Plural Halogens Containing Patents (Class 568/35)
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Patent number: 6657086Abstract: Embodiments of the invention relate to C2-substituted indan-1-ols and to their physiologically acceptable salts and physiologically functional derivatives. Compounds of embodiments of the invention may include compounds of formula I in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparation. The compounds are suitable, for example, for use as anorectics.Type: GrantFiled: August 30, 2002Date of Patent: December 2, 2003Assignee: Aventis Pharma Deutschland GmbHInventors: Gerhard Jaehne, Volker Krone, Martin Bickel, Matthias Gossel
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Patent number: 6580006Abstract: The present invention provides a catalytic process for preparing perfluoroethanesulfonyl fluoride and/or perfluorodiethylsulfone using a two-part catalytic process comprising a metal fluoride and a crown ether.Type: GrantFiled: May 2, 2002Date of Patent: June 17, 2003Assignee: 3M Innovative Properties CompanyInventors: William M. Lamanna, Michael D. Barrera, Gerald L. Bauer, Yuri Cheburkov
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Patent number: 6528232Abstract: A sulfonium salt compound designated by a general formula (I), a photoresist composition containing the sulfonium salt compound and a method for patterning by employing the sulfonium salt compound.Type: GrantFiled: October 31, 2000Date of Patent: March 4, 2003Assignee: NEC CorporationInventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
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Publication number: 20020068765Abstract: This invention describes the new benzocycloheptenes of general formula I 1Type: ApplicationFiled: July 19, 1999Publication date: June 6, 2002Inventors: ROLF BOHLMANN, JORG KROLL, HERMANN KUENZER, CHRISTA HEGELE-HARTUNG, MONIKA LESSL, ROSEMARIE LICHTNER, YUKISHIGE NISHINO
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Patent number: 6399833Abstract: A process for producing a purified aryl vinyl sulfone solution, characterized in that an aryl vinyl sulfone is crystallized from an organic solvent solution of a crude aryl vinyl sulfone to give a crystallization mixture, and a wet cake of the aryl vinyl sulfone obtained by the separation of the solution from the said mixture is dissolved in a solution-forming solvent selected from ethers of 4 to 8 carbon atoms, aromatic hydrocarbons of 6 to 10 carbon atoms, halogenated hydrocarbons of 1 to 6 carbon atoms, ketones of 3 to 8 carbon atoms, esters of 3 to 6 carbon atoms, and nitrites of 2 to 6 carbon atoms.Type: GrantFiled: July 31, 2000Date of Patent: June 4, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Akio Kurihara, Isao Kurimoto, Naoyuki Takano
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Method for making unsymmetrically substituted fluorenyl compounds for nonlinear optical applications
Patent number: 6379590Abstract: A new method for producing unsymmetrically substituted fluorenyl compounds, one step of which is the preparation of 2,7-disubstituted fluoren-9-one derivatives via the nucleophilic substitution of a compound of the formula D wherein A′ is selected from the group consisting of —Br, —Cl, —F, —NO2, and —CN; A is selected from the group consisting of —NO2, —CN, —CO2R, —C(O)R, —SO2R, —SO2RF, —C(CN)═C(CN)2 and —CH═C(CN)2; RF is —CpF2p+1, p=from about 0 to about 10; R is an straight, branched or cyclic aliphatic alkyl group having about 1 to 10 carbon atoms, or an aromatic group such as phenyl or naphthyl; and is a carbonyl or a protected carbonyl such as a ketal or thio-ketal such as wherein R′ is —CrH2r+1; R″ is —(CH2)r—; and r is independently 2 or 3, with a nucleophilic reagent in the presence of an aprotic solventType: GrantFiled: December 2, 1994Date of Patent: April 30, 2002Assignee: AlliedSignal Inc.Inventors: Chengjiu Wu, Jianhui Shan -
