C-metal Patents (Class 260/665R)
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Patent number: 5202499Abstract: Liquid telechelic polymers are made from dienes and are produced via anionic polymerization. While having low molecular weight, for example less than 15,000, the telechelic polymers are generally gel-free, have high amounts of trans-1,4 structure, low vinyl unsaturation and low bulk viscosities. The liquid telechelic polymers are made utilizing a trimetallic initiator comprised of (1) an organopolylithium compound and (2) a complex of a trialiphatic substituted aluminum compound or derivative thereof and a barium salt of an aromatic alcohol.Type: GrantFiled: January 8, 1991Date of Patent: April 13, 1993Assignee: GenCorp Inc.Inventors: I. Glen Hargis, Hubert J. Fabris, John A. Wilson, Russell A. Livigni
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Patent number: 5171847Abstract: Novel metallo-organic complexes of the formula (M.sub.x X.sub.z. nL)y where M is an alkaline earth metal, a transition metal(at. Nos. 21-30, 39-48 and 72-80 inclusive) or a rare earth metal (at. Nos. 57-71 inclusive), X is an anion e.g. Cl.sup.-, Br.sup.-, NO.sub.3 -, NCS.sup.- etc. and L is a Lewis base, are prepared by reacting a source of the metal M under anhydrous conditions with an anhydrous ammonium salt of the anion X in the presence of the Lewis base, and cooling the reaction mixture to precipitate the complex.Type: GrantFiled: July 5, 1990Date of Patent: December 15, 1992Assignee: The Associated Octel Company LimitedInventors: Ronald Snaith, Dominic S. Wright, Alan T. Brooker, Simon R. Drake
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Patent number: 5171467Abstract: A process for producing organometallic and/or organobimetallic compositions by reacting an organic halide, an alkali metal and magnesium halide in a liquid hydrocarbon solvent containing a limited amount of a Lewis base to produce a dialkyl magnesium compound or a dialkyl magnesium compound complexed with an alkali metal organic compound.Type: GrantFiled: March 6, 1990Date of Patent: December 15, 1992Assignee: FMC CorporationInventors: Vijay C. Mehta, Robert C. Morrison, Conrad W. Kamienski
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Patent number: 5141676Abstract: Organic-solvent soluble magnesium hydrides of the formulas(MgH.sub.2).sub.n. MgQ.sub.2 (II)(MgH.sub.2).sub.n. RMgX (III) ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 19 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: April 17, 1991Date of Patent: August 25, 1992Assignee: Studiengesellschaft Kohle mbHInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5110962Abstract: Manganese bromide solution for use in the formation of organomanganese compounds, applicable to the synthesis of organic products, particularly ketones.Type: GrantFiled: August 15, 1990Date of Patent: May 5, 1992Assignee: Societe Nationale Elf AquitaineInventors: Gerard Cahiez, Blandine Laboue, Pierre Tozzolino
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Patent number: 5104997Abstract: This invention provides a process for deacidifying paper by contacting the paper with hydrocarbon or halocarbon solutions of certain magnesium and/or zinc alkoxyalkoxides which may have been treated with carbon dioxide to yield low viscosity solutions.Type: GrantFiled: December 20, 1990Date of Patent: April 14, 1992Assignee: FMC CorporationInventors: Conard W. Kamienski, Robert S. Wedinger
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Patent number: 5091536Abstract: Organic-solvent soluble magnesium hydrides of the formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamide, aralkyl, aryl or diarylamide group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamide, diarylamide or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.Type: GrantFiled: February 9, 1988Date of Patent: February 25, 1992Assignee: Studiengesellschaft Kohle mbhInventors: Borislav Bogdanovic, Manfred Schwickardi
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Patent number: 5089572Abstract: A process for blanking a reaction mixture utilizing as a blanking agent a difunctional lithium composition.Type: GrantFiled: August 18, 1989Date of Patent: February 18, 1992Assignee: The Dow Chemical CompanyInventors: Gary R. Marchand, Joseph G. Schell, Jr., Brian W. Walther, Corwin J. Bredeweg
