Carbocyclic Ring Contains Six Carbon Atoms Patents (Class 570/131)
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Patent number: 7029730Abstract: The invention relates to CF2O-bridged cyclohexane derivatives, in particular compounds of formula (I), R1-(-A1-Z1-)k1-Q-CF2O-A2-(-Z3-A3-)K3-R2, wherein Q represents group (a); W1, W2 represent —CH2— and/or —O— independendy from each other, X1, X2, X3, X4 represent H, F, —CH3—CH2F—CH2F and/or —CF3 independently from each other, provided that at least one substituent X1, X2, X3 and/or X4 does not represent H, Z2 represents a simple bond, —CH2—CH2— or —CF2—CF2—, m represents 0 or 1 and R1, R2, A1, A2, A3, Z1, Z3, k1 and k3 have the meaning cited in the description. The invention further relates to liquid crystal substances such as optical and electro-optical display elements.Type: GrantFiled: May 2, 2002Date of Patent: April 18, 2006Assignee: Merck Patent GmbHInventors: Peer Kirsch, Andreas Taugerbeck, Detlef Pauluth, Joachim Krause, Kazuaki Tarumi, Georg Lüssem
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Patent number: 7026021Abstract: Compounds of the general formula (I) where: R1, R2 are each independently a) H b) -M1-A1-R5 c) a straight-chain or branched alkyl radical having from 1 to 16 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 16 carbon atoms, where c1) one or more nonadjacent and nonterminal CH2 groups may be replaced by —O—, —C(?O)O—, —O—C(?O)—, —O—C(?O)—O—, —C(?O)— or —Si(CH3)2—, and/or c2) one CH2 group may be replaced by —C?C—, cyclopropane-1,2-diyl, cyclobutane-1,3-diyl, cyclohexane-1,4-diyl or phenylene-1,4-diyl, and/or c3) one or more hydrogen atoms may be replaced by F and/or Cl, p, q are each independently 0 or 1 G1-G2 is —CH2CH—, —CH?C—, —CH2CH2CH— or —CH?CH—CH— M1 is —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CF2—O—, —O—CF2—, —CH?CH—, —CF?CF—, —C?C—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2—, —CH2—CH2—, —CF2—CF2—, —(CH2)4—, —OC(?O)CF?CF— or a single bond, A1 is 1,4-phenylene where one or two hydrogen atoms may be replaced by F, Cl, CN and/or OCF3, or up to three hydrogen atoms may be replaced byType: GrantFiled: July 30, 2004Date of Patent: April 11, 2006Assignee: Merck Patent GmbHInventors: Rainer Wingen, Barbara Hornung, Wolfgang Schmidt
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Patent number: 6916513Abstract: The invention relates to 2,4?-substituted 6-cyclohexyl-trans-decalins of the general formula I in which R1, R2 and Z are as defined in Claim 1, to the use thereof as components of liquid-crystalline media, and to a liquid-crystal display element and an electro-optical display element.Type: GrantFiled: March 22, 2002Date of Patent: July 12, 2005Assignee: Merck Patent GmbHInventors: Matthias Bremer, Detlef Pauluth, Georg Lüssem
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Patent number: 6903230Abstract: It is to provide a process for synthesizing an intended fluorine-containing compound having a geminal difluoro structure with a high yield, by subjecting a carbonyl compound which is readily available to a two-stage reaction.Type: GrantFiled: July 30, 2003Date of Patent: June 7, 2005Assignee: Asahi Glass Company, LimitedInventors: Shuzhong Wang, Kazuhiko Hayashi, Shinsuke Kaga, Kazuya Oharu
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Publication number: 20040169159Abstract: Novel phenylcyclohexanes of the formula I 1Type: ApplicationFiled: September 28, 2001Publication date: September 2, 2004Applicant: MERCK KGAAInventors: Andreas Wachtler, Reinhard Hittich, Eike Poetsch, Herbert Plach, David Coates, Bernhard Rieger, Joachim Krause
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Patent number: 6780477Abstract: The invention relates to liquid-crystalline compounds of the formula I in which R1, R2, A1, A2, A3, A4, Z1, Z2, a, b and c are as defined in claim 1, and to liquid-crystalline media comprising at least compound of the formula I and to electro-optical displays containing a liquid-crystalline medium of this type.Type: GrantFiled: June 12, 2003Date of Patent: August 24, 2004Assignee: Merck Patent GmbHInventors: Peer Kirsch, Detlef Pauluth, Joachim Krause, Michael Heckmeier, Georg Lüssem, Dagmar Klement
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Patent number: 6713135Abstract: The present invention provides novel polyimides, poly(amic acids) and poly(amide esters) thereof, and optical alignment layers derived therefrom, for inducing alignment of liquid crystals and liquid crystal displays. The novel compositions comprise side-chain polymers of the general formula I —L1—D—L2—Cf wherein D comprises 1 to 4 carbon-carbon double bonds, Cf is a monovalent C4 to C20 fluorocarbon radical and L1 and L2 are linking groups. The invention further describes liquid crystal displays and other liquid crystal devices.Type: GrantFiled: December 19, 2000Date of Patent: March 30, 2004Assignee: Elsicon, Inc.Inventors: Wayne M. Gibbons, Patricia A. Rose, Paul J. Shannon, Hanxing Zheng
