Halogen In Acid Moiety Patents (Class 560/65)
  • Patent number: 7083832
    Abstract: The invention provides LC compositions that exhibit V-shaped switching when aligned in an analog device configuration and exhibit bistability when aligned in a bookshelf-type device configuration. The invention more specifically provides LC compositions of formula 1 and particularly chiral nonracemic compounds of formula 1 which exhibit bistable switching as well as V-shaped switching when aligned in appropriate device configurations. The invention also provides methods of using the compounds of the invention in making LC compositions and electooptical devices comprising an aligned layer of the compositions of this invention.
    Type: Grant
    Filed: May 11, 2001
    Date of Patent: August 1, 2006
    Assignee: Displaytech, Inc.
    Inventors: Michael Wand, Neil Gough, Xin Hua Chen
  • Patent number: 7074462
    Abstract: The invention relates to compounds of the formula I and to a liquid-crystalline medium based on a mixture of polar compounds of positive dielectric anisotropy, characterized in that it comprises one or more compounds of the general formula I in which R, A1, A2, Z1, Y, Z, L1, L2 and m are as defined herein.
    Type: Grant
    Filed: September 22, 2000
    Date of Patent: July 11, 2006
    Assignee: Merck Patent GmbH
    Inventors: Matthias Bremer, Michael Heckmeier, Joachim Krause, Detlef Pauluth, Achim Götz, Brigitte Schuler
  • Patent number: 7070838
    Abstract: The present invention provides a compound represented by formula (1) defined in the specification and a liquid crystal composition comprising the compound. The invention further provides a polymer obtained by polymerization of compound or composition above, and further the present invention provides a film, an optical anisotropic material, A ¼ or ½ wavelength functional plate, an optical compensation element, an optical element and a liquid crystal display element employing the polymer.
    Type: Grant
    Filed: June 23, 2004
    Date of Patent: July 4, 2006
    Assignees: Chisso Petrochemical Corporation, Chisso Corporation
    Inventors: Yasuyuki Sasada, Motoki Yanai
  • Patent number: 7005535
    Abstract: The present invention relates a chiral compound, comprising a general formula as formula (I): wherein A, B independently are, ?X, Y independently are fluorine, hydrogen or chlorine; m represents an integral from 6 to 18; n represents 0; p represents 0, 3 or 4; and q represents 2, 3 or 4.
    Type: Grant
    Filed: March 15, 2004
    Date of Patent: February 28, 2006
    Assignee: Tatung Co., Ltd.
    Inventors: Shune-Long Wu, Cho-Ying Lin
  • Patent number: 6936739
    Abstract: This invention relates to 1,2-di(4-hydroxyaryl)tetrafluoroethanes of the general formula (I) wherein R are each, independently of one another, hydrogen, F, Cl, Br, I, CN, COOR2, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-perfluoroalkyl, C1-C4-perfluoroalkoxy, C1-C4-perfluoroalkylthio, C1-C4-polyfluoroalkyl, C1-C4-polyfluoroalkoxy, or C1-C4-polyfluoroalkylthio, R2 is C1-C4-alkyl, and n is an integer from 0 to 4. This invention further relates to the preparation of such compounds as well as to precursors and intermediates that can be used in their preparation.
    Type: Grant
    Filed: May 29, 2002
    Date of Patent: August 30, 2005
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Käthe Baumann
  • Patent number: 6913629
    Abstract: Compounds of the formula 1 OCN—R1—NHCOX—R2—(Y)n??(1), where X is a covalent bond to R2 or is O, S or NR3, Y is a hydrogen atom or a free functional group and n is an integer from 1 to 20, can be used for functionalizing or modifying compounds or solid surfaces which have at least one group which is reactive toward isocyanate.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: July 5, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Bruchmann, Ulrich Treuling
  • Patent number: 6908645
    Abstract: The invention relates to liquid-crystalline compounds of the formula I and to a liquid-crystalline medium based on a mixture of polar compounds, characterized in that it comprises one or more compounds of the general formula I in which R1, L1, L2, L3, L4, L5, L6, Z1, Z2, X, v and u are as defined in claim 1.
    Type: Grant
    Filed: September 30, 2003
    Date of Patent: June 21, 2005
    Assignee: Merck Patent GmbH
    Inventors: Peer Kirsch, Marc Lenges, Michael Heckmeier
  • Patent number: 6828466
    Abstract: A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.
    Type: Grant
    Filed: July 15, 2003
    Date of Patent: December 7, 2004
    Assignee: Board of Trustees of Michigan State University
    Inventors: Robert E. Maleczka, Jr., Milton R. Smith, III, Daniel Holmes, Feng Shi
  • Patent number: 6759101
    Abstract: Compounds that are useful as components in liquid crystal compositions, particularly in ferroelectric liquid crystal compositions. Compounds of the invention are rod-like molecules with a mesogenic (generally linear) core to which an alkene tail and an alkyl or alkoxy tail with a perfluoroalkyl terminal portion are bonded. Compounds of the invention can contain a variety of one, two or three ring cores, wherein the rings maybe aromatic or alicyclic. Alkenes of the invention are useful as components to improve LC properties of mixtures, for example, to lower melting point of lower freezing point, of LC compositions.