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Patent number: 5080835Abstract: Hydrocarbon soluble polymetalated 1-alkene compositions are described, and these compositions may be characterized by the formula ##STR1## wherein R is hydrogen, a hydrocarbyl group or R.sup.1 M, M is an alkali metal, R.sup.1 is a divalent oligomeric hydrocarbyl group comprising moieties derived from a conjugated diene, and wherein the total number moieties derived from a conjugated diene in all of the R.sup.1 groups in Formula I is from about 2 to about 30. Preferably, the alkali metal is lithium.Hydrocarbon soluble polymetalated 1-alkene catalysts for anionic polymerizations are also described which comprise the reaction product of a 1-alkyne, an organometallic compount R.degree.M, and a 1,3-conjugated diene wherein R.degree. is a hydrocarbyl group, M is an alkali metal, the mole ratio of conjugated diene to 1-alkyne is at least about 2:1, and the reaction is conducted at a temperature of at least about 70.degree. C.Type: GrantFiled: September 21, 1990Date of Patent: January 14, 1992Assignee: Bridgestone/Firestone, Inc.Inventor: Jung W. Kang
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Patent number: 5068368Abstract: A process for the preparation of ethynyl carbinols of the formula: ##STR1## wherein R" is hydrogen, a substituted or unsubstituted aliphatic or aromatic hydrocarbon, R'" is a substituted or unsubstituted aliphatic or aromatic hydrocarbon or R" and R'" together to the carbon atom to which they are joined represent a steroid, which comprises the steps ofA. reacting in a solvent system comprising an aromatic hydrocarbon, at least one lithium alkylamide selected from the group consisting of: ##STR2## wherein R is a hydrogen or lower alkyl, R' is hydrogen, lower alkyl, a substituted or unsubstituted aliphatic, alicyclic or aromatic hydrocarbon, x is an integer of 2 to 8, y and z are each 0 to 1, with acetylene to form a monolithium acetylideB. reacting in a solvent system comprising an aromatic hydrocarbon, the monolithium acetylene from Part A with a ketone of the formula R"R'"C.dbd.O, wherein R" and R'" are as hereinbefore defined, and thenC.Type: GrantFiled: May 10, 1990Date of Patent: November 26, 1991Assignee: Cyprus Foote Mineral CompanyInventors: W. Novis Smith, Christopher Louer
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Patent number: 5062998Abstract: A process is provided for making metallated and substituted alkynes from feedstocks which include alkadienes containing allenic unsaturation or such alkadienes in a mixture with alkynes having either internal or terminal unsaturation, such as a mixture of propadiene and propyne. This reaction involves an initial step in which the allenic hydrocarbon and any internal alkyne is isomerized and simultaneously the resultant terminal alkynes are metallated with an alkali metal. The reaction is carried out at relatively low temperatures in a suitable inert solvent such as diethylether. When metallation is complete the reaction mixture can be contacted directly with any suitable electrophile, such as a halo silane, for example, chlorotrimethylsilane, and the alkali metal on the terminal alkyne is replaced with the desired substituent. The products thus formed are useful as monomers for preparing polymers having a variety of properties, for example, as asymmetric membranes for gas separation.Type: GrantFiled: April 23, 1990Date of Patent: November 5, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Frederick L. Herman, Ann C. L. Savoca, Mark L. Listemann
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Patent number: 5041573Abstract: A carboalkylated amino alcohol having each of the below shown formulae is novel and optically active. A separating agent comprising the alcohol and a support is effectively useful to separate a variety of racemates for example with chromatography. The alcohol may be chemically or physically combined with the support. ##STR1## [wherein Ph represents a phenyl group, R represents a hydrogen atom, an alkyl group having the carbon number of 1 to 10, or an aryl group having the carbon number of 6 to 10, X represents an --O-- group or a --S-- group, and Z represents a hydrogen atom, an alkyl group having the carbon number of 1 to 10 or a metal element].Type: GrantFiled: October 18, 1989Date of Patent: August 20, 1991Assignee: Daicel Chemical Industries, Ltd.Inventors: Masaki Hasegawa, Kazuhiko Saigo, Yoichi Yuki, Kouzou Tachibana
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Patent number: 4861742Abstract: Bifunctional initiators for anionic polymerization are prepared by reacting an alkenylaromatic compound of the general formula I ##STR1## where Ar is aromatic hydrocarbyl which may be substituted by alkyl or another group inert toward organoalkali metal compounds and may contain nitrogen,R.sup.1 is linear or branched alkyl, cycloalkyl, alkenyl or aralkyl or from 1 to 22 carbon atoms where at least the carbon adjacent to the double bond is saturated and aliphatic,R.sup.2 is hydrogen or is likewise linear or branched alkyl, cycloalkyl, alkenyl or aralkyl or from 1 to 22 carbon atoms where at least the carbon adjacent to the double bond is saturated and aliphatic, and where R.sup.1 and R.sup.2 may be part of a common cycloaliphatic ring, in the presence of one or more ethers and of tertiary amines and in the presence or absence of a further inert aliphatic, alicyclic or aromatic solvent, at from -20.degree. to +70.degree. C.Type: GrantFiled: September 1, 1988Date of Patent: August 29, 1989Assignee: BASF AktiengesellschaftInventors: Klaus Bronstert, Siegbert Bohnet, Walter Himmele, Kaspar Bott
