Halogen Containing Patents (Class 568/647)
  • Patent number: 7758931
    Abstract: Such a liquid crystal compound is provided that has stability to heat, light and so forth, has a nematic phase in a wide temperature range, has a small viscosity, a suitable optical anisotropy, and suitable elastic constants K33 and K11 (K33: bend elastic constant, K11: splay elastic constant), and has suitable negative dielectric anisotropy and excellent compatibility with other liquid crystal compounds. A liquid crystal composition containing the liquid crystal compound, and a liquid crystal display device containing the liquid crystal composition are also provided.
    Type: Grant
    Filed: June 29, 2009
    Date of Patent: July 20, 2010
    Assignees: Chisso Corporation, Chisso Petrochemical Corporation
    Inventors: Yasuyuki Goto, Teru Shimada, Teruyo Sugiura
  • Patent number: 7744968
    Abstract: The present invention relates to cyclobutane and spiro[3.3]heptane compounds, to a process for the preparation thereof, to the use thereof as components in liquid-crystalline media, and to electro-optical display elements which contain these liquid-crystalline media.
    Type: Grant
    Filed: August 16, 2006
    Date of Patent: June 29, 2010
    Assignee: Merck Patent GmbH
    Inventors: Volker Reiffenrath, Matthias Bremer, Melanie Klasen-Memmer
  • Patent number: 7648743
    Abstract: The disclosed is a liquid crystal compound and method for manufacturing the same. The liquid crystal compound can be used alone or mixed with commercially available liquid crystal compounds. Because low rotational viscosity of the liquid crystal compound of the invention, it can be used as positive or negative dielectric anisotropic liquid crystal composition.
    Type: Grant
    Filed: April 3, 2008
    Date of Patent: January 19, 2010
    Assignee: Industrial Technology Research Institute
    Inventors: An-Cheng Chen, Pei-Chen Huang, Kung-Lung Cheng, Shih-Hsien Liu
  • Publication number: 20090302273
    Abstract: A liquid crystal compound represented by formula (1), a liquid crystal composition comprising the compound, and a liquid crystal display device comprising the composition: For example, R1 is alkyl having 1 to 20; ring A1, ring A2, ring A3, ring A4, ring A5, and ring A6 are 1,4-cyclohexylene or 1,4-phenylene; Z1, Z2, Z3, Z4, Z5, and Z6 is a single bond; X1 is hydrogen or halogen; l, m, n, o, p, and q are 0 or 1, and l+m+n+o+p+q is 3.
    Type: Application
    Filed: June 4, 2009
    Publication date: December 10, 2009
    Applicants: CHISSO CORPORATION, CHISSO PETROCHEMICAL CORPORATION
    Inventor: HIROYUKI TANAKA
  • Publication number: 20090264683
    Abstract: Such a liquid crystal compound is provided that has stability to heat, light and so forth, has a nematic phase in a wide temperature range, has a small viscosity, a suitable optical anisotropy, and suitable elastic constants K33 and K11 (K33: bend elastic constant, K11: splay elastic constant), and has suitable negative dielectric anisotropy and excellent compatibility with other liquid crystal compounds. A liquid crystal composition containing the liquid crystal compound, and a liquid crystal display device containing the liquid crystal composition are also provided.
    Type: Application
    Filed: June 29, 2009
    Publication date: October 22, 2009
    Applicants: CHISSO CORPORATION, CHISSO PETROCHEMICAL CORPORATION
    Inventors: YASUYUKI GOTO, Teru Shimada, Teruyo Sugiura
  • Publication number: 20090230356
    Abstract: A compound represented by the following formula (1), a liquid crystal composition containing the compound and a liquid crystal display device containing the composition: all the symbols in the formula (1) are defined in the specification.
    Type: Application
    Filed: March 18, 2009
    Publication date: September 17, 2009
    Applicants: CHISSO CORPORATION, CHISSO PETROCHEMICAL CORPORATION
    Inventor: Yasuyuki SASADA
  • Publication number: 20090123666
    Abstract: The disclosed is a liquid crystal compound and method for manufacturing the same. The liquid crystal compound can be used alone or mixed with commercially available liquid crystal compounds. Because low rotational viscosity of the liquid crystal compound of the invention, it can be used as positive or negative dielectric anisotropic liquid crystal composition.
