One Of The Two Carbons Is Part Of A Substituent On The Oxygen, Which Substituent Contains Halogen And Does Not Contain Silicon Or A Benzene Ring Patents (Class 556/448)
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Patent number: 11535579Abstract: A hydrofluoroolefin ether represented by the general Formula (I), compositions that include such compounds, and apparatuses and methods for use that include such compositions and compounds, wherein Formula (I) is represented by: Rf—O—CH2CH?CHCH2—O—Rf (I) wherein each Rf group is independently a linear, branched, and/or cyclic perfluoroalkyl group having 2 to 9 carbon atoms and optionally further including 1 to 3 nitrogen and/or oxygen catenary heteroatoms.Type: GrantFiled: December 12, 2018Date of Patent: December 27, 2022Assignee: 3M INNOVATIVE PROPERTIES COMPANYInventor: Sean M. Smith
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Publication number: 20150118502Abstract: The present invention provides a novel perfluoropolyether group containing silane compound wherein the compound is represented by any one of the following general formulae (1a), (1b) (2a) and (2b), has a number average molecular weight of 6×103 to 1×105 and can form a layer having water-repellency, oil-repellency, antifouling repellency and high friction durability.Type: ApplicationFiled: June 12, 2013Publication date: April 30, 2015Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Hisashi Mitsuhashi, Akinari Sugiyama
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Publication number: 20140302332Abstract: To provide a fluorinated ether compound, a fluorinated ether composition and a coating liquid, whereby it is possible to form a surface-treated layer which has high initial water/oil repellency and which is excellent in abrasion resistance and fingerprint stain removability, and a substrate having a surface-treated layer and a method for its production. A fluorinated ether compound which has a poly(oxyperfluoroalkylene) chain ((??)n) made of at least two units (??) linked to one another, and which has a hydrolysable silyl group on at least one terminal of the chain ((??)n) via a linking group, wherein each unit (??) is a poly(oxyperfluoroalkylene) group comprising one to three groups (?) made of at least one type of a C1-2 oxyperfluoroalkylene group and one to three groups (?) made of at least one type of a C3-6 oxyperfluoroalkylene group.Type: ApplicationFiled: June 23, 2014Publication date: October 9, 2014Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Eisuke MUROTANI, Taiki Hoshino, Akinobu Kunimoto, Daisuke Jomuta, Nobuyuki Otozawa
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Publication number: 20140155350Abstract: A new class of neuramidase inhibitor prodrugs is provided characterized by a prodrug moiety of a carboxyl group modified to form a carbonyl ethoxy amino acid, a carbonyl ethoxy dipeptide or a carbonyl ethoxy tripeptide, a guanidine group modified to form a carbonyl ethoxy amino acid, a carbonyl ethoxy dipeptide, a carbonyl ethoxy tripeptide; a primary alcohol modified to form an esterified single amino acid, dipeptide or tripeptide of zanavimir of the unaltered therapeutic agent. Exemplary therapeutic agents so modified to form prodrugs include zanavimir, oseltamivir and peramivir. The prodrug has increased oral bioavailability relative to the unaltered neuraminidase inhibitor and is effective in the inhibition of viral infections involving neuraminidase in the viral reproductive cycle.Type: ApplicationFiled: November 26, 2013Publication date: June 5, 2014Applicant: SineVir Therapeutics LLCInventors: John Hilfinger, Gordon Amidon
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Patent number: 8519078Abstract: A polyether-modified polysiloxane containing a perfluoropolyether group and its production method are provided. The polysiloxane has both the properties of a perfluoropolyether and the properties of a polyether-modified silicone, and it also has high affinity for organic solvents as well as coating compositions, cosmetics, and various coating materials. The polysiloxane is represented by the following general formula (1): wherein Rf is a perfluoroalkyl group; X is fluorine atom or trifluoromethyl group; Q is a divalent organic group, R is hydrogen atom, an alkyl group, or acyl group; R1 and R2 are an alkyl group, aryl group, or an aralkyl group; a, b, c, d are 0 to 200; a+b+c+d is at least 1; e is 0 or 1; p and q are 0 to 50 with the proviso that p+q is at least 2; and k is 1 to 3.Type: GrantFiled: June 27, 2011Date of Patent: August 27, 2013Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hiromasa Yamaguchi, Yasunori Sakano
