Magnesium-containing Reactant Patents (Class 556/480)
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Patent number: 11066427Abstract: The invention provides an organosilane compound having a more bulky substituent group than the existing organosilane compounds. The compound is represented by formula (1) wherein R1 is a C4-C10 tertiary hydrocarbon group, R2 is a C1-C10 alkyl group, and LG is halogen or trifluoromethanesulfonyloxy.Type: GrantFiled: June 4, 2020Date of Patent: July 20, 2021Assignee: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Shotaro Aoki, Ayumu Kiyomori
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Patent number: 9534001Abstract: An organomagnesium synthesis agent, a process for preparing this synthesis agent, and its use.Type: GrantFiled: March 5, 2007Date of Patent: January 3, 2017Assignee: Chemetall GmbHInventors: Steffen Haber, Dieter Hauk, Ulrich Wietelmann, Dirk Dawidowski, Peter Rittmeyer, Jens Roder
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Patent number: 9260458Abstract: A method of producing an organic silicon compound includes a step of reaction of the following: (A) a reactive silane compound represented by General Formula (1) below: R1mSiY(4-m) (wherein R1 is a monovalent organic group (except for the group represented by Y) or a hydrogen atom; Y indicates a chlorine atom or a group represented by —OR2; R2 indicates a monovalent hydrocarbon group having 1 to 30 carbon atoms; and m is a number in the range of 0 to 3), (B) a halogenated organic compound represented by General Formula (2) below: R3—X (wherein R3 indicates a monovalent organic group; and X is a halogen atom), and (C) metallic magnesium (Mg) in the presence of (D) an organic solvent containing at least one type of ether type compound.Type: GrantFiled: December 25, 2012Date of Patent: February 16, 2016Assignee: Dow Corning CorporationInventors: Yasushi Sugiura, Yoshinori Taniguchi
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Publication number: 20150141689Abstract: A method of producing an organic silicon compound includes a step of reaction of the following: (A) a reactive silane compound represented by General Formula (1) below: R1mSiY(4-m) (wherein R1 is a monovalent organic group (except for the group represented by Y) or a hydrogen atom; Y indicates a chlorine atom or a group represented by —OR2; R2 indicates a monovalent hydrocarbon group having 1 to 30 carbon atoms; and m is a number in the range of 0 to 3), (B) a halogenated organic compound represented by General Formula (2) below: R3-X (wherein R3 indicates a monovalent organic group; and X is a halogen atom), and (C) metallic magnesium (Mg) in the presence of (D) an organic solvent containing at least one type of ether type compound.Type: ApplicationFiled: December 25, 2012Publication date: May 21, 2015Inventors: Yasushi Sugiura, Yoshinori Taniguchi
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Patent number: 8859797Abstract: A SiH[CH2—Si(OEt)3]3 carbosilane compound is synthesized by reacting a Grignard reagent having the formula Si(OEt)3(CH2MgCl) with a quenching agent having the formula SiHCl3.Type: GrantFiled: August 22, 2013Date of Patent: October 14, 2014Assignees: Air Liquide Electronics U.S. LP, L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude, American Air Liquide, Inc.Inventors: Zhiwen Wan, Ziyun Wang, Ashulosh Misra, Jean-Marc Girard, Claudia Fafard, Andrey V. Korolev
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Patent number: 8809568Abstract: The present disclosure provides a method of preparing silylethynyl compounds in which two of the hydrocarbyl groups bonded to the silicon exclusive of the ethynyl group, are the same and one is different, that may be used in preparing novel silylethynyl functionalized acene semiconductor chromophores.Type: GrantFiled: May 25, 2011Date of Patent: August 19, 2014Assignee: 3M Innovative Properties CompanyInventors: Robert S. Clough, John E. Anthony, Marcia M. Payne
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Patent number: 8779179Abstract: The present disclosure provides a method of preparing silylethynyl compounds in which two of the hydrocarbyl groups bonded to the silicon exclusive of the ethynyl group, are the same and one is different, that may be used in preparing novel silylethynyl functionalized acene semiconductor chromophores.Type: GrantFiled: May 18, 2011Date of Patent: July 15, 2014Assignee: 3M Innovative Properties CompanyInventors: Robert S. Clough, John E. Anthony, Marcia M. Payne
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Patent number: 8497392Abstract: A process for producing functionalized carbon nanotubes, which can organically modify carbon nanotubes with high efficiency, and in particular, can introduce different organic groups into carbon nanotubes with high efficiency through a series of chemical reactions, is provided. Carbon nanotubes are allowed to react with at least one reagent selected from a silyl-substituted organometallic compound and an organometallic compound to obtain a functionalized carbon nanotube reductant, and this functionalized carbon nanotube reductant is then allowed to react with at least one reagent selected from a silyl halide compound and an organohalogen compound to obtain functionalized carbon nanotubes.Type: GrantFiled: March 11, 2010Date of Patent: July 30, 2013Assignee: Japan Science and Technology AgencyInventors: Yutaka Maeda, Takeshi Akasaka
