Benzene Ring Containing Patents (Class 570/127)
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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: 5792892Abstract: 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: GrantFiled: October 22, 1996Date of Patent: August 11, 1998Assignee: Bayer AktiengesellschaftInventor: Hermann Hagemann
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Patent number: 5789634Abstract: 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: GrantFiled: February 5, 1997Date of Patent: August 4, 1998Assignee: Boulder Scientific CompanyInventors: Jeffrey M. Sullivan, Hamlin H. Barnes
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Patent number: 5780672Abstract: 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: GrantFiled: July 11, 1996Date of Patent: July 14, 1998Assignee: Hoechst AktiengesellschaftInventors: Sergej Pasenok, Wolfgang Appel
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Patent number: 5776367Abstract: 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: GrantFiled: June 19, 1996Date of Patent: July 7, 1998Assignee: Chisso CorporationInventors: Shuichi Matsui, Yasuyuki Koizumi, Takashi Kato, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 5777181Abstract: 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: GrantFiled: April 10, 1996Date of Patent: July 7, 1998Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Uwe Petersen, Klaus Grohe
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Patent number: 5763699Abstract: 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: GrantFiled: November 27, 1996Date of Patent: June 9, 1998Assignee: Nippon Mektron, LimitedInventors: Lev Solomonovich German, deceased, Valerii Romanovich Polishchuk, deceased, Riichi Iwa, Haruyoshi Tatsu
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Patent number: 5760282Abstract: 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: GrantFiled: June 2, 1995Date of Patent: June 2, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Richard Paul Beatty, William Brown Farnham, Robert Lewis Wallace, Jr.
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Patent number: 5760255Abstract: 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: GrantFiled: June 25, 1996Date of Patent: June 2, 1998Assignee: Bayer AGInventors: Helmut Vorbruggen, Barbel Bennua-Skalmowski
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Patent number: 5756834Abstract: 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: GrantFiled: November 7, 1996Date of Patent: May 26, 1998Assignee: Hoechst AktiengesellschaftInventors: Sergej Pasenok, Wolfgang Appel
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Patent number: 5739361Abstract: 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: GrantFiled: April 23, 1997Date of Patent: April 14, 1998Assignee: Proteos S.r.L.Inventors: Angelo Signor, Alfredo Guerrato, Giovanni Signor
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Patent number: 5739388Abstract: 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: GrantFiled: May 2, 1996Date of Patent: April 14, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Hans Schubert
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Patent number: 5720899Abstract: 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: GrantFiled: December 30, 1996Date of Patent: February 24, 1998Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Kazutoshi Miyazawa, Atsuko Fujita, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5714088Abstract: 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: GrantFiled: March 22, 1996Date of Patent: February 3, 1998Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuko Sekiguchi, Etsuo Nakagawa
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Patent number: 5693261Abstract: 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: GrantFiled: August 9, 1995Date of Patent: December 2, 1997Assignee: Albemarle CorporationInventors: Niomi L. Krzystowczyk, Steven P. Diefenbach, Wendy L. Lemoine
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Patent number: 5679285Abstract: 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: GrantFiled: February 15, 1996Date of Patent: October 21, 1997Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Sabine Schoen, Kazuaki Tarumi
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Patent number: 5672765Abstract: 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: GrantFiled: July 14, 1995Date of Patent: September 30, 1997Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Marianne Lohr, Heinrich Wamhoff
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Patent number: 5670085Abstract: 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: GrantFiled: January 18, 1996Date of Patent: September 23, 1997Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5665270Abstract: 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: GrantFiled: May 4, 1994Date of Patent: September 9, 1997Assignee: Chisso CorporationInventors: Masatoshi Fukushima, Shinichi Saito
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Patent number: 5658489Abstract: 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: GrantFiled: October 13, 1994Date of Patent: August 19, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Yukari Fujimoto, Masayoshi Minai, Tsutomu Matsumoto
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Patent number: 5653911Abstract: 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: GrantFiled: April 27, 1995Date of Patent: August 5, 1997Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Kazutoshi Miyazawa, Atsuko Fujita, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5651919Abstract: 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: GrantFiled: February 23, 1996Date of Patent: July 29, 1997Assignee: Citizen Watch Co., Ltd.Inventors: Tomijiro Naito, Yumiko Sakamaki, Hisato Sato
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Patent number: 5648567Abstract: 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: GrantFiled: August 14, 1995Date of Patent: July 15, 1997Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Peter Andres
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Patent number: 5643495Abstract: 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: GrantFiled: September 12, 1995Date of Patent: July 1, 1997Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Ekkehard Bartmann, Ulrich Finkenzeller
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Patent number: 5637257Abstract: 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: GrantFiled: June 5, 1995Date of Patent: June 10, 1997Assignee: Merck Patent Gesellschaft MLT Beschrankter HaftungInventors: David Coates, Ian C. Sage, Simon Greenfield, Graham Smith, David W. Baxter
