Plural Unsaturated Five-membered Carbocyclic Rings Bonded Directly To The Metal (e.g., Ferrorcenes, Bis Indenyl Iron, Etc.) Patents (Class 556/143)
  • Patent number: 6664409
    Abstract: Ferrocenaldehyde or ferrocenyl methyl ketone and allyl bromide are reacted in an ether solvent and in the presence of magnesium metal as a catalyst. The liquid portion of the reaction mixture is introduced into a silica gel column, wherein the weak acidity of the silica gel is able to dehydrate the reaction intermediate 1-ferrocenyl-3-buten-1-ol product. The column is eluted with n-hexane, and after evaporating the solvent from the eluate collected, a purified ferrocenyl-1,3-butadiene product is obtained.
    Type: Grant
    Filed: May 6, 2003
    Date of Patent: December 16, 2003
    Assignee: Chung-Shan Institute of Science & Technology
    Inventor: Shean-Jeng Jong
  • Patent number: 6664407
    Abstract: The invention provides compounds for detecting sacchharides by electrochemistry. The compounds have a structure that includes a first boronic acid group attached by a first linker group to a first tertiary amine. The first tertiary amine is attached to a reporter group that includes an organometalic reporter moiety. A spacer group attaches the first tertiary amine to a second tertiary amine. The second tertiary amine is attached to an R group and a second linker group. The second linker group is attached to a second boronic acid group. In preferred embodiments, the compound selectively detects glucose and has a higher relative stability constant for glucose than for other saccharides.
    Type: Grant
    Filed: January 30, 2002
    Date of Patent: December 16, 2003
    Assignee: Beckman Coulter, Inc.
    Inventors: Tony D. James, Susumu Arimori
  • Publication number: 20030216529
    Abstract: Compounds and metal complexes comprising a polycyclic, fused ring ligand or inertly substituted derivative thereof having up to 60 atoms other than hydrogen, said ligand comprising at least: (1) a cyclopentadienyl ring, (2) a 6, 7, or 8 membered ring other than a 6-carbon aromatic ring, and (3) an aromatic ring, with the proviso that said 6, 7, or 8 membered ring (2), is fused to both the cyclopentadienyl ring (1), and the aromatic ring (3), polymerization catalysts, a process to prepare the novel compounds and complexes, and olefin polymerization processes using the same are disclosed.
    Type: Application
    Filed: May 13, 2003
    Publication date: November 20, 2003
    Inventors: Richard E. Campbell, Jerzy Klosin, Ravi B. Shankar, Francis J. Timmers, Robert K. Rosen
  • Publication number: 20030188474
    Abstract: The present invention relates to iron-organo compounds and the use of such compounds in the regeneration of particulate filter traps in combustion systems such as high-compression spontaneous ignition engines.
    Type: Application
    Filed: February 28, 2003
    Publication date: October 9, 2003
    Inventors: Stephen Leonard Cook, Werner Kalischewski, Gabriele Lohmann, Armin Marschewski
  • Patent number: 6593437
    Abstract: A process for preparing 1,2-diimine compounds of the formula I where R1 and R2 are, independently of one another, alkyl, aryl or metallocenyl radicals, and R3, R4 are, independently of one another, H, alkyl or aryl radicals or R3 and R4 are joined so as to form, with inclusion of the two imine carbon atoms, a 5- to 8-membered ring which may be saturated or unsaturated and may be unsubstituted or substituted by any hydrocarbon radicals. The process involves reacting 1,2-dicarbonyl compounds with primary amines, which have been activated with trialkylaluminum compounds prior to the reaction with the 1,2-dicarbonyl compounds. 1,2-Diimine compounds of the formula I in which R1 and R2 are, independently of one another, metallocenyl radicals can be used to prepare metal complexes which can be used as catalysts in a process for the polymerization of unsaturated compounds.
    Type: Grant
    Filed: October 24, 2001
    Date of Patent: July 15, 2003
    Assignee: Basell Polyolefine GmbH
    Inventors: Andrei Gonioukh, Wolfgang Micklitz, Benno Bildstein, Michael Malaun, Andreas Hradsky
  • Patent number: 6576159
    Abstract: The invention is related to ionic compounds, derivatives of malononitrile, in which the anionic load has been displaced. An ionic compound disclosed by the invention includes an anionic portion combined with at least one cationic portion M+m in sufficient number to ensure overall electronic neutrality; the compound is further comprised of M as a hydroxonium, a nitrosonium NO+, an ammonium —NH4+, a metallic cation with the valence m, an organic cation with the valence m, or an organometallic cation with the valence m. The anionic portion corresponds to one of the formulas RD—Y—C(C≡N)2− or Z—C(C≡N)2− in which Z is an electroattractive group, RD is an organic radical, and Y is a carbonyl, a thiocarbonyl, a sulfonyl, a sulfinyl, or a phosphonyl. The compounds can be used notably for ionic conducting materials, electronic conducting materials, colorants, and the catalysis of various chemical reactions.
