Contains Compound Of Nitrogen Patents (Class 526/180)
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Patent number: 4960842Abstract: Narrow molecular weight telechelic and/or block copolymers are prepared by anionic polymerization using an initiator composition comprising a multifunctional lithium initiator in combination with an organic diamine or triamine and optionally a metal alkoxide.Type: GrantFiled: May 9, 1989Date of Patent: October 2, 1990Assignee: The Dow Chemical CompanyInventors: Grace Y. Lo, Eric W. Otterbacher, Massimo D. Bezoari, Brian W. Walther
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Patent number: 4933401Abstract: A catalyst composition for polymerizing a conjugated diene which comprises the following (a), (b) and (c) components:(a) an organolithium-aluminum compound represented by the formula:LiAlR.sup.1 R.sup.2 R.sup.3 R.sup.4(b) an organobarium-aluminum compound represented by the formula:Ba(AlR.sup.1 R.sup.2 R.sup.3 R.sup.4).sub.2 or Ba[AlR.sup.1 R.sup.2 R.sup.3 (OR.sup.4)].sub.2(c) a lithium alkoxide represented by the formula:LiOR.sup.5The conjugated diene polymer or copolymer obtained by polymerizing a conjugated diene alone or in combination with other monomer with the above catalyst composition in an inert organic solvent has a high trans-1,4 bond content, a low vinyl bond content and a low cis-1,4 bond content.Type: GrantFiled: February 23, 1989Date of Patent: June 12, 1990Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Iwakazu Hattori, Noboru Shimada, Noboru Oshima, Mitsuhiko Sakakibara
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Patent number: 4889900Abstract: A process is disclosed for treatment of alkyl methacrylate monomers for subsequent polymerization by an anionic initiator to produce a polymer with a molecular weight distribution between about 1.20 and about 1.01. The process involves treatment of the monomer with an aluminum hydrocarbyl or boron hydrocarbyl in quantities which permit polymerization in the presence of the by-products of the reaction between the impurities and the aluminum hydrocarbyl or boron hydrocarbyl.Type: GrantFiled: June 12, 1989Date of Patent: December 26, 1989Assignee: Shell Oil CompanyInventor: Donn A. DuBois
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Patent number: 4731424Abstract: A process for producing an alkenylsilyl group-containing polymer compound, comprising polymerizing a vinyl monomer compound containing an alkenylsilyl group-containing styrene compound represented by General Formula (I): ##STR1## wherein R.sup.1 represents hydrogen atom, methyl group or ethyl group; R.sup.2 and R.sup.3 may be the same or different and each represent an alkyl group having 1 to 3 carbon atoms or phenyl group; and n is an integer of 0 to 4, by using an organic metallic compound as an initiator, wherein the polymerization is carried out in the presence of N-methylpyrrolidine.There can be obtained a monodisperse alkenylsilyl group-containing high molecular compound in which only the unsaturated bond in the styrene moiety of the compound of Formula (I) has been predominantly polymerized.Type: GrantFiled: March 13, 1987Date of Patent: March 15, 1988Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Teruo Fujimoto, Mikio Shiono, Osamu Watanabe, Koichi Ito
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Patent number: 4710554Abstract: A polybutadiene having an average 1,2-bond content of 18 to 32% by mole, a branched polymer chain content of 60% by weight or more and a Mooney viscosity at 100.degree. C. of 40 to 90, the viscosity of a 5% by weight concentration solution of this polybutadiene in styrene at 25.degree. C. being 60 to 90 cps, and a process for preparing the polybutadiene comprising starting the polymerization of 1,3-butadiene in an inert hydrocarbon solvent in the presence of a Lewis basic compound and an organolithium compound, the latter compound being in an amount of 0.5 to 3 millimoles per 100 g of 1,3-butadiene, at a temperature selected from the range of 30.degree. to 80.degree. C., carrying out the polymerization by controlling the temperature so that the temperature at the end of polymerization may be 5.degree. to 40.degree. higher than the temperature at the start of polymerization, and adding to the resulting polymer solution a polyfunctional halogen compound in an amount of 0.Type: GrantFiled: February 14, 1986Date of Patent: December 1, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Akio Imai, Yasushi Okamoto, Masatoshi Saito
