Plural Halogens Containing Patents (Class 568/35)
  • Patent number: 6657086
    Abstract: Embodiments of the invention relate to C2-substituted indan-1-ols and to their physiologically acceptable salts and physiologically functional derivatives. Compounds of embodiments of the invention may include compounds of formula I in which the radicals are as defined, and their physiologically acceptable salts and processes for their preparation. The compounds are suitable, for example, for use as anorectics.
    Type: Grant
    Filed: August 30, 2002
    Date of Patent: December 2, 2003
    Assignee: Aventis Pharma Deutschland GmbH
    Inventors: Gerhard Jaehne, Volker Krone, Martin Bickel, Matthias Gossel
  • Patent number: 6580006
    Abstract: 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: Grant
    Filed: May 2, 2002
    Date of Patent: June 17, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: William M. Lamanna, Michael D. Barrera, Gerald L. Bauer, Yuri Cheburkov
  • Patent number: 6528232
    Abstract: 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: Grant
    Filed: October 31, 2000
    Date of Patent: March 4, 2003
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
  • Publication number: 20020068765
    Abstract: This invention describes the new benzocycloheptenes of general formula I 1
    Type: Application
    Filed: July 19, 1999
    Publication date: June 6, 2002
    Inventors: ROLF BOHLMANN, JORG KROLL, HERMANN KUENZER, CHRISTA HEGELE-HARTUNG, MONIKA LESSL, ROSEMARIE LICHTNER, YUKISHIGE NISHINO
  • Patent number: 6399833
    Abstract: 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: Grant
    Filed: July 31, 2000
    Date of Patent: June 4, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akio Kurihara, Isao Kurimoto, Naoyuki Takano
  • Patent number: 6379590
    Abstract: 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 solvent
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: April 30, 2002
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan
  • Patent number: 6358665
    Abstract: 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: Grant
    Filed: July 3, 2000
    Date of Patent: March 19, 2002
    Assignee: Clariant International Ltd.
    Inventors: Georg Pawlowski, Hiroshi Okazaki, Yoshiaki Kinoshita, Naoko Tsugama, Aritaka Hishida, Xiao-Ming Ma, Yuko Yamaguchi
  • Patent number: 6348297
    Abstract: 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 i
    Type: Grant
    Filed: March 24, 2000
    Date of Patent: February 19, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Kenji Oohashi, Hiroki Inoue
  • Publication number: 20020009650
    Abstract: 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: Application
    Filed: May 16, 2001
    Publication date: January 24, 2002
    Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Yves Choquette
  • Patent number: 6300511
    Abstract: 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: Grant
    Filed: March 27, 2000
    Date of Patent: October 9, 2001
    Assignee: F2 Chemicals Limited
    Inventors: Richard Dickinson Chambers, John Hutchinson, John Stewart Moilliet
  • Patent number: 6118016
    Abstract: A process for preparing phenoxyphenylsulfonyl halides, which are useful intermediates for the preparation of matrix metalloproteinase inhibitors.
    Type: Grant
    Filed: April 7, 1999
    Date of Patent: September 12, 2000
    Assignee: Pfizer Inc.
    Inventor: Joel M. Hawkins
  • Patent number: 6111143
    Abstract: 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: Grant
    Filed: August 27, 1998
    Date of Patent: August 29, 2000
    Assignee: Korea Kumbo Petrochemical Co., Ltd.
    Inventors: Joo-Hyeon Park, Dong-Chul Seo, Sun-Yi Park, Seong-Ju Kim
  • Patent number: 6015911
    Abstract: 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: Grant
    Filed: March 24, 1998
    Date of Patent: January 18, 2000
    Assignee: Dow AgroSciences LLC
    Inventors: Thomas L. Siddall, Mark V. M. Emonds, Karl L. Krumel, Jennifer M. Schomaker, Mark W. Zettler
  • Patent number: 6013838
    Abstract: 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: Grant
    Filed: January 26, 1999
    Date of Patent: January 11, 2000
    Assignee: Alliedsignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5959152
    Abstract: 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: Grant
    Filed: October 2, 1998
    Date of Patent: September 28, 1999
    Assignee: Sumitomo Seika Chemicals Co., Ltd.
