Hydroxy Bonded Directly To Silicon (h Of Hydroxy May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Patents (Class 556/459)
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Patent number: 5576408Abstract: Hydrolysis of an alkoxysiloxane of the formula: R.sup.1.sub.a (R.sup.2 O).sub.b SiO.sub.(4-a-b)/2 wherein R.sup.1 is a monovalent hydrocarbon group, R.sup.2 is an alkyl group having 1 to 4 carbon atoms, letter a=0 to 2.2, b=0.2 to 3, 2.ltoreq.a+b.ltoreq.3, and the number of silicon atoms in a molecule is 2 to 5, is effected in the presence of a cation exchange resin by adding water therereto in an amount of 1 to 10 mol per mol of the alkoxy group in the alkoxysiloxane and agitating the mixture. Low molecular weight, linear organosiloxanes having a silanol terminal group including dimer diol and trimer diol are produced in high yields.Type: GrantFiled: August 24, 1995Date of Patent: November 19, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Minoru Igarashi, Masaharu Takahashi
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Patent number: 5563231Abstract: This invention relates to water-dispersible compounds that are useful as lubricants for textile wet processing having formula (I): ##STR1## wherein R is C.sub.1 -C.sub.10 alkylene;R.sup.1 is an m-functional group having the formula ##STR2## R.sup.2 and R.sup.3 are independently C.sub.1 -C.sub.10 alkyl or groups having the formula ##STR3## R.sup.4 is hydrogen, acyl, or trialkylsilyl; R.sup.5 and R.sup.6 are independently alkyl, alkoxy, --Z--(O--B).sub.s --OR.sup.4, or --Y--(O--A).sub.r --;R.sup.7 and R.sup.8 are independently alkyl, alkoxy, or --Z--(O--B).sub.s --OR.sup.4 ;X is hydrogen, (cyclo)alkyl, (cyclo)alkenyl, --NR.sup.c R.sup.d, --NR.sup.c R.sup.d R.sup.e+ Q.sup.-, --OR.sup.f, --SR.sup.g, --NH--CO--NH--R.sup.h, --O--CO--NH--R.sup.i, --NH--CO--O--R.sup.j, --CN, or halogen;A and B are independently alkylene;Y and Z are independently a direct bond or alkylene;m is from 1 to 20;r and s are independently from 0 to 20; andn and p are from 0 to 100 and the total (n+p) is from 10 to 100.Type: GrantFiled: June 6, 1995Date of Patent: October 8, 1996Assignee: Bayer CorporationInventors: Lloyd Barringer, Jr., Thomas P. Bellina, Brad A. Ziegler
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Patent number: 5539137Abstract: A method is provided for making silicone fluids having a high refractive index by effecting a hydrosilylation reaction between an arylacetylene such as phenylacetylene and a silicon hydride substrate, such as a cyclic or linear hyridosiloxane in the presence of a platinum catalyst.Type: GrantFiled: June 7, 1995Date of Patent: July 23, 1996Assignee: General Electic CompanyInventors: Larry N. Lewis, Susan A. Nye
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Patent number: 5508369Abstract: Novel organopolysiloxanes having one silanol group within a molecule and the method for manufacturing them at high purity and high yield. The organopolysiloxanes having a silanol group are expressed by the formula (1) below: ##STR1## wherein R.sup.1 is a monovalent hydrocarbon group with 1 to 8 carbon atoms, each of R.sup.2, R.sup.3 and R.sup.4 is a monovalent hydrocarbon group with 1 to 8 carbon atoms or a siloxyl group expressed by --OSiR.sup.5 R.sup.7, wherein R.sup.5, R.sup.6 and R.sup.7 are monovalent hydrocarbon groups with 1 to 8 carbon atoms, Y is either a hydrogen atom, a halogen atom, or a monovalent hydrocarbon group with 1 to 12 carbon atoms, n is an integer of from 0 to 12, and a is either 0 or 1, with the proviso that the grouping Y--(CH.sub.2).sub.n --Si does not includes H--Si, CH.sub.3 --Si or a hydrolyzable silyl group.Type: GrantFiled: August 17, 1994Date of Patent: April 16, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshio Yamazaki, Nobuyuki Suzuki, Shinichi Morioka, Shoji Ichinohe
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Patent number: 5492992Abstract: A process for making liquid polymers by condensing monomers and/or oligomers, mixing them with a catalyst where required, and dispersing the mixture via an atomizing device to form small droplets suspended in a reaction chamber. The reagents are caused to polymerize in the dispersed state. The process is preferably carried out in a spray dryer using an atomizing device and is particularly useful for polymerizing organosilicon compounds by condensation.Type: GrantFiled: December 5, 1994Date of Patent: February 20, 1996Assignee: Dow Corning S.A.Inventor: Jean M. Gilson
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Patent number: 5476916Abstract: The present invention describes a process wherein dimethyldichlorosilane is reacted, in a first step, with water present in hydrochloric acid to give a crude hydrolysate comprising cyclic and linear, chlorine-containing polydimethylsiloxanes and gaseous hydrogen chloride and, in a second step, the crude hydrolysate is treated with steam to reduce the chlorine content and form hydrochloric acid, with the hydrochloric acid formed in the second step being used in the first step.Type: GrantFiled: November 29, 1994Date of Patent: December 19, 1995Assignee: Wacker-Chemie GmbHInventors: Bernd Pachaly, Gerhard Nagy, Wolfgang Jacques, Robert Christa
