Halogen Containing Patents (Class 568/16)
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Patent number: 6841304Abstract: The invention concerns novel ionic compounds with low melting point whereof the onium type cation having at least a heteroatom such as N, O, S or P bearing the positive charge and whereof the anion includes, wholly or partially, at least an ion imidide such as (FX1O)N?(OX2F) wherein X1 and X2 are identical or different and comprise SO or PF, and their use as solvent in electrochemical devices. Said composition comprises a salt wherein the anionic charge is delocalised, and can be used, inter alia, as electrolyte.Type: GrantFiled: November 9, 2001Date of Patent: January 11, 2005Assignees: ACEP, Inc., Centre National de la Recherche Scientifique, Universite de MontrealInventors: Christophe Michot, Michel Armand, Michel Gauthier, Nathalie Ravet
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Patent number: 6841301Abstract: The present invention relates to fluoroalkyl phosphates, to a process for the preparation, and to their use as conductive salts in batteries, capacitors, supercapacitors and galvanic cells.Type: GrantFiled: August 1, 2001Date of Patent: January 11, 2005Assignee: Merck Patent GmbHInventors: Udo Heider, Michael Schmidt, Andreas Kühner, Peter Sartori, Nikolai Ignatyev
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Publication number: 20040191635Abstract: A non-aqueous electrolyte cell comprises a positive electrode, a negative electrode and a non-aqueous electrolyte containing a support salt. The non-aqueous electrolyte further comprises a phosphazene derivative. The phosphazene derivative having a specified structure functions as an electrode stabilizing agent or a non-combustion agent.Type: ApplicationFiled: January 5, 2004Publication date: September 30, 2004Inventors: Masashi Otsuki, Shigeki Endo, Takao Ogino, Yasuo Horikawa
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Publication number: 20040110631Abstract: Zwitterionic compositions of matter comprising cations [Ct]+ and anions connected together with substantially rigid fluorinated linking groups are described. These zwitterionic compositions serve as cocatalysts. They activate olefin polymerization catalysts, and can dissolve in aliphatic solvents. Synthesis and polymerization are illustrated.Type: ApplicationFiled: April 24, 2003Publication date: June 10, 2004Inventor: George Rodriguez
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Patent number: 6727390Abstract: A method of increasing the fluorous nature of a compound includes the step of reacting the compound with or tagging the compound with at least one of a second compound having the formula: wherein R is an alkyl group or an aryl group, n is 1, 2 or 3 and Rs is a spacer group and Rf is a branched fluorous group. A chemical compound having the general formula: wherein n, Rs and Rf are defined above.Type: GrantFiled: September 14, 2001Date of Patent: April 27, 2004Assignee: University of PittsburghInventors: Dennis P. Curran, Qisheng Zhang
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Publication number: 20030199704Abstract: Disclosed are methods of preparing monoalkyl Group VA metal dihalide compounds in high yield and high purity by the reaction of a Group VA metal trihalide with an organo lithium reagent or a compound of the formula RnM1X3-n where R is an alkyl, M1 is a Group IIIA metal, X is a halogen and n is an integer fro 1 to 3. Such monoalkyl Group VA metal dihalide compounds are substantially free of oxygenated impurities, ethereal solvents and metallic impurities.Type: ApplicationFiled: November 23, 2002Publication date: October 23, 2003Applicant: Shipley Company, L.L.C.Inventors: Deodatta Vinayak Shenai-Khatkhate, Michael Brendan Power, Artashes Amamchyan
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Publication number: 20030170548Abstract: The present invention provides an additive for a non-aqueous electrolyte comprising a phosphazene derivative represented by the following formula (1):Type: ApplicationFiled: May 5, 2003Publication date: September 11, 2003Inventors: Masashi Otsuki, Shigeki Endo, Takao Ogino
