Carbon To Carbon Unsaturation Reduced By Addition Of A Silicon Hydride Patents (Class 556/479)
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Patent number: 5922895Abstract: A hydrosilation method comprising contacting a silicon hydride with an unsaturated reactant in the presence of a catalysts selected from the group consisting of amine borane complexes and phoshineborane complexes. The catalysts are especially useful for selectively hydrosilating unsaturated organic compounds with an internal unsaturated bond to increase the desired hydrosilation product yield.Type: GrantFiled: April 17, 1998Date of Patent: July 13, 1999Assignee: Dow Corning CorporationInventors: Ming-Shin Tzou, Yasushi Sugiura
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Patent number: 5914422Abstract: A method for producing a fluorine-containing silicone compound, which comprises subjecting a compound of the following formula (I) and a hydrosilicone compound having at least one hydrogen atom bonded to a silicon atom to hydrosilylation to obtain a fluorine-containing silicone compound having a R.sup.f --Q--CR.sup.1 R.sup.2 CR.sup.3 HCR.sup.4 R.sup.5 -- group bonded to the silicon atom:R.sup.f --Q--CR.sup.1 R.sup.2 CR.sup.3 .dbd.CR.sup.4 R.sup.5(I)wherein R.sup.f is a monovalent fluorine-containing organic group, Q is a single bond or a bivalent organic group containing no fluorine atom, and each of R.sup.1 to R.sup.5 which are independent of one another, is a hydrogen atom or a monovalent organic group.Type: GrantFiled: November 7, 1997Date of Patent: June 22, 1999Assignee: Asahi Glass Company Ltd.Inventors: Yutaka Furukawa, Mami Kotera, Seisaku Kumai, Kazuya Oharu, Toshihiko Toma
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Patent number: 5908951Abstract: A catalyst enables hydrosilylation of aliphatically unsaturated carbon-carbon bonds by silicon-bonded hydrogen to be conducted rapidly in water. The catalyst provides a rapid method of carrying out hydrosilylation in water. An emulsion form of catalyst includes a dispersion in water of liquid catalyst, the main component of which is a platinum and alkenylsiloxane complex. The volumetric average particle size of liquid catalyst dispersed is less than or equal to 1 .mu.m. Hydrosilylation of an aliphatically unsaturated carbon-carbon bond by silicon-bonded hydrogen is carried out in water using the catalyst.Type: GrantFiled: September 14, 1998Date of Patent: June 1, 1999Assignee: Dow Corning Toray Silicone Co., Ltd.Inventors: Kazuo Kobayashi, Yoshitsugu Morita
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Patent number: 5869728Abstract: Fluoroalkyl organosilicon compounds are prepared by reacting fluoroolefins with organosilicon compounds that contain at least one H--Si group, in the presence of a Pt(0) complex catalyst. Further, fluoroalkylalkoxy organosilicon compounds are prepared by esterifying fluoroalkyl organosilicon compounds. The process proceeds uniformly under mild conditions with high yields and selectivities.Type: GrantFiled: October 21, 1997Date of Patent: February 9, 1999Assignee: Huels AktiengesellschaftInventors: Peter Jenker, Albert-Johannes Frings, Michael Horn, Jaroslaw Monkiewicz, Burkhard Standke
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Patent number: 5834614Abstract: A method for producing a fluorine-containing silicone compound, which comprises subjecting a fluorine-containing unsaturated compound of the following formula (1) and a hydrosilicone compound having at least one hydrogen atom bonded to a silicon atom to hydrosilylation in the presence of a catalyst to obtain a fluorine-containing silicone compound having a R.sup.f --Q--CR.sup.1 R.sup.2 --CHR.sup.3 --CR.sup.4 R.sup.5 -- group bonded to the silicon atom:R.sup.f --Q--CR.sup.1 R.sup.2 --CR.sup.3 .dbd.CR.sup.4 R.sup.5( 1)wherein R.sup.f is a monovalent fluorine-containing organic group, Q is a single bond or a bivalent organic group, and each of R.sup.1 to R.sup.5 which are independent of one another, is a hydrogen atom or a monovalent organic group, wherein the hydrosilylation is carried out substantially in the absence of a solvent.Type: GrantFiled: April 23, 1997Date of Patent: November 10, 1998Assignees: Asahi Glass Company Ltd., OSi Specialties IncorporatedInventors: Yutaka Furukawa, Mami Kotera, Seisaku Kumai, Gerald J. Murphy
