Contains Compound Of Nitrogen Patents (Class 526/180)
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Patent number: 6566478Abstract: 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: GrantFiled: April 30, 2002Date of Patent: May 20, 2003Assignee: The Goodyear Tire & Rubber CompanyInventors: Steven Kristofer Henning, Michael Lester Kerns, Zhengfang Xu
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Patent number: 6552141Abstract: The invention relates to a method for producing water-soluble or water-swellable polymerizates with a low residual monomer content from acrylic acid and/or acrylic acid derivatives. The method is characterized by the addition of a nitrogen compound to the monomer solution to be polymerized, an in that the polymerizate is subsequently heated at temperature of 120 to 240° C. The polymerizates produced according to the inventive method are suitable as flocculants, dispersants and absorbers.Type: GrantFiled: June 14, 2000Date of Patent: April 22, 2003Assignee: Stockhausen GmbH & Co. KGInventors: Miroslav Chmelir, Kurt Dahmen
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Patent number: 6521733Abstract: A tapered aromatic vinyl-conjugated diene copolymer rubber having a ratio W0.6Mp/WMp in the range of 0.65-0.9 or 1.1-1.3 wherein Mp is molecular weight of a copolymer molecule corresponding to the peak of a molecular weight distribution curve obtained by gel permeation chromatography, WMp is a weight fraction of aromatic vinyl monomer units in the copolymer molecule having a molecular weight Mp, and W0.6Mp is a weight fraction of aromatic vinyl monomer units in a copolymer molecule having a molecular weight of Mp×0.6. A coupled tapered rubber comprised of a plurality of tapered copolymer molecules which are bound together at molecule terminal. A rubber composition comprising this tapered rubber or coupled tapered rubber and natural rubber or a synthetic rubber. This rubber composition exhibits reduced heat build-up, and high wet skid resistance, tensile strength and abrasion resistance.Type: GrantFiled: February 11, 2002Date of Patent: February 18, 2003Assignee: Zeon CorporationInventor: Takeshi Karato
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Publication number: 20030032745Abstract: Hetero-telechelic polymers having the formula:Type: ApplicationFiled: March 27, 2000Publication date: February 13, 2003Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
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Publication number: 20030032746Abstract: Hetero-telechelic polymers having the formula:Type: ApplicationFiled: June 21, 2002Publication date: February 13, 2003Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
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Patent number: 6515087Abstract: 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: GrantFiled: December 6, 2001Date of Patent: February 4, 2003Assignee: The Goodyear Tire & Rubber CompanyInventors: Wen-Liang Hsu, Adel Farhan Halasa, Scott McDowell Christian, Michael Lester Kerns
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Publication number: 20030013827Abstract: Hetero-telechelic polymers having the formula:Type: ApplicationFiled: June 21, 2002Publication date: January 16, 2003Inventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
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Publication number: 20020120082Abstract: 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: ApplicationFiled: December 6, 2001Publication date: August 29, 2002Inventors: Wen-Liang Hsu, Adel Farhan Halasa, Scott McDowell Christian, Michael Lester Kerns
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Patent number: 6429273Abstract: 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: GrantFiled: September 14, 1998Date of Patent: August 6, 2002Assignee: Asahi Kasei Kabushiki KaishaInventor: Kenji Ebara
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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: 6221991Abstract: 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 consistingType: GrantFiled: June 30, 1998Date of Patent: April 24, 2001Assignee: FMC CorporationInventors: Robert J. Letchford, James A. Schwindeman, Conrad W. Kamienski, Roderic P. Quirk
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Patent number: 6184338Abstract: The present invention provides novel anionic polymerization amine initiators having a tertiary amine group pendant to the polymer chain and processes for making the same. The initiators can be useful in the preparation of tertiary amine containing polymers, including linear, homotelechelic, heterotelechelic and radial polymers.Type: GrantFiled: August 24, 1998Date of Patent: February 6, 2001Assignee: FMC CorporationInventors: James A. Schwindeman, Robert J. Letchford
