Chalcogen Attached Indirectly To The Sulfonate Group By Acyclic Nonionic Bonding Patents (Class 562/108)
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Publication number: 20150087521Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.Type: ApplicationFiled: March 13, 2013Publication date: March 26, 2015Applicant: Stepan CompanyInventors: David R. Allen, Marcos Alonso, Mary Beddaoui, Randal J. Bernhardt, Aaron Brown, Scott Dillavou, Xue Min Dong, Wilma Gorman, John C. Hutchison, Gary Luebke, Renee Luka, Franz Luxem, Andrew D Malec, Ronald A. Masters, Dennis S. Murphy, Nicholas Pendleton, Irma Ryklin, Patti Skelton, Brian Sook, Chris Spaulding, Krista Turpin, Gregory Wallace, Michael Wiester, Patrick Shane Wolfe
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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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Patent number: 8889888Abstract: A fluorine-containing sulfonic acid salt or a compound having a fluorine-containing sulfonic acid group, either of which having a structure represented by the following general formula (1), is provided. Such a salt or compound can act as a suitable photo-acid generator, and can form a resist pattern having excellent sensitivity, resolution and mask-dependence. [In general formula (1), R represents a substituted or unsubstituted linear or branched monovalent hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted monovalent hydrocarbon group having 3 to 30 carbon atoms and a cyclic or a partially cyclic structure, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic organic group having 4 to 30 carbon atoms.Type: GrantFiled: July 6, 2009Date of Patent: November 18, 2014Assignee: Central Glass Company, LimitedInventors: Masashi Nagamori, Masaki Fujiwara, Kazunori Mori, Satoru Narizuka
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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: 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: 8716518Abstract: A monomer compound has the formula (I): where each R1, R2, and R3 is independently H, F, C1-10 alkyl, fluoro-substituted C1-10 alkyl, C1-10 cycloalkyl, or fluoro-substituted C1-10 cycloalkyl, provided that at least one of R1, R2, or R3 is F; n is an integer of from 1 to 10, A is a halogenated or non-halogenated C2-30 olefin-containing polymerizable group, and G+ is an organic or inorganic cation. The monomer is the reaction product of a sultone precursor and the oxyanion of a hydroxy-containing halogenated or non-halogenated C2-30 olefin-containing compound. A polymer includes the monomer of formula (I).Type: GrantFiled: December 29, 2011Date of Patent: May 6, 2014Assignees: Rohm and Haas Electronic Materials LLC, Dow Global Technologies LLCInventors: Suzanne M. Coley, David R. Wilson, Francis J. Timmers
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Patent number: 8686166Abstract: A 2,2-bis(fluoroalkyl)oxirane (A) is prepared by reacting a fluorinated alcohol (1) with a chlorinating, brominating or sulfonylating agent under basic conditions to form an oxirane precursor (2) and subjecting the oxirane precursor to ring closure under basic conditions. R1 and R2 are fluoroalkyl groups, R3 and R4 are hydrogen or monovalent hydrocarbon groups, X is chlorine, bromine or —OSO2R5 group, and R5 is alkyl or aryl.Type: GrantFiled: June 19, 2012Date of Patent: April 1, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayoshi Sagehashi, Takeru Watanabe, Youichi Ohsawa, Koji Hasegawa, Masaki Ohashi
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Patent number: 8597869Abstract: A sulfonium salt of a naphthyltetrahydrothiophenium cation having a fluoroalkoxy chain with a specific anion is provided. The sulfonium salt is used as a photoacid generator to form a resist composition which when processed by immersion lithography, offers advantages of restrained dissolution in the immersion water and less pattern dependence or dark/bright bias.Type: GrantFiled: September 23, 2011Date of Patent: December 3, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Takeshi Kinsho, Tomohiro Kobayashi
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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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Patent number: 8557500Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, L2 represents a single bond or a C1-C6 alkanediyl group in which one or more —CH2— can be replaced by —O— or —CO—, Y represents a C3-C18 alicyclic hydrocarbon group which can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O—, —CO— or —SO2—, and Z+ represents an organic counter ion.Type: GrantFiled: February 28, 2012Date of Patent: October 15, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
