Benzene Ring Containing Patents (Class 570/182)
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Publication number: 20080275253Abstract: A practical and efficient method for halogenation of activated carbon atoms using readily available N-haloimides and a Lewis acid catalyst has been disclosed. This methodology is applicable to a range of compounds and any halogen atom can be directly introduced to the substrate. The mild reaction conditions, easy workup procedure and simple operation make this method valuable from both an environmental and preparative point of view.Type: ApplicationFiled: February 29, 2008Publication date: November 6, 2008Inventors: Yanhua Zhang, Hisashi Yamamoto, Kazutaka Shibatomi
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Patent number: 7408088Abstract: Bromine is scrubbed from a gaseous mixture of bromine and hydrogen bromide by passing the mixture into a mixture formed from (i) diphenylethane and/or partially brominated diphenylethane with average bromine number less than about 2 and (ii) a catalytic quantity of iron and/or iron halide in which the halogen atoms are bromine atoms and/or chlorine atoms. Component (i) is brominated, and during such bromination, the mixture is kept hot enough to melt the organics to provide a liquid phase in the scrubber. Gaseous mixtures of bromine and hydrogen bromide are formed in processes of the invention in which decabromodiphenylethane products are produced using the partially brominated diphenylethane as feed to the bromination, which is conducted using an aluminum-based catalyst. Effective ways of removing iron catalyst residues from partially brominated diphenylethane or from decabromodiphenylethane product are also described.Type: GrantFiled: August 17, 2007Date of Patent: August 5, 2008Assignee: Albemarle CorporationInventor: Bonnie Gary McKinnie
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Patent number: 7316738Abstract: A method of milling chlorothalonil to form a sub-micron product having a narrow particle size distribution is presented. The milling involves wet milling of the chlorothalonil with high density milling media having a diameter between 0.1 mm and 0.8 mm, preferably between 0.2 mm and 0.7 mm, and a density equal to or greater than 3.8 g/cc, preferably greater than 5.5 g/cc, in a ball mill using between about 40% and 80% loading of the mill volume with milling media, and having the chlorothalonil suspended in an aqueous milling liquid which comprises one or more surface active agents. The milling speed is preferably high, for example from about 1000 rpm to about 4000 rpm. The milled product can be used in foliar applications at a lower effective dosage than prior art formulations, can be used in improved antifouling paint formulations, and can be used in new applications such as the direct injection of solid chlorothalonil particulates in wood to act as a long lasting wood preservative.Type: GrantFiled: October 12, 2004Date of Patent: January 8, 2008Assignee: Phibro-Tech, Inc.Inventors: Hugh W. Richardson, Robert L. Hodge
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Patent number: 7312288Abstract: Polymerizable fluorinated ester compounds having formulae (1) and (2) are novel wherein R1 is H, methyl or trifluoromethyl, R2 and R3 are H or a monovalent hydrocarbon group, R2 and R3 may form a ring, R4 is H, OH or a monovalent hydrocarbon group, and R5 is an acid labile group.Type: GrantFiled: October 6, 2004Date of Patent: December 25, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeshi Kinsho, Takeru Watanabe
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Patent number: 7282615Abstract: A method for ring-halogenating an aromatic compound comprises contacting the aromatic compound with chlorine or bromine in the presence of a catalyst composition, where the catalyst composition comprises at least one salt comprising a metal selected from the group consisting of Group 13 metal; and a counterion derived from an acid having a pKa relative to water of 0 or greater; and at least one organic sulfur compound.Type: GrantFiled: June 16, 2004Date of Patent: October 16, 2007Inventors: Dan Hancu, Robert Edgar Colborn, Richard Joseph Kilmer, John Patrick Lemmon
