C-metal Patents (Class 260/665R)
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Patent number: 4196154Abstract: Highly desirable organic liquid soluble multifunctional lithium containing initiators are prepared by reacting an organo lithium compound with an organic compound containing at least one group of the configuration 1,3-bis(1-phenylethenyl)benzene. Such initiators can be prepared in the absence of polar solvents and are very desirable for the polymerization of dienes such as butadiene to a desirable 1,4 configuration.Type: GrantFiled: August 7, 1978Date of Patent: April 1, 1980Assignee: The Dow Chemical CompanyInventors: Lu H. Tung, Grace Y-S. Lo, Douglas E. Beyer
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Patent number: 4187254Abstract: An organometallic halide having the formula:(RMX)(MX.sub.2).sub.a (MR.sub.2).sub.b (MH.sub.2).sub.cwherein a.ltoreq.0.45, b.ltoreq.0.15, and c.ltoreq.0.30, X is a halogen, R is a hydrocarbon radical, and M is a metal selected from the group consisting of magnesium, zinc, beryllium, and calcium is prepared by a continuous dry process by reacting an organic monohalide RX and a metal M in the form of convex solid grains of a size between 1 and 15 mm. The reaction temperature is lower than the temperature at which decomposition of the organometallic halide RMX begins and at least 10.degree. C. higher than the boiling point of the organic monohalide. The reaction may also take place in the presence of an organometallic derivative comprising a hydroxy group or an enolysable ketone group. The resulting organometallic halide may be used for the synthesis of anhydrous magnesium halide or for the reduction of titanium tetrachloride.Type: GrantFiled: November 2, 1977Date of Patent: February 5, 1980Assignee: Societe Chimique des Charbonnages - CdF ChimieInventors: Karel Bujadoux, Jean-Marie Neyer, Jean-Pierre Houzeaux
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Patent number: 4182818Abstract: Very desirable polyfunctional lithium containing polymerization initiators are prepared by reacting an adduct of an organo lithium compound and styrene with an organic compound containing at least two 1,1-diphenylethylene groups in the proportion of about two moles of the adduct to one mole of the organic compound. A difunctional lithium initiator is prepared thereby. The difunctional initiator may be reacted with styrene and subsequently an additional quantity of the diphenylethylene compound which in turn is reacted with the styrene-organo lithium adduct to form a trifunctional initiator. The process can be repeated to obtain an initiator having any desired degree of lithium functionality. Such initiators can be prepared in the absence of polar solvents and are very desirable for the polymerization of dienes such as butadiene to a desirable 1,4 configuration and preparation of block copolymers.Type: GrantFiled: August 15, 1977Date of Patent: January 8, 1980Assignee: The Dow Chemical CompanyInventors: Lu H. Tung, Grace Y-S. Lo
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Patent number: 4172190Abstract: Highly desirable organic liquid soluble multifunctional lithium containing initiators are prepared by reacting on organo lithium compound with an organic compound containing at least one group of the configuration 1,3-bis(1-phenylethenyl)benzene. Such initiators can be prepared in the absence of polar solvents and are very desirable for the polymerization of dienes such as butadiene to a desirable 1,4 configuration.Type: GrantFiled: October 11, 1977Date of Patent: October 23, 1979Assignee: The Dow Chemical CompanyInventors: Lu H. Tung, Grace Y. Lo, Douglas E. Beyer
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Patent number: 4167616Abstract: Polymerizable monomers are polymerized in a reaction mixture containing as catalysts (A) an oxygen source and (B) an organic boron compound which is soluble in the reaction mixture, the boron compound being (1) a diborane adduct wherein the boron atoms are linked by a hydrocarbyl group having an aliphatic carbon atom bonded to at least one of the boron atoms, or (2) oligomers based on repeating units containing at least two boron atoms linked by hydrocarbyl groups having an aliphatic carbon atom bonded to at least one of the boron atoms. The diborane adducts include the adduct of borane or a dialkylborane and 1,3-butadiene. The oligomers include polymers of diborane/propadiene adducts. The organoboron catalysts provide rapid initiation of polymerization and the polymerization is relatively insensitive to oxygen concentration, thereby permitting polymerization at ambient temperatures.Type: GrantFiled: August 22, 1977Date of Patent: September 11, 1979Assignee: Rohm and Haas CompanyInventor: Joseph M. Bollinger