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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: 6632484Abstract: Described are dialkyne compounds of the formula I in which n, m, R1, R2, X1, X2, X3, X4, Z1, Z2, A1, A2, Q, Y1 and Y2 are as defined herein and the use of such compounds in liquid-crystal media.Type: GrantFiled: July 19, 2001Date of Patent: October 14, 2003Assignee: Merck Patent Gesellschaft mit beschränkter HaftungInventors: Volker Reiffenrath, Georg Lüssem
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Patent number: 6630210Abstract: The invention relates to pentafluorosulfuranylbenzene derivatives of the formula I in which R1, A1, A2, Z1, L1, L2, L3 and n are as defined herein and to the use thereof in liquid-crystalline media.Type: GrantFiled: June 27, 2001Date of Patent: October 7, 2003Assignee: Merck GmbHInventors: Peer Kirsch, Joachim Krause, Michael Heckmeier
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Patent number: 6610219Abstract: Functional optical materials for optical systems that are typically useful in optical waveguides, optical switching systems, optical modulators, optical computing systems and the like. Included are polymer systems and electrooptical chromophores. Polymers are thermoplastic and/or thermosetting polymers and are blended or co-polymerized with the electrooptic chromophore. The thermoplastic or thermosetting polymer selected from an acrylic/methacrylic, polyester, polyurethane, polyimide, polyamide, epoxy resin, or hybrid (organic-inorganic) or nanocomposite polyester polymer. The electrooptic chromophore is selected from a substituted aniline, substituted azobenzene, substituted stilbene, or substituted imine. Methods for improving adhesion promotion for the various novel materials are also provided.Type: GrantFiled: February 6, 2001Date of Patent: August 26, 2003Assignee: Battelle Memorial InstituteInventors: Vincent D. McGinniss, Steven M. Risser
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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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Publication number: 20030003245Abstract: Chiral nonracemic, chiral racemic and achiral compounds useful as component of LC compositions which have a silane tail group which is partially fluorinated. The silane tail group comprises a perfluoroalkyl group.Type: ApplicationFiled: January 3, 2001Publication date: January 2, 2003Inventors: Neil Gough, Xin Hua Chen, William N. Thurmes, Michael Wand
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Publication number: 20020166994Abstract: There is provided a liquid crystalline compound having a high voltage holding ratio which has a very small degree of temperature dependence, a low threshold voltage which has a very small degree of temperature dependence, a high &Dgr;n, and excellent miscibility with other liquid crystal materials at low temperature; a liquid crystal composition; and a liquid crystal display element, and the liquid crystalline compound is a substituted benzene derivative represented by general formula (1), 1Type: ApplicationFiled: July 30, 2001Publication date: November 14, 2002Inventors: Tomoyuki Kondo, Shuichi Matsui, Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki takeshita, Etsuo Nakagawa
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Patent number: 6475595Abstract: Fluorocyclohexene derivatives of formula I R1—(A1—Z1)n—A—(Z2—A2)m—Z3—B—(Z4—A3)p—R2 I, in which n, m, p, R1, R2, Z1, Z2, Z3, Z4, A1, A2, A3, A and B are as defined herein, are suitable for use in liquid crystal mediums. Also, difluorocyclohexanes of formula III R3—A*—(Z6—A7)m—Z7—Qr—R7 III, where R3, A*, Z6, A7, m, Z7, Q, r, and R4 are as defined herein, are suitable for use in liquid crystal mediums.Type: GrantFiled: March 31, 2000Date of Patent: November 5, 2002Assignee: Merck GmbHInventors: Matthias Bremer, Detlef Pauluth, Joachim Krause, Michael Heckmeier, Peer Kirsch
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Publication number: 20020142108Abstract: The instant invention relates to liquid crystal media comprising a strongly dielectrically positive component A, preferably comprising isothiocyanate compounds, most preferably compounds of formula I, as given in the text, and a further dielectrically positive component B, preferably comprising terminally polar substituted bi- or terphenyl compounds, most preferably comprising compounds of formula II, as given in the text, further to novel isothiocyanato compounds as well as to liquid crystal displays comprising these media, in particular to PDLC display and most particular to holographic PDLC displays.Type: ApplicationFiled: February 2, 2001Publication date: October 3, 2002Inventors: Eike Poetsch, Atsutaka Manabe, Volker Reiffenrath, Marcus Reuter, Volker Meyer, Joachim Krause, Detlef Pauluth