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Patent number: 5808127Abstract: This invention provides a hydrosilylation method in which hydrosilyl groups are added to olefin using a metal catalyst, which comprises controlling the hydrosilylation reaction by allowing a compound selected from thiazoles and phosphines to coexist in the reaction system, and a process making use thereof for the production of a hydrosilyl group-containing organic curing agent. This invention gives a method for easy control of hydrosilylation reaction and a process making use thereof for the production of an organic compound modifying silicon compound having 2 or more hydrosilyl groups in the molecule. This compound is used as a curing agent of addition type curable compositions. As an accompanying effect, storage stability of the produced curing agent is improved when a catalyst and additives of this invention remain therein, in comparison with the case in which only the catalyst remains.Type: GrantFiled: May 16, 1997Date of Patent: September 15, 1998Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Yoshiki Nakagawa, Masato Kusakabe
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Patent number: 5756838Abstract: The present invention relates to water soluble chiral sulfonated 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl and its use as organometallic catalysts for asymmetric synthesis of optically active compounds. Asymmetric reactions of the present invention include those reactions in which organometallic catalysts are commonly used. Such reactions include, but are not limited to, reduction and isomerization reactions on unsaturated substrates and carbon--carbon bond forming reactions. Examples of such reactions include, but are not limited to, hydrogenation, hydroboration, hydrosilylation, hydride reduction, hydroformylation, alkylation, allylic alkylation, arylation, alkenylation, epoxidation, hydrocyanation, disilylation, cyclization and isomerization reactions.The catalysts of the present invention provide the advantage of functioning in the presence of water without loss in enantioselectivity relative to the nonsulfonated BINAP catalyst in an organic solvent.Type: GrantFiled: August 16, 1995Date of Patent: May 26, 1998Assignee: California Institute of TechnologyInventors: Mark E. Davis, Kam To Wan
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Patent number: 5756795Abstract: A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an accelerator selected from the group consisting of 1,7-octadiyne, 1,5-hexadiyne, cyclooctadiene, 5-vinyl-2-norbornene, 4-vinyl-1-cyclohexene, 2,5-bis(t-butylperoxy)-2,5-dimethylhexane, furan, 4H-Pyran-4-one, cis-4,7-dihydro-1,3-dioxepin, maleic anhydride, and dimethyldiallylmalonate. The accelerators are especially useful for facilitating the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene.Type: GrantFiled: December 30, 1996Date of Patent: May 26, 1998Assignee: Dow Corning CorporationInventors: Howard Marvin Bank, Aroop Kumar Roy
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Patent number: 5747172Abstract: Silicone release agents comprising propenyl-ether functionalized silicones exhibit a rapid cationic induce photo-cure. Such propenyl-ether functionalized silicones are synthesized by the hydrosilation of various .alpha.-allyloxy-.omega.-(1-propenoxy) alkanes with various linear and cyclic hydrogen functional siloxanes.Type: GrantFiled: August 30, 1995Date of Patent: May 5, 1998Assignee: General Electric CompanyInventor: James V. Crivello
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Patent number: 5696192Abstract: A polyoxyalkylene-modified organopolysiloxane that generates almost no odor with the passage of time, and a method for preparation of the polyoxyalkylene-modified organopolysiloxane. This organopolysiloxane bears polyoxyalkylene bonded to silicon across alkylene, and contains 5-1,000 ppm by weight of an antioxidant. It also has a peroxide value not exceeding 5 meq/kg, and a total content of aldehyde plus ketone not exceeding 100 ppm.Type: GrantFiled: November 15, 1996Date of Patent: December 9, 1997Assignee: Dow Corning Toray Silicone Co., Ltd.Inventor: Asao Harashima
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Patent number: 5679755Abstract: The present invention relates to new carbosilane dendrimers, to a method of preparing them, and to their use.Type: GrantFiled: May 2, 1996Date of Patent: October 21, 1997Assignee: Bayer AGInventors: Michael Mager, Aloys Eiling, Martin Schloh
