Halogen Containing Patents (Class 568/661)
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Publication number: 20030069433Abstract: The invention relates to a process for the preparation of compounds having at least one —CF2O— bridge in the molecule, which comprises initially reacting a bis(alkylthio)carbenium salt with a compound containing at least one hydroxyl group in the presence of a base followed by oxidative fluorination, preferably in situ, with a fluorinating agent and an oxidizing agent to form the compound having at least one —CF2O— bridge in the molecule.Type: ApplicationFiled: September 3, 2002Publication date: April 10, 2003Inventors: Peer Kirsch, Andreas Taugerbeck, Detlef Pauluth, Matthias Bremer
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Patent number: 6515163Abstract: The invention concerns hydrogenated phenanthrenes of formula I wherein the parameters have the meanings given in the text and their use in liquid crystal compositions.Type: GrantFiled: June 8, 2001Date of Patent: February 4, 2003Assignee: Merck Patent GesellschaftInventors: Rainer Wingen, Barbara Hornung, Wolfgang Schmidt
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Publication number: 20020183540Abstract: The present invention seeks to provide novel tetraarylethylene compounds which are substituted on the aryl rings ortho to the ethylenic carbon atoms and processes for the preparation for such compounds. The compounds have potential use as molecular templates.Type: ApplicationFiled: June 21, 2002Publication date: December 5, 2002Applicant: THE GOVERNORS OF THE UNIVERSITY OF ALBERTAInventors: Jeffrey Mark Stryker, Udo Hendrick Verkerk, Megumi Fujita, Makoto Yasuda
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Publication number: 20020120168Abstract: The present invention provides a difluoromethyl ether derivative which shows various suitable physical properties as a liquid crystal compound, a liquid crystal composition comprising the compound and a liquid crystal display element containing the composition, and also provides a simple and efficient process for producing the difluoromethyl ether derivative.Type: ApplicationFiled: August 10, 2001Publication date: August 29, 2002Inventors: Tomoyuki Kondo, Kouki Sagou, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
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Publication number: 20020062049Abstract: A two-step process for the preparation of fluoroolefin compounds of formula I 1Type: ApplicationFiled: September 12, 2001Publication date: May 23, 2002Applicant: BASF AktiengesellschaftInventor: William Wakefield Wood
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Patent number: 6388146Abstract: The polymerizable compound of this invention is represented by general formula (I): where R is H, R′, R′O, R′COO, or R′OCO, R′ is a linear or branched alkyl group or alkenyl group having 1 to about 15 carbon atoms, A1 and A2 are independently a cyclohexane ring or a benzene ring which may include a substituent represented by formula (II) below; X is H or CH3; and Y1, Y2, Y3, and Y4 are independently H, F, Cl, CH3, CH3O, CF3, or CF3O wherein at least two of Y1, Y2, Y3, and Y4 are H and, if both A1 and A2 are cyclohexane rings, at least one of Y1, Y2, Y3, and Y4 is not H: where Y5, Y6, Y7, and Y8 are independently H, F, Cl, CH3, CH3O, CF3, or CF3O, at least two of Y5, Y6, Y7, and Y8 are H.Type: GrantFiled: January 27, 1999Date of Patent: May 14, 2002Assignees: Sharp Kabushiki Kaisha, Kanto Kagaku Kabushiki KaishaInventors: Noriaki Onishi, Aya Miyazaki, Hoyo Mizobe, Masahiko Yoshida, Kenji Suzuki
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Patent number: 6344247Abstract: The present invention provides liquid crystalline compounds having a high voltage holding ratio and a low threshold voltage, little variation of these properties depending on temperature change, high &Dgr;n, and good compatibility with other liquid crystal materials particularly under a low temperature; liquid crystal compositions containing these crystalline compounds; and liquid crystal display devices comprising these liquid crystal compositions.Type: GrantFiled: March 25, 1999Date of Patent: February 5, 2002Assignee: Chisso CorporationInventors: Tomoyuki