Silicon And The Oxy Of The -coo- Group Are Bonded Directly To The Same Hydrocarbon Group Patents (Class 556/440)
  • Patent number: 5446183
    Abstract: The invention discloses novel ester emulsifiers. Compounds of the invention are made by reacting (a) a carboxy silicone, and (b) a fatty alcohol alkoxylate containing 4 to 20 carbon atoms. The compounds of the invention by virtue of (i) the silicone group, (ii) the fatty alcohol group and (iii) the polyoxyalkylene present in the compound are extremely efficient emulsifiers for a variety of oils at heretofore unknown levels.
    Type: Grant
    Filed: February 15, 1995
    Date of Patent: August 29, 1995
    Assignee: Siltech Inc.
    Inventor: Anthony J. O'Lenick, Jr.
  • Patent number: 5430166
    Abstract: Silanes of the general formula ##STR1## are prepared wherein R.sup.1, R.sup.2 and R.sup.3 in the molecule are the same or different and represent aliphatic hydrocarbon groups,R.sup.4 is a divalent hydrocarbon group with 3 to 14 carbon atoms,R.sup.5 is a group having the formula --O(CH.sub.2).sub.b -- or a polyether group having the formula --(OC.sub.n H.sub.2n).sub.c --, wherein b has a value of 1 to 6, n has an average value of 2 to 2.5 and c has a value of 1 to 10,R.sup.6 is an --OSO.sub.3 X group or an --OR.sup.7 group, wherein X is a hydrogen, an alkali or an optionally substituted ammonium ion and R.sup.7 is an alkyl group with 1 to 4 carbon atoms or an acetyl group,a is 0 or 1,with the proviso that, when R.sup.6 represents the --OR.sup.7 group, a=1. The silanes are biologically degradable, resistant to hydrolysis and have pronounced surfactant properties.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: July 4, 1995
    Assignee: Th. Goldschmidt AG
    Inventors: Klaus-Dieter Klein, Wilfried Knott, Gotz Koerner
  • Patent number: 5412134
    Abstract: The protected cyclobutanone of the formula ##STR1## is treated with a dialkylaluminum chloride, an alkylaluminum dichloride, a trialkylaluminum compound, diphenylsilane in the presence of tris(triphenylphosphine) rhodium (I) chloride, or iridium tetrachloride to yield the corresponding diprotected cyclobutanol. This compound is useful as an intermediate in the preparation of antiviral agents.
    Type: Grant
    Filed: May 26, 1992
    Date of Patent: May 2, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Janak Singh, Gregory S. Bisacchi, Richard H. Mueller
  • Patent number: 5399651
    Abstract: Adhesion additives for curable organosiloxane compositions comprise (I) a silane containing at least one alkoxy or enoloxy group, the remaining valences of the silicon atom being satisfied by groups bonded to silicon through oxygen and containing at least one H.sub.2 C.dbd.CR-- radical, where R is hydrogen or monovalent hydrocarbon, and (II) at least one organosilicon compound comprising (a) at least one group capable of participating in a hydrosilation reaction, and (b) at least one silicon-bonded alkoxy, enoloxy or silanol group.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: March 21, 1995
    Assignee: Dow Corning Corporation
    Inventors: Theresa E. Gentle, Michael A. Lutz
  • Patent number: 5391677
    Abstract: A novel acrylic-functional organopolysiloxane is proposed which has a plural number of silicon-bonded (meth)acryloxyalkyl groups at each molecular chain end along with one or more of silicon-bonded alkoxy groups. The organopolysiloxane exhibits high curability by the irradiation with ultraviolet light or dual curability either by the ultraviolet irradiation or by the dealcoholation condensation reaction in a moisture-containing atmosphere. The acrylic-functional organopolysiloxane is prepared by the dealcoholation condensation reaction between a starting organopolysiloxane having a plural number of silicon-bonded alkoxy groups at each molecular chain end and a (meth)acryloxyalkyl dimethyl silanol compound in the presence of a specific condensation catalyst which is a divalent tin compound such as tin (II) dioctoate promoting the dealcoholation condensation but suppressing the silanol condensation reaction between the moleculaes of the (meth)acryloxyalkyl dimethyl silanol compound.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: February 21, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masatoshi Arai, Takafumi Sakamoto, Kazutoshi Fujioka
  • Patent number: 5387105
    Abstract: Disclosed in the present application is a method of curing a dental impression material by passing actinic light through a tray while the tray is in contact with the impression making composition, a new dental impression composition that is polymerizable by having an initiator activated by actinic light within the visible light range of 360 to 600 nanometers, a new composition of matter that is a compound having at least two terminal acrylate unsaturations and an organosilicone containing backbone and a new method of forming dental prosthetics by directly forming against the soft tissue of the oral cavity and then setting with visible light curing.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: February 7, 1995
    Assignee: Dentsply Research & Development Corp.
