Halogen Containing Patents (Class 568/56)
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Patent number: 10752708Abstract: A curable composition capable of manufacturing a cured product having a high refractive index is provided. The curable composition contains a polymerizable compound represented by formula (1) and inorganic particles. In formula (1), La represents a divalent linking group, and the divalent linking group includes at least one of a divalent aromatic group, a divalent polycyclic aliphatic group and an alkylene group having an aromatic group, Ar represents an aromatic group, and R represents an aromatic group optionally having one or more substituents or a polycyclic aliphatic group optionally having one or more substituents.Type: GrantFiled: September 28, 2018Date of Patent: August 25, 2020Assignees: NIKON CORPORATION, ESSILOR INTERNATIONALInventors: Hideki Obara, Toshiaki Murai, Guillaume Cantagrel
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Patent number: 10450253Abstract: A simple production process is provided of a perfluoroalkyl compound that uses monohydroperfluoroalkane as a starting material, the perfluoroalkyl compound being an important intermediate of organic electronic materials, medicine, agricultural chemicals, functional polymer materials and the like. With monohydroperfluoroalkane is reacted a base and then a carbonyl compound to produce an alcohol having a perfluoroalkyl group. For example, potassium hydroxide is made to interact with trifluoromethane, and a reaction with a carbonyl compound is induced to produce an alcohol having a trifluoromethyl group.Type: GrantFiled: February 16, 2017Date of Patent: October 22, 2019Assignees: KANTO DENKA KOGYO CO., LTD., NATIONAL UNIVERSITY CORPORATION GUNMA UNIVERSITYInventors: Hideki Amii, Kazuki Komoda, Masafumi Kobayashi, Yutaka Nakamura, Ryusuke Obinata, Akinori Harada
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Patent number: 9598340Abstract: The coupling of aryl, heteroaryl, and vinyl halides with ?,?-difluoroketones or silyl ethers or siylenol ethers of ?,?-difluoroketones and ?,?-difluoroamides and esters are described. Further derivatization of the coupling products (such as ketone cleavage and Baeyer-Villiger oxidation) is also described.Type: GrantFiled: April 7, 2014Date of Patent: March 21, 2017Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIAInventors: John F. Hartwig, Shaozhong Ge, Wojciech Chaładaj
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Patent number: 9068047Abstract: Disclosed is a process for producing poly(arylene sulfide) which includes: a polymerization step of polymerizing a dihalogenated aromatic compound and at least one sulfur source selected from the group consisting of alkali metal sulfides and alkali metal hydrogen sulfides in an organic amide solvent, preferably in the presence of a phase separating agent; a separation step of separating a polymer from a reaction liquid containing a produced polymer after the polymerization step; a washing step of washing the polymer with a washing liquid that consists of water and/or an organic solvent; and a separated liquid treatment step of bringing both a separated liquid that has been recovered after the separation of the polymer in the separation step and a separated liquid containing a wash waste liquid that has been recovered after the separation of the polymer in the washing step into contact with an alkaline compound. Also disclosed is poly(arylene sulfide).Type: GrantFiled: April 21, 2011Date of Patent: June 30, 2015Assignee: KUREHA CORPORATIONInventors: Yoshihiro Ichinose, Masanori Kobayashi, Tomoyoshi Koizumi, Mitsuhiro Matsuzaki
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Publication number: 20150132223Abstract: One aspect of the present invention relates to a method of preparing radiofluorinated substituted alkyl, cycloalkyl, aryl, and alkenyl compounds. In a preferred embodiment, potassium fluoride-18 is used. Another aspect of the invention relates to arylammnonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the ammonium compound is a tetraaryl ammonium salt. Another aspect of the invention relates to arylsulfonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the sulfonium compound is a triaryl sulfonium salt. Another aspect of the present invention relates to a method of obtaining a positron emission image of a mammal, comprising the steps of administering to a mammal a compound of the invention, and acquiring a positron emission spectrum of the mammal.Type: ApplicationFiled: November 25, 2014Publication date: May 14, 2015Inventors: David R. Elmaleh, Alan J. Fischman, Timothy M. Shoup