    Inventors: Kazuyoshi Hirako, Satoshi Kimura, Michio Suzuki
  • Patent number: 5925788
    Abstract: 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: Grant
    Filed: May 14, 1998
    Date of Patent: July 20, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Albrecht Marhold, Ernst Kysela
  • Patent number: 5831114
    Abstract: 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: Grant
    Filed: May 28, 1997
    Date of Patent: November 3, 1998
    Assignee: Novartis Finance Corporation
    Inventors: Hermann Rempfler, Fredrik Cederbaum, Felix Spindler, Willy Urs Lottenbach
  • Patent number: 5780682
    Abstract: 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: Grant
    Filed: September 19, 1997
    Date of Patent: July 14, 1998
    Assignee: Haldor Topsoe A/S
    Inventors: John Zavilla, Sven Ivar Hommeltoft
  • Patent number: 5696224
    Abstract: 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: Grant
    Filed: July 28, 1995
    Date of Patent: December 9, 1997
    Assignees: Centre National de la Recherche Scientifique, Hydro-Quebec
    Inventors: Djamila Benrabah, Michel Armand, Didier Delabouglise
  • Patent number: 5676884
    Abstract: 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: Grant
    Filed: November 20, 1996
    Date of Patent: October 14, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: George V. Tiers, Robert J. Koshar, Louis M. Leichter
  • Patent number: 5672626
    Abstract: 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: Grant
    Filed: July 9, 1996
    Date of Patent: September 30, 1997
    Assignee: G. D. Searle & Co.
    Inventors: Horng-Chih Huang, David R. Reitz
  • Patent number: 5672627
    Abstract: 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: Grant
    Filed: July 9, 1996
    Date of Patent: September 30, 1997
    Assignee: G.D. Searle & Co.
    Inventors: Horng-Chih Huang, David R. Reitz
  • Patent number: 5633409
    Abstract: 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: Grant
    Filed: January 27, 1995
    Date of Patent: May 27, 1997
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Satoshi Watanabe, Youichi Ohsawa, Toshinobu Ishihara, Kazumasa Maruyama, Yoshihumi Takeda, Junji Shimada, Fujio Yagihashi, Katsuya Takemura
  • Patent number: 5614525
    Abstract: The present invention is directed to the use of disulfonyl methane compounds for the control off parasites in vertebrate animals.
    Type: Grant
    Filed: May 4, 1995
    Date of Patent: March 25, 1997
    Assignee: Eli Lilly and Company
    Inventor: David I. Wickiser
  • Patent number: 5596122
    Abstract: The present invention is directed to disulfonyl methane compounds for the control of parasites in vertebrate animals.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: January 21, 1997
    Assignee: Eli Lilly and Company
    Inventor: David I. Wickiser
  • Patent number: 5578251
    Abstract: 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: Grant
    Filed: August 5, 1994
    Date of Patent: November 26, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Gary T. Boyd, George V. Tiers, Cecil V. Francis, Eugene P. Janulis, Robert J. Koshar, Louis M. Leichter
  • Patent number: 5538812
    Abstract: 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: Grant
    Filed: March 17, 1995
    Date of Patent: July 23, 1996
    Assignee: Moltech Corporation
    Inventors: Hung-Sui Lee, Lin Geng, Terje A. Skotheim
  • Patent number: 5502083
    Abstract: 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: Grant
    Filed: June 8, 1994
    Date of Patent: March 26, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5480568
    Abstract: 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: Grant
    Filed: July 22, 1994
    Date of Patent: January 2, 1996
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, Bassam S. Nader
  • Patent number: 5468903
    Abstract: 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: Grant
    Filed: March 1, 1993
    Date of Patent: November 21, 1995
    Assignee: Zeneca Limited
    Inventors: Kenneth R. Randles, Brian G. Gott, Stephen T. A. K. Daley
  • Patent number: 5446134
    Abstract: 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: Grant
    Filed: July 8, 1993
    Date of Patent: August 29, 1995
    Assignees: Centre National de la Recherche Scientifique, Hydro Quebec
    Inventors: Michel Armand, Djamila Benrabah, Jean-Yves Sanchez
  • Patent number: 5393776
    Abstract: 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: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5354511
    Abstract: 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: Grant
    Filed: November 27, 1992
    Date of Patent: October 11, 1994
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
  • Patent number: 5352706
    Abstract: 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: Grant
    Filed: July 22, 1993
    Date of Patent: October 4, 1994
    Assignee: Betz Laboratories, Inc.