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Patent number: 5436360Abstract: The present invention relates to novel cyclic or linear allylpolysiloxane type silicone fluids having allylalkylsiloxy and diorganosiloxy groups as represented by the formula I and their preparation methods by hydrolyzing mixtures of allyldichlorosilane and diorganodichlorosilane as represented by the formula II and formula III respectively. ##STR1## wherein R is selected from the group consisting of hydrogen alkyl(C.sub.3 -C.sub.20), chloroalkyl, cyanoalkyl, fluoroalkyl, and phenylalkyl group; R.sup.x and R.sup.2 represent independentlhydrogen, methyl or phenyl group; M represents H or SiMe.sub.3 group wherein Me is methyl group and when M is hydrogen, the silanol groups at the both ends of the molecule easily undergo dehydration and cyclize to form the cyclic silicone fluids as represented by the following formula I'; the mixing ratio (x/y) of the compounds as represented in formula I and formula HI respectively can be 1:0.01-1:100; CH.sub.2 CH.sub.2 R.sup.3 of formula II equals to R of formula I or I'.Type: GrantFiled: September 8, 1994Date of Patent: July 25, 1995Assignee: Korea Institute of Science and TechnologyInventors: Il N. Jung, Bok R. Yoo, Bong W. Lee, Seung H. Yeon
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Patent number: 5436358Abstract: The present invention relates to novel cyclic or linear 2-(aryl)propylalkylpolysiloxane type silicone fluids as represented by the formula I and their preparation methods by hydrolyzing mixtures of 2-(aryl)propylalkyldichlorosilane and diorganodichlorosilane as represented by the formula II and formula III respectively. ##STR1## wherein, X.sub.1 and X.sub.2 represent independently hydrogen or alkyl(C.sub.1 -C.sub.3), phenyl, phenoxy, fluoro, chloro, bromo, mercapto, mercaptomethyl group; R.sup.2 and R.sup.3 represent independently methyl or phenyl group; R.sup.1 in the formula I is same as CH.sub.2 CH.sub.2 R in formula II or cyclohexyl wherein R is C.sub.n H.sub.2n+2 (n=1-16), chloromethylene, cyanomethylene, phenyl, or cyano group; M represents H or SiMe.sub.3 group wherein Me is methyl group and when M is hydrogen, the silanol groups at the both ends of the molecule easily undergo dehydration and cyclize to form the cyclic silicone fluids; n and m can be 2-200 and the ratio n/m can be 1:0.01-1:100.Type: GrantFiled: September 8, 1994Date of Patent: July 25, 1995Assignee: Korea Institute of Science and TechnologyInventors: Il N. Jung, Bok R. Yoo, Bong W. Lee
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Patent number: 5369206Abstract: A diorganopolysiloxane terminated only at one of the molecular chain ends with a (meth)acryloxyalkyl group bonded to the terminal silicon atom is prepared, instead of the prior art method in which a diorganopolysiloxane obtained by the anionic ring-opening living polymerization reaction of, for example, hexamethyl cyclotrisiloxane by using a lithium catalyst is subjected to a desalinating condensation reaction with a (meth)acryloxyalkyl dimethyl chlorosilane, by a novel method in which the diorganopolysiloxane obtained by the anionic ring-opening living polymerization reaction of, for example, hexamethyl cyclotrisiloxane is hydrolyzed and the thus obtained monofunctionally silanol-terminated diorganopolysiloxane is reacted with a (meth)acryloxyalkyl dimethyl dialkylamino silane to effect a deamination reaction.Type: GrantFiled: January 31, 1994Date of Patent: November 29, 1994Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masanao Kamei, Tomohisa Suzuki
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Patent number: 5276173Abstract: The present invention is a method for reducing the ionic chloride content of hydroxyl-terminated siloxanes. The method involves contacting the hydroxyl-terminated siloxanes with a molecular sieve effective in removing residual water from the siloxanes. Since ionic chloride strongly partitions into the water phase, ionic chloride is removed along with the water phase. In a preferred embodiment of the present method as aprotic solvent is employed to facilitate water removal from the hydroxyl-terminated siloxanes.Type: GrantFiled: October 5, 1992Date of Patent: January 4, 1994Assignee: Dow Corning CorporationInventors: Ollie W. Marko, Robert D. Steinmeyer
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Patent number: 5262558Abstract: There is disclosed a method for making organo-silicon polymers from alkyldisiloxanes and alkylsilicates wherein the alkyl groups of the disiloxanes have two or more carbons. Gelling of the organo-silicon polymers is avoided by; first mixing the disiloxane with the alkylsilicate and adding thereto a strong protic acid; and, after reaction has occurred in the aforementioned mixture, adding thereto, in a drop-wise manner, a solution of hydrochloric acid.Type: GrantFiled: August 20, 1992Date of Patent: November 16, 1993Assignee: Dow Corning Toray Silicone Co., Ltd.Inventors: Hideki Kobayashi, Wataru Nishiumi
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Patent number: 5254654Abstract: The molecular weight distribution of polydimethylsiloxane-.alpha., .omega.-diol fluids is reduced by contacting the fluid with an alkaline earth metal hydride or hydroxide. Molecular weight distributions lower than Poisson distributions may be obtained. The resulting monodispersed polydimethylsiloxane.alpha., .omega.-diol fluids may be substituted by reaction with common silanating reagents to prepare telechelic polydimethylsiloxanes which are nearly monodispersed.Type: GrantFiled: July 10, 1992Date of Patent: October 19, 1993Assignee: Temple University of the Commonwealth System of Higher EducationInventors: Mark A. Buese, Sejal Patel