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Patent number: 7102023Abstract: One aspect of the present invention relates to optionally substituted halogenated benzyl halides and the like. These compounds are useful as halogenated benzyl ether-based protecting groups for a variety of functional groups. Another aspect of the present invention relates to use of said protecting groups in an orthogonal protecting group strategy for the synthesis of complex molecules that comprise a number of suitable functional groups. Another aspect of the present invention relates to saccharides bearing various arrays of protecting groups of the present invention. Another aspect of the present invention relates to a method of synthesizing an oligosaccharide or glycoconjugate, comprising the steps of: using a saccharide bearing at least one protecting group of the present invention to glycosylate a second molecule to give a product comprising said saccharide; and removing a protecting group of the present invention from said product.Type: GrantFiled: February 6, 2004Date of Patent: September 5, 2006Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Obadiah J. Plante, Peter H. Seeberger
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Patent number: 7060862Abstract: A method of synthesizing a high purity product of ?,?,??,??-tetrachloro-p-xylene is disclosed. The method includes carrying out a first stage reaction of terephthaldicarboxaldehyde with a mixture of SOCl2 and dimethylformamide (DMF) to obtain a product mixture containing ?,?,??,??-tetrachloro-p-xylene as a major product and 4-dichloromethyl benzaldehyde as a side product; adding SOCl2 and DMF to the product mixture of the first stage reaction to undergo a second stage reaction; and to a cool water adding the resulting product mixture from the second stage reaction to obtain a solid product of ?,?,??,??-tetrachloro-p-xylene with a purity of 90-99 mol %.Type: GrantFiled: December 30, 2003Date of Patent: June 13, 2006Assignee: Chung-Shan Institute of Science & TechnologyInventors: Shean-Jeng Jong, Chun-Hsu Lin, Chao-chou Tu, Chung-Chien Chang
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Patent number: 6992231Abstract: A synthesis method of ?,?,??,??-tetrachloro-p-xylene is disclosed. The method includes reacting terephthaldicarboxaldehyde with a mixture of SOCl2 and dimethylformamide (DMF) to obtain a product mixture containing ?,?,??,??-tetrachloro-p-xylene as a major product and 4-dichloromethyl benzaldehyde as a side product, which can be separated by silica column chromatography.Type: GrantFiled: December 30, 2003Date of Patent: January 31, 2006Assignee: Chung-Shan Institute of Science & TechnologyInventors: Shean-Jeng Jong, Chun-Hsu Lin, Ming-Te Shih, Chung-Chien Chang
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Patent number: 6943257Abstract: The present invention provides a process for preparing an aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite anion and halodimethylsulfonium halide generated in situ from hydrobromic acid/DMSO or hydriodic acid/DMSO. The process for producing compounds of the formula (1) is disclosed (1) wherein X is bromine or iodine: Y is carbon or nitrogen; R1, R2, R3, R4 and R5 which may be the same or different and are selected independently from the group consisting of a hydrogen, a hologen, a C1-C8 alkyl, a C1-C10 alkoxy, a nitro, a formyl, an aryl, a benzyl, a C2-C10 alkylcarbonyl and an arylcarbonyl, provided that adjacent groups as selected from R1, R2, R3, R4 and R5 may combine to form a ring.Type: GrantFiled: September 21, 2001Date of Patent: September 13, 2005Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
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Patent number: 6743825Abstract: An additive mixture useful as a flame retardant is described. The mixture is comprised of (i) a poly(bromophenyl)alkane having in the molecule in the range of 13 to 60 carbon atoms and in the range of two to four aryl groups and (ii) a poly(bromophenyl)bromoalkane having in the molecule in the range of 13 to 60 carbon atoms and in the range of two to four aryl groups, said poly(bromophenyl)bromoalkane being in an amount which is greater than 25 wt %, based on the total weight of the additive mixture. A facile process for making the poly(bromophenyl)bromoalkane is also described.Type: GrantFiled: August 5, 2002Date of Patent: June 1, 2004Assignee: Albemarle CorporationInventors: Raymond B. Dawson, Saadat Hussain