    Type: Grant
    Filed: January 3, 2001
    Date of Patent: July 6, 2004
    Assignee: Displaytech, Inc.
    Inventors: Neil Gough, Rohini Vohra, Michael Wand, Kundalika More, William N. Thurmes
  • Patent number: 6730371
    Abstract: An optically active compound of the following general formula (1) useful as a chiral dopant, and use thereof, wherein each of X and Y is independently a hydrogen atom or a fluorine atom, R is (C2H5)2CHCH2C*H(CH3)— or Ph—C*H(CH3)—, A is —Ph(W)—COO—Ph—, —Ph—Ph—COO—, —Cy—COO—Ph—, —Ph(W)—OOC—Ph—COO—, —Ph(W)—OOC—Cy—COO—, —Ph(W)—OOC—Np—COO— or —Np—OOC—, in which Ph— is a phenyl group, —Ph— is a 1,4-phenylene group, —Ph(W)— is —Ph— or monofluoro substituted —Ph—, Cy— is a trans-1,4-cyclohexylene group and —Np— is a 2,6-naphthylene group, and C* is an asymmetric carbon.
    Type: Grant
    Filed: April 9, 2002
    Date of Patent: May 4, 2004
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yasumasa Norisue, Takakiyo Mine, Masahiro Johno
  • Patent number: 6706338
    Abstract: The invention relates to liquid-crystalline compounds of the formula I, and to liquid-crystalline media comprising at least one compound of the formula I and to electro-optical displays containing such a liquid-crystalline medium.
    Type: Grant
    Filed: December 21, 2001
    Date of Patent: March 16, 2004
    Assignee: Merck Patent GmbH
    Inventors: Peer Kirsch, Florian Huber, Joachim Krause, Michael Heckmeier, Detlef Pauluth
  • Patent number: 6685995
    Abstract: Liquid crystalline compounds suitable for driving at a low voltage and at a wide temperature range, and suitable for high speed response, liquid crystal compositions comprising the compound, and liquid crystal display devices comprising the liquid crystal composition. The crystalline compounds are ester compounds expressed by the general formula (1) wherein R1 represents e.g. a hydrogen atom; A1 to A5 each independently represent e.g. 1,4-cyclohexylene, 1,4-phenylene, 1-cyclohexene-1,4-diyl, 3-cyclohexene-1,4-diyl, 1-sila-1,4-cyclohexylene, or 4-sila-1,4-cyclohexylene; bonding groups Za to Zd each independently represent e.g. a single bond, —CH2—, —O—, —C≡C—, or an alkylene group or alkenylene group having 2 to 4 carbon; bonding group Ze represents e.g.
    Type: Grant
    Filed: July 7, 2000
    Date of Patent: February 3, 2004
    Assignee: Chisso Corporation
    Inventors: Yasuhiro Haseba, Shuichi Matsui, Hiroyuki Takeuchi, Yoshitaka Yagi, Fusayuki Takeshita, Etsuo Nakagawa
  • Patent number: 6677475
    Abstract: Optically active compounds of the following general formula (1) useful as chiral dopant, wherein n is an integer of 0 to 5, provided that when n is 0, A is a single bond (—) and that when n is 1 to 5, A is a single bond (—), —O—, —COO—, —Cy— or —Cy—COO— in which —Cy— is a trans-1,4-cyclohexylene group, each of X and Y is independently a hydrogen atom or a fluorine atom, B is a single bond (—), —COO—, —COO—Ph— or —Ph—COO— in which —Ph— is a 1,4-phenylene group, and C* is an asymmetric carbon. The chiral dopant of the present invention have a high helical twisting power of at least 9 and suitably have a feature that the helical pitch induced by them decreases in length with an increase in temperature so that they are advantageous for use in a nematic liquid crystal composition.
    Type: Grant
    Filed: January 17, 2002
    Date of Patent: January 13, 2004
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Yasumasa Norisue, Takakiyo Mine, Masahiro Johno
  • Publication number: 20030230737
    Abstract: The invention relates to liquid-crystalline compounds of the formula I, 1
    Type: Application
    Filed: December 21, 2001
    Publication date: December 18, 2003
    Applicant: Merck GmbH
    Inventors: Peer Kirsch, Florian Huber, Joachim Krause, Michael Heckmeier, Detlef Pauluth
  • Patent number: 6639093
    Abstract: The invention relates to the preparation of hydroxybenzoic benzyl esters by reacting benzyl chloride with hydroxybenzoic acids in the presence of one or more amides.
