6alkylene, R5 and R6 together form a straight-chain C2-C6alkylene; R7, R8, R9 and R10 ifor example are C1-C20alkyl; M for example is C1-C20alkylene, C2-C20alkenylene, C2-C20alkynylene; R25 and R26 are for example hydrogen, C1-C20alkyl; R27, R28, R29, R30 and R31 are for example hydrogen, C1-C20alkyl, C2-C20alkenyl, C3-C20cycloalkyl, or two radicals R27 and R28, R28 and R29, R29 and R30 and/or R30 and R31 toget
    Type: Application
    Filed: April 17, 2013
    Publication date: February 12, 2015
    Applicant: BASF SE
    Inventors: Kazuhiko Kunimoto, Hisatoshi Kura
  • Publication number: 20140377667
    Abstract: The invention relates to lithium-2-methoxy-1,1,2,2-tetrafluoro-ethanesulfonate, to the use thereof as conductive salt in lithium-based energy accumulators, and ionic liquids comprising 2-methoxy-1,1,2,2-tetrafluoro-ethanesulfonate as an anion.
    Type: Application
    Filed: July 25, 2012
    Publication date: December 25, 2014
    Applicants: JACOBS UNIVERSITY BREMEN gGMBH, WESTFALISCHE WILHELMS UNIVERSITAT MUNSTER
    Inventors: Gerd-Volker Roschenthaler, Martin Winter, Katja Vlasov, Nataliya Kalinovich, Christian Schreiner, Raphael Wilhelm Schmitz, Romek Ansgar Muller, Rene Schmitz, Alexandra Lex-Balducci, Miriam Kunze
  • Publication number: 20140339096
    Abstract: In this method, RH2ORH1SO2F is added to hydrofluoric acid so as to form a thick solution (hydrogen bonded complex), and the solution is directly supplied to a liquid phase reaction system, in which an F2 gas is used. Alternatively, RH2ORH1SO2Cl is added to hydrofluoric acid so as no be converted into RH1ORH2SO2F by disc barging HCl, and the RH1ORH2SO2F is directly supplied to a liquid phase reaction system in which an F2 gas is used. Consequently, fluorination can be carried out safely and a compound having an objective structure can be produced at low cost without causing isomerization or the like.
    Type: Application
    Filed: August 4, 2014
    Publication date: November 20, 2014
    Inventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
  • Patent number: 8889901
    Abstract: A photoacid generator represented by the following formula (1), a method for producing the photoacid generator, and a resist composition containing the photoacid generator are provided. wherein in the formula (1), Y, X, R1, R2, n1, n2 and A+ have the same meanings as defined in the detailed description of the invention. The photoacid generator can maintain an appropriate contact angle at the time of ArF liquid immersion lithography, can reduce defects occurring during liquid immersion lithography, and has excellent solubility in resist solvents and excellent compatibility with resins. Furthermore, the photoacid generator can be produced by an efficient and simple method using an epoxy compound that is industrially easily available.
    Type: Grant
    Filed: February 7, 2012
    Date of Patent: November 18, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon Oh, Dae Kyung Yoon, Yong Hwa Hong, Seung Duk Cho
  • Patent number: 8791293
    Abstract: 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: Grant
    Filed: August 2, 2012
    Date of Patent: July 29, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Kazunori Mori, Satoru Narizuka, Fumihiro Amemiya, Masaki Fujiwara
  • Patent number: 8779184
    Abstract: The present invention provides a method for efficiently producing a sulfonic acid group-containing ether compound having a high purity and a good polymerizability while preventing production of a byproduct, and provides a sulfonic acid group-containing ether compound containing fewer impurities and having a good radical (co)polymerizability. The present invention provides a method of producing a sulfonic acid group-containing ether compound by reacting a sulfurous acid compound with a compound represented by the formula (1): wherein R1 represents a single bond, a CH2 group, or a CH2CH2 group, and R2 represents H, or a CH3 group, the method comprising the steps of: adjusting pH of a reaction system to 5.5 or greater with use of an alkaline substance; and adding the compound represented by the formula (1) to a reaction vessel containing the sulfurous acid compound.
