Plural Halogens Containing Patents (Class 568/35)
  • Patent number: 9354515
    Abstract: A resist composition containing a compound represented by general formula (m0), wherein R1 and R2 each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or an alkenyl group which may have a substituent, provided that R1 and R2 may be mutually bonded to form a ring with the sulfur atom; R3 represents an aromatic hydrocarbon group which may have a substituent, an alkenyl group which may have a substituent, or an alkynyl group which may have a substituent; V1 represents a single bond or an alkylene group, provided that, when R3 is an aromatic hydrocarbon group which may have a substituent, V1 is an alkylene group; and X0? represents a monovalent organic anion.
    Type: Grant
    Filed: July 23, 2014
    Date of Patent: May 31, 2016
    Assignee: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Takashi Nagamine, Yoshitaka Komuro, Masatoshi Arai, Yoshiyuki Utsumi
  • Patent number: 9005871
    Abstract: Compounds of the formula (I), wherein Ar1 is for example phenylene or biphenylene both unsubstituted or substituted; Ar2 and Ar3 are for example independently of each other phenyl, naphthyl, biphenylylyl or heteroaryl, all optionally substituted; or Ar1 and Ar2 for example together with a direct bond, O, S or (CO), form a fused ring system; R is for example hydrogen, C3-C30cycloalkyl or C1-C18alkyl; and R1, R2 and R3 independently of each other are for example C1-C10haloalkyl; are effective photoacid generators (PAG).
    Type: Grant
    Filed: October 8, 2009
    Date of Patent: April 14, 2015
    Assignee: BASF SE
    Inventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
  • Publication number: 20140342288
    Abstract: The present invention provides a radiation-sensitive resin composition that contains a polymer having a structural unit that includes an acid-labile group; and an acid generator, wherein the acid generator includes a compound including a sulfonate anion having SO3?, wherein a hydrogen atom or an electron-donating group bonds to an ? carbon atom with respect to SO3?, and an electron-withdrawing group bonds to a ? carbon atom with respect to SO3?; and a radiation-degradable onium cation. The compound preferably has a group represented by the following formula (1-1) or (1-2). In the following formulae (1-1) and (1-2), R1 and R2 each independently represent a hydrogen atom or a monovalent electron-donating group. R3 represent a monovalent electron-withdrawing group. R4 represents a hydrogen atom or a monovalent hydrocarbon group.
    Type: Application
    Filed: May 20, 2014
    Publication date: November 20, 2014
    Applicant: JSR CORPORATION
    Inventors: Hiroshi TOMIOKA, Takakazu KIMOTO, Yusuke ASANO
  • Patent number: 8722005
    Abstract: The invention provides a method for producing hydrogen bis(fluorosulfonyl)imide (HFSI) by reacting hydrogen bis(halosulfonyl)imide (HXSI) with hydrogen fluoride, where each X is independently a nonfluoro-halide, such as Cl, Br, or I.
    Type: Grant
    Filed: July 26, 2013
    Date of Patent: May 13, 2014
    Assignee: Boulder Ionics Corporation
    Inventors: Joseph Carl Poshusta, Jerry Lynn Martin, Rajendra P. Singh
  • Publication number: 20140017559
    Abstract: The object is to provide a secondary battery which has an excellent cycle property even in high-temperature environment and which has small resistance increase even when it is used in high-temperature environment. An exemplary embodiment of the invention is a secondary battery, comprising: a positive electrode, a negative electrode, and an electrolyte liquid; wherein the electrolyte liquid comprises a chain-type fluorinated sulfone compound represented by a predetermined formula.
    Type: Application
    Filed: September 27, 2011
    Publication date: January 16, 2014
    Inventors: Daisuke Kawasaki, Kenichi Shimura, Yoko Hashizume
  • Patent number: 8580486
    Abstract: There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: November 12, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
  • Publication number: 20130274463
    Abstract: The present invention relates to macrolactam compounds, intermediates useful in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing and modifying macrolactams. One use of the compounds and methods described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity. An example of an HCV inhibitory compound that can be synthesized using the procedures described herein is Compound A and derivative thereof.