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Publication number: 20130034514Abstract: Hair treatment agents having in addition to at least one hair-setting polymer, at least one polyether of formula (I) T-K-A-K?-T???(I), wherein A is a polyoxyalkylene chain comprising ethylene oxide units or ethylene oxide units and propylene oxide units, having a maximum of 50 wt % propylene oxide units based on the weight of A, K and K? are, mutually independently, a connectivity chosen from a covalent bond or a molecule fragment having two free valences, T and T? are, mutually independently, a molecule fragment having at least one substituent chosen from anionic residue or —Si(OR)x(R?)3-x residue, wherein R and R? are, mutually independently, a (C1 to C4) alkyl group, and x is 1, 2, or 3, wherein at most one residue from T or T? can also be a (C1 to C6) alkyl group, aryl group, aryl-(C1 to C6) alkyl group, (C1 to C6) alkoxy group, or (C2 to C6) acyl group.Type: ApplicationFiled: February 3, 2012Publication date: February 7, 2013Inventor: Matthias Schweinsberg
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Publication number: 20120264964Abstract: Alkoxysilane compounds having two fluoroalkyl groups and represented by the formula (1): wherein Rf and Rf? are each a fluoroalkyl group of 1 to 10 carbon atoms, R1 is a hydrogen atom or an aliphatic monovalent hydrocarbon group of 1 to 6 carbon atoms, R2 and R3 are each methyl group or ethyl group, X and Y are each an ether linkage or an ester linkage, a and b are each 0 or 1, m, n and p are each an integer of 0 to 6, q is an integer of 1 to 6, and r is an integer of 0 to 2. By treating an inorganic material with the alkoxysilane compound having ether linkage and two fluoroalkyl groups, high water and oil repellency and high sliding properties are imparted to the inorganic material. The alkoxysilane compounds are easily purified, owing to enhanced volatility by the branched structure.Type: ApplicationFiled: April 11, 2012Publication date: October 18, 2012Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Takayuki Honma, Ayumu Kiyomori, Tohru Kubota, Daijitsu Harada, Hiroyuki Yamazaki, Masaki Takeuchi
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Publication number: 20120165565Abstract: The subject of invention is the method of synthesis of fluorocarbofunctional alkoxysilanes and chlorosilanes of the general formula HCF2(CF2)n(CH2)mOC3H7SiR1R2R3 in which -n takes values from 1 to 12, m takes values from 1 to 4,—R1 stands for an alkoxy group or halogen, if R1 stands for an alkoxy group, then R2 and R3 can be the same or different and stand for an alkoxy group containing C=1-4, alkyl group containing C=1-12 or an aryl group, if R1 stands for a halogen, then R2 and R3 can be the same or different and stand for based on hydrosilylation of an appropriate fluoroalkyl-allyl ether with an appropriate trisubstituted silane of the general formula HSiR1R2R3 in the presence of siloxide rhodium complex [{Rh(OSiMe3)(cod)}2] as a catalyst.Type: ApplicationFiled: August 16, 2010Publication date: June 28, 2012Applicant: ADAM MICKIEWICZ UNIVERSITYInventors: Bogdan Marciniec, Hieronim Maciejewski, Michal Dutkiewicz, Izabela Dabek, Joanna Karasiewicz
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Publication number: 20110118427Abstract: Disclosed are a transition metal complex represented by the formula (1) and a method for producing the same; a substituted fluorene compound represented by the formula (2) and a method for producing the same; an olefin polymerization catalyst including the transition metal complex as a constituent component; and a method for producing a polyolefin resin, which includes polymerizing an olefin in the presence of the olefin polymerization catalyst.Type: ApplicationFiled: July 7, 2009Publication date: May 19, 2011Inventors: Takahiro Hino, Hidenori Hanaoka, Taichi Senda
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Publication number: 20080139766Abstract: Disclosed herein are a perfluoroalkyleneoxy group-substituted phenylethylsilane compound and a polymer thereof. The perfluoroalkyleneoxy group-substituted phenylethylsilane compound represented by Formula 1 has excellent thermal and chemical stability to be solution-processed in a monomer state, and the polymer prepared by thermally crosslinking the compound has a high resistance to organic solvents. Moreover, since an insulating layer prepared by applying the same shows improved thermal and physical properties, it is possible to manufacture organic thin-film transistors having a high on/off ratio in a simple process such as a photolithography for a large-size substrate: wherein R1, R2, R3, Z1, Z2, Z3, and n are the same as defined in the detailed description of the invention.Type: ApplicationFiled: August 31, 2007Publication date: June 12, 2008Inventors: Dong-Yu Kim, Ji-Eun Ghim, Chae-Min Chun, Bo-Gyu Lim
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Patent number: 7081508Abstract: A primer composition comprises (a) a fluoroalkylene or fluoropolyether compound having at least one alkenyl radical and at least one hydrolyzable silyl radical, (b) an organic titanic acid ester, (c) an organic tin compound, and (d) a silane compound. The primer composition is fully adherent to various substrates of metals, glass, ceramics, cement, mortar, carbon, and plastics, and is particularly suited for use with a thermosetting elastomer composition based on a polymer having at least two alkenyl radicals and a perfluoropolyether structure in its backbone.Type: GrantFiled: June 25, 2004Date of Patent: July 25, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takashi Matsuda, Yasuhisa Osawa