    Type: Grant
    Filed: September 14, 2009
    Date of Patent: July 15, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Masato Nakano, Akihiko Kanzaki, Takahiro Tsumori
  • Patent number: 8748672
    Abstract: By using an organic base when a carboxylic acid bromodifluoroethyl ester is sulfinated by using a sulfinating agent, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt. By oxidizing the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt. By using the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt as a raw material and exchanging it into an onium salt directly or through saponification/esterification, there can be obtained a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid onium salt.
    Type: Grant
    Filed: July 5, 2013
    Date of Patent: June 10, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
  • Patent number: 8716519
    Abstract: The invention relates to novel cross-linkable monomers that may be polymerized with ethylenically unsaturated comonomers to form cross-linkable copolymers. Said copolymers may particularly be used in the form of aqueous dispersions as formaldehyde-free adhesives or as coatings with good water resistance.
    Type: Grant
    Filed: July 11, 2008
    Date of Patent: May 6, 2014
    Assignee: Celanese Emulsions GmbH
    Inventors: Martin Jakob, Stefan Nogai
  • Patent number: 8581009
    Abstract: By using an organic base when a carboxylic acid bromodifluoroethyl ester is sulfinated by using a sulfinating agent, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt. By oxidizing the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt. By using the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt as a raw material and exchanging it into an onium salt directly or through saponification/esterification, there can be obtained a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid onium salt.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: November 12, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
  • Publication number: 20130190417
    Abstract: The disclosure provides anionic Gemini surfactants comprising at least two carbonyl moieties and at least two aliphatic moieties. In some aspects, at least two of the aliphatic moieties comprise at least seven carbon atoms and at least one pair of conjugated carbon-to-carbon double bonds. The anionic Gemini surfactants are polymerizable and may be used to prepare triply periodic multiply continuous lyotropic phase and polymers thereof that substantially retain triply periodic multiply continuous lyotropic phase structure.
    Type: Application
    Filed: January 23, 2013
    Publication date: July 25, 2013
    Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATION
    Inventor: Wisconsin Alumni Research Foundation
  • Patent number: 8465668
    Abstract: Surfactants with polyether sulfonate structure, which have a propanonylsulfonic acid group as a head group, a process for preparing such surfactants and their use for tertiary mineral oil extraction.
    Type: Grant
    Filed: October 15, 2008
    Date of Patent: June 18, 2013
    Assignee: BASF SE
    Inventors: Christian Bittner, Oetter Günter, Ulrich Steinbrenner, Jürgen Huff, Marcus Guzmann
  • Patent number: 8461378
    Abstract: A process for the purification of fluoroalkanesulfonate salt comprising (a) contacting a mixture of said salt and an inorganic salt contaminant with a solvent to selectively dissolve said fluoroalkanesulfonate salt in solution, and (b) isolating the solution, to yield a fluoroalkanesulfonate salt containing less than 500 micrograms of inorganic salt contaminant per gram of fluoroalkanesulfonate salt, or containing less than a maximum of 0.3% by weight of individual solvent.
    Type: Grant
    Filed: September 10, 2010
    Date of Patent: June 11, 2013
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Allen Capron Sievert, Lee Grant Sprague, James A. Schultz, Katelyn Rae Walck
  • Patent number: 8415085
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).
    Type: Grant
    Filed: May 23, 2012
    Date of Patent: April 9, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 8399703
    Abstract: The invention provides a compound which is useful in production of a fluoropolymer and easy to be removed from the produced fluoropolymer, a method of producing the compound, and a method of producing a fluoropolymer using the compound. The invention provides a compound which is represented by Rf1—CH2O—CF2—CHF—Rf2—X, wherein Rf1 represents a fluoroalkyl group containing 1 to 5 carbon atoms, Rf2 represents a fluoroalkylene group containing 1 to 3 carbon atoms, X represents —COOM or —SO3M, and M represents one of H, K, Na, and NH4.