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Publication number: 20150069297Abstract: A liquid crystal compound having high stability to heat and light, etc., a high clearing point, a low minimum temperature of liquid crystal phase, a low viscosity, a suitable optical anisotropy, a large dielectric anisotropy, a suitable elastic constant, and good compatibility with other liquid crystal compounds, a liquid crystal composition containing the compound, and a LCD element using the composition are described. The compound is represented by formula (1): wherein, for example, R1 is C1-10 alkyl, ring A1, ring A2, ring A3, ring A4 and ring B1 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is substituted with halogen, 1,3-dioxane-2,5-diyl, or tetrahydropyran-2,5-diyl, Z1, Z2, Z3 and Z4 are single bonds, l, m, n and o are independently 0 or 1, and l+m+n+o?1.Type: ApplicationFiled: February 7, 2013Publication date: March 12, 2015Inventor: Hiroyuki Tanaka
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Publication number: 20140243404Abstract: This disclosure is related to halonium compounds useful for cyclization of polyenes, alkenoic acids, and alkenyl alkyl ethers, and halogenation of aromatic compounds. The synthesis of such halonium compounds, compounds made using such halonium compounds, and synthesis of natural compounds, including decalins, using the halonium compounds is also disclosed.Type: ApplicationFiled: September 13, 2011Publication date: August 28, 2014Applicant: The Trustees of Columbia University in the City of New YorkInventors: Scott Alan Snyder, Daniel S. Treitler, Alexandria P. Brucks, Andreas Gollner, Maria I. Chiriac, Nathan E. Wright, Jason J. Pflueger, Steven P. Breazzano
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Publication number: 20140235898Abstract: Novel substituted phenylsulfur trifluorides that act as fluorinating agents are disclosed. Also disclosed are methods for their preparation and methods for their use in introducing one or more fluorine atoms into target substrate compounds. Finally, various intermediate compounds for use in preparing substituted phenylsulfur trifluorides are provided.Type: ApplicationFiled: March 14, 2014Publication date: August 21, 2014Applicant: UBE INDUSTRIES, LTD.Inventor: Teruo UMEMOTO
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Publication number: 20140128560Abstract: Described herein is a trifluorostyrene compound that can be used as a monomer to form crosslinkable polymers, and their use as polymer electrolyte membranes.Type: ApplicationFiled: January 10, 2014Publication date: May 8, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Mark Gerrit Roelofs, MARK F. TEASLEY
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Patent number: 8703969Abstract: A trifluoromethylthiophenium derivative salt useful as synthetic intermediates for pharmaceuticals and agrochemicals, a method for producing the same, and a method for producing trifluoromethyl-containing compounds using the same are provided. An S-(trifluoromethyl)-benzo[b]thiophenium derivative salt is represented by the following general formula (1): wherein R1, R2, R3, and R4 are each independently a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkyloxy group having 3 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, or a cyano group, R5 is a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a phenyl group, or a substituted phenyl group, and X? represents an anion.Type: GrantFiled: July 13, 2010Date of Patent: April 22, 2014Assignees: Nagoya Institute of Technology, Tosoh F-Tech, Inc.Inventors: Norio Shibata, Takumi Kagawa
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Publication number: 20130115168Abstract: One aspect of the present invention relates to a method of preparing radiofluorinated substituted alkyl, cycloalkyl, aryl, and alkenyl compounds. In a preferred embodiment, potassium fluoride-18 is used. Another aspect of the invention relates to arylammonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the ammonium compound is a tetraaryl ammonium salt. Another aspect of the invention relates to arylsulfonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the sulfonium compound is a triaryl sulfonium salt. Another aspect of the present invention relates to a method of obtaining a positron emission image of a mammal, comprising the steps of administering to a mammal a compound of the invention, and acquiring a positron emission spectrum of the mammal.Type: ApplicationFiled: September 4, 2012Publication date: May 9, 2013Applicant: The General Hospital CorporationInventors: David R. Elmaleh, Alan J. Fischman, Timothy M. Shoup