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Patent number: 6706906Abstract: A water repellent composition comprising a compound of the following formula 1, and a compound of the following formula 4 and/or a compound of the following formula 5: RfSi(R)p(X)3−p Formula 1 RFSi(R1)q(X1)3−q Formula 4 SiX24 Formula 5 wherein Rf is a fluorine-containing organic group having an etheric oxygen atom, RF is a fluorine-containing organic group having no etheric oxygen atom, each of R and R1 which are independent of each other, is a C1-6 hydrocarbon group containing no fluorine atom, each of X, X1 and X2 which are independent of one another, is a halogen atom or a hydrolyzable group, and each of p and q which are independent of each other, is 0, 1 or 2.Type: GrantFiled: January 25, 2002Date of Patent: March 16, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashige Yoneda, Yutaka Furukawa, Noriko Torimoto
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Patent number: 6703378Abstract: Fluorosilicone fluids useful as high-density fluid ocular tamponades and methods of producing, purifying and using the fluorosilicone fluids in an ocular surgical procedure for retinal treatment.Type: GrantFiled: September 19, 2002Date of Patent: March 9, 2004Assignee: Bausch & Lomb IncorporatedInventors: Jay F. Kunzler, Richard M. Ozark, Joseph C. Salamone
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Publication number: 20020198308Abstract: A curable resin composition comprising an oxyalkylene base copolymer having at least one silicone atom containing group to the silicone atom of which a hydroxyl group and/or hydrolyzable group is attached and which is cross-linked through formation of a siloxane bond.Type: ApplicationFiled: January 31, 2002Publication date: December 26, 2002Inventor: Gary M. Lucas
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Patent number: 6448428Abstract: A fluorine-containing organic silicon compound represented by the following formula (1): (1) provided that the symbols in the formula (1) have the following meanings: R1 and R2: respectively independently monovalent hydrocarbon groups; Af: a group represented by the following formula (2), (3), (4) or (5): A1—X1— (2) A2—X2—O—X1— (3) A1—X2—O—X1— (4) A2—X1— (5) provided that the symbols in the formulae (2), (3), (4) and (5) have the following meanings: A1: a monovalent polyfluorohydrocarbon group; A2: a monovalent polyfluorohydrocarbon group containing an etheric oxygen atom; X1: —(CH2)a— (a is an integer of at least 3); X2: a bivalent hydrocarbon group.Type: GrantFiled: December 5, 2001Date of Patent: September 10, 2002Assignee: Asahi Glass Company, LimitedInventors: Yutaka Furukawa, Takashige Yoneda
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Patent number: 6291623Abstract: This invention relates to new fluoroalkyl substituted cyclotrisiloxanes, their use in the preparation of new homopolymers, block copolymers and random copolymers, and to such new homopolymers, block copolymers and random copolymers.Type: GrantFiled: October 12, 1999Date of Patent: September 18, 2001Assignee: University of Southern CaliforniaInventors: Jyri Kalevi Paulasaari, William P. Weber
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Patent number: 6150548Abstract: The invention relates to a compound having the formula I ##STR1## wherein R.sup.1 is hydroxy, (1-6C)alkoxy or NR.sup.4 R.sup.5, R.sup.4 and R.sup.5 being independently hydrogen, (1-6C)alkyl, (3-7C)cycloalkyl, (2-6C)alkenyl, (4-6C)aryl or (5-7C)aralkyl, the aryl groups of which may be optionally substituted with halogen, (1-6C)alkyl or (1-6C)alkoxy;R.sup.2 is a halo atom, (1-8C)acyloxy, --O--C(O)--O-(1-6C)alkyl, --O--C(O)--O-(5-7C)aralkyl, --SR.sup.6, --S(O)R.sup.6, --SeR.sup.6 or --Se(O)R.sup.6, R.sup.6 being (1-6C)alkyl or (4-6C)aryl; andR.sup.3 is --Si(R.sup.7).sub.3, R.sup.7 being independently (1-6C)alkyl or (4-6C)aryl. The compounds of the invention may be used as protective groups or as linkers in solid phase organic chemistry.Type: GrantFiled: February 9, 1999Date of Patent: November 21, 2000Assignee: Akzo Nobel, N.V.Inventor: Wim-Jan Koot
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Patent number: 6114562Abstract: Novel organosilicon compounds having a perfluoroalkyl or perfluoropolyether group and at least one ethynyl group are useful as an agent for controlling hydrosilylation reaction between a --SiH group-bearing compound and a --CH.dbd.CH.sub.2 group-bearing compound.Type: GrantFiled: August 4, 1999Date of Patent: September 5, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Kenichi Fukuda, Hirofumi Kishita
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Patent number: 5948929Abstract: A fluorinated organosilicon compound is represented by formula (I).Type: GrantFiled: January 8, 1998Date of Patent: September 7, 1999Assignee: FSO LimitedInventor: Vladimir Mileshkevich