    Inventors: Emery W. Dougherty, Wu-Lan Wang
  • Patent number: 5380901
    Abstract: The present invention provides a process for converting a hydrophobic siloxane diacrylate, an aromatic fluorinated diacrylate and a hydrophilic polyethylene glycol diacrylate to their respective multifunctional oligomers. Bis(4-acryloxybutyl)tetramethyldisiloxane, prepared from the corresponding diol, is converted to relatively low viscosity, multifunctional oligomers with the use of DMSO. The hydrophilic monomer, polyethylene glycol 400 diacrylate, formed more viscous, water soluble oligomeric products without the need for a solvent. Characterization of these oligomers by infrared spectroscopy and .sup.1 H NMR supports the assigned structures. Because of the predominant 1,6-arrangement of double bonds in these oligomers, they have a propensity to undergo cyclopolymerization as well as the usual crosslinking associated with the free radical polymerization of multifunctional monomers and oligomers.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: January 10, 1995
    Assignee: The United States of America as represented by the Secretary of Commerce
    Inventors: Joseph M. Antonucci, Jeffrey W. Stansbury, Guo-Wei Cheng
  • Patent number: 5376294
    Abstract: An electrorheological fluid comprising a dielectric particle as the dispersed phase, an insulating oil as the dispersing medium, and an additive, the additive being substantially insoluble in the dispersing medium, and being a composite containing a polysiloxane-containing structural unit (A), and at least one dispersed phase absorbing chain-containing structural unit (B) selected from the group consisting of an alkylene oxide chain-containing structural unit (B-1), a nitrogen atom chain-containing structural unit (B-2), and a long hydrocarbon chain-containing structural unit (B-3).
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: December 27, 1994
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Izuho Okada, Yoshinobu Asako, Kiyomi Arimatsu, Minoru Kobayashi, Satoru Ono, Ryuji Aizawa
  • Patent number: 5371262
    Abstract: Novel hydroxymethyltrialkoxysilanes of the formula: ##STR1## are produced by transesterifying a carboxylic acid ester of hydroxymethyltrialkoxysilane with an alcohol, and distilling the reaction mixture to remove the carboxylate of the alcohol. The carboxylic acid ester of hydroxymethyltrialkoxysilane is prepared by the reaction of an alkali metal carboxylate with chloromethyltrialkoxysilane, which in turn is prepared by the reaction of a trialkylorthoester with chloromethyltrichlorosilane by heating to reflux with removal of alkylchloride, followed by distillation to remove alkyl ester. The hydroxymethyltrialkoxysilanes and carboxylic acid esters thereof, as well as carboxymethyltrialkoxysilanes, are particularly useful in sol-gel processing by undergoing hydrolysis to yield hydroxymethylsilanetriol, and subsequent hydrolysis and polycondensation products.
    Type: Grant
    Filed: March 10, 1993
    Date of Patent: December 6, 1994
    Assignee: Gelest, Inc.
    Inventor: Barry C. Arkles
  • 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: 5359101
    Abstract: Anionically polymerizable monomers containing at least one silicon or titanium atom form polymeric photoresists having good dry etch resistance for use in microlithography. The monomers are of the formula ##STR1## wherein A is --H or --CH.dbd.CH.sub.2 ; X is a strong electron withdrawing group;Y is a strong electron withdrawing group containing at least one silicon or titanium atom.Preferably Y is ##STR2## wherein n is 1-5 and R.sup.2, R.sup.3 and R.sup.4 are C.sub.1 -C.sub.10 alkyl. A particularly preferred monomer is 3-trimethylsilylpropyl 2-cyanoacrylate.Methods for applying a resist coating by vapor deposition of these monomers and exposure to radiation are described. A positive or negative tone image can be produced, depending upon the imaging method employed. The imaging layer may be applied over a planarizing layer to form a multilayer photoresist.
    Type: Grant
    Filed: October 1, 1991
    Date of Patent: October 25, 1994
    Assignee: Loctite Ireland, Ltd.