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Patent number: 5247043Abstract: Low-molecular-weight phenylpolysilsesquioxanes that have narrow molecular weight distribution and a method for the preparation of the same.Type: GrantFiled: July 24, 1992Date of Patent: September 21, 1993Assignee: Dow Corning Toray Silicone Co., Ltd.Inventor: Hisataka Nakashima
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Patent number: 5233067Abstract: A method for metallizing a polymeric substrate is disclosed. The method includes contacting a surface of an etched polymeric substrate with a silane coupling agent and depositing a metallic layer over the surface. The silane coupling agent forms a chemical linkage between the substrate and the metallic layer. A coupling agent composition and a metallized polymeric substrate are also described.Type: GrantFiled: May 8, 1990Date of Patent: August 3, 1993Assignee: Rogers CorporationInventors: Gwo Swei, Kenneth W. Kristal
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Patent number: 5169970Abstract: A method for hydrolyzing an organochlorosilane to produce an organopolysiloxane, which comprisesa first-stage hydrolysis of hydrolyzing the organochlorosilane using a substantially stoichiometrically equivalent amount of water, thereby producing a hydrolyzate, anda second-stage hydrolysis of hydrolyzing the hydrolyzate obtained in the first-state hydrolysis using a stoichiometrically excess amount of aqueous hydrogen chloride solution having a predetermined hydrogen chloride concentration, thereby to produce an organopolysiloxane as a hydrolyzate and, at the same time, regulate the viscosity of the organopolysiloxane.Type: GrantFiled: June 26, 1989Date of Patent: December 8, 1992Assignee: Toshiba Silicone Co., Ltd.Inventor: Nobuaki Ohkawa
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Patent number: 5079291Abstract: There is provided a fluorosilicone composition comprising:(1) a cyclic trimer represented by the general formula: ##STR1## wherein R.sup.1 is C.sub.1-8 alkyl, preferably methyl; R.sup.2 is C.sub.1-8 haloalkyl, preferably trifluoropropyl; and x ranges from 3 to 10 and averages about 6;(2) water; and(3) a mixture comprising by weight about 20% to about 52% of a polar aprotic solvent and about 80% to about 48% of an organic nonaprotic solvent.Type: GrantFiled: November 20, 1989Date of Patent: January 7, 1992Assignee: General Electric CompanyInventor: Edwin R. Evans
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Patent number: 5057620Abstract: A process for producing a linear organotetrasiloxane comprises the step of hydrolyzing a dihalotetrasiloxane in the presence of an organic compound having at least one epoxy radical. The process prevents effectively the by-production of high molecular weight or cyclic condensates, and yields a linear organotetrasiloxane having a high OH number and high activity.Type: GrantFiled: August 7, 1990Date of Patent: October 15, 1991Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yoshio Inoue, Naoki Omura
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Patent number: 5011962Abstract: Organosiloxanes (1) of the general formulaR.sup.1.sub.4-n Si(OSiR.sub.3).sub.n,in which R is the same or different and represents a hydrogen atom or a monovalent hydrocarbon radical having from 1 to 18 carbon atom(s) per radical or a substituted monovalent hydrocarbon radical having from 1 to 18 carbon atom(s) per radical, R.sup.1 represents R or a chlorine atom, and n is 3 or 4, are prepared by reacting organodisiloxanes (2) of the general formula(R.sub.3 Si).sub.2 O,with chlorosilanes (3) of the general formulaR.sub.4-n SiCl.sub.n,in which R and n are the same as above, in the presence of phosphonitrile chlorides (4) and cocatalysts (5), in which the cocatalysts (5) are used concomitantly with the phosphonitrile chlorides (4) and are selected from the group consisting of amides of the general formulaX--C(O)--R.sup.2,in which R.sup.Type: GrantFiled: May 30, 1990Date of Patent: April 30, 1991Assignee: Wacker-Chemie GmbHInventors: Gerhard Staiger, Johann Muller, Walter Doskocil
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Patent number: 4977289Abstract: Sodium fluorosilanolate catalyst is disclosed which has improved effectiveness as a catalyst to produce fluorosilicone polymer and which at the same time improves fluorosilicone polymer purity.Type: GrantFiled: November 16, 1989Date of Patent: December 11, 1990Assignee: General Electric CompanyInventor: Edwin R. Evans
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Patent number: 4977290Abstract: There is provided a process for producing low molecular weight silanol end-stopped diorganopolysiloxanes containing an average of 3 to 10 diorganosiloxy units and averaging 5 diorganosiloxy units comprising contacting a cyclic trimer of the formula:(R.sup.2 SiO).sub.3where R.sup.2 is a halogenated monovalent hydrocarbon radical and R is selected from the class consisting of monovalent hydrocarbon radicals and halogenated monovalent hydrocarbon radicals with a mixture comprising an aprotic solvent and water and separating the desired product after the hydrolysis.Type: GrantFiled: November 20, 1989Date of Patent: December 11, 1990Assignee: General Electric CompanyInventors: Edwin R. Evans, Paul Maitoza
