Carbon-metal Bond Patents (Class 526/92)
  • Patent number: 10737255
    Abstract: A chemical reaction is catalyzed in an organic solvent using a water soluble N-heterocyclic carbene homogeneous catalyst to form a reaction mixture. An aqueous phase in the reaction mixture. A solvent in which the catalyst is insoluble is added to the reaction mixture, causing the catalyst to migrate to the aqueous phase to form a catalyst-laden aqueous phase. The catalyst is extracted from the catalyst-laden aqueous phase.
    Type: Grant
    Filed: April 3, 2019
    Date of Patent: August 11, 2020
    Assignee: Florida State University Research Foundation, Inc.
    Inventor: Hoyong Chung
  • Patent number: 10300470
    Abstract: This describes homogeneous catalysts that are recoverable from solution by being phase selective and through host-guest interactions. An example of a method includes separating a water soluble N-heterocyclic carbene homogeneous catalyst from a solution by: (a) forming a host-guest compound between the catalyst and an inclusion compound in the solution; and (b) isolating the host-guest compound from the solution.
    Type: Grant
    Filed: August 22, 2017
    Date of Patent: May 28, 2019
    Assignee: Florida State University Research Foundation, Inc.
    Inventor: Hoyong Chung
  • Patent number: 8992801
    Abstract: The present invention relates to a novel electroactive material which comprises a graphitic carbon phase C and a (semi)metal phase and/or a (semimetal) oxide phase (MOx phase) and also to the use of the electroactive material in anodes for lithium ion cells. The invention further relates to a process for producing such materials. The electroactive material comprises: a) a carbon phase C; b) at least one MOx phase, where M is a metal or semimetal, x is from 0 to <k/2, where k is the maximum valence of the metal or semimetal. In the electroactive material of the invention, the carbon phase C and the MOx phase form essentially co-continuous phase domains, with the average distance between two neighboring domains of identical phases being not more than 10 nm, in particular not more than 5 nm and especially not more than 2 nm.
    Type: Grant
    Filed: April 1, 2010
    Date of Patent: March 31, 2015
    Assignee: BASF SE
    Inventors: Hannah Maria König, Kirill Bramnik, Arno Lange, Phillip Hanefeld
  • Patent number: 8604141
    Abstract: Ruthenium and osmium carbene compounds that are stable in the presence of a variety of functional groups and can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins are disclosed. Also disclosed are methods of making the carbene compounds. The carbene compounds are of the formula where M is Os or Ru; R1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X1 are independently selected from any anionic ligand; and L and L1 are independently selected from any neutral electron donor. The ruthenium and osmium carbene compounds of the present invention may be synthesized using diazo compounds, by neutral electron donor ligand exchange, by cross metathesis, using acetylene, using cumulated olefins, and in a one-pot method using diazo compounds and neutral electron donors.
    Type: Grant
    Filed: April 24, 2012
    Date of Patent: December 10, 2013
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
  • Patent number: 8481658
    Abstract: A method for transitioning from a Ziegler-Natta to a Phillips catalyst system for the olefin polymerization reaction in one reactor, preferably a gas phase reactor, is described. The method comprises the steps of a) discontinuing a first olefin polymerization reaction performed in the presence of the Ziegler-Natta catalyst system; b) performing a second olefin polymerization reaction in the presence of a further catalyst system comprising catalyst components (A) and (B) producing, respectively, a first and a second polyolefin fraction, wherein the Mw of the first polyolefin fraction is less than the Mw of the second polyolefin fraction and the initial activity of catalyst component (A) exceeds the initial activity of catalyst component (B); and c) performing a third olefin polymerization reaction the presence of the Phillips catalyst system.
    Type: Grant
    Filed: December 17, 2009
    Date of Patent: July 9, 2013
    Assignee: Basell Polyolefine GmbH
    Inventors: Gerhardus Meier, Shahram Mihan
  • Patent number: 8304502
    Abstract: Disclosed is a copolymer coordination compound including two or more kinds of complexes, and a method of preparing the same. Herein, each of the complexes includes an organic ligand and a metal ion, and the two or more kinds of complexes are arranged in a line in a regular or irregular order, and are coordinated to each other. Also, the disclosed copolymer coordination compound functions as a gelator in a solvent, and is formed into a gel.
    Type: Grant
    Filed: February 15, 2008
    Date of Patent: November 6, 2012
    Assignee: LG Chem, Ltd.
    Inventor: Sung Ho Yoon
  • Patent number: 8013085
    Abstract: Process for preparing an aqueous polymer dispersion by polymerizing at least one ethylenically unsaturated monomer B in an aqueous medium in the presence of polymer particles A and at least one dispersant.
