Halogen Attached Indirectly To The Sulfonate Group By Acyclic Nonionic Bonding Patents (Class 562/113)
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Patent number: 7514202Abstract: A thermal acid generator of generating an acid on heating above 100° C. has formula: CF3CH(OCOR)CF2SO3?(R1)4N+ wherein R is alkyl or aryl, R1 is hydrogen, alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl, or R1 may bond together to form a ring with N. The sulfonic acid generated possesses an ester site within molecule so that less bulky acyl groups to bulky groups may be incorporated therein. The thermal acid generator provides a sufficient acid strength, is less volatile due to a high molecular weight, and ensures film formation. Upon disposal of used resist liquid, it may be converted into low accumulative compounds.Type: GrantFiled: May 9, 2007Date of Patent: April 7, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeru Watanabe, Jun Hatakeyama
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Patent number: 7511169Abstract: Sulfonate salts have the formula: CF3—CH(OCOR)—CF2SO3?M+ wherein R is C1-C20 alkyl or C6-C14 aryl, and M+ is a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.Type: GrantFiled: April 5, 2006Date of Patent: March 31, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
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Patent number: 7321054Abstract: 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: GrantFiled: February 6, 2007Date of Patent: January 22, 2008Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Rie Azuma, Tadashi Hiramine
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Patent number: 7276624Abstract: 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: GrantFiled: May 9, 2003Date of Patent: October 2, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Victor Filippovich Cherstkov, Nina Ivanova Delyagina, Richard E. Fernandez, Viacheslav A. Petrov, Paul R. Resnick
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Patent number: 7220914Abstract: Zwitterionic compounds, photovoltaic cell charge carrier layers containing such compounds, photovoltaic cells including such charge carrier layers, and related methods are disclosed.Type: GrantFiled: November 30, 2004Date of Patent: May 22, 2007Assignee: Konarka Technologies, Inc.Inventors: Kethinni G. Chittibabu, Savvas Hadjikyriacou, David Waller
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Patent number: 7169333Abstract: 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: GrantFiled: April 30, 2001Date of Patent: January 30, 2007Assignee: Bayer AktiengesellschaftInventors: Martin Döbler, Walter Köhler, Siegfried Neumann
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Patent number: 6849374Abstract: 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: GrantFiled: November 3, 2001Date of Patent: February 1, 2005Assignee: Shipley Company, L.L.C.Inventors: James F. Cameron, Thomas M. Zydowsky
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Patent number: 6765112Abstract: 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: GrantFiled: March 25, 2003Date of Patent: July 20, 2004Assignee: E. I. du Pont de Nemours and CompanyInventor: James A. Schultz
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Patent number: 6632960Abstract: 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: GrantFiled: June 21, 2002Date of Patent: October 14, 2003Assignees: Goldschmidt AG, Polyset Chemical Company Inc.Inventors: James V. Crivello, Georg Feldmann-Krane, Sascha Oestreich
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Publication number: 20030187233Abstract: 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: ApplicationFiled: September 11, 2002Publication date: October 2, 2003Inventors: Masanobu Onishi, Kenichi Ikeda, Takashi Shimaoka, Masanori Yoshida
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Publication number: 20030153780Abstract: 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: ApplicationFiled: July 24, 2002Publication date: August 14, 2003Inventors: Marlon Haniff, Ted Deisenroth, John Jennings, Karl Friedrich Mueller
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Publication number: 20030096189Abstract: 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: ApplicationFiled: March 11, 1997Publication date: May 22, 2003Inventors: FUJIO YAGIHASHI, TOMOYOSHI FURIHATA, JUN WATANABE, AKINOBU TANAKA, YOSHIO KAWAI, TADAHITO MATSUA
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Publication number: 20030027061Abstract: 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: ApplicationFiled: November 3, 2001Publication date: February 6, 2003Applicant: Shipley Company, L.L.C.Inventors: James F. Cameron, Thomas M. Zydowsky
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Patent number: 6509495Abstract: 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: GrantFiled: July 19, 2001Date of Patent: January 21, 2003Assignee: Rhodia ChimieInventors: Georges Cordier, Roland Jacquot
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Patent number: 6479698Abstract: 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: GrantFiled: March 20, 2002Date of Patent: November 12, 2002Assignee: Rhodia ChimieInventors: Virginie Pevere, Pierre Danerol
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Publication number: 20020102491Abstract: A positive photosensitive composition comprises a compound capable of generating a specified sulfonic acid upon irradiation with one of an actinic ray and radiation and (B) a resin capable of decomposing under the action of an acid to increase the solubility in an alkali developer.Type: ApplicationFiled: October 17, 2001Publication date: August 1, 2002Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kunihiko Kodama, Toshiaki Aoai
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Patent number: 6365769Abstract: 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: GrantFiled: February 15, 2000Date of Patent: April 2, 2002Assignee: 3M Innovative Properties CompanyInventors: Frederick E. Behr, Rudolf J. Dams, Johan E. DeWitte, Donald F. Hagen
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Patent number: 6172238Abstract: A process manufactures of a compound of formula: and unique intermediates.Type: GrantFiled: December 13, 1999Date of Patent: January 9, 2001Assignee: Hoffmann-La Roche Inc.Inventors: Paul Anthony Brown, Hans Hilpert
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Patent number: 6140436Abstract: 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: GrantFiled: November 9, 1999Date of Patent: October 31, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Christopher Marc Doyle, William Brown Farnham, Andrew Edward Feiring, Peter Arnold Morken, Mark Gerrit Roelofs
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Patent number: 6111136Abstract: 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: GrantFiled: September 4, 1998Date of Patent: August 29, 2000Assignees: Electricite de France Service National, Centre National de la Recherche ScientifiqueInventors: Hatem Marzouk, Laurent Petit, Marc Tordeux, Amaya Berecibar, Claude Wakselman
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Patent number: 5859288Abstract: 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: GrantFiled: March 22, 1996Date of Patent: January 12, 1999Assignee: Rhone-Poulenc ChimieInventors: Gerard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