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Patent number: 8263693Abstract: The present invention provides a flame retardant resin composition comprising (A) 100 weight part of a basic resin comprising acrylonitrile-butadiene-styrene copolymer resin and styrene-acrylonitrile copolymer resin; and (B) 10-30 weight part of a bromine-based organic compound flame retardant, and selectively comprising (C) 1-20 weight part of an antimony-based auxiliary flame retardant and (D) 1-10 weight part of one or more compounds selected from the group consisting of metalstearate and stearamide compounds, wherein the bromine-based organic compound flame retardant (B) is octabromodiphenyl ethane. The flame retardant resin composition of the present invention has excellent flame retardancy, impact strength and melt flow index.Type: GrantFiled: August 29, 2008Date of Patent: September 11, 2012Assignee: LG Chem, Ltd.Inventors: You-seok Seo, Ki-young Nam, Yong-yeon Hwang, Je-sun Yoo, Hyeon-gook Kim, Myeong-soo Song
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Patent number: 8246859Abstract: The invention describes a process for reducing the surface energy of organic materials such as for example increasing the oil and water repellency and stain release of organic materials, which comprises treating the organic material with at least a compound of the formula I wherein the general symbols are as defined in claim 1; especially wherein at least one of the radicals R2, R3 or R4 is —CH(R11)—S(O)p—R12; R11 is hydrogen, C1-C8alkyl, unsubstituted or with C1-C4alkyl substituted phenyl; R12 is a monovalent perfluorinated alkyl or alkenyl, linear or branched organic radical having four to twenty fully fluorinated carbon atoms, and p is 0, 1 or 2.Type: GrantFiled: June 4, 2007Date of Patent: August 21, 2012Assignee: BASF SEInventors: Michèle Gerster, Manuel Mihalic
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Publication number: 20120172615Abstract: A substituted alkenylbenzene compound of formula (4): wherein X1 is a halogen atom, —SF5, C1-C6haloalkyl, hydroxy C1-C6haloalkyl, C1-C6alkoxy C1-C6haloalkyl, C3-C8halocycloalkyl, C1-C6haloalkoxy, C1-C3haloalkoxy C1-C3haloalkoxy, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl or C1-C6haloalkylsulfonyl; X3 is a hydrogen, halogen, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6alkylthio; X4 is a hydrogen, halogen, cyano, C1-C4alkyl, C1-C4alkoxy or C1-C4haloalkoxy; R3 is —C(R3a)(R3b)R3c, where R3a and R3b are a halogen, or R3a and R3b together form a 3- to 6-membered ring together with the carbon bonding them by forming a C2-C5haloalkylene chain, and R3c is a hydrogen, halogen, C1-C5alkyl, C1-C5haloalkyl, C1-C4haloalkoxy or C1-C4haloalkylthio, with a proviso that where X1 is a fluorine, chlorine or trifluoromethyl, and X2 and X3 are hydrogen, where X1 and X2 are fluorine and X3 is a hydrogen, or where X1 and X2 are trifluoromethyl and X3 is a hydrogen, R3c is a hydrogen, chlorine, bromine, iodine,Type: ApplicationFiled: January 13, 2012Publication date: July 5, 2012Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.Inventors: Takeshi MITA, Takamasa KIKUCHI, Takashi MIZUKOSHI, Manabu YAOSAKA, Mitsuaki KOMODA
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Publication number: 20120130090Abstract: A trifluoromethylthiophenium derivative salt useful as synthetic intermediates for pharmaceuticals and agrochemicals, a method for producing the same, and a method for producing trifluoromethyl-containing compounds using the same are provided. An S-(trifluoromethyl)-benzo[b]thiophenium derivative salt is represented by the following general formula (1): wherein R1, R2, R3, and R4 are each independently a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkyloxy group having 3 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, or a cyano group, R5 is a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a phenyl group, or a substituted phenyl group, and X? represents an anion.Type: ApplicationFiled: July 13, 2010Publication date: May 24, 2012Inventors: Norio Shibata, Takumi Kagawa
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Publication number: 20110251432Abstract: The invention relates to new processes for preparation of 18F-labelled alkylation reagents that can be used in the alkylation of amines that are suitable for use in labelling of Positron Emission Tomography (PET) radiotracers.Type: ApplicationFiled: August 27, 2008Publication date: October 13, 2011Inventors: Bengt Langstrom, Tor Kihlberg
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Patent number: 7951602Abstract: Mass defect labeled peptides and methods of identifying peptides are provided. In particular, embodiments of the present disclosure include mass defect labels for polypeptides that include at least one cysteine and/or at least one tryptophan and methods of using the mass defect labels to identify polypeptides. One embodiment, among others, includes a mass defect labeled peptide including at least one cysteine residue labeled with 2,4-dibromo-acetanilide. Another embodiment, among others, includes a mass defect labeled peptide including at least one tryptophan residue labeled with 4,6-dibromo-2-trifluoromethylphenylsulfenyl chloride.Type: GrantFiled: August 28, 2007Date of Patent: May 31, 2011Assignee: University of Georgia Research Foundation, Inc.Inventors: I. Jonathan Amster, Robert S. Phillips
