Contains Phosphorus Atom Patents (Class 526/179)
  • Publication number: 20150126675
    Abstract: Embodiments provide polydienes and diene copolymers having organophosphines functionality. Specific embodiments employ phosphorus-containing organometal initiators and copolymers prepared by anionically polymerizing conjugated diene monomer and vinyl organophosphine.
    Type: Application
    Filed: May 1, 2013
    Publication date: May 7, 2015
    Applicants: Bridgestone Corporation
    Inventors: Terrence E. Hogan, William L. Hergenrother, David M. Roggeman
  • Publication number: 20130296480
    Abstract: A method for preparing a functionalized polymer, the method comprising: polymerizing conjugated diene monomer, optionally together with comonomer, using a phosphorus-containing organometal initiator.
    Type: Application
    Filed: May 1, 2013
    Publication date: November 7, 2013
    Inventors: Terrence E. Hogan, William L. Hergenrother
  • 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: 8124699
    Abstract: The present invention relates to a method for the polymerization of fluoromonomers using non-fluorinated alkyl phosphonate surfactants, and to the fluoropolymers formed thereby. Specifically, the method of the polymerization uses one or more alkyl phosphonic acids or salts thereof.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 28, 2012
    Assignee: Arkema Inc.
    Inventors: Mehdi Durali, Lotfi Hedhli, Roice Wille
  • 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: 7709598
    Abstract: To obtain a polymerization initiator (acid generating agent) having excellent power for initiation of cationic polymerization without containing arsenic or antimony. Provided is a specific onium salt or transition metal complex salt of a fluorinated alkyl fluorophosphoric acid.
    Type: Grant
    Filed: May 27, 2005
    Date of Patent: May 4, 2010
    Assignee: San-Apro Limited
    Inventors: Hideki Kimura, Jiro Yamamoto, Shinji Yamashita, Mitsuo Kurumaya, Takaaki Sonoda
  • Publication number: 20090036607
    Abstract: A polymer particle is obtained by polymerizing a monomer in the presence of a phosphate salt represented by the following formula (1). The polymer particle contains 0.01 to 1.0 part by mass of the phosphate salt to 100 parts by mass of the polymer particle. A resin composition and a molded article using such a polymer particle are excellent in thermal stability and resistance to moist heat, and the color tone of the resin has little change before and after the blending of the polymer particle. In the formula (1), R1 represents an alkyl group having 10 to 18 carbon atoms, R2 represents an alkylene group having 2 to 3 carbon atoms, M represents an alkaline metal or an alkaline earth metal, m represents an integer of 1 to 20, and n represents 1 or 2.
    Type: Application
    Filed: March 3, 2006
    Publication date: February 5, 2009
    Applicant: Mitsubishi Rayon Co., Ltd.
    Inventors: Shinya Hirai, Toshihiro Kasai, Masaki Nakayama
  • 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: 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
  • Publication number: 20040063879
    Abstract: There is disclosed a process for polymerizing a cationically polymerizable olefin comprising the step of polymerizing at least one cationically polymerizable olefin at a subatmospheric pressure in the presence of a cationic polymerization catalyst system which comprises an initiator and an activator, which together form a reactive cation and non-co-ordinating anion, the activator being prepared by the reaction of a metalloid compound of formula (R1R2R3)M with a co-initiator, the co-initiator being selected from the group consisting of an alcohol, a thiol, a carboxylic acid, a thiocarboxylic acid and the like.
    Type: Application
    Filed: November 12, 2003
    Publication date: April 1, 2004
    Inventors: Michael C. Baird, Mark J. Drewitt, Kumar K. Rajesh
  • Publication number: 20030217808
    Abstract: Adhesive compositions are disclosed which cure rapidly and completely on confinement between passive substrates, such as magnesium alloys, that are deficient in transition metals and transition metal ions. The compositions include one or more acrylate resins, one or more peroxy free radical initiators, one or more onium salts, and an accelerator such as acetylphenyl hydrazine desirably in an amount of about 1.0% or less by weight of the composition. These compositions provide exceptional bonding to such substrates without the need for a transition metal primer. Methods of making and using such compositions are also disclosed.