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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: 8431326Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, ring W represents a C3-C36 aliphatic ring in which one or more —CH2— can be replaced by —O—, —S—, —CO— or —SO2— and in which one or more hydrogen atoms can be replaced by a hydroxyl group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C12 alicyclic hydrocarbon group or a C6-C10 aromatic hydrocarbon group, Rf is independently in each occurrence a fluorine atom or a C1-C6 fluorinated alkyl group, n represents an integer of 1 to 10, and Z+ represents an organic counter ion.Type: GrantFiled: October 3, 2011Date of Patent: April 30, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Mitsuyoshi Ochiai, Takashi Hiraoka
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Patent number: 8420294Abstract: The present invention provides a salt represented by the formula (I): wherein R1 and R2 independently each represent a C1-C6 alkyl group or R1 and R2 are bonded each other to form a C5-C20 aliphatic ring together with the carbon atom to which they are bonded, R3 and R4 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO— and which may be substituted with one or more fluorine atoms, and Z1+ represents an organic counter ion.Type: GrantFiled: November 25, 2011Date of Patent: April 16, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
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Publication number: 20130005997Abstract: A 2,2-bis(fluoroalkyl)oxirane (A) is prepared by reacting a fluorinated alcohol (1) with a chlorinating, brominating or sulfonylating agent under basic conditions to form an oxirane precursor (2) and subjecting the oxirane precursor to ring closure under basic conditions. R1 and R2 are fluoroalkyl groups, R3 and R4 are hydrogen or monovalent hydrocarbon groups, X is chlorine, bromine or —OSO2R5 group, and R5 is alkyl or aryl.Type: ApplicationFiled: June 19, 2012Publication date: January 3, 2013Inventors: Masayoshi SAGEHASHI, Takeru WATANABE, Youichi OHSAWA, Koji HASEGAWA, Masaki OHASHI
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Patent number: 8283491Abstract: The present invention is directed to an isomerized alpha olefin sulfonate and a method of making the same wherein the isomerized alpha olefin sulfonate is derived from sulfonating an isomerized alpha olefin with sulfur trioxide in the presence of air thereby producing an isomerized alpha olefin sulfonic acid, wherein the isomerized alpha olefin is derived from the isomerization of C12-C40 normal alpha olefins; and neutralizing the isomerized alpha olefin sulfonic acid with a source of a mono-valent cation.Type: GrantFiled: October 23, 2008Date of Patent: October 9, 2012Assignee: Chevron Oronite Company LLCInventors: Curtis Bay Campbell, Theresa Ann Denslow
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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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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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Patent number: 8030515Abstract: Sulfonate salts have the formula: HOCH2CH2CF2CF2SO3?M+ wherein M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oxime sulfonates and sulfonyloxyimides derived from these salts are effective photoacid generators in chemically amplified resist compositions.Type: GrantFiled: March 9, 2011Date of Patent: October 4, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
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Publication number: 20110217654Abstract: The invention pertains to a compound generating an acid of the formula I or II, for instance corresponding sulfonium and iodonium salts, as well as corresponding sulfonyloximes wherein X is CH2 or CO; Y is O, NR4, S, O(CO), O(CO)O, O(CO)NR4, OSO2, O(CS), or O(CS)NR4; R1 is for example C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alkyl, interrupted C2-C18alkyl, interrupted C3-C30cycloalkyl, interrupted C3-C30cycloalkyl-C1-C18alkyl, interrupted C4-C30cycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or heteroaryl, all unsubstituted or are substituted; or R1 is NR12R13; R2 and R3 are for example C3-C30cycloalkylene, C3-C30cycloalkyl-C1-C18alkylene, C1-C18alkylene, C1-C10haloalkylene, C2-C12alkenylene, C4-C30cycloalkenylene, phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or heteroarylene; all unsubstituted or substituted; R4 is for example C3-C30cycloalkyl, C3-C30cycloalkyl-C1-C18alType: ApplicationFiled: February 16, 2011Publication date: September 8, 2011Applicant: BASF SEInventors: Hitoshi Yamato, Toshikage Asakura, Akira Matsumoto, Keita Tanaka, Yuichi Nishimae