    Type: Grant
    Filed: April 5, 2002
    Date of Patent: October 28, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Bernd-Ulrich Schenke
  • Patent number: 6565769
    Abstract: To improve switching times, especially at low temperatures, one or more reactive liquid crystalline compounds is added to a liquid crystal mixture used in an electrooptical system. The electrooptical system comprises a PDLC film comprising a liquid crystal mixture forming micro- droplets in an optically isotropic, transparent polymer matrix between 2 electrode layers, one of the refractive indices of the liquid crystal mixture is matched to the refractive index of the polymer matrix, the PDLC film exhibits an electrically switching transparency essentially independent of the polarization of the incident light, the precursor of the PDLC film comprises one or more monomers, oligomers and/or prepolymers and a photoinitiator, and is cured photoradically, the liquid crystal mixture comprises one or more compounds of the formula I  wherein R, A1, A2, Z1, Z2, X1, X2, Q, Y and n are as defined herein.
    Type: Grant
    Filed: December 29, 2000
    Date of Patent: May 20, 2003
    Assignee: Merck Patent GmbH
    Inventors: David Coates, Owain Llyr Parri, Simon Greenfield, Martin David Tillin, Mark John Goulding, Patrick Nolan
  • Patent number: 6551666
    Abstract: The invention relates to cyclohexane derivatives of the formula I in which n, m, p, R1, X1, X2, Z1, Z2, Z3, A1 A2 and Y are as defined above.
    Type: Grant
    Filed: June 28, 2001
    Date of Patent: April 22, 2003
    Assignee: Merck Patent Gesellschaft Mit
    Inventors: Peer Kirsch, Joachim Krause, Michael Heckmeier
  • Patent number: 6544604
    Abstract: The present invention provides a liquid crystalline compound having a difluoropropyleneoxy group as a bonding group, which is represented by Formula (1): wherein R1 and R2 each independently represent hydrogen, halogen, a cyano group or an alkyl group having 1 to 20 carbon atoms; rings A1 to A5 each independently represent a 1,4-cyclohexylene group, a 1,4-cyclohexenylene group or a 1,4-phenylene group; Z1 to Z4 each independently represent a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OCO—, —CH═CH—, —C≡C—, —CF2O— or —OCF2—; Y1, Y2, Y3 and Y4 each independently represent hydrogen or fluorine; and k, l, m and n each independently represent 0 or 1. This liquid crystalline compound has a large absolute value (|&Dgr;&egr;|) of a dielectric anisotropy and shows a relatively small refractive anisotropy.
    Type: Grant
    Filed: August 10, 2001
    Date of Patent: April 8, 2003
    Assignees: Chisso Corporation, Chisso Petrochemical Corporation
    Inventors: Shuichi Matsui, Yasuyuki Sasada, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Katsuyuki Kawano, Yasuhiro Kubo, Etsuo Nakagawa, Mayumi Furuya
  • Patent number: 6538138
    Abstract: The invention relates to processes for the preparation of compounds of the formula wherein R is a 2-piperidyl or 2-pyridyl radical, and pharmaceutically acceptable salts thereof, the process comprising the steps of: a) reacting 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid or a salt thereof with a haloacetonitrile to form a cyanomethyl ester of formula b) reacting the ester with an amine of the formula RCH2NH2, where R is as defined above.
    Type: Grant
    Filed: April 3, 2000
    Date of Patent: March 25, 2003
    Assignee: FineTech Ltd.
    Inventors: Arie L. Gutman, Genady Nisnevich, Eleonora Shkolnik, Igor Zaltzman
  • Publication number: 20030054119
    Abstract: An optically active compound of the following general formula (1) useful as a chiral dbpant, and use thereof, 1
    Type: Application
    Filed: April 9, 2002
    Publication date: March 20, 2003
    Applicant: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Yasumasa Norisue, Takakiyo Mine, Masahiro Johno
  • Patent number: 6514578
    Abstract: Polymerizable tolanes of formula I wherein P, Sp, X, n, A1, A2, Z1, Z2, m1, m2, L1, L2, r and R have the meanings defined herein, polymerizable liquid crystal compositions comprising at least one compound of formula I, linear or crosslinked liquid crystal polymers obtainable from these compounds and compositions, are suitable for use in optical elements such as polarizers, retardation and compensation films, alignment layers, color filters or holographic elements. They are also suitable for use in liquid crystal displays such as PDLC, polymer gel or polymer stabilized cholesteric texture (PSCT) displays, as well as for use in adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics or liquid crystal pigments, for decorative and security applications, and for nonlinear optics or optical information storage.
