Contains Oxygen Atom Patents (Class 526/181)
  • 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: 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: 6670435
    Abstract: The process and catalyst system of this invention can be utilized to synthesize polybutadiene rubber having a high trans content and a low melting point by solution polymerization. The trans-polybutadiene rubber made by the process of this invention can be utilized in tire tread rubbers that exhibit outstanding wear characteristics. More importantly, the trans-polybutadiene rubber of this invention can be easily processed because of its low level of crystallinity. In fact, the trans-polybutadiene made by the process of this invention does not need to be heated in a “hot-house” before being used in making rubber compounds.
    Type: Grant
    Filed: December 2, 2002
    Date of Patent: December 30, 2003
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Adel Farhan Halasa
  • Patent number: 6657028
    Abstract: A batch process for the anionic polymerization of a styrenic monomer is described. The process brings together a liquid saturated hydrocarbon diluent, an ether promoter, an organolithium initiator and a styrenic monomer in such a way so as to maintain the reaction mixture at or below about 55° C. and so that the amount of organolithium initiator employed is in the range of about 1 to about 10 mol %, based upon the total amount of styrenic monomer to be added. Favorable polydispersity and molecular weight polymer characteristics are obtained.
    Type: Grant
    Filed: August 1, 2002
    Date of Patent: December 2, 2003
    Assignee: Albemarle Corporation
    Inventors: J. Todd Aplin, Charles H. Kolich, W. Dirk Klobucar, Kimberly A. Maxwell
  • Publication number: 20030134997
    Abstract: This invention discloses a rubbery polymer which is comprised of repeat units that are derived from (1) at least one conjugated diolefin monomer, and (2) at least one functionalized monomer having of the structural formula: 1
    Type: Application
    Filed: December 26, 2002
    Publication date: July 17, 2003
    Applicant: The Goodyear Tire & Rubber Company
    Inventors: Stephan Rodewald, Steven Kristofer Henning, Brian Earl Burkhart
  • Patent number: 6566478
    Abstract: This invention is based upon the discovery that rubbery polymers having a high vinyl content and a low degree of branching can be synthesized with an initiator system that is comprised of (a) a lithium initiator selected from the group consisting of allylic lithium compounds and benzylic lithium compounds, (b) a Group I metal alkoxide, and (c) a polar modifier; wherein the molar ratio of the Group I metal alkoxide to the polar modifier is within the range of about 0.1:1 to about 10:1; and wherein the molar ratio of the Group I metal alkoxide to the lithium initiator is within the range of about 0.01:1 to about 20:1. These high vinyl polymers offer reduced levels of hysteresis and better functionalization efficiency.
    Type: Grant
    Filed: April 30, 2002
    Date of Patent: May 20, 2003
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Steven Kristofer Henning, Michael Lester Kerns, Zhengfang Xu
  • 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: 20030032746
    Abstract: Hetero-telechelic polymers having the formula:
    Type: Application
    Filed: June 21, 2002
    Publication date: February 13, 2003
    Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 6515087
    Abstract: It is important for rubbery polymers that are used in tires, hoses, power transmission belts and other industrial products to have good compatibility with fillers, such as carbon black, silica, clay (including organoclays), and mixtures thereof. To attain improved interaction with fillers such rubbery polymers can be functionalized with various compounds, such as amines. The present invention discloses a process for synthesizing a rubbery polymer that is functionalized to attain improved compatibility with fillers.
    Type: Grant
    Filed: December 6, 2001
    Date of Patent: February 4, 2003
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Adel Farhan Halasa, Scott McDowell Christian, Michael Lester Kerns
  • 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: 6489415
    Abstract: The process and catalyst system of this invention can be utilized to synthesize polybutadiene rubber having a high trans content and a low melting point by solution polymerization. The trans-polybutadiene rubber made by the process of this invention can be utilized in tire tread rubbers that exhibit outstanding wear characteristics. More importantly, the trans-polybutadiene rubber of this invention can be easily processed because of its low level of crystallinity. In fact, the trans-polybutadiene made by the process of this invention does not need to be heated in a “hot-house” before being used in making rubber compounds.
