Contains Compound Of Nitrogen Patents (Class 526/180)
  • Patent number: 11525049
    Abstract: The present invention relates to the use of N,N?,N?-substituted hexahydro-1,3,5-triazine in the anionic polymerization of conjugated diene monomer and vinylaromatic monomer. Use of this polar additive produces copolymers having both high vinylaromatic and low vinyl contents, while the blockiness of the vinylaromatic unit can be tailored.
    Type: Grant
    Filed: March 28, 2018
    Date of Patent: December 13, 2022
    Assignees: SYNTHOS S.A., SYNTHOS DWORY 7 SPÓLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA SPÓLKA JAWNA
    Inventors: Radoslaw Kozak, Robert Bogacz, Malgorzata Walenia, Pawel Weda
  • Patent number: 11254801
    Abstract: The present invention relates to a modified polymerization initiator for a conjugated diene-based polymer, and a modified conjugated diene-based polymer including a functional group derived from the modified polymerization initiator.
    Type: Grant
    Filed: August 21, 2018
    Date of Patent: February 22, 2022
    Inventors: Jung Yong Lee, Jae Hoon Choe, Dong Cheol Choe, Jong Young Choi, Won Jae Lee, Hyeon Hui Kim
  • Patent number: 10618994
    Abstract: An ethylenically unsaturated polymer includes at a terminus the radical of a compound that is the reaction product of a secondary amine and a vinyl aromatic compound. The secondary amine portion of the compound can be a cyclic compound with N as one of its ring atoms, while the vinyl aromatic compound can include one or more substituents. The polymer can be used as a component of a variety of elastomeric compounds used in the production of vulcanizates.
    Type: Grant
    Filed: October 8, 2016
    Date of Patent: April 14, 2020
    Assignee: Bridgestone Corporation
    Inventors: Yuan-Yong Yan, David M. Roggeman
  • Patent number: 9000109
    Abstract: A process for polymerization of a polymer containing monomeric units derived from a styrene monomer and a 1,3-butadiene monomer includes polymerizing the monomeric units in the presence of an initiator, a first polar agent, and a second polar agent. The first polar agent includes a structure (I): R1?R2?N-Q-NR3?R4?; and the second polar agent comprises a structure (II): R1?, R2?, R3?, and R4? are each independently selected from the group consisting of an alkyl group and hydrogen; Q contains an alkylene group; R1 and R2 are each independently an alkyl group; and R3, R4, R5, R6, R7 and R8 are each independently selected from the group consisting of an alkyl group and hydrogen. Polymers prepared by the above process are described, as are compositions containing such a polymer, and articles containing at least one component formed from such a composition.
    Type: Grant
    Filed: March 1, 2012
    Date of Patent: April 7, 2015
    Assignee: Styron Europe GmbH
    Inventors: Evemarie Hamann, Silvia Valenti, Karin Schmiedel
  • Patent number: 8933159
    Abstract: Described are a particular group of novel aromatic hydrocarbon telomers that, on bromination, result in the formation of novel flame retardants having a uniquely beneficial combination of properties. The resultant flame retardants and uses thereof are also described. The disclosure includes descriptions of methods for preparing both the aromatic hydrocarbon telomers and the brominated flame retardant polymers.
    Type: Grant
    Filed: November 30, 2009
    Date of Patent: January 13, 2015
    Assignee: Albemarle Corporation
    Inventors: William J. Layman, Jr., Charles H. Kolich, Arthur G. Mack, Jonathan P. McCarney, Govindarajulu Kumar, Jorge Morice, Zhongxin Ge, Bo Liu, Douglas W. Luther, Kimberly M. White, Bruce C. Berris, Junzuo Wang
  • Patent number: 8916665
    Abstract: Metallated aminosilane compounds for use as functional initiators in anionic polymerizations and processes for producing an aminosilane-functionalized polymer using the metallated aminosilane compounds to initiate anionic polymerization of at least one type of anionically polymerizable monomer. Preferred use of the metallated aminosilane compounds results in rubber compositions for use in tires comprising an aminosilane functionalized polymer. A telechelic polymer may result from use of the metallated aminosilane compound as a functional terminator.