    Type: Grant
    Filed: July 24, 2008
    Date of Patent: March 19, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Nobuhiko Tsuda, Akinari Sugiyama
  • Publication number: 20130066105
    Abstract: A method of making modified carbon materials for use in fabricating fuel cell components. The modified carbon may comprise pendant fluorocarbon groups bonded covalently bonded thereto. In one embodiment, a mixture is formed and comprises carbon material suitable for use in a fuel cell component, an organic solvent, a compound having the general formula I-R wherein R is a fluorocarbon, and a reductant.
    Type: Application
    Filed: September 12, 2011
    Publication date: March 14, 2013
    Applicant: GM GLOBAL TECHNOLOGY OPERATIONS LLC
    Inventor: Ping Liu
  • Patent number: 8283492
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: January 20, 2011
    Date of Patent: October 9, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • Patent number: 8247160
    Abstract: A resist composition including a base component that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator consisting of a compound represented by general formula (b1). In formula (b1), Y1 represents a fluorinated alkylene group of 1 to 4 carbon atoms, X represents an aliphatic cyclic group of 3 to 30 carbon atoms, R11? to R13? each represents an aryl group or alkyl group, provided that at least one of R11? to R13? is an aryl group having a substituent represented by general formula (b1-0), and two alkyl groups among R11? to R13? may be bonded to each other to form a ring with the sulfur atom in the formula. In formula (b1-0), R52 represents a chain-like or cyclic hydrocarbon group, and f and g each represents 0 or 1.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: August 21, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Akiya Kawaue, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Publication number: 20120184763
    Abstract: In this method, RH2ORH1SO2F is added to hydrofluoric acid so as to form a thick solution (hydrogen bonded complex), and the solution is directly supplied to a liquid phase reaction system in which an F2 gas is used. Alternatively, RH2ORH1SO2Cl is added to hydrofluoric acid so as to be converted into RH1ORH2SO2F by discharging HCl, and the RH1ORH2SO2F is directly supplied to a liquid phase reaction system in which an F2 gas is used. Consequently, fluorination can be carried out safely and a compound having an objective structure can be produced at low cost without causing isomerization or the like.
    Type: Application
    Filed: September 29, 2010
    Publication date: July 19, 2012
    Applicants: Mitsubishi Materials Electronic Chemicals Co., Ltd, MITSUBISHI MATERIALS CORPORATION
    Inventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
  • Publication number: 20120125777
    Abstract: Sulfonate- or sulfate-capped, alkoxylated anti-misting agents having the structures: R((AO)nX)m((AO)nH)p and R3C(O)NH(CH2)zN+(CH3)2CH2CHR4CH2SO3?, and to methods of suppressing mist from electrolyte solutions by adding a mist-suppressing amount of one or more of said compounds to electrolyte solutions.
    Type: Application
    Filed: September 19, 2007
    Publication date: May 24, 2012
    Inventors: MICHAEL VIRNIG, Jack Bender, Louis Rebrovic
  • Patent number: 8114570
    Abstract: Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. ROC(?O)R1—COOCH2CF2SO3?H+??(1a) RO is OH or C1-C20 organoxy, R1 is a divalent C1-C20 aliphatic group or forms a cyclic structure with RO. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.
    Type: Grant
    Filed: March 24, 2009
    Date of Patent: February 14, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
  • Patent number: 8110711
    Abstract: Disclosed is a process for producing 2-bromo-2,2-difluoroethanol, which comprises reducing a bromodifluoroacetic acid derivative represented by the formula [1] by using an ate hydride complex as a reducing agent. 2-Bromo-2,2-difluoroethanol thus produced can be used as the starting material to carry out the esterification step, the sulfination step and the oxidation step in this order, thereby producing a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid salt, wherein A represents a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 15 carbon atoms, a heteroaryloxy group having 4 to 15 carbon atoms, or a halogen atom.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: February 7, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Jonathan Joachim Jodry, Masashi Nagamori, Yuji Hagiwara, Masaki Fujiwara, Satoru Narizuka
  • Patent number: 8057985
    Abstract: A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C1-C20 organic group, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: November 15, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana
  • Patent number: 8048604
    Abstract: Hydrofluoroalkanesulfonates of the general formula R—O—CXH—CX2—SO3M, where R is selected from the group consisting of alkyl groups, functionalized alkyl groups, and alkenyl groups; X is selected from the group consisting of hydrogen and fluorine with the proviso that at least one X is fluorine; and M is a cation, are made by reacting fluorovinyl ether with aqueous sulfite solution. Organic onium hydrofluoroalkanesulfonates are useful as ionic liquids and photoacid generators.
