Benzene Ring Containing Patents (Class 570/127)
  • Patent number: 5831102
    Abstract: 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: Grant
    Filed: February 8, 1996
    Date of Patent: November 3, 1998
  • Patent number: 5792892
    Abstract: The present invention relates to processes for the preparation of bromine-containing aromatic compounds, to novel bromine-containing compounds and to their use as intermediates in the synthesis of active substances. Processes according to the invention for the preparation of known and novel bromine-containing compounds are characterized by specific conditions.
    Type: Grant
    Filed: October 22, 1996
    Date of Patent: August 11, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Hagemann
  • Patent number: 5789634
    Abstract: Novel 2-substituted 7-haloindenes and methods for synthesizing such indenes are described. The 2-substituted 7-haloindenes may be coupled with any aryl group to produce a metallocene catalyst intermediate.
    Type: Grant
    Filed: February 5, 1997
    Date of Patent: August 4, 1998
    Assignee: Boulder Scientific Company
    Inventors: Jeffrey M. Sullivan, Hamlin H. Barnes
  • Patent number: 5780672
    Abstract: A process for the preparation of compounds of the formula (1) in which R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, which includes reacting alcohols or carboxylic acids of the formula (2) in which R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, with a fluorinating agent of the formula (3) as defined in the specification.
    Type: Grant
    Filed: July 11, 1996
    Date of Patent: July 14, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Sergej Pasenok, Wolfgang Appel
  • Patent number: 5776367
    Abstract: A novel liquid crystalline compound having a low viscosity and a high elastic constant ratio and at the same time, a superior compatibility with other known liquid crystalline compounds, and a liquid crystal composition and a liquid crystal display element containing the novel compound, are provided.The compound is an alkenylcyclohexane derivative expressed by the formula (1): ##STR1## wherein R.sup.1 and R.sup.2 represent a linear or branched alkyl group of 1 to 15 carbon atoms or alkenyl group of 2 to 15 carbon atoms; at least one of R.sup.1 and R.sup.2 represents an alkenyl group; in these groups, one or more non-adjacent CH.sub.2 groups may be replaced by oxygen atom, sulfur atom or --C.tbd.C-- group; ring A.sup.1, ring A.sup.2 and ring A.sup.3 each independently represent 1,4-cyclohexylene group wherein one or more CH.sub.2 groups on the ring may be replaced by oxygen atom or sulfur atom, or 1,4-phenylene group wherein one or more CH groups on the ring may be replaced by nitrogen atom; Z.sup.1 and Z.sup.
    Type: Grant
    Filed: June 19, 1996
    Date of Patent: July 7, 1998
    Assignee: Chisso Corporation
    Inventors: Shuichi Matsui, Yasuyuki Koizumi, Takashi Kato, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
  • Patent number: 5777181
    Abstract: 2,4,5-Trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: July 7, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Uwe Petersen, Klaus Grohe
  • Patent number: 5763699
    Abstract: 2,2-diphenylhexafluoropropanes are prepared by condensation reaction of benzene or benzenes substituted with a halogen atom or atoms, a lower alkyl group or groups or a hydroxyl group or groups with hexafluoroacetone in the presence of trifluoromethane sulfonic acid. Among the 2,2-diphenylhexafluoropropanes, 2,2-diphenylhexafluoropropane and 2,2-bis(p-chlorophenyl)hexafluoropropane are novel compounds.
    Type: Grant
    Filed: November 27, 1996
    Date of Patent: June 9, 1998
    Assignee: Nippon Mektron, Limited
    Inventors: Lev Solomonovich German, deceased, Valerii Romanovich Polishchuk, deceased, Riichi Iwa, Haruyoshi Tatsu
  • Patent number: 5760282
    Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: June 2, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Thomas Baker, Richard Paul Beatty, William Brown Farnham, Robert Lewis Wallace, Jr.
  • Patent number: 5760255
    Abstract: The invention is drawn to a process for the conversion of primary and secondary alcohols into the corresponding fluorine compounds in the presence of an organic solvent, 2-3 equivalents of a strong base and perfluoroalkylsulphonyl fluorides, such as perfluorobutanesulphonyl fluoride or higher homologues.
