Acyclic Hydrocarbyl Group Bonded Directly To The Benzene Ring Patents (Class 568/658)
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Patent number: 11434367Abstract: A polyphenylene ether resin of Formula (1) and a resin composition including the polyphenylene ether resin of Formula (1) are provided. The resin composition is useful for making different articles, including a prepreg, a resin film, a laminate or a printed circuit board, which may achieve excellent multi-layer board thermal resistance and excellent height of impact whitening, in addition to the desirable properties such as fully dissolvable varnish, absence of branch-like pattern or dry board on laminate appearance, high glass transition temperature, low dissipation factor, low Z-axis ratio of thermal expansion and high copper foil peeling strength.Type: GrantFiled: October 14, 2020Date of Patent: September 6, 2022Assignee: ELITE ELECTRONIC MATERIAL (KUNSHAN) CO., LTD.Inventor: Yan Zhang
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Patent number: 11111336Abstract: A poly(phenylene ether) copolymer of 2-methyl-6-phenylphenol and a dihydric phenol having an absolute number average molecular weight of 1,000 to 10,000 grams/mole is made by polymerization of 2-methyl-6-phenylphenol and a dihydric phenol in the presence of molecular oxygen, a polymerization catalyst comprising a metal ion and at least one amine ligand, and a solvent composed of at least 95 weight percent of a C1-C3 alcohol selected from methanol, ethanol, 1-propanol, and 2-propanol. The poly(phenylene ether) copolymer can be, for example, a copolymer of 2-methyl-6-phenylphenol, 2,2-bis(3,5-dimethyl-4-hydroxyphenol)propane, and optionally 2,6-dimethylphenol. The poly(phenylene ether) copolymer finds utility in curable compositions, cured compositions, and articles.Type: GrantFiled: March 27, 2018Date of Patent: September 7, 2021Assignee: SHPP GLOBAL TECHNOLOGIES B.V.Inventors: Eylem Tarkin-Tas, Huseyin Tas, Mark R. Denniston
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Patent number: 8921611Abstract: The invention provides a method for preparing 1,4-di-tert-butyl-2,5-bis(2-methoxyethoxy)benzene, the method comprising reacting 2,5-di-tert-butylbenzene-1,4-diol with cesium carbonate and halogenated ether in dimethyl formamide. The method yields 500 gram batches at a time, or multiples thereof. The method enables the industrial production of redox shuttles for use in lithium ion battery systems.Type: GrantFiled: April 13, 2012Date of Patent: December 30, 2014Assignee: Uchicago Argonne, LLCInventors: Krzysztof Z. Pupek, Trevor L. Dzwiniel, Gregory K. Krumdick
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Publication number: 20140336270Abstract: Methods of producing substituted and non-substituted beta-methyl styrene by a cross-coupling reaction are provided. The disclosure also provides for methods of preparing (E)-Anethol and related compounds by a cross coupling reaction of potassium allyltrifluoroborate and 4-bromoanisole and aryl halides. Compounds, compositions, and methods of treating disorders utilizing beta-methyl styrene are also provided.Type: ApplicationFiled: March 6, 2014Publication date: November 13, 2014Applicant: Tennessee Board of RegentsInventor: Mohammad AL-MASUM
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Patent number: 8865775Abstract: An anti-inflammatory agent or cancer-preventive agent comprising 4-vinyl-2,6-dimethoxyphenol of the formula (1): or a PD thereof.Type: GrantFiled: January 20, 2012Date of Patent: October 21, 2014Inventors: Hiroshi Maeda, Tetsuya Tsukamoto, Masae Tatematsu
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Publication number: 20130324745Abstract: A process is provided which allows the synthesis of a large number of styrene derivatives with formation of C—C bonds, with use being possible of economically advantageous substrates, readily available carbon nucleophiles, and both inexpensive and environmentally unproblematic catalyst systems, permitting reaction under mild conditions and a high compatibility with functional groups on the reactants involved.Type: ApplicationFiled: May 31, 2013Publication date: December 5, 2013Inventors: Matthias GOTTA, Bernd Wilhelm LEHNEMANN, Axel VON WANGELIN JACOBI, Samet GUELAK