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Publication number: 20130172595Abstract: The present invention relates to a method for preparing di-organo-dialkoxysilanes, in particular di-organo-dialkoxysilanes wherein one or both of the organic substituents are bulky. The method comprises reacting a tetraalkoxysilane compound with a first Grignard reagent to form a mono-organo-tri-alkoxysilane compound, which is then reacted with a chlorinating agent to form a chlorinated mono-organo-di-alkoxysilane which is then reacted with a second Grignard reagent to form the di-organo-di-alkoxysilane compound.Type: ApplicationFiled: December 21, 2012Publication date: July 4, 2013Applicant: SAUDI BASIC INDUSTRIES CORPORATIONInventor: Saudi Basic Industries Corporation
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Patent number: 8163950Abstract: A silane containing a bulky hydrocarbon group or groups R therein and having the formula (III) R3?(x+y)(R1)x(R2)ySi(OR3) can be produced by reacting a silane of the formula (I) (R1)x(R2)ySiCl3?(x+y)(OR3) with a Grignard reagent of the formula (II) RMgX Further, a tri-organo-chlorosilane of the formula (XIIa) (R1)(R2)(R3)SiCl can be produced by reacting a tri-organo-silane of the formula (XIa) (R1)(R2)(R3)SiZ1 with hydrochloric acid. Furthermore, a tri-organo-monoalkoxysilane of the formula (XXIII) R3?(x+y)(R1)x(R2)ySi(OR3) can be produced when a silane of the formula (XXI) (R1)x(R2)ySiCl4?(x+y) is reacted with a Grignard reagent of the formula (XXII) RMgX with addition of and reaction with an alcohol or an epoxy compound during the reaction.Type: GrantFiled: July 19, 2011Date of Patent: April 24, 2012Assignees: Shin-Etsu Chemical Co., Ltd., Hokko Chemical Industry Co., Ltd.Inventors: Tadashi Bannou, Shin Masaoka, Yoshiki Hayakawa
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Patent number: 7741393Abstract: Provided are an organic silicon compound of the following formula (I): (wherein, R1 to R20 represent each independently alkyl, alkoxy, aryloxy, cycloalkyl, alkylcycloalkyl, aryl, dialkylamino or the like, and the aryloxy and aryl may be substituted with a substituent selected from the group consisting of alkyl, alkoxy and alkoxyalkyl.) which can be used for suppression of coloration and thermal deterioration of an organic material in molding, and an organic material composition containing the organic silicon compound and a method of producing the organic silicon compound.Type: GrantFiled: March 10, 2005Date of Patent: June 22, 2010Assignee: Sumitomo Chemical Company, LimitedInventors: Taketoshi Kikuchi, Atsushi Higo, Hideaki Awa, Kunihito Miyake
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Method for obtaining halogenated monoorganoxysilanes useful in particular as synthesis intermediates
Patent number: 7709672Abstract: The invention concerns the preparation of halogenated monoorganoxysilanes, of formula (I), said compounds being useful as synthesis intermediate in organic chemistry. Said method for preparing monoorganoxysilanes consists in: using as starting product halogenoalkylsilanes of the (CH3)2SiCl2 type and in substituting the silicon with a radical bearing a divalent unit bound to an electrophilic reactive group capable of reacting with at least an appropriate nucleophilic agent to form a functionalised monoorganoxysilane of formula (II) with, for example: R<1>=C1-C4 alkyl; R<2>, R<3>=C1-C6 alkyl; B=C1-C10 alkylene; m=1 or 2; Hal=halogen; W=amino, mercapto, (organosilyl)-organopolythio radical.Type: GrantFiled: September 10, 2002Date of Patent: May 4, 2010Assignee: Rhodia ChimieInventors: Nathalie Guennouni, Gérard Mignani, Virginie Pevere -
Publication number: 20100048934Abstract: The present invention provides a method for producing a fullerene derivative, comprising the organic group addition step B in which an organic group is further added by reacting at least a basic compound and a halogen compound with a fullerene derivative, which is obtained by addition of a hydrogen atom and an organic group in the organic group addition step A, in which an organic group is added by reacting at least a Grignard reagent and a polar substance with a fullerene or fullerene derivative.Type: ApplicationFiled: November 6, 2007Publication date: February 25, 2010Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCYInventors: Eiichi Nakamura, Yutaka Matsuo, Akihiko Iwashita