    Type: Application
    Filed: December 13, 2011
    Publication date: October 17, 2013
    Inventors: Cheng Chen, Jongrock Kong, Guy Humphrey, Sarah Dolman, Hongmei Li, Matthew T. Tudge, Kelvin Yong, Bangping Xiang, Michael Zacuto
  • Publication number: 20130267658
    Abstract: There is provided oligomers comprising a highly fluorinated sulfinate oligomers.
    Type: Application
    Filed: December 6, 2011
    Publication date: October 10, 2013
    Applicant: 3M Innovative Properties Company
    Inventors: Miguel A. Guerra, Gregg D. Dahlke, Denis Duchesne, Tatsuo Fukushi, Werner M.A. Grootaert, Zai-Ming Qiu
  • Patent number: 8512897
    Abstract: Provided are (1) a novel phenyl sulfonate compound, (2) a nonaqueous electrolytic solution comprising an electrolyte salt dissolved in a nonaqueous solvent and containing a phenyl sulfonate compound of the following general formula (II) in an amount of from 0.01 to 10% by mass of the nonaqueous electrolytic solution, and (3) a lithium battery containing the nonaqueous electrolytic solution and excellent in low-temperature cycle property. (wherein X1 to X5 each independently represents a fluorine atom or a hydrogen atom, and from one to four of these are fluorine atoms; R2 represents a linear or branched alkyl group having from 1 to 6 carbon atoms, a linear or branched alkyl group having from 1 to 6 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom, or an aryl group having from 6 to 9 carbon atoms).
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: August 20, 2013
    Assignee: Ube Industries, Ltd.
    Inventors: Koji Abe, Kazuhiro Miyoshi
  • 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: 8377406
    Abstract: The present invention provides methods for producing bis(fluorosulfonyl) compounds of the formula: F—S(O)2—Z—S(O)2—F??I by contacting a nonfluorohalide compound of the formula: X—S(O)2—Z—S(O)2—X with bismuth trifluoride under conditions sufficient to produce the bis(fluorosulfonyl) compound of Formula I, where Z and X are those defined herein.
    Type: Grant
    Filed: August 29, 2012
    Date of Patent: February 19, 2013
    Assignee: Boulder Ionics Corporation
    Inventors: Rajendra P. Singh, Jerry Lynn Martin, Joseph Carl Poshusta
  • Patent number: 8304580
    Abstract: There is provided a method for producing a tris(perfluoroalkanesulfonyl)methide acid salt represented by formula [1], including the steps of (a) reacting a methylmagnesium halide represented by formula [2] with a perfluoroalkanesulfonyl fluoride represented by formula [3], thereby obtaining a reaction mixture; and (b) directly reacting the obtained reaction mixture with at least one selected from the group consisting of alkali metal halides, quaternary ammonium salts, and quaternary phosphonium salts. By this method, it is possible to easily produce the target methide acid salt with high yield.
    Type: Grant
    Filed: December 18, 2007
    Date of Patent: November 6, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Tsutomu Nanmyo, Shintaro Sasaki, Takashi Kume
  • Patent number: 8263811
    Abstract: Process for preparing one or more iodinated organic substances having a molecular mass of less than 2000 (substances (S)) using (A) at least one free-radical-generating substance chosen from peroxides, diazo compounds, dialkyldiphenylalkanes, substances derived from tetraphenylethane, boranes and iniferter substances comprising at least one thiuram disulphide group, (B) an ethylenically unsaturated substance capable of adding a free radical to its ethylenic double bond, (C) molecular iodine, which comprises the steps according to which at least a fraction of (A), at least a fraction of (B) and at least a fraction of (C) are introduced into a reactor, and then the contents of the reactor are caused to react, while introducing therein the possible remainder of (A), the possible remainder of (B) and the possible remainder of (C), until a moment is reached when the content of the reactor is a mixture comprising one or more substances (S).
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: September 11, 2012
    Assignee: Solvay (Société Anonyme)
    Inventors: Patrick Lacroix-Desmazes, Romain Severac, Bernard Boutevin, Vincent Bodart, Vincent Kurowski
  • Patent number: 8247612
    Abstract: There is provided an organic sulfur compound having an excellent controlling effect on harmful arthropods represented by the formula (I): wherein, R1 represents a C1-C5 haloalkyl group having at least one fluorine atom, R2 represents a C1-C4 alkyl group optionally substituted with at least one halogen atom or the like, R3 represents a hydrogen atom or the like, R4 represents a cyano group or the like, R5 represents a hydrogen atom or the like, m represents an integer of 1 to 4, and n represents 0, 1 or 2.