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Patent number: 4680407Abstract: Multifunctional anionic initiators of the general formula ##STR1## Process for their synthesis, and use of them in polymerization processes.Type: GrantFiled: December 3, 1984Date of Patent: July 14, 1987Assignee: Enichem Elastomeri S.p.A.Inventor: Arnaldo Roggero
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Patent number: 4677165Abstract: A rubber composition for a tire tread comprising a novel modified styrene-butadiene copolymer rubber, carbon black, and aromatic oil.Type: GrantFiled: October 17, 1986Date of Patent: June 30, 1987Assignees: The Yokohama Rubber Co., Ltd., Nippon Zeon Co., Ltd.Inventors: Yasushi Kikuchi, Kazuyoski Kayama, Akinori Tokieda, Hiroyuki Watanabe, Shuichi Akita
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Patent number: 4668746Abstract: A complex of an alkyllithium compound and 1,2-dipyrrolidinoethane is useful as an initiator for the polymerization of ethylene and ethylene block copolymers.Type: GrantFiled: February 21, 1986Date of Patent: May 26, 1987Assignee: The Dow Chemical CompanyInventors: Mark S. Delaney, William B. Marshall, James L. Brewbaker
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Patent number: 4554334Abstract: An optically active polymer is obtained by polymerizing a vinyl monomer in the presence of a catalyst which comprises an asymmetric ligand compound of the formula (I) or (II): ##STR1## in which R.sub.1 and R.sub.4 each are --O--R.sub.7, --S--R.sub.7, ##STR2## R.sub.2, R.sub.3, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 each are an alkyl group having 1 to 10 carbon atoms; X is hydrogen, an alkyl group having 1 to 10 carbon atoms or a halogen; and n is a number of 1 to 4; and an anionic initiator to form a complex with said ligand compound.Type: GrantFiled: August 10, 1984Date of Patent: November 19, 1985Assignee: Daicel Chemical Industries, Ltd.Inventors: Heimei Yuki, Yoshio Okamoto
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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: 4522990Abstract: Anionic polymerization initiator which is a 2,2,6,6-tetramethylpiperidinyl alkali metal or an alkali metal 2,6-dimethyl-2,6-dialkyl-4-piperidinoxide.Type: GrantFiled: December 16, 1983Date of Patent: June 11, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gerald D. Andrews
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Patent number: 4521578Abstract: The present invention relates to new compositions and methods of preparation of deflocculents for water-base mud additives. The disclosed materials are low molecular weight terpolymers and graft copolymers consisting essentially of monovalent salts of (1) 5 to 50% by weight of tetrahydrophthalic acid (THPA); (2) 10 to 70% by weight of acrylic acid (AA); (3) 5 to 50% by weight of 2-acrylamido-2-methylpropane sulfonic acid (AMPS); and (4) 0 to 70% by weight of lignosulfonate units. The unique compositions and processes of terpolymers and graft copolymers provide excellent drilling fluid additives which significantly control the viscosity, yield point, gel strength, and fluid loss of drilling fluids over a wide range of temperatures and in the presence of contaminants such as salt, lime, cement, gypsum and drilled solids.Type: GrantFiled: September 26, 1983Date of Patent: June 4, 1985Assignee: Dresser Industries, Inc.Inventors: Robert G. Chen, Arvind D. Patel, Thomas E. Sample, Jr.