Patent number: 6358665Abstract: Disclosed is a chemically amplified radiation sensitive composition containing a hydroxystyrene resin and an onium salt precursor which generates a fluorinated alkanesulfonic acid as a photoacid generator, wherein the photoacid generator is a sulfonium or iodonium salt of a fluorinated alkane sulfonic acid, represented by formula (I): Y+ASO3− (I) wherein A represents CF3CHFCF2 or CF3CF2CF2CF2; and Y represents wherein R1, R2, R3, R4, and R5 each independently represent an alkyl group, a monocyclic or bicyclic alkyl group, a cyclic alkylcarbonyl group, a phenyl group, a naphthyl group, an anthryl group, a peryl group, a pyryl group, a thienyl group, an aralkyl group, or an arylcarbonylmethylene group, or any two of R1, R2, and R3 or R4 and R5 together represent an alkylene or an oxyalkylene which forms a five- or six-membered ring together with the interposing sulfur or iodine, said ring being optionally condensed with aryl groups.Type: GrantFiled: July 3, 2000Date of Patent: March 19, 2002Assignee: Clariant International Ltd.Inventors: Georg Pawlowski, Hiroshi Okazaki, Yoshiaki Kinoshita, Naoko Tsugama, Aritaka Hishida, Xiao-Ming Ma, Yuko Yamaguchi
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Patent number: 6348297Abstract: A chemical amplification type positive resist composition which is good in resolution, provide a good pattern profile under exposure using light of wavelength of 220 nm or shorter even when applied on a basic substrate or a low reflectance substrate and which comprises an acid generator comprising an aliphatic sulfonium salt represented by the following formula (I): wherein Q1 represents an alkyl group, Q2 represents an alkyl or a residue of an alicyclic hydrocarbon and m represents an integer of 1 to 8; and onium salt selected from triphenylsulfonium salts represented by the following formula (IIa) and diphenyliodonium salts represented by the following formula (IIb): wherein Q3, Q4, Q5, Q6 and Q7each independently represent a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and q and p represent a integer of 4 to 8; and (2) a resin which has a polymerization unit with a group unstable to an acid, and iType: GrantFiled: March 24, 2000Date of Patent: February 19, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Yasunori Uetani, Kenji Oohashi, Hiroki Inoue
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Publication number: 20020009650Abstract: The invention concerns ionic compounds in which the anionic load has been delocalized. A compound disclosed by the invention is comprised of an amide or one of its salts, including an anionic portion combined with at least one cationic portion M+m in sufficient numbers to ensure overall electronic neutrality; the compound is further comprised of M as a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation with the valence m, an organic cation with the valence m, or an organometallic cation with the valence m. The anionic portion matches the formula RF—SOx—N−Z, wherein RF is a perfluorinated group, x is 1 or 2, and Z is an electroattractive substituent. The compounds can be used notably for ionic conducting materials, electronic conducting materials, colorants, and the catalysis of various chemical reactions.Type: ApplicationFiled: May 16, 2001Publication date: January 24, 2002Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Yves Choquette
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Patent number: 6300511Abstract: The present invention provides a method of substituting a carbonyl compound with fluorine at the &agr;-position, comprising reaching the carbonyl compound with a fluorinating present of a metal-containing catalyst. The reaction results in replacement of a hydrogen atom by fluorine. The catalyst, which is used in a catalytically effective amount, is preferably a transition metal. In one class of methods the catalyst is a transition metal compound. In another class of methods, the catalyst is an elemental metal, in which case the carbonyl compound has an activating group attached to the carbon atom which is substituted by fluorine.Type: GrantFiled: March 27, 2000Date of Patent: October 9, 2001Assignee: F2 Chemicals LimitedInventors: Richard Dickinson Chambers, John Hutchinson, John Stewart Moilliet
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Patent number: 6118016Abstract: A process for preparing phenoxyphenylsulfonyl halides, which are useful intermediates for the preparation of matrix metalloproteinase inhibitors.Type: GrantFiled: April 7, 1999Date of Patent: September 12, 2000Assignee: Pfizer Inc.Inventor: Joel M. Hawkins