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Patent number: 6733883Abstract: This invention relates to novel fluorinated dendrons and to a universal strategy for producing functional fluorinated dendrons programmed to self-assemble into supramolecular nanocylinder compositions containing p-stacks of high electron or hole mobility donors (D), acceptors (A), or D-A complexes in the core. Such nanocylinder compositions are uniquely applicable to devices spanning from single supramolecule to nanoscopic and to macroscopic scales including transistors, photovoltaics, photoconductors, photorefractives, light emissives, and optoelectronics.Type: GrantFiled: November 12, 2002Date of Patent: May 11, 2004Assignee: The Trustees of the University of PennsylvaniaInventor: Virgil Percec
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Patent number: 6710217Abstract: The invention relates to a process for preparing 4-chlorobiphenyl by (a) reacting biphenyl and chlorine in the presence of one or more ring-chlorination catalysts, and (b) subjecting the reaction mixture obtained in step (a) to fractional distillation to obtain 4-chlorobiphenyl.Type: GrantFiled: November 13, 2001Date of Patent: March 23, 2004Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Alexander Klausener, Paul Wagner, Lothar Puppe
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Publication number: 20030235782Abstract: The present invention relates to a novel photoresist composition that can be developed with an aqueous alkaline solution, and is capable of being imaged at exposure wavelengths in the deep ultraviolet. The invention also relates to a process for imaging the novel photoresist as well as novel photoacid generators.Type: ApplicationFiled: May 16, 2003Publication date: December 25, 2003Inventors: Munirathna Padmanaban, Takanori Kudo, Sangho Lee, Ralph R. Dammel, M. Dalil Rahman
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Publication number: 20030181690Abstract: One aspect of the present invention relates to optionally substituted halogenated benzyl halides and the like. These compounds are useful as halogenated benzyl ether-based protecting groups for a variety of functional groups. Another aspect of the present invention relates to use of said protecting groups in an orthogonal protecting group strategy for the synthesis of complex molecules that comprise a number of suitable functional groups. Another aspect of the present invention relates to saccharides bearing various arrays of protecting groups of the present invention. Another aspect of the present invention relates to a method of synthesizing an oligosaccharide or glycoconjugate, comprising the steps of: using a saccharide bearing at least one protecting group of the present invention to glycosylate a second molecule to give a product comprising said saccharide; and removing a protecting group of the present invention from said product.Type: ApplicationFiled: May 15, 2002Publication date: September 25, 2003Inventors: Stephen L. Buchwald, Obadiah J. Plante, Peter H. Seeberger
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Patent number: 6610219Abstract: Functional optical materials for optical systems that are typically useful in optical waveguides, optical switching systems, optical modulators, optical computing systems and the like. Included are polymer systems and electrooptical chromophores. Polymers are thermoplastic and/or thermosetting polymers and are blended or co-polymerized with the electrooptic chromophore. The thermoplastic or thermosetting polymer selected from an acrylic/methacrylic, polyester, polyurethane, polyimide, polyamide, epoxy resin, or hybrid (organic-inorganic) or nanocomposite polyester polymer. The electrooptic chromophore is selected from a substituted aniline, substituted azobenzene, substituted stilbene, or substituted imine. Methods for improving adhesion promotion for the various novel materials are also provided.Type: GrantFiled: February 6, 2001Date of Patent: August 26, 2003Assignee: Battelle Memorial InstituteInventors: Vincent D. McGinniss, Steven M. Risser
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Patent number: 6605409Abstract: A positive resist composition comprising (A) a compound generating a specific sulfonimide compound by irradiation with an actinic ray or a radiation and (B) a resin having a group, which is decomposed by the action of an acid to increase the solubility of the composition in an alkali developer. The resist composition has an improved resolving power and an improved process allowance such as exposure margin and the depth of focus in a lithographic technique using a light source of short wavelengths capable of super fine working and a positive chemically amplified resist.Type: GrantFiled: May 21, 2001Date of Patent: August 12, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Kunihiko Kodama, Shinichi Kanna