    Type: Grant
    Filed: June 22, 2011
    Date of Patent: December 23, 2014
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Terrence E. Hogan, Christine Rademacher, David M. Roggeman, Fuminori Ota
  • Patent number: 8877832
    Abstract: The present invention provides a process for producing a conjugated diene-based polymer comprising polymerizing a monomer component comprising a conjugated diene compound and a silicon-containing vinyl compound using the following compounds (I) and (II), as a polymerization initiator component, (I) an organic alkali metal compound (II) a compound represented by the following formula (I) wherein R11 and R12 represent a hydrocarbyl group having 1 to 20 carbon atoms optionally having a substituent.
    Type: Grant
    Filed: January 23, 2012
    Date of Patent: November 4, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mana Ito, Katsunari Inagaki, Mayumi Oshima
  • Publication number: 20140309390
    Abstract: A stabilized initiator solution comprising a multi-valent lithiated containing initiator and an aliphatic or cycloaliphatic solvent.
    Type: Application
    Filed: December 17, 2012
    Publication date: October 16, 2014
    Inventor: Yuan-Yong Yan
  • Patent number: 8815977
    Abstract: The present invention provides a process for producing a conjugated diene-based polymer, comprising polymerizing a monomer component containing a conjugated diene compound and a silicon-containing vinyl compound using a polymerization initiator represented by the following formula (1) wherein, R11 represents a hydrocarbylene group having 6 to 100 carbon atoms, R12 and R13 represent a hydrocarbyl group optionally having a substituent, or a trihydrocarbylsilyl group, or R12 and R13 are bonded to represent a hydrocarbylene group optionally having, as a hetero atom, at least one kind atom selected from the atomic group consisting of a silicon atom, a nitrogen atom and an oxygen atom.
    Type: Grant
    Filed: January 24, 2012
    Date of Patent: August 26, 2014
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Mana Ito, Katsunari Inagaki, Mayumi Oshima
  • Patent number: 8750762
    Abstract: To provide a charging member that can have a uniform electrical resistance, can not easily change in electrical resistance even by any long-term continuous electrification and, as a result thereof, may cause less change in its charging performance with time. A charging member having a conductive support and an elastic-material layer; the elastic-material layer comprising a vulcanized rubber; the vulcanized rubber being a vulcanized product of a composition which comprises i) a binder polymer comprising a polymer having a butadiene skeleton and ii) carbon black as electrically conductive particles; and the polymer having a butadiene skeleton has a molecular terminal modified with an atomic group having a specific structure.
    Type: Grant
    Filed: February 15, 2011
    Date of Patent: June 10, 2014
    Assignee: Canon Kabushiki Kaisha
    Inventors: Masaaki Harada, Hiroaki Watanabe, Keiji Nose
  • Patent number: 8729204
    Abstract: Compositions and methods for producing polymerization initiators comprising at least two protected primary amine groups. Polymers prepared using such polymerization initiators can comprise a residue of the polymerization initiator and can initially comprise the at least two protected primary amine groups. Such polymers can undergo a deprotection process thereby yielding a polymer having one or more unprotected primary amine groups. Polymers having primary amine groups can be employed in rubber compositions, which have a variety of potential applications, such as, for example, in tire manufacturing.
    Type: Grant
    Filed: September 10, 2010
    Date of Patent: May 20, 2014
    Assignee: Bridgestone Corporation
    Inventors: Eiju Suzuki, Terrence E. Hogan
  • Patent number: 8710164
    Abstract: A process for the preparation of diene polymers or vinylarene-diene statistical (random) copolymers which comprises the anionic (cp) polymerization, in hydrocarbon solvents, of at least one monomer of a conjugated diene, optionally in the presence of a vinyl aryl monomer, and using a compound belonging to the group of lithium alkyls as initiator, characterized in that the total lithium alkyl initiator is modified in situ by means of a reaction with a compound having general formula (I): Rm—(X—H)n (I) wherein R is a C2-C20 (cyclo) alkyl or C6-C20 aromatic radical, X is a heteroatom belonging to group VA or group VIA of the periodic system, n is an integer higher than or equal to 1, m is an integer>1 which depends on the valence of the heteroatom X.
    Type: Grant
    Filed: September 29, 2011
    Date of Patent: April 29, 2014
    Assignee: Polimeri Europa S.p.A.