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Patent number: 4837358Abstract: Process for the production of 9-alkenyl acetates is provided. The process comprises first disproportionating cyclooctene with an .alpha.-olefin to give a 1,9-alkadiene. The alkadiene is metallated to form a 1-metallo-9-alkene, which is then contacted with oxygen to produce a 9-alkenyl-1-oxymetallo compound, which is optionally hydrolyzed to the corresponding alcohol, with the alcohol being esterified to the desired 9-alkenyl ester or the 9-alkenyl-1-oxymetallo compound can be directly esterified, to produce the desired 9-alkenyl esters.Type: GrantFiled: February 26, 1986Date of Patent: June 6, 1989Assignee: Phillips Petroleum CompanyInventors: Jim D. Byers, Charles A. Drake
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Patent number: 4835272Abstract: A process for formation of a base, which comprises reacting an acetylide compound with a salt. The acetylide compound has the following formula:(R--C.tbd.C--).sub.n Mwherein R is a monovalent group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group and a heterocyclic group, each of which may have one or more substituent groups; M is an n-valent transition metal atom; and n is 1, 2 or 3. The salt is composed of an anion having an affinity for the transition metal (M) (the affinity of the anion for the transition metal is more than that of the acetylide anion (R--C.tbd.C.crclbar.)), and a cation derived from one selected from the group consisting of an alkali metal, an alkaline earth metal, ammonia and an organic base. A light-sensitive material containing the acetylide compound and the salt is also disclosed.Type: GrantFiled: July 16, 1987Date of Patent: May 30, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Shunichi Ishikawa, Ken Kawata
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Patent number: 4822530Abstract: Oligomeric polyfunctional initiators for anionic polymerization of dienes and/or alkenylaromatics are prepared by a process in which a mixture of dialkenylaromatics and alkenylaromatics in a molar ratio of from 1:4 to 1:100, in an inert solvent, is run, at from 25.degree. to 100.degree. C., continuously or in small portions, with thorough mixing, into an initially taken mixture which contains from 1.2 to 3.0 molar equivalents, based on the dialkenylaromatics, of one or more organolithium compounds and an inert solvent, and is polymerized completely. The resulting oligomeric initiators are used for the preparation of unfunctionalized or functionalized polymers or block copolymers from dienes and/or alkenylaromatics, and the functionalized polymers thus prepared are used as prepolymers for other resins.Type: GrantFiled: April 1, 1988Date of Patent: April 18, 1989Assignee: BASF AktiengesellschaftInventors: Klaus Bronstert, Siegbert Bohnet
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Patent number: 4728706Abstract: Process for preparing "living" polymer, the process comprising contacting one or more acrylic monomers under polymerizing conditions with a polymerization-initiating amount of a tetra-coordinate organotitanium, organozirconium or organo-hafnium polymerization initiatior, and "living" polymers produced thereby.Type: GrantFiled: August 29, 1986Date of Patent: March 1, 1988Assignee: E. I. Du Pont De Nemours and CompanyInventors: William B. Farnham, Walter R. Hertler
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Patent number: 4707462Abstract: The viscosity of hydrocarbon solutions of dialkylmagnesium compounds is reduced by including as the viscosity reducing agent a nitrogen-containing compound which is a piperidine substituted with a hydrocarbyl group (preferably a C.sub.1 -C.sub.6 alkyl, C.sub.6 -C.sub.9 aryl or C.sub.5 -C.sub.6 cycloalkyl group) at the 2-position and optionally further substituted, triethylamine, cyclohexylamine, dicyclohexylamine, or N-N-dimethylformamide, or a mixture of two or more of these nitrogen-containing compounds. The viscosity reducing agent may be used as such or in the form of a substance produced by reacting such a nitrogen-containing compound with magnesium or with a dialkylmagnesium compound. The viscosity reducing agent may be used alone, or in a mixture with an organoaluminum viscosity reducing agent.Type: GrantFiled: April 24, 1986Date of Patent: November 17, 1987Assignee: Texas Alkyls, Inc.Inventors: Dennis B. Malpass, Loyd W. Fannin, Clark C. Crapo, Kelly B. Triplett