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Patent number: 6160054Abstract: 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: GrantFiled: July 18, 1996Date of Patent: December 12, 2000Assignee: FMC CorporationInventors: James A. Schwindeman, Robert J. Letchford, Conrad W. Kamienski, Roderic P. Quirk
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Patent number: 6153706Abstract: 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: GrantFiled: July 28, 1998Date of Patent: November 28, 2000Assignee: FMC CorporationInventors: Robert James Letchford, James Anthony Schwindeman
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Patent number: 6140434Abstract: 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: GrantFiled: January 8, 1999Date of Patent: October 31, 2000Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel Farhan Halasa, Wen-Liang Hsu
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Patent number: 6133388Abstract: This invention relates to a process for preparing styrene-butadiene rubber or butadiene rubber with both ends of the polymer chain modified by solution polymerization, wherein styrene-butadiene rubber or butadiene rubber is polymerized using a monofunctional anionic polymerization initiator modified with amines or the like, and then the active anion at the ends of the polymer chain is reacted with the commonly available modifier. Unlike a bifunctional initiator that shows a poor solubility in a nonpolar solvent, an increase in viscosity and loss of modification efficiency induced by impurity, styrene-butadiene rubber or butadiene rubber by solution polymerization can be prepared using the modified anionic polymerization initiator of the invention.Type: GrantFiled: September 20, 1999Date of Patent: October 17, 2000Assignee: Hankook Tire Co., Ltd.Inventors: Ki Young Lee, Bum Jae Lee
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Patent number: 6107408Abstract: 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: GrantFiled: February 26, 1998Date of Patent: August 22, 2000Assignee: FMC CorporationInventors: Roderic Paul Quirk, Robert James Letchford, James Anthony Schwindeman
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Patent number: 6084025Abstract: A functionalized polymer prepared by a process comprising the steps of preparing a solution of a cyclic amine compound, an organolithium compound, and from 3 to about 300 equivalents, based upon one equivalent of lithium, of a monomer selected from the group including diene monomers, vinyl aromatic monomers, and mixtures thereof, where the cyclic amine compound is defined by the formula where R.sub.2 is selected from the group consisting of an alkylene, substituted alkylene, oxy- or N-alkylamino-alkylene group having from about 3 to about 16 methylene groups, N is a nitrogen atom, and H is a hydrogen atom, thereby forming a polymerization initiator having the formula where Li is a lithium atom, SOL is a divalent hydrocarbon group having from 3 to about 300 polymerized monomeric units, y is from 0.5 to about 3, and A is a cyclic amine radical derived from the cyclic amine, charging the solution containing (A)Li(SOL)y with from about 0.Type: GrantFiled: March 15, 1999Date of Patent: July 4, 2000Assignee: Bridgestone CorporationInventors: Takashi Kitamura, David F. Lawson, Koichi Morita, Yoichi Ozawa
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Patent number: 6046288Abstract: 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: GrantFiled: September 24, 1997Date of Patent: April 4, 2000Assignee: Bridgestone CorporationInventors: David F. Lawson, Michael L. Kerns, John R. Schreffler
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Patent number: 6025450Abstract: A functionalized polymer includes a polymer chain carrying at least one functional group selected from alkyl, dialkyl and cycloalkyl amine radicals having the general formula ##STR1## and cyclic amine radicals having the general formula ##STR2## where R.sub.1 is an alkyl, cycloalkyl or aralkyl having from 1 to about 12 carbon atoms, and R.sub.2 is an alkylene, substituted alkylene, oxy- or N-alkylamino-alkylene group having from about 3 to about 16 methylene groups. The invention also provides products based upon such polymers.Type: GrantFiled: July 9, 1998Date of Patent: February 15, 2000Assignee: Bridgestone CorporationInventors: David F. Lawson, Mark L. Stayer, Jr., David Saffles, Koichi Morita, Yoichi Ozawa, Ryota Fujio, Thomas A. Antkowiak