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Patent number: 6583307Abstract: A Pd(OAc)2/diazabutadiene system has been developed for the catalytic cross-coupling of aryl halides with arylboronic acids. A combination of the diazabutadiene DAB-Cy (1, N,N′-Dicyclohexyl-1,4-dizabutadiene) and Pd(OAc)2 was found to form an excellent catalyst for the Suzuki-Miyaura cross-coupling of various aryl bromides and activated aryl chlorides with arylboronic acids.Type: GrantFiled: March 7, 2002Date of Patent: June 24, 2003Assignee: University of New Orleans Research and Technology Foundation, Inc.Inventors: Steven P. Nolan, Gabriela Grasa
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Patent number: 6566546Abstract: A process for preparing 4-substituted 2-alkylbiphenyls and 2-alkoxybiphenyls of the formula (I),Type: GrantFiled: February 11, 2002Date of Patent: May 20, 2003Assignee: Clariant GmbHInventors: Andreas Meudt, Stefan Scherer, Frank Vollmüller, Heinz Georg Kautz
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Patent number: 6509507Abstract: A process for preparing polymerizable biaryl derivatives comprises reacting an aromatic comprising a 6-membered ring which bears ester or benzylic OH groups in the 1,4 position with a second aromatic in a palladium-catalyzed cross-coupling reaction to give a biaryl and converting the ester or benzylic OH groups into polymerizable groups in one or more steps. The biaryls obtained are suitable for preparing polymers which are used as electroluminescence materials.Type: GrantFiled: October 16, 2001Date of Patent: January 21, 2003Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
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Patent number: 6489524Abstract: Aromatic substrates are Ar-brominated in high yield and selectivity by reacting the substrate with a brominating agent in the presence of at least about 0.19 gram per mmol of substrate of a zeolite catalyst which has an absorbed water content of no greater than about 7.5 weight percent.Type: GrantFiled: October 27, 1997Date of Patent: December 3, 2002Assignee: Albemarle CorporationInventors: Mahmood Sabahi, Hassan Y. Elnagar, Robert L. Davis
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Patent number: 6388123Abstract: The present invention relates to novel compounds of the formula (I) in which Het represents one of the groups in which A, B, D, G, V, W, X, Y and Z are as defined in the description, processes and intermediates for their preparation, and to their use as pesticides and herbicides.Type: GrantFiled: June 1, 2001Date of Patent: May 14, 2002Assignee: Bayer AktiengesellschaftInventors: Volker Lieb, Hermann Hagemann, Arno Widdig, Michael Ruther, Reiner Fischer, Thomas Bretschneider, Christoph Erdelen, Ulrike Wachendorff-Neumann, Alan Graff, Udo Schneider
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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: 20010056210Abstract: Compounds of formula III, 1Type: ApplicationFiled: July 6, 2001Publication date: December 27, 2001Inventors: Benoit Pugin, Ivo Steiner, Rhony Niklaus Aufdenblatten, Antonio Togni
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Patent number: 6323373Abstract: A process for preparing polymerizable biaryl derivatives comprises reacting an aromatic comprising a 6-membered ring which bears ester or benzylic OH groups in the 1,4 position with a second aromatic in a palladium-catalyzed cross-coupling reaction to give a biaryl and converting the ester or benzylic OH groups into polymerizable groups in one or more steps. The biaryls obtained are suitable for preparing polymers which are used as electroluminescence materials.Type: GrantFiled: June 9, 1999Date of Patent: November 27, 2001Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
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Patent number: 6284894Abstract: A process for the preparation of an allylic aromatic compound in which an aromatic amine is reacted first with a nitrite and then with an allylic olefin having an eliminatable terminal substituent. Novel allylic derivatives of disubstituted benzene compounds are also described.Type: GrantFiled: December 17, 1999Date of Patent: September 4, 2001Assignee: Nycomed Imaging ASInventors: Fredrik Ek, Lars Goran Wistrand