Kondou, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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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: 6320085Abstract: The subject matter of the invention is the process for the preparation of mixed ethers of formula I, wherein Ar represents an aromatic or one or more heteroatom-containing moiety, optionally substituted by one or more C1-4 alkoxy, methylenedioxy, C1-4 alkyl, halogen, C1-4 haloalkyl or nitro-group, and/or condensed with a benzene ring; R1 and R2 independently mean hydrogen, C1-4 alkyl, C1-4 haloalkyl, C2-4 alkenyl, phenyl, substituted phenyl, C3-6 cycloalkyl group, R3 means C3-6 alkynyl, optionally substituted by one or more C1-6 alkyl, C3-6 alkenyl, C3-6 alkynyl, C1-6 haloalkyl group, or halogen atom, R3 also means a C1-4 alkyloxy-C1-4 alkyloxy-C1-4 alkyl group.Type: GrantFiled: July 13, 1999Date of Patent: November 20, 2001Assignee: Agro-Chemie Novenyvedoszer Gyarto Ertekesito est Forgalmazo Kft.Inventors: Geza Arvai, Bela Bertok, Zsuzsanna Kuruczne Ribai, Laszlo Pap, Istvan Szekely
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Patent number: 6312618Abstract: A new class of asymmetric polar diphenyldiacetylene liquid crystal compounds and method for preparation are disclosed. The new class of liquid crystal compounds comprises the basic structure: Wherein R1 is an alkenyl group having the general formula (C2H2n−1), X is a cyano group, a fluoro group, CF3, OCF3, or a chloro group, Y1 is unsubstituted, a fluoro group, a chloro group or a methyl group, Y2 is unsubstituted, a fluoro group, a chloro group, or a methyl group, Z1 is unsubstituted, a fluoro group, or a methyl group, and Z2 is unsubstituted, a fluoro group, or a methyl group. The compounds disclosed exhibit high birefringence, low rotational viscosity, and have unexpectedly broad nematic ranges. Also disclosed are eutectic mixtures comprising at least one polar diphenyldiacetylene having the general structure described above. The eutectic mixtures also have unexpectedly broad nematic ranges.Type: GrantFiled: April 3, 2000Date of Patent: November 6, 2001Assignee: HRL LaboratoriesInventors: Shin-Tson Wu, Mary E. Neubert
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Patent number: 6291721Abstract: An improved process for the preparation of 2-arylvinyl alkyl ether compounds of the structural formula I In addition, the present invention provides an improved process for the preparation of 1,4-diaryl-2-fluoro-2-butene compounds of the structural formula VType: GrantFiled: August 12, 1999Date of Patent: September 18, 2001Assignee: American Cyanamid Co.Inventors: Yulin Hu, David Allen Hunt, Weiguo Liu
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Patent number: 6281250Abstract: The present invention is directed to retinyl ethers, derivatives and analogues and their use in inhibiting breast carcinogenesis or breast cancer cell growth.Type: GrantFiled: April 12, 1999Date of Patent: August 28, 2001Assignee: Southern Research InstituteInventor: Y. Fulmer Shealy
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Patent number: 6147224Abstract: Compounds of Formula 1, Formula 2 or Formula 3 where X is O, S, or (CR.sub.1 R.sub.1).sub.n where n is 0, 1 or 2; Y is a bivalent radical having Formula 4 or Formula 5 where o is an integer from 1 to 4 ##STR1## or Y is a bivalent aryl or 5 or 6 membered heteroaryl radical having 1 to 3 heteroatoms selected from N, S and O, said aryl or heteroaryl groups being unsubstituted, or substituted with 1 to 3 C.sub.1-6 alkyl or with 1 to 3 C.sub.1-6 fluoroalkyl groups; and the remaining symbols have the meaning described in the specification, have RXR selective retinoid agonist-like activity.Type: GrantFiled: October 1, 1998Date of Patent: November 14, 2000Assignee: Allergan Sales, Inc.Inventors: Vidyasagar Vuligonda, Kwok Yin Tsang, Jayasree Vasudevan, Roshantha A. Chandraratna
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Patent number: 6127579Abstract: A method of manufacturing the useful substance 1-indanone from easily obtainable materials consists of reacting an indanyl ether represented by the generic formula ##STR1## under basic conditions to give a novel substance which is the indenyl ether derivative represented by the generic formula ##STR2## and hydrolyzing this to give the 1-indanone represented by the generic formula ##STR3##Type: GrantFiled: July 1, 1999Date of Patent: October 3, 2000Assignee: Ichikawa Gosei Chemical Co., Ltd.Inventors: Shigeru Nakano, Noriko Yoneta, Takashi Tate