    Type: Grant
    Filed: June 22, 2000
    Date of Patent: February 4, 2003
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventor: Louise Diane Farrand
  • Patent number: 6511719
    Abstract: The invention relates to chiral compounds of formula I wherein R1, R2, MG1, MG2, Sp, X, Y, a, b, c and d have the meaning given in claim 1, to a liquid crystalline mixture comprising at least one chiral compound of formula I, to a polymerizable liquid crystalline mixture comprising at least one chiral compound of formula I and optionally at least one polymerizable mesogenic compound, to the use of such a liquid crystalline mixture or a polymerizable liquid crystalline mixture for the preparation of anisotropic polymer films with a chiral liquid crystalline phase, for active and passive optical elements like polarizers, compensators or color filters and for liquid crystal displays, for example STN, TN, AMD-TN, temperature compensation, guest-host or phase change displays, or surface stabilized or polymer stabilized cholesteric texture (SSCT, PSCT) displays, to cholesteric liquid crystal displays comprising liquid crystalline mixtures comprising chiral compounds of formula I and to polymer fil
    Type: Grant
    Filed: August 13, 1998
    Date of Patent: January 28, 2003
    Assignee: Merck Patent Gesellschaft
    Inventor: Louise Farrand
  • Patent number: 6468606
    Abstract: A liquid crystal composition which comprises at least one phenylbenzoate derivative represented by formula (1) wherein R1 is a hydrogen atom or an alkyl group of 1-10 carbons and others; X is a hydrogen atom or a halogen atom; A and B each independently represent a 1,4-phenylene group or a trans-1,4-cyclohexylene group and others; Z1 and Z2 each independently represent —CH2CH2—, —CO—O—, a covalent bond and others; m and n each independently represent 0 or 1.
    Type: Grant
    Filed: January 21, 1999
    Date of Patent: October 22, 2002
    Assignee: Chisso Corporation
    Inventors: Shuichi Matsui, Tomoyuki Kondo, Kazutoshi Miyazawa, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
  • Patent number: 6465687
    Abstract: Novel thyroid receptor ligands are provided which have the general formula (I) where R1 is alkyl of 1 to 4 carbons or cycloalkyl of 3 to 7 carbons; R2 and R3 are the same or different and are hydrogen, halogen, alkyl of 1 to 3 carbons or cycloalkyl of 3 to 5 carbons, at least one of R2 and R3 being other than hydrogen; n is an integer from 0 to 4; R4 is an aliphatic hydrocarbon, an aromatic hydrocarbon, carboxylic acid ester thereof, alkenyl carboxylic acid or ester thereof, hydroxy, halogen, cyano, or a phosphonic acid or an ester thereof, or a pharmaceutically acceptible salt thereof. A method for treating diseases associated with metabolism dysfunction or which are dependent on the expression of a T3 regulated gene, such as obesity, hypercholesterolemia, osteoporosis, hypothyroidism, and goiter, is also provided.
    Type: Grant
    Filed: March 20, 2000
    Date of Patent: October 15, 2002
    Assignee: Karo Bio AB
    Inventors: Yi-Lin Li, Ye Liu, Asa Hedfors, Johan Malm, Charlotta Mellin, Minsheng Zhang
  • Patent number: 6436312
    Abstract: A liquid crystal composition comprises a host material capable of exhibiting a smectic C phase, and a chiral dopant material which imparts or enhances chirality in the host material. The composition exhibits &tgr;-Vmin curves. The chiral dopant material comprises at least first and second chiral centers. The chiral centers individually produce, in the liquid crystal composition, different and complementary temperature coefficients of spontaneous polarization within a predetermined temperature range. The chiral centers are present in the liquid crystal composition in relative amounts such that regions of the &tgr;-Vmin curves across the predetermined temperature range are substantially coincident.
    Type: Grant
    Filed: April 13, 2000
    Date of Patent: August 20, 2002
    Assignees: Sharp Kabushiki Kaisha, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britian and Northern Ireland
    Inventors: Rachel Patricia Tuffin, Andrew John Slaney, John Clifford Jones, Mitsuhiro Koden
  • Patent number: 6417407
    Abstract: A 2-bromo-4-chloro substituted phenol is prepared from a first composition of a substituted phenol and benzotrifluoride in a weight ratio to the substituted phenol of about 2 to about 4. Into the first composition is sparged about 1 to about 1.5 equivalents of chlorine gas, whereby the substituted phenol is chlorinated to form a 4-chloro substituted phenol. The first composition is cooled to precipitate the 4-chloro substituted phenol, which can be isolated by filtration. A second composition is formed of the 4-chloro substituted phenol, acetic acid in an weight ratio to the 4-chloro substituted phenol of about 1 to about 2, about 1 to about 2 equivalents of a salt of a strong base and a weak acid, and about 1 to about 5 equivalents of a brominating agent, whereby the 4-chloro substituted phenol is brominated to form a 2-bromo-4-chloro substituted phenol.
