Halogen Attached Indirectly To The Sulfonate Group By Acyclic Nonionic Bonding Patents (Class 562/113)
  • Patent number: 11822245
    Abstract: A resist composition comprising a base polymer and a quencher containing a compound having the formula (A) is provided.
    Type: Grant
    Filed: March 10, 2021
    Date of Patent: November 21, 2023
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Tomomi Watanabe
  • Patent number: 11401239
    Abstract: Embodiments of the present disclosure generally relate to processes for converting disulfides to conversion products and to processes for producing cysteic acid. In an embodiment, a process for converting cystine to a conversion product is provided. The process include introducing an organic peroxide and water to cystine to form a mixture. The process further includes reacting the mixture, under conversion conditions, to form the conversion product, wherein the conversion product comprises cysteic acid, an amount of cysteic acid in the conversion product is greater than about 90 wt % based on a total weight of the conversion product, and the conversion conditions comprise a conversion temperature from about 15° C. to about 50° C. The process further includes heating the conversion product to remove the organic peroxide.
    Type: Grant
    Filed: May 13, 2021
    Date of Patent: August 2, 2022
    Assignee: FXI INC. LIMITED
    Inventors: Andrius Stanulis, Andrew R. Barron
  • Patent number: 11355362
    Abstract: A washing method, a washing device, a storage medium, and a washing composition for enabling effective removal of a layer to be processed by decomposing or degenerating the layer to be processed at a higher temperature than conventionally. In a state where a substrate provided with a layer to be processed is heated, the substrate is supplied with vapor of a component that can decompose the layer to be processed, and thereafter the layer to be processed that has reacted with the component is removed from the substrate. As the component, a nitric acid or a sulfonic acid is preferable. As the sulfonic acid, a fluorinated alkyl sulfonic acid is preferable.
    Type: Grant
    Filed: February 2, 2018
    Date of Patent: June 7, 2022
    Assignees: Tokyo Ohka Kogyo Co., Ltd., Tokyo Electron Limited
    Inventors: Isao Hirano, Shoichi Terada, Junji Nakamura, Takayuki Toshima
  • Patent number: 9944593
    Abstract: A process for the preparation of the fluoroalkyl sulfonate salt of a nitrogen-based organic base said process comprising the step of reacting a fluoroalkyl sulfonyl halide with an organic base selected from the group consisting of tertiary amines, pyridines, amidines and guanidines.
    Type: Grant
    Filed: September 30, 2014
    Date of Patent: April 17, 2018
    Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Cristiano Monzani, Vito Tortelli
  • Patent number: 9419300
    Abstract: The description includes materials that may be useful for fuel cell applications such as in the manufacture of fuel cell electrodes, proton exchange membranes (PEM), as catalyst additives or in tie layers designed to be thermally and chemically robust while operating within a fuel cell's harsh environment at higher temperatures and to conduct protons, with significantly higher levels of bound acidic groups, while in a low hydration state. Methods of making the materials are also described.
    Type: Grant
    Filed: March 23, 2011
    Date of Patent: August 16, 2016
    Assignee: 3M Innovative Properties Company
    Inventors: Steven Joseph Hamrock, Mark Steven Schaberg
  • Patent number: 9376379
    Abstract: The present invention provides a process for preparation of tetrafluoroethanesulfonic acid.
    Type: Grant
    Filed: July 29, 2013
    Date of Patent: June 28, 2016
    Assignee: SRF Limited
    Inventors: Sarathy Iyengar, Radha Kumaraswamy, Mariano Patrick Philiphs, Vardaraj Ganeshan, Rahul Saxena, Rajdeep Anand
  • Patent number: 9040220
    Abstract: A resist composition including a base component which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component which generates acid upon exposure, the acid-generator including an acid generator consisting of a compound represented by general formula (b1-1) shown below: In which RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: March 2, 2012
    Date of Patent: May 26, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9034556
    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) which generates acid upon exposure, the acid-generator component (B) including an acid generator (B1) consisting of a compound represented by general formula (b1-1) shown below: wherein RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: December 18, 2008
    Date of Patent: May 19, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9023579
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes any of the compounds (A) of general formula (I) below that when exposed to actinic rays or radiation, generates an acid and a resin (B) whose rate of dissolution into an alkali developer is increased by the action of an acid. (The characters used in general formula (I) have the meanings mentioned in the description.
