Aryl-oxy-alkenyl Or Aryl-oxy-alkynyl Patents (Class 568/657)
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Patent number: 9284201Abstract: The present invention relates to amine modified clay sorbents and methods for their use. The sorbents of the present invention have particular application for the sorption of hydrophobic contaminants, particularly constituents of AFFFs, surfactants and/or perfluorinated or polyfluorinated compounds.Type: GrantFiled: December 7, 2010Date of Patent: March 15, 2016Assignee: CRC CARE Pty LtdInventors: Venkata Subba Rao Kambala, Ravendra Naidu
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Publication number: 20110084230Abstract: The present application discloses a process for preparing a compound of the general formula R1-M1-Ad.zLiX (I) by reacting a compound R1-A (III) with an element M1 in the presence of lithium salts. The application also discloses a process for preparing a compound of the general formula R1m-M3-Tm.zLiX (II) by reacting a compound R1-A (III) with an M3-containing compound in the presence of lithium salts and in the presence of an elemental metal M2. The metal M3 may be selected from Al, Mn, Cu, Zn, Sn, Ti, In, La, Ce, Nd, Y, Li, Sm, Bi, Mg, B, Si and S.Type: ApplicationFiled: April 3, 2007Publication date: April 14, 2011Inventors: Paul Knochel, Andrei Gavryushin, Vladimir Malakhov, Arkady Krasovskiy
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Patent number: 7842843Abstract: To provide a C4 fraction that contains significantly reduced amounts of butynes and methylallene and to provide a process for low-cost and effective production of ethers in which the C4 fraction is used as the starting material for a telomerization process. A mixture containing 25 to 80 mass % 1,3-butadiene, 13 to 68 mass % butenes and 2 to 15 mass % butanes with butynes and methylallene being contained in amounts of 50 ppm or less and 5 to 800 ppm, respectively.Type: GrantFiled: November 29, 2006Date of Patent: November 30, 2010Assignee: Kuraray Co., Ltd.Inventors: Jin Tokuyasu, Hideharu Iwasaki
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Publication number: 20100261936Abstract: A process of producing ?,?-unsaturated ethers includes pyrolyzing an acetal represented by Formula (2) below in a gas phase in the presence of a catalyst and a compound having at least one hydrogen atom capable of hydrogen bonding to produce an ?,?-unsaturated ether represented by Formula (3) below: R1R2CH—CR3(OR4)2??(2) R1R2C?C—R3(OR4)??(3) In Formulae (2) and (3), R1, R2 and R3 are each independently a hydrogen atom, an alkyl group, an alkenyl group or an aryl group; R4 is an alkyl group, an alkenyl group or an aryl group; the plurality of R4 in Formula (2) may be the same or different from each other.Type: ApplicationFiled: November 6, 2008Publication date: October 14, 2010Applicant: SHOWA DENKO K.K.Inventors: Yoshikuni Okumura, Hiroto Kouka, Takanori Aoki
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Patent number: 7622616Abstract: A process for obtaining vinyl compounds by dehalogenation of halofluorinated compounds having a linear, branched or cyclic structure, said halofluorinated compounds containing in the molecule at least one group: wherein Y1 and Y2, equal to or different from each other, are selected from Cl, Br, I; wherein the halofluorinated compounds are dehalogenated in the presence of a transition metal, or of transition metal couples, by operating in a biphasic system of solvents immiscible among each other, formed of a (per)fluorinated solvent and a dipolar aprotic or protic solvent (co-solvent), wherein the ratio moles co-solvent/equivalents of the halofluorinated compound ranges from 0.5 to 10, preferably from 0.5 to 5, still more preferably from 1 to 3.Type: GrantFiled: May 4, 2006Date of Patent: November 24, 2009Assignee: Solvay Solexis S.p.A.Inventors: Ivan Wlassics, Vito Tortelli
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Patent number: 7119222Abstract: A method for producing an allyl compound having a compositional formula different from that of an allyl starting material compound, which comprises reacting the allyl starting material compound with an oxygen nucleophilic agent in the presence of a catalyst containing at least one transition metal compound containing a transition metal selected from the group consisting of transition metals belonging to Group 8 to Group 10 of the Periodic Table and a multidentate phosphite compound.Type: GrantFiled: August 27, 2003Date of Patent: October 10, 2006Assignee: Mitsubishi Chemical CorporationInventors: Masaki Takai, Yoshiyuki Tanaka