    Inventors: Luca Soddu, Gabriele Veneri
  • Publication number: 20130345379
    Abstract: A process for polymerization of a polymer containing monomeric units derived from a styrene monomer and a 1,3-butadiene monomer includes polymerizing the monomeric units in the presence of an initiator, a first polar agent, and a second polar agent. The first polar agent includes a structure (I): R1?R2?N-Q-NR3?R4?; and the second polar agent comprises a structure (II): R1?, R2?, R3?, and R4? are each independently selected from the group consisting of an alkyl group and hydrogen; Q contains an alkylene group; R1 and R2 are each independently an alkyl group; and R3, R4, R5, R6, R7 and R8 are each independently selected from the group consisting of an alkyl group and hydrogen. Polymers prepared by the above process are described, as are compositions containing such a polymer, and articles containing at least one component formed from such a composition.
    Type: Application
    Filed: March 1, 2012
    Publication date: December 26, 2013
    Inventors: Evemarie Hamann, Silvia Valenti, Karin Schmiedel
  • Patent number: 8436097
    Abstract: A process for producing a modified polymer rubber comprising the steps of: (1) polymerizing a conjugated diene monomer or a combination thereof with an aromatic vinyl monomer in a hydrocarbon solvent, in the presence of an alkali metal catalyst or a specified alkali metal compound, to form an alkali metal end-carrying active polymer, and (2) reacting the alkali metal end-carrying active polymer with a specified isocyanurate compound or a combination thereof with a specified coupling agent in a hydrocarbon solvent.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: May 7, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Katsunari Inagaki, Seiichi Mabe, Mayumi Oshima
  • Patent number: 8389644
    Abstract: A functionalized polymer includes a directly bonded moiety, which can be located at a terminus of the polymer, defined by the formula —NH—NR1R2 where R1 and R2 independently are substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, allyl, aralkyl, alkaryl, or alkynyl groups, or together form a substituted or unsubstituted alkylene, alkenylene, cycloalkylene, cycloalkenylene, or arylene group. The functionalized polymer can be provided by reacting a living polymer with a hydrazone. Such polymers can be used in the production of compositions that include particulate fillers.
    Type: Grant
    Filed: October 23, 2007
    Date of Patent: March 5, 2013
    Assignee: Bridgestone Corp.
    Inventors: Dennis R. Brumbaugh, Steven Luo, Christine Rademacher, Yuan-Yong Yan
  • Patent number: 8362181
    Abstract: A sulfur-containing anionic polymerization initiator defined by the formula: R1S—R2aR3?Li? where R1 is a monovalent organic group, R2 is a divalent organic group, R3 is a divalent organic group or a bond, and a is an integer from 1 to about 5.
    Type: Grant
    Filed: September 28, 2011
    Date of Patent: January 29, 2013
    Assignee: Bridgestone Corporation
    Inventors: Terrence E. Hogan, William L. Hergenrother
  • Publication number: 20120190771
    Abstract: The present invention provides a process for producing a conjugated diene-based polymer, comprising polymerizing a monomer component containing a conjugated diene compound and a silicon-containing vinyl compound using a polymerization initiator represented by the following formula (1) wherein, R11 represents a hydrocarbylene group having 6 to 100 carbon atoms, R12 and R13 represent a hydrocarbyl group optionally having a substituent, or a trihydrocarbylsilyl group, or R12 and R13 are bonded to represent a hydrocarbylene group optionally having, as a hetero atom, at least one kind atom selected from the atomic group consisting of a silicon atom, a nitrogen atom and an oxygen atom.
    Type: Application
    Filed: January 24, 2012
    Publication date: July 26, 2012
    Inventors: Mana Ito, Katsunari Inagaki, Mayumi Oshima
  • 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
  • Patent number: 8207282
    Abstract: A novel polymeric compound is provided. The polymeric compound is highly compatible with reinforcing materials. Particularly, the polymeric compound is highly miscible with inorganic reinforcing materials in the manufacture of a tire. Further provided is a novel bifunctional initiator necessary to prepare the polymeric compound. The bifunctional initiator contains amine moieties. Active ends of the polymer are modified with an alkoxysilane compound. The polymer has an improved affinity for carbon black and silica as reinforcing materials in the manufacture of a tire. Therefore, the use of the polymer can achieve desired physical properties required in a tire, e.g., high wet traction, low rolling resistance and high tread wear.