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Publication number: 20090270590Abstract: A surface-modified inorganic material and a preparation method thereof. A surface-modified inorganic material is provided which is obtained by allowing an organosilane compound having allyl or an allyl derivative to react with an inorganic material, particularly solid silica or ITO glass, in the presence of an acid and an organic solvent, to introduce an organic group into the inorganic material even at room temperature, as well as a preparation method thereof. The invention can effectively introduce the organic group into the inorganic material even at room temperature, and thus is very effective in introducing compounds having a thermally sensitive functional group, for example, natural compounds or proteins. It is possible to introduce various organic groups into an inorganic material and to separate and purify organic molecule-bonded organosilane compounds using a silica gel column to effectively bond them to inorganic materials. Accordingly, the invention is very useful in the chemical industry.Type: ApplicationFiled: May 16, 2006Publication date: October 29, 2009Applicant: Industry-Academic Cooperation Foundation Yonsei UniversityInventors: Chul-Ho Jun, Ye-Lim Yeon, Ji-Sung Lee, Young-Jun Park
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Patent number: 7456308Abstract: A Grignard process for preparing phenyl-containing chlorosilane products, in particular diphenylchlorosilanes, is carried out in three embodiments. In the first embodiment, the reactants of the Grignard process are a phenyl Grignard reagent, an ether solvent, a trichlorosilane, and an aromatic hydrocarbon coupling solvent. In the second embodiment, the reactants of the Grignard process are a phenyl Grignard reagent, an ether solvent, a phenylchlorosilane, and an aromatic hydrocarbon coupling solvent. In the third embodiment, the reactants of the Grignard process are a phenyl Grignard reagent, an ether solvent, a trichlorosilane, a phenylchlorosilane, and an aromatic hydrocarbon coupling solvent. In each embodiment, the reactants are present in a particular mole ratio.Type: GrantFiled: December 17, 2004Date of Patent: November 25, 2008Assignee: Dow Corning CorporationInventors: Binh Thanh Nguyen, Curtis John Bedbury, Roger Edwin Humburg, Susan Mary Jacob, Sarah Jane Ratcliff, John Dennis Waterman
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Publication number: 20080139834Abstract: Phenylmethyldichlorosilanes and diphenylmethylchlorosilanes are prepared by a Grignard process involving the step of contacting a phenyl Grignard reagent, an ether solvent, a trichlorosilane, and an aliphatic or cycloparaffinic hydrocarbon coupling solvent; in a mole ratio of the ether solvent to the phenyl Grignard reagent is 2 to 5, the mole ratio of the trichlorosilane to the phenyl Grignard reagent is 0.1 to 10, and the mole ratio of the aliphatic or cycloparaffinic hydrocarbon coupling solvent to the phenyl Grignard reagent is 3 to 7. Preferred reactants include phenylmagnesium chloride as the phenyl Grignard reagent; diethyl ether as solvent; n-heptane as the aliphatic hydrocarbon coupling solvent, or cyclohexane as the cycloparaffinic hydrocarbon coupling solvent; and methyltrichlorosilane.Type: ApplicationFiled: January 25, 2006Publication date: June 12, 2008Applicant: DOW CORNING CORPORATIONInventors: Dana C. Bauer, Curtis John Bedbury, Binh Thanh Nguyen
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Patent number: 7351847Abstract: Three improved Grignard processes are used for preparing phenyl-containing chlorosilane products wherein the yield of diphenylchlorosilanes as a product is maximized, while the yield of phenylchlorosilanes as a product is minimized. In one embodiment, the process involves contacting a phenyl Grignard reagent, an ether solvent, an aromatic halogenated coupling solvent and a trichlorosilane. In another embodiment, the process involves contacting a phenyl Grignard reagent, an ether solvent, an aromatic halogenated coupling solvent, a trichlorosilane, and a phenylchlorosilane. In yet another embodiment, the process involves contacting a phenyl Grignard reagent, an ether solvent, an aromatic halogenated coupling solvent, and a phenylchlorosilane. In each embodiment, the reactants are present in particular mole ratios of the components.Type: GrantFiled: December 17, 2004Date of Patent: April 1, 2008Assignee: Dow Corning CorporationInventor: Binh Thanh Nguyen
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Patent number: 6984747Abstract: The invention relates to a method for preparing silanes comprising styryl groups, said silanes being represented by the general formula (I): (St)bSiR?aR4?a?b with improved yields through a reaction with magnesium in a solvent mixture comprising from 30:70 to 70:30 (v/v) of diethyl ether and tetrahydrofuran.Type: GrantFiled: December 6, 2002Date of Patent: January 10, 2006Assignee: Fraunhofer-Gesellschaft zur Forderung der Angewandten Forschung e.V.Inventors: Stéphane Jacob, Lothar Fröhlich, Konrad Olma, Michael Popall, Frank Kahlenberg
