Plural Halogens Containing Patents (Class 568/35)
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Patent number: 11535589Abstract: The present invention relates to novel compounds containing fluorinated end groups, to the use thereof as surface-active substances, and to compositions comprising these compounds.Type: GrantFiled: November 1, 2017Date of Patent: December 27, 2022Assignee: MERCK PATENT GMBHInventors: Reiner Friedrich, Fabian Koch
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Patent number: 9354515Abstract: 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: GrantFiled: July 23, 2014Date of Patent: May 31, 2016Assignee: TOKYO OHKA KOGYO CO., LTD.Inventors: Takashi Nagamine, Yoshitaka Komuro, Masatoshi Arai, Yoshiyuki Utsumi
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Patent number: 9005871Abstract: 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: GrantFiled: October 8, 2009Date of Patent: April 14, 2015Assignee: BASF SEInventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
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Publication number: 20140342288Abstract: 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: ApplicationFiled: May 20, 2014Publication date: November 20, 2014Applicant: JSR CORPORATIONInventors: Hiroshi TOMIOKA, Takakazu KIMOTO, Yusuke ASANO
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Patent number: 8722005Abstract: 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: GrantFiled: July 26, 2013Date of Patent: May 13, 2014Assignee: Boulder Ionics CorporationInventors: Joseph Carl Poshusta, Jerry Lynn Martin, Rajendra P. Singh
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Publication number: 20140017559Abstract: 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: ApplicationFiled: September 27, 2011Publication date: January 16, 2014Inventors: Daisuke Kawasaki, Kenichi Shimura, Yoko Hashizume
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Patent number: 8580486Abstract: 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: GrantFiled: March 10, 2009Date of Patent: November 12, 2013Assignee: Central Glass Company, LimitedInventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
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Publication number: 20130274463Abstract: 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: ApplicationFiled: December 13, 2011Publication date: October 17, 2013Inventors: Cheng Chen, Jongrock Kong, Guy Humphrey, Sarah Dolman, Hongmei Li, Matthew T. Tudge, Kelvin Yong, Bangping Xiang, Michael Zacuto
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Publication number: 20130267658Abstract: There is provided oligomers comprising a highly fluorinated sulfinate oligomers.Type: ApplicationFiled: December 6, 2011Publication date: October 10, 2013Applicant: 3M Innovative Properties CompanyInventors: Miguel A. Guerra, Gregg D. Dahlke, Denis Duchesne, Tatsuo Fukushi, Werner M.A. Grootaert, Zai-Ming Qiu
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Patent number: 8512897Abstract: 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: GrantFiled: October 24, 2008Date of Patent: August 20, 2013Assignee: Ube Industries, Ltd.Inventors: Koji Abe, Kazuhiro Miyoshi
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Patent number: 8435717Abstract: 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: GrantFiled: February 14, 2008Date of Patent: May 7, 2013Assignee: Central Glass Company, LimitedInventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
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Patent number: 8377406Abstract: 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: GrantFiled: August 29, 2012Date of Patent: February 19, 2013Assignee: Boulder Ionics CorporationInventors: Rajendra P. Singh, Jerry Lynn Martin, Joseph Carl Poshusta
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Patent number: 8304580Abstract: 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: GrantFiled: December 18, 2007Date of Patent: November 6, 2012Assignee: Central Glass Company, LimitedInventors: Tsutomu Nanmyo, Shintaro Sasaki, Takashi Kume
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Patent number: 8263811Abstract: 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: GrantFiled: May 6, 2010Date of Patent: September 11, 2012Assignee: Solvay (Société Anonyme)Inventors: Patrick Lacroix-Desmazes, Romain Severac, Bernard Boutevin, Vincent Bodart, Vincent Kurowski
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Patent number: 8247612Abstract: 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: GrantFiled: May 16, 2008Date of Patent: August 21, 2012Assignee: Sumitomo Chemical Company, LimitedInventor: Hiroyuki Miyazaki
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Patent number: 8236920Abstract: 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: GrantFiled: September 6, 2006Date of Patent: August 7, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Noriyuki Hida, Seiji Oda, Takashi Kamikawa, Katsuhiro Suenobu
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Publication number: 20110263903Abstract: 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: ApplicationFiled: April 21, 2011Publication date: October 27, 2011Applicant: BASF SEInventors: Patrick Deck, Heiner Schelling, Florian Garlichs
