Acyclic Hydrocarbyl Group Bonded Directly To The Benzene Ring Patents (Class 568/658)
  • Patent number: 11434367
    Abstract: 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: Grant
    Filed: October 14, 2020
    Date of Patent: September 6, 2022
    Assignee: ELITE ELECTRONIC MATERIAL (KUNSHAN) CO., LTD.
    Inventor: Yan Zhang
  • Patent number: 11111336
    Abstract: 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: Grant
    Filed: March 27, 2018
    Date of Patent: September 7, 2021
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: Eylem Tarkin-Tas, Huseyin Tas, Mark R. Denniston
  • Patent number: 8921611
    Abstract: 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: Grant
    Filed: April 13, 2012
    Date of Patent: December 30, 2014
    Assignee: Uchicago Argonne, LLC
    Inventors: Krzysztof Z. Pupek, Trevor L. Dzwiniel, Gregory K. Krumdick
  • Publication number: 20140336270
    Abstract: 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: Application
    Filed: March 6, 2014
    Publication date: November 13, 2014
    Applicant: Tennessee Board of Regents
    Inventor: Mohammad AL-MASUM
  • Patent number: 8865775
    Abstract: An anti-inflammatory agent or cancer-preventive agent comprising 4-vinyl-2,6-dimethoxyphenol of the formula (1): or a PD thereof.
    Type: Grant
    Filed: January 20, 2012
    Date of Patent: October 21, 2014
    Inventors: Hiroshi Maeda, Tetsuya Tsukamoto, Masae Tatematsu
  • Publication number: 20130324745
    Abstract: 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: Application
    Filed: May 31, 2013
    Publication date: December 5, 2013
    Inventors: Matthias GOTTA, Bernd Wilhelm LEHNEMANN, Axel VON WANGELIN JACOBI, Samet GUELAK
  • Publication number: 20130204037
    Abstract: 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: Application
    Filed: February 7, 2012
    Publication date: August 8, 2013
    Applicant: Carter Technologies
    Inventor: Melvin Keith Carter
  • Publication number: 20130178632
    Abstract: 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: Application
    Filed: February 15, 2013
    Publication date: July 11, 2013
    Applicant: Massachusetts Institute of Technology
    Inventor: Massachusetts Institute of Technology
  • Patent number: 8465850
    Abstract: 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: Grant
    Filed: April 5, 2011
    Date of Patent: June 18, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Viacheslav A. Petrov, Daniel David Lecloux
  • Publication number: 20130149399
    Abstract: 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: Application
    Filed: May 26, 2011
    Publication date: June 13, 2013
    Inventors: Keiko Mori, Shinichiro Haze, Yoko Gozu, Atsushi Joichi
  • Publication number: 20130115654
    Abstract: 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: Application
    Filed: November 9, 2011
    Publication date: May 9, 2013
    Applicant: Thesis Chemistry, LLC
    Inventors: John R. Peterson, Christopher M. Yost, Jian Wu
  • Publication number: 20130115653
    Abstract: 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: Application
    Filed: November 9, 2011
    Publication date: May 9, 2013
    Applicant: Thesis Chemistry, LLC
    Inventors: John R. Peterson, Christopher M. Yost, Jian Wu
  • Patent number: 8287766
    Abstract: 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: Grant
    Filed: June 16, 2005
    Date of Patent: October 16, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Viacheslav A. Petrov, Daniel David Lecloux
  • Publication number: 20120010298
    Abstract: 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: Application
    Filed: July 6, 2011
    Publication date: January 12, 2012
    Inventor: Mohammad AL-MASUM
  • Publication number: 20110206720
    Abstract: 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: Application
    Filed: February 23, 2010
    Publication date: August 25, 2011
    Applicant: Taiwan Leader Biotech Corp
    Inventor: Sheng-Yang WANG
  • Publication number: 20110201840
    Abstract: Disclosed is a process for preparing terminal 1,1-disubstituted alkenes and is to compounds prepared therewith.
