Contains Phosphorus Atom Patents (Class 526/179)
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Publication number: 20150126675Abstract: 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: ApplicationFiled: May 1, 2013Publication date: May 7, 2015Applicants: Bridgestone CorporationInventors: Terrence E. Hogan, William L. Hergenrother, David M. Roggeman
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Publication number: 20130296480Abstract: 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: ApplicationFiled: May 1, 2013Publication date: November 7, 2013Inventors: Terrence E. Hogan, William L. Hergenrother
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Patent number: 8227562Abstract: 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: GrantFiled: March 15, 2009Date of Patent: July 24, 2012Assignee: Bridgestone CorporationInventors: Yuan-Yong Yan, Michael W. Hayes
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Patent number: 8124699Abstract: 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: GrantFiled: August 4, 2006Date of Patent: February 28, 2012Assignee: Arkema Inc.Inventors: Mehdi Durali, Lotfi Hedhli, Roice Wille
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Patent number: 7981990Abstract: 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: GrantFiled: August 28, 2008Date of Patent: July 19, 2011Assignee: Bridgestone CorporationInventor: Yuan-Yong Yan
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Patent number: 7709598Abstract: 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: GrantFiled: May 27, 2005Date of Patent: May 4, 2010Assignee: San-Apro LimitedInventors: Hideki Kimura, Jiro Yamamoto, Shinji Yamashita, Mitsuo Kurumaya, Takaaki Sonoda
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Publication number: 20090036607Abstract: 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: ApplicationFiled: March 3, 2006Publication date: February 5, 2009Applicant: Mitsubishi Rayon Co., Ltd.Inventors: Shinya Hirai, Toshihiro Kasai, Masaki Nakayama
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Patent number: 7405262Abstract: A process for preparing a functionalized polymerization initiator, the process comprising combining a functionalized styryl compound and an organolithium compound.Type: GrantFiled: July 11, 2003Date of Patent: July 29, 2008Assignee: Bridgestone CorporationInventors: Thomas Antkowiak, Christine Rademacher, Anthony Ramic, David F. Lawson
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Patent number: 6762259Abstract: 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: GrantFiled: June 12, 2002Date of Patent: July 13, 2004Assignee: 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
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Publication number: 20040063879Abstract: 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: ApplicationFiled: November 12, 2003Publication date: April 1, 2004Inventors: Michael C. Baird, Mark J. Drewitt, Kumar K. Rajesh
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Publication number: 20030217808Abstract: 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: ApplicationFiled: October 29, 2002Publication date: November 27, 2003Inventors: John Woods, Susanne Morrill, Rick Danheiser
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Patent number: 6649711Abstract: 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: GrantFiled: December 29, 2000Date of Patent: November 18, 2003Assignee: Imperial Chemical Industries PLCInventors: Paul Alexander Cameron, Vernon Charles Gibson, Derek John Irvine
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Patent number: 6646075Abstract: 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: GrantFiled: November 30, 2000Date of Patent: November 11, 2003Assignee: 3M Innovative Properties CompanyInventors: Shane S. Mao, Allen Raymond Siedle
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Patent number: 6384164Abstract: 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: GrantFiled: April 25, 2001Date of Patent: May 7, 2002Assignee: Michelin Recherche et Technique S.A.Inventors: Jean-Luc Cabioch, Nicole Dajoux
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Publication number: 20020032290Abstract: 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: ApplicationFiled: September 24, 2001Publication date: March 14, 2002Applicant: Kuraray Co., Ltd.Inventors: Naohiko Uchiumi, Kenichi Hamada, Masaji Kato, Tomohiro Ono, Sachie Yaginuma, Kazushige Ishiura
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Patent number: 6271324Abstract: 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: GrantFiled: May 12, 1999Date of Patent: August 7, 2001Assignee: BASF AktiengesellschaftInventors: Stephan Jüngling, Christof Mehler, Horst Weiss, Susanne Steiger, Axel Müller, Helmut Schlaad, Bardo Schmitt
