Material Contains Elemental Alkali Metal, Hydride Thereof, Or Alkali Metal To Carbon Atom Bond (li, Na, K, Rb, Cs, Fr) Patents (Class 526/173)
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Patent number: 6878789Abstract: 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): AlR1R2R3??(I) wherein R1 represents an alkyl group having at least 3 carbon atoms, an alkoxy group having at least 3 carbon atoms or an aryloxy group, R2 and R3 each independently represent an aryloxy group or may be coupled together to form an arylenedioxy group. The process makes it possible to heighten the reaction rate and living properties upon polymerization and heighten the block formation efficiency upon block copolymerization.Type: GrantFiled: September 24, 2001Date of Patent: April 12, 2005Assignee: Kuraray Co., Ltd.Inventors: Naohiko Uchiumi, Kenichi Hamada, Masaji Kato, Tomohiro Ono, Sachie Yaginuma, Kazushige Ishiura
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Patent number: 6878797Abstract: A process for producing alkali metal polymaleimide salts by alkaline hydrolysis of maleimide polymers prepared by polymerization of maleimide monomers in the presence of a metal oxide and alcohol initiator or a base. In particular, the process produces alkali metal polymaleimide salts with particular ratios of C—N and C—C connected maleimide-derived monomer units which are dependent on the particular initiator used to synthesize the maleimide polymer. The alkali metal polymaleimide salts, which have chelating and anti-scaling properties, are useful as chelating agents and detergent builders and as such are suitable biodegradable replacements for synthetic polymers and sodium polyaspartate.Type: GrantFiled: April 19, 2002Date of Patent: April 12, 2005Assignees: Board of Trustees of Michigan State University, Applied CarboChemicalsInventors: Kris A. Berglund, Parminder Agarwal, Qiuyue Yu, Adam Harant
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Patent number: 6872783Abstract: A continuous process for manufacture of a polymer including branched and linear components comprising first polymerizing conjugated diene(s) in the presence of an organometallic initiator to a conversion that is at least 90% complete. A coupling agent is added to obtain a polymer including branched and linear components. The coupling agent is added at a ratio of about 0.3 to about 0.6 coupling equivalents to initiator equivalents.Type: GrantFiled: November 26, 2002Date of Patent: March 29, 2005Assignee: Firestone Polymers, LLCInventor: Mark N. Dedecker
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Patent number: 6869678Abstract: A removable pressure-sensitive adhesive which, even when applied to metal sheets or to metallic members which have undergone a coating treatment, is inhibited from increasing in adhesive force with the lapse of time and can be easily removed therefrom and which has satisfactory weatherability and satisfactory pot life contains 100 parts by weight on a solid basis of an aqueous dispersion type acrylic copolymer obtained by polymerizing a monomer mixture in an aqueous medium in the presence of a nonionic surfactant and/or an anionic surfactant each having an ethylenic double bond and 0.1 to 3 parts by weight of a hindered-amine light stabilizer having a piperidine ring in which the nitrogen atom has a tertiary amine structure; and an adhesive sheet is produced with the adhesive.Type: GrantFiled: December 10, 2002Date of Patent: March 22, 2005Assignee: Nitto Denko CorporationInventors: Takeshi Yamanaka, Shinetsu Itou, Kenichi Shibata, Takeshi Suto, Isamu Miyoshi
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Patent number: 6835269Abstract: A laminated film exhibiting excellent interlayer adhesiveness obtained by extrusion-laminating a resin directly on a polyester film without effecting anchor-coating or without treating the molten film of the extrusion-laminated resin with ozone. The laminated film is obtained by extrusion-laminating, onto the polyester film, an ethylene copolymer containing an unsaturated carboxylic acid and a (meth)acrylic acid ester, which may be further blended with a small amount of an ethylene/&agr;-olefin copolymer having a density of 840 to 900 kg/m3, the amount of the unsaturated carboxylic acid component being from 1 to 12% by weight and the amount of the (meth)acrylic acid ester component being from 2 to 25% by weight.Type: GrantFiled: March 29, 2001Date of Patent: December 28, 2004Assignee: DuPont-Mitsui Polychemicals Co., Ltd.Inventors: Kenji Miharu, Naozumi Suzuki
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Publication number: 20040260002Abstract: The present invention relates in particular to a preparation process for a copolymer having two blocks usable in a sulphur-cross-linkable rubber composition of reduced hysteresis in the cross-linked state, such a block copolymer in which one of the blocks is constituted of a polyisoprene and the other of a diene elastomer other than a polyisoprene, and this rubber composition for tyre treads.Type: ApplicationFiled: April 30, 2004Publication date: December 23, 2004Applicant: MICHELIN RECHERCHE ET TECHNIQUE S.A.Inventors: Pierre Robert, Jean-Michel Favrot, Pierre Lesage
