Benzene Ring Containing Patents (Class 568/17)
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Patent number: 6664427Abstract: The invention relates to a process for the making organic aldehyde compounds from an unsaturated compound by hydroformylation and in the presence of a catalyst system comprising a Group VIII metal and a bidentate phosphorus ligand having two trivalent phosphorus atoms bound to salicylanilide groups.Type: GrantFiled: August 29, 2002Date of Patent: December 16, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Patrick M. Burke, James Michael Garner, Wilson Tam
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Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catalytic reactions
Patent number: 6653485Abstract: 3,3′-Substituted chiral biaryl phosphine and phosphinite ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition, epoxidation, kinetic resolution and [m+n] cycloaddition. The metal complexes are particularly effective in Ru-catalyzed asymmetric hydrogenation of beta-ketoesters to beta-hydroxyesters and Ru-catalyzed asymmetric hydrogenation of enamides to beta amino acids.Type: GrantFiled: November 16, 2001Date of Patent: November 25, 2003Assignee: The Penn State Research FoundationInventor: Xumu Zhang -
Patent number: 6639114Abstract: Ethylenically unsaturated compounds are hydroformylated in the presence of a hydroformylation catalyst comprising at least one complex of a metal of transition group VIII with at least one phosphorus-containing compound as ligand, where this compound contains two groups which contain P atoms and are bound to a molecular skeleton derived from bisphenol A.Type: GrantFiled: February 13, 2002Date of Patent: October 28, 2003Assignee: BASF AktiengesellschaftInventors: Wolfgang Ahlers, Rocco Paciello, Dieter Vogt, Jarl Ivar van der Vlugt
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Publication number: 20030199084Abstract: The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).Type: ApplicationFiled: March 6, 2003Publication date: October 23, 2003Inventors: Eliana Saxon, Carolyn Ruth Bertozzi
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Patent number: 6630604Abstract: Novel phosphine and phosphine oxide ligands are prepared using polymeric supports. These compounds can be easily cleaved from the support, and along with the corresponding supported compounds, used as ligands in the preparation of novel, metal-complexed catalysts. The ligands are obtained by combinatorial synthesis. A process for preparing coumarin by contacting salicylaldehyde with an acrylate is also provided.Type: GrantFiled: April 9, 2001Date of Patent: October 7, 2003Assignee: E. I. du Pont de Nemours and CompanyInventor: George Y. Li
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Patent number: 6624320Abstract: A novel phosphine compound having excellent properties (chemical selectivity, enantioselectivity, catalytic activity) as a catalyst for asymmetric syntheses, especially asymmetric hydrogenation. A phosphine-phosphorane compound represented by the following general formula: (wherein R1 represents hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, R2, R3, R4, and R5 are the same or different, and each represents hydrogen atom, or an alkyl group having 1 to 6 carbon atoms, etc., and each of R2 and R3, R3 and R4, and R4 and R5 may be together combined to form a ring which may contain one or more (preferably 1 to 2) oxygen atoms, and R6 and R7 are the same or different, and each represents a linear or branched alkyl group having 1 to 6 carbon atoms, etc.).Type: GrantFiled: November 12, 2002Date of Patent: September 23, 2003Assignee: Takasago International CorporationInventors: Kazuhiko Matsumura, Takao Saito
