Phosphorus Containing Patents (Class 568/8)
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Patent number: 5902904Abstract: 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: August 21, 1998Date of Patent: May 11, 1999Assignee: Monsanto CompanyInventors: Scott A. Laneman, David J. Ager, Amihia Eisenstadt
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Patent number: 5892120Abstract: A highly pure monoalkylphosphine which is useful as a starting material for producing a compound semiconductor, and a method for producing same in high yield are provided. A highly pure monoalkylphosphine represented by the general formula RPH.sub.2 (wherein R is an alkyl group having 1 to 8 carbon atoms) has a purity of not less than five nines, and is substantially free of sulfur and silica. In the method of producing said highly pure monoalkylphosphine, anhydrous hydrofluoric acid is used as a catalyst for a reaction between phosphine and an alkene, and the reaction is carried out in the presence of an organic solvent having a boiling point higher than that of the resulting monoalkylphosphine; the resulting reaction mixture is contacted with an alkali solution so that the remaining catalyst is removed into an aqueous phase in the form of a fluoride salt; next, the obtained reaction mixture is contacted with an alkali hydride and the impurities are removed, then distillation is carried out.Type: GrantFiled: November 25, 1997Date of Patent: April 6, 1999Assignees: Nippon Chemical Industrial Co., Ltd., Shin-Etsu Chemical Co., Ltd.Inventors: Masashi Sugiya, Tsutomu Watanabe, Natsuhiro Sano
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Patent number: 5872279Abstract: A bis(1,1,3,3-tetramethylbutyl)phosphinic acid compound represented by the formula (1) and an extracting agent using the same for separating Co from an aged electroless Ni plating solution. A di(1,1,3,3-tetramethylbutyl)phosphine is produced by carrying out a reaction between phosphine and trimethylpentene in the presence of an organic solvent and a catalyst, then said phosphine is reacted with an oxidizing agent or sulfur to obtain the compound (1): ##STR1## (wherein X.sup.1 and X.sup.2 are O or S).Type: GrantFiled: March 19, 1998Date of Patent: February 16, 1999Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Masashi Sugiya, Tsutomu Watanabe, Kaoru Takeuchi
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Patent number: 5866720Abstract: (1) Alkali metal diarylphosphides are formed by mixing triarylphosphine with, and preferably introducing triarylphosphine into, a two-phase mixture one or more alkali metals, preferably a mixture or alloy of sodium and potassium, in an anhydrous organic liquid diluent in the presence of molecular hydrogen. (2) To form a cycloalkyldiarylphosphine, at least a portion of the reaction mixture formed as in (1) (or alkali metal diarylphosphide recovered therefrom) and cycloalkyl mesylate or tosylate are mixed together and maintained under suitable reaction conditions. Reaction (2) is driven by the presence of residual sodium from reaction (1). Conduct of reaction (2) under a hydrogen atmosphere suppresses undesirable side reactions.Type: GrantFiled: April 29, 1998Date of Patent: February 2, 1999Assignee: Albemarle CorporationInventors: William J. Layman, Jr., George W. Welsh
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Patent number: 5855867Abstract: A compound and method of making a compound for use as a diagnostic or therapeutic pharmaceutical comprises at least one functionalized hydroxyalkyl phosphine donor group and one or more sulfur or nitrogen donor and a metal combined with the ligand.Type: GrantFiled: March 14, 1997Date of Patent: January 5, 1999Assignee: The Curators of the University of MissouriInventors: Kattesh V. Katti, Srinivasa Rao Karra, Douglas E. Berning, C. Jeffrey Smith, Wynn A. Volkert, Alan R. Ketring
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Patent number: 5854227Abstract: Novel chemotherapeutic agents having utility in treating infectious diseases such as periodontal disease, certain urinary tract infections, infectious urinary tract stones, and bone cancer, are obtained by combining chemically a diphosphonate compound with a therapeutic agent effective against the foregoing diseases.Type: GrantFiled: June 7, 1995Date of Patent: December 29, 1998Inventors: John F. Hartmann, Dan Farcasiu