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Patent number: 6825306Abstract: The present invention relates to a rubbery polymer which is comprised of repeat units that are derived from (1) at least one conjugated diolefin monomer, and (2) at least one functionalized monomer of the structural formula: wherein the R′ groups in repeat units and in different repeat units can be the same or different and represent hydrogen atoms or alkyl groups containing from 1 to about 4 carbon atoms, wherein x represents an integer from 1 to about 10, and wherein the R groups in repeat units and in different repeat units can be the same or different and represent alkyl groups containing from 1 to about 10 carbon atoms or alkoxy groups containing from 1 to about 10 carbon atoms.Type: GrantFiled: September 12, 2003Date of Patent: November 30, 2004Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel Farhan Halasa, Wen-Liang Hsu
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Publication number: 20040235647Abstract: The present invention provides protected functionalized polymerization initiators having less than one molar equivalent chain extension agent introduced therein to provide hydrocarbon solubility.Type: ApplicationFiled: July 2, 2004Publication date: November 25, 2004Inventors: James A. Schwindeman, Randy W. Hall
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Patent number: 6812307Abstract: This invention is based upon the unexpected finding that random copolymers of 1,3-butadiene monomer and 3-(2-pyrrolidinoethyl) styrene and/or 4-(2-pyrrolidinoethyl) styrene having a low vinyl content can be synthesized by anionic polymerization at normal polymerization temperatures without the need for a conventional polar modifier. The subject invention more specifically discloses a process for synthesizing a rubbery polymer that comprises copolymerizing at least one conjugated diolefin monomer and at least one functionalized monomer in an organic solvent at a temperature which is within the range of 20° C. to about 100° C., wherein the polymerization is initiated with an anionic initiator, wherein the functionalized monomer is of the structural formula: wherein n represents an integer from 4 to about 10, and wherein the polymerization is conducted in the absence of conventional polar modifiers.Type: GrantFiled: July 22, 2003Date of Patent: November 2, 2004Assignee: The Goodyear Tire & Rubber CompanyInventors: Adel Farhan Halasa, Wen-Liang Hsu
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Patent number: 6790921Abstract: This invention discloses a rubbery polymer which is comprised of repeat units that are derived from (1) at least one conjugated diolefin monomer, and (2) at least one functionalized monomer having of the structural formula: wherein R represents an alkyl group containing from 1 to about 10 carbon atoms or a hydrogen atom, and wherein R1 and R2 can be the same or different and represent hydrogen atoms or a moiety of the structural formula: wherein the R3 groups in repeat units and in different repeat units can be the same or different and represent hydrogen atoms or alkyl groups containing from 1 to about 4 carbon atoms, wherein n and x represents integers from 1 to about 10, with the proviso that R1 and R2 can not both be hydrogen atoms.Type: GrantFiled: June 30, 2003Date of Patent: September 14, 2004Assignee: The Goodyear Tire & Rubber CompanyInventors: Stephan Rodewald, Steven Kristofer Henning, Brian Earl Burkhart
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Patent number: 6790920Abstract: Removing silicon species from hydrocarbon solvents such as cyclohexane by flowing the hydrocarbon solvent through a selective adsorbent selected from the group consisting of aluminas, silicon-aluminas, ion exchange resins, zeolite Y, and combinations thereof.Type: GrantFiled: September 12, 2002Date of Patent: September 14, 2004Assignee: KRATON Polymers U.S. LLCInventors: Zaida Diaz, Grant W. Haddix
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Patent number: 6787661Abstract: The present invention relates to a tin-containing organolithium compound which can be used as anionic polymerization initiators, represented by the following formula (1): R4−xSn(Ya—Zm—Yb—Li)x (1) Wherein R, Z and Y are defined as in the specification; x represents a value of 1 or 2; m represents a value of 0 or 1; a represents a value of 0 to 6, b represents a value of 0 to 6, a+b is from 0 to 6, provided that m=1 when x=1. The tin-containing organolithium compounds according to the present invention can be used as initiators to initiate the polymerization of conjugated dienes and/or monovinyl aromatic hydrocarbons, thereby synthesizing various linear, star or telechelic polymers. The present invention also relates to a method for preparing the tin-containing organolithium compounds according to the present invention.Type: GrantFiled: June 11, 2002Date of Patent: September 7, 2004Assignees: China Petroleum and Chemical Corporation, Research Institute of Beijing YanshanInventors: Chuanqing Li, Aimin Liang, Wei Li, Liyun Zhao, Song Lu, Lin Xu, Qing Liu