    Type: Grant
    Filed: June 25, 1996
    Date of Patent: June 2, 1998
    Assignee: Bayer AG
    Inventors: Helmut Vorbruggen, Barbel Bennua-Skalmowski
  • Patent number: 5756834
    Abstract: It is known to prepare fluorinated aromatic compounds of the formula I ##STR1## in which X, Y and Z can have the meaning specified in the description, by reacting aromatic compounds of the formula II ##STR2## in which X, Y and Z have the meaning specified for formula I, with fluorine in a reaction medium.According to the invention, the direct fluorination is carried out in a reaction medium containing polyfluoroalkanesulfonic acids of the formula IIICF.sub.n H.sub.3-n (CFY).sub.m --SO.sub.3 H (III)in whichm, n and Y have the meaning specified in the description.By this means, it is possible, particularly advantageously to provide a process, which improves the known processes not only with regard to the selectivity and the yield, but also with respect to the quality of the resulting products of the process in a manner not readily predictable.Fluorinated aromatic compounds of the formula I as intermediates for active compound synthesis.
    Type: Grant
    Filed: November 7, 1996
    Date of Patent: May 26, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Sergej Pasenok, Wolfgang Appel
  • Patent number: 5739361
    Abstract: A new process for the preparation of furosemide ?4-chloro-N-(2-furylmethyl)-5-sulfamoyl-anthranilic acid!comprising the photochlorination of 4-chloro-2-fluoro-toluene to give 4-chloro-2-fluoro-benzotrichloride, the aminosulfonylation of the same and the subsequent condensation with furfurylamine.
    Type: Grant
    Filed: April 23, 1997
    Date of Patent: April 14, 1998
    Assignee: Proteos S.r.L.
    Inventors: Angelo Signor, Alfredo Guerrato, Giovanni Signor
  • Patent number: 5739388
    Abstract: The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are COOH, H, F, Cl, Br, CF.sub.3, OH, an alkoxy or alkyl radical having in each case 1 to 4 carbon atoms or a radical --NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 are identical or different and are H, an alkyl radical having 1 to 4 carbon atoms or a phenyl radical, by dissolving in water a compound of the formula ##STR2## in which the radicals R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and have the abovementioned meaning or, in departure therefrom, instead of H can be COOH, admixing the aqueous solution with a water-insoluble amine which is inert under the reaction conditions and carrying out the decarboxylation at a pH of 3 to 9 and a temperature of 70.degree. to 210.degree. C.
    Type: Grant
    Filed: May 2, 1996
    Date of Patent: April 14, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Hans Schubert
  • Patent number: 5720899
    Abstract: A novel liquid crystalline compound having a high elastic constant ratio (K.sub.33 /K.sub.11) and an improved solubility thereof in other liquid crystal materials, at low temperatures, and a liquid crystal composition containing the same are provided. The liquid crystalline compound is expressed by the formula (1): ##STR1## wherein Q represents CF.sub.3, CF.sub.2 H or CFH.sub.2 ; A.sub.1, A.sub.2 and A.sub.3 each independently represent trans-1,4-cyclohexylene group, 1,4-phenylene group, wherein one or more hydrogen atoms on its six-membered ring may be replaced by F, Cl or CN, pyridine-2,5-diyl group or 1,3-pyrimidine-2,5-diyl; ring B represents 1,4-phenylene group or trans-1,4-cyclohexylene group; Z.sub.1, Z.sub.2 and Z.sub.3 each independently represent covalent bond, --C.dbd.C--, --C.tbd.C--, --OCO--, --COO--, --CH.sub.2 O--, --OCH.sub.2 --, --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.4 --; l and m each independently represent an integer of 0 to 5; o and p each independently represent 0 or 1; L.sub.1 and L.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: February 24, 1998
    Assignee: Chisso Corporation
    Inventors: Tomoyuki Kondo, Kazutoshi Miyazawa, Atsuko Fujita, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
  • Patent number: 5714088
    Abstract: Liquid crystalline compounds are disclosed which are expressed by the following general formula (1) ##STR1## wherein R.sub.1 represents a branched alkyl group having 3 to 10 carbon atoms, ring A represents 1,4-phenylene group or 1,4-cyclohexylene group, Z.sub.1 and Z.sub.2 independently represent a single bond or 1,2-ethylene group, respectively, X.sub.1, X.sub.2, X.sub.3, and X.sub.4 independently represent fluorine atom or hydrogen atom, respectively, and Y.sub.1 represents oxygen atom or a single bond. The compounds are excellent in compatibility with other liquid crystalline compounds, and have a large positive value of dielectric anisotropy, extremely low viscosity, extremely high specific resistance (high voltage holding ratio), and excellent UV stability.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: February 3, 1998
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuko Sekiguchi, Etsuo Nakagawa
  • Patent number: 5693261
    Abstract: Pentafluorophenylmagnesium halides are prepared by a Grignard exchange reaction of hydrocarbylmagnesium halide with pentafluorochlorobenzene. The pentafluorophenylmagnesium halides are converted to pentafluorophenyl metal or metalloid derivatives by reacting them with metal or metalloid halides such as BF.sub.3.