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Patent number: 5849954Abstract: The present invention relates to a process for forming an N-.alpha.-amino protected amino acid fluoride in situ by reacting an N-.alpha.-amino protected amino acid with an ionic fluoride salt in the presence of a peptide coupling agent. It is also directed to the use of the amino acid fluoride thus formed in peptide synthesis.Type: GrantFiled: January 18, 1996Date of Patent: December 15, 1998Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, Dumitru Ionesou
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Patent number: 5831102Abstract: Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; andR.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sup.1 and R.sub.Type: GrantFiled: February 8, 1996Date of Patent: November 3, 1998
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Patent number: 5792884Abstract: Tertiary phosphines (I) are prepared by reducing the corresponding phosphine oxides (IIa) or phosphine dihalides (IIb) using silicon or a silicon alloy as reducing agent.Type: GrantFiled: December 21, 1993Date of Patent: August 11, 1998Assignee: BASF AktiengesellschaftInventor: Thomas Wettling
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Patent number: 5789608Abstract: The composition and methods of synthesis of phosphorus prodrugs are described. These methods can be used to convert negatively charged phosphorous bearing drugs into neutrally charged; lipid soluble prodrugs which are able to passively diffuse into cells and into tissues in vivo. Prodrugs for a variety of antiviral and anti-leukemic agents are described.Type: GrantFiled: December 11, 1996Date of Patent: August 4, 1998Assignee: Drug Innovation and Design, Inc.Inventor: Arnold Glazier
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Patent number: 5767276Abstract: A chiral ligand having the following structure: ##STR1## wherein AR is any aromatic and/or ring structure, and R is selected from the group consisting of aryl, oxygenated aryl, alkyl, oxygenated alkyl, AR, oxygenated AR and combinations thereof.Type: GrantFiled: October 11, 1996Date of Patent: June 16, 1998Assignee: The Penn State Research FoundationInventor: Xumu Zhang
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Patent number: 5756847Abstract: Preparation of methylene-bridged compounds of the formula I ##STR1## where R.sup.1 to R.sup.4 are identical or different and are each saturated C.sub.1 -C.sub.30 -hydrocarbyl, unsubstituted phenyl, phenyl substituted by substituents inert under the reaction conditions, or hydrogen, E.sup.1 and E.sup.2 are identical or different and are each phosphorus, arsenic or antimony, and X is a chemical bond or oxygen by reacting a tin compound of the general formula IIR.sub.3.sup.5 Sn--CH.sub.2 M II,where R.sup.5 is C.sub.1 -C.sub.20 -hydrocarbyl and M is an alkali metal, with a compound of the general formula III ##STR2## where Y is halogen, metallating the thus-obtained tin compound of the general formula IV ##STR3## with an alkali organometallic, and reacting the product with a compound of the general formula V ##STR4## to give a methylene-bridged compound of the formula I. And novel 45 bis(diorganophosphino)methanes.Type: GrantFiled: June 13, 1997Date of Patent: May 26, 1998Assignee: BASF AktiengesellschaftInventors: Arthur Hohn, Justin Wolf
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Patent number: 5744461Abstract: Lipid-containing prodrugs are provided for treating viral infections due to herpes, influenza, hepatitis B, Epstein-Barr, and varicella zoster viruses, as well as cytomegalovirus and derivatives of antiviral agents. The compounds comprise phosphonoacids having antiviral activity which are linked, either through the phosphate group or carboxyl group of the phosphonoacid, to one of a selected group of lipids. Phosphonoacetic acid and phosphonoformic acid are thus linked to phospholipids, glycerolipids, sphingolipids, glycolipids, or fatty acids. The compounds persist, after intracellular hydrolysis, as the antiviral phosphonoacids. The lipid prodrugs are effective in improving the efficacy of antiviral phosphonoacids by prolonging their antiviral activity following administration.Type: GrantFiled: May 26, 1995Date of Patent: April 28, 1998Assignee: NeXstar Pharmaceuticals, Inc.Inventors: Karl Y. Hostetler, Raj Kumar
