With Preservative Or Stabilizer Patents (Class 556/401)
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Patent number: 5202459Abstract: The present invention relates to a process for producing cyclobutane derivatives represented by general formula (28): ##STR1## (wherein R represents a substituent; R.sub.2 represents an electron attracting group and Nu represents a substituent corresponding to nucleophilic reagent), by reacting a compound represented by general formula (27): ##STR2## (wherein R has the same significance as defined above and R.sub.1 represents an electron attracting group) with nucleophilic reagents Nu.sup..crclbar. in a solvent.The compounds of formula (28) are useful as intermediates for synthesis of, for example, 9-[2,3-bis(hydroxymethyl)cyclobutan-1-yl]guanine which is expected to be useful as an antiviral agent.Type: GrantFiled: October 16, 1990Date of Patent: April 13, 1993Assignee: Nippon Kayaku Kabushiki KaishaInventors: Chikara Kaneko, Nobuya Katagiri
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Patent number: 5185391Abstract: The invention is a composition containing a polymer formed by side ring opening of an arylcyclobutene compound and an effective amount of an antioxidant.Type: GrantFiled: November 27, 1991Date of Patent: February 9, 1993Assignee: The Dow Chemical CompanyInventor: Theodore M. Stokich, Jr.
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Patent number: 5103032Abstract: Compositions containing an acryloxysilane or a methacryloxysilane and an N,N-dialkylaminomethylene phenol in an amount at least sufficient to inhibit polymerization of the silane during its formation, purification and storage. Methods for producing such compositions are also provided.Type: GrantFiled: June 27, 1991Date of Patent: April 7, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Scot M. Turner, George M. Omietanski
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Patent number: 5099051Abstract: Siloxanyl-phosphate mixtures are prepared by reacting cyclopolydimethylsiloxane and a silylphosphate mixture. The siloxanyl-phosphate mixture is a mixture of 5 to 30 weight percent of a monosiloxanyl-phosphate of the formula ##STR1## 70 to 85 weight percent of a disiloxanyl-phosphate of the formula ##STR2## 2 to 11 weight percent of a trisiloxanyl-phosphate of the formula wherein x has an average value of from 3 to 30.These siloxanyl-phosphate mixtures are useful in stabilizing basic polymerization catalyst such as potassium hydroxide or potassium silanolate and can either be used effectively per se or in combination with carbon dioxide.Type: GrantFiled: August 16, 1991Date of Patent: March 24, 1992Assignee: Dow Corning CorporationInventors: James A. Beck, Peter Lamont
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Patent number: 5087714Abstract: Discoloration of vinylacetoxysilanes is prevented by adding thereto 25 to 500 ppm, based on the amount of vinylacetoxysilane, of 3,5-di-tert.-butylpyrocatechol, 2,6-di-tert.-butyl-4-methylphenol, 2-mercaptobenzimidazole or a mixture thereof.Type: GrantFiled: June 3, 1991Date of Patent: February 11, 1992Assignee: Huels AktiengesellschaftInventors: Claus-Dietrich Seiler, Hartwig Rauleder, Albert Frings, Hans-Joachim Kotzsch
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Patent number: 5034446Abstract: Organopolysiloxane fluids, thiofunctional polysiloxane fluids, or blends of organopolysiloxane fluids and thiofunctional polysiloxane fluids are stabilized against degradation in the presence of kaolin clays at elevated temperatures by adding an epoxy containing compound.Type: GrantFiled: September 20, 1990Date of Patent: July 23, 1991Assignee: Genesee Polymers CorporationInventors: Steven S. Kendall, Charles Piskoti
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Patent number: 5034445Abstract: Organopolysiloxane fluids, thiofunctional polysiloxane fluids, or blends of organopolysiloxane fluids and thiofunctional polysiloxane fluids are stabilized against degradation in the presence of kaolin clays at elevated temperatures by adding an epoxy containing compound.Type: GrantFiled: September 21, 1990Date of Patent: July 23, 1991Assignee: Genesee Polymers CorporationInventors: Steven S. Kendall, Charles Piskoti