    Type: Grant
    Filed: August 9, 1995
    Date of Patent: December 2, 1997
    Assignee: Albemarle Corporation
    Inventors: Niomi L. Krzystowczyk, Steven P. Diefenbach, Wendy L. Lemoine
  • Patent number: 5679285
    Abstract: Vinylene compounds of the formula I ##STR1## in which R, A.sup.1, Z.sup.1, X, L.sup.1, L.sup.2 and m have the meaning given in claim 1 are suitable as components of liquid-crystalline media.
    Type: Grant
    Filed: February 15, 1996
    Date of Patent: October 21, 1997
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ekkehard Bartmann, Sabine Schoen, Kazuaki Tarumi
  • Patent number: 5672765
    Abstract: Aromatic, ring-fluorinated compounds are prepared by reaction of corresponding chlorine compounds or bromine compounds with alkali metal fluorides using a diamide as solvent. Most of the diamides which can be used are novel compounds.
    Type: Grant
    Filed: July 14, 1995
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Marianne Lohr, Heinrich Wamhoff
  • Patent number: 5670085
    Abstract: A liquid crystalline compound expressed by the formula ##STR1## wherein R.sub.1 represents an alkyl group of 1 to 12 carbon atoms, and one or two not adjacent CH.sub.2 group excluding the terminal in this group may be replaced by --CO-- group, --OCO-- group, --COO-- group or --CH.dbd.CH group; X and Z each represents H, F or Cl; Y represents perfluoroalkyl group or perfluoroalkyloxy group of 1 to 4 carbon atoms, and one or two F atoms in this group may be replaced by H; one of A, B and C represents cyclohexene ring and the others thereof are chosen from among covalent bond or cyclohexane group and benzene ring and these rings may be substituted by F or Cl; and l, m and n each are 0 or 1, independently of each other, but when m=0, then l=0.EffectivenessIt is possible to provide a liquid crystal composition having a large .DELTA.n, a low viscosity and a high voltage-holding ratio, and exhibiting a nematic liquid crystal phase within a broad temperature range and having a very high .DELTA..epsilon.
    Type: Grant
    Filed: January 18, 1996
    Date of Patent: September 23, 1997
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
  • Patent number: 5665270
    Abstract: An optically active compound derived from a novel trifluorolactic acid, useful as a component of a ferroelectric liquid crystal composition, and a liquid crystal composition. A compound represented by general formula (I), wherein R.sup.1 represents C.sub.1 to C.sub.18 alkyl, alkoxy, C.sub.2 to C.sub.18 alkanoyl, alkanoyloxy or alkoxycarbonyl; R.sup.2 represents optionally alkoxy-substituted alkyl (where the total number of the carbon atoms is 1 to 15); A, B and C represent each independently the group (a) or (b); v and w represent each independently --COO--, --OCO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.dbd.C-- or a single bond; and x and y together represent any of the following combinations: --COO-- and --COO--; --COO-- and --CO--; --COO-- and --CH.sub.2 O--; --COO-- and --CH.sub.2 OCO--; --COO-- and --CH.sub.2 OCOO--; --O-- and --CH.sub.2 O--; --O-- and --CH.sub.2 OCO--; and --O-- and --CH.sub.2 OCOO--.
    Type: Grant
    Filed: May 4, 1994
    Date of Patent: September 9, 1997
    Assignee: Chisso Corporation
    Inventors: Masatoshi Fukushima, Shinichi Saito
  • Patent number: 5658489
    Abstract: A diphenylacetylene compound of the formula [1]: ##STR1## wherein R is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group or a C.sub.2 -C.sub.16 alkoxyalkyl group; X.sup.1, X.sup.2, X.sup.3, X.sup.4, Y.sup.1, Y.sup.2, Y.sup.3 and Y.sup.4 are independently from each other a --CH-- group, a --CF-- group or a nitrogen atom;A is a hydrogen atom, a fluorine atom, a trifluoromethyl group, a trifluoromethoxy group, a cyano group, a 4-R.sup.1 -(cycloalkyl) group, 4-R.sup.1 -(cycloalkenyl) group or a R.sup.1 --(O).sub.m group in which R.sup.1 is a C.sub.1 -C.sub.12 alkyl group, a C.sub.2 -C.sub.12 alkenyl group or a C.sub.2 -C.sub.12 alkynyl group; and m is 0 or 1, which has an excellent anisotropy of refractive index and a low viscosity and is useful as a component of a liquid crystal composition.