    Type: Grant
    Filed: August 9, 2000
    Date of Patent: June 10, 2003
    Assignees: Hydro-Quebec, Centre National de la Recherche Scientifique
    Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Yves Choquette
  • Patent number: 6576475
    Abstract: A Bis (cyclopentadienyl) metal complex of a derivative thereof is used as a label in an assay utilizing electrichemiluminescence or fluorescence detection means. The Bis (cyclopentadienyl) metal complex may comprise ferrocene or a derivative thereof which gives rise to a ferricinium ion on electrochemical oxidation.
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: June 10, 2003
    Assignee: University of Liverpool
    Inventors: David Schiffrin, Robert Wilson
  • Patent number: 6517795
    Abstract: A process for producing high-purity hydrotalcites by reacting alcohols or alcohol mixtures with at least one or more divalent metal(s) and at least one or more trivalent metal(s) and hydrolyzing the resultant alcoholate mixture with water. The corresponding metal oxides can be produced by calcination.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: February 11, 2003
    Assignee: Sasol Germany GmbH
    Inventors: Klaus Noweck, Klaus Diblitz, Jan Sohiefler, Andrea Brasch
  • Patent number: 6479646
    Abstract: A metallocene compound having an indenyl ligand substituted by a heteroaromatic group, which is useful as an olefin polymerization catalyst. The metallocene compound has the following structure wherein M is a transition metal atom; each Ra is a monocyclic or polycyclic heteroaromatic group; each R1 is halogen, a hydrocarbon group of 1-20 carbons, a halogenated hydrocarbon group of 1-20 carbons, etc., or adjacent R1's may be joined together to form a ring of 6-8 carbons; p and q are each 1-7; n and l are each 0 or 1-6; and each X is halogen, a hydrocarbon group of 1-20 carbons, a halogenated hydrocarbon group of 1-20 carbons, etc.
    Type: Grant
    Filed: October 12, 2000
    Date of Patent: November 12, 2002
    Assignees: Chisso Corporation, Chisso Petrochemical Corporation
    Inventors: Masato Nakano, Tsutomu Ushioda, Seiki Mitani, Hiroshi Yamazaki
  • Publication number: 20020161253
    Abstract: A process for preparing a cyclopentadienyl or indenyl ruthenium complex by treatment of a cyclopentadienyl or indenyl compound with ruthenium trichloride trihydrate and magnesium powder in an alkanol at 0° C. to −30° C. is described.
    Type: Application
    Filed: August 24, 2001
    Publication date: October 31, 2002
    Applicant: Boulder Scientific Company
    Inventors: Karin A. Voll, Jeffrey M. Sullivan, Dawn A. Arkin, Fredric R. Askham
  • Patent number: 6458983
    Abstract: A process for synthesizing complexes of platinum(II) with iminoethers having the formula: [PtIIX2(L)(L′)], where X is a monoanionic ligand, L is an iminoether ligand and L′ is an amine group or, exclusively for the case of cyclic iminoethers, a second iminoether ligand. The platinum(II) complexes according to the present invention are suitable for the production of medical remedies having a broad antitumoral spectrum. The complexes of platinum(II) with iminoethers according to the invention are furthermore suitable as agents for modifying nucleotide bases into antisense and/or antigene oligonucleotides.
    Type: Grant
    Filed: July 21, 1999
    Date of Patent: October 1, 2002
    Assignee: Universita' Degli Studi di Bari
    Inventors: Francesco Paolo Intini, Giovanni Natile, Angelina Boccarelli, Mauro Coluccia
  • Publication number: 20020115560
    Abstract: 1.