    Inventors: John Woods, Pauline Coakley
  • Patent number: 5348684
    Abstract: The novel silylalkyl or silylalkenyl compounds correspond to the general formula (I) ##STR1## Here the symbols A.sup.1, A.sup.2, A.sup.3 denote aromatic or heteroaromatic molecular units such as 1,4-phenylene or pyrimidine-2,5-diyl which are combined via a single bond (for k, m=0) or via functional groups M.sup.1,M.sup.2 such as CO--O or CH.sub.2 --O; j, k, l, m, n are zero or 1 (j+l+n=2 or 3). The radicals R.sup.2, R.sup.3, R.sup.4, R.sup.5 are hydrogen or alkyl/alkenyl, cycloalkyl, and the radicals R.sup.6, R.sup.7, R.sup.8 have a comparable meaning (hydrogen); R.sup.1 is alkyl/alkenyl or one of the substituents known from LC chemistry such as an .alpha.-haloalkanoic radical. In some cases compounds have wide and polymorphous liquid crystalline phases.
    Type: Grant
    Filed: August 20, 1992
    Date of Patent: September 20, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Hemmerling, Hans-Rolf Dubal, Claus Escher, Gerhard Illian, Yoshio Inoguchi, Ingrid Muller, Mikio Murakami, Dieter Ohlendorf, Rainer Wingen
  • Patent number: 5338877
    Abstract: A fluoroalkyl group-containing organosilicon oligomer is represented by the following formula (I) or (IV) of: ##STR1## wherein R, R.sub.1, R.sub.2, X and Y each are the same or different groups and stand for an alkyl, alkoxy or alkylcarbonyloxy group having 1 to 10 carbon atoms, n represents an integer of 1 to 3, m.sub.1 and m.sub.3 represent an integer of 1 to 10, m.sub.2 represents an integer of 0 to 10, m.sub.4 represents an integer of 1 to 5 and R.sub.F represents ##STR2## where A stands for a hydrogen atom, a fluorine atom or a chlorine atom, n.sub.1 represents an integer of 1 to 10 and n.sub.2 represents an integer of 0 to 8. A surface treating agent contains the oligomer defined by the formula (I) or (IV).
    Type: Grant
    Filed: August 24, 1993
    Date of Patent: August 16, 1994
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Hideo Sawada, Motohiro Mitani, Masaharu Nakayama, Takeo Matsumoto
  • Patent number: 5336797
    Abstract: Siloxane macromonomers are disclosed which can be copolymerized with hydrophilic monomers or hydrophobic monomers to prepare polymeric materials useful as biomedical devices. The copolymers made from hydrophilic monomers exhibit good oxygen permeability and are particularly suitable for use in contact lenses.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: August 9, 1994
    Assignee: Bausch & Lomb Incorporated
    Inventors: Joseph A. McGee, Paul L. Valint, Jr.
  • Patent number: 5334737
    Abstract: The present invention provides a liquid silicone ester having a melting point of up to about 30.degree. C., and comprising (A) units of the general formula R.sub.a R.sup.E.sub.b SiO.sub.[4-(a+b)]/2 or (B) R.sub.x R.sup.E.sub.y SiO.sub.1/2 units and SiO.sub.4/2 units; R.sup.E being an ester-containing organic group. The silicone ester is liquid at ambient skin temperature and has improved workability, improved payout, improved emollient properties, greater solubility in organic compounds, greater substantivity to surfaces and improved water resistance.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: August 2, 1994
    Assignee: General Electric Company
    Inventors: Raymond J. Thimineur, Frank J. Traver, Virgina M. Van Valkenburgh
  • Patent number: 5329034
    Abstract: A silanol compound having a mesogenic group, of the following formula (III): ##STR1## wherein each of R.sup.5 and R.sup.6, which may be the same or different, is an alkyl group or a phenyl group, X is a single bond, an oxygen atom, or a group of the formula --COO--or "OCO--, Q is a mesogenic group, and p is an integer of from 2 to 20, and a process for its production. Also disclosed are a polymerizable monomer of the following formula (I) and a polymer having repeating units of the following formula (II). ##STR2## wherein R is a hydrogen atom, a halogen atom, an alkyl group or a phenyl group, each of R.sup.1 to R.sup.6 which may be the same or different, is an alkyl group or a phenyl group, m is an integer of from 2 to 20, n is an integer of from 0 to 50, and X, Q and p are as defined above.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: July 12, 1994
    Assignee: Sagami Chemical Research Center
    Inventors: Yu Nagase, Yuriko Takamura
  • Patent number: 5326844
    Abstract: A primer composition has blended therein an organic silicon compound having in a molecule at least one group of the formula: ##STR1## wherein R.sup.1 is a monovalent hydrocarbon group or a group represented by QSi( R.sup.4 O).sub.a (R.sup.5).sub.3-a, Q is a divalent organic group, R.sup.4 and R.sup.5 each are a monovalent hydrocarbon group, a is an integer of 0 to 3, R.sup.2 and R.sup.3 each are a hydrogen atom or a monovalent hydrocarbon group, and n is 0, 1 or 2. The primer composition is a useful adhesive since it is effective for joining silicone elastomers and similar adherends to supports such as paint coated metals and resins.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: July 5, 1994