    Type: Application
    Filed: October 29, 2002
    Publication date: November 27, 2003
    Inventors: John Woods, Susanne Morrill, Rick Danheiser
  • Patent number: 6649711
    Abstract: A polymerisation process for the preparation of vinylic polymers from the corresponding vinylic monomers which process comprises the step of reacting a vinylic monomer in the presence of a catalyst system comprising a) a metal complex of general formula (I) where A is selected from the group consisting of nickel, iron, cobalt, chromium, manganese, titanium, zirconium, vanadium and the rare earth metals; L1, L2, L3 and L4 are ligands and b) a Lewis acid of general formula (II) wherein at least one of W, Y or Z is capable of forming a co-ordination bond with A and the others of W, Y and Z are bulky groups; D is selected from the group consisting of aluminium, magnesium, zinc and boron.
    Type: Grant
    Filed: December 29, 2000
    Date of Patent: November 18, 2003
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul Alexander Cameron, Vernon Charles Gibson, Derek John Irvine
  • Patent number: 6646075
    Abstract: This invention relates to high molecular weight perfluorocyclobutane polymers and methods of polymerizing trifluorovinyl monomers to form high molecular weight perfluorocyclobutane polymers in the presence of a catalyst or initiator.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: November 11, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Shane S. Mao, Allen Raymond Siedle
  • Patent number: 6384164
    Abstract: The present invention provides a process for preparing a branched diene elastomer having a high proporation of starred chains comprising anionically polymerizing at least one conjugated diene monomer having 4 to 12 carbons in a polymerization medium comprising a hydrocarbon solvent, such as cyclohexane, and an organometallic initiator, such as n-butyllithium, wherein tris-(2,4-di-tert-butylphenyl)phosphite is added to the polymerization medium as a starring agent during or at the end of polymerization in an amount such that the molar ratio of the starring agent to the initiator is between 0.1 and 1.5, preferably between 0.2 and 0.5. The process produces a branched diene elastomer having a high proportion of starred chains. The elastomer can be a homopolymer, such as polybutadiene or polyisoprene or a copolymer, such as polystyrene/polybutadiene.
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: May 7, 2002
    Assignee: Michelin Recherche et Technique S.A.
    Inventors: Jean-Luc Cabioch, Nicole Dajoux
  • Publication number: 20020032290
    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):
    Type: Application
    Filed: September 24, 2001
    Publication date: March 14, 2002
    Applicant: Kuraray Co., Ltd.
    Inventors: Naohiko Uchiumi, Kenichi Hamada, Masaji Kato, Tomohiro Ono, Sachie Yaginuma, Kazushige Ishiura
  • 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: 6143847
    Abstract: The present invention concerns a novel method for preparing polymers (preferably (meth)acrylate polymers and copolymers) having a narrow molecular weight distribution by metal-free anionic polymerization in the presence of a phosphonium cation containing at least one annellated aromatic ring as substituent on the phosphorous atom.