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Patent number: 6777570Abstract: A process for producing a norbornene derivative having an organosilyl group suitable as a synthetic intermediate for pesticides and medicaments and for production of polyolefin polymers, particularly polyolefin polymers having a good adhesiveness with metals or insulating inorganic materials in high yields with a satisfactory purity. A process for producing a norbornene derivative having an organosilyl group represented by the general formula (3): wherein R each represents an alkyl group or an aryl group, R′ represents an alkyl group or an aryl group, n represents an integer of 0 to 2 and m represents an integer of 0 or more, which comprises reacting a compound represented by the general formula (1): wherein R, n and m have the same meanings as above, and X represents a halogen atom, with a Grignard agent represented by the general formula (2): R′MgCl (2) wherein R′ has the same meaning as above.Type: GrantFiled: September 26, 2003Date of Patent: August 17, 2004Assignee: Mitsubishi Chemical CorporationInventors: Hiroko Takahashi, Takako Takahashi, Taketoshi Naito, Shuji Ichikawa
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Patent number: 6730802Abstract: The compound 2,4,6-trimethyl-2,4,6-trisila heptane, the preparation thereof, and the use thereof as a silicon carbide precursor in chemical vapor deposition and infiltration procedures are disclosed.Type: GrantFiled: July 9, 2002Date of Patent: May 4, 2004Assignee: Starfire Systems, Inc.Inventors: Qionghua Shen, Leo Spitz MacDonald
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Patent number: 6686492Abstract: A one-step process for the preparation of organosilicon intermediates. The organosilicon intermediates comprise a group which includes such intermediates as 1,4-bis(dimethylsilyl)benzene, 1,4-bis(dimethylchlorosilyl)benzene, and their derivatives. The process comprises: combining a dihalobenzene with magnesium metal in a co-solvent mixture of an ether and an organic solvent and reacting them with an organosilicon compound of the general formula, R2bHcSiXd. The resulting mixture is allowed to react to completion. The resulting mixture is passed through a filtration device. The liquid, now free of solid magnesium halide, is subjected to a separation technique to recover the subject organosilicon intermediates and their derivatives.Type: GrantFiled: June 13, 2002Date of Patent: February 3, 2004Assignee: Dow Corning CorporationInventor: Binh T. Nguyen
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Publication number: 20030233005Abstract: A one-step process for the preparation of organosilicon intermediates. The organosilicon intermediates comprise a group which includes such intermediates as 1,4-bis(dimethylsilyl)benzene, 1,4-bis(dimethylchlorosilyl)benzene, and their derivatives. The process comprises: combining a dihalobenzene with magnesium metal in a co-solvent mixture of an ether and an organic solvent and reacting them with an organosilicon compound of the general formula, R2bHcSiXd. The resulting mixture is allowed to react to completion. The resulting mixture is passed through a filtration device. The liquid, now free of solid magnesium halide, is subjected to a separation technique to recover the subject organosilicon intermediates and their derivatives.Type: ApplicationFiled: June 13, 2002Publication date: December 18, 2003Inventor: Binh T. Nguyen
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Patent number: 6541651Abstract: Processes for the preparation of phenyl Grignard reagents in co-solvents of toluene and ether and, the preparation of phenylchlorosilane intermediates using co-solvents of toluene and ether essentially in a one step process. The phenylchlorosilanes in the processes of this invention are important intermediates for the preparation of various silicone materials.Type: GrantFiled: April 4, 2002Date of Patent: April 1, 2003Assignee: Dow Corning CorporationInventors: Curtis J. Bedbury, John P. Cannady, Binh T. Nguyen
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Patent number: 6465668Abstract: A method for easily and inexpensively producing and purifying a fluoroaryl metal compound such as bis(pentafluorophenyl)dialkyltin which is less colored and has no impurities is provided. Hydrocarbon magnesium halide is reacted with fluoroaryl halide in a solvent including an ether solvent so as to obtain fluoroaryl magnesium halide, which is then reacted with an organic metal compound so as to produce a fluoroaryl metal compound. Tin is more preferable as a metal atom included in the organic metal compound. As for the ether solvent, chain ether solvents are preferable, more specifically, diisopropyl ether, dibutyl ether, and t-butylmethyl ether are more preferable. Besides, it is preferable that magnesium halide, which is a by-product of the fluoroaryl metal compound, is precipitated and removed, or treated with an acid.Type: GrantFiled: November 27, 2001Date of Patent: October 15, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Ikuyo Ikeno, Hitoshi Mitsui, Toshiya Iida, Toshimitsu Moriguchi
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Patent number: 6429327Abstract: Processes for the synthesis of substituted silanes from alkyl magnesium compounds using a mixture of catalysts. The catalyst systems include both a copper halide and a salt of a Group IA, IIA, IIA, or IVA element or a transition metal.Type: GrantFiled: January 20, 2000Date of Patent: August 6, 2002Assignee: FMC CorporationInventors: Philip Franklin Sims, James Anthony Schwindeman