    Type: Application
    Filed: January 18, 2002
    Publication date: August 22, 2002
    Inventors: Pascual Royo Gracia, Jesus Cano Sierra, Miguel Angel Flores De Paco, Begona Pena Garcia
  • Patent number: 6399768
    Abstract: There was found a metallocenyl-phthalocyanine or its metal complex of a divalent metal, oxometal, halogenometal or hydroxymetal, in which at least one of the four phenyl rings of the phthalocyanine contains, bound via a bridge unit E, at least one metallocene radical as substituent, E being composed of a chain of at least two atoms or atom groups selected from the group consisting of —CH2—, —C(═O)—, —CH(C1-C4alkyl)—, —C(C1-C4alkyl)2—, —NH—, —S—, —O— and —CH═CH—, as well as mixtures of the novel compounds which comprise, inter alia, isomers, a process for the production, the use and recording media comprising the novel compounds.
    Type: Grant
    Filed: August 2, 1999
    Date of Patent: June 4, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Heinz Wolleb, Annemarie Wolleb, Beat Schmidhalter, Jean-Luc Budry
  • Patent number: 6376629
    Abstract: A single-site olefin polymerization catalyst and method of making it are disclosed. The catalyst comprises an activator and an organometallic complex. The complex comprises a Group 3 to 10 transition or lanthanide metal, M, and at least one indenoindolyl ligand that is &pgr;-bonded to M. The key ligand is made in two steps from readily available indanones and aryl hydrazines. Reaction of its anion with a source of the metal completes a remarkably simple synthetic route to a new family of single-site olefin polymerization catalysts.
    Type: Grant
    Filed: January 29, 2001
    Date of Patent: April 23, 2002
    Assignee: Equistar Chemicals, LP
    Inventors: Sandor Nagy, Bradley P. Etherton, Ramesh Krishnamurti, John A. Tyrell
  • Patent number: 6255507
    Abstract: Described are methods of preparing organometallic complexes, including cyclopentadienyliron (II) arene complexes.
    Type: Grant
    Filed: September 18, 1998
    Date of Patent: July 3, 2001
    Assignee: 3M Innovative Properties Company
    Inventor: Roger A. Mader
  • Patent number: 6239299
    Abstract: The invention relates to metallocenes of formula (I), in which M is a metal from the Ti, Zr, Hf, V, Nb, Ta group or an element from the lanthanide group, X1 and X2 stand for an alkyl-, aryl-, alkenyl-, arylalkyl-, alkylaryl- or arylalkenyl group and L1 and L2 are hydrocarbon capable of forming a sandwich structure with M. R stands for C, Si, Ge or Sn, A and B are ferrocenyl-substituted radicals, or B is optionally a radical X1 of X2. The metallocenes are preferably used as catalysts in the polymerization of olefins.
    Type: Grant
    Filed: March 24, 2000
    Date of Patent: May 29, 2001
    Assignee: Borealis Technology Oy
    Inventors: Herwig Schottenberger, Ingo Wartusch, Eberhard Ernst, Jens Reussner
  • Patent number: 6211356
    Abstract: The invention concerns metallocene-phosphoramidite conjugates comprising one or a plurality of metallocenes and one or a plurality of phosphoramidites. The invention further concerns a process for preparing the metallocene-phosphoramidite conjugates and their use.
    Type: Grant
    Filed: October 21, 1998
    Date of Patent: April 3, 2001
    Assignee: Deutsches Krebsforschungszentrum Stiftung des Offentlichen Rechts
    Inventors: Manfred Wiessler, Dagmar Schütte
  • Patent number: 6211392
    Abstract: The present invention relates to a method of manufacturing ferrocenyl-1,3-butadiene, in which a ferrocenecarbonyl is reacted with an allyl halide in a polar aprotic solvent lacking a carbonyl group and containing a samarium diiodide in a temperature range.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: April 3, 2001
    Assignee: National Science Council
    Inventors: Jim-Min Fang, Shean-Jeng Jong
  • Patent number: 6191284
    Abstract: A ferroceneylphosphine ligand and complexes prepared therefrom for homogeneous catalytic enantioselective hydrogenation, the ligand having the formula (I): Another aspect of the invention is directed to a ferroceneylphosphine ligand of formula (II),
    Type: Grant
    Filed: December 20, 1999
    Date of Patent: February 20, 2001
    Assignee: Degussa-Huels Aktiengesellschaft
    Inventors: Paul Knochel, Tanja Ireland, Gabriele Grossheimann, Karlheinz Drauz, Ingo Klement
  • Patent number: 6169192
    Abstract: The invention relates to 1,2-ferrocenyldiphosphines which contain a functional group in the 1′ position either directly or via a bridging group, and also a process for their preparation. The compounds are important for transition metal complexes containing d-8 metals such as Rh, Ru, Pd or Ir. These transition metal complexes are widely used in the hydrogenation of organic double or triple bonds, in particular olefinic double bonds and carbon-heteroatom double bonds. The complexes are particularly suitable for enantioselective hydrogenation using chiral ferrocenyldiphosphines and corresponding prochiral unsaturated compounds. Ferrocenyldiphosphines having a functional group in the 1′ position are also important intermediates for ferrocenyldiphosphine ligands and their metal complexes of d-8 metals such as rhodium, ruthenium, palladium or iridium which are bound to inorganic polymeric supports via this functional group.