    Assignee: Shin-Etsu Chemical Company, Limited
    Inventors: Hironao Fujiki, Masanobu Miyakoshi, Takeo Yoshida, Yoshifumi Inoue, Masatoshi Arai
  • Patent number: 5321108
    Abstract: Novel fluorosiloxane-containing monomers are disclosed which are especially useful for the preparation of biomedical materials such as contact lenses.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: June 14, 1994
    Assignee: Bausch & Lomb Incorporated
    Inventors: Jay Kunzler, Richard Ozark
  • Patent number: 5315022
    Abstract: A silicone type cinnamic acid derivative which is a siloxane having at least one unit represented by the formula (I): ##STR1## and having the other units which may exist in the siloxane being represented by the formula:O.sub.(4-m)/2 SiR.sub.m.sup.3wherein R.sup.1 represents an alkyl group having 1 to 4 carbon atoms, a phenyl group, or a trimethylsiloxy group, R.sup.2 is a divalent hydrocarbon group having at least two carbon atoms, which may include a heteroatom, O, X is an alkoxy group, n is an integer of 0 to 3, a is an integer of 2 or 3, R.sup.3 is an alkyl group having 1 to 4 carbon atoms, a phenyl group, or a trimethylsiloxy group, and m is an integer of 0 to 3.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: May 24, 1994
    Assignee: Shiseido Company Ltd.
    Inventors: Masashi Yoshida, Kenichi Umishio, Keiichi Uehara, Tomiyuki Nanba
  • Patent number: 5296625
    Abstract: The invention relates to a series of novel silicone alkoxylated esters which contain terminal carboxyl groups. This class of compounds provides unique solubility in many organic solvents as well as very substantive salts of the carboxylic acid when neutralized with base. The compounds of the present invention are prepared by reacting a the hydroxyl group in a silicone polymer with an anhydride.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: March 22, 1994
    Assignee: Siltech Inc.
    Inventors: Anthony J. O'Lenick, Jr., Jeff K. Parkinson, Robert T. Torbush
  • Patent number: 5288890
    Abstract: A fluorine-containing organosilicon compound having the formula (1): ##STR1## wherein X is a hydrolizable group, R.sup.1 is a monovalent organic group, R.sup.2 is a methyl group or a hydrogen atom, n is an integer of 1, 2 or 3, and m is an integer of 0 or 1, and a process of producing said compound. The compound may be used as a silane coupling agent capable of improving not only the strength of laminated sheets of polyester resin and glass and polyester resin concrete but also water and heat resistances.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: February 22, 1994
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hiroshi Inomata, Yasuo Tarumi, Hiromasa Yamaguchi, Kenichi Fukuda, Kazutoshi Munezawa
  • Patent number: 5266670
    Abstract: A process comprising the steps of:1) reacting a norbornene compound of the formula: ##STR1## where R is H or methyl, R.sup.1 is a direct bond or --C(.dbd.O)O-- and R.sup.2 is vinyl, ethynyl, allyl or propargyl, with a silicon hydride functional compound in the presence of hydrosilation catalyst at a temperature of at least 60 degrees; and2) recovering a product which consists essentially of the addition products of the silicon hydride functional compound to the R.sup.2 group of the norbornene compound and which is substantially free of addition products of the silicon hydride functional compound to the internal ring double bond of the norbornene compound.The products of this process can be used to produce norbornene functional prepolymers which are useful in cureable silicone formulations based on thiolene or hydrosilation cure chemistry.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: November 30, 1993
    Assignee: Loctite Corporation
    Inventors: Steven T. Nakos, Anthony F. Jacobine, David M. Glaser
  • Patent number: 5262555
    Abstract: The instant invention pertains to a high-productivity. high-yield method for the preparation of acryloxy group-containing or methacryloxy group-containing organosilicon compounds. The method of the instant invention comprises an addition reaction, in the presence of a hydrosilylation-reaction catalyst, between (A) an ester of acrylic acid with aliphatic ally unsaturated alcohol or aliphatically unsaturated phenol; or (B) an ester of methacrylic acid with aliphatically unsaturated alcohol or aliphatically unsaturated phenol; and (C) a silicon compound that contains silicon-bonded hydrogen and by then distilling the reaction mixture in the presence of a metal halide.