    Type: Grant
    Filed: May 31, 2012
    Date of Patent: May 5, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Shuhei Yamaguchi, Akinori Shibuya
  • Patent number: 9017931
    Abstract: A negative pattern is formed by coating a resist composition comprising a polymer comprising recurring units having a tertiary ester type acid labile group having a plurality of methyl or ethyl groups on alicycle and an acid generator onto a substrate, prebaking, exposing to high-energy radiation, baking, and developing in an organic solvent developer so that the unexposed region of resist film is dissolved away and the exposed region of resist film is not dissolved. The resist composition exhibits a high dissolution contrast during organic solvent development and forms a fine hole or trench pattern of dimensional uniformity.
    Type: Grant
    Filed: August 16, 2013
    Date of Patent: April 28, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Jun Hatakeyama, Masayoshi Sagehashi, Teppei Adachi
  • Patent number: 9005872
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid, a basic-compound component (C) and an acid-generator component (B) which generates acid upon exposure, the component (B) including a compound represented by formula (b1), and the component (C) including at least one compound represented by formulas (c1) to (c3) (wherein Z1 represents a ring skeleton-containing hydrocarbon group, Q1 represents a divalent linking group containing oxygen, Y1 represents a fluorinated alkylene group, M+ represents an organic cation, R1 represents a fluorinated alkyl group or a hydrocarbon group, L1+ and L2+ represents a sulfonium or an iodonium, Z2 represents a hydrogen atom or a hydrocarbon group, Y2 represents a single bond or a divalent linking group containing no fluorine, R2 represents an organic group, Y3 represents an alkylene group or an arylene group; and Rf represents a fluorine-containing hydrocarbon group).
    Type: Grant
    Filed: February 16, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Sho Abe, Hideto Nito
  • Patent number: 8993212
    Abstract: A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; R1 represents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in R1 may be substituted with a substituent; R2 represents RAO or RBRCN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.
    Type: Grant
    Filed: October 14, 2011
    Date of Patent: March 31, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Ryozo Takihana, Satoru Narizuka
  • 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: 8987507
    Abstract: Disclosed is a method for producing a fluoroalkanesulfonic acid including (1) the step of reacting concentrated sulfuric acid and/or fuming sulfuric acid with a fluoroalkanesulfonate to cause an acid decomposition, thereby obtaining a reaction mixture containing the fluoroalkanesulfonic acid and a sulfur component; and (2) the step of adding an oxidizing agent to the reaction mixture obtained by the above step and then conducting a distillation, thereby obtaining the fluoroalkanesulfonic acid from the reaction mixture. It is possible by this method to efficiently reduce the sulfur component, thereby industrially advantageously obtaining fluoroalkanesulfonic acid of high purity.
    Type: Grant
    Filed: August 2, 2012
    Date of Patent: March 24, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Tatsuya Irie, Kenji Isoyama, Tatsuo Miyazaki, Takashi Kashiwaba, Tsutomu Nanmyo
  • Publication number: 20150065746
    Abstract: To address the problem of insufficient biodegradability of perfluorinated surfactants, the present invention provides biodegradable fluorosurfactants derived from olefins having —CHR, —CHRf, —CHF, and/or —CH2 groups, where R is an alkyl group and Rf is a perfluoro or fluroroalkyl group. Preferably, the —CHR, —CHRf, —CHF, and/or —CH2 groups are contained within partially fluorinated alkenes.
    Type: Application
    Filed: August 14, 2014
    Publication date: March 5, 2015
    Inventors: Haridasan K. Nair, Yian Zhai, Andrew J. Poss, Rajiv R. Singh, David Nalewajek
  • 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
  • Patent number: 8932797
    Abstract: A photoacid generator compound has formula (I): G+Z???(I) wherein G has formula (II): In formula (II), X is S or I, each R0 is commonly attached to X and is independently C1-30 alkyl; polycyclic or monocyclic C3-30 cycloalkyl; polycyclic or monocyclic C6-30 aryl; or a combination comprising at least one of the foregoing groups. G has a molecular weight greater than 263.4 g/mol, or less than 263.4 g/mol. One or more R0 groups are further attached to an adjacent R0 group, a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 2 or 3. Z in formula (I) comprises the anion of a sulfonic acid, a sulfonimide, or a sulfonamide. A photoresist and coated film also includes the photoacid generator, and a method of forming an electronic device uses the photoresist.