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Patent number: 4687867Abstract: Process for the production of the insect sex attractant, gossyplure, is provided. The process comprises first disproportionating 1,5-cyclooctadiene and 1-hexene to give 1,5,9-tetradecatriene, then metallating the triene to form a 1-metallo-5,9-tetradecadiene, and finally treating the organometal compound with a C.sub.2 -synthon to give directly 7,11-hexadecadienyl acetate or a substituted 7,11-hexadecadienyl moiety which can readily be converted to the desired acetate.Type: GrantFiled: April 14, 1986Date of Patent: August 18, 1987Assignee: Phillips Petroleum CompanyInventors: Dennis S. Banasiak, Edward C. Mozdzen, Jim D. Byers
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Patent number: 4681918Abstract: "Living" polymers and their preparation from acrylic-type or maleimide monomers and organosilicon, -tin or -germanium initiators.Type: GrantFiled: November 21, 1981Date of Patent: July 21, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Owen W. Webster
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Patent number: 4678614Abstract: Stable alkali metal trialkylmagnesiate compositions are produced in high yields by simultaneously adding to a stirred dispersion of an alkali metal in an inert liquid hydrocarbon solvent a soluble dialkylmagnesium compound and an alkyl halide. By using a 2-alkyl substituted C.sub.4 -C.sub.18 primary alkyl chloride as the alkyl halide, alkali metal trialkylmagnesiates are produced which have excellent solubility, even at low temperatures, and good thermal stability over a wide range of temperatures. Moreover, the trialkylmagnesiates are soluble in liquid aliphatic or cycloaliphatic solvents in the absence of aromatic solvents or Lewis bases, which makes these compositions especially useful for certain applications, such as catalysts in anionic polymerization, where the presence of aromatic solvents or Lewis bases is undesirable.Type: GrantFiled: November 27, 1985Date of Patent: July 7, 1987Assignee: Lithium Corporation of America, Inc.Inventors: Conrad W. Kamienski, B. Troy Dover
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Patent number: 4634786Abstract: Stable liquid hydrocarbon-soluble novel magnesium dialkoxide compositions, and complexes thereof with, for example, n-alkyllithiums, organomagnesiums, and the like, useful as or in the preparation of polymerization catalysts and initiators for the polymerization of alpha-olefins and diolefins, which are prepared, for instance, by reacting certain organomagnesium compounds in liquid hydrocarbon solvents with (a) aliphatic 2-alkyl-substituted C.sub.4 -C.sub.12 monohydric primary alcohols, or (b) mixtures of (a) with 2-alkyl-substituted C.sub.3 -C.sub.12 aliphatic secondary or tertiary alcohols, or (c) mixtures of (a) with C.sub.1 -C.sub.12 aliphatic primary linear alcohols. Such dialkoxides and complexes thereof are commonly advantageously prepared in the presence of minor amounts of organoaluminum, organolithium or organopotassium compounds, e.g., trialkylaluminums, alkyllithiums or potassium dialkoxides. An illustrative example of the novel magnesium dialkoxides is 2-methyl-1-pentyloxide.Type: GrantFiled: September 27, 1984Date of Patent: January 6, 1987Assignee: Lithium Corporation of AmericaInventor: Conrad W. Kamienski
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Patent number: 4615843Abstract: Post-precipitation of solids from a hydrocarbon solution of an organomagnesium compound is prevented by addition of an appropriate amount of an alkyllithium compound.Type: GrantFiled: September 5, 1984Date of Patent: October 7, 1986Assignee: Texas Alkyls, Inc.Inventors: Loyd W. Fannin, Clark C. Crapo, Dennis L. Deavenport
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Patent number: 4616027Abstract: Compounds of the general formula ##STR1## or a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein R is 5-chloro-2-pyridyl, phenyl or phenyl substituted by from one to three substituents, each independently selected from F, Cl, Br, I, CF.sub.3, (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy; and n is zero or an integer from 1 to 5; method for their use in combatting fungal infections in plants, seeds and animals, including humans; and pharmaceutical and agricultural compositions containing them.Type: GrantFiled: July 25, 1983Date of Patent: October 7, 1986Assignee: Pfizer Inc.Inventors: Kenneth Richardson, Peter J. Whittle
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Patent number: 4616026Abstract: Compounds of the formula ##STR1## a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein R is 5-chloro-2-pyridyl, phenyl or phenyl substituted by from 1 to 3 substituents, each independently selected from F, Cl, Br, I, CF.sub.3, (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy; and R.sup.1 is H, Cl, phenyl, phenyl substituted by from 1 to 3 substituents each independently selected from F, Cl, Br, I and CF.sub.3 or a heterocyclic group linked to the adjacent CF.sub.2 group by a ring carbon atom; method for their use in combatting fungal infections in plants, seeds and animals, including humans, and pharmaceutical and agricultural compositions containing them.Type: GrantFiled: July 25, 1983Date of Patent: October 7, 1986Assignee: Pfizer Inc.Inventors: Kenneth Richardson, Peter J. Whittle