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Patent number: 5728886Abstract: Phosphines of the formula (I) and the preparation of these phosphines ##STR1## where Ar--Ar is a biphenyl radical, a 1-phenylnaphthyl radical or a 1,1'-binaphthyl radical, the CH.sub.2 group and the CH.sub.3 radical are each in the ortho position to the Ar--Ar bond, R is F, an alkyl radical or alkoxy radical each having from 1 to 8 carbon atoms, n is an integer from 0 to 4, R.sup.1 and R.sup.2 independently of one another, are an alkyl radical having from 1 to 10 carbon atoms, a cycloaliphatic radical having from 5 to 10 carbon atoms, or a radical Ar.sup.1 -(R.sup.3).sub.m, where Ar.sup.1 is a phenyl or naphthyl radical, R.sup.3 is F, Cl, CF.sub.3, SO.sub.3 H, SO.sub.3 Me (Me=Li, Na or K), a dialkylamino radical having from 2 to 8 carbon atoms, an alkyl radical or alkoxy radical each having from 1 to 8 carbon atoms and m is an integer from 0 to 5, or R.sup.1 and R.sup.2 together with the phosphorus atom form a 4-membered to 8-membered ring to which can be fused.Type: GrantFiled: August 3, 1995Date of Patent: March 17, 1998Assignee: Hoechst AGInventors: Christoph Naumann, Dieter Regnat
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Patent number: 5723678Abstract: Acetylenic compounds of the general formula IR.sup.1 --C.tbd.C--CHR.sup.2 --CH.sub.2 --X Iwhere the substituents have the following meanings:R.sup.1 hydrogen, unsubstituted or substituted alkyl or aryl;R.sup.2 hydrogen or C.sub.1 -C.sub.4 -alkyl;X CN; COOR.sup.3 where R.sup.3 is C.sub.1 -C.sub.6 -alkyl or benzyl; C(O)R.sup.4 where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl,are prepared by reacting an alkyne of the formula IIR.sup.1 --C.tbd.C--H IIwith an .alpha.,.beta.-unsaturated compound of the formula IIIR.sup.2 HC.dbd.CH--X IIIin the presence of a homogeneous rhodium-phosphine catalyst, in a process wherein a catalyst with a bidentate or tridentate phosphine compound is used.Type: GrantFiled: April 12, 1996Date of Patent: March 3, 1998Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Peter Hofmann
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Patent number: 5723642Abstract: Optically active phosphines of the general formula I or II ##STR1## where the variables have the following meanings: X is an optically active terpene radical,R is an unsubstituted or substituted phenyl radical,Y is a bridge member having 1-10 C atoms in the formula In is 1,2 or 3 andm is 0,1 or 2 with the proviso that n+m=3 in the formula IIn is 1 or 2 andm is 0 or 1 with the proviso that n+m=2, their preparation and use are described.Type: GrantFiled: May 6, 1996Date of Patent: March 3, 1998Assignee: BASF AktiengesellschaftInventors: Rainer Sturmer, Lothar Laupichler, Paul Knochel, Falk Langer
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Patent number: 5717083Abstract: Compounds are provided having structure (I), wherein the L groups are backbone segments, the Y and T groups are functional groups for interacting with target molecules of interest, the X groups are oxygen or sulfur and the E groups are H, conjugate groups or intermediate groups used during the synthesis of the compounds and wherein the compounds are prepared using H phosphonate type chemistry wherein the functional groups are added during an oxidation step or during a coupling step.Type: GrantFiled: August 19, 1996Date of Patent: February 10, 1998Assignee: ISIS Pharmaceuticals, Inc.Inventors: Phillip Dan Cook, Oscar Acevedo, Normand Hebert
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Patent number: 5698743Abstract: Preparation of methylene-bridged compounds of the formula I ##STR1## where R.sup.1 to R.sup.4 are identical or different and are each saturated C.sub.1 -C.sub.30 -hydrocarbyl, unsubstituted phenyl, phenyl substituted by substituents inert under the reaction conditions, or hydrogen, E.sup.1 and E.sup.2 are identical or different and are each phosphorus, arsenic or antimony, and X is a chemical bond or oxygen by reacting a tin compound of the general formula IIR.sub.3.sup.5 Sn--CH.sub.2 M, IIwhere R.sup.5 is C.sub.1 --C.sub.20 -hydrocarbyl and M is an alkali metal, with a compound of the general formula III ##STR2## where Y is halogen, metallating the thus-obtained tin compound of the general formula IV ##STR3## with an alkali organometallic, and reacting the product with a compound of the general formula V ##STR4## to give a methylene-bridged compound of the formula I. And novel bis(diorganophosphino)methanes.Type: GrantFiled: November 26, 1996Date of Patent: December 16, 1997Assignee: BASF AktiengesellschaftInventors: Arthur Hohn, Justin Wolf
