And Carbon Bonded Directly To The Heavy Metal Patents (Class 556/22)
  • Patent number: 6403772
    Abstract: New metallocene compounds are described where the ligand contains at least one open-pentadienyl containing radical characterized by a cyclic or acyclic, six &pgr; electron, delocalized, five atomic center structure. These metallocenes can advantageously be used in catalyst systems for the polymerization of olefins to generate a wide variety of different polymers including HDPE, LLDPE, ethylenelpropylene/(diene) elastomers, tactiospecific C3+&agr;-olefin polymers, intimate mixture thereof and the like.
    Type: Grant
    Filed: March 6, 1998
    Date of Patent: June 11, 2002
    Assignee: Montell Technology Company, BV
    Inventors: John A. Ewen, Robert W. Strozier, Robert L. Jones, Jr., Michael J. Elder
  • Patent number: 6342621
    Abstract: Penta-coordinated ruthenium catalysts for the metathesis reactions of olefins, in particular ring opening metathesis polymerization (ROMP) of cyclo-olefin monomers, which are cationic complexes represented by formula I, II or III: wherein each of X1 and X2, which may be the same or different, is an optionally substituted C3-C20 hydrocarbon group having an allyl moiety as an end group bonded to the ruthenium atom, or X1 and X2 together form a group, optionally substituted, which results from dimerization of an alkene and has at each end an allyl group bonded to the ruthenium atom; L1 and L2 are mono-dentate neutral electron donor ligands, preferably highly sterically encumbered neutral electron donor ligands such as alkyl phosphines or amines; L{circumflex over ( )}L is a bidentate neutral electron donor ligand, preferably phosphine, amino, imino, arsine or arphos; L3 is a solvent molecule or a neutral mono-dentate electron donor ligand; L{circumflex over ( )}L{circumflex over ( )}L is a trid
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: January 29, 2002
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shakti L. Mukerjee, Vernon L. Kyllingstad
  • Patent number: 6342605
    Abstract: Bidentate phosphine ligands of the formula wherein the substituents are as defined in the specification and a process for preparing linear aldehydes by hydroformylating internal olefins using such phosphine ligands.
    Type: Grant
    Filed: August 18, 1999
    Date of Patent: January 29, 2002
    Assignee: Celanese GmbH
    Inventors: Holger Geissler, Petrus W. N. M. van Leeuwen, Paul C. J. Kamer, Lars A. van der Veen
  • Patent number: 6313331
    Abstract: The present invention relates to novel complexes of (transition) metals containing ligands having phosphorus centers supporting a carbene structure or heteroalkane radical bonded to the (transition) metal.
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: November 6, 2001
    Assignee: The Governors of the University of Alberta
    Inventors: Ronald G. Cavell, Qinyan Wang, Ruppa P. Kamalesh Babu, Aparna Kasani
  • Patent number: 6310121
    Abstract: Compositions including fibers, fillers, reinforcing agents or other property-enhancing agents added to a polymeric matrix formed from DCPD monomer or related compounds such as norbornene and norbornadiene are disclosed. The composition has a mechanically forgiving matrix due to the polymer with the inherent strength and other physical properties of the enhancement agent according to the invention. Enhancement agents according to the invention generally include inorganic, organic and metallic substances in a variety of forms.
    Type: Grant
    Filed: August 7, 1998
    Date of Patent: October 30, 2001
    Assignee: Cymetech, LLC
    Inventors: Charles S. Woodson, Jr, Robert H. Grubbs
  • Patent number: 6306988
    Abstract: A method for the cross-metathesis of terminal olefins is disclosed. The method describes making disubstituted internal olefin products by contacting a first terminal olefin with another first terminal olefin to form a dimer and then contacting the dimer with a second terminal olefin in the presence of a catalyst having the formula where M may be Os or Ru, R and R1 may be the same or different and may be hydrogen or a substitutent group selected from C1-C20 alkyl, C2-C20 alkenyl,C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl. X and X1 may be the same or different and may be any anionic ligand. L and L1 may be the same or different and may be any neutral electron donor.
    Type: Grant
    Filed: January 26, 2000
    Date of Patent: October 23, 2001
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Daniel J. O'Leary, Helen E. Blackwell
  • Patent number: 6306987
    Abstract: Disclosed is a compound of formula (I), and its use in preparing metathesis polymers of dicyclopentadiene and/or other strained cycloolefins in which Me is ruthenium or osmium; X1 and X2 independently of one another are anionic ligands, or X1 and X2 together are a bis-anionic ligand; Y is oxygen, sulfur or the groups —NR7— or —PR7—, where R7 is hydrogen or a substituent selected from the group C1-C6alkyl, C6-C13aralkyl, sulfonyl and —C(═O)Rs2 and Rs2 is hydrogen or a substituent selected from the group C1-C12alkyl, C2-C12alkenyl, C3-C12cycloalkyl, C3-C12cycloalkenyl, C2-C11heterocycloalkyl, C2-C11heterocycloalkenyl, C5-C12aryl, C1-C9heteroaryl, C6-C14aralkyl, C2-C13heteroaralkyl, C6-C14aralkenyl and C3-C13heteroaralkenyl; n is 0 or 1; L1 is tertiary phosphine; and L2 is a neutral e− donor ligand which is coordinated to the metal atom and is attached via the bridge group C* to the carbon atom of the carbene group if n is 0 and to Y if n is 1.