    Type: Application
    Filed: April 3, 2008
    Publication date: May 14, 2009
    Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: An-Cheng Chen, Pei-Chen Huang, Kung-Lung Cheng, Shih-Hsien Liu
  • Patent number: 7510749
    Abstract: A liquid crystal compound selected from a group of compounds represented by formula (a): wherein Ra and Rb are each independently hydrogen, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, provided that in the alkyl, —CH2— may be replaced by —O—, but plural —O— are not adjacent to each other, and hydrogen may be replaced by fluorine; ring A1 and ring A2 are each independently trans-1,4-cyclohexylene or 1,4-phenylene, provided that one or two hydrogens of the 1,4-phenylene may be replaced by halogen, and in a 6-membered ring of these groups, one —CH2— or two —CH2— that are not adjacent to each other may be replaced by —O—, and one or two —CH? may be replaced by —N?; Z1 and Z2 are each independently a single bond, —(CH2)2—, —(CH2)4—, —CH?CH—, —C?—, —CH2O—, —OCH2—, —COO—, —OCO— or —OCF2—; l and m are each independently 0, 1 or 2, provided that l+m is 0, 1, 2 or 3; and n is an integer of from 0 to 6, provided that in —(CH2)n—, —CH2— may be replaced by —O—, but plural —O— are not adjacent to eac
    Type: Grant
    Filed: September 6, 2007
    Date of Patent: March 31, 2009
    Assignees: Chisso Corporation, Chisso Petrochemical Corporation
    Inventor: Teru Shimada
  • Publication number: 20090030198
    Abstract: Methods of synthesizing sodium glucose co-transporter 2 inhibitors, as well as compounds useful therein, are disclosed.
    Type: Application
    Filed: July 17, 2008
    Publication date: January 29, 2009
    Inventors: Nicole Cathleen Goodwin, Bryce Alden Harrison, Shinya Iimura, Ross Mabon, Qiuling Song, Wenxue Wu, Jie Yan, Haiming Zhang, Matthew Mangzhu Zhao
  • Publication number: 20080260971
    Abstract: The present invention relates to a liquid-crystalline medium comprising 1,2-difluoroethene compounds of the general formula I, in which R1, ring A, Z1, Z2, m, X and L1-6 are as defined in claim 1. The invention also relates to the use of the medium for electro-optical purposes and to displays containing this medium. Novel 1,2-difluoroethene compounds having 3 or more rings are disclosed.
    Type: Application
    Filed: May 18, 2006
    Publication date: October 23, 2008
    Inventors: Michael Wittek, Markus Czanta, Harald Hirschmann, Volker Reiffenrath
  • Publication number: 20080221230
    Abstract: The invention is a flame retardant for styrene foams. The flame retardant contains both aromatic bromine and an olefin. The olefin is an internal olefin. Desirable flame retardants are selected from: formula I: wherein R1 is C1-C6 and optionally containing a heteroatom or olefin; R2 is C1-C6 and optionally containing a heteroatom or olefin; and R3-R12 is H, C1-C6 (optionally containing a heteroatom), or halogen; and further wherein the compound of formula I is present in a concentration of at least 50 percent of a trans isomer; formula II: wherein R1 is Halogen, C1-C6 and optionally containing a heteroatom or olefin; R2 is Halogen, C1-C6 and optionally containing a heteroatom or olefin; and R3-R7 is H, C1-C6 (optionally containing a heteroatom), or halogen; and formula III: wherein R1 is Halogen, C1-C6 and optionally containing a heteroatom or olefin; R2 is Halogen, H, C1-C6 and optionally containing a heteroatom or olefin; and R3-R6 is H, halogen.
    Type: Application
    Filed: November 30, 2007
    Publication date: September 11, 2008
    Inventors: Mark V. Hanson, Stephen B. Falloon, Wayne Meyer
  • Publication number: 20080206490
    Abstract: The present invention relates to cyclobutane and spiro[3.3]heptane compounds, to a process for the preparation thereof, to the use thereof as components in liquid-crystalline media, and to electro-optical display elements which contain these liquid-crystalline media.
    Type: Application
    Filed: August 16, 2006
    Publication date: August 28, 2008
    Inventors: Volker Reiffenrath, Matthias Bremer, Melanie Klasen-Memmer
  • Patent number: 7351452
    Abstract: A compound of formula (I) or a dimer thereof; where R1 and R2 are independently selected from optionally substituted alkyl, optionally substitituted alkenyl, optionally substituted alkynyl, a functional group or a group of sub-formula (i) —(O)m—(CH2)p—R7??(i) where m is 0 or 1; p is an integer of from 1 to 12; R7 is a group of formula —CqX2q+1 where q is an integer of from 1 to 12 and X is halogen such as fluoro, or R7 a group of sub-formula (ii) where k is an integer of from 1 to 10, R8, R10, and R12 and each R9 and R11 are independently selected from alkyl, alkenyl or aryl, such as lower alkyl and in particular methyl; provided that at least one of R1 or R2 is a group of sub-formula (i); R3, R4, R5 and R6 are independently selected from hydrogen or halogen, and in particular fluorine, n is 0 or 1, and A is a ring structure as specified. Compounds of formula (I) may have liquid crystal properties and/or be useful in liquid crystal devices.