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Patent number: 5677410Abstract: The present invention relates to novel functional carbosilane-dendrimers, organic-inorganic carbosilane-hybrid materials, methods for manufacturing them, methods for manufacturing coatings from the functional carbosilane-dendrimers and the use thereof.Type: GrantFiled: May 2, 1996Date of Patent: October 14, 1997Assignee: Bayer AGInventors: Michael Mager, Jorg-Dietrich Jentsch, Christoph Schild
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Patent number: 5663400Abstract: Di- and trialkylsilanes of the formulaR.sub.a R.sup.1 R.sup.2.sub.b SiX.sub.c (I),which comprises reacting mono- and dialkylsilanes of the formulaR.sup.1 R.sup.2.sub.b SiH.sub.a X.sub.c (II),with alkenes A having at least 4 carbon atoms, which alkenes are unsubstituted or substituted by fluorine, chlorine or bromine atoms or cyano groups, in the presence of a transition metal catalyst and a hydrocarbon as activator, which hydrocarbon has at least one functional group selected from among aldehyde, keto and epoxy groups or halogen atoms, where in the above formulae (I) and (II),R is a branched or cyclic hydrocarbon radical having at least 4 carbon atoms, which radical is unsubstituted or substituted by fluorine, chlorine or bromine atoms or cyano groups,R.sup.1 is an alkyl radical having at least 2 carbon atoms, which radical is unsubstituted or substituted by fluorine, chlorine or bromine atoms or cyano groups,R.sup.Type: GrantFiled: March 6, 1996Date of Patent: September 2, 1997Assignee: Wacker-Chemie GmbHInventors: Rudolf Reitmeier, Hermann Braunling, Tassilo Lindner, Hartmut Menzel
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Patent number: 5663399Abstract: A method for producing a fluorine-containing silicone compound, which comprises subjecting a compound of the following formula (I) and a hydrosilicone compound having at least one hydrogen atom bonded to a silicon atom to hydrosilylation to obtain a fluorine-containing silicone compound having a R.sup.f --Q--CR.sup.1 R.sup.2 CR.sup.3 HCR.sup.4 R.sup.5 -- group bonded to the silicon atom:R.sup.f --Q--CR.sup.1 R.sup.2 CR.sup.3 =CR.sup.4 R.sup.5 (I)wherein R.sup.f is a monovalent fluorine-containing organic group, Q is a single bond or a bivalent organic group containing no fluorine atom, and each of R.sup.1 to R.sup.5 which are independent of one another, is a hydrogen atom or a monovalent organic group.Type: GrantFiled: October 25, 1995Date of Patent: September 2, 1997Assignee: Asahi Glass Company Ltd.Inventors: Yutaka Furukawa, Mami Kotera, Seisaku Kumai, Kazuya Oharu, Toshihiko Toma
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Patent number: 5661202Abstract: There is disclosed a heat-resistant agent which exhibits good solubility in various organopolysiloxanes and which confers superior heat-resistance thereto, said heat-resistant agent having the formula ##STR1## wherein R.sup.2 is independently selected from hydrocarbon or halogenated hydrocarbon groups having 1 to 10 carbon atoms, R.sup.1 is independently selected from R.sup.2 or a eugenol residue, m is an integer having an average value of 5 to 500 and n is an integer having an average value of 0 to 500, with the proviso that there is at least one eugenol residue in the molecule. Also disclosed is a composition comprising an organopolysiloxane and the above described heat-resistant agent.Type: GrantFiled: October 28, 1996Date of Patent: August 26, 1997Assignee: Dow Corning Toray Silicone Co., Ltd.Inventors: Shoji Akamatsu, Haruhiko Furukawa, Toshinori Watanabe
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Patent number: 5654455Abstract: Catalyst systems which comprise a transition metal and a tris(organophosphite) ligand are particularly effective as catalysts for hydrosilation reactions.Type: GrantFiled: December 21, 1995Date of Patent: August 5, 1997Assignee: Ciba-Geigy CorporationInventors: Stephen D. Pastor, Sai P. Shum
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Patent number: 5646326Abstract: Alkylhydrogenchlorosilanes of formula IR.sub.(4-n-m) SiCl.sub.n H.sub.m (I),wherein m and n are each equal to 1 or 2 and m+n.ltoreq.3 and R is an alkyl group having from 1 to 5 carbon atoms, are prepared by reacting alkylchlorosilanes of formula IIR.sub.(4-p) SiCl.sub.p (II),wherein p is equal to 1, 2 or 3, with hydrogen.The alkylhydrogenchlorosilanes are employed as a starting material in hydrosilylation reactions.Type: GrantFiled: November 21, 1995Date of Patent: July 8, 1997Assignee: Huels AktiengesellschaftInventor: Joachim Schuler