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Patent number: 6111143Abstract: This invention relates to a sulfonium salt, including its manufacturing method, which is effectively used as a photoacid initiator or radical photoinitiator during polymerization and a photoacid generator, leaving the protection groups of organic compounds, especially as an useful photoacid generator of the chemically amplified photoresist employed in semiconductor materials. Since the sulfonium salt of this invention, so prepared via one-step reaction between sulfoxide compound and aromatic compound in the presence of perfluoroalkanesulfonic anhydride, has the advantages in that by overcoming some shortcomings of the prior art to prepare the sulfonium salt via two steps using Grinard reagent, this invention may provide a novel sulfonium salt with higher yield which cannot be achieved in the prior art and also to prepare even any conventional sulfonium salt having better yield.Type: GrantFiled: August 27, 1998Date of Patent: August 29, 2000Assignee: Korea Kumbo Petrochemical Co., Ltd.Inventors: Joo-Hyeon Park, Dong-Chul Seo, Sun-Yi Park, Seong-Ju Kim
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Patent number: 6015911Abstract: Herbicidal 1-alkyl-4-(2-chloro-3-alkoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole compounds, as well as 1-halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene compounds and 2-chloro-3-alkoxy-4-alkylsulfonylbenzoic acid compounds, were prepared in good yield by the reaction of the corresponding 3-chloro compound with an alkali metal alkoxide compound. 1-Halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene and 1-halo-2,3-dichloro-4-alkylsulfonylbenzene compounds were converted to compounds having hydroxycarbonyl, alkoxycarbonyl, or 1-alkyl-5-hydroxypyrazole-4-carbonyl substituents in place of the 1-halo substituent by reaction with carbon monoxide and water, an alcohol, or a 1-alkyl-5-hydroxypyrazole compound, respectively, in the presence of a palladium II salt:trihydrocarbylphosphine complex type catalyst.Type: GrantFiled: March 24, 1998Date of Patent: January 18, 2000Assignee: Dow AgroSciences LLCInventors: Thomas L. Siddall, Mark V. M. Emonds, Karl L. Krumel, Jennifer M. Schomaker, Mark W. Zettler
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Patent number: 6013838Abstract: Novel trifluoromethylated intermediates are provided which are useful in synthesizing trifluoromethylated organic compounds. Specifically, compounds of the formula CF.sub.3 CR are provided, wherein R is (Cl).dbd.CHCH.sub.2 SO.sub.2 Ph, (Cl).dbd.CHCH.sub.2 CH.sub.2 C(.dbd.O)CH.sub.3, (Cl).dbd.CHCH.sub.2 CH(COCH.sub.3).sub.2, (Cl).dbd.CHCH.sub.2 NR'R" or H.dbd.CHCH.dbd.NR'; R' and R" are the same or different and are selected from the group consisting of hydrogen, unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, unsubstituted or substituted C.sub.3 to C.sub.7 cycloalkyl, unsubstituted or substituted C.sub.2 to C.sub.12 alkenyl, a benzyl group unsubstituted or substituted with R'", or a phenyl group unsubstituted or substituted with R'"; or R' and R" taken together form a five- or six-membered ring; and R'" is an unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, an unsubstituted or substituted C.sub.1 to C.sub.Type: GrantFiled: January 26, 1999Date of Patent: January 11, 2000Assignee: Alliedsignal Inc.Inventor: Michael Van Der Puy
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Patent number: 5959152Abstract: A novel substituted benzenedithiol metal complex represented by the general formula (1) is provided. The substituted benzenedithiol metal complex is useful as a singlet oxygen quencher and as an optical data recording medium per se. ##STR1## wherein M is a transition metal; A.sup.+ is a quaternary ammonium group; and R is an organic group selected from the group consisting of organic groups represented by the formulae (i), (ii), (iii) and (iv): ##STR2## (wherein R.sup.1 is an alkyl group having 1 to 4 carbon atoms) ##STR3## (wherein n is 3, 4 or 5), ##STR4## (wherein R.sup.2 is one of a hydrogen atom and a substitutent having 1 to 4 carbon atoms).Type: GrantFiled: October 2, 1998Date of Patent: September 28, 1999Assignee: Sumitomo Seika Chemicals Co., Ltd.Inventors: Kazuyoshi Hirako, Satoshi Kimura, Michio Suzuki