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Patent number: 6121330Abstract: The novel 5-hydroxy-alkyl-substituted phenyls are prepared by either reacting the corresponding benzaldehydes with the Grignard compounds and subsequently reducing the other functional groups or by reducing the corresponding benzoic esters by customary methods to give the corresponding hydroxyl compounds. The 5-hydroxy-alkyl-substituted phenyls are suitable for use as active compounds in medicaments, in particular for the treatment of dyslipidaemia.Type: GrantFiled: September 2, 1999Date of Patent: September 19, 2000Assignee: Bayer AktiengesellschaftInventors: Matthias Muller-Gliemann, Rolf Angerbauer, Arndt Brandes, Michael Logers, Carsten Schmeck, Gunter Schmidt, Klaus-Dieter Bremm, Hilmar Bischoff, Delf Schmidt
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Patent number: 6025310Abstract: The invention provides novel organic compounds, and more particularly those having excellent lubricity, compatible with lubricating organic compounds having a benzene ring and a phosphazine ring and retaining stability free of hydrolysis for a prolonged period of time. The organic compounds are represented by the formula R.sub.1 --R.sub.0 --R.sub.1 or R.sub.0 --R.sub.1. R.sub.0 is a chain saturated organic group containing a chain of carbon atoms or a chain of carbon atom C and oxygen atom O, and filled with fluorine atoms F or trifluoromethyl groups CF.sub.3 except at one end or both ends of the chain. R.sub.1 is --CH.sub.2 --O--(CH.sub.2).sub.p --{CH(CH.sub.3)}.sub.k --{C(CH.sub.3).sub.2 }.sub.t --R.sub.2 wherein p, k and t are each an integer of 0 or not smaller than 1, and R.sub.2 is phenyl or a functional group corresponding to phenyl in which at least one of the hydrogen atoms is substituted with a compound of at least two elements selected from the group consisting of C, H, O and F or with F, Br or Cl.Type: GrantFiled: March 23, 1998Date of Patent: February 15, 2000Assignee: Kubota CorporationInventors: Ikuzo Nishiguchi, Hiroki Hara, Sigeru Tsuboi, Seiki Sugi, Kazuhiro Higuchi
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Patent number: 5942648Abstract: Naphthalene derivatives of the fomula I ##STR1## in which: R.sup.1 is an alkyl or alkenyl radical which is unsubstituted, monosubstituted by CH or CF.sub.3 or monosubstituted by halogen and has 1 to 15 carbon atoms, it also being possible for one or more CH.sub.2 groups in these radicals to be replaced, in each case independently of one another, by --O--, --S--, ##STR2## --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in such a manner that oxygen atoms are not linked directly to one another, ##STR3## m is 0, 1 or 2, n is 0 or 1, wherem+n is 1 or 2,Z.sup.1 and Z.sup.2 are each, independently of one another, --CH.sub.2 CH.sub.2 --, --C.tbd.C-- or a single bond,L.sup.1 and L.sup.2 independently of one another, are H or F,x is an alkyl or alkoxy radical which is unsubstituted, monosubstituted by CN or CF.sub.3 or substituted bi halogen and has 1 to 15 carbon atoms, or is OH, CN, SCN, OCN, NCS or Q--Y,whereQ is a single bond, (CF.sub.2).sub.r or O(CF.sub.2).sub.Type: GrantFiled: March 4, 1997Date of Patent: August 24, 1999Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: David Coates, Mark Goulding, Simon Greenfield, Volker Reiffenrath, Reinhard Hittich, Herbert Plach
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Patent number: 5911912Abstract: Halovinyl ethers of the general formula I ##STR1## in which R, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2, X.sup.1, X.sup.2, l, m and n are as defined herein are suitable as components of liquid-crystalline media.Type: GrantFiled: November 20, 1997Date of Patent: June 15, 1999Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Peer Kirsch, Joachim Krause, Kazuaki Tarumi