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Patent number: 5973086Abstract: 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: GrantFiled: December 27, 1996Date of Patent: October 26, 1999Assignee: Council of Scientific & Industrial ResearchInventors: Durairaj Baskaran, Swaminathan Sivaram
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Patent number: 5959048Abstract: An acyclic alkane soluble anionic polymerization initiator includes a mixture of from about 90 to about 10 parts by weight of a lithio amine having the general formula A.sub.1 Li and from about 10 to about 90 parts by weight of at least one other lithio amine having the general formula A.sub.2 Li. A.sub.1 and A.sub.2 are selected from the dialkyl, alkyl, cycloalkyl and dicycloalkyl amine radicals and cyclic amine radicals. There is also provided a method of forming a mixture of anionic polymerization initiators, a functionalized polymer and a method of forming a functionalized polymer.Type: GrantFiled: July 1, 1997Date of Patent: September 28, 1999Assignee: Bridgestone CorporationInventors: David F. Lawson, James E. Hall, Yoichi Ozawa
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Patent number: 5932662Abstract: A functionalized polymer according to the invention includes a polymer molecule having the general formula AYLi where A is a cyclic amine-containing radical having the general formula ##STR1## wherein R.sub.1 is a divalent alkylene, an oxy- or amino-alkylene, or substituted alkylene having from 6 to about 20 carbon atoms; R.sub.2 is a linear-, branched-, or cyclo-alkylene having from about 2 to about 20 carbon atoms; and Y is a divalent polymer radical and Li is a lithium atom bonded to a carbon atom of Y.Type: GrantFiled: November 7, 1996Date of Patent: August 3, 1999Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
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Patent number: 5916961Abstract: The reduction of hysteresis in a silica-filled, vulcanized elastomeric compound is produced by mixing diene monomer and optionally monovinyl aromatic monomer with a lithium amine initiator and, optionally, a modifier; effecting polymerization conditions; terminating polymerization with an amino group producing terminator to form an amine functionalized diene elastomer; compounding the amine functionalized diene elastomer with an amorphous silica filler and a vulcanization agent; and, effecting vulcanization. A pneumatic tire tread stock incorporating the vulcanized elastomer compound exhibits decreased rolling resistance in the tire.Type: GrantFiled: July 11, 1997Date of Patent: June 29, 1999Assignee: Bridgestone CorporationInventors: William L. Hergenrother, Thomas J. Lynch
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Patent number: 5906956Abstract: 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: GrantFiled: April 3, 1997Date of Patent: May 25, 1999Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel Farhan Halasa, Wen-Liang Hsu
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Patent number: 5900464Abstract: 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: GrantFiled: July 10, 1996Date of Patent: May 4, 1999Assignee: FMC CorporationInventors: Robert J. Letchford, James A. Schwindeman, Conrad W. Kamienski, Roderic P. Quirk
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Patent number: 5883183Abstract: The present 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)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: GrantFiled: June 6, 1995Date of Patent: March 16, 1999Assignee: Bridgestone CorporationInventors: Takashi Kitamura, David F. Lawson, Koichi Morita, Yoichi Ozawa
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Patent number: 5852189Abstract: Relatively pure tertiaryaminoalkyllithium initiators suitable for anionic polymerization reactions are prepared at low temperatures in an organic ether by reacting an equivalent excess of lithium metal with a tertiaryaminoalkylhalide. The lithium initiators are very stable at moderate temperatures when the ether is replaced by an aliphatic, a cycloaliphatic, or an aromatic solvent. Yields of the initiator in excess of 98% are readily achieved.Type: GrantFiled: December 31, 1996Date of Patent: December 22, 1998Assignee: Bridgestone CorporationInventors: William L. Hergenrother, Michael L. Kerns, David F. Lawson