    Type: Grant
    Filed: October 21, 2010
    Date of Patent: November 1, 2011
    Assignee: E.I.du Pont de Nemours and Company
    Inventors: Christopher P. Junk, Mark Andrew Harmer, Andrew Edward Feiring, Frank Leonard Schadt, III, Zoe Schnepp
  • Publication number: 20110172459
    Abstract: The present invention provides a method for efficiently producing a sulfonic acid group-containing ether compound having a high purity and a good polymerizability while preventing production of a byproduct, and provides a sulfonic acid group-containing ether compound containing fewer impurities and having a good radical (co)polymerizability. The present invention provides a method of producing a sulfonic acid group-containing ether compound by reacting a sulfurous acid compound with a compound represented by the formula (1): wherein R1 represents a single bond, a CH2 group, or a CH2CH2 group, and R2 represents H, or a CH3 group, the method comprising the steps of: adjusting pH of a reaction system to 5.5 or greater with use of an alkaline substance; and adding the compound represented by the formula (1) to a reaction vessel containing the sulfurous acid compound.
    Type: Application
    Filed: September 14, 2009
    Publication date: July 14, 2011
    Applicant: NIPPON SHOKUBAI CO., LTD
    Inventors: Masato Nakano, Akihiko Kanzaki, Takahiro Tsumori
  • Publication number: 20110152537
    Abstract: The present invention relates to chemical compounds comprising a [Y(CHRa)n—CH(Ra)SO3]? anion, their preparation and application. The chemical compounds are preferably ionic liquids.
    Type: Application
    Filed: May 12, 2009
    Publication date: June 23, 2011
    Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG
    Inventors: Peter Wasserscheid, Natalia Paape, Andreas Boesmann, Peter Schulz
  • Patent number: 7919226
    Abstract: Sulfonate salts have the formula: CF3—CH(OCOR)—CF2SO3?M+ wherein R is C1-C20 alkyl or C6-C14 aryl, and M+ is a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: August 13, 2008
    Date of Patent: April 5, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
  • Patent number: 7897807
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: February 22, 2010
    Date of Patent: March 1, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • Publication number: 20110039203
    Abstract: Hydrofluoroalkanesulfonates of the general formula R—O—CXH—CX2—SO3M, where R is selected from the group consisting of alkyl groups, functionalized alkyl groups, and alkenyl groups; X is selected from the group consisting of hydrogen and fluorine with the proviso that at least one X is fluorine; and M is a cation, are made by reacting fluorovinyl ether with aqueous sulfite solution. Organic onium hydrofluoroalkanesulfonates are useful as ionic liquids and photoacid generators.
    Type: Application
    Filed: October 21, 2010
    Publication date: February 17, 2011
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: CHRISTOPHER P. JUNK, MARK ANDREW HARMER, ANDREW EDWARD FEIRING, FRANK LEONARD SCHADT, III, ZOE SCHNEPP
  • Publication number: 20110015431
    Abstract: Disclosed is a process for producing 2-bromo-2,2-difluoroethanol, which comprises reducing a bromodifluoroacetic acid derivative represented by the formula [1] by using an ate hydride complex as a reducing agent. 2-Bromo-2,2-difluoroethanol thus produced can be used as the starting material to carry out the esterification step, the sulfination step and the oxidation step in this order, thereby producing a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid salt, wherein A represents a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 15 carbon atoms, a heteroaryloxy group having 4 to 15 carbon atoms, or a halogen atom.