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Patent number: 7115784Abstract: The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate.Type: GrantFiled: January 4, 2005Date of Patent: October 3, 2006Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Artis Klapars, Jon C. Antilla, Gabriel E. Job, Martina Wolter, Fuk Y. Kwong, Gero Nordmann, Edward J. Hennessy
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Patent number: 7094918Abstract: Novel ultraviolet absorbing compounds that are liquid in nature, are low in color (and thus permit use without the concomitant necessity of adding large amounts of other coloring agents to combat such discoloring), and are highly effective in providing protection in wavelength ranges for which previous attempts at low-color ultraviolet absorbers have failed are provided herein. Such compounds provide such excellent, inexpensive, and beneficial protection from ultraviolet exposure within various media, including, but not limited to, clear thermoplastics. The particular compounds are generally polymeric in nature including various chain lengths of polyoxyalkylenes thereon and are liquid in nature to facilitate handling and introduction within the target media. In addition, such ultraviolet absorbers also exhibit extremely low migratory properties thereby providing long-term protective benefits to the target media as well.Type: GrantFiled: April 28, 2003Date of Patent: August 22, 2006Assignee: Milliken & CompanyInventors: Jusong Xia, Mary E. Mason, Eric B. Stephens
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Patent number: 6891058Abstract: Novel ultraviolet absorbing compounds that are liquid in nature, are extremely low in color (and thus permit use without the concomitant necessity of adding large amounts of other coloring agents to combat such discoloring), and are highly effective in providing protection in wavelength ranges for which previous attempts at low-color ultraviolet absorbers have failed are provided herein. Such compounds provide such excellent, inexpensive, and beneficial protection from ultraviolet exposure within various media, including, but not limited to, clear thermoplastics. The particular compounds are generally polymeric in nature including various chain lengths of polyoxyalkylenes thereon and are liquid in nature to facilitate handling and introduction within the target media. In addition, such ultraviolet absorbers also exhibit extremely low migratory properties thereby providing long-term protective benefits to the target media as well.Type: GrantFiled: January 3, 2003Date of Patent: May 10, 2005Assignee: Milliken & CompanyInventors: Xiaodong E. Zhao, Todd D. Danielson, Mary E. Mason, Daniel M. Connor, Eric B. Stephens, Jason D. Sprinkle, Jusong Xia
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Patent number: 6809223Abstract: An improved method is described for making 9-deoxy-PGF1-type compounds. In contrast to the prior art, the method is stereoselective and requires fewer steps than the known methods for making these compounds. “Also described are novel intermediate compounds used in the process described for making 9-deoxy-PGF1-type compounds.Type: GrantFiled: August 27, 2003Date of Patent: October 26, 2004Assignee: United Therapeutics CorporationInventors: Robert M. Moriarty, Hitesh Bhatra
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Patent number: 6559216Abstract: Novel ultraviolet absorbing compounds that are liquid in nature, are extremely low in color (and thus permit use without the concomitant necessity of adding large amounts of other coloring agents to combat such discoloring), and are highly effective in providing protection in wavelength ranges for which previous attempts at low-color ultraviolet absorbers have failed are provided herein. Such compounds provide such excellent, inexpensive, and beneficial protection from ultraviolet exposure within various media, including, but not limited to, clear thermoplastics. The particular compounds are generally polymeric in nature including various chain lengths of polyoxyalkylenes thereon and are liquid in nature to facilitate handling and introduction within the target media. In addition, such ultraviolet absorbers also exhibit extremely low migratory properties thereby providing long-term protective benefits to the target media as well.Type: GrantFiled: August 21, 2001Date of Patent: May 6, 2003Assignee: Milliken & CompanyInventors: Xiaodong E. Zhao, Todd D. Danielson, Mary E. Mason, Daniel M. Connor, Eric B. Stephens, Jason D. Sprinkle, Jusong Xia