    Type: Grant
    Filed: November 30, 2011
    Date of Patent: January 13, 2015
    Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
  • Patent number: 8921029
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, R2, RII1, RII2, LII1, YII1, RII3, RII4, RII5, RII6, RII7, n, s and RII8 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: December 30, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8900794
    Abstract: A photoacid generator compound has the formula (I): [A-(CHR1)p]k-(L)-(CH2)m—(C(R2)2)n—SO3?Z+??(I) wherein A is a substituted or unsubstituted, monocyclic, polycyclic, or fused polycyclic C5 or greater cycloaliphatic group optionally comprising O, S, N, F, or a combination comprising at least one of the foregoing, R1 is H, a single bond, or a substituted or unsubstituted C1-30 alkyl group, wherein when R1 is a single bond, R1 is covalently bonded to a carbon atom of A, each R2 is independently H, F, or C1-4 fluoroalkyl, wherein at least one R2 is not hydrogen, L is a linking group comprising a sulfonate group, a sulfonamide group, or a C1-30 sulfonate or sulfonamide-containing group, Z is an organic or inorganic cation, p is an integer of 0 to 10,k is 1 or 2, m is an integer of 0 or greater, and n is an integer of 1 or greater.
    Type: Grant
    Filed: September 28, 2012
    Date of Patent: December 2, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, Shintaro Yamada, William Williams, III
  • Patent number: 8900796
    Abstract: The present invention provides an acid generator generates a sulfonic acid represented by the following general formula (1) in response to high-energy beam or heat: To provide a novel acid generator which is suitably used as an acid generator for a resist composition, which solves the problems of LER and a depth of focus and can be effectively and widely used particularly without degradation of a resolution, a chemically amplified resist composition using the same, and a patterning process.
    Type: Grant
    Filed: February 15, 2013
    Date of Patent: December 2, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Masayoshi Sagehashi
  • Patent number: 8889333
    Abstract: A salt represented by 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 a methylene group may be replaced by an oxygen atom or a carbonyl group, L2 and L3 respectively represent a single bond or a C1-C6 divalent saturated alkyl group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, ring W1 and ring W2 respectively represent a C3-C36 hydrocarbon ring, R1 and R2 respectively represent a hydrogen atom or C1-C6 alkyl group, R3 represents C1-C6 alkyl group, t represents an integer of 0 to 2 and Z+ represents an organic counter ion.
    Type: Grant
    Filed: April 10, 2012
    Date of Patent: November 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida, Yuko Yamashita
  • Patent number: 8871423
    Abstract: A photoresist composition for fabricating a probe array is provided. The photoresist composition includes a photoacid generator having an onium salt and an i-line reactive sensitizer.
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: October 28, 2014
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim, Jin-A Ryu, Myung-Sun Kim, Se-Kyung Baek, Soo-Kyung Kim, Ji-Yun Ham
  • Patent number: 8852846
    Abstract: 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-C20 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, W represents a group represented by the formula (W1), (W2), (W3), (W4) or (W5): and Z+ represents an organic counter ion.
    Type: Grant
    Filed: April 4, 2012
    Date of Patent: October 7, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Anryu, Koji Ichikawa
  • Patent number: 8853441
    Abstract: A sulfonium compound represented by the following formula (1), a photoacid generator containing the sulfonium compound, and a resist composition containing the photoacid generator are provided: wherein X represents an electron donor group; R1 and R2 each independently represent an alkyl group or the like; R4 to R6 each independently represent an alkyl group, or the like; R3 represents a cyclic alkenediyl group or the like; and ?A represents an anion. The sulfonium compound has a photon yield that is controllable by introducing different absorbers to the cation region in one molecule, can address the inconvenience of using a mixture of different photoacid generators when the sulfonium compound is applied as a photoacid generator, has excellent miscibility in a resist, and has enhanced resolution and line edge roughness.
    Type: Grant
    Filed: July 25, 2012
    Date of Patent: October 7, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon Oh, Dae Kyung Yoon, Seung Duk Cho, So Jeong Park
  • Patent number: 8846291
    Abstract: A resist composition including: a base component (A) which exhibits changed solubility in a developing solution under action of acid; a nitrogen-containing organic compound component (C) containing a compound (C1) represented by general formula (c1) shown below; and an acid generator component (B) which generates acid upon exposure, provided that the compound (C1) is excluded from the acid generator component (B): wherein RN represents a nitrogen-containing heterocyclic group which may have a substituent; X0 represents a linear or branched divalent aliphatic hydrocarbon group of 1 to 10 carbon atoms, a cyclic divalent aliphatic hydrocarbon group of 3 to 20 carbon atoms or a divalent aliphatic hydrocarbon group of 3 to 20 carbon having a cyclic partial structure, or any one of these groups in which some or all of the hydrogen atoms thereof have been substituted with fluorine atoms; and M+ represents an organic cation.