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Publication number: 20110046247Abstract: Described herein is a trifluorostyrene compound that can be used as a monomer to form crosslinkable polymers.Type: ApplicationFiled: December 18, 2008Publication date: February 24, 2011Applicant: E.I. Du Pont De Nemours and CompanyInventors: Mark Gerrit Roelofs, Mark F. Teasley
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Publication number: 20110028725Abstract: The present disclosure provides methods of synthesizing alkylating agents and methods of use.Type: ApplicationFiled: August 17, 2010Publication date: February 3, 2011Applicant: The Queen's Medical CenterInventor: John L. Lim
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Publication number: 20100234605Abstract: New methods for producing difluoromethylene-containing compounds with phenylsulfur trifluoride or a primary alkyl-substituted phenylsulfur trifluoride are disclosed. Also, new methods for producing trifluoromethyl-containing compounds with phenylsulfur trifluoride or primary alkyl-substituted phenylsulfur trifluoride are also disclosed.Type: ApplicationFiled: December 9, 2008Publication date: September 16, 2010Applicant: IM&T RESEARCH, INC.Inventors: Teruo Umemoto, Rajendra P. Singh
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Publication number: 20100137608Abstract: Methods for carbon-sulfur (C—S) or carbon-oxygen (C—O) coupling reactions are provided. The methods involve the use of a transition metal complex comprising a heterocyclic carbene ligand complexed with a transition metal. Transition metal complexes comprising a heterocyclic carbene ligand complexed with nickel are also provided. The nickel heterocylic carbene complexes may be used for C—S or C—O coupling reactions.Type: ApplicationFiled: May 2, 2008Publication date: June 3, 2010Inventor: Yugen Zhang
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Patent number: 7709548Abstract: A monosulfonium salt in which very little unreacted raw material remains, which has a purity of at least 96%, and which has one sulfonio group in its molecule is manufactured without a refining step. After (a) an aryl compound, (b) a sulfoxide compound, (c) a dehydrating agent, and (d) a BF4, PF6, AsF6, or SbF6 salt of an alkali metal or an alkaline earth metal are introduced into a reaction system, (e) an inorganic acid is added, so that the aryl compound (a) and the sulfoxide compound (b) are subjected to dehydration condensation.Type: GrantFiled: December 17, 2007Date of Patent: May 4, 2010Assignee: San-Apro LimitedInventors: Masashi Date, Hideki Kimura, Shinji Yamashita, Jiro Yamamoto
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Patent number: 7659317Abstract: Methods and reagents for labeling synthesis of organohalides by transition metal mediated carbonylation reactions using carbon-isotope labeled carbon monoxide are provided. The resultant carbon-isotope labeled organohalides are useful as radiopharmaceuticals, especially for use as precursors in Positron Emission Tomography (PET). Associated PET tracers and kits for PET studies are also provided.Type: GrantFiled: March 10, 2005Date of Patent: February 9, 2010Assignee: GE Healthcare LimitedInventors: Jonas Eriksson, Bengt Langstrom, Gunnar Antoni
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Publication number: 20080262238Abstract: A dendron or dendrimer, which has, as a recurring unit of each branch, a structure of formula (I): wherein TC designates a linkage to a former generation in the direction to a focal point of the dendron or a core of the dendrimer; TT designates a linkage to a next generation in the direction to a terminal; X is a divalent group comprised of at least one heteroatom; L1 and L2 each are a divalent linking group; R is a hydrogen atom or a substituent; and a method of producing a dendron or a dendrimer; and a method of producing a thioacetal compound.Type: ApplicationFiled: March 28, 2005Publication date: October 23, 2008Inventor: Koki Nakamura
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Publication number: 20080255370Abstract: The chemistry of [13C]methyl phenyl sulfide is exploited to produce new isotopically labeled precursors that allow for the facile assembly of a wide range of labeled molecules from simple and relatively inexpensive starting materials. These compounds are applicable to a variety of research areas such as quantum computing, metabolism and materials science.Type: ApplicationFiled: April 4, 2008Publication date: October 16, 2008Inventor: Rodolfo A. Martinez