    Type: Application
    Filed: February 16, 2010
    Publication date: August 18, 2011
    Applicant: THE CHINESE UNIVERSITY OF HONG KONG
    Inventor: Chun Yu HO
  • Patent number: 7951877
    Abstract: 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: Grant
    Filed: June 17, 2008
    Date of Patent: May 31, 2011
    Assignee: Mitaubishi Gas Chemical Company, Inc.
    Inventors: Jun Nakano, Takeru Horino, Makoto Miyamoto, Atsushi Hirashima, Yasumasa Norisue
  • Publication number: 20110061563
    Abstract: 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: Application
    Filed: May 12, 2009
    Publication date: March 17, 2011
    Inventors: Cecilia Calisti, Giulio Zanaroli, Fabio Fava, Alessandra Bontempi Di Roccaspada, Maurizio Ruzzi
  • Patent number: 7893304
    Abstract: 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: Grant
    Filed: February 23, 2006
    Date of Patent: February 22, 2011
    Assignee: Meiji Dairies Corporation
    Inventors: Bang Luu, Dominique Bagnard, Mazen Hanbali, Masashi Yamada, Hiroto Suzuki
  • Publication number: 20100331566
    Abstract: 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: Application
    Filed: June 25, 2010
    Publication date: December 30, 2010
    Inventors: Leslie S. Jimenez, Ahalya Ramanathan
  • Publication number: 20100305313
    Abstract: 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: Application
    Filed: December 16, 2008
    Publication date: December 2, 2010
    Applicant: Bayer CropScience AG
    Inventors: Michael Baeuerlein, Joseph Miller
  • Publication number: 20100249246
    Abstract: 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: Application
    Filed: May 8, 2008
    Publication date: September 30, 2010
    Applicant: PharmacoFore, Inc.
    Inventor: Thomas E. Jenkins
  • Publication number: 20100121062
    Abstract: 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: Application
    Filed: September 25, 2009
    Publication date: May 13, 2010
    Applicant: The Board of Trustees of the University of Illinois
    Inventors: Martin D. Burke, David M. Knapp, Eric P. Gillis
  • Patent number: 7686978
    Abstract: 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: Grant
    Filed: September 24, 2003
    Date of Patent: March 30, 2010
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Viacheslav A. Petrov, Daniel David Lecloux
  • Patent number: 7531700
    Abstract: 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: Grant
    Filed: September 24, 2003
    Date of Patent: May 12, 2009
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Viacheslav A. Petrov
  • Publication number: 20090012331
    Abstract: 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: Application
    Filed: June 17, 2008
    Publication date: January 8, 2009
    Inventors: Jun Nakano, Takeru Horino, Makoto Miyamoto, Atsushi Hirashima, Yasumasa Norisue
  • Publication number: 20080269514
    Abstract: 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: Application
    Filed: October 11, 2005
    Publication date: October 30, 2008
    Applicant: SALTIGO GMBH
    Inventors: Paul Knochel, Ioannis Sapountzis, Tobias Korn, Wenwei Lin, Christiane Charlotte Kofink
  • Patent number: 7230141
    Abstract: 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: Grant
    Filed: January 20, 2003
    Date of Patent: June 12, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Nils Bottke, Rolf-Hartmuth Fischer, Thomas Nöbel, Markus Rösch
  • Patent number: 7105707
    Abstract: 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: Grant
    Filed: December 17, 2003
    Date of Patent: September 12, 2006
    Assignee: PharmaCore, Inc.
    Inventors: Joseph A. Miller, Jonathan M. Penney
  • Patent number: 6992226
    Abstract: 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: Grant
    Filed: April 24, 2002
    Date of Patent: January 31, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf-Hartmuth Fischer, Markus Rösch, Norbert Götz
  • Patent number: 6881868
    Abstract: 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: Grant
    Filed: June 26, 2001
    Date of Patent: April 19, 2005
    Assignee: Speedel Pharma AG
    Inventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
  • Patent number: 6821308
    Abstract: 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: Grant
    Filed: April 2, 1997
    Date of Patent: November 23, 2004
    Assignee: Bayer Antwerp N.V.