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Patent number: 6777511Abstract: An industrially excellent process for producing a poly(meth)acrylate having a reduced metal content which comprises contacting a mixture of a poly(meth)acrylate and an organic solvent with an acidic aqueous solution, such as an aqueous solution obtained by dissolving a polyprotic carboxylic acid having about 2 to 12 carbon atoms in water, is provided, and, by this invention, contents of metals such as sodium, potassium, iron and the like can be remarkably reduced.Type: GrantFiled: September 21, 2001Date of Patent: August 17, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Koshiro Ochiai, Akira Kamabuchi
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Publication number: 20040147696Abstract: The present invention relates to a linear or branched diene elastomer having cyclic vinyl units. A linear diene elastomer according to the invention results from at least one conjugated diene and it comprises cyclic vinyl units in a mass content of greater than or equal to 15% while having a number-average molecular weight falling within a range of from 10,000 to 300,000 g/mol.Type: ApplicationFiled: January 14, 2004Publication date: July 29, 2004Applicant: MICHELIN RECHERCHE ET TECHNIQUE S.A.Inventors: Jean-Luc Cabioch, Laurent Coissieux, Nicole Dajoux
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Patent number: 6767976Abstract: (1) A methacrylic ester or an acrylic ester is anionically polymerized, using a polymerization initiator compound comprising an addition reaction product of a conjugated diene compound and an organic alkali metal compound, in the presence of a tertiary organoaluminum compound having in the molecule thereof a chemical structure represented by a formula: Al—O—Ar wherein Ar represents an aromatic ring; or (2) a methacrylic ester or an acrylic ester is anionically polymerized, using a polymerization initiator compound comprising an addition reaction product of an organic alkali metal compound and a compound having a 1,1-diaryl-1-alkene structure, by adding the ester in the form of a mixture with the above-mentioned specific tertiary organoaluminum compound to the polymerization system.Type: GrantFiled: June 3, 2003Date of Patent: July 27, 2004Assignee: Kuraray Co., Ltd.Inventors: Kenichi Hamada, Kazushige Ishiura, Toru Takahashi, Sachie Yaginuma, Makoto Akai, Tomohiro Ono, Kenji Shachi
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Patent number: 6765065Abstract: There is provided a process for producing a modified polymer rubber having modified both ends, which comprises the steps of: (1) reacting a compound represented by the following formula (1) with an organic alkali metal compound to produce a chemical species, (2) polymerizing a conjugated diene monomer or a combination of a conjugated diene monomer with an aromatic vinyl monomer in the presence of the chemical species to produce an active polymer having an alkali metal at an end thereof, and (3) reacting the active polymer with a functional group-carrying modifying agent in a hydrocarbon solvent to produce the modified polymer rubber having modified both ends.Type: GrantFiled: October 10, 2002Date of Patent: July 20, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Mayumi Oshima, Seiichi Mabe, Katsunari Inagaki
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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: 20040132916Abstract: The present invention relates to a process for polymer hydrogenation that includes: polymerizing or copolymerizing at least one conjugated diene in a hydrocarbon solvent using an organic alkali metal polymerization initiator to generate a living polymer; adding a terminating agent selected from amines, esters, ketones, or halogen compounds to deactivate the active terminal of the living polymer; and selectively hydrogenating the conjugated diene polymer using at least one organotitanium compound and a lithium hydride, which is prepared from a reactor equipped with a high-speed injection nozzle and thereby precisely controlled in regard to particle diameter.Type: ApplicationFiled: September 2, 2003Publication date: July 8, 2004Applicant: Korea Kumho Petrochemical Co., Ltd.Inventors: Young-Hoon Ko, Hoo-Chae Kim, Jae-Yun Kim, Jin-Man Hwang
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Patent number: 6759498Abstract: A process for producing a styrenic resin with a small content of low molecular weight components, comprising a continuous anionic polymerization process wherein a raw material system having the following composition (A) is continuously fed, either collectively or in a divided manner, from one end of a reactor tank R1 having a back mixing flow and the product system is continuously discharged from the other end of the reactor tank R1, the internal temperature of the reactor tank R1 being controlled to a range of 40-120° C., the average proportion of styrene monomers to the sum total of the styrene monomers, hydrocarbon solvent and styrenic polymers present in the reactor tank R1 being controlled to less than 10 wt. %, and the resulting styrenic polymer solution being devolatilized and dried: (A) Styrene monomer 1.0 kg Hydrocarbon solvent 0.1-3 kg Organolithium compound 0.5-200 mmoles.Type: GrantFiled: November 8, 2002Date of Patent: July 6, 2004Assignee: Asahi Kadei Kabushiki KaishaInventors: Takeshi Ikematsu, Kiyoshi Kawakami, Hironori Suezawa, Hiroshi Shirai
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Publication number: 20040127659Abstract: 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: ApplicationFiled: September 24, 2003Publication date: July 1, 2004Inventors: Michael Lester Kerns, Steven Kristofer Henning
