Halogen In Acid Moiety Patents (Class 560/65)
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Patent number: 7083832Abstract: 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: GrantFiled: May 11, 2001Date of Patent: August 1, 2006Assignee: Displaytech, Inc.Inventors: Michael Wand, Neil Gough, Xin Hua Chen
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Patent number: 7074462Abstract: 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: GrantFiled: September 22, 2000Date of Patent: July 11, 2006Assignee: Merck Patent GmbHInventors: Matthias Bremer, Michael Heckmeier, Joachim Krause, Detlef Pauluth, Achim Götz, Brigitte Schuler
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Patent number: 7070838Abstract: 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: GrantFiled: June 23, 2004Date of Patent: July 4, 2006Assignees: Chisso Petrochemical Corporation, Chisso CorporationInventors: Yasuyuki Sasada, Motoki Yanai
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Patent number: 7005535Abstract: 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: GrantFiled: March 15, 2004Date of Patent: February 28, 2006Assignee: Tatung Co., Ltd.Inventors: Shune-Long Wu, Cho-Ying Lin
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Patent number: 6936739Abstract: 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: GrantFiled: May 29, 2002Date of Patent: August 30, 2005Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Käthe Baumann
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Patent number: 6913629Abstract: 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: GrantFiled: November 30, 2000Date of Patent: July 5, 2005Assignee: BASF AktiengesellschaftInventors: Bernd Bruchmann, Ulrich Treuling
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Patent number: 6908645Abstract: 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: GrantFiled: September 30, 2003Date of Patent: June 21, 2005Assignee: Merck Patent GmbHInventors: Peer Kirsch, Marc Lenges, Michael Heckmeier
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Patent number: 6828466Abstract: 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: GrantFiled: July 15, 2003Date of Patent: December 7, 2004Assignee: Board of Trustees of Michigan State UniversityInventors: Robert E. Maleczka, Jr., Milton R. Smith, III, Daniel Holmes, Feng Shi
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Patent number: 6759101Abstract: 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: GrantFiled: January 3, 2001Date of Patent: July 6, 2004Assignee: Displaytech, Inc.Inventors: Neil Gough, Rohini Vohra, Michael Wand, Kundalika More, William N. Thurmes
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Patent number: 6730371Abstract: 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: GrantFiled: April 9, 2002Date of Patent: May 4, 2004Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yasumasa Norisue, Takakiyo Mine, Masahiro Johno
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Patent number: 6706338Abstract: 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: GrantFiled: December 21, 2001Date of Patent: March 16, 2004Assignee: Merck Patent GmbHInventors: Peer Kirsch, Florian Huber, Joachim Krause, Michael Heckmeier, Detlef Pauluth
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Patent number: 6685995Abstract: 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: GrantFiled: July 7, 2000Date of Patent: February 3, 2004Assignee: Chisso CorporationInventors: Yasuhiro Haseba, Shuichi Matsui, Hiroyuki Takeuchi, Yoshitaka Yagi, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6677475Abstract: 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: GrantFiled: January 17, 2002Date of Patent: January 13, 2004Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Yasumasa Norisue, Takakiyo Mine, Masahiro Johno
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Publication number: 20030230737Abstract: The invention relates to liquid-crystalline compounds of the formula I, 1Type: ApplicationFiled: December 21, 2001Publication date: December 18, 2003Applicant: Merck GmbHInventors: Peer Kirsch, Florian Huber, Joachim Krause, Michael Heckmeier, Detlef Pauluth
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Patent number: 6639093Abstract: 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: GrantFiled: April 5, 2002Date of Patent: October 28, 2003Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Bernd-Ulrich Schenke
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Patent number: 6565769Abstract: 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: GrantFiled: December 29, 2000Date of Patent: May 20, 2003Assignee: Merck Patent GmbHInventors: David Coates, Owain Llyr Parri, Simon Greenfield, Martin David Tillin, Mark John Goulding, Patrick Nolan
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Patent number: 6551666Abstract: 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: GrantFiled: June 28, 2001Date of Patent: April 22, 2003Assignee: Merck Patent Gesellschaft MitInventors: Peer Kirsch, Joachim Krause, Michael Heckmeier