    Type: Grant
    Filed: April 7, 1997
    Date of Patent: November 7, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Thieo E. Hogen-Esch, Dimo K. Dimov, Stephan Jungling, Volker Warzelhan, Hermann Gausepohl
  • Patent number: 5932638
    Abstract: The present invention provides adhesive compositions which include free radical polymerizable compounds and a redox catalyst system to accelerate polymerization thereof. The redox catalyst includes an aniline derivative substituted in the para position by halogen as an accelerator. The use of para-halogenated aniline derivatives as an accelerator in the cure of free radical polymerizable compounds results in good bond strength and greatly improved surface cure of the adhesive composition.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: August 3, 1999
    Assignee: Lord Corporation
    Inventors: Robin F. Righettini, Terrence H. Dawdy
  • Patent number: 5929181
    Abstract: A method of preparing amorphous copolymers of ethylene and at least one norbornene (NB)-type comonomer is disclosed. These polymers may be random or alternating depending on the choice of catalyst and/or the relative ratio of the monomers used. This method comprises polymerizing said monomers in a diluent or in bulk in the presence of a neutral nickel catalyst which may be represented by the formula ##STR1## wherein Y may be a saturated or unsaturated hydrocarbyl chain, X may be oxygen or sulfur, E may be phosphorus, arsenic, antimony, oxygen or nitrogen, R and R' independently each is hydrogen or a hydrocarbyl group, L is a ligand containing a heteroatom P, N or O or L and R together with L may form part of a chelating structure in which case L is an ethylenic double bond.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: July 27, 1999
    Assignees: The B.F.Goodrich Co., A.V. Topchiev Institute of Petrochemical Synthesis
    Inventors: Kiryll Lvovich Makovetsky, Eugeny Shmerovich Finkelshtein, Viktor Ivanovich Bykov, Andrey Khristoforovich Bagdasaryan, Brian Leslie Goodall, Larry Funderburk Rhodes
  • Patent number: 5741869
    Abstract: Addition polymers derived from norbornene-functional monomers are terminated with an olefinic moiety derived from a chain transfer agent selected from a compound having a terminal olefinic double bond between adjacent carbon atoms, excluding styrenes, vinyl ethers, and conjugated dienes and at least one of said carbon atoms has two hydrogen atoms attached thereto. The addition polymers of this invention are prepared from a single or multicomponent catalyst system including a Group VIII metal ion source. The catalyst systems are unique in that they catalyze the insertion of the chain transfer agent exclusively at a terminal end of the polymer chain.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 21, 1998
    Assignee: The B.F. Goodrich Company
    Inventors: Brian Leslie Goodall, George Martin Benedikt, Lester Howard McIntosh, III, Dennis Allen Barnes, Larry Funderburk Rhodes
  • Patent number: 5728782
    Abstract: There is provided a process comprising polymerizing a compound selected from the group consisting of a conjugated diene, a vinyl-substituted aromatic compound, and mixtures thereof in a gas phase fluidized polymerization vessel under polymerization conditions in the presence of at least one anionic initiator, optionally in the presence of an inert particulate material. A novel resin particle produced by the process is also provided.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: March 17, 1998
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Monika Brady, Kevin Joseph Cann, David Joseph Dovedytis
  • Patent number: 5717042
    Abstract: A process and catalyst system for the preparation of diene oligomers and copolymeric oligomers is disclosed. The oligomers and copolymers are prepared in an alkane solvent from one or more 1,3-diene monomers using a secondary amine transfer agent and an anionic initiator. A catalyst system including a secondary amine transfer agent and an anionic initiator is also provided.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: February 10, 1998
    Assignee: Bridgestone/Firestone, Inc.
    Inventor: James E. Hall
  • Patent number: 5610248
    Abstract: The present invention concerns a novel method for preparing polymers (preferably (meth)acrylate polymers and copolymers) having a narrow molecular weight distribution by metal-free anionic polymerization in the presence of a phosphonium cation. The present invention also concerns block copolymers and methods of making the same using anionic polymerization in the presence of a phosphonium cation to prepare at least one block of the copolymer.