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Patent number: 4609498Abstract: Process for the production of the insect sex attractant, gossyplure, is provided. The process comprises first disproportionating 1,5-cyclooctadiene and 1-hexene to give 1,5,9-tetradecatriene, then metallating the triene to form a 1-metallo-5,9-tetradecadiene, and finally treating the organometal compound with a C.sub.2 -synthon to give directly 7,11-hexadecadienyl acetate or a substituted 7,11-hexadecadienyl moiety which can readily be converted to the desired acetate.Type: GrantFiled: March 14, 1985Date of Patent: September 2, 1986Assignee: Phillips Petroleum CompanyInventors: Dennis S. Banasiak, Edward C. Mozdzen, Jim D. Byers
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Patent number: 4526720Abstract: The process of the present invention uses an amine to prepare monolithium acetylide which is sufficiently stable at up to 0.degree. and yet is sufficiently reactive to react with 16-substituted-17-keto steroids producing the useful 17.alpha.-ethynyl-17.beta.-hydroxy-16-substituted steroids.Type: GrantFiled: January 5, 1984Date of Patent: July 2, 1985Assignee: The Upjohn CompanyInventors: Verlan H. Van Rheenen, Dae Y. Cha
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Patent number: 4515709Abstract: A novel ternary intercalation compound of a graphite with an alkali metal fluoride and fluorine, which is represented by the formula C.sub.x F(MF).sub.y wherein M is an alkali metal is produced by reacting a graphite material with an alkali metal fluoride in an atmosphere of fluorine gas at a temperature of 0.degree. C. to 250.degree. C. for at least a period of time to effect a weight increase in the graphite. The ternary graphite intercalation compound thus obtained has not only an excellent stability to humidity or moisture but also a high electrical conductivity. The novel ternary graphite intercalation compound according to the present invention may be practically used as a novel electrically conductive material and a catalyst of organic reactions.Type: GrantFiled: March 9, 1983Date of Patent: May 7, 1985Assignee: Central Glass Co., Ltd.Inventors: Nobuatsu Watanabe, Tsuyoshi Nakajima, Masayuki Kawaguchi
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Patent number: 4497748Abstract: Divinyl benzene and/or diisopropenyl benzene in hydrocarbon solvent is added over a period of time at low temperature to a hydrocarbon solvent containing a C.sub.2-20 normal, secondary or tertiary alkyl or cycloalkyl lithium compound and a tertiary alkylamine having 2-4 carbon atoms prepared at low temperature to provide an initiator having an average of from 4 to 9 C-Li sites and a VPO Mn of from about 750 to 4,000. These initiators are useful in polymerizing dienes and vinyl monomers to provide star polymers having an average of from about 4 to 9 arms or branches. These star polymers among other things are useful low profile or low shrink additives for FRPs, e.g., glass fiber reinforced plastics.Type: GrantFiled: September 22, 1982Date of Patent: February 5, 1985Assignee: The General Tire & Rubber CompanyInventors: Francis J. Vitus, Ivan G. Hargis, Russell A. Livigni, Sundar L. Aggarwal
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Patent number: 4460515Abstract: Hydrocarbon, especially aliphatic and/or cycloaliphatic hydrocarbon, solvent solutions of complexes of sec-butyllithium and ethyllithium, exemplified by (a) equimolar solutions of sec-butyllithium and ethyllithium in n-hexane or cyclohexane, (b) 35 mole % sec-butyllithium and 65 molar % ethyllithium in n-hexane or cyclohexane, and (c) 1 mole % sec-butyllithium and 3 mole % ethyllithium in n-hexane or cyclohexane. The thermal stability of the complexes of sec-butyllithium and ethyllithium in the solutions thereof in hydrocarbon solvents has been found to be outstanding. The hydrocarbon solvent solutions, especially where said solvents are aliphatic or cycloaliphatic, have marked advantages over conventionally used hydrocarbon solvent solutions of sec-butyllithium as catalysts or initiators in polymerization reactions, telomerization reactions, metalation reactions, halogen-metal interchange reactions, and in the preparation of magnesium alkyls and other organometallics.Type: GrantFiled: July 6, 1982Date of Patent: July 17, 1984Assignee: Lithium Corporation of AmericaInventor: Robert C. Morrison
