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)
  • Patent number: 5576408
    Abstract: 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: Grant
    Filed: August 24, 1995
    Date of Patent: November 19, 1996
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Minoru Igarashi, Masaharu Takahashi
  • Patent number: 5563231
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: October 8, 1996
    Assignee: Bayer Corporation
    Inventors: Lloyd Barringer, Jr., Thomas P. Bellina, Brad A. Ziegler
  • Patent number: 5539137
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: July 23, 1996
    Assignee: General Electic Company
    Inventors: Larry N. Lewis, Susan A. Nye
  • Patent number: 5508369
    Abstract: 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: Grant
    Filed: August 17, 1994
    Date of Patent: April 16, 1996
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Yamazaki, Nobuyuki Suzuki, Shinichi Morioka, Shoji Ichinohe
  • Patent number: 5492992
    Abstract: 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: Grant
    Filed: December 5, 1994
    Date of Patent: February 20, 1996
    Assignee: Dow Corning S.A.
    Inventor: Jean M. Gilson
  • Patent number: 5476916
    Abstract: 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: Grant
    Filed: November 29, 1994
    Date of Patent: December 19, 1995
    Assignee: Wacker-Chemie GmbH
    Inventors: Bernd Pachaly, Gerhard Nagy, Wolfgang Jacques, Robert Christa
  • Patent number: 5436360
    Abstract: 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: Grant
    Filed: September 8, 1994
    Date of Patent: July 25, 1995
    Assignee: Korea Institute of Science and Technology
    Inventors: Il N. Jung, Bok R. Yoo, Bong W. Lee, Seung H. Yeon
  • Patent number: 5436358
    Abstract: 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: Grant
    Filed: September 8, 1994
    Date of Patent: July 25, 1995
    Assignee: Korea Institute of Science and Technology
    Inventors: Il N. Jung, Bok R. Yoo, Bong W. Lee
  • Patent number: 5369206
    Abstract: 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: Grant
    Filed: January 31, 1994
    Date of Patent: November 29, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masanao Kamei, Tomohisa Suzuki
  • Patent number: 5276173
    Abstract: 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: Grant
    Filed: October 5, 1992
    Date of Patent: January 4, 1994
    Assignee: Dow Corning Corporation
    Inventors: Ollie W. Marko, Robert D. Steinmeyer
  • Patent number: 5262558
    Abstract: 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: Grant
    Filed: August 20, 1992
    Date of Patent: November 16, 1993
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventors: Hideki Kobayashi, Wataru Nishiumi
  • Patent number: 5254654
    Abstract: 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: Grant
    Filed: July 10, 1992
    Date of Patent: October 19, 1993
    Assignee: Temple University of the Commonwealth System of Higher Education
    Inventors: Mark A. Buese, Sejal Patel
  • Patent number: 5247043
    Abstract: Low-molecular-weight phenylpolysilsesquioxanes that have narrow molecular weight distribution and a method for the preparation of the same.
    Type: Grant
    Filed: July 24, 1992
    Date of Patent: September 21, 1993
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventor: Hisataka Nakashima
  • Patent number: 5233067
    Abstract: 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: Grant
    Filed: May 8, 1990
    Date of Patent: August 3, 1993
    Assignee: Rogers Corporation
    Inventors: Gwo Swei, Kenneth W. Kristal
  • Patent number: 5169970
    Abstract: 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: Grant
    Filed: June 26, 1989
    Date of Patent: December 8, 1992
    Assignee: Toshiba Silicone Co., Ltd.