    Type: Grant
    Filed: December 16, 1999
    Date of Patent: October 23, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Paul Adriaan Van Der Schaaf, Andreas Hafner, Andreas Mühlebach
  • Patent number: 6225488
    Abstract: Penta-coordinated ruthenium or osmium catalysts for metathesis reactions of olefins, which are cationic complexes represented by formulas I, II or III: wherein M is ruthenium or osmium; each of X1 and X2, which may be the same or different, is an optionally substituted C3-C20 hydrocarbon group having an allyl moiety as an end group bonded to the central metal atom M, or X1 and X2 together form a group, optionally substituted, which results from dimerization of an alkene and has at each end an allyl moiety bonded to the central metal atom M, L1 is a neutral electron donor ligand; L2 is a carbene group; L3 is a neutral electron donor ligand which may be the same as or different from L1, or L3 is a halide group; L11 is a neutral electron donor ligand; L12 is a solvent molecule capable of coordination to the central metal atom M; L13 is an alkyl group; L14 is an alkyl, a carbene, a solvent molecule capable of coordination to the central metal atom M, or a halide; L{circumflex over ( )}L is a bid
    Type: Grant
    Filed: April 2, 1999
    Date of Patent: May 1, 2001
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shakti L. Mukerjee, Vernon L. Kyllingstad
  • Patent number: 6197716
    Abstract: The present invention relates to a hydrogenation process for the production of aromatic halogen-amino compounds by means of catalytic hydrogenation on noble metal catalysts of corresponding aromatic halonitro compounds, characterised in that a rhodium, ruthenium, iridium, platinum or palladium catalyst which is modified with an inorganic or organic phosphorus compound with a degree of oxidation of less than V, is used, in the presence of a vanadium compound.
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: March 6, 2001
    Assignee: Novartis AG
    Inventors: Peter Baumeister, Urs Siegrist, Martin Studer
  • Patent number: 6191294
    Abstract: A new process is disclosed, particularly simple, convenient and practical, for the direct synthesis of metallocenes of formula (I): (CP)(ZR1m)n(A)rMLpL′q wherein (ZR1m)n is a divalent group bridging Cp and A; Cp is a substituted or unsubstituted cyclopentadieryl group; A is —O—, —S—, —N(R2)—, wherein R2 is hydrogen, alkyl, cycloalkyl aryl, alkylaryl or arylalkyl, or A has the same meaning of Cp; M is a transition metal belonging to group 3, 4, 5, 6 or to the lanthanide or actinide groups; L is a monoanionic sigma ligand, such as alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl, optionally containing Si or Ge; L′ is halogen or —OR5, R5 being a hydrocarbon radical; m is 1 or 2; n is 0-4; r is 0 or 1; p is 1-3; q is 0-2.
    Type: Grant
    Filed: September 13, 1999
    Date of Patent: February 20, 2001
    Assignee: Montell Technology Company BV
    Inventors: Luigi Resconi, Davide Balboni, Giansiro Prini
  • Patent number: 6175025
    Abstract: A di-substituted metallocene compound having good quality can be synthesized completely at a low cost in a high yield in a easy manner by reacting a metallocene dihalide with a Grignard reagent which is a compound represented by formula (I): RMgX (wherein R represents an aryl, benzyl or diaryl phosphinomethylene group which may have a substituent and X represents a halogen element) under specified conditions.
    Type: Grant
    Filed: February 23, 2000
    Date of Patent: January 16, 2001
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Yuichi Kitagawa, Koji Otaka, Tomoya Kubo, Eiji Takeichi
  • Patent number: 6172249
    Abstract: An enantiomerically enriched compound of formula (4) or the opposite enantiomer thereof, wherein R is C1-10 alkyl. This compound, in the form of a transition metal complex, is useful as a catalyst for stereoselective hydrogenation.
    Type: Grant
    Filed: November 4, 1999
    Date of Patent: January 9, 2001
    Assignee: Chirotech Technology, Ltd.
    Inventors: Ulrich Berens, Mark Joseph Burk, Arne Gerlach
  • Patent number: 6171994
    Abstract: A novel multiply crosslinked transition metal compound represented by the formula (I): wherein M is a metallic element of the Groups 3 to 10 or the lanthanide series of the Periodic Table; E1 and E2 are each a &sgr;-bonding or &pgr;-bonding ligand; X is a &sgr;-bonding ligand; Y is a Lewis base; A1, A2, . . . An and D are each a crosslinking group, and at least one of A1, A2, . . . An comprises a crosslink consisting of carbon alone; n is 2 to 4; p is 1 to 4; q is 1 to 5 and equal to the valence of M minus 2; r is 0 to 3; and s is 0 to 4, and a production process thereof. The transition metal compound is useful as a component of a polymerization catalyst for catalyzing the production of an olefin polymer having a uniform composition and a narrow molecular weight distribution in a high yield.