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Patent number: 6613717Abstract: Phosphorus-containing benzoyl derivatives of the formula I where: P(═X)R1R2X is an organic phosphorus radical; R3 is hydrogen, nitro, cyano, halogen, unsub. or sub. alkyl, alkylcarbonyl, alkoxycarbonyl, unsub. or sub. alkoxy, unsub. or sub. alkylthio, unsub. or sub. alkylsulfinyl, unsub. or sub. alkylsulfonyl, unsub. or sub. aminosulfonyl, unsub. or sub. amino, P(═X)R1R2, unsub. or sub. phenyl or unsub. or sub. heterocyclyl; R4 is nitro, cyano, halogen, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl; l is 0, 1 or 2; Q is unsub. or sub. 1-hydroxy-3-oxocyclohex-1-en-2-yl, unsub. or sub. 5-hydroxypyrazol-4-yl, unsub. or sub. isoxazol-4-yl or unsub. or sub. 2-cyano-1-oxoeth-2-yl; and their agriculturally useful salts; processes and intermediates for preparing the phosphorus-containing benzoyl derivatives; compositions comprising them and the use of these derivatives or the compositions comprising them for controlling undesirable plants are described.Type: GrantFiled: October 29, 2001Date of Patent: September 2, 2003Assignee: BASF AktiengesellschaftInventors: Klaus Langemann, Thorsten Volk, Ernst Baumann, Wolfgang von Deyn, Steffen Kudis, Guido Mayer, Ulf Misslitz, Ulf Neidlein, Matthias Witschel, Martina Otten, Karl-Otto Westphalen, Helmut Walter
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Patent number: 6613848Abstract: A hardener for an epoxy resin comprises a phenolic, thiophenolic, aminophenyl, tris-phenolic, tris-thiophenolic, tris-aminophenyl, tetrakis-phenolic, tetrakis-thiophenolic, or tetrakis-aminophenyl compounds; or phenol-formaldehyde or phenol-formaldehyde/melamine-formaldehyde resins wherein the phenyl rings are substituted with at least one of the structures wherein R1 and R2 independently are H, C1-C18 alkyl, C6-C18 aryl, C6-C18 substituted aryl, C6-C18 aryl methylene, or C6-C18 substituted aryl methylene; X is O, S or NH and Ar is wherein R is C1-C4 alkyl and n=0-5.Type: GrantFiled: May 16, 2000Date of Patent: September 2, 2003Assignee: National Science CouncilInventors: Chun-Shan Wang, Jeng-Yueh Shieh
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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: 6579997Abstract: A metallacrown ether ligand chelates a transition metal atom to form a catalyst well suited to perform hydroformylation in the presence of carbon monoxide, hydrogen and an unsaturated substrate compound.Type: GrantFiled: July 3, 2002Date of Patent: June 17, 2003Assignee: UAB Research FoundationInventors: Gary M. Gray, Maheswaran Harihara Sarma, Dale C. Smith
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Patent number: 6576684Abstract: Disclosed are compositions from which radically initiated oligomers/polymers having a controlled molecular weight, low polydispersity and a vinyl or dienyl end group are prepared. Further subjects of the invention are a process for controlled radical polymerization, oligomers/polymers obtainable by said process and the use of specific addition fragmentation agents for the polymerization process. The addition fragmentation agents are new in part and these are also subject of the present invention. The addition fragmentation agents are of the formula (Ia), (Ib) or (Ic) where Y is a group which activates the double bond towards Michael addition.Type: GrantFiled: February 15, 2001Date of Patent: June 10, 2003Assignee: Ciba Specialty Chemicals CorporationInventors: Vincent Desobry, Peter Murer, Anne Schuwey
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Patent number: 6570040Abstract: The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).Type: GrantFiled: March 16, 2001Date of Patent: May 27, 2003Assignee: The Regents of the University of CaliforniaInventors: Eliana Saxon, Carolyn Bertozzi
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Patent number: 6563005Abstract: Mono- and di-arylphosphines are prepared by reacting an aryl compound that has a leaving group attached to a carbon atom of the aromatic ring with phosphine in the presence of a Group VIII metal catalyst.Type: GrantFiled: February 1, 2002Date of Patent: May 13, 2003Assignee: Cytec Technology Corp.Inventors: John Henry Hillhouse, William Andrew Rickleton
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Publication number: 20030088128Abstract: One aspect of the present invention relates to novel reaction conditions that allow the efficient synthesis of diaryl ethers from arenes bearing a leaving group and arenols under relatively mild conditions. Another aspect of the present invention relates to the dramatic effects of acidic activators on Ullmann-type couplings involving electron-poor and/or relatively insoluble substrates.Type: ApplicationFiled: April 25, 2002Publication date: May 8, 2003Inventors: Jean-Francois Marcoux, Sven Doye, Stephen Buchwald