    Type: Grant
    Filed: September 18, 2009
    Date of Patent: June 26, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Du Weon Yoon, Tae Chul Lee, Jeong Hyun Noh
  • Publication number: 20120035336
    Abstract: The embodiments of the invention relate to a multifunctional lithiated amine-containing compound comprising at least two molecules of lithiated amine in a molecule of the compound. In one embodiment, the compound has a formula where x is an integer of 1 or more, Q is (a) an element selected from the group consisting of O, S, N, P and Si or (b) an alkylene group having from 1 to 20 methylene groups, and R1 and R2 are the same or different and are selected from the group consisting of alkyls, cycloalkyls and aralkyls containing from 1 to 20 carbon atoms. In another embodiment, the compound comprises cyclic lithio amines and has a formula: where x is 1 or more, R3, R4 and R5 are the same or different and represent alkylene groups containing from 3 to 20 carbon atoms.
    Type: Application
    Filed: October 12, 2011
    Publication date: February 9, 2012
    Applicant: BRIDGESTONE CORPORATION
    Inventor: YUAN-YONG YAN
  • Patent number: 8063165
    Abstract: A method for forming a polymer including a sulfur-containing functional group, the method comprising introducing a sulfur-containing initiator defined by the formula with conjugated diene monomer and optionally copolymerizable monomer within a polymerization medium and allowing the sulfur-containing initiator to initiate the polymerization of the conjugated diene monomer and the optional copolymerizable monomer, where R1 is a monovalent organic group, R2 is a divalent organic group, R3 is a divalent organic group or a bond, and a is an integer from 1 to about 5.
    Type: Grant
    Filed: June 16, 2008
    Date of Patent: November 22, 2011
    Assignee: Bridgestone Corporation
    Inventors: Terrence E. Hogan, William L. Hergenrother
  • Patent number: 7981990
    Abstract: A method comprising: (a) forming a living liquid polymer, wherein said living liquid polymer is anionically initiated and comprises a cation; (b) adding a functional initiator precursor of the formula FI-H, wherein H is hydrogen and FI is a functional group, said H terminates said living liquid polymer resulting in said liquid polymer having a number average molecular weight of about 20,000 (g/mole) to about 100,000 (g/mole), and said FI and said cation form a functional initiator; (c) adding monomer, wherein said functional initiator initiates anionic polymerization of said monomer; and (d) terminating the polymerization reaction initiated in step (c). Steps (a) through (c) may be conducted in a single reactor, allowing a liquid polymer to be dispersed in a functionalized polymer in a single polymerization step. Thus, the liquid polymer does not have to be handled separately and processing efficiency is improved.
    Type: Grant
    Filed: August 28, 2008
    Date of Patent: July 19, 2011
    Assignee: Bridgestone Corporation
    Inventor: Yuan-Yong Yan
  • 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: 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
  • Publication number: 20090326176
    Abstract: The embodiments of the invention relate to a multifunctional lithiated amine-containing compound comprising at least two molecules of lithiated amine in a molecule of the compound. In one embodiment, the compound has a formula where x is an integer of 1 or more, Q is (a) an element selected from the group consisting of O, S, N, P and Si or (b) an alkylene group having from 1 to 20 methylene groups, and R1 and R2 are the same or different and are selected from the group consisting of alkyls, cycloalkyls and aralkyls containing from 1 to 20 carbon atoms. In another embodiment, the compound comprises cyclic lithio amines and has a formula: where x is 1 or more, R3, R4 and R5 are the same or different and represent alkylene groups containing from 3 to 20 carbon atoms.
    Type: Application
    Filed: December 29, 2008
    Publication date: December 31, 2009
    Inventor: Yuan-Yong Yan
  • Publication number: 20090082534
    Abstract: The present invention relates to a linear or branched diene elastomer having cyclic vinyl units. A linear diene elastomer according to the invention results from at least one conjugated diene and it comprises cyclic vinyl units in a mass content of greater than or equal to 15% while having a number-average molecular weight falling within a range of from 10,000 to 300,000 g/mol.
    Type: Application
    Filed: November 20, 2008
    Publication date: March 26, 2009
    Applicant: MICHELIN RECHERCHE ET TECHNIQUE S.A.
    Inventors: Jean-Luc Cabioch, Laurent Coissieux, Nicole Dajoux
  • Patent number: 7470760
    Abstract: The present invention relates to a linear or branched diene elastomer having cyclic vinyl units. A linear diene elastomer according to the invention results from at least one conjugated diene and it comprises cyclic vinyl units in a mass content of greater than or equal to 15% while having a number-average molecular weight falling within a range of from 10,000 to 300,000 g/mol.