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Patent number: 6399837Abstract: A method of polymerizing at least one olefin comprising contacting the olefin with a catalyst composition comprising: 1) a procatalyst composition comprising a magnesium and titanium-containing component and an electron donor compound of the structure: wherein R1 is ethoxy, and R2 is an alkoxy group having from one to ten carbon atoms, and R3-R6 are each individually, hydrogen, hydrocarbyl, hydrocarboxy, nitro, a silyl group or a halogen, 2) a cocatalyst and optionally 3) a selectivity control agent.Type: GrantFiled: June 5, 2000Date of Patent: June 4, 2002Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stanley Edward Wilson, Robert Converse Brady, III
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Patent number: 6271423Abstract: A process for preparing butenyl ethers of the formula I CH3—CH═CH—CH2—OR I by reacting butadiene or butadiene-containing hydrocarbon streams with alcohols of the formula II ROH II at elevated temperature and superatmospheric pressure in the presence of transition metal complexes containing ligands of compounds of elements of group V of the Periodic Table of the Elements to form an isomer mixture of butenyl ethers of the formula I and butenyl ethers of the formula III CH2═CH—CH(OR)—CH3 III and, optionally, isomerizing the butenyl ethers of the formula III to butenyl ethers of the formula I, where R is as defined in the specification and the catalyst used is a complex of a transition metal of group VIII of the Periodic Table of the Elements with ligands of the formula IV where M is an iron, cobalt, nickel, or ruthenium atom, X is a bridge and where n, y and R1-R6 are as defined in the specification.Type: GrantFiled: December 8, 1999Date of Patent: August 7, 2001Assignee: BASF AktiengesellschaftInventor: Jürgen Dahlhaus
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Patent number: 6211416Abstract: Enol ethers of the formula I where R1 is an aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radical which may carry further substituents which do not react with acetylenes or allenes, and the radicals R, independently of one another, are hydrogen or aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic radicals, which may be bonded to one another to form a ring, and m is 0 or 1, are prepared by reacting an acetal or ketal of the formula II with an acetylene or allene of the formula III or IV where R and R1 have the abovementioned meanings, in the gas phase at elevated temperatures in the presence of a zinc- or cadmium- and silicon- and oxygen-containing heterogeneous catalyst.Type: GrantFiled: December 6, 1999Date of Patent: April 3, 2001Assignee: BASF AktiengesellschaftInventors: Joaquim Henrique Teles, Norbert Rieber, Klaus Breuer, Dirk Demuth, Hartmut Hibst, Heinz Etzrodt, Udo Rheude
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Patent number: 6166226Abstract: A method for preparing an aryl ether compound is provided in which an alcohol is reacted with an aromatic compound in the presence of a base, and a transition metal catalyst selected from the group consisting of platinum and nickel to form an aryl ether. The aromatic compound comprises an activated substituent, X, said activated substituent being a moiety such that its conjugate acid HX has a pKa of less than 5.0. The catalyst is preferably a soluble palladium complex in the presence of supporting ligands.Type: GrantFiled: December 8, 1998Date of Patent: December 26, 2000Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, John P. Wolfe, Michael Palucki