    Type: Grant
    Filed: June 4, 2004
    Date of Patent: September 6, 2011
    Assignee: BASF Aktiengesellschaft
    Inventors: Markus Schmid, Mubarik Mahmood Chowdhry, Dieter Distler, Reinhold J. Leyrer
  • Publication number: 20110112261
    Abstract: Process for the preparation of polybutadiene effected by the polymerization of butadiene in an aliphatic and/or cyclo-aliphatic solvent in the presence of a catalytic system prepared in situ which comprises: (i) a carboxylate of neodymium soluble in the process solvent containing a variable quantity of water, the H2O/Nd molar ratio ranging from 0.001/1 to 0.50/1; (ii) an alkyl compound of aluminum; (iii) an alkyl compound of aluminum in which at least one bond of Al consists of an Al—Cl bond; The total Al/Nd molar ratio ranging from 4/1 to 12/1, and the Cl/Nd molar ratio ranging from 2/1 to 6/1.
    Type: Application
    Filed: March 19, 2009
    Publication date: May 12, 2011
    Applicant: POLIMERI EUROPA S.P.A.
    Inventors: Gian Tommaso Viola, Marianna Zinna
  • Patent number: 7863394
    Abstract: A method of polymerizing poly(cyclic)olefin monomers encompassing (a) combining a monomer composition containing the poly(cyclic)olefin monomers, a non-olefinic chain transfer agent and an activator compound to form a mixture; (b) heating the mixture; and (c) adding a polymerization catalyst containing Ni and/or Pd. The non-olefinic chain transfer agent includes one or more compounds selected from H2, alkylsilanes, alkylalkoxysilanes, alkylgermanes, alkylalkoxygermanes, alkylstannanes, and alkylalkoxystannanes. The activator is characterized as having an active hydrogen with a pKa of at least 5. The resulting poly(cyclic)olefin polymers can be used in photoresist compositions.
    Type: Grant
    Filed: September 7, 2006
    Date of Patent: January 4, 2011
    Assignee: Promerus LLC
    Inventors: Larry F. Rhodes, Dennis A. Barnes, Andrew Bell, Brian K. Bennett, Chun Chang, John-Henry Lipian, Xiaoming Wu
  • Patent number: 7750172
    Abstract: Ruthenium and osmium carbene compounds that are stable in the presence of a variety of functional groups and can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins are disclosed. Also disclosed are methods of making the carbene compounds. The carbene compounds are of the formula where M is Os or Ru; R1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X1 are independently selected from any anionic ligand; and L and L1 are independently selected from any neutral electron donor. The ruthenium and osmium carbene compounds of the present invention may be synthesized using diazo compounds, by neutral electron donor ligand exchange, by cross metathesis, using acetylene, using cumulated olefins, and in a one-pot method using diazo compounds and neutral electron donors.
    Type: Grant
    Filed: October 30, 2007
    Date of Patent: July 6, 2010
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
  • Publication number: 20090227746
    Abstract: A production process of a polymerization catalyst component includes contacting compound (a) such as diethyl zinc represented by the defined formula [1], a compound (b) such as pentafluorophenol, represented by the defined formula [2], a compound (c) such as water, represented by the defined formula [3], and particles (d), such as silica, with one another in a hydrocarbon solvent under an agitator power of 0.05 kW/m3 or greater.
    Type: Application
    Filed: March 4, 2009
    Publication date: September 10, 2009
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Takeshi HATAKEYAMA, Takuya OGANE
  • Publication number: 20090143548
    Abstract: A method for producing a polybutadiene, which comprises subjecting 1,3-butadiene to cis-1,4 polymerization, and subsequently subjecting a resultant in the resulting polymerization system to syndiotactic-1,2 polymerization, the method being characterized in that there is added, after the polymerization, a halogen acid or halogen acid salt.
    Type: Application
    Filed: May 17, 2007
    Publication date: June 4, 2009
    Inventors: Koji Shiba, Michinori Suzuki, Masato Murakami, Yuji Matsudaira
  • Patent number: 7300993
    Abstract: The invention relates to a process for the preparation of polyether polyols, which process involves: (a) contacting a phosphorus containing compound having at least one hydroxyl group with alkylene oxide to obtain alkoxylated initiator, (b) contacting the alkoxylated initiator with further alkylene oxide in the presence of a double metal cyanide complex catalyst.
    Type: Grant
    Filed: June 1, 2005
    Date of Patent: November 27, 2007
    Assignee: Shell Oil Company
    Inventors: Michiel Barend Eleveld, Jan Hermen Hendrik Meurs, Peter Alexander Schut
  • Patent number: 7196142
    Abstract: Various novel block cationomers comprising polyisobutylene (PIB) and poly(2-dimethylamino)ethyl methacrylate) (PDMAEMA) segments have been synthesized and characterized. The specific targets were various molecular weight diblocks (PDMAEMA+) and triblocks (PDMAEMA+-b-PIB-b-PDMAEMA+) with the PIB blocks in the DPn=50–200?(Mn=3,000–9,000 g/mol) range connected to blocks of PDMAEMA+ cations in the DPn=5–20 range. The overall synthetic strategy for the preparation of these block cationomers comprised four steps: 1) Synthesis by living cationic polymerization of mono- and di-allyltelechelic polyisobutylenes, 2) End group transformation to obtain PIBs fitted with termini capable of mediating the atom transfer radical polymerization (ATRP) of DMAEMA, 3) ATRP of DMAEMA and 4) Quaternization of PDMAEMA to PDMAEMA+I? by CH3I. Kinetic and model experiments provided guidance to develop convenient synthesis methods.