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Patent number: 5017715Abstract: A composition comprising iodotrimethylsilane in admixture with a polysiloxane is shelf stable for a long time and effective in various organic synthetic reactions.Type: GrantFiled: May 16, 1990Date of Patent: May 21, 1991Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuyuki Oikawa, Toshinobu Ishihara, Mikio Endo, Tohru Kubota
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Patent number: 5013858Abstract: A power transmission medium having improved resistance to oxidation and heat comprising polyorganosiloxanes and an effective amount of a mixture of anthraquinone compounds and methyl hydrogen siloxanes.Type: GrantFiled: April 25, 1990Date of Patent: May 7, 1991Assignee: Bayer AktiengesellschaftInventors: Gerwig Marquardt, Peter Preiss
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Patent number: 4990552Abstract: A silicone oil used, for example, as an electric insulation oil can be imparted with greatly increased flame retardancy when it is compounded with a soluble platinum compound, e.g., chloroplatinic acid, and an alkynyloxy, e.g., ethynyloxy, containing compound or, in particular, an ethynyloxy-containing organosilicon compound. The heat resistance of the silicone oil composition can be further improved by admixing the composition with an organosilicon compound having at least one imino-containing aromatic group such as a 4-anilinophenoxy group bonded to the silicon atom.Type: GrantFiled: January 25, 1989Date of Patent: February 5, 1991Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Shigeru Mori, Satoshi Kuwata, Motohiko Hirai
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Patent number: 4973620Abstract: A composition and method for treating fibers is based on a mixture of an organopolysiloxane having at least one amino-substituted hydrocarbon radical directly bonded to a silicon atom and a carboxylic acid containing at least one ethylene oxide unit. The carboxylic acid reacts with the amino radicals to reduce yellowing and oxidation of the fiber treatment. The composition and method provide non-yellowing fibers and a treatment agent that does not gel during use, such as when exposed to carbon dioxide and/or used to treat carbon fibers.Type: GrantFiled: May 26, 1989Date of Patent: November 27, 1990Assignee: Toray Silicone Company, Ltd.Inventors: Isao Ona, Masaru Ozaki, Hidetoshi Kurusu
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Patent number: 4927948Abstract: Organosilanes comprising methacryloxy groups or acryloxy groups are stabilized with a mixture consisting of at least one N,N'-di-substituted-p-phenylenediamine and at least one substituted phenol, which yields products with high purity and high yields.Type: GrantFiled: September 19, 1989Date of Patent: May 22, 1990Assignee: Huels AktiengesellschaftInventors: Gunther Bernhardt, Jurgen Amort, Heinz Kragl, Margret Haas
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Patent number: 4921987Abstract: Aqueous solutions of alkyltrialoxysilanes are stabilized by adding an alkali metal aluminate and an alkali metal hydroxide thereto.Type: GrantFiled: August 17, 1989Date of Patent: May 1, 1990Assignee: Huels AktiengesellschaftInventors: Reiner Hitze, Hans-Jurgen Hass
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Patent number: 4912239Abstract: A method for stabilizing an unsaturated organosilicone is disclosed wherein a stabilizing amount of a hydroxylamine compound is added to the organosilicone to prevent thermal polymerization of the latter. The organosilicone may be an alkoxysilane or an organopolysiloxane having in its molecule a reactive organic group bearing at least one radical selected from acryloxy, methacryloxy, acrylamide, methacrylamide, styryl or vinylbenzyl radicals. The hydroxylamine compound may be added either to the organosilicone or during the preparation of the alkoxysilane from its respective reactants.Type: GrantFiled: September 19, 1988Date of Patent: March 27, 1990Assignee: Dow Corning CorporationInventors: Howard M. Bank, Edwin P. Plueddemann