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Patent number: 5914420Abstract: Compositions of unstrained perfluorinated organo substituted cyclosiloxanes of formula (I): ##STR1## wherein m is an integer of 1 to 12; n is an integer of 1 to 4; X is a divalent radical which may include O, NH, N(CH.sub.3), OC(O), NHC(O), N(CH.sub.3)C(O)CH.sub.2 ; and R.sup.F is a perfluorinated straight chain or branched chain monovalent alkyl radical of 1 to 25 carbon atoms; or R.sup.F is a perfluorinated ether radical of the general formula (II): ##STR2## wherein p is an integer of 1 to 10 are described, along with copolymer compositions prepared from these cyclopolysiloxanes and from mixtures of these cyclosiloxanes and other siloxanes.Type: GrantFiled: May 29, 1998Date of Patent: June 22, 1999Assignee: PCR, Inc.Inventors: Mark A. Buese, John Scott Shaffer
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Patent number: 5908950Abstract: Polyether modified fluoroalkylsiloxanes having the general structure of Formula (I), Formula (II) or Formula (III): ##STR1## wherein x is about 0 to 500, y is about 1 to 50, z is about 1 to 50, R=C.sub.p H.sub.2p --(OC.sub.2 H.sub.4).sub.n --(OC.sub.3 H.sub.6).sub.n).sub.m --OR' in which p is about 2 to 5, n is about 0 to 50, N is about 0 to 50, and one of n or m must be >0, and R'=H, an alkyl group with 1-4 carbons, or an acetyl group and R.sub.f =C.sub.a H.sub.2a --O.sub.b --C.sub.c H.sub.2c --C.sub.d F.sub.2d+1 in which a is 3 or 4, b is 0 or 1, c is 0 or 2-4 and d is 4-12 with the provisos that if b=0, then c=0, and that if b=1, then c=2-4; z.sub.1 is about 0 to 50 and y.sub.1 is about 0 to 50, are useful to reduce the coefficient of friction and to increase mar resistance of coatings, to increase spreadability and wettability of coating formulations, and as foam control agents.Type: GrantFiled: May 29, 1997Date of Patent: June 1, 1999Assignee: Witco CorporationInventors: Jeffrey A. Cooke, Gerald J. Murphy, Yutaka Furukawa, Seisaku Kumai
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Patent number: 5892086Abstract: Compositions of unstrained perfluorinated ether organo substituted cyclosiloxanes of formula (I): ##STR1## wherein m is an integer of 1 to 12; n is an integer of 1 to 4; X is a divalent radical which may include O, NH, N(CH.sub.3), OC(O), NHC(O), N(CH.sub.3)C(O)CH.sub.2 ; and R.sup.F is a perfluorinated ether radical of the general formula (II): ##STR2## wherein p is an integer of 1 to 10 are described, along with copolymer compositions prepared from these cyclopolysiloxanes and from mixtures of these cyclosiloxanes and other siloxanes.Type: GrantFiled: May 29, 1998Date of Patent: April 6, 1999Assignee: PCR, Inc.Inventors: Mark A. Buese, John Scott Shaffer
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Patent number: 5834612Abstract: A fluorine-containing organic compound of the following formula (1):R.sup.f CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CH.dbd.CH.sub.2 ( 1)wherein R.sup.f is a C.sub.1-20 fluoroalkyl group.Type: GrantFiled: May 14, 1997Date of Patent: November 10, 1998Assignees: Asahi Glass Company Ltd., OSI Specialties, Inc.Inventors: Yutaka Furukawa, Seisaku Kumai, Jeffery A. Cooke, Gerald J. Murphy, George A. Policello
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Patent number: 5700898Abstract: The present invention is directed to a fluorine-modified silicone derivative the organopolysiloxane chain which is partly substituted by the siloxane chain of the following general formula (1), (2) or (3), a preparation process thereof, intermediates useful for the preparation thereof and cosmetic compositions containing this derivative. ##STR1## wherein Rf and Rf' mean individually a perfluoroalkyl group having 1-20 carbon atoms or a .omega.-H-perfluoroalkyl group represented by the formula H(CF.sub.2).sub.t -- in which t stands for an integer of 1-20, R.sup.1 may be identical with or different from each other and means a straight-chain or branched aliphatic hydrocarbon group having 1-20 carbon atoms, or an alicyclic or aromatic hydrocarbon group having 5-10 carbon atoms, R.sup.2 denotes a hydrogen atom, a straight-chain or branched aliphatic hydrocarbon group having 1-20 carbon atoms, an alicyclic or aromatic hydrocarbon group having 5-10 carbon atoms, a perfluoroalkyl group having 1-20 carbon atoms, or a .Type: GrantFiled: February 23, 1996Date of Patent: December 23, 1997Assignee: Kao CorporationInventors: Jouji Okada, Akira Kawamata, Tadayuki Tokunaga, Noboru Nagatani, Makoto Torizuka, Masahiko Asahi
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Patent number: 5698728Abstract: Novel alkene intermediates useful in the preparation of 1,2-dioxetanes.Type: GrantFiled: May 15, 1995Date of Patent: December 16, 1997Assignee: Board of Governors of Wayne State UniversityInventors: Arthur Paul Schaap, Hashem Akhavan-Tafti
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Patent number: 5548054Abstract: A fluorine-modified silicone derivative having an organopolysiloxane chain which is partly substituted by the siloxane chain of the following general formula (1), (2) or (3), ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sub.f, R.sub.f ', l, m, n and r are as described herein, a preparation process thereof, intermediates useful for the preparation thereof and cosmetic compositions containing this derivative.Type: GrantFiled: August 29, 1994Date of Patent: August 20, 1996Assignee: Kao CorporationInventors: Jouji Okada, Akira Kawamata, Tadayuki Tokunaga, Noboru Nagatani, Makoto Torizuka, Masahiko Asahi