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Patent number: 5925788Abstract: 2-Trifluoromethoxy-benzenesulphonamide, of the formula (I), ##STR1## which can be used as intermediate for the preparation of certain herbicidally active compounds is obtained in very high yield and high purity by a process in which halogenated trifluoromethoxy-benzenesulphonamides of the general formula (II) ##STR2## in which X.sup.1 represents halogen and X.sup.2 represents hydrogen or halogenare reacted with hydrogen in the presence of a catalyst and in the presence of a diluent and, if appropriate, in the presence of an acid acceptor at temperatures between 0.degree. C. and 200.degree. C. ("dehalogenated"), the resulting compound of the formula (I) is isolated in the customary manner in the event that "X.sup.2 =halogen" and converted into a pure, crystalline product by treating it with a protic polar organic liquid and isolated by removing the liquid component by means of filtration with suction in the event that "X.sup.2 =H".Type: GrantFiled: May 14, 1998Date of Patent: July 20, 1999Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Albrecht Marhold, Ernst Kysela
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Patent number: 5831114Abstract: Substituted N-phenyl- and N-heteroarylalkylcarbamates of formula (I), in which Q is a group (1), (2) or (3); R is halogen, trifluoromethyl, cyano, nitro or C.sub.1 -C.sub.3 haloalkoxy; Z is hydrogen or halogen; or Z and R together in the 2- and 3-position of the phenyl ring form a group --OCF.sub.2 O--; R.sub.1 is C.sub.1 -C.sub.5 alkyl; R.sub.2, R.sub.3, R.sub.4 and R.sub.5, independently of one another, are hydrogen, methyl or ethyl; X is oxygen, sulfur, --SO-- or --SO.sub.2 --, Y is hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or cyano; n is 0, 1 or 2; n.sub.1 is 0 or 1; and m is 0 or 1, with the proviso that m is 1 if Q is group (1) or (2); and the diastereomers and enantiomers thereof, exhibit pre- and post-emergence herbicidal properties. The preparation of these compounds and their use as herbicidally active ingredients are described.Type: GrantFiled: May 28, 1997Date of Patent: November 3, 1998Assignee: Novartis Finance CorporationInventors: Hermann Rempfler, Fredrik Cederbaum, Felix Spindler, Willy Urs Lottenbach
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Patent number: 5780682Abstract: Preparation of fluorinated alkyl sulphonyl halides having the general formula: ##STR1## where R.sup.I.sub.f is fluorinated alkyl group and R.sup.II.sub.f is a fluorinated alkyl group or fluorine, X is a halogen atom, and Y is a proton, a halogen atom, or a fluorinated alkyl groups, by reaction of a corresponding fluorinated unsaturated hydrocarbon with sulphuryl halide, wherein the reaction is carried out in the presence of at least catalytic amounts of a fluoride in a solvent comprising compounds having one or more SO and/or SO.sub.2 groups incorporated in the compound structure.Type: GrantFiled: September 19, 1997Date of Patent: July 14, 1998Assignee: Haldor Topsoe A/SInventors: John Zavilla, Sven Ivar Hommeltoft
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Patent number: 5696224Abstract: A macromolecular material having a linear, branched or crosslinked framework, and substituted with ionic substituents, wherein the ionic substituents are incorporated by reaction of a group, Y, of one or more ionic monomers having the formula (I):M?Y--(O--(CHR).sub.p --(CH.sub.2).sub.q).sub.n --C(SO.sub.2 R.sub.F).sub.2).sub.m (I)whereinM, m, R.sub.F, R, Y, n, p and q are as described herein;and the use of the macromolecular material in the production of a variety of electrochemical systems.Type: GrantFiled: July 28, 1995Date of Patent: December 9, 1997Assignees: Centre National de la Recherche Scientifique, Hydro-QuebecInventors: Djamila Benrabah, Michel Armand, Didier Delabouglise
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Patent number: 5676884Abstract: Nonlinear optical (NLO) compositions are disclosed which contain polar disulfone-functionalized molecules (PDFMs) incorporated in a polymeric material. when aligned noncentrosymmetrically in the polymeric material, the PDFMs generate a second-order NLO response. There is also disclosed: a method of preparing a NLO composition; novel PDFMs and novel polymers; and a new process for preparing PDFMs.Type: GrantFiled: November 20, 1996Date of Patent: October 14, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: George V. Tiers, Robert J. Koshar, Louis M. Leichter
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Patent number: 5672626Abstract: A class of substituted spirodienes is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.4 and R.sup.5 is hydrido; wherein R.sup.3 is methylsulfonyl or sulfamyl; and wherein each of R.sup.6 through R.sup.10 is independently selected from hydrido, halo, alkyl, alkoxy, alkylthio, cyano, haloalkyl, haloalkoxy, hydroxyalkyl, alkoxyalkyl, hydroxyl, and mercapto; and wherein n is 1, 2 or 3; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: July 9, 1996Date of Patent: September 30, 1997Assignee: G. D. Searle & Co.Inventors: Horng-Chih Huang, David R. Reitz