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Patent number: 4898956Abstract: Thermo-oxidatively stable polysiloxanes are prepared by adding certain zirconium compounds to the fluid. These zirconium compounds are of the organozirconium or siloxyzirconium types. Two methods for preparation of the fluids is discussed. The fluids of this invention are useful as heat transfer fluids, lubricants, or damping fluids. They have particular usefulness in applications that have a low surface area to volume ratio.Type: GrantFiled: June 27, 1989Date of Patent: February 6, 1990Assignee: Dow Corning CorporationInventor: Terrence K. Hilty
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Patent number: 4871788Abstract: Novel ionomeric silane coupling agents are disclosed and their use in bonding a matrix polymer to a mineral substrate is described. The coupling agents comprise amic acid-functional silanes which are partially neutralized with metal cations and are prepared by reacting a mixture of (I) an amine-functional silane, (II) a stoichiometric excess of a dicarboxylic organic acid and (III) an ionic compound containing a metal cation, wherein 10% to 80% of the excess carboxylic acid functionality is neutralized by the metal cations. The coupling agents greatly improve bonding to the matrix polymer in moist environments and are particularly suitable for use in formulating filled injection molding compositions.Type: GrantFiled: June 3, 1988Date of Patent: October 3, 1989Assignee: Dow Corning CorporationInventor: Edwin P. Plueddemann
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Patent number: 4857583Abstract: An improved process is provided for the preparation of siloxane-oxyalkylene block copolymer surfactant compositions which utilized a hydrosilation reaction with high boiling point polar polyols as the reaction solvent. The reaction solvent need not be removed from the block copolymer, particularly when the block copolymer is used as a surfactant for polyurethane foam formulations. Dipropylene glycol is the preferred polar solvent and when used in the preparation of the surfactants need not be removed when the surfactants are employed in the preparation of urethane foams.Type: GrantFiled: July 2, 1987Date of Patent: August 15, 1989Assignee: Union Carbide CorporationInventors: Paul E. Austin, David D. Farris, James D. Reedy, Charles Blevins, Philbert E. Ramdatt
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Patent number: 4798889Abstract: A method for stabilizing an unsaturated organosilicone is disclosed wherein a stabilizing amount of a hydroxylamine compound is added to the organosilicone to prevent thermal polymerization of the latter. The organosilicone may be an alkoxysilane or an organopolysiloxane having in its molecule a reactive organic group bearing at least one radical selected from acryloxy, methacryloxy, acrylamide, methacrylamide, styryl or vinylbenzyl radicals. The hydroxylamine compound may be added either to the organosilicone or during the preparation of the alkoxysilane from its respective reactants.Type: GrantFiled: November 13, 1987Date of Patent: January 17, 1989Assignee: Dow Corning CorporationInventors: Edwin P. Plueddemann, Howard M. Bank
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Patent number: 4780555Abstract: There is disclosed a method for preparing acryl-functional halosilanes by reacting a halosilane with an acryloxy or methacryloxy-functional organic compound in the presence of a platinum hydrosilation catalyst and a stabilizing amount of phenothiazine, wherein the reaction mixture is contacted with an oxygen-containing inert gas. The present invention further discloses a method for stabilizing the above reaction mixture by contacting it with the oxygen-containing gas.Type: GrantFiled: January 4, 1988Date of Patent: October 25, 1988Assignee: Dow Corning CorporationInventor: Howard M. Bank
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Patent number: 4754046Abstract: There is provided a silyl ketene acetal mixture which has a reduced susceptibility to oxidation on exposure to ambient air. The silyl ketene acetal mixture comprises a silyl ketene acetal to which is added a phenolic compound, the phenolic compound being present in an amount sufficient to be effective as an oxidation inhibitor.Type: GrantFiled: June 25, 1987Date of Patent: June 28, 1988Assignee: Dow Corning CorporationInventor: Anthony Revis