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: March 27, 2007
    Assignee: The University of Akron
    Inventors: Joseph P. Kennedy, Zheng Fang
  • Patent number: 7108958
    Abstract: Anti-reflective compositions and methods of using these compositions to form circuits are provided. The compositions comprise a polymer dissolved or dispersed in a solvent system. Preferred polymers include polycarbonates, polysulfonyl esters, polycarbonate sulfones, and mixtures thereof. The compositions can be applied to a silicon wafer or other substrate to form a cured or hardened layer which is initially insoluble in typical photoresist developing solutions. Upon exposure to light, the cured or hardened layers become soluble in photoresist developing solutions so that the layer can be selectively removed along with the developed photoresist layer, thus eliminating the need for a separate removal step.
    Type: Grant
    Filed: July 25, 2003
    Date of Patent: September 19, 2006
    Assignee: Brewer Science Inc.
    Inventor: Douglas J. Guerrero
  • Patent number: 7102047
    Abstract: Ruthenium and osmium carbene compounds that are stable in the presence of a variety of functional groups and can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins are disclosed. Also disclosed are methods of making the carbene compounds. The carbene compounds are of the formula where M is Os or Ru; R1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X1 are independently selected from any anionic ligand; and L and L1 are independently selected from any neutral electron donor. The ruthenium and osmium carbene compounds of the present invention may be synthesized using diazo compounds, by neutral electron donor ligand exchange, by cross metathesis, using acetylene, using cumulated olefins, and in a one-pot method using diazo compounds and neutral electron donors.
    Type: Grant
    Filed: October 18, 2004
    Date of Patent: September 5, 2006
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
  • Patent number: 6887956
    Abstract: A catalyst system suitable for use in the production of high cis polybutadiene is disclosed. The catalyst system includes a cobalt salt of the formulaCoAx?, where A is a monovalent or divalent anion and x is 1 or 2; an alkyl aluminum chloride compound of the structure R2AlCl, where R is an alkyl group containing 2-8 carbon atoms; a trialkyl aluminum compound of the formula R3Al, where R is an alkyl group containing 2-8 carbon atoms; and a catalytic amount of water.
    Type: Grant
    Filed: October 2, 2001
    Date of Patent: May 3, 2005
    Assignee: Dow Global Technologies Inc.
    Inventors: Adriaan A. van der Huizen, Jean-Marc Potlet, Alain Sabatier, Patrick Le Roy
  • Patent number: 6888018
    Abstract: The present invention provides an organometallic compound represented by the general formula (1) or (2), process for producing the same, metathesis reaction catalyst containing the same, polymerization process using the same catalyst and polymer produced by the same polymerization process:
    Type: Grant
    Filed: August 20, 2001
    Date of Patent: May 3, 2005
    Assignee: Sekisui Chemical Co., Ltd.
    Inventors: Takeharu Morita, Hiroshi Hiraike, Nobuhiro Goto, Masafumi Nakatani, Fumiyuki Ozawa, Hiroyuki Katayama
  • Patent number: 6806325
    Abstract: Ruthenium and osmium carbene compounds that are stable in the presence of a variety of functional groups and can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins are disclosed. Also disclosed are methods of making the carbene compounds. The carbene compounds are of the formula where M is Os or Ru; R1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X1 are independently selected from any anionic ligand; and L and L1 are independently selected from any neutral electron donor. The ruthenium and osmium carbene compounds of the present invention may be synthesized using diazo compounds, by neutral electron donor ligand exchange, by cross metathesis, using acetylene, using cumulated olefins, and in a one-pot method using diazo compounds and neutral electron donors.
    Type: Grant
    Filed: December 19, 2002
    Date of Patent: October 19, 2004
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
  • Patent number: 6753390
    Abstract: A gas phase polymerization process for producing a polyolefin composition is described, which includes passing a gaseous stream containing hydrogen gas and one or more monomers, including ethylene monomers, through a reactor that includes a fluidized bed, under reactive conditions, in the presence of a catalyst that includes metallocene, to provide a polyolefin composition, wherein in one embodiment the fluidized bulk density is 60% or more of the settled bulk density (or, a voidage of 40% or less); and wherein the voidage is controlled by a number of factors including, in certain embodiments, (a) the reactor temperature being maintained at 100° C. or below; (b) the molar ratio of hydrogen gas to ethylene introduced into the reactor being 0.015 or below.