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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: 6534038Abstract: This invention relates to novel highly functionalized phosphine ligands as ancillary ligands in radiopharmaceuticals. Also, this invention provides radiopharmaceuticals comprised of highly functionalized phosphine ligated 99mTc labeled HYNIC-conjugated biomolecules that selectively localize at sites of disease and thus allow an image to be obtained of the loci using gamma scintigraphy. The invention also provides methods of use of the radiopharmaceuticals as imaging agents for the diagnosis of cardiovascular disorders such as thromboembolic disease or atherosclerosis, infectious disease and cancer.Type: GrantFiled: April 5, 2001Date of Patent: March 18, 2003Assignee: Bristol-Myers Squibb Pharma CompanyInventor: Shuang Liu
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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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Patent number: 6515183Abstract: Compounds of formula III, wherein R6 und R7 signify identical or different secondary phosphino; R8 is —CH2—OH, —CH2—NH2, —CH2—O—B—FU, —CH2—NH2—B—FU, or —O—B—FU; R9 has the same significance as R8 or is C1-C4-alkyl or C1-C4-alkoxy; or R8 and R9 together signify HOCH(CH2—O—)2, H2NCH—(CH2—O—)2, FU—B—OCH(CH2—O—)2 or FU-B-HNCH(CH2—O—)2; B is a bridging group; and FU is a functional group. The compounds may be bonded to inorganic or organic carriers. Their d-8 metal complexes are valuable catalysts for the enantioselective hydrogenation of prochiral organic compounds with carbon multiple bonds or carbon/hetero atom multiple bonds.Type: GrantFiled: July 6, 2001Date of Patent: February 4, 2003Assignee: Solvias AGInventors: Benoît Pugin, Ivo Steiner, Rhony Niklaus Aufdenblatten, Antonio Togni
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Patent number: 6508753Abstract: A novel phosphine ligand is an enantiomerically enriched compound of formula 5 or the opposite enantiomer thereof, wherein Ar1 and Ar2 represent the same or different aromatic groups of up to 20 C atoms. A transition metal complex of this ligand is useful as a catalyst in stereoselective hydrogenation.Type: GrantFiled: June 4, 2001Date of Patent: January 21, 2003Assignee: Chirotech Technology LimitedInventors: Mark Joseph Burk, Christophe Guillaume Malan
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Patent number: 6489513Abstract: The invention relates to the preparation of enantiomerically pure bis-diphenylphosphine oxides in a particularly advantageous manner by (1) reacting an aromatic bromine compound with a diphenylphosphinic chloride in a mixture of tetrahydrofuran and an aromatic hydrocarbon to give a diphenylphosphine oxide, which is isolated from a solution in an aromatic hydrocarbon by adding a saturated aliphatic hydrocarbon; (2) metalating the resulting diphenylphosphine oxide in the 6-position and reacting the metalated diphenylphosphine oxide with iodine at temperatures not less than −25° C.Type: GrantFiled: November 13, 2001Date of Patent: December 3, 2002Assignee: Bayer AktiengesellschaftInventors: Torsten Pohl, Thomas Prinz, Guido Giffels, Wolfram Sirges
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Patent number: 6476272Abstract: Organophosphines of the formula (R)aP(H)3−a( where R is C1-C20 alkyl, alkenyl, alkaryl or styryl and a is 1, 2, or 3) are produced by (i) reacting a tris(hydroxyorgano)phosphine (THP) with an organic halogen containing compound; (ii) reacting the product of (i) with a base; (iii) removing aldehydes from the product of (ii) and adding an organic phase, followed by distillation or phase-separation to obtain the desired product.Type: GrantFiled: June 18, 2001Date of Patent: November 5, 2002Assignee: Rhodia Consumer Specialties LimitedInventors: Gary Woodward, Ranbir Singh Padda, Christian Thomas Regius