    Type: Grant
    Filed: February 10, 2000
    Date of Patent: July 9, 2002
    Assignee: Gabriel Performance Products, LLC
    Inventors: Bao-Guo Huang, Lawrence B. Fertel
  • Patent number: 6369188
    Abstract: Polyfunctional polymerizable urethane- or urea-containing oligomers allow the design, adjustment, and regulation of chemical and physical properties of the described oligomers. The invention discloses the formulas and compositions of these oligomers, methods of their synthesis, and methods of converting the described oligomers into useful polymeric products. The described oligomers can be used for many purposes, both directly and in combination with other chemicals in multiple applications such as adhesives, sealants, coatings, composites, etc., as well as in castable and moldable materials.
    Type: Grant
    Filed: March 27, 1999
    Date of Patent: April 9, 2002
    Assignee: Polymeright, Inc.
    Inventors: Leonid Rappoport, Alex Vainer, Aleksandr Yam
  • Patent number: 6326066
    Abstract: 1,4-disubstituted 2,6-difluorobenzene compound of formula I wherein R is an alkyl or alkenyl radical, A1 and A2 are independently (a) a trans-1,4-cyclohexylene radical in which a CH2 group may be replaced by -O- and/or -S, (b) a 1,4-phenylene radical in which a CH group may be replaced by N, (c) 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, Z1 and Z2 are —CO—O—, —O—CO—, —CH2O—,—OCH2—, —CH2CH2—, —CH═CH—,—C≡C—or a single bond m and n are 0, 1, 2 or 3, (m+n) is 1, 2 or 3, X is R or F, Cl, CF3, —OCF3, or —OCHF2, —OCF5, —CN or —NCS with the provisos that at least one of the radicals A1 and A2 present in the molecule is  and at least one of Z1 or Z2 is —COO—, are suitable as components of liquid-
    Type: Grant
    Filed: February 28, 2000
    Date of Patent: December 4, 2001
    Assignee: Merck Patent Gesellschaft mit Reschankter Haftung
    Inventors: Eike Poetsch, Volker Meyer, Volker Reiffenrath, Andreas Wachtler, Ulrich Finkenzeller, Hans Adolf Kurmeier, Reinhard Hittich, Bernhard Rieger, David Coates, Simon Greenfield, Robert William Clemitson
  • Patent number: 6319570
    Abstract: The invention is to provide liquid crystalline compounds which have a low viscosity, high negative dielectric anisotropy, high resistivity, and high voltage holding ratio, and are stable against heat and ultraviolet light; to provide liquid crystal compositions comprising the liquid crystalline compound; and to provide liquid crystal display devices using the liquid crystal composition therein; the liquid crystalline compound is expressed by the general formula (1)  wherein R1 and Y1 represent an alkyl group having 1 to 20 carbon atoms; X1, X2, and X3 independently represent single bond, 1,2-ethylene group, vinylene group, —COO—, —CF2O—, or —OCF2—; ring A1, ring A2, ring A3, and ring A4 independently represent trans-1,4-cycloliexylene, or 1,4-phenylene hydrogen atom on the ring may be replaced by fluorine atom or chlorine atom provided that at least one of ring A2, ring A3, and ring A4 represents 2,3-difluoro-1,4-phenylene; m and n are 0 or 1, and ea
    Type: Grant
    Filed: June 19, 2000
    Date of Patent: November 20, 2001
    Assignee: Chisso Corporation
    Inventors: Tugumiti Andou, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuyuki Koizumi, Yasuko Sekiguchi, Etsuo Nakagawa, Fusayuki Takeshita
  • Patent number: 6262293
    Abstract: &ohgr;-Cycloalkyl-prostaglandin E2 derivatives of formula (I) (wherein all symbols are as defined in the description); and non-toxic salts thereof, prodrugs thereof and cyclodextrin clathrates thereof. Compounds of formula (I) strongly bind on the EP2 subtype receptor. Therefore, they are useful for prevention and/or treatment of immunological diseases (autoimmune diseases, organ transplantation etc.), asthma, abnornmal bone formation, neuronal cell death, liver damage, abortion, premature birth or retina neuropathy of glaucoma etc.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: July 17, 2001
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Kousuke Tani, Shuichi Ohuchida
  • Patent number: 6258296
    Abstract: A fluorine-substituted compound of the following general formula (1) or (2), and a ferrielectric liquid crystal composition comprising the above compound and a specific ferrielectric liquid crystal compound, wherein, in the formula (1), each of X1 and X2 is a hydrogen atom, or one of them is a hydrogen atom and the other is a fluorine atom, p is an integer of 0 to 3 and q is an integer of 1 to 3, and in the formula (2), each of X1 and x2 is a hydrogen atom, or one of them is a hydrogen atom and the other is a fluorine atom, p is an integer of 1 to 3 and q is an integer of 1 to 3.
    Type: Grant
    Filed: January 19, 2000
    Date of Patent: July 10, 2001
    Assignee: Mitsubishi Gas Chemical Company INC
    Inventors: Masahiro Johno, Yuki Motoyama, Takahiro Matsumoto, Hiroshi Mineta, Tomoyuki Yui
  • Patent number: 6242636
    Abstract: An electoclinic device having two spaced cell walls each bearing electrode structures and treated on at least one facing surface with an alignment layer, a layer of a smectic liquid crystal material enclosed between the cell walls, where the liquid crystal material contains one or more of the compounds described by formula I as defined in the specification.