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Patent number: 4962221Abstract: The instant invention is a process for reducing residual chloride content of polysiloxane fluids, without detrimental effects on the polysiloxane polymer. The process comprises contacting the polysiloxane fluid, containing residual chloride, with selected weakly-basic alkaline metal compounds at a temperature less than 100.degree. C. After an appropriate contact time, the polysiloxane fluid is separated from the solid alkaline metal compounds. In a preferred embodiment of the present invention, water is added to the process to facilitate removal of residual chloride.Type: GrantFiled: March 12, 1990Date of Patent: October 9, 1990Assignee: Dow Corning CorporationInventors: Arnold R. Huntress, Daryl D. Landis, Donald E. McVannel, Timothy Allen
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Patent number: 4923950Abstract: Composition based on derivatives of silica modified by organic groups, characterized in that said derivatives are amorphous solids having formula (I) SiO.sub.2-0.5(x+y) (Z.sup.1.sub.x (Z.sup.2).sub.y .multidot.(XA).sub.z, wherein Z.sup.1 is a group having formula (II), R.sup.1 being an alkylene having from 3 to 8 carbon atoms optionally interrupted by a heteroatomic group --NH--, R.sup.3 and R.sup.4 representing each --H or representing together a group --CH.dbd.CH--N.dbd.CH--, Z.sup.2 is a group --R.sup.2 --SO.sub.3 H, R.sup.2 being an alkylene having from 3 to 8 carbon atoms optionally interrupted by a heteroatomic group --NH--; XZ is an acid (case where X.dbd.H) or a salt (case where X.dbd.metal) soluble in water x is a number different from 0 and lower or equal to 1; z is a number which may vary from 0 to 0.Type: GrantFiled: April 28, 1988Date of Patent: May 8, 1990Assignee: Centre National de la Recherche Scientifique (CNRS)Inventors: Lucienne Ravaine, Michel B. Armand, Yves Charbouillot, Abdelkader Hammou
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Patent number: 4902813Abstract: A process for preparing diorganopolysiloxanes having terminal Si-bonded hydroxyl groups which comprises reacting an organosilicon compound selected from a cyclic diorganopolysiloxane, a diorganodichlorosilane hydrolysis product and mixtures thereof with from 0.1 to 3 percent by weight of a diorganodichlorosilane, based on the weight of the organosilicon compound, i.e., the cyclic diorganopolysiloxane and/or diorganodichlorosilane hydrolysis product employed, in the presence of from 1 to 50 ppm by weight of phosphonitrile chloride, based on the total weight of the organosilicon compound and diorganodichlorosilane employed, to form diorganopolysiloxanes containing an Si-bonded chlorine atom in each of the terminal units, then treating the reaction mixture with water or an aqueous solution, separating off the aqueous phase from the diorganopolysiloxanes containing an Si-bonded hydroxyl group in each of the terminal units and thereafter removing the low boiling constituents by distillation.Type: GrantFiled: December 7, 1988Date of Patent: February 20, 1990Assignee: Wacker-Chemie GmbHInventors: Karl-Heinrich Wegehaupt, Karl Braunsperger, Gunter von Au, Fridolin Stary
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Patent number: 4897459Abstract: Sodium fluorosilanolate catalyst is disclosed which has improved effectiveness as a catalyst to produce fluorosilicone polymer and which at the same time improves fluorosilicone polymer purity.Type: GrantFiled: November 25, 1987Date of Patent: January 30, 1990Assignee: General Electric CompanyInventor: Edwin R. Evans
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Patent number: 4855472Abstract: Oligomeric siloxanol mixtures containing siloxanolsof the formulaHO--SiR.sub.2 O[SiR.sub.2 O--.sub.n Hand those of the formulaR.sub.3 SiO--[SiR.sub.2 O--.sub.m Hwhere R represents the same or different monovalent hydrocarbon radicals, monovalent halogenated hydrocarbon radicals having from 1 to 18 carbon atoms or hydrogen atoms and n and m are the same or different integers are prepared by hydrolyzing a mixture containing at least one compound of the formula R.sub.3 SiCl and at least one compound of the formula R.sub.2 SiCl.sub.2. These oligomeric siloxanol mixtures can be reacted with the terminal Si-bonded hydroxyl groups of .alpha., .omega.-dihydroxypolyorganosiloxanes.Type: GrantFiled: June 19, 1987Date of Patent: August 8, 1989Assignee: Wacker- Chemie GmbHInventor: Jurgen Burkhardt
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Patent number: 4772737Abstract: Admixtures of cyclic and linear diorganopolysiloxanes, relatively rich in cyclic species, are produced by hydrolyzing a diorganodichlorosilane, in an aqueous hydrochloric acid medium, in the presence of an effective amount of at least one amphoteric surface-active agent, characteristically at least one compound of the formula: ##STR1## The medium of hydrolysis is facilely separated into an aqueous phase and a cyclic oligomer-enriched siloxane phase essentially devoid of surfactant(s).Type: GrantFiled: October 23, 1987Date of Patent: September 20, 1988Assignee: Rhone-Poulenc ChimieInventors: Francoise Lartigue-Peyrou, Hugues Porte