    Type: Grant
    Filed: January 8, 1999
    Date of Patent: January 2, 2001
    Assignee: Novartis AG
    Inventors: Beno{circumflex over (i)}t Pugin, Heidi Landert
  • Patent number: 6028150
    Abstract: The present invention relates to a novel fullerene-derived metallocene. Such fullerene-derived metallocene can be used as the catalyst for preparing olefin polymers.
    Type: Grant
    Filed: October 9, 1998
    Date of Patent: February 22, 2000
    Assignee: Chinese Petroleum Corporation
    Inventors: Long Y. Chiang, Taizoon A. Canteenwala
  • Patent number: 6015919
    Abstract: The invention relates to a compound of formula I ##STR1## R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl substituted by from 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy substituents;R.sub.2 and R.sub.3 are each independently of the other hydrogen or C.sub.1 -C.sub.12 alkyl; andHal is F, Cl, Br or I.Compounds of formula I are valuable intermediates for compounds of formula III which are also a subject of this invention: ##STR2## R.sub.1, R.sub.2, R.sub.3 and Hal are as defined above; R.sub.10 and R.sub.11 are identical or different and are C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, C.sub.5 -C.sub.12 cycloalkyl substituted by C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl substituted by from one to three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --SiR.sub.4 R.sub.5 R.sub.6, halogen, --SO.sub.3 M, --CO.sub.2 M, --PO.sub.3 M, --NR.sub.7 R.sub.8, --[.sup.+ NR.sub.7 R.sub.8 R.sub.9 ]X.sup.- or C.sub.1 -C.sub.5 fluoroalkyl substituents; orthe group --PR.
    Type: Grant
    Filed: February 8, 1999
    Date of Patent: January 18, 2000
    Assignee: Novartis AG
    Inventor: Benoit Pugin
  • Patent number: 6008394
    Abstract: A novel metallocene catalyst for the polymerization of olefin (co)polymers is of the general formula:R--SO.sub.2 --L--M--(X).sub.m T.sub.nwherein,M is a metal selected from Groups 3-10;T is a polymerization-stable anionic ancillary ligand;m+n is the valency of M minus 1;R is a C.sub.1 -C.sub.20 alkyl group, a C.sub.6 -C.sub.20 aryl ring or a C.sub.6 -C.sub.20 alkaryl or aralkyl group, optionally substituted with a halogen or an alkoxy group up to 10 carbon atoms;X is a halogen, alkoxy from C.sub.1 to C.sub.20, siloxy from C.sub.1 to C.sub.20, N(R).sub.2, a hydrocarbyl group containing up to about 12 carbon atoms, hydrogen or another univalent anionic ligand, or mixtures thereof;L is T as defined above with the proviso that one of the sites available for substitution is the attachment site of the sulfonyl group; andwherein L and T may be bridged.
    Type: Grant
    Filed: August 7, 1998
    Date of Patent: December 28, 1999
    Assignee: ARCO Chemicals Technology, L.P.
    Inventors: Sandor Nagy, John Tyrell, Bradley P. Etherton
  • Patent number: 6002035
    Abstract: The present invention relates to a novel fullerene-containing metallocene. Such a fullerene-containing metallocene can be used as the catalyst for preparing olefin polymers.
