Contains Heavy Metal Atom Patents (Class 526/176)
  • Patent number: 9776178
    Abstract: The invention relates to a ruthenium alkylidene complex comprising a 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligand, the cycloalkyl group of said 1-aryl-3-cycloalkyl-imidazolin-2-ylidene ligand being a cyclic secondary aliphatic alkyl.
    Type: Grant
    Filed: December 11, 2013
    Date of Patent: October 3, 2017
    Assignees: Ecole Nationale Superieure De Chimie De Rennes, Centre National De La Recherche Scientifique CNRS
    Inventors: Marc Mauduit, Mathieu Rouen
  • Patent number: 9416202
    Abstract: Processes of forming catalyst systems, catalyst systems and polymers formed therefrom are described herein. The processes generally include providing a first compound including a magnesium dialkoxide, contacting the first compound with a second compound to form a solution of reaction product “A”, wherein the second compound is generally represented by the formula: Ti(OR1)4; wherein R1 is selected from C1 to C10 linear to branched alkyls, contacting the solution of reaction product “A” with a first metal halide to form a solid reaction product “B”, contacting solid reaction product “B” with a second metal halide, to form reaction product “C” and contacting reaction product “C” with reducing agent to form a catalyst component.
    Type: Grant
    Filed: December 12, 2011
    Date of Patent: August 16, 2016
    Assignee: TINA TECHNOLOGY, INC.
    Inventors: Kayo Vizzini, David Knoeppel, Lei Zhang
  • Patent number: 8791284
    Abstract: It is an object of the present invention to provide a novel organometallic compound functioning usefully as a chain transfer agent and the like in polymerization reaction of a double-bond containing compound. The present invention provides an organometallic compound represented by the following general formula (1) and a production method thereof.
    Type: Grant
    Filed: June 30, 2010
    Date of Patent: July 29, 2014
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Takashi Ochiai, Haruyuki Makio
  • Patent number: 8394903
    Abstract: The present invention relates to a novel initiating system for the preparation of a living diene elastomer functionalized at the chain end by an amine group by anionic polymerization. The novel initiating system comprises an organolithium compound and a tin amide. The invention also relates to processes for the preparation of modified elastomers comprising an amine group at the chain end. These modified elastomers prove to be particularly advantageous in reinforced rubber compositions for tyres as they confer improved dynamic and mechanical properties in the vulcanized state.
    Type: Grant
    Filed: December 22, 2009
    Date of Patent: March 12, 2013
    Assignees: Compagnie Generale des Etablissements Michelin, Michelin Recherche et Technique S.A.
    Inventor: Jean-Marc Marechal
  • Patent number: 8227562
    Abstract: A polymer includes at a terminus a cyclic amine radical bonded to the polymer through a ring nitrogen atom. The polymer can be provided by using a lithiated version of the cyclic amine to initiate polymerization of one or more ethylenically unsaturated monomers. The polymer can be used in the production in a variety of vulcanizates.
    Type: Grant
    Filed: March 15, 2009
    Date of Patent: July 24, 2012
    Assignee: Bridgestone Corporation
    Inventors: Yuan-Yong Yan, Michael W. Hayes
  • Publication number: 20120130033
    Abstract: Provided herein are polyfarnesenes such as farnesene homopolymers derived from a farnesene and farnesene interpolymers derived from a farnesene and at least a vinyl monomer; and the processes of making and using the polyfarnesenes. The farnesene homopolymer can be prepared by polymerizing the farnesene in the presence of a catalyst such as a Ziegler-Natta catalyst, a Kaminsky catalyst, a metallocene catalyst, an organolithium reagent or a combination thereof. In some embodiments, the farnesene is prepared from a sugar by using a microorganism.
    Type: Application
    Filed: February 2, 2012
    Publication date: May 24, 2012
    Applicant: AMYRIS, INC.
    Inventor: Derek James MCPHEE
  • Publication number: 20110251354
    Abstract: The present invention relates to a novel initiating system for the preparation of a living diene elastomer functionalized at the chain end by an amine group by anionic polymerization. The novel initiating system comprises an organolithium compound and a tin amide. The invention also relates to processes for the preparation of modified elastomers comprising an amine group at the chain end. These modified elastomers prove to be particularly advantageous in reinforced rubber compositions for tyres as they confer improved dynamic and mechanical properties in the vulcanized state.