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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: 5585036Abstract: 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: GrantFiled: June 5, 1995Date of Patent: December 17, 1996Assignee: Displaytech, Inc.Inventors: Michael D. Wand, Kundalika M. More, William N. Thurmes
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Patent number: 5582767Abstract: 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: GrantFiled: November 8, 1993Date of Patent: December 10, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt
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Patent number: 5565140Abstract: 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: GrantFiled: June 5, 1995Date of Patent: October 15, 1996Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Reinhard Hittich, Eike Poetsch, Volker Reiffenrath, Bernhard Rieger, Andreas Wachtler, David Coates, Herbert Plach
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Patent number: 5565612Abstract: 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: GrantFiled: May 5, 1995Date of Patent: October 15, 1996Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Thomas Schach
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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: 5545769Abstract: 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: GrantFiled: September 29, 1994Date of Patent: August 13, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
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Patent number: 5536442Abstract: 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: GrantFiled: July 6, 1992Date of Patent: July 16, 1996Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Hans A. Kurmeier, Eike Poetsch, Herbert Plach, Ulrich Finkenzeller, Ekkehard Bartmann, Joachim Krause, Bernhard Scheuble, Dieter Dorsch, Georg Weber
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Patent number: 5536892Abstract: 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: GrantFiled: October 18, 1995Date of Patent: July 16, 1996Assignee: Specialty Coating Systems, Inc.Inventors: William R. Dolbier, Jr., Xiao X. Rong
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Patent number: 5534187Abstract: 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: GrantFiled: March 24, 1995Date of Patent: July 9, 1996Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5502260Abstract: 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: GrantFiled: July 19, 1994Date of Patent: March 26, 1996Assignee: Hoechst AktiengesellschaftInventors: Thomas Schach, Theodor Papenfuhs
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Patent number: 5498807Abstract: 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: GrantFiled: November 9, 1994Date of Patent: March 12, 1996Assignee: Hoechst AktiengesellschaftInventors: Thomas Schach, Theodor Papenfuhs
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Patent number: 5487846Abstract: 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: GrantFiled: October 4, 1994Date of Patent: January 30, 1996Assignee: Union Chemical Co., Ltd.Inventor: Shigeru Otomo
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Patent number: 5484551Abstract: 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: GrantFiled: May 12, 1995Date of Patent: January 16, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Stephen Kelly, Martin Schadt
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Patent number: 5478964Abstract: 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: GrantFiled: December 10, 1992Date of Patent: December 26, 1995Assignee: Allied-Signal Inc.Inventor: Edmond Differding
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Patent number: 5476976Abstract: 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: GrantFiled: July 19, 1994Date of Patent: December 19, 1995Assignee: Hoechst AGInventors: Thomas Schach, Theodor Papenfuhs
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Patent number: 5468421Abstract: 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: GrantFiled: April 28, 1993Date of Patent: November 21, 1995Assignee: Chisso CorporationInventors: Shuichi Matsui, Yasuyuki Goto, Yuichi Onji, Atsuko Fujita
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Patent number: 5453218Abstract: 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: GrantFiled: February 8, 1994Date of Patent: September 26, 1995Assignee: Displaytech, Inc.Inventors: Michael D. Wand, Kundalika M. More, William N. Thurmes
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Patent number: 5449831Abstract: 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: GrantFiled: January 5, 1994Date of Patent: September 12, 1995Assignee: Central Glass Company, LimitedInventors: Takayuki Nishimiya, Masatomi Kanai, Toshikazu Kawai
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Patent number: 5447657Abstract: 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: GrantFiled: March 8, 1994Date of Patent: September 5, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Martin Schadt, Alois Villiger
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Patent number: 5445764Abstract: 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: GrantFiled: July 20, 1994Date of Patent: August 29, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Eike Poetsch, Werner Binder, Volker Meyer, Ulrich Finkenzeller, Bernhard Rieger
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Patent number: 5437815Abstract: 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: GrantFiled: September 29, 1992Date of Patent: August 1, 1995Assignee: Seiko Epson CorporationInventors: Shuhei Yamada, Shuji Ikukawa, Jitsuko Nakayama
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Patent number: 5422035Abstract: 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: GrantFiled: May 9, 1994Date of Patent: June 6, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach, Andreas Ruhl
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Patent number: 5419851Abstract: 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: GrantFiled: April 20, 1994Date of Patent: May 30, 1995Assignee: Asahi Glass Company Ltd.Inventors: Osamu Yokokoji, Jun Irisawa, Hidemasa Koh
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Patent number: 5399292Abstract: 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: GrantFiled: May 2, 1994Date of Patent: March 21, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt