Halogen Attached Indirectly To The Sulfonate Group By Acyclic Nonionic Bonding Patents (Class 562/113)
  • Patent number: 7514202
    Abstract: A thermal acid generator of generating an acid on heating above 100° C. has formula: CF3CH(OCOR)CF2SO3?(R1)4N+ wherein R is alkyl or aryl, R1 is hydrogen, alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl, or R1 may bond together to form a ring with N. The sulfonic acid generated possesses an ester site within molecule so that less bulky acyl groups to bulky groups may be incorporated therein. The thermal acid generator provides a sufficient acid strength, is less volatile due to a high molecular weight, and ensures film formation. Upon disposal of used resist liquid, it may be converted into low accumulative compounds.
    Type: Grant
    Filed: May 9, 2007
    Date of Patent: April 7, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Jun Hatakeyama
  • Patent number: 7511169
    Abstract: Sulfonate salts have the formula: CF3—CH(OCOR)—CF2SO3?M+ wherein R is C1-C20 alkyl or C6-C14 aryl, and M+ is a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: April 5, 2006
    Date of Patent: March 31, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
  • Patent number: 7321054
    Abstract: Poly(ortho-methylphenol) is obtainable at high purities and yields using industrial processes by causing a secondary amine and formaldehyde to react with a polyphenol (first step), and then breaking down the aminomethyl group of the obtained poly(ortho-aminomethyl)phenol by means of hydrogenolysis in the presence of a hydrogenation catalyst (second step).
    Type: Grant
    Filed: February 6, 2007
    Date of Patent: January 22, 2008
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Rie Azuma, Tadashi Hiramine
  • Patent number: 7276624
    Abstract: Hexafluoroisobutylene and its higher homologs are easily reacted with SO3 to give fluorosulfates of the formula CH2?C(R)CF2OSO2F, wherein R is a linear, branched or cyclic fluoroalkyl group comprised of 1 to 10 carbon atoms and may contain ether oxygen. These compounds react under mild conditions with many nucleophiles to give CH2?C(R)CF2X, where X is derived from the nucleophile. This reaction provides a route to many substituted hexafluoroisobutylenes, which copolymerize easily with other fluoro- and hydrocarbon monomers such as vinylidene fluoride and ethylene.
    Type: Grant
    Filed: May 9, 2003
    Date of Patent: October 2, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Victor Filippovich Cherstkov, Nina Ivanova Delyagina, Richard E. Fernandez, Viacheslav A. Petrov, Paul R. Resnick
  • Patent number: 7220914
    Abstract: Zwitterionic compounds, photovoltaic cell charge carrier layers containing such compounds, photovoltaic cells including such charge carrier layers, and related methods are disclosed.
    Type: Grant
    Filed: November 30, 2004
    Date of Patent: May 22, 2007
    Assignee: Konarka Technologies, Inc.
    Inventors: Kethinni G. Chittibabu, Savvas Hadjikyriacou, David Waller
  • Patent number: 7169333
    Abstract: The present invention provides an antistatic agent of the formula (I) R—SO3NR?R?R??R?? ??(I) wherein R represents a perfluorinated cyclic or linear, branched or unbranched carbon chain having 1 to 30 carbon atoms, R? represents a cyclic or linear, branched or unbranched carbon chain having 1 to 30 carbon atoms, which is unsubstituted or substituted with halogen, hydroxy, cycloalkyl or alkyl, and R?, R??, R?? independently represent a cyclic or linear, branched or unbranched carbon chain having 1 to 30 carbon atoms, which is unsubstituted or substituted with halogen, hydroxy, cycloalkyl or alkyl, with the proviso that at least one of the radicals R?, R?, R?? and R?? must not represent ethyl. The antistatic agent of the present invention may be incorporated in plastic molding materials to provide antistatic properties thereto.
