Plural Unsaturated Five-membered Carbocyclic Rings Bonded Directly To The Metal (e.g., Ferrorcenes, Bis Indenyl Iron, Etc.) Patents (Class 556/143)
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Patent number: 6664409Abstract: 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: GrantFiled: May 6, 2003Date of Patent: December 16, 2003Assignee: Chung-Shan Institute of Science & TechnologyInventor: Shean-Jeng Jong
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Patent number: 6664407Abstract: 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: GrantFiled: January 30, 2002Date of Patent: December 16, 2003Assignee: Beckman Coulter, Inc.Inventors: Tony D. James, Susumu Arimori
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Publication number: 20030216529Abstract: 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: ApplicationFiled: May 13, 2003Publication date: November 20, 2003Inventors: Richard E. Campbell, Jerzy Klosin, Ravi B. Shankar, Francis J. Timmers, Robert K. Rosen
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Publication number: 20030188474Abstract: 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: ApplicationFiled: February 28, 2003Publication date: October 9, 2003Inventors: Stephen Leonard Cook, Werner Kalischewski, Gabriele Lohmann, Armin Marschewski
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Patent number: 6593437Abstract: 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: GrantFiled: October 24, 2001Date of Patent: July 15, 2003Assignee: Basell Polyolefine GmbHInventors: Andrei Gonioukh, Wolfgang Micklitz, Benno Bildstein, Michael Malaun, Andreas Hradsky
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Patent number: 6576159Abstract: 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: GrantFiled: August 9, 2000Date of Patent: June 10, 2003Assignees: Hydro-Quebec, Centre National de la Recherche ScientifiqueInventors: Christophe Michot, Michel Armand, Michel Gauthier, Yves Choquette
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Patent number: 6576475Abstract: 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: GrantFiled: December 23, 1998Date of Patent: June 10, 2003Assignee: University of LiverpoolInventors: David Schiffrin, Robert Wilson
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Patent number: 6517795Abstract: 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: GrantFiled: July 31, 1997Date of Patent: February 11, 2003Assignee: Sasol Germany GmbHInventors: Klaus Noweck, Klaus Diblitz, Jan Sohiefler, Andrea Brasch
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Patent number: 6479646Abstract: 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: GrantFiled: October 12, 2000Date of Patent: November 12, 2002Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Masato Nakano, Tsutomu Ushioda, Seiki Mitani, Hiroshi Yamazaki
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Publication number: 20020161253Abstract: 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: ApplicationFiled: August 24, 2001Publication date: October 31, 2002Applicant: Boulder Scientific CompanyInventors: Karin A. Voll, Jeffrey M. Sullivan, Dawn A. Arkin, Fredric R. Askham
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Patent number: 6458983Abstract: 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: GrantFiled: July 21, 1999Date of Patent: October 1, 2002Assignee: Universita' Degli Studi di BariInventors: Francesco Paolo Intini, Giovanni Natile, Angelina Boccarelli, Mauro Coluccia
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Publication number: 20020115560Abstract: 1.Type: ApplicationFiled: January 18, 2002Publication date: August 22, 2002Inventors: Pascual Royo Gracia, Jesus Cano Sierra, Miguel Angel Flores De Paco, Begona Pena Garcia
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Patent number: 6399768Abstract: 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: GrantFiled: August 2, 1999Date of Patent: June 4, 2002Assignee: Ciba Specialty Chemicals CorporationInventors: Heinz Wolleb, Annemarie Wolleb, Beat Schmidhalter, Jean-Luc Budry
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Patent number: 6376629Abstract: 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: GrantFiled: January 29, 2001Date of Patent: April 23, 2002Assignee: Equistar Chemicals, LPInventors: Sandor Nagy, Bradley P. Etherton, Ramesh Krishnamurti, John A. Tyrell
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Patent number: 6255507Abstract: Described are methods of preparing organometallic complexes, including cyclopentadienyliron (II) arene complexes.Type: GrantFiled: September 18, 1998Date of Patent: July 3, 2001Assignee: 3M Innovative Properties CompanyInventor: Roger A. Mader
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Patent number: 6239299Abstract: 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: GrantFiled: March 24, 2000Date of Patent: May 29, 2001Assignee: Borealis Technology OyInventors: Herwig Schottenberger, Ingo Wartusch, Eberhard Ernst, Jens Reussner