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Publication number: 20110193068Abstract: A composite film, a flexible substrate, and an organic light emitting device, the composite film including a composite including a sulfonic acid group containing moiety connected by an ether linkage (—O—) to an inorganic material having a nano-sized interlayer distance.Type: ApplicationFiled: December 8, 2010Publication date: August 11, 2011Inventors: Jin-O Lim, Kie-Hyun Nam
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Publication number: 20110160481Abstract: Sulfonate salts have the formula: HOCH2CH2CF2CF2SO3?M+ wherein M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oxime sulfonates and sulfonyloxyimides derived from these salts are effective photoacid generators in chemically amplified resist compositions.Type: ApplicationFiled: March 9, 2011Publication date: June 30, 2011Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Katsuhiro KOBAYASHI, Youichi OHSAWA, Takeshi KINSHO, Takeru WATANABE
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Publication number: 20110138888Abstract: The present disclosure relates to the treatment, e.g. reduction, of body fat mass levels for example in overweight and obese subjects. The present disclosure also relates to weight control in a subject where obesity should be avoided. Disclosed herein are methods of reducing body fat mass e.g reducing obesity or preventing weight gain and agents used in such methods whereby the agents inhibit a sulphur containing amino acid. Also included in the present disclosure include, without being limited to, methods for determining regimes for the treatment of obesity as well as other subject matter.Type: ApplicationFiled: July 21, 2009Publication date: June 16, 2011Inventors: Amany Elshorbagy, Helga Margareta Refsum
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Publication number: 20110112306Abstract: A fluorine-containing sulfonic acid salt or a compound having a fluorine-containing sulfonic acid group, either of which having a structure represented by the following general formula (1), is provided. Such a salt or compound can act as a suitable photo-acid generator, and can form a resist pattern having excellent sensitivity, resolution and mask-dependence. [In general formula (1), R represents a substituted or unsubstituted linear or branched monovalent hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted monovalent hydrocarbon group having 3 to 30 carbon atoms and a cyclic or a partially cyclic structure, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic organic group having 4 to 30 carbon atoms.Type: ApplicationFiled: July 6, 2009Publication date: May 12, 2011Applicant: CENTRAL GLASS COMPANY, LIMITEDInventors: Masashi Nagamori, Masaki Fujiwara, Kazunori Mori, Satoru Narizuka
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Patent number: 7928262Abstract: Sulfonate salts have the formula: HOCH2CH2CF2CF2SO3?M+ wherein M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oxime sulfonates and sulfonyloxyimides derived from these salts are effective photoacid generators in chemically amplified resist compositions.Type: GrantFiled: June 25, 2007Date of Patent: April 19, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
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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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Publication number: 20100324329Abstract: A compound is shown by the following formula (5) in which at least one of Rf groups represents a fluorine atom or a linear or branched perfluoroalkyl group having 1 to 10 carbon atoms, A? represents a substituted or unsubstituted, linear or branched alkylene group having 1 to 20 carbon atoms, an alkylene group having at least one hetero atom, or a single bond, G represents a divalent organic group having a fluorine atom or a single bond, Mm+ represents an onium cation, m represents a natural number of 1 to 3, and p represents a natural number of 1 to 8.Type: ApplicationFiled: August 31, 2010Publication date: December 23, 2010Applicant: JSR CorporationInventors: Tomoki Nagai, Eiji Yoneda, Takuma Ebata, Takanori Kawakami, Makoto Sugiura, Tsutomu Shimokawa, Makoto Shimizu