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Patent number: 4478953Abstract: An optically active polymer is obtained by polymerizing a vinyl monomer in the presence of a catalyst which comprises an asymmetric ligand compound of the formula (I) or (II): ##STR1## in which R.sub.1 and R.sub.4 each are ##STR2## R.sub.2, R.sub.3, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 each are an alkyl group having 1 to 10 carbon atoms; X is hydrogen, an alkyl group having 1 to 10 carbon atoms or a halogen; and n is a number of 1 to 4; and an anionic initiator to form a complex with said ligand compound.Type: GrantFiled: March 3, 1983Date of Patent: October 23, 1984Assignee: Daicel Chemical Industries, Ltd.Inventors: Heimei Yuki, Yoshio Okamoto
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Patent number: 4451576Abstract: Specific catalyst modifiers, namely unsaturated diazobicyclo compounds in association with anionic initiators such as organo-lithium compounds are utilized during the polymerization of conjugated diene monomers and comonomers therewith to unexpectantly yield polymers or copolymers having a broad molecular weight distribution, a significant vinyl microstructure, and good processability.Type: GrantFiled: June 17, 1983Date of Patent: May 29, 1984Assignee: The Firestone Tire & Rubber CompanyInventors: Delmar F. Lohr, Donald N. Schulz
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Patent number: 4424323Abstract: Specific catalyst modifiers, namely unsaturated diazobicyclo compounds in association with anionic initiators such as organo-lithium compounds are utilized during the polymerization of conjugated diene monomers and comonomers therewith to unexpectantly yield polymers or copolymers having a broad molecular weight distribution, a significant vinyl microstructure, and good processability.Type: GrantFiled: July 9, 1982Date of Patent: January 3, 1984Assignee: The Firestone Tire & Rubber CompanyInventors: Delmar F. Lohr, Donald N. Schulz
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Patent number: 4424322Abstract: A process for producing polymers of a conjugated diene, copolymers of a conjugated diene and another conjugated diene, or copolymers of conjugated diene and a vinyl aromatic hydrocarbon, which comprises polymerizing the corresponding monomers in the presence of a complex initiator consisting of components (a) and (b) described below, or (a) and (b) together with one or more components selected from components (c) and (d);(a) An organic compound of barium, strontium or calcium;(b) An organolithium-beryllium compound or an organolithiummagnesium compound;(c) An organolithium compound, an organoberyllium compound or an organomagnesium compound; and(d) An organoaluminum compound or an organozinc compound.The polymers of a conjugated diene containing relatively high trans-1,4 linkage, or the copolymers of a conjugated diene and a vinyl aromatic compound highly randomized and having high bound styrene and high trans-1,4 linkage can be produced at good yields.Type: GrantFiled: September 25, 1981Date of Patent: January 3, 1984Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Yasuo Hattori, Takeshi Ikematu, Toshio Ibaragi, Makoto Honda
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Patent number: 4397994Abstract: High vinyl polybutadiene or styrene-butadiene copolymer obtained by polymerizing 1,3-butadiene alone or with styrene in a hydrocarbon solvent using an organolithium compound as an initiator and coupling the resulting polymer, characterized in that(1) the polybutadiene or styrene-butadiene copolymer comprises at least 20% by weight of a polymer having in its molecular chain a linkage between butadienyl and at least one metal selected from the group consisting of silicon, germanium, tin and lead,(2) the styrene content of said copolymer is 40% by weight or less, and(3) the polybutadiene or the butadiene portion of the styrene-butadiene copolymer has a vinyl content of 50 to 95%.Said polybutadiene or styrene-butadiene copolymer has low rolling resistance, high wet skid resistance, highly improved fracture property and, an excellent processability.Type: GrantFiled: September 18, 1981Date of Patent: August 9, 1983Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yasumasa Takeuchi, Yoshito Yoshimura, Noboru Ohshima, Mitsuhiko Sakakibara, Akira Tsuji
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Patent number: 4367325Abstract: Styrene-butadiene random copolymers having an average vinyl content of at least 70%, a breadth of the distribution of vinyl contents of at least 20%, a Mooney viscosity (ML.sub.1+4, 100.degree. C.) of 10 to 150, and a styrene content of about 3 to 30% by weight. They are prepared by copolymerizing styrene and butadiene in a hydrocarbon solvent in the presence of an organolithium initiator and a Lewis base and, if necessary, an anionic surface active agent containing --SO.sub.3 M or --OSO.sub.3 M (wherein M is Na, K, Rb or Cs) under temperature-raising conditions. They are rubber materials having low rolling resistance and high wet skid resistance.Type: GrantFiled: April 15, 1981Date of Patent: January 4, 1983Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yasumasa Takeuchi, Noboru Ohshima, Mitsuhiko Sakakibara, Funio Tsutsumi
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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: 4311803Abstract: A continuous solution polymerization process for polymerizing conjugated dienes alone or with a copolymerizable monovinylarene in the presence of a gel inhibitor employing a first stirred reactor in series with a following plug-flow tube reactor.Type: GrantFiled: August 26, 1980Date of Patent: January 19, 1982Assignee: Phillips Petroleum CompanyInventors: Richard L. Smith, Ralph C. Farrar, Richard J. Sonnenfeld
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Patent number: 4309517Abstract: Hydrocarbyl esters of N-cyclopropyl-N-hydrocarbylcarbamic acids, such as ethyl N-benzyl-N-cyclopropylcarbamate, are effective coupling agents for conjugated diene polymerization systems employing an alkali metal-based initiator.Type: GrantFiled: October 23, 1980Date of Patent: January 5, 1982Assignee: Phillips Petroleum CompanyInventor: Kishore Udipi
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Patent number: 4280927Abstract: The catalyst system disclosed herein comprises a combination or a chelate of a hydrocarbyl lithium compound with a dialkylaminoaldehyde dialkyl acetal having the formula R'.sub.2 N-A-CH(OR.sub.2) wherein R and R'are alkyl groups of 1-3 carbon atoms and A is a divalent aliphatic group of 1-10, preferably 1-3 carbon atoms, with a direct linkage of no more than 3 carbon atoms between the N and the --CH(OR).sub.2 group. 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 1,2-polybutadiene structure are produced.Type: GrantFiled: May 27, 1980Date of Patent: July 28, 1981Assignee: The Firestone Tire & Rubber CompanyInventor: Delmar F. Lohr, Jr.