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Patent number: 6156889Abstract: The subject matter of the present invention relates to a reagent and a process useful for cleaving a functional group protected by an alkoxycarbonyl group during an organic synthesis. This reagent comprises: a) an aqueous phase; b) a catalyst comprising at least one group VIII element in the periodic table of elements and at least one water-soluble ligand, wherein the group VIII element in the periodic table is maintained in the aqueous phase by the formation of a complex with at least one water-soluble ligand; and c) a nucleophilic compound soluble in the aqueous phase; and optionally d) an organic phase.Type: GrantFiled: October 9, 1998Date of Patent: December 5, 2000Assignee: Rhodia ChimieInventors: Jean-Marie Bernard, Errol Blart, Jean-Pierre Genet, Monique Savignac, Sandrine Lemaire-Audoire
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Patent number: 6124507Abstract: Novel compositions of the structure ##STR1## wherein R.sup.1 and R.sup.2 are each an alkoxy group which may be the same or different and have from one to ten carbon atoms, and R.sup.3 -R.sup.6 are each individually, hydrogen, hydrocarbyl, hydrocarboxy, nitro, a silyl group or a halogen, with the provisos that if either R.sup.1 or R.sup.2 are methoxy, then at least one of R.sup.3 -R.sup.6 is not hydrogen, if R.sup.1 and R.sup.2 are both ethoxy, then at least one of R.sup.3 -R.sup.6 is not hydrogen, and R.sup.1 and R.sup.2 cannot both be methoxy, are taught herein, which may be used as electron donors, either internal or external, for catalysts used in the polymerization of olefins.Type: GrantFiled: December 10, 1997Date of Patent: September 26, 2000Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stanley Edward Wilson, Robert Converse Brady, III
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Patent number: 6106908Abstract: Liquid crystalline compounds useful in super twisted nematic liquid crystal displays are described and have the formula: ##STR1## wherein n is 1-5;m is 0-5;p is 0, 1 or 2;q is 0, 1 or 2p+q is less than or equal to 3;A.sub.1, A.sub.2, A.sub.3 are independently chosen from 1,4-disubstituted benzene 2,5-disubstituted pyrimidine, 1,5-disubstituted pyridine, 2,6-disubstituted naphthalene which may be laterally substituted with F, Cl, Br or CN, trans-1,4-disubstituted cyclohexane 2,5-disubstituted dioxane, 2,5-disubstituted thiophene, 2,5-disubstituted furan, 2,5-disubstituted thiodiazoleZ.sub.1 may be COO, OOC, OCH.sub.2, O;Z.sub.2, Z.sub.3 are independently chosen from a direct bond, COO, OOC, C.sub.2 H.sub.4, CH.sub.2 O, OCH.sub.2, C.sub.4 H.sub.8, C.sub.3 H.sub.6 O, (E)--CH.dbd.CHC.sub.2 H.sub.4, (E)--CH.dbd.CHCH.sub.2 O, --C.tbd.C--;R.sub.1 is alkyl, and may contain up to 20 carbon atoms and may be branched or a straight chain; provided that at least one of, A.sub.1, A.sub.2, A.sub.Type: GrantFiled: March 19, 1999Date of Patent: August 22, 2000Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Warren L Duffy, John W Goodby, Stephen M Kelly
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Patent number: 5986137Abstract: A process and reagent for allylating a nucleophile preferably of formula (V).(R).sub.n Ar--Y--H (V)The nucleophile is reacted with a reagent containing an allyl derivative and a catalyst in an aqueous phase containing at least lone element of group VIII of the Classification of the elements. A water-soluble phosphine may also be present in the reagent, and the reagent may also contain at least one organic phase.Type: GrantFiled: June 12, 1998Date of Patent: November 16, 1999Assignee: Rhodia ChimieInventors: Jean-Michel Grosselin, Hubert Kempf, Jean-Pierre LeCouve
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Patent number: 5847166Abstract: A method for preparing an aryl ether compound is provided in which an alcohol is reacted with an aromatic compound in the presence of a base, and a transition metal catalyst selected from the group consisting of platinum and nickel to form an aryl ether. The aromatic compound comprises an activated substituent, X, said activated substituent being a moiety such that its conjugate acid HX has a pKa of less than 5.0. The catalyst is preferably a soluble palladium complex in the presence of supporting ligands.Type: GrantFiled: October 10, 1996Date of Patent: December 8, 1998Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, John P. Wolfe, Michael Palucki