    Type: Grant
    Filed: March 6, 1995
    Date of Patent: March 11, 1997
    Assignee: The University of Southern California
    Inventors: Thieo Hogen-Esch, Angela Zagala
  • Patent number: 5571881
    Abstract: Addition polymers derived from norbornene-functional monomers are terminated with an olefinic moiety derived from a chain transfer agent selected from a compound having a terminal olefinic double bond between adjacent carbon atoms, excluding styrenes, vinyl ethers, and conjugated dienes and at least one of said carbon atoms has two hydrogen atoms attached thereto. The addition polymers of this invention are prepared from a single or multicomponent catalyst system including a Group VIII metal ion source. The catalyst systems are unique in that they catalyze the insertion of the chain transfer agent exclusively at a terminal end of the polymer chain.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: November 5, 1996
    Assignee: The B. F. Goodrich Company
    Inventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes, Larry F. Rhodes
  • Patent number: 5569730
    Abstract: Addition polymers derived from norbornene-functional monomers are terminated with an olefinic moiety derived from a chain transfer agent selected from a compound having a terminal olefinic double bond between adjacent carbon atoms, excluding styrenes, vinyl ethers, and conjugated dienes and at least one of said carbon atoms has two hydrogen atoms attached thereto. The addition polymers of this invention are prepared from a single or multicomponent catalyst system including a Group VIII metal ion source. The catalyst systems are unique in that they catalyze the insertion of the chain transfer agent exclusively at a terminal end of the polymer chain.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: October 29, 1996
    Assignee: The B. F. Goodrich Company
    Inventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes, Larry F. Rhodes
  • Patent number: 5468819
    Abstract: A single component ionic catalyst consists essentially of an organonickel complex cation, and a weakly coordinating neutral counteranion. The cation is a neutral bidentate ligand removably attached to a Group VIII transition metal in an organometal complex. The ligand is easily displaced by a norbornene-type (NB-type) monomer in an insertion reaction which results in an unexpectedly facile addition polymerization. A NB-type monomer includes NB or substituted NB, or a multi-ringed cycloolefin having more than three rings in which one or more of the rings has a structure derived from NB, and a ring may have an alicyclic alkyl, alkylene or alkylidene substituent. The insertion reaction results in the formation of a unique propagating species more soluble in a polar than in a non-polar solvent and devoid of an available .beta.-hydrogen for termination. The ensuing propagation of a polymer chain proceeds without measurable unsaturation.
    Type: Grant
    Filed: November 16, 1993
    Date of Patent: November 21, 1995
    Assignee: The B.F. Goodrich Company
    Inventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes
  • Patent number: 5411998
    Abstract: A process for sealing or adhering two surfaces having gaps of more than 100 micrometers between the surfaces which comprises:(A) applying to at least one of said surfaces an anaerobic composition comprising:(i) a room temperature polymerizable (meth)acrylic monomer,(ii) a peroxy free radical initiator, and(iii) an amount effective as an accelerator of a combination of saccharin and at least one onium salt (other than an iodide); and(B) placing said surfaces in an abutting relationship until the composition has cured through the gaps.Exemplified onium salts are phosphonium salts of the formula IV and quaternary ammonium salts of the formula II: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which may be the same or different, are hydrocarbyl, hydrocarbylaryl, aryl or a substituted derivative thereof;X is Cl, Br or F, or a soft anion.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: May 2, 1995
    Assignee: Loctite Limited
    Inventors: Ciaran B. McArdle, Joseph Burke
  • Patent number: 5284927
    Abstract: The subject invention relates to a technique for synthesizing rubbery terpolymers of styrene, isoprene and butadiene. These rubbery terpolymers exhibit an excellent combination of properties for utilization in tire tread rubber compounds. By utilizing such terpolymers in tire treads, tires having improved wet skid resistance can be built without sacrificing rolling resistance or tread wear characteristics. The subject invention specifically discloses a process for preparing a rubbery terpolymer of styrene, isoprene, and butadiene having multiple glass transition temperatures and having an excellent combination of properties for use in making tire treads which comprises: terpolymerizing styrene, isoprene and 1,3-butadiene in an organic solvent at a temperature of no more than about 40.degree. C. in the presence of (a) tripiperidino phosphine oxide, (b) an alkali metal alkoxide and (c) an organolithium compound.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: February 8, 1994