    Type: Grant
    Filed: March 15, 1993
    Date of Patent: November 16, 1993
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventors: Tadashi Okawa, Shuji Yamada
  • Patent number: 5256754
    Abstract: Hydrogenpolysiloxanes having a (meth)acryloxypropyl group on a side chain are useful intermediates. They are prepared by equilibration reaction of siloxane compounds.
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: October 26, 1993
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Mitsuhiro Takarada, Yuji Yoshikawa, Kenichi Isobe
  • Patent number: 5233071
    Abstract: Alpha-fluorinated olefins are hydrosilated using selected cobalt compounds as catalysts. The products are useful in coatings, and as chemical intermediates, elastomers, and caulks.
    Type: Grant
    Filed: March 17, 1992
    Date of Patent: August 3, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Lech Wilczek
  • 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: 5214077
    Abstract: New organosilicon compounds are disclosed which contain (meth)acryloxy groups and consist of average units of the formula ##STR1## in which the radicals R are the same or different and represent monovalent, optionally halogenated hydrocarbon radicals having from 1 to 18 carbon atom(s) per radical, X is a radical which may be the same or different and represents a chlorine atom or a radical of the formula --OR.sup.1, where R.sup.1 represents an alkyl radical having from 1 to 8 carbon atom(s) per radical, which can be substituted by an ether oxygen atom, a is 0 or 1, with an average of from 0.01 to 1.0, b is 0, 1, 2 or 3, with an average of from 0.0 to 3.0, c is 0, 1, 2 or 3, with an average of from 0.0 to 3.0, the sum of a+b+c.ltoreq.4, and is an average of from 1.5 to 4.0, and A is a radical of the formula ##STR2## where x is 0 or 1 and y is 0 or 1, with the proviso that the sum of x+y is 1, z is 1, 2, 3 or 4, R.sup.2 represents a hydrogen atom or a methyl radical, R.sup.
    Type: Grant
    Filed: April 13, 1992
    Date of Patent: May 25, 1993
    Assignee: Wacker-Chemie GmbH
    Inventors: Christian Herzig, Bernard Deubzer, Inge Sigl
  • Patent number: 5194646
    Abstract: A silicone compound of the rational formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently a hydrogen atom or a hydrocarbon radical free from acetylenic unsaturaiton; Z is --O--, --S-- or --NH--; Y is a divalent organic group; R.sup.3 is a hydrogen atom, an akyl, alkenyl, alkoxy or phenyl group; and m and n are rational numbers satisfy the ration of 4>m+n.gtoreq.2. The compound is useful as a precursor of nonemanating, self-curing and heat resistant silicone resins.
    Type: Grant
    Filed: January 15, 1992
    Date of Patent: March 16, 1993
    Inventors: Mitsuo Yamada, Hiroharu Ohsugi, Ryuzo Mizuguchi
  • Patent number: 5189180
    Abstract: Seco-mevinic acid derivatives are provided which have the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis.New intermediates for preparing the above seco-mevinic acid derivatives are also provided.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: February 23, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Donald S. Karanewsky
  • Patent number: 5153332
    Abstract: An organocyclosiloxane is disclosed which has both silicon-bonded alkoxy groups and organofunctional groups within each molecule. This cyclic siloxane finds utility as a coupling agent and has the general formula ##STR1## wherein R.sup.1 is independently selected from the group consisting of a monovalent hydrocarbon group having 1 to 8 carbon atoms and a monovalent halogen-substituted hydrocarbon group having 1 to 8 carbon atoms, R.sup.2 is selected from the group consisting of an alkoxy group and an alkoxysilylalkyl group, R.sup.3 is an organofunctional group selected from the group consisting of glycidoxyalkyl groups, methacryloxyalkyl groups, N-(trialkylsilyl)aminoalkyl groups, (hydroxyphenyl)alkyl groups, and haloalkyl groups and n and m each represent an integer having a value of 1 to 6 with the proviso that n+m is an integer with a value of 3 to 8.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: October 6, 1992
    Assignee: Dow Corning Toray Silicone Company, Ltd.