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Patent number: 6756448Abstract: The present invention relates to a styrene copolymer and the method of preparing the same through the steps described in the following: a step of making a living polymer with an active anion by polymerizing an anionically polymerizable monomer in a non polar solvent in the presence of alkyllithum catalyst; a step of preparing a macro monomer by reacting the abovementioned living polymer with a terminal modifier represented by the structure of formula 1; and a step of copolymerizing the above macro monomer with styrene monomer with transition catalyst and co-catalyst.Type: GrantFiled: May 15, 2003Date of Patent: June 29, 2004Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Kwanyoung Lee, Namsun Choi
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Publication number: 20040122194Abstract: This invention discloses a process for synthesizing an amine functionalized monomer that comprises (1) reacting a secondary amine with a 2,3-dihalopropene to produce a vinyl halide containing secondary amine having a structural formula selected from the group consisting of 1Type: ApplicationFiled: December 9, 2003Publication date: June 24, 2004Applicant: The Goodyear Tire & Rubber CompanyInventors: Adel Farhan Halasa, Wen-Liang Hsu, Jin-Ping Zhou, Chad Aaron Jasiunas, Corey Stanton Yon
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Publication number: 20040097634Abstract: This invention discloses a process for making dilithium initiators in high purity. This process can be conducted in the absence of amines which is desirable since amines can act as modifiers for anionic polymerizations. The dilithium compounds made are highly desirable because they are soluble in aromatic solvents. The present invention more specifically discloses a process for synthesizing a dilithium initiator which comprises reacting diisopropenylbenzene with a tertiary alkyl lithium compound in an aromatic solvent at a temperature which is within the range of about 0° C. to about 100° C. The present invention further discloses a process for synthesizing m-di-(1-lithio-1-methyl-3,3-dimethylbutyl) benzene which comprises reacting diisopropenylbenzene with tertiary-butyllithium in an aromatic solvent at a temperature which is within the range of about 0° C. to about 100° C.Type: ApplicationFiled: November 14, 2003Publication date: May 20, 2004Applicant: The Goodyear Tire & Rubber CompanyInventors: Adel Farhan Halasa, Wen-Liang Hsu
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Patent number: 6737486Abstract: A process for polymerization of vinyl monomers is described comprising polymerizing vinyl monomers in the presence of an initiating system comprising (i) an organic iodide, organic bromide, organic chloride, or an organic sulfur initiator compound, and (ii) a layered material catalyst, and wherein when the initiator compound comprises an organic bromide or organic chloride compound, the initiating system further comprises an iodide or sulfur containing salt compound or a transition metal salt. The present invention provides a novel method for living polymerization of vinyl monomers, which provides a high level of macromolecular control over the polymerization process and which leads to uniform and controllable polymeric products, which may include well-defined structures and complex architectures.Type: GrantFiled: July 16, 2002Date of Patent: May 18, 2004Assignee: Eastman Kodak CompanyInventor: Jin-Shan Wang
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Patent number: 6727335Abstract: The invention relates to polymeric phosphinic acids and their salts of the formula (I) in which X is hydrogen or a 1/m metal of valency m, R1 and R2 are identical or different and are hydrogen, a carboxyl group, a carboxylic acid derivative, an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, phenyl, benzyl or alkyl-substituted aromatics, R3 and R4 are identical or different and are hydrogen or a vinyl group of the formula (VI) —CR1═CHR2 (VI) in which R1 and R2 have the abovementioned meaning, and {overscore (u)} is the average number of monomer units. The invention also relates to a process for the preparation of the abovementioned compounds and their use.Type: GrantFiled: April 17, 2003Date of Patent: April 27, 2004Assignee: Clariant GmbHInventors: Martin Sicken, Norbert Weferling, Hans-Peter Schmitz
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Patent number: 6716935Abstract: The present invention discloses a continuous process for the production of polymerized controlled architectures materials under high solids loading conditions. The materials are made under stirred, plug-flow and temperature-controlled conditions.Type: GrantFiled: December 19, 2002Date of Patent: April 6, 2004Assignee: 3M Innovative Properties CompanyInventors: James Michael Nelson, Ryan E. Marx, Michael John Annen, Duane Douglas Fansler, Maureen Ann Kavanagh, Babu Nana Gaddam
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Publication number: 20040059075Abstract: The present invention relates to a styrene copolymer and the method of preparing the same through the steps described in the following:Type: ApplicationFiled: May 15, 2003Publication date: March 25, 2004Applicant: KOREA KUMHO PETROCHEMICAL CO., LTD.Inventors: Kwanyoung Lee, Namsun Choi