    Inventors: George Combs, Kenneth G. McDaniel
  • Patent number: 6624334
    Abstract: 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: Grant
    Filed: April 8, 2002
    Date of Patent: September 23, 2003
    Assignees: Haarmann & Reimer GmbH, Bayer Aktiengesellschaft
    Inventors: Efim Biller, Edgar Fuhrmann, Detlef Hagena, Heinz Günter Janneck, Jörg Talbiersky, Lutz Walther
  • Patent number: 6479709
    Abstract: 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: Grant
    Filed: January 28, 1999
    Date of Patent: November 12, 2002
    Assignee: Tosoh Corporation
    Inventors: Shin-ichi Ishikawa, Hisao Eguchi
  • Patent number: 6472567
    Abstract: 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: Grant
    Filed: August 8, 2001
    Date of Patent: October 29, 2002
    Assignee: Tosoh Corporation
    Inventors: Shin-ichi Ishikawa, Hisao Eguchi
  • Patent number: 6274635
    Abstract: 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: Grant
    Filed: March 22, 2000
    Date of Patent: August 14, 2001
    Assignee: Immugen Pharmaceuticals Inc.
    Inventor: Craig A. Travis
  • Patent number: 6184381
    Abstract: 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: Grant
    Filed: September 29, 1998
    Date of Patent: February 6, 2001
    Assignees: 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
  • Patent number: 6063940
    Abstract: 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: Grant
    Filed: February 13, 1997
    Date of Patent: May 16, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroaki Fujishima, Yasunobu Miyamoto, Masayoshi Minai, Tsutomu Matsumoto, Hideki Ushio, Takayuk Higashii
  • Patent number: 5986137
    Abstract: 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: Grant
    Filed: June 12, 1998
    Date of Patent: November 16, 1999
    Assignee: Rhodia Chimie
    Inventors: Jean-Michel Grosselin, Hubert Kempf, Jean-Pierre LeCouve
  • Patent number: 5817886
    Abstract: 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: Grant
    Filed: December 24, 1996
    Date of Patent: October 6, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kimio Ariyoshi, Yuuichi Satoh, Noboru Saito
  • Patent number: 5635108
    Abstract: 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: Grant
    Filed: March 22, 1996
    Date of Patent: June 3, 1997
    Assignee: Chisso Corporation
    Inventors: Atsuko Fujita, Shuichi Matsui, Kazutoshi Miyazawa
  • Patent number: 5610133
    Abstract: 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: Grant
    Filed: May 9, 1996
    Date of Patent: March 11, 1997
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael G. Monteleone, Richard A. Weiss, Marc D. Evans, Marie R. Hanna
  • Patent number: 5583264
    Abstract: 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: Grant
    Filed: February 26, 1996
    Date of Patent: December 10, 1996
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael G. Monteleone, Richard A. Weiss, Marc D. Evans, Marie R. Hanna
  • Patent number: 5536870
    Abstract: 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: Grant
    Filed: February 17, 1995
    Date of Patent: July 16, 1996
    Assignee: Albemarle Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 5510541
    Abstract: 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: Grant
    Filed: February 25, 1994
    Date of Patent: April 23, 1996
    Assignee: Snamprogetti S.p.A.
    Inventors: Renata Patrini, Mario Marchionna
  • Patent number: 5502031
    Abstract: 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: Grant
    Filed: September 22, 1994
    Date of Patent: March 26, 1996
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Olivier J. Gillotin
  • Patent number: 5462923
    Abstract: 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: Grant
    Filed: September 2, 1994
    Date of Patent: October 31, 1995
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael G. Monteleone, Richard A. Weiss, Mark D. Evans, Marie R. Hanna
  • Patent number: 5422417
    Abstract: 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: Grant
    Filed: March 31, 1994
    Date of Patent: June 6, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, James R. Sounik, William W. Wilkison, III
  • Patent number: 5387718
    Abstract: 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: Grant
    Filed: July 14, 1992
    Date of Patent: February 7, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Gunther Kohler, Peter Bickert
  • Patent number: 5346983
    Abstract: 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: Grant
    Filed: May 28, 1993
    Date of Patent: September 13, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, James R. Sounik, Bret F. Hann, William W. Wilkison, III