    Type: Grant
    Filed: May 16, 2008
    Date of Patent: August 21, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Hiroyuki Miyazaki
  • Patent number: 8236920
    Abstract: A dihalobiphenyl compound represented by the formula (1): wherein A represents an amino group substituted with one or two C1-C20 hydrocarbon groups or a C1-C20 alkoxy group, R1 represents a fluorine atom, a C1-C20 alkyl group, etc., X1 represents a chlorine atom, a bromine atom or an iodine atom, an k represents an integer of 0 to 3, and a polyarylene comprising a repeating unit represented by the formula (2): wherein A, R1 and k represent the same meanings as defined above.
    Type: Grant
    Filed: September 6, 2006
    Date of Patent: August 7, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyuki Hida, Seiji Oda, Takashi Kamikawa, Katsuhiro Suenobu
  • Publication number: 20110263903
    Abstract: The invention relates to a process for preparing 4,4?-dichlorodiphenyl sulfone proceeding from monochlorobenzene, wherein the content in the monochlorobenzene used of hydrocarbons having from 5 to 8 carbon atoms is at most 100 ppm; based on the total weight of the monochlorobenzene used, including the secondary components. The present invention further relates to the use of monochlorobenzene with the properties mentioned for preparation of 4,4?-dichlorodiphenyl sulfone.
    Type: Application
    Filed: April 21, 2011
    Publication date: October 27, 2011
    Applicant: BASF SE
    Inventors: Patrick Deck, Heiner Schelling, Florian Garlichs
  • Patent number: 8043786
    Abstract: The invention provides novel acid generators which are unproblematic in combustibility and accumulation inside the human body and can generate acids having high acidities and high boiling points and exhibiting properly short diffusion lengths in resist coating films and which permit the formation of resist patterns excellent smoothness with little dependence on the denseness of a mask pattern; sulfonic acids generated from the acid generators; sulfonyl halides useful as raw material in the synthesis of the acid generators; and radiation-sensitive resin compositions containing the acid generators. The acid generators have structures represented by the general formula (I), wherein R1 is a monovalent substituent such as alkoxycarbonyl, alkylsulfonyl, or alkoxysulfonyl; R2 to R4 are each hydrogen or alkyl; k is an integer of 0 or above; and n is an integer of 0 to 5.
    Type: Grant
    Filed: February 20, 2004
    Date of Patent: October 25, 2011
    Assignee: JSR Corporation
    Inventors: Satoshi Ebata, Yong Wang, Isao Nishimura
  • Patent number: 8017656
    Abstract: A compound given by the formula (I): has an excellent controlling activity against noxious arthropods.
    Type: Grant
    Filed: November 1, 2006
    Date of Patent: September 13, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Hiroyuki Miyazaki
  • Patent number: 8008358
    Abstract: The present invention relates to the use of end groups Y, where Y stands for CF3O— or F5S—, as hydrophobic end group in surface-active compounds, corresponding novel compounds, and processes for the preparation of these compounds.
    Type: Grant
    Filed: December 22, 2005
    Date of Patent: August 30, 2011
    Assignee: Merck Patent GmbH
    Inventors: Peer Kirsch, Klaus-Dieter Franz, Andreas Ruhl
  • Patent number: 7977284
    Abstract: A method of making phenol and alkylphenol ethoxylates non-estrogenic by inserting 1 mole of propylene oxide onto the phenolic group before proceeding with the addition of ethylene oxide or mixtures of ethylene and propylene oxide. The final phenolic products can be further reacted to form sulfates, sulfonates, phosphate esters, condensed alkylphenol alkoxylates and other derivatives of alkylphenol or phenol. Non-estrogenic phenol and alkylphenol alkoxylates and their derivatives have been found to be excellent salt tolerant, high temperature stable surfactants for oil recovery from subterranean reservoirs. These products are also useful in forming emulsions of heavy crude for transportation through pipelines.