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Patent number: 5763681Abstract: A novel synthesis of compound having the formula: ##STR1## wherein T is a stabilizing spiro-linked polycycloalkylidene group, R.sup.3 is a C.sub.1 -C.sub.20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromophore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula:(R.sup.1 O).sub.3 Pwherein R.sup.1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula:R.sup.3 OHwherein R.sup.Type: GrantFiled: July 2, 1993Date of Patent: June 9, 1998
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Patent number: 5693251Abstract: An optically active phenol useful in the preparation of liquid crystalline compounds which is represented by the formula (V): ##STR1## wherein R.sub.2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms optionally substituted by halogen atoms; Z' represents ##STR2## wherein q represents a number of 1 to 5 and * indicates asymmetric carbon atom; l represents a number of 2; t represents a number of 1 to 5; s represents a number of 0 or 1.Type: GrantFiled: November 23, 1994Date of Patent: December 2, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa
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Patent number: 5686020Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 denotes a linear or branched alkyl group having 1-18 carbon atoms capable of including one or non-neighboring two or more methylene groups which can be replaced with at least one species of ##STR2## with the proviso that X denotes O or S and Y denotes halogen; R.sub.2 denotes a linear or branched alkyl group having 1-18 carbon atoms; A, B and D independently denote ##STR3## wherein Z.sub.1 and Z.sub.2 independently denote hydrogen, halogen, --CH.sub.3, --CN or --CF.sub.3 ; E denotes --CH.sub.3, --CH.sub.2 F or --CF.sub.3 ; and f and g independently denote 0 or 1. The mesomorphic compound is effective for providing a ferroelectric liquid crystal composition showing an improved response speed and also effective for suppressing occurrence of reverse domain.Type: GrantFiled: May 15, 1995Date of Patent: November 11, 1997Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shinichi Nakamura, Koji Noguchi
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Patent number: 5541351Abstract: Processes are disclosed for preparing compounds of the formula Z--R--Z where each Z can be selected from cyclopentadienyl type radicals such as substituted or unsubstituted cyclopentadienyl, indenyl, fluorenyl or tetrahydroindenyl or where one Z is Cl, Br, or I by reacting specific Z precursors with a dihaloalkylene compound. Also new cyclopentadienyl-type compounds are disclosed.Type: GrantFiled: August 15, 1994Date of Patent: July 30, 1996Assignee: Phillips Petroleum CompanyInventors: Konstantinos Patsidis, Syriac J. Palackal, Helmut G. Alt
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Patent number: 5494605Abstract: The p-terphenyl derivatives of the formula shown below are useful in preparing practical ferroelectric liquid crystalline compositions. The derivatives exhibit excellent chemical stability and display the chiral smectic C or smectic C phase over a wide temperature range. ##STR1## wherein each of R.sub.1 and R.sub.2 is a straight or branched chain alkyl group having 1-18 carbon atoms; each of Y and Z is a single bond, O, COO or OCO; and any two of X.sub.1, X.sub.2, and X.sub.3 are fluorine atoms and the remainder is a hydrogen atom.Type: GrantFiled: November 24, 1993Date of Patent: February 27, 1996Assignee: Kanto Kagaku Kabushiki KaishaInventors: Makoto Kurihara, Hiromi Inoue, Atsushi Sugiura, Kenji Suzuki, Tsunenori Fujii
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Patent number: 5492917Abstract: Novel compounds of the general structural formula I: ##STR1## have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.Type: GrantFiled: September 29, 1993Date of Patent: February 20, 1996Assignee: Merck & Co., Inc.Inventors: Ralph A. Rivero, Peter D. Williams, Daniel F. Veber