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Patent number: 6605736Abstract: A condensed phosphoric ester having a very low content of volatile components is provided by a process including a first step of reacting a phosphorus oxytrihalide with a bisphenol-based compound to prepare a phosphorohalidate; a second step of removing unreacted phosphorus oxytrihalide; and a third step of reacting the phosphorohalidate with a monophenol-based compound at a specific ratio.Type: GrantFiled: April 15, 2002Date of Patent: August 12, 2003Assignee: Daihachi Chemical Industry Co., Inc.Inventors: Shin Nakamura, Kazuo Noguchi, Taku Fujisawa, Takafumi Ohkawa
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Patent number: 6590100Abstract: The present invention provides a process for preparing a polyaromatic compound comprising at least one sequence of two aromatic rings. The process of the invention, which consists in reacting an aromatic compound bearing a leaving group and an arylboronic acid and/or its derivatives in the presence of a base and an effective amount of a nickel catalyst, is characterized in that the reaction is conducted in a reaction solvent which is water optionally in a mixture with an organic solvent and in the presence of an effective amount of a catalyst based on nickel with at least one water-soluble phosphine ligand.Type: GrantFiled: May 15, 2002Date of Patent: July 8, 2003Assignee: Rhodia ChimieInventors: Jean-Christophe Galland, Monique Savignac, Jean-Pierre Genet
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Patent number: 6590125Abstract: A light-emitting polymer and its preparation method, the polymer being excellent in electron injection and transport ability as well as hole injection and transport ability in an EL device, the EL device manufactured from the polymer being also emittable in the blue emission region, in which the EL device from an inorganic material is not mostly emittable. The light-emitting polymer of the invention is an alternated copolymer having repeated units (arylenevinylene units) excellent in hole injection and transport ability and repeated units (fluorinated tetraphenyl units) excellent in electron injection and transport ability with alternated order, as shown in formula (II). An EL device manufactured from the light-emitting polymer, a fluorinated tetraphenyl derivative of formula (I), which is used as a monomer to prepare the light-emitting polymer, and their preparation methods.Type: GrantFiled: April 3, 2001Date of Patent: July 8, 2003Assignee: Electronics and Telecommunications Research InstituteInventors: Do Hoon Hwang, Tae Hyoung Zyung, Lee Mi Do, Hye Yong Chu
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Patent number: 6548708Abstract: This invention relates to processes for making phosphorus compounds R2P—X—PR2, R2P—M, R2P—L and R3P, and the novel cation R2P+(L)—X—P+(L)R2, where R represents an optionally substituted hydrocarbyl group, X represents a bridging group, L represents a leaving group and M represents an alkali metal atom. The invention relates further to a process for making a compound R2P—L from a compound R—H via a new process for making the compound R—Li followed by its reaction with a compound Hal2P—L. The compound R2P—X—PR2 is a ligand suitable for making catalysts for copolymerizing carbon monoxide and a olefinically unsaturated compound.Type: GrantFiled: February 2, 2001Date of Patent: April 15, 2003Assignee: SRI InternationalInventors: Roelof Van Ginkel, Alexander Van Der Made, Jan De With, Wolf Eilenberg
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Patent number: 6538115Abstract: The present invention relates to novel complexes of (transition) metals containing ligands having phosphorus centers supporting a carbene atom or heteroalkane radical bonded to the (transition) metal.Type: GrantFiled: January 26, 2001Date of Patent: March 25, 2003Assignee: The Governors of the University of AlbertaInventors: Ronald G. Cavell, Ruppa P. Kamalesh Babu, Aparna Kasani
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Patent number: 6534684Abstract: A method for preparing tris[(1H,1H,2H,2H-perfluoroalkyl)aryl]phosphites consists in preparing a grignard reagent from an alkoxyhalogenobenzene, then reacting it with a iodo-1H,1H,2H,2H-perfluoroalkane; transforming the alkoxy function of (1H,1H,2H,2H,2H-perfluoroalkyl)alkoxybenzene obtained into a hydroxy function, then reacting (1H,1H,2H,2H-perfluoroalkyl)hydroxybenzene with PCl3. The invention also concerns fluorinated arylphosphites and their use as transition metal ligand for making catalysts to be used in two-phase catalysis with fluorinated phase.Type: GrantFiled: December 7, 2001Date of Patent: March 18, 2003Assignee: Centre National de la Recherche Scientifique (C.N.R.S.)Inventors: Jean-Luc Couturier, Thomas Mathivet, Eric Monflier, Yves Castanet, André Mortreux