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Patent number: 6143847Abstract: 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: GrantFiled: April 7, 1997Date of Patent: November 7, 2000Assignee: BASF AktiengesellschaftInventors: Thieo E. Hogen-Esch, Dimo K. Dimov, Stephan Jungling, Volker Warzelhan, Hermann Gausepohl
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Patent number: 5932638Abstract: 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: GrantFiled: September 29, 1997Date of Patent: August 3, 1999Assignee: Lord CorporationInventors: Robin F. Righettini, Terrence H. Dawdy
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Patent number: 5929181Abstract: 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: GrantFiled: June 9, 1997Date of Patent: July 27, 1999Assignees: The B.F.Goodrich Co., A.V. Topchiev Institute of Petrochemical SynthesisInventors: Kiryll Lvovich Makovetsky, Eugeny Shmerovich Finkelshtein, Viktor Ivanovich Bykov, Andrey Khristoforovich Bagdasaryan, Brian Leslie Goodall, Larry Funderburk Rhodes
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Patent number: 5741869Abstract: 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: GrantFiled: June 7, 1995Date of Patent: April 21, 1998Assignee: The B.F. Goodrich CompanyInventors: Brian Leslie Goodall, George Martin Benedikt, Lester Howard McIntosh, III, Dennis Allen Barnes, Larry Funderburk Rhodes
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Patent number: 5728782Abstract: 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: GrantFiled: December 6, 1996Date of Patent: March 17, 1998Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Monika Brady, Kevin Joseph Cann, David Joseph Dovedytis
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Patent number: 5717042Abstract: 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: GrantFiled: July 28, 1994Date of Patent: February 10, 1998Assignee: Bridgestone/Firestone, Inc.Inventor: James E. Hall
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Patent number: 5610248Abstract: 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: GrantFiled: March 6, 1995Date of Patent: March 11, 1997Assignee: The University of Southern CaliforniaInventors: Thieo Hogen-Esch, Angela Zagala
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Patent number: 5571881Abstract: 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: GrantFiled: June 7, 1995Date of Patent: November 5, 1996Assignee: The B. F. Goodrich CompanyInventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes, Larry F. Rhodes
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Patent number: 5569730Abstract: 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: GrantFiled: November 15, 1994Date of Patent: October 29, 1996Assignee: The B. F. Goodrich CompanyInventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes, Larry F. Rhodes
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Patent number: 5468819Abstract: 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: GrantFiled: November 16, 1993Date of Patent: November 21, 1995Assignee: The B.F. Goodrich CompanyInventors: Brian L. Goodall, George M. Benedikt, Lester H. McIntosh, III, Dennis A. Barnes
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Patent number: 5411998Abstract: 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: GrantFiled: July 19, 1993Date of Patent: May 2, 1995Assignee: Loctite LimitedInventors: Ciaran B. McArdle, Joseph Burke
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Patent number: 5284927Abstract: 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: GrantFiled: July 31, 1992Date of Patent: February 8, 1994Assignee: The Goodyear Tire & Rubber CompanyInventors: Wen-Liang Hsu, Adel F. Halasa
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Patent number: 5173550Abstract: 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: GrantFiled: April 5, 1991Date of Patent: December 22, 1992Assignee: The Goodyear Tire & Rubber CompanyInventors: Wen-Liang Hsu, Adel F. Halasa
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Patent number: 5171810Abstract: 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: GrantFiled: September 12, 1991Date of Patent: December 15, 1992Assignee: University of Southern CaliforniaInventors: William P. Weber, Stephen Q. Zhou
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Patent number: 5169916Abstract: 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: GrantFiled: December 31, 1990Date of Patent: December 8, 1992Assignee: University of South CaliforniaInventors: William P. Weber, Stephen Q. Zhou
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Patent number: 5137998Abstract: 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: GrantFiled: November 4, 1991Date of Patent: August 11, 1992Assignee: The Goodyear Tire & Rubber CompanyInventors: Wen-Liang Hsu, Adel F. Halasa
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Patent number: 5130390Abstract: 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: GrantFiled: September 10, 1991Date of Patent: July 14, 1992Assignee: University of Southern CaliforniaInventors: William P. Weber, Xiugao Liao
