Oxirane Ring Containing Patents (Class 549/215)
  • Patent number: 4861901
    Abstract: A new group of silane compounds in which silicon atoms are linked together by a hydrocarbon chain and which comprise phenyl groups substituted with an epoxy group or an ethenyl group. The compounds of the present invention have the formula ##STR1## where R.sub.1 is selected from the group consisting of:(a) an aliphatic hydrocarbon group containing 2 to 10 carbon atoms, and(b) a group having the formula ##STR2## where n=1 to 3m=0 to 5;R.sub.2 and R.sub.2 ' are each selected from the group consisting of an alkyl group containing 1 to 4 carbon atoms, an unsubstituted aryl group, and a substituted aryl group;and R.sub.3 is selected from the group consisting of: ##STR3## where R.sub.4, R.sub.5, and R.sub.6 are each selected from the group consisting of H, an alkyl group containing 1 to 4 carbon atoms, and an aryl group; and n=0 to 10.
    Type: Grant
    Filed: May 5, 1987
    Date of Patent: August 29, 1989
    Assignee: Hughes Aircraft Company
    Inventors: Kreisler S. Y. Lau, Susan L. Oldham, William E. Elias, Stephen J. Bigus
  • Patent number: 4855466
    Abstract: Disclosed are compounds having the formula ##STR1## wherein Prot is a hydroxyl protecting group. The compounds are useful as intermediates in the preparation of compounds of the formula ##STR2## which in turn are useful as antiviral agents.
    Type: Grant
    Filed: December 28, 1987
    Date of Patent: August 8, 1989
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Robert Zahler, Glenn A. Jacobs
  • Patent number: 4855456
    Abstract: This invention discloses intermediates and a process for the preparation of 6-desmethyl-6-.alpha.-hydroxymethyl derivatives of lovastatin and analogs thereof at the 8-acyl side chain.
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: August 8, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Ta Jyh Lee, William F. Hoffman
  • Patent number: 4851428
    Abstract: The present invention relates to novel derivatives of LL-F28249 compounds wherein the 23-hydroxyl group is eliminated to form a double bond at the C(22,23)-position (.DELTA..sup.22), and the double bond at the C(26,27)-position is epoxidized concomitant with or without epoxidation of the double bond at the C(14,15)-position. These LL-F28249 compounds (collectively) are isolates from the fermentation broth of Streptomyces cyaneogriseus subspecies noncyanogenus having deposit accession number NRRL 15773. The compounds of the present invention are derived by regioselective epoxidation of 5,23-O,O-bissilylated LL-F28249 compounds at low temperature, desilylation, re-silylation of the 5-hydroxyl group, thiocarbonylation of the 23-hydroxyl group, desilylation and thermalization. The novel compounds of the invention have anthelmintic, insecticidal, ectoparasiticidal, nematicidal and acaricidal activity. Compositions containing these described derivatives as active ingredients thereof are described herein.
    Type: Grant
    Filed: March 6, 1987
    Date of Patent: July 25, 1989
    Assignee: American Cyanamid Company
    Inventors: Goro Asato, Susan Y. Tamura
  • Patent number: 4845258
    Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using quaternary ammonium bifluorides, quaternary phosphonium bifluorides or alkali metal bifluorides as catalysts. The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: July 4, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4845238
    Abstract: An epoxy group-containing disilazane having the formula, ##STR1## wherein A is ##STR2## is described. Also described is a process for producing the epoxy group-containing disilazane. The process comprises reacting a disilazane having the formula, ##STR3## with an epoxy compound selected from a group consisting of allyl glycidyl ether and vinylcyclohexene oxide in the presence of a platinum-type catalyst.
    Type: Grant
    Filed: September 28, 1987
    Date of Patent: July 4, 1989
    Assignee: Toray Silicone Co., Ltd.