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Patent number: 4161494Abstract: New organo-lithium initiators, their synthesis, and their use. The initiators have the formula: ##STR1## IN WHICH R" is either a hydrogen atom or a methyl radial; either n is 1, in which case R' = H and m and p are integers, the sum of which is between 0 and 10 inclusive, or n is 2, R' then being an alkyl radical of 2 to 8 carbon atoms and m = p = 0; and R is an alkyl radical of 1 to 4 carbon atoms.The initiators are prepared by reacting compounds of the formula: ##STR2## WITH AN ALKYL-LITHIUM RLi in a non-polar solvent in the absence of any polar solvent or complexing agent.The initiators are used to prepare polydienes of high stereoregularity by reacting with a diene, and the polydiene is used to prepare a three-block or star copolymer by reacting with an anionically polymerizable monomer.Type: GrantFiled: June 17, 1977Date of Patent: July 17, 1979Assignees: Societe Chimique des Charbonnages CDF Chimie, Agence Nationale de Valorisation de la RechercheInventors: Pierre Sigwalt, Patrick Guyot, Michel Fontanille
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Patent number: 4155942Abstract: A process of transmetalating organoalkali metals is disclosed, wherein organoalkali metal compounds are reacted with hydrocarbon compounds in the presence of predetermined amounts of oxygen.Type: GrantFiled: December 12, 1977Date of Patent: May 22, 1979Assignee: Nippon Oil Company, LimitedInventors: Hajime Hara, Atsushi Kaiya, Yoshihiko Araki
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Patent number: 4127507Abstract: A composition of matter comprising di-n-butylmagnesium and diethylmagnesium with a n-butyl:ethyl alkyl group ratio of about 0.25:1 to about 4:1 which is soluble in aliphatic, cycloaliphatic, and aromatic hydrocarbon solvents is disclosed. The composition is prepared in the substantial absence of oxygen and moisture by the simultaneous or consecutive reactions of ethyl and n-butyl halides with metallic magnesium in the presence of the hydrocarbon solvent, followed by separation of the insoluble magnesium chloride and any unreacted magnesium metal from the resulting solution.Type: GrantFiled: June 29, 1977Date of Patent: November 28, 1978Assignee: Texas Alkyls, Inc.Inventors: Loyd W. Fannin, Dennis B. Malpass
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Patent number: 4107282Abstract: The present invention relates to the manufacturing of novel hydrogenating fuel alloys evolving liquid and gaseous hydrocarbons when submitted to atmospheric or pressured hydrolysis. Said fuel alloys produce quality engine fuel and are an important and inexpensive new source of energy.Type: GrantFiled: October 22, 1976Date of Patent: August 15, 1978Inventor: Van Michaels Christopher
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Patent number: 4084061Abstract: Phenylacetic acid is produced by reacting chlorotoluene with sodium to form tolylsodium, rearranging the product to benzyl sodium and then reacting the benzyl sodium with a carboxylating agent.Type: GrantFiled: July 26, 1976Date of Patent: April 11, 1978Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Teiichi Kanazawa, Masamichi Shimizu, Susumu Shimoyama
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Patent number: 4075253Abstract: A stable and non-polar solvent soluble alpha-methylstyrene-conjugated diene oligomer dilithium as a polymerization initiator is obtained by preparing a dilithium initiator solution by reacting lithium metal with alpha-methylstyrene in a polar solvent at low temperature, thereafter adding gradually a small amount of a conjugated diene to the dilithium initiator solution to consume completely the alpha-methylstyrene, and then adding additional conjugated diene in a certain amount so as to prepare the stable and non-polar solvent soluble alpha-methylstyrene-conjugated diene oligomer dilithium.Type: GrantFiled: May 15, 1975Date of Patent: February 21, 1978Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Shigeki Horiie, Shin-Ichiro Asai, Takashi Torikoshi, Kazuhiro Shirakawa, Minoru Handa
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Patent number: 4069267Abstract: Stable diorganomagnesiums are prepared which are soluble in acyclic liquid hydrocarbons and represent novel and highly useful compositions. They are prepared, for instance, by forming a mixture of magnesium metal powder in an acyclic liquid hydrocarbon to which are added a C.sub.1 -C.sub.4 n-alkyl halide, such as n-butyl chloride, and a n-alkyl halide containing at least 6 carbon atoms, such as n-octyl chloride, and effecting reaction to convert them to their corresponding dialkylmagnesiums. Then, a secondary or tertiary organolithium compound, such as sec- or tert-butyllithium, is added, in the form of a solution in an acyclic liquid hydrocarbon, and the byproduct halide salts which were formed and are present in the reaction mixture are separated from the resulting stable solution of the diorganomagnesium complex by filtration or by equivalent separation procedures.Type: GrantFiled: October 27, 1976Date of Patent: January 17, 1978Assignee: Lithium Corporation of AmericaInventors: Conrad W. Kamienski, Bobby Joe McElroy, Ricardo O. Bach