    Type: Grant
    Filed: January 14, 2004
    Date of Patent: December 30, 2008
    Assignee: Michelin Recherche Et Technique, S.A.
    Inventors: Jean-Luc Cabioch, Laurent Coissieux, Nicole Dajoux
  • Patent number: 7462677
    Abstract: An initiator is presented for anionically polymerizing monomers, to provide a functional head group on the polymer. A polymer having a functional head group derived from a sulfur containing anionic initiator, and optionally as additional functional group resulting from the use of a functional terminating reagent, coupling agent or linking agent is also provided. A method is presented for anionically polymerizing monomers comprising the step of polymerizing the monomers with a sulfur containing anionic initiator to provide a functional head group on the polymer. An elastomeric compound, comprising a functional polymer and filler is also described. Also provided is a tire having decreased rolling resistance resulting from a tire component containing a vulcanizable elastomeric compound.
    Type: Grant
    Filed: September 13, 2007
    Date of Patent: December 9, 2008
    Assignee: Bridgestone Corporation
    Inventors: Terrence E. Hogan, William Hergenrother, Yuan-Yong Yan, David Lawson
  • 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
  • Publication number: 20080161519
    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: Application
    Filed: December 28, 2006
    Publication date: July 3, 2008
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu
  • Patent number: 7342070
    Abstract: Disclosed are a conjugated diolefin (co) polymer rubber formed from either a conjugated diolefin or a conjugated diolefin and an aromatic vinyl compound, wherein the (co) polymer rubber has a primary amino group and an alkoxysilyl group which are bonded to a (co) polymer chain; a process for producing the same; a rubber composition; a composite; and a tire. The (co) polymer rubber has satisfactory processability, and can give an automotive tire tread having a balance among wear resistance, failure characteristics, low hysteresis loss and wet-skid characteristics.
    Type: Grant
    Filed: September 25, 2002
    Date of Patent: March 11, 2008
    Assignee: JSR Corporation
    Inventors: Keisuke Tsukimawashi, Naokazu Kobayashi, Tsukasa Toyoshima, Toshihiro Tadaki, Kouta Taniguchi
  • 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
  • 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: 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: 7153919
    Abstract: An initiator is presented for anionically polymerizing monomers, to provide a functional head group on the polymer. A polymer having a functional head group derived from a sulfur containing anionic initiator, and optionally as additional functional group resulting from the use of a functional terminating reagent, coupling agent or linking agent is also provided. A method is presented for anionically polymerizing monomers comprising the step of polymerizing the monomers with a sulfur containing anionic initiator to provide a functional head group on the polymer. An elastomeric compound, comprising a functional polymer and filler is also described. Also provided is a tire having decreased rolling resistance resulting from a tire component containing a vulcanizable elastomeric compound.
    Type: Grant
    Filed: October 30, 2003
    Date of Patent: December 26, 2006
    Assignee: Bridgestone Corporation
    Inventors: Terrence E. Hogan, William Hergenrother, Yuan-Yong Yan, David Lawson
  • 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
  • Patent number: 6891019
    Abstract: Anionic polymerization initiators useful in the preparation of polymers having a protected amine functional group. The amine functionality includes a first protecting group, which can be aralkyl, methyl, allyl or tertiary alkyl group. The other of the amine protecting groups can be the same as the first protecting group. Alternatively, the second protecting group can be different from the first protecting group, in which case it is selected to have differential stability to agents used to remove the aralkyl, methyl, allyl or tertiary alkyl protecting group.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: May 10, 2005
    Assignee: FMC Corporation
    Inventors: Thorsten Werner Brockmann, Randy W. Hall
  • Patent number: 6818710
    Abstract: There is provided a process for producing a modified polymer rubber, which comprises the steps of: (1) reacting one part by mol of an organoalkali metal compound with n±0.7 (n is an integer of 3 or more) parts by mol of a specific diphenyl compound to produce a reaction mixture, (2) polymerizing in the presence of the produced reaction mixture an aromatic vinyl monomer and a conjugated diene monomer in a hydrocarbon solvent, and after completion of the polymerizing, stirring for at least 30 minutes, to produce a polymerization reaction mixture, and (3) repeating such an operation n−2 times that (i) an aromatic vinyl monomer and a conjugated diene monomer are added to the produced polymerization reaction mixture, and polymerized, and (ii) after completion of the polymerizing, stirring is carried out for at least 30 minutes, and thereby producing a modified polymer rubber, whose both ends and n−2 positions in its chain are modified by the compound represented by the formula (1).