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Publication number: 20130204037Abstract: A catalytic process is taught for non-oxidative alkylation of organic compounds, comprising alcohols, alkanes, glycols, ethers, aldehydes, ketones, carboxylic acids, esters, amines, thiols or phosphines, by alkyl groups produced from alcohols or glycols, forming products comprising ethers and other higher molecular weight alkylated compounds. The process is conducted at a reflux temperature below 200° C. in the presence of an acid, alkali or neutral salt dehydrating agent comprising sulfuric acid, phosphoric acid or their salts, lime or anhydrous calcium sulfate in the absence of zero valent metals and air. Specifically, this catalytic process converts ethanol to ethyl butyl ethers, ethyl hexyl ethers and dibutyl ethers or oxygenated gasoline as well as amines comprising n-butyl amine plus butanol to dibutyl amine and butyl hexyl amines at ambient pressure.Type: ApplicationFiled: February 7, 2012Publication date: August 8, 2013Applicant: Carter TechnologiesInventor: Melvin Keith Carter
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Publication number: 20130178632Abstract: One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in various transition-metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition-metal-catalyzed reactions, including the range of suitable substrates, number of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition metal-catalyzed: aryl amination reactions; aryl amidation reactions; Suzuki couplings; and Sonogashira couplings. In certain embodiments, the invention relates to catalysts and methods of using them that operate in aqueous solvent systems.Type: ApplicationFiled: February 15, 2013Publication date: July 11, 2013Applicant: Massachusetts Institute of TechnologyInventor: Massachusetts Institute of Technology
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Patent number: 8465850Abstract: The invention provides methods for the application of active materials onto active surfaces useful in organic electronic devices. The methods of the invention include selecting a liquid composition including an active material and a suitable liquid medium whereby when the liquid composition is deposited on the desired active surface it has no greater than about a 40° contact angle; treating the active surface to raise its surface tension before the deposition of a liquid composition containing the desired active material is deposited thereon; and combination thereof. The invention also provides organic electronic devices having at least two active layers, wherein at least one active layer comprises an active material that was deposited using at least one practice of the method of the invention.Type: GrantFiled: April 5, 2011Date of Patent: June 18, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Daniel David Lecloux
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Publication number: 20130149399Abstract: An object of the present invention is to provide a skin temperature elevating agent that can further effectively raise a skin temperature. Another object is to provide a cosmetic composition, a food and a sundry article having a skin temperature elevating effect. A skin temperature elevating agent of the present invention is selected from one or more selected from a group consisting of: an extract of Japanese peppermint; an extract of clary sage; dihydro-?-ionol; and geraniol, and thus it can raise a skin temperature of a cheek. The skin temperature elevating agent according to the present invention is also selected from one or more selected from a group consisting of: an extract of Japanese peppermint; an extract of juniper berry; and 4-methoxystyrene, and thus it can raise a skin temperature of a hand fingertip. Hence, the skin temperature elevating agent according to the present invention can further effectively raise a skin temperature.Type: ApplicationFiled: May 26, 2011Publication date: June 13, 2013Inventors: Keiko Mori, Shinichiro Haze, Yoko Gozu, Atsushi Joichi
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Publication number: 20130115654Abstract: A method for utilizing agricultural biomass components, namely cellulose, hemicellose, and lignin, and converting them to value-added biobased chemical products is described herein. The present method provides treatments to obtain a plurality of component streams from agricultural biomass for producing derivative products while minimizing waste products.Type: ApplicationFiled: November 9, 2011Publication date: May 9, 2013Applicant: Thesis Chemistry, LLCInventors: John R. Peterson, Christopher M. Yost, Jian Wu