    Type: Grant
    Filed: October 13, 1994
    Date of Patent: August 19, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashii, Yukari Fujimoto, Masayoshi Minai, Tsutomu Matsumoto
  • Patent number: 5653911
    Abstract: A novel liquid crystalline compound having a high elastic constant ratio (K.sub.33 /K.sub.11) and an improved solubility thereof in other liquid crystal materials, at low temperatures, and a liquid crystal composition containing the same are provided. The liquid crystalline compound is expressed by the formula (1): ##STR1## wherein Q represents CF.sub.3, CF.sub.2 H or CFH.sub.2 ; A.sub.1, A.sub.2 and A.sub.3 each independently represent trans-1,4-cyclohexylene group, 1,4-phenylene group, wherein one or more hydrogen atoms on its six-membered ring may be replaced by F, Cl or CN, pyridine-2,5-diyl group or 1,3-pyrimidine-2,5-diyl; ring B represents 1,4-phenylene group or trans-1,4-cyclohexylene group; Z.sub.1, Z.sub.2 and Z.sub.3 each independently represent covalent bond, --C.dbd.C--, --C.tbd.C--, --OCO--, --COO--, --CH.sub.2 O--, --OCH.sub.2 --, --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.4 --; l and m each independently represent an integer of 0 to 5; o and p each independently represent 0 or 1; L.sub.1 and L.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: August 5, 1997
    Assignee: Chisso Corporation
    Inventors: Tomoyuki Kondo, Kazutoshi Miyazawa, Atsuko Fujita, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
  • Patent number: 5651919
    Abstract: Disclosed are a benzyl ether derivative represented by the following formula (I), useful as a liquid crystal display material, and a liquid crystal composition containing the same and a liquid crystal display device utilizing the composition. ##STR1## [wherein A represents a 4-alkylcyclohexyl group or an alkyl group, B represents a di- or tri-fluorophenyl group, a 4-(di- or tri-fluorophenyl)phenyl group, a 4-alkylphenyl group or a 4-alkoxyphenyl group].The compound (I) of the present invention has good compatibility with other compounds, and can be used in a liquid crystal composition by combining with many liquid crystal materials as a constitutional component of the liquid crystal composition. It has functions of lowering a C-N point of a liquid crystal composition, lowering a threshold voltage by enlarging a dielectric anisotropy, and also lowering a viscosity and increasing a N-I point of the liquid crystal composition.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: July 29, 1997
    Assignee: Citizen Watch Co., Ltd.
    Inventors: Tomijiro Naito, Yumiko Sakamaki, Hisato Sato
  • Patent number: 5648567
    Abstract: The new fluoro-trifluoromethylbenzoic acid derivatives of the general formula (I) ##STR1## wherein the substituents R, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meaning given in the description, are suitable as starting substances for the preparation of antibacterial agents and feed additives.
    Type: Grant
    Filed: August 14, 1995
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Peter Andres
  • Patent number: 5643495
    Abstract: 1,2,2,2-Tetrafluoroethyl ethers of the formula IR--(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Z.sup.2 A.sup.3 --O--CHF--CF.sub.3(I)are suitable as components of liquid-crystalline media whereinR is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: July 1, 1997
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Ekkehard Bartmann, Ulrich Finkenzeller
  • Patent number: 5637257
    Abstract: Disclosed are compounds of formula I ##STR1## wherein R is C.sub.1-12 -alkyl or halogenoalkyl wherein one or two non-adjacent CH.sub.2 groups are optionally replaced by --O--,A is ##STR2## Q is a bivalent radical of formula (2), and L.sup.0, L.sup.1 and L.sup.2 are each independently H or F, with the proviso that at least one of L.sup.0, L.sup.1 and L.sup.2 present in the molecule denotes F.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: June 10, 1997
    Assignee: Merck Patent Gesellschaft MLT Beschrankter Haftung
    Inventors: David Coates, Ian C. Sage, Simon Greenfield, Graham Smith, David W. Baxter
  • Patent number: 5589102
    Abstract: 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: Grant
    Filed: September 5, 1995
    Date of Patent: December 31, 1996
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ekkehard Bartmann, Kazuaki Tarumi
  • Patent number: 5585036
    Abstract: This invention provides chiral nonracemic compounds of general formula I which are useful as components of FLC compositions in SSFLC and DHFLC devices: ##STR1## wherein Z is a C.dbd.O group or a CH.sub.2 group, R.sub.F is a partially or fully fluorinated alkyl or alkenyl group, R.sub.2 is selected from an alkyl, alkenyl or alkynyl group in which one or more CH.sub.2 groups can optionally be substituted with one or two halogen atoms or in which one or more non-neighboring CH.sub.2 can be replaced with an O, S or an alkyl silyl group, S.sub.1 (R.sub.A)(R.sub.B), in which R.sub.A and R.sub.B, independently of one another, are small alkyl or alkenyl groups having from one to six carbon atoms, * indicates the chiral carbon and where Ar can be a one, two, or three aromatic ring LC core moieties. In particular, the core can have one to three, aromatic rings which are optionally linked by linking groups including O, S, CH.sub.2 S, SCH.sub.2, CH.sub.2 CH.sub.2, CH.sub.2 O, OCH.sub.2, CH.sub.2 CO.sub.2, CH.sub.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 17, 1996
    Assignee: Displaytech, Inc.