    Type: Grant
    Filed: December 6, 2011
    Date of Patent: September 30, 2014
    Assignee: Tokyo Ohka Kogyo Co. Ltd.
    Inventors: Yoshiyuki Utsumi, Kenichiro Miyashita, Akiya Kawaue
  • 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
  • Publication number: 20140171678
    Abstract: Disclosed is a method for producing a fluoroalkanesulfonic acid including (1) the step of reacting concentrated sulfuric acid and/or fuming sulfuric acid with a fluoroalkanesulfonate to cause an acid decomposition, thereby obtaining a reaction mixture containing the fluoroalkanesulfonic acid and a sulfur component; and (2) the step of adding an oxidizing agent to the reaction mixture obtained by the above step and then conducting a distillation, thereby obtaining the fluoroalkanesulfonic acid from the reaction mixture. It is possible by this method to efficiently reduce the sulfur component, thereby industrially advantageously obtaining fluoroalkanesulfonic acid of high purity.
    Type: Application
    Filed: August 2, 2012
    Publication date: June 19, 2014
    Applicant: Central Glass Company, Limited
    Inventors: Tatsuya Irie, Kenji Isoyama, Tatsuo Miyazaki, Takashi Kashiwaba, Tsutomu Nanmyo
  • Patent number: 8703998
    Abstract: A process comprising polymerizing in an aqueous medium at least one fluorinated olefin monomer other than vinylidene fluoride in the presence of a compound of formula (1): Rf(CH2CF2)m—(CH2)nSO3M??(1) wherein Rf is a C1 to C4 linear or branched perfluoroalkyl group, m is an integer of from 1 to 6, n is from 0 to 4, M is H, NH4, Li, Na or K, and a method of altering the surface behavior of a liquid comprising adding to the liquid the composition of a compound of formula (1).
    Type: Grant
    Filed: June 20, 2011
    Date of Patent: April 22, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Sheng Peng, Phan Linh Tang
  • Patent number: 8691490
    Abstract: There is disclosed a sulfonium salt represented by the following general formula (1). In the formula, X and Y each represents a group having a polymerizable functional group; Z represents a divalent hydrocarbon group having 1 to 33 carbon atoms optionally containing a hetero atom; R1 represents a divalent hydrocarbon group having 1 to 36 carbon atoms optionally containing a hetero atom; and R2 and R3 each represents a monovalent hydrocarbon group having 1 to 30 carbon atoms optionally containing a hetero atom or R2 and R3 may be bonded with each other to form a ring together with a sulfur atom in the formula. There can be provided a sulfonium salt usable as a resist composition providing high resolution and excellent in LER in photolithography using a high energy beam such as an ArF excimer laser, an EUV light and an electron beam as a light source, a polymer obtained from the sulfonium salt, a resist composition containing the polymer and a patterning process using the resist composition.
    Type: Grant
    Filed: January 25, 2011
    Date of Patent: April 8, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Satoshi Watanabe, Youichi Ohsawa, Keiichi Masunaga, Takeshi Kinsho
  • Patent number: 8633334
    Abstract: The present invention relates to a method for preparing a highly pure trifluoromethanesulphinic acid. The method of the invention for preparing a highly pure trifluoromethanesulphinic acid, starting from an aqueous mixture comprising a trifluoromethanesulphinic acid salt, a trifluoroacetic acid salt and saline impurities resulting from the method for preparing same, is characterized in that said mixture is subjected to the following operations: —acidification such that the trifluoroacetic acid salt and the triflinic acid salt are released in an acid form, —separation of the trifluoroacetic acid and trifluoromethanesulphinic acid by distillation enabling the trifluoroacetic acid to be recovered at the top of the distillation and the trifluoromethanesulphinic acid to be recovered at the bottom of the distillation, —separation by distillation of the trifluoromethanesulphinic acid present in the distillation residue previously obtained.