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Patent number: 8043786Abstract: 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: GrantFiled: February 20, 2004Date of Patent: October 25, 2011Assignee: JSR CorporationInventors: Satoshi Ebata, Yong Wang, Isao Nishimura
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Patent number: 8017656Abstract: A compound given by the formula (I): has an excellent controlling activity against noxious arthropods.Type: GrantFiled: November 1, 2006Date of Patent: September 13, 2011Assignee: Sumitomo Chemical Company, LimitedInventor: Hiroyuki Miyazaki
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Patent number: 8008358Abstract: 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: GrantFiled: December 22, 2005Date of Patent: August 30, 2011Assignee: Merck Patent GmbHInventors: Peer Kirsch, Klaus-Dieter Franz, Andreas Ruhl
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Patent number: 7977284Abstract: 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: GrantFiled: March 9, 2010Date of Patent: July 12, 2011Assignee: Oil Chem Technologies, IncInventors: Paul Berger, Christie Berger
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Publication number: 20110020712Abstract: 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: ApplicationFiled: October 4, 2010Publication date: January 27, 2011Applicant: Arizona Board of Regents for and on behalf of Arizona State UniversityInventors: Charles Austen Angell, Xiao-Guang Sun
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Publication number: 20100291437Abstract: 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: ApplicationFiled: October 24, 2008Publication date: November 18, 2010Applicant: UBE INDUSTRIES, LTD.Inventors: Koji Abe, Kazuhiro Miyoshi
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Patent number: 7834209Abstract: Hydrofluoroalkanesulfonates of the general formula R—O—CXH—CX2—SO3M, where R is selected from the group consisting of alkyl groups, functionalized alkyl groups, and alkenyl groups; X is selected from the group consisting of hydrogen and fluorine with the proviso that at least one X is fluorine; and M is a cation, are made by reacting fluorovinyl ether with aqueous sulfite solution. Organic onium hydrofluoroalkanesulfonates are useful as ionic liquids and photoacid generators.Type: GrantFiled: June 6, 2006Date of Patent: November 16, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Christopher P. Junk, Mark Andrew Harmer, Andrew Edward Feiring, Frank Leonard Schadt, III, Zoe Schnepp
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Patent number: 7833690Abstract: The present invention relates to photoacid generating compounds, lithographic resists comprising photoacid generating compounds, and to various lithographic processes techniques, and applications.Type: GrantFiled: October 6, 2006Date of Patent: November 16, 2010Assignee: The University of North Carolina at CharlotteInventors: Kenneth E. Gonsalves, Mingxing Wang
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Patent number: 7833666Abstract: 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: GrantFiled: July 19, 2007Date of Patent: November 16, 2010Assignee: Arizona Board of Regents for and behalf of Arizona State UniversityInventors: Charles Austen Angell, Xiao-Guang Sun
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Patent number: 7812194Abstract: 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: GrantFiled: August 30, 2006Date of Patent: October 12, 2010Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Toshiaki Aoai
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Publication number: 20100022803Abstract: 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: ApplicationFiled: December 18, 2007Publication date: January 28, 2010Applicant: Central Glass Company, LimitedInventors: Tsutomu Nanmyo, Shintaro Sasaki, Takashi Kume
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Publication number: 20090181319Abstract: 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: ApplicationFiled: January 16, 2008Publication date: July 16, 2009Applicant: INTERNATIONAL BUSINESS MACHINES CORPORATIONInventors: Wenjie Li, Sen Liu, Wu-Song Huang, Pushkara R. Varanasi, Irene Popova
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Publication number: 20090176175Abstract: 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: ApplicationFiled: January 8, 2008Publication date: July 9, 2009Applicant: International Business Machines CorporationInventor: Martin Glodde
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Publication number: 20090137773Abstract: 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: ApplicationFiled: July 28, 2006Publication date: May 28, 2009Inventors: Andrew Jackson, Vimal Sharma, Bradley E. Edwards, Janet Boggs, Victoria Hedrick, Stephan Brandstadter, John Chien, Edward Norman, Robert Kaufman, Bruno Ameduri, George K. Kostov
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Patent number: 7435526Abstract: 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: GrantFiled: June 14, 2004Date of Patent: October 14, 2008Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Toshiaki Aoai
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Publication number: 20080161612Abstract: Partially fluorinated ionic compounds are prepared. They are useful in the preparation of partially fluorinated dienes, in which the repeat units are cycloaliphatic.Type: ApplicationFiled: December 13, 2007Publication date: July 3, 2008Inventors: Zhen-Yu Yang, Amy Qi Han