    Type: Grant
    Filed: April 30, 2001
    Date of Patent: January 30, 2007
    Assignee: Bayer Aktiengesellschaft
    Inventors: Martin Döbler, Walter Köhler, Siegfried Neumann
  • Patent number: 6849374
    Abstract: This invention relates to new photoacid generator compounds and photoresist compositions that comprise such compounds. In particular, the invention relates to photoacid generator compounds that generate an ?,?-difluoroalkyl sulfonic acid upon exposure to activating radiation. Positive- and negative-acting chemically amplified resists that contain such PAGs are particularly preferred. The invention also includes methods for synthesis of such PAGs and ?,?-difluoroalkyl sulfonic acids.
    Type: Grant
    Filed: November 3, 2001
    Date of Patent: February 1, 2005
    Assignee: Shipley Company, L.L.C.
    Inventors: James F. Cameron, Thomas M. Zydowsky
  • Patent number: 6765112
    Abstract: A process that can be used for manufacturing a tetraalkylonium perfluoroalkylsulfonate is provided. The process comprises contacting a tetraalkylonium halide with a metal perfluoroalkyl sulfonate to produce a mixture; allowing the second mixture to produce an aqueous upper layer and a separate lower liquid layer; separating the lower liquid layer from the upper aqueous layers to produce a product layer; optionally washing the product layer with 1 to 10 volumes of water, based on the volume of the product layer at a temperature of about 50° C. to about 100° C. to produce a washed product layer; and drying the product layer or washed product.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: July 20, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: James A. Schultz
  • Patent number: 6632960
    Abstract: Diaryliodonium salts are disclosed, as well as a method for preparing them, in which one of the aryl groups bonded to the positively-charged iodine ion contains a methyl substituent, and the other one contains a hydroxyl-substituted alkoxy group. The salts are synthesized from (o, m, or p)-iodotoluene, as opposed to iodobenzene, and therefore do not pose a carcinogenic risk. In addition, the present salts are unexpectedly more soluble in most organic solvents, as well as in nonpolar monomers, than the corresponding benzene catalysts. The salts are useful as cationic photoinitiators, cationic thermal initiators (often combined with a cocatalyst, e.g. copper), and as starting materials in the synthesis of urethane-containing iodonium salts.
    Type: Grant
    Filed: June 21, 2002
    Date of Patent: October 14, 2003
    Assignees: Goldschmidt AG, Polyset Chemical Company Inc.
    Inventors: James V. Crivello, Georg Feldmann-Krane, Sascha Oestreich
  • Publication number: 20030187233
    Abstract: Perfluoroisopropylbenzene derivatives of the general formula (I) or salts thereof, useful as intermediates or raw materials in the synthesis of various industrial materials including agricultural chemicals, drugs and surfactants, wherein X1 is H, halogeno, formyl, optionally halogenated C1-6 alkyl, —C(═O)—R1 (wherein R1 is H, halogeno, hydroxyl, C1-6 alkyl, or NR2R3, with R2 and R3 being each H, C1-6 alkyl, or the like), or the like; X3 is H, halogeno, hydroxyl, cyano, isocyanato, hydrazino, diazo, —C(═O)—R1, —SO2—R4 (wherein R4 is halogeno, hydroxyl, C1-6 alkyl, or NR5R6, with R5 and R6 being each H or C1-6 alkyl), or the like; and X4 is H, halogeno, C1-6 alkyl, or C1-6 alkoxy, with publicly known compounds being excepted.
    Type: Application
    Filed: September 11, 2002
    Publication date: October 2, 2003
    Inventors: Masanobu Onishi, Kenichi Ikeda, Takashi Shimaoka, Masanori Yoshida
  • Publication number: 20030153780
    Abstract: Perfluoroalkyl-substituted amines, acids, amino acids and thioether acid compounds containing a perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkene group as well as derivatives thereof, are described. They are useful as surfactants in a variety of applications where low surface tensions are required, including coating formulations for glass, wood, metal, cement, paper, textiles, as foam control agents in polyurethane foams and especially in aqueous fire-fighting formulations.