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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: 20100209827Abstract: There is disclosed a sulfonate shown by the following general formula (2). R1—COOC(CF3)2—CH2SO3?M+??(2) (In the formula, R1 represents a linear, a branched, or a cyclic monovalent hydrocarbon group having 1 to 50 carbon atoms optionally containing a hetero atom. M+ represents a cation.) There can be provided: a novel sulfonate which is effective for a chemically amplified resist composition having a sufficiently high solubility (compatibility) in a resist solvent and a resin, a good storage stability, a PED stability, a further wider depth of focus, a good sensitivity, in particular a high resolution and a good pattern profile form; a photosensitive acid generator; a resist composition using this; a photomask blank, and a patterning process.Type: ApplicationFiled: February 16, 2010Publication date: August 19, 2010Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Masaki OHASHI, Takeshi KINSHO, Youichi OHSAWA
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Publication number: 20100150804Abstract: One aspect of the present invention relates to amine-functionalized task-specific ionic liquids (TSILs). In certain embodiments, the ionic liquids of the invention comprise beta-hydroxy amines, aryl amines or tertiary amines. The TSILs may be used for gas capture, capitalizing on their non-volatile nature. In certain embodiments, the captured gas is selected from the group consisting of CO2, SO2, CS2, and NO2. Another aspect of the present invention relates to a library of CO2-philic salts, which library facilitates reactive gas separation. In certain embodiments, the CO2-philic salts are CO2-reactive TSILs. In certain embodiments, the CO2-philic salts are resinous or plastic in nature.Type: ApplicationFiled: April 2, 2008Publication date: June 17, 2010Applicant: University of South AlabamaInventor: James H. Davis, JR.
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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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Publication number: 20080227032Abstract: Novel classes of ionic photoacid generator (PAGs) compounds having relatively environmentally friendly anions with no perfluorooctyl sulfonate (no-PFOS) are provided and photoresist composition that comprise such compounds. The new PAGs produce a photoacid having a short or no perfluoro alkyl chain (i.e., no-PFOS) attached to a variety of functional groups. The PAGs of the invention are useful as photoactive component in the chemically amplified resist compositions used for microfabrication.Type: ApplicationFiled: May 29, 2008Publication date: September 18, 2008Applicant: Cornell Research Foundation, Inc.Inventors: Christopher K. Ober, Ramakrishnan Ayothi, Kyung-Min Kim, Xiang-Qian Liu
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Patent number: 7319096Abstract: This invention relates to novel compounds which are thyroid receptor ligands, preferably antagonists, and to methods for using such compounds in the treatment of cardiac and metabolic disorders, such as cardiac arrhythmias, thyrotoxicosis, subclinical hyperthyrodism and liver diseases.Type: GrantFiled: April 15, 2002Date of Patent: January 15, 2008Assignee: Karo Bio ABInventors: Johan Malm, Peter Brandt, Karin Edvinsson, Thomas Ericsson, Sandra Gordon
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Publication number: 20070298352Abstract: Sulfonate salts have the formula: HOCH2CH2CF2CF2SO3?M+ wherein M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oxime sulfonates and sulfonyloxyimides derived from these salts are effective photoacid generators in chemically amplified resist compositions.Type: ApplicationFiled: June 25, 2007Publication date: December 27, 2007Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Katsuhiro KOBAYASHI, Youichi OHSAWA, Takeshi KINSHO, Takeru WATANABE