    Inventors: Hiroji Enami, Shoji Akamatsu
  • Patent number: 5145979
    Abstract: There are provided processes for the preparation of .gamma.-methacryloxypropylsilane compounds which comprise carrying out the reaction of allyl methacrylate with a hydrosilane compound in the presence of a platinum catalyst, while allowing at least one of a hindered phenol compound and an aromatic amine compound to coexist in the reaction system with an alkylamine compound or an amide compound, or with a gas containing molecular oxygen, or with a phenol compound having an aminoalkylene group. By using these processes as provided, gelation of the reaction mixture in the reaction system and during the course of purification thereof by distillation can effectively be avoided, and the desired .gamma.-methacryloxypropylsilane compounds can be obtained in good yield.
    Type: Grant
    Filed: August 22, 1991
    Date of Patent: September 8, 1992
    Assignee: Tonen Corporation
    Inventors: Kazutoshi Takatsuna, Masaaki Ishii, Hideaki Ogawa, Akihito Shinohara, Kouji Shiozawa, Yoshiharu Okumura, Masako Ishikawa
  • Patent number: 5142037
    Abstract: The platinum catalyst composition comprises a diolefin component represented by the following general formulaCH.sub.2 .dbd.CH--R--CH.dbd.CH.sub.2wherein R is a divalent saturated hydrocarbon radical, and a platinum compound component. The platinum catalyst composition is extremely useful for hydrosilylation of an organosilicon compound having a .tbd.SiH radical with an olefin. When used for the hydrosilylation reaction, it inhibits effectively the isomerization of the starting material olefin, thereby enabling the intended organosilicon compound to be obtained in a high yield.
    Type: Grant
    Filed: December 16, 1991
    Date of Patent: August 25, 1992
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Yamazaki, Masaaki Yamaya, Hideyoshi Yanagisawa, Masayuki Takahashi
  • Patent number: 5136065
    Abstract: Novel propargyl esters are prepared by a base catalyzed condensation reaction of propargyl esters of carboxylic acids containing a labile hydrogen atom at the alpha position relative to the carboxy group, and a terminal aromatic hydrocarbon radical that is linked to the carboxy group through a sequence of carbon atoms containing at least one carbon-to-carbon double bond. If more than one of these double bonds are present they form a conjugated sequence. Novel organosilicon compounds are prepared by reacting these propargyl esters with an organohydrogensilane or an organohydrogensiloxane. The organosilicon compounds undergo a reversible crosslinking reaction in the presence of ultraviolet light.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: August 4, 1992
    Assignee: Dow Corning Corporation
    Inventor: Ming-Hsiung Yeh
  • Patent number: 5136063
    Abstract: The invention relates to a series of novel silicone fatty esters. This class of compounds, provide outstanding softening and lubricating when applied to textiles and fibers. The compounds of the present invention are prepared by reacting a the hydroxyl group in a silicone polymer with a fatty carboxylic acid, ester or anhydride.
    Type: Grant
    Filed: June 18, 1990
    Date of Patent: August 4, 1992
    Assignee: Siltech Inc.
    Inventor: Anthony J. O'Lenick, Jr.
  • Patent number: 5117027
    Abstract: A quaternary pyridinium halide is used as the phase transfer catalyst in a process for the preparation of an organosilane containing methacryloyloxy or acryloyloxy groups by reacting an alkali metal methacrylate or alkali metal acrylate with a chloroalkylsilane.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: May 26, 1992
    Assignee: Huls Aktiengesellschaft
    Inventors: Gunther Bernhardt, Klaus-Dieter Steffen, Margret Haas, Heinz Kragl
  • Patent number: 5113004
    Abstract: Organosilicon compounds represented by the following general formula, which acquire high thermal resistance suitable for silane coupling agents by containing a phenylene group between an alkoxysilyl group and a (metha)acrylic group; ##STR1## (wherein R.sup.1 represents a monovalent hydrocarbon residue containing one or two carbon atoms, R.sup.2 represents a divalent hydrocarbon residue containing two or three carbon atoms, R.sup.3 represents a hydrogen atom or a methyl group, m represents an integer from 1 to 3, and n represents 0 to 1).