    Type: Grant
    Filed: February 18, 2003
    Date of Patent: June 22, 2004
    Assignee: Univation Technologies, LLC
    Inventors: Fred David Ehrman, Michael Elroy Muhle, Pradeep Pandurang Shirodkar, Keith Wesley Trapp
  • Patent number: 6716929
    Abstract: Superabsorbent polymers having a slow rate of absorption, and a process for their preparation. The superabsorbent polymer has a slow rate of absorption, is crosslinked with a covalent crosslinking agent and the metal of a polyvalent metal coordination compound, has the metal of the coordination compound distributed essentially homogeneously throughout the polymer, and has an Absorption Rate Index of at least about 5 minutes.
    Type: Grant
    Filed: July 3, 2002
    Date of Patent: April 6, 2004
    Assignee: The Dow Chemical Company
    Inventor: Larry R. Wilson
  • Patent number: 6610802
    Abstract: The present invention relates to a process for synthesis of polymer compositions with reduced catalyst content, wherein ethylenically unsaturated monomers containing less than 0.5 wt % of ethylenically unsaturated monomers with at least one carboxylic group, sulfonic acid group and/or at least one phosphonic acid group relative to the total weight of the ethylenically unsaturated monomers are polymerized by means of initiators containing a transferable group of atoms and of one or more catalysts comprising at least one transition metal in the presence of ligands which can form a coordination compound with the metal catalyst or catalysts and, after the polymerization, the catalyst contained in the polymer is at least partly separated. For this purpose, the polymer composition is filtered, after the polymerization, in the presence of at least one filter aid which contains at least 0.
    Type: Grant
    Filed: May 29, 2001
    Date of Patent: August 26, 2003
    Assignee: RohMax Additives GmbH
    Inventors: Sebastian Roos, Boris Eisenberg, Carolin Harpe
  • Patent number: 6579958
    Abstract: Superabsorbent polymers having a slow rate of absorption, and a process for their preparation. The superabsorbent polymer has a slow rate of absorption, is crosslinked with a covalent crosslinking agent and the metal of a polyvalent metal coordination compound, has the metal of the coordination compound distributed essentially homogeneously throughout the polymer, and has an Absorption Rate Index of at least about 5 minutes. Prepare water-swellable, water-insoluble polymer particles having a slow rate of water absorption by polymerizing a monomer in the presence of a covalent crosslinking agent and a polyvalent metal coordination compound under conditions such that there is formed a polymer having reversible cationic crosslinks and such that the metal is distributed essentially homogeneously throughout the polymer particles.
    Type: Grant
    Filed: December 7, 1999
    Date of Patent: June 17, 2003
    Assignee: The Dow Chemical Company
    Inventor: Larry R. Wilson
  • Patent number: 6559252
    Abstract: Catalysts for the polymerization of olefins are disclosed, which comprise the product obtained by contacting: (A) a bridged and/or substituted cyclopentadienyl compound of titanium, zirconium or hafnium; (B) an organometallic aluminium compound of the formula: Al(CH2—CR4R5—CR6R7R8)wR9qHz wherein R4 is a C1-C10 alkyl, alkenyl, or arylalkyl group; R5 is hydrogen or a C1-C10 alkyl, alkenyl, or arylalkyl group; R6 and R7 are C1-C10 alkyl, alkenyl, aryl, arylalkyl or alkylaryl groups; R8 is hydrogen or a C1-C10 alkyl, alkenyl, aryl, arylalkyl or alkylaryl group; R9 is a C1-C10 alkyl, alkenyl, or arylalkyl group, a carbon atom in the compound of formula (II) being optionally replaced by a Si or Ge atom; w is 1-3, z is 0 or 1, q=3−w−z, and (C) water; the molar ratio (B)/(C) being comprised between 1:1 and 100:1. These catalysts show an improved activity with respect to known catalysts, wherein different aluminium compounds are used.
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: May 6, 2003
    Assignee: Basell Technology Company BV
    Inventors: Andrew D. Horton, Jan F. van Baar, Peter A. Schut, Gerard M. M. van Kessel, Klaas L. von Hebel
  • Patent number: 6515084
    Abstract: Ruthenium and osmium carbene compounds that are stable in the presence of a variety of functional groups and can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins are disclosed. Also disclosed are methods of making the carbene compounds. The carbene compounds are of the formula where M is Os or Ru; R1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X1 are independently selected from any anionic ligand; and L and L1 are independently selected from any neutral electron donor. The ruthenium and osmium carbene compounds of the present invention may be synthesized using diazo compounds, by neutral electron donor ligand exchange, by cross metathesis, using acetylene, using cumulated olefins, and in a one-pot method using diazo compounds and neutral electron donors.