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Patent number: 6265628Abstract: In a process for the continuous preparation of mono- and/or bis(mono- and/or di- and/or trichloromethyl) benzenes by gradual chlorination of the corresponding mono-or dimethylbenzenes in several reactors in cascade, the first reactor has a greater volume than each of the other reactors.Type: GrantFiled: April 9, 1999Date of Patent: July 24, 2001Assignee: Elf Atochem, S.A.Inventors: Raymond Commandeur, Régis Loze
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Patent number: 6252001Abstract: Compounds of ethynyl aromatic compounds form polymers which have high thermal stability. The monomers are useful for coating a wide variety of substances such as dielectric coatings where high thermal resistance is desirable including electronic components such as computer chips.Type: GrantFiled: January 13, 2000Date of Patent: June 26, 2001Assignee: The Dow Chemical CompanyInventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
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Patent number: 6121495Abstract: Compounds of ethynyl aromatic compounds form polymers which have high thermal stability. The monomers are useful for coating a wide variety of substances such as dielectric coatings where high thermal resistance is desirable including electronic components such as computer chips.Type: GrantFiled: September 12, 1996Date of Patent: September 19, 2000Assignee: The Dow Chemical CompanyInventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
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Patent number: 6117361Abstract: A compound represented by the following general formula (1) is provided. This has broader temperature range of nematic phase, lower viscosity and higher miscibility with other liquid crystal compounds at low temperature than those of conventional liquid crystal compounds, and the compounds have high chemical stability. ##STR1## wherein H.sub.1 to H.sub.8 represent independently a hydrogen atom or a halogen atom, provided that at least one of them is a halogen atom; R.sub.1 represents a moiety which is an alkyl group having 2 to 20 carbon atoms provided that one or more methylene groups (--CH.sub.2 --) which are not successive in the alkyl group are replaced with an oxygen atom (--O--) in the form of ether; Y.sub.1 represents an alkyl group having 1 to 20 carbon atoms, and one or more methylene groups in Y.sub.1 independently may be replaced with an oxygen atom, a sulfur atom, a dihydroxysilyl group, a dimethylsililene group, --CH.dbd.CH-- or --C.tbd.C--; X.sub.1 to X.sub.Type: GrantFiled: August 31, 1998Date of Patent: September 12, 2000Assignee: Chisso Corp.Inventors: Koichi Shibata, Tomoyuki Kondo, Shuichi Matsui, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 6057006Abstract: The invention relates to fluorocyclohexane derivatives of the formula I ##STR1## in which R.sup.1, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2, L.sup.3 and X are as defined as below:X is alkyl or alkoxy having 1 to 10 carbon atoms which is unsubstituted or substituted by halogen, alkenyl or alkenyloxy having 2 to 10 carbon atoms which is unsubstituted or substituted by --CN, --CF.sub.3 or --F, or is --CN, --F, --OCHF.sub.2, --OCF.sub.3, --OCHFCF.sub.3 or --OCF.sub.2 CF.sub.3,L.sup.1, L.sup.2 and L.sup.3 are each, independently of one another, H or F,R.sup.1 is H, an alkyl or alkenyl radical having 1-12 carbon atoms which is unsubstituted, monosubstituted by CN or CF.sub.3 or substituted by halogen, where one or more non-adjacent CH.sub.2 groups in these radicals may also, in each case independently of one another, be replaced by --O--, --S--, --CO--, --.diamond.--, --CO--O--, --O--CO-- or --O--CO--O--,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --O--, --O--CH.sub.Type: GrantFiled: June 4, 1998Date of Patent: May 2, 2000Assignee: Merck Patent GesellschaftInventors: Peer Kirsch, Kazuaki Tarumi, Joachim Krause
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Patent number: 6008283Abstract: Flame retardants comprising oligomeric bromine-containing compounds comprising aryl groups that are connected by aliphatic chains are described. Flame retardant compositions comprising the flame retardants of the present invention and flame retardant aids are also described. Polymeric compositions comprising the flame retardants of the present invention optionally combined with a flame retardant aid, along with a method of fireproofing a material, are further described.Type: GrantFiled: March 19, 1998Date of Patent: December 28, 1999Assignee: Great Lakes Chemical CorporationInventors: Richard S. Rose, Gurudas Zingde, David M. Hemmerly