    Inventor: Akihiko Shirahata
  • Patent number: 4819953
    Abstract: A cylinder head cover wherein the pan-shaped metallic body has a marginal portion with a groove for a portion of a gasket which is formed on the marginal portion prior to attachment of the cover to the cylinder head of an internal combustion engine. The underside of the marginal portion is coated with one or more layers of a coupling agent and a mold is placed over the marginal portion to define therewith an endless cavity which receives a supply of plasticized silicon rubber at an elevated temperature. The injected material is then heated to vulcanization temperature and is thereupon allowed or caused to set by cooling so that it forms an elastic sealing ring which is bonded to the marginal portion of the cover by the coupling agent. The mold is then removed from the marginal portion and the cover is secured to the cylinder head by fasteners which extend through the bottom wall of the pan-shaped body and are surrounded by noise-damping elastic sealing rings.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: April 11, 1989
    Assignee: Karl Joh Gummiwarenfabrik GmbH
    Inventor: Gunter Joh
  • Patent number: 4804773
    Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using an aminopyridine as catalyst. The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsilyloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: February 14, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4804774
    Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using trialkylphosphites or hexahydrocarbylphosphorous triamides, or both as catalysts. The reaction --which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: February 14, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4804768
    Abstract: There is disclosed a process for producing certain epoxyorganoalkoxysilanes through the rhodium catalyzed hydrosilation of ethylenically unsaturated epoxides and alkoxysilanes in the presence of nitrogenous impurities.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: February 14, 1989
    Assignee: Union Carbide Corporation
    Inventors: Jennifer M. Quirk, Bernard Kanner
  • Patent number: 4804772
    Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts devoid of fluorine (e.g., LiN.sub.3, NaN.sub.3, KN.sub.3, NaCN KCN, CsCN, NaOH, KOH, K.sub.2 CO.sub.3, and Cs.sub.2 CO.sub.3). The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: February 14, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4788268
    Abstract: Epoxysilicone compounds are prepared by first reacting a dibromobenzene compound with magnesium in anhydrous ether solvent to form a Grignard reagent and subsequently reacting the Grignard reagent with allyl bromide to form a (bromophenyl)propene compound. Next, the (bromophenyl)propene compound is converted to the corresponding Grignard reagent, which is then reacted with a compound of the formula I below ##STR1## where n=1 to 6,R.sub.1 and R.sub.2 are each chosen from the group consisting of a C.sub.1 to C.sub.4 alkyl group, a substituted aryl group, and an unsubstituted aryl group.in tetrahydrofuran solvent to form an allyl-terminated silicone compound of formula II below ##STR2## Finally, the allyl-terminated silicone compound is reacted with a chosen epoxidizing agent to form the epoxysilicone compound of formula III below.
    Type: Grant
    Filed: May 5, 1987
    Date of Patent: November 29, 1988
    Assignee: Hughes Aircraft Company
    Inventors: Kreisler S. Y. Lau, Susan L. Oldham, William E. Elias
  • Patent number: 4740595
    Abstract: A multistep process is disclosed for preparing azetidinone intermediates used in the making penems and carbapenems wherein intermediates containing ##STR1## R' is independently hydrogen or 1, 2 or 3 of lower alkyl or lower alkoxy, preferably hydrogen, wherein R" is methyl, ethyl, a phenyl or alkyl, preferably ethyl, as a readily removable nitrogen protecting group are made.
    Type: Grant
    Filed: March 13, 1986
    Date of Patent: April 26, 1988
    Assignee: Schering Corporation
    Inventor: Samuel Chackalamannil
  • Patent number: 4731458
    Abstract: Compounds of the formula ##STR1## are described wherein X is a C.sup.2-11 -alkyl group, optionally substituted by a protected hydroxy, protected oxo or protected carboxy group.
    Type: Grant
    Filed: April 25, 1986
    Date of Patent: March 15, 1988
    Assignee: CBD Corporation
    Inventor: Walter J. Kasha
  • Patent number: 4709068
    Abstract: Compounds containing a dimethylsilane core and a phenoxybenzyl substituent are found to exhibit pyrethroid-like activity toward insects with low toxicity to fish.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: November 24, 1987
    Assignee: FMC Corporation
    Inventor: Scott M. Sieburth
  • Patent number: 4709055
    Abstract: There is described a novel process for producing hydroquinone derivatives of the formula ##STR1## wherein R is an ether protecting group, and their conversion into d-.alpha.-tocopherol, starting from compounds of the formula ##STR2## wherein R is an ether protecting group and R.sup.1 is hydrogen or an ether protecting group.
    Type: Grant
    Filed: January 13, 1986
    Date of Patent: November 24, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4705868
    Abstract: A process for the preparation of expoxidized organosilicon compounds by reacting the corresponding unsaturated organosilicon compounds with perpropionic acid in benzene solution. The said solution can also be employed in purified form with maximum contents of hydrogen peroxide, water, or mineral acid.