    Type: Grant
    Filed: April 1, 2003
    Date of Patent: November 16, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mayumi Oshima, Seiichi Mabe, Katsunari Inagaki
  • 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: 6765065
    Abstract: There is provided a process for producing a modified polymer rubber having modified both ends, which comprises the steps of: (1) reacting a compound represented by the following formula (1) with an organic alkali metal compound to produce a chemical species, (2) polymerizing a conjugated diene monomer or a combination of a conjugated diene monomer with an aromatic vinyl monomer in the presence of the chemical species to produce an active polymer having an alkali metal at an end thereof, and (3) reacting the active polymer with a functional group-carrying modifying agent in a hydrocarbon solvent to produce the modified polymer rubber having modified both ends.
    Type: Grant
    Filed: October 10, 2002
    Date of Patent: July 20, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mayumi Oshima, Seiichi Mabe, Katsunari Inagaki
  • Patent number: 6762259
    Abstract: The purpose of the present invention is to provide polymerization catalyst which can produce quite efficiently (co)polymer having number average molecular weight and number of molecules which are accurately controlled in producing method of (co)polymer by the polymerization of polar unsaturated compound, and provide living polymerized (co)polymer obtained according to the producing method. For the purpose, polymerization catalyst composition which comprises the composition comprising organic oxysalt compound and hydroxycarbonyl compound having at least both an alcoholic hydroxyl group and a carbonyl group in the same molecule is provided and the polar unsaturated compound is polymerized by using the polymerization catalyst composition. The composition containing the obtained (co)polymer were able to provide thermosetting powder coating composition having particularly excellent characteristics.
    Type: Grant
    Filed: June 12, 2002
    Date of Patent: July 13, 2004
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tadahito Nobori, Katsuhiko Funaki, Atsushi Shibahara, Makoto Suzuki, Kazumi Mizutani, Hiromi Jouyama, Isao Hara, Takaomi Hayashi, Shinji Kiyono, Setsuko Fujiyoshi, Hiroyuki Sakayama, Mitsuyuki Mizoguchi, Tsuyoshi Matsumoto, Yoshiharu Hirose
  • 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
  • Patent number: 6699939
    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 2, 2004
    Assignee: FMC Corporation, Lithium Division
    Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 6686423
    Abstract: In a process for the anionic polymerization of vinylaromatic monomers or dienes in the presence of a lithium organyl or lithium alcoholate and a magnesium and/or an aluminum compound, a sterically hindered phenol or amine is added.
    Type: Grant
    Filed: May 6, 2002
    Date of Patent: February 3, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Philippe Desbois, Volker Warzelhan, Christian Schade, Michel Fontanille, Alain Deffieux, Stephane Menoret
  • Patent number: 6660819
    Abstract: The invention relates to a process for producing water-soluble or water-swellable polymer products with low levels of residual monomers using acrylic acid and/or acrylic acid derivatives, which process is characterized by adding a nitrogen compound to the monomer solution to be polymerized and subsequent heating of the polymer product at temperatures of from 120 to 240° C. The polymers produced accordingly are suitable for use as flocculants, dispersants and absorbents.
    Type: Grant
    Filed: October 1, 2002
    Date of Patent: December 9, 2003
    Assignee: Stockhausen GmbH & Co. KG
    Inventors: Miroslav Chmelir, Kurt Dahmen
  • Publication number: 20030187164
    Abstract: The invention relates to solutions of lithium pyrrolidine in a mixture consisting of tetrahydrofuran (THF) and of hydrocarbons, whereby the lithium pyrrolidine concentration ranges from 2 to 30 wt. %, and the molar ratio Li pyrrolidine: THF=1: 0.5 to 1: 1.5. The invention also relates to methods for preparing these solutions and to uses of these solutions.
    Type: Application
    Filed: January 3, 2003
    Publication date: October 2, 2003
    Inventors: Wilfried Weiss, Ute Emmel, Franz Totter, Ulrich Wietelmann
  • 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
  • Patent number: 6624267
    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: January 6, 2000
    Date of Patent: September 23, 2003
    Assignee: Michelin Recherche et Technique S.A.
    Inventors: Jean-Michel Favrot, Philippe Laubry