    Type: Grant
    Filed: November 2, 1998
    Date of Patent: January 9, 2001
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Nobuhiro Yabunouchi, Kiyohiko Yokota, Masami Watanabe, Takuji Okamoto, Noriyuki Tani
  • 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: 6133464
    Abstract: The invention relates to chiral ferrocenyls of formula (I) ##STR1## wherein R.sub.a is --P(R.sub.10 R.sub.11) or --SR.sub.12 ;R.sub.b is --P(R'.sub.10 R'.sub.11), --SR'.sub.12, --CH.dbd.NR.sub.12, --CH.sub.2 --NH--R.sub.12 or --CH.sub.2 --O--P(R.sub.10 R.sub.11); and the other substituents are as defined in claim 1,which may be used as ligands for transition metal catalysts in enantioselective reactions.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: October 17, 2000
    Assignee: Novartis AG
    Inventors: Benoit Pugin, Heidi Landert, Giorgio Pioda
  • Patent number: 6127563
    Abstract: Disclosed is a process for preparing bridged Group 4 metal complexes containing a neutral diene ligand starting from the corresponding novel, metal diene containing complexes by reaction thereof with the divalent derivative of a bridged bidentate ligand compound. The novel, intermediate metal diene complexes, their formation from tetravalent metal salts and an integrated process combining both process steps are claimed.
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: October 3, 2000
    Assignee: The Dow Chemical Company
    Inventors: Eugene Y. Chen, David D. Devore, Richard E. Campbell, Jr., D. Patrick Green, Jasson T. Patton, Jorge Soto, David R. Wilson
  • Patent number: 6096912
    Abstract: Abstract of the Disclosure: Catalyst systems for the polymerization of C.sub.2 -C.sub.10 -alk-1-enes contain, as active components,a) a metallocene complex of the general formula I ##STR1## where M is titanium, zirconium, hafnium, vanadium, niobium or tantalum, X is halogen or C.sub.1 -C.sub.8 -alkyl, Y is carbon, phosphorus, sulfur, silicon or germanium, Z is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.10 -cycloalkyl or C.sub.6 -C.sub.10 -aryl, R.sup.1 and R.sup.2 are identical or different and are each C.sub.1 -C.sub.4 -alkyl, R.sup.3 to R.sup.6 are identical or different and are each hydrogen or C.sub.1 -C.sub.8 -alkyl, or two adjacent radicals R.sup.3 and R.sup.4 and R.sup.5 and R.sup.6 in each case together form a hydrocarbon ring system of 4 to 15 carbon atoms and n is 0, 1 or 2, andb) an open-chain or cyclic alumoxane compound of the general formula II or III ##STR2## where R.sup.7 is C.sub.1 -C.sub.4 -alkyl and n is from 5 to 30.
    Type: Grant
    Filed: May 3, 1996
    Date of Patent: August 1, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Karl, Werner Roell, Hans Brintzinger, Bernhard Rieger, Udo Stehling
  • Patent number: 6090739
    Abstract: The present invention relates to a transition metal compound of the formula I ##STR1## where M.sup.1 is a metal of group IIIb, IVb or Vb of the Periodic Table of the Elements,R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and are each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an --SiR.sup.5.sub.3, --NR.sup.5.sub.2, --Si(OR.sup.5).sub.3, --Si(SR.sup.5).sub.3 or --PR.sup.5.sub.2 radical, where R.sup.5 are identical or different and are each a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.10 -aryl group, or two or more radicals R.sup.1, R.sup.2, R.sup.3 or R.sup.4 together with the atoms connecting them form a ring system,Y are identical or different and are each a hydrogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an OH group, a halogen atom or an NR.sup.5.sub.2 group,k is an integer which corresponds to the valence of the transition metal atom M.sup.1 minus two and if Y is a butadiene unit, k is 1,A is a bridge,R.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: July 18, 2000
    Assignee: Targor GmbH
    Inventors: Michael Riedel, Gerhard Erker, Lothar Duda
  • Patent number: 6084115
    Abstract: Disclosed is a process for preparing bridged Group 4 metal complexes containing a neutral diene ligand starting from the corresponding novel, metal diene containing complexes by reaction thereof with the divalent derivative of a bridged bidentate ligand compound. The novel, intermediate metal diene complexes, their formation from tetravalent metal salts and an integrated process combining both process steps are claimed.