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Patent number: 5412135Abstract: A novel organic silicon compound having at least one .tbd.SiH group in a molecule and a fluorinated organic group at either end is a useful crosslinking agent for various resins, especially fluorinated resins. An organopolysiloxane composition comprising (A) an organopolysiloxane having in a molecule at least two alkenyl groups and at least one fluorinated substituent, (B) an organohydrogenpolysiloxane having at least two .tbd.SiH groups in a molecule and a fluorinated organic group at either end, and (C) a platinum catalyst is readily curable to products having solvent and moisture resistance.Type: GrantFiled: April 20, 1994Date of Patent: May 2, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Kenichi Fukuda, Kouichi Yamaguchi, Shinichi Sato, Hirofumi Kishita, Masatoshi Arai, Hironao Fujiki
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Patent number: 5374760Abstract: A fluorine-containing organosilicon compound and a method for its preparation are disclosed, said compound having the general formula ##STR1## in which R.sup.1 represents a monovalent hydrocarbon group, excluding alkenyl group, R.sup.2 represents a divalent organic group, a is 2 or 3, and m is an integer having a value of 4 to 12.Type: GrantFiled: March 14, 1994Date of Patent: December 20, 1994Assignee: Dow Corning Toray Silicone Co., Ltd.Inventor: Hideki Kobayashi
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Patent number: 5288891Abstract: 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 --CF.sub.2).sub.n.sbsb.1 A or ##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: GrantFiled: November 14, 1991Date of Patent: February 22, 1994Assignee: Nippon Oil and Fats Co. Ltd.Inventors: Hideo Sawada, Motohiro Mitani, Masaharu Nakayama, Takeo Matsumoto
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Patent number: 5262557Abstract: A fluorine containing organosilicon compound represented by the following general formula: ##STR1## wherein R represents an alkyl group or an aryl group, a is an integer of 1 to 7, b is an integer of 2 to 8, and c is an integer of 1 to 3. This compound is useful as a surface treating agent for silicas, an adhesive improver for resists, an oil or water-repellent treating agent, and a raw material for synthesis of various silicone compounds.Type: GrantFiled: October 16, 1992Date of Patent: November 16, 1993Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hirofumi Kishita, Kouichi Yamaguchi, Shuji Suganuma
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Patent number: 5247112Abstract: The present invention is a method for separating silyl ketene acetals from carbonyl by-products having a terminal olefinic bond and a boiling point similar to that of the silyl ketene acetals. The method employs a platinum catalyst which specifically effects hydrosilation of the carbonyl by-product's terminal olefinic bond by an organohydrosilane. The platinum catalyst is the reaction product of hexachloroplatinic acid and sym-tetramethyldivinyldisiloxane. In a preferred method the silyl ketene acetal is separated from the hydrosilated carbonyl by-product by distillation.Type: GrantFiled: February 8, 1993Date of Patent: September 21, 1993Assignee: Dow Corning CorporationInventors: Paul C. Dinh, Peter Y. K. Lo
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Patent number: 5214177Abstract: Fluorinated organic silicon compound of the general formula: ##STR1## wherein R is an alkyl group having 1 to 6 carbon atoms, n is an integer of from 1 to 6, and m is equal to 1, 2 or 3 are novel and useful as treating agents and intermediates for the synthesis of fluorinated cyclic organic silicon compounds. The fluorinated organic silicon compounds are prepared by reacting a chlorosilane with a fluorinated olefin.Type: GrantFiled: October 1, 1991Date of Patent: May 25, 1993Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayuki Oyama, Toshio Takago, Hideki Fujii, Hitoshi Kinami
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Patent number: 5210253Abstract: Fluorine-containing organosilicon compound according to the present invention is expressed by the general formula: ##STR1## wherein Rf is a perfluoropolyether group having 3 to 17 carbon atoms, R is an alkylene group having 1 to 6 carbon atoms or a group of the general formula, --R.sup.2 --O--R.sup.3 --, wherein R.sup.2 and R.sup.3 may be the same or different and are each alkylene groups having 1 to 6 carbon atoms. The present compound is useful as a curing catalyst for organo-polysiloxane compounds that are condensation curable at room temperature. The compositions added with the fluorine-containing organosilicon compound have excellent characteristics such as water and oil repellencies, chemical resistance and contamination resistance and offer a variety of uses such as high performance sealing, coating and electric insulating materials.Type: GrantFiled: October 15, 1992Date of Patent: May 11, 1993Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hitoshi Kinami, Kouichi Yamaguchi, Hideki Fujii, Shuji Suganuma