    Type: Application
    Filed: December 22, 2009
    Publication date: October 13, 2011
    Applicants: Michelin Recherche et Technique S.A., Societe De Technologie Michelin
    Inventor: Jean-Marc Marechal
  • Patent number: 7943712
    Abstract: The present invention is directed to a catalyst system for synthesizing rubbery polymers, such as polybutadiene rubber, styrene-butadiene rubber, isoprene-butadiene rubber, or styrene-isoprene-butadiene rubber, that are amine functionalized and have a high trans microstructure. The catalyst system, in one embodiment, includes (a) an organolithium amine compound, (b) a group IIa metal salt of an amino glycol or a glycol ether, (c) an organoaluminum compound, and optionally (d) an amine compound. The amine functionalized rubbery polymers can be utilized in tire tread rubbers where the rubbery polymers may provide desirable wear properties without substantially sacrificing other performance characteristic(s), e.g., traction properties.
    Type: Grant
    Filed: December 28, 2006
    Date of Patent: May 17, 2011
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu, Laurie Elizabeth Austin, Chad Aaron Jasiunas, Steven Kristofer Henning
  • Patent number: 7834112
    Abstract: A process for the polymerization of olefins using a metal complex of group 3, 4, 5, 6, 7, 8, 9 or 10 of the Periodic Table comprising at least one group C?NR1, C?PR1, C?O, C?S or a heteroaromatic ring system containing at least one atom from the group consisting of N, P, O and S, can be used for controlling the width of the molar mass distribution of the resulting polymers.
    Type: Grant
    Filed: September 10, 2002
    Date of Patent: November 16, 2010
    Assignee: Basell Polyolefine GmbH
    Inventors: Shahram Mihan, Birgit Dorer, Markus Enders, Pablo Fernandez
  • Patent number: 7825203
    Abstract: The present invention is directed to a catalyst system for synthesizing rubbery polymers, such as polybutadiene rubber, styrene-butadiene rubber, isoprene-butadiene rubber, or styrene-isoprene-butadiene rubber, that are amine functionalized and have a high trans or high vinyl microstructure. The catalyst system, in one embodiment, includes an organolithium amine compound, and one or more of (a) a group IIa metal salt of an amino glycol or a glycol ether, (b) an organoaluminum compound, or (c) an amine compound. The amine functionalized rubbery polymers can be utilized in tire tread rubbers where the rubbery polymers may provide desirable wear properties without substantially sacrificing other performance characteristic(s), e.g., traction properties.
    Type: Grant
    Filed: December 28, 2006
    Date of Patent: November 2, 2010
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu
  • Patent number: 7737218
    Abstract: Provided is a method comprising reacting the anionic living end of a polymer with a compound selected from the group consisting of tin halides and silicon halides to produced a polymer with a homolytically cleavable group containing a Sn—C bond or a Si—C bond. An engineered plastic may then be produced by adding the polymer containing a homolytically cleavable group containing a Sn—C bond or a Si—C bond to a solvent comprising at least one vinyl monomer; (b) optionally adding at least one additional inert solvent; (c) optionally adding additives selected from the group consisting of extender oils, modifiers, and antioxidants; and (d) initiating polymerization of the at least one vinyl monomer by the use of an initiator and/or heat, wherein a free radical is produced from the polymer containing a homolytically cleavable group containing a Sn—C bond or a Si—C bond.
    Type: Grant
    Filed: December 29, 2006
    Date of Patent: June 15, 2010
    Assignee: Bridgestone Corporation
    Inventors: James E. Hall, David F. Lawson
  • Publication number: 20100004414
    Abstract: A method for preparing a functionalized polymer, the method comprising the steps of preparing a reactive polymer and reacting the reactive polymer with an imide compound containing a protected amino group.
    Type: Application
    Filed: July 3, 2008
    Publication date: January 7, 2010
    Inventor: STEVEN LUO
  • Publication number: 20090311453
    Abstract: Molding composition comprising polyethylene and having a density in the range from 0.915 to 0.955 g/cm, an MI in the range from 0 to 3.5 g/10 min, an MFR in the range from 5 to 50, a polydispersity Mw/Mn in the range from 5 to 20, and a z-average moiar mass Mz of less than 1 million g/mol, a process for preparing such a composition, a catalyst suitable for the preparation of the same, as well as films comprising this molding composition.
    Type: Application
    Filed: April 15, 2006
    Publication date: December 17, 2009
    Applicant: BASELL POLYOLEFINE GMBH
    Inventors: Shahram Mihan, Dieter Lilge, Heinz Vogt, Jennifer Kipke, Rainer Karer
  • Publication number: 20080207858
    Abstract: A process for preparing a catalyst which process comprises preparing a mixture comprising iron oxide and at least one Column 1 metal or compound thereof, wherein the iron oxide is obtained by heating a mixture comprising an iron halide and at least 0.05 millimoles of a Column 6 metal per mole of iron; a catalyst made by the above described process; an iron oxide composition; a process for the dehydrogenation of an alkylaromatic compound which process comprises contacting the alkylaromatic compound with the catalyst; and a method of using an alkenylaromatic compound for making polymers or copolymers, in which the alkenylaromatic compound has been produced by the dehydrogenation process.