    Type: Grant
    Filed: July 30, 1986
    Date of Patent: November 10, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Ulrich Deschler, Andreas Grund, Guenter Prescher
  • Patent number: 4701536
    Abstract: Disclosed are a compound of Formula I: ##STR1## wherein R.sub.1 represents a hydrogen atom or a protective group for a hydroxyl group; and Z represents a direct bond (2,3-cis-5R*, 8S*) or an oxygen atom which forms an oxirane ring having a configuration of (2R*, 3R*, 5R*, 8S*),and a process for preparing the same.By use of the above compound as an intermediate, there can be synthesized periplanone-B which is a sex pheromone of periplaneta.
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: October 20, 1987
    Assignee: UBE Industries, Ltd.
    Inventors: Jiro Tsuji, Takashi Takahashi
  • Patent number: 4673750
    Abstract: An auto-adhering one-component room temperature vulcanizable silicone sealant utilizes a gylcidoxyalkyl substituted mixed alkoxy-oxime silane as an adhesion promoter. The sealant bonds to a variety of substrates including glass, metal, ceramics; does not require a primer to be applied to the substrate; has a low odor and is non-corrosive to ferrous substrates. The sealant is useful as a formed-in-place gasket material as for example, an internal combustion engine and has good oil resistance for an RTV silicone gasketing material.
    Type: Grant
    Filed: April 27, 1986
    Date of Patent: June 16, 1987
    Assignee: Loctite Corporation
    Inventors: M. Dale Beers, James E. Thompson
  • Patent number: 4670421
    Abstract: This invention is concerned with novel 4-[(trialkylsilyl)alkylamino]phenyl compounds and their use as antiatherosclerotic agents.
    Type: Grant
    Filed: July 12, 1982
    Date of Patent: June 2, 1987
    Assignee: American Cyanamid Company
    Inventors: Vern G. DeVries, Janis Upeslacis
  • Patent number: 4652662
    Abstract: A process for preparing organofunctional organopolysiloxanes which comprises reacting a cyclic diorganopolysiloxane with a silane having a SiC-bonded monovalent organic radical with at least one functional group and at least one SiOC-bonded monovalent hydrocarbon radical which can be substituted by an ether oxygen atom, or with an oligomer of such a silane having a maximum of 10 silicon atoms per molecule, in the presence of a quaternary ammonium hydroxide.
    Type: Grant
    Filed: May 14, 1985
    Date of Patent: March 24, 1987
    Assignee: Wacker-Chemie GmbH
    Inventors: Gunther von Au, Karl Braunsperger, Karl Huhn, Ingomar Kovar
  • Patent number: 4652663
    Abstract: A class of novel organosilane compounds are disclosed as represented by the general formulaRSi(OCH.sub.2 CF.sub.3).sub.3,in which R is an atom or group selected from the class consisting of a hydrogen atom, unsaturated monovalent aliphatic hydrocarbon groups having from 2 to 20 carbon atoms, monovalent aryl groups and monovalent organic groups having from 3 to 20 carbon atoms and containing at least one hetero atom, i.e. an atom other than carbon and hydrogen atoms, such as oxygen, halogens, sulfur and nitrogen, the said hetero atom-containing organic group being bonded to the silicon atom through a carbon-to-silicon linkage. Several particular compounds belonging to the class were synthesized and identified.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: March 24, 1987
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Toshio Takago, Yasushi Yamamoto, Koichi Yamaguchi, Hideto Kato
  • Patent number: 4640967
    Abstract: Epoxy- and/or acrylic-functional polysiloxanes are disclosed which, when combined with onium salt photoinitiating catalysts or free-radical photoinitiating catalysts or both, form ultraviolet radiation-curable release coating compositions which render surfaces non-adherent to other surfaces which would normally adhere thereto. The compositions will cure to such an adhesive state upon brief exposure to ultraviolet radiation. Cure and substrate adhesion may be enhanced by the addition of epoxy monomers where onium salt photocatalysts are included. Preparation of the polymers, coating compositions, catalysts and catalyst blends are also disclosed.
    Type: Grant
    Filed: December 18, 1985
    Date of Patent: February 3, 1987
    Assignee: General Electric Company
    Inventor: Richard P. Eckberg
  • Patent number: 4576999
    Abstract: Epoxy- and/or acrylic-functional polysiloxanes are disclosed which, when combined with onium salt photoinitiating catalysts or free-radical photoinitiating catalysts, or both, form ultraviolet radiation-curable release coating compositions which render surfaces non-adherent to other surfaces which would normally adhere thereto. The compositions will cure to such an adhesive state upon brief exposure to ultraviolet radiation. Cure and substrate adhesion may be enhanced by the addition of epoxy monomers where onium salt photocatalysts are included. Preparation of the polymers, coating compositions, catalysts and catalyst blends are also disclosed.
    Type: Grant
    Filed: May 6, 1982
    Date of Patent: March 18, 1986
    Assignee: General Electric Company
    Inventor: Richard P. Eckberg
  • Patent number: 4559407
    Abstract: There is described a novel process for the manufacture of hydroquinone derivatives of the formula ##STR1## wherein R represents an ether protecting group, and their conversion into d-.alpha.-tocopherol starting from compounds of the formula ##STR2## wherein R has the above significance.
    Type: Grant
    Filed: October 11, 1983
    Date of Patent: December 17, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4551541
    Abstract: The present invention relates to new organosilane esters which can be characterized by the formula Y-(CH.sub.2).sub.n Si(CH.sub.3).sub.p -X.sub.m Z.sub.3-(m+p). In this formula, Y represents either a substituted or unsubstituted amino group, or it represents the mercapto moiety or the moiety ##STR1## X represents an alkoxy group with 1 to 4 carbon atoms and Z a glycol ether moiety. The index n can assume the numerical values from 1 to 3, m can be 0 or 1 and p can be 0 or 1 or 2, on the condition that m+p is equal to or less than 2. The new silanes yield very stable hydrolyzates and have good adhesion-improving properties. They are therefore particularly well suited for use in sealing compositions.
    Type: Grant
    Filed: February 1, 1983
    Date of Patent: November 5, 1985
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventor: Horst Hanisch
  • Patent number: 4496745
    Abstract: Compounds of formula (I): ##STR1## (in which: R.sup.1 and R.sup.2 are the same or different and each represents hydrogen or a hydroxy-protecting group:R.sup.3 represents an alkyl group having from 1 to 12 carbon atoms which is optionally substituted, an alkenyl group having from 2 to 12 carbon atoms, an alkynyl group having from 2 to 6 carbon atoms or a cycloalkyl group which is optionally substituted; andX represents an ethylene group, a trans-vinylene group or an ethynylene group) and salts and esters thereof are useful intermediates in the conversion of 5Z-carbacyclin derivatives to their 5E-isomers and in the preparation of certain other carbacyclin compounds.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: January 29, 1985
    Assignee: Sankyo Company, Limited
    Inventors: Shigeo Amemiya, Koichi Kojima
  • Patent number: 4417068
    Abstract: In a process for the addition of silanes or siloxanes having SiH groups to compounds with olefinic double bonds, the invention relates to the use of catalysts of the general formulaYX.sub.2 (NH.sub.3).sub.2in which Y is a platinum or palladium radical, andX is a chlorine, bromine or iodine radical or the NO.sub.2 group.The catalysts have a high selectivity. Side reactions and disproportionation reactions are avoided.
    Type: Grant
    Filed: August 12, 1982
    Date of Patent: November 22, 1983
    Assignee: Th. Goldschmidt AG
    Inventors: Hans-Joachim Kollmeier, Rolf-Dieter Langenhagen
  • Patent number: 4341710
    Abstract: A method is provided for preparing compounds of the formulae ##STR1## wherein A may be --C.dbd.C-- or --C.tbd.C--, by reducing an epoxy lactone of the structure ##STR2## to form the corresponding epoxy hemiacetal, reacting the epoxy hemiacetal with a silyl compound to form an epoxy silyl acetal, reacting the epoxy silyl acetal with an acetylenic derivative to form a silyl acetal, removing the silyl protecting group to form a hemiacetal, reacting the hemiacetal compound with an appropriate Wittig reagent to form a protected difluoro PGF.sub.2.alpha. type compound, removing the protecting group, reacting the difluoro PGF.sub.2.alpha. with an iodine compound to form an iodoether and reacting the iodoether with a base to form the desired compounds.Novel intermediates produced in the above method are also provided.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: July 27, 1982
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Martin F. Haslanger