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Patent number: 4455387Abstract: A process for making mixed dialkylmagnesiums wherein magnesium metal is reacted with ethylene and an alkyl halide in the presence of a hydrocarbon solvent and in a substantially moisture-free and ether-free atmosphere, under relatively high pressure and at a relatively high temperature followed by separation of undissolved solids from the resulting solution. A composition of matter produced by the process comprising dialkylmagnesium compounds having at least four different alkyl groups, a hydrocarbon solvent and a small amount of an alkyl or alkoxy aluminum compound.Type: GrantFiled: September 27, 1982Date of Patent: June 19, 1984Assignee: Ethyl CorporationInventors: Bonnie G. McKinnie, Gene C. Robinson
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Patent number: 4450259Abstract: Multifunctional anionic initiators having the general formula: ##STR1## and process for synthesizing said initiators and their use in polymerizing dienic monomers and for making block polymers.Type: GrantFiled: December 16, 1982Date of Patent: May 22, 1984Assignee: Enoxy Chimica, S.p.A.Inventors: Arnaldo Roggero, Mario Bruzzone, Alberto Gandini
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Patent number: 4447369Abstract: A method of effectively increasing the settling rate of solid co-products from relatively viscous dialkyl magnesium solutions and thereby reducing the viscosity of such solutions wherein a small quantity of bis(cyclopentadienyl)magnesium or other cyclopentadienyl compound is added thereto. Alternatively, the bis(cyclopentadienyl)magnesium may be prepared in situ by adding cyclopentadiene directly to the dialkyl magnesium.Type: GrantFiled: April 25, 1983Date of Patent: May 8, 1984Assignee: Ethyl CorporationInventor: Eugene C. Ashby
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Patent number: 4429054Abstract: Hydrocarbon, especially aliphatic and/or cycloaliphatic hydrocarbon, solvent solutions of complexes of isopropyllithium and ethyllithium, exemplified by (a) equimolar solutions of isopropyllithium and ethyllithium in n-hexane or cyclohexane, and (b) 25 mole % isopropyllithium and 75 mole % ethyllithium in n-hexane or cyclohexane. The hydrocarbon solvent solutions of said complexes, especially where said solvents are aliphatic or cycloaliphatic, have various advantages over conventionally used hydrocarbon solvent solutions of isopropyllithium as catalysts or initiators in polymerization reactions, telomerization reactions, metalation reactions, halogen-metal interchange reactions, and in the preparation of magnesium alkyls and other organometallics.Type: GrantFiled: July 9, 1982Date of Patent: January 31, 1984Assignee: Lithium Corporation of AmericaInventor: Robert C. Morrison
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Patent number: 4404216Abstract: 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol and its pharmaceutically acceptable acid addition salts are disclosed. This particular bis-triazole derivative and its aforesaid salts are useful for treating fungal infections in animals, including humans. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: June 1, 1982Date of Patent: September 13, 1983Assignee: Pfizer Inc.Inventor: Kenneth Richardson
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Patent number: 4399078Abstract: Hydrocarbon, especially aliphatic and/or cycloaliphatic hydrocarbon, solvent solutions of complexes of n-butyllithium and ethyllithium, exemplified by (a) equimolar solutions of n-butyllithium and ethyllithium in n-hexane or cyclohexane, (b) 36 molar % n-butyllithium and 64 mole % ethyllithium in n-hexane or cyclohexane, and (c) 25 mole % n-butyllithium and 75 mole % ethyllithium in n-hexane or cyclohexane. The thermal stability of the complexes of n-butyllithium and ethyllithium in the solutions thereof in hydrocarbon solvents has been found to be outstanding. The hydrocarbon solvent solutions of said complexes, especially where said solvents are aliphatic or cycloaliphatic, have marked advantages over conventionally used hydrocarbon solvent solutions of n-butyllithium as catalysts or initiators in polymerization reactions, telomerization reactions, metalation reactions, halogen-metal interchange reactions, and in the preparation of magnesium alkyls and other organometallics.Type: GrantFiled: July 6, 1982Date of Patent: August 16, 1983Assignee: Lithium Corporation of AmericaInventor: Robert C. Morrison
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Patent number: 4396554Abstract: A composition of matter comprising di-isoamylmagnesium and diethylmagnesium, with an isoamyl: ethyl alkyl group ratio of about 1.4 to about 4:1, which is soluble in aliphatic, cycloaliphatic, and aromatic hydrocarbon solvents is disclosed, as is a process for making such mixed dialkylmagnesium wherein magnesium metal is reacted with an ethyl halide and an isoamyl halide in the presence of the hydrocarbon solvent and in a substantially moisture-free and ether-free atmosphere, followed by separation of undissolved solids from the resulting solution.Type: GrantFiled: December 28, 1981Date of Patent: August 2, 1983Assignee: Ethyl CorporationInventors: Gene C. Robinson, Bonnie G. McKinnie