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Patent number: 4762937Abstract: Linear organopolysiloxanediols are prepared by continuously introducing cyclic organopolysiloxanes, water in an amount of at least 14 mols per gram atom of silicon contained in the cyclic organopolysiloxanes used and water-soluble acid into a recirculating reactor and thereafter separating the aqueous phase from the organopolysiloxanediols more or less immediately after the reaction mixture exits from the recirculating reactor.Type: GrantFiled: August 6, 1987Date of Patent: August 9, 1988Assignee: Wacker-Chemie GmbHInventors: Ralph Ottlinger, Rudolf Reitmeier
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Patent number: 4722987Abstract: An oligomer or a mixture of organopolysiloxane oligomers is polymerized in the presence of a strong acid, e.g. trifluoromethane sulfonic acid, as the catalyst to give an organopolysiloxane containing a considerable amount of silanolic hydroxy groups at the molecular chain ends. Thereafter, the mixture is admixed with water and a hexaorganodisilazane or triorganosilyl amine compound in combination so as to neutralize the acid catalyst by the ammonia produced by the hydrolysis of the disilazane or silyl amine compound with simultaneous silylation of the terminal hydroxy groups. Thus, the organopolysiloxane contains a greatly decreased amount of the residual silanolic hydroxy groups at the molecular chain ends to be imparted with remarkably improved heat stability.Type: GrantFiled: August 14, 1986Date of Patent: February 2, 1988Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayuki Ikeno, Hiroshi Inomata
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Patent number: 4694040Abstract: The invention provides a novel means for providing a highly heat-resistant and corrosion-resistant coating film on the surface of a substrate such as a semiconductor silicon wafer or glass plate by coating the surface with a liquid coating composition which is a solution of an oligomeric organopolysiloxane as a partial dehydration-condensation product of a monohydrocarbylsilane triol RSi(OH).sub.3, optionally, with admixture of a dihydrocarbylsilane diol R.sub.2 Si(OH).sub.2, R being a monovalent hydrocarbon group, e.g. methyl or phenyl, in an organic solvent followed by baking of the coated substrate to convert the coating layer into a cured resin film.Type: GrantFiled: August 25, 1986Date of Patent: September 15, 1987Assignee: Tokyo Denshi Kagaku Kabushiki KaishaInventors: Akira Hashimoto, Toshihiro Nishimura, Muneo Nakayama, Hisashi Nakane, Shozo Toda
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Patent number: 4642356Abstract: New organosilicon compounds of the formula ##STR1## R represents a hydrogen radical with 1 to 6 carbon atoms, or a phenyl radical;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and represent hydrogen or methyl radicals;R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are the same or different and represent hydrogen, fluorine or hydrocarbon radicals with 1 to 8 carbon atoms, or fluorinated hydrocarbon radicals, in which at least one R.sup.5, R.sup.6 R.sup.7 or R.sup.8 radicals must be a fluorine or a fluorinated hydrocarbon radical;Y is a hydrolyzable radical, hydroxyl radical or organosiloxanyl radical;A represents ##STR2## in which R.sup.9 may be the same or different and represents a hydrogen or a methyl radical; anda has a value of 0, 1, 2, or 3.Type: GrantFiled: June 14, 1985Date of Patent: February 10, 1987Assignee: Th. Goldschmidt AGInventors: Jaroslav Langner, Christian Weitemeyer
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Patent number: 4618665Abstract: A method of preparing a copolymer of methyl(2-phenylpropyl)siloxy units and dialkylsiloxy units is disclosed. The method hydrolyzes methyl(2-phenylpropyl)dichlorosilane to yield a reaction product of primarily methyl(2-phenylpropyl)disiloxanediol, then copolymerizes the reaction product with dialkylcyclosiloxane to give the copolymer. The copolymer has a crystallinity point of less than -50.degree. C. It is useful in producing silicone elastomers and sealants having a comparably low crystallinity point.Type: GrantFiled: January 13, 1986Date of Patent: October 21, 1986Assignee: Dow Corning CorporationInventors: Joseph T. Braun, Schuyler B. Smith
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Patent number: 4611042Abstract: A xylene-soluble, resinous copolymer containing SiO.sub.2 units, trimethylsiloxane units, and alkenyldimethylsiloxane units such as 5-hexenyldimethylsiloxane units is disclosed. The resinous copolymer is useful as a component in silicone coatings, especially silicone release coatings, to provide intermediate range release forces against adhesives. The higher alkenyl functionality provides faster reaction with other coating components and reduced odor during cure of UV curable mercaptosilicone compositions.Type: GrantFiled: October 3, 1985Date of Patent: September 9, 1986Assignee: Dow Corning CorporationInventors: Stacia A. Rivers-Farrell, Antony P. Wright