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Adel F. Halasa
  • Patent number: 5173550
    Abstract: The subject invention relates to a process for synthesizing random styrene-isoprene copolymers having a medium vinyl microstructure. These random styrene-isoprene rubbers have physical properties which make them highly desirable for utilization in tire tread rubber compounds. The utilization of such random styrene-isoprene rubbers in tire tread rubber results in improved tread wear, rolling resistance and traction characteristics. This invention more specifically relates to a process for preparing a random styrene-isoprene rubber having a medium vinyl microstructure which comprises copolymerizing isoprene and styrene in the presence of (a) at least one organolithium compound and (b) at least one modifier slected from the group consisting of 1,2-dipiperidinoethane, dipiperidinomethane, and tripiperidinophosphine oxide.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: December 22, 1992
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Adel F. Halasa
  • Patent number: 5171810
    Abstract: Random or block copolymers with (1-hydro-1-R-1-sila-cis-pent-3-ene), poly(1-hydro-1-R-3,4 benzo-1-sila pent-3-ene), and disubstituted 1-silapent-3-ene repeating units of the general formula ##STR1## where R is hydrogen, an alkyl radical containing from one to four carbon atoms or phenyl, R.sup.1 is hydrogen, an alkyl radical containing from one to four carbon atoms, phenyl or a halogen and R.sup.2 is hydrogen, or R.sup.1 and R.sup.2 are combined to form a phenyl ring, are prepared by the anionic ring opening polymerization of silacyclopent-3-enes or 2-silaindans with an organometallic base and cation coordinating ligand catalyst system or a metathesis ring opening catalyst system.
    Type: Grant
    Filed: September 12, 1991
    Date of Patent: December 15, 1992
    Assignee: University of Southern California
    Inventors: William P. Weber, Stephen Q. Zhou
  • Patent number: 5169916
    Abstract: Poly(1-hydro-1-R-1-sila-cis-pent-3-ene) and poly(1-hydro-1-R-3,4 benzo-1-sila pent-3-ene) polymers having repeating units of the general formula ##STR1## where R is hydrogen, an alkyl radical containing from one to four carbon atoms or phenyl, R.sup.1 is hydrogen, an alkyl radical containing from one to four carbon atoms, phenyl or a halogen and R.sup.2 is hydrogen, or R.sup.1 and R.sup.2 are combined to form a phenyl ring, are prepared by the anionic ring opening polymerization of silacyclopent-3-enes or 2-silaindans with an organometallic base and cation coordinating ligand catalyst system.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: December 8, 1992
    Assignee: University of South California
    Inventors: William P. Weber, Stephen Q. Zhou
  • Patent number: 5137998
    Abstract: The subject invention relates to a technique for synthesizing rubbery terpolymers of styrene, isoprene and butadiene. These rubbery terpolymers exhibit an excellent combination of properties for utilization in tire tread rubber compounds. By utilizing such terpolymers in tire treads, tires having improved wet skid resistance can be built without sacrificing rolling resistance or tread wear characteristics. The subject invention specifically discloses a process for preparing a rubbery terpolymer of styrene, isoprene, and butadiene having multiple glass transition temperatures and having an excellent combination of properties for use in making tire treads which comprises: terpolymerizing styrene, isoprene and 1,3-butadiene in an organic solvent at a temperature of no more than about 40.degree. C. in the presence of (a) at least one member selected from the group consisting of tripiperidino phosphine oxide and alkali metal alkoxides and (b) an organolithium compound.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: August 11, 1992
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Wen-Liang Hsu, Adel F. Halasa
  • Patent number: 5130390
    Abstract: Crosslinkable saturated and unsaturated carbosilane polymers are prepared by polymerizing vinyl substituted 1-silacyclo-pent-3-ene or vinyl substituted 1-silacyclobutane monomers in the presence of an anionic ring opening catalyst.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: July 14, 1992
    Assignee: University of Southern California
    Inventors: William P. Weber, Xiugao Liao
  • Patent number: 5112929
    Abstract: A method for preparing a diene polymer or copolymer having increased amounts of 1,2-microstructure is provided. The method involves polymerizing a diene monomer or mixture of a diene monomer and a vinyl aromatic hydrocarbon monomer in a hydrocarbon solvent in the presence of a catalytically effective amount of a catalyst composition comprising: (a) an organolithium initiator and (b) an oxolanyl cyclic acetal having the structural formula: ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl groups containing from 1 to 4 carbon atoms and X is 0 or 1.