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Patent number: 5849847Abstract: 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: GrantFiled: July 29, 1996Date of Patent: December 15, 1998Assignee: FMC CorporationInventor: Roderic P. Quirk
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Patent number: 5830965Abstract: Disclosed is a polymer containing a modified cyclic monomer unit, comprising a polymer chain represented by the following formula (I): ##STR1## wherein A to F are monomer units constituting a main chain of the polymer chain, in which monomer units A to F are arranged in any order, and l to q are, respectively, weight percentages of monomer units A to F, based on the total weight of monomer units A to F; A is selected from cyclic olefin monomer units, B is selected from cyclic conjugated diene monomer units, and C to F are monomer units copolymerizable with monomer units A and B, wherein each of S to X, which are modifying groups, is a functional group or an organic compound residue containing the functional group, with the functional group containing at least one member selected from oxygen, nitrogen, sulfur, silicon, phosphorus and halogen; and wherein s to x are, respectively, weight percentages of modifying groups S to X, based on the weight of the polymer, and wherein the polymer has a number average moleType: GrantFiled: June 5, 1996Date of Patent: November 3, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Kimio Imaizumi, Itaru Natori, Hideyuki Yamagishi, Kiyoo Kato
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Patent number: 5827929Abstract: 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: GrantFiled: April 12, 1996Date of Patent: October 27, 1998Assignee: FMC CorporationInventors: James A. Schwindeman, Eric J. Granger, John F. Engel, Conrad W. Kamienski
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Patent number: 5795945Abstract: Disclosed is a polymer containing a cyclic olefin monomer unit, comprising a main chain represented by the formula: ##STR1## wherein A to F are monomer units constituting the main chain in which A to F are arranged in any order, and a to f are, respectively, weight percentages of A to F, based on the total weight of A to F; A to F are selected from cyclic olefin monomer units, cyclic conjugated diene monomer units, chain conjugated diene monomer units, vinyl aromatic monomer units, polar monomer units, and an ethylene monomer unit and .alpha.-olefin monomer units, respectively; and a to f satisfy the following requirements: 0.001.ltoreq.a.ltoreq.100, and 0.ltoreq.b, c, d, e, f.ltoreq.100, with the proviso that monomer unit A is present in an amount of from 0.Type: GrantFiled: December 21, 1995Date of Patent: August 18, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventor: Itaru Natori
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Patent number: 5792820Abstract: An organolithium compound according to the present invention containing a cyclic amino group, has the general formula: ##STR1## wherein R.sub.1 is a divalent alkylene, an oxy- or amino-alkylene, or substituted alkylene having from 6 to about 20 carbon atoms; R.sub.2 is a linear-, branched-, or cyclo-alkylene having from about 2 to about 20 carbon atoms; and the lithium, Li, is bonded directly to a carbon atom of R.sub.2. A method of preparing an organolithium compound containing a cyclic amino group, comprising reacting a cyclic amino organo halide having the general formula ##STR2## where R.sub.1 and R.sub.2 are as above, and X is bromine or chlorine bonded directly to a carbon atom of R.sub.2, with a lithium reactant selected from lithium metal or an organolithium compound.Type: GrantFiled: February 23, 1996Date of Patent: August 11, 1998Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
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Patent number: 5792824Abstract: Disclosed is a cyclic conjugated diene polymer comprising a main chain represented by the formula (I): ##STR1## wherein A to E are monomer units constituting the main chain in which A to E are arranged in any order, and l to p are, respectively, weight percentages of A to E, based on the total weight of A to E; A is selected from cyclic conjugated diene monomer units, B is selected from chain conjugated diene monomer units, C is selected from vinyl aromatic monomer units, D is selected from polar monomer units, and E is selected from an ethylene monomer unit and .alpha.-olefin monomer units; and l to p satisfy the following requirements: 0.5.ltoreq.l.ltoreq.100, 0.ltoreq.Type: GrantFiled: December 8, 1995Date of Patent: August 11, 1998Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventor: Itaru Natori
