Phosphorus Containing Patents (Class 568/8)
  • Patent number: 5902904
    Abstract: 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: Grant
    Filed: August 21, 1998
    Date of Patent: May 11, 1999
    Assignee: Monsanto Company
    Inventors: Scott A. Laneman, David J. Ager, Amihia Eisenstadt
  • Patent number: 5892120
    Abstract: 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: Grant
    Filed: November 25, 1997
    Date of Patent: April 6, 1999
    Assignees: Nippon Chemical Industrial Co., Ltd., Shin-Etsu Chemical Co., Ltd.
    Inventors: Masashi Sugiya, Tsutomu Watanabe, Natsuhiro Sano
  • Patent number: 5872279
    Abstract: 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: Grant
    Filed: March 19, 1998
    Date of Patent: February 16, 1999
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Masashi Sugiya, Tsutomu Watanabe, Kaoru Takeuchi
  • Patent number: 5866720
    Abstract: (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: Grant
    Filed: April 29, 1998
    Date of Patent: February 2, 1999
    Assignee: Albemarle Corporation
    Inventors: William J. Layman, Jr., George W. Welsh
  • Patent number: 5855867
    Abstract: 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: Grant
    Filed: March 14, 1997
    Date of Patent: January 5, 1999
    Assignee: The Curators of the University of Missouri
    Inventors: Kattesh V. Katti, Srinivasa Rao Karra, Douglas E. Berning, C. Jeffrey Smith, Wynn A. Volkert, Alan R. Ketring
  • Patent number: 5854227
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: December 29, 1998
    Inventors: John F. Hartmann, Dan Farcasiu
  • Patent number: 5849954
    Abstract: 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: Grant
    Filed: January 18, 1996
    Date of Patent: December 15, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Dumitru Ionesou
  • Patent number: 5831102
    Abstract: 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: Grant
    Filed: February 8, 1996
    Date of Patent: November 3, 1998
  • Patent number: 5792884
    Abstract: 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: Grant
    Filed: December 21, 1993
    Date of Patent: August 11, 1998
    Assignee: BASF Aktiengesellschaft
    Inventor: Thomas Wettling
  • Patent number: 5789608
    Abstract: 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: Grant
    Filed: December 11, 1996
    Date of Patent: August 4, 1998
    Assignee: Drug Innovation and Design, Inc.
    Inventor: Arnold Glazier
  • Patent number: 5767276
    Abstract: 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: Grant
    Filed: October 11, 1996
    Date of Patent: June 16, 1998
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 5756847
    Abstract: 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: Grant
    Filed: June 13, 1997
    Date of Patent: May 26, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Arthur Hohn, Justin Wolf
  • Patent number: 5744461
    Abstract: 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: Grant
    Filed: May 26, 1995
    Date of Patent: April 28, 1998
    Assignee: NeXstar Pharmaceuticals, Inc.
    Inventors: Karl Y. Hostetler, Raj Kumar
  • Patent number: 5728886
    Abstract: 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: Grant
    Filed: August 3, 1995
    Date of Patent: March 17, 1998
    Assignee: Hoechst AG
    Inventors: Christoph Naumann, Dieter Regnat
  • Patent number: 5723678
    Abstract: 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: Grant
    Filed: April 12, 1996
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Peter Hofmann
  • Patent number: 5723642
    Abstract: 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: Grant
    Filed: May 6, 1996
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Sturmer, Lothar Laupichler, Paul Knochel, Falk Langer
  • Patent number: 5717083
    Abstract: 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: Grant
    Filed: August 19, 1996
    Date of Patent: February 10, 1998
    Assignee: ISIS Pharmaceuticals, Inc.