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Patent number: 5457235Abstract: The present invention provides liquid crystals that are diphenyldiacetylenes of the general formulas: ##STR1## where W, X, Y and Z are, independently of one another, a halogen atom, a hydrogen atom or a trihalomethyl group, T.sub.1 and T.sub.2, independently of one another can be an alkyl, alkene, alkoxy, alkenoxy, ether, thioalkyl, thioalkenyl, haloalkyl, haloalkoxy or haloalkylether groups having from three to twenty carbon atoms or a silylalkyl, silylalkenyl, silylalkoxy or silylthioalkyl group having from three to twenty-eight carbon atoms and wherein M.sub.1 and M.sub.2 can both be single bonds or one of M.sub.1 or M.sub.2 can be a trans-1,4-cyclohexylene or a --CH.sub.2 CH.sub.2 -trans-1,4-cyclohexylene.Type: GrantFiled: January 11, 1993Date of Patent: October 10, 1995Assignee: Displaytech, Inc.Inventors: Michael D. Wand, Sean D. Monahan, William N. Thurmes, Kundalika M. More
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Process for producing (E)-alkoxyimino or hydroxyimino-acetamide compounds and intermediates therefor
Patent number: 5442063Abstract: The present invention relates to a process for producing (E)-alkoxyiminoacetamide compounds useful as agricultural fungicides and a process for producing (E)-hydroxyiminoacetamide compounds useful as intermediates for producing them. The present invention also relates to an industrial process for producing (E)-methoxyiminoacetamide compounds useful as agricultural fungicides. This process is advantageous in terms of the cost, safety and the like.Type: GrantFiled: November 2, 1993Date of Patent: August 15, 1995Assignee: Shionogi & Co., Ltd.Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Kuniyoshi Nishida -
Patent number: 5416243Abstract: Cyclofluoralkylated fullerene compounds are prepared by reacting the fullerenes with a fluoroalkene as exemplified by tetrafluoroethylene or perfluoromethyl vinyl ether under thermolysis conditions as exemplified by temperatures of 200.degree. C., pressure and a halocarbon solvent, the products being useful as lubricants or additive thereto as well as in cooling systems, adhesives and polymers.Type: GrantFiled: August 29, 1994Date of Patent: May 16, 1995Assignee: E. I. DuPont de Nemours and CompanyInventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
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Patent number: 5403512Abstract: Vinyl compounds of the formula I ##STR1## in which the variables are as described in the claims. The compounds are useful as components in liquid-crystalline media.Type: GrantFiled: August 5, 1992Date of Patent: April 4, 1995Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach, Rudolf Eidenschink, Volker Reiffenrath, Detlef Pauluth, Eike Poetsch, Sabine Schoen, Volker Meyer, Michael Junge, Reinhard Hittich
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Patent number: 5399689Abstract: The present invention is concerned with novel chlorophenylalkoxyalkyl compounds of the general formula ##STR1## wherein R denotes an alkyl residue with 1 to 12 carbon atoms; n is a whole number of 2 to 7, ring A denotes trans-1,4-cyclohexylene or 1,4-phenylene; m is either 0 or 1; ring B is trans-1,4-cyclohexylene, 1,4-phenylene in which optionally one CH group or two non-adjacent CH groups is/are replaced by nitrogen or, when m stands for 1, also trans-1,3-dioxane-2,5-diyl; Y.sup.1 and Y.sup.2 each independently represent a single covalent bond or --CH.sub.2 CH.sub.2 --; and X denotes hydrogen, fluorine or chlorine, their manufacture, liquid crystalline mixtures which contain these compounds, their production and use for electro-optical purposes.Type: GrantFiled: February 11, 1993Date of Patent: March 21, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt, Haruyoshi Takatsu
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Patent number: 5389295Abstract: Benzene derivatives of the formula I ##STR1## in which n is 1 to 7, Q is --CO or --(CH.sub.2).sub.r --, where r is 1 to 5, s is 0, 1 or 2, t is 0 or 1, where s+t.gtoreq.1, X is F, Cl, --CF.sub.3, --CN, --OCF.sub.3 or --OCHF.sub.2, and Y, L and Z are each, independently of one another, H or F.Type: GrantFiled: October 6, 1992Date of Patent: February 14, 1995Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Andreas Wachtler, Reinhard Hittich, Eike Poetsch, Herbert Plach, David Coates, Ulrich Finkenzeller, Thomas Geelhaar, Volker Reiffenrath, Bernhard Rieger