    Type: Grant
    Filed: December 21, 2000
    Date of Patent: February 4, 2003
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
  • Patent number: 6486279
    Abstract: Activation of ruthenium based catalyst compounds with acid to improve reaction rates and yields of olefin metathesis reactions, including ROMP, RCM, ADMET and cross-methasis reactions is disclosed. The ruthenium catalyst compounds are ruthenium carbene complexes of the general formula AxLyXzRu═CHR′ where x=0, 1 or 2, y=0, 1 or 2, and z=1 or 2 and where R′ is hydrogen or a substituted or unsubstituted alkyl or aryl, L is any neutral electron donor, X is any anionic ligand, and A is a ligand having a covalent structure connecting a neutral electron donor and an anionic ligand. The use of acid with these catalysts allows for reactions with a wide range of olefins in a variety of solvents, including acid-initiated RIM processes and living ROMP reactions of water-soluble monomers in water.
    Type: Grant
    Filed: June 14, 2001
    Date of Patent: November 26, 2002
    Assignee: California Institute of Technology
    Inventors: David M. Lynn, Eric L. Dias, Robert H. Grubbs, Bernard Mohr
  • Patent number: 6476163
    Abstract: Catalysts for the polymerization of olefins are disclosed, comprising the product obtainable by contacting: (A) a bridged and/or substituted cyclopentadienyl compound of Ti, Zr or Hf; (B) one or more organometallic aluminium compounds of formula (II): AlR43−zHz wherein the substituents R4, same or different from each other, are linear or branched, saturated or unsaturated C1-C20 alkyl or alkylaryl radicals, optionally containing Si or Ge atoms, wherein at least one of the substituents R4 is different from a straight alkyl group; z is 0 or 1; and (C) water, the molar ratio between the organometallic aluminium compound and water being comprised between 1:1 and 100:1; said catalyst being obtainable by a process comprising the following steps: (i) contacting component (A) with part of component (B) in the absence of component (C); (ii) contacting part of component (B) with component (C) in the absence of component (A) and successively (iii) contacting the products obtained in steps (i) and (ii).
    Type: Grant
    Filed: June 29, 1999
    Date of Patent: November 5, 2002
    Assignee: Basell Technology Company BV
    Inventors: Jan F. Van Baar, Maurizio Galimberti, Klaas L. Von Hebel, Andrew D. Horton, Gerard M. M. Van Kessel, Peter A. Schut, Tiziano Dall'occo
  • Patent number: 6455645
    Abstract: A novel process for the production of oligomeric and polymeric telechelic compositions, to the telechelic compositions produced in this manner and to use thereof in the plastics, fibres or lacquer sectors.
    Type: Grant
    Filed: March 18, 1999
    Date of Patent: September 24, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Martin Melchiors, Dieter Margotte, Hartwig Höcker, Helmut Keul, Andreas Neumann
  • Publication number: 20020103320
    Abstract: A novel process for the production of oligomeric and polymeric telechelic compositions, to the telechelic compositions produced in this manner and to use thereof in the plastics, fibers or lacquer sectors.
    Type: Application
    Filed: March 18, 1999
    Publication date: August 1, 2002
    Inventors: MARTIN MELCHIORS, DIETER MARGOTTE, HARTWIG HOCKER, HELMUT KEUL, ANDREAS NEUMANN
  • Publication number: 20020091062
    Abstract: Catalysts for the polymerization of olefins are disclosed, comprising the product obtainable by contacting: (A) a bridged and/or substituted cyclopentadienyl compound of Ti, Zr or Hf; (B) one or more organometallic aluminium compounds of formula (II): AlR 43−z Hz wherein the substituents R4, same or different from each other, are linear or branched, saturated or unsaturated C1-C20 alkyl or alkylaryl radicals, optionally containing Si or Ge atoms, wherein at least one of the substituents R4 is different from a straight alkyl group; z is 0 or 1; and (C) water; the molar ratio between the organometallic aluminium compound and water being comprised between 1:1 and 100:1; said catalyst being obtainable by a process comprising the following steps: (i) contacting component (A) with part of component (B) in the absence of component (C), (ii) contacting part of component (B) with component (C) in the absence of component (A) and successively (iii) contacting the products obtained in steps (i) and (ii).
    Type: Application
    Filed: June 29, 1999
    Publication date: July 11, 2002
    Inventors: JAN F. VAN BAAR, MAURIZIO GALIMBERTI, KLAAS L. VON HEBEL, ANDREW D. HORTON, GERARD M. M. VAN KESSEL, PETER A. SCHUT
  • Patent number: 6395846
    Abstract: The invention relates to high-activity catalysts for olefin polymerization, to efficient methods for producing them, and to efficient methods of using the catalysts for producing high-quality polyolefins. The olefin polymerization with the catalysts does not require a large amount of an organic aluminium compound, and the residual metal in the polyolefins produced is much reduced. The catalysts are characterized by containing a product as prepared by contacting any of clay, a clay mineral and an ion-exchanging layered compound, an organic silane compound, and water with each other, or by containing a silane compound-processed clay.