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Patent number: 5847117Abstract: The subject matter of the present invention relates to a reagent and a process useful for cleaving a functional group protected by an alkoxycarbonyl group during an organic synthesis. This reagent comprises: a) an aqueous phase; b) a catalyst comprising at least one group VIII element in the periodic table of elements and at least one water-soluble ligand, wherein the group VIII element in the periodic table is maintained in the aqueous phase by the formation of a complex with at least one water-soluble ligand; and c) a nucleophilic compound soluble in the aqueous phase; and optionally d) an organic phase.Type: GrantFiled: August 18, 1993Date of Patent: December 8, 1998Assignee: Rhone-Poulenc ChimieInventors: Jean-Marie Bernard, Errol Blart, Jean-Pierre Genet, Monique Savignac, Sandrine Lemaire-Audoire
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Patent number: 5786520Abstract: Carbocyclic/aliphatic ethers, for example anisole, quaicol, guaethol, p-methoxyphenol and ethylene dioxybenzene, are selectively prepared, in good yield, by reacting a phenolic compound, for example a phenol, hydroquinone, pyrocatechin, naphthol, or the like, with an alcohol, for example methanol, ethanol, isopropanol, ethylene glycol, etc., in gaseous phase, in the presence of a catalytically effective amount of a trivalent rare earth metal orthophosphate, for example a lanthanum, cerium or samarium orthophosphate, optionally doped with an alkali or alkaline earth metal, preferably cesium.Type: GrantFiled: October 15, 1996Date of Patent: July 28, 1998Assignee: Rhone-Poulenc ChimieInventors: Laurent Gilbert, Marcelle Janin, Anne-Marie Le Govic, Philippe-Jean Tirel
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Patent number: 5633411Abstract: Allylic styrene ether compounds of the formula: ##STR1## where R.sup.1 is an optionally substituted allylic or propargyl hydrocarbon group, and R.sup.2, R.sup.3, and R.sup.4 are independently H, C.sub.1-6 hydrocarbon or C.sub.1-6 hydrocarbonoxy groups, are prepared in a single pot reaction from relatively low cost materials. The method includes the steps of reacting a 4-acyloxystyrene of the formula ##STR2## where R is an acyl group, with at least one mole of a base which can readily saponify or hydrolyze the phenolic ester bond per mole of acyloxystyrene, and then adding to the reaction mixture an alloylating agent of the formula R.sup.1 X, where R.sup.1 is as previously defined and X is chloride, bromide, iodide, a sulfonic ester or a hydrocarbon sulfate group, to form said allylic styrene ether compound. The method may be employed to prepare mono-styryl functional compounds or di-styryl functional compounds such as 1,4-bis(4'-vinylphenoxy)but-2-ene.Type: GrantFiled: May 28, 1996Date of Patent: May 27, 1997Assignee: Loctite CorporationInventors: John G. Woods, Maria Masterson
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5242996Abstract: A modified epoxy resin or compound of the formula: ##STR1## wherein A is the backbone reside of a glycidyl ether epoxy resin with removal of the glycidyloxy groups; R.sup.1 and R.sup.2 are independently a hydrogen atom or C.sub.1 -C.sub.12 alkyl; R.sup.3 is a glycidyl group; and n is an integer of greater than 1. A method for producing the modified epoxy resin is also disclosed.Type: GrantFiled: May 22, 1991Date of Patent: September 7, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
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Patent number: 5141970Abstract: A method of forming high-temperature resistant polymers by a 2 step curing process comprising(a) curing a polymerizable composition at least one aromatic compound having alpha and/or beta instruction which is not substantially reactive under the curing condition of step a, particularly allyl or properyl, and(b) heating the cured composition of step a in the presence of acid to form a crosslinked resin.Type: GrantFiled: December 10, 1990Date of Patent: August 25, 1992Assignee: Loctite (Ireland) LimitedInventors: Ciaran B. McArdle, Joseph Burke, John G. Woods, Edward K. Welch, II