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Patent number: 5998595Abstract: Azidohalogenobenzyl derivatives of the formula (I) ##STR1## wherein A is a halogen atom, B is a halogen atom or a hydrogen atom, and X is a group reactive with a hydroxy group, methods of protecting hydroxy group(s) using said derivatives, and sugar compounds wherein a hydrogen atom of at least one hydroxy group is substituted by an azidohalogenobenzyl group. According to the present invention, there are provided novel derivatives capable of introducing a group into a compound having hydroxy group(s), which group is useful as a stable hydroxy-protecting group even in solid phase synthesis for the purpose of the extension of sugar chain under continuous acidic conditions and of being removed under mild conditions; sugar compounds protected by using said derivatives; and methods of protecting hydroxy group(s) using said derivatives.Type: GrantFiled: October 30, 1997Date of Patent: December 7, 1999Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Shoichi Kusumoto, Koichi Fukase
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Patent number: 5977419Abstract: The invention relates to novel processes for the preparation of phenyl acetic acid derivatives of the formula (I) some of which are known ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently of each other each represent hydrogen, alkyl or alkoxy by ozonolysis of compounds of the formula (II) ##STR2## in which R.sup.4 represents hydrogen or methyl and oxidation of the reaction products obtained therefrom. The invention further relates to novel intermediates and a process for the preparation thereof.Type: GrantFiled: December 22, 1997Date of Patent: November 2, 1999Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Rainer Fuchs
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Patent number: 5886242Abstract: The invention relates to chiral compounds containing at least one divalent or polyvalent chiral group, at least one polymerizable group, at least one spacer and at least one mesogenic group, and to their use as polymerizable, chiral dopes for the preparation of cholesteric networks.The novel compounds are suitable for use in electro-optical displays or as chiral dopes for nematic or cholesteric liquid crystals in order to produce layers which reflect in colors.Type: GrantFiled: January 12, 1998Date of Patent: March 23, 1999Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Etzbach, Paul Delavier, Karl Siemensmeyer, Gerhard Wagenblast, Lothar Laupichler, Volkmar Vill
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Patent number: 5841004Abstract: A novel 3-substituted .alpha.,.beta.-dibromoethylbenzene of formula (I): ##STR1## wherein X represents a halogen atom or a trihalomethyl group, which is useful as an intermediate for pharmaceuticals or agricultural chemicals, is prepared by a simple and high yield process which comprises reacting a 3-substituted .alpha.-bromoethylbenzene represented by formula (II): ##STR2## wherein X is as defined above, or a 3-substituted ethylbenzene represented by formula (III): ##STR3## wherein X is as defined above, with bromine in the presence of a quaternary ammonium salt.Type: GrantFiled: July 17, 1996Date of Patent: November 24, 1998Assignee: Mitsubishi Chemical CorporationInventors: Ken Tanaka, Manabu Katsurada, Akemi Hosokawa
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Patent number: 5833879Abstract: A novel liquid crystalline compound having a sufficiently large .DELTA.n, a superior, low temperature compatibility with other liquid crystals and a chemical stability; a liquid crystal composition containing the above compound; and a display element using the above liquid crystal composition are provided,which liquid crystalline compound is expressed by the formula (1): ##STR1## wherein R.sub.1 is an alkyl group or alkoxy group of 1 to 10C, cyano group or a halogen atom; R.sub.2 is an alkyl group of 1 to 5C wherein one methylene group (--CH.sub.2 --) may be replaced by oxygen atom; X.sub.1 and X.sub.2 each independently are hydrogen atom or a halogen atom; A and B each independently are single bond, 1,4-phenylene ring or 1,4-cyclohexylene ring which may be substituted by halogen atom may be; and p is 1 to 5.Type: GrantFiled: February 12, 1996Date of Patent: November 10, 1998Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuko Sekiguchi, Etsuo Nakagawa