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Patent number: 7339081Abstract: A process for preparing bromo-1-oxypentafluorosulfanylbenzene is provided, the process including the step of brominating pentafluorosulfanyloxybenzene with a bromination agent to provide the bromo-1-oxypentafluorosulfanylbenzene. The process is more effective than prior art processes for preparing such compounds.Type: GrantFiled: July 10, 2006Date of Patent: March 4, 2008Assignee: Air Products and Chemicals, Inc.Inventors: Robert George Syvret, Gauri Sankar Lal
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Patent number: 7323602Abstract: A process for preparing an intermediate compound of formula (II) where n is an integer of from 3 to 14; R1 is haloC1-10alkyl, C1-10alkyl, C2-10alkenyl, C2-10cycloalkyl, carboxyC1-10alkyl, C1-10alkoxycarbonylC1-10alkyl, aryl (such as phenyl), aryl(C1-10)alkyl (such as phenyl(C1-10)alkyl) or di(C1-6alkyl)amino; and R2 is a halo group; the process comprising halogenation of a compound of formula (III) where n and R1 are as defined above. Novel compounds are also described and claimed.Type: GrantFiled: October 3, 2002Date of Patent: January 29, 2008Assignee: AstraZeneca ABInventors: Kenneth Edwin Herbert Warren, Anne Margaret Lamont Kane
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Patent number: 7087764Abstract: A process for producing a compound of the formula (II): wherein Hal1 represents halogen and R1 and R2 each independently represents halogen, alkyl, alkoxy, nitro or cyano, which comprises allowing a halogenating agent to react with a compound of the formula (I): wherein Alk represents branched alkyl and R1 and R2 are as defined above.Type: GrantFiled: February 14, 2003Date of Patent: August 8, 2006Assignee: Shionogi & Co., Ltd.Inventors: Tsutomu Aoki, Toshiro Konoike
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Patent number: 7087789Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“?CF2?”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.Type: GrantFiled: January 12, 2004Date of Patent: August 8, 2006Assignee: University of Southern CaliforniaInventors: G. K. Surya Prakash, Jinbo Hu, George A. Olah
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Publication number: 20040230079Abstract: A novel, convenient and efficient method for trifluoromethylation of substrate compounds is disclosed. Particularly, alkoxide and hydroxide induced nucleophilic trifluoromethylation of carbonyl compounds, disulfides and other electrophiles, using phenyl trifluoromethyl sulfone PhSO2CF3 (or sulfoxide PhSOCF3) is disclosed. A method of both symmetrical and unsymmetrical anti-2,2-difluoropropan-1,3-diols with high diastereoselectivity (up to 94% de) is disclosed using difluoromethyl phenyl sulfone. This unusual type of high diastereoselectivity was obtained via an intramolecular charge-charge repulsion effect rather than the traditional steric control (based on the Cram's rule). Thus, difluoromethyl phenyl sulfone can be used as a novel difluoromethylene dianion species (“−CF2−”), which can couple two electrophiles (such as diphenyl disulfide or non-enolizable aldehydes) to give new difluoromethylenated products.Type: ApplicationFiled: January 12, 2004Publication date: November 18, 2004Inventors: G.K.Surya Prakash, Jinbo Hu, George A. Olah
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Patent number: 6770776Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.Type: GrantFiled: September 25, 2001Date of Patent: August 3, 2004Assignee: Rhone-Poulenc ChimieInventors: Robert Janin, Laurent Saint-Jalmes
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Publication number: 20030187233Abstract: Perfluoroisopropylbenzene derivatives of the general formula (I) or salts thereof, useful as intermediates or raw materials in the synthesis of various industrial materials including agricultural chemicals, drugs and surfactants, wherein X1 is H, halogeno, formyl, optionally halogenated C1-6 alkyl, —C(═O)—R1 (wherein R1 is H, halogeno, hydroxyl, C1-6 alkyl, or NR2R3, with R2 and R3 being each H, C1-6 alkyl, or the like), or the like; X3 is H, halogeno, hydroxyl, cyano, isocyanato, hydrazino, diazo, —C(═O)—R1, —SO2—R4 (wherein R4 is halogeno, hydroxyl, C1-6 alkyl, or NR5R6, with R5 and R6 being each H or C1-6 alkyl), or the like; and X4 is H, halogeno, C1-6 alkyl, or C1-6 alkoxy, with publicly known compounds being excepted.Type: ApplicationFiled: September 11, 2002Publication date: October 2, 2003Inventors: Masanobu Onishi, Kenichi Ikeda, Takashi Shimaoka, Masanori Yoshida