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Patent number: 6455720Abstract: A novel 2,2-(diaryl)vinylphosphine compound represented by the following general formula (1): (wherein R1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc.; R2, R3, R4, R5, R6, and R7 may be the same or different and each is an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc., provided that R4 and R5 taken together and/or R6 and R7 taken together may represent a fused benzene ring, a substituted fused benzene ring, a trimethylene group, etc.; and p, q, r, and s each is 0 to 5, provided that p+q and r+s each is in the range of from 0 to 5); a palladium-phosphine catalyst obtained by causing a palladium compound to act on the novel 2,2-(diaryl)vinylphosphine compound; and a process for obtaining an arylamine, a diaryl and an arylalkyne in the presence of the palladium-phosphine catalyst.Type: GrantFiled: June 27, 2001Date of Patent: September 24, 2002Assignee: Takasago International CorporationInventors: Ken Suzuki, Tohru Kobayashi, Takenobu Nishikawa, Yoji Hori, Toshimitsu Hagiwara
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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: 6410746Abstract: Compounds having the formula: are disclosed. M1 and M2 are the same or different and are transition metal atoms or ions; Z2 and Z3, independently, are the atoms necessary to complete a 3-12 membered heterocyclic ring; Z1 is an alkylene or arylene group; Q1 and Q2 are the same or different and are electron withdrawing groups; L1 and L3, taken together, represent —O—CR13—O—; L2 and L4, taken together, represent —O—CR14—O—; and R13 and R14 are the same or different and are selected from the group consisting of alkyl groups and aryl groups or R13 and R14 represent alkylene or arylene groups that are directly or indirectly bonded to one another. Methods for making such compounds are also disclosed, as are intermediates which can be used in their preparation. Also disclosed are methods for carrying out C—H insertion reactions using bis-transition metal catalysts, such as the above compounds.Type: GrantFiled: March 8, 2000Date of Patent: June 25, 2002Assignee: Research Foundation of State University of New York, TheInventor: Huw M. L. Davies
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Patent number: 6395916Abstract: One aspect of the present invention relates to novel, electron-rich bidentate ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.Type: GrantFiled: July 10, 1998Date of Patent: May 28, 2002Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, John P. Wolfe, David W. Old, Ken Kamikawa, Michael Palucki
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Patent number: 6395939Abstract: One aspect of the present invention relates to novel reaction conditions that allow the efficient synthesis of diaryl ethers from arenes bearing a leaving group and arenols under relatively mild conditions. Another aspect of the present invention relates to the dramatic effects of acidic activators on Ullmann-type couplings involving electron-poor and/or relatively insoluble substrates.Type: GrantFiled: October 5, 1998Date of Patent: May 28, 2002Assignee: Massachusetts Institute of TechnologyInventors: Jean-Francois Marcoux, Sven Doye, Stephen Buchwald
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Publication number: 20020058837Abstract: A novel 2,2-(diaryl)vinylphosphine compound represented by the following general formula (1): 1Type: ApplicationFiled: June 27, 2001Publication date: May 16, 2002Inventors: Ken Suzuki, Tohru Kobayashi, Takenobu Nishikawa, Yoji Hori, Toshimitsu Hagiwara
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Patent number: 6388130Abstract: The invention provides a metal complex comprising a ligand and a metal. The ligand is an aminophosphine compound represented by the following formula (1) The metal is rhodium, ruthenium, iridium or nickel.Type: GrantFiled: June 7, 2001Date of Patent: May 14, 2002Assignee: Takasago International CorporationInventors: Sumi Kenzo, Noyori Ryoji, Ikariya Takao
