Patents Examined by Paul F. Shaver
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Patent number: 4276426Abstract: This invention relates to the preparation of organosilicon compounds by the addition of a silicon compound containing Si-bonded hydrogen to a compound having an aliphatic multiple bond in the presence of a catalyst which promotes the addition of Si-bonded hydrogen to compounds containing an aliphatic multiple bond. In this process the reactants and the catalyst are continuously introduced into a pipe-shaped reactor while the contents of the reactor, which are maintained in a liquid phase by the application of pressure are circulated in the reactor at a rate of at least 1,000 cm per minute and while the reaction mixture is continuously being removed from the reactor.Type: GrantFiled: November 28, 1979Date of Patent: June 30, 1981Assignee: Wacker-Chemie GmbHInventors: Tassilo Lindner, Norbert Zeller, Volker Frey, Rudolf Riedle, Peter John, Georg Engelsberger
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Patent number: 4276425Abstract: Cyclic dimethylpolysiloxanes are prepared by heating a mixture containing linear or branched organopolysiloxanes consisting of at least 50 mol percent dimethylsiloxane units and aqueous sulfuric acid in which the aqueous sulfuric acid contains from 50 to 85 percent by weight of sulfuric acid, while simultaneously recovering the cyclic dimethylpolysiloxanes thus formed.Type: GrantFiled: July 11, 1979Date of Patent: June 30, 1981Assignee: Wacker-Chemie GmbHInventors: Jurgen Burkhardt, Eckhart Louis
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Patent number: 4276424Abstract: Organic polysilanes may be produced in a simpler, safer and more economic manner by reacting an organohalosilicon hydride with lithium metal or lithium-alkali metal alloy. According to the reaction the silicon-silicon bonds of the organopolysilane are formed by the removal of halogen and hydrogen from the hydride. Particularly important is the formation of dodecamethylcyclohexasilane by the reaction of dimethyl chlorosilane with lithium metal. Simpler polysilanes may be produced by adding to the reaction mixture endcappers such as trifunctional organohalosilanes without an Si-H bond.Type: GrantFiled: December 3, 1979Date of Patent: June 30, 1981Assignee: Petrarch SystemsInventors: William R. Peterson, Jr., Barry C. Arkles
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Patent number: 4269991Abstract: Novel mercaptoorganosiloxane compounds of the formula ##STR1## wherein n has a value of from 1 to 3 inclusive, are useful as components of primer compositions for enchancing the adhesion of silicone elastomers to substrates.Type: GrantFiled: December 3, 1979Date of Patent: May 26, 1981Assignee: Dow Corning CorporationInventors: Gary R. Homan, Louis H. Toporcer
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Patent number: 4269993Abstract: Novel diaralkyldichlorosilanes expressed by the general formula (I) ##STR1## (wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represent hydrogen atom or an alkyl group having 1.about.4 carbon atoms, but a case where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are all hydrogen atom is excluded),and a process for producing the same are provided.They are useful as monomers for producing polysiloxanes and as intermediates for synthesizing novel organosilicon compounds.Type: GrantFiled: October 15, 1979Date of Patent: May 26, 1981Assignee: Chisso CorporationInventors: Nobumasa Ohtake, Isao Koga, Yohji Terui
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Patent number: 4269768Abstract: Chlorozincate salts of thiazolium azo compounds are prepared by reacting thiazolium azo compounds with an dialkylsulfate having from 1 to 4 carbon atoms in the alkyl radicals, which process comprises carrying out the reaction in an aqueous medium at a temperature of from about 10.degree. to 50.degree. C. in the presence of a zinc compound capable of binding acid, and with the use of from 1.8 to 2.5 mols of the dialkylsulfate, calculated on the starting azo dyestuff, at a pH not exceeding 8, preferably at 3-7. The prepared thiazolium azo compound is precipitated as chlorozincate salt, especially by means of an alkali metal chloride. According to this process, the chlorozincate salts are obtained in higher purity. A perceptible decomposition of the thiazolium azo compound does not occur. Chemicals, for example the alkylation agent and acid-binding agents need be used in a small quantity.Type: GrantFiled: July 6, 1979Date of Patent: May 26, 1981Assignee: Hoechst AktiengesellschaftInventors: Rudolf Neeb, Kurt Hohmann, Reinhard Mohr