    Type: Grant
    Filed: December 5, 2000
    Date of Patent: December 3, 2002
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Adel Farhan Halasa
  • Patent number: 6451949
    Abstract: Disclosed is a process for the production of poly(trimethylene carbonate) which comprises reacting trimethylene carbonate, a catalyst, and an alcohol, preferably a polyhydric alcohol, under nitrogen at atmospheric pressure and a moderate temperature, in a stoichiometric ratio to give the desired molecular weight of poly(trimethylene carbonate) in the presence of a catalyst selected from the group consisting of a salt, preferably an acetate, of an element of Group IA or IIA of the Periodic Table. In an alternative embodiment, high molecular weight poly(trimethylene carbonate) is produced without the use of an initiator, using the same catalyst and longer reaction times.
    Type: Grant
    Filed: February 9, 2001
    Date of Patent: September 17, 2002
    Assignee: Shell Oil Company
    Inventors: Wyndham Henry Boon, Roy Frank Smith, David Eric Gwyn, Thomas Clayton Forschner
  • Patent number: 6429273
    Abstract: A process for producing a vinyl polymer which comprises carrying out anionic polymerization under the condition that the polymerization temperature is not lower than 45° C. and not higher than 250° C. and the concentration of the vinyl monomer based on the polymerization solvent is 45-100% by weight, wherein the metal of the cation forming a counterpart to the carbonic anion at the polymerization propagating species consists essentially of Mg, or Mg and M1 wherein M1 is at least one alkali metal selected from the group consisting of Li, Na and K, and the molar concentrations of the metals of Mg and M1 satisfy the relation of [Mg]/[M1]≧4, the invention also relates to a vinyl monomer polymerization initiator comprising (R2)2Mg wherein R2 is a hydrocarbon group.
    Type: Grant
    Filed: September 14, 1998
    Date of Patent: August 6, 2002
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventor: Kenji Ebara
  • Publication number: 20020068798
    Abstract: Rubbery polymers made by anionic polymerization can be coupled with tin halides or silicon halides to improve the characteristics of the rubber for use in some applications, such as tire treads. In cases where the rubbery polymer is synthesized by anionic polymerization utilizing a polar modifier it is difficult to attain a high level of coupling.
    Type: Application
    Filed: October 10, 2001
    Publication date: June 6, 2002
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu
  • Patent number: 6277936
    Abstract: Chlorotrifluoroethylene (CTFE) thermoplastic copolymers, comprising: (a) from 0.15 to 4% by moles of one or more fluorodioxoles having the general formula:  wherein: X1 and X2, equal to or different from each other, are selected among —F or —CF3; Z is selected among —F, —H, —Cl; Y is equal to ORf and Rf is a perfluoroalkyl having from 1 to 5 carbon atoms, or Y=Z; (b) CTFE, forming the remaining part to 100% by moles.
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: August 21, 2001
    Assignee: Auismont S.p.A.
    Inventors: Julio A. Abusleme, Claudia Manzoni
  • Patent number: 6271324
    Abstract: Homopolymers, copolymers or block copolymers are prepared by anionic polymerization of acrylates and/or methacrylates in the presence of an initiator composition containing A) an organic alkali metal compound, B) an organic aluminum compound and C) an additive which forms a complex with the alkali metal cation and is selected from the group consisting of open-chain ethers having at least two ether oxygen atoms, macrocyclic ethers and cryptands, or from the group consisting of quaternary cations of the general formula I  where A is N, P, As or Sb and Ra, Rb, Rc and Rd, independently of one another, are each unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, where two neighboring radicals, together with the heteroatom A, may form a 5- or 6-membered heterocyclic structure which may contain one or two further heteroatoms selected from nitrogen, oxygen and sulfur atoms.