    Type: Grant
    Filed: March 9, 2010
    Date of Patent: July 12, 2011
    Assignee: Oil Chem Technologies, Inc
    Inventors: Paul Berger, Christie Berger
  • Publication number: 20110020712
    Abstract: Electrolytic solvents and applications of such solvents including electric current-producing devices. For example, a solvent can include a sulfone compound of R1—SO2—R2, with R1 being an alkyl group and R2 a partially oxygenated alkyl group, to exhibit high chemical and thermal stability and high oxidation resistance. For another example, a battery can include, between an anode and a cathode, an electrolyte which includes ionic electrolyte salts and a non-aqueous electrolyte solvent which includes a non-symmetrical, non-cyclic sulfone. The sulfone has a formula of R1—SO2—R2, wherein R1 is a linear or branched alkyl or partially or fully fluorinated linear or branched alkyl group having 1 to 7 carbon atoms, and R2 is a linear or branched or partially or fully fluorinated linear or branched oxygen containing alkyl group having 1 to 7 carbon atoms. The electrolyte can include an electrolyte co-solvent and an electrolyte additive for protective layer formation.
    Type: Application
    Filed: October 4, 2010
    Publication date: January 27, 2011
    Applicant: Arizona Board of Regents for and on behalf of Arizona State University
    Inventors: Charles Austen Angell, Xiao-Guang Sun
  • Publication number: 20100291437
    Abstract: Provided are (1) a novel phenyl sulfonate compound, (2) a nonaqueous electrolytic solution comprising an electrolyte salt dissolved in a nonaqueous solvent and containing a phenyl sulfonate compound of the following general formula (II) in an amount of from 0.01 to 10% by mass of the nonaqueous electrolytic solution, and (3) a lithium battery containing the nonaqueous electrolytic solution and excellent in low-temperature cycle property. (wherein X1 to X5 each independently represents a fluorine atom or a hydrogen atom, and from one to four of these are fluorine atoms; R2 represents a linear or branched alkyl group having from 1 to 6 carbon atoms, a linear or branched alkyl group having from 1 to 6 carbon atoms in which at least one hydrogen atom is substituted with a halogen atom, or an aryl group having from 6 to 9 carbon atoms).
    Type: Application
    Filed: October 24, 2008
    Publication date: November 18, 2010
    Applicant: UBE INDUSTRIES, LTD.
    Inventors: Koji Abe, Kazuhiro Miyoshi
  • Patent number: 7833666
    Abstract: Electrolytic solvents and applications of such solvents including electric current-producing devices. For example, a solvent can include a sulfone compound of R1—SO2—R2, with R1 being an alkyl group and R2 a partially oxygenated alkyl group, to exhibit high chemical and thermal stability and high oxidation resistance. For another example, a battery can include, between an anode and a cathode, an electrolyte which includes ionic electrolyte salts and a non-aqueous electrolyte solvent which includes a non-symmetrical, non-cyclic sulfone. The sulfone has a formula of R1—SO2—R2, wherein R1 is a linear or branched alkyl or partially or fully fluorinated linear or branched alkyl group having 1 to 7 carbon atoms, and R2 is a linear or branched or partially or fully fluorinated linear or branched oxygen containing alkyl group having 1 to 7 carbon atoms. The electrolyte can include an electrolyte co-solvent and an electrolyte additive for protective layer formation.
    Type: Grant
    Filed: July 19, 2007
    Date of Patent: November 16, 2010
    Assignee: Arizona Board of Regents for and behalf of Arizona State University
    Inventors: Charles Austen Angell, Xiao-Guang Sun
  • Patent number: 7833690
    Abstract: The present invention relates to photoacid generating compounds, lithographic resists comprising photoacid generating compounds, and to various lithographic processes techniques, and applications.
    Type: Grant
    Filed: October 6, 2006
    Date of Patent: November 16, 2010
    Assignee: The University of North Carolina at Charlotte
    Inventors: Kenneth E. Gonsalves, Mingxing Wang
  • Patent number: 7834209
    Abstract: Hydrofluoroalkanesulfonates of the general formula R—O—CXH—CX2—SO3M, where R is selected from the group consisting of alkyl groups, functionalized alkyl groups, and alkenyl groups; X is selected from the group consisting of hydrogen and fluorine with the proviso that at least one X is fluorine; and M is a cation, are made by reacting fluorovinyl ether with aqueous sulfite solution. Organic onium hydrofluoroalkanesulfonates are useful as ionic liquids and photoacid generators.