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Patent number: 5672627Abstract: A class of substituted spirodienes is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula III: ##STR1## wherein R.sup.3 is methylsulfonyl or sulfamyl; and wherein R.sup.8 is selected from hydrido, fluoro, chloro, bromo, iodo, methyl, ethyl, n-propyl, isopropyl, butyl, tert-butyl, isobutyl, methoxy, ethoxy, propoxy, butoxy, hydroxyl, mercapto, methylthio, ethylthio, cyano, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, pentafluoroethyl, heptafluoropropyl, difluorochloromethyl, dichlorofluoromethyl, difluoroethyl, difluoropropyl, dichloroethyl, dichloropropyl, trifluoromethoxy, hydroxymethyl, methoxymethyl and ethoxymethyl; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: July 9, 1996Date of Patent: September 30, 1997Assignee: G.D. Searle & Co.Inventors: Horng-Chih Huang, David R. Reitz
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Patent number: 5633409Abstract: Trifluoromethanesulfonic and p-toluenesulfonic acid bis- or tris(p-tert-butoxyphenyl)sulfonium salts are novel. They are prepared from bis(p-tert-butoxyphenyl)sulfoxide which is also novel. A chemically amplified positive resist composition which contains the sulfonium salt as a photo-acid generator is highly sensitive to deep-UV rays, electron beams and X-rays, can be developed with alkaline aqueous solution to form a pattern, and is thus suitable for use in a fine patterning technique.Type: GrantFiled: January 27, 1995Date of Patent: May 27, 1997Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Youichi Ohsawa, Toshinobu Ishihara, Kazumasa Maruyama, Yoshihumi Takeda, Junji Shimada, Fujio Yagihashi, Katsuya Takemura
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Patent number: 5614525Abstract: The present invention is directed to the use of disulfonyl methane compounds for the control off parasites in vertebrate animals.Type: GrantFiled: May 4, 1995Date of Patent: March 25, 1997Assignee: Eli Lilly and CompanyInventor: David I. Wickiser
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Patent number: 5596122Abstract: The present invention is directed to disulfonyl methane compounds for the control of parasites in vertebrate animals.Type: GrantFiled: April 25, 1995Date of Patent: January 21, 1997Assignee: Eli Lilly and CompanyInventor: David I. Wickiser
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Patent number: 5578251Abstract: A process for preparing polar disulfone-functionalized molecules, which process comprises performing one or more of the following reactions:(i) reacting a vinyl ether disulfone molecule with an activated aromatic molecule, an activated heterocyclic molecule, a dye base, or a dye olefin;(ii) reacting an enamine disulfone molecule with a dye base or a dye olefin; and(iii) reacting an alkenyl disulfone molecule having a vinylogous methyl or methylene group conjugatively located relative to the disulfone group with an aldehyde or an acetal derived from an aldehyde.Type: GrantFiled: August 5, 1994Date of Patent: November 26, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gary T. Boyd, George V. Tiers, Cecil V. Francis, Eugene P. Janulis, Robert J. Koshar, Louis M. Leichter
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Patent number: 5538812Abstract: The present invention relates to metal ion salts which can be used in electrolytes for producing electrochemical devices, including both primary and secondary batteries, photoelectrochemical cells and electrochromic displays. The salts have a low energy of dissociation and may be dissolved in a suitable polymer to produce a polymer solid electrolyte or in a polar aprotic liquid solvent to produce a liquid electrolyte. The anion of the salts may be covalently attached to polymer backbones to produce polymer solid electrolytes with exclusive cation conductivity.Type: GrantFiled: March 17, 1995Date of Patent: July 23, 1996Assignee: Moltech CorporationInventors: Hung-Sui Lee, Lin Geng, Terje A. Skotheim
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Patent number: 5502083Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3):MQ.sub.m (OH).sub.l (3)where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.Type: GrantFiled: June 8, 1994Date of Patent: March 26, 1996Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