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Patent number: 5753776Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: May 19, 1998Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5710320Abstract: 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: GrantFiled: January 16, 1996Date of Patent: January 20, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Dennis E. Vogel, Kim M. Vogel
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Patent number: 5674949Abstract: This invention pertains to a method for liquid-phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: October 7, 1997Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5672741Abstract: 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: GrantFiled: February 1, 1996Date of Patent: September 30, 1997Assignee: Haldor Topsoe A/SInventors: Sven Ivar Hommeltoft, Ole Ekelund
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Patent number: 5585507Abstract: 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: GrantFiled: June 7, 1995Date of Patent: December 17, 1996Assignee: NEC CorporationInventors: Kaichiro Nakano, Katsumi Maeda, Shigeyuki Iwasa, Etsuo Hasegawa
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Patent number: 5539059Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.Type: GrantFiled: June 6, 1995Date of Patent: July 23, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5510510Abstract: 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: GrantFiled: June 28, 1994Date of Patent: April 23, 1996Assignee: Bristol-Meyers Squibb CompanyInventors: Dinesh V. Patel, Scott A. Biller
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Patent number: 5498754Abstract: 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: GrantFiled: April 18, 1994Date of Patent: March 12, 1996Assignee: Central Glass Co., Ltd.Inventors: Tamio Nakamura, Takashi Yokoyama, Yoshiyuki Kobayashi
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Patent number: 5488147Abstract: 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: GrantFiled: July 21, 1994Date of Patent: January 30, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Dennis E. Vogel, Kim M. Vogel
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Patent number: 5461117Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 13, 1994Date of Patent: October 24, 1995Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5380923Abstract: 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: GrantFiled: April 29, 1993Date of Patent: January 10, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Bradford B. Wright, Omar Farooq, Robert J. DeVoe
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Patent number: 5332790Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: July 26, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322904Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322903Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: January 17, 1992Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5302757Abstract: 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: GrantFiled: September 14, 1992Date of Patent: April 12, 1994Assignee: Eastman Kodak CompanyInventor: Franklin D. Saeva
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Patent number: 5256815Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises a) reacting a tetrahydrofuran of formula ##STR2## with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, andb) then reacting the compound of formula III with an aqueous bisulfite solution to form a bisulfite adduct of formula ##STR4## in which X is halogen and Y is a cation equivalent of an alkali metal or alkaline earth metal ion, andc) then cyclising the adduct, in the presence of a base, with a thiolate of formula ##STR5## in which R.sub.1 is C.Type: GrantFiled: November 12, 1992Date of Patent: October 26, 1993Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 5243099Abstract: 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: GrantFiled: September 9, 1992Date of Patent: September 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Diane L. Packett
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Patent number: 5169981Abstract: 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: GrantFiled: December 6, 1991Date of Patent: December 8, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Diane L. Packett
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Patent number: 5105006Abstract: 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: GrantFiled: May 25, 1989Date of Patent: April 14, 1992Assignee: The Dow Chemical CompanyInventor: Theodore L. Parker
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Patent number: 5093432Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: September 28, 1989Date of Patent: March 3, 1992Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5059711Abstract: 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: GrantFiled: March 24, 1988Date of Patent: October 22, 1991Assignee: Bayer AktiengesellschaftInventors: Dietmar Bielefeldt, Albrecht Marhold
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Patent number: 5047568Abstract: 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: GrantFiled: November 18, 1988Date of Patent: September 10, 1991Assignee: International Business Machines CorporationInventors: Raymond W. Angelo, Jeffrey D. Gelorme, Joseph P. Kuczynski, William H. Lawrence, Socrates P. Pappas, Logan L. Simpson
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Patent number: 5045632Abstract: 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: GrantFiled: December 19, 1990Date of Patent: September 3, 1991Assignee: The Dow Chemical CompanyInventor: Theodore L. Parker
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Patent number: 5011983Abstract: 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: GrantFiled: January 23, 1987Date of Patent: April 30, 1991Assignee: Minnesota Mining and Manufacturing CompanyInventor: Fred E. Behr
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Patent number: 5004829Abstract: (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: GrantFiled: April 9, 1990Date of Patent: April 2, 1991Assignee: Central Glass Company, LimitedInventors: Minoru Aramaki, Takashi Suenaga, Hiroaki Sakaguchi, Takanori Hamana
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Patent number: 4983747Abstract: 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: GrantFiled: March 15, 1990Date of Patent: January 8, 1991Assignee: Tokuyama Soda Kabushiki KaishaInventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
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Patent number: 4933377Abstract: 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: GrantFiled: February 29, 1988Date of Patent: June 12, 1990Inventors: Franklin D. Saeva, David T. Breslin
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Patent number: 4927962Abstract: 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: GrantFiled: August 29, 1988Date of Patent: May 22, 1990Assignee: Central Glass Company, LimitedInventors: Minoru Aramaki, Hiroaki Sakaguchi, Tamio Nakamura
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Patent number: 4925975Abstract: 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: GrantFiled: April 21, 1989Date of Patent: May 15, 1990Assignee: Central Glass Company, LimitedInventors: Minoru Aramaki, Kimitaka Okamoto, Hiroaki Sakaguchi, Tamio Nakamura