    Type: Grant
    Filed: April 5, 1991
    Date of Patent: May 12, 1992
    Assignee: Bridgestone Corporation
    Inventor: James E. Hall
  • Patent number: 4843120
    Abstract: It has been determined that certain rubbery polymers having multiple glass transition temperatures can be utilized in making tires which have improved rolling resistance, improved wet skid resistance, and outstanding tread wear. These rubbery polymers are derived from at least one conjugated diolefin monomer, have a first glass transition temperature which is between -110.degree. C. and -20.degree. C. and have a second glass transition temperature which is between -50.degree. C. and 0.degree. C. These rubber polymers can be homopolymers of conjugated diolefin monomers, copolymers of more than one conjugated diolefin monomer, or copolymers derived from at least one conjugated diolefin monomer and at least one vinyl aromatic monomer.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: June 27, 1989
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Adel F. Halasa, Bill B. Gross, Joel L. Cox, George F. Balogh
  • Patent number: 4783516
    Abstract: This invention is concerned with novel polysilanes containing olefinic groups which are prepared by reactions of halogen-containing organosilane monomers or mixtures thereof with sodium metal in an appropriate solvent or mixture of solvents. Such polysilane polymers are soluble and thermoplastic, and can be directly converted to silicon carbide compositions by pyrolysis at atmospheric pressure.
    Type: Grant
    Filed: November 22, 1983
    Date of Patent: November 8, 1988
    Assignee: Union Carbide Corporation
    Inventors: Curtis L. Schilling, Jr., Bernard Kanner
  • Patent number: 4537939
    Abstract: A process and catalyst system is disclosed herein for the preparation of (co)polymers having a 1,2-microstructure of between about 20 and about 65 percent. These (co)polymers are prepared in a hydrocarbon or non-polar solvent from a monomer system which contains at least one 1,3-diene monomer. The catalyst system which is employed in the production of the (co)polymer is a combination of an anionic initiator based on lithium and a phosphine oxide modifier which is substituted with three saturated heterocyclic rings, each hetero ring containing one nitrogen atom and either four, five or six carbon atoms.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: August 27, 1985
    Assignee: The Firestone Tire & Rubber Company
    Inventors: James E. Hall, Donald N. Schulz
  • Patent number: 4530984
    Abstract: A process and catalyst system is disclosed herein for the preparation of (co)polymers having a 1,2-microstructure ranging between about 20 and about 65 percent. These (co)polymers are prepared in a hydrocarbon or non-polar solvent from a monomer system which contains at least one 1,3-diene monomer and optionally other copolymerizable monomers. The catalyst system which is employed in the production of the (co)polymer is a combination of (1) an anionic initiator based on lithium; (2) a dialkyl magnesium compound or a trialkyl aluminum compound or a mixture thereof; and (3) a phosphine oxide modifier which is substituted with three saturated heterocyclic rings, each hetero ring containing one nitrogen atom and either four, five or six carbon atoms.