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Publication number: 20130115653Abstract: A method for utilizing woody biomass components, namely cellulose, hemicellose, and lignin, and converting them to value-added biobased chemical products is described herein. The present method provides treatments to obtain a plurality of component streams from woody biomass for producing derivative products while minimizing waste products.Type: ApplicationFiled: November 9, 2011Publication date: May 9, 2013Applicant: Thesis Chemistry, LLCInventors: John R. Peterson, Christopher M. Yost, Jian Wu
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Patent number: 8287766Abstract: The invention provides methods for the application of active materials onto active surfaces useful in organic electronic devices. The methods of the invention include selecting a liquid composition including an active material and a suitable liquid medium whereby when the liquid composition is deposited on the desired active surface it has no greater than about a 40° contact angle; treating the active surface to raise its surface tension before the deposition of a liquid composition containing the desired active material is deposited thereon; and combination thereof. The invention also provides organic electronic devices having at least two active layers, wherein at least one active layer comprises an active material that was deposited using at least one practice of the method of the invention.Type: GrantFiled: June 16, 2005Date of Patent: October 16, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Daniel David Lecloux
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Publication number: 20120010298Abstract: Methods of producing substituted and non-substituted beta-methyl styrene by a cross-coupling reaction are provided. The disclosure also provides for methods of preparing (E)-Anethol and related compounds by a cross coupling reaction of potassium allyltrifluoroborate and 4-bromoanisole and aryl halides. Compounds, compositions, and methods of treating disorders utilizing beta-methyl styrene are also provided.Type: ApplicationFiled: July 6, 2011Publication date: January 12, 2012Inventor: Mohammad AL-MASUM
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Publication number: 20110206720Abstract: The present invention is related to the usage of Antrodia cinnamomea fruit body derivatives. The fruit body derivatives comprise acetic acid extract, acetic ether extract and Antrocamphin A. The acetic acid extract, acetic ether extract and Antrocamphin A can reduce the expression of iNOS and COX-2 and therefore inhibit the production of pro-inflammatory molecules.Type: ApplicationFiled: February 23, 2010Publication date: August 25, 2011Applicant: Taiwan Leader Biotech CorpInventor: Sheng-Yang WANG
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Publication number: 20110201840Abstract: Disclosed is a process for preparing terminal 1,1-disubstituted alkenes and is to compounds prepared therewith.Type: ApplicationFiled: February 16, 2010Publication date: August 18, 2011Applicant: THE CHINESE UNIVERSITY OF HONG KONGInventor: Chun Yu HO
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Patent number: 7951877Abstract: A process, advantageous in producibility, for the production of a vinyl compound containing very small amounts of ionic impurities and hydrolysable halogens, which is capable of curing by means of heat and/or light and giving a cured product having excellent dielectric characteristics and heat resistance, which process can efficiently remove a generated salt and comprises reacting a non-protonic polar solvent solution of a specific bifunctional phenylene ether oligomer with a vinylbenzyl halide in the presence of an alkoxide of an alkali metal, wherein the thus-obtained reaction solution is acidified with a specific amount of an acidic substance, then a salt generated is removed, an alkali substance containing a specific amount of an alkali metal is added to the thus-obtained solution, then a salt generated is removed, and the thus-obtained solution is mixed with water or a water-alcohol mixed solution, to precipitate a solid.Type: GrantFiled: June 17, 2008Date of Patent: May 31, 2011Assignee: Mitaubishi Gas Chemical Company, Inc.Inventors: Jun Nakano, Takeru Horino, Makoto Miyamoto, Atsushi Hirashima, Yasumasa Norisue
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Publication number: 20110061563Abstract: An ecologically compatible anti-microbial-adhesion agent is described, which is particularly suitable for use in anti-fouling paints, preferably for boats, characterized in that it comprises a compound selected from eugenol, vanillin, benzaldehyde substituted with one or two substituents selected from the groups —OH (hydroxy) and —OCH3 (methoxy), or any combination thereof. An anti-fouling paint is also described, particularly for boats, comprising the anti-microbial-adhesion agent mentioned above and other components selected from conventional biocides, solvents, resins, pigments, charges and fillings, and combinations thereof.Type: ApplicationFiled: May 12, 2009Publication date: March 17, 2011Inventors: Cecilia Calisti, Giulio Zanaroli, Fabio Fava, Alessandra Bontempi Di Roccaspada, Maurizio Ruzzi