    Type: Grant
    Filed: May 4, 1998
    Date of Patent: December 14, 1999
    Assignee: Chinese Petroleum Corporation
    Inventors: Long Y. Chiang, Taizoon A. Canteenwala
  • Patent number: 5925778
    Abstract: The invention relates to a compound of formula (I), wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl substituted by from 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy substituents; R.sub.2 and R.sub.3 are each independently of the other hydrogen or C.sub.1 -C.sub.12 alkyl; and Hal is F, Cl, Br or I. Compounds of formula (I) are valuable intermediates for compounds of formula (III) which are also a subject of this invention, wherein R.sub.1, R.sub.2, R.sub.3 and Hal are as defined above; R.sub.10 and R.sub.11 are identical or different and are C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, C.sub.5 -C.sub.12 cycloalkyl substituted by C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl substituted by from one to three C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --SiR.sub.4 R.sub.5 R.sub.6, halogen, --SO.sub.3 M, --CO.sub.2 M, --PO.sub.3 M, --NR.sub.7 R.sub.8, --?.sup.+ NR.sub.7 R.sub.8 R.sub.9 !X.sup.- or C.sub.1 -C.sub.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: July 20, 1999
    Assignee: Novartis AG
    Inventor: Benoit Pugin
  • Patent number: 5872328
    Abstract: New ferrocene derivatives with the general formula: ##STR1## are described with X=H or OHY=H or CH.sub.2 0HZ=(CH2).sub.s --CH.sub.2 OHR=straight-chain or branched alkyl residue with 2 to 6 C atomsr=0 to 8, preferably 0 to 2s=0 to 8, preferably 1 and 2These ferrocene derivatives are best suited as burning rate modifiers in posite solid propellants for rocket engines and gas generators.
    Type: Grant
    Filed: March 4, 1997
    Date of Patent: February 16, 1999
    Assignees: Chemische Betriebe Pluto GmbH, Fraunhofer Gesellschaft zur Forderung der angewandte Forschung e.v.
    Inventors: Klaus Menke, Jutta Bohnlein-Mauss, Klaus-Peter Brehler, Jubert Jungbluth, Horst Neitsch
  • Patent number: 5866497
    Abstract: A catalyst precursor of the formula: ##STR1## wherein: R.sup.1 is a cycloalkadienyl ligand;R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are independently hydrogen, a hydrocarbyl group containing 1 to 20 carbon atoms, or a silyl group, and may be connected to R.sup.1 through a bridging group comprising at least two Group IVA atoms; with the proviso that one of R.sup.3, R.sup.4, and R.sup.5 is a negative charge stabilizing group selected from the group consisting of Group IVA trialkyl groups, aryl groups, heteroaromatic groups, ethylenically unsaturated hydrocarbon groups, acetylenically unsaturated hydrocarbon groups, ketonic groups, and aromatic organometallic moieties, is provided. When combined with a compound comprising a metal from Groups IIIB to VIII or the Lanthanide series of the Periodic Table of elements and an activating cocatalyst, the catalyst precursor is useful for the polymerization of olefins.
    Type: Grant
    Filed: June 26, 1997
    Date of Patent: February 2, 1999
    Assignee: Univation Technologies LLC
    Inventor: Rex Eugene Murray
  • Patent number: 5863911
    Abstract: Diarylethylene metallocene derivatives, processes for preparing the same and pharmaceutical compositions which contain the derivatives are disclosed. The compounds of the invention can exhibit anti-tumor activity, and can be particularly useful in the treatment of estrogen-dependent cancers.
    Type: Grant
    Filed: August 11, 1997
    Date of Patent: January 26, 1999
    Assignee: Modelisation et Mise au Point de Molecules Medicinales
    Inventors: Gerard Jaouen, Siden Top
  • Patent number: 5850086
    Abstract: A bleach and oxidation catalyst is provided comprising a catalytically active iron complex which can activate hydrogen peroxide or peroxy acids, for example.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: December 15, 1998
    Assignee: Regents of the University of Minnesota
    Inventors: Lawrence Que, Jr., Cheal Kim, Jinheung Kim, Yan Zang
  • Patent number: 5760263
    Abstract: The present invention relates to ferrocenes containing silylalkyl groups, represented by formula(I) and their preparation methods by reacting ferrocene with allylchlorosilanes represented by formula(II) in the presence of Lewis acid catalysts such as aluminum chloride: ##STR1## wherein R.sup.1 represents hydrogen, C.sub.1 -C.sub.12 alkyl, or C.sub.1 -C.sub.12 alkyl containing phenyl group; R.sup.2 represents chloro, C.sub.1 -C.sub.12 alkyl, or C.sub.1 -C.sub.12 alkyl containing phenyl group; and n and m are 0, 1 or 2, respectively, and at least one of n and m is not zero.