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Patent number: 4732994Abstract: This invention relates to a method for stabilizing organopolysiloxane oils containing triorganosiloxy groups in their terminal units, in which the organopolysiloxane oils are contacted with compounds having the formulas:R.sub.3.sup.' SiX or (R.sub.3.sup.' Si).sub.2 Y,where R' represents the same or different hydrocarbon radicals having from 1 to 18 carbon atoms and halogenated hydrocarbon radicals having from 1 to 18 carbon atoms; X is a halogen atom, a hydrogen atom, a hydroxyl group or a monovalent radical that consists of nitrogen, hydrogen, oxygen and from 0 to 6 carbon atoms and which is bonded to the silicon atom via an oxygen or a nitrogen atom; Y is a divalent radical selected from the group consisting of an oxygen atom, an NH radical, an NR" radical, or a divalent radical consisting of nitrogen, hydrogen, oxygen and from 0 to 6 carbon atoms, which is bonded to the silicon atoms via oxygen and/or nitrogen atoms; and R" is a hydrocarbon radical having from 1 to 8 carbon atoms.Type: GrantFiled: June 15, 1987Date of Patent: March 22, 1988Assignee: Wacker-Chemie GmbHInventors: Manfred Riederer, Martin Piehler
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Patent number: 4722807Abstract: A stabilizer useful for inhibiting polymerization of .gamma.-acryloyloxypropyltrimethoxysilane and .gamma.-methacryloyloxypropyltrimethoxysilane comprising 2,5-di-t-butylhydroquinone and an alcohol.Type: GrantFiled: June 21, 1984Date of Patent: February 2, 1988Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Takahisa Iwahara, Tetsu Katsutani
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Patent number: 4701490Abstract: A method for stablizing organopolysiloxanes containing phosphonitrilic chlorides and/or their reaction products against viscosity changes by reacting the phosphorus compounds present in the organopolysiloxanes with at least one oxide, hydroxide or carbonate of a divalent or trivalent metal, and thereafter separating the solid from the organopolysiloxanes.Type: GrantFiled: May 15, 1986Date of Patent: October 20, 1987Assignee: Wacker-Chemie GmbHInventors: Jurgen Burkhardt, Werner Rauchberger
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Patent number: 4683319Abstract: A thermal stabilizer for organopolysiloxane oils is disclosed. The stabilizer is formed by the reaction of (A) an organopolysiloxane with (B) an aromatic aminophenol in the presence of (C) a quaternary phosphonium hydroxide, or in the presence of both the quaternary phosphonium hydroxide comprising component (C) and (D) an organopolysiloxane cyclic. Organopolysiloxane oils containing said thermal stabilizer are not subject to viscosity increases or gelation in long-term heating at high temperatures. Furthermore, such combinations show very little viscosity decline in long-term heating at high temperatures.Type: GrantFiled: October 9, 1986Date of Patent: July 28, 1987Assignee: Toray Silicone Co., Ltd.Inventors: Makoto Yoshitake, Keiichi Kishimoto
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Patent number: 4644074Abstract: Organopolysiloxane fluids are stabilized against degradation in the presence of kaolin clays at elevated temperatures by adding an amine containing compound to the organopolysiloxane fluids.Type: GrantFiled: April 10, 1985Date of Patent: February 17, 1987Assignee: SWS Silicones CorporationInventors: Paul A. Manis, Eugene R. Martin, Ronald L. Muntz
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Patent number: 4637889Abstract: A mixture of an organopolysiloxane fluid, a zirconium-containing organosiloxane compound having at least one zirconium atom and at least one siloxane unit, and a cerium-containing organosiloxane compound having at least one cerium atom and at least one siloxane unit is an organopolysiloxane viscous coupler fluid which can be used in gear systems. These coupler fluids undergo little viscosity increase or decrease and little torque variation at elevated temperature and under high shear over long periods of time.Type: GrantFiled: February 3, 1986Date of Patent: January 20, 1987Assignee: Toray Silicone Co., Ltd.Inventors: Keiichi Kishimoto, Makoto Yoshitake