    Type: Grant
    Filed: June 6, 2006
    Date of Patent: November 16, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Christopher P. Junk, Mark Andrew Harmer, Andrew Edward Feiring, Frank Leonard Schadt, III, Zoe Schnepp
  • Patent number: 7812194
    Abstract: 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: Grant
    Filed: August 30, 2006
    Date of Patent: October 12, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Toshiaki Aoai
  • Publication number: 20100022803
    Abstract: There is provided a method for producing a tris(perfluoroalkanesulfonyl)methide acid salt represented by formula [1], including the steps of (a) reacting a methylmagnesium halide represented by formula [2] with a perfluoroalkanesulfonyl fluoride represented by formula [3], thereby obtaining a reaction mixture; and (b) directly reacting the obtained reaction mixture with at least one selected from the group consisting of alkali metal halides, quaternary ammonium salts, and quaternary phosphonium salts. By this method, it is possible to easily produce the target methide acid salt with high yield.
    Type: Application
    Filed: December 18, 2007
    Publication date: January 28, 2010
    Applicant: Central Glass Company, Limited
    Inventors: Tsutomu Nanmyo, Shintaro Sasaki, Takashi Kume
  • Publication number: 20090181319
    Abstract: Fluorine-free photoacid generators and photoresist compositions containing fluorine-free photoacid generators are enabled as alternatives to PFOS/PFAS photoacid generator-containing photoresists. The photoacid generators are characterized by the presence of a fluorine-free aromatic sulfonate anionic component having one or more electron withdrawing groups. The photoacid generators preferably contain a fluorine-free onium cationic component, more preferably a sulfonium cationic component. The photoresist compositions preferably contain an acid sensitive imaging polymer having a lactone functionality. The compositions are especially useful for forming material patterns using 193 nm (ArF) imaging radiation.
    Type: Application
    Filed: January 16, 2008
    Publication date: July 16, 2009
    Applicant: INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: Wenjie Li, Sen Liu, Wu-Song Huang, Pushkara R. Varanasi, Irene Popova
  • Publication number: 20090176175
    Abstract: A photoacid generator P+ A? comprises (a) an antenna group P+ comprising atoms with high EUV photoabsorption cross-sections according to FIG. 1 and A? anions; or (b) an antenna group P+ and A? comprising anions with low photoabsorption cross-sections for EUV; or (c) an antenna group P+, comprising atoms with high EUV photoabsorption cross-sections according to FIG. 1 and A? comprising anions with low photoabsorption cross-sections for EUV. Novel compounds comprise DTFPIO PFBuS, and DTBPIO CN5.
    Type: Application
    Filed: January 8, 2008
    Publication date: July 9, 2009
    Applicant: International Business Machines Corporation
    Inventor: Martin Glodde
  • Publication number: 20090137773
    Abstract: Compositions and methods for making compositions such as RF(R?)nQ are provided. The RF group can include at least two —CF3 groups, the R? group can be a group having at least two carbons, n can be at least 1, and the Q group can include one or more atoms of the periodic table of elements. RF-intermediates (RF(RT)nQg); Surfactants (RF(RT)nQs); Foam stabilizers (RF(RT)IIQFS); Metal complexes (RF(RT)IIQMC); Phosphate ester (RF(RT)HQPE); Polymers (RF(RT)IIQMU); Monomers (RF(RT)IIQM); Urethanes (RF(R?)nQu); and/or Glycols (RF(RT)IIQH) and methods for making the same are provided.
    Type: Application
    Filed: July 28, 2006
    Publication date: May 28, 2009
    Inventors: Andrew Jackson, Vimal Sharma, Bradley E. Edwards, Janet Boggs, Victoria Hedrick, Stephan Brandstadter, John Chien, Edward Norman, Robert Kaufman, Bruno Ameduri, George K. Kostov
  • Patent number: 7435526
    Abstract: 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: Grant
    Filed: June 14, 2004
    Date of Patent: October 14, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Toshiaki Aoai
  • Publication number: 20080161612
    Abstract: Partially fluorinated ionic compounds are prepared. They are useful in the preparation of partially fluorinated dienes, in which the repeat units are cycloaliphatic.
    Type: Application
    Filed: December 13, 2007
    Publication date: July 3, 2008
    Inventors: Zhen-Yu Yang, Amy Qi Han
  • Publication number: 20080149878
    Abstract: The present invention relates to the use of end groups Y, where Y stands for CF3O— or F5S—, as hydrophobic end group in surface-active compounds, corresponding novel compounds, and processes for the preparation of these compounds.