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Patent number: 5208358Abstract: The present invention is a process for preparation of silyl ketene acetals. The process comprises contacting a mixture containing an organosilane having a silicon-bonded hydrogen (organohydrosilane) and a vinylic compound with RhCl(di-tert-butylsulfide).sub.2 as catalyst at a temperature within a range of about 20.degree. C. to 100.degree. C. The RhCl(di-tert-butylsulfide).sub.2 catalyst demonstrates higher activity than that typically described for rhodium catalysts, allowing for lower concentrations of catalyst and lower reaction temperatures to be used while maintaining high conversion to the desired silyl ketene acetals.Type: GrantFiled: July 13, 1992Date of Patent: May 4, 1993Assignee: Dow Corning CorporationInventors: Paul C. Dinh, Jeff A. Gray, Peter Y. K. Lo
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Patent number: 5202453Abstract: Fluorinated cyclic organic silicon compounds of the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are independently selected from alkyl groups having 1 to 6 carbon atoms and n is an integer of from 1 to 6 are novel and susceptible to ring-opening polymerization to form chain siloxane polymers having improved properties. The cyclic compounds are produced by reacting disiloxane diols with fluorinated organic silicon compounds in the presence of amine catalysts.Type: GrantFiled: October 1, 1991Date of Patent: April 13, 1993Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hirofumi Kishita, Kouji Takano, Koichi Yamaguchi, Toshio Takago
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Patent number: 5183913Abstract: The invention provides novel cyclic triketone compounds of the formulae ##STR1## wherein S is H, alkyl or alkoxy and R* is a group of the formule ##STR2## wherein R.sup.1 is methyl and R.sub.2 is an alkyl group containing at least 2 carbon atoms or R.sup.1 is an alkyl group having 1-4 carbon atoms and R.sup.2 is an aryl group, a hetero aryl group, a --CH.sub.2 OR' group, a --CH.sub.2 N<group, a --CH.sub.2 SR" group or a --CH.sub.2 CH.dbd.CH.sub.2 group, wherein R' and R" are alkyl groups having 1-4 carbon atoms.These compounds can be used for preparing daunomycinone and derivatives thereof. Daunomycinone is used for preparing daunomycin and adriamycin.By introducing chirality at C-1 of ring A in the preparation of said novel compounds by using a novel diene of formula (1) in a Diels-Alder reaction for said preparation, the chirality of C-3 is established in the subsequent reaction with LiC.tbd.CSi(CH.sub.3).sub.3 in the synthesis of daunomycinone and deriviatives thereof.Type: GrantFiled: December 20, 1991Date of Patent: February 2, 1993Assignee: Pharmachemie B.V.Inventors: Johan W. Scheeren, Joannes F. Martinus De Bie, Dirk De Vos
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Patent number: 5124467Abstract: The instant invention relates to polysiloxane polyoxyalkylene compounds containing at least one perfluoroalkyl terminated polyoxyalkylene group. These compounds are useful as surfactants and improve or impart properties such as wetting, penetration, spreading, levelling, foam stability, flow properties, dispersion properties and oil and water repellency.Type: GrantFiled: July 20, 1990Date of Patent: June 23, 1992Assignee: Ciba-Geigy CorporationInventors: Juliana Rodgers, Athanasios Karydas
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Patent number: 5099053Abstract: Fluorine-containing organic silicon compounds represented by the following general formula: ##STR1## wherein n is any integer of 1 to 4, and x is any integer or 0 to 3; and a method of manufacturing the same compounds consisting of hydrosilylization between a hexafluoropropeneoxide oligoether derivative having an isopropenyl group at one end represented by the following formula: ##STR2## wherein n is any integer from 1 to 4, and a silane represented by the following formula: ##STR3## wherein x is any integer from 0 to 3.Type: GrantFiled: May 25, 1990Date of Patent: March 24, 1992Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Akio Takaoka, Noriyuki Koike, Hideki Fujii
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Patent number: 5043464Abstract: The fluorine-surfactant of the present invention has a fluorine-containing group and a hydrophilic polyether group bonded to each other through a silicon atom, and this is obtained by reacting an organosilicon compound of the formula: ##STR1## wherein R.sub.f is a fluorine-containing organic group, l and m are each an integer of 0 or 1, and n is an integer of 1 to 3, with a polyether compound represented by the formula:CH.sub.2 .dbd.CH--CH.sub.2 O--Q--Rwherein Q is a polyether group, and R is either a hydrogen atom, the allyl group or an acyl group, in the presence of a platinum catalyst.Type: GrantFiled: April 24, 1990Date of Patent: August 27, 1991Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Yasushi Yamamoto