    Type: Grant
    Filed: November 25, 2008
    Date of Patent: January 21, 2014
    Assignee: Rhodia Operations
    Inventors: Vincent Schanen, Olivier Buisine, François Metz, Bernard Besson
  • Patent number: 8609891
    Abstract: New photoacid generator compounds are provided that comprise a nitrogen-base functional component of the structure —C(?O)N<. Photoresist compositions also are provided that comprise one or more PAGs of the invention.
    Type: Grant
    Filed: April 27, 2011
    Date of Patent: December 17, 2013
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Young Cheol Bae, Thomas Cardolaccia, Yi Liu
  • Patent number: 8597869
    Abstract: 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: Grant
    Filed: September 23, 2011
    Date of Patent: December 3, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Takeshi Kinsho, Tomohiro Kobayashi
  • Publication number: 20130316248
    Abstract: The invention relates to a method for producing perfluoroalkanesulfonic acid esters and for further transforming the same into the salts thereof. The invention also relates to the use of the produced compounds in electrolytes, batteries, capacitors, supercapacitors, and galvanic cells.
    Type: Application
    Filed: July 8, 2009
    Publication date: November 28, 2013
    Inventors: Nikolai Ignatyev, Michael Schmidt, Udo Heider, Peter Sartori, Andry Kucheryna
  • Publication number: 20130288179
    Abstract: A radiation-sensitive resin composition includes a compound represented by a formula (1), and a polymer that includes a structural unit having an acid-labile group. R1 and R4 each independently represent a hydrogen atom, or the like. R2 and R3 each independently represent a hydrogen atom or the like. X1 and X2 each independently represent a hydrogen atom, or the like, or X1 and X2 taken together represent —S—, —O—, —SO2—, or the like. A represents an ethanediyl group, wherein at least one hydrogen atom included in X1, X2 and A is substituted by —Y—SO3?M+. Y represents an alkanediyl group having 1 to 10 carbon atoms, or the like. M+ represents a monovalent onium cation. In the case where —Y—SO3?M+ is present in a plurality of number, a plurality of Ys are each identical or different and a plurality of M+s are each identical or different.
    Type: Application
    Filed: June 27, 2013
    Publication date: October 31, 2013
    Inventors: Kazuo NAKAHARA, Ken MARUYAMA
  • Patent number: 8557500
    Abstract: 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: Grant
    Filed: February 28, 2012
    Date of Patent: October 15, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
  • Publication number: 20130244185
    Abstract: A radiation-sensitive resin composition includes an acid generating agent to generate an organic acid by irradiation with a radioactive ray. The organic acid has a cyclic hydrocarbon group and an organic group including a bond that is cleavable by an acid or a base to produce a polar group. The organic acid is preferably represented by a following formula (I). Z represents an organic acid group. R1 represents an alkanediyl group, wherein a part or all of hydrogen atoms of the alkanediyl group represented by R1 are optionally substituted by a fluorine atom. X represents a single bond, O, OCO, COO, CO, SO3 or SO2. R2 represents a cyclic hydrocarbon group. R3 represents a monovalent organic group having a functional group represented by a following formula (x). n is an integer of 1 to 3.
    Type: Application
    Filed: September 14, 2012
    Publication date: September 19, 2013
    Applicant: JSR Corporation
    Inventors: Yasuhiko MATSUDA, Takanori Kawakami
  • Patent number: 8471059
    Abstract: The present invention relates to a method for preparing a salt of trifluoromethanesulphinic acid termed “triflinic acid”. More specifically, the invention relates to a method for preparing a highly pure triflinic acid salt.
    Type: Grant
    Filed: November 25, 2008
    Date of Patent: June 25, 2013
    Assignee: Rhodia Operations
    Inventors: Vincent Schanen, Olivier Buisine, François Metz, Bernard Besson
  • Publication number: 20130149644
    Abstract: A radiation-sensitive composition includes a photoacid generator represented by a general formula (1), and a solvent. Each R0 independently represents a hydrogen atom, a fluorine atom, or a substituted or unsubstituted monovalent organic group. R1 represents a fluorine atom or a substituted or unsubstituted monovalent organic group. R2 represents a fluorine atom or a substituted or unsubstituted monovalent organic group. Rf represents a fluoromethylene group or a divalent fluoroalkylene group. M+ represents a monovalent onium cation. Optionally R1 bonds to Rf or R2 to form a cyclic structure.
    Type: Application
    Filed: February 5, 2013
    Publication date: June 13, 2013
    Applicant: JSR Corporation
    Inventor: JSR Corporation
  • 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: 8435717
    Abstract: A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.