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Patent number: 5382380Abstract: New p-terphenyl derivatives useful as components for preparing practical ferroelectric liquid crystalline compositions and excellent in chemical stability, as well as liquid crystalline compositions containing at least one of the p-terphenyl derivatives.Type: GrantFiled: June 1, 1992Date of Patent: January 17, 1995Assignee: Kanto Kagaku Kabushiki KaishaInventors: Makoto Kurihara, Hiromi Inoue, Atsushi Sugiura, Kenji Suzuki, Tsunenori Fujii
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Patent number: 5382718Abstract: Mixtures of cyclofluoroalkylated fullerenes are provided by the thermal 2+2 cycloaddition of fluoroalkenes to a solution or slurry of a fullerene. The cyclofluoroalkylated fullerene mixtures are useful as lubricants or additives to lubricants; in fluorocarbon and/or chlorofluorocarbon based cooling systems; in adhesives for fluorocarbon based polymers and in gas separation membranes.Type: GrantFiled: September 16, 1993Date of Patent: January 17, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
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Patent number: 5382379Abstract: A novel liquid crystal material having an alkenyl group at the end of the molecule, and having a low viscosity is provided. When the compound is added to a display element it is able to reduce the threshold voltage of the resulting display element. The compound is expressed by the formula (I), ##STR1## wherein X is a F atom, a trifluoromethyl group, a trifluoromethoxy group or a difluoromethoxy group, --A-- is 1,4-cyclohexylene or 1,4-phenylene, --B-- is 1,4-cyclohexylene, l is 0, 1 or 2, m is 0, 1 or 2, l+m.gtoreq.1, Z is --CH.sub.2 CH.sub.2 -- or single bond, n is an integer of 0 to 4, R is a H atom or a linear or branched alkyl group of 1-7C, and when R is an alkyl group, the double bond has a trans-configuration. The compounds of the present invention are suitable as liquid crystal material for STN display element, and further are chemically stable; hence it is possible to prepare a composition having a superior multiplex characteristic and capable of effecting a low voltage drive.Type: GrantFiled: October 7, 1993Date of Patent: January 17, 1995Assignee: Chisso CorporationInventors: Yuichi Onji, Makoto Ushioda, Shuichi Matsui, Tomoyuki Kondo, Yasuyuki Goto
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Patent number: 5364560Abstract: An antiferroelectric liquid crystal compound which is a compound represented by ##STR1## wherein R denotes a linear aliphatic alkyl group having 6 to 14 carbon atoms; A denotes a single bond or an oxygen atom; X and Y independently denote a hydrogen atom or a fluorine atom but they are not hydrogen atoms at the same time; h and i are independently 1 or 2; m is an integer of 3 to 10; Z denotes CH.sub.3, C.sub.2 H.sub.5 or CF.sub.3 ; k is 0 or an integer of 5 to 8; l is 0 or 1; n is an integer of 1 to 6; W denotes CH.sub.3 or CF.sub.3 ; when W is CH.sub.3, p and q are both 0 and r is 8; when W is CF.sub.3, p is 5 to 8, q is 1 and r is 1 to 4; and C* denotes an asymmetric carbon atom,and a liquid crystal display device using same.Type: GrantFiled: January 29, 1992Date of Patent: November 15, 1994Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Masamichi Mizukami, Tomoyuki Yui, Masahiro Johno, Yoshihisa Arai, Hiroshi Mineta
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Patent number: 5326898Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 2 to 10 carbons, cyclo or branch-chained alkyl of 3 to 10 carbons, and straight chain alkenyl having 2 to 10 carbons, or cyclo or branched chained alkenyl of 3 to 10 carbons, and the Z-Y substituent is in a 1,2 (ortho) or 1,3 (meta) position on the phenyl ring relative to the ethene moiety; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.Type: GrantFiled: February 11, 1992Date of Patent: July 5, 1994Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5324449Abstract: Substituted phenyl trifluoromethyl ethers of the formula IR.sup.1 --(A.sup.1 --Z.sup.1).sub.n --A.sup.2 --Z.sup.2 --A.sup.3 --OCF.sub.3 Iin which R.sup.1, A.sup.1, Z.sup.1, n, A.sup.2, Z.sup.2 and A.sup.3 have the meaning given in claim 1, are suitable as components of liquid-crystalline phases.Type: GrantFiled: February 22, 1993Date of Patent: June 28, 1994Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Hans-Adolf Kurmeier, Bernhard Scheuble, Eike Poetsch, Ulrich Finkenzeller