    Type: Grant
    Filed: May 12, 1999
    Date of Patent: August 7, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Stephan Jüngling, Christof Mehler, Horst Weiss, Susanne Steiger, Axel Müller, Helmut Schlaad, Bardo Schmitt
  • Patent number: 6262204
    Abstract: The present invention relates to an initiation system comprising at least one initiator, with the exception of amides of alkaline metals, and at least one alkaline metal alcoholate of the formula ROM, in which M is an alkaline metal and R represents a group Q—R1—(OR2—)m wherein Q is a heterocyclic compound with 5 or 6 chain links, substituted or not, having 1 or 2 oxygen atoms as heteroatoms, R1 and R2 represent an alkylene group, linear or branched at C1-C4, and m is equal to 0, 1, 2 or 3. The present invention also relates to the application of the initiation system to the preparation of (meth)acrylic (co)polymers and, possibly, ethylenically unsaturated monomers that can be copolymerized with (meth)acrylic monomers.
    Type: Grant
    Filed: April 10, 1998
    Date of Patent: July 17, 2001
    Assignee: Atofina
    Inventors: Axel H. E. Müller, Andreas R. Maurer, Christophe Navarro
  • Patent number: 6221991
    Abstract: Polar polymers having the following formula: FG-(Q)d-Rn-Z-J-[A(R1R2R3)]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 nitrites 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(R1R2R3)]x is a protecting group, in which 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
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: April 24, 2001
    Assignee: FMC Corporation
    Inventors: Robert J. Letchford, James A. Schwindeman, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 6218485
    Abstract: A process for producing a monodisperse polymer which has a number-average molecular weight from 1,000 to 100,000 and a molecular weight distribution Mw (weight-average molecular weight)/Mn (number-average molecular weight)=1.00 through 1.50 is disclosed. This process comprises: homopolymerizing or random copolymerizing an anionic polymerizable compound by living anionic polymerization using an organic alkali metal and/or an alkali metal as a polymerization initiator, wherein a target molecular weight is obtained by adding the compound divided into multiple steps.
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: April 17, 2001
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Hiroo Muramoto, Yukikazu Nobuhara, Eiichiro Kobayashi
  • Patent number: 6166160
    Abstract: There is a need for odorless rubbery polymers that offer high heat resistance, ultraviolet light resistance and low fogging characteristics. For instance, rubbery polymers of this type are needed by the automotive and construction industries. The deodorized rubbery polymers of this invention are of particular value because they can be blended with polyvinyl chloride to make leathery compositions having good heat and ultraviolet light resistance.
    Type: Grant
    Filed: February 4, 1999
    Date of Patent: December 26, 2000
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Hung Dang Ngoc
  • Patent number: 6160054
    Abstract: Hetero-telechelic polymers having the formula:FG--(Q).sub.d --Z--J--[A(R.sup.1 R.sup.2 R.sup.3)].sub.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(R.sup.1 R.sup.2 R.sup.3)].sub.x is a protecting group, wherein 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 18, 1996
    Date of Patent: December 12, 2000
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
  • Patent number: 6153706
    Abstract: This invention provides novel protected, multi-functionalized multi-arm polymers, their optionally hydrogenated analogues and optionally deprotected analogues thereof, and processes for making these compounds. In the invention, monomers are polymerized using a protected functionalized initiator to form living polymer anions, the living anions coupled to form multi-arm polymers, additional monomer added to form additional polymer arms, and the multi-arm polymer functionalized using electrophiles.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: November 28, 2000
    Assignee: FMC Corporation
    Inventors: Robert James Letchford, James Anthony Schwindeman
  • Patent number: 6153675
    Abstract: A water-dispersible, water- and oil-repellent agent, which comprises an aqueous emulsion comprising a copolymer of a fluoroalkyl group-containing monomer with vinylidene chloride or benzyl (meth)acrylate and a carboxyl group-containing, water-soluble polymer, dispersed in water by a nonionic surfactant, preferably the carboxyl group-containing, water-soluble polymer is used together with a sugar alcohol, contains no organic solvent and has a distinguished freeze-thaw stability.