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Patent number: 6509100Abstract: The present invention discloses hydrogen bond stabilized surface modifying agents having a fluorinated or semi-fluorinated carbon-containing tail group, an internal moiety capable of intermolecular hydrogen bonding or related acid-base interactions and a head group capable of reacting or interacting with surfaces such as metal, non-metallic, ceramic, other inorganic oxide or organic surfaces. The present invention also discloses cost effective method for making the agents, methods for treating surfaces therewith, the treated surfaces and devices made therefrom.Type: GrantFiled: August 18, 1999Date of Patent: January 21, 2003Assignee: The University of Houston SystemInventors: T. Randall Lee, Michael Graupe
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Publication number: 20020193619Abstract: Diaryliodonium salts are disclosed, as well as a method for preparing them, in which one of the aryl groups bonded to the positively-charged iodine ion contains a methyl substituent, and the other one contains a hydroxyl-substituted alkoxy group. The salts are synthesized from (o, m, or p)- iodotoluene, as opposed to iodobenzene, and therefore do not pose a carcinogenic risk. In addition, the present salts are unexpectedly more soluble in most organic solvents, as well as in nonpolar monomers, than the corresponding benzene catalysts. The salts are useful as cationic photoinitiators, cationic thermal initiators (often combined with a cocatalyst, e.g. copper), and as starting materials in the synthesis of urethane-containing iodonium salts.Type: ApplicationFiled: June 21, 2002Publication date: December 19, 2002Applicant: Polyset Company, Inc.Inventors: James V. Crivello, Georg Feldmann-Krane, Sascha Oestreich
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Publication number: 20020122979Abstract: Fluoroalkylphosphate salts of Formula I, described herein, are suitable for use, alone or in mixtures with, e.g., other salts, in electrolytes, primary batteries, secondary batteries, capacitors, supercapacitors or galvanic cells.Type: ApplicationFiled: February 25, 2002Publication date: September 5, 2002Applicant: Merck Patent GmbHInventors: Michael Schmidt, Andreas Kuh ner, Nikolai Ignatyev, Peter Sartori
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Patent number: 6437187Abstract: Novel chemical compounds have an ionic structure and in combination with an organometallic transition metal compound form a catalyst system which is advantageously used for the polymerization of olefins.Type: GrantFiled: August 16, 2000Date of Patent: August 20, 2002Assignee: Targor GmbHInventors: Hans Bohnen, Cornelia Fritze, Frank Kueber
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Patent number: 6380277Abstract: The present invention relates to iodonium salts containing urethane groups of reduced crystallization tendency, to a process for their preparation, and to their use for the radiation curing of cationically curing compositions.Type: GrantFiled: September 19, 2000Date of Patent: April 30, 2002Assignee: Goldschmidt AGInventors: Sascha Oestreich, Andreas Weier, Stefanie Volkmer
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Publication number: 20020015883Abstract: An ionic liquid of the formula K+A−, wherein K and A are as defined herein, can be used in such things as electrochemical cells, supercapacitors, hydraulic liquids, solvents, organic syntheses.Type: ApplicationFiled: May 30, 2001Publication date: February 7, 2002Applicant: Merck Patent GmbHInventors: Volker Hilarius, Udo Heider, Michael Schmidt
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Publication number: 20020015884Abstract: An ionic liquid of the formula K+A− wherein K+ and A− are as defined herein, are suitable for use in electrochemical cells and capacitors. These ionic liquids can also be used in catalysis, as inert solvents, and as hydraulic liquids.Type: ApplicationFiled: June 11, 2001Publication date: February 7, 2002Applicant: Merck Patent GmbHInventors: Michael Schmidt, Udo Heider, Winfried Geissler, Nikolai Ignatyev, Volker Hilarius
