Plural Carbons Bonded Directly To The Chalcogen (e.g., Ethers, Etc.) Patents (Class 562/111)
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Patent number: 11155661Abstract: 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: GrantFiled: September 22, 2016Date of Patent: October 26, 2021Assignee: 3M Innovative Properties CompanyInventors: Gregg D. Dahlke, Denis Duchesne, Klaus Hintzer, Markus E. Hirschberg, Kai H. Lochhaas, Arne Thaler, Tilman C. Zipplies
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Patent number: 9843074Abstract: 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: GrantFiled: February 27, 2013Date of Patent: December 12, 2017Assignee: WESTFÄLISCHE WILHELMS-UNIVERSITÄT MÜNSTERInventors: 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
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Patent number: 9315404Abstract: 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 percType: GrantFiled: December 5, 2011Date of Patent: April 19, 2016Assignee: Dow Global Technologies LLCInventors: Mark R. Smit, Edward D. Daugs, Raymond M. Collins
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Patent number: 9035089Abstract: 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: GrantFiled: September 12, 2011Date of Patent: May 19, 2015Assignee: GM Global Technology Operations LLCInventor: Ping Liu
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Patent number: 8993210Abstract: 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: GrantFiled: February 15, 2011Date of Patent: March 31, 2015Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Hiromu Sakamoto
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Patent number: 8969437Abstract: The invention provides a compound which is useful in production of a fluoropolymer and easy to be removed from the produced fluoropolymer, a method of producing the compound, and a method of producing a fluoropolymer using the compound. The invention provides a compound which is represented by Rf1—CH2O—CF2—CHF—Rf2—X, wherein Rf1 represents a fluoroalkyl group containing 1 to 5 carbon atoms, Rf2 represents a fluoroalkylene group containing 1 to 3 carbon atoms, X represents —COOM or —SO3M, and M represents one of H, K, Na, and NH4.Type: GrantFiled: January 18, 2013Date of Patent: March 3, 2015Assignee: Daikin Industries, Ltd.Inventors: Nobuhiko Tsuda, Akinari Sugiyama
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Patent number: 8956799Abstract: 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: GrantFiled: December 12, 2012Date of Patent: February 17, 2015Assignee: Rohm and Haas Electronic Materials LLCInventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, William Williams, III
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Publication number: 20150044509Abstract: 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 togetType: ApplicationFiled: April 17, 2013Publication date: February 12, 2015Applicant: BASF SEInventors: Kazuhiko Kunimoto, Hisatoshi Kura
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Publication number: 20140377667Abstract: 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: ApplicationFiled: July 25, 2012Publication date: December 25, 2014Applicants: JACOBS UNIVERSITY BREMEN gGMBH, WESTFALISCHE WILHELMS UNIVERSITAT MUNSTERInventors: Gerd-Volker Roschenthaler, Martin Winter, Katja Vlasov, Nataliya Kalinovich, Christian Schreiner, Raphael Wilhelm Schmitz, Romek Ansgar Muller, Rene Schmitz, Alexandra Lex-Balducci, Miriam Kunze
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Publication number: 20140339096Abstract: 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: ApplicationFiled: August 4, 2014Publication date: November 20, 2014Inventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
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Patent number: 8889901Abstract: 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: GrantFiled: February 7, 2012Date of Patent: November 18, 2014Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Jung Hoon Oh, Dae Kyung Yoon, Yong Hwa Hong, Seung Duk Cho
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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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Patent number: 8779184Abstract: 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: GrantFiled: September 14, 2009Date of Patent: July 15, 2014Assignee: Nippon Shokubai Co., Ltd.Inventors: Masato Nakano, Akihiko Kanzaki, Takahiro Tsumori
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Patent number: 8748672Abstract: 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: GrantFiled: July 5, 2013Date of Patent: June 10, 2014Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
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Patent number: 8716519Abstract: 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: GrantFiled: July 11, 2008Date of Patent: May 6, 2014Assignee: Celanese Emulsions GmbHInventors: Martin Jakob, Stefan Nogai
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Patent number: 8581009Abstract: 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: GrantFiled: September 5, 2008Date of Patent: November 12, 2013Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Masashi Nagamori, Masaki Fujiwara, Jonathan Joachim Jodry, Satoru Narizuka
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Publication number: 20130190417Abstract: 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: ApplicationFiled: January 23, 2013Publication date: July 25, 2013Applicant: WISCONSIN ALUMNI RESEARCH FOUNDATIONInventor: Wisconsin Alumni Research Foundation
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Patent number: 8465668Abstract: 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: GrantFiled: October 15, 2008Date of Patent: June 18, 2013Assignee: BASF SEInventors: Christian Bittner, Oetter Günter, Ulrich Steinbrenner, Jürgen Huff, Marcus Guzmann
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Patent number: 8461378Abstract: 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: GrantFiled: September 10, 2010Date of Patent: June 11, 2013Assignee: E.I. du Pont de Nemours and CompanyInventors: Allen Capron Sievert, Lee Grant Sprague, James A. Schultz, Katelyn Rae Walck
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Patent number: 8415085Abstract: 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: GrantFiled: May 23, 2012Date of Patent: April 9, 2013Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
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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: 20130066105Abstract: 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: ApplicationFiled: September 12, 2011Publication date: March 14, 2013Applicant: GM GLOBAL TECHNOLOGY OPERATIONS LLCInventor: Ping Liu
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Patent number: 8283492Abstract: 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: GrantFiled: January 20, 2011Date of Patent: October 9, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
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Patent number: 8247160Abstract: 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: GrantFiled: July 13, 2009Date of Patent: August 21, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Akiya Kawaue, Hiroaki Shimizu, Tsuyoshi Nakamura