    Type: Grant
    Filed: June 23, 1997
    Date of Patent: June 2, 1998
    Assignee: Korea Institute of Science and Technology
    Inventors: Il Nam Jung, Sam Young Ahn, Bok Ryul Yoo, Joon Soo Han
  • Patent number: 5708150
    Abstract: A process for preparing transition metal complexes containing disubstituted cyclopentadienyl ligands of the general formula (1) ##STR1## in which a monomeric, monosubstituted cyclopentadiene is reacted using a mixture of an alkali metal oxide or hydroxide and an alkaline earth metal oxide or hydroxide as a metallating agent in polyoxyalkylene polyethers as the reaction medium with organic halides or pseudohalides to give the intermediate disubstituted cyclopentadiene which is, in situ, metallated and reacted with a transition metal halide to give the end product.
    Type: Grant
    Filed: November 15, 1995
    Date of Patent: January 13, 1998
    Assignee: Witco GmbH
    Inventor: Richard Lisowsky
  • Patent number: 5679814
    Abstract: Metallocenes, such as silicon bridged ansa-metallocenes, are purified by heating a slurry of the metallocene at elevated temperature in an aprotic, polar solvent so as to extract impurities from the metallocene into the solvent and then separating the impurity containing solvent from the metallocene.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: October 21, 1997
    Assignee: Albemarle Corporation
    Inventors: Jamie R. Strickler, John M. Power
  • Patent number: 5668192
    Abstract: Novel onium borates of an element of Groups 15 to 17 of the Periodic Table, or borates of an organometallic complex of an element of Groups 4 to 10 of the Periodic Table, well suited for the photochemical/electron beam cationic initiation of polymerization/crosslinking, the anionic borate moiety of which having the formula:[BX.sub.a R.sub.b ].sup.-in which a and b are integers ranging from 0 to 4 and a+b=4; the symbols X are each a halogen atom when a ranges up to 3 and an OH functional group when a ranges up to 2; and the symbols R, which may be identical or different, are each a phenyl radical substituted by at least one element or electron-withdrawing substituent or by at least two halogen atoms, or an aryl radical containing at least two aromatic ring members, or such aryl radical bearing at least one electron-withdrawing substituent.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: September 16, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Frederic Castellanos, Jacques Cavezzan, Jean-Pierre Fouassier, Christian Priou
  • Patent number: 5583241
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl which is substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups; R.sub.2 is a radical of formula II ##STR2## wherein R.sub.12 is C.sub.1 -C.sub.5 alkyl which is partially or completely fluorinated;R.sub.13 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --SiR.sub.4 R.sub.5 R.sub.6, halogen, --SO.sub.3 M, CO.sub.2 M, --PO.sub.3 M, --NR.sub.7 R.sub.8 or --[.sup..sym. NR.sub.7 R.sub.8 R.sub.9 ]X.sup..crclbar. ;m is an integer from 1 to 3, n is 0 or an integer from 1 to 4, and the sum of m+n is 1 to 5;R.sub.3, R.sub.10, R.sub.11 have each independently of one another the same meaning as R.sub.2 or are each independently of one another C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: December 10, 1996
    Assignee: Ciba-Geigy Corporation
    Inventor: Felix Spindler
  • Patent number: 5578741
    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: November 26, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
  • Patent number: 5569746
    Abstract: A process for making a metallocene, said process comprising the steps of (a) reacting an alkylsubstituted cyclopentadiene ligand, which contains a mixture of endo- and exo-isomers, with up to about a 10% excess over a stoichiometric amount of a deprotonation agent based on the amount of endo-isomers, so as to form a salt of said endo-isomers, (b) reacting the endo-isomer salt with a transition or actinide metal compound so as to form said metallocene and (c) optionally separating said exo-isomers and trace amounts of unreacted endo-isomers from said metallocene by distillation.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: October 29, 1996
    Assignee: Albemarle Corporation
    Inventors: John Y. Lee, Edward A. Burt
  • Patent number: 5550265
    Abstract: Novel onium borates of an element of Groups 15 to 17 of the Periodic Table, or borates of an organometallic complex of an element of Groups 4 to 10 of the Periodic Table, well suited for the photochemical/electron beam cationic initiation of polymerization/crosslinking, the anionic borate moiety of which having the formula:[BX.sub.a R.sub.b ].sup.-which a and b are integers ranging from 0 to 4 and a+b=4; the symbols X are each a halogen atom when ranges up to 3 and an OH functional group when a ranges up to 2; and the symbols R, which may be identical or different, are each a phenyl radical substituted by at least one element or electron-withdrawing substituent or by at least two halogen atoms, or an aryl radical containing at least two aromatic ring members, or such aryl radical bearing at least one electron-withdrawing substituent.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: August 27, 1996
    Assignee: Rhone-Poulenc Chimie
    Inventors: Frederic Castellanos, Jacques Cavezzan, Jean-Pierre Fouassier, Christian Priou
  • Patent number: 5495054
    Abstract: A method for the enantioselective reduction of prochiral ketones using catalytic amounts of tetrahydroindeno[1,2-d][1,3,2] oxazaboroles of formula II is disclosed. ##STR1## The oxazaboroles can be generated in situ from the corresponding cis-1-amino-2-indanols or imino indanols (III) ##STR2## Novel compounds of formulas II and III are also disclosed.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: February 27, 1996