    Inventor: Nobuaki Ohkawa
  • Patent number: 5079291
    Abstract: 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: Grant
    Filed: November 20, 1989
    Date of Patent: January 7, 1992
    Assignee: General Electric Company
    Inventor: Edwin R. Evans
  • Patent number: 5057620
    Abstract: 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: Grant
    Filed: August 7, 1990
    Date of Patent: October 15, 1991
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yoshio Inoue, Naoki Omura
  • Patent number: 5011962
    Abstract: 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: Grant
    Filed: May 30, 1990
    Date of Patent: April 30, 1991
    Assignee: Wacker-Chemie GmbH
    Inventors: Gerhard Staiger, Johann Muller, Walter Doskocil
  • Patent number: 4977289
    Abstract: 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: Grant
    Filed: November 16, 1989
    Date of Patent: December 11, 1990
    Assignee: General Electric Company
    Inventor: Edwin R. Evans
  • Patent number: 4977290
    Abstract: 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: Grant
    Filed: November 20, 1989
    Date of Patent: December 11, 1990
    Assignee: General Electric Company
    Inventors: Edwin R. Evans, Paul Maitoza
  • Patent number: 4962221
    Abstract: 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: Grant
    Filed: March 12, 1990
    Date of Patent: October 9, 1990
    Assignee: Dow Corning Corporation
    Inventors: Arnold R. Huntress, Daryl D. Landis, Donald E. McVannel, Timothy Allen
  • Patent number: 4923950
    Abstract: 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: Grant
    Filed: April 28, 1988
    Date of Patent: May 8, 1990
    Assignee: Centre National de la Recherche Scientifique (CNRS)
    Inventors: Lucienne Ravaine, Michel B. Armand, Yves Charbouillot, Abdelkader Hammou
  • Patent number: 4902813
    Abstract: 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: Grant
    Filed: December 7, 1988
    Date of Patent: February 20, 1990
    Assignee: Wacker-Chemie GmbH
    Inventors: Karl-Heinrich Wegehaupt, Karl Braunsperger, Gunter von Au, Fridolin Stary
  • Patent number: 4897459
    Abstract: 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: Grant
    Filed: November 25, 1987
    Date of Patent: January 30, 1990
    Assignee: General Electric Company
    Inventor: Edwin R. Evans
  • Patent number: 4855472
    Abstract: 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: Grant
    Filed: June 19, 1987
    Date of Patent: August 8, 1989
    Assignee: Wacker- Chemie GmbH
    Inventor: Jurgen Burkhardt
  • Patent number: 4772737
    Abstract: 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: Grant
    Filed: October 23, 1987
    Date of Patent: September 20, 1988
    Assignee: Rhone-Poulenc Chimie
    Inventors: Francoise Lartigue-Peyrou, Hugues Porte
  • Patent number: 4762937
    Abstract: 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: Grant
    Filed: August 6, 1987
    Date of Patent: August 9, 1988
    Assignee: Wacker-Chemie GmbH
    Inventors: Ralph Ottlinger, Rudolf Reitmeier
  • Patent number: 4722987
    Abstract: 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: Grant
    Filed: August 14, 1986
    Date of Patent: February 2, 1988
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayuki Ikeno, Hiroshi Inomata
  • Patent number: 4694040
    Abstract: 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: Grant
    Filed: August 25, 1986
    Date of Patent: September 15, 1987
    Assignee: Tokyo Denshi Kagaku Kabushiki Kaisha
    Inventors: Akira Hashimoto, Toshihiro Nishimura, Muneo Nakayama, Hisashi Nakane, Shozo Toda
  • Patent number: 4642356
    Abstract: 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: Grant
    Filed: June 14, 1985
    Date of Patent: February 10, 1987
    Assignee: Th. Goldschmidt AG
    Inventors: Jaroslav Langner, Christian Weitemeyer
  • Patent number: 4618665
    Abstract: 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: Grant
    Filed: January 13, 1986
    Date of Patent: October 21, 1986
    Assignee: Dow Corning Corporation
    Inventors: Joseph T. Braun, Schuyler B. Smith
  • Patent number: 4611042
    Abstract: 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: Grant
    Filed: October 3, 1985
    Date of Patent: September 9, 1986
    Assignee: Dow Corning Corporation
    Inventors: Stacia A. Rivers-Farrell, Antony P. Wright
  • Patent number: 4609751
    Abstract: 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: Grant
    Filed: August 18, 1983
    Date of Patent: September 2, 1986
    Assignee: General Electric Company
    Inventor: Abraham L. Hajjar
  • Patent number: 4539232
    Abstract: 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: Grant
    Filed: August 29, 1983
    Date of Patent: September 3, 1985
    Assignee: Owens-Illinois, Inc.