    Type: Grant
    Filed: January 5, 1999
    Date of Patent: June 5, 2001
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britian and Northern Ireland of Defence Evaluation and Research Agency
    Inventors: Andrew John Slaney, Damien Gerard McDonnell, Amarjit Kaur Samra, Maurice Stanley, Victoria Minter, John William Goodby, Michael Hird, Simon John Cross, Chu Chuan Dong
  • Patent number: 6201020
    Abstract: This invention relates to compounds, pharmaceutical compositions, and methods of using compounds of the formula: A is O or S; R is C1-C10 straight or branched chain alkyl, C2-C10 straight or branched chain alkenyl, C2-C10 straight or branched chain alkynyl, aryl, heteroaryl, carbocycle, or heterocycle; D is a bond, or a C1-C3 straight or branched chain alkyl, C2-C3 straight or branched chain alkenyl, C2-C3 straight or branched chain alkynyl, wherein any of the carbon atoms of said alkyl, alkenyl, or alkynyl of D are optionally replaced with oxygen, nitrogen, or sulfur; and X is aryl, heteroaryl, carbocycle, or heterocycle.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: March 13, 2001
    Assignee: Guilford Pharmaceuticals, Inc.
    Inventors: Jie Zhang, Larisa E. Serdyuk, Jia-He Li
  • Patent number: 6197216
    Abstract: A novel ferrielectric liquid crystal compound of the formula (1), wherein R is a linear alkyl group having 6 to 12 carbon atoms, X is a hydrogen atom or a fluorine atom, m is an integer of 1 to 3, n is an integer of 1 to 3, and C* is an asymmetric carbon atom. The ferrielectric liquid crystal compound of the invention characteristically has a ferrielectric phase in a broad temperature range and shows a high speed optical response in spite of a small spontaneous polarization.
    Type: Grant
    Filed: September 28, 1999
    Date of Patent: March 6, 2001
    Assignee: Mitsubishi Gas Chemical Co INC
    Inventors: Takakiyo Mine, Masahiro Johno, Tomoyuki Yui
  • Patent number: 6187950
    Abstract: Compounds of the formula Y3(R4)—X—Y1(R1R2)—Z—Y2(R2)—A—B where the symbols have the meaning defined in the specification, have retinoid, retinoid antagonist or retinoid inverse agonist type biological activity.
    Type: Grant
    Filed: March 12, 1999
    Date of Patent: February 13, 2001
    Inventors: Tae K. Song, Min Teng, Roshantha A. Chandraratna
  • Patent number: 6183822
    Abstract: The invention relates to polymerizable fluorophenylenes of formula I wherein P, Sp, X, n, L, Z1, Z2, A, B, m and R have the meaning of claim 1, to a polymerizable liquid crystalline composition comprising at least one polymerizable mesogenic fluorophenylene of formula I, to the use of the inventive mesogenic fluorophenylenes and compositions comprising them for the preparation of linear or crosslinked liquid crystalline polymers, and to the use of inventive compounds, compositions and polymers in liquid crystal displays, polarizers, compensators, alignment layers, color filters or holographic elements, adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, for decorative and security applications, in nonlinear optics, optical information storage or as chiral dopants.
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: February 6, 2001
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Louise Diane Farrand, Gabrielle Frances Egan
  • Patent number: 6174573
    Abstract: A novel tolan compound of the formula (I): wherein A is C1-10 alkyl, C1-10 alkoxy, cyclohexyl substituted by C1-10 alkyl at 4 position, cyclohexyl substituted by C1-10 alkoxy group at 4 position or a group of the formula: wherein Y is hydrogen or halogen and Z is C1-10 alkyl or halogen; B is a single bond or —CO—O— or —O—CO—; D is hydrogen, C1-10 alkyl, cyclohexyl substituted by C1-10 alkyl at 4 position; and Z represents a hydrogen atom or a halogen atom. The tolan compound can increase the N-I point, decrease the viscosity, and increase the double refractive index of a liquid crystal composition without affecting the viscosity and threshold voltage Vth, and is mutually soluble with various other liquid crystal compounds, so that the compound can be used as a constituent of a liquid crystal composition in combination with these other liquid crystal materials to improve the properties of the composition.
    Type: Grant
    Filed: May 19, 1999
    Date of Patent: January 16, 2001
    Assignee: Citizen Watch Co., Ltd.