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Patent number: 4609751Abstract: A method is provided for hydrolyzing chlorosilanes, for example, dimethyldichlorosilane, to produce dimethylpolysiloxane hydrolyzate and an aqueous solution of hydrogen chloride along with anhydrous hydrogen chloride. Chlorosilane hydrolysis is effected in the presence of a substantially stoichiometric equivalence of water which results in the direct generation of anhydrous hydrogen chloride and a saturated aqueous hydrogen chloride solution. The saturated aqueous solution of hydrogen chloride can be recycled to the chlorosilane hydrolysis step.Type: GrantFiled: August 18, 1983Date of Patent: September 2, 1986Assignee: General Electric CompanyInventor: Abraham L. Hajjar
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Patent number: 4539232Abstract: A method for producing solventless liquid organopolysiloxanes is disclosed. The method involves hydrolyzing an organo silicon composition comprising at least one compound having the general formulaY.sub.(4-n) Si(OR).sub.nwhere Y is phenyl or a primary or secondary alkyl group having from one to four carbon atoms, R is an alkyl group having from one to three carbon atoms, and n is an integer from one to four, and wherein the ratio of OR groups to silicon atoms in the composition is from 2.3:1 to 3.1:1. The products of hydrolysis are then heated to cause substantial siloxane formation by condensation and to distill water and alcohol by-products. Heating is continued until the water content of the resulting siloxane composition is less than 1 percent. The purity of the organo silicon composition, the amount of water used for hydrolysis, the amount of acid present during hydrolysis, and the heating of the organopolysiloxane are so controlled that the solventless organopolysiloxane has a viscosity at 25.degree. C.Type: GrantFiled: August 29, 1983Date of Patent: September 3, 1985Assignee: Owens-Illinois, Inc.Inventors: Alfred J. Burzynski, Edward J. Stengle
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Patent number: 4497942Abstract: A method is provided for hydrolyzing chlorosilanes utilizing a static tubular reactor. A substantial reduction in hydrolysis residence time is achieved.Type: GrantFiled: December 14, 1983Date of Patent: February 5, 1985Assignee: General Electric CompanyInventors: Yaw D. Yeboah, Michael P. Venditti
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Patent number: 4474933Abstract: The present invention relates to resin mixtures which are fluid at temperatures up to 100.degree. C. and which crosslink either at elevated temperature or under the influence of moisture. Thermal crosslinking takes place at temperatures of 100.degree. C. and up, preferably at about 120.degree. C. The mixtures contain one or more mutually compatible polymers containing hydroxyl groups, in which at least 5% and not more than 90% of the hydroxyl groups are replaced by alkoxysilyl groups. The introduction of the alkoxysilyl groups is accomplished by the reaction of a diisocyanate with a hydroxyl group on the polymer, on the one hand, and with an aminosilane or mercaptosilane ester on the other. On the basis of their fluid-to-viscous consistency at room temperature or moderately elevated temperature, the resins can be applied in a thin coating and easily crosslinked in situ.Type: GrantFiled: June 2, 1983Date of Patent: October 2, 1984Assignee: Dynamit Nobel AGInventors: Hans Huber, Eduard Hansel, Gerhard Geier
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Patent number: 4448981Abstract: An improved process for making an alkyl halide and organosiloxanes from a dialkyldialkoxysilane and a hydrogen halide is disclosed. Dialkyldialkoxysilane and hydrogen halide are simultaneously introduced at respective feed points into a column containing hydrogen halide under reflux in such proportions that the amount of hydrogen halide introduced into the column is at a stoichiometric excess over the dialkyldialkoxysilane. In preferred embodiments, the hydrogen halide is hydrogen chloride; the dialkyldialkoxysilane is dimethyldimethoxysilane; the alkyl halide is methyl chloride; and the organosiloxanes are predominantly of the cyclic type.Type: GrantFiled: May 13, 1983Date of Patent: May 15, 1984Assignee: General Electric CompanyInventor: Luisito A. Tolentino
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Patent number: 4443351Abstract: Compositions are disclosed consisting essentially of: (A) a polydiorganosiloxane fluid in which the organic radicals are predominantly or wholly methyl radicals; (B) a chlorendate diester; (C) a lubricant compound which is an antimony or lead compound of a dialkyldithiocarbamate or dialkylphosphorodithioate; and (D) a block copolymer comprising blocks of polydimethylsiloxane and blocks of polybutadiene or hydrogenated polybutadiene. These compositions are useful as concentrates for replenishing polydiorganosiloxane hydraulic fluids that have become depleted in additives (B) and (C), and as hydraulic fluids having improved resistance to settling of the lubricant compound at low temperatures.Type: GrantFiled: November 1, 1982Date of Patent: April 17, 1984Assignee: Dow Corning CorporationInventor: Joseph W. Keil