    Type: Application
    Filed: January 16, 2008
    Publication date: August 28, 2008
    Inventors: Ruth Mary Kowaleski, David Morris HAMILTON
  • Patent number: 7405262
    Abstract: A process for preparing a functionalized polymerization initiator, the process comprising combining a functionalized styryl compound and an organolithium compound.
    Type: Grant
    Filed: July 11, 2003
    Date of Patent: July 29, 2008
    Assignee: Bridgestone Corporation
    Inventors: Thomas Antkowiak, Christine Rademacher, Anthony Ramic, David F. Lawson
  • Patent number: 7321017
    Abstract: The present invention is directed to an amine containing catalyst system for synthesizing rubbery polymers, such as polybutadiene rubber and styrene-butadiene rubber, having a high trans microstructure. The catalyst system, in one embodiment, includes (a) an organolithium compound, (b) a group IIa metal salt, (c) an organoaluminum compound, and (d) an amine compound which can be selected from (1) a heterocyclic aromatic compound which includes a ring structure with one or more nitrogen atoms as part of the ring; (2) a heterocyclic non-aromatic compound which includes a ring structure with two or more nitrogen atoms as part of the ring; (3) an aromatic compound including a ring structure substituted with at least one amine and at least one polar functionality containing group selected from a carboxyl group or a hydroxyl group; (4) a bicyclic chelating diamine compound; or (5) an aliphatic amine which includes a C5-C20 alkyl group.
    Type: Grant
    Filed: August 24, 2006
    Date of Patent: January 22, 2008
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu, Chad Aaron Jasiunas, John Robert Zuppo, III, Lauire Elizabeth Austin
  • Publication number: 20070299224
    Abstract: Methods of forming polyolefins and catalysts are described herein. Such methods generally include forming Ziegler-Natta catalyst compounds in the absence of one or more blended compounds typically used to form such catalyst.
    Type: Application
    Filed: June 23, 2006
    Publication date: December 27, 2007
    Applicant: Fina Technology, Inc.
    Inventors: Kayo Vizzini, David Knoeppel, Steven Gray, David Rauscher, Tim Coffy, Henry Enriquez
  • Patent number: 7291687
    Abstract: The present invention is directed to a catalyst system for synthesizing rubbery polymers, such as polybutadiene rubber and styrene-butadiene rubber, having a high trans microstructure. The catalyst system, in one embodiment, includes (a) a barium salt of an alcohol that is soluble in a hydrocarbon solvent, and (b) an organomagnesium compound. In one example, the alcohol is a primary or secondary alcohol. The catalyst system can further optionally include an alkali metal alkoxide, an organolithium compound, an amine compound, or mixtures thereof.
    Type: Grant
    Filed: August 31, 2006
    Date of Patent: November 6, 2007
    Assignee: The Goodyear Tire and Rubber Company
    Inventors: Adel Farhan Halasa, Laurie Elizabeth Austin, Wen-Liang Hsu
  • Patent number: 7285605
    Abstract: The present invention is directed to a batch process for synthesizing rubbery polymers, such as styrene-butadiene rubber, having a high trans microstructure. In one embodiment, the batch process involves mixing a catalyst system with styrene and butadiene monomers in a single reactor, with additional butadiene monomer being added after a desired period of time to further drive styrene conversion and, thus, provide a desirable high trans rubbery polymer, e.g., styrene-butadiene rubber. The copolymerization process can be conducted at a temperature in the range of about 20° C. to about 180° and over a period of about 1 to about 4 hours. The catalyst system can include (a) an organolithium compound, (b) a group IIa metal salt, and (c) an organoaluminum compound. The catalyst system may further optionally include an amine compound and/or an organomagnesium compound.
    Type: Grant
    Filed: August 30, 2006
    Date of Patent: October 23, 2007
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu, Jean Steininger Clites, Timothy John Wolfgang
  • Patent number: 7279531
    Abstract: The present invention is directed to rubbery polymers, such as polybutadiene rubber or styrene-butadiene rubber, that contain tin coupling agents and provide desirable dispersion of carbon black in rubber compounds, such as for use in tire treads. The tin coupling agents are defined by the general formulas (I) (X3Sn)2O or (II) (X3Sn)O—(CH2)n—O(X3Sn), wherein X is a halogen and n is 1 to 20. A method of rubbery polymer synthesis, in one embodiment, involves mixing anionically polymerizable conjugated diene monomers with optional vinyl aromatic and an anionic-polymerization initiator, i.e., an organolithium compound, to form a mixture of living polymers. A tin coupling agent is added to the mixture of living polymers effecting polymerization conditions to form the tin coupled rubbery polymer. Such tin coupled rubbery polymers can be utilized in tire tread rubbers where the rubbery polymers may provide desirable wear properties without substantially sacrificing other performance characteristics.