    Type: Grant
    Filed: November 7, 2002
    Date of Patent: April 1, 2008
    Assignee: Qinetiq Limited
    Inventors: John W Goodby, Michael Hird, Kenneth J Toyne, Chu C Dong, Robert D. C Richards
  • Publication number: 20080063814
    Abstract: A liquid crystal compound selected from a group of compounds represented by formula (a): wherein Ra and Rb are each independently hydrogen, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, provided that in the alkyl, —CH2— may be replaced by —O—, but plural —O— are not adjacent to each other, and hydrogen may be replaced by fluorine; ring A1 and ring A2 are each independently trans-1,4-cyclohexylene or 1,4-phenylene, provided that one or two hydrogens of the 1,4-phenylene may be replaced by halogen, and in a 6-membered ring of these groups, one —CH2— or two —CH2— that are not adjacent to each other may be replaced by —O—, and one or two —CH? may be replaced by —N?; Z1 and Z2 are each independently a single bond, —(CH2)2—, —(CH2)4—, —CH?CH—, —C?—, —CH2O—, —OCH2—, —COO—, —OCO— or —OCF2—; l and m are each independently 0, 1 or 2, provided that l+m is 0, 1, 2 or 3; and n is an integer of from 0 to 6, provided that in —(CH2)n—, —CH2— may be replaced by —O—, but plural —O— are not adjacent to eac
    Type: Application
    Filed: September 6, 2007
    Publication date: March 13, 2008
    Inventor: Teru Shimada
  • Patent number: 6949579
    Abstract: The present invention relates to the novel indazole derivatives of general formula (I): in which: R is either O, S or NH; R3 is an alkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, aryl, heterocycle, cycloalkyl, alkenyl, etc. radical; these radicals being optionally substituted with one or more substituents; R4, R5, R6 and R7 are chosen, independently of each other, from the following radicals: hydrogen, halogen, CN, NO2, NH2, OH, COOH, C(O)OR8, —O—C(O)R8, NR8R9, NHC(O)R8, C(O)NR8R9, NHC(S)R8, C(S)NR8R9, SR8, S(O)R8, SO2R8, NHSO2R8, SO2NR8R9, trifluoromethyl, trifluoromethoxy, alkyl, alkoxy, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocycle, cycloalkyl, alkenyl, etc.; these radicals being optionally substituted with one or more substituents.
    Type: Grant
    Filed: March 11, 2003
    Date of Patent: September 27, 2005
    Assignee: Aventis Pharma S.A.
    Inventors: Gilles Dutruc-Rosset, Dominique Lesuisse, Thomas Rooney, Franck Halley
  • Patent number: 6864397
    Abstract: The present invention provides a process for producing a difluoromethyl ether derivative simple and efficient process for producing the difluoromethyl ether derivative represented by Formula (1d?) or a difluoromethyl ether derivative represented by Formula (1c?): wherein all the variables are defined in the specification.
    Type: Grant
    Filed: June 18, 2003
    Date of Patent: March 8, 2005
    Assignees: Chisso Corporation, Chisso Petrochemical Corporation
    Inventors: Tomoyuki Kondo, Kouki Sagou, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
  • Patent number: 6844462
    Abstract: The invention relates to the biphenyldiols of the formula (V) The corresponding racemic and enantiomerically pure triflate compounds thereof, where R1 and R2 are H, R3 is chlorine, and R4 is methoxy. In an alternate embodiment, R1 and R2 are hydrogen and R3 and R4 are C1-C4-alkoxy, fluorine, or chlorine.
    Type: Grant
    Filed: April 7, 2003
    Date of Patent: January 18, 2005
    Assignee: Bayer Aktiengesellschaft
    Inventors: Birgit Drieben-Hölscher, Joachim Kralik, Inga Ritzkopf, Christian Steffens, Guido Giffels, Claus Dreisbach, Thomas Prinz
  • Patent number: 6827876
    Abstract: A liquid crystalline compound represented by Formula (1c′): wherein R1 and R2, rings A1, A2, A3, A4 and A5, Z1, Z2, Z3 and Z4, Y1, Y2, Y3 and Y4, and k, l, m and n are as defined in the specification. Also provided is a liquid crystal composition containing at least one of these liquid crystalline compounds.