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Patent number: 7893304Abstract: The present invention provides compounds that are useful for preventing or treating brain dysfunctions, motor dysfunctions, or urinary dysfunctions caused by the degeneration and/or loss of the central nervous system or peripheral nervous system cells.Type: GrantFiled: February 23, 2006Date of Patent: February 22, 2011Assignee: Meiji Dairies CorporationInventors: Bang Luu, Dominique Bagnard, Mazen Hanbali, Masashi Yamada, Hiroto Suzuki
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Publication number: 20100331566Abstract: The invention provides synthetic methods that utilize bromo or chloro substituents as blocking groups during the functionalization of aromatic rings, as well as compounds that are prepared from such methods.Type: ApplicationFiled: June 25, 2010Publication date: December 30, 2010Inventors: Leslie S. Jimenez, Ahalya Ramanathan
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Publication number: 20100305313Abstract: The present invention relates to a process for the extraction of plant ingredients, which comprises a) comminuting plant material b) adding a solvent to the comminuted plant material c) subjecting the mixture of comminuted plant material and solvent to an ultrahigh temperature treatment at 95-150° C. over a period of 5-300 seconds.Type: ApplicationFiled: December 16, 2008Publication date: December 2, 2010Applicant: Bayer CropScience AGInventors: Michael Baeuerlein, Joseph Miller
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Publication number: 20100249246Abstract: A (?)-stereoisomer of formula (I): (formula I), wherein X is H or F; or a pharmaceutically acceptable salt or prodrug thereof, is useful as an anesthetic.Type: ApplicationFiled: May 8, 2008Publication date: September 30, 2010Applicant: PharmacoFore, Inc.Inventor: Thomas E. Jenkins
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Publication number: 20100121062Abstract: A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture: R1—B-T ??(I); where R1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.Type: ApplicationFiled: September 25, 2009Publication date: May 13, 2010Applicant: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, David M. Knapp, Eric P. Gillis
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Patent number: 7686978Abstract: The invention provides methods for the application of active materials onto active surfaces useful in organic electronic devices. The methods of the invention include selecting a liquid composition including an active material and a suitable liquid medium whereby when the liquid composition is deposited on the desired active surface it has no greater than about a 40° contact angle; treating the active surface to raise its surface tension before the deposition of a liquid composition containing the desired active material is deposited thereon; and combination thereof. The invention also provides organic electronic devices having at least two active layers, wherein at least one active layer comprises an active material that was deposited using at least one practice of the method of the invention.Type: GrantFiled: September 24, 2003Date of Patent: March 30, 2010Assignee: E. I. du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Daniel David Lecloux
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Patent number: 7531700Abstract: The invention provides new fluorinated solvents that have many uses. One such use is as a solvent useful in the deposition of organic active materials in the manufacture of organic electronic devices. The new fluorinated solvents are fluorinated arylethers and can be readily prepared from corresponding phenols and fluorinated olefins.Type: GrantFiled: September 24, 2003Date of Patent: May 12, 2009Assignee: E.I. du Pont de Nemours and CompanyInventor: Viacheslav A. Petrov