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Patent number: 5786441Abstract: A functionalized polymer comprising a polymeric segment, having at least one cyclic amine end group, defined according to formula (I) ##STR1## where Z is an anionically-polymerized polymer; R.sub.1 is selected from the group consisting of organic groups containing from 1 to about 12 carbon atoms and a bridging bond; each R.sub.2 is independently selected from the group consisting of hydrogen, organic groups containing from 1 to about 12 carbon atoms, and a bridging bond; each R.sub.3 is independently selected from the group consisting of hydrogen and organic groups containing from 1 to about 12 carbon atoms; a is an integer from 4 to about 16; and b is an integer from 0 to about 12; and optionally including a bridge, formed by the selection of two of said bridging bonds, the bridge having 0 to about 6 carbon atoms between the bridging ring members; said polymer having been crosslinked. Also provided are vulcanizable compositions of matter, vulcanizates, and tires of the functionalized polymers.Type: GrantFiled: December 31, 1996Date of Patent: July 28, 1998Assignee: Bridgestone CorporationInventors: David F. Lawson, William L. Hergenrother, Michael L. Kerns
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Patent number: 5785778Abstract: A functionalized polymer according to the invention includes a polymer molecule having the general formula AYLi where A is a cyclic amine-containing radical having the general formula ##STR1## wherein R.sub.1 is a divalent alkylene, an oxy- or amino-alkylene, or substituted alkylene having from 6 to about 20 carbon atoms; R.sub.2 is a linear-, branched-, or cyclo-alkylene having from about 2 to about 20 carbon atoms; and Y is a divalent polymer radical and Li is a lithium atom bonded to a carbon atom of Y.Type: GrantFiled: March 7, 1997Date of Patent: July 28, 1998Assignee: Bridgestone CorporationInventors: David F. Lawson, Thomas A. Antkowiak, James E. Hall, Mark L. Stayer, Jr., John R. Schreffler
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Patent number: 5723533Abstract: An acyclic alkane soluble anionic polymerization initiator includes a mixture of from about 90 to about 10 parts by weight of a lithio amine having the general formula A.sub.1 Li and from about 10 to about 90 parts by weight of at least one other lithio amine having the general formula A.sub.2 Li. A.sub.1 and A.sub.2 are selected from the dialkyl, alkyl, cycloalkyl and dicycloalkyl amine radicals and cyclic amine radicals. There is also provided a method of forming a mixture of anionic polymerization initiators, a functionalized polymer and a method of forming a functionalized polymer.Type: GrantFiled: November 26, 1996Date of Patent: March 3, 1998Assignee: Bridgestone CorporationInventors: David F. Lawson, James E. Hall, Yoichi Ozawa
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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: 5717043Abstract: 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: GrantFiled: October 16, 1996Date of Patent: February 10, 1998Assignee: Bridgestone CorporationInventors: Atushi Nakayama, Koichi Morita, Masaaki Izuchi
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Patent number: 5708092Abstract: 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: GrantFiled: April 12, 1996Date of Patent: January 13, 1998Assignee: FMC CorporationInventors: James A. Schwindeman, Conrad W. Kamienski, Robert C. Morrison
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Patent number: 5700888Abstract: 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: GrantFiled: November 10, 1996Date of Patent: December 23, 1997Assignee: Bridgestone CorporationInventor: James E. Hall
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Patent number: 5698646Abstract: 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: GrantFiled: June 6, 1995Date of Patent: December 16, 1997Assignee: Bridgestone CorporationInventors: Takashi Kitamura, Mark L. Stayer, Jr., Akira Matsuda
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Patent number: 5677402Abstract: 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: GrantFiled: July 24, 1996Date of Patent: October 14, 1997Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel Farhan Halasa, Wen-Liang Hsu