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Patent number: 6331532Abstract: The invention provides mitochondrially targeted antioxidant compounds. A compound of the invention comprises a lipophilic cation covalently coupled to an antioxidant moiety. In preferred embodiments, the lipophilic cation is the triphenyl phosphonium cation, and the compound is of the formula P(Ph3)+XR•Z− where X is a linking group, Z is an anion and R is an antioxidant moiety. Also provided are pharmaceutical compositions containing the mitochondrially targeted antioxidant compounds, and methods of therapy or prophylaxis of patients who would benefit from reduced oxidative stress, which comprise the step of administering the compounds of the invention.Type: GrantFiled: May 25, 2000Date of Patent: December 18, 2001Assignee: University of OtagoInventors: Michael P. Murphy, Robin A. J. Smith
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Publication number: 20010047114Abstract: An efficient process for the production of substituted 10-chloro-phenoxaphosphines or 10 bromo-phenoxaphosphines by reaction of substituted diphenyl ethers with phosphorus trihalogenide in the presence of at least one Lewis acid and subsequent treatment with an amine.Type: ApplicationFiled: April 30, 2001Publication date: November 29, 2001Inventors: Jurgen Herwig, Peter Skutta, Stefanie Sturm
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Patent number: 6306555Abstract: Radiation-sensitive compositions comprising (a1) a cationically or acid-catalytically polymerisable or crosslinkable compound or (a2) a compound that increases its solubility in a developer under the action of acid; and (b) at least one diaryliodonium salt of formula I X is branched C3-C20alkyl or C3-C8cycloalkyl; X1 is hydrogen, linear C1-C20alkyl, branched C3-C20alkyl or C3-C8cycloalkyl; with the proviso that the sum of the carbon atoms in X and X1 is at least 4; Y is linear C1-C10alkyl, branched C3-C10alkyl or C3-C8cycloalkyl; A− is a non-nucleophilic anion, selected from the group (BF4)−, (SbF6)−, (PF6)−, (B(C6F5))4−, C1-C20alkylsulfonate, C2-C20haloalkylsulfonate, unsubstituted C6-C10arylsulfonate, camphorsulfonate, and C6-C10arylsulfonate substituted by halogen, NO2, C1-C12alkyl, C1-C12halo-alkyl, C1-C12alkoxy or by COOR1; and R1 is C1-C20alkyl, phenyl, benzyl; or phenyl mono- or poly-substituted by C1-C12alkyl, C1-C12alkoxy or by halogen; with theType: GrantFiled: December 18, 2000Date of Patent: October 23, 2001Assignee: CIBA Specialty Chemicals Corp.Inventors: Reinhard Schulz, Jean-Luc Birbaum, Jean-Pierre Wolf, Stephan Ilg, Hitoshi Yamato, Toshikage Asakura
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Patent number: 6235727Abstract: Compounds of the formula I are suitable for the production of pharmaceuticals for the prophylaxis and therapy of disorders in the course of which an increased activity of matrix-degrading enzymes is involved.Type: GrantFiled: July 15, 1999Date of Patent: May 22, 2001Assignee: Aventis Pharma Deutschland GmbHInventors: Manfred Schudok, Wilfried Schwab, Gerhard Zoller, Eckart Bartnik, Frank Büttner, Klaus-Ulrich Weithmann
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Patent number: 6225504Abstract: A process for the preparation of the formula Ar13−xP[(Ar2(OZ)y]x I wherein Ar1 and Ar2 are individually aromatic of 6 to 20 carbon atoms or heteroaromatic of 4 to 9 carbon atoms, each unsubstituted or substituted with at least one member of the group consisting of halogen, carboxyl, —OH, alkyl of 1 to 6 carbon atoms, phenyl and naphthyl, Ar1 has one valence and R2 has y+1 valences, x is an integer of 1, 2 or 3, y is 1 or 2, Z is carbohydrate with a glycosidic bond comprising reacting a hydrocarbon halide of the formula Z′—X II when Z′ has the definition of Z with —OH protected and X is chlorine, bromine or fluorine with a phosphane of the formula Ar13−xP[(Ar2 (OH)y]x III in a multi-phase reaction medium in the presence of a base and a phase transfer catalyst to form a phosphane of the formula Ar13−xP[(Ar2(OZ1)y]x IV and removal of the protective groups to form a compound of FoType: GrantFiled: June 23, 1999Date of Patent: May 1, 2001Assignee: Celanese GmbHInventors: Sandra Bogdanovic, Matthias Beller, Alexander Zapf, Jurgen Krauter