    Inventors: Tomijiro Naito, Kikuo Yamamoto, Katsuji Niino, Yumiko Sakamaki
  • Patent number: 6149990
    Abstract: A compound represented by the following general formula (I), a liquid crystal composition comprising the same, and a liquid crystal element using this liquid crystal composition. ##STR1## (wherein B.sub.1 and B.sub.2 represent independently a trans-1,4-cyclohexylene group or a 1,4-phenylene group wherein at least one hydrogen atom on the six-membered ring is optionally substituted by a halogen atom, Y represents a halogen-substituted alkyl group having 1 to 3 carbon atoms, a halogen-substituted alkoxy group having 1 to 3 carbon atoms, a cyano group, a fluorine atom or a chlorine atom, X represents a fluorine atom, a chlorine atom or a hydrogen atom, R.sub.1 represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, n and m represent independently 1 or 2 and p represents 0 or 1.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: November 21, 2000
    Assignee: Chisso Corporation
    Inventors: Yoshiji Egami, Masatoshi Fukushima, Yasuko Sekiguchi, Makoto Tanimoto, Etsuo Nakagawa
  • Patent number: 6133469
    Abstract: A novel anti-ferroelectric liquid crystal compounds of the formula (1), ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms, X is a hydrogen atom or a fluorine atom, m is an integer of 1 to 3, n is an integer of 1 or 2, and C* is an asymmetric carbon atom.The above anti-ferroelectric liquid crystal compounds have an anti-ferroelectric phase in a broad temperature range, so that they can be advantageously used as a main component for a liquid crystal material for practical use or as a component for a liquid crystal composition.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: October 17, 2000
    Assignee: Mitsubishi Gas Chemical Company
    Inventors: Takakiyo Mine, Masahiro Johno, Tomoyuki Yui
  • Patent number: 6128065
    Abstract: A ferrielectric liquid crystal compound of the general formula (1), ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms, either each of X and Y is a hydrogen atom or one of X and Y is a hydrogen atom and the other is a fluorine atom, m is an integer of 1 to 2, n is 1 and C* is an asymmetric carbon. The above liquid crystal compound shows a ferrielectric phase in a wide temperature range and exhibits a fast response in spite of its small spontaneous polarization, and it is therefore remarkably useful for an active-matrix liquid crystal display device.
    Type: Grant
    Filed: February 12, 1999
    Date of Patent: October 3, 2000
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takakiyo Mine, Masahiro Johno, Tomoyuki Yui
  • Patent number: 6057006
    Abstract: The invention relates to fluorocyclohexane derivatives of the formula I ##STR1## in which R.sup.1, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2, L.sup.3 and X are as defined as below:X is alkyl or alkoxy having 1 to 10 carbon atoms which is unsubstituted or substituted by halogen, alkenyl or alkenyloxy having 2 to 10 carbon atoms which is unsubstituted or substituted by --CN, --CF.sub.3 or --F, or is --CN, --F, --OCHF.sub.2, --OCF.sub.3, --OCHFCF.sub.3 or --OCF.sub.2 CF.sub.3,L.sup.1, L.sup.2 and L.sup.3 are each, independently of one another, H or F,R.sup.1 is H, an alkyl or alkenyl radical having 1-12 carbon atoms which is unsubstituted, monosubstituted by CN or CF.sub.3 or substituted by halogen, where one or more non-adjacent CH.sub.2 groups in these radicals may also, in each case independently of one another, be replaced by --O--, --S--, --CO--, --.diamond.--, --CO--O--, --O--CO-- or --O--CO--O--,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --O--, --O--CH.sub.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: May 2, 2000
    Assignee: Merck Patent Gesellschaft
    Inventors: Peer Kirsch, Kazuaki Tarumi, Joachim Krause
  • Patent number: 6051288
    Abstract: An object of the present invention is to provide a novel liquid crystalline compound having a large dielectric anisotropy, small change in threshold voltage depending on temperature, and an improved solubility to other liquid crystal materials at low temperatures, and expressed by the following general formula (1): ##STR1## wherein R represents, for example, an alkyl group or alkoxy group having 1 to 10 carbon atoms, m and n are independently 0 or 1, A.sub.1, A.sub.2, and A.sub.3 are independently, for example, trans-1,4-cyclohexylene group, 1,4-phenylene group one or more hydrogen atoms on the ring of which may be replaced by F, Z.sub.1, Z.sub.2, and Z.sub.3 independently represent --COO--, --OCO--, --(CH.sub.2).sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, or a covalent bond provided that at least one of Z.sub.1, Z.sub.2, and Z.sub.3 represents ester bond, --CH.sub.2 O--, or --OCH.sub.2 --, X represents, for example, CF.sub.3, CF.sub.2 H, and Y represents H or F.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: April 18, 2000
    Assignee: Chisso Corporation
    Inventors: Tomoyuki Kondo, Yasuhiro Haseba, Yasuyuki Koizumi, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
  • Patent number: 6043360
    Abstract: The instant invention provides intermediates and processes for the preparation of compounds of formula IV ##STR1## wherein: n is 0, 1, or 2;R is hydrogen or C.sub.1 -C.sub.4 alkyl;X.sup.1 is hydrogen, cyano, 4-hydroxybenzoyl, 4-halobenzoyl, or 4-(C.sub.1 -C.sub.4 alkoxy)benzoyl;Y is NR.sup.4 R.sup.5, 4-hydroxyphenyl, or 4-(C.sub.1 -C.sub.4 alkoxy)phenyl;and R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl.