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
  • Patent number: 5466844
    Abstract: Compounds of the formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl which is substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups; R.sub.2 and R.sub.3 are each independently of the other typically C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.12 cycloalkyl, or phenyl which is substituted by one to three identical or different members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen; R.sub.10 and R.sub.11 are identical and are typically C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.12 cycloalkyl or phenyl which is substituted by 1 to 3 identical or different members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen; or R.sub.10 and R.sub.11 are different and are C.sub.1 -C.sub.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: November 14, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Felix Spindler, Amina Wirth-Tijani, Heidi Landert
  • Patent number: 5432274
    Abstract: Ferricinium or ferricinium-based compounds are useful as blue redox dyes suitable for monitoring various enzymatic oxidation processes. A process for preparing such dyes is proposed which involves complexing ferrocene or its derivative with a cyclodextrin. The resulting yellow inclusion complex, an intermediate of the redox dye, is then oxidized electrochemically or by a reaction with bilirubin oxidase to form blue redox dyes which exhibit absorption peaks at 620 or 650 nm. Both the reduced form and the oxidized form of the dye are water-soluble.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: July 11, 1995
    Assignee: National Research Council of Canada
    Inventors: John H. T. Luong, Keith B. Male, Shishan Zhao, R. Stephen Brown
  • Patent number: 5371256
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl which is substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups; R.sub.2 and R.sub.3 are identical and are C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl or C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.12 cycloalkyl, or phenyl which is substituted by one to three identical or different members selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --SiR.sub.4 R.sub.5 R.sub.6, halogen, --SO.sub.3 M, --CO.sub.2 M, --PO.sub.3 M,--NR.sub.7 R.sub.8 and --[.sup..sym. NR.sub.7 R.sub.8 R.sub.9 ]X.sup..crclbar. ; or R.sub.2 and R.sub.3 are different and are C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy-substituted C.sub.5 -C.sub.12 cycloalkyl, phenyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C.sub.
    Type: Grant
    Filed: March 26, 1993
    Date of Patent: December 6, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Antonio Togni, Felix Spindler, Nadia Zanetti, Amina Tijani
  • Patent number: 5349100
    Abstract: There are provided enantiomerically enhanced chiral substituted cyclopentadienyl ligands, and compounds thereof, and a process for their making comprising contacting an optionally substituted fulvene having a prochiral carbon 6 with a lithium salt of an amine, amino acid or amide to effectuate enantioselective hydride addition to the carbon 6 of the fulvene so as to create a chiral center. There are further provided enantiomerically enhanced chiral organometallic complexes having one or more chiral substituted cyclopentadienyl groups.
    Type: Grant
    Filed: January 2, 1991
    Date of Patent: September 20, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventor: Eric A. Mintz
  • Patent number: 5245064
    Abstract: The present invention provides a compound of the formula: ##STR1## wherein R.sup.1 is (C.sub.1 -C.sub.5)perfluoroalkyl, R.sup.2 is (C.sub.1 -C.sub.5)perfluoroalkyl or (C.sub.1 -C.sub.5)alkyl, R.sup.3 is (C.sub.1 -C.sub.5)perfluoroalkyl or (C.sub.1 -C.sub.5)alkyl, R.sup.4 is (C.sub.1 -C.sub.5)alkyl and R.sup.5 is (C.sub.1 -C.sub.5)alkyl, with the proviso that no more than two of R.sup.1, R.sup.2 and R.sup.3 can be (C.sub.1 -C.sub.5)perfluoroalkyl; and transition metal complexes thereof.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: September 14, 1993
    Inventors: Paul G. Gassman, John R. Sowa, John W. Mickelson
  • Patent number: 5214175
    Abstract: The present invention relates to a process for the synthesis of a monohaloalkylferrocene by reaction of hydrogen with a monohaloalkanoylferrocene in the presence of PtO.sub.2 and SnCl.sub.2 as catalyst in an acetic acid medium.In this manner, a crude, particularly pure synthetic product is obtained in a high yield, simply and inexpensively.The monohaloalkylferrocenes are especially useful as surfactants or as intermediates for the synthesis of combustion catalysts for propergols.The present invention also relates to a novel monohaloalkylferrocene, namely 4-chlorobutylferrocene.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: May 25, 1993
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Jean-Claude Gautier, Jean-Guy Melin, Jean-Claude Mondet
  • Patent number: 5208357
    Abstract: There are provided enantiomerically enhanced chiral substituted cyclopentadienyl ligands and compounds thereof, and a process for their making comprising contacting a substituted fulvene or derivative thereof with an enantiomerically enhanced or pure nucleophile having at least one chiral center. There are further provided enantiomerically enhanced chiral organometallic complexes having one or more chiral substituted cyclopentadienyl groups.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: May 4, 1993
    Assignee: Exxon Chemical Patents, Inc.