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Patent number: 5696277Abstract: Lipid prodrugs of phosphonoacids and their analogs that have increased antiviral activity over the parent drugs in inhibiting cytomegalovirus and other susceptible viruses.Type: GrantFiled: November 15, 1994Date of Patent: December 9, 1997Assignee: Karl Y. HostetlerInventors: Karl Y. Hostetler, Ganesh D. Kini
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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: 5693799Abstract: A compound of formula ##STR1## where R.sup.1 and R.sup.2 are independently a C.sub.1 -C.sub.10 aliphatic radical, or R.sup.1 is a C.sub.1 -C.sub.10 aliphatic radical and R.sup.2 is a C.sub.6 -C.sub.10 aromatic radical, and R.sup.3 is a C.sub.1 -C.sub.8 aliphatic radical, a C.sub.3 -C.sub.8 cycloaliphatic radical, a C.sub.6 -C.sub.15 aromatic radical or a C.sub.7 -C.sub.13 araliphatic radical, provided that R.sup.3 is not methyl when R.sup.1 and R.sup.2 are each methyl, that R.sup.3 is not ethyl when R.sup.1 and R.sup.2 are each methyl and that R.sup.2 is not p-aminophenyl when R.sup.1 is methyl and R.sup.3 is ethyl with an organic compound having at least one group reactive with a P--H bond.Type: GrantFiled: July 8, 1996Date of Patent: December 2, 1997Assignee: Novartis Corp.Inventor: Eric Keith Baylis
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Patent number: 5689005Abstract: A process for the deoxygenation of organic oxo compounds, in particular phosphine oxides to phosphines and nitrobenzene to aniline, with reduced redox catalysts in a non-steady-state reaction with decoupled reductive regeneration of the redox catalyst entails the redox catalyst being reduced to a lower oxidation state and being reused for the deoxygenation.Type: GrantFiled: November 28, 1995Date of Patent: November 18, 1997Assignee: BASF AktiengesellschaftInventors: Alfred Hagemeyer, Christopher William Rieker, Thomas Lautensack, Dieter Hermeling
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Patent number: 5679863Abstract: The preparation of .alpha.-carbonylphosphine oxides by oxidizing an .alpha.-hydroxyalkyl phosphine oxide with an organic hydroperoxide or of an organic peroxy acid in the presence of a compound of a Group IV to Group VIII metal in the periodic table, and novel .alpha.-hydroxybenzyl phosphine oxides. .alpha.-Carbonylphosphine oxides are used as photoinitiators for polymerizable compositions.Type: GrantFiled: October 16, 1995Date of Patent: October 21, 1997Assignee: BASF AktiengesellschaftInventors: Martin Fischer, Eckhard Hickmann, Rudolf Kropp, Jochen Schroeder, Beate Trentmann
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Patent number: 5670440Abstract: A catalyst composition comprisinga) a palladium compound,b) an anion, andc) an asymmetric phosphorus bidentate ligand of the general formula R.sup.5 R.sup.6 P-Q-CHR.sup.9 -PR+7R.sup.8, wherein Q is a 1,2-ferrocenyl bridging group, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are identical or different optionally polar substituted hydrocarbyl groups and R.sup.9 is hydrogen or an optionally polar substituted hydrocarbyl group;a process for the preparation of linear alternating copolymers of carbon monoxide with an aliphatic -olefin having at least 3 and at most 10 carbon atoms, which process comprises contacting a mixture of the monomers with a said catalyst composition; and a linear alternating copolymer of carbon monoxide with an aliphatic -olefin having at least 3 and at most 10 carbon atoms which copolymer has an isotacticity of 95% or more.Type: GrantFiled: October 22, 1996Date of Patent: September 23, 1997Assignee: Shell Oil CompanyInventors: Simona Bronco, Giambattista Consiglio, Silvia Di Benedetto, Eit Drent, Hero Jan Heeres, Johannes Adrianus Maria Van Broekhoven, Marinus Johannes Reynhout
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Patent number: 5637684Abstract: Compounds are provided having the structure: ##STR1## wherein the L groups are spanner or linker units, the Y and T group are functional groups for interacting with target molecules of interest, the X groups are oxygen or sulfur and the E groups are H, conjugate groups or intermediate groups used during the synthesis of the compounds are prepared using H phosphonate type chemistry wherein the functional groups are added during an oxidization step.Type: GrantFiled: February 23, 1994Date of Patent: June 10, 1997Assignee: ISIS Pharmaceuticals, Inc.Inventors: Phillip D. Cook, Oscar Acevedo, Normand Hebert