    Type: Application
    Filed: December 22, 2005
    Publication date: June 26, 2008
    Inventors: Peer Kirsch, Klaus-Dieter Franz, Andreas Ruhl
  • Publication number: 20080131810
    Abstract: The present application relates to a compound of formula Ai Xi Bi where Ai and Bi are each individually an organic onium cation; and Xi is anion of the formula ?O3S—CF2CF2OCF2CF2—SO3?. The compounds are useful as photoactive materials.
    Type: Application
    Filed: December 4, 2006
    Publication date: June 5, 2008
    Inventors: M. Dalil Rahman, David L. Rentkiewicz
  • Patent number: 7339082
    Abstract: The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmetric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfinic acid anhydride, and an arylbis (trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.
    Type: Grant
    Filed: November 22, 2004
    Date of Patent: March 4, 2008
    Assignee: Japan Science and Technology Corporation
    Inventors: Kazuaki Ishihara, Hisashi Yamamoto
  • Publication number: 20080032184
    Abstract: A monomer comprising the structure (1a) or (1b) wherein Z comprises S, SO2, or POR wherein R comprises a linear or branched perfluoroalkyl group of 1 to 14 carbon atoms optionally containing oxygen or chlorine, an aryl or substituted aryl group of 6 to 12 carbon atoms, or an alkyl of 1 to 8 carbon atoms; RFcomprises a linear or branched perfluoroalkene group of 1 to 20 carbon atoms, optionally containing oxygen or chlorine; Q is chosen from F, —OM, NH2, —N(M)SO2R2F, and —C(M)(SO2R2F)2, wherein M comprises H, an alkali cation, or ammonium; and R2F groups comprise perfluorinated or partially fluorinated alkyl, and may optionally include ether oxygens; and n is 1 or 2 for (1a), and n is 1, 2, or 3 for (1b). These monomers are used in the preparation of homopolymers and copolymers that are useful in preparing polymer electrolyte membranes. Electrochemical cells, such as fuel cells, containing these membranes are also described.
    Type: Application
    Filed: June 25, 2004
    Publication date: February 7, 2008
    Inventors: Zhen-yu Yang, Mark Roelofs
  • Patent number: 7217492
    Abstract: An onium salt compound having a cation moiety of the following formula (1) is disclosed. wherein A represents I or S, m is 1 or 2, n is 0 or 1, x is 1–10, and Ar1 and Ar2 are (substituted) aromatic hydrocarbon group, and P represents —O—SO2R, —O—S(O)R, or —SO2R, wherein R represents a hydrogen atom, a (substituted) alkyl group, or a (substituted) alicyclic hydrocarbon group. The onium salt compound is suitable as a photoacid generator for photoresists of a positive-tone radiation-sensitive resin composition. The positive-tone radiation-sensitive resin composition containing this compound is useful as a chemically-amplified photoresist exhibiting high resolution at high sensitivity, responsive to various radiations, and having outstanding storage stability.
    Type: Grant
    Filed: December 24, 2003
    Date of Patent: May 15, 2007
    Assignee: JSR Corporation
    Inventors: Eiji Yoneda, Yong Wang, Yukio Nishimura
  • Patent number: 7193113
    Abstract: The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmertric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfonic acid anhydride, and an arylbis(trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.
    Type: Grant
    Filed: December 14, 2001
    Date of Patent: March 20, 2007
    Assignee: Japan Science and Technology Corporation
    Inventors: Kazuaki Ishihara, Hisashi Yamamoto
  • Patent number: 7157600
    Abstract: A process for preparing (per)fluorohalogenethers containing the —SO2F group, having general formula (I): FSO2—R—CF2OCAF—CA?F2??(I) wherein: A and A?, equal to or different from each other, are Cl or Br; R has the following meanings: a (per)fluorinated, preferably perfluorinated, substituent, optionally containing one or more oxygen atoms; by reaction of carbonyl compounds having formula (II): FSO2—R—COF??(II) wherein R is as above; in liquid phase with elemental fluorine and with olefinic compounds having formula (III): CAF?CA?F??(III) wherein A and A? are as above, operating at temperatures from ?120° C. to ?20° C., optionally in the presence of a solvent inert under the reaction conditions.