    Inventor: Eric A. Mintz
  • Patent number: 5203974
    Abstract: A process for producing a thin film comprising electrotreating a dispersion or solution obtained by dispersing or dissolving a hydrophobic substance powder in an aqueous medium with a surfactant having a HLB value of 10.0 to 20.0, under conditions for forming a thin film of the hydrophobic substance on a cathode. The thin film of a hydrophobic substance can be formed on base metals such as aluminum, which can be applied to photosensitive materials and the like.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: April 20, 1993
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Hiroshi Kokado, Katsuyoshi Hoshino, Tetsuo Saji, Seiichiro Yokoyama
  • Patent number: 5189192
    Abstract: Addition polymerization catalysts comprising a derivative of a Group 4-8 metal compound prepared by metal center oxidation.
    Type: Grant
    Filed: January 16, 1991
    Date of Patent: February 23, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert E. LaPointe, Robert K. Rosen, Peter N. Nickias
  • Patent number: 5144052
    Abstract: A class of ligands capable of solution recognition of anions is defined by a cobalticinium moiety and an adjacent --CO--NH-amide linkage. This class is formed of redox responsive anion receptors, wherein the cobalticinium moiety is acyclic or macrocyclic.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: September 1, 1992
    Assignee: Metre International, Inc.
    Inventors: Paul D. Beer, Jana Hodacova, Sally Stokes
  • Patent number: 5135637
    Abstract: A process for producing an organic thin film, wherein a hydrophobic organic substance is admixed with a ferrocene compound in an aqueous medium to solubilize the hydrophobic organic substance and form a micelle solution. The micelle solution is electrolyzed to form thin film of the hydrophobic organic substance on an anode. The ferrocene compound has the formula: ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and are a hydrogen, a methyl group, a methoxyl group, an amino group, a dimethylamino group, a hydroxyl group or halogen, X is ##STR2## M is an alkali metal or an alkaline earth metal, a is an integer of 1 to 4, b is an integer of 1 to 5, k is an integer of 1 to 18 and m is an integer of 0 to 4.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: August 4, 1992
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Mitsuru Eida, Seiichiro Yokoyama
  • Patent number: RE37344
    Abstract: Compounds of formula I wherein R1 is C1-C8alkyl, phenyl or phenyl which is substituted by 1 to 3 C1-C4alkyl or C1-C4alkoxy groups; R2 and R3 are identical and are C1-C12alkyl, C5-C12cycloalkyl or C1-C4alkyl- or C1-C4alkoxy-substituted C5-C12cycloalkyl, or phenyl which is substituted by one to three identical or different members selected from the group consisting of C1-C4alkyl, C1-C4alkoxy, —SiR4R5R6, halogen, —SO3M, —CO2M, —PO3M, —NR7R8 and —[⊕NR7R8R9]X⊖; or R2 and R3 are different and are C1-C12alkyl, C5-C12cycloalkyl, C1-C4alkyl- or C1-C4-alkoxy-substituted C5-C12cycloalkyl, phenyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C1-C4alkyl, C1-C4alkoxy, —SiR4R5R6, halogen, —SO3M, —CO2M, —PO3M2, —NR7R8 and —[⊕NR7R8R9]X⊖; or the group —PR2R3 is a radical of formula II and R4, R5 and R
    Type: Grant
    Filed: May 18, 2000
    Date of Patent: August 28, 2001
    Assignee: Novartis Corporation
    Inventors: Antonio Togni, Felix Spindler, Nadia Zanetti, Amina Tijani