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Patent number: 5639845Abstract: A novel and very efficient method is disclosed for the introduction of perfluoroalkyl groups into an organopolysiloxane by utilizing the hydrosilation reaction with an organohydrogenpolysiloxane. Different from the conventional but inefficient hydrosilation reaction using a perfluoroalkyl-substituted ethylene as the olefin compound, the inventive method utilizes a propene-1 3-substituted by a perfluoroalkyl group compound as the olefin compound to react with an organohydrogenpolysiloxane by which a very high efficiency in the hydrosilation reaction can be obtained without side reactions which otherwise greatly decrease the yield of the desired perfluoroalkyl-containing organopolysiloxane product.Type: GrantFiled: November 1, 1995Date of Patent: June 17, 1997Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hiroshi Inomata, Yasushi Yamamoto, Yasuo Tarumi, Noriyuki Koike, Kouichi Ishida
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Patent number: 5623083Abstract: A hydrosilation process where a siloxyhydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an accelerator selected from a group consisting of acetylenic alcohols and acetylenic ethers. The accelerators are especially useful for the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene.Type: GrantFiled: March 28, 1996Date of Patent: April 22, 1997Assignee: Dow Corning CorporationInventors: Howard M. Bank, Gary T. Decker
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Patent number: 5621129Abstract: A tertiary phosphine compound of the formula (1): ##STR1## in which R.sup.1 and R.sup.1' are hydrogen atoms or together form --CH.dbd.CH--CH.dbd.CH--; R.sup.2 and R.sup.3 together form a group of the formula (a): ##STR2## in which --.circle-solid. represent a bond to be bonded to the R.sup.3 group, and --.smallcircle. represents a bond to be bonded to the R.sup.2 group when R.sup.1 and R.sup.1 ' together form --CH.dbd.CH--CH.dbd.CH--, or when R.sup.1 is a hydrogen atom, R.sup.2 and R.sup.3 together form --CH.dbd.CH--CH.dbd.CH-- or R.sup.2 is a hydrogen atom and R.sup.3 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group; A.sup.1 is a 3-trifluoromethylphenyl group or a 3,5-bis(trifluoromethyl)phenyl group when R.sup.1 is a hydrogen atom and R.sup.2 and R.sup.3 together form --CH.dbd.CH--CH.dbd.CH--, or a substituted or unsubstituted phenyl group when R.sup.1 is not a hydrogen atom or when R.sup.2 and R.sup.3 do not together form --CH.dbd.CH--CH.dbd.CH--.Type: GrantFiled: March 7, 1996Date of Patent: April 15, 1997Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Hayashi, Masayoshi Minai, Kazunori Iwakura
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Patent number: 5616762Abstract: 3-Halo- and pseudohalo-alkylsilane esters are prepared by reacting an allyl X compound or a compound containing an allyl X structure with a hydridosilane ester in the presence of an iridium catalyst prepared under specific conditions and/or the reaction medium containing a 0.01-100 mol % excess of the allyl X compound or compound containing the allyl X unit relative to the amount of hydridosilane ester reactant.Type: GrantFiled: October 25, 1995Date of Patent: April 1, 1997Assignee: Huels AktiengesellschaftInventors: Frank Kropfgans, Albert Frings, Michael Horn, Hans-Joachim Koetzsch, Jaroslaw Monkiewicz, Claus-Dietrich Seiler, Hans-Guenther Srebny, Burkhard Standke
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Patent number: 5616763Abstract: A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an aldehyde accelerator. The aldehyde accelerators are especially useful for facilitating the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene.Type: GrantFiled: January 29, 1996Date of Patent: April 1, 1997Assignee: Dow Corning CorporationInventors: Howard M. Bank, Gary T. Decker
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Patent number: 5578692Abstract: Linear or straight-chain trimethylsiloxy endcapped methylhydrogen polysiloxanes are made by contacting hexamethyldisiloxane with a highly pure methylhydrogen cyclic siloxane, in the presence of anhydrous trifluoromethane sulfonic acid catalyst at room temperature. Trimethylsiloxy endcapped alkylmethyl siloxanes are made by reacting the linear or straight-chain trimethylsiloxy endcapped methylhydrogen polysiloxanes with an alpha-olefin, in the presence of a platinum catalyst. Alkylmethyl cyclic siloxanes containing zero parts per million residual .tbd.SiH, are made by reacting anhydrous alpha-olefins and a highly pure methylhydrogen cyclic siloxane, in the presence of dried platinum supported on carbon catalyst.Type: GrantFiled: February 5, 1996Date of Patent: November 26, 1996Assignee: Dow Corning CorporationInventors: Timothy N. Biggs, Gary E. Le Grow