    Type: Grant
    Filed: June 18, 2003
    Date of Patent: December 7, 2004
    Assignees: Chisso Corporation, Chisso Petrochemical Corporation
    Inventors: Tomoyuki Kondo, Kouki Sagou, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
  • Patent number: 6770463
    Abstract: There is provided a process for the preparation of a chiral insecticidal and acaricidal compound of formula I. Also provided are intermediate compounds useful in the process of the present invention.
    Type: Grant
    Filed: August 2, 2001
    Date of Patent: August 3, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: John Francis Chiarello, Brian Lee Buckwalter, Timothy Claude Barden
  • Patent number: 6605747
    Abstract: 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. According to the present invention, a process for producing a difluoromethyl ether derivative represented by Formula (1d): wherein the variables are defined in the specification, is characterized by using an &agr;&agr;-difluorocyclohexylidene derivative represented by Formula (1a): wherein R1, rings A1 and A2, Z1, Z2, k and l have the same meanings as defined in the specification, as a starting material.
    Type: Grant
    Filed: August 10, 2001
    Date of Patent: August 12, 2003
    Assignees: Chisso Corporation, Chisso Petrochemical Corporation
    Inventors: Tomoyuki Kondo, Kouki Sagou, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
  • Patent number: 6576303
    Abstract: Novel liquid crystal compound having a negative and absolutely large value of dielectric anisotropy, being excellent in compatibility with other liquid crystalline compounds at a low temperature and being stable chemically and physically, as well as a liquid crystal composition comprising this compound, and a liquid crystal display device comprising this liquid crystal composition are provided, said compound is expressed by the general formula (1): R1—A1—B1—A2—B2—A3—B3—Z—B4—A4—R2  (1) wherein A1, A2, A3 and A4 represent a single bond, 1,4-cyclohexylene, 1,4-phenylene which may be substituted with a fluorine atom(s) or the like; B1, B2, B3 and B4 represent a single bond, 1,2-ethylene, 1,2-ethenylene, 1,2-ethynylene, oxymethylene, methyleneoxy or the like; R1 and R2 represent an alkyl group having 1 to 10 carbon atoms or the like; and Z represents (I) to (VI): wherein X represents H or F, and Y represents difluoromethyl gr
    Type: Grant
    Filed: August 24, 2000
    Date of Patent: June 10, 2003
    Assignee: Chisso Corporation
    Inventors: Norio Tamura, Atsuko Fujita, Hiroyuki Tekeuchi, Fusayuki Takeshita, Etsuo Nakagawa
  • Patent number: 6534135
    Abstract: The invention relates to a process of preparing a discotic liquid crystalline compound by intramolecular oxidative cyclisation of a diaryl compound in an organic solvent in the presence of a strong acid, characterized in that an oxidative agent comprising a chrom(VI)oxide derivative is used, to discotic liquid crystalline compounds obtainable from said process, to liquid crystalline media, (co)polymers or polymer networks with columnar phases comprising said discotic liquid crystalline compounds, and to the use of said discotic liquid crystalline compounds, liquid crystalline media or liquid crystalline (co)polymers with columnar phases for liquid crystal displays, optical elements like polarizers, compensators or colour filters, chemical sensors, charge transport materials, optical storage media, nonlinear optics, decorative pigments, adhesive or synthetic resins with anisotropic mechanical properties.
    Type: Grant
    Filed: September 14, 2000
    Date of Patent: March 18, 2003
    Assignee: Merck Patent Gesellschaft
    Inventor: Mohammed Cherkaoui
  • Patent number: 6342642
    Abstract: The present invention provides novel 1,4-diaryl-2-fluoro-1-buten-3-ol compounds of the structural formula I a method for the preparation of those formula I compounds, and the use of those formula I compounds in the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds of formula II and 1,4-diaryl-2-fluoro-2-butene compounds of formula III
    Type: Grant
    Filed: August 13, 2001
    Date of Patent: January 29, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Yulin Hu, David Allen Hunt
  • Patent number: 6329555
    Abstract: Described is a process for preparing substituted butenes of the formula I and/or II, where the radical R is unsubstituted or mono- or di-C1-C10-alkoxy-substituted or mono- or dihydroxy-substituted C2-C20-alkyl or alkenyl or is C6-C10-aryl, C7-C11-aralkyl or methyl by reacting 1,3-butadiene with an alcohol of the formula ROH in which R is as defined in the presence of an acidic particulate catalyst insoluble in the reaction medium, which involves contacting the butadiene, the alcohol and the catalyst in a fluidized bed reactor which is flow-approached from below and is operated at above the loosening point.