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Publication number: 20030166971Abstract: It is an object of the present invention to provide a process for producing highly pure 4-bromothioanisole, which is useful in the manufacture of medicinal chemicals, agrochemicals or functional materials, in a simple and industrially advantageous manner.Type: ApplicationFiled: March 25, 2003Publication date: September 4, 2003Inventors: Kenichi Wakimura, Hitoshi Karino, Hirokazu Kagano
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Patent number: 6596905Abstract: The invention concerns a method for preparing aromatic diphenyl thioethers. More particularly the invention concerns the preparation of 4-chloro-4′-thiomethyldiphenylether. The inventive method for preparing an aromatic diphenyl thioether is characterised in that it consists in reacting in an aqueous medium a diazonium salt of an aromatic diphenyl compound with a disulphide sulphur compound, in the presence of an efficient amount of a coupling catalyst.Type: GrantFiled: August 27, 2001Date of Patent: July 22, 2003Assignee: Rhodia ChimieInventors: Thierry Schlama, Jean-Christophe Bigouraux
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Publication number: 20030100785Abstract: The present invention provides an intermediate compound used for synthesis of polyene chain structure, that is an important moiety of carotenoid compounds, a process for preparing the same, and carotenoid polyene chain compounds prepared by using the intermediate, and, in particular, a process for preparing lycopene. The process for preparing the carotenoid polyene chain compound employs an allylic sulfone compound as starting material, which is reacted with C-5 sulfide compound to extend the carbon chain. The resultant thio-sulfone compound is oxidized, and the obtained disulfone compound is combined with C-10 di(haloallylic) sulfide compound to form a chain compound containing the desired number of carbon atoms. Then, the diallylic sulfone obtained by oxidation of the diallylic sulfide is subjected to Ramberg-Baklund reaction in order to form the central triene bond. After removal of sulfonyl groups, carotenoid polyene chain compound is obtained.Type: ApplicationFiled: August 30, 2002Publication date: May 29, 2003Inventors: Sangho Koo, Minkoo Ji
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Publication number: 20030073847Abstract: The dihalopropene compounds of the general formula (I) have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.Type: ApplicationFiled: March 4, 2002Publication date: April 17, 2003Applicant: Sumitomo Chemical Company, LimitedInventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
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Patent number: 6518460Abstract: This invention provides processes for the preparation of a compound of Formula I: Y—C(═O)—C(R1)(R2)—CH2—S(O)nR3 wherein: Y is hydroxy or XONX, where each X is independently hydrogen, lower alkyl or lower acyl; R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, or R1 and R2 together with the carbon atom to which they are attached form a cycloalkyl or heterocyclo group; R3 is aryl; and n is 0, 1 or 2. The invention also provides novel aryl haloalkyl sulfide intermediates useful for the preparation of compounds of Formula I and novel methods of preparing aryl alkyl sulfides.Type: GrantFiled: May 8, 2002Date of Patent: February 11, 2003Assignee: Syntex (U.S.A.) LLCInventors: Jeffrey Allen Campbell, Lawrence Emerson Fisher, Charles Alois Dvorak, Paul Leo McGrane
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Patent number: 6506286Abstract: A reagent comprising a compound of formula (I): Rf—M(X)(Z)n—Y—R, wherein R is a hydrocarbon radical advantageously having at most 10 carbon atoms and being selected from alkyls and aryls; Rf is a radical of formula II: R1—(C&Xgr;2)m—CF2—, where R1 is a fluorine or chlorine atom or a carbon radical, m is 0 or a integer from 0-12, and each &Xgr;, which may be the same or different, is a chlorine or preferably fluorine atom, with the proviso that when m is 0, R1 is electroattractive, preferably a fluorine atom; n is 0 or 1; M is a non-metal selected from carbon and chalcogens with an atomic number than oxygen; and each of X, Y and Z, which are the same or different, is a chalcogen; as well as a generator, for consecutive or simultaneous addition. The reagent is useful for organic synthesis.Type: GrantFiled: August 24, 2000Date of Patent: January 14, 2003Assignee: Rhodia ChimieInventors: Bernard Langlois, Nicolas Roques, Claude Wakselman, Marc Tordeux, Gérard Forat