    Type: Grant
    Filed: March 10, 1999
    Date of Patent: July 4, 2000
    Assignee: The Dow Chemical Company
    Inventors: Eugene Y. Chen, Richard E. Campbell, Jr., David D. Devore, D. Patrick Green, Jasson T. Patton, Jorge Soto, David R. Wilson
  • Patent number: 6084114
    Abstract: The invention relates to palladaphosphacyclobutanes of the formula (I) ##STR1## where R.sup.1, R.sup.2 are, independently of one another, hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, N[(C.sub.1 -C.sub.4)-alkyl].sub.2, CO.sub.2 -(C.sub.1 -C.sub.4)-alkyl, OCO-(C.sub.1 -C.sub.4)-alkyl or aryl;R.sup.3, R.sup.4, R.sup.5, R.sup.6 are, independently of one another, (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl or aryl;or where R.sup.1 and R.sup.2, R.sup.1 or R.sup.2 and R.sup.3 or R.sup.4, R.sup.3 and R.sup.4, R.sup.3 or R.sup.4 and R.sup.5 or R.sup.6, or R.sup.5 and R.sup.6 together form an aliphatic ring; or where R.sup.5 and R.sup.6, R.sup.3 or R.sup.4 and R.sup.5 or R.sup.6 together form an aromatic ring; andY is an anion of an inorganic or organic acid, with the exception of the compoundsdi-.mu.-chloro-bis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]d ipalladium(II)di-.mu.
    Type: Grant
    Filed: July 19, 1999
    Date of Patent: July 4, 2000
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Holger Geissler, Peter Gross, Bianca Guckes
  • Patent number: 6077805
    Abstract: Hexacoordinated ruthenium and osmium catalysts of the formulae ##STR1## in which M and M' independently of one another are ruthenium or osmium;X, X', Y and Y' independently of one another are anionic ligands, or X and Y and X' and Y' in each case together are bis-anionic ligandsL.sup.1 and L.sup.1' independently of one another are tertiary phosphine;L.sup.2 and L.sup.3 independently of one another are a monodentate ligand, or L.sup.2 and L.sup.3 together are bidentate, neutral electron donor ligands;L.sup.4 is tetradentate, neutral electron donor ligand;L.sup.5 is a bidentate, neutral electron donor ligand; andT and T' indepedently of one another are H or organic substituents, are useful for the synthesis of custom-tailored polymers and for the ring-closing metathesis of olefins.
    Type: Grant
    Filed: March 2, 1998
    Date of Patent: June 20, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Paul Adriaan Van Der Schaaf, Andreas Hafner, Andreas Muhlebach
  • Patent number: 6069264
    Abstract: The present invention relates to a transition metal compound of the formula I ##STR1## where M.sup.1 is a transition metal of group IIIb, IVb, Vb or VIb of the Periodic Table of the Elements,Y are identical or different and are each a hydrogen atom, an OH group, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group or an NR.sup.15.sub.2 group, where R.sup.15 is a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.10 -aryl group, k is an integer which corresponds to the valence of the transition metal atom M.sup.1 minus two and, if Y is a butadiene unit, k is 1,R.sup.1, R.sup.2, R.sup.3, R.sup.7, R.sup.8 and R.sup.9 are identical or different and are each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an --SiR.sup.15.sub.3, --NR.sup.15.sub.2, --SiOR.sup.15.sub.3, --SiSR.sup.15.sub.3 or --PR.sup.15.sub.2 radical, where R.sup.15 is a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.
    Type: Grant
    Filed: June 12, 1997
    Date of Patent: May 30, 2000
    Assignee: Targor GmbH
    Inventors: Michael Riedel, Gerhard Erker, Martin Konnemann
  • Patent number: 6069237
    Abstract: New metallocene ligand systems and catalysts/catalyst precursors are described where the ligand system contains at least one open-pentadienyl ligand characterized by an acyclic six .pi. electron delocalized, five atomic center structure. The open pentadienyl ligand is bonded to either another pentadienyl ligand or a Cp ligand by a bridging group. The metal is from group 3-5 or the Lanthanides. These metallocene catalysts/catalyst precursors optionally in combination with co-catalysts can be used to generate a wide variety of different polymer types including HDPE, LLDPE, LHDPE, ethylene/propylene elastomers, tactiospecific C3+ .alpha.-olefins, intimate mixture thereof and the like.
    Type: Grant
    Filed: September 11, 1995
    Date of Patent: May 30, 2000
    Assignee: Montell Technology Company BV
    Inventors: John A. Ewen, Robert W. Strozier
  • Patent number: 6060568
    Abstract: The present invention relates to novel complexes of (transition) metals containing ligands having phosphorus centers supporting a carbene structure or heteroalkane radical bonded to the (transition) metal.