    Type: Application
    Filed: July 24, 2002
    Publication date: August 14, 2003
    Inventors: Marlon Haniff, Ted Deisenroth, John Jennings, Karl Friedrich Mueller
  • Publication number: 20030096189
    Abstract: Disclosed are novel onium salts represented by general formula (R) 3S+M, wherein three R's may be the same or different, each being an aryl group, provided that at least one of R's is a t-alkoxy substituted phenyl group, and M is an anion capable of foxing the sulfonium salts; and high energy radiation-responsive positive resist materials using said novel onium salts as acid generator.
    Type: Application
    Filed: March 11, 1997
    Publication date: May 22, 2003
    Inventors: FUJIO YAGIHASHI, TOMOYOSHI FURIHATA, JUN WATANABE, AKINOBU TANAKA, YOSHIO KAWAI, TADAHITO MATSUA
  • Publication number: 20030027061
    Abstract: This invention relates to new photoacid generator compounds and photoresist compositions that comprise such compounds. In particular, the invention relates to photoacid generator compounds that generate an &agr;,&agr;-difluoroalkyl sulfonic acid upon exposure to activating radiation. Positive- and negative-acting chemically amplified resists that contain such PAGs are particularly preferred.
    Type: Application
    Filed: November 3, 2001
    Publication date: February 6, 2003
    Applicant: Shipley Company, L.L.C.
    Inventors: James F. Cameron, Thomas M. Zydowsky
  • Patent number: 6509495
    Abstract: The invention concerns a selective hydrodehalogenation method characterised in that it comprises a step which consists in contacting a substrate including a sp 3 hybridisation carbon atom bearing an electro-attracting group and at least a fluorine atom, and a halogen atom heavier than fluorine, with a reagent comprising: an aqueous phase, a base, a group VIII metal as hydrogenation catalyst, and hydrogen dissolved in the aqueous phase, at a concentration in equilibrium with a gas phase whereof the partial pressure in hydrogen is not less than 50 kPa, advantageously ranging between 50 kPa and 2.10 7 Pa. The invention is applicable to organic synthesis.
    Type: Grant
    Filed: July 19, 2001
    Date of Patent: January 21, 2003
    Assignee: Rhodia Chimie
    Inventors: Georges Cordier, Roland Jacquot
  • Patent number: 6479698
    Abstract: The invention concerns a method for preparing sulphonate salts, alkaline or alkaline-earth, corresponding to anion of general formula (I):(R—CF2—SO3−)n, through alkaline hydrolysis of sulphonyl chlorides corresponding to formula (II). The invention is characterized in that it comprises at least a step which consists in alkaline hydrolysis of sulphonyl chloride carried out in the presence of a phase-transfer agent.
    Type: Grant
    Filed: March 20, 2002
    Date of Patent: November 12, 2002
    Assignee: Rhodia Chimie
    Inventors: Virginie Pevere, Pierre Danerol
  • Publication number: 20020102491
    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: Application
    Filed: October 17, 2001
    Publication date: August 1, 2002
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Kunihiko Kodama, Toshiaki Aoai
  • Patent number: 6365769
    Abstract: Novel mixtures of perfluoroalkyl halides and derivatives thereof are described. These mixtures contain some compounds with a straight perfluoroalkyl group and some with a branched perfluoroalkyl group. Methods of preparation and use are also described.
    Type: Grant
    Filed: February 15, 2000
    Date of Patent: April 2, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: Frederick E. Behr, Rudolf J. Dams, Johan E. DeWitte, Donald F. Hagen
  • Patent number: 6172238
    Abstract: A process manufactures of a compound of formula: and unique intermediates.
    Type: Grant
    Filed: December 13, 1999
    Date of Patent: January 9, 2001
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Paul Anthony Brown, Hans Hilpert
  • Patent number: 6140436
    Abstract: This invention concerns ionomers comprising a substantially fluorinated, but not perfluorinated, polyethylene backbone having pendant groups of fluoroalkoxy sulfonic acids and the metal salts thereof, and with the uses of said ionomers in electrochemical applications such as batteries, fuel cells, electrolysis cells, ion exchange membranes, sensors, electrochemical capacitors, and modified electrodes.