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Publication number: 20020055584Abstract: A method of preparing a sterile article is disclosed. A polymer having a halogen-containing repeating unit is prepared that contains about 0.Type: ApplicationFiled: October 9, 2001Publication date: May 9, 2002Applicant: Occidental Chemical CorporationInventors: Qi Wang, Sandor Nagy
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Patent number: 6376715Abstract: A method of manufacturing a compound of general formula (R3—C)2P—L1—X—L2—P—(C—R3)2, in which each R is independently a pendant, optionally substituted, organic group through which the group is linked to tertiary carbon atom C; L1, L2 are independently a linking group selected from an optionally substituted lower alkylene chain connecting the respective phosphorus atom to the group X and X is a bridging group comprising an optionally substituted aryl moiety to which the phosphorus atoms are linked on available adjacent carbon atoms, comprises: i) reacting together a compound of formula H—L1—X—L2—H with an organometallic compound to form an intermediate compound of formula M—L1—X—L2—M, where M is an alkali metal atom; ii) reacting said intermediate compound with a compound of formula (R3—C)2P—A, where A is a halogen atom, to form said compound of general formula (R3—C)2P—L1—X—L2—P&Type: GrantFiled: December 1, 2000Date of Patent: April 23, 2002Assignee: Ineos Acrylics U.K. LimitedInventors: Paul David Newman, Richard Anthony Campbell, Robert Paul Tooze, Graham Ronald Eastham, Jamie Michael Thorpe, Peter Gerald Edwards
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Patent number: 6368369Abstract: Disclosed are liquid hydrocarbon fuel concentrates, including low sulfur liquid hydrocarbon fuel concentrates containing at least 5,000 ppm boric acid suspended in the liquid hydrocarbon fuel. The liquid hydrocarbon fuels include gasoline, diesel fuel, aviation fuel, jet fuel, boat or motorcycle fuel. Also disclosed are liquid hydrocarbon fuels compositions formed by diluting the concentrate to form compositions containing only from about 10 ppm to about 50,000 ppm boric acid. Also disclosed are liquid hydrocarbon fuel compositions formed of a reaction product of boric acid having a particle size of about 65 microns or less, associated with a liquid hydrocarbon fuel having a monomer or prepolymer chemically grafted thereon.Type: GrantFiled: January 20, 2000Date of Patent: April 9, 2002Assignee: Advanced Lubrication Technology, Inc.Inventors: Mohan L. Sanduja, Carl Horowitz, Satyabrata Mukherjee, Paul Thottahil, William Olliges, Charles T. Foscue
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Patent number: 6359091Abstract: This invention is a polyarylene composition in which resin does not undergo a significant drop in modulus at temperatures above 300° C. during cure. This feature enables one to form porous films by avoiding pore collapse and/or using a wider variety of poragen materials.Type: GrantFiled: November 22, 1999Date of Patent: March 19, 2002Assignee: The Dow Chemical CompanyInventors: James P. Godschalx, Kenneth J. Bruza, Qing Shan J. Niu, Clark H. Cummins, Paul H. Townsend, III
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Patent number: 6353125Abstract: Described are bis(perfluoro-n-alkane-sulfonate) compounds, methods for preparing these compounds and use of these compounds, for example as starting materials for the synthesis of chiral and phosphine ligands for transition metal catalysts.Type: GrantFiled: September 25, 2000Date of Patent: March 5, 2002Assignee: Merck Patent GmbHInventors: Andreas Wächtler, Karl-Heinz Derwenskus, Andreas Meudt
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Patent number: 6346324Abstract: Disclosed is a cis-bridged metal complex of the formula (I) where R5 is an electron-withdrawing radical, and catalyst systems based on these complexes for copolymerizing carbon monoxide and olefinically unsaturated compounds.Type: GrantFiled: September 18, 2000Date of Patent: February 12, 2002Assignee: BASF AktiengesellschaftInventors: Joachim Queisser, Michael Slany, Ansgar Schäfer, Michael Schulz