    Type: Grant
    Filed: August 19, 1999
    Date of Patent: May 9, 2000
    Assignee: The Governors of the University of Alberta
    Inventors: Ronald G. Cavell, Qinyan Wang, Ruppa P. Kamalesh Babu, Aparna Kasani
  • Patent number: 6057466
    Abstract: Compounds, for initiating the polymerization of ethylenically unsaturated compounds, having the formula ##STR1## where E is nitrogen, phosphorus, arsenic or antimony,X is oxygen, NR.sup.1 or sulphur,L is R.sup.8 R.sup.9 R.sup.10 E.sup.1 (Y).sub.n, alkyl ether, ester, alkyl and aryl nitrites, pyridine, piperidine, sulphoxides, sulphones, sulphimides, sulphodiimides or sulphur ylides, and R.sup.1 -R.sup.5 are as defined in the specification.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: May 2, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Heinz Aleksander Ostoja Starzewski, Uwe Denninger
  • Patent number: 6051727
    Abstract: A very effective catalyst system for the polymerization or copolymerization of olefins comprises a cocatalyst, preferably an aluminoxane or a supported aluminoxane, and a metallocene of the formula I ##STR1## in which, in the preferred form, M.sup.1 in Zr or Hf, R.sup.1 and R.sup.2 are halogen or alkyl, R.sup.3 is alkyl, R.sup.4 to R.sup.12 are alkyl or hydrogen and R.sup.13 is a (substituted) alkylene or heteroatom bridge. The metallocenes, in particular the zirconocenes, produce polymers of very high molecular weight, in the case of prochiral monomers polymers of very high molecular weight, very high stereotacticity and very high melting point, at high catalyst activities in the industrially particularly interesting temperature range between 50 and 80.degree. C. In addition, reactor deposits are avoided by means of supported catalyst systems.
    Type: Grant
    Filed: December 31, 1997
    Date of Patent: April 18, 2000
    Assignee: Targor GmbH
    Inventors: Frank Kuber, Bernd Bachmann, Walter Spaleck, Andreas Winter, Jurgen Rohrmann
  • Patent number: 6043387
    Abstract: New chiral biphosphines, e.g., ##STR1## are useful as key components in catalysts for asymmetric reactions, providing desirably high enantiomeric excess (ee).
    Type: Grant
    Filed: February 3, 1999
    Date of Patent: March 28, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Philip Pye, Ralph P. Volante, Kai Rossen
  • Patent number: 6013819
    Abstract: Metal complexes having constrained geometry and a process for preparation thereof, addition polymerization catalysts formed therefrom, processes for preparation of such addition polymerization catalysts, methods of use, and novel polymers formed thereby, including ElPE resins and pseudo-random copolymers, are disclosed and claimed.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: January 11, 2000
    Assignee: The Dow Chemical Company
    Inventors: James C. Stevens, Robert K. Rosen
  • Patent number: 5990331
    Abstract: The present invention relates to a metallocene of the formula I, ##STR1## for preparing polyolefins, where M.sup.1 is preferably Zr, Hf or Ti, R.sup.1 and R.sup.2 are each a hydrogen atom, a C.sub.1 -C.sub.3 -alkyl group, a C.sub.1 -C.sub.3 -alkoxy group, a C.sub.6 -C.sub.8 -aryl group, a C.sub.6 -C.sub.8 -aryloxy group, a C.sub.2 -C.sub.4 -alkenyl group, a C.sub.7 -C.sub.10 -arylalkyl group, a C.sub.7 -C.sub.12 -alkylaryl group, a C.sub.8 -C.sub.12 -arylalkenyl group or chlorine, R.sup.3 is a chlorine atom, a C.sub.1 -C.sub.3 -alkyl group, a C.sub.2 -C.sub.4 -alkenyl group, a C.sub.6 -C.sub.8 -aryl group, an NR.sup.16.sub.2, SR.sup.16, OSiR.sup.16.sub.3, SiR.sup.16.sub.3 or PR.sup.16.sub.2 radical where R.sup.16 is chlorine, a C.sub.1 -C.sub.4 -alkyl group or a C.sub.6 -C.sub.8 -aryl group. R.sup.4 is a hydrogen atom, R.sup.13 is --(R.sup.14 M.sup.2 R.sup.15)--, --(R.sup.14 CR.sup.15)--(R.sup.14 CR.sup.15)--, --(R.sup.14 CR.sup.15)--(R.sup.14 M.sup.2 R.sup.15)-- or --(R.sup.14 CR.sup.15)--, where R.sup.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: November 23, 1999
    Assignee: Targor GmbH
    Inventors: Andreas Winter, Roland Zenk, Volker Fraaije, Frank Kuber
  • Patent number: 5969170
    Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on strained and unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and substituent groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each substituent group optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.
    Type: Grant
    Filed: May 23, 1997
    Date of Patent: October 19, 1999
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen, Lynda K. Johnson
  • Patent number: 5965758
    Abstract: A method for producing a bridged type transition metal complex represented by the following formula (1), comprising the following steps (i) and (ii):step (i); a step for reacting a specific cyclopentadiene compound with an organic alkaline metal compound or an organomagnesium compound to produce an alkaline metal salt compound or a magnesium salt compound of the cyclopentadiene compound; andstep (ii); a step for reacting the alkaline metal salt compound or magnesium salt compound of the cyclopentadiene compound with a specific transition metal compound, wherein at least the step (ii) is performed in the presence of an amine compound.According to the present invention, there can be provided a method for producing a bridged type transition metal complex having one cyclopentadiene type anion skeleton on an industrial scale in high yield without requiring an industrially disadvantageous low temperature and replacement of the solvent, which is capable of reducing the number of the steps.