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Patent number: 5112929Abstract: 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: GrantFiled: April 5, 1991Date of Patent: May 12, 1992Assignee: Bridgestone CorporationInventor: James E. Hall
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Patent number: 4843120Abstract: 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: GrantFiled: September 29, 1986Date of Patent: June 27, 1989Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel F. Halasa, Bill B. Gross, Joel L. Cox, George F. Balogh
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Patent number: 4783516Abstract: 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: GrantFiled: November 22, 1983Date of Patent: November 8, 1988Assignee: Union Carbide CorporationInventors: Curtis L. Schilling, Jr., Bernard Kanner
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Patent number: 4537939Abstract: 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: GrantFiled: June 4, 1984Date of Patent: August 27, 1985Assignee: The Firestone Tire & Rubber CompanyInventors: James E. Hall, Donald N. Schulz
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Patent number: 4530984Abstract: 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: GrantFiled: April 2, 1984Date of Patent: July 23, 1985Assignee: The Firestone Tire & Rubber CompanyInventor: James E. Hall
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Patent number: 4476240Abstract: 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: GrantFiled: July 1, 1982Date of Patent: October 9, 1984Assignee: The Firestone Tire & Rubber CompanyInventors: James E. Hall, Donald N. Schulz
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Patent number: 4473661Abstract: 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: GrantFiled: July 1, 1982Date of Patent: September 25, 1984Assignee: The Firestone Tire & Rubber CompanyInventor: James E. Hall
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Patent number: 4336361Abstract: 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: GrantFiled: November 17, 1980Date of Patent: June 22, 1982Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Teiji Tsuruta, Yoshiaki Nitadori
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Patent number: 4264753Abstract: 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: GrantFiled: May 20, 1980Date of Patent: April 28, 1981Assignee: The Firestone Tire & Rubber CompanyInventors: Adel F. Halasa, James E. Hali
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Patent number: 4230841Abstract: 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: GrantFiled: January 31, 1979Date of Patent: October 28, 1980Assignee: The Goodyear Tire & Rubber CompanyInventor: Robert T. Prudence
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Patent number: 4208498Abstract: 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: GrantFiled: September 29, 1978Date of Patent: June 17, 1980Assignee: Compagnie Generale des Etablissements MichelinInventor: Jean-Marie Massoubre
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Patent number: 4202954Abstract: 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: GrantFiled: September 29, 1978Date of Patent: May 13, 1980Assignee: Compagnie Generale des Etablissements MichelinInventor: Jean-Marie Massoubre
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Patent number: 4189555Abstract: 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: GrantFiled: September 15, 1976Date of Patent: February 19, 1980Assignee: Compagnie Generale des Etablissements MichelinInventor: Jean-Marie Massoubre
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Patent number: 4180637Abstract: 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: GrantFiled: November 7, 1977Date of Patent: December 25, 1979Assignee: The Dow Chemical CompanyInventors: Syamalarao Evani, Russell J. Raymond
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Patent number: 4091198Abstract: 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: GrantFiled: September 10, 1976Date of Patent: May 23, 1978Assignee: Phillips Petroleum CompanyInventors: Richard L. Smith, Ralph C. Farrar, Daniel H. Willis
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Patent number: 3959100Abstract: Ultraviolet polymerization of photopolymerizable binders or vehicles is improved by incorporating thereinto a sensitizer composition comprising an activated halogenated azine compound.Type: GrantFiled: September 23, 1974Date of Patent: May 25, 1976Assignee: SCM CorporationInventor: Vincent Daniel McGinniss
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Patent number: 3954700Abstract: 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: GrantFiled: July 11, 1975Date of Patent: May 4, 1976Assignee: The Firestone Tire & Rubber CompanyInventor: Adel Farhan Halasa