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: May 12, 1992
    Assignee: Shin-Etsu Chemical Company, Limited
    Inventors: Hideyoshi Yanagisawa, Masaaki Yamaya
  • Patent number: 5113000
    Abstract: An organosilicon compound represented by the general formula: ##STR1## where R.sup.1 represents a substituted or non-substituted monovalent hydrocarbon group, X represents a chloromethyl group, (meth)acryloxymethyl group, glycidoxymethyl group or aminomethyl group, Y represents a hydrolyzable group or hydroxyl group, n represents a number of 1, 2 or 3. The compound is useful, for example, for the improvement of adhesion between the organic and inorganic materials.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: May 12, 1992
    Assignee: Toshiba Silicone Co., Ltd.
    Inventors: Hisao Motegi, Takeshi Sunaga, Michio Zembayashi
  • Patent number: 5101059
    Abstract: This invention relates to compounds of the formula a compound of the formula ##STR1## wherein X is O, CR.sub.7 R.sub.8, S or NR.sub.9 wherein R.sub.7 and R.sub.8 are independently hydrogen, or lower alkyl, and R.sub.9 is lower alkyl;n is 0 or 1;R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, monoorganosilyl, diorganosilyl, triorganosilyl, halogen, aryl, or nitro;R.sub.3 is hydrogen, lower alkyl, monoorganosilyl, diorganosilyl, triorganosilyl, halogen, 9-fluorenylalkyl, cycloalkyl, aryl or aralkyl;R.sub.4 and R.sub.5 are independently hydrogen, lower alkyl, or aryl or one of R.sub.4 and R.sub.5 is 9-fluorenyl;R.sub.6 is H or COZ wherein Z is an amino acid, a peptide residue or a leaving group; andwith the provisos that when n is 0 and R.sub.3 is hydrogen, R.sub.1 and R.sub.2 are not hydrogen, halogen or nitro; that when n is 0 and R.sub.3 is lower alkyl, R.sub.1 and R.sub.2 are not hydrogen; and that when X is O or CR.sub.7 R.sub.8 wherein R.sub.7 and R.sub.8 are H, that R.sub.1, R.sub.2, R.sub.
    Type: Grant
    Filed: December 5, 1989
    Date of Patent: March 31, 1992
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, An-Chuu Wu
  • Patent number: 5098981
    Abstract: A novel polyorganosiloxane is provided which has a fluorine atom-containing substituent at one terminal of its molecular chain and an unsaturated double bond-containing substituent at the other terminal thereof. The polyorgansiloxane of the present invention is represented by the general formula (I) ##STR1## wherein j is an integer of 1 to 2000, and R.sup.1 is an unsaturated double bond-containing group, each of R.sup.2 and R.sup.3 is an alkyl group having 1 to 4 carbon atoms, phenyl group, vinyl group, straight-chain or branched alkenyl group having 3 to 20 carbon atoms, or a siloxane chain which is similar to ##STR2## and R.sup.4 is a fluorine atom-containing substituent, ##STR3## wherein R.sup.10 is similar to R.sup.4 and is the fruorine atom-containing substituent, R.sup.
    Type: Grant
    Filed: February 7, 1991
    Date of Patent: March 24, 1992
    Assignee: Chisso Corporation
    Inventors: Takahiro Saho, Yoshinori Akutsu, Takaharu Nakano, Nobumasa Ohtake
  • Patent number: 5093511
    Abstract: A silicone type cinnamic acid derivative which is a siloxane having at least one unit represented by the formula (I): ##STR1## and having the other units which may exist in the siloxane being represented by the formula:O.sub.(4-m)/2 SiR.sup.3.sub.mwherein R.sup.1 represents an alkyl group having 1 to 4 carbon atoms, a phenyl group, or a trimethylsiloxy group, R.sup.2 is a divalent hydrocarbon group having at least two carbon atoms, which may include a heteroatom O, X is an alkoxy group, n is an integer of 0 to 3, a is an integer of 2 or 3, R.sup.3 is an alkyl group having 1 to 4 carbon atoms, a phenyl group, or a trimethylsiloxy group, and m is an integer of 0 to 3.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: March 3, 1992
    Assignee: Shiseido Company, Ltd.
    Inventors: Masashi Yoshida, Tomiyuki Nanba, Keiichi Uehara
  • Patent number: 5070215
    Abstract: Novel monomers of the general formula ##STR1## where b is 0 or 1, a is 1, 2, 3 or 4, R.sup.2 is a monovalent alkyl radical and R is an organic radical. The novel monomers may be employed to produce novel copolymers useful as hydrogel, soft non-hydrogel and/or rigid gas permeable contact lens materials.