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Publication number: 20120184763Abstract: 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: ApplicationFiled: September 29, 2010Publication date: July 19, 2012Applicants: Mitsubishi Materials Electronic Chemicals Co., Ltd, MITSUBISHI MATERIALS CORPORATIONInventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
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Publication number: 20120125777Abstract: 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: ApplicationFiled: September 19, 2007Publication date: May 24, 2012Inventors: MICHAEL VIRNIG, Jack Bender, Louis Rebrovic
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Patent number: 8114570Abstract: 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: GrantFiled: March 24, 2009Date of Patent: February 14, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
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Patent number: 8110711Abstract: 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: GrantFiled: September 5, 2008Date of Patent: February 7, 2012Assignee: Central Glass Company, LimitedInventors: Jonathan Joachim Jodry, Masashi Nagamori, Yuji Hagiwara, Masaki Fujiwara, Satoru Narizuka
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Patent number: 8057985Abstract: 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: GrantFiled: August 27, 2009Date of Patent: November 15, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana
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Patent number: 8048604Abstract: 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: GrantFiled: October 21, 2010Date of Patent: November 1, 2011Assignee: E.I.du Pont de Nemours and CompanyInventors: Christopher P. Junk, Mark Andrew Harmer, Andrew Edward Feiring, Frank Leonard Schadt, III, Zoe Schnepp
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Publication number: 20110172459Abstract: 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: ApplicationFiled: September 14, 2009Publication date: July 14, 2011Applicant: NIPPON SHOKUBAI CO., LTDInventors: Masato Nakano, Akihiko Kanzaki, Takahiro Tsumori
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Publication number: 20110152537Abstract: 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: ApplicationFiled: May 12, 2009Publication date: June 23, 2011Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNGInventors: Peter Wasserscheid, Natalia Paape, Andreas Boesmann, Peter Schulz
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Patent number: 7919226Abstract: 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: GrantFiled: August 13, 2008Date of Patent: April 5, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
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Patent number: 7897807Abstract: 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: GrantFiled: February 22, 2010Date of Patent: March 1, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
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Publication number: 20110039203Abstract: 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: ApplicationFiled: October 21, 2010Publication date: February 17, 2011Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: CHRISTOPHER P. JUNK, MARK ANDREW HARMER, ANDREW EDWARD FEIRING, FRANK LEONARD SCHADT, III, ZOE SCHNEPP
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Publication number: 20110015431Abstract: 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: ApplicationFiled: September 5, 2008Publication date: January 20, 2011Applicant: CENTRAL GLASS COMPANY, LIMITEDInventors: Jonathan Joachim Jodry, Masashi Nagamori, Yuji Hagiwara, Masaki Fujiwara, Satoru Narizuka
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Patent number: 7834209Abstract: 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: GrantFiled: June 6, 2006Date of Patent: November 16, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Christopher P. Junk, Mark Andrew Harmer, Andrew Edward Feiring, Frank Leonard Schadt, III, Zoe Schnepp
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Publication number: 20100120980Abstract: 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: ApplicationFiled: November 13, 2008Publication date: May 13, 2010Inventors: Sheng Peng, Ming-Hong Hung, Christopher P. Junk, Phan Linh Tang
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Patent number: 7683209Abstract: 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: GrantFiled: June 6, 2006Date of Patent: March 23, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
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Publication number: 20090292126Abstract: 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: ApplicationFiled: May 27, 2009Publication date: November 26, 2009Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Mark Andrew Harmer, Christopher P. Junk, Jemma Vickery
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Patent number: 7569326Abstract: 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: GrantFiled: October 25, 2007Date of Patent: August 4, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
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Patent number: 7524609Abstract: 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: GrantFiled: March 9, 2007Date of Patent: April 28, 2009Assignee: FUJIFILM CorporationInventor: Kenji Wada
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Patent number: 7514202Abstract: 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: GrantFiled: May 9, 2007Date of Patent: April 7, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeru Watanabe, Jun Hatakeyama
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Patent number: 7511169Abstract: 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: GrantFiled: April 5, 2006Date of Patent: March 31, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
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Publication number: 20080171895Abstract: 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: ApplicationFiled: January 12, 2007Publication date: July 17, 2008Inventors: Paul Daniel Berger, Christie Huimin Berger
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Patent number: 7148375Abstract: 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: GrantFiled: April 2, 2004Date of Patent: December 12, 2006Assignee: Shell Oil CompanyInventors: Charles Lee Edwards, Kirk Herbert Raney, Paul Gregory Shpakoff
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Patent number: 6649790Abstract: 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: GrantFiled: April 19, 2002Date of Patent: November 18, 2003Assignee: Daikin Industries, Ltd.Inventor: Masayoshi Tatemoto
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Patent number: 6459003Abstract: 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: GrantFiled: March 31, 2000Date of Patent: October 1, 2002Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 6121222Abstract: 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: GrantFiled: December 27, 1996Date of Patent: September 19, 2000Assignee: Rhodia Inc.Inventors: Ruoxin Li, David James Tracy, Jiang Yang, Manilal S. Dahanayake
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Patent number: 5814110Abstract: 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: GrantFiled: November 23, 1994Date of Patent: September 29, 1998Assignee: 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