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Patent number: 4067917Abstract: Organo-lithium compounds of the formula: ##STR1## wherein R is an alkyl group of up to 5 carbon atoms, R' is either hydrogen or an alkyl group of up to 5 carbon atoms and n is an integer from 2 to 10. These bifunctional organo-lithium compounds are prepared without the use of any polar or complexing agent and are useful as polymerization initiators for the production of block copolymers.Type: GrantFiled: June 7, 1976Date of Patent: January 10, 1978Assignees: Societe Chimique des Charbonnages-Cdf Chimie, Agence Nationale de Valorisation de la RechercheInventors: Pierre Sigwalt, Patrick Guyot, Michel Fontanille, Jean-Pierre Vairon
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Patent number: 4060567Abstract: Hydrocarbon fraction containing diolefins and .alpha.-acetylenes are treated with an alkali amide to reduce the .alpha.-acetylene content.Type: GrantFiled: September 10, 1976Date of Patent: November 29, 1977Assignee: The Goodyear Tire & Rubber CompanyInventors: James J. Tazuma, Angelo Bergomi
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Patent number: 4034000Abstract: This invention relates to a method of making polymeric materials having isocyanate reactive groups by polymerizing conjugated diolefins and other olefins with a lithium catalyst in the presence of an ether consisting of diethyl ether, dimethoxy ethane and tetrahydrofuran, then reacting the lithium polymeric adduct with a functionality imparting compound such as carbon dioxide, ethylene oxide, propylene oxide, aldehydes, ketones and carbon disulfide.Type: GrantFiled: July 1, 1970Date of Patent: July 5, 1977Assignee: The Goodyear Tire & Rubber CompanyInventor: Emanuel Schoenberg
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Patent number: 4006187Abstract: Process of metalating benzene containing alkyl, alkoxy or dialkylamino substituents, such as toluene, anisole and N,N-dimethyl-aniline, with an organolithium compound such as sec-butyllithium adducts with styrene, in the presence of a tertiary alkyl amine (containing no methyl groups) such as triethylamine, the ratio of lithium in said organolithium compound to the tertiary alkyl amine being 1 gram atom of the lithium to from about 0.25 to about 4 gram moles of the tertiary alkyl amine.Type: GrantFiled: October 6, 1971Date of Patent: February 1, 1977Assignee: Lithium Corporation of AmericaInventors: Conrad W. Kamienski, Robert C. Morrison, Kenneth R. Martin
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Patent number: 3993674Abstract: This disclosure describes novel 15-hydroxy prostanoic acid derivatives having anti-ulcer, bronchodilator, and hypotensive activity.Type: GrantFiled: March 4, 1975Date of Patent: November 23, 1976Assignee: American Cyanamid CompanyInventors: Robert Eugene Schaub, Martin Joseph Weiss
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Patent number: 3985817Abstract: Preparation of magnesium acetylene complex and its use in preparing ethynyl carbinols.Type: GrantFiled: April 15, 1974Date of Patent: October 12, 1976Assignee: Hoffmann-La Roche Inc.Inventor: John Nicholson Gardner
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Patent number: 3983182Abstract: Alkali metal organic compounds including perlithiated organic compounds are produced by contacting an organic compound having a carbon to hydrogen bond or a carbon to halogen bond in its molecular structure or carbon vapor with a vaporous alkali metal under dry conditions and in the absence of a gas that reacts with the alkali metal other than the organic compound. The alkali metal is activated such as thermally or by being passed through a radio frequency field so that it has sufficient energy to break at least one of the bonds. Perlithiated compounds are formed from alkanes, alkenes, cycloalkanes and aromatic hydrocarbons.Type: GrantFiled: August 23, 1973Date of Patent: September 28, 1976Assignee: Massachusetts Institute of TechnologyInventor: Richard J. Lagow
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Patent number: 3975453Abstract: Butynyllithium is prepared by passing a gaseous unsaturated hydrocarbon selected from the group consisting of 1,2-butadiene or a mixture of 1,2-butadiene, 1,3-butadiene, 1-butyne and 2-butyne into a slurry of lithium metal dispersed in a strong coordinating ether solvent, said slurry being under a substantially oxygen-free atmosphere.Type: GrantFiled: February 24, 1975Date of Patent: August 17, 1976Assignee: Foote Mineral CompanyInventor: William Novis Smith, Jr.