    Type: Grant
    Filed: November 9, 1999
    Date of Patent: October 31, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Christopher Marc Doyle, William Brown Farnham, Andrew Edward Feiring, Peter Arnold Morken, Mark Gerrit Roelofs
  • Patent number: 6111136
    Abstract: The invention consists of a new method for preparing perfluoroalcanecarboxylic and perfluoroalcanesulfonic acids in which ozone is made to react, in a protic environment, upon a perfluoroalkyl chain comprising at least one oxydizable chemical group.
    Type: Grant
    Filed: September 4, 1998
    Date of Patent: August 29, 2000
    Assignees: Electricite de France Service National, Centre National de la Recherche Scientifique
    Inventors: Hatem Marzouk, Laurent Petit, Marc Tordeux, Amaya Berecibar, Claude Wakselman
  • Patent number: 5859288
    Abstract: The invention relates to a reagent which is useful for the synthesis of oxysulphide-containing fluorine-containing organic derivatives by reacting with an oxide of sulphur, especially sulphur dioxide, characterized in that it comprises:a) a fluorocarboxylic acid of formula E.sub.w --CF.sub.2 --COOH where E.sub.w is an electron-withdrawing group or atom which is at least partially salified by an organic or inorganic cation, andb) an aprotic polar solvent; andin that the content of releasable protons carried by its various components, including their impurities, is at most equal to half the initial molar concentration of the said fluorocarboxylic acid.This reagent can be used by heating in order to form fluorine-containing sulphinic or sulphonic acids.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: January 12, 1999
    Assignee: Rhone-Poulenc Chimie
    Inventors: Gerard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
  • Patent number: 5753776
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 19, 1998
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5710320
    Abstract: The present invention provides a convenient, simple, safe and efficient one-pot method for the synthesis of a number of diarlyiodonium triflate salts which does not involve sulfuric acid and which eliminates the need for any counter-ion exchange processes.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: January 20, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Dennis E. Vogel, Kim M. Vogel
  • Patent number: 5674949
    Abstract: This invention pertains to a method for liquid-phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 7, 1997
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5672741
    Abstract: A process for base hydrolysis of a fluorinated sulphonyl fluoride by treatment of the fluoride with at least one mole equivalent of water in a basic solvent for a sufficient time to obtain a salt of a corresponding fluorinated sulphonic acid with the basic solvent and separating the obtained salt from the solution, wherein the basic solvent is selected from the group of tertiary amines.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: September 30, 1997
    Assignee: Haldor Topsoe A/S
    Inventors: Sven Ivar Hommeltoft, Ole Ekelund
  • Patent number: 5585507
    Abstract: A photoresist composition containing an alkylsulfonium salt compound represented by the following general formula (I): ##STR1## Wherein R.sup.1 and R.sup.2 may be the same or different, each being a linear, branched or cyclic C.sub.1 to C.sub.8 alkyl radical, R.sup.3 is a linear, branched or cyclic C.sub.1 to C.sub.8 alkyl radical, a C.sub.5 to C.sub.7 2-oxocycloalkyl radical, or a linear or branched C.sub.3 to C.sub.8 2-oxoalkyl radical, and Y.sup.- represents a counter ion. The photoresist composition has high transparency to deep U.V. light having wavelengths of 220 nm or less and is capable of forming good fine patterns with high sensitivity, thus being useful as chemically amplified type resist which is exposed to the deep U.V. light from an ArF excimer laser.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 17, 1996
    Assignee: NEC Corporation
    Inventors: Kaichiro Nakano, Katsumi Maeda, Shigeyuki Iwasa, Etsuo Hasegawa
  • Patent number: 5539059
    Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 23, 1996
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5510510