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Patent number: 6210830Abstract: The invention relates to novel lithium fluorophosphates of the general formula Li+[PFa(CHbFc(CF3)d)e]−, (I) wherein a is 1, 2, 3, 4 or 5, b is 0 or 1, c is 0, 1, 2 or 3, d is 0, 1, 2 or 3 and e is 1, 2, 3 or 4, with the condition that the sum of a+e is equal to 6, the sum of b+c+d is equal to 3 and b and c are not simultaneously 0, with the proviso that the ligands (CHbFc(CF3)d) may be different, a process for producing said compounds, their use in electrolytes, and also lithium batteries produced using said electrolytes.Type: GrantFiled: March 8, 2000Date of Patent: April 3, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Peter Sartori, Nikolai Ignatyev
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Patent number: 6211397Abstract: A process for the preparation of &agr;-chloromethylene-triorganylphosphorane derivatives I (radicals R are C-organic substituents and A stands for CN or CO-B where B is a C-organic or O-organic radical which is inert under chlorination conditions) by chlorination of phosphoranes II with chlorine, wherein the chlorination is carried out in the presence of a mineral base as hydrogen chloride acceptor and the chlorine and base are fed to the reaction mixture concurrently but separately at the rates at which they are consumed. The reaction products I are important intermediates for plant protectants.Type: GrantFiled: March 2, 1994Date of Patent: April 3, 2001Assignee: BASF AktiengesellschaftInventors: Bernd Schaefer, Ernst Buschmann, Gernot Reissenweber
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Patent number: 6169179Abstract: A method for manufacturing (3S,4R)-4-[(R)-1′-formylethyl]azetidin-2-one derivatives represented by formula (3) wherein R1 represents a hydrogen atom or a protective group, through asymmetric hydroformylation of 4-vinylazetidin-2-one represented by formula (1) wherein R1 has the same meaning as described above; in the presence of a rhodium complex and a (2S,4S)-diphosphine compound represented by formula (2) wherein R2 represents a phenyl group which may be substituted with 1-5 substituent(s) selected from a lower alkyl group, a lower alkoxy group, and a halogen atom. By use of both an inexpensive optically active diphosphine compound and a rhodium complex as catalysts, intermediate compounds important for carbapenem antibiotics can be manufactured with high selectivity and efficiency.Type: GrantFiled: June 10, 1999Date of Patent: January 2, 2001Assignee: Takasago International CorporationInventors: Howard Alper, Takao Saito, Takashi Miura
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Patent number: 6075154Abstract: A novel phosphine compound usable as a catalyst in various asymmetric synthetic reactions is disclosed. The compound is a 2,2'-bis(diarylphosphino)-6,6'-bis(trifluoromethyl)-1,1'-biphenyl of (1): ##STR1## where R is a phenyl group or a phenyl group substituted by lower alkyl group, lower alkoxy group, halogen atom, or lower haloalkyl group.Type: GrantFiled: July 30, 1998Date of Patent: June 13, 2000Assignee: Takasago International CorporationInventors: Yoshiharu Gonda, Yoji Hori, Akio Yamaguchi, Toshimitsu Hagiwara
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Patent number: 6040461Abstract: The invention relates to a process for the preparation of vitamin D.sub.3 compounds of formula I. ##STR1## Wherein A is a single or a double bond; B is a single, cis-double, trans double or a triple bond; R.sub.1 and R.sub.2 are independently hydrogen, a lower alkyl, e.g., a C.sub.1 -C.sub.4 alkyl; R.sub.3 and R.sub.4 are independently a lower alkyl, e.g., C.sub.1 -C.sub.4 alkyl, a hydroxyalkyl, and a haloalkyl, e.g., a fluoroalkyl; and X and Y are independently hydrogen or hydroxy in the case when B is a single or a double bond.Type: GrantFiled: May 11, 1999Date of Patent: March 21, 2000Assignees: Hoffmann-La Roche Inc., Syntex (U.S.A.)Inventors: Andrew David Batcho, Percy Sarwood Manchand, Milan Radoje Uskokovic