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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: 4258150Abstract: Monovinyl aromatic polymers are modified by reacting with elemental alkali metal and a conjugated diene to produce polymers having branches containing olefinic unsaturation. The olefinically unsaturated branches provide reactive sites which are readily reacted with various substances to obtain numerous variations in the properties of the monovinyl aromatic polymers.Type: GrantFiled: July 20, 1979Date of Patent: March 24, 1981Assignee: Phillips Petroleum CompanyInventor: Raymond L. Cobb
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Patent number: 4254247Abstract: An initiator for the anionic polymerization of vinyl monomers and dienic monomers comprises the product from the association of an alkali metal amide and the salt from at least one hydroxylated compound with the same alkali metal in an aprotic solvent. The hydroxylated compound is a primary, secondary, or tertiary alcohol. The hydroxylated compound may be a member selected from the group consisting of an alcohol substituted by an heterocyclic group, alcohols containing ethylenic unsaturation, alcohols substituted by an aromatic group, alicyclic alcohols, aromatic alcohols, polyhydroxy compounds, ether-alcohols, polyether-alcohols, and enols from ketones and amino acids.Type: GrantFiled: May 24, 1977Date of Patent: March 3, 1981Assignee: Societe Nationale des Poudres et ExplosifsInventors: Sylvie L. Boileau, Paul J. Caubere, Serge L. Lecolier, Serge F. Raynal
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Patent number: 4243787Abstract: The invention relates to a process for the anionic polymerization and copolymerization of vinyl, dienic and heterocyclic monomers.According to the invention, the process consists in carrying out the reaction in the presence of an initiator consisting of a molecular combination of an alkali metal amide and the salt of the same alkali metal with at least one hydroxylic compound and in the absence of solvent. The initiator can be prepared by intimately mixing its constituents or in the presence of a solvent of low polarity which is subsequently evaporated off, or in situ in the monomer.Application to the synthesis of special or widely used polymers and copolymers.Type: GrantFiled: November 6, 1978Date of Patent: January 6, 1981Assignee: Societe Nationale des Poudres et ExplosifsInventors: Sylvie L. Boileau, Paul J. Caubere, Gilberte Ndebeka, Serge L. Lecolier, Serge F. Raynal
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Patent number: 4237246Abstract: A 1,3-cyclodiene-monovinylaromatic copolymer is produced by polymerizing a monomer mixture comprising a 1,3-cyclodiene, a monovinylaromatic compound and a polyvinylaromatic hydrocarbon in the presence of an organolithium initiator.Type: GrantFiled: July 15, 1976Date of Patent: December 2, 1980Assignee: Phillips Petroleum CompanyInventor: Henry L. Hsieh
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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: 4152505Abstract: Homopolymers of conjugated dienes and copolymers of conjugated dienes with other conjugated dienes or with vinyl aromatic compounds having an elastomeric character are prepared by use of a catalytic system formed of the reaction product of (a) an organometallic compound of a metal of Group IIIA of the Mendeleev periodic table of elements with (b) at least one electron-donor compound containing at least one hetero-atom.Type: GrantFiled: April 29, 1977Date of Patent: May 1, 1979Assignee: Compagnie Generale des Etablissements MichelinInventor: Yves de Zarauz
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Patent number: 4148985Abstract: Homopolymers of conjugated dienes and copolymers of conjugated dienes with other conjugated dienes or with vinyl aromatic compounds having an elastomeric character are prepared by use of a catalytic system formed of the reaction product of (a) an organometallic compound of a metal of Group IIIA of the Mendeleev periodic table of elements with (b) at least one electron-donor compound containing at least one hetero-atom.Type: GrantFiled: April 29, 1977Date of Patent: April 10, 1979Assignee: Compagnie Generale des Etablissements MichelinInventor: Yves de Zarauz