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Patent number: 4612055Abstract: Siloxane fluid blends containing a thiofunctional polysiloxane fluid and an organopolysiloxane fluid are stabilized against degradation in the presence of kaolin clays at elevated temperatures by adding an amine containing compound to blends of siloxane fluids.Type: GrantFiled: April 10, 1985Date of Patent: September 16, 1986Assignee: SWS Silicones CorporationInventors: Paul A. Manis, Eugene R. Martin, Ronald L. Muntz
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Patent number: 4604476Abstract: The present invention relates to mercaptoalkyl alkoxysilanes and the permanent removal of the odorants contained in these compounds. These odorants form during the preparation of the said mercaptosilanes from halogen alkylsilanes with thiourea and ammonia. The removal of the odorants is performed by the admixture of compounds which contain oxirane groups. A subsequent purification, e.g., by distillation, after the addition of these compounds in accordance with the invention, is not necessary. The additive used in accordance with the invention also brings about a sustaining of the freedom from odor for several months.Type: GrantFiled: December 19, 1984Date of Patent: August 5, 1986Assignee: Dynamit Nobel AGInventors: Claus-Dietrich Seiler, Hans-Joachim Vahlensieck
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Patent number: 4588771Abstract: Thiofunctional polysiloxane fluids are stabilized against degradation in the presence of kaolin clay by adding an amine containing compound to the thiofunctional polysiloxane fluids.Type: GrantFiled: April 10, 1985Date of Patent: May 13, 1986Assignee: SWS Silicones CorporationInventors: Paul A. Manis, Eugene R. Martin, Ronald L. Muntz
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Patent number: 4564693Abstract: A process for stabilizing organopolysiloxanes against changes in viscosity which comprises reacting organopolysiloxanes containing phosphonitrile chlorides or reaction products thereof with at least one lithium compound which forms lithium chloride when reacted with the chlorine bonded to the phosphorous compound.Type: GrantFiled: August 2, 1985Date of Patent: January 14, 1986Assignee: Wacker-Chemie GmbHInventor: Manfred Riederer
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Patent number: 4563538Abstract: A process for stabilizing a silicon-containing methacrylate having the formula (I): ##STR1## wherein X is Si(OCH.sub.3).sub.3, Si(OCH.sub.3).sub.2 CH.sub.3, Si(OCH.sub.3)(CH.sub.3).sub.2 or Si(CH.sub.3).sub.3 which comprises adding 2,5-di-t-butylbenzoquinone to the silicon-containing methacrylate, whereby polymerization of the silicon-containing methacrylate can be inhibited. As a result, the silicon-containing methacrylate can be stabilized without any trouble in distillation step.Type: GrantFiled: May 6, 1985Date of Patent: January 7, 1986Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hiroshi Wakabayashi, Takahisa Iwahara
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Patent number: 4560784Abstract: The organopolysiloxane composition, e.g. silicone fluid, of the invention is imparted with high heat resistance by admixing with a specific heat-resistance improver which is prepared by a heat treatment of a mixture composed of (a) 100 parts by weight of an organopolysiloxane having a specified viscosity, (b) a carboxylate of cerium such as 2-ethylhexoate in an amount of 0.05 to 5 parts by weight as cerium and (c) an alkoxide compound of titanium or zirconium such as tetrabutyl titanate in an amount to give 0.1 to 5 times by weight of the titanium or zirconium element based on the cerium content in the component (b) at a temperature of, for example, 150.degree. to 310.degree. C. for 30 minutes to 10 hours.Type: GrantFiled: February 4, 1985Date of Patent: December 24, 1985Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Shigeru Mori, Yasuo Tarumi