    Inventors: Michael D. Wand, Kundalika M. More, William N. Thurmes
  • Patent number: 5582767
    Abstract: The invention relates to liquid crystalline, multiply-substituted fluorinated tolane derivatives, their preparation, liquid crystalline mixtures which comprise such compounds and the use of these compounds and mixtures for electro-optical purposes.
    Type: Grant
    Filed: November 8, 1993
    Date of Patent: December 10, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Martin Schadt
  • Patent number: 5565140
    Abstract: The invention relates to novel halogenated benzene derivatives of the formula I ##STR1## in which n is 1 to 7 [sic], the rings A and B are each trans-1,4-cyclohexylene, or one of the rings A and B is alternatively 1,4-phenylene or 3-fluoro-l,4-phenylene, X is F, C1, CHF.sub.2, --CF.sub.3, --CN, --OCF.sub.3 or --OCHF.sub.2, Y and Z are each, independently of one another, H or F, r=1 or, in the case where s=1, B=trans-1,4-cyclohexylene and simultaneously X=--CHF.sub.2, --CF.sub.3, --OCF.sub.3 or --OCHF.sub.2, r is alternatively 0, and s=1 or, in the case where B=1,4-phenylene or 3-fluoro-1,4-phenylene, s=0.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: October 15, 1996
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Reinhard Hittich, Eike Poetsch, Volker Reiffenrath, Bernhard Rieger, Andreas Wachtler, David Coates, Herbert Plach
  • Patent number: 5565612
    Abstract: The present invention relates to substituted 2-chloro-3,4,5-trifluorobenzenes of the formula ##STR1## in which R is NO.sub.2, NH.sub.2, CN or Cl, and to a process for the preparation of substituted 2-chloro-3,4,5-trifluorobenzenes of the formula given above, in which R is NO.sub.2, NH.sub.2, CN, Cl or Br, which involves reacting 2,3,4-trifluorochlorobenzene with a nitrating agent in the presence or absence of a water-insoluble solvent at from -10.degree. C. to 50.degree. C., reducing 2-chloro-3,4,5-trifluoronitrobenzene or a mixture which contains 2-chloro-3,4,5-trifluoronitrobenzene and 5-chloro-2,3,4-trifluoronitrobenzene, in the presence of an organic solvent, isolating 2-chloro-3,4,5-trifluoroaniline or a mixture which contains 2-chloro-3,4,5-trifluoroaniline and 5-chloro-2,3,4-trifluoroaniline, diazotizing this product, if desired, and exchanging the diazotized group for a chloride atom, bromide atom or cyanide radical.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: October 15, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Thomas Schach
  • Patent number: 5545768
    Abstract: 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: Grant
    Filed: December 22, 1992
    Date of Patent: August 13, 1996
    Assignee: Hoechet AG
    Inventors: Theodor Papenfhus, Andreas Kanschik-Conradsen, Wilfried Pressler
  • Patent number: 5545769
    Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: August 13, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
  • Patent number: 5536442
    Abstract: The invention relates to liquid crystal compounds having a terminal structure in accordance with formula 1, 2, 3 or 4:--A.sup.3 --OCF.sub.3 1--A.sup.2 --Q--CHF.sub.2 2--3,5-difluoro-1,4-phenylene-X.sup.1 3--3-fluoro-1,4-phenylene-X.sup.2 4wherein A.sup.2, A.sup.3, X.sup.1 and X.sup.2 and are defined herein. The invention further relates liquid crystal phases containing the above components as well as electrooptical displays containing same.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: July 16, 1996
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Hans A. Kurmeier, Eike Poetsch, Herbert Plach, Ulrich Finkenzeller, Ekkehard Bartmann, Joachim Krause, Bernhard Scheuble, Dieter Dorsch, Georg Weber
  • Patent number: 5536892
    Abstract: A process for the preparation of octafluoro-[2,2]paracyclophane includes contacting a reactant selected from the group consisting of 1,4-bis (bromodifluoromethyl)benzene (dibromide), 1,4-bis (chlorodifluoromethyl)benzene (dichloride), and 1,4-bis (iododifluoromethyl)benzene (diiodide) with trimethylsilyltributyltin (TMSTBT) (a reducing agent) and fluoride ions in a refluxing solution of hexamethylphosphoramide (HMPA) or dimethylsulfoxide (DMSO) in tetrahydrofuran (THF) at conditions effective to promote a reaction product comprising octafluoro-[2,2]paracyclophane.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: July 16, 1996
    Assignee: Specialty Coating Systems, Inc.