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Patent number: 4148986Abstract: Homopolymers of conjugated dienes and copolymers of conjugated dienes with other conjugated dienes or with vinyl aromatic compounds having an elastomeric character are prepared by use of a catalytic system formed of the reaction product of (a) an organometallic compound of a metal of Group IIIA of the Mendeleev periodic table of elements with (b) at least one electron-donor compound containing at least one hetero-atom.Type: GrantFiled: April 29, 1977Date of Patent: April 10, 1979Assignee: Compagnie Generale des Etablissements MichelinInventor: Yves DeZarauz
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Patent number: 4145498Abstract: Continuous or incremental addition of a coupling agent, such as silicon tetrachloride, during the polymerization step of organolithium initiated polymerization processes results in polymers of improved processability, as well as other improved properties such as high green strength, low die swell, and minimal shrinkage on extrusion.Type: GrantFiled: January 26, 1977Date of Patent: March 20, 1979Assignee: Phillips Petroleum CompanyInventor: Ralph C. Farrar
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Patent number: 4139690Abstract: A process for preparing conjugated diene polymers by either polymerization of one or more monomers selected from a group of conjugated diene compounds or copolymerization of a conjugated diene compound with an alkenyl aromatic compound, using an organolithium initiator in a hydrocarbon solvent, characterized in that the polymerization is carried out in the presence of(1) one or more anionic surface active agent having a group --SO.sub.3 M or --OSO.sub.3 M (where M is an alkali metal) and(2) one or more Lewis bases.Type: GrantFiled: February 16, 1977Date of Patent: February 13, 1979Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshikazu Torigoe, Noboru Ohshima, Masaaki Watanabe, Eitaro Okuya
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Patent number: 4138536Abstract: A 1,3-cyclodiene is polymerized with a vinylaromatic hydrocarbon in the presence of a paraffin or cycloparaffin hydrocarbon diluent and an organolithium initiator. Further, polymerization of a 1,3-cyclodiene with a vinylaromatic hydrocarbon employing an organolithium initiator having a functionally greater than 1 produces a new and useful copolymer. Hydrogenated copolymers are provided.Type: GrantFiled: November 15, 1977Date of Patent: February 6, 1979Assignee: Phillips Petroleum CompanyInventor: Henry L. Hsieh
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Patent number: 4137391Abstract: Processable substantially random conjugated diene/monovinylaromatic compound copolymers are produced by continuous polymerization employing an alkoxysilicon treating agent in the first of a series of reactor means.Type: GrantFiled: September 10, 1976Date of Patent: January 30, 1979Assignee: Phillips Petroleum CompanyInventors: Richard L. Smith, Ralph C. Farrar
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Patent number: 4136245Abstract: 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: January 27, 1977Date of Patent: January 23, 1979Assignee: Compagnie Generale des Etablissements MichelinInventor: Jean-Marie Massoubre
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Patent number: 4136244Abstract: Continuous solution polymerizaton 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: January 27, 1977Date of Patent: January 23, 1979Assignee: Compagnie Generale des Etablissements MichelinInventor: Jean-Maire Massoubre
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Patent number: 4129705Abstract: Homopolymers of conjugated dienes and copolymers of conjugated dienes with vinyl aromatic compounds or with other conjugated dienes having improved properties and an elastomeric character are prepared by use of a catalytic composition which comprises (a) an organo-lithium initiator and (b) a tercatalyst system comprising (b.sub.1) a compound of barium or strontium or calcium, (b.sub.2) an organometallic compound of a metal of Group 2B or 3A of the Mendeleev periodic table of elements and (b.sub.3) an alkali metal alcoholate ether or amine.Type: GrantFiled: January 13, 1977Date of Patent: December 12, 1978Assignee: Compagnie Generale des Etablissements MichelinInventor: Yves de Zarauz