    Type: Grant
    Filed: August 13, 1998
    Date of Patent: November 28, 2000
    Assignee: Nippon Mektron, Limited
    Inventors: Kazuhiro Yamamoto, Yuzuru Ishida
  • Patent number: 6140434
    Abstract: Metal salts of saturated aliphatic alcohols can be used as modifiers in lithium initiated solution polymerizations of diene monomers into rubbery polymers. Sodium t-amylate is a preferred modifiers because of its exceptional solubility in non-polar aliphatic hydrocarbon solvents that are employed as the medium for such solution polymerizations. However, using sodium t-amylate as the polymerization modifier in commercial operations where recycle is required can lead to certain problems. These problems arise due to the fact that sodium t-amylate reacts with water to form t-amyl alcohol during steam stripping in the polymer finishing step. Since t-amyl alcohol forms an azeotrope with hexane, it co-distills with hexane and thus contaminates the feed stream. The present invention solves the problem of recycle stream contamination. This invention is based upon the discovery of highly effective modifiers that do not co-distill with hexane or-form-compounds during steam stripping which co-distill with hexane.
    Type: Grant
    Filed: January 8, 1999
    Date of Patent: October 31, 2000
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu
  • Patent number: 6107408
    Abstract: Processes for the synthesis of star or multi-branched polymers and the resultant polymers. One or more alkadiene monomers are polymerized in the presence of suitable organometallic initiators and subsequently coupled to form star polymers. Prior to coupling, one or more alkenylsubstituted aromatic hydrocarbons are incorporated at the living ends of the polydienyl anions to provide increased linking efficiencies.
    Type: Grant
    Filed: February 26, 1998
    Date of Patent: August 22, 2000
    Assignee: FMC Corporation
    Inventors: Roderic Paul Quirk, Robert James Letchford, James Anthony Schwindeman
  • 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: 6046288
    Abstract: A method for reducing the amount of aliphatic solvent needed for maintaining aminoalkyllithium initiators in solution comprising the step of combining at least one aminoalkyllithium compound with a second, dissimilar lithioamine.
    Type: Grant
    Filed: September 24, 1997
    Date of Patent: April 4, 2000
    Assignee: Bridgestone Corporation
    Inventors: David F. Lawson, Michael L. Kerns, John R. Schreffler
  • Patent number: 5973086
    Abstract: A process for the living anionic polymerization of alkyl(meth)acrylic monomers, involving polymerizing the monomers in the presence of an initiator comprising a carbanion and a metal or nonmetal salt of perchloric acid. The initiator has the formula (I): ##STR1## wherein R.sub.1 =a linear or branched alkyl group having one to six carbon atoms, R.sub.2 =a phenyl or alkyl group having one to six carbon atoms, R.sub.3 =a phenyl or an ester group and M.sup.+ is an alkali, alkaline earth metal or quarternary ammonium cation containing 1-8 carbon atoms in an alkyl group thereof.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: October 26, 1999
    Assignee: Council of Scientific & Industrial Research
    Inventors: Durairaj Baskaran, Swaminathan Sivaram
  • Patent number: 5919870
    Abstract: Protected functional initiators have been demonstrated to polymerize dienes and alkenyl substituted aromatics. The resultant living anions were linked with a coupling agent, such as divinylbenzene or tin tetrachloride, to afford a protected functionalized star polymer. Subsequent deprotection afforded a star polymer, with functional groups on the end of each arm of the star. The star polymer could be hydrogenated before or after removal of the protecting groups. The newly liberated functional groups can participate in further polymerization chemistry.