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Patent number: 6339174Abstract: A catalyst composition comprising a) more than 70% by weight of a polyethylene glycol of the formula H—(OCH2—CH2)n—OH, where n is an integer of 3 to 16 and the number average molecular weight is less than 650 b) rhodium in elemental form or bound form and c) 2 to 25% by weight of water soluble sulfonated triarylphosphine ligand having 1 to 2 phophorus atoms and not more than 25% by weight of water based on the total amount of the catalyst and its use for the hydroformylation of olefins to aldehydes is described.Type: GrantFiled: May 16, 2000Date of Patent: January 15, 2002Assignee: Celanese Chemicals Europe GmbHInventor: Sandra Bogdanovic
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Patent number: 6335471Abstract: A method of preparing a compound (I) of general formula (R3—C)2P—L1—X—L2—P—(C—R3)2, in which R is independently a pendant, optionally substituted, organic group through which the group is linked to tertiary carbon atoms C; L1 and L2 are independently, a linking group selected from an optionally substituted lower alkylene chain connecting the respective phosphorous atom to the group X, and X is a bridging group comprising an optionally substituted aryl moiety to which the phosphorous atoms are linked on available adjacent carbon atoms; comprising: (i) reacting together a compound (II) of formula A—L1—X—L2—A, in which A is a halogen atom, with a metal M in a suitable solvent or form an intermediate compound (III) of formula: A—M—L1—X—L2—M—A; (ii) reacting said intermediate compound (III) with a compound (IV) of formula: (R3—C)2P—A1, wherein A1 is a halogen atom which may be the same as or differentType: GrantFiled: April 13, 2000Date of Patent: January 1, 2002Assignee: Ineos Acrylics UK LimitedInventors: Graham Ronald Eastham, Jamie Michael Thorpe, Robert Paul Tooze
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Patent number: 6333291Abstract: This invention provides a novel diphosphine compound which is useful as a ligand of catalysts for asymmetric synthesis reactions, particularly asymmetric hydrogenation reaction. Particularly, it provides a diphosphine compound represented by a general formula (1): wherein R1 and R2 each independently represents a cycloalkyl group, an unsubstituted or substituted phenyl group or a five-membered aromatic heterocycle residue.Type: GrantFiled: October 30, 2000Date of Patent: December 25, 2001Assignee: Takasago International CorporationInventors: Tohru Yokozawa, Noboru Sayo, Takao Saito, Takero Ishizaki
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Patent number: 6333435Abstract: A process of synthesizing a compound of the formula 1: is disclosed, which comprises reacting a compound of the formula 2: with diphenylphosphine in the presence of an amine base and a nickel catalyst to produce a compound of formula 1.Type: GrantFiled: May 18, 1995Date of Patent: December 25, 2001Assignee: Merck & Co., Inc.Inventors: Dongwei Cai, David L. Hughes, Sylvain Levac, Thomas R. Verhoeven
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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: 6281390Abstract: Compounds of formula III, wherein R6 und R7 signify identical or different secondary phosphino; R8 is —CH2—OH, —CH2—NH2—, —CH2O——B—FU, —CH2—NH2—B—FU, or —O—B—FU; R9 has the same significance as R8 or is C1-C4-alkyl or C1-C4-alkoxy; or R8 and R9 together signify HOCH(CH2—O—)2, H2NCH—(CH2—O—)2, FU—B—OCH(CH2—O—)2 or FU—B—HNCH(CH2—O—)2; B is a bridging group; and FU is a functional group. The compounds may be bonded to inorganic or organic carriers. Their d-8 metal complexes are valuable catalysts for the enantioselective hydrogenation of prochiral organic compounds with carbon multiple bonds or carbon/hetero atom multiple bonds.Type: GrantFiled: November 17, 1999Date of Patent: August 28, 2001Assignee: Solvias AGInventors: Benoît Pugin, Ivo Steiner, Rhony Niklaus Aufdenblatten, Antonio Togni
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Patent number: 6278024Abstract: This invention is to develop novel transition metal catalysts for the practical synthesis of important chiral molecules.Type: GrantFiled: March 13, 2000Date of Patent: August 21, 2001Assignee: The Penn State Research FoundationInventor: Xumu Zhang