    Abstract: Inhibition of farnesyl transferase, which is an enzyme involved in ras oncogene expression, and inhibition of cholesterol biosynthesis, are effected by compounds of the formula ##STR1## their enantiomers, diastereomers, and pharmaceutically acceptable salts, prodrugs, and solvates, wherein:x is --ONR.sup.1 C(O)--, --N(OR.sup.1)C(O)--, --NR.sup.1 C(O)--, --C(O)NR.sup.1 --, --NR.sup.1 S(O.sub.2)--, --C(O)O--, --OC(O)--, --C(O)--, --O--, --NR.sup.1 -- or --(S).sub.q --;Y is --CO.sub.2 R.sup.2, --SO.sub.3 R.sup.2 or --P(O) (OR.sup.2) (R.sup.3);R is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkenylene or aryl;R.sup.3 is --(O).sub.t R.sup.4 ;R.sup.1, R.sup.2 and R.sup.4 are each independently hydrogen, alkyl, aryl or aralkyl;m and n are each independently 0 or an integer from 1 to 5;p and t are each independently 0 or 1; andq is an integer from 1 to 2.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: April 23, 1996
    Assignee: Bristol-Meyers Squibb Company
    Inventors: Dinesh V. Patel, Scott A. Biller
  • Patent number: 5498754
    Abstract: A process for refining a crude fluoroalkylsulfonic acid represented by the general formula RfSO.sub.3 H wherein Rf is a fluoroalkyl group having 1 to 4 carbon atoms into a highly refined one substantially free of impurities, said process comprising the steps of: (a) providing said crude fluoroalkylsulfonic acid, (b) mixing said crude fluoroalkylsulfonic acid with water or said water and an active silica to obtain a mixture, (c) stirring said mixture while maintaining said mixture at a higher temperature than room temperature, and (d) subjecting the mixture treated in said step (c) to distillation.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: March 12, 1996
    Assignee: Central Glass Co., Ltd.
    Inventors: Tamio Nakamura, Takashi Yokoyama, Yoshiyuki Kobayashi
  • Patent number: 5488147
    Abstract: The present invention provides a convenient, simple, safe and efficient one-pot method for the synthesis of a number of diarlyiodonium triflate salts which does not involve sulfuric acid and which eliminates the need for any counter-ion exchange processes.
    Type: Grant
    Filed: July 21, 1994
    Date of Patent: January 30, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Dennis E. Vogel, Kim M. Vogel
  • Patent number: 5461117
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: October 24, 1995
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5380923
    Abstract: Polymeric triarylsulfonium salts are provided having a repeating structural unit with the formula: ##STR1## where R represents a substituted or unsubstituted aryl group, X.sup.- represents a non-nucleophilic anion, n represents an integer greater than or equal to 0 and p represents an integer greater than or equal to 2 and may be prepared by combining (a) an arylbis(p-fluorophenyl)substituted sulfonium salt with a bis(trimethylsilylated)dithiol in a polar aprotic solvent.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: January 10, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Bradford B. Wright, Omar Farooq, Robert J. DeVoe
  • Patent number: 5332790
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: July 26, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322904
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322903
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5302757
    Abstract: A composition of matter including an onium salt and a method of forming images. The onium salt has a chromophore which absorbs ultraviolet radiation, an S, Se, As, N or P atom which is free of substituents exhibiting a higher energy occupied molecular orbital than the chromophore; an insulating group which links the chromophore to the S, Se, As, N or P atom of the salt and substantially prevents .pi. resonance from the chromophore through the S, Se, As, N or P atom; and an anion. The onium salt is capable of forming a Bronsted acid upon exposure to ultraviolet radiation in the presence of a proton source. In the method of forming images, the onium salt is exposed to ultraviolet radiation in the presence of a proton source, to convert said onium salt to a Bronsted acid.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: April 12, 1994
    Assignee: Eastman Kodak Company
    Inventor: Franklin D. Saeva
  • Patent number: 5256815
    Abstract: 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: Grant
    Filed: November 12, 1992
    Date of Patent: October 26, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ruedi Kanel, John G. Dingwall
  • Patent number: 5243099
    Abstract: Organic polymer additive containing polar functional groups enhances the stability of palladium-containing catalysts for the telomerization of conjugated diolefins in the presence of active hydrogen-containing telomerization agent to produce alpha-substituted alkadienes.