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Publication number: 20040053776Abstract: A method for making single-site catalysts useful for olefin polymerization is disclosed. A nitrogen-functional heterocycle is first deprotonated with an alkyllithium compound, followed by reaction of this anionic ligand precursor with about 0.5 equivalents of a Group 4 transition metal tetrahalide in a hydrocarbon solvent at a temperature greater than about 10° C. to give an organometallic complex-containing mixture. When combined with exceptionally low levels of an activator (e.g., methyl alumoxane), the mixture actively polymerizes olefins to give polymers with a favorable balance of physical properties, including low density and narrow molecular weight distribution.Type: ApplicationFiled: September 18, 2003Publication date: March 18, 2004Applicant: EQUISTAR CHEMICALS, LPInventor: Jia-Chu Liu
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Publication number: 20040044157Abstract: This invention discloses a process for synthesizing an amine functionalized monomer that comprises (1) reacting a secondary amine with a 2,3-dihalopropene to produce a vinyl halide containing secondary amine having a structural formula selected from the group consisting of 1Type: ApplicationFiled: March 14, 2003Publication date: March 4, 2004Inventors: Adel Farhan Halasa, Wen-Liang Hsu, Jin-Ping Zhou, Chad Aaron Jasiunas, Corey Stanton Yon
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Patent number: 6686420Abstract: The invention is directed to a pneumatic tire having at least one component comprising a vulcanizable rubber composition, wherein the vulcanizable rubber composition comprises, based on 100 parts by weight of elastomer (phr), from about 30 to 100 phr of high trans random SIBR, and from about zero to about 70 phr of at least one additional elastomer, wherein the high trans random SIBR comprises from about 3 to about 30 percent by weight of styrene.Type: GrantFiled: December 19, 2002Date of Patent: February 3, 2004Assignee: The Goodyear Tire & Rubber CompanyInventors: David John Zanzig, Adel Farhan Halasa, John Robert Zuppo, III, John Joseph Andre Verthe
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Publication number: 20040006187Abstract: Process for the production of statistic elastomeric conjugated diene-vinyl arene copolymers having a branched structure which comprises: (1) anionic copolymerization in solution of the conjugated diene and vinyl arene monomers, in the presence of randomizing agents and an initiator selected from the group of Lithium alkyls, the copolymerization being carried out until the almost total disappearance of the monomers; (2) addition to the solution of step (1) of a quantity of Lithium alkyl from 1 to 4 times the molar quantity of the Lithium alkyl of step (1); (3) addition to the polymeric solution of step (2) of a compound having the general formula R—Br, the molar ratio between R—Br and the total Lithium alkyl ranging from 0.6/1 to 1/1, preferably from 0.7/1 to 0.9/1, thus obtaining an elastomeric branched copolymer.Type: ApplicationFiled: June 2, 2003Publication date: January 8, 2004Inventors: Gian Tommaso Viola, Luca Soddu, Sabrina Isidori, Attilio Taccioli, Francesco Masi
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Patent number: 6664357Abstract: An improved process for manufacturing a dual cure anaerobic/ultraviolet adhesive. The process includes the first step of mixing a polymerizable (meth)acrylate ester monomer, such as methacrylic acid, a chelating agent and an accelerator. The second step is heating the mixture sufficiently to provide anaerobic curing properties. Next, one or more photoinitiators are added to the composition. No chelating agent is added during the addition of the photoinitiators.Type: GrantFiled: January 21, 2003Date of Patent: December 16, 2003Assignee: National Starch and Chemical Investment Holding CorporationInventor: Robert Edelman
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Patent number: 6660800Abstract: A process for making crosslinked polyvinylpyrrolidone (PVP-P) is disclosed. Crosslinker generation, followed by polymerization of NVP, gives a polymer containing up to 4 wt. % of residual NVP. An aqueous mixture of the polymer is then heated in the presence of a protic acid at pH<4 to eliminate NVP. Finally, the PVP-P is neutralized with aqueous alkali metal hydroxide. The process generates a reduced volume of low-toxicity aqueous waste (<20 L/kg PVP-P) and gives PVP-P that meets important product specifications.Type: GrantFiled: October 17, 2002Date of Patent: December 9, 2003Assignee: Arco Chemical Technology, L.P.Inventors: Beth M. Steinmetz, Manish K. Nandi
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Patent number: 6657028Abstract: A batch process for the anionic polymerization of a styrenic monomer is described. The process brings together a liquid saturated hydrocarbon diluent, an ether promoter, an organolithium initiator and a styrenic monomer in such a way so as to maintain the reaction mixture at or below about 55° C. and so that the amount of organolithium initiator employed is in the range of about 1 to about 10 mol %, based upon the total amount of styrenic monomer to be added. Favorable polydispersity and molecular weight polymer characteristics are obtained.Type: GrantFiled: August 1, 2002Date of Patent: December 2, 2003Assignee: Albemarle CorporationInventors: J. Todd Aplin, Charles H. Kolich, W. Dirk Klobucar, Kimberly A. Maxwell