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Patent number: 6380415Abstract: A process for producing an octafluoro[2,2]paracyclophane includes the steps of (a) reacting 1,4-bis(trifluoromethyl)benzene with a halogenated silane represented by the general formula (1), in the presence of a low valence metal, thereby obtaining a novel compound (precursor) represented by the general formula (2); and (b) conducting in the presence of a fluoride ion a dimerization of the compound into the octafluoro[2,2]paracyclophane, R3SiX (1) where each R is independently an alkyl group or aryl group, and X is a halogen atom, where R is defined as above. It is possible to produce octafluoro[2,2]paracyclophane with a high yield from 1,4-bis(trifluoromethyl)benzene, which is easily available, via the above compound.Type: GrantFiled: February 14, 2001Date of Patent: April 30, 2002Assignee: Central Glass Company, LimitedInventors: Kenji Uneyama, Hideki Amii
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Patent number: 6255515Abstract: An alkali metal- or alkali earth metal-containing organic compound (i) is reacted with a leaving group- and silicon- or germanium-containing compound (ii) in the presence of a nitrogen-containing aromatic heterocyclic compound. By such a method, it is possible to produce a silicon- or germanium-containing organic compound, for example, a cyclopentadienyl compound cross-linked by a silicon atom or a germanium atom, typically a cyclopentadienyl compound which is substituted with a substituted or unsubstituted silyl or germyl group, for a short time with a high yield.Type: GrantFiled: August 31, 1999Date of Patent: July 3, 2001Assignee: Mitsubishi Chemical CorporationInventors: Taku Kato, Kazuya Okano, Toshihiko Sugano, Yutaka Ohtani, Hirohisa Kitagawa, Sugio Nishimura
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Patent number: 6160151Abstract: Diphenyl-dialkoxysilanes and phenylmethyl-dialkoxysilanes where the alkoxy group has 1 to 10 carbons, preferably 1 or 2 carbons, are prepared by the reactions shown in Schemes 1 through 4.Type: GrantFiled: December 8, 1999Date of Patent: December 12, 2000Assignee: Nusil TechnologyInventors: Richard A. Compton, Alfred V. Belanger
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Patent number: 6156918Abstract: The invention relates to a process for the preparation of silanes of the general formula 1R.sub.m R.sup.1.sub.n SiX.sub.4-m-n (1)by reaction of Grignard reagents of the general formula 2R.sup.1 MgX.sup.1 (2)with silanes of the general formula 3R.sub.m SiX.sub.4-m (3)whereinR denotes C.sub.1 - to C.sub.10 -hydrocarbon radicals optionally substituted by fluorine, chlorine or cyano radicals,R.sup.1, in the .alpha.-position relative to the silicon atom, denotes tertiary C.sub.4 - to C.sub.30 -hydrocarbon radicals optionally substituted by fluorine, chlorine or cyano radicals,X and X.sup.1 each denote chlorine, bromine or iodine,m denotes the values 2 or 3 andn denotes the values 1 or 2,in the presence of a transition metal catalyst and an inert, aprotic, and chelating compound.Type: GrantFiled: July 29, 1999Date of Patent: December 5, 2000Assignee: Wacker-Chemie GmbHInventors: Joern Winterfeld, Bors Cajus Abele
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Patent number: 6127565Abstract: The following class of glycidyl and allyl ethers are found to cure at room temperature much faster than their glycidyl and allyl analogs: ##STR1## where: R.sub.1 is selected from the group consisting of:(a) an aliphatic hydrocarbon group containing 2 to 10 carbon atoms; and(b) a group having the formula ##STR2## wherein n=1 to 3,m=0 to 5R.sub.2 and R.sub.2 ' are each selected from the group consisting of an alkyl group containing 1 to 4 carbon atoms, an unsubstituted aryl group, and a substituted aryl group, and R.sub.Type: GrantFiled: December 4, 1998Date of Patent: October 3, 2000Assignee: Raytheon CompanyInventor: T. Kirk Dougherty
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Patent number: 5872274Abstract: A method for the preparation of tertiary-hydrocarbylsilyl compounds. The method comprises contacting a mixture comprising diethylene glycol dibutyl ether, and a Grignard reagent described by formula RMgX with a silicon compound described by formula R.sup.1.sub.a SiX.sub.4-a, where R is a tertiary-hydrocarbyl group comprising four to about 20 carbon atoms, each R.sup.1 is an independently selected substituted or unsubstituted monovalent hydrocarbon group comprising one to about 20 carbon atoms, each X is an independently selected halogen atom, and a is an integer with a value of zero to three, in the presence of an effective amount of a copper compound catalyst. The present invention provides a method for making sterically hindered organosilicon intermediates useful in the pharmaceutical industry.Type: GrantFiled: June 11, 1998Date of Patent: February 16, 1999Assignee: Dow Corning CorporationInventors: John Patrick Cannady, Binh Thanh Nguyen