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Patent number: 5565596Abstract: An improved process for hydrosilating alkynes with organodihalosilanes and trihalosilanes in the presence of a platinum catalyst selected from a group consisting of platinum halides and reaction product of platinum halides with organosilicon compounds having terminal aliphatic unsaturation. The process uses a cycloalkene comprising about six to 20 carbon atoms as a catalyst modifier to reduce formation of the bis-silated adduct of the alkynes.Type: GrantFiled: January 17, 1996Date of Patent: October 15, 1996Assignee: Dow Corning CorporationInventor: Aroop K. Roy
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Patent number: 5563287Abstract: An improved process for hydrosilating alkynes with hydridosilane in the presence of a platinum catalyst selected from a group consisting of platinum halides and reaction product of platinum halides with organosilicon compounds having terminal aliphatic unsaturation. The process uses a cycloalkadiene comprising about six to 20 carbon atoms as a catalyst modifier to reduce formation of the bis-silated adduct of the alkynes.Type: GrantFiled: January 17, 1996Date of Patent: October 8, 1996Assignee: Dow Corning CorporationInventor: Aroop K. Roy
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Patent number: 5561231Abstract: Transition metal-containing organosiloxanes of at least three organosiloxane units, comprising at least one transition metal complex, chemically bonded via ligands selected from among amino, phosphino or sulfido groups of Pt, Pd, Rh, Ru, Os or Ir, excluding those organosiloxanes which contain exclusively Pt(O) complexes bonded via amino ligands, are used as homogeneous hydrosilylation catalysts.Type: GrantFiled: July 19, 1994Date of Patent: October 1, 1996Assignee: Wacker-Chemie GmbHInventors: Jochen Dauth, Bernward Deubzer, Hans Bindl, Udo Peetz
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Patent number: 5559264Abstract: A method for preparing chloroalkylalkoxysilanes by reacting an allylic chloride with a small molar excess of a hydromethoxysilane in the presence of a ruthenium catalyst and preferably in the substantial absence of an inert solvent.Type: GrantFiled: February 14, 1995Date of Patent: September 24, 1996Assignee: OSi Specialities, Inc.Inventors: Mark P. Bowman, Curtis L. Schilling, Jr.
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Patent number: 5550272Abstract: A method for silating unsaturated monomers by contacting a system having at least one SiH group, an unsaturated monomer, a transition metal catalyst and a free radical polymerization inhibitor is described.Type: GrantFiled: October 2, 1995Date of Patent: August 27, 1996Assignee: General Electric CompanyInventors: Larry N. Lewis, Terrell W. Carothers
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Patent number: 5548051Abstract: Single component inorganic/organic network materials incorporating the physical properties of glasses with the flexibility of organic materials of empirical formula X(SiO.sub.1.5).sub.n wherein X is one or more flexible organic linkages and n is greater than or equal to 2, as well as precursors thereof, are disclosed.Type: GrantFiled: August 7, 1995Date of Patent: August 20, 1996Assignee: E. I Du Pont de Nemours and CompanyInventors: Michael J. Michalczyk, Kenneth G. Sharp
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Patent number: 5536860Abstract: Aminopropylalkoxysilanes of formula (I):R.sup.2 R.sup.3 NCH.sub.2 CHR.sup.4 CH.sub.2 Si(OR).sub.3-n (R.sup.1).sub.n(I)are prepared by reacting hydrogensilanes of formula (II):HSi(OR).sub.3n (R.sup.1).sub.n (II)with an amine of formula (III):R.sup.2 R.sup.3 NCH.sub.2 CR.sup.4 .dbd.CH.sub.2 (III),where R and R.sup.1 are alkyl radicals having from 1 to 8 carbon atoms and n is equal to 0, 1 or 2 andR.sup.2 and R.sup.3 are hydrogen, alkyl radicals having from 1 to 8 carbon atoms, .omega.-alkenyl radicals having from 3 to 8 carbon atoms or combinations thereof, andR.sup.4 is hydrogen or an alkyl radical having from 1 to 8 carbon atoms, in the presence of a shaped polymeric rhodium complex catalyst containing organosiloxanemonophenylphosphine ligands.Type: GrantFiled: October 4, 1995Date of Patent: July 16, 1996Assignee: Huels AktiengesellschaftInventors: Jaroslaw Monkiewicz, Albert Frings, Michael Horn, Hans-Joachim Koetzsch, Frank Kropfgans, Claus-Dietrich Seiler, Hans-Guenther Srebny, Burkhard Standke