    Type: Grant
    Filed: September 9, 1992
    Date of Patent: September 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Diane L. Packett
  • Patent number: 5169981
    Abstract: Organic polymer additive containing polar functional groups enhances the stability of palladium-containing catalysts for the telomerization of conjugated diolefins in the presence of active hydrogen-containing telomerization agent to produce alpha-substituted alkadienes.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: December 8, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Diane L. Packett
  • Patent number: 5105006
    Abstract: The invention is a novel phosphonium salt, useful as an initiator or catalyst in the reaction of oxirane groups in an epoxy resin with aromatic carbonate and/or ester linkages in monomeric, oligomeric, or polymeric carbonates, esters, or estercarbonates.
    Type: Grant
    Filed: May 25, 1989
    Date of Patent: April 14, 1992
    Assignee: The Dow Chemical Company
    Inventor: Theodore L. Parker
  • Patent number: 5093432
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: March 3, 1992
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5059711
    Abstract: Trifluoromethanesulphonic acid is prepared from bis-(trifluoromethyl) disulphane in the liquid phase and in acidic medium by means of an oxygen-containing oxidizing agent.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: October 22, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Bielefeldt, Albrecht Marhold
  • Patent number: 5047568
    Abstract: Sulfonium salts of the formula: ##STR1## wherein Ar is a fused aromatic radical; R.sub.1 is a divalent organic bridge; each R.sub.2 and R.sub.3 individually is an alkyl, aryl, alkaryl, aralkyl or substituted aryl, provided thatn not more than one of R.sub.2 and R.sub.3 is alkyl; and A is a non-nucleophilic anion; use thereof and preparation thereof.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: September 10, 1991
    Assignee: International Business Machines Corporation
    Inventors: Raymond W. Angelo, Jeffrey D. Gelorme, Joseph P. Kuczynski, William H. Lawrence, Socrates P. Pappas, Logan L. Simpson
  • Patent number: 5045632
    Abstract: The invention is a novel bis(phosphoranylidene) ammonium salt useful as an initiator/catalyst in the reaction of oxirane groups in an epoxy resin with aromatic carbonate and/or ester linkages in monomeric, oligomeric, or polymeric carbonates, esters, or estercarbonates.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: September 3, 1991
    Assignee: The Dow Chemical Company
    Inventor: Theodore L. Parker
  • Patent number: 5011983
    Abstract: Omega-chlorosulfonyl perfluoroalkanesulfonates and omega-fluorosulfonyl perfluoroalkane sulfonates. These compounds can be used to prepare esters, amides, or latent catalysts for the polymerization of cationically-sensitive monomers. The .omega.-chlorosulfonyl perfluoroalkanesulfonates can be reacted with ethylenically unsaturated compounds to incorporate hydrophilic perfluoroalkanesulfonate groups into the ethylenically unsaturated compound.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: April 30, 1991
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Fred E. Behr
  • Patent number: 5004829
    Abstract: (CF.sub.3 SO.sub.2).sub.2 O is formed by reaction of CF.sub.3 SO.sub.3 H with P.sub.2 O.sub.5 and taken out of the reaction system by distillation, but the residue of the distillation contains a considerable amount of unreacted CF.sub.3 SO.sub.3 H. From the residue unreacted by adding water or a phosphoric acid solution, preferably the latter, to the residue to obtain a fluidic mixture containing an adequate amount of water and subjecting the mixture to distillation, preferably under reduced pressure at temperatures ranging from 180.degree. to 280.degree. C. It is possible to form additional CF.sub.3 SO.sub.3 H during the recovery process by adding a metal salt of CF.sub.3 SO.sub.3 H to the aformentioned mixture since the metal salt is decomposed by phosphoric acid contained in the mixture.