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Patent number: 5480568Abstract: Alkyl aryl sulfones are disclosed which are useful as high temperature and magnetic recording media lubricants. Also disclosed are lubricating mixtures containing the alkyl aryl sulfones, magnetic recording media containing the alkyl aryl sulfones, and a process for lubricating the magnetic recording media with the alkyl aryl sulfones.Type: GrantFiled: July 22, 1994Date of Patent: January 2, 1996Assignee: The Dow Chemical CompanyInventors: Chester E. Pawloski, Bassam S. Nader
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Patent number: 5468903Abstract: A process for preparing a compound comprising a monocyclic aromatic ring having at least a first substituent and a substituted sulphonyl group at the position para to the first substituent, the process comprising mixing a reactant comprising the monocyclic aromatic ring with the first substituent and hydrogen in the position of the ring para to the first substituent, with a sulphonic acid halide derivative in the presence of a naturally occurring or synthetic zeolite capable of catalyzing a sulphonylation reaction between the reactant and the sulphonic acid halide, under conditions in which the reaction will occur.Type: GrantFiled: March 1, 1993Date of Patent: November 21, 1995Assignee: Zeneca LimitedInventors: Kenneth R. Randles, Brian G. Gott, Stephen T. A. K. Daley
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Patent number: 5446134Abstract: Bis(perfluorosulphonyl)methanes, process for preparing same and uses thereof. The compounds of the invention are based on the formula (1/nM)+[(R.sub.F SO.sub.2).sub.2 CY].sup.- in which Y denotes an electron-attracting group chosen from --C.dbd.N and RZ groupings in which Z denotes a carbonyl grouping, sulphonyl grouping or a phosphonyl grouping and R denotes an organic monovalent grouping, M denotes a metal having valency n or an organic group capable of existing in the cationic form, R.sub.F denotes a perfluoroalkyl or perfluoroaryl grouping. Said compounds are especially useful in the production of electrochemical devices.Type: GrantFiled: July 8, 1993Date of Patent: August 29, 1995Assignees: Centre National de la Recherche Scientifique, Hydro QuebecInventors: Michel Armand, Djamila Benrabah, Jean-Yves Sanchez
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5354511Abstract: Compounds having non-linear optical activity of the general formula ##STR1## wherein D and A are electron donor and acceptor groups, respectively, R.sup.1 and R.sup.2 are aromatic bridging groups, X and Y are preferably groups capable of partaking in polymerization reactions are suitable for use in polymer-based light modulator devices.Type: GrantFiled: November 27, 1992Date of Patent: October 11, 1994Assignee: AlliedSignal Inc.Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
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Patent number: 5352706Abstract: A microbial inhibiting composition and method is disclosed. The composition comprises an amount, effective for the intended purpose of diiodomethyl-p-tolylsulfone and alkyl dimethyl benzyl ammonium chloride. The method comprises administering an amount of this combined treatment to the particular water containing system for which treatment is desired.Type: GrantFiled: July 22, 1993Date of Patent: October 4, 1994Assignee: Betz Laboratories, Inc.Inventors: Deborah K. Donofrio, Wilson K. Whitekettle
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Patent number: 5296634Abstract: The present invention provides a method for preparing a 4-alkylsulfonyl-2-chloro-m-xylene useful as an intermediate for agricultural chemicals.Type: GrantFiled: August 19, 1992Date of Patent: March 22, 1994Assignee: Nissan Chemical Industries Ltd.Inventors: Masatoshi Baba, Eiichi Oya
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Patent number: 5206440Abstract: A process for production of fluorinated sulfones from fluorinated organic sulfides by oxidation of the sulfides with an oxidizing reagent made from fluorine, water and acetonitrile. The sulfones are useful as second order nonlinear optical dyes.Type: GrantFiled: July 28, 1992Date of Patent: April 27, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard Beckerbauer, Shlomo Rozen