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Patent number: 4354982Abstract: A catalytic system is provided for the lithiation of .alpha.-olefins and .alpha.,.omega.-diolefins with concurrent production of lithium hydride. The catalysts include oxygen and sulfur containing organic compounds and polycyclic aromatics which can be combined with alkali metals and/or transition metal compounds. High yields of pure and stereospecific lithiated olefins are obtainable.Type: GrantFiled: March 4, 1980Date of Patent: October 19, 1982Assignee: Studiengesellschaft Kohle m.b.H.Inventor: Borislav Bogdanovic
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Patent number: 4348300Abstract: Agglomeration of dispersions of an alkali metal in an organic liquid is reduced by adding at least about 2.5% of an aryl halide, e.g., chlorobenzene.Type: GrantFiled: July 28, 1980Date of Patent: September 7, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert F. McCartney, Nicholas Nazarenko
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Patent number: 4342708Abstract: Novel hydrocarbon-soluble isopropyl group-containing diorganomagnesium compounds and hydrocarbon solutions thereof are disclosed. The compound of the present invention has a high weight percent of Mg per one mol thereof, and the hydrocarbon solution of the present invention has a very low viscosity as compared with the conventional solutions. The hydrocarbon solution of the present invention can be prepared according any of various processes. If the reaction is carried out in an ether medium, the ether is substituted with a hydrocarbon solvent by removing the ether from the reaction mixture by distillation in the presence of the hydrocarbon solvent.Type: GrantFiled: July 16, 1980Date of Patent: August 3, 1982Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hisaya Sakurai, Yoshihiko Katayama, Tadashi Ikegami, Shigeo Tsuyama
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Patent number: 4339397Abstract: The invention provides a novel and improved method for the preparation of a sodium salt of a 1-alkyne of the general formula ##STR1## in which R.sup.1 and R.sup.2 are each a hydrogen atom or a monovalent hydrocarbon group free from aliphatic unsaturation, by the reaction of a corresponding 1,2-alkadiene with metallic sodium in an inert organic solvent. According to the invention, the metallic sodium is dispersed in the inert solvent as finely as possible to have a particle diameter not exceeding 1000 .mu.m so as that the reaction velocity is very much increased even under atmospheric pressure to give an improved yield of the product.Type: GrantFiled: November 21, 1980Date of Patent: July 13, 1982Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshinobu Ishihara, Kenichi Taguchi, Akira Yamamoto
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Patent number: 4329301Abstract: A method of preparing a di-organo-magnesium compound of the formula R.sub.2 M.sub.g in which R is an organic radical bonded to Mg by carbon, comprising reacting magnesium hydride MgH.sub.2 or magnesium and hydrogen with an olefin in the presence of a catalyst comprising a compound of a transition metal of the 4th to 8th secondary group and an organometallic compound or a hydride of a metal of the 1st to 3rd principal groups of the periodic system. Advantageously there is also present a polycyclic aromatic compound or a tertiary amine as activator and the reaction is effected in the presence of tetrahydrofuran as solvent at a pressure of about 1 to 300 bars at about 0.degree. to 200.degree. C., the atomic ratio of Mg:transition metal being from about 10.sup.4 to 10:1, the molar ratio of transition metal compound:organometal compound or metal hydride being from about 0.1 to 10:1, the molar ratio of olefin:magnesium being from about 2 to 10:1 and the olefin being of the formula CH.sub.2 .dbd.Type: GrantFiled: February 21, 1980Date of Patent: May 11, 1982Assignee: Studiengesellschaft Kohle mbHInventor: Borislav Bogdanovic