    Type: Grant
    Filed: April 9, 1990
    Date of Patent: April 2, 1991
    Assignee: Central Glass Company, Limited
    Inventors: Minoru Aramaki, Takashi Suenaga, Hiroaki Sakaguchi, Takanori Hamana
  • Patent number: 4983747
    Abstract: Disclosed is a process for the preparation of a perfluoroorganic compound, which comprises fluorinating a partially fluorinated or unfluorinated organic compound having carbon-to-fluorine bonds under mild conditions and then, contacting the resulting reaction mixture with a fluorine gas at a temperature of 110.degree. to 180.degree. C.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: January 8, 1991
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
  • Patent number: 4933377
    Abstract: Sulfonium and oxysulfonium salts, useful as photoinitiators, have directly attached to the sulfur atom thereof:at least one aromatic or heterocyclic aromatic substituent containing at least 14 aromatic atoms and having a removable positive hydrogen ion, said substituent exhibiting a higher energy occupied molecular orbital than at least one other substituent directly attached to said sulfur atom;and at least one substituent comprising an electron withdrawing group and exhibiting a lower energy unoccupied molecular orbital than at least one other substituent directly attached to said sulfur atom;said salt being capable, upon exposure to visible radiation, of undergoing irreversible intramolecular rearrangement to form a Bronsted acid comprising the anion of said salt and said removable positive hydrogen ion.
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: June 12, 1990
    Inventors: Franklin D. Saeva, David T. Breslin
  • Patent number: 4927962
    Abstract: A fluorocarbon carboxylic acid Rf(COOH).sub.m (Rf is C.sub.1 -C.sub.10 perfluoroalkyl group, m is 1 or 2) is prepared by the steps of hydrolyzing Rf(COF).sub.m with water to obtain an acidic solution, neutralizing the acidic solution with aqueous solution of KOH to form Rf(COOK).sub.m, precipitating and separating Rf(COOK).sub.m from the solution and converting Rf(COOK).sub.m into Rf(COOH).sub.m by acid decomposition. The content of free fluorine can extremely be reduced by treating Rf(COOK).sub.m with sulfuric acid and silica. The mother liquor is recycled after removing KF by treatment with a metal hydroxide and replenishing with KOH. In preparing a fluorocarbon sulfonic acid RfSO.sub.3 H (Rf is C.sub.1 -C.sub.3 perfluoroalkyl group) in substantially the same way, RfSO.sub.3 K is formed in aqueous solution of KOH by bringing gaseous RfSO.sub.2 F into contact with the KOH solution under normal pressure, while controlling the feed rate of RfSO.sub.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: May 22, 1990
    Assignee: Central Glass Company, Limited
    Inventors: Minoru Aramaki, Hiroaki Sakaguchi, Tamio Nakamura
  • Patent number: 4925975
    Abstract: In preparing a fluoroalkylsulfonate RfSO.sub.3 M, where Rf is a perfluoroalkyl gruop having not more than 6 carbon atoms and M is an alkali metal, by neutralization reaction between a fluoroalkylsulfonic acid RfSO.sub.3 H and an alkali metal carbonate or hydroxide, the reaction is carried out under acidic conditions such that at the end of the reaction pH of the reaction liquid is lower than 6, and preferably not higher than 3. By so maintaining the reaction liquid acidic, the obtained RfSO.sub.3 M becomes very low in the concentrations of anionic impurities such as free fluorine, free chlorine and carbonate radical and, besides becomes low in moisture absorbency.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: May 15, 1990
    Assignee: Central Glass Company, Limited
    Inventors: Minoru Aramaki, Kimitaka Okamoto, Hiroaki Sakaguchi, Tamio Nakamura