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Patent number: 6544604Abstract: 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: GrantFiled: August 10, 2001Date of Patent: April 8, 2003Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Shuichi Matsui, Yasuyuki Sasada, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Katsuyuki Kawano, Yasuhiro Kubo, Etsuo Nakagawa, Mayumi Furuya
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Patent number: 6538138Abstract: 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: GrantFiled: April 3, 2000Date of Patent: March 25, 2003Assignee: FineTech Ltd.Inventors: Arie L. Gutman, Genady Nisnevich, Eleonora Shkolnik, Igor Zaltzman
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Publication number: 20030054119Abstract: An optically active compound of the following general formula (1) useful as a chiral dbpant, and use thereof, 1Type: ApplicationFiled: April 9, 2002Publication date: March 20, 2003Applicant: Mitsubishi Gas Chemical Co., Inc.Inventors: Yasumasa Norisue, Takakiyo Mine, Masahiro Johno
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Patent number: 6514578Abstract: 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: GrantFiled: June 22, 2000Date of Patent: February 4, 2003Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventor: Louise Diane Farrand
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Patent number: 6511719Abstract: 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 filType: GrantFiled: August 13, 1998Date of Patent: January 28, 2003Assignee: Merck Patent GesellschaftInventor: Louise Farrand
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Patent number: 6468606Abstract: 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: GrantFiled: January 21, 1999Date of Patent: October 22, 2002Assignee: Chisso CorporationInventors: Shuichi Matsui, Tomoyuki Kondo, Kazutoshi Miyazawa, Noriyuki Ohnishi, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 6465687Abstract: 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: GrantFiled: March 20, 2000Date of Patent: October 15, 2002Assignee: Karo Bio ABInventors: Yi-Lin Li, Ye Liu, Asa Hedfors, Johan Malm, Charlotta Mellin, Minsheng Zhang
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Patent number: 6436312Abstract: 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: GrantFiled: April 13, 2000Date of Patent: August 20, 2002Assignees: Sharp Kabushiki Kaisha, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britian and Northern IrelandInventors: Rachel Patricia Tuffin, Andrew John Slaney, John Clifford Jones, Mitsuhiro Koden
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Patent number: 6417407Abstract: 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: GrantFiled: February 10, 2000Date of Patent: July 9, 2002Assignee: Gabriel Performance Products, LLCInventors: Bao-Guo Huang, Lawrence B. Fertel
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Patent number: 6369188Abstract: 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: GrantFiled: March 27, 1999Date of Patent: April 9, 2002Assignee: Polymeright, Inc.Inventors: Leonid Rappoport, Alex Vainer, Aleksandr Yam
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Patent number: 6326066Abstract: 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: GrantFiled: February 28, 2000Date of Patent: December 4, 2001Assignee: Merck Patent Gesellschaft mit Reschankter HaftungInventors: Eike Poetsch, Volker Meyer, Volker Reiffenrath, Andreas Wachtler, Ulrich Finkenzeller, Hans Adolf Kurmeier, Reinhard Hittich, Bernhard Rieger, David Coates, Simon Greenfield, Robert William Clemitson
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Patent number: 6319570Abstract: 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 eaType: GrantFiled: June 19, 2000Date of Patent: November 20, 2001Assignee: Chisso CorporationInventors: Tugumiti Andou, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuyuki Koizumi, Yasuko Sekiguchi, Etsuo Nakagawa, Fusayuki Takeshita
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Patent number: 6262293Abstract: &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: GrantFiled: June 23, 2000Date of Patent: July 17, 2001Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Kousuke Tani, Shuichi Ohuchida
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Patent number: 6258296Abstract: 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: GrantFiled: January 19, 2000Date of Patent: July 10, 2001Assignee: Mitsubishi Gas Chemical Company INCInventors: Masahiro Johno, Yuki Motoyama, Takahiro Matsumoto, Hiroshi Mineta, Tomoyuki Yui
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Patent number: 6242636Abstract: 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: GrantFiled: January 5, 1999Date of Patent: June 5, 2001Assignee: 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 AgencyInventors: Andrew John Slaney, Damien Gerard McDonnell, Amarjit Kaur Samra, Maurice Stanley, Victoria Minter, John William Goodby, Michael Hird, Simon John Cross, Chu Chuan Dong
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Patent number: 6201020Abstract: 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: GrantFiled: December 31, 1998Date of Patent: March 13, 2001Assignee: Guilford Pharmaceuticals, Inc.Inventors: Jie Zhang, Larisa E. Serdyuk, Jia-He Li