    Type: Grant
    Filed: April 18, 2000
    Date of Patent: May 28, 2002
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Haruhito Sato, Masahiko Kuramoto
  • Patent number: 6348554
    Abstract: The invention concerns a method for preparation of a liquid polymer composition, where ethylenically unsaturated monomers are polymerized by means of initiators that have a transferable atomic group, and one or more catalysts that contain at least one transition metal, in the presence of ligands that can form a coordination compound with the metallic catalysts, the catalyst is oxidized after the polymerization and then the catalyst is separated by filtration, where the composition contains a solvent with a dielectric constant less than or equal to 4.
    Type: Grant
    Filed: November 30, 1999
    Date of Patent: February 19, 2002
    Assignee: RohMax Additives GmbH
    Inventors: Sebastian Roos, Boris Eisenberg, Michael Mueller
  • Publication number: 20020004566
    Abstract: A novel process for the polymerization of olefins is provided. The process involves contacting at least one olefin with at least one metallocene catalyst in the presence of a specified compound that results in the production of polymeric products having a narrower molecular weight distribution. Also provided is a process for narrowing the molecular weight distribution of a polyolefin comprising contacting an olefin, at least one metallocene catalyst and a compound specified herein. Further provided are novel polyolefins, and films and articles produced therefrom.
    Type: Application
    Filed: August 22, 2001
    Publication date: January 10, 2002
    Inventors: Randal Ray Ford, Richard Kingsley Stuart
  • Patent number: 6320004
    Abstract: A catalyst composition that is the combination of or the reaction product of ingredients comprising a iron-containing compound, an organomagnesium compound, and a silyl phosphonate.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: November 20, 2001
    Assignee: Bridgestone Corporation
    Inventor: Steven Luo
  • Patent number: 6284852
    Abstract: Activation of ruthenium based catalyst compounds with acid to improve reaction rates and yields of olefin metathesis reactions, including ROMP, RCM, ADMET and cross-metathesis reactions is disclosed. The ruthenium catalyst compounds are ruthenium carbene complexes of the general formula AxLyXzRu═CHR′ where x=0, 1 or 2, y=0, 1 or 2, and z=1 or 2 and where R′ is hydrogen or a substituted or unsubstituted alkyl or aryl, L is any neutral electron donor, X is any anionic ligand, and A is a ligand having a covalent structure connecting a neutral electron donor and an anionic ligand. The use of acid with these catalysts allows for reactions with a wide range of olefins in a variety of solvents, including acid-initiated RIM processes and living ROMP reactions of water-soluble monomers in water.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: September 4, 2001
    Assignee: California Institute of Technology
    Inventors: David M. Lynn, Eric L. Dias, Robert H. Grubbs, Bernard Mohr
  • Patent number: 6087458
    Abstract: An initiator composition for polymerizing unsaturated monomers, comprising a component (A) which is a mixture ofi) at least one salt of a metal in the second sub-group of the periodic table, optionally in solution in an aromatic solvent or in an .alpha.,.beta.-unsaturated ester, andii) at least one salt of a metal in the seventh and eighth sub-group of the periodic table, optionally in solution in an aromatic solvent or in an .alpha.,.beta.-unsaturated ester; anda component (B) which is at least one organic peroxy ester,wherein the components (A) and (B) are kept separate from one another until they are brought together to initiate polymerization of the unsaturated monomers.Also, polymerizable compositions containing the initiator composition together with polymerizable unsaturated monomers. The initiator composition can be used to homopolymerize and copolymerize various unsaturated monomers, such as methacrylic and acrylic acid esters, at lower temperatures.
    Type: Grant
    Filed: January 30, 1998
    Date of Patent: July 11, 2000
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Shin-ichi Nonaka, Rainer B. Frings, Carola Jaroszewski, Gerwald F. Grahe
  • Patent number: 6080819
    Abstract: Blends of olefin polymers and syndiotactic vinyl polymers are produced by the catalytic polymerization of olefins and aromatic vinyl compounds or methacrylate esters as vinyl compounds in inert diluents in the presence of a catalyst mixture of transition metal compounds, metalloxane compounds and metal alkyl compounds.The blends have a finely dispersed distribution of the blending components and are suitable for the production of films, sheets, fibers, panels, coatings, pipes, hollow objects, injection molded products and foams.
    Type: Grant
    Filed: June 11, 1998
    Date of Patent: June 27, 2000
    Assignee: Borealis AG
    Inventors: Manfred Raetzsch, Manfred Arnold, Jana Knorr
  • Patent number: 5905125
    Abstract: A high cis-1,4-polybutadiene is produced, with reduced gel formation, by preparing a catalyst from (A) a cobalt compound, (B) a trialkyl (C.sub.1-10) aluminum compound, (C) a halide compound selected from those of formulae (1) and (2): (1) AlR.sup.2.sub.m X.sub.3-m, and (2) R.sup.3 --X, wherein R.sup.2 =C.sub.1-10 hydrocarbon, X=halogen, m=0 to 2, R.sup.3 =C.sub.1-40 hydrocarbon, and (D) water in an amount of 0.77 to 1.45 moles per mole of total Al in components (B) and (C); and polymerizing 1,3-butadiene in the presence of the resultant catalyst in a polymerization medium including an alkane, cycloalkane and/or olefin hydrocarbon.