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Patent number: 5635158Abstract: The peptides described are modified with the phosphine group and are useful for marking with .sup.99m Tc and .sup.186-188 Re or paramagnetic agents for use in diagnosis and radiotherapy; in particular chelating compounds having the co-ordinating sets PN.sub.2 X, where X is --S, --O, COO--, PN.sub.3, P.sub.2 N.sub.3 and P.sub.2 N.sub.2 are described.Type: GrantFiled: June 23, 1995Date of Patent: June 3, 1997Assignee: Sorin Radiofarmaci SRLInventors: Ulderico Mazzi, Fabio Lunghi
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Patent number: 5627165Abstract: The composition and methods of synthesis of phosphorus prodrugs are described. These methods can be used to convert negatively charged phosphorous bearing drugs into neutrally charged; lipid soluble prodrugs which are able to passively diffuse into cells and into tissues in vivo. Prodrugs for a variety of antiviral and anti-leukemic agents are described.Type: GrantFiled: September 23, 1994Date of Patent: May 6, 1997Assignee: Drug Innovation & Design, Inc.Inventor: Arnold Glazier
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Patent number: 5601800Abstract: A class of diagnostic and therapeutic compounds derived from phosphinimines that include ligands containing either a single phosphinimine functionality or both a phosphinimine group and a phosphine or arsine group, or an aminato group, or a second phosphinimine moiety. These phosphinimine ligands are complexed to early transition metal radionuclides (e.g. .sup.99m Tc or .sup.186 Re/.sup.188 Re) or late transition metals (e.g., .sup.105 Rh or .sup.109 Pd). The complexes with these metals .sup.186 Re/.sup.188 Re, .sup.99m Tc and .sup.109 Pd exhibit a high in vitro and high in vivo stability. The complexes are formed in high yields and can be neutral or charged. These ligands can also be used to form stable compounds with paramagnetic transition metals (e.g. Fe and Mn) for potential use as MRI contrast agents. Applications for the use of ligands and making the ligands are also disclosed.Type: GrantFiled: July 29, 1994Date of Patent: February 11, 1997Assignee: Curators of the University of MissouriInventors: Kattesh V. Katti, Wynn A. Volkert, Alan R. Ketring, Prahlad R. Singh
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Patent number: 5580991Abstract: The disclosure describes a method for separating a ruthenium complex, which comprises removing an objective hydrogenation reaction product from a hydrogenation reaction solution of an organic carbonyl compound in the presence of a ruthenium complex having a tertiary organic phosphorus compound as ligand to obtain a catalyst solution, contacting said catalyst solution with a polar solvent, and carrying out a phase-separation into a liquid phase substantially composed of the polar solvent and an another liquid phase substantially containing the ruthenium complex.Type: GrantFiled: April 4, 1995Date of Patent: December 3, 1996Assignee: Mitsubishi Chemical CorporationInventors: Hitoshi Sugiyama, Kazunari Takahashi, Haruhiko Kusaka
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Patent number: 5554795Abstract: In accordance with the present invention there is provided a cyclopentadienyl-type ligand represented by the formula ZA, wherein Z is a cyclopentadienyl-type group, wherein A is --YPR.sub.2, --YNR.sub.2, or --NR.sub.2, wherein Y is an alkylene group containing 1 to 24 carbon atoms, wherein each R is individually selected from alkyl groups containing 1 to 20 carbon atoms. Another aspect of the invention is to provide a metallocene represented by the formula ZAMX.sub.3, wherein Z and A are as described above, M is a Group IVB or VB transition metal, and X is a halide. Other aspects of the present invention include catalyst systems comprising the metallocenes and an organoaluminoxane, processes for preparing the above defined ligands, metallocenes and catalyst systems, and polymerization processes employing the catalyst systems.Type: GrantFiled: May 19, 1995Date of Patent: September 10, 1996Assignee: Phillips Petroleum CompanyInventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