    Type: Grant
    Filed: March 5, 2007
    Date of Patent: October 9, 2007
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Steven Kristofer Henning, Scott K. Armstrong, Jacob Gerhan
  • Patent number: 7205360
    Abstract: A preparation process for a copolymer having two blocks usable in a sulphur-cross-linkable rubber composition of reduced hysteresis in the cross-linked state, such a block copolymer in which one of the blocks is a polyisoprene and the other a diene elastomer other than a polyisoprene, and this rubber composition for tire treads. A process for the preparation of this copolymer involves copolymerizing one or more monomers including a conjugated diene other than isoprene using a catalytic system including at least one hydrocarbon solvent, a compound A of a metal of group IIIA, a compound B of an alkaline-earth metal and a polymeric initiator C having a C—Li bond which is constituted of a monolithiated polyisoprene intended to form the polyisoprene block, the number-average molecular weight Mn1 of the polyisoprene block being between 2,500 and 20,000 g/mol.
    Type: Grant
    Filed: April 30, 2004
    Date of Patent: April 17, 2007
    Assignee: Michelin Recherche et Technique S.A.
    Inventors: Pierre Robert, Jean-Michel Favrot, Pierre Lesage
  • Patent number: 7189792
    Abstract: The process and catalyst of this invention can be utilized to synthesize homo and copolymers of conjugated diene monomers and vinyl aromatic monomers having high trans contents of greater than 60% with low melting points. These homo and copolymers of conjugated diene monomers and vinyl aromatic monomers can be utilized in tire tread and sidewall rubbers that exhibit outstanding wear and tear characteristics in the tread and excellent flexing properties in the sidewall. The rubber polymers of this invention are made utilizing an improved catalyst system. This catalyst system is comprised of (a) organo aluminum compounds, (b) organo lithium compounds, (c) a barium compound selected from barium salts of (i) di(ethylene glycol) ethyl ether, (ii) di(ethylene glycol) propyl ether, (iii) di(ethylene glycol) hexyl ether, (iv) di(N,N-dimethyl amino glycol) ethyl ether, (v) menthol and thymol in the presence of polar modifier consisting of water, alcohols, amines, thiols, phosphates and phosphites.
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: March 13, 2007
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu, Chad Aaron Jasiunas, Laurie Elizabeth Austin
  • Patent number: 7125940
    Abstract: Disclosed is a process for preparing polymers and copolymer blocks of conjugated dienes with varying amounts of branching comprising the use of a microstructure control agent and a microstructure control agent deactivant. The polymerization can be started with or without a microstructure control agent. At some point in the polymerization prior to the completion of the addition of the conjugated diene to the polymer, the microstructure control agent can be deactivated, either partially or completely, resulting in a polymer or copolymer block having a region of less branching adjacent to a region of more branching. Preferred microstructure control agent deactivants are metal alkyls such as triethyl aluminum.
    Type: Grant
    Filed: December 19, 2003
    Date of Patent: October 24, 2006
    Assignee: Kraton Polymers U.S. LLC
    Inventor: Carl L. Willis
  • Patent number: 7048023
    Abstract: The invention is directed to a pneumatic tire having at least one component comprising a vulcanizable rubber composition, wherein the vulcanizable rubber composition comprises, based on 100 parts by weight of elastomer (phr), from about 30 to 100 phr of high trans random SBR, and from about zero to about 70 phr of at least one additional elastomer, wherein the high trans random SBR comprises from about 3 to about 30 percent by weight of styrene.
    Type: Grant
    Filed: May 10, 2004
    Date of Patent: May 23, 2006
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: James Robert Herberger, Sr., Kenneth Allen Bates, John Joseph Andre Verthe
  • Publication number: 20040210005
    Abstract: The invention is directed to a pneumatic tire having at least one component comprising a vulcanizable rubber composition, wherein the vulcanizable rubber composition comprises, based on 100 parts by weight of elastomer (phr), from about 30 to 100 phr of high trans random SBR, and from about zero to about 70 phr of at least one additional elastomer, wherein the high trans random SBR comprises from about 3 to about 30 percent by weight of styrene.
    Type: Application
    Filed: May 10, 2004
    Publication date: October 21, 2004
    Applicant: The Goodyear Tire & Rubber Company
    Inventors: James Robert Herberger, Kenneth Allen Bates, John Joseph Andre Verthe
  • Patent number: 6800582
    Abstract: The present invention provides a process for preparing amino functionalized diene polymers with 1,4-trans linkage content equal to or greater than 70%. The invention also concerns polymers of such type, a rubber composition and a tire casing containing those polymers. The process of preparation according to the invention comprises polymerizing at least one diene monomer by means of a lithium catalytic system, which comprises at least one hydrocarbon solvent, one compound A of a IIIA group metal, one compound B of an alkaline earth metal and one aminolithium initiator C. Amino functionalized diene polymers with high 1,4-trans linkage content according to the invention are such that the amino function, situated at the end of the polymer chain, is a tertiary amino function, the rate of functionalization of said polymers being equal to or greater than 50% and the 1,4-trans linkage content being equal to or greater than 70%.