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Patent number: 5831102Abstract: Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; andR.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sup.1 and R.sub.Type: GrantFiled: February 8, 1996Date of Patent: November 3, 1998
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Patent number: 5746998Abstract: A radiographic imaging agent including a plurality of block copolymers forming a micelle, the block copolymers including a hydrophilic polymer linked to a hydrophobic polymer, and the hydrophobic polymer including a backbone incorporating radiopaque molecules via covalent bonds.Type: GrantFiled: August 8, 1996Date of Patent: May 5, 1998Assignee: The General Hospital CorporationInventors: Vladimir P. Torchilin, Vladimir S. Trubetskoy, Gerald L. Wolf, G. Scott Gazelle
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Patent number: 5686608Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium as catalyst comprises adding to the reactiona) at least one water-soluble complexing ligand andb) sufficient water for the reaction mixture to form an aqueous phase.The reaction of the invention proceeds chemoselectively so that even electrophilic groups such as esters or nitriles do not have an adverse effect on the course of the reaction.The use according to the invention of a water-soluble complexing ligand in an aqueous phase enables polycyclic aromatic compounds to be prepared in very good yields and at the same time very high purity, in particular without contamination by the complexing ligands.Type: GrantFiled: April 24, 1995Date of Patent: November 11, 1997Assignee: Hoechst AktiengesellschaftInventors: Steffen Haber, Javier Manero
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Patent number: 5589102Abstract: Benzene derivatives of the formula I ##STR1## in which R, A.sup.1, A.sup.2 X, L.sup.1, L.sup.2 m and n are as defined in claim are suitable as components of liquid-crystalline media.Type: GrantFiled: September 5, 1995Date of Patent: December 31, 1996Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Kazuaki Tarumi
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Patent number: 5567410Abstract: A radiographic imaging agent including a plurality of block copolymers forming a micelle, the block copolymers including a hydrophilic polymer linked to a hydrophobic polymer, and the hydrophobic polymer including a backbone incorporating radiopaque molecules via covalent bonds.Type: GrantFiled: June 24, 1994Date of Patent: October 22, 1996Assignee: The General Hospital CorporationInventors: Vladimir P. Torchilin, Vladimir S. Trubetskoy, Gerald L. Wolf, G. Scott Gazelle
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Patent number: 5550236Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boronic acids with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium, if desired applied to a support material, as catalyst, wherein the coupling is carried out in the presence of a ligand and a base. The process of the invention allows the yield of polycyclic aromatic compounds to be significantly increased in comparison with processes not using a ligand and thus allows a yield optimum for the Pd(0)-catalyzed cross-coupling of aromatic boronic acids with aromatic halogen compounds to be achieved.Type: GrantFiled: April 24, 1995Date of Patent: August 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Hubert Schlosser, Rainer Wingen, Javier Manero
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Patent number: 5545768Abstract: A process for the preparation of chlorofluoronitrobenzenes and difluoronitrobenzenes, which comprises heating dichloronitrobenzene to not more than 200.degree. C. in excess with an alkali metal fluoride having a total water content of about 0.2 to about 2.5% by weight in the presence of a quaternary ammonium and/or phosphonium salt, crown ether and/or polyethylene glycol dimethyl ether as catalyst in the absence of a solvent.Type: GrantFiled: December 22, 1992Date of Patent: August 13, 1996Assignee: Hoechet AGInventors: Theodor Papenfhus, Andreas Kanschik-Conradsen, Wilfried Pressler