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Patent number: 6252001Abstract: Compounds of ethynyl aromatic compounds form polymers which have high thermal stability. The monomers are useful for coating a wide variety of substances such as dielectric coatings where high thermal resistance is desirable including electronic components such as computer chips.Type: GrantFiled: January 13, 2000Date of Patent: June 26, 2001Assignee: The Dow Chemical CompanyInventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
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Patent number: 6248848Abstract: A 2′-diarylphosphino-1,1′-biphenylen-2-yloxy(6,6′-divinyl-1,1′-binaphthalene-2,2′-diyloxy)phosphine derivative is disclosed, which is represented by general formula (I): wherein Ar is an optionally substituted phenyl or naphthyl; R1 and R2 each independently is a hydrogen atom, a lower alkyl, a lower alkoxy, etc.; and R3 is a lower alkyl, a lower alkoxy, etc.; provided that R2 and R3 may be bonded to each other to form a hydrocarbon ring, which may have one or more substituents selected from lower alkyl groups, halogen atoms, vinyl, etc. Also disclosed are a polymer having structural units derived from the phosphine derivative and a transition metal complex obtained by causing a transition metal compound to act on the phosphine derivative.Type: GrantFiled: June 27, 2000Date of Patent: June 19, 2001Assignee: Takasago International CorporationInventors: Kyoko Tamao, Yohei Itoi
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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: 6225487Abstract: A new ligand having a backbone comprised of PCCC, where the last carbon atom is sp3 hybridized can be combined with a metal or metal precursor compound or formed into a metal-ligand complex to catalyze a number of different chemical transformations, including C—N bond formation.Type: GrantFiled: April 17, 1998Date of Patent: May 1, 2001Assignee: Symyx Technologies, Inc.Inventor: Anil Guram
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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: 6215026Abstract: Substituted sodium salts of phosphides are prepared by reacting a triarylphosphine with sodium in an aliphatic amine or diamine as a solvent or co-solvent. The resultant phosphides may be further treated with appropriate halides to produce unsymmetrical phosphines.Type: GrantFiled: January 11, 2000Date of Patent: April 10, 2001Assignee: Great Lakes (UK) LimitedInventors: Robert Gandy, Peter John Cremins, Allan William Timms
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Patent number: 6204414Abstract: The invention provides an intermediate compound (5-[2-hydroxy-5-(1-hydroxy-1-methylethyl)-2-methyl-cyclopentyl]-3-methyl-penta-2,4-dienyl)triphenylphosphonium salt for use in a multi-stage process for making an oxidative metabolite of the carotenoid, lycopene 2,6-cyclolycopene-1,5-diol. The intermediate compound has the formula: wherein Ph is phenyl and X1− is chloride, bromide, or hydrogen sulphate.Type: GrantFiled: October 12, 1999Date of Patent: March 20, 2001Assignee: Roche Vitamins Inc.Inventors: Hanspeter Pfander, Bruno Traber
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Patent number: 6194593Abstract: An optically active 1,2-bis(dialkylphosphino) benzene derivative represented by the general formula (1) which is suitable as a ligand for a transition metal catalyst in asymmetrical hydrogenation is provided. Also provided is a process for producing such a benzene derivative, and a rhodium metal complex having such a benzene derivative as a ligand which is useful as an asymmetric catalyst for use in asymmetrical hydrogenation. (where R1 denotes a straight or branched alkyl group having 2-6 carbon atoms, and each of the asterisks denotes an asymmetric phosphorus atom).Type: GrantFiled: January 28, 2000Date of Patent: February 27, 2001Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Tsuneo Imamoto, Tomoya Miura, Hironari Yamada