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Patent number: 4399193Abstract: Hydrophilic coatings are obtained by applying to a substrate a composition containing an aqueous soluble organopolysiloxane which is capable of being crosslinked by the addition of Si-bonded hydrogen atoms to SiC-bonded aliphatic multiple bonds, and having at least one oxyalkylene unit bonded to a silicon atom and an aqueous soluble catalyst which promotes the addition of Si-bonded hydrogen atoms to the SiC-bonded aliphatic multiple bonds and thereafter crosslinking the organopolysiloxane by the addition of the Si-bonded hydrogen atoms to the SiC-bonded aliphatic multiple bonds to form a hydrophilic coating on the substrate. The aqueous soluble organopolysiloxane may be obtained from a mixture consisting of equal parts of a mixed hydrolysate, prepared from 1.7 moles of dimethyldichlorosilane, 1 mole of [acetoxy-(hexaethyleneoxy)propyl]-methyldichlorosilane and 0.Type: GrantFiled: August 24, 1981Date of Patent: August 16, 1983Assignee: Wacker-Chemie GmbHInventors: Gerhard Preiner, Johann Muller, Karl-Heinrich Wegehaupt
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Patent number: 4399266Abstract: A laddery lower alkylpolysilsesquioxane represented by the formula: ##STR1## wherein R and R' represent same or different lower alkyl groups, and n represents an average degree of polymerization, said laddery lower alkylpolysilsesquioxane having a heat-resistant thin film-formability, characterized in that 15 to 30% by weight of the lower alkylpolysilsesquioxane is occupied by the portion having a standard polystyrene-reduced molecular weight of 20,000 or less as measured by gel permeation chromatography. Said silicone resin in which R and R' are methyl is prepared by dissolving CH.sub.3 SiCl.sub.3 in a ketone or an ether, adding water to this solution with stirring to hydrolyze CH.sub.3 SiCl.sub.3, condensing the hydrolyzate and, if necessary, subjecting the resulting condensate to a treatment for adjusting the proportion of the low molecular weight portion in the product.Type: GrantFiled: March 2, 1982Date of Patent: August 16, 1983Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshio Matsumura, Ikuo Nozue, Osahiko Tomomitsu, Takashi Ukachi, Taro Suminoe
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Patent number: 4395563Abstract: Alkoxysilanes are hydrolyzed with water in the presence of various hydrolysis catalysts. The hydrolysis catalysts include the solid oxides of the Group IIa metals and solid acid catalysts. The solid acid catalysts are used in conjunction with neutralizing agents and optionally with condensation catalysts.Generally, the process for hydrolyzing alkoxysilanes comprises: mixing an alkoxysilane, a stoichiometric excess of water and an effective catalytic amount of hydrolysis catalyst selected from the group consisting of a solid oxide of a Group IIa metal, a solid acid catalyst and mixtures thereof; neutralizing the hydrolysis mixture with a sufficient amount of neutralizing agent, for example, magnesium oxide; and separating the hydrolysis product from the mixture. When a Group IIa metal oxide hydrolysis catalyst is used, the liquid portion of the hydrolysate is neutral, and no additional neutralizing agent is required in the mixture.Type: GrantFiled: October 29, 1981Date of Patent: July 26, 1983Assignee: General Electric CompanyInventor: Susan E. Hayes
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Patent number: 4376210Abstract: Novel radiation-curable, liquid vinyl organosilicon polymers and coating compositions which are free of volatile solvent(s) and which are adapted to be applied to a substrate and cured rapidly by exposure to radiation to form release coatings having good release properties with respect to adhesives, and methods for producing such polymers and compositions and for applying and curing such release coatings.Type: GrantFiled: February 2, 1981Date of Patent: March 8, 1983Assignee: Pitney Bowes Inc.Inventor: Mike S. H. Chang
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Patent number: 4366324Abstract: The invention provides a novel continuous process for concurrently producing methyl chloride and organosiloxanes by the reaction of an organochlorosilane and methyl alcohol in an aqueous reaction medium at 70.degree. to 150.degree. C. Different from conventional processes, the aqueous reaction medium contains no catalyst so that the problems inherent to the use of a large amount of a catalyst can be avoided. In the inventive process, the feed rates of the reactants are controlled so as to keep the concentration of hydrogen chloride in the aqueous reaction medium not to exceed the azeotropic concentration thereof at the temperature and under the pressure of operation. These conditions are critical to reduce the loss of hydrogen chloride by dissipation into the gaseous phase resulting in a remarkably high yield of methyl chloride from the standpoint of both the conversion of chlorine content and the space-time yield of the reaction vessel.Type: GrantFiled: November 18, 1981Date of Patent: December 28, 1982Assignee: Shin-Etsu Chemical Co. Ltd.Inventors: Kiichi Habata, Kesazi Ichikawa, Mutsuo Shimizu