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Patent number: 5264511Abstract: Monomers, B-stage polymers, C-stage polymers, cured polymers and electricy conducting polymers of acetylene-terminated aromatic monomers containing three benzene rings separated by ethylene groups are disclosed. These new polymers can withstand aggressive environments and are particularly adapted for use in high temperature composites in addition to the utilization of their electrical conducting properties. Preparation of these materials is accomplished by melt polymerization and heat treatment at high temperatures.Type: GrantFiled: June 30, 1992Date of Patent: November 23, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Theordore R. Walton
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Patent number: 5264150Abstract: A liquid crystal compound represented by formula (II) ##STR1## wherein R denotes a linear alkyl group having 6 to 14 carbon atoms, X denotes a single bond or an oxygen atom, K and L are independently 1 or 2, m is an integer of 5 to 7, n is an integer of 1 to 4, and C* denotes an asymmetric carbon atom,said compound having an antiferroelectric phase.Type: GrantFiled: November 5, 1991Date of Patent: November 23, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomoyuki Yui, Hiroshi Mineta, Masahiro Johno, Yoshihisa Arai
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Patent number: 5258544Abstract: Disclosed is a process for the preparation of 2-aryl-1-cyclohexene-1-carboxaldehydes from 1-arylcyclohexenes which are intermediates for trans-6-[(2-arylsubstituted cycloalkenyl and substituted cycloalkyl)alkenyl and alkyl]-3,4,5,6-tetrahydro-2H-pyran-2-ones.Type: GrantFiled: March 5, 1991Date of Patent: November 2, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Laurence W. Reilly, Jr., Ching T. Tsuei, Walter Rodriquez, Thomas Goetzen
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Patent number: 5238600Abstract: Compounds of the formulaR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.n --R.sup.2 Iwherein Z.sup.1 denotes the group --CH.sub.2 CH.sub.2 CH.sub.2 O-- or --OCH.sub.2 CH.sub.2 CH.sub.2 --; n stands for the number 0 or 1; R.sup.1 represents a group R.sup.3 or R.sup.3 --A.sup.4 --Z.sup.3 --; R.sup.2 represents a group R.sup.4 or R.sup.4 --A.sup.5 --Z.sup.4 --; Z.sup.2, Z.sup.3 and Z.sup.4 each independently are a single covalent bond. --CH.sub.2 --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --COO--, --OOC--, --CH.sub.2 CH.sub.2 CH.sub.2 O-- or --OCH.sub.2 CH.sub.2 CH.sub.2 --; A.sup.1, A.sup.2, A.sup.3, A.sup.4 and A.sup.5 each independently denote unsubstituted or methyl, halogen and/or cyano-substituted 1,4-phenylene, in which optionally 1-4 CH groups are replaced by nitrogen, unsubstituted or methyl- and/or cyano-substituted trans-1,4-cyclohexylene, in which optionally 2 CH.sub.2 groups are replaced by oxygen and/or sulfur, bicyclo[2.2.Type: GrantFiled: May 2, 1989Date of Patent: August 24, 1993Assignee: Hoffmann-La Roche Inc.Inventor: Stephen Kelly
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Patent number: 5238598Abstract: Disclosed in the present invention are the optically active aromatic compounds having a trifluoromethyl group useful as a component of ferroelectric liquid crystal compositions, a process for preparing the above compounds, liquid crystal compositions having the above compounds as an active ingredient, and liquid crystal elements using the above compositions. The optically active aromatic compounds of the Present invention represented by the formula: ##STR1## have the very excellent properties as a liquid crystal material and are useful for the preparation of liquid crystal compositions and the liquid crystal elements using such compositions.Type: GrantFiled: December 13, 1990Date of Patent: August 24, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Isao Kurimoto, Takayuki Higashii, Shoji Toda, Masayoshi Minai, Chizu Sekine, Takeshi Tani, Koichi Fujisawa
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Patent number: 5210278Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.Type: GrantFiled: August 25, 1992Date of Patent: May 11, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5210322Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.Type: GrantFiled: September 20, 1990Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson
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Patent number: 5208386Abstract: A fluorine-substituted compound containing an ether bond is disclosed, which is represented by formula ##STR1## wherein R represents a straight chain alkyl group having from 1 to 5 carbon atoms; m represents an integer of from 1 to 7; X represents hydrogen atom or fluorine atom; Y represents a connecting group selected from a group consisting of ##STR2## and the cyclohexane ring represents a trans(equatorial-equatorial) cyclohexane ring.Type: GrantFiled: August 9, 1991Date of Patent: May 4, 1993Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Makoto Sasaki, Haruyoshi Takatsu, Kiyofumi Takeuchi
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Patent number: 5198567Abstract: A compound of formula (I) ##STR1## its isomers and its salts in which R.sub.1, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, halogen, C.sub.1 -C.sub.8 -acyloxy or hydroxyl;R' is hydrogen or C.sub.1 -C.sub.6 -alkyl;R" is either a polyene chain or a benzene ringare useful in cosmetics and in the treatment of various dermatological and other complaints.Type: GrantFiled: July 23, 1991Date of Patent: March 30, 1993Assignee: L'OrealInventors: Gerard Lang, Jean Maignan, Serge Restle, Braham Shroot
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Patent number: 5196610Abstract: A compound of formula: ##STR1## wherein W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Z represents a fluoroalkyl group of up to two carbon atoms; Y represents a substituted aryl group where such substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; and either X' is hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and aryloxy, or X and X' together represent a second bond between the adjacent carbon atoms. The compounds have useful insecticidal properties.Type: GrantFiled: July 31, 1986Date of Patent: March 23, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Alan J. Whittle, Robin A. E. Carr
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Patent number: 5166365Abstract: A novel fluorine-containing aromatic compound of the formula: ##STR1## wherein X is ##STR2## in which R.sub.f is a perfluoroalkyl group having 1 to 10 carbon atoms,R.sub.f ' is a perfluoroalkyl group having 1 to 12 carbon atoms,p is an integer of 1 to 3,q is an integer of 0 to 3,r is 0 or 1,s is an integer of 0 to 5and t is an integer of 0 to 5,Y is X, a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a fluoroalkyl group having 1 to 8 carbon atoms, andeach A is independently ##STR3## in which D is an amino, carboxyl, hydroxyl, methyl or haloformyl group, and n is an integer of 1 or 2, or ##STR4## can be used to derive various compounds, some of which are useful for preparing a fluorine-containing epoxy compound of polyimide with good properties.Type: GrantFiled: May 10, 1990Date of Patent: November 24, 1992Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Tsutomu Kobayashhi, Motonobu Kubo
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Patent number: 5130435Abstract: Vinyl ethers of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are identical to or different from one another, each being hydrogen, straight-chain or branched alkyl or alkenyl of up to 12 carbon atoms, cycloalkyl or cycloalkylene of from 5 to 8 carbon atoms, aryl, alkylaryl, alkenylaryl, aralkyl and aralkenyl of from 6 to 16 carbon atoms, halogen-substituted aryl or heterocyclyl, and in addition the radicals R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, can form a cycloalkane, cycloalkene or a heterocycle, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by eliminating an alcohol from an acetal/ketal of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: August 9, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 5130462Abstract: Cyclobutane derivatives of the formulas ##STR1## wherein P is a hydroxy protecting group and X is a leaving group are useful intermediates in the preparation of antiviral compounds.Type: GrantFiled: February 19, 1991Date of Patent: July 14, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: William A. Slusarchyk, Robert Zahler
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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