    Type: Grant
    Filed: June 5, 1996
    Date of Patent: July 6, 1999
    Assignee: FMC Corporation
    Inventors: Robert J. Letchford, Conrad W. Kamienski, James A. Schwindeman
  • Patent number: 5916962
    Abstract: A rubber composition having good breaking properties, high tan.delta., good wear resistance and a method for preparing a copolymer used in the rubber composition. The copolymer is a butadiene-styrene copolymer prepared in the presence of an organopotassium compound, an oxolanyl alkane and an organolithium initiator compound. The copolymer may be modified. A vulcanite of the rubber composition including 20 parts or more of the copolymer of the present invention has good properties.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: June 29, 1999
    Assignee: Bridgestone Corporation
    Inventors: Tadashi Shibata, Ryota Fujio
  • Patent number: 5914378
    Abstract: Process for the preparation of a polymer by the polymerization of:(A) from 50 to 100 percent by weight of at least one diene monomer,(B) from 0 to 50 percent by weight of at least one ethylenically unsaturated monomer,the above polymerization being carried out in an inert solvent in the presence of a catalytic system which comprises:(a) at least one anionic initiator essentially consisting of a Lithium derivative,(b) at least one modifier belonging to the group of tetrahydropyranyl ethers.
    Type: Grant
    Filed: May 7, 1997
    Date of Patent: June 22, 1999
    Assignee: Enichem S.p.A.
    Inventors: Gian Tommaso Viola, Claudio Trombini, Lorenzo Musiani
  • Patent number: 5906956
    Abstract: This invention reveals an initiator system which is comprised of (a) a lithium initiator, (b) a sodium alkoxide and (c) a polar modifier; wherein the molar ratio of the sodium alkoxide to the lithium initiator is within the range of about 0.05:1 to about 3:1; and wherein the molar ratio of the polar modifier to the lithium initiator is within the range of about 0.25:1 to about 5:1. The subject invention also discloses a process for preparing 3,4-polyisoprene rubber which comprises polymerizing isoprene monomer with a lithium initiator at a temperature which is within the range of about 30.degree. C. to about 100.degree. C. in the presence of a sodium alkoxide and a polar modifier, wherein the molar ratio of the sodium alkoxide to the lithium initiator is within the range of about 0.05:1 to about 3:1; and wherein the molar ratio of the polar modifier to the lithium initiator is within the range of about 0.25:1 to about 5:1.
    Type: Grant
    Filed: April 3, 1997
    Date of Patent: May 25, 1999
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu
  • 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: 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: 5827929
    Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Z--O--C(R.sup.1 R.sup.2 R.sup.3)wherein M is an alkali metal; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkoxy, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkoxy, lower alkylthio, and lower dialkylamino groups, and their employment as initiators in the anionic polymerization of olefin containing monomers in an inert, hydrocarbon solvent comprising reacting an omega-protected-1-haloalkyl with lithium metal dispersion having a particle size between 10 and 300 millimicrons in size, at a temperature between 35.degree. and 130.degree. C. in an alkane solvent containing 5 to 10 carbon atoms.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: October 27, 1998
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Eric J. Granger, John F. Engel, Conrad W. Kamienski
  • Patent number: 5798418
    Abstract: The present invention provides novel, multi-arm or star-shaped polymers having mixed protected functional and non-functional ends, their optionally hydrogenated analogues, and the polymers produced by removal of the protecting groups. The invention also provides a process for the preparation of novel multi-arm or star-shaped polymers having branched-end functionality on some, but not all, of the branches. The multi-arm or star polymers of this invention are produced from more than one type of initiator, i.e., from both functional and non-functional initiators which, by design, incorporates both desired physical properties associated with multi-arm or star polymers with non-functional branch-ends and the versatility of functional branch end multi-arm or star polymers.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: August 25, 1998
    Assignee: FMC Corporation
    Inventor: Roderic P. Quirk
  • Patent number: 5795944
    Abstract: A process for the polymerization of dienes which comprises anionically polymerizing dienes in the presence of an anionic polymerization initiator and a microstructure control agent is improved by adding the control agent to the polymerization mixture in two or more doses to closely control the vinyl content of the polymer produced.