    Type: Application
    Filed: September 5, 2008
    Publication date: January 20, 2011
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Jonathan Joachim Jodry, Masashi Nagamori, Yuji Hagiwara, Masaki Fujiwara, Satoru Narizuka
  • Patent number: 7834209
    Abstract: Hydrofluoroalkanesulfonates of the general formula R—O—CXH—CX2—SO3M, where R is selected from the group consisting of alkyl groups, functionalized alkyl groups, and alkenyl groups; X is selected from the group consisting of hydrogen and fluorine with the proviso that at least one X is fluorine; and M is a cation, are made by reacting fluorovinyl ether with aqueous sulfite solution. Organic onium hydrofluoroalkanesulfonates are useful as ionic liquids and photoacid generators.
    Type: Grant
    Filed: June 6, 2006
    Date of Patent: November 16, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Christopher P. Junk, Mark Andrew Harmer, Andrew Edward Feiring, Frank Leonard Schadt, III, Zoe Schnepp
  • Publication number: 20100120980
    Abstract: A compound of Formula (1) Rf—O—(CXX?)m—(CY2)nSO3M ??(1) wherein Rf is a C1 to C4 linear or branched perfluoroalkyl group, X and X? are each independently H or F, provided that at least one of X or X? is F, each Y is independently H or F, m is an integer from 1 to 4, n is an integer from 1 to 2, and M is H, NH4, Li, Na or K, provided that when CXX? is CHF or CFH, then n is 2.
    Type: Application
    Filed: November 13, 2008
    Publication date: May 13, 2010
    Inventors: Sheng Peng, Ming-Hong Hung, Christopher P. Junk, Phan Linh Tang
  • Patent number: 7683209
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: June 6, 2006
    Date of Patent: March 23, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • Publication number: 20090292126
    Abstract: The present invention relates to compositions of matter that are ionic liquids, the compositions comprising any of eleven cations combined with any of three fluorinated sulfonated anions. Compositions of the invention should be useful as solvents and, perhaps, as catalysts for many reactions, including aromatic electrophilic substitution, nitration, acylation, esterification, etherification, oligomerization, transesterification, isomerization and hydration.
    Type: Application
    Filed: May 27, 2009
    Publication date: November 26, 2009
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Jemma Vickery
  • Patent number: 7569326
    Abstract: A sulfonium salt having a polymerizable anion generates a strong sulfonic acid upon exposure to high-energy radiation so that it facilitates effective scission of acid labile groups in chemically amplified resist compositions. It is useful as a monomer from which a base resin for use in radiation-sensitive resist compositions is derived.
    Type: Grant
    Filed: October 25, 2007
    Date of Patent: August 4, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
  • Patent number: 7524609
    Abstract: A photosensitive composition, which comprises (A) a compound capable of generating an organic acid represented by formula (I) upon irradiation with actinic ray or radiation: Z—A—X—B—R—(Y)n??(I) wherein Z represents an organic acid group; A represents a divalent linking group; X represents a divalent linking group having a hetero atom; B represents an oxygen atom or —N(Rx)—; Rx represents a hydrogen atom or a monovalent organic group; R represents a monovalent organic group substituted with Y, and when B represents —N(Rx)—, R and Rx may be bonded to each other to form a cyclic structure; Y represents —COOH or —CHO, and when a plurality of Y's are present, the plurality of Y's may be the same or different; and n represents an integer of from 1 to 3.