    Type: Grant
    Filed: June 18, 1998
    Date of Patent: October 12, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaaki Nabika, Kotohiro Nomura
  • Patent number: 5965756
    Abstract: Group 4 metal constrained geometry complexes comprising a fused ring indenyl derivative ligand, catalytic derivatives thereof, processes for preparing the same and their use as components of olefin polymerization catalysts are disclosed.
    Type: Grant
    Filed: October 14, 1997
    Date of Patent: October 12, 1999
    Assignee: The Dow Chemical Company
    Inventors: Mark H. McAdon, Jasson T. Patton, Peter N. Nickias, Ravi B. Shankar, Francis J. Timmers, Brian W. Kolthammer, Daniel D. VanderLende, Steven M. Ueligger
  • Patent number: 5939504
    Abstract: Compositions and methods for catalyzing and controlling the rate of olefin metathesis reactions including Ring Opening Metathesis Polymerization (ROMP) reactions. The molding of polymer articles using ROMP polymers. The composition includes a Ruthenium or Osmium carbene complex catalyst and a gel modification additive. The Ruthenium or Osmium carbene complex catalyst having the formula ##STR1## where M may be Os or Ru; R and R.sup.1 may be the same or different and may be hydrogen or a substituent group including C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.1 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl and C.sub.1 -C.sub.20 alkylsulfinyl; X and X.sup.1 may be the same or different and may be any anionic ligand; and L and L.sup.1 may be the same or different and may be neutral electron donor.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: August 17, 1999
    Assignee: Advanced Polymer Technologies
    Inventors: Charles S. Woodson, Jr., Robert H. Grubbs
  • Patent number: 5919961
    Abstract: Chiral compounds of the formula I ##STR1## where the variables are as described in the specification.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: July 6, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Sturmer, Jun Okuda, Kurt Ritter
  • Patent number: 5912310
    Abstract: Metallocene complexes of the formula I ##STR1## where M is titanium, zirconium, hafnium, vanadium, niobium or tantalum,n is an integer from 0 to 10,R.sup.5 is ##STR2## R.sup.11 to R.sup.14 are as designated in the disclosure, n.sup.1 is an integer from 0 to 10,X.sup.1 to X.sup.4 are each fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl, alkylaryl having 1 to 10 carbon atoms in the alkyl radical and 6 to 20 carbon atoms in the aryl radical, --OR.sup.15 --, --NR.sup.15 R.sup.16 or ##STR3## R.sup.15 to R.sup.21 are as designated in the disclosure, and o, p, q, r are each an integer from 0 to 4, the sum o+p+q+r+1 corresponding to the valency of M,which were used as active catalyst components in the preparation of polymers of C.sub.2 -C.sub.10 -alkenes, are recovered by a process wherein the polymerization is stopped by adding an acid and the metallocene complexes of the formula I are recovered by extraction from the reaction mixture.
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: June 15, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Marc Oliver Kristen, Peter Jutzi, Thomas Redeker
  • Patent number: 5912376
    Abstract: A process for the preparation of a metal carbene, in which a metal salt is first reacted in the presence of a base and a secondary or tertiary alcohol with a tertiary phosphine or phosphite or a ditertiary diphosphine or diphosphite and then reacted in the presence of an acid with an alkyne and, if desired, an alkene.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: June 15, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Paul Adriaan Van Der Schaaf, Roman Kolly, Andreas Hafner, Andreas Muhlebach
  • Patent number: 5883277
    Abstract: Metallocene complexes having a cationic bridge of the formula ##STR1## where the substituents have the following meanings: M is a metal of transition group III, IV, V or VI of the Periodic Table of the Elements or a metal of the lanthanide group,X is fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or --OR.sup.5,R.sup.1 to R.sup.12, Y, Z and n having the meanings set out in the specification, said complexes can be prepared via ligand systems of the formula II ##STR2## as intermediates.
    Type: Grant
    Filed: August 14, 1997
    Date of Patent: March 16, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: David Fischer, Franz Langhauser, Gunther Schweier, Hans-Herbert Brintzinger, Nadine Leyser
  • Patent number: 5883275
    Abstract: The present invention relates to a process for the hydrogenation of metallocenes, which comprises treating at least one metallocene containing at least one double bond and/or at least one aromatic substituent in at least one nonhalogenated solvent with hydrogen in the presence of at least one hydrogenation catalyst.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: March 16, 1999
    Assignee: Targor GmbH
    Inventors: Carsten Bingel, Erich Hubscher, Claus-Peter Niesert, Roland Zenk
  • Patent number: 5856540
    Abstract: The present invention relates to optically active and racemic C.sub.2 -symmetric 2,2'-disubstituted 1,1'-diphosphino-ferrocenes of the formula Ia, to optically active and racemic asymmetric 1',2-disubstituted 1-phosphino-ferrocenes of the formula Ib and to achiral 2,2'-disubstituted 1,1'-diphosphino-ferrocenes of the formula II, to processes for preparing them, especially in accordance with the principle of asymmetric ortho-lithiation, to their use as ligands for transition metal complexes, to transition metal complexes comprising them, and to the use of the transition metal complexes as catalysts, especially in asymmetric syntheses.