    Type: Grant
    Filed: April 2, 1984
    Date of Patent: July 23, 1985
    Assignee: The Firestone Tire & Rubber Company
    Inventor: James E. Hall
  • Patent number: 4476240
    Abstract: A process and catalyst system is disclosed herein for the preparation of (co)polymers having a 1,2-microstructure of between about 20 and about 65 percent. These (co)polymers are prepared in a hydrocarbon or non-polar solvent from a monomer system which contains at least one 1,3-diene monomer. The catalyst system which is employed in the production of the (co)polymer is a combination of an anionic initiator based on lithium and a phosphine oxide modifier which is substituted with three saturated heterocyclic rings, each hetero ring containing one nitrogen atom and either four, five or six carbon atoms.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: October 9, 1984
    Assignee: The Firestone Tire & Rubber Company
    Inventors: James E. Hall, Donald N. Schulz
  • Patent number: 4473661
    Abstract: A process and catalyst system is disclosed herein for the preparation of (co)polymers having a 1,2-microstructure ranging between about 20 and about 65 percent. These (co)polymers are prepared in a hydrocarbon or non-polar solvent from a monomer system which contains at least one 1,3-diene monomer and optionally other copolymerizable monomers. The catalyst system which is employed in the production of the (co)polymer is a combination of (1) an anionic initiator based on lithium; (2) a dialkyl magnesium compound or a trialkyl aluminum compound or a mixture thereof; and (3) a phosphine oxide modifier which is substituted with three saturated heterocyclic rings, each hetero ring containing one nitrogen atom and either four, five or six carbon atoms.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: September 25, 1984
    Assignee: The Firestone Tire & Rubber Company
    Inventor: James E. Hall
  • Patent number: 4336361
    Abstract: A linear polydivinylbenzene having recurring units of Formula (A), ##STR1## and a number average molecular weight of about 500 to about 1,000,000; a linear copolymer having at least about 1% by weight of recurring units of Formula (A) as described above and at most about 99% by weight of recurring units of at least one of Formulae (B) and (C), ##STR2## wherein R.sub.1 and R.sub.2 may be the same or different and each represents a hydrogen atom, a C.sub.1-20 alkyl group, a C.sub.3-10 cycloalkyl group, a C.sub.7-12 arylalkyl group, a C.sub.3-8 alkenyl group, a C.sub.6-15 aryl group, a H.sub.2 N--CH.sub.2).sub.n group wherein n is an integer of 1 to 15 or a H--(NH--CH.sub.2 --CH.sub.2).sub.n group wherein m is an integer of 2 to 8; and R.sub.3 represents a hydrogen atom, a C.sub.1-12 alkyl group, a C.sub.3-10 cycloalkyl group, a C.sub.7-12 arylalkyl group or a C.sub.
    Type: Grant
    Filed: November 17, 1980
    Date of Patent: June 22, 1982
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Teiji Tsuruta, Yoshiaki Nitadori
  • Patent number: 4264753
    Abstract: The catalyst system disclosed herein comprises a combination or a chelate of a hydrocarbyl lithium compound with a bicyclic amine compound bridged together through nitrogen in each cyclic ring by means of 1-4, preferably 2-carbon atoms and each cyclic ring having at least one nitrogen and at least one other heteroatom in its cyclic structure selected from the class consisting of NR, O, S and PR. This catalyst system is particularly useful in the polymerization of vinyl compounds such as ethylene, propylene, styrene, butadiene, etc. The process for the polymerization of conjugated dienes produces polymers of excellent properties. For example, with butadiene-1,3 and other appropriate conditions, polybutadiene with high percentages of syndiotactic crystalline structure may be produced.
    Type: Grant
    Filed: May 20, 1980
    Date of Patent: April 28, 1981
    Assignee: The Firestone Tire & Rubber Company
    Inventors: Adel F. Halasa, James E. Hali
  • Patent number: 4230841
    Abstract: There is disclosed a process for the preparation of medium vinyl polybutadiene which comprises copolymerizing butadiene with small amounts of divinylbenzene in a hydrocarbon solvent system employing as a catalyst an alkyl lithium compound which has been modified by mixtures of polar compounds, at least one of which polar compound is selected from the group consisting of hexamethylphosphoric acid triamide (HMPA), N,N,N'N'-tetramethylethylene diamine (TMEDA), ethylene glycol dimethyl ether (glyme), diethylene glycol dimethyl ether (diglyme), triethylene glycol dimethyl ether (triglyme) and tetraethylene glycol dimethyl ether (tetraglyme), and at least one of which polar compound is selected from the group consisting of tetrahydrofuran (THF), 1,4diazabicyclo [2.2.2] octane (DABCO), diethyl ether, triethylamine, tri-n-butylamine, tri-n-butylphosphine and p-dioxane, in which the temperature is maintained constant throughout the polymerization.