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Publication number: 20090012331Abstract: A process, advantageous in producibility, for the production of a vinyl compound containing very small amounts of ionic impurities and hydrolysable halogens, which is capable of curing by means of heat and/or light and giving a cured product having excellent dielectric characteristics and heat resistance, which process can efficiently remove a generated salt and comprises reacting a non-protonic polar solvent solution of a specific bifunctional phenylene ether oligomer with a vinylbenzyl halide in the presence of an alkoxide of an alkali metal, wherein the thus-obtained reaction solution is acidified with a specific amount of an acidic substance, then a salt generated is removed, an alkali substance containing a specific amount of an alkali metal is added to the thus-obtained solution, then a salt generated is removed, and the thus-obtained solution is mixed with water or a water-alcohol mixed solution, to precipitate a solid.Type: ApplicationFiled: June 17, 2008Publication date: January 8, 2009Inventors: Jun Nakano, Takeru Horino, Makoto Miyamoto, Atsushi Hirashima, Yasumasa Norisue
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Publication number: 20080269514Abstract: The present invention relates to a process for the formation of carbon-carbon bonds starting from a copper compound of an aryl, heteroaryl, alkene or alkine and an aryl, heteroaryl, alkene or alkine compound having a suitable leaving group. The copper compounds can be prepared inter alia by means of transmetalliziation from a Grignard or lithium compound. Cross-coupling of these compounds with e.g. a halogen-substituted aryl compound is carried out by means of an iron or cobalt catalyst using suitable solvents and suitable additives.Type: ApplicationFiled: October 11, 2005Publication date: October 30, 2008Applicant: SALTIGO GMBHInventors: Paul Knochel, Ioannis Sapountzis, Tobias Korn, Wenwei Lin, Christiane Charlotte Kofink
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Patent number: 7230141Abstract: A process for preparing toluene derivatives of the formula I, where R1, R2 and R3 independently of one another are hydrogen, halogen, C1–C6-alkyl, hydroxyl or C1–C6-alkoxy, by hydrogenating benzaldehydes and/or benzyl alcohols of the formula II, with hydrogen in the presence of a catalyst, which is described in more detail in the description.Type: GrantFiled: January 20, 2003Date of Patent: June 12, 2007Assignee: BASF AktiengesellschaftInventors: Nils Bottke, Rolf-Hartmuth Fischer, Thomas Nöbel, Markus Rösch
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Patent number: 7105707Abstract: Mono- and disubstituted aryl or heterocyclic acetylenes are produced by a process comprising reacting an aryl nitrile with an alkynylzinc compound, a bis-alkynylzinc compound, or an alkynylmagnesium compound, in the presence of a nickel/phosphine catalyst.Type: GrantFiled: December 17, 2003Date of Patent: September 12, 2006Assignee: PharmaCore, Inc.Inventors: Joseph A. Miller, Jonathan M. Penney
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Patent number: 6992226Abstract: A process for preparing toluene derivatives of the formula I where R1, R2 and R3 are, independently of one another, hydrogen, alkyl radicals, hydroxyl groups and/or alkoxy groups, comprises reacting the corresponding benzoic acids, benzoic esters or benzoic anhydrides with hydrogen in the presence of a catalyst.Type: GrantFiled: April 24, 2002Date of Patent: January 31, 2006Assignee: BASF AktiengesellschaftInventors: Rolf-Hartmuth Fischer, Markus Rösch, Norbert Götz
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Patent number: 6881868Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H,C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yiedls by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leaving group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and reduction to corresponding 3-R-2-R3-allyl alcohols and their enantioselective hydrogenation, wherein R is (a).Type: GrantFiled: June 26, 2001Date of Patent: April 19, 2005Assignee: Speedel Pharma AGInventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
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Patent number: 6821308Abstract: Oleophilic polyoxyalkylene monoethers having reduced water affinity are disclosed. The monoethers have a hydrocarbyl residue, a polyoxyalkylene moiety, and a hydroxyl end group. The monoethers contain less than about 6 mole percent of alkoxylated unsaturates, and preferably less than about 5 mole percent of polyoxyalkylene diols. The monoethers offer substantial advantages for fuel compositions, particularly reduced water affinity. By using deposit-control additives based on the monoethers, formulators can offer better fuels for cleaner engines.Type: GrantFiled: April 2, 1997Date of Patent: November 23, 2004Assignee: Bayer Antwerp N.V.Inventors: George Combs, Kenneth G. McDaniel