    Type: Grant
    Filed: May 2, 1989
    Date of Patent: December 3, 1991
    Assignee: Bausch & Lomb Incorporated
    Inventors: Ronald E. Bambury, David E. Seelye
  • Patent number: 5049617
    Abstract: Organopolysiloxane compounds represented by the following general formula (I), which can fully achieve their effects as functional group when introduced as cross-linking groups into moisture cross-linkable polymers: ##STR1## (wherein R' represents methyl group or hydrogen atom; R.sup.2 represents methyl group or ethyl group; m represents an integer from 1 to 3; n represents an integer from 3 to 50; k represents 1 or 2 and l represents 2 or 3).
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: September 17, 1991
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hiroshi Yoshioka, Ichiro Ono, Hitoshi Uehara
  • Patent number: 5041588
    Abstract: Chemically reactive fluorinated organosilicon compounds as described for use as, e.g., lubricants, sealants and elastomers, are described corresponding to the formulaeX.sub.2 R.sup.1.sub.2 Si IorXR.sup.2.sub.2 Si(R.sup.3 SiR.sup.2.sub.2).sub.z X IIwhere X a represents a reactive group selected from a halogen, hydroxyl, alkoxy, acetoxy, amino, alkyl amino or dialkyl amino, z is from 1 to 5, inclusive, at least one of the R.sup.1 radicals and at least one of the R.sup.
    Type: Grant
    Filed: July 3, 1989
    Date of Patent: August 20, 1991
    Assignee: Dow Corning Corporation
    Inventor: Gerardo Caporiccio
  • Patent number: 5041587
    Abstract: A process for preparing an organic silicon compound is here disclosed which comprises the step of reacting a halogenated hydrocarbon selected from the group consisting ##STR1## wherein each of X.sup.1 to X.sup.16 is selected from the group consisting of hydrogen, an alkyl group, alkenyl group, phenyl group, naphthyl group, alkoxy group, acyl group, alkylamino group and dialkylamino group having 1 to 20 carbon atoms which are unsubstituted or substituted and a halogen atom; and each of at least one of X.sup.1 to X.sup.4, at least one of X.sup.8 to X.sup.10 and at least one of X.sup.11 to X.sup.16 is a halogen atom,with a silane selected from the group consisting of SiH.sub.4, Si.sub.2 H.sub.6 and Si.sub.3 H.sub.8.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: August 20, 1991
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masayoshi Itoh, Kenji Iwata, Noriyuki Yanagawa, Tetsura Utsumi, Mineo Kobayashi, Ryo Takeuchi, Tomohiro Abe
  • Patent number: 5041593
    Abstract: Silyl-functional fumarates are formed through the reaction of a methyl ester of a maleate with a chloroalkyl silane or disiloxane in the presence of an amine or phosphine catalyst. These materials are useful as adhesion promoters for polyolefins.
    Type: Grant
    Filed: July 19, 1989
    Date of Patent: August 20, 1991
    Assignee: Dow Corning Corporation
    Inventor: Edwin P. Plueddemann
  • Patent number: 5039761
    Abstract: Novel methacryl functional dimethylpolysiloxanes are provided. Graft copolymers thereof with vinyl monomers exhibit water repellency, mold release properties, slip properties, weatherability, and gas permeability.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: August 13, 1991
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ichiro Ono, Hiroshi Yoshioka
  • Patent number: 5017718
    Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: May 21, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami
  • 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: 4981986
    Abstract: Disclosed herein is a new organosilicon compound having a .beta.-diketone or .beta.-ketoester structures and a hydrolyzable group. The new organosilicon compound can be effectively used for the production of an immobilized catalyst, an adsorbent for metal recovery, a curing catalyst for organosiloxane and epoxy resins, and an adhesion promoter.
    Type: Grant
    Filed: April 6, 1988
    Date of Patent: January 1, 1991
    Assignee: Shin-Etsu Chemical Co.
    Inventors: Hiroshi Yoshioka, Masaaki Yamaya, Kazuharu Sato, Akinari Itagaki
  • Patent number: 4977291
    Abstract: A process of producing a silanic or siloxanic compound containing at least one cycloalkyl ring by the hydrogenation of a corresponding compound containing at least one aromatic ring, in the presence of a Raney nickel catalyst having a granulometry comprised essentially between 10 and 150 micrometers and a surface area of at least 80 m.sup.2 /g.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: December 11, 1990
    Assignee: Istituto Guido Donegani S.p.A.
    Inventors: Francesco Gementi, Loris Sogli, Raffaele Ungarelli