    Type: Grant
    Filed: June 25, 1997
    Date of Patent: May 18, 1999
    Assignee: UBE Industries, Ltd.
    Inventors: Nobuhiro Tsujimoto, Takefumi Yano, Kazuhiro Akikawa, Chikara Kotani, Kei Tsukahara
  • Patent number: 5886202
    Abstract: Bridged fluorenyl/indenyl metallocenes having substituents at the 3 position of the indenyl and the use thereof in the polymerization of olefins are disclosed. Also a new method for preparing bridged fluorenyl/indenyl ligands wherein the indenyl has a substituent in the 3 position and the preparation of metallocenes with such ligands.
    Type: Grant
    Filed: September 12, 1997
    Date of Patent: March 23, 1999
    Inventors: Michael Jung, Helmut G. Alt, M. Bruce Welch
  • Patent number: 5880231
    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 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 functional 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 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: October 26, 1995
    Date of Patent: March 9, 1999
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen, Marc A. Hillmyer
  • Patent number: 5691429
    Abstract: A process for the manufacture of linear, substantially gel free, high cis 1,4 poly(butadiene) comprising polymerization in the presence of (a) a catalyst comprising at least one cobalt compound, at least one organoaluminium compound, and water, and (b) a cycloalkane as main solvent component, and (c) at least one substituted benzene as polymerization regulator of the general formula ##STR1## wherein n is an integer in the range of from 3 to 5, and wherein each R represents a lower alkoxy group containing from 1 to 6 carbon atoms.
    Type: Grant
    Filed: October 17, 1996
    Date of Patent: November 25, 1997
    Assignee: Shell Oil Company
    Inventors: Johannes Cornelis Maria Van Der Arend, Marijke De Boer-Wildschut, Adriaan Albert Van Der Huizen, Maria Johanna Elisabeth Kersten
  • Patent number: 5677400
    Abstract: In a process for producing syndiotactic-1,2-polybutadiene by suspension polymerization wherein a mixture composed of 1,3-butadiene, a cobalt compound, and an organometallic compound or metal hydride containing a metal of group I, II or III of the periodic table is contacted with an initiator selected from the group consisting of carbon disulfide, phenyl isothiocyanate and xanthogenic compounds in an aqueous medium, the improvement comprising, after the preparation of the mixture, adding thereto an anti gelling agent selected from the group consisting of alcohols, aldehydes, ketones, carboxylic acid esters, nitriles, sulfoxides, amides and phosphoric acid esters, whereby the formation of a rubber-like gelation product in the mixture is inhibited.
    Type: Grant
    Filed: May 1, 1996
    Date of Patent: October 14, 1997
    Assignee: UBE Industries, Ltd.
    Inventors: Nobuhiro Tsujimoto, Yoshisuke Baba, Osamu Kimura, Shuichi Sakaue
  • Patent number: 5627244
    Abstract: Disclosed is a process for producing a polymer of an unsaturated carboxylic acid or a derivative thereof, the process comprising polymerizing an unsaturated carboxylic acid or a derivative thereof in a water-soluble organic solvent-water mixture in the presence of at least one polymerization catalyst selected from the group consisting of a metal compound of the formulaL.sub.p.M.X.sub.q ( 1)wherein M is Ti, Zr, Hf or V, L is cyclopentazienyl, indenyl, fluorenyl or a derivative of these, X is halo, H, lower alkyl, lower alkoxyl, aryloxy, phenyl or benzyl, p and q each represents an integer including 0 and p+q is equal to the valence of M, and a metal compound of the formulaR.M.Y.sub.r ( 2)wherein M is defined above, R is a group formed by bonding, via a lower alkylene or di(lower alkyl)silylene group, two groups being cyclopentadienyl, indenyl, fluorenyl or a derivative of these, Y is halo, H, lower alkyl, lower alkoxyl, aryloxy, phenyl or benzyl, r is equal to the valence number of M minus 2.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: May 6, 1997
    Assignees: Sumitomo Chemical Co., Ltd., Nichia Chemical Industries Ltd.
    Inventor: Tsuneyuki Sato
  • Patent number: 5525678
    Abstract: A bimetallic catalyst produces broad or bimodal molecular weight distribution polyolefin resin whose composition depends on the ratio of the concentration of the two metals of the catalyst producing the HMW and LMW components. The bimetallic catalyst produces a broad/bimodal MWD resin whose HMW and LMW components depend on the relative productivity of each of the transition metal sites of the catalyst. Water and/or carbon dioxide are cofed to the polymerization reactor at levels necessary to modify the weight fractions of the HMW and LMW components, thus achieving a target molecular weight distribution, MWD. The invention allows the resin MWD to be adjusted in the reactor. The weight fraction of the high molecular weight component decreases with the addition of the water and or the carbon dioxide and the FI of the overall product increases with a decrease in the HMW component weight fraction in the product.