    Inventors: Alfred J. Burzynski, Edward J. Stengle
  • Patent number: 4497942
    Abstract: A method is provided for hydrolyzing chlorosilanes utilizing a static tubular reactor. A substantial reduction in hydrolysis residence time is achieved.
    Type: Grant
    Filed: December 14, 1983
    Date of Patent: February 5, 1985
    Assignee: General Electric Company
    Inventors: Yaw D. Yeboah, Michael P. Venditti
  • Patent number: 4474933
    Abstract: 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: Grant
    Filed: June 2, 1983
    Date of Patent: October 2, 1984
    Assignee: Dynamit Nobel AG
    Inventors: Hans Huber, Eduard Hansel, Gerhard Geier
  • Patent number: 4448981
    Abstract: 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: Grant
    Filed: May 13, 1983
    Date of Patent: May 15, 1984
    Assignee: General Electric Company
    Inventor: Luisito A. Tolentino
  • Patent number: 4443351
    Abstract: 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: Grant
    Filed: November 1, 1982
    Date of Patent: April 17, 1984
    Assignee: Dow Corning Corporation
    Inventor: Joseph W. Keil
  • Patent number: 4399193
    Abstract: 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: Grant
    Filed: August 24, 1981
    Date of Patent: August 16, 1983
    Assignee: Wacker-Chemie GmbH
    Inventors: Gerhard Preiner, Johann Muller, Karl-Heinrich Wegehaupt
  • Patent number: 4399266
    Abstract: 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: Grant
    Filed: March 2, 1982
    Date of Patent: August 16, 1983
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Yoshio Matsumura, Ikuo Nozue, Osahiko Tomomitsu, Takashi Ukachi, Taro Suminoe
  • Patent number: 4395563
    Abstract: 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: Grant
    Filed: October 29, 1981
    Date of Patent: July 26, 1983
    Assignee: General Electric Company
    Inventor: Susan E. Hayes
  • Patent number: 4376210
    Abstract: 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: Grant
    Filed: February 2, 1981
    Date of Patent: March 8, 1983
    Assignee: Pitney Bowes Inc.
    Inventor: Mike S. H. Chang
  • Patent number: 4366324
    Abstract: 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: Grant
    Filed: November 18, 1981
    Date of Patent: December 28, 1982
    Assignee: Shin-Etsu Chemical Co. Ltd.
    Inventors: Kiichi Habata, Kesazi Ichikawa, Mutsuo Shimizu
  • Patent number: 4348533
    Abstract: 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: Grant
    Filed: October 13, 1981
    Date of Patent: September 7, 1982
    Assignee: Dow Corning Corporation
    Inventors: Allan M. Alanko, David R. Salverson
  • Patent number: 4321401
    Abstract: 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: Grant
    Filed: August 25, 1980
    Date of Patent: March 23, 1982
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Heinz Nestler, Friedhelm Schnippering
  • Patent number: 4308393
    Abstract: 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: Grant
    Filed: October 8, 1980
    Date of Patent: December 29, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David Apotheker
  • Patent number: 4287353
    Abstract: 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: Grant
    Filed: November 9, 1979
    Date of Patent: September 1, 1981
    Assignee: General Electric Company
    Inventor: Ben A. Bluestein
  • Patent number: 4281147
    Abstract: 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: Grant
    Filed: March 3, 1980
    Date of Patent: July 28, 1981
    Assignee: Th. Goldschmidt AG
    Inventors: Gotz Koerner, Vaclav Kropac, Harald Rau
  • Patent number: 4272624
    Abstract: 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: Grant
    Filed: June 10, 1975
    Date of Patent: June 9, 1981
    Assignee: General Electric Company
    Inventor: John S. Razzano
  • Patent number: RE31324
    Abstract: 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: Grant
    Filed: April 12, 1982
    Date of Patent: July 26, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: David Apotheker, deceased