    Type: Grant
    Filed: April 24, 1997
    Date of Patent: January 5, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Joachim-Heiner Jendralla
  • Patent number: 5831107
    Abstract: A palladacycle of the formula (I) ##STR1## where: R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are, independently of one another, hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, NH.sub.2, NH-alkyl(C.sub.1 -C.sub.4), N(alkyl).sub.2 -(C.sub.1 -C.sub.4), CO.sub.2 -(C.sub.1 -C.sub.4)alkyl, OCO-alkyl-(C.sub.1 -C.sub.4), or phenyl,R.sup.7 and R.sup.8 are, independently of one another, (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cyloalkyl, substituted or unsubstituted arylor where R.sup.1, and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.5 and R.sup.6 together form an aliphatic or aromatic ring, andY is an anion of an inorganic or organic acid.
    Type: Grant
    Filed: December 10, 1996
    Date of Patent: November 3, 1998
    Assignee: Aventis Research & Technology Deutschland
    Inventors: Matthias Beller, Hartmut Fischer, Wolfgang Anton Herrmann, Christoph Brossmer
  • Patent number: 5808121
    Abstract: There is disclosed a catalyst composition prepared by reacting together:(a) a source of a Group VIII metal,(b) a compound of the formula (I)R.sup.1 R.sup.2 PR.sup.4 CO.sub.2 R.sup.3 (I)where R.sup.1 and R.sup.2 are independently an unsubstituted or substituted alkyl, cycloalkyl or aryl group, R.sup.3 is hydrogen, an unsubstituted or substituted alkyl, cycloalkyl or aryl group and R.sup.4 is a divalent organic group and(c) a source of an anion which is either non-coordinating or weakly-coordinating to the Group VIII metal.The catalyst compositions are used in the preparation of polyketones from carbon monoxide and one or more olefins. Novel compounds of the formula ?(.eta..sup.3 -allyl)Pd(R.sub.1 R.sup.2 PR.sup.4 CO.sub.2 R.sup.3)!A where A is a weakly or non-coordinating anion are useful as such catalysts.
    Type: Grant
    Filed: February 12, 1996
    Date of Patent: September 15, 1998
    Assignee: BP Chemicals Limited
    Inventors: Wilhelm Keim, Stefan Mecking
  • Patent number: 5780701
    Abstract: An improved process is described for the catalytic dehydrogenation of organic molecules having a ##STR1## group to produce a ##STR2## group. The organic molecules are: ##STR3## wherein: A.sup.1, A.sup.2, A.sup.3, and A.sup.4 are each independently P, As or N: E.sup.2 is independently C or N; E.sup.3 is independently C, Si or Ge; E.sup.4 is independently C, Si, or Ge; and E.sup.5 is independently C, Si or Ge; M.sup.1, M.sup.2, M.sup.3, and M.sup.4 each is a metal atom independently selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum; Q.sup.1, Q.sup.2, Q.sup.3, and Q.sup.4 are each independently a direct bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, or CH.dbd.CH--;in structure I, structure II or structure IV, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each independently selected from alkyl, alkenyl, cycloalkyl, and aryl, or R.sup.1 and R.sup.2 together and R.sup.3 and R.sup.4 together form a ring structure having from 4 to 10 carbon atoms, orin structure III, R.sup.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: July 14, 1998
    Assignees: The Regents of the University of California, University of Hawaii
    Inventors: William C. Kaska, Craig M. Jensen
  • Patent number: 5770753
    Abstract: Metallocenes containing aryl-substituted indenyl derivatives as ligands, process for their preparation, and their use as catalysts.A very effective catalyst system for the polymerization or copolymerization of olefins comprises a cocatalyst, preferably an aluminoxane or a supported aluminoxane, and a metallocene of the formula I ##STR1## in which, in the preferred form, M.sup.1 is Zr or Hf, R.sup.1 and R.sup.2 are halogen or alkyl, R.sup.3 is alkyl, R.sup.4 to R.sup.12 are alkyl or hydrogen and R.sup.13 is a (substituted) alkylene or heteroatom bridge.The metallocenes, in particular the zirconocenes, produce polymers of very high molecular weight, in the case of prochiral monomers polymers of very high molecular weight, very high stereotacticity and very high melting point, at high catalyst activities in the industrially particularly interesting temperature range between 50.degree. and 80.degree. C. In addition, reactor deposits are avoided by means of supported catalyst systems.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 23, 1998
    Assignee: Targor GmbH
    Inventors: Frank Kuber, Bernd Bachmann, Walter Spaleck, Andreas Winter, Jurgen Rohrmann
  • Patent number: 5760264
    Abstract: Disclosed is a novel method of producing optically active metallocenyl phosphines of the general formula shown In the formula (Ia) (Ib), M represents iron, ruthenium or nickel; R.sup.1 and R.sup.1' both represent C.sub.1 -C.sub.4 alkyl groups; R.sup.2 and R.sup.3 each represent independently of each other either hydrogen or a C.sub.1 -C.sub.4 alkyl group, or, together with the nitrogen atom, form a five- or six member saturated heterocyclic ring which may optionally contain further heteroatoms; R.sup.4 and R.sup.5 each represent independently of each other a C.sub.1 -C.sub.4 alkyl group (for example) or an aryl group which is optionally substituted with one or more methyl or methoxy groups or with one or more fluorine atoms.