    Type: Grant
    Filed: September 22, 1994
    Date of Patent: June 11, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Robert I. Mink, Thomas E. Nowlin, Pradeep P. Shirodkar, Sandra D. Schregenberger, Grace O. Tsien
  • Patent number: 5397851
    Abstract: A process for producing high cis-1,4-polybutadienes wherein there is reduced gel formation is provided which process comprises: polymerizing 1,3-butadiene in a polymerization medium comprising an inert hydrocarbon solvent and water at a temperature of from about -30.degree. C. to about 60.degree. C. in the presence of a catalyst system which is a mixture of (1) a substantially anhydrous divalent cobalt salt, (2) diethyl aluminum chloride or ethyl aluminum sesquichloride and (3) an organo aluminum compound of the formula R.sub.3 Al wherein R is an alkyl group having from 8 to 12 carbon atoms and, optionally triethylaluminum, the molar ratio of chloride in the diethyl aluminum chloride plus (3) being from about 0.7:1 to about 1 and the molar ratio of chloride in the ethyl aluminum sesquichloride plus (3) being from about 0.7:1 to about 1.
    Type: Grant
    Filed: November 9, 1993
    Date of Patent: March 14, 1995
    Assignee: Polysar Rubber Corporation
    Inventors: Thomas F. Knauf, Akhtar Osman
  • Patent number: 5342909
    Abstract: Processes for the synthesis of several new carbene compounds of ruthenium and osmium are provided. These novel complexes function as stable, well-defined catalysts for the metathesis polymerization of cyclic olefins.
    Type: Grant
    Filed: August 13, 1993
    Date of Patent: August 30, 1994
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Lynda K. Johnson, Sonbinh T. Nguyen
  • Patent number: 5239023
    Abstract: Crystallizable 3,4-polyisoprene and isoprene-butadiene copolymers having high vinyl contents can be synthesized in organic solvents to quantitative yields after short polymerization times by utilizing the catalyst systems of this invention. The 3,4-polyisoprene made utilizing this catalyst system is strain crystallizable and can be employed in tire treads which provide improved traction and improved cut growth resistance. This invention specifically discloses a process for the synthesis of 3,4-polyisoprene which comprises polymerizing isoprene monomer in an organic solvent at a temperature which is within the range of about -10.degree. C. to about 100.degree. C.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: August 24, 1993
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Adel F. Halasa
  • Patent number: 5117327
    Abstract: Electrical devices, e.g. molded circuit boards, connectors and capacitors, fabricated from electrical insulating component, comprising norbornene dicarboximide thermoplastic polymer exhibiting a glass transition temperature greater than about 200.degree. C., moisture absorption after equilibrating in boiling water of less than about 3 weight percent and an electrical permittivity at 1000 hertz measured at 25.degree. C. and 50 percent relative humidity of less than 2.8. Preferred polymers comprise N-methyl norbornene dicarboximide, N-ethyl norbornene dicarboximide, N-propyl norbornene dicarboximide, N-butyl norbornene dicarboximide, N-trifluoroethyl norbornene dicarboximide, N-phenyl norbornene dicarboximide, N-trifluoromethylphenyl norbornene dicarboximide, N-cyclohexyl norbornene dicarboximide, N-cycloheptyl norbornene dicarboximide, N-cyclooctyl norbornene dicarboximide.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: May 26, 1992
    Assignee: Monsanto Company
    Inventors: Jawed Asrar, Christopher J. Hardiman
  • Patent number: 5061765
    Abstract: Isoprene-butadiene copolymers having high vinyl contents can be synthesized in organic solvents to high yields after short polymerization times by utilizing the process of this invention. The isoprene-butadiene copolymers made utilizing the process of this invention have a glass transition temperature which is within the range of about 0.degree. C. to about -60.degree. C. and can be employed in tire treads which provide improved traction and improved cut growth resistance. This invention specifically discloses a process for the synthesis of isoprene-butadiene copolymers having a high vinyl content which comprises copolymerizing isoprene monomer and butadiene monomer in an organic solvent at a temperature which is within the range of about -10.degree. C. to about 100.degree. C.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: October 29, 1991
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Adel F. Halasa
  • Patent number: 5011896
    Abstract: Pure syndiotactic 1,2-polybutadiene is a thermoplastic resin which has double bonds attached in an alternating fashion to its polymeric backbone. Films, fibers and molded articles can be made utilizing syndiotactic 1,2-polybutadiene. It can also be blended into rubbers and cocured therewith. Syndiotactic 1,2-polybutadiene can be made by solution, emulsion or suspension polymerization. It typically has a melting point which is within the range of about 195.degree. C. to about 215.degree. C. However, it is often desirable for the syndiotactic 1,2-polybutadiene to have a melting point of less than about 195.degree. C. This invention discloses a process for preparing syndiotactic 1,2-polybutadiene having a melting point of less than about 195.degree. C.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: April 30, 1991
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Anthony J. Bell, Eilert A. Ofstead