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Patent number: 5084490Abstract: Styryloxy compounds of the formula IV ##STR1## wherein R.sup.1 and R.sup.2 are H, or one of R.sup.1 and R.sup.2 is H and the other is methyl;R.sup.7 and R.sup.8 (which may be the same or different) are H, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkenyl; or one of R.sup.7 and R.sup.8 may be --OR.sup.6 or C.sub.1 -C.sub.5 alkoxy or C.sub.1 -C.sub.5 alkenyloxy if R.sup.2 is not methyl;R.sup.6 is selected from the group consisting of: ##STR2## where R.sup.10 is C.sub.1 -C.sub.5 alkyl; and R.sup.11, R.sup.12 and R.sup.13, which may be the same or different, are H or C.sub.1 -C.sub.5 alkyl, are described as new low viscosity liquid styryloxy monomers which can be photocured and which form transparent polymers. They have an advantageous effect in a mixture with 4-allyloxystyrene, and this mixture has a synergistic effect in combination with divinyl ethers of a polyalkylene oxide.Type: GrantFiled: December 10, 1990Date of Patent: January 28, 1992Assignee: Loctite (Ireland) LimitedInventors: Ciaran B. McArdle, Joseph Burke, John G. Woods
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Patent number: 4931589Abstract: A compound of formula (I) ##STR1## its isomers and its salts in which R.sub.1, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.8 acyloxy or hydroxyl;R' is hydrogen or C.sub.1 -C.sub.6 -alkyl;R" is either a polyene chain or a benzene ring are useful in cosmetics and in the treatment of various dermatological and other complaints.Type: GrantFiled: July 13, 1988Date of Patent: June 5, 1990Assignee: L'OrealInventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
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Patent number: 4847429Abstract: Process is disclosed for the preparation of phenylhydroquinones by the alkylation of hydroquinone (or derivatives thereof) with the cyclohexyl moieties, cyclohexanol or cyclohexene (or derivatives thereof), followed by dehydrogenation of the intermediate cyclohexylhydroquinone.Type: GrantFiled: August 3, 1987Date of Patent: July 11, 1989Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, Bruce L. Gustafson, Dale E. Van Sickle, Joseph S. Bowers, Jr.
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Patent number: 4846998Abstract: Cyclohexane derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 Iin whichR.sup.1 and R.sup.2 are each an alkyl group having 1-10 C atoms, in which one or two non-adjacent CH.sub.2 groups can also be replaced by O atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH.dbd.CH-- groups, one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, CN or R.sup.3 --A.sup.3 --Z.sup.2 --,A.sup.1 is --A--, A.sup.4 --A-- or --A--A.sup.4 --,A is a trans-1,4-cyclohexylene group which can be substituted in the 2-, 3-, 5- and/or 6-position one or more times by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group which each have 1-10 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, and which may also be substituted in the 1- and/or 4-position,A.sup.2, A.sup.3 and A.sup.Type: GrantFiled: November 21, 1986Date of Patent: July 11, 1989Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ludwig Pohl, Bernhard Scheuble, Reinhard Hittich, Rudolf Eidenschink, Hans A. Kurmeier, Andreas Wachtler
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Patent number: 4835272Abstract: A process for formation of a base, which comprises reacting an acetylide compound with a salt. The acetylide compound has the following formula:(R--C.tbd.C--).sub.n Mwherein R is a monovalent group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group and a heterocyclic group, each of which may have one or more substituent groups; M is an n-valent transition metal atom; and n is 1, 2 or 3. The salt is composed of an anion having an affinity for the transition metal (M) (the affinity of the anion for the transition metal is more than that of the acetylide anion (R--C.tbd.C.crclbar.)), and a cation derived from one selected from the group consisting of an alkali metal, an alkaline earth metal, ammonia and an organic base. A light-sensitive material containing the acetylide compound and the salt is also disclosed.Type: GrantFiled: July 16, 1987Date of Patent: May 30, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Shunichi Ishikawa, Ken Kawata