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Patent number: 5756796Abstract: A method for preparation of alkenylsilanes comprising contacting magnesium metal with a mixture comprising diethylene glycol dibutyl ether, an alkenyl halide, and a halosilane at a temperature within a range of about 5.degree. C. to 200.degree. C. The method provides a high yield of alkenylsilane product that is easily recoverable and also provides for high ratios of alkenylsilane to diethylene glycol dibutyl ether.Type: GrantFiled: May 19, 1997Date of Patent: May 26, 1998Assignee: Dow Corning CorporationInventors: Sean Patrick Davern, Binh Thanh Nguyen
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Patent number: 5629439Abstract: A method for the preparation of allylsilanes. The method comprises contacting magnesium metal with a mixture comprising diethylene glycol dibutyl ether, allyl halide, and a halosilane at a temperature within a range of about 5.degree. C. to 20.degree. C. The method provides a high yield of allylsilane product that is easily recoverable and also provides for high ratios of allylsilane to hexadiene by-product.Type: GrantFiled: March 28, 1996Date of Patent: May 13, 1997Assignee: Dow Corning CorporationInventors: Howard M. Bank, Sean P. Davern, Binh T. Nguyen
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Patent number: 5596120Abstract: A one-step process for preparation of organosilanes. The process comprises contacting magnesium metal with a mixture comprising an organic halide and a halosilane in a co-solvent comprising about one to 15 moles of a dialkyl ether comprising less than seven carbon atoms, per mole of the allyl chloride; and about 0.05 to less than two moles of a liquid aromatic hydrocarbon solvent per mole of the dialkyl ether; at a temperature within a range of about 5.degree. C. to 200.degree. C.Type: GrantFiled: October 23, 1995Date of Patent: January 21, 1997Assignee: Dow Corning CorporationInventors: Howard M. Bank, Binh T. Nguyen
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Patent number: 5550269Abstract: A method for the redistribution of trichlorosilane in the presence of N,N,N',N'-tetraethylethylenediamine (TEEDA) to form a complex comprising dichlorosilane and TEEDA. The dichlorosilane can be disassociated from the TEEDA by a means such as heating and then used in standard processes requiring dichlorosilane. Alternatively, the complex comprising the dichlorosilane and TEEDA can be used as a reactant for hydrosilation of .alpha.,.beta.-unsaturated olefinic nitriles or reacted with Grignard type reagents to make organosilanes.Type: GrantFiled: November 17, 1995Date of Patent: August 27, 1996Assignee: North Dakota State University Research FoundationInventors: Philip Boudjouk, Steven D. Kloos
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Patent number: 5486638Abstract: The present invention relates to a novel process for preparing 1-halo-3-trialkylsilanyl-benzenes from 1,3-dihalo-benzenes which are useful intermediates in the preparation of 1-(3-trialkylsilylphenyl)-2,2,2-trifluoromethyl ethanones which are useful for the treatment of Alzheimer's disease and senile dementia.Type: GrantFiled: November 8, 1994Date of Patent: January 23, 1996Assignee: Marion Merrell Dow Inc.Inventors: Dennis K. Klipa, Robert T. Keaten
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Patent number: 5294727Abstract: A method for preparing a tertiary hydrocarbon-silyl compound comprises the step of reacting a grignard reagent represented by the general formula: R.sup.1 MgX.sup.1 (wherein R.sup.1 represents a tertiary hydrocarbon group and X.sup.1 is a halogen atom) with a silicon atom-containing compound represented by the general formula: X.sup.2.sub.m R.sup.2.sub.n SiH.sub.4-m-n (wherein X.sup.2 is a halogen atom and may be identical to or different from X.sup.1 ; R.sup.2 is a monovalent hydrocarbon group; m is 1, 2 or 3; and n is 0, 1 or 2, provided that m+n is not more than 3 and that if n is 2, R.sup.2 's may be identical to or different from one another) in an aprotic inert organic solvent in the presence of a copper compound and/or a quaternary ammonium salt. According to this method, the tertiary hydrocarbon-silyl compounds can industrially efficiently and rapidly produced in high yields.Type: GrantFiled: November 12, 1992Date of Patent: March 15, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tohru Kubota, Toshinobu Ishihara, Mikio Endo
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Patent number: 5286862Abstract: The present invention relates to a process for the preparation of compounds of the formula I ##STR1## where X is CH.dbd.CH, N.dbd.CH, CH.dbd.N or S,R.sup.1 and R.sup.2 independently of one another are H, halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio or the bivalent methylenedioxy group,R.sup.3 is a radical of the formulae (A), (B) or (C) ##STR2## where R.sup.4 and R.sup.5 independently of one another are H, halogen, alkyl, alkoxy or a radical of the formula (D) ##STR3## in which R.sup.6 is H or halogen andY is CH.sub.2, O or S, andm, n, o, p and q are 0, 1, or 2, which comprises reacting a compound of the formula IIH.sub.2 C.dbd.CH--CH.sub.2 --R.sup.3 (II)where R.sup.3 is as defined in formula I, with dichloromethylsilane in the presence of a catalyst suitable for hydrosilylation reactions, and reacting the resulting intermediate of the formula III ##STR4## where R.sup.Type: GrantFiled: August 24, 1989Date of Patent: February 15, 1994Assignee: Hoechst AktiengesellschaftInventor: Hans H. Schubert