    Type: Grant
    Filed: March 9, 2007
    Date of Patent: April 28, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kenji Wada
  • Patent number: 7514202
    Abstract: A thermal acid generator of generating an acid on heating above 100° C. has formula: CF3CH(OCOR)CF2SO3?(R1)4N+ wherein R is alkyl or aryl, R1 is hydrogen, alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl, or R1 may bond together to form a ring with N. The sulfonic acid generated possesses an ester site within molecule so that less bulky acyl groups to bulky groups may be incorporated therein. The thermal acid generator provides a sufficient acid strength, is less volatile due to a high molecular weight, and ensures film formation. Upon disposal of used resist liquid, it may be converted into low accumulative compounds.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: April 7, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Jun Hatakeyama
  • Patent number: 7511169
    Abstract: Sulfonate salts have the formula: CF3—CH(OCOR)—CF2SO3?M+ wherein R is C1-C20 alkyl or C6-C14 aryl, and M+ is a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: April 5, 2006
    Date of Patent: March 31, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
  • Publication number: 20080171895
    Abstract: Novel compositions of matter and the process of preparing these surfactants having the structure: R1[—(O—(R2O)m—(R3O)n—(R4)]y where: R1=alkyl, alkenyl, amine, alkylamine, dialkylamine, trialkylamine, aromatic, polyaromatic, cycloalkane, cycloalkene, R2=C2H4 or C3H6 or C4H8, R3=C2H4 or C3H6 or C4H8, R4=linear or branched C7H14SO3X to C30H60 SO3X when y=1, R4=linear or branched C7H14SO3X to C30H60 SO3X or H when y>1 but at least one R4 must be linear or branched C7H14SO3X to C30H60 SO3X, m?1, n?0, n+m=1 to 30+, y?1, X=alkali metal or alkaline earth metal or ammonium or amine. These novel ether sulfonate surfactants have excellent surfactant properties making them suitable for a variety of applications as surfactants including agriculture, adhesives, coatings, deinking, detergents, emulsion polymerization, laundry, lubricants, metal working, mining, oilfield, personal care, pharmaceuticals, and soil remediation.
    Type: Application
    Filed: January 12, 2007
    Publication date: July 17, 2008
    Inventors: Paul Daniel Berger, Christie Huimin Berger
  • Patent number: 7148375
    Abstract: A detergent composition having cold water solubility and exhibiting high calcium tolerance can be produced from biodegradable branched ether derivative compositions derived from a branched ether primary alcohol represented by the formula: wherein R1 represents hydrogen or a hydrocarbyl radical having from 1 to 3 carbon atoms, R2 represents a hydrocarbyl radical having from 1 to 7 carbon atoms, x is a number ranging from 0 to 16, preferably from 3 to 13, wherein the total number of carbon atoms in the alcohol ranges from 9 to 24.
    Type: Grant
    Filed: April 2, 2004
    Date of Patent: December 12, 2006
    Assignee: Shell Oil Company
    Inventors: Charles Lee Edwards, Kirk Herbert Raney, Paul Gregory Shpakoff
  • Patent number: 6649790
    Abstract: A process for preparing a monomer compound represented by formula (II): [wherein M represents an alkali metal or alkaline earth metal; and n is 0, 1 or 2.] by pyrolysis of a compound represented by formula (I) below: [wherein M and n are as defined above.], the pyrolysis being conducted in the presence of a catalyst which has coordinating properties to a metal ion M.
    Type: Grant
    Filed: April 19, 2002
    Date of Patent: November 18, 2003
    Assignee: Daikin Industries, Ltd.
    Inventor: Masayoshi Tatemoto
  • Patent number: 6459003
    Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: October 1, 2002
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Patent number: 6121222
    Abstract: A novel class of anionic surfactants with improved surfact active properties is comprised of two hydrophilic and two hydrophobic groups represented by the formula: ##STR1## The surfactants exhibit unusually low critical micelle concentration (cmc) and pC-20 values in aqueous media.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: September 19, 2000
    Assignee: Rhodia Inc.
    Inventors: Ruoxin Li, David James Tracy, Jiang Yang, Manilal S. Dahanayake
  • Patent number: 5814110
    Abstract: Distillate fuel is treated with additives whose structure match the crystal planes of the wax which crystallizes from the fuel to produce crystals below 4000 nanometres in size, suitable additive include novel sulpho-carboxylic materials particularly their esters and amine derivatives such as the amine salts and/or amides of ortho-sulpho benzoic acid.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: September 29, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Kenneth William Bartz, Jacqueline Dawn Bland, David Paul Gillingham, Richard Dix Kerwood, Edwin William Lehmann, Kenneth Lewtas, John Edward Maddox, Albert Rossi, Robert Dryden Tack