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Patent number: 5674798Abstract: 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: GrantFiled: December 19, 1994Date of Patent: October 7, 1997Assignee: Bridgestone CorporationInventors: Takashi Kitamura, David F. Lawson, Koichi Morita, Yoichi Ozawa
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Patent number: 5670592Abstract: The invention concerns the anionic polymerization of alkyl methacrylate in the presence of a priming system. The priming system comprises an organolithium primer and an organic compound of aluminum and pyridine. This priming system allows better polymerization control.Type: GrantFiled: August 25, 1995Date of Patent: September 23, 1997Assignee: Elf Atochem S.A.Inventors: Philippe Teyssie, Bruno Vuillemin, Jinshan Wang
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Patent number: 5654384Abstract: 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: GrantFiled: March 27, 1996Date of Patent: August 5, 1997Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel Farhan Halasa, Wen-Liang Hsu, David John Zanzig, Paul Harry Sandstrom, Steven Kristofer Henning, Danielle Lucas
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Patent number: 5643848Abstract: An acyclic alkane soluble anionic polymerization initiator includes a mixture of from about 90 to about 10 parts by weight of a lithio amine having the general formula A.sub.1 Li and from about 10 to about 90 parts by weight of at least one other lithio amine having the general formula A.sub.2 Li. A.sub.1 and A.sub.2 are selected from the dialkyl, alkyl, cycloalkyl and dicycloalkyl amine radicals and cyclic amine radicals. There is also provided a method of forming a mixture of anionic polymerization initiators, a functionalized polymer and a method of forming a functionalized polymer.Type: GrantFiled: May 3, 1995Date of Patent: July 1, 1997Assignee: Bridgestone CorporationInventors: David F. Lawson, James E. Hall, Yoichi Ozawa
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Patent number: 5629256Abstract: The subject invention relates to an anionic polymerization technique for synthesizing rubbery polymers of conjugated diolefin monomers, such as rubbery copolymer of .alpha.-methylstyrene and 1,3-butadiene. These rubbery copolymers exhibit an excellent combination of properties for utilization in tire tread rubber compounds. They have high trans-isomer contents which leads to good treadwear characteristics and a broad molecular weight distribution which enhances processability.Type: GrantFiled: July 29, 1996Date of Patent: May 13, 1997Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel F. Halasa, Laurie E. Austin, Susan A. Weakland
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Patent number: 5625017Abstract: A process for preparing a polymer comprises polymerizing a conjugated diene monomer and/or a vinylaromatic hydrocarbon monomer in a hydrocarbon solvent in the presence of or in the absence of a randomizer by using a lithium polymerization initiator which is formed by bringing an organolithium compound and at least one secondary amine compound into contact with each other in the polymerization system in the presence of at least said monomer, wherein the polymerization conversion at the time of contact is less than 5%. The secondary amine is an amine compound having two hydrocarbon groups bonded to N or an imine compound in which an NH group and a saturated or unsaturated cyclic structure group form a cyclic structure. The cyclic structure group comprises a hydrocarbon group as the ring member and may also comprise N or O.Type: GrantFiled: September 21, 1995Date of Patent: April 29, 1997Assignee: Bridgestone CorporationInventors: Koichi Morita, Atsushi Nakayama, Yoichi Ozawa, Ryota Fujio
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Patent number: 5623035Abstract: The subject invention relates to an anionic polymerization technique for synthesizing rubbery polymers of conjugated diolefin monomers, such as a rubbery copolymer of .alpha.-methylstyrene and 1,3-butadiene. These rubbery copolymers exhibit an excellent combination of properties for utilization in tire tread rubber compounds. They have high trans-isomer contents which leads to good treadwear characteristics and a broad molecular weight distribution which enhances processability.Type: GrantFiled: July 21, 1995Date of Patent: April 22, 1997Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel F. Halasa, Laurie E. Austin, Susan A. Weakland