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Publication number: 20080149878Abstract: 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: ApplicationFiled: December 22, 2005Publication date: June 26, 2008Inventors: Peer Kirsch, Klaus-Dieter Franz, Andreas Ruhl
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Publication number: 20080131810Abstract: 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: ApplicationFiled: December 4, 2006Publication date: June 5, 2008Inventors: M. Dalil Rahman, David L. Rentkiewicz
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Patent number: 7339082Abstract: 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: GrantFiled: November 22, 2004Date of Patent: March 4, 2008Assignee: Japan Science and Technology CorporationInventors: Kazuaki Ishihara, Hisashi Yamamoto
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Publication number: 20080032184Abstract: 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: ApplicationFiled: June 25, 2004Publication date: February 7, 2008Inventors: Zhen-yu Yang, Mark Roelofs
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Patent number: 7217492Abstract: 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: GrantFiled: December 24, 2003Date of Patent: May 15, 2007Assignee: JSR CorporationInventors: Eiji Yoneda, Yong Wang, Yukio Nishimura
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Patent number: 7193113Abstract: 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: GrantFiled: December 14, 2001Date of Patent: March 20, 2007Assignee: Japan Science and Technology CorporationInventors: Kazuaki Ishihara, Hisashi Yamamoto
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Patent number: 7157600Abstract: 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: GrantFiled: March 10, 2004Date of Patent: January 2, 2007Assignee: Solvay Solexis S.p.A.Inventors: Vito Tortelli, Pierangelo Calini, Stefano Millefanti
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Patent number: 7094501Abstract: 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: GrantFiled: September 25, 2001Date of Patent: August 22, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: Hanne Anna Katharina Blau, Pui-Yan Lin, José Manuel Rodriguez-Parada
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Patent number: 7087788Abstract: The present invention relates to new fluorosulfone compounds. These fluorosulfone compounds have utility in preventing, controlling and extinguishing fire.Type: GrantFiled: August 11, 2004Date of Patent: August 8, 2006Assignee: E.I. du Pont de Nemours and CompanyInventors: Allen C. Sievert, Mario J. Nappa, Velliyur Nott Mallikarjuna Rao, Paul R. Resnick
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Patent number: 7053123Abstract: (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 consistinType: GrantFiled: October 5, 2001Date of Patent: May 30, 2006Assignee: Temple University-of the Commonwealth System of Higher EducationInventors: E. Premkumar Reddy, M. V. Ramana Reddy
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Patent number: 6991888Abstract: 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: GrantFiled: May 16, 2003Date of Patent: January 31, 2006Assignee: AZ Electronic Materials USA Corp.Inventors: Munirathna Padmanaban, Takanori Kudo, Sangho Lee, Ralph R. Dammel, M. Dalil Rahman
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Patent number: 6887624Abstract: 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: GrantFiled: September 25, 2001Date of Patent: May 3, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Hanne Anna Katharina Blau, Pui-Yan Lin, José Manuel Rodriguez-Parada
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Patent number: 6833480Abstract: 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: GrantFiled: August 21, 2003Date of Patent: December 21, 2004Assignee: Temple University - Of The Commonwealth System of Higher EducationInventors: E. Premkumar Reddy, M. V. Ramana Reddy
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Patent number: 6727386Abstract: 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: GrantFiled: October 25, 2001Date of Patent: April 27, 2004Assignee: 3M Innovative Properties CompanyInventor: Steven Joseph Hamrock
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Patent number: 6723483Abstract: 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: GrantFiled: December 7, 2000Date of Patent: April 20, 2004Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Keiji Oono, Kazuhito Fukasawa, Kazunori Sakamoto, Fumiyoshi Urano, Motoshige Sumino, Shigeaki Imazeki
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Patent number: 6692893Abstract: 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: GrantFiled: October 23, 2001Date of Patent: February 17, 2004Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Jun Watanabe, Takeshi Nagata, Jun Hatakeyama
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Arylbis(perfluoroalkylsulfonyl) methane and metallic salt thereof and methods for producing the same
Publication number: 20040030192Abstract: 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: ApplicationFiled: June 12, 2003Publication date: February 12, 2004Inventors: Kazuaki Ishihara, Hisashi Yamamoto