    Type: Grant
    Filed: February 14, 2008
    Date of Patent: May 7, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
  • Patent number: 8431326
    Abstract: 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: Grant
    Filed: October 3, 2011
    Date of Patent: April 30, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Mitsuyoshi Ochiai, Takashi Hiraoka
  • Patent number: 8420294
    Abstract: 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: Grant
    Filed: November 25, 2011
    Date of Patent: April 16, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • 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: 20130065186
    Abstract: A radiation-sensitive resin composition includes an acid generating agent to generate an organic acid by irradiation with a radioactive ray. The organic acid has a cyclic hydrocarbon group and an organic group including a bond that is cleavable by an acid or a base to produce a polar group. The organic acid is preferably represented by a following formula (I). Z represents an organic acid group. R2 represents an alkanediyl group, wherein a part or all of hydrogen atoms of the alkanediyl group represented by R1 are optionally substituted by a fluorine atom. X represents a single bond, O, OCO, COO, CO, SO3 or SO2. R2 represents a cyclic hydrocarbon group. R3 represents a monovalent organic group having a functional group represented by a following formula (x). n is an integer of 1 to 3.
    Type: Application
    Filed: September 14, 2012
    Publication date: March 14, 2013
    Applicant: JSR Corporation
    Inventors: Yasuhiko MATSUDA, Takanori Kawakami
  • Publication number: 20130037753
    Abstract: Disclosed is an organic electronic material comprising charge transporting compounds and ionic compounds having electron-accepting properties and high solubility in a solvent. The organic electronic material is characterized by comprising charge transporting compounds and ionic compounds, and in that at least one of the ionic compounds is any one kind of compounds represented by general formulas (1b)-(3b). (In the formulas Y1-Y6 each independently represent a divalent linking group, R1-R6 each independently represent an electron-attracting organic substituent (these structures can further have substituents and hetero-atoms, and R1, R2 and R3, or, R4-R6 can respectively combine and become a ring shape or a polymer shape) and L+ represents a monovalent cation.
    Type: Application
    Filed: April 20, 2011
    Publication date: February 14, 2013
    Applicant: HITACHI CHEMICAL COMPANY, LTD
    Inventors: Kenichi Ishitsuka, Shigeaki Funyuu, Yousuke Hoshi
  • Publication number: 20120316058
    Abstract: The present invention relates to salts having thiouronium or uronium cations, to processes for the preparation thereof, and to the use thereof as ionic liquids.
    Type: Application
    Filed: August 21, 2012
    Publication date: December 13, 2012
    Applicant: MERCK PATENT GMBH
    Inventors: Nikolai (Myloka) IGNATYEV, Urs WELZ-BIERMANN, German BISSKY, Helge WILLNER, Andriy KUCHERYNA
  • Publication number: 20120302787
    Abstract: A process for producing a perfluorobutanesulfonic acid salt (PFBS salt) is provided. By the process, the yield is improved and PFOS salt content is reduced. Electrochemical fluorination is conducted in a reaction solution comprising anhydrous hydrogen fluoride to generate perfluorobutanesulfonyl fluoride, and the fluoride is hydrolyzed to produce a perfluorobutanesulfonic acid salt. The process for producing a perfluorobutanesulfonic acid salt includes: a step in which liquid phase components generated in the electrochemical fluorination cell are withdrawn and a first a perfluorobutanesulfonic acid salt fraction is prepared therefrom; and a step in which gaseous phase components discharged from the electrochemical fluorination cell are collected and a second perfluorobutanesulfonic acid salt fraction is prepared therefrom.
    Type: Application
    Filed: January 27, 2011
    Publication date: November 29, 2012
    Applicants: Mitsubishi Materials Electronic Chemicals Co., Ltd, MITSUBISHI MATERIALS CORPORATION
    Inventors: Masakazu Uotani, Takeshi Kamiya, Tsunetoshi Honda
  • Patent number: 8318404
    Abstract: A salt represented by the formula (a1): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents —CO—O—Xa1— or —CH2—O—Xa2— wherein Xa1 and Xa2 independently each represent a C1-C15 alkylene group and one or more —CH2— in the alkylene group can be replaced by —O— or —CO—, Y1 represents a C3-C36 alicyclic hydrocarbon group or a C6-C24 aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O— or —CO—, and Z+ represents an organic cation.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: November 27, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Hiromu Sakamoto