    Type: Grant
    Filed: March 28, 2003
    Date of Patent: October 5, 2004
    Assignee: Michelin Recherche et Technique S.A.
    Inventors: Jean-Michel Favrot, Philippe Laubry
  • Patent number: 6787661
    Abstract: The present invention relates to a tin-containing organolithium compound which can be used as anionic polymerization initiators, represented by the following formula (1): R4−xSn(Ya—Zm—Yb—Li)x  (1) Wherein R, Z and Y are defined as in the specification; x represents a value of 1 or 2; m represents a value of 0 or 1; a represents a value of 0 to 6, b represents a value of 0 to 6, a+b is from 0 to 6, provided that m=1 when x=1. The tin-containing organolithium compounds according to the present invention can be used as initiators to initiate the polymerization of conjugated dienes and/or monovinyl aromatic hydrocarbons, thereby synthesizing various linear, star or telechelic polymers. The present invention also relates to a method for preparing the tin-containing organolithium compounds according to the present invention.
    Type: Grant
    Filed: June 11, 2002
    Date of Patent: September 7, 2004
    Assignees: China Petroleum and Chemical Corporation, Research Institute of Beijing Yanshan
    Inventors: Chuanqing Li, Aimin Liang, Wei Li, Liyun Zhao, Song Lu, Lin Xu, Qing Liu
  • Patent number: 6777511
    Abstract: An industrially excellent process for producing a poly(meth)acrylate having a reduced metal content which comprises contacting a mixture of a poly(meth)acrylate and an organic solvent with an acidic aqueous solution, such as an aqueous solution obtained by dissolving a polyprotic carboxylic acid having about 2 to 12 carbon atoms in water, is provided, and, by this invention, contents of metals such as sodium, potassium, iron and the like can be remarkably reduced.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: August 17, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koshiro Ochiai, Akira Kamabuchi
  • Patent number: 6767976
    Abstract: (1) A methacrylic ester or an acrylic ester is anionically polymerized, using a polymerization initiator compound comprising an addition reaction product of a conjugated diene compound and an organic alkali metal compound, in the presence of a tertiary organoaluminum compound having in the molecule thereof a chemical structure represented by a formula: Al—O—Ar wherein Ar represents an aromatic ring; or (2) a methacrylic ester or an acrylic ester is anionically polymerized, using a polymerization initiator compound comprising an addition reaction product of an organic alkali metal compound and a compound having a 1,1-diaryl-1-alkene structure, by adding the ester in the form of a mixture with the above-mentioned specific tertiary organoaluminum compound to the polymerization system.
    Type: Grant
    Filed: June 3, 2003
    Date of Patent: July 27, 2004
    Assignee: Kuraray Co., Ltd.
    Inventors: Kenichi Hamada, Kazushige Ishiura, Toru Takahashi, Sachie Yaginuma, Makoto Akai, Tomohiro Ono, Kenji Shachi
  • Patent number: 6758251
    Abstract: The invention is directed to a pneumatic tire having at least one component comprising a vulcanizable rubber composition, wherein the vulcanizable rubber composition comprises, based on 100 parts by weight of elastomer (phr), from about 30 to 100 phr of high trans random SBR, and from about zero to about 70 phr of at least one additional elastomer, wherein the high trans random SBR comprises from about 3 to about 30 percent by weight of styrene.
    Type: Grant
    Filed: August 21, 2002
    Date of Patent: July 6, 2004
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Kenneth Allen Bates, Brian David Holden, John Joseph Andre Verthe
  • Patent number: 6703446
    Abstract: Hetero-telechelic polymers having the formula: FG—(Q)d—Z—J—[A(R1R2R3)]x  (I) wherein FG is a protected or non-protected functional group; Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic hydrocarbons, and mixtures thereof; d is an integer from 10 to 200; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; J is oxygen, sulfur, or nitrogen; [A(R1R2R3)]x is a protecting group, wherein A is an element selected from Group IVa of the Periodic Table of Elements; R1, R2, and R3 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylam
    Type: Grant
    Filed: June 21, 2002
    Date of Patent: March 9, 2004
    Assignee: FMC Corporation, Lithium Division
    Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
  • Publication number: 20030216529
    Abstract: Compounds and metal complexes comprising a polycyclic, fused ring ligand or inertly substituted derivative thereof having up to 60 atoms other than hydrogen, said ligand comprising at least: (1) a cyclopentadienyl ring, (2) a 6, 7, or 8 membered ring other than a 6-carbon aromatic ring, and (3) an aromatic ring, with the proviso that said 6, 7, or 8 membered ring (2), is fused to both the cyclopentadienyl ring (1), and the aromatic ring (3), polymerization catalysts, a process to prepare the novel compounds and complexes, and olefin polymerization processes using the same are disclosed.