    Inventors: William R. Dolbier, Jr., Xiao X. Rong
  • Patent number: 5534187
    Abstract: A liquid crystalline compound expressed by the formula ##STR1## wherein R.sub.1 represents an alkyl group of 1 to 12 carbon atoms, and one or two not adjacent CH.sub.2 group excluding the terminal in this group may be replaced by --CO-- group, --OCO-- group, --COO-- group or --CH.dbd.CH group; X and Z each represents H, F or Cl; Y represents perfluoroalkyl group or perfluoroalkyloxy group of 1 to 4 carbon atoms, and one or two F atoms in this group may be replaced by H; one of A, B and C represents cyclohexene ring and the others thereof are chosen from among covalent bond or cyclohexane group and benzene ring and these rings may be substituted by F or Cl; and l, m and n each are 0 or 1, independently of each other, but when m=0, then l=0. It is possible to provide a liquid crystal composition having a large .DELTA.n, a low viscosity and a high voltage-holding ratio, and exhibiting a nematic liquid crystal phase within a broad temperature range and having a very high .DELTA..epsilon.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: July 9, 1996
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
  • Patent number: 5502260
    Abstract: Multiply, preferably doubly or triply, fluorinated nitrobenzenes are prepared in an advantageous way from the corresponding chloronitrobenzenes and an alkali metal fluoride in a chlorine-fluorine exchange reaction by catalyzing the reaction with a quaternary ammonium compound comprising at least one alkoxypolyoxyalkyl radical.
    Type: Grant
    Filed: July 19, 1994
    Date of Patent: March 26, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5498807
    Abstract: The invention relates to a process for the preparation of aromatic fluoro compounds of the formula IF.sub.n ArR.sup.1 R.sup.2 R.sup.3 (I)in which Ar is phenyl, naphthyl or pyridyl, R.sup.1, R.sup.2 and R.sup.3 independently of one another are hydrogen, halide, (C.sub.1 -C.sub.4)-alkyl, phenyl, NR.sub.2, OR, CN, COH or COR, where R is hydrogen or (C.sub.1 -C.sub.6)-alkyl, and n=1, 2, 3, 4 or 5,which comprises reacting aromatic fluoro compounds of the formula IIX.sub.m F.sub.n ArR.sup.1 R.sup.2 R.sup.3 (II)in which Ar, R.sup.1, R.sup.2, R.sup.3 and n have the abovementioned meaning, each X is a chlorine or bromine atom and m=1, 2, 3, 4 or 5, with hydrogen in the presence of a palladium catalyst, a water-insoluble amine which also does not form water-soluble hydrohalides, and if desired an inert solvent.
    Type: Grant
    Filed: November 9, 1994
    Date of Patent: March 12, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5487846
    Abstract: A general-purpose organic rust initiator which can effectively prevent corrosion of metals comprising a compound of formula (1): ##STR1## wherein R.sub.1 is a perfluoroalkyl group having 1 to 6 carbon atoms; R.sub.2 is a hydrogen atom or a group defined for R.sub.1 ; R.sub.4 is an acid group selected from --OH, --COOH, --SH, --SO.sub.2 OH, --PO(OH).sub.2, --SCH.sub.2 COOH, --SO.sub.2 NHCH.sub.2 COOH or a salt thereof; R.sub.3 is a hydrogen atom or a group defined for R.sub.4 ; or R.sub.3 and R.sub.4 together form an acid group selected from --N.dbd.N--NH--, --CH.dbd.N--N--, --SO.sub.2 --NH--CO--, --S--C(SH).dbd.N-- or a salt thereof.
    Type: Grant
    Filed: October 4, 1994
    Date of Patent: January 30, 1996
    Assignee: Union Chemical Co., Ltd.