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Patent number: 4325840Abstract: Organomagnesium complexes, which have the formula:(R'.sub.2 Mg).sub.m .multidot.(RM).sub.nwherein RM is an organozinc or organoboron compound, R' is a primary alkyl or aryl group, and having an m:n ratio of about 1 or greater, are disclosed. These complexes are prepared by reacting magnesium with an organohalide selected from primary alkyl halides or aryl halides in the presence of a hydrocarbon solvent and subsequently adding an organozinc or organoboron compound. Alternately, the organozinc or organoboron compound can be generated in situ by adding a zinc or boron salt which is alkylated by the magnesium alkyl. The organozinc and organoboron compounds function as solubilizing agents for organomagnesium compounds which are normally only slightly soluble or insoluble in hydrocarbon media. These complexes are characterized by very low halide content, lack of ether contamination, magnesium to metal ratios of from about 1:1 to about 20:1, and hydrocarbon solubility. Even higher ratios are conceivably obtainable.Type: GrantFiled: November 30, 1979Date of Patent: April 20, 1982Assignee: Texas Alkyls, Inc.Inventor: Dennis B. Malpass
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Patent number: 4299781Abstract: A low viscosity liquid solution is described, comprising(a) a hydrocarbon-soluble dialkylmagnesium compound of 4 to 20 carbon atoms per molecule(b) a solvent selected from the group consisting of aliphatic, alicyclic, and aromatic hydrocarbons of 5 to 20 carbon atoms, and(c) an organometallic additive selected from the group consisting of R.sub.3 Ga, R.sub.3 In, and RLi, in which R is C.sub.1 -C.sub.12 alkyl or C.sub.5 -C.sub.7 cycloalkyl.Also disclosed is a method of preparing such a solution by in situ generation of the dialkylmagnesium compound via the reaction between metallic magnesium and the appropriate alkyl halide in the presence of both the solvent and the organometallic additive.Type: GrantFiled: May 12, 1980Date of Patent: November 10, 1981Assignee: Texas Alkyls, Inc.Inventors: Loyd W. Fannin, Dennis B. Malpass, Ramiro Sanchez
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Patent number: 4267363Abstract: Synthesis and intermediates for making an insect pheromone useful in the control of the yellow scale.Type: GrantFiled: June 26, 1978Date of Patent: May 12, 1981Assignee: Zoecon CorporationInventors: Richard J. Anderson, Clive A. Henrick
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Patent number: 4222969Abstract: A composition of matter comprising di-n-butylmagnesium and dimethylmagnesium, to the exclusion of dialkylmagnesium compounds containing alkyl groups other than n-butyl or methyl, with an n-butyl:methyl alkyl group ratio of about 0.2:1 to about 5:1 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 methyl 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: April 5, 1979Date of Patent: September 16, 1980Assignee: Texas Alkyls, Inc.Inventors: Loyd W. Fannin, Dennis B. Malpass
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Patent number: 4207207Abstract: A composition of matter is disclosed comprising dimethylmagnesium, di-n-propylmagnesium and optionally diethylmagnesium. The composition is soluble in aliphatic, cycloaliphatic, and aromatic hydrocarbon solvents without the aid of solubilizing agents. The composition is prepared in the substantial absence of oxygen and moisture by the simultaneous or consecutive reactions of methyl, ethyl, and n-propyl halides with metallic magnesium in the presence of the hydrocarbon solvent, followed by separation of the insoluble magnesium halide and any unreacted magnesium metal from the resulting solution.Type: GrantFiled: January 17, 1979Date of Patent: June 10, 1980Assignee: Texas Alkyls, Inc.Inventors: Ramiro Sanchez, Loyd W. Fannin, Dennis B. Malpass
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Patent number: 4205016Abstract: Highly desirable multifunctional lithium containing initiators are prepared by reacting a compound such as an organo lithium with an organic compound containing at least two 1,1-diphenylethylene groups. 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. Several di-lithium compounds have been employed to initiate polymerization of various unsaturated organic monomers.Type: GrantFiled: August 7, 1978Date of Patent: May 27, 1980Assignee: The Dow Chemical CompanyInventors: Lu H. Tung, Grace Y-S. Lo, Joseph W. Rakshys, Douglas E. Beyer
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Patent number: 4201729Abstract: Highly desirable multifunctional lithium containing initiators are prepared by reacting a compound such as an organo lithium with an organic compound containing at least two 1,1-diphenylethylene groups. 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. Several di-lithium compounds have been employed to initiate polymerization of various unsaturated organic monomers.Type: GrantFiled: August 7, 1978Date of Patent: May 6, 1980Assignee: The Dow Chemical CompanyInventors: Lu H. Tung, Grace Y-S. Lo, Joseph W. Rakshys, Douglas E. Beyer
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Patent number: 4196153Abstract: 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 7, 1978Date of Patent: April 1, 1980Assignee: The Dow Chemical CompanyInventors: Lu H. Tung, Grace Y-S Lo