    Type: Application
    Filed: May 13, 2003
    Publication date: November 20, 2003
    Inventors: Richard E. Campbell, Jerzy Klosin, Ravi B. Shankar, Francis J. Timmers, Robert K. Rosen
  • Patent number: 6630554
    Abstract: (1) A methacrylic ester or an acrylic ester is anionically polymerized, using a polymerization initiator compound comprising an addition reaction product of a conjugated diene compound and an organic alkali metal compound, in the presence of a tertiary organoaluminum compound having in the molecule thereof a chemical structure represented by a formula: Al—O—Ar wherein Ar represents an aromatic ring; or (2) a methacrylic ester or an acrylic ester is anionically polymerized, using a polymerization initiator compound comprising an addition reaction product of an organic alkali metal compound and a compound having a 1,1-diaryl-1-alkene structure, by adding the ester in the form of a mixture with the above-mentioned specific tertiary organoaluminum compound to the polymerization system.
    Type: Grant
    Filed: September 18, 2000
    Date of Patent: October 7, 2003
    Assignee: Kuraray Co., Ltd.
    Inventors: Kenichi Hamada, Kazushige Ishiura, Toru Takahashi, Sachie Yaginuma, Makoto Akai, Tomohiro Ono, Kenji Shachi
  • Patent number: 6627715
    Abstract: The group IIa metal containing catalyst system of this invention can be utilized to synthesize rubbery polymers having a high trans microstructure by solution polymerization. Such rubbery polymers having a high trans microstructure content, such as polybutadiene rubber, styrene-isoprene-butadiene rubber, styrene-butadiene rubber, can be utilized in tire tread rubbers that exhibit improved wear and tear characteristics. This invention more specifically reveals a catalyst system which is comprised of (a) an organolithium compound, including organolithium functionalized compounds, (b) a group IIa metal salt selected from the group consisting of group IIa metal salts of di(alkylene glycol)alkylethers and group IIa metal salts of tri(alkylene glycol) alkylethers, and (c) an organoaluminum compound, and optionally an organomagnesium compound.
    Type: Grant
    Filed: April 17, 2002
    Date of Patent: September 30, 2003
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu, Chad Aaron Jasiunas, John Robert Zuppo, III, Laurie Elizabeth Austin
  • Publication number: 20030032745
    Abstract: Hetero-telechelic polymers having the formula:
    Type: Application
    Filed: March 27, 2000
    Publication date: February 13, 2003
    Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
  • Publication number: 20030013827
    Abstract: Hetero-telechelic polymers having the formula:
    Type: Application
    Filed: June 21, 2002
    Publication date: January 16, 2003
    Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 6455651
    Abstract: The present invention is an improvement in a method of anionically polymerizing monomers by contacting them with an anionic polymerization initiator which is an organo-substituted alkali metal compound in the presence of low amounts of an accelerator/promoter and/or a highly active microstructure modifier. The improvement comprises adding from 0.1 to 1.0 equivalents of a metal alkyl compound per equivalent of alkali metal initiator wherein alkyl groups of the metal alkyl compound are chosen so that they will not exchange with the organo substituents of the alkali metal compound. The preferred initiator for use herein is the sec-butyl lithium adduct of diisopropenyl benzene and the preferred metal alkyl is triethyl aluminum.
    Type: Grant
    Filed: March 14, 2000
    Date of Patent: September 24, 2002
    Assignee: KRATON Polymers U.S. LLC
    Inventors: Carl Lesley Willis, Daniel Earl Goodwin
  • Patent number: 6410654
    Abstract: An anionically polymerized impact-modified polystyrene has a yield stress of at least 24 MPa, measured at 23° C. to DIN 53455 and a hole impact strength of at least 11 kJ/m2, measured at 23° C. to DIN 53753, measured in each case on a specimen produced to ISO 3167. A preparation process is described.
    Type: Grant
    Filed: December 18, 2000
    Date of Patent: June 25, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Philippe Desbois, Christian Schade, Hermann Gausepohl, Volker Warzelhan
  • Patent number: 6388032
    Abstract: A cyclic olefin polymer having a small content of a catalyst residue, a production process for the same and use of the same as an optical material. Catalysts used for polymerization and/or hydrogenation reaction for forming the cyclic olefin polymer are decomposed efficiently by adding at least one compound selected from the group consisting of an &agr;-oxyacid and &bgr;-oxyacid having one hydroxyl group and one carboxyl group in the molecule and derivatives obtained by substituting hydroxyl group thereof by an alkoxyl group, and the decomposition products are removed by rendering them insoluble in a reaction solvent used for the polymerization and/or hydrogenation reaction and precipitating them efficiently.