    Type: Grant
    Filed: March 12, 1997
    Date of Patent: August 18, 1998
    Assignee: Shell Oil Company
    Inventors: Teunis Graafland, Arthur Robinson Bean, Jr.
  • Patent number: 5792815
    Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Z--O--C(R.sup.1 R.sup.2 R.sup.3)wherein M is an alkali metal; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl, aryl or substituted aryl groups, and their employment as initiators in the anionic polymerization of olefin containing monomers in an inert, hydrocarbon solvent comprising reacting an omega-protected-1-haloalkyl with lithium metal dispersion having a particle size between 10 and 300 millimicrons in size, at a temperature between 35.degree. and 130.degree. C. in an alkane solvent containing 5 to 10 carbon atoms.
    Type: Grant
    Filed: June 19, 1997
    Date of Patent: August 11, 1998
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Eric J. Granger, John F. Engel, Conrad W. Kamienski
  • Patent number: 5717043
    Abstract: In a polymerization process of at least one of monomers selected from the group consisting of conjugated diene compounds such as butadiene and vinylaromatic compounds such as styrene, an organolithium compound such as butyllithium is added to the polymerization system first in the presence of the monomer, and thereafter a secondary amine compound such as saturated cyclic imine is added thereto to produce a soluble initiator by bringing the both compound into contact with each other. Polymerization is carried out with the soluble initiator formed. The obtained high molecular weight polymer is modified with a coupling agent such as tin tetrachloride. The polymer obtained has a high molecular weight, a narrow molecular weight distribution, and controlled molecular weight, and exhibits remarkable coupling property, low hysteresis loss. The process provides a polymer having a consistent characteristic, regardless of production scale and procedures of adding materials.
    Type: Grant
    Filed: October 16, 1996
    Date of Patent: February 10, 1998
    Assignee: Bridgestone Corporation
    Inventors: Atushi Nakayama, Koichi Morita, Masaaki Izuchi
  • Patent number: 5708092
    Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from carbon and silicon; R.sup.1, R.sup.2, and R.sup.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: January 13, 1998
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
  • Patent number: 5700888
    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: November 10, 1996
    Date of Patent: December 23, 1997
    Assignee: Bridgestone Corporation
    Inventor: James E. Hall
  • Patent number: 5698646
    Abstract: The present invention is directed toward anionic polymerization employing lithio aldimines mixed with an organic alkali metal compound and optionally, a chelating reagent. The lithio aldimines have the general formula (A)Li, where A is derived from a substituted aldimine. The invention is also directed toward polymers and other products made using the initiator, and methods therefor. Further, the invention contemplates a polymer, a polymer composition and products therefrom, which include a functional group from the reaction product of a substituted aldimine and an organolithium compound. The resulting polymers may be modified with a terminating, coupling or linking agent, which may provide the polymer with a multifunctionality.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: December 16, 1997
    Assignee: Bridgestone Corporation
    Inventors: Takashi Kitamura, Mark L. Stayer, Jr., Akira Matsuda
  • Patent number: 5677402
    Abstract: This invention reveals an initiator system which is comprised of (a) a lithium initiator, (b) a sodium alkoxide and (c) a polar modifier; wherein the molar ratio of the sodium alkoxide to the lithium initiator is within the range of about 0.05:1 to about 3:1; and wherein the molar ratio of the polar modifier to the lithium initiator is within the range of about 0.25:1 to about 5:1. The subject invention also discloses a process for preparing 3,4-polyisoprene rubber which comprises polymerizing isoprene monomer with a lithium initiator at a temperature which is within the range of about 30.degree. C. to about 100.degree. C. in the presence of a sodium alkoxide and a polar modifier, wherein the molar ratio of the sodium alkoxide to the lithium initiator is within the range of about 0.05:1 to about 3:1; and wherein the molar ratio of the polar modifier to the lithium initiator is within the range of about 0.25:1 to about 5:1.