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Patent number: 6624334Abstract: Aryl alkyl ethers can be produced by the reaction of hydroxyaromatics with an alcohol in the presence of a catalyst. This process achieves higher yields of aryl alkyl ethers and the formation of ring-alkylated products and dialkyl ethers is markedly reduced.Type: GrantFiled: April 8, 2002Date of Patent: September 23, 2003Assignees: Haarmann & Reimer GmbH, Bayer AktiengesellschaftInventors: Efim Biller, Edgar Fuhrmann, Detlef Hagena, Heinz Günter Janneck, Jörg Talbiersky, Lutz Walther
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Patent number: 6479709Abstract: A process for the production of a styrene derivative is provided. The process comprises reacting a Grignard reagent prepared from an aromatic halogen compound with a vinyl halide in the presence of a catalyst, wherein the catalyst is at least one member selected from the group consisting of manganese catlyst, iron catalyst, cobalt catalyst and rhodium catalyst.Type: GrantFiled: January 28, 1999Date of Patent: November 12, 2002Assignee: Tosoh CorporationInventors: Shin-ichi Ishikawa, Hisao Eguchi
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Patent number: 6472567Abstract: A process for the production of a styrene compound is provided. The process comprises reacting a Grignard reagent prepared from a tertiary butoxyphenyl halide with a vinyl halide in the presence of a catalyst, wherein the catalyst is at least one member selected from the group consisting of manganese catalyst, iron catalyst, cobalt catalyst and rhodium catalyst. The process overcomes the problems involved in the prior art, and is economical and safe. The styrene compound by the process is free from biphenyl.Type: GrantFiled: August 8, 2001Date of Patent: October 29, 2002Assignee: Tosoh CorporationInventors: Shin-ichi Ishikawa, Hisao Eguchi
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Patent number: 6274635Abstract: The present invention provides a method, compounds, and compositions for treating a disease associated with immune dysfunction. In accordance with the method, a pharmacologically-acceptable composition including at least one compound selected from the group of compounds consisting of 5-alkyl-resorcinol derivatives, cannabinol derivatives, cannabidiol derivatives, cannabigerol derivatives, and combinations thereof is administered to a patient under conditions sufficient to attenuate the dysfunction within the immune system. The invention also provides an antiviral cannabinol derivative that can be used in the inventive method. The invention also provides an alkylated resorcinol derivative and a method of using the alkylated resorcinol derivative to attenuate the growth of a neoplasm. The method and compound are useful for treating diseases of the immune system, such as HIV disease and neoplastic disorders.Type: GrantFiled: March 22, 2000Date of Patent: August 14, 2001Assignee: Immugen Pharmaceuticals Inc.Inventor: Craig A. Travis
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Patent number: 6184381Abstract: This document describes a novel and practically excellent process for the preparation of optically active compounds, such as optically active alcohols or amines which are useful for various applications, for example, as synthetic intermediates of pharmaceuticals, liquid crystal materials, and reagents for optical resolution, wherein a hydrogen transfer type asymmetric reduction is carried out in the presence of both a transition metal complex and an optically active nitrogen compound or a transition metal complex having an optically active nitrogen compounds as an asymmetric ligand, and a hydrogen-donating organic or inorganic compound.Type: GrantFiled: September 29, 1998Date of Patent: February 6, 2001Assignees: Japan Science & Technology Corp., NKK Corp., Takeda Chemical Industries, Asahi Kasei Kogyo Kabushiki Kaisha, Takasago Intl. Corp.Inventors: Takao Ikariya, Shohei Hashiguchi, Jun Takehara, Nobuyuki Uematsu, Kazuhiko Matsumura, Ryoji Noyori, Akio Fujii