    Type: Grant
    Filed: April 14, 2000
    Date of Patent: May 14, 2002
    Assignee: Teijin Limited
    Inventors: Michio Yamaura, Kiyonari Hashidzume, Hideaki Nitta, Masaki Takeuchi, Kaoru Iwata
  • Patent number: 6329480
    Abstract: A process for the preparation of an acrylic acid ester polymer, includes carrying out polymerization of an acrylic acid ester or block copolymerization of an acrylic acid ester and another (meth)acrylic monomer in the presence of an organolithium compound and an organoaluminum compound represented by the following formula (I): AlR1R2R3  (I) wherein R1 represents an alkyl group having at least 3 carbon atoms, an alkoxy group having at least 3 carbon atoms or an aryloxy group, R2 and R3 each independently represent an aryloxy group or may be coupled together to form an arylenedioxy group. The process makes it possible to increase the reaction rate and living properties upon polymerization and increase the block formation efficiency upon block copolymerization.
    Type: Grant
    Filed: March 23, 1999
    Date of Patent: December 11, 2001
    Assignee: Kuraray Co., Ltd.
    Inventors: Naohiko Uchiumi, Kenichi Hamada, Masaji Kato, Tomohiro Ono, Sachie Yaginuma, Kazushige Ishiura
  • Patent number: 6303721
    Abstract: The anionic polymerization of dienes or copolymers of dienes and vinylaromatic monomers in a vinylaromatic monomer or monomer mixture to give homopolydienes or copolymers or mixed homopolydienes and copolymers is carried out in the presence of a metal alkyl or aryl of an element having a valence of at least two without addition of Lewis bases.
    Type: Grant
    Filed: February 17, 1999
    Date of Patent: October 16, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Lätsch, Wolfgang Fischer, Hermann Gausepohl, Volker Warzelhan, Christian Schade
  • Patent number: 6150487
    Abstract: This invention relates to a multifunctional organic alkali metal initiator for the preparation of various kinds of star polymers by anionic polymerization, a process for making the initiator, a process using said initiator for making star polymers and the polymers obtained. The initiator can be represented by the formula: M.sub.a (RMe).sub.b, wherein M is selected from Sn, Ti, Al, Si and/or B; R is a hydrocarbyl group containing 8-100 carbon atoms, a=1-3, b=2.5-6.5, Me is an alkali metal which may be selected from Na and Li. The initiator was synthesized by reacting an organic alkali metal with a conjugated diene and/or a mono-olefin monomer, and then adding hetero-atom containing halide. The star polymer obtained has a radial molecular structure consisting of several macromolecular chain arms radiating from the initiator core, and its molecular weight distribution expressed by GPC presents a uniform singlet.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: November 21, 2000
    Assignee: China Petrochemical Corporation
    Inventors: Xingying Zhang, Guantai Jin, Suhe Zhao
  • Patent number: 6103846
    Abstract: The preparation of di- or polyfunctional polymers by anionic polymerization using functionalized initiators having the structure R.sup.1 R.sup.2 R.sup.3 Si--A--B, wherein each R is methyl and A is a hydrocarbon bridging group containing from 1 to 25 carbon atoms, and B is an alkali metal, is improved when polymerization occurs in the presence of a polymerization termination inhibitor which is a metal alkyl which has been added at a concentration to afford a molar ratio of the termination inhibitor to living polymer chain ends of about 0.1:1 to about 10:1.
    Type: Grant
    Filed: May 5, 1999
    Date of Patent: August 15, 2000
    Assignee: Shell Oil Company
    Inventors: Carl Lesley Willis, Robert Charles Bening, Michael Wayne Potter, Grant Wesley Haddix, David Karl Schisla, Thomas Carl Semple, Daniel Earl Goodwin
  • Patent number: 6103842
    Abstract: The process and catalyst system of this invention can be utilized to synthesize a highly random styrene-butadiene rubber having a high trans content by solution polymerization. The styrene-butadiene rubber made by the process of this invention can be utilized in tire tread rubbers that exhibit improved wear characteristics. This invention more specifically reveals a catalyst system for use in exothermal polymerizations which consists essentially of (a) an organolithium compound, (b) a barium alkoxide and (c) a lithium alkoxide. The subject invention further discloses a process for synthesizing a random styrene-butadiene rubber having a low vinyl content by a process which comprises copolymerizing styrene and 1,3-butadiene under isothermal conditions in an organic solvent in the presence of a catalyst system which consists essentially of (a) an organolithium compound, (b) a barium alkoxide and (c) a lithium alkoxide.