    Type: Grant
    Filed: November 2, 1999
    Date of Patent: December 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Maik Aron, Ralf Böhling, Peter Zehner
  • Patent number: 6210603
    Abstract: Liquid crystalline compounds are provided which have an extremely high voltage holding ratio, altered only slightly by change of temperature, and which have a low threshold voltage and a high &Dgr;n. Also provided are liquid crystal compositions containing the liquid crystalline compound; and liquid crystal display devices containing the liquid crystal composition. The liquid crystalline compound is expressed by the general formula (1) wherein R, Y1 to Y16, X and Z1 to Z3 are defined in claim 1.
    Type: Grant
    Filed: May 28, 1999
    Date of Patent: April 3, 2001
    Assignee: Chisso Corporation
    Inventors: Tomoyuki Kondo, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Shuichi Matsui, Yasusuke Hisatsune, Fusayuki Takeshita, Etsuo Nakagawa
  • Patent number: 6171664
    Abstract: The invention relates to tolan derivatives of the formula I in which R1, R2, A, Z, L1, L2, L3, L4, L5, L6, Q, m and n are as defined herein.
    Type: Grant
    Filed: June 17, 1999
    Date of Patent: January 9, 2001
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Matthias Bremer, Detlef Pauluth, Harald Hirschmann
  • Patent number: 6139771
    Abstract: This invention provides LC compositions useful as birefringent materials in electrooptic devices which exhibit zero or low negatively sloped birefringence dispersion (e.g., exhibiting positive birefringence dispersion significantly lower than that of currently available LC compositions) or more preferably positively sloped birefringence dispersion in which birefringence of the material increases with wavelength. The invention provides compounds useful as components of LC compositions which exhibit negative birefringence where n.sub.o is higher than n.sub.e. The compounds of this invention are dimers of LC-like compounds in which the monomers are linked to each other through a high birefringence moiety (dimerization linker). The LC monomers consist of an LC core and one or two tail groups. Preferred monomers for this invention have low birefringence in comparison to the birefrigence of the monomer linking moiety.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: October 31, 2000
    Assignee: Displaytech, Inc.
    Inventors: David M. Walba, Daniel J. Dyer, Uwe Muller, Peter Cobben, Xin Hua Chen, William Thurmes, Michael Wand
  • Patent number: 6056893
    Abstract: A dopant compound of the formula IR.sup.1 -(A.sup.1 -Z.sup.1).sub.n -A.sup.2 -W Iin which ##STR1## and R.sup.1, A.sup.1, A.sup.2, Z.sup.1 n, X and R.sup.a are as defined in claim 1, and to the use thereof as chiral dopants in liquid-crystalline media for electro-optical displays, and to electro-optical displays containing such media.
    Type: Grant
    Filed: October 30, 1997
    Date of Patent: May 2, 2000
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Georg Weber
  • Patent number: 6030546
    Abstract: The present invention relates to trans-olefin compounds represented by the general formula (1) useful as an ingredient of liquid crystal composition, trans-olefin compounds useful as intermediate of pesticides, medical drugs, liquid crystal materials and the like, a process for producing those trans-olefin compounds, a liquid crystal composition containing the trans-olefin compound as an active ingredient, and a liquid crystal element using the liquid crystal composition. ##STR1## (In the general formula (1), R.sup.1, A.sup.1, A.sup.2, A.sup.3, Z and R.sup.2 are same as defined in the specification. Also, m, p, q, n, r, s and t are each an integer as defined in the specification.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: February 29, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukari Fujimoto, Naoyuki Takano, Takayuki Higashii, Masayoshi Minai, Chizu Sekine, Kayoko Ueda, Koichi Fujisawa, Kyoko Endo, Takeshi Tani
  • Patent number: 6015508
    Abstract: Disclosed are (A) a liquid crystalline compound of the general formula: ##STR1## wherein X.sub.1 stands for a hydrogen atom, cyano group, a halogen atom, or an alkyl group with 1-20 carbon atoms, and one or more methylene groups in the alkyl group may be replaced by --CH.dbd.CH--, --.tbd.C--, or oxygen atoms and one or more hydrogen atoms may be substituted by halogen atoms; X.sub.2 stands for a hydrogen atom, an alkyl group with 1-10 carbon atoms, or a substituent of --(A.sub.4 --Z.sub.4).sub.s --A.sub.6 --X.sub.3 ; l, m, n and s each stands for an integer of 0 or 1, and p, and q each stands for an integer of 0-5; X.sub.3 for an alkyl group with 1-10 carbon atoms; Z.sub.1 -Z.sub.4 each independently stands for a covalent bond or an alkylene group with 1-5 carbon atoms, and one or more methylene groups in the alkylene group may be replaced by --CH.dbd.CH--, --C.tbd.C--, or an oxygen atom and one or more hydrogen atoms i the alkylene group may be substituted by halogen atoms; the ring A.sub.1 -A.sub.