    Type: Grant
    Filed: January 31, 1979
    Date of Patent: October 28, 1980
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Robert T. Prudence
  • Patent number: 4208498
    Abstract: Continuous solution polymerization in an open type reactor of one or more conjugated dienes or of one or more conjugated dienes with one or more vinyl aromatic compounds, initiated by an organolithium initiator, without clogging of the reactor due to gel formation can be achieved by conducting the polymerization in the presence of a deactivating system which inhibits the formation of gels.
    Type: Grant
    Filed: September 29, 1978
    Date of Patent: June 17, 1980
    Assignee: Compagnie Generale des Etablissements Michelin
    Inventor: Jean-Marie Massoubre
  • Patent number: 4202954
    Abstract: Continuous solution polymerization in an open type reactor of one or more conjugated dienes or of one or more conjugated dienes with one or more vinyl aromatic compounds, initiated by an organolithium initiator, without clogging of the reactor due to gel formation can be achieved by conducting the polymerization in the presence of a deactivating system which inhibits the formation of gels.
    Type: Grant
    Filed: September 29, 1978
    Date of Patent: May 13, 1980
    Assignee: Compagnie Generale des Etablissements Michelin
    Inventor: Jean-Marie Massoubre
  • Patent number: 4189555
    Abstract: Continuous solution polymerization in an open type reactor of one or more conjugated dienes or of one or more conjugated dienes with one or more vinyl aromatic compounds, initiated by an organolithium initiator, without clogging of the reactor due to gel formation can be achieved by conducting the polymerization in the presence of a deactivating system which inhibits the formation of gels.
    Type: Grant
    Filed: September 15, 1976
    Date of Patent: February 19, 1980
    Assignee: Compagnie Generale des Etablissements Michelin
    Inventor: Jean-Marie Massoubre
  • Patent number: 4180637
    Abstract: Low molecular weight polymers of an unsaturated dicarboxylic anhydride monomer (e.g., maleic anhydride) and a copolymerizable monomer (e.g., styrene) are prepared by an improved process which comprises polymerizing the monomers in the presence of the hydroxide or a nucleophilic salt of a monovalent cation (e.g., a nucleophilic salt or the hydroxide of an ammonium compound or of an alkali metal). By the practice of this process, low molecular weight polymers are conveniently and economically obtained without the use of high catalyst concentrations, high temperatures, conventional chain transfer agents, high boiling chain transfer solvents or combinations thereof.
    Type: Grant
    Filed: November 7, 1977
    Date of Patent: December 25, 1979
    Assignee: The Dow Chemical Company
    Inventors: Syamalarao Evani, Russell J. Raymond
  • Patent number: 4091198
    Abstract: Gel formation in the first reactor means of a multireactor process is suppressed by the employment of a silicon halide in the first reactor means in an organolithium-initiated, solution-polymerized, randomized, conjugated diene/monovinyl-substituted aromatic compound copolymerization.
    Type: Grant
    Filed: September 10, 1976
    Date of Patent: May 23, 1978
    Assignee: Phillips Petroleum Company
    Inventors: Richard L. Smith, Ralph C. Farrar, Daniel H. Willis
  • Patent number: 3959100
    Abstract: Ultraviolet polymerization of photopolymerizable binders or vehicles is improved by incorporating thereinto a sensitizer composition comprising an activated halogenated azine compound.
    Type: Grant
    Filed: September 23, 1974
    Date of Patent: May 25, 1976
    Assignee: SCM Corporation
    Inventor: Vincent Daniel McGinniss
  • Patent number: 3954700
    Abstract: Shortcomings in the use of metallic sodium as a catalyst for the polymerization of dienes are overcome by carrying the polymerization out in a hydrocarbon solvent with organosodium as the catalyst, using a chelating amide such as hexamethylphosphorotriamide.
    Type: Grant
    Filed: July 11, 1975
    Date of Patent: May 4, 1976
    Assignee: The Firestone Tire & Rubber Company
    Inventor: Adel Farhan Halasa