    Inventors: Deborah K. Donofrio, Wilson K. Whitekettle
  • Patent number: 5296634
    Abstract: The present invention provides a method for preparing a 4-alkylsulfonyl-2-chloro-m-xylene useful as an intermediate for agricultural chemicals.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: March 22, 1994
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Masatoshi Baba, Eiichi Oya
  • Patent number: 5206440
    Abstract: 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: Grant
    Filed: July 28, 1992
    Date of Patent: April 27, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Richard Beckerbauer, Shlomo Rozen
  • Patent number: 5196604
    Abstract: Polymers comprising fluorine-containing poly(ether sulfones) and monomers comprising aromatic fluorine-containing sulfones used in the preparation of these polymers.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: March 23, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Andrew E. Feiring, Samuel D. Arthur
  • Patent number: 5189224
    Abstract: 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: Grant
    Filed: October 9, 1991
    Date of Patent: February 23, 1993
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Masatoshi Baba, Eiichi Oya
  • Patent number: 5152826
    Abstract: 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: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5144080
    Abstract: 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: Grant
    Filed: August 30, 1991
    Date of Patent: September 1, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Scott A. Biller, Cornelia Forster
  • Patent number: 5136097
    Abstract: 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: Grant
    Filed: December 3, 1990
    Date of Patent: August 4, 1992
    Assignees: Centre National de la Recherche Scientifique, Hydro-Quebec
    Inventor: Michel Armand
  • Patent number: 5123953
    Abstract: 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: Grant
    Filed: April 10, 1990
    Date of Patent: June 23, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philipe Desbordes, Michel Euvrard, Francois De Reinach Hirtzbach, Christopher Pearson
  • Patent number: 5100460
    Abstract: 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: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5095136
    Abstract: 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: Grant
    Filed: August 27, 1990
    Date of Patent: March 10, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Scott A. Biller, Cornelia Forster
  • Patent number: 5089647
    Abstract: 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: Grant
    Filed: April 11, 1990
    Date of Patent: February 18, 1992
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5084548
    Abstract: Polymers comprising fluorine-containing poly(ether sulfones) and monomers comprising aromatic fluorine-containing sulfones used in the preparation of these polymers.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: January 28, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Andrew E. Feiring, Samuel D. Arthur
  • Patent number: 5068397
    Abstract: 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: Grant
    Filed: August 15, 1990
    Date of Patent: November 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirkland P. Clark, Michael Jacobson, Athanasios Karydas, Juliana Rodgers
  • Patent number: 5023380
    Abstract: 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: Grant
    Filed: June 9, 1989
    Date of Patent: June 11, 1991
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, Bobby R. Ezzell, Katherine S. Clement
  • Patent number: 5017228
    Abstract: 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: Grant
    Filed: December 9, 1988
    Date of Patent: May 21, 1991
    Assignee: Fuji Kagakushi Kogyo Co., Ltd.
    Inventor: Hitoshi Goda
  • Patent number: 5015775
    Abstract: 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: Grant
    Filed: March 31, 1988
    Date of Patent: May 14, 1991
    Assignee: Atochem North America, Inc.
    Inventors: James L. Reilly, Gordon R. Leader