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Patent number: 6020528Abstract: Compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 independently of one another are hydrogen, halogen, C.sub.1 -C.sub.20 alkyl, cyclopentyl, cyclohexyl, C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.18 alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C.sub.1 -C.sub.4 alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy with the provisos that at least one of the radicals R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is other than hydrogen and that, if R.sub.1 and R.sub.2 are methyl, R.sub.3 and R.sub.6 are not methyl, and mixtures of such compounds with .alpha.-hydroxy ketones, benzophenones and .alpha.-amino ketones, are suitable as photoinitiators.Type: GrantFiled: February 26, 1997Date of Patent: February 1, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: David George Leppard, Manfred Kohler, Andreas Valet
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Patent number: 5969195Abstract: A process for hydrolyzing alkyl monohalides comprises using activated carbon impregnated with alkali metal hydroxide or alkaline earth metal hydroxide in the presence of water and converting the alkyl monohalides virtually quantitatively into the corresponding alcohols. Apparatus for carrying out the process comprises at least one, preferably two, especially three, reactors (2), especially tubular reactors. The process is also particularly useful for preparing alcohols.Type: GrantFiled: May 12, 1998Date of Patent: October 19, 1999Assignee: BASF AktiengesellschaftInventors: Uwe Stabel, Gerhard Fahrbach, Werner Neumann
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Patent number: 5945521Abstract: Methods and intermediates for the preparation of oligomers containing diastereomerically enriched phosphorothioate linkages are disclosed.Type: GrantFiled: October 9, 1997Date of Patent: August 31, 1999Assignee: McGill UniversityInventors: George Just, Zhili Xin, Eric Marsault, Yi Jin
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Patent number: 5919983Abstract: A catalyst activator, comprising a cation which is a Bronsted acid capable of donating a proton, and an inert, compatible, noncoordinating, anion, characterized by a solubility constant at 25.degree. C. in hexane, cyclohexane or methylcyclohexane of at least 5 weight percent.Type: GrantFiled: March 14, 1997Date of Patent: July 6, 1999Assignee: The Dow Chemical CompanyInventors: Robert K. Rosen, Daniel D. VanderLende
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Patent number: 5908931Abstract: The present invention relates particularly to novel preorganized hexadentate ligands that are suitable for completing with a radionuclide, and are useful as general imaging agents for diagnostic purposes.Type: GrantFiled: December 14, 1990Date of Patent: June 1, 1999Assignee: Mallinckrodt Inc.Inventors: Raghavan Rajagopalan, William L. Neumann, Dennis L. Nosco
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Patent number: 5874628Abstract: The invention is an improved method for the preparation of tertiary phosphines by way of cross-coupling of aryl, alkenyl, cycloalkenyl or aralkyl halides or aryl, alkenyl, cycloalkenyl or aralkyl sulfonate esters with chlorophosphines in the presence of a catalyst and a reductant. The general reaction scheme is shown below: ##STR1## wherein R.sup.1 is aryl, alkenyl, cycloalkenyl or aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl, or CONR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; R.sup.2 and R.sup.3 are independently aryl, alkyl, aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl or CoNR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; and n is 2 where R.Type: GrantFiled: March 26, 1997Date of Patent: February 23, 1999Assignee: Monsanto CompanyInventors: Scott A. Laneman, David J. Ager, Amihia Eisenstadt
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Patent number: 5861540Abstract: Synthetic procedures to tetraalkyls, tetraacids and dianhydrides substituted 1,1,1-triaryl-2,2,2-trifluoroethanes which comprises: (1) 1,1-bis(dialkylaryl)-1-aryl-2,2,2 -trifluoroethane, (2) 1,1-bis(dicarboxyaryl)-1-aryl-2,2,2-trifluoroethane or (3) cyclic dianhydride or diamine of 1,1-bis(dialkylaryl)-1-aryl-2,2,2-trifluoroethanes. The synthesis of (1) is accomplished by the condensation reaction of an aryltrifluoromethyl ketone with a dialkylaryl compound. The synthesis of (2) is accomplished by oxidation of (1). The synthesis dianhydride of (3) is accomplished by the conversion of (2) to its corresponding cyclic dianhydride. The synthesis of the diamine is accomplished by the similar reaction of an aryltrifluoromethyl ketone with aniline or alkyl substituted or disubstituted anilines. Also, other derivatives of the above are formed by nucleophilic displacement reactions.Type: GrantFiled: April 15, 1994Date of Patent: January 19, 1999Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: William B. Alston, Roy F. Gratz