    Inventors: Phillip Dan Cook, Oscar Acevedo, Normand Hebert
  • Patent number: 5698743
    Abstract: 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: Grant
    Filed: November 26, 1996
    Date of Patent: December 16, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Arthur Hohn, Justin Wolf
  • Patent number: 5696277
    Abstract: Lipid prodrugs of phosphonoacids and their analogs that have increased antiviral activity over the parent drugs in inhibiting cytomegalovirus and other susceptible viruses.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: December 9, 1997
    Assignee: Karl Y. Hostetler
    Inventors: Karl Y. Hostetler, Ganesh D. Kini
  • Patent number: 5693868
    Abstract: 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: Grant
    Filed: October 30, 1996
    Date of Patent: December 2, 1997
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Xiaoyong Zhang, Tatsuya Ohmoto, Akifumi Yoshida, Tohru Yokozawa
  • Patent number: 5693799
    Abstract: 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: Grant
    Filed: July 8, 1996
    Date of Patent: December 2, 1997
    Assignee: Novartis Corp.
    Inventor: Eric Keith Baylis
  • Patent number: 5689005
    Abstract: 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: Grant
    Filed: November 28, 1995
    Date of Patent: November 18, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Hagemeyer, Christopher William Rieker, Thomas Lautensack, Dieter Hermeling
  • Patent number: 5679863
    Abstract: 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: Grant
    Filed: October 16, 1995
    Date of Patent: October 21, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Fischer, Eckhard Hickmann, Rudolf Kropp, Jochen Schroeder, Beate Trentmann
  • Patent number: 5670440
    Abstract: 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: Grant
    Filed: October 22, 1996
    Date of Patent: September 23, 1997
    Assignee: Shell Oil Company
    Inventors: Simona Bronco, Giambattista Consiglio, Silvia Di Benedetto, Eit Drent, Hero Jan Heeres, Johannes Adrianus Maria Van Broekhoven, Marinus Johannes Reynhout
  • Patent number: 5637684
    Abstract: 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: Grant
    Filed: February 23, 1994
    Date of Patent: June 10, 1997
    Assignee: ISIS Pharmaceuticals, Inc.
    Inventors: Phillip D. Cook, Oscar Acevedo, Normand Hebert
  • Patent number: 5635158
    Abstract: 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: Grant
    Filed: June 23, 1995
    Date of Patent: June 3, 1997
    Assignee: Sorin Radiofarmaci SRL
    Inventors: Ulderico Mazzi, Fabio Lunghi
  • Patent number: 5627165
    Abstract: 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: Grant
    Filed: September 23, 1994
    Date of Patent: May 6, 1997
    Assignee: Drug Innovation & Design, Inc.
    Inventor: Arnold Glazier
  • Patent number: 5601800
    Abstract: 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: Grant
    Filed: July 29, 1994
    Date of Patent: February 11, 1997
    Assignee: Curators of the University of Missouri
    Inventors: Kattesh V. Katti, Wynn A. Volkert, Alan R. Ketring, Prahlad R. Singh
  • Patent number: 5580991
    Abstract: 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: Grant
    Filed: April 4, 1995
    Date of Patent: December 3, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hitoshi Sugiyama, Kazunari Takahashi, Haruhiko Kusaka
  • Patent number: 5554795
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: September 10, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
  • Patent number: 5536880
    Abstract: 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: Grant
    Filed: December 20, 1994
    Date of Patent: July 16, 1996
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Masashi Sugiya, Seiji Shimura
  • Patent number: 5530162
    Abstract: 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: Grant
    Filed: July 21, 1993
    Date of Patent: June 25, 1996
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Ian P. Rothwell, S. Joyce Yu
  • Patent number: 5523437
    Abstract: 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: Grant
    Filed: July 26, 1994
    Date of Patent: June 4, 1996
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamio Hayashi, Yasuhiro Uozumi, Kazunori Iwakura, Isao Kurimoto, Masayoshi Minai
  • Patent number: 5508273
    Abstract: Compounds represented by the formula I: ##STR1## are disclosed as agents for use in treating bone wasting diseases.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: April 16, 1996
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Scott Beers, Elizabeth A. Malloy, Charles Schwender
  • Patent number: 5498797
    Abstract: 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: Grant
    Filed: November 14, 1994
    Date of Patent: March 12, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dieter Regnat, Hans-Jerg Kleiner
  • Patent number: 5488171
    Abstract: 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: Grant
    Filed: February 28, 1994
    Date of Patent: January 30, 1996
    Assignee: Ciba-Geigy Corporation
    Inventor: Eric K. Baylis
  • Patent number: 5474716
    Abstract: 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: Grant
    Filed: February 22, 1995
    Date of Patent: December 12, 1995
    Assignee: Witco GmbH
    Inventor: Richard Lisowsky
  • Patent number: 5453221
    Abstract: 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: Grant
    Filed: February 22, 1995
    Date of Patent: September 26, 1995
    Assignee: Witco GmbH
    Inventor: Richard Lisowsky
  • Patent number: 5436280
    Abstract: 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: Grant
    Filed: November 17, 1993
    Date of Patent: July 25, 1995
    Assignee: Edison Polymer Innovation Corp.