    Type: Grant
    Filed: February 26, 1998
    Date of Patent: January 18, 2000
    Assignee: Chisso Corporation
    Inventors: Noriyuki Ohnishi, Hiroyuki Takeuchi, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
  • Patent number: 5998673
    Abstract: Pesticidal 1,4-diaryl-2-fluoro-2-butene compounds having the structural formula I ##STR1## and compositions and methods comprising those compounds for the control of insect and acarid pests.
    Type: Grant
    Filed: May 29, 1997
    Date of Patent: December 7, 1999
    Assignee: American Cyanamid Company
    Inventors: Keith D. Barnes, Yulin Hu
  • Patent number: 5928562
    Abstract: A process for controlling the cone tilt angle of a tilted smectic liquid crystal composition comprises the step of combining (a) at least one liquid crystal composition comprising at least one smectic or latent smectic liquid crystal compound comprising (i) an aliphatic fluorocarbon terminal portion comprising a terminal fluoroalkyl or fluoroether group and an alkylene group having at least two carbon atoms and containing at least one catenary ether oxygen atom, (ii) an aliphatic hydrocarbon terminal portion, and (iii) a central core connecting the terminal portions; and (b) at least one liquid crystal composition comprising at least one smectic or latent smectic liquid crystal compound; with the provisos that at least one of the compositions (a) and (b) comprises at least one chiral liquid crystal compound and that the combining of compositions (a) and (b) provides an optically active, tilted chiral smectic liquid crystal composition.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: July 27, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: John F. Kistner, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad
  • Patent number: 5910605
    Abstract: The invention relates to a process for the preparation of 3-hydroxy-2-methylbenzoic acid and 3-acetoxy-2-methylbenzoic acid, which comprises reacting 3-chloro-2-methylphenol (3) with benzyl chloride to give 2-benzyloxy-6-chlorotoluene (4) subjecting this to a Grignard reaction with magnesium to give (3-benzyloxy-2-methylphenyl)magnesium chloride (5) reacting this with CO.sub.2 to give 3-benzyloxy-2-methylbenzoic acid (6) hydrogenating this or its alkali metal salts in the presence of a hydrogenation catalyst to give 3-hydroxy-2-methylbenzoic acid (2) and optionally acetylating this to give 3-acetoxy-2-methylbenzoic acid.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: June 8, 1999
    Assignee: Clariant GmbH
    Inventors: Robert Cosmo, Andreas Dierdorf
  • Patent number: 5888423
    Abstract: Flourobenzyl ether derivatives of the formula ##STR1## and liquid crystalline mixtures which contain such compounds are prepared and employed in electro-optical display devices.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: March 30, 1999
    Assignee: Rolic Ag
    Inventors: Richard Buchecker, Alfred Germann
  • Patent number: 5872301
    Abstract: Bifunctional compounds of the formula (I), ##STR1## in which: ##STR2## are naphthalene-2,6-diyl or ##STR3## is naphthalene-2,6-diyl or ##STR4## U, X, Y and Z are --CH.dbd., --CF.dbd. and --N.dbd., with the proviso that --CF.dbd. and --N.dbd. may each only be represented at most twice per six-membered ring, and that --CF.dbd. and --N.dbd. may not at the same time be represented twice in a six-membered ring;Hal is Cl, Br or I; or H, if X and/or Y are --CF.dbd.R.sup.3 is CH.sub.3 or OCH.sub.3l is 0 or 1m and n are 0, 1, 2 or 3.The compounds of the formula I are useful intermediates for the preparation of liquid-crystalline mixtures.
    Type: Grant
    Filed: June 13, 1995
    Date of Patent: February 16, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Schlosser, Rainer Wingen, Javier Manero
  • Patent number: 5855812
    Abstract: A process for controlling the cone tilt angle of a tilted smectic liquid crystal composition comprises the step of combining (a) at least one liquid crystal composition comprising at least one smectic or latent smectic liquid crystal compound comprising (i) an aliphatic fluorocarbon terminal portion comprising a terminal fluoroalkyl or fluoroether group and an alkylene group having at least two carbon atoms and containing at least one catenary ether oxygen atom, (ii) an aliphatic hydrocarbon terminal portion, and (iii) a central core connecting the terminal portions, wherein the alkylene group of the aliphatic fluorocarbon terminal portion is directly linked to the central core by a moiety selected from the group consisting of a covalent bond, --CH.dbd.CH--, and --C.tbd.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: January 5, 1999
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 5851424
    Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds of the general formula ##STR1## wherein A.sup.1 and A.sup.2 each represent a cross-linkable, mesogenic residue,liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.
