Oxirane Ring Containing Patents (Class 549/215)
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Patent number: 4861901Abstract: 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: GrantFiled: May 5, 1987Date of Patent: August 29, 1989Assignee: Hughes Aircraft CompanyInventors: Kreisler S. Y. Lau, Susan L. Oldham, William E. Elias, Stephen J. Bigus
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Patent number: 4855466Abstract: 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: GrantFiled: December 28, 1987Date of Patent: August 8, 1989Assignee: E. R. Squibb & Sons, Inc.Inventors: Robert Zahler, Glenn A. Jacobs
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Patent number: 4855456Abstract: 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: GrantFiled: February 29, 1988Date of Patent: August 8, 1989Assignee: Merck & Co., Inc.Inventors: Ta Jyh Lee, William F. Hoffman
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Patent number: 4851428Abstract: 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: GrantFiled: March 6, 1987Date of Patent: July 25, 1989Assignee: American Cyanamid CompanyInventors: Goro Asato, Susan Y. Tamura
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Patent number: 4845258Abstract: 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: GrantFiled: April 4, 1988Date of Patent: July 4, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4845238Abstract: 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: GrantFiled: September 28, 1987Date of Patent: July 4, 1989Assignee: Toray Silicone Co., Ltd.Inventor: Akihiko Shirahata
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Patent number: 4819953Abstract: 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: GrantFiled: November 12, 1987Date of Patent: April 11, 1989Assignee: Karl Joh Gummiwarenfabrik GmbHInventor: Gunter Joh
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Patent number: 4804773Abstract: 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: GrantFiled: April 4, 1988Date of Patent: February 14, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4804774Abstract: 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: GrantFiled: April 4, 1988Date of Patent: February 14, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4804768Abstract: 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: GrantFiled: September 30, 1986Date of Patent: February 14, 1989Assignee: Union Carbide CorporationInventors: Jennifer M. Quirk, Bernard Kanner
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Patent number: 4804772Abstract: 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: GrantFiled: April 4, 1988Date of Patent: February 14, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4788268Abstract: 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: GrantFiled: May 5, 1987Date of Patent: November 29, 1988Assignee: Hughes Aircraft CompanyInventors: Kreisler S. Y. Lau, Susan L. Oldham, William E. Elias
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Patent number: 4740595Abstract: 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: GrantFiled: March 13, 1986Date of Patent: April 26, 1988Assignee: Schering CorporationInventor: Samuel Chackalamannil
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Patent number: 4731458Abstract: 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: GrantFiled: April 25, 1986Date of Patent: March 15, 1988Assignee: CBD CorporationInventor: Walter J. Kasha
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Patent number: 4709068Abstract: Compounds containing a dimethylsilane core and a phenoxybenzyl substituent are found to exhibit pyrethroid-like activity toward insects with low toxicity to fish.Type: GrantFiled: June 2, 1986Date of Patent: November 24, 1987Assignee: FMC CorporationInventor: Scott M. Sieburth
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Patent number: 4709055Abstract: 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: GrantFiled: January 13, 1986Date of Patent: November 24, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4705868Abstract: 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: GrantFiled: July 30, 1986Date of Patent: November 10, 1987Assignee: Degussa AktiengesellschaftInventors: Ulrich Deschler, Andreas Grund, Guenter Prescher
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Patent number: 4701536Abstract: 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: GrantFiled: July 7, 1986Date of Patent: October 20, 1987Assignee: UBE Industries, Ltd.Inventors: Jiro Tsuji, Takashi Takahashi
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Patent number: 4673750Abstract: 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: GrantFiled: April 27, 1986Date of Patent: June 16, 1987Assignee: Loctite CorporationInventors: M. Dale Beers, James E. Thompson
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Patent number: 4670421Abstract: This invention is concerned with novel 4-[(trialkylsilyl)alkylamino]phenyl compounds and their use as antiatherosclerotic agents.Type: GrantFiled: July 12, 1982Date of Patent: June 2, 1987Assignee: American Cyanamid CompanyInventors: Vern G. DeVries, Janis Upeslacis
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Patent number: 4652662Abstract: 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: GrantFiled: May 14, 1985Date of Patent: March 24, 1987Assignee: Wacker-Chemie GmbHInventors: Gunther von Au, Karl Braunsperger, Karl Huhn, Ingomar Kovar
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Patent number: 4652663Abstract: 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: GrantFiled: May 13, 1986Date of Patent: March 24, 1987Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Toshio Takago, Yasushi Yamamoto, Koichi Yamaguchi, Hideto Kato
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Patent number: 4640967Abstract: 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: GrantFiled: December 18, 1985Date of Patent: February 3, 1987Assignee: General Electric CompanyInventor: Richard P. Eckberg
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Patent number: 4576999Abstract: 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: GrantFiled: May 6, 1982Date of Patent: March 18, 1986Assignee: General Electric CompanyInventor: Richard P. Eckberg
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Patent number: 4559407Abstract: 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: GrantFiled: October 11, 1983Date of Patent: December 17, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4551541Abstract: 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: GrantFiled: February 1, 1983Date of Patent: November 5, 1985Assignee: Dynamit Nobel AktiengesellschaftInventor: Horst Hanisch
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Patent number: 4496745Abstract: 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: GrantFiled: October 25, 1983Date of Patent: January 29, 1985Assignee: Sankyo Company, LimitedInventors: Shigeo Amemiya, Koichi Kojima
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Patent number: 4417068Abstract: 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: GrantFiled: August 12, 1982Date of Patent: November 22, 1983Assignee: Th. Goldschmidt AGInventors: Hans-Joachim Kollmeier, Rolf-Dieter Langenhagen
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Patent number: 4341710Abstract: 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: GrantFiled: October 5, 1981Date of Patent: July 27, 1982Assignee: E. R. Squibb & Sons, Inc.Inventor: Martin F. Haslanger