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Patent number: 5847222Abstract: The present invention provides a ligand for a novel catalyst superior in such characteristics as selectivity (chemoselectivity and enantioselectivity) and catalytic activity in asymmetric synthesis reactions and a ligand for a novel catalyst effective in an asymmetric hydrogenation reaction in particular. The ligand is an optically active diphosphine compound represented by the following formula: ##STR1## where Ph is a phenyl group, X is a chlorine or bromine atom, and R.sup.1 and R.sup.2 are each an alkyl group having 1 to 3 carbon atoms.Type: GrantFiled: August 26, 1997Date of Patent: December 8, 1998Assignee: Takasago International CorporationInventors: Tohru Yokozawa, Noboru Sayo, Kazuhiko Matsumura, Hidenori Kumobayashi
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Patent number: 5808163Abstract: The invention relates to chiral tertiary alkyldiarylphosphines of the formula (I), ##STR1## where: R.sup.1 is (C.sub.1 -C.sub.4)alkyl, which can also be substituted by F, CF.sub.3, OCH.sub.3,Ar.sup.1, Ar.sup.2 are phenyl, naphthyl, anthracenyl, which can also bear one or more substituents selected from the group consisting of (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, CF.sub.3, F,* designates the chiral carbon atom which can have either an (R) or an (S) configuration,and also a process for preparing these compounds.Type: GrantFiled: July 17, 1996Date of Patent: September 15, 1998Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Hans Millauer, Peter Brungs
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Patent number: 5789623Abstract: The present invention relates to a hydroxybiarylphosphines of the formula ##STR1## in which Ar-Ar is biphenyl, 1-phenyinaphthyl or 1,1'-binaphthyl, R.sup.1 and R.sup.2 are identical or different and are F or alkoxy having in each case 1 to 8 carbon atoms or are substituted or unsubstituted aryl, a and b are identical or different and are an integer from 0 to 4, in which R.sup.3 and R.sup.4 are identical or different and are alkyl having 1 to 8 carbon atoms, cycloalkyl having 4 to 10 carbon atoms, alkaryl having 7 to 9 carbon atoms, Ar.sup.3 --(R.sup.5).sub.n, in which A.sup.3 is an aryl radical having 6 to 10 carbon atoms, R.sup.5 is CF.sub.3, dialkylamino having a total of 2 to 8 carbon atoms or --CH.sub.2 N(alkyl).sub.2 having 1 to 3 carbon atoms per alkyl and n is an integer from 0 to 5, or --R.sup.3 --R.sup.Type: GrantFiled: June 11, 1996Date of Patent: August 4, 1998Assignee: Hoechst AktiengesellschaftInventors: Dieter Regnat, Hans-Jerg Kleiner
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Patent number: 5789624Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbomane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.Type: GrantFiled: April 10, 1996Date of Patent: August 4, 1998Assignee: Hoechst Celanese CorporationInventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
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Patent number: 5777087Abstract: The present invention provides novel aryl diphosphines having the formula ##STR1## wherein X, Y, R.sub.1-18, m, m' and n are defined herein, and which can be complexed with a transition metal to form a novel catalyst useful in such applications as hydroformylation.Type: GrantFiled: April 18, 1996Date of Patent: July 7, 1998Assignee: Celanese International CorporationInventors: Christian W. Kohlpaintner, Brian E. Hanson, Hao Ding
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Patent number: 5773661Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.Type: GrantFiled: September 2, 1997Date of Patent: June 30, 1998Assignee: Celanese International CorporationInventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
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Patent number: 5710338Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.Type: GrantFiled: April 10, 1996Date of Patent: January 20, 1998Assignee: Hoechst Celanese CorporationInventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