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Patent number: 4831183Abstract: A process for the telomerization of a conjugated alkadiene with an organic hydroxy compound to produce an organo-oxyalkadiene is disclosed. A palladium catalyst having an ionic ligand is employed in a substantially oxygen-free environment in the presence of an aprotic polar solvent so that the reaction products may be separated from the catalyst by solvent extraction with a hydrocarbon solvent.Type: GrantFiled: October 17, 1988Date of Patent: May 16, 1989Assignee: National Distillers and Chemical CorporationInventor: Ronnie M. Hanes
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Patent number: 4825005Abstract: The invention relates to a novel process for the preparation of ether and thioether compounds of formula ##STR1## by reacting compounds of formula ##STR2## with compounds of formulaR.sub.1 --Ywherein R, R.sub.1, X, Y and n are as defined in claim 1, in the presence of an acid acceptor and in an aliphatic ketone, which process is carried out under pressure in the temperature range from 115.degree. to 200.degree. C.Type: GrantFiled: August 24, 1987Date of Patent: April 25, 1989Assignee: Ciba-Geigy CorporationInventors: Christian Frey, Bernd Dill
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Patent number: 4740330Abstract: The aromatic hydroxyl groups of aromatic hydroxyl-containing compounds can be allylated to greater than 95% conversion by reacting the alkali metal salt of said aromatic hydroxyl-containing compounds with an allyl halide such as allyl chloride in the presence of a polar aprotic solvent such as dimethylformamide. These compounds are useful in preparing epoxy resins containing a low halogen content.Type: GrantFiled: September 3, 1986Date of Patent: April 26, 1988Assignee: The Dow Chemical CompanyInventors: Chun S. Wang, Zeng-kun Liao
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Patent number: 4663478Abstract: By reacting a phenol compound with an organic halide selected from the group consisting of a haloform, a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, using as a catalyst a fixed cyclodextrin having hydroxyl groups crosslinked with a bivalent hydrocarbon group having free valences at its both ends, said hydrocarbon group having at least one hydrogen atom substituted or unsubstituted with a member selected from the group consisting of an alkyl group, a halogen atom and a hydroxyl group and containing or not containing at least one combination of two neighboring carbon atoms having therebetween at least one member selected from the group consisting of an oxygen atom, a sulfur atom and a phenylene, various useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: April 18, 1985Date of Patent: May 5, 1987Assignee: Hidefuni HiraiInventors: Hidefuni Hirai, Makoto Komiyama, Izuru Sugiura
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Patent number: 4642392Abstract: A process for the telomerization of a conjugated alkadiene with an alkanol is disclosed for the production of an organo-oxyalkadiene. A palladium catalyst having a phosphine or stibene ligand is employed in a substantially oxygen-free environment and in the presence of a high boiling solvent so that the reaction products may be separated from the catalyst by distillation. Vacuum fractional distillation is a preferred method for separating the products.Type: GrantFiled: September 30, 1985Date of Patent: February 10, 1987Assignee: National Distillers and Chemical CorporationInventor: Ronnie M. Hanes
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Patent number: 4642349Abstract: Aromatic ethers or polyethers are prepared by reacting an organic halide such as a hydrocarbon halide with an aryl lower alkyl carbonate in the presence of an initiator.Type: GrantFiled: May 24, 1982Date of Patent: February 10, 1987Assignee: The Dow Chemical CompanyInventor: James M. Renga
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Patent number: 4613703Abstract: An isomeric mixture of C- and O-allylated aromatic compounds is prepared by contacting an allyl halide, a hydroxyaromatic reactant, an alkaline agent, water and a quaternary salt catalyst. This mixture may be thermally isomerized to obtain the C-allylated compounds in high yield.Type: GrantFiled: April 5, 1982Date of Patent: September 23, 1986Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.