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Publication number: 20030212223Abstract: The present invention provides a process for preparing amino functionalized diene polymers with 1,4-trans linkage content equal to or greater than 70%. The invention also concerns polymers of such type, a rubber composition and a tire casing containing those polymers. The process of preparation according to the invention comprises polymerizing at least one diene monomer by means of a lithium catalytic system, which comprises at least one hydrocarbon solvent, one compound A of a IIIA group metal, one compound B of an alkaline earth metal and one aminolithium initiator C. Amino functionalized diene polymers with high 1,4-trans linkage content according to the invention are such that the amino function, situated at the end of the polymer chain, is a tertiary amino function, the rate of functionalization of said polymers being equal to or greater than 50% and the 1,4-trans linkage content being equal to or greater than 70%.Type: ApplicationFiled: March 28, 2003Publication date: November 13, 2003Inventors: Jean-Michel Favrot, Philippe Laubry
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Publication number: 20030195309Abstract: The present invention provides a process for preparing amino functionalized diene polymers with 1,4-trans linkage content equal to or greater than 70%. The invention also concerns polymers of such type, a rubber composition and a tire casing containing those polymers. The process of preparation according to the invention comprises polymerizing at least one diene monomer by means of a lithium catalytic system, which comprises at least one hydrocarbon solvent, one compound A of a IIIA group metal, one compound B of an alkaline earth metal and one aminolithium initiator C. Amino functionalized diene polymers with high 1,4-trans linkage content according to the invention are such that the amino function, situated at the end of the polymer chain, is a tertiary amino function, the rate of functionalization of said polymers being equal to or greater than 50% and the 1,4-trans linkage content being equal to or greater than 70%.Type: ApplicationFiled: March 28, 2003Publication date: October 16, 2003Inventors: Jean-Michel Favrot, Philippe Laubry
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Patent number: 6630552Abstract: This invention discloses a rubbery polymer which is comprised of repeat units that are derived from (1) at least one conjugated diolefin monomer, and (2) at least one functionalized monomer having of the structural formula: wherein R represents an alkyl group containing from 1 to about 10 carbon atoms or a hydrogen atom, and wherein R1 and R2 can be the same or different and represent hydrogen atoms or a moiety selected from the group consisting of wherein R3 groups can be the same or different and represent alkyl groups containing from 1 to about 10 carbon atoms, aryl groups, allyl groups, and alkyloxy groups of the structural formula —(CH2)y—O—(CH2)z—CH3, wherein Z represents a nitrogen containing heterocyclic compound, wherein R4 represents a member selected from the group consisting of alkyl groups containing from 1 to about 10 carbon atoms, aryl groups, and allyl groups, and wherein n, x, y and z represents integers from 1 to about 10, with theType: GrantFiled: December 30, 2002Date of Patent: October 7, 2003Assignee: The Goodyear Tire & Rubber CompanyInventors: Stephan Rodewald, Steven Kristofer Henning, Brian Earl Burkhart
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Publication number: 20030181610Abstract: A process for producing a styrenic resin with a small content of low molecular weight components, comprising a continuous anionic polymerization process wherein a raw material system having the following composition (A) is continuously fed, either collectively or in a divided manner, from one end of a reactor tank R1 having a back mixing flow and the product system is continuously discharged from the other end of the reactor tank R1, the internal temperature of the reactor tank R1 being controlled to a range of 40-120° C., the average proportion of styrene monomers to the sum total of the styrene monomers, hydrocarbon solvent and styrenic polymers present in the reactor tank R1 being controlled to less than 10 wt. %, and the resulting styrenic polymer solution being devolatilized and dried: 1 (A) Styrene monomer 1.0 kg Hydrocarbon solvent 0.1-3 kg Organolithium compound 0.Type: ApplicationFiled: November 8, 2002Publication date: September 25, 2003Inventors: Takeshi Ikematsu, Kiyoshi Kawakami, Hironori Suezawa, Hiroshi Shirai