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Patent number: 6211356Abstract: 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: GrantFiled: October 21, 1998Date of Patent: April 3, 2001Assignee: Deutsches Krebsforschungszentrum Stiftung des Offentlichen RechtsInventors: Manfred Wiessler, Dagmar Schütte
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Patent number: 6211392Abstract: 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: GrantFiled: March 8, 2000Date of Patent: April 3, 2001Assignee: National Science CouncilInventors: Jim-Min Fang, Shean-Jeng Jong
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Patent number: 6191284Abstract: 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: GrantFiled: December 20, 1999Date of Patent: February 20, 2001Assignee: Degussa-Huels AktiengesellschaftInventors: Paul Knochel, Tanja Ireland, Gabriele Grossheimann, Karlheinz Drauz, Ingo Klement
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Patent number: 6169192Abstract: 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: GrantFiled: January 8, 1999Date of Patent: January 2, 2001Assignee: Novartis AGInventors: Beno{circumflex over (i)}t Pugin, Heidi Landert
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Patent number: 6028150Abstract: 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: GrantFiled: October 9, 1998Date of Patent: February 22, 2000Assignee: Chinese Petroleum CorporationInventors: Long Y. Chiang, Taizoon A. Canteenwala
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Patent number: 6015919Abstract: 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: GrantFiled: February 8, 1999Date of Patent: January 18, 2000Assignee: Novartis AGInventor: Benoit Pugin
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Patent number: 6008394Abstract: 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: GrantFiled: August 7, 1998Date of Patent: December 28, 1999Assignee: ARCO Chemicals Technology, L.P.Inventors: Sandor Nagy, John Tyrell, Bradley P. Etherton
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Patent number: 6002035Abstract: 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: GrantFiled: May 4, 1998Date of Patent: December 14, 1999Assignee: Chinese Petroleum CorporationInventors: Long Y. Chiang, Taizoon A. Canteenwala
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Patent number: 5925778Abstract: 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: GrantFiled: October 9, 1997Date of Patent: July 20, 1999Assignee: Novartis AGInventor: Benoit Pugin
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Patent number: 5872328Abstract: 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: GrantFiled: March 4, 1997Date of Patent: February 16, 1999Assignees: 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
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Patent number: 5866497Abstract: 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: GrantFiled: June 26, 1997Date of Patent: February 2, 1999Assignee: Univation Technologies LLCInventor: Rex Eugene Murray
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Patent number: 5863911Abstract: 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: GrantFiled: August 11, 1997Date of Patent: January 26, 1999Assignee: Modelisation et Mise au Point de Molecules MedicinalesInventors: Gerard Jaouen, Siden Top
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Patent number: 5850086Abstract: A bleach and oxidation catalyst is provided comprising a catalytically active iron complex which can activate hydrogen peroxide or peroxy acids, for example.Type: GrantFiled: June 21, 1996Date of Patent: December 15, 1998Assignee: Regents of the University of MinnesotaInventors: Lawrence Que, Jr., Cheal Kim, Jinheung Kim, Yan Zang
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Patent number: 5760263Abstract: 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: GrantFiled: June 23, 1997Date of Patent: June 2, 1998Assignee: Korea Institute of Science and TechnologyInventors: Il Nam Jung, Sam Young Ahn, Bok Ryul Yoo, Joon Soo Han
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Patent number: 5708150Abstract: 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: GrantFiled: November 15, 1995Date of Patent: January 13, 1998Assignee: Witco GmbHInventor: Richard Lisowsky
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Patent number: 5679814Abstract: 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: GrantFiled: December 11, 1995Date of Patent: October 21, 1997Assignee: Albemarle CorporationInventors: Jamie R. Strickler, John M. Power
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Patent number: 5668192Abstract: 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: GrantFiled: April 18, 1996Date of Patent: September 16, 1997Assignee: Rhone-Poulenc ChimieInventors: Frederic Castellanos, Jacques Cavezzan, Jean-Pierre Fouassier, Christian Priou