    Type: Grant
    Filed: July 9, 1997
    Date of Patent: June 2, 1998
    Assignee: Lonza, AG
    Inventor: Walter Brieden
  • Patent number: 5750752
    Abstract: The present invention relates to a stereorigid transition metal compound having as ligands a cyclopentadienyl group and a substituted or unsubstituted heteroatom which are connected to one another via a monocyclic or polycyclic ring system, with the cyclopentadienyl group being fused onto the monocyclic or polycyclic ring system. The transition metal compound of the invention is suitable as a catalyst component for olefin polymerization.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: May 12, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Riedel, Frank Kuber, Michael Aulbach, Gerhard Erker, Martin Konemann
  • Patent number: 5726115
    Abstract: A catalyst composition comprising a bis-amide compound represented by the formula ##STR1## wherein M is zirconium, hafnium or titanium; each N is a three coordinate nitrogen atom; each e is Si, Ge or Sn; each Z is, independently, a hydride or R; each R is, independently, a hydrocarbyl one or more carbon atoms of which may be substituted by an element selected from Si, O, P, N and S; L is a neutral Lewis base and m is a number from 0 to 2; or a dimer thereof and a second component. Preferably the second component is a compound which is capable of providing a bulky and labile anion ?A!.sup.-, which anion is substantially non-coordinating under the reaction conditions and contains at least one boron atom. Also provided is a process for oligomerizing or co-oligomerizing alpha olefins in the presence of this catalyst composition.
    Type: Grant
    Filed: March 11, 1996
    Date of Patent: March 10, 1998
    Assignee: Shell Oil Company
    Inventors: Andrew David Horton, Jan De With
  • Patent number: 5710298
    Abstract: Methods of preparing carbene compounds of the formula ##STR1## are disclosed wherein M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and a functional group selected from the group consisting of C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.1 are independently selected from any anionic ligand; and L and L.sup.
    Type: Grant
    Filed: August 30, 1996
    Date of Patent: January 20, 1998
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen, Lynda K. Johnson
  • Patent number: RE37208
    Abstract: The novel metallocenes of the formula I in which, preferably, M1 is Zr or Hf, R1 and R2 are alkyl or halogen, R3 and R4 are hydrogen, R5 and R6 are alkyl or haloalkyl, —(CR8R9)m—R7—(CR8R9)n— is a single- or multi-membered chain in which R7 may also be a (substituted) hetero atom, m+n is zero or 1, and R10 is hydrogen, form, together with aluminoxanes as cocatalysts, a very effective catalyst system for the preparation of polyolefins or high stereospecificity and high melting point. Polyolefins with unique or improved properties are obtained by polymerizing an olefin in the presence of a metallocene combined with a cocatalyst, wherein the metallocene is preferably a zirconocene or a hafnocene, and the Zr or Hf central atom is coordinated with two ligands which are derivatives of 2-substituted indenyl nuclei and which are substituted with at least one and up to four groups (e.g. aliphatic or aromatic groups) on the six-member rings of the indenyl nuclei.
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: June 5, 2001
    Assignee: Targor GmbH
    Inventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jürgen Rohrmann, Volker Dolle
  • 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
  • Patent number: RE37384
    Abstract: The novel metallocenes of the formula I in which, preferably, M1 is Zr or Hf, R1 and R2 are alkyl or halogen, R3 and R4 are hydrogen, R5 and R6 are alkyl or haloalkyl, —(CR8R9)m—R7—(CR8R9)n— is a single- or multi-membered chain in which R7 may also be a (substituted) hetero atom, and m+n is zero or 1, form, together with aluminoxanes as cocatalysts, a very effective catalyst system for the preparation of polyolefins of high molecular weight.
    Type: Grant
    Filed: July 13, 1999
    Date of Patent: September 18, 2001
    Assignee: Targor GmbH
    Inventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jürgen Rohrmann, Volker Dolle