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Patent number: 6063940Abstract: A 1-bromoalkylbenzene derivative is prepared by reacting a phenylalkene derivative with hydrogen bromide in the presence of a non-polar solvent. The phenylalkene derivative is prepared by reacting an alkenyl halide with metal magnesium to form a Grignard reagent, and then reacting the Grignard reagent with a benzyl halide derivative. An allyl Grignard reagent is prepared by reacting continuously an allyl halide derivative with metal magnesium in an organic solvent, in which the allyl halide derivative and metal magnesium are continuously added to the reaction system and the allyl Grignard reagent formed is continuously removed from the reaction system. The processes provide the intended compounds in high yields, high selectivities and high purities.Type: GrantFiled: February 13, 1997Date of Patent: May 16, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroaki Fujishima, Yasunobu Miyamoto, Masayoshi Minai, Tsutomu Matsumoto, Hideki Ushio, Takayuk Higashii
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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: 5817886Abstract: The present invention provides a process for producing an alkyl ether of a phenol from a phenol and an alcohol at a selectivity and a yield higher than in conventional processes, stably over a long period of time. The process is characterized by alkyl-etherifying a phenol with an alcohol in the presence of an oxide catalyst comprising an alkali metal as a constituent element.Type: GrantFiled: December 24, 1996Date of Patent: October 6, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Kimio Ariyoshi, Yuuichi Satoh, Noboru Saito
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Liquid crystalline compound having conjugated carbon chain and liquid crystal composition containing
Patent number: 5635108Abstract: A hexynediene derivative expressed by the following general formula I and liquid crystal compositions containing the derivative are disclosed: ##STR1## wherein R.sup.1 and R.sup.2 independently represent an alkyl group or alkoxy group each having 1 to 10 carbon atoms, ring A and ring B independently represent 1,4-cyclohexylene or 1,4-phenylene.Type: GrantFiled: March 22, 1996Date of Patent: June 3, 1997Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Kazutoshi Miyazawa -
Patent number: 5610133Abstract: Described are compounds defined according to the structure: ##STR1## wherein Z represents meta or para cyclohexylene or meta or para phenylene and wherein R.sub.1 and R.sub.2 are the same or different methyl or hydrogen; and wherein R.sub.3 represents C.sub.1 -C.sub.3 alkyl; and wherein the moiety: ##STR2## is ortho with respect to R.sub.2 and para or meta with respect to the moiety: ##STR3## with the proviso that the sum of the number of carbon atoms in R.sub.1, R.sub.2 and R.sub.3 is 3 or 4; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing alkyl-substituted-C.sub.1 -C.sub.3 alkoxy-C.sub.6 -cycloaliphatic compounds.Type: GrantFiled: May 9, 1996Date of Patent: March 11, 1997Assignee: International Flavors & Fragrances Inc.Inventors: Michael G. Monteleone, Richard A. Weiss, Marc D. Evans, Marie R. Hanna
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Patent number: 5583264Abstract: Described are compounds defined according to the structure: ##STR1## wherein Z represents para cyclohexylene or para phenylene and wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different methyl or hydrogen; and wherein R.sub.4 represents hydrogen, methyl or ethyl with the proviso that the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is 2. Also described are para-C.sub.5 alkyl-substituted ethoxycyclohexanes defined according to the structure: ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 represent the same or different methyl or hydrogen; and wherein R.sub.4 represents hydrogen, methyl or ethyl with the proviso that the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: February 26, 1996Date of Patent: December 10, 1996Assignee: International Flavors & Fragrances Inc.Inventors: Michael G. Monteleone, Richard A. Weiss, Marc D. Evans, Marie R. Hanna
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Patent number: 5536870Abstract: A process for preparing olefin compounds of the formula ##STR1## where A is aryl, substituted aryl, heteroaryl, substituted heteroaryl, benzyl, substituted benzyl, vinyl or substituted vinyl and R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkyl, cycloalkyl, alkyl-substituted cycloalkyl, aryl, substituted aryl, alkoxy, alkythio, heteroaryl, substituted heteroaryl, alkanoyl, aroyl, substituted aroyl, heteroarylcarbonyl, substituted heteroarylcarbonyl, trifluoromethyl or halo, which comprises reacting an organic halide of the formula A-X where X is chloro, bromo or iodo with a vinyl or substituted vinyl compound of the formula ##STR2## where R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: February 17, 1995Date of Patent: July 16, 1996Assignee: Albemarle CorporationInventor: Tse-Chong Wu