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Patent number: 5530152Abstract: Disclosed is a process for manufacturing organosilanes by contacting an olefin with a silane in the presence of an azo compound.Type: GrantFiled: February 17, 1995Date of Patent: June 25, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Hasan Dindi, Stuart N. Milligan
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Patent number: 5527936Abstract: A method for hydrosilylating an olefinically unsaturated compound comprising contacting the unsaturated compound with a source of silicon in the presence of an azo-containing free-radical catalyst, the hydrosilylated product being a useful crosslinking agent.Type: GrantFiled: February 17, 1995Date of Patent: June 18, 1996Assignee: E. I. du Pont de Nemours and CompanyInventors: Hasan Dindi, Basil Gregorovich, Isidor Hazan, Stuart Milligan
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Patent number: 5523436Abstract: Novel catalysts of the general formulaMX.sub.a Y.sub.b,in whichM is Pt, Pd, Rh, Ru, Os or Ir,X is a triazene, tetrazene, tetrazadiene or pentazadiene ligand,Y is a ligand selected from Cl, Br, I, NH.sub.3, P(C.sub.2 H.sub.5).sub.3, P(C.sub.6 H.sub.5).sub.3, H, CO, 1,5-cyclooctadiene, pyridine, bipyridine, acetate, acetylacetonate, phenylnitrile, ethylenediamine, acetonitrile, 2,5-norbornadiene, nitrate, nitrite, H.sub.2 O, benzene, diphenylphosphinoethane and 1,3-divinyl-1,1,3,3-tetramethyldisiloxane,a is 1, 2, 3 or 4 andb is 0 or an integer from 1 to 6, are described.The catalysts promote the addition of Si-bonded hydrogen onto an aliphatic multiple bond, in which the catalysts are activated by heating at temperatures of 50.degree. to 250.degree. C., by irradiation with light, by addition of Bronsted acids and/or by addition of acid-forming agents.Type: GrantFiled: December 10, 1993Date of Patent: June 4, 1996Assignee: Wacker-Chemie GmbHInventors: Jochen Dauth, Udo Peetz, Bernward Deubzer
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Patent number: 5516870Abstract: Linear or straight-chain trimethylsiloxy endcapped methylhydrogen polysiloxanes are made by contacting hexamethyldisiloxane with a highly pure methylhydrogen cyclic siloxane, in the presence of anhydrous trifluoromethane sulfonic acid catalyst at room temperature. Trimethylsiloxy endcapped alkylmethyl siloxanes are made by reacting the linear or straight-chain trimethylsiloxy endcapped methylhydrogen polysiloxanes with an alpha-olefin, in the presence of a platinum catalyst. Alkylmethyl cyclic siloxanes containing zero parts per million residual .ident.SiH, are made by reacting anhydrous alpha-olefins and a highly pure methylhydrogen cyclic siloxane, in the presence of dried platinum supported on carbon catalyst.Type: GrantFiled: May 3, 1995Date of Patent: May 14, 1996Assignee: Dow Corning CorporationInventors: Timothy N. Biggs, Gary E. Le Grow
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Patent number: 5496961Abstract: Organosilicon compounds having Si-bonded hydrogen atoms are reacted with organic compounds having aliphatic multiple bonds in the presence of triazene oxide-transition metal complexes. The triazene oxide-transition metal complexes are activated by heating at temperatures of from 50.degree. C. to 250.degree. C. and/or by irradiation with light.Type: GrantFiled: May 10, 1995Date of Patent: March 5, 1996Assignee: Wacker-Chemie GmbHInventors: Jochen Dauth, Josef Wolferseder, Bernward Deubzer
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Patent number: 5493045Abstract: A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an accelerator selected from a group consisting of ene-yne unsaturated compounds. The accelerators are especially useful for facilitating the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene.Type: GrantFiled: June 26, 1995Date of Patent: February 20, 1996Assignee: Dow Corning CorporationInventors: Howard M. Bank, Gary T. Decker, Peter Y. K. Lo
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Patent number: 5486637Abstract: A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an accelerator selected from a group consisting of unsaturated secondary and tertiary alcohols and silated unsaturated secondary and tertiary alcohols. The accelerators are especially useful for the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene. The accelerators are believed to be effective in the presence or absence of oxygen.Type: GrantFiled: April 17, 1995Date of Patent: January 23, 1996Assignee: Dow Corning CorporationInventors: Howard M. Bank, Gary T. Decker