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Patent number: 5231158Abstract: Alkynyl substituted organopolysiloxanes having alkynyl radicals attached to silicon by carbon-silicon bonds can be used in combination with a hydride siloxane crosslinker and a Group 8-10 catalyst to make one part heat curable organopolysiloxane compositions.Type: GrantFiled: May 28, 1992Date of Patent: July 27, 1993Assignee: General Electric CompanyInventors: Larry N. Lewis, Chris A. Sumpter
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Patent number: 5153295Abstract: Polycarbosilane compositions, which can serve as silicon carbide precursors, are formed by a Grignard coupling reaction of a halomethylcarbosilane followed by reduction using a metal hydride. The polycarbosilane compositions that result have a substantially 1:1 silicon to carbon stoichiometry, are substantially non-cyclic and branched, and comprise the repeat units SiH.sub.3 CH.sub.2 --, --SiH.sub.3 CH.sub.2 --, .dbd.SiHCH.sub.2 --, and .tbd.SiCH.sub.2 --.Type: GrantFiled: July 20, 1990Date of Patent: October 6, 1992Assignee: Rensselaer Polytechnic InstituteInventors: Christopher K. Whitmarsh, Leonard V. Interrante
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Patent number: 5124470Abstract: The present invention relates to a process for the preparation of arylalkylmethylsilanes of the formula I ##STR1## where X is CH.dbd.CH, N.dbd.CH, CH.dbd.N or S,R.sup.1 and R.sup.2 independently of one another are H, halogen, (C.sub.1 to C.sub.4)alkyl, (C.sub.1 to C.sub.4)alkoxy, (C.sub.1 to C.sub.4)alkylthio, (C.sub.1 to C.sub.4)haloalkyl, (C.sub.1 to C.sub.4)haloalkoxy or (C.sub.1 to C.sub.4)haloalkylthio,R.sup.3 is (C.sub.1 to C.sub.6)alkyl andm and n are 0, 1 or 2,which comprises reacting dichloromethylsilane II ##STR2## first with an arylmagnesium halide of the formula III ##STR3## where R.sup.1, R.sup.2, m, n and X are as defined in Formula I and Hal is halogen, at temperatures of from -78.degree. to 0.degree. C., and subsequently with an alkylmagnesium halide of the formula IVR.sup.3 --Mg Hal (IV),where R.sup.3 is as defined in formula I and Hal is halogen, if appropriate in the presence of a solvent.Type: GrantFiled: July 19, 1991Date of Patent: June 23, 1992Assignee: Hoechst AktiengesellschaftInventor: Stephen Lachhein
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Patent number: 5068386Abstract: The present invention relates to a method for the preparation of tertiary-hydrocarbylsilyl compounds through a Grignard reaction. A Grignard reagent of formula RMgX, in which R is a tertiary-hydrocarbyl group and X is a halogen atom, is reacted with a silicon compound of formula R.sup.1.sub.a SiX.sub.4-a ; where R.sup.1 is a substituted or unsubstituted monovalent hydrocarbon group and a is an integer with a value of zero to three. The process is ran in the presence of a catalytic quantity of a cyano compound or a thiocyanate compound.Type: GrantFiled: June 1, 1990Date of Patent: November 26, 1991Assignee: Dow Corning Toray Silicone Company, Ltd.Inventor: Akihiko Shirahata
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Patent number: 4958041Abstract: In a method for the selective production of diorganodialkoxysilanes of the general formula ##STR1## by reaction of tetraalkoxysilanes of the formula Si(OR.sup.3).sub.4 and monoorganotrialkoxysilanes of the formula R.sup.1 Si(OR.sup.3).sub.3 respectively with Grignard reagents, the desired reaction products are produced in high yield and without undesirable by-products and in high yield.Type: GrantFiled: June 26, 1989Date of Patent: September 18, 1990Assignee: Schering AktiengesellschaftInventors: Jurgen Graefe, Wolfram Uzick, Udo Weinberg
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Patent number: 4824918Abstract: Vinyl-containing polysilanes are described wherein the vinyl groups are attached to endblocking sites of intermediate reactivity. These vinyl-containing polysilanes are prepared by reacting a halogen-endblocked polysilane with, first, a non-vinyl-containing Grignard reagent or a non-vinyl organolithium compound whereby the most reactive halogen endblocking groups are replaced; then, second, reacting the resulting polysilane with vinyl Grignard reagent or vinyllithium whereby the halogen endblocking groups of intermediate reactivity are replaced; and, third, reacting the resulting polysilane with a non-vinyl-containing Grignard reagent or a non-vinyl organolithium compound whereby the least reactive halogen endblocking groups are replaced. The vinyl-containing polysilanes can be coverted to ceramic materials, including ceramic fibers, by pyrolysis.Type: GrantFiled: September 4, 1987Date of Patent: April 25, 1989Assignee: Dow Corning CorporationInventors: Duane R. Bujalski, Gary E. LeGrow, Jonathan Lipowitz, Thomas F. Lim