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Patent number: 4268455Abstract: Chelating tertiary amino metal amides selected from compounds having the formulae: Mg.sup. ++ [Chel N].sub.2.sup..crclbar. wherein [Chel N].sup..crclbar. is not ##STR1## [Chel N].sup..crclbar. M.sup..sym., [Chel N].sup..crclbar. M.sup..sym. M'H.sub.m R.sub.n X.sub.p, Z Mg.sup..sym. [Chel N--M'H.sub.m R.sub.n X.sub.p ].sup..crclbar., Mg.sup. ++ --[Chel N--M'H.sub.m R.sub.n X.sub.p ].sup..crclbar. [M'H.sub.m R.sub.n X.sub.p Z].sup..crclbar., Chel N-Mg.sym.[N--Mg.sup..sym. H.sub.m R.sub.n X.sub.p Z].sup..crclbar. and Mg.sup. ++ [Chel N--M'H.sub.m R.sub.n X.sub.p ].sub.2 .sup..crclbar., wherein M is a Group IA metal, M' is a metal selected from the group consisting of Li, Na, Mg, Be, Zn, Cd, B, Al, Ga, In, Zr, Ti, Sn and Cu and m and n=0 to 4, p=0 to 3 and (m+n+ p)=the valence of M' and (m+n)= at least 1 and X is a nonreactive group selected from the group consisting of chlorine, bromine, iodine, C.sub.1 to C.sub.20 alkoxide, C.sub.1 to C.sub.20 thioalkoxide, C.sub.2 to C.sub.40 hydrocarbyl secondary amide and C.Type: GrantFiled: August 12, 1976Date of Patent: May 19, 1981Assignee: Exxon Research & Engineering Co.Inventors: Arthur W. Langer, Jr., Thomas A. Whitney
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Patent number: 4268682Abstract: Novel .omega.alkenyl silane monoadducts and bis-.alpha., .omega.-silyl alkanes are disclosed. The .omega.-alkenyl silanes or bis-.alpha.,.omega.-silyl alkanes are prepared by the selective addition of silane having chlorine, alkoxy or acyloxy groups to an .alpha.,.omega.-diene. The additions may be carried out in the liquid phase in the presence of free radical and/or metal and/or metal salt catalyst.Type: GrantFiled: December 12, 1977Date of Patent: May 19, 1981Assignee: Exxon Research & Engineering Co.Inventors: Alexis A. Oswald, Lawrence L. Murrell
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Patent number: 4267172Abstract: The present invention presents a novel class of compounds bis(triorganosilylalkyl) phosphites, e.g. bis(trimethylsilylmethyl) phosphite. The compound is readily prepared by the reaction of a corresponding triorganosilyl alkanol with phosphorus trichloride or by the partial hydrolysis of a corresponding tris(triorganosilylalkyl) phosphite with an equimolar amount of water followed by distillation of the reaction mixture.The compound has a remarkable anti-transplanted tumor effectiveness as established by the test with mice as the test animals for preventing the growth of Ehrlich's cancer cells and Sarcoma 180 cells. The compound has very low toxicity when orally administrated.Type: GrantFiled: September 25, 1979Date of Patent: May 12, 1981Assignee: Shin-Etsu Chemical Co. Ltd.Inventors: Shigeshi Toyoshima, Ryuichi Sato, Koichi Ito, Toshio Shinohara, Masatoshi Arai
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Patent number: 4267356Abstract: A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1 to 4 carbon atoms, this process being based on the reaction of a corresponding 2,6-dialkylaniline with a corresponding alkyl 2-chloropropionate or alkyl 2-bromopropionate. The process is carried out by carrying out the reaction of the 2,6-dialkylaniline with the 2-halogenopropionic acid ester at 110.degree.-130.degree. C. in the presence of an alkali metal iodide as the catalyst, and of an alkali metal carbonate or alkali metal bicarbonate as an acid acceptor, in excess 2,6-dialkylaniline as the solvent, removing, by distillation, the water formed during the reaction and working up the organic phase, which is obtained after adding water and separating the phases, by distillation.Type: GrantFiled: June 9, 1980Date of Patent: May 12, 1981Assignee: Ciba-Geigy CorporationInventors: Alfred Grieder, Klaus-Jurgen Coers, Peter Labuhn