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Patent number: 6420573Abstract: This invention provides processes for the preparation of a compound of Formula I: Y—C(═O)—C(R1)(R2)—CH2—S(O)nR3 wherein: Y is hydroxy or XONX, where each X is independently hydrogen, lower alkyl or lower acyl; R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, or R1 and R2 together with the carbon atom to which they are attached form a cycloalkyl or heterocyclo group; R3 is aryl; and n is 0, 1 or 2. The invention also provides novel aryl haloalkyl sulfide intermediates useful for the preparation of compounds of Formula I and novel methods of preparing aryl alkyl sulfides.Type: GrantFiled: November 9, 2001Date of Patent: July 16, 2002Assignee: Syntex (U.S.A.) LLPInventors: Jeffrey Allen Campbell, Lawrence Emerson Fisher, Charles Alois Dvorak, Paul Leo McGrane
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Publication number: 20020052530Abstract: Indane dimer compounds of general formula 5, 6 or 9 and their pharmaceutical use, particularly to achieve smooth muscle relaxing activity and/or mast cell stabilizing activity and/or antiinflammatory activity are described, wherein in formulae 5 and 9, R1 and R3 to R15, and in formula 6, R1, R2 and R4 to R15, are selected from one or more of the same or different of: H, halo, hydroxy, alkoxy, aryloxy, acetoxy, carboxy, alkyl carbonyl, hydro carbonyl, amino, amido, alkylamino, hydroxylamino, amine oxide groups, azo groups, cyano, hydrazino groups, hydrazide groups, hydrazone groups, imide groups, iminoether groups, ureyl groups, oximc, nitro, nitrate, nitrite, nitroso groups, nitrile, heterocyclic groups containing one or more heteroatoms selected from N, O or S, aralkyl groups, mono and polybenzoid aryl groups, substituted aryl groups, thiol, thioureyl, phenylthiol groups, sulphonic acid groups, sulphoxide groups, sulphone groups, alkyl containing 1 to 10 carbon atoms or cycloalkyl groups containing 3 to 8 caType: ApplicationFiled: June 8, 1998Publication date: May 2, 2002Inventors: JOHN WALSH, NEIL FRANKISH, HELEN SHERIDAN, WILLIAM BYRNE
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Method for making unsymmetrically substituted fluorenyl compounds for nonlinear optical applications
Patent number: 6379590Abstract: A new method for producing unsymmetrically substituted fluorenyl compounds, one step of which is the preparation of 2,7-disubstituted fluoren-9-one derivatives via the nucleophilic substitution of a compound of the formula D wherein A′ is selected from the group consisting of —Br, —Cl, —F, —NO2, and —CN; A is selected from the group consisting of —NO2, —CN, —CO2R, —C(O)R, —SO2R, —SO2RF, —C(CN)═C(CN)2 and —CH═C(CN)2; RF is —CpF2p+1, p=from about 0 to about 10; R is an straight, branched or cyclic aliphatic alkyl group having about 1 to 10 carbon atoms, or an aromatic group such as phenyl or naphthyl; and is a carbonyl or a protected carbonyl such as a ketal or thio-ketal such as wherein R′ is —CrH2r+1; R″ is —(CH2)r—; and r is independently 2 or 3, with a nucleophilic reagent in the presence of an aprotic solventType: GrantFiled: December 2, 1994Date of Patent: April 30, 2002Assignee: AlliedSignal Inc.Inventors: Chengjiu Wu, Jianhui Shan -
Patent number: 6369275Abstract: The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases.Type: GrantFiled: November 17, 2000Date of Patent: April 9, 2002Assignee: Merck & Co., Inc.Inventors: Ian W. Davies, Michel Journet, Linda Gerena, Robert D. Larsen, Philip J. Pye, Kai Rossen
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Publication number: 20020015826Abstract: Photoresist compositions, or photoacids, are used in etching circuit pathways on the surface of microelectronic components. Iodonium compounds generate a strong acid under short wavelength irradiation, which is capable of etching the polymeric surface coating of a silicon wafer. The strong acid is the conjugate acid of the counteranion. Larger counterions generate acids that diffuse to a lesser extent in the polymer resist matrix, producing better image resolution. Given the particular anion, the solubility of its diary iodonium salts will depend upon which aromatic rings are used on the iodonium molecule. A zwitterionic structure of the iodonium molecule, having both positive and negative charges on the same molecular species, can be used as photoacid composition in the photoresist step of microchip manufacturing.Type: ApplicationFiled: April 10, 2001Publication date: February 7, 2002Inventors: Darryl Desmarteau, Vitorio Montanari, Brian H. Thomas