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Patent number: 5583241Abstract: 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: GrantFiled: September 27, 1994Date of Patent: December 10, 1996Assignee: Ciba-Geigy CorporationInventor: Felix Spindler
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Patent number: 5578741Abstract: 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: November 26, 1996Assignee: Phillips Petroleum CompanyInventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
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Patent number: 5569746Abstract: 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: GrantFiled: January 23, 1995Date of Patent: October 29, 1996Assignee: Albemarle CorporationInventors: John Y. Lee, Edward A. Burt
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Patent number: 5550265Abstract: 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: GrantFiled: March 8, 1995Date of Patent: August 27, 1996Assignee: Rhone-Poulenc ChimieInventors: Frederic Castellanos, Jacques Cavezzan, Jean-Pierre Fouassier, Christian Priou
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Patent number: 5495054Abstract: 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: GrantFiled: May 31, 1994Date of Patent: February 27, 1996Assignee: Sepracor, Inc.Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
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Patent number: 5466844Abstract: 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: GrantFiled: September 27, 1994Date of Patent: November 14, 1995Assignee: Ciba-Geigy CorporationInventors: Felix Spindler, Amina Wirth-Tijani, Heidi Landert
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Patent number: 5432274Abstract: 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: GrantFiled: July 28, 1993Date of Patent: July 11, 1995Assignee: National Research Council of CanadaInventors: John H. T. Luong, Keith B. Male, Shishan Zhao, R. Stephen Brown
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Patent number: 5371256Abstract: 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: GrantFiled: March 26, 1993Date of Patent: December 6, 1994Assignee: Ciba-Geigy CorporationInventors: Antonio Togni, Felix Spindler, Nadia Zanetti, Amina Tijani
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Patent number: 5349100Abstract: 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: GrantFiled: January 2, 1991Date of Patent: September 20, 1994Assignee: Exxon Chemical Patents Inc.Inventor: Eric A. Mintz
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Patent number: 5245064Abstract: 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: GrantFiled: August 14, 1992Date of Patent: September 14, 1993Inventors: Paul G. Gassman, John R. Sowa, John W. Mickelson
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Patent number: 5214175Abstract: 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: GrantFiled: September 27, 1991Date of Patent: May 25, 1993Assignee: Societe Nationale des Poudres et ExplosifsInventors: Jean-Claude Gautier, Jean-Guy Melin, Jean-Claude Mondet
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Patent number: 5208357Abstract: 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: GrantFiled: December 31, 1990Date of Patent: May 4, 1993Assignee: Exxon Chemical Patents, Inc.Inventor: Eric A. Mintz
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Patent number: 5203974Abstract: 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: GrantFiled: January 24, 1992Date of Patent: April 20, 1993Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hiroshi Kokado, Katsuyoshi Hoshino, Tetsuo Saji, Seiichiro Yokoyama
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Patent number: 5189192Abstract: Addition polymerization catalysts comprising a derivative of a Group 4-8 metal compound prepared by metal center oxidation.Type: GrantFiled: January 16, 1991Date of Patent: February 23, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. LaPointe, Robert K. Rosen, Peter N. Nickias
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Patent number: 5144052Abstract: 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: GrantFiled: August 30, 1991Date of Patent: September 1, 1992Assignee: Metre International, Inc.Inventors: Paul D. Beer, Jana Hodacova, Sally Stokes
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Patent number: 5135637Abstract: 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: GrantFiled: May 9, 1991Date of Patent: August 4, 1992Assignee: Idemitsu Kosan Co., Ltd.Inventors: Mitsuru Eida, Seiichiro Yokoyama
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Patent number: RE37344Abstract: 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 RType: GrantFiled: May 18, 2000Date of Patent: August 28, 2001Assignee: Novartis CorporationInventors: Antonio Togni, Felix Spindler, Nadia Zanetti, Amina Tijani