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Patent number: 6624267Abstract: The present invention provides a process for preparing amino functionalized diene polymers with 1,4-trans linkage content equal to or greater than 70%. The invention also concerns polymers of such type, a rubber composition and a tire casing containing those polymers. The process of preparation according to the invention comprises polymerizing at least one diene monomer by means of a lithium catalytic system, which comprises at least one hydrocarbon solvent, one compound A of a IIIA group metal, one compound B of an alkaline earth metal and one aminolithium initiator C. Amino functionalized diene polymers with high 1,4-trans linkage content according to the invention are such that the amino function, situated at the end of the polymer chain, is a tertiary amino function, the rate of functionalization of said polymers being equal to or greater than 50% and the 1,4-trans linkage content being equal to or greater than 70%.Type: GrantFiled: January 6, 2000Date of Patent: September 23, 2003Assignee: Michelin Recherche et Technique S.A.Inventors: Jean-Michel Favrot, Philippe Laubry
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Patent number: 6613858Abstract: A block copolymer having narrow molecular weight distribution and excellent symmetrical property or a telechelic polymer having, equally at both terminals thereof, a functional group can be produced by using a polymerization initiator solution which comprises a dilithium polymerization initiator having an average number of functional groups of 1.8 to 2.0/molecule and a solvent selected from aliphatic hydrocarbon compounds and alicyclic compounds and is free of a polar substance.Type: GrantFiled: January 10, 2002Date of Patent: September 2, 2003Assignee: Asahi Kasei Kabushiki KaishaInventors: Masahiro Sasagawa, Jurgen Hofmans, Marcel Van Beylen
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Publication number: 20030153698Abstract: The group IIa metal containing catalyst system of this invention can be utilized to synthesize rubbery polymers having a high trans microstructure by solution polymerization. Such rubbery polymers having a high trans microstructure content, such as polybutadiene rubber, styrene-isoprene-butadiene rubber, styrene-butadiene rubber, can be utilized in tire tread rubbers that exhibit improved wear and tear characteristics. This invention more specifically reveals a catalyst system which is comprised of (a) an organolithium compound, including organolithium functionalized compounds, (b) a group IIa metal salt selected from the group consisting of group IIa metal salts of di(alkylene glycol)alkylethers and group IIa metal salts of tri(alkylene glycol) alkylethers, and (c) an organoaluminum compound, and optionally an organomagnesium compound.Type: ApplicationFiled: April 17, 2002Publication date: August 14, 2003Inventors: Adel Farhan Halasa, Wen-Liang Hsu, Chad Aaron Jasiunas, John Robert Zuppo, Laurie Elizabeth Austin
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Publication number: 20030153709Abstract: The process for the continuous preparation of homopolymers or copolymers by free-impinging-jet micromixing of fluids formed (1) of monomer(s) and (2) of an initiator system consists in micromixing the said fluids (1) and (2) and in recovering the mixture of these fluids in the form of a resultant jet Jr, originating from the point of impingement (I), the micromixture being obtained by:Type: ApplicationFiled: December 31, 2002Publication date: August 14, 2003Applicant: ATOFINAInventors: Xavier Marcarian, Christophe Navarro, Laurent Falk, Fernand Pla
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Patent number: 6590052Abstract: The process for the continuous preparation of homopolymers or copolymers by free-impinging-jet micromixing of fluids formed (1) of monomer(s) and (2) of an initiator system consists in micromixing the said fluids (1) and (2) and in recovering the mixture of these fluids in the form of a resultant jet Jr, originating from the point of impingement (I).Type: GrantFiled: July 25, 2001Date of Patent: July 8, 2003Assignee: AtofinaInventors: Xavier Marcarian, Christophe Navarro, Laurent Falk, Fernand Pla
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Patent number: 6579949Abstract: A vulcanized elastomeric composition of matter comprises the reaction product of a sulfur-containing reagent with an anionic living polymer, the reagent being selected from the group consisting of R3—Si—S—R′—X, where R can all be the same or different and is selected from the group consisting of alkyls having from 1 to 8 carbon atoms, cycloalkyls having from 3 to 11 carbon atoms, or an arylene having from 6 to 14 carbon atoms, and X is a halogen, to form a R3—Si—S—R′ ended polymer; a filler; processing oil; and a cure package containing a deprotecting agent and at least one sulfur cure accelerator.Type: GrantFiled: October 30, 2001Date of Patent: June 17, 2003Assignee: Bridgestone CorporationInventors: William L. Hergenrother, Christine M. Rademacher, James D. Ulmer
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Patent number: 6576728Abstract: This invention is based upon the discovery of certain anionic initiator systems can be used to initiate the solution polymerization of conjugated diolefin monomers into rubbery polymers having a low vinyl content. For instance, such initiator systems can be used in the copolymerization of styrene and isoprene to produce low vinyl styrene-isoprene rubber having a random distribution of repeat units that are derived from styrene. These initiator systems are comprised of (a) a lithium initiator and (b) a member selected from the group consisting of (1) a sodium alkoxide, (2) a sodium salt of a sulfonic acid, and (3) a sodium salt of a glycol ether. It is important for the initiator system to be free of polar modifiers, such as Lewis bases.Type: GrantFiled: October 31, 2001Date of Patent: June 10, 2003Assignee: The Goodyear Tire & Rubber CompanyInventors: Chad Aaron Jasiunas, Adel Farhan Halasa, John Robert Zuppo, III