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Patent number: 4560786Abstract: .DELTA..sup.8,9 -Prostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH;B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR4## wherein the OH--group can be in the .alpha.-- or .beta.-- position; D and E jointly are a direct bond orD is straight chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen, sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine or alkyl;R.sub.4 is free or functionally modified hydroxy andR.sub.Type: GrantFiled: June 24, 1982Date of Patent: December 24, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4523031Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with an organic halide selected from the group consisting of a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, a substituent group derived from said organic halide can be introduced to the para-position of the phenol compound with high selectivity, whereby various useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: September 7, 1983Date of Patent: June 11, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hidefumi Hirai, Makoto Komiyama
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Patent number: 4523037Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with a haloform in the presence of an alkali metal hydroxide, while maintaining the molar ratio of the cyclodextrin to the haloform at 0.5 to 10, a substituent group derived from the haloform can be introduced to the para-position of the phenol compound with high selectivity, whereby useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: September 7, 1983Date of Patent: June 11, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hidefumi Hirai, Makoto Komiyama
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Patent number: 4507492Abstract: Allyl derivatives of phenols, thiophenols and arylamines are prepared by contacting such aromatic reactant with an allyl lower alkyl carbonate in the presence of a molybdenum, tungsten or Group VIII metal.Type: GrantFiled: May 6, 1983Date of Patent: March 26, 1985Assignee: The Dow Chemical CompanyInventor: Edmund P. Woo
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Patent number: 4399301Abstract: Methylenically-substituted undecadiene compounds having the structural formula: ##STR1## wherein X is selected from the group consisting of lower acyloxy, aryloxy having from 6 to 14 carbon atoms, lower alkoxy and hydroxy, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are independently selected from the group consisting of hydrogen and lower alkyl, with the proviso that at least one of R.sub.3, R.sub.5 and R.sub.6 and at least one of R.sub.9, R.sub.10, R.sub.11 and R.sub.12 must be hydrogen, are prepared by reacting a diene having the structural formula: ##STR2## with a conjugated diene having the structural formula: ##STR3## in the presence of a rhodium/trivalent phosphorus catalyst, with the atomic ratio of the trivalent phosphorus to the rhodium therein being at least 1.5. The compounds can be hydrogenated and saponified to form known alcohols which are precursors for biodegradable detergents.Type: GrantFiled: September 13, 1979Date of Patent: August 16, 1983Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4393249Abstract: A process for removing alkynes from hydrocarbon mixtures, particularly those containing butadiene by reacting the alkynes with hydroxyl group containing organic compounds in the presence of a silver exchanged ion-exchange resin and separating the products formed from the unreacted components of said mixture.Type: GrantFiled: October 23, 1981Date of Patent: July 12, 1983Assignee: The Dow Chemical CompanyInventors: Albert Heuvelsland, Fritz F. F. Jann, Greet de Block-Martens
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Patent number: 4314086Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Daniel Michelet
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Patent number: 4219677Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.Type: GrantFiled: July 19, 1978Date of Patent: August 26, 1980Assignee: Rhone-Poulenc IndustriesInventor: Emile Kuntz
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Patent number: 4209639Abstract: This disclosure describes novel 13-thia prostanoic acids and derivatives thereof useful in causing prostaglandin-like biological responses.Type: GrantFiled: September 22, 1975Date of Patent: June 24, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4142060Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.Type: GrantFiled: July 21, 1977Date of Patent: February 27, 1979Assignee: Rhone-Poulenc IndustriesInventor: Emile Kuntz
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Patent number: 4138411Abstract: Aromatic alkenyl compounds, for example, eugenol and safrole, are isomerized, for example to isoeugenol and isosafrole, by contact with a ruthenium or osmium catalyst.Type: GrantFiled: April 14, 1976Date of Patent: February 6, 1979Assignee: Rhone-Poulenc S. A.Inventor: Pierre Gandilhon