    Inventor: Shigeru Otomo
  • Patent number: 5484551
    Abstract: Compounds containing a 4-[(E)-alk-2-enoyloxy]benzoate group and liquid crystalline mixtures which contain such compounds and the use of such compounds and, respectively, mixtures in electro-optical indicating devices.The compounds are of the formula ##STR1## wherein R.sup.1 is alkyl with 1 to 12 carbon atoms;X.sup.1, X.sup.3 each independently are halogen or hydrogen; andX.sup.2 is halogen or cyano.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: January 16, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Stephen Kelly, Martin Schadt
  • Patent number: 5478964
    Abstract: The invention describes N-fluorosulfonimides which are useful as fluorinating agents. The N-fluorosulfonimides are stable, easily synthesized, and allow the introduction of fluorine into organic compounds under mild conditions.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: December 26, 1995
    Assignee: Allied-Signal Inc.
    Inventor: Edmond Differding
  • Patent number: 5476976
    Abstract: Fluoronitrobenzenes are prepared in an advantageous way from the corresponding chloronitrobenzenes and an alkali metal fluoride by means of a chlorine-fluorine exchange reaction with replacement of a chlorine atom by a fluorine atom, by catalyzing the reaction with a quaternaryammonium compound which comprises at least one alkoxypolyoxyalkyl radical.
    Type: Grant
    Filed: July 19, 1994
    Date of Patent: December 19, 1995
    Assignee: Hoechst AG
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5468421
    Abstract: A liquid crystalline compound which has a low viscosity and is electrically and chemically stable and compatible with other known liquid crystalline compounds at low temperatures, and a liquid crystal composition containing the same, which compound is a phenyl-4-cyclohexylbutylcyclohexane derivative expressed by the formula: ##STR1## wherein R represents a hydrogen atom or a linear or branched alkyl group of 1 to 15 carbon atoms, and X.sub.1, X.sub.2 and X.sub.3 are each independent and X.sub.1 and X.sub.3 each represent a hydrogen atom or a halogen atom and X.sub.2 represents a hydrogen atom or a linear or branched alkyl group of 1 to 15 carbon atoms (wherein one --CH.sub.2 CH.sub.2 -- bond may be replaced by a --CH.dbd.CH-- bond and one non-adjacent --CH.sub.2 -- bond may be replaced by an oxygen atom), a halogen atom, a cyano group, a trifluoromethyl group or a trifluoromethoxy group.
    Type: Grant
    Filed: April 28, 1993
    Date of Patent: November 21, 1995
    Assignee: Chisso Corporation
    Inventors: Shuichi Matsui, Yasuyuki Goto, Yuichi Onji, Atsuko Fujita
  • Patent number: 5453218
    Abstract: This invention provides chiral nonracemic compounds of formula ##STR1## wherein * indicates a chiral carbon, R.sub.1 and R.sub.2, independently of one another, can be an alkyl, alkenyl or alkynyl group wherein one or more non-neighboring CH.sub.2 groups can be replaced with an O, S or a silyl group (R.sub.A SiR.sub.B) wherein R.sub.A and R.sub.B, independently of one another, are alkyl or alkenyl having from one to six carbon atoms; R.sub.1 having from about 3 to 20 carbon atoms, and R.sub.2 having from 1 to about 18 carbon atoms; X is O, S, CO, COO, OCO, COS or a single bond where Ar is a liquid crystal core moiety having two or three aromatic rings of the formula--(Cyc).sub.n --(A).sub.a --Ph.sub.1 --(B).sub.b --Ph.sub.2 --(C).sub.c --(Ph.sub.3).sub.m --whereinPh.sub.1, Ph.sub.2 and Ph.sub.
    Type: Grant
    Filed: February 8, 1994
    Date of Patent: September 26, 1995
    Assignee: Displaytech, Inc.
    Inventors: Michael D. Wand, Kundalika M. More, William N. Thurmes
  • Patent number: 5449831
    Abstract: 2-methyl-3-aminobenzo-trifluoride is prepared with high yields and high productivity by first halogenating o-trifluoromethylbenzalhalide, then secondly hydrogenating 2-trifluoromethyl-4-halogeno-benzalhalide formed by the first reaction, then thirdly nitrating 2-methyl-monohalogenobenzotrifluoride formed by the second reaction, and then fourthly hydrogenating 2-methyl-3-nitro-5-halogenobenzotrifluoride formed by the third reaction.