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Patent number: 4266071Abstract: A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1 to 4 carbon atoms, this process being based on the reaction of a corresponding 2,6-dialkylaniline with a corresponding alkyl 2-bromopropionate. The process is carried out by carrying out the reaction of the 2,6-dialkylaniline with the alkyl 2-bromopropionate at 110.degree. to 125.degree. C. in excess 2,6-dialkylaniline as the solvent, in the presence of a quaternary compound of nitrogen or of phosphorus, and in the presence of an alkali metal carbonate or alkali metal bicarbonate as an acid acceptor, distilling off the water formed during the reaction and working up the organic phase, which is obtained after adding water and separating the phases, by distillation.Type: GrantFiled: June 9, 1980Date of Patent: May 5, 1981Assignee: Ciba-Geigy CorporationInventors: Alfred Grieder, Klaus-Jurgen Coers
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Patent number: 4265813Abstract: Azo dyestuffs which, in the form of the free acid, correspond to the formula ##STR1## wherein R.sub.1 denotes hydrogen, methyl or chlorine,R.sub.2 denotes hydrogen, chlorine, acetylamino, methoxy, ethoxy, nitro or carboxyl,R.sub.3 denotes hydrogen, sulpho-C.sub.1 -C.sub.2 -alkyl, carboxy-C.sub.1 -C.sub.2 -alkyl or C.sub.1 -C.sub.4 -alkyl,R.sub.4 denotes hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sub.5 denotes hydrogen or acyl andR.sub.6 denotes hydrogen, methyl, methoxy, ethoxy, chlorine, carboxyl, nitro or sulpho,and their preparation and use for dyeing substrates which can be dyed with direct dyestuffs.Type: GrantFiled: October 27, 1978Date of Patent: May 5, 1981Assignee: Bayer AktiengesellschaftInventors: Horst Nickel, Karl H. Schundehutte
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Patent number: 4266068Abstract: An improved process for producing tetramethyldisilane by Lewis acid catalyzed redistribution of hexamethyldisilane with a crude mixture of methylchlorodisilane which comprises the distillation of the mixed redistributed product with collection of a middle distillate cut containing at least 95% pure tetramethyldichlorodisilane.Type: GrantFiled: July 28, 1980Date of Patent: May 5, 1981Assignee: Nalco Chemical CompanyInventors: Ronald J. Allain, Joseph P. Maniscalco
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Patent number: 4264496Abstract: The present invention provides concentrated aqueous acid solutions of the colorant having the formula: ##STR1## in which A.sup..crclbar. represents the formate, acetate or propionate anion. The solutions are prepared starting with the corresponding chloride or sulfomethylate by forming the m- or p-nitrobenzoate, dissolving said salt in formic, acetic or propionic acid and eliminating the nitrobenzoic acid which is precipitated. The solutions of the invention can be used for coloring and printing fibers containing acid groups, and particularly acrylic fibers.Type: GrantFiled: November 15, 1979Date of Patent: April 28, 1981Assignee: Produits Chimiques Ugine KuhlmannInventor: Marcel Durant
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Patent number: 4264459Abstract: Stabilized organopolysiloxane oils having at least one aliphatic hydrocarbon radical with at least two carbon atoms and containing rubidium and/or cesium compounds which are at least partially soluble in the oil, in which the amount of rubidium and/or cesium present in the oil is from 0.01 to 3 percent by weight, based on the weight of the oil.The stabilized organopolysiloxane oils are useful as lubricants or as additives for lubricating compositions.Type: GrantFiled: January 24, 1980Date of Patent: April 28, 1981Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Walter Hafner, Erich Markl, Dietrich Samrowski