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Patent number: 4806612Abstract: Preceramic actylenic polysilanes are described which contain --(CH.sub.2).sub.w C.tbd.CR' groups attached to silicon where w is an integer from 0 to 3 and where R' is hydrogen, an alkyl radical containing 1 to 6 carbon atoms, a phenyl radical, or an --SiR"'.sub.3 radical wherein R"' is an alkyl radical containing 1 to 4 carbon atoms. The acetylenic polysilanes are prepared by reacting chlorine- or bromine-containing polysilanes with either a Grignard reagent of general formula R'C.tbd.C(CH.sub.2).sub.w MgX' where w is an integer from 0 to 3 and X' is chlorine, bromine, or iodine or an organolithium compound of general formula R'C.tbd.C(CH.sub.2).sub.w Li where w is an integer from 0 to 3. The acetylenic polysilanes can be converted to ceramic materials by pyrolysis at elevated temperatures under an inert atmosphere.Type: GrantFiled: August 10, 1987Date of Patent: February 21, 1989Assignee: Dow Corning CorporationInventors: Grish Chandra, Gregg A. Zank
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Patent number: 4788268Abstract: Epoxysilicone compounds are prepared by first reacting a dibromobenzene compound with magnesium in anhydrous ether solvent to form a Grignard reagent and subsequently reacting the Grignard reagent with allyl bromide to form a (bromophenyl)propene compound. Next, the (bromophenyl)propene compound is converted to the corresponding Grignard reagent, which is then reacted with a compound of the formula I below ##STR1## where n=1 to 6,R.sub.1 and R.sub.2 are each chosen from the group consisting of a C.sub.1 to C.sub.4 alkyl group, a substituted aryl group, and an unsubstituted aryl group.in tetrahydrofuran solvent to form an allyl-terminated silicone compound of formula II below ##STR2## Finally, the allyl-terminated silicone compound is reacted with a chosen epoxidizing agent to form the epoxysilicone compound of formula III below.Type: GrantFiled: May 5, 1987Date of Patent: November 29, 1988Assignee: Hughes Aircraft CompanyInventors: Kreisler S. Y. Lau, Susan L. Oldham, William E. Elias
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Patent number: 4777278Abstract: Alkyl cycloalkyl dialkoxysilanes (e.g., methyl cyclohexyl dimethoxysilane) can be prepared by reaction of an alkyl trialkoxysilane (e.g., methyl trimethoxysilane) with a Grignard reagent containing the cycloalkyl moiety derived in the final end-product (e.g., a reagent formed by reacting cyclohexyl chloride and magnesium metal). The reaction is run in the absence of ether solvent, the Grignard reagent is preferably formed in situ by the reaction of magnesium metal and cyclohexyl halide, and agitation is used to promote the reaction. Advantageously, a catalyst, such as iodine, is used to promote the reaction.Type: GrantFiled: October 8, 1987Date of Patent: October 11, 1988Assignee: Akzo America Inc.Inventors: Elliot I. Band, Suzanne T. Eberhart
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Patent number: 4748262Abstract: The invention provides organosilane compounds of a novel class having one or two (phenyl dimethyl carbinyl) groups bonded to the silicon atom as represented by the general formula (PhMe.sub.2 C).sub.p R.sub.q X.sub.r Si, in which Ph is a phenyl group, Me is a methyl group, R is a monovalent hydrocarbon group selected from the class consisting of alkyl, alkenyl and aryl groups, X is a halogen atom or an alkoxy group, p is 1 or 2, q is zero, 1 or 2 and r is zero, 1, 2 or 3 with the proviso that p+q+r=4. The compound can be prepared by the reaction of a Grignard reagent PhMe.sub.2 C. MgY, in which Y is a halogen atom, with a silane compound represented by the general formula R.sub.q SiX.sub.4-q in an organic solvent.Type: GrantFiled: September 1, 1987Date of Patent: May 31, 1988Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshinobu Ishihara, Minoru Takamizawa, Mikio Endo, Toru Kubota
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Patent number: 4677216Abstract: A novel 2-substituted-1,3-butadiene compound which may be used as a coupling agent is disclosed, i.e. a 2-substituted-1,3-butadiene compound of the general formula (I) ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently represent a halogen, a lower alkyl group, or a lower alkoxy group with the exception of those compounds wherein R.sup.1, R.sup.2 and R.sup.3 are all lower alkyl groups.Type: GrantFiled: February 22, 1985Date of Patent: June 30, 1987Assignee: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 4672135Abstract: Silahydrocarbons such as tetraorganosilanes prepared from halo-substituted silanes and an organomagnesium compound in the presence of a catalytically effective amount of a thiocyanate.Type: GrantFiled: May 2, 1986Date of Patent: June 9, 1987Assignee: Monsanto CompanyInventor: Patrick J. Lennon