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Publication number: 20030065195Abstract: 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: ApplicationFiled: July 26, 2002Publication date: April 3, 2003Applicant: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 6500981Abstract: The present invention provides water soluble ethylenically unsaturated monomers selected from the group consisting of formula I and II wherein R1, R2, R3, R4, R5, and R6 are independently selected from the group consisting of hydrogen, and C1-C5 primary, secondary or tertiary lower alkyl group; B is a monovalent or multivalent metal selected from the group consisting of alkali metals, alkaline earth metals and transition metals; and x represents the stoichiometric valence requirement of the molecule. The invention also provides polymers and emulsions derived from the above monomers.Type: GrantFiled: August 2, 2000Date of Patent: December 31, 2002Assignee: Ethox Chemicals LLCInventor: Paul David Weipert
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Publication number: 20020102491Abstract: A positive photosensitive composition comprises a compound capable of generating a specified sulfonic acid upon irradiation with one of an actinic ray and radiation and (B) a resin capable of decomposing under the action of an acid to increase the solubility in an alkali developer.Type: ApplicationFiled: October 17, 2001Publication date: August 1, 2002Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kunihiko Kodama, Toshiaki Aoai
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Patent number: 6326512Abstract: Disclosed is a method of producing an optically active &bgr;-hydroxy sulfonic acid compound comprising hydrogenating a &bgr;-keto sulfonic acid compound represented by formula 1: where R1 represents an alkyl or a phenyl group, which may be substituted, and R2 represents sodium or an alkyl group, in an acidic solvent, in the presence of an asymmetric catalyst comprising a complex of bivalent Ru, having 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl as a ligand, to produce a compound represented by formula 2: where R1 and R2 are as defined above, and * designates an asymmetric carbon atom.Type: GrantFiled: June 1, 2000Date of Patent: December 4, 2001Assignee: President of Nagoya UniversityInventors: Masato Kitamura, Masahiro Yoshimura, Naoki Kanda, Ryoji Noyori
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Patent number: 6316396Abstract: The invention relates to amphiphilic compounds of the general formula (I) with at least two hydrophilic and at least two hydrophobic groups based on di, oligo or polyolethers. The amphiphilic compounds of this invention are highly surface active and are suitable as emulsifiers, demulsifiers, detergents, dispersants and hydrotropes for industrial and domestic purposes, e.g. in the fields of metalworking, ore separation, surface treatment, washing and cleaning, cosmetics, medicine and food processing and preparation.Type: GrantFiled: April 9, 1999Date of Patent: November 13, 2001Assignee: RWE-DEA Aktiengesellschaft fuer Mineraloel und ChemieInventors: Klaus Kwetkat, Wolfgang Schröder
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Patent number: 6160167Abstract: This invention relates to novel compositions of matter which either terminate in a sulfhydryl moiety or are disulfides. The compounds also include a terminal sulfonate or phosphonate moiety, and have many uses, such as toxicity reducing agents when administered with many antineoplastic agents.Type: GrantFiled: September 1, 1998Date of Patent: December 12, 2000Assignee: BioNumerik Pharmaceuticals, Inc.Inventors: Frederick H. Hausheer, Kochat Haridas, Qiuli Huang
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Patent number: 5912385Abstract: This invention relates to a process for the production of an alkanesulfionic acid such as isethionic acid with a high purity in a high yield and at a low cost by oxidation of a (hydroxy)alkylmercaptan with hydrogen peroxide characterized in that a whole amount beyond a stoichiometric amount of a solution of hydrogen peroxide having a H.sub.2 O.sub.2 concentration of not less than 50% by weight is charged into a reaction vessel, said mercaptan is continuously fed at a temperature of 50.degree. C. or lower, aging is carried out, distillation with boiling is carried out and then the reaction mixture is contacted with an anion exchanger.Type: GrantFiled: January 20, 1998Date of Patent: June 15, 1999Assignee: Tokai Denka Kogyo Kabushiki KaishaInventors: Kazuyoshi Kushibe, Hiromitsu Kobayashi, Hirohisa Nitoh, Hirotsugu Kitamura