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Patent number: 4348533Abstract: High yields of linear dimethylpolysiloxanes are obtained by reacting dimethyldichlorosilane with methanol in contact with certain quarternary ammonium halides, such as methyl pyridinium chloride, at a pressure of 15 to 100 psi.Type: GrantFiled: October 13, 1981Date of Patent: September 7, 1982Assignee: Dow Corning CorporationInventors: Allan M. Alanko, David R. Salverson
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Patent number: 4321401Abstract: A process for the preparation of partial hydrolyzates of orthosilicic acid tetra(alkoxyalkyl) ester having a stable shelf life is described by hydrolysis of a silicic acid tetra(alkoxyalkyl) ester with water, suitably in the presence of an acid and optionally in the presence of a solvent, wherein the stoichiometrically necessary amount of water is present at the commencement of the reaction.Type: GrantFiled: August 25, 1980Date of Patent: March 23, 1982Assignee: Dynamit Nobel AktiengesellschaftInventors: Heinz Nestler, Friedhelm Schnippering
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Patent number: 4308393Abstract: Addition to organosilicon compounds having at least one alkyl group attached to a silicon atom, at least one hydrogen atom being attached to the carbon atom adjacent the silicon atom, of a fluorocompound, which may be a fluoroolefin, a perfluoroketone, or a perfluoroether having a carbon-carbon double bond in .alpha.-position to the ether oxygen atom, give fluorine-containing organosilicon compounds. These adducts may be liquid or solid and are useful as (1) lubricants and sealants for automotive and aerospace industries (2) fire-resistant hydraulic fluids, and (3) siloxane elastomers having good oil and lubricant resistance.Type: GrantFiled: October 8, 1980Date of Patent: December 29, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Apotheker
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Patent number: 4287353Abstract: A method for producing silanol chain-stopped fluoroalkyl polysiloxane fluids is disclosed. Fluoroalkyl substituted cyclic trisiloxanes are reacted with water, a catalyst and a polyethyleneglycol ether promoter to produce a fluorosilicone polymer of the desired molecular weight and viscosity.Type: GrantFiled: November 9, 1979Date of Patent: September 1, 1981Assignee: General Electric CompanyInventor: Ben A. Bluestein
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Patent number: 4281147Abstract: A process for the preparation of aqueous solutions of alkali organosiliconates in which organoalkoxypolysiloxanes of the formula ##EQU1## in which R.sup.1 is an alkyl residue with 1 to 3 carbon atoms, a vinyl residue and/or a phenyl residue,R.sup.2 is an alkyl residue with 1 to 4 carbon atoms,a is a number .ltoreq.2, andx is 1 to 1.25,are reacted with aqueous solutions of sodium hydroxide or potassium hydroxide having a concentration of 0.7 to 0.9 mole/100 g at temperatures .gtoreq.80.degree. C. The liberated alcohol R.sup.2 OH may be distilled and/or the concentration adjusted to the desired value by the addition of water. With the present invention, alkali chloride-free alkali organosiliconate solutions having high concentration can be obtained while avoiding a filtration step.Type: GrantFiled: March 3, 1980Date of Patent: July 28, 1981Assignee: Th. Goldschmidt AGInventors: Gotz Koerner, Vaclav Kropac, Harald Rau
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Patent number: 4272624Abstract: A process for producing diorganopolysiloxane gums having a viscosity from 1,000 to 100,000,000 centipoise at 25.degree. C., where at least one of the organo substituent groups on the silicon atoms is an aliphatic radical of more than three carbon atoms comprising reacting a cyclic tetrasiloxane or a mixture of cyclic tetrasiloxanes at a temperature in the range of 0.degree. to 90.degree. C. and in the presence of 5 to 300 parts per million of a catalyst selected from the class consisting of cesium hydroxide and ##STR1## where R.sup.2 is selected from the class consisting of alkyl radicals of 1 to 8 carbon atoms, cycloalkyl radicals of 4 to 8 carbon atoms and phenyl, B is selected from the class consisting of nitrogen and phosphorous, R.sup.3 is selected from the class consisting of alkyl radicals of 1 to 8 carbon atoms, cycloalkyl radicals of 4 to 8 carbon atoms, phenyl, siloxane chains of the unit formula R.sub.a.sup.4 SiO.sub.(4-a/2) and mixtures thereof, where R.sup.Type: GrantFiled: June 10, 1975Date of Patent: June 9, 1981Assignee: General Electric CompanyInventor: John S. Razzano
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Patent number: RE31324Abstract: Addition to organosilicon compounds having at least one alkyl group attached to a silicon atom, at least one hydrogen atom being attached to the carbon atom adjacent the silicon atom, of a fluorocompound, which may be a fluoroolefin.[., a perfluoroketone,.]. or a perfluoroether having a carbon-carbon double bond in .alpha.-position to the ether oxygen atom, give fluorine-containing organosilicon compounds. These adducts may be liquid or solid and are useful as (1) lubricants and sealants for automotive and aerospace industries (2) fire-resistant hydraulic fluids, and (3) siloxane elastomers having good oil and lubricant resistance.Type: GrantFiled: April 12, 1982Date of Patent: July 26, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Apotheker, deceased