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Patent number: 4996344Abstract: A fluorine-containing organosilicon compound represented by Formula (I): ##STR1## wherein R.sup.1 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms; R.sup.f represents a fluorine-containing group represented by the formula: C.sub.p F.sub.2p+1 -, where p is an integer of 3 to 6, ##STR2## where q is an integer of 1 or 2, or ##STR3## where q is as defined above; m is an integer of 0 to 2; and n is an integer of 3 or 4.This novel compound is useful for the preparation of fluorosilicone polymers having a good thermal resistance, chemical resistance and weathering resistance.Type: GrantFiled: February 10, 1989Date of Patent: February 26, 1991Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hiroshi Inomata, Hirofumi Kishita, Akira Yoshida
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Patent number: 4968828Abstract: A fluorine-containing organosilicon compound represented by the following general formula: ##STR1## wherein R.sub.f represents a perfluoroalkyl group or a perfluoroalkyl ether group, and m and n are each an integer of 0 or 1. This fluorine-containing organic silicon compound is useful as a modifier for improving properties of various materials, such as heat resistance, chemical resistance and surface properties.Type: GrantFiled: October 20, 1989Date of Patent: November 6, 1990Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Yasushi Yamamoto
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Patent number: 4927950Abstract: A fluorine-containing silane compound of the formula: ##STR1## wherein R.sub.f is a fluorine-containing C.sub.4 --C.sub.18 aliphatic group, R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl group, A is a straight or branched C.sub.1 -C.sub.12 alkylene group or a group of the formula: ##STR2## in which R.sup.2 is hydrogen or a C.sub.1 -C.sub.3 acyl group, R.sup.3 is a C.sub.1 -C.sub.6 acyl group, A' is a C.sub.2 -C.sub.8 alkylene group, A" is a C.sub.1 -C.sub.4 alkylene group, and Q is --CO-- or --SO.sub.2 --, B is a group of the formula: ##STR3## in which R.sup.4 and R.sup.5 are each a straight or branched C.sub.2 or C.sub.3 alkylene group, and p is 2 or 3, X is chlorine or a C.sub.1 -C.sub.3 alkoxy group, X' is chlorine or a C.sub.1 -C.sub.3 alkyl or alkoxy group, a phenyl group or a glycidyl group, m is 0 or 1, and n is an integer of 0 to 40, which modifies surface characteristics of a solid substrate.Type: GrantFiled: March 8, 1985Date of Patent: May 22, 1990Assignee: Daikin Industries, Ltd.Inventors: Iwao Hisamoto, Masaru Hirai, Sueyoshi Ishikawa
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Patent number: 4898958Abstract: An organosilicon compound represented by general formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 may be the same or different and each represent an alkyl group having 1 to 4 carbon atoms; R.sub.f represents --C.sub.1 F.sub.2l+1 where l represents an integer of 3 to 10, ##STR2## where q represents an integer of 1 to 5, or ##STR3## where q is as defined above; and X represents --O-- or --CH.sub.2 --; provided that n is 3 and m is an integer of 0 to 2 when X represents --O--, and n is 0 and m is 1 when X represents --CH.sub.2 --. The compound is useful for preparing silicone polymers having a high thermal resistance, chemical resistance and weathering resistance and have a small surface energy.Type: GrantFiled: September 9, 1988Date of Patent: February 6, 1990Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hirofumi Kishita, Koichi Yamaguchi, Akira Yoshida
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Patent number: 4895966Abstract: The organosilane compound of the invention is represented by the general formulaCIFC.dbd.CF--O--(R.sup.1 --O--).sub.m --(--R.sup.2 --).sub.n --CHR.sup.3 --CH.sub.2 --SiR.sub.3,in which, for example, each R.sup.1 is an ethylene group, R.sup.2 is a methylene group, R.sup.3 is a hydrogen atom, each R is an alkyl or alkoxy group, the subscript m is zero, 1, 2 or 3 and the subscript n is zero or 1. The terminal group of CIFC.dbd.CF--O-- has copolymerizability with conventional fluorine-containing polymerizable unsaturated compounds, e.g., tetrafluoroethylene, so that it is useful as a modifying agent of fluorine-containing polymers. A synthetic method for the compound is disclosed.Type: GrantFiled: August 1, 1989Date of Patent: January 23, 1990Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tohru Kubota, Toshinobu Ishihara, Mikio Endo
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Patent number: 4864027Abstract: The compounds of the formula (I) ##STR1## in which X denotes CH.sub.2, O, S or NR.sup.6,R.sup.1 denotes alkyl, cycloalkyl, alkenyl, (substituted) phenyl, or (substituted) naphthyl,R.sup.2 and R.sup.3 denote alkyl, alkenyl or phenyl, or R.sup.2 and R.sup.3 together denote an alkylene chain,R.sup.4 denotes --H, --CN, --CCl.sub.3, --C.tbd.CH, alkyl, F, or --C(S)--NH.sub.2,R.sup.5 denotes pyridyl, furyl, thienyl, phthalimidyl, di(C.sub.1 -C.sub.4)alkylmaleinimidyl, thiophthalimidyl, dihydrophthalimidyl or tetrahydrophthalimidyl, which may all be substituted, or substituted phenyl, orR.sup.4 and R.sup.5 --together with the carbon atom bridging them--denote an optionally substituted indanyl, cyclopentenoyl or cyclopentenyl radical,with the proviso that compounds of the formula I in whichR.sup.1 denotes phenyl which is substituted in the para-position by (C.sub.1 -C.sub.4)alkoxy, halogen or (C.sub.1 -C.sub.4)alkyl;R.sup.2 and R.sup.3 denote CH.sub.3 ;X denotes O;R.sup.4 denotes H andR.sup.Type: GrantFiled: June 22, 1988Date of Patent: September 5, 1989Assignee: Hoechst AktiengesellschaftInventors: Hans H. Shubert, Gerhard Salbeck, Walter Luders, Werner Knauf