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Patent number: 5196604Abstract: Polymers comprising fluorine-containing poly(ether sulfones) and monomers comprising aromatic fluorine-containing sulfones used in the preparation of these polymers.Type: GrantFiled: November 4, 1991Date of Patent: March 23, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Samuel D. Arthur
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Patent number: 5189224Abstract: The present invention provides a method for preparing a 4-alkylsulfonyl-2-chloro-m-xylene useful as an intermediate for agricultural chemicals, and an intermediate for the production thereof. The method of the present invention is to produce (E) from (C) by way of novel intermediates (D-1) and (D-2).Type: GrantFiled: October 9, 1991Date of Patent: February 23, 1993Assignee: Nissan Chemical Industries Ltd.Inventors: Masatoshi Baba, Eiichi Oya
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Patent number: 5152826Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: October 16, 1991Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventor: Christopher G. Knudsen
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Patent number: 5144080Abstract: A process is provided for preparing isoprenoid cyclopropane 1,1-dicarboxylates and derivatives thereof including the corresponding monocarboxylate, monocarboxylic acid and alcohol derivatives thereof, all of which are useful in preparing squalene synthetase inhibitors which inhibit cholesterol biosynthesis, and also useful in preparing pyrethrin insecticides.Type: GrantFiled: August 30, 1991Date of Patent: September 1, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Scott A. Biller, Cornelia Forster
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Patent number: 5136097Abstract: The invention relates to a process for the synthesis of sulfonylmethanes and derivatives thereof of the formula M[(RSO.sub.2).sub.2 CH].sub.m (I), in which M represents H, an alkali metal or alkaline earth metal or NR'.sub.4, R' and R are monovalent organic radicals and m represents the valence of M.The process comprises reacting an ionic carbide with a sulfonyl halide, hydrolyzing the product obtained, adding a compound M.sub.y Y.sub.m, in which Y represents an anion capable of reacting with the cation of the ionic carbide to the reaction medium before or after hydrolysis to give a compound which can be separated from compound (I), and y represents the valence of Y.Type: GrantFiled: December 3, 1990Date of Patent: August 4, 1992Assignees: Centre National de la Recherche Scientifique, Hydro-QuebecInventor: Michel Armand
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Patent number: 5123953Abstract: Compounds of formula: ##STR1## in which: n=0, 1, 2f=0, 1Ar is an optionally substituted phenyl or pyridyl groupU a chlorine or bromine atomV a bromine or chlorine or iodine atomB is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl, which are optionally substituted by 1 to 6 halogen atoms, phenyl or pyridyl or oxidized pyridyl, which are optionally substituted.Use of these compounds as herbicides which are selective but especially antigraminaceous at preemergence.Type: GrantFiled: April 10, 1990Date of Patent: June 23, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philipe Desbordes, Michel Euvrard, Francois De Reinach Hirtzbach, Christopher Pearson
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Patent number: 5100460Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.Type: GrantFiled: July 13, 1989Date of Patent: March 31, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philippe Desbordes, Michel Euvrard
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Patent number: 5095136Abstract: A process is provided for preparing isoprenoid cyclopropane 1,1-dicarboxylates and derivatives thereof including the corresponding monocarboxylate, monocarboxylic acid and alcohol derivatives thereof, all of which are useful in preparing squalene synthetase inhibitors which inhibit cholesterol biosynthesis, and also useful in preparing pyrethrin insecticides.Type: GrantFiled: August 27, 1990Date of Patent: March 10, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Scott A. Biller, Cornelia Forster
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Method for preparing intermediates for the synthesis of steroid side chains in optically active form