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Patent number: 6197216Abstract: 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: GrantFiled: September 28, 1999Date of Patent: March 6, 2001Assignee: Mitsubishi Gas Chemical Co INCInventors: Takakiyo Mine, Masahiro Johno, Tomoyuki Yui
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Patent number: 6187950Abstract: 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: GrantFiled: March 12, 1999Date of Patent: February 13, 2001Inventors: Tae K. Song, Min Teng, Roshantha A. Chandraratna
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Patent number: 6183822Abstract: 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: GrantFiled: July 15, 1999Date of Patent: February 6, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Louise Diane Farrand, Gabrielle Frances Egan
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Patent number: 6174573Abstract: 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: GrantFiled: May 19, 1999Date of Patent: January 16, 2001Assignee: Citizen Watch Co., Ltd.Inventors: Tomijiro Naito, Kikuo Yamamoto, Katsuji Niino, Yumiko Sakamaki
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Carboxylate derivatives comprising an ether group and liquid crystal composition comprising the same
Patent number: 6149990Abstract: 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: GrantFiled: August 4, 1998Date of Patent: November 21, 2000Assignee: Chisso CorporationInventors: Yoshiji Egami, Masatoshi Fukushima, Yasuko Sekiguchi, Makoto Tanimoto, Etsuo Nakagawa -
Patent number: 6133469Abstract: 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: GrantFiled: August 3, 1999Date of Patent: October 17, 2000Assignee: Mitsubishi Gas Chemical CompanyInventors: Takakiyo Mine, Masahiro Johno, Tomoyuki Yui
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Patent number: 6128065Abstract: 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: GrantFiled: February 12, 1999Date of Patent: October 3, 2000Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takakiyo Mine, Masahiro Johno, Tomoyuki Yui
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Patent number: 6057006Abstract: 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: GrantFiled: June 4, 1998Date of Patent: May 2, 2000Assignee: Merck Patent GesellschaftInventors: Peer Kirsch, Kazuaki Tarumi, Joachim Krause
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Patent number: 6051288Abstract: 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: GrantFiled: September 26, 1997Date of Patent: April 18, 2000Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Yasuhiro Haseba, Yasuyuki Koizumi, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 6043360Abstract: 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: GrantFiled: April 29, 1998Date of Patent: March 28, 2000Assignee: Eli Lilly and CompanyInventors: Tony Yantao Zhang, John Paul Gardner
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Patent number: 6031126Abstract: 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: GrantFiled: April 23, 1998Date of Patent: February 29, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Victor Eliu, Werner Kanert, Adriano Indolese, Philipp Wyser, Anita Schnyder
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Patent number: 6030546Abstract: 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: GrantFiled: April 4, 1997Date of Patent: February 29, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Yukari Fujimoto, Naoyuki Takano, Takayuki Higashii, Masayoshi Minai, Chizu Sekine, Kayoko Ueda, Koichi Fujisawa, Kyoko Endo, Takeshi Tani
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Patent number: 6005136Abstract: 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: GrantFiled: December 30, 1998Date of Patent: December 21, 1999Assignee: Hansotech IncInventors: Anthony J. O'Lenick, Jr., Jeff K. Parkinson, Robert T. Torbush
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Patent number: 5976408Abstract: 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: GrantFiled: December 19, 1997Date of Patent: November 2, 1999Assignee: Chisso CorporationInventors: Atsuko Fujita, Shuichi Matsui, Koichi Shibata, Kazutoshi Miyazawa, Yasuko Sekiguchi, Etsuo Nakagawa
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Patent number: 5976409Abstract: 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: GrantFiled: June 19, 1998Date of Patent: November 2, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hiroshi Mineta, Masahiro Johno, Tomoyuki Yui, Takahiro Matsumoto
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Patent number: 5972241Abstract: 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: GrantFiled: November 6, 1997Date of Patent: October 26, 1999Assignee: 3M Innovative Properties CompanyInventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5972244Abstract: 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: GrantFiled: January 13, 1998Date of Patent: October 26, 1999Assignee: Citizen Watch Co., Ltd.Inventors: Tomijiro Naito, Kikuo Yamamoto, Katsuji Niino, Yumiko Sakamaki