    Type: Grant
    Filed: May 4, 1998
    Date of Patent: August 15, 2000
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu, Laurie Elizabeth Austin
  • Patent number: 5936029
    Abstract: The present invention provides a method of anionic synthesis of stable macrocyclic polymers that are compounded to form vulcanizable elastomeric compounds exhibiting reduced hysteresis properties. Cyclic organometallic compounds containing divalent metal atoms of Groups IIA and IIB of the Periodic System are employed as initiators of anionic polymerization of conjugated diene, vinyl aromatic and/or triene monomers. Coupling of the living ends of the resulting macrocyclic polymers or copolymers with a coupling agent or a coupling agent that is also a functionalizing agent results in stable macrocyclic polymers with improved hysteresis properties.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: August 10, 1999
    Assignee: Bridgestone Corporation
    Inventor: James E. Hall
  • Patent number: 5900464
    Abstract: Polar polymers having the following formula:FG--(Q).sub.d --R.sub.n --Z--J--?A(R.sup.1 R.sup.2 R.sup.3)!.sub.x(I)wherein FG is H or a protected or non-protected functional group; Q is a polar hydrocarbyl group derived by incorporation of a polar compound selected from group consisting of esters, amides, and nitriles of acrylic and methacrylic acid, and mixtures thereof; d is an integer from 10 to 2000; R is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic hydrocarbons, and mixtures thereof; n is an integer from 0 to 5; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; J is oxygen, sulfur, or nitrogen; ?A(R.sup.1 R.sup.2 R.sup.3)!.sub.x is a protecting group, in which A is an element selected from Group IVa of the Periodic Table of Elements; R.sup.1, R.sup.2, and R.sup.
    Type: Grant
    Filed: July 10, 1996
    Date of Patent: May 4, 1999
    Assignee: FMC Corporation
    Inventors: Robert J. Letchford, James A. Schwindeman, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 5877336
    Abstract: Triorgano substituted-tin lithium initiators are made in a dimethyl ether solvent. The substitution of dimethyl ether as the solvent for the traditional tetrahydrofuran solvent results in an initiator for anionic polymerizations that can produce less 1,2-vinyl repeat units. The dimethyl ether is also easier to remove from the polymerization media because it has a boiling point at one atmosphere of minus 24.8.degree. C. and thus is a gas at 25.degree. C.
    Type: Grant
    Filed: December 31, 1996
    Date of Patent: March 2, 1999
    Assignee: Bridgestone Corporation
    Inventors: William L. Hergenrother, Tristram W. Bethea
  • Patent number: 5859159
    Abstract: An improved process for the homopolymerization and copolymerization of .alpha.-olefins utilizing highly dilute .alpha.-olefin feedstreams to effect high conversions and catalyst efficiencies in the production of non-ethylene copolymers. The instant invention is particularly adaptable to polymerizing the .alpha.-olefin content of commercially available refinery feedstreams such as Raffinate-2.
    Type: Grant
    Filed: March 14, 1997
    Date of Patent: January 12, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Albert Rossi, Salvatore Rea, Jon E. Stanat, Linda K. Wright, Kenneth L. Kaufman, Jeffrey W. Frederick, Robert Martin Koros, Harold Wilbur Margo
  • Patent number: 5849847
    Abstract: Polyalkenylaromatic-polyethylene copolymers are prepared using protected functional organolithium initiators. Polymerization of an alkenylsubstituted aromatic monomer followed by ethylene, results in a protected functional block polystyrene-co-polyethylenyllithium. Termination with a functionalizing agent followed by deprotection produces polymeric products with high functionalization at the initiating chain-end and at least partial functionalization at the terminal chain-end.
    Type: Grant
    Filed: July 29, 1996
    Date of Patent: December 15, 1998
    Assignee: FMC Corporation
    Inventor: Roderic P. Quirk
  • Patent number: 5753579
    Abstract: The process of this invention can be utilized to synthesize polymers having a high trans microstructure. The polymers which can be prepared utilizing the procedure of this invention include high trans-1,4-polybutadiene, styrene-isoprene-butadiene terpolymers with high trans-1,4-polybutadiene microstructures, high trans-isoprene-butadiene copolymers, and styrene-butadiene copolymers having high trans-1,4-polybutadiene microstructures. Such polymers can be utilized in tire tread rubber compounds which exhibit improved wear characteristics, tear resistance and low temperature performance characteristics. This invention more specifically reveals a process for synthesizing a high trans polymer which comprises adding (a) at least one organolithium initiator or organomagnesium initiator, (b) an organoaluminum compound, (c) a barium alkoxide, and (d) an organozinc compound to a polymerization medium which is comprised of an organic solvent and at least one conjugated diene monomer.
    Type: Grant
    Filed: December 26, 1995
    Date of Patent: May 19, 1998
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: George Jalics, Adel Farhan Halasa