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Patent number: 4116887Abstract: A novel process for polymerization or copolymerization of monomers is described, according to which the reaction is carried out in the presence of an anionic initiator and a macroheterocyclic complexing agent of formula ##STR1## in which: EACH R.sub.1 is a hydrogen atom, a hydrocarbon group or an alkoxycarbonyl group, or the two R.sub.1 together can form a group of the general formula: ##STR2## THAT IS TO SAY FORMING A THIRD BRIDGE BETWEEN THE TWO NITROGEN ATOMS IN THE MOLECULE, A is a hydrocarbon group,D is an oxygen or sulfur atom or a hydrocarbon group, with the proviso that at least two of the groups D are oxygen or sulfur atoms and that, if each R.sub.1 is hydrogen, a hydrocarbon group or an alkoxycarbonyl group, one of these two groups D is oxygen or sulfur and the other is oxygen,n and p are integers ranging from 1 to 3, andm is 2 or 3.Type: GrantFiled: January 9, 1975Date of Patent: September 26, 1978Assignee: Societe Nationale des Poudres et ExplosifsInventors: Jean-Marie Lehn, Francois Schue, Sylvia Boileau, Bernd Kaempf, Alain Andre Cau, Jean Robert Moinard, Serge Fernand Raynal
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Patent number: 4104465Abstract: The invention relates to the production of high molecular weight polymers of broad molecular weight distribution by using a sodium catalyst in the presence of a chelating diamine in the polymerization of (1) conjugated dienes, (2) a mixture of conjugated dienes and (3) a mixture of conjugated diene and vinyl monomer. Lithium and potassium alkoxides speed up the reaction.Type: GrantFiled: January 31, 1977Date of Patent: August 1, 1978Assignee: The Firestone Tire & Rubber CompanyInventor: Adel Farhan Halasa
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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: 4085265Abstract: When a lower polymer of butadiene or a lower copolymer of butadiene with a conjugated diolefin other than butadiene or a vinyl-substituted aromatic comonomer is reacted at 0 to 200.degree. C. in the presence of a combination catalyst including an organic alkali metal compound and a specific diamino compound, the non-conjugated double bonds are effectively isomerized to the conjugated diene double bonds at a very high conversion, and a polymer having a high reactivity, which is useful as a paint vehicle, a thermosetting material, an adhesive, a rubber compounding material and an intermediate for various synthetic reactions, can be obtained.Type: GrantFiled: October 29, 1976Date of Patent: April 18, 1978Assignee: Nippon Oil Company, LimitedInventors: Yutaka Otsuki, Hirosuke Imai, Atsushi Kaiya, Hideo Horii
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Patent number: 4085262Abstract: A high polymeric substance having isocyanate group is produced by reacting a liquid high polymeric substance containing carbon-to-carbon unsaturated double bond or a solution of said high polymeric substance with a cyanate, an alkyl hypohalite and an organic carboxylic acid.Type: GrantFiled: November 1, 1976Date of Patent: April 18, 1978Assignee: Bridgestone Tire Company LimitedInventors: Toshio Honda, Itsuo Tanuma, Shoji Tanaka, Koichi Iwami, Yukio Fukuura, Shoson Shibata, Yoshikatsu Suzuki
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Patent number: 4022959Abstract: Homopolymers of butadiene having a vinyl content which varies substantially and decreasingly along the longitudinal axis of the macromolecule toward an end thereof are produced by conducting an organolithium-Lewis base catalyzed polymerization at a substantially constantly increasing polymerization temperature throughout the polymerization.Type: GrantFiled: June 4, 1975Date of Patent: May 10, 1977Assignee: Chemische Werke Huels AktiengesellschaftInventors: Neithart Sommer, Karl-Heinz Nordsiek
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Patent number: 4020258Abstract: Continuous or incremental addition of a coupling agent, such as silicon tetrachloride, during the polymerization step of organolithium initiated polymerization processes results in polymers of improved processability, as well as other improved properties such as high green strength, low die swell, and minimal shrinkage on extrusion.Type: GrantFiled: March 1, 1974Date of Patent: April 26, 1977Assignee: Phillips Petroleum CompanyInventor: Ralph C. Farrar
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Patent number: 4020251Abstract: A copolymer is produced by polymerization of a mixture comprising a 1,3-cyclodiene and an acyclic conjugated diene wherein a substantial percentage by weight of the acyclic conjugated diene units of the copolymer is in the trans and vinyl configurations. A method for producing the copolymer is provided employing an organolithium initiator. A hydrogenated copolymer and method of its production is also provided.Type: GrantFiled: March 17, 1975Date of Patent: April 26, 1977Assignee: Phillips Petroleum CompanyInventor: Henry L. Hsieh