    Type: Grant
    Filed: March 10, 2004
    Date of Patent: January 2, 2007
    Assignee: Solvay Solexis S.p.A.
    Inventors: Vito Tortelli, Pierangelo Calini, Stefano Millefanti
  • Patent number: 7094501
    Abstract: Disclosed are compositions prepared by free-radical-driven grafting onto hydrocarbons or hydrocarbon ethers of olefinically unsaturated fluorocarbons containing sulfonyl fluoride, fluorosulfonate, fluorosulfonimide, or fluorosulfonyl methide groups, wherein the grafting step is followed by a hydrolysis step in the case of sulfonyl fluoride.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: August 22, 2006
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Hanne Anna Katharina Blau, Pui-Yan Lin, José Manuel Rodriguez-Parada
  • Patent number: 7087788
    Abstract: The present invention relates to new fluorosulfone compounds. These fluorosulfone compounds have utility in preventing, controlling and extinguishing fire.
    Type: Grant
    Filed: August 11, 2004
    Date of Patent: August 8, 2006
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Allen C. Sievert, Mario J. Nappa, Velliyur Nott Mallikarjuna Rao, Paul R. Resnick
  • Patent number: 7053123
    Abstract: (E)-Styryl benzylsulfones useful as antiproliferative agents, including, for example, anticancer agents, are provided according to formula I: wherein: R1 is selected from the group consisting of halogen, C1–C6 alkoxy, nitro, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2–C6 alkoxy); and R2 and R3 are independently selected from the group consisting of halogen, C1–C6 alkoxy, C1–C6 alkyl, nitro, cyano, hydroxyl, phosphonato, amino, sulfamyl, carboxy, acetoxy, and dimethylamino (C2–C6 alkoxy); provided: R1 may not be halogen when R2 and R3 are both halogen; R2 may not be 2-halogen when R3 is 4-halogen; or a pharmaceutically acceptable salt thereof; or formula II: wherein: R4 is selected from the group consisting of C1–C6 alkoxy, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2–C6 alkoxy); R6 is selected from the group consisting of nitro, hydrogen, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2–C6 alkoxy); and R7 is selected from the group consistin
    Type: Grant
    Filed: October 5, 2001
    Date of Patent: May 30, 2006
    Assignee: Temple University-of the Commonwealth System of Higher Education
    Inventors: E. Premkumar Reddy, M. V. Ramana Reddy
  • Patent number: 6991888
    Abstract: The present invention relates to a novel photoresist composition that can be developed with an aqueous alkaline solution, and is capable of being imaged at exposure wavelengths in the deep ultraviolet. The invention also relates to a process for imaging the novel photoresist as well as novel photoacid generators. The novel photoresist comprises a) a polymer containing an acid labile group, and b) a novel mixture of photoactive compounds, where the mixture comprises a lower absorbing compound selected from structure 1 and 2, and a higher absorbing compound selected from structure 4 and 5, where, R1 and R2 R5, R6, R7, R8, and R9 are defined herein; m=1–5; X? is an anion, and Ar is selected from naphthyl, anthracyl, and structure 3, where R30, R31, R32, R33, and R34 are defined herein.
    Type: Grant
    Filed: May 16, 2003
    Date of Patent: January 31, 2006
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Munirathna Padmanaban, Takanori Kudo, Sangho Lee, Ralph R. Dammel, M. Dalil Rahman
  • Patent number: 6887624
    Abstract: Disclosed are compositions prepared by free-radical-driven grafting onto hydrocarbons or hydrocarbon ethers of olefinically unsaturated fluorocarbons containing sulfonyl fluoride, fluorosulfonate, fluorosulfonimide, or fluorosulfonyl methide groups, wherein the grafting step is followed by a hydrolysis step in the case of sulfonyl fluoride.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: May 3, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Hanne Anna Katharina Blau, Pui-Yan Lin, José Manuel Rodriguez-Parada
  • Patent number: 6833480
    Abstract: Substituted (Z)-styrylbenzyl sulfones of the formulae (I, II, III, IV), pharmaceutically acceptable salts thereof, and compositions thereof are provided as cell antiproliferative agents, including, for example, anticancer agents.