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Patent number: 5481016Abstract: A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an accelerator selected from a group consisting of tertiary alcohols, silated tertiary alcohols, benzyl alcohol, and silated benzyl alcohol. The accelerators are especially useful for the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene. The accelerators are believed to be effective in the presence or absence of oxygen.Type: GrantFiled: April 17, 1995Date of Patent: January 2, 1996Assignee: Dow Corning CorporationInventors: Howard M. Bank, Gary T. Decker
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Patent number: 5473038Abstract: The invention relates to a series of novel silicone polymers containing both fluorinated and alkyl side chains. This class of compounds provides very thin breathable barriers which are very durable when applied to textiles and paper. The compounds of the present invention are prepared by reacting a silanic hydrogen containing silicone polymer with a vinyl containing fluoro compound and an alpha olefin.Type: GrantFiled: April 28, 1995Date of Patent: December 5, 1995Assignee: Siltech Inc.Inventor: Anthony J. O'Lenick, Jr.
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Patent number: 5468816Abstract: A release modifier which comprises (i) a MQ resin consisting essentially of units of the formulae SiO.sub.2 and R.sub.3 SiO.sub.1/2 wherein R denotes a monovalent hydrocarbon group having up to 3 carbon atoms, a hydrogen atom, a c.sub.2-5 alkenyl group of the formula --R'CH.dbd.CH.sub.2, provided there is at least one group --R'CH.dbd.CH.sub.2 present per MQ molecule and (ii) a .alpha.,.omega.-diolefin having the general formula CH.sub.2 .dbd.CH--(CH.sub.2).sub.n --CH.dbd.CH.sub.2, wherein n denotes an integer with a value of from 4 to 18 gives improved release force over prior art controlled release additives. Also claimed is a solventless release composition based on siloxanes having SiH groups and a catalyst in addition to the release modifier.Type: GrantFiled: October 28, 1994Date of Patent: November 21, 1995Assignee: Dow Corning LimitedInventors: Simon R. Hurford, Bhukandas Parbhoo
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Patent number: 5463009Abstract: A fluorine-modified silicon compound having a polymerization degree of from 1 to 400 and containing at least one siloxane unit represented by formula (1): ##STR1## wherein R.sup.1 represents an aliphatic straight-chain or branched hydrocarbon group having 1 to 20 carbon atoms or an alicyclic hydrocarbon group having 5 to 10 carbon atoms or an aromatic hydrocarbon compound having 6 to 10 carbon atoms; and m represents 0 or an integer of from 1 to 10; a process for preparing the same; and a cosmetic containing the same are disclosed. The fluorine-modified silicone derivative exhibits high water- and oil-repellency to provide cosmetics which wear long and have a good feel on use.Type: GrantFiled: December 8, 1994Date of Patent: October 31, 1995Assignee: Kao CorporationInventors: Jouji Okada, Akira Kawamata, Tadayuki Tokunaga, Makoto Torizuka, Masahiko Asahi
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Patent number: 5449802Abstract: A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an accelerator selected from a group consisting of acetylenic alcohols, silated acetylenic alcohols, and acetylenic ethers. The accelerators are especially useful for the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene. The unsaturated ketone accelerators are effective in the presence or absence of oxygen.Type: GrantFiled: December 27, 1994Date of Patent: September 12, 1995Assignee: Dow Corning CorporationInventors: Howard M. Bank, Gary T. Decker
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Patent number: 5424470Abstract: A hydrosilation process where a silicon hydride is reacted with an unsaturated reactant in the presence of a platinum catalyst and an unsaturated ketone accelerator. The described unsaturated ketone accelerators are especially useful for the hydrosilation of unsaturated reactants where the unsaturation is in the internal portion of the reactant's structure, for example, as in cyclopentene and cyclohexene. The unsaturated ketone accelerators are effective in the absence of oxygen activation of the platinum catalyst and are synergetic with oxygen activation of platinum catalyst.Type: GrantFiled: October 27, 1994Date of Patent: June 13, 1995Assignee: Dow Corning CorporationInventors: Howard M. Bank, Gary T. Decker