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Patent number: 4264527Abstract: A process for preparing cyclopropylmethyl-n-propylamine from the reaction of cyclopropylmethylamine with propionitrile is described. The reaction takes place in the presence of a hydrogenation catalyst, preferably a mixture of rhodium on carbon and platinum on carbon. The process is particularly useful as it consumes the cyclopropylmethylamine by-product from another scheme for the synthesis of cyclopropylmethyl-n-propylamine.Type: GrantFiled: August 1, 1979Date of Patent: April 28, 1981Assignee: Ciba-Geigy CorporationInventor: Edwyn A. Curtis
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Patent number: 4263226Abstract: 5-Amino-5,6-dihydro-dicyclopentadiene is prepared by reacting 5-isothiocyano-5,6-dihydro-dicyclopentadiene and an aqueous caustic medium at a temperature in excess of the melting point of 1,3-bis[5-(5,6-dihydro-dicyclopentadiene)]-2-thiourea while establishing and maintaining a pressure sufficient to maintain the water in the reaction mixture in a liquid state.Type: GrantFiled: January 22, 1980Date of Patent: April 21, 1981Assignee: Boots Hercules Agrochemicals Co.Inventor: Melvin M. Pombo
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Patent number: 4261915Abstract: Compositions for protecting materials from growth of pestiferous organisms, and particularly for protecting marine surfaces from fouling organisms, are formed from precursors having the formula ##STR1## where m is from 1 to about 10, where each X is independently selected from the group consisting of alkyl and alkoxyalkyl radicals containing less than about 6 carbon atoms and Y, where Y has the formula ##STR2## where R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of alkyl, cycloalkyl, and aryl radicals, where R.sub.1, R.sub.2 and R.sub.3 contain in combination up to about 18 carbon atoms. The ratio of the tin atoms to silicon atoms in the precursors is at least about 1:50.The precursors can be directly used as an additive for coatings. The precursors can also be used by subjecting them to hydrolysis and polycondensation to form an organotin substituted polysiloxane for use as an additive and a binder for coatings.Type: GrantFiled: February 19, 1980Date of Patent: April 14, 1981Assignee: Ameron, Inc.Inventors: Gabriel H. Law, Albert P. Gysegem
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Patent number: 4260715Abstract: In the production of linear and branched equilibrated acyloxy-containing organopolysiloxanes by reacting a chlorosilane of the formulaR.sub.a R'.sub.b SiCl.sub.(4-a-b)in whicha is 0,1,2 or 3,b is 0,1,2 or 3, anda+b.ltoreq.3,or a partial hydrolysate thereof, with at least one organosiloxane containing the componentsR.sub.2 R"--SiO.sub.1/2,R R"--SiO,R"--SiO.sub.3/2 andSiO.sub.2in whichR and R" each independently is H or an optionally halogen- or cyano-substituted monovalent hydrocarbon radical having up to 12 carbon atoms, andR" is Cl, OH, H or an optionally halogen- or cyano-substituted monovalent hydrocarbon radical having up to 12 carbon atoms,in the presence of an equilibration catalyst, the improvement which comprises employing as the equilibration catalyst a salt of a fluorinated alkane sulphonic acid plus a monobasic carboxylic acid, the total number of Si--Cl groups exceeding the total number of Si--OH groups in the reactants and the monobasic carboxylic acid being present in at least about 1.Type: GrantFiled: December 7, 1979Date of Patent: April 7, 1981Assignee: Bayer AktiengesellschaftInventors: Armand de Montigny, Hans Niederprum
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Patent number: 4260782Abstract: A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1-4 carbon atoms. According to this process, a 2-chloropropionic acid ester having 1-4 carbon atoms in the alkyl group is reacted in the presence of water and of a quaternary ammonium or phosphonium salt with an alkali metal iodide to give a mixture of the 2-chloropropionic acid ester and the 2-iodopropionic acid ester, and this mixture is subsequently reacted, after separating off the aqueous phase, at 110-130.degree. C.Type: GrantFiled: June 9, 1980Date of Patent: April 7, 1981Assignee: Ciba-Geigy CorporationInventors: Alfred Grieder, Klaus-Jurgen Coers