    Inventors: Robert E. Medsker, II, H. James Harwood
  • Patent number: 5426248
    Abstract: 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: Grant
    Filed: August 3, 1994
    Date of Patent: June 20, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Robert J. Sarama, Michael R. Sevenants, Robert A. Sanders
  • Patent number: 5366727
    Abstract: 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: Grant
    Filed: October 21, 1992
    Date of Patent: November 22, 1994
    Assignee: Nippon Chemical Industrial Co., Ltd.
    Inventors: Akihiko Kanazawa, Takeshi Endo, Tomiki Ikeda
  • Patent number: 5360886
    Abstract: 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: Grant
    Filed: October 27, 1993
    Date of Patent: November 1, 1994
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
  • Patent number: 5357037
    Abstract: This invention relates to new phosphorus-containing duromers of oligophosphites and epoxides or bisacrylates or unsaturated polyesters.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: October 18, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Burkhard Kohler, Wolfgang Ebert
  • Patent number: 5354894
    Abstract: 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: Grant
    Filed: October 14, 1993
    Date of Patent: October 11, 1994
    Assignee: Eastman Chemical Company
    Inventor: Thomas J. Devon
  • Patent number: 5354918
    Abstract: 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: Grant
    Filed: July 15, 1993
    Date of Patent: October 11, 1994
    Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Chemical Industrial Co., Ltd.
    Inventors: Hiromi Ohsaki, Kazuyuki Asakura, Masashi Sugiya, Yutaka Demura, Tomio Yanai
  • Patent number: 5310853
    Abstract: 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: Grant
    Filed: January 21, 1993
    Date of Patent: May 10, 1994
    Assignee: The Dow Chemical Company
    Inventors: Ha Q. Pham, Michael B. Cavitt, Pamela A. Hardcastle
  • Patent number: 5284977
    Abstract: 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: Grant
    Filed: April 28, 1992
    Date of Patent: February 8, 1994
    Assignee: Nippon Mining Company Limited
    Inventors: Toru Imori, Takayuki Ninomiya, Kazuhiro Kondoh, Kouichi Nakamura, Kouhei Ushikubo
  • Patent number: 5268492
    Abstract: 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: Grant
    Filed: August 27, 1992
    Date of Patent: December 7, 1993
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Keiji Yamamoto, Masahiro Miyazawa, Satoru Momose
  • Patent number: 5260485
    Abstract: 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: Grant
    Filed: March 9, 1992
    Date of Patent: November 9, 1993
    Assignee: American Cyanamid Company
    Inventors: C. Joseph Calbick, Mark A. Kuck, Donald H. Valentine
  • Patent number: 5250736
    Abstract: 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: Grant
    Filed: August 11, 1992
    Date of Patent: October 5, 1993
    Assignee: Cyanamid Canada Inc.
    Inventors: Colleen E. Micklethwaite, Allan J. Robertson