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Patent number: 5536880Abstract: A monoalkylphosphine represented by the following formula (1): ##STR1## wherein m indicates 1 or 2, and n indicates an integer of 0 to 2. The monoalkylphosphine can effectively be obtained by reaction between phosphine and an alkene in the presence of an organic solvent and an anhydrous alkanesulfonic acid catalyst.Type: GrantFiled: December 20, 1994Date of Patent: July 16, 1996Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Masashi Sugiya, Seiji Shimura
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Patent number: 5530162Abstract: A process for making a cycloalkyl phosphine comprising hydrogenating an aryl phosphine in the presence of an effective amount of an aryloxide of a metal selected from the group consisting of niobium and tantalum is disclosed. Cycloalkyl phosphine products of this process, useful as ligands in a complex of a transition metal which acts as a catalyst in the formation of stereoisomers, are also set forth. Furthermore, niobium or tantalum organometallic compounds, generated in this process, useful in the catalytic hydrogenation of aryl phosphines and arene-containing polymers, is also described.Type: GrantFiled: July 21, 1993Date of Patent: June 25, 1996Assignee: Research Corporation Technologies, Inc.Inventors: Ian P. Rothwell, S. Joyce Yu
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Patent number: 5523437Abstract: A tertiary phosphine compound of the formula (1): ##STR1## wherein R.sup.1 and R.sup.2 represent independently from each other a hydrogen atom or a methyl group, or together form --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is a hydrogen atom or a cycloalkyl group having 5 to 7 carbon atoms or a lower alkyl group which may be substituted with a halogen atom, a lower alkoxy group, a lower alkoxyalkoxy group or a phenyl group; X.sup.1 is a halogen atom when both R.sup.1 and R.sup.2 are hydrogen atoms, or a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group when at least one of R.sup.1 and R.sup.2 is not a hydrogen atoms; and m is an integer of 1 to 5, which is useful as a ligand of a transition metal complex that can catalyze various reactions.Type: GrantFiled: July 26, 1994Date of Patent: June 4, 1996Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Hayashi, Yasuhiro Uozumi, Kazunori Iwakura, Isao Kurimoto, Masayoshi Minai
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Patent number: 5508273Abstract: Compounds represented by the formula I: ##STR1## are disclosed as agents for use in treating bone wasting diseases.Type: GrantFiled: December 30, 1993Date of Patent: April 16, 1996Assignee: Ortho Pharmaceutical CorporationInventors: Scott Beers, Elizabeth A. Malloy, Charles Schwender
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Patent number: 5498797Abstract: The present invention relates to phosphorus compounds of the formula ##STR1## in the (RS), (R) and (S) forms, in which Ar.sup.1 --Ar.sup.1 is a bipheny1 radical, 1-phenylnaphthyl radical or 1,1'-binaphthyl radical, each R', if present, independently of the others, is F, an alkyl or alkoxy radical each having 1 to 8 carbon atoms, m is an integer from 0 to 4, k is an integer from I to 4, Ar.sup.2 is a phenyl radical, each R", if present, is, independently of the others, F, Cl, CF.sub.3, SO.sub.3 H, SO.sub.3, SO.sub.3 Me (Me is Li, Na, K), a dialkylamino radical having 2 to 8 carbon atoms, an alkyl or alkoxy radical each having 1 to 8 carbon atoms and n is an integer from 0 to 5, and to a process for their preparation.Type: GrantFiled: November 14, 1994Date of Patent: March 12, 1996Assignee: Hoechst AktiengesellschaftInventors: Dieter Regnat, Hans-Jerg Kleiner
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Patent number: 5488171Abstract: A compound of formula ##STR1## where R.sup.1 and R.sup.2 are independently a C.sub.1 -C.sub.10 aliphatic radical, or R.sup.1 is a C.sub.1 -C.sub.10 aliphatic radical and R.sup.2 is a C.sub.6 -C.sub.10 aromatic radical, and R.sup.3 is a C.sub.1 -C.sub.8 aliphatic radical, a C.sub.3 -C.sub.8 cycloaliphatic radical, a C.sub.6 -C.sub.15 aromatic radical or a C.sub.7 -C.sub.13 araliphatic radical, provided that R.sup.3 is not methyl when R.sup.1 and R.sup.2 are each methyl, that R.sup.3 is not ethyl when R.sup.1 and R.sup.2 are each methyl and that R.sup.2 is not p-aminophenyl when R.sup.1 is methyl and R.sup.3 is ethyl.Type: GrantFiled: February 28, 1994Date of Patent: January 30, 1996Assignee: Ciba-Geigy CorporationInventor: Eric K. Baylis