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Patent number: 3966638Abstract: Organometallic compounds of high carbanion yield are prepared by metallation with barium, strontium or calcium or mixture of the same of certain acidic organic compounds having a pKa value of between about 15 and 35 on the MSAD scale in the presence of aprotic polar solvents, e.g., barium reacted with xanthene in 1,2-dimethoxyethane to yield dixanthenyl barium. Such organometallic compounds formed by metal-hydrogen exchange reaction are useful in initiating anionic growth-type polymerization of monomers, e.g., alkylene oxides and vinyl compounds, to form homopolymers and copolymers. The persistence of polymer carbanions created by such catalysts makes possible the controlled preparation of a variety of polymers, including block copolymers.Type: GrantFiled: November 15, 1974Date of Patent: June 29, 1976Inventors: Ivan Glen Hargis, Russell Anthony Livigni
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Patent number: 3959324Abstract: Pesticidal and anti-inflammatory cyclopropyl compounds, cyclopropyl intermediates for the preparation of pesticidal compounds, especially chrysanthemic acid-like intermediates, and a process for preparing same.Type: GrantFiled: August 20, 1973Date of Patent: May 25, 1976Assignee: The Procter & Gamble CompanyInventors: Donald John Peterson, Medford Dwight Robbins
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Patent number: 3957913Abstract: Polyfunctional anionic initiators for the preparation of elastomeric block copolymers are prepared by reacting a monofunctional anionic initiator, such as secondary butyl lithium, with a monovinyl aromatic compound, such as styrene, or a conjugated diene, such as butadiene or isoprene or mixtures thereof to form a polyuric reaction product which in turn, is reacted with a polyvinyl aromatic compound, such as divinyl benzene. The cross-linked reaction product, prior to use, is reacted with styrene or another monovinyl aromatic compound. The resulting polyfunctional anionic initiators are useful in producing elastomeric block co-polymers of the A-B-(A)n type exhibiting good elastomeric properties.Type: GrantFiled: April 12, 1974Date of Patent: May 18, 1976Assignee: Stamicarbon N.V.Inventors: Bernard C. Roest, Herman A. J. Schepers
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Patent number: 3954894Abstract: Preparation of novel organotrilithium initiators, which are soluble in hydrocarbon media, from disubstituted vinylaromatic compounds and mono- and dilithium organic compounds, said initiators being useful in the polymerization of conjugated dienes and copolymerization of these with vinylaromatic compounds.Type: GrantFiled: May 18, 1973Date of Patent: May 4, 1976Assignee: Lithium Corporation of AmericaInventors: Conrad W. Kamienski, Robert C. Morrison
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Patent number: 3952017Abstract: 1-Methyl(or acetyl)-5H-dibenzo[a,d]cycloheptenes and 1-methyl(or acetyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptenes bearing a basic side chain at the 5-position, such as a 3-mono- or dimethylaminopropylidene, a 3-mono- or dimethylaminopropyl or a 3-dimethylaminopropylidene(or propyl)-N-oxide, intermediates and processes for their preparation, are described. The end products are useful antidepressants.Type: GrantFiled: August 30, 1974Date of Patent: April 20, 1976Assignee: Hoffmann-La Roche Inc.Inventors: Emilio Kyburz, Hans Spiegelberg
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Patent number: 3950446Abstract: An ethynylating agent formed from mixing an anhydrous magnesium compound with sodium acetylide and its use in preparing ethynyl carbinols.Type: GrantFiled: April 15, 1974Date of Patent: April 13, 1976Assignee: Hoffmann-La Roche Inc.Inventors: John Nicholson Gardner, George McClelland Whitesides
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Patent number: 3932545Abstract: An alkali metal-containing, organometallic product, which is hydrocarbon-soluble, is prepared by reacting an organo-alkali metal reactant in which the alkali metal atom is bonded to a carbon atom, e.g. cyclohexyl-lithium, with a di(organooxy)-alkaline earth metal reactant, e.g. di-n-butoxy-magnesium, in an organic solvent at about -20.degree. to +120.degree.C. The organo-alkali metal reactant can be prepared by reacting an organo halide with an alkali metal, and this can be done in situ, i.e. in the presence of the di(organooxy)-alkaline earth metal reactant. The organometallic product has approximately the same chemical reactivity as the organo-alkali metal reactant from which it is prepared, but is more soluble in hydrocarbon solvents.Type: GrantFiled: April 8, 1974Date of Patent: January 13, 1976Assignee: The National Hellenic Research FoundationInventor: Constantinos G. Screttas