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Patent number: 5510541Abstract: Mono-alkadienyl alkyl ethers and di-alkadienyl alkyl ethers are prepared by telomerization of a conjugated diene, by causing said conjugated diene to react with an aliphatic alcohol or an aliphatic diol respectively, by operating in an aqueous/organic biphasic liquid system, in the presence of a catalytic system formed by:(a) a palladium salt or complex;(b) an alkyl-, alkylcycloalkyl-, or alkylarylphosphine ligand, bearing an acidic or neutral hydrophylic moiety, having the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, x and y are as defined in the disclosure; and(c) an either inorganic or organic base.Type: GrantFiled: February 25, 1994Date of Patent: April 23, 1996Assignee: Snamprogetti S.p.A.Inventors: Renata Patrini, Mario Marchionna
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Patent number: 5502031Abstract: Described are methyl, substituted propyl-substituted pentamethyl indane derivatives defined according to the structure: ##STR1## wherein R.sub.1 represents chloro, hydroxyl or OR.sub.6 ; and R.sub.5 represents methyl or hydrogen with the proviso that when R.sub.1 is chloro, R.sub.5 is hydrogen, and wherein the structure represents a mixture wherein in the mixture in one of the compounds R.sub.4 and R.sub.4 ' are both methyl and R.sub.7 is methyl (about 90% by weight); and in the other compounds one of R.sub.4 or R.sub.4 ' is methyl and the other is ethyl (about 10% by weight of the compounds) and R.sub.7 is hydrogen; and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions.Also described are processes for preparing such methyl, substituted propyl-substituted pentamethyl indane derivatives using as a starting material the mixture of compounds defined according to the structure: ##STR2## also know as GALAXOLIDE.RTM. (trademark of International Flavors & Fragrances Inc.).Type: GrantFiled: September 22, 1994Date of Patent: March 26, 1996Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Olivier J. Gillotin
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Patent number: 5462923Abstract: Described are 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes and mixtures thereof with bicyclopentadiene derivatives, wherein the 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes are defined according to the structure: ##STR1## wherein Y.sub.1 represents one of the moieties: ##STR2## and wherein the bicyclopentadiene derivatives are defined according to the structure: ##STR3## wherein Z.sub.1 and Z.sub.2 represent hydrogen, C.sub.1 -C.sub.3 lower alkyl or C.sub.2 -C.sub.3 acyl and Z.sub.3 represents methyl or hydrogen with the proviso that Z.sub.1 and Z.sub.2 are not both hydrogen, and uses thereof in augmenting, enhancing or imparting aromas in and to perfume compositions, colognes, perfumed polymers and perfumed articles.Type: GrantFiled: September 2, 1994Date of Patent: October 31, 1995Assignee: International Flavors & Fragrances Inc.Inventors: Michael G. Monteleone, Richard A. Weiss, Mark D. Evans, Marie R. Hanna
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Patent number: 5422417Abstract: Substituted phenyl compounds endowed with chain extension activity for formulations such as polyurethanes are disclosed, and which have the general formula: ##STR1## wherein n is 1-1000 and m is 1-100; and R.sub.1 and R.sub.2 are each independently selected from the group --C.sub.2 H.sub.4 -- and --C.sub.3 H.sub.6 --; and R.sub.3 is from the group consisting of: ##STR2## and the diasteromeric salts thereof.Type: GrantFiled: March 31, 1994Date of Patent: June 6, 1995Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik, William W. Wilkison, III
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Patent number: 5387718Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.Type: GrantFiled: July 14, 1992Date of Patent: February 7, 1995Assignee: Huels AktiengesellschaftInventors: Gunther Kohler, Peter Bickert
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Patent number: 5346983Abstract: Substituted phenyl compounds endowed with chain extension activity for formulations such as polyurethanes are disclosed, and which have the general formula: ##STR1## wherein n is 1-1000; R.sub.1 .dbd.R.sub.2, and R.sub.1 and R.sub.2 are from the group --CH.sub.2 --CH.sub.2, --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3)H--CH.sub.2 --; and R.sub.3 is from the group consisting of: ##STR2## and the diasteromeric salts thereof.Type: GrantFiled: May 28, 1993Date of Patent: September 13, 1994Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III