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Patent number: 5416233Abstract: This invention relates to a novel process for preparing vinylsilane-BCBs (vinylsilane-benzocyclobutenes) comprising reacting a hydrosilating reagent with an acetylene-BCB in the presence of a catalyst.The invention also relates to a novel mixture of isomers of DVS-bisBCB (1,3-divinyl-1,1,3,3-tetramethyldisiloxane bisbenzocyclobutene) as well as novel partially or fully cured polymers derived from the vinylsilane BCBs.Type: GrantFiled: January 25, 1994Date of Patent: May 16, 1995Assignee: The Dow Chemical CompanyInventors: Robert A. DeVries, Edmund J. Stark
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Patent number: 5403947Abstract: A method of producing dicyclopentyldichlorosilane which comprises reacting cyclopentene and dichlorosilane with each other by using a platinum catalyst and/or a rhodium catalyst in the presence of 1,3-diethinyl-1,1,3,3-tetramethyldisiloxane.Type: GrantFiled: June 27, 1994Date of Patent: April 4, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Toshio Shinohara
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Patent number: 5386048Abstract: The invention provides silicon substituted fullerene compounds. The compounds can form polymers or wrapped fullerenes. The compounds may be made by reacting an organo-silicon compound with a fullerene in the presence of a catalyst by a hydrosilylation reaction.Type: GrantFiled: November 24, 1993Date of Patent: January 31, 1995Assignee: Wisconsin Alumni Research FoundationInventors: Robert C. West, Kunio Oka
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Patent number: 5359112Abstract: Process for producing organosilicon compounds having silicon-bonded substituents, e.g. hexenyl, containing terminal olefinic unsaturation. Process comprises reacting .tbd.SiH with a diene in the presence of a mixture, and/or a reaction product, of a compound or complex of platinum and a compound having at least one amino group e.g. octylamine.Type: GrantFiled: November 2, 1993Date of Patent: October 25, 1994Assignee: Dow Corning LimitedInventor: Robert A. Drake
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Patent number: 5359111Abstract: This invention discloses a method of controlling hydrosilylations in a reaction mixture by controlling the solution concentration of oxygen in the reaction mixture, relative to any platinum present in the reaction mixture. This invention further discloses a method for controlling isomerization in linear or branched alkenyl compounds having at least 4 carbon atoms during a hydrosilylation reaction by introducing a controlled amount of oxygen into the alkenyl compounds during the hydrosilylation. This invention further discloses a method for producing dicycloalkylsubstituted silanes by reacting a halo-or alkoxy-silane with a unsaturated cycloalkenyl compound in the presence of oxygen and a hydrosilylation catalyst.Type: GrantFiled: July 30, 1993Date of Patent: October 25, 1994Assignee: Dow Corning CorporationInventors: Don L. Kleyer, Binh T. Nguyen, Dale E. Hauenstein, Sean P. Davern, William J. Schulz, Jr.
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Patent number: 5359113Abstract: A method for maintaining catalytic activity during a hydrosilylation reaction between a silicon hydride and an unsaturated compound is disclosed. The method comprises reacting a silicon hydride and an unsaturated compound in the presence of a platinum catalyst wherein a peroxide is added into the reaction mixture to maintain the catalytic activity of the platinum catalyst.Type: GrantFiled: November 8, 1993Date of Patent: October 25, 1994Assignee: Dow Corning CorporationInventor: Howard M. Bank
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Patent number: 5347027Abstract: The present invention provides an electroless process for making a catalyst in a liquid or gaseous medium comprising contacting a base metal with a chemical cleaning agent and simultaneously or sequentially treating said base metal under reducing conditions with a noble metal-containing material, the catalyst prepared using the process, and a method of using the catalyst.Type: GrantFiled: April 22, 1993Date of Patent: September 13, 1994Assignee: OSi Specialties, Inc.Inventors: James S. Ritscher, Wei T. Yang, George M. Omietanski, Robert L. Ocheltree, Earl E. Malson