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Patent number: 6342639Abstract: This invention provides processes for the preparation of a compound of Formula I: Y—C(═O—C(R1)(R2)—CH2—S(O)nR3 wherein: Y is hydroxy or XONX, where each X is independently hydrogen, lower alkyl or lower acyl; R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, or R1 and R2 together with the carbon atom to which they are attached form a cycloalkyl or heterocyclo group; R3 is aryl; and n is 0, 1 or 2. The invention also provides novel aryl haloalkyl sulfide intermediates useful for the preparation of compounds of Formula I and novel methods of preparing aryl alkyl sulfides.Type: GrantFiled: June 17, 1999Date of Patent: January 29, 2002Assignee: Syntex (U.S.A.) LLCInventors: Jeffrey Allen Campbell, Lawrence Emerson Fisher, Charles Alois Dvorak, Paul Leo McGrane
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Patent number: 6326519Abstract: Diallylic sulfides represented by Formula I wherein: R1 and R2 are independently chosen from the group consisting of —CHO, —CH2Cl, —CH2Br, —CH2I, —CH2OH, CH2OSO2CF3, —CH2OSO2Ph, —CH2OSO2C6H4CH3 and —CH2OSO2CH3 and processes for making the same.Type: GrantFiled: June 4, 2001Date of Patent: December 4, 2001Inventors: Sangho Koo, Hojin Choi, Minsoo Park, Minkoo Ji
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Patent number: 6326337Abstract: An oxidation-corrosion additive for enhancing the stability of PFPAEs which has the formula: wherein Q is —Rf or —S—Rf, Rf is a perfluoroalkyl or perfluoroalkylether group having 1 to 30 carbon atoms, x and y are integers, each having a value of 0-5, wherein the sum of x and y is in the range of 1 to 10. In the formula above, Rf may be linear or branched. The additive can be a single component or a mixture of components varying in the number and relative positions of x and y. The additive can be used alone or with other suitable additives in PFPAE base fluids.Type: GrantFiled: April 4, 2001Date of Patent: December 4, 2001Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: Kalathil C. Eapen, Grace J. Chen, Wayne E. Ward, Harvey L. Paige
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Patent number: 6316636Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.Type: GrantFiled: February 28, 1996Date of Patent: November 13, 2001Assignee: Rhone-Poulenc ChimieInventors: Robert Janin, Laurent Saint-Jalmes
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Patent number: 6225505Abstract: The present invention lies in a process for producing a trifluoromethylthiomethylbenzene derivative represented by the following general formula (2): (wherein R is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group, a nitro group, or a benzoyl group which may be substituted with halogen atom, alkyl group, alkoxy group, aliphatic or aromatic acyl group, nitro group, cyano group or alkoxycarbonyl group; n is an integer of 1 to 5; when n is an integer of 2 or more, a plurality of R's may be the same of each independently different), which process comprises reacting, in acetonitrile, a benzyl halide derivative represented by the following general formula (1): (wherein R and n have the same definitions as given above; and X is a halogen atom, an alkylsulfonyloxy group or an arylsulfonyloxy group which may be substituted with alkyl group or halogen atom) with thiophosgene and potassium fluoride.Type: GrantFiled: February 1, 2000Date of Patent: May 1, 2001Assignees: Ihara Chemical Industry Co., LTD, Kumiai Chemical Industry Co., LTDInventors: Yoshikazu Kimura, Hidetaka Hiyoshi, Keiji Toriyabe, Nobuhide Wada
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Patent number: 6175042Abstract: This invention relates to a process for preparing perfluoroalkyl aryl sulfides by reaction of disulfides with alkali metal salts of aliphatic perfluorocarboxylic acids in the presence of a high-boiling aprotic solvent at elevated temperature and reduced pressure, wherein the product formed is distilled off at the rate at which it is formed. This invention further relates to the novel compounds 2-nitrophenyl pentafluoroethyl sulfide and 2-aminophenyl pentafluoroethyl sulfide.Type: GrantFiled: May 28, 1999Date of Patent: January 16, 2001Assignee: Bayer AktiengesellschaftInventors: Vera Yakovlevna Popkova, Albrecht Marhold
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Patent number: 6140515Abstract: Described is a process of preparing 3-aryl, 4-aryloxy furan-5-ones which are useful as inhibitors of cyclooxygenase-2 (COX-2). Such compounds are useful as anti-inflammatory agents. The process is directed to an asymmetric synthesis which involves: a trisubstituted styrene derivative preparation via Horner-Wadsworth-Emmons reaction and subsequent one pot trifluoromethylation of the allylic alcohol; preparation of the .alpha.-hydroxyl ketone using Sharpless asymmetric dihydroxylation and Swern oxidation; the esterification of the .alpha.-hydroxyl ketone with the phenoxy acetic acid; and the Dieckman condensation of the resulting ester.Type: GrantFiled: September 15, 1998Date of Patent: October 31, 2000Assignee: Merck & Co., Inc.Inventors: Cheng Y. Chen, Lushi Tan, Robert D. Larsen