    Type: Grant
    Filed: January 5, 1994
    Date of Patent: September 12, 1995
    Assignee: Central Glass Company, Limited
    Inventors: Takayuki Nishimiya, Masatomi Kanai, Toshikazu Kawai
  • Patent number: 5447657
    Abstract: The present invention provides compounds of the general formula: ##STR1## wherein R is an alkyl group with 1 to 12 carbon atoms or a group of the formula ##STR2## Ring A.sup.1 is 1,4-phenylene, which is unsubstituted or substituted with fluorine, pyridine-2,5-diyl or pyrimidine-2,5-diyl;Ring A.sup.2 is trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;R.sup.1 is an alkyl, alkenyl or alkoxyalkyl group with 1 to 12 and, respectively, 2 to 12 carbon atoms;X.sup.1 is fluorine, chlorine, bromine, trifluoromethyl, trifluoromethoxy or difluoromethoxy; andX.sup.2, X.sup.3 each independently are hydrogen or fluorine.The invention is also concerned with liquid crystal mixtures which contain these compounds and with the use of these compounds and mixtures for electro-optical purposes.
    Type: Grant
    Filed: March 8, 1994
    Date of Patent: September 5, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Schadt, Alois Villiger
  • Patent number: 5445764
    Abstract: The invention relates to methylenecyclobutane benzene derivatives of the formula I ##STR1## in which R.sup.1, A.sup.1, Z.sup.1, L.sup.1, L.sup.2, m, V, W, Y and n have the meaning given in claim 1, and to their use as components of liquid-crystalline media for electrooptical displays.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: August 29, 1995
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Eike Poetsch, Werner Binder, Volker Meyer, Ulrich Finkenzeller, Bernhard Rieger
  • Patent number: 5437815
    Abstract: A tolan derivative of a formula: ##STR1## where R represents a linear alkyl group having from 1 to 10 carbon atoms; X.sub.1, X.sub.2 and X.sub.3 independently represent a fluorine atom or a hydrogen atom, provided that one of them is necessarily a fluorine atom and the others are hydrogen atoms; and Y represents a nitrile group or a linear alkyl group having from 1 to 10 carbon atoms; and a liquid crystal composition containing the derivatives; and a liquid crystal display device having the composition are produced. The compound is compatible with other liquid crystal compounds, and by blending the compound with ordinary liquid crystal compounds, a liquid crystal composition having a broadened practical temperature range and an enlarged double refraction anisotropy is obtained.
    Type: Grant
    Filed: September 29, 1992
    Date of Patent: August 1, 1995
    Assignee: Seiko Epson Corporation
    Inventors: Shuhei Yamada, Shuji Ikukawa, Jitsuko Nakayama
  • Patent number: 5422035
    Abstract: A liquid-crystalline medium based on a mixture of polar compounds having positive dielectric anisotropy, comprising one or more compounds of the formula I ##STR1## in which R, A.sup.1,. A.sup.2, Z.sup.1, Z.sup.2, m, n, L.sup.1, L 2 and L.sup.3 are as defined in claim 1.
    Type: Grant
    Filed: May 9, 1994
    Date of Patent: June 6, 1995
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ekkehard Bartmann, Herbert Plach, Andreas Ruhl
  • Patent number: 5419851
    Abstract: The present invention provides a difluoro-derivative compound of the formula R.sup.1 --(A.sup.1 --Y.sup.1).sub.m --A.sup.2 --CF.dbd.CF--C.tbd.C--A.sup.3 --(Y.sup.2 --A.sup.4).sub.n --R.sup.2 (wherein each of A.sup.1 to A.sup.4 is a trans-1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group, each of m and n is 0 or 1, and each of R.sup.1 and R.sup.2 is a C.sub.1-10 alkyl group, a halogen atom or a cyano group).The compound of the present invention has a low viscosity and is stable against lights, and a high speed response is expected by using it for a liquid crystal composition.
    Type: Grant
    Filed: April 20, 1994
    Date of Patent: May 30, 1995
    Assignee: Asahi Glass Company Ltd.
    Inventors: Osamu Yokokoji, Jun Irisawa, Hidemasa Koh
  • Patent number: 5399292
    Abstract: Fluoro-substituted phenyl-cyclohexylacetylenes have the formula: ##STR1## wherein R signifies alkyl, alkoxy, alkenyl or alkenyloxy with 1 or, respectively, 2 to 12 carbon atoms in which one CH.sub.2 group can be replaced by oxygen and/or one or more hydrogen atoms can be replaced by fluorine atoms, with the proviso that two oxygen atoms are not directly adjacent;A.sup.1 represents 1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;A.sup.2 signifies trans-1,4-cyclohexylene or 1,4-phenylene which is optionally substituted with fluorine;Z.sup.1 signifies a single covalent bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.4 --, --O(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 O-- or, when ring A.sup.1 represents a saturated ring, also the trans form of --CH.dbd.CH(CH.sub.2).sub.2 -- or --CH.dbd.CHCH.sub.2 O--;Z.sup.2 signifies a single covalent bond, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O--, --(CH.sub.2).sub.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: March 21, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Martin Schadt