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Patent number: 5474716Abstract: Disclosed are processes for the preparation of new bridged cyclopentadienylmagnesium compounds of the general formula Q(CpR.sub.a)(Cp'R'.sub.a ')Mg, and the use thereof for preparing bridged metallocenes.Type: GrantFiled: February 22, 1995Date of Patent: December 12, 1995Assignee: Witco GmbHInventor: Richard Lisowsky
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Patent number: 5453221Abstract: Disclosed are new bridged cyclopentadienylmagnesium compounds of the general formula Q(CpR.sub.a) (Cp'R'.sub.a')Mg, processes for the preparation thereof, and the use thereof for preparing bridged metallocenes.Type: GrantFiled: February 22, 1995Date of Patent: September 26, 1995Assignee: Witco GmbHInventor: Richard Lisowsky
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Patent number: 5436280Abstract: Vinyl monomers are polymerized in the presence of bi(phosphine oxides) and bi(phosphine sulfides) which can function as photoinitiators and chain transfer agents in the polymerization of vinyl monomers. The incorporation of such organo-phosphorous compounds into such polymers either as an integral part thereof, or as an admixture, results in improved thermal stability of the polymers.Type: GrantFiled: November 17, 1993Date of Patent: July 25, 1995Assignee: Edison Polymer Innovation Corp.Inventors: Robert E. Medsker, II, H. James Harwood
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Patent number: 5426248Abstract: A process for purifying vitamin A consisting of heating a vitamin A preparation in an inert atmosphere, at a temperature below 170.degree. C. and a pressure of less than 4 mm of mercury, said heating taking place in a vessel shielded from light is disclosed. The vitamin A obtained from this process is mixed with from 0.5:1 to 2:1 parts of tocopherol to vitamin A. The vitamin A and tocopherol mixture can be encapsulated in acacia gum, starch, pectins or other suitable materials. Other antioxidants can be added.Type: GrantFiled: August 3, 1994Date of Patent: June 20, 1995Assignee: The Procter & Gamble CompanyInventors: Robert J. Sarama, Michael R. Sevenants, Robert A. Sanders
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Patent number: 5366727Abstract: An antibacterial agent comprising as an active ingredient a vinylbenzyl phosphonium salt of the general formula (I), ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each represent a hydrogen atom, a linear or branched alkyl group having 1 to 18 carbon atoms, an aryl group, a hydroxyl group, or an alkoxyl-substituted alkyl, aryl or aralkyl group, and X.sup.- is an anion; and/or a phosphonium salt polymer in which the vinylbenzyl phosphonium salt, a monomer, is polymerized.Type: GrantFiled: October 21, 1992Date of Patent: November 22, 1994Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Akihiko Kanazawa, Takeshi Endo, Tomiki Ikeda
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Patent number: 5360886Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorous atom per molecule.Type: GrantFiled: October 27, 1993Date of Patent: November 1, 1994Assignee: The Dow Chemical CompanyInventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
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Patent number: 5357037Abstract: This invention relates to new phosphorus-containing duromers of oligophosphites and epoxides or bisacrylates or unsaturated polyesters.Type: GrantFiled: April 8, 1994Date of Patent: October 18, 1994Assignee: Bayer AktiengesellschaftInventors: Burkhard Kohler, Wolfgang Ebert
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Patent number: 5354894Abstract: Disclosed is a process for the preparation of alkali metal diarylphosphide compounds wherein at least one of the aryl radicals is substituted with an alkyl group. Also disclosed is the preparation of alkyl(diaryl)phosphine compounds which are obtained by the reaction of the alkali metal diarylphosphide compounds with alkyl halide alkylating agents.Type: GrantFiled: October 14, 1993Date of Patent: October 11, 1994Assignee: Eastman Chemical CompanyInventor: Thomas J. Devon