    Type: Grant
    Filed: July 24, 1996
    Date of Patent: October 14, 1997
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu
  • Patent number: 5677399
    Abstract: The invention is a practical process for anionically synthesizing commercially significant quantities of macrocyclic polymers from polar and/or non-polar monomers by using Group IIA and IIB metal cyclic organometallic initiators. Activation of the ring metal atom results in anionic polymerization of the monomers by addition into the initiator ring at the bonds between the atom and its two adjacent carbon atoms, the metal atom acting as a bridge between the two living ends of the propagating chain. Coupling of the cyclic polymer living ends by coupling agents produces macrocyclic polymers that are stable in air and moisture and that exhibit desirable properties, such as low viscosities at high molecular weights. Such macrocyclic polymers provide enhanced polymer processability during molding, extruding and the forming of films.
    Type: Grant
    Filed: November 7, 1996
    Date of Patent: October 14, 1997
    Assignee: Bridgestone Corporation
    Inventor: James E. Hall
  • Patent number: 5674798
    Abstract: The invention is directed toward anionic polymerization employing lithio amines mixed with an organic alkali metal compound and optionally, a chelating reagent. The lithio amines have the general formula (A)Li(SOL).sub.y, where SOL is a solubilizing component, A is an alkyl, dialkyl, cycloalkyl or dicycloalkyl amine radical or a cyclic amine, and y is 0 or is from about 0.5 to about 3. The invention is also directed toward polymers and other products made using the initiator, and methods therefor. Further, the invention contemplates a polymer, a polymer composition and products therefrom, which include a functional group from the reaction product of an amine and an organolithium compound. The resulting polymers may be terminated with a terminating, coupling or linking agent, which may provide the polymer with a multifunctionality.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: October 7, 1997
    Assignee: Bridgestone Corporation
    Inventors: Takashi Kitamura, David F. Lawson, Koichi Morita, Yoichi Ozawa
  • Patent number: 5654384
    Abstract: This invention reveals a process for preparing high vinyl polybutadiene rubber which comprises polymerizing 1,3-butadiene monomer with a lithium initiator at a temperature which is within the range of about 5.degree. C. to about 100.degree. in the presence of a sodium alkoxide and a polar modifier, wherein the molar ratio of the sodium alkoxide to the polar modifier is within the range of about 0.1:1 to about 10:1; and wherein the molar ratio of the sodium alkoxide to the lithium initiator is within the range of about 0.05:1 to about 10:1.
    Type: Grant
    Filed: March 27, 1996
    Date of Patent: August 5, 1997
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu, David John Zanzig, Paul Harry Sandstrom, Steven Kristofer Henning, Danielle Lucas
  • Patent number: 5654371
    Abstract: A process for the preparation of hydrocarbon solutions of monofunctional ether initiators of the following general structure:M--Q.sub.n --Z--OA(R.sup.1 R.sup.2 R.sup.3) (II)wherein M is defined as an alkali metal, selected from the group consisting of lithium, sodium and potassium, Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons and alkenylsubstituted aromatic hydrocarbons; Z is defined as a branched or straight chain hydrocarbon tether or connecting group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups; A is an element selected from Group IVa of the periodic table and R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl, aryl or substituted aryl groups, and n is an integer from 1 to 5.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: August 5, 1997
    Assignee: FMC Corporation
    Inventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
  • Patent number: H2030
    Abstract: Random copolymers of a conjugated diene and at least 50% by weight of a vinyl aromatic compound are prepared by slowly reacting the monomers in a non-polar solvent in the presence of a chelating modifier such as ethylene glycol diethyl ether which results in at least 50% 1,2-polymerization of the conjugated diene.
    Type: Grant
    Filed: June 29, 1993
    Date of Patent: June 4, 2002
    Assignee: Shell Oil Company
    Inventor: Ronald James Hoxmeier