    Type: Grant
    Filed: July 25, 1996
    Date of Patent: December 22, 1998
    Assignee: Rolic AG
    Inventor: Stephen Kelly
  • Patent number: 5849959
    Abstract: The present invention relates to compounds of the formula (1) ##STR1## where R is H, a straight-chain or branched alkyl radical with 1 to 6 carbons, a fluorinated straight-chain or branched alkyl radical with 1 to 6 carbons, a benzyl radical, or a benzyl radical substituted by an alkyl group or alkoxy group with 1 to 4 carbons each, or by halogen, X is H, Cl, Br or I, and X is different from R, and a process for their preparation.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: December 15, 1998
    Assignee: Clariant GmbH
    Inventors: Ralf Pfirmann, Rainer Wingen
  • Patent number: 5840209
    Abstract: ?I! An optically active compound of the formula (1), ##STR1## wherein R.sup.1 is a linear alkyl group, each of X.sup.1 and X.sup.2 is a hydrogen atom or one of X.sup.1 and X.sup.2 is a hydrogen atom and the other is a fluorine atom, each of Y.sup.1 and Y.sup.2 is a hydrogen atom or one of Y.sup.1 and Y.sup.2 is a hydrogen atom and the other is a fluorine atom, m is an integer of 3 to 10, and C* is an asymmetric carbon atom,?II! an anti-ferroelectric liquid crystal composition consisting essentially of the optically active compound of the above formula (1) and a compound of the formula (2), ##STR2## and ?III! a ferrielectric liquid crystal composition consisting essentially of the optically active compound of the formula (1) and a compound of the formula (3).
    Type: Grant
    Filed: May 14, 1997
    Date of Patent: November 24, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiroshi Mineta, Tomoyuki Yui, Masahiro Johno, Seiji Adachi, Yuki Motoyama
  • Patent number: 5800734
    Abstract: A compound of the formula ##STR1## wherein R is C.sub.1 -C.sub.7 alkyl or C.sub.2 -C.sub.12 alkenyl; rings A and B each independently are 1,4-phenylene,trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;Z.sup.1 is a single bond or --CH.sub.2 CH.sub.2 --; andZ.sup.2 is a single bond, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --,--C.tbd.C--, --COO-- or --OOC--; andm, n are 0 or 1, with the proviso that m+n.ltoreq.1;as well as liquid crystalline mixtures which contain such compounds and the use of such compounds and, respectively, mixtures for electro-optical display devices.
    Type: Grant
    Filed: March 4, 1996
    Date of Patent: September 1, 1998
    Assignee: Rolic AG
    Inventors: Richard Buchecker, Guy Marck
  • Patent number: 5772914
    Abstract: Chiral benzene derivatives of formula I ##STR1## in which R.sup.1*, R.sup.2*, X.sup.1, X.sup.2, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2, L.sup.3, m, n and k are as defined in claim 1, and their use as chiral dopes in liquid-crystalline media, particularly for electrooptical displays, and to electrooptical displays containing such media.
    Type: Grant
    Filed: November 18, 1996
    Date of Patent: June 30, 1998
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Detlef Pauluth, Matthias Bremer, Herbert Plach, Georg Weber
  • Patent number: 5770108
    Abstract: A novel pyrimidine compound represented by the following Formulas (1) and (2), a liquid crystal composition containing said compound and a liquid crystal element having excellent characteristics such as high speed response, orientation and high contrast ratio. ##STR1## wherein R.sub.1 and R.sub.2 each represent a linear or branched alkyl or alkenyl group, an alkoxyl or alkenyloxy group; R.sub.3 and R.sub.4 each represent a linear or branched alkyl group or alkenyl group; A.sub.1 and A.sub.2 each represent a substituted or unsubstituted 1,4-phenylene group, a pyridine-2,5-diyl or trans-1,4-cyclohexylene group; X.sub.1 and X.sub.2 each represent a single bond, --COO--, --OCO--, --OCH.sub.2 or --CH.sub.2 O-- group; Y.sub.1 and Y.sub.2 each represent --COO-- or --OCO-- group; and a, b, p, q, m and n each represent 0 or 1, provided that a+b+p+q is not 0.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: June 23, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Yoshiyuki Totani, Motokazu Hirao, Atsuo Otsuji, Tsutomu Ishida, Hiroe Kayashima, Masakatsu Nakatsuka
  • Patent number: 5759443
    Abstract: Objects of this invention are cyclopentyl compounds of the general formula ##STR1## wherein k signifies a whole number of 4 to 18;n signifies 0 or 1;Y.sup.1, Y.sup.2 signify a single bond, --O--, --COO-- or --OOC--;rings A, B, C each independently signify optionally mono- or difluorinated 1,4-phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, pyrazine-2,5-diyl, naphthalene-2,6-diyl, quinoline-2,6-diyl, thiophene-2,5-diyl, thiazole-2,5-diyl or 1,3,4-thiadiazole-2,5-diyl and ring C also signifies trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl;Z.sup.1 signifies a single bond, --COO--,--OOC-- or --C.tbd.C--;Z.sup.2 signifies --COO--, --OOC--, --OCH.sub.2 --, --CH.sub.2 O-- or --(CH.sub.2).sub.