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Publication number: 20030100690Abstract: This invention is based upon the discovery of certain anionic initiator systems can be used to initiate the solution polymerization of conjugated diolefin monomers into rubbery polymers having a low vinyl content. For instance, such initiator systems can be used in the copolymerization of styrene and isoprene to produce low vinyl styrene-isoprene rubber having a random distribution of repeat units that are derived from styrene. These initiator systems are comprised of (a) a lithium initiator and (b) a member selected from the group consisting of (1) a sodium alkoxide, (2) a sodium salt of a sulfonic acid, and (3) a sodium salt of a glycol ether. It is important for the initiator system to be free of polar modifiers, such as Lewis bases.Type: ApplicationFiled: October 31, 2001Publication date: May 29, 2003Inventors: Chad Aaron Jasiunas, Adel Farhan Halasa, John Robert Zuppo
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Patent number: 6562923Abstract: The present invention relates to a process for the preparation of a dilithiated initiator usable in anionic polymerization, a process for the preparation by anionic polymerization of a living diene elastomer which is provided with a carbon-lithium group at each of its chain ends, and a process for the preparation of a copolymer having three blocks starting from said living diene elastomer. The process for the preparation of a dilithiated initiator according to the invention involves of reacting a first reagent, a dialkenyl benzene, and a second reagent, secondary butyllithium, in the presence of a diamine, in an aliphatic or alicyclic hydrocarbon solvent, such that the ratio of the number of moles of first reagent to the number of moles of second reagent is substantially equal to 0.5, so that the initiator obtained is essentially a bi-adduct resulting from the addition of a molecule of secondary butyllithium to each of the two double bonds in the dialkenyl benzene.Type: GrantFiled: May 13, 2002Date of Patent: May 13, 2003Assignee: Michelin Recherche et Technique S.A.Inventors: Pierre Robert, Corinne Fradin-Cohas
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Publication number: 20030083446Abstract: A continuous process for manufacture of a polymer including branched and linear components comprising first polymerizing conjugated diene(s) in the presence of an organometallic initiator to a conversion that is at least 90% complete. A coupling agent is added to obtain a polymer including branched and linear components. The coupling agent is added at a ratio of about 0.3 to about 0.6 coupling equivalents to initiator equivalents.Type: ApplicationFiled: November 26, 2002Publication date: May 1, 2003Inventor: Mark N. Dedecker
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Publication number: 20030078351Abstract: The process and catalyst system of this invention can be utilized to synthesize polybutadiene rubber having a high trans content and a low melting point by solution polymerization. The trans-polybutadiene rubber made by the process of this invention can be utilized in tire tread rubbers that exhibit outstanding wear characteristics. More importantly, the trans-polybutadiene rubber of this invention can be easily processed because of its low level of crystallinity. In fact, the trans-polybutadiene made by the process of this invention does not need to be heated in a “hot-house” before being used in making rubber compounds.Type: ApplicationFiled: December 2, 2002Publication date: April 24, 2003Applicant: The Goodyear Tire & Rubber CompanyInventors: Wen-Liang Hsu, Adel Farhan Halasa
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Publication number: 20030073792Abstract: The extremely rapid anionic polymerization rate of polystyrene has made polymerization difficult to control and has prevented large-scale development. This invention uses batch polymerization to utilize the rapid rate of polymerization to complete polymerization from zero to 100% conversion in minutes and turns this rapid rate into an advantage. Polystyrene itself is used as a heat sink to limit and control the maximum temperature reached during polymerization. Adiabatic polymerization increases the polymer temperature to the desired processing temperature of the polymer for either removal of volatile compounds or for direct pellet formation when no solvent is employed. The polystyrene to be used as a heat sink is added either as pellets or is first formed at a low controllable temperature. Extremely low levels of residual monomer are found in the product. This invention also demonstrates techniques to prevent gel formation or to reduce formation to an acceptable level.Type: ApplicationFiled: August 8, 2002Publication date: April 17, 2003Inventor: Eugene R. Moore