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Patent number: 4503242Abstract: Alkali siliconates of silylorganosulfonates are capable of stabilizing solutions of water soluble silicates and enhancing their usefulness as corrosion inhibitors for metals that come in contact with aqueous, alcoholic or aqueous-alcoholic solutions. The disclosed alkali siliconates of silylorganosulfonates are also useful stabilizers for aqueous silicates in such applications as treating boiler water, geothermal water and cooling coil water. Methods of using the alkali siliconates of silylorganosulfonates to provide corrosion inhibiting antifreeze and coolant solutions are disclosed.Type: GrantFiled: February 18, 1983Date of Patent: March 5, 1985Assignee: Dow Corning CorporationInventor: Edwin P. Plueddemann
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Patent number: 4460726Abstract: A method for stabilizing organopolysiloxanes containing phosphonitrile chlorides or their reaction products which promote the condensation and/or equilibration of organopolysiloxanes which comprises reacting at least one compound containing at least one epoxy group per molecule with the phosphorus compounds present in the organopolysiloxanes.Type: GrantFiled: September 16, 1983Date of Patent: July 17, 1984Assignee: Wacker-Chemie GmbHInventors: Peter Huber, Rudolf Kaufmann, Juurgen Burkhardt
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Patent number: 4379094Abstract: Ferrosiloxane compounds prepared by reacting iron carboxylates and N,N-disubstituted silylamines are useful as thermal stabilizers for diorganopolysiloxanes. The thermally stable diorganopolysiloxanes find utility as heat transfer fluids, high temperature lubricants, hydraulic fluids and electric insulating fluids, to name but a few.Type: GrantFiled: December 30, 1981Date of Patent: April 5, 1983Assignee: Union Carbide CorporationInventors: Gail D. DiSalvo, James D. Reedy
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Patent number: 4344860Abstract: Salts of substituted nitrogen or sulfur containing siliconates are effective stabilizers for aqueous silicates in such applications as treating boiler water, geothermal water and other aqueous silicates. They are also useful in antifreeze and coolant solutions.Type: GrantFiled: March 30, 1981Date of Patent: August 17, 1982Assignee: Dow Corning CorporationInventor: Edwin P. Plueddemann
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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: 4230632Abstract: Heat stable silicone fluids are prepared by adding to silicone fluids from 10 to 50 percent by weight of an aminofunctional silicone fluid based on the total weight of the composition. The resultant composition is stable at temperatures above 400.degree. F. for more than 300 hours.Type: GrantFiled: March 7, 1979Date of Patent: October 28, 1980Assignee: SWS Silicones CorporationInventor: Dwain R. Chapman
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Patent number: 4203913Abstract: A method for stabilizing organopolysiloxanes which are obtained from the condensation and/or equilibration of organosilicon compounds in the presence of phosphoronitrile chlorides which comprises treating the organopolysiloxanes with ammonia or an amine of the general formulaYHNC(CH.sub.3).sub.n (CH.sub.2 X).sub.3-nin which each X represents a hydrogen atom or a radical of the formulae --OCH.sub.3, --N(CH.sub.3).sub.2, --C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 NHY and --OC(CH.sub.3).sub.3 ; Y represents a hydrogen atom or a trimethylsilyl radical and n represents 0, 1, 2 or 3.Type: GrantFiled: May 17, 1976Date of Patent: May 20, 1980Assignee: Wacker-Chemie GmbHInventors: Jurgen Burkhardt, Karl-Heinrich Wegehaupt
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Patent number: RE32250Abstract: Salts of substituted nitrogen or sulfur containing siliconates are effective stabilizers for aqueous silicates in such applications as treating boiler water, geothermal water and other aqueous silicates. They are also useful in antifreeze and cooland solutions.Type: GrantFiled: July 11, 1983Date of Patent: September 23, 1986Assignee: Dow Corning CorporationInventor: Edwin P. Plueddemann