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Patent number: 5478497Abstract: Compounds of the formula ##STR1## wherein rings A, B and C, Z.sup.1, Z.sup.2, Z.sup.3, R.sup.1, R.sup.2 and R.sup.3 are defined in the specification, their manufacture, liquid crystalline mixtures which contain such compounds and the use of these compounds for electro-optical purposes.Type: GrantFiled: February 1, 1995Date of Patent: December 26, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt, Alois Villiger
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Patent number: 5401493Abstract: Organic compounds for diagnostic imaging which contain at least one aryl group which has been derivatized to contain at least one perfluoro-1H,1H-neopentyl moiety are provided. The perfluoro-1H,1H-neopentyl groups produce a single magnetic resonance to insure a maximum signal to noise ratio. One compound disclosed is 2-O-oleoylglycerol 1,3-bis(7'-{3",5"-di[2"',2"'-di(trifluoromethyl)3"', 3"',3"'-trifluoropropyl]phenyl}heptanoate). In the preferred embodiment, a lipid emulsion is provided as a carrier vehicle to deliver the derivitized analog to a mammalian recipient. Methods to use these compounds in MRI and computerized tomography are provided.Type: GrantFiled: March 26, 1993Date of Patent: March 28, 1995Assignee: Molecular Biosystems, Inc.Inventors: Rolf Lohrmann, Ashwin Krishnan
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Patent number: 5401896Abstract: Relatively long chain alkyl aromatic compounds are prepared by alkylating an alkylatable aromatic compound with a relatively long chain alkylating agent under alkylation reaction conditions in the presence of catalyst comprising zeolite MCM-49.Type: GrantFiled: November 23, 1992Date of Patent: March 28, 1995Assignee: Mobil Oil Corp.Inventors: Guenter H. Kuehl, Daria N. Lissy, Hye Kyung C. Timken
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Patent number: 5389294Abstract: The invention relates to chlorobenzene derivatives of formula I ##STR1## wherein R.sup.1 denotes an alkyl residue with up to 12 carbon atoms wherein one or two non-adjacent CH.sub.2 -groups may also be replaced by --O--, --O--CO--, --CO--O-- and/or --CH.dbd.CH--.Type: GrantFiled: June 22, 1990Date of Patent: February 14, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: David Coates, Simon Greenfield
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Patent number: 5356893Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a halogen or hydrogen atom or a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group;R.sup.2 represents a phenyl group optionally substituted by one or two substituents;R.sup.3 represents the group ##STR2## R.sup.4 and R.sup.5, which may be the same or different, each independently represent a hydrogen atom or a halogen atom, or a group selected from hydroxy, C.sub.1-6 alkoxy or C.sub.1-6 alkyl.The compounds may be used in the treatment or prophylaxis of depression and other CNS disorders.Type: GrantFiled: September 17, 1992Date of Patent: October 18, 1994Assignee: Glaxo Group LimitedInventors: John Bradshaw, John W. Clitherow, Ian B. Campbell
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Patent number: 5334754Abstract: Provided is a process for preparing 2,5-diphenylterephthalic acid, which is useful in preparing certain polyesters, especially liquid-crystalline polyesters. In this process, p-xylene is di-alkylated with cyclohexene to provide 2,5-dicyclo-hexyl-p-xylene, which is in turn dehydrogenated to provide 2,5-diphenylxylene. 2,5-Diphenylxylene is then oxidized to provide 2,5-diphenylterephthalic acid by utilization of a cobaltous/manganous/bromide oxidation system.Type: GrantFiled: August 14, 1992Date of Patent: August 2, 1994Assignee: Eastman Chemical CompanyInventors: Charles E. Sumner, Jr., Bruce L. Gustafson, Ernest W. Arnold, III, Eric J. Fugate, Dewey W. Fuller, Jr.
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Patent number: RE36849Abstract: Anisotropic compounds of the formula (1) specified in claim 1 are suitable, owing to their low .DELTA..epsilon./.epsilon..perp. values for liquid crystal displays which have high information densities of for examples up to 10.sup.6 image dots and accordingly need to be highly multiplexible; compared with known compounds they offer improved application properties and are relatively simple to synthesize.Type: GrantFiled: April 1, 1993Date of Patent: September 5, 2000Assignee: Merck Patent GmbHInventors: Hans P. Schad, Stephen M. Kelly, Eike Poetsch, Reinhard Hittich, Georg Weber