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Patent number: 5866040Abstract: A novel complex containing an ampholytic and/or semi-polar surfactant as well as a higher fatty acid, and if necessary, a clay mineral, and an emulsified composition containing this complex.Type: GrantFiled: July 27, 1994Date of Patent: February 2, 1999Assignee: Shiseido Company, Ltd.Inventors: Yasunari Nakama, Michihiro Yamaguchi, Kiyoshi Miyazawa, Takayuki Ohmura
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Patent number: 5808140Abstract: A process for synthesizing disulfides and sulfhydryl compounds which are useful pharmaceuticals. The process includes a two step, single pot process for preparing disulfides from an alkenyl sulfonate salt. The disulfides are useful as toxicity mitigating agents of chemotherapeutic drugs, such as certain platinum complexes, and as use therapeutic drugs for a variety of conditions in mammals.The two step process involves first the conversion of the starting reagent to a mercaptane sulfonate, then an oxidation to the desired disulfide.Type: GrantFiled: September 24, 1997Date of Patent: September 15, 1998Assignee: BioNumerik Pharmaceuticals, Inc.Inventor: Kochat Haridas
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Patent number: 5516461Abstract: A process for preparing alkoxylated alkyl glyceryl ether sulfonates which comprises reacting in the presence of water and the absence of ethanol a mixture of alkoxylated glycidyl ethers having as the major quantity of alkoxylated material ##STR1## with a salt of a sulfite bisulfite salt mixture at a temperature below about 110.degree. C. wherein R is an alkyl or alkenyl of 10 to 20 carbon atoms, inclusive, R' is hydrogen or methyl and n has an average value of 1 to 10 and obtaining a sulfonated alkoxylated product having as a major quantity of the alkoxylated material a salt ofR(OCH.sub.2 CHR.sup.1).sub.n OCH.sub.2 CHOHCH.sub.2 SO.sub.Type: GrantFiled: September 28, 1994Date of Patent: May 14, 1996Assignee: Colgate-Palmolive CompanyInventors: Ravi Subramanyam, Suman K. Chopra
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Patent number: 5436366Abstract: A process for preparing an alkoxylated alkyl glyceryl ether sulfonate which comprises reacting a terminal glycidate (epoxy) of the structure ##STR1##with a sulfite salt, a bisulfite salt or a sulfite/bisulfite salt mixture at a temperature at or below about 110.degree. C. wherein R is an alkyl or alkenyl of 10 to 20 carbon atoms, inclusive, R' is hydrogen or methyl and n is an integer having an average value of 1 to 10 and obtaining the sulfonate of the structureR(OCH.sub.2 CHR.sup.1).sub.n OCH.sub.2 CHOHCH.sub.2 SO.sub.3.sup.Type: GrantFiled: October 15, 1993Date of Patent: July 25, 1995Assignee: Colgate-Palmolive CompanyInventors: Ravi Subramanyam, Suman K. Chopra
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Patent number: 5344949Abstract: Surface active anion-cation complexes are synthesized where an organic or organosilicon compound with at least one epoxide group is reacted with a quaternary ammonium hydrogen sulfite of the general formulaHN.sup.+ (R.sup.1).sub.3 SO.sub.3 H.sup.- IwhereinR.sup.1 within the molecule is the same or different and can be(1) an alkyl or hydroxyalkyl group with 1 to 18 carbon atoms,(2) a phenyl group, or(3) a group of the formula C.sub.n H.sub.2n+1 CONH--(CH.sub.2).sub.m --, in which n can be a number from 7 to 17 and m is 2 or 3,in the presence of a polar solvent in such amounts so that the molar ratio of the epoxide group to HN.sup.+ (R.sup.1).sub.3 SO.sub.3 H.sup.- is 2:1.Type: GrantFiled: July 14, 1993Date of Patent: September 6, 1994Assignee: Th. Goldschmidt AGInventors: Gotz Koerner, Klaus-Dieter Klein, Dietmar Schaefer
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Patent number: 5256815Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises a) reacting a tetrahydrofuran of formula ##STR2## with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, andb) then reacting the compound of formula III with an aqueous bisulfite solution to form a bisulfite adduct of formula ##STR4## in which X is halogen and Y is a cation equivalent of an alkali metal or alkaline earth metal ion, andc) then cyclising the adduct, in the presence of a base, with a thiolate of formula ##STR5## in which R.sub.1 is C.Type: GrantFiled: November 12, 1992Date of Patent: October 26, 1993Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 5053530Abstract: Synthesis of isethionic acid comprising contacting an alkali metal isethionate and an organic acid.Type: GrantFiled: April 10, 1990Date of Patent: October 1, 1991Assignee: Phillips Petroleum CompanyInventors: John S. Roberts, Harold W. Mark