    Type: Grant
    Filed: June 26, 1997
    Date of Patent: June 2, 1998
    Assignee: Rolic AG
    Inventors: Jurg Funfschilling, Alois Villiger
  • Patent number: 5755994
    Abstract: A novel liquid crystalline compound having a large dielectric anisotropy value, a small change in the threshold voltage depending upon temperatures, and an improved solubility in other liquid crystal materials at low temperatures, and a liquid crystal composition containing the compound are provided,which liquid crystalline compound is expressed by the formula (1) ##STR1## wherein R is H or an alkyl group of 1 to 10C; l is an integer of 1 to 9; m, n and o are each independently 0 or 1; A.sub.1, A.sub.2 and A.sub.3 are each independently trans-1,4-cyclohexylene group, 1,4-phenylene group, one or more H atoms on the ring of which group may be replaced by F, or the like group; Z.sub.1, Z.sub.2 and Z.sub.3 are each independently --COO--, etc., but at least one of them is --COO--; X is CF.sub.3, etc.; and Y.sub.1, and Y.sub.2 are each independently H or F.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: May 26, 1998
    Assignee: Chisso Corporation
    Inventors: Tomoyuki Kondo, Shuichi Matsui, Yasuyuki Koizumi, Koichi Shibata, Yasuhiro Haseba, Norihisa Hachiya, Etsuo Nakagawa, Kazutoshi Miyazawa
  • Patent number: 5741438
    Abstract: Optically active biphenyl derivatives including optically active biphenyl carboxylic acid derivative, hydroxybiphenyl derivative, alkoxybiphenylalkanol derivative and alkoxybiphenylalkanol derivative have the following structural formula: ##STR1## wherein R.sup.1 represents an alkyl group of 3-20 carbon atoms, R.sup.2 represents an alkyl group or alkoxyalkyl group of 1-20 carbon atoms which may optionally be substituted with at least one halogen atom. X represents --O--, --COO-- or --OCO--, m represents 0 or 1, n represents an integer of 1-6 and p represents 0 or 1, and the * mark represents an asymmetric carbon atom. These optically active biphenyl derivatives are useful as a ferroelectric liquid crystal material or its component having a sufficient spontaneous polarization and by which a high speed response is possible and which further exhibits a ferroelectric liquid crystal phase in a temperature region around room temperature.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: April 21, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Isao Kurimoto, Takayuki Higashii, Shoji Toda, Masayoshi Minai, Chizu Sekine, Takeshi Tani
  • Patent number: 5707544
    Abstract: The present invention is concerned with chromophore-containing photo cross-linkable liquid crystalline compounds having the formula ##STR1## wherein A.sup.1 and A.sup.2 each represent a cross-linkable, mesogenic group; andA.sup.3 represents a dichroic group.as well as liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.
    Type: Grant
    Filed: May 20, 1996
    Date of Patent: January 13, 1998
    Assignee: Rolic AG
    Inventor: Stephen Kelly
  • Patent number: 5705095
    Abstract: Compounds of the formula I ##STR1## in which R.sup.1, R.sup.2, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2, L.sup.3, m and n are as defined herein, are suitable as component of liquid-crystalline media.
    Type: Grant
    Filed: February 12, 1996
    Date of Patent: January 6, 1998
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Ekkehard Bartmann, Ulrich Finkenzeller
  • Patent number: 5700393
    Abstract: The present invention is concerned with photo cross-linkable liquid crystalline compounds of the general formula ##STR1## wherein A.sup.1 and A.sup.2 each are a cross-linkable mesogenic residue; andA.sup.3 is (R,R)- or (S,S)-trans-1,2-cyclohexyl-diyl,liquid crystalline mixtures which contain such compounds and their use in the cross-linked state as optical components.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: December 23, 1997
    Assignee: Rolic AG
    Inventor: Stephen Kelly
  • Patent number: 5658951
    Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: Research Corporation Technologies
    Inventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
  • Patent number: RE36849
    Abstract: 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: Grant
    Filed: April 1, 1993
    Date of Patent: September 5, 2000
    Assignee: Merck Patent GmbH
    Inventors: Hans P. Schad, Stephen M. Kelly, Eike Poetsch, Reinhard Hittich, Georg Weber