    Type: Grant
    Filed: April 29, 1998
    Date of Patent: March 28, 2000
    Assignee: Eli Lilly and Company
    Inventors: Tony Yantao Zhang, John Paul Gardner
  • Patent number: 6031126
    Abstract: A process for the production of a fluorescent whitening agent of formula: ##STR1## in which X and Z are as defined herein, comprising A) rearranging a hydrazobenzene compound having the formula: ##STR2## in which Z is as defined herein, to produce in situ a compound having the formula: ##STR3## B) diazotising the compound of formula (3) to produce a compound having the formula: ##STR4## in which Z has its previous significance and G.sub.1 is a counter ion; and C) reacting the compound of formula (4) with 2 moles of a compound having the formula: ##STR5## in which X and n have their previous significance, in the presence of an inorganic or organic palladium salt, or a mixture thereof, as catalyst-precursor, to produce a compound having the formula (1).
    Type: Grant
    Filed: April 23, 1998
    Date of Patent: February 29, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Victor Eliu, Werner Kanert, Adriano Indolese, Philipp Wyser, Anita Schnyder
  • 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: 6005136
    Abstract: The invention relates to a series of novel alkoxylated fluoro esters which contain a terminal carboxy group. This class of compounds provides unique solubility in many organic solvents as well as very substantive salts of the carboxylic acid when neutralized with base. In addition, the compounds of the present invention have tremendous spreadability when applied to substrate. The compounds of the present invention are prepared by reacting a the hydroxyl group in a fluoro alcohol with an anhydride.
    Type: Grant
    Filed: December 30, 1998
    Date of Patent: December 21, 1999
    Assignee: Hansotech Inc
    Inventors: Anthony J. O'Lenick, Jr., Jeff K. Parkinson, Robert T. Torbush
  • Patent number: 5976408
    Abstract: An acrylonitrile derivative expressed by the following general formula I, a composition comprising the derivative and having an improved viscosity and optical anisotropy, and a liquid crystal display device: ##STR1## wherein rings A.sup.1 to A.sup.3 represent phenylene, cyclohexylene, dioxane, or pyrimidine, R.sup.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: November 2, 1999
    Assignee: Chisso Corporation
    Inventors: Atsuko Fujita, Shuichi Matsui, Koichi Shibata, Kazutoshi Miyazawa, Yasuko Sekiguchi, Etsuo Nakagawa
  • Patent number: 5976409
    Abstract: A swallow-tail-shaped liquid crystal compound of the following general formula (1), ##STR1## wherein A is --O--, --COO-- or a single bond (--), m is an integer of 4 to 12, and n is an integer of 2 to 4.The above swallow-tail-shaped liquid crystal compound of the present invention is a novel achiral anti-ferroelectric liquid crystal and can be converted to an optically active anti-ferroelectric liquid crystal by mixing it with an optically active compound as a chiral dopant.
    Type: Grant
    Filed: June 19, 1998
    Date of Patent: November 2, 1999
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiroshi Mineta, Masahiro Johno, Tomoyuki Yui, Takahiro Matsumoto
  • Patent number: 5972241
    Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion containing at least one methylene group and optionally containing at least one catenary ether oxygen atom; (b) a saturated, chiral or achiral, hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: November 6, 1997
    Date of Patent: October 26, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 5972244
    Abstract: A novel tolan compound of the formula (I): ##STR1## wherein A is C.sub.1-10 alkyl, C.sub.1-10 alkoxy, cyclohexyl substituted by C.sub.1-10 alkyl at 4 position, cyclohexyl substituted by C.sub.1-10 alkoxy group at 4 position or a group of the formula: ##STR2## wherein Y is hydrogen or halogen and Z is C.sub.1-10 alkyl or halogen; B is a single bond or --CO--O-- or --O--CO--; D is hydrogen, C.sub.1-10 alkyl, cyclohexyl substituted by C.sub.1-10 alkyl at 4 position; and Z represents a hydrogen atom or a halogen atom. The tolan compound can increase the N-I point, decrease the viscosity, and increase the double refractive index of a liquid crystal composition without affecting the viscosity and threshold voltage Vth, and is mutually soluble with various other liquid crystal compounds, so that the compound can be used as a constituent of a liquid crystal composition in combination with these other liquid crystal materials to improve the properties of the composition.
    Type: Grant
    Filed: January 13, 1998
    Date of Patent: October 26, 1999
    Assignee: Citizen Watch Co., Ltd.
    Inventors: Tomijiro Naito, Kikuo Yamamoto, Katsuji Niino, Yumiko Sakamaki