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Patent number: 4778909Abstract: Fast high resolution separations of biopolymers with retention of biological activity have been achieved by hydrophobic interaction chromatography using trialkoxy silyl ethers of the general formula(RO).sub.3 Si--(CH.sub.2).sub.m --O--(CH.sub.2 CH.sub.2 O).sub.n --(CH.sub.2).sub.p R'chemically bonded to silica-based chromatographic supports. In the formula R is alkyl of from one to five carbons, m is an integer from two to five, n is an integer from one to five, p is an integer from zero of ten, and R' is methyl, phenyl, or substituted phenyl. Stable and reproducible bonded phases are prepared in a novel solventless procedure by a bonding process which uses a defined and controlled amount of water on the silica surface and a gaseous or volatile basic catalyst such as ammonia to produce a controlled amount of silane polymerization and cross-linking in addition to extensive bonding between silane and silica.Type: GrantFiled: May 11, 1984Date of Patent: October 18, 1988Assignee: Northeastern UniversityInventors: Barry L. Karger, Binyamin Feibush, Neil T. Miller, Alvaro Figueroa
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Patent number: 4775664Abstract: The compounds of the formula (I) ##STR1## in which X denotes CH.sub.2 or O,R.sup.1 denotes (subst.) pyridyl or (subst.) pyrimidyl,R.sup.2 and R.sup.3 denote alkyl or alkenyl or R.sup.2 and R.sup.3 denote an alkylene chain,R.sup.4 denotes --H, --CN, --CCl.sub.3, --C.tbd.CH, alkyl, F, or --C(S)--NH.sub.2,R.sup.5 denotes pyridyl, furyl, thienyl, phthalimidyl, di(C.sub.1 -C.sub.4)alkylmaleimidyl, thiophthalimidyl, dihydrophthalimidyl or tetrahydrophthalimidyl, which may all be substituted, or substituted phenyl, orR.sup.4 and R.sup.5 --together with the carbon atom bridging them--denote an optionally substituted indanyl, cyclopentenoyl or cyclopentenyl radical,have advantageous insecticidal, acaricidal and nematocidal properties.Type: GrantFiled: April 10, 1987Date of Patent: October 4, 1988Assignee: Hoechst AktiengesellschaftInventors: Hans H. Schubert, Gerhard Salbeck, Walter Luders, Werner Knauf, Anna Waltersdorfer
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Patent number: 4730904Abstract: Organosilicon compounds of the formula IR.sup.1 --A.sup.1 --A.sup.2 --O--C.sub.n H.sub.2n --SiX.sub.a Y.sub.b Z.sub.c Iwherein R.sup.1, A.sup.1, A.sup.2, X, Y, Z, n, a, b and c have the meaning given can be used for producing a homotropic orientation of liquid crystal phases on surfaces.Type: GrantFiled: June 13, 1986Date of Patent: March 15, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Detlef Pauluth, Klaus Bofinger, Michael Romer, Bernhard Scheuble, Georg Weber
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Patent number: 4678283Abstract: Trialkanoyloxysilanes of the formula IR.sup.1 --A.sup.1 --A.sup.2 --O--C.sub.n H.sub.2n --Si(OOCR.sup.2) 3 Iwherein R.sup.1 is H or an alkyl group of 1-10 c atoms, wherein one or two non-adjacent CH.sub.2 groups may also be replaced by oxygen atoms, or is F, Cl, Br or CN, R.sup.2 is an alkyl group of 1-5 atoms, A.sup.1 and A.sup.2 are each 1,4-phenylene or 1,4-cyclohexylene groups and n is 2, 3, 4, 5 or 6, can be used for generating a homeotropic orientation of liquid-crystalline phases on surfaces.Type: GrantFiled: September 4, 1984Date of Patent: July 7, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Franz-Heinrich Kreuzer, Rudolf Eidenschink, Georg Weber
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Patent number: 4489201Abstract: This invention relates to fluoroalkyloxyalkyl diorganopolysiloxanes having the general formula ##STR1## where R.sup.1 represents fluoroalkyloxyalkyl groups of the general formula--(CH.sub.2).sub.a --O--C.sub.b R.sub.2b Hin which the hydrogen atom is in the beta position to the ether oxygen, a is 2, 3 or 4; b is an integer having a value of from 1 to 6; R.sup.2 represents an alkyl group having from 1 to 8 carbon atoms whose terminal units may also contain an amino or a thiol group, or an alkenyl group having 2 or 3 carbon atoms, or an aryl group having from 6 to 8 carbon atoms or hydrogen; R.sup.3 represents the group having the formula--(CH.sub.2).sub.c --C.sub.d F.sub.(2d-e+l) Hal.sub.e ,in which Hal represents a terminal chlorine, bromine or iodine atom, c is 2, 3 or 4; d is an integer having a value of from 1 to 18; e is 0 or 1; R.sup.4, R.sup.5 and R.sup.6 are the same as R.sup.Type: GrantFiled: November 21, 1983Date of Patent: December 18, 1984Inventors: Gunter von Au, Ernst Innertsberger, Jakob Schmidlkofer, Wolfgang Kaiser