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Patent number: 5354918Abstract: The method for preparing a monoalkylphosphine of high purity comprises reacting phosphine and an alkene in the presence of an anhydrous alkanesulfonic acid as a catalyst in a solvent having a boiling point higher than that of the monoalkylphosphine produced. The resulting monoalkylphosphine is brought into contact with an alkali solution to remove the catalyst, which is a sulfur atom-containing compound, remaining in the solution. The reaction solution from which the remaining catalyst is removed is then brought into contact with alkali metal hydrides or alkaline earth metal hydrides to eliminate any moisture remaining in the reaction solution. The alkali metal hydride is preferably sodium hydride or lithium aluminum hydride, while the alkaline earth metal hydride is preferably calcium hydride.Type: GrantFiled: July 15, 1993Date of Patent: October 11, 1994Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Chemical Industrial Co., Ltd.Inventors: Hiromi Ohsaki, Kazuyuki Asakura, Masashi Sugiya, Yutaka Demura, Tomio Yanai
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Patent number: 5310853Abstract: The reaction between epoxy compounds and active hydrogen-containing compounds or anhydrides is catalyzed with a phosphine or phosphonium compound containing at least three C.sub.1 to C.sub.4 alkyl phenyl groups attached to the phosphorous atom per molecule.Type: GrantFiled: January 21, 1993Date of Patent: May 10, 1994Assignee: The Dow Chemical CompanyInventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
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Patent number: 5284977Abstract: A high-purity organic phosphine is obtained by washing organic phosphine or an organic solvent solution thereof with water, an alkaline aqueous solution or an acidic aqueous solution, whereby impurities, particularly, silicon compounds, 2-methoxy ethanol, and organic halides, contained in organic phosphine can be removed, so that such high-purity organic phosphine may be used as a raw material for high-performance compound semiconductor thin film with Groups III and V elements of the Periodic Table.Type: GrantFiled: April 28, 1992Date of Patent: February 8, 1994Assignee: Nippon Mining Company LimitedInventors: Toru Imori, Takayuki Ninomiya, Kazuhiro Kondoh, Kouichi Nakamura, Kouhei Ushikubo
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Patent number: 5268492Abstract: An optically active diphosphine having a bicyclo[2.2.1]heptane of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are difined in the specification and a metal complex comprising said optically active diphosphine are disclosed. A process for producing or purifying said optically active diphosphine is disclosed.Type: GrantFiled: August 27, 1992Date of Patent: December 7, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Keiji Yamamoto, Masahiro Miyazawa, Satoru Momose
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Patent number: 5260485Abstract: Alkylphosphines are made by a reaction of gaseous phosphine and the corresponding gaseous olefin in contact with at least one non-oxidizing acid catalyst. Products produced thereby are alkylphosphines which contain substantially no metallic or oxygenating impurities. The process is a continuous process and employs a mineral acid catalyst either in solid form or as a liquid supported on a solid, inert material.Type: GrantFiled: March 9, 1992Date of Patent: November 9, 1993Assignee: American Cyanamid CompanyInventors: C. Joseph Calbick, Mark A. Kuck, Donald H. Valentine
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Patent number: 5250736Abstract: Allylphosphines and vinylphosphines are prepared by reaction of a phosphine with an allylhalide or a vinylhalide, respectively. Preferably the phosphine is a secondary phosphine, so that there is formed an allyldialkylphosphine or a dialkylvinylphosphine. The allyldialkylphosphine can be reacted further with dialkylphosphine under free radical conditions to yield a 1,3-bis-(dialkylphosphino)propane. The dialkylvinylphosphine can be reacted further with dialkylphosphine under free radical conditions to yield a 1,2 bis-(dialkylphosphino)ethane. These compounds are useful as bidentate ligands.Type: GrantFiled: August 11, 1992Date of Patent: October 5, 1993Assignee: Cyanamid Canada Inc.Inventors: Colleen E. Micklethwaite, Allan J. Robertson