    Type: Grant
    Filed: August 21, 2003
    Date of Patent: December 21, 2004
    Assignee: Temple University - Of The Commonwealth System of Higher Education
    Inventors: E. Premkumar Reddy, M. V. Ramana Reddy
  • Patent number: 6727386
    Abstract: A method is provided for making aromatic-imide and aromatic-methylidynetrissulfonyl species by reaction of aromatic species with a reactant according to formula (I): (X—SO2—)m—QH—(—SO2—R1)n  (I) wherein Q is C or N; wherein each X is independently selected from the group consisting of halogens, typically F or Cl; wherein each R1 is independently selected from the group consisting of aliphatic and aromatic groups, which may or may not be saturated, unsaturated, straight-chain, branched, cyclic, heteroatomic, polymeric, halogenated, fluorinated or substituted; wherein m is greater than 0; wherein m+n=2 when Q is N; and wherein m+n=3 when Q is C. Ar may be derived from an aromatic polymeric compound.
    Type: Grant
    Filed: October 25, 2001
    Date of Patent: April 27, 2004
    Assignee: 3M Innovative Properties Company
    Inventor: Steven Joseph Hamrock
  • Patent number: 6723483
    Abstract: A triphenyl sulfonium salt compound shown by the general formula [1] or [3]. (wherein R1 and R2 are each independently a hydrogen atom or a lower alkyl group, provided that at least one of R1 and R2 are a lower alkyl group, R3s are each independently an alkyl group, n is an integer of 0 to 3, i is an integer of 1 to 3, j is an integer of 0 to 2, provided that i+j=3, Y− is an anion derived from a sulfonic acid shown by the general formula [2] R4—SO3H  [2] [wherein R4 is an alkyl group or an aryl group which may have as a substituent an alkyl group]). (wherein X is a phenyl group which has a substituent at an ortho- and/or a meta-position, m is an integer of 1 to 3, q is an integer of 0 to 2, provided that m+q=3, p is 1 or 2 and Zp− is an anion derived from a carboxylic acid).
    Type: Grant
    Filed: December 7, 2000
    Date of Patent: April 20, 2004
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Keiji Oono, Kazuhito Fukasawa, Kazunori Sakamoto, Fumiyoshi Urano, Motoshige Sumino, Shigeaki Imazeki
  • Patent number: 6692893
    Abstract: Onium salts of arylsulfonyloxynaphthalenesulfonate anions with iodonium or sulfonium cations are novel. A chemically amplified resist composition comprising the onium salt as a photoacid generator is suited for microfabrication, especially by deep UV lithography because of many advantages including improved resolution, improved focal latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris after coating, development and peeling, and improved pattern profile after development.
    Type: Grant
    Filed: October 23, 2001
    Date of Patent: February 17, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Jun Watanabe, Takeshi Nagata, Jun Hatakeyama
  • Publication number: 20040030192
    Abstract: The present invention provides a method for producing various types of arylbis(perfluoroalkylsulfonyl)methane having a bulky aryl group and an electron-accepting aryl group in which synthesis was conventionally considered to be difficult, at high efficiency; a novel arylbis(perfluoroalkylsulfonyl)methane that can be widely applied to asymmertric catalyst, various types of functional materials and the like; and a metallic salt thereof. In addition, excellent catalysts are also provided. An aryl halomethane is reacted with a sodium trifluoromethane sulfinate, the arylmethyl triflone produced thereby is reacted with a t-BuLi and the like, the lithium salt of the arylmethyl triflone obtained is reacted with a trifluoromethane sulfonic acid anhydride, and an arylbis(trifluoromethylsulfony)methane such as pentafluorophenylbis(triflyl)methane, {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane and the like are obtained at a high yield.
    Type: Application
    Filed: June 12, 2003
    Publication date: February 12, 2004
    Inventors: Kazuaki Ishihara, Hisashi Yamamoto
  • Patent number: 6657086
    Abstract: Embodiments of the invention relate to C2-substituted indan-1-ols and to their physiologically acceptable salts and physiologically functional derivatives. Compounds of embodiments of the invention may include compounds of formula I in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparation. The compounds are suitable, for example, for use as anorectics.
    Type: Grant
    Filed: August 30, 2002
    Date of Patent: December 2, 2003
    Assignee: Aventis Pharma Deutschland GmbH
    Inventors: Gerhard Jaehne, Volker Krone, Martin Bickel, Matthias Gossel