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Patent number: 5710339Abstract: The invention relates to enantiomerically pure bisphosphines of the general formula (I) ##STR1## where R is as defined in the description,a process for their preparation and their use in metal complexes as catalysts for asymmetric reactions, in particular asymmetric hydrogenations.Type: GrantFiled: June 13, 1996Date of Patent: January 20, 1998Assignee: Bayer AktiengesellschaftInventors: Christian Laue, Georg Schroder, Dieter Arlt
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Patent number: 5710337Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.Type: GrantFiled: April 10, 1996Date of Patent: January 20, 1998Assignee: Hoechst Celanese CorporationInventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
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Patent number: 5696296Abstract: A diphosphine of the formula (I) ##STR1## in which Ar--Ar is a biphenyl radical, a 1-phenyl-naphthyl radical or a 1,1'-binaphthyl radical, the CH.sub.2 groups am each located in the ortho-position relative to the Ar--Ar bond, R is F or an alkyl radical or alkoxy radical having in each case 1 to 8 carbon atoms, n is an integer from 0 to 4, the radicals PR.sup.1 R.sup.2 and PR.sup.3 R.sup.4 differ from one another, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each an alkyl radical having 1 to 10 carbon atoms, a cycloaliphatic radical having 5 to 10 carbon atoms, or a radical Ar.sup.1 --(R.sup.5).sub.m, in which AR.sup.1 is a phenyl radical, R.sup.5 is F, CF.sub.3, or an alkyl radical having 1 to 4 carbon atoms and m is 0 to 1, or R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: September 27, 1995Date of Patent: December 9, 1997Assignee: Hoechst AktiengesellschaftInventors: Christoph Naumann, Dieter Regnat
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Patent number: 5693807Abstract: The invention relates to substituted hydroquinone derivatives of the general formula I ##STR1## wherein R.sub.4 is lower alkyl and either R.sub.1 is hydroxy, halogen, a group of the formula --P(=O)(R.sub.5)R.sub.6 (Ia), a group of the formula --P.sup.+ (R.sub.7)(R.sub.8)R.sub.9 X.sup.- (Ib) or a group of the formula --Si(R.sub.7)(R.sub.8)R.sub.9 (Ic), M is methylene, R.sub.2 is hydrogen or a group of the formula ##STR2## and R.sub.3 is hydrogen or halogen, or .sub.1 is hydroxy or lower alkoxy, M is carbonyl, R.sub.2 is hydrogen and R.sub.3 is halogen, each of R.sub.5 and R.sub.6, independently of the other, is lower alkyl, lower alkoxy Or N,N-di-lower alkylamino, or is benzyl, benzyloxy, phenyl or phenoxy, each of which is unsubstituted or mono- or di-substituted at the phenyl ring, to a process for the preparation of those compounds and to the use of those compounds, and to a process in which those compounds are used.Type: GrantFiled: June 5, 1995Date of Patent: December 2, 1997Assignee: Ciba-Geigy CorporationInventors: Gottfried Sedelmeier, Gerhard Fischer
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Patent number: 5693868Abstract: The present invention provides a method for producing novel optically active diphosphine compounds ?2,2'-bis(di-substituted phosphino)-1,1'-binaphthyl compounds! having a selectivity (chemoselectivity or enantioselectivity) and catalytic activity different from those of conventional BINAP compounds. In a method of the present invention for producing an optically active diphosphine compound (i.e., 2,2-bis(di-substituted phosphino)-1,1'-binaphthyl), 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl is reacted, in the presence of a transition metal-phosphine complex, with a phosphineoxide compound represented by the following general formula:A.sub.Type: GrantFiled: October 30, 1996Date of Patent: December 2, 1997Assignee: Takasago International CorporationInventors: Noboru Sayo, Xiaoyong Zhang, Tatsuya Ohmoto, Akifumi Yoshida, Tohru Yokozawa
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Patent number: 5623089Abstract: Novel triphenylbis(fluoroalkoxy)phosphoranes and a process for their preparation are disclosed. Also disclosed is a process for making fluorinated ketals by reacting phosphoranes with fluorinated ketones.Type: GrantFiled: May 22, 1995Date of Patent: April 22, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Zhen-Yu Yang