Patent number: 5089647Abstract: This invention provides a novel method for the preparation of optically active arylalykylsulfone derivatives, having a chiral center in the alkyl moiety in either the (R)- or the (S)-configuration. These optically active sulfones find use in the stereospecific synthesis of steroid or vitamin D compounds having chiral center at either carbon 24 or carbon 25 of the side chain. The method comprises the steps of reacting an optically active sulfinate ester having a chiral center at sulfur with a racemic alkyl Grignard reagent to obtain a mixture of diastereomeric sulfoxides, separating the mixture of diastereomeric sulfoxides, and oxidizing separately each of the diastereomers to obtain the desired optically active sulfone.Type: GrantFiled: April 11, 1990Date of Patent: February 18, 1992Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman -
Patent number: 5084548Abstract: Polymers comprising fluorine-containing poly(ether sulfones) and monomers comprising aromatic fluorine-containing sulfones used in the preparation of these polymers.Type: GrantFiled: November 9, 1989Date of Patent: January 28, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Samuel D. Arthur
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Patent number: 5068397Abstract: Tris-perfluoroalkyl terminated neopentyl alcohols of the formula (R.sub.f --E.sub.n --X--CH.sub.2).sub.3 CCH.sub.2 OH prepared from halogenated neopentyl alcohols and thiols of the formula R.sub.f --E.sub.n --SH, amines of the formula R.sub.f --E.sub.n --NH--R, alcohols of the formula R.sub.f --E.sub.n --OH, perfluoro-acids or amides, are described. The alcohols react with isocyanates to prepare urethanes; with acids or derivatives, to prepare esters or carbonates; with epoxides to form ethers. Further, they may be converted to halide intermediates. The products all contain the residue of at least one R.sub.f -neopentyl alcohol containing three perfluoroalkyl hetero groups.Type: GrantFiled: August 15, 1990Date of Patent: November 26, 1991Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirkland P. Clark, Michael Jacobson, Athanasios Karydas, Juliana Rodgers
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Patent number: 5023380Abstract: Compounds have a structure represented by Formula I:CF.sub.2 =CF-X-R-(X-CF=CF.sub.2).sub.mwherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF=CF.sub.2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of:(a) forming a salt having anion corresponding to a compound of Formula II:HX--R--(XH).sub.m ;wherein X, R and m are as defined for Formula I;(b) reacting the salt with a 1,2-dihalo-1,1,2, 2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III:Z-CF.sub.2 CF.sub.2 -X-R-(X-CF.sub.2 CF.sub.2 - Z).sub.Type: GrantFiled: June 9, 1989Date of Patent: June 11, 1991Assignee: The Dow Chemical CompanyInventors: David A. Babb, Bobby R. Ezzell, Katherine S. Clement
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Patent number: 5017228Abstract: A liquid ink composition for selective printing comprising a coloring agent and a vehicle comprising a non-drying oil as a main component and a dispersing agent, wherein an iodine-containing antifungal agent having the general formula (I): ##STR1## wherein R is a lower alkyl group or a halogen atom is contained. The ink composition has an excellent fungus resistance and retains a desired ink flowability on storage. Accordingly, an ink ribbon or ink roller impregnated with the ink composition can be stored without impairing printing properties such as printing durability while being kept from getting moldy.Type: GrantFiled: December 9, 1988Date of Patent: May 21, 1991Assignee: Fuji Kagakushi Kogyo Co., Ltd.Inventor: Hitoshi Goda
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Patent number: 5015775Abstract: Alkyl aryl sulfones of the formula R--SO.sub.2 --AR--Y.sub.n, wherein Ar is an aryl compound, Y is a substituent on the aryl compound and R is alkyl or cycloalkyl, and liquid mixtures of positional isomers of the same are prepared by reacting an aryl compound of the formula Ar--Y.sub.n, with an alkyl sulfonic acid of the formula R--SO.sub.3 H and a phosphorus reagent, preferably under heat. Particularly good yields and pure products are obtained using phosphorus pentoxide. Alkyl aryl sulfones produced by this method are a liquid mixture preferably containing at least two positional isomers, wherein no isomer is present in an amount of more than about 50% of the isomer mixture.Type: GrantFiled: March 31, 1988Date of Patent: May 14, 1991Assignee: Atochem North America, Inc.Inventors: James L. Reilly, Gordon R. Leader