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Patent number: 6458433Abstract: Disclosed are liquid crystalline compounds which (i) are characterized in that the compounds have a wide temperature range in which the compounds exhibit a liquid crystal phase, are low in viscosity, and have a negative and large &Dgr;&egr;, (ii) are readily mixed with other various liquid crystal materials even at low temperatures, and (iii) are useful as component of liquid crystal compositions suitable both for TFT type display mode and IPS mode; and liquid crystal composition comprising the liquid crystalline compound; the compounds are expressed by the general formula (1) wherein R1 represents an alkyl group having 1 to 15 carbon atoms; ring A1, ring A2, and ring A3 independently represent trans-1,4-cyclohexylene group, trans-1,4-silacyclohexylene group, pyrimidine-2,5-diyl group, pyridine-2,5-diyl group, 1,3-dioxane-2,5-diyl group, tetrahydropyran-2,5-diyl group, 1,3-dithian-2,5-diyl group, or tetrahydrothiopyran-2,5-diyl group, or 1,4-phenylene group in which one or more hydrogen atomType: GrantFiled: June 16, 1999Date of Patent: October 1, 2002Assignee: Chisso CorporationInventors: Takashi Kato, Shuichi Matsui, Kazutoshi Miyazawa, Fusayuki Takeshita, Etsuo Nakagawa
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Publication number: 20020110650Abstract: There are disclosed novel compounds, liquid crystal compositions, polymers, optically anisotropic products, and optical or liquid crystal elements that have large refractive index anisotropy, mix easily with other liquid crystals, have advantageous stability against light, and exhibit absorption at practically short wavelength in the ultraviolet region. The compounds are represented by the formula (1) and have a phenylacetylene structure, wherein difference &Dgr;E in energy of HOMO of parts (1-1), (1-2) and (1-3) calculated by the method of molecular orbitals is not less than 0.3 electronvolt, and the polarizability anisotropy &Dgr;&agr; of a molecule represented by the formula (1) calculated in the same way is not lower than 500 A.U.Type: ApplicationFiled: February 8, 2002Publication date: August 15, 2002Inventors: Chizu Sekine, Masamitsu Ishitobi, Koichi Fujisawa, Kazunori Iwakura, Masayoshi Minai
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Patent number: 6391397Abstract: A fluorinated phenyl compound having the general formula [1]: wherein each of s, v and x=0 or 1, each of t and u=1, 2 or 3, and each of y and z=0, 1 or 2; A, B and C are independently selected from conjugated cyclic moieties including heterorings and fused rings; R1 and R3 may be independently cyano, or (C1-C12)alkyl, (C1-C12)alkoxy, (C1-C11) alkoxycarbonyl or (C1-C11)alkylcarbonyloxy which may be fluoro- and/or cyano-substituted; R2=H or F; R4=H or F; and R5=H or F. Such compounds have high transverse dipole moments and are potentially useful in liquid crystal compositions and in devices including same.Type: GrantFiled: April 5, 2000Date of Patent: May 21, 2002Assignees: Sharp Kabushiki Kaisha, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: John Clifford Jones, Ian Charles Sage, John William Goodby, Michael Hird, Robert Andrew Lewis, Kenneth Johnson Toyne
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Patent number: 6380432Abstract: The present invention provides novel aromatic diamines useful in preparing polyimides for optical alignment layers in liquid crystal displays. The novel compositions comprise side-chains general formula I —L1—D—L2—Cf wherein D comprises 1 to 4 carbon-carbon double bonds, Cf is a monovalent C4 to C20 fluorocarbon radical and L1 and L2 are linking groups.Type: GrantFiled: December 20, 2000Date of Patent: April 30, 2002Assignee: Elsicon Inc.Inventors: Wayne M. Gibbons, Patricia A. Rose, Paul J. Shannon, Hanxing Zheng
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Publication number: 20020043646Abstract: Novel phenylcyclohexanes of the formula I 1Type: ApplicationFiled: September 28, 2001Publication date: April 18, 2002Applicant: MERCK KGAAInventors: Andreas Wachtler, Reinhard Hittich, Eike Poetsch, Herbert Plach, David Coates, Bernhard Rieger, Joachim Krause
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Publication number: 20020038858Abstract: Disclosed are liquid crystalline compounds which (i) are characterized in that the compounds have a wide temperature range in which the compounds exhibit a liquid crystal phase, are low in viscosity, and have a negative and high &Dgr;&egr;, (ii) are readily mixed with other various liquid crystal materials even at low temperatures, and (iii) are useful as component of liquid crystal compositions suitable both for TFT type display mode and IPS mode; and liquid crystal composition comprising the liquid crystalline compound; the compounds are expressed by the general formula (1) 1Type: ApplicationFiled: June 16, 1999Publication date: April 4, 2002Inventors: TAKASHI KATO, SHUICHI MATSUI, KAZUTOSHI MIYAZAWA, FUSAYUKI TAKESHITA, ETSUO NAKAGAWA
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Patent number: 6348244Abstract: An object of the present invention is to provide novel liquid crystalline compounds having a negative and extremely large dielectric anisotropy value and a small optical anisotropy value together, to provide liquid crystal compositions comprising the liquid crystalline compound, and to provide liquid crystal display devices fabricated by using the liquid crystal composition; the liquid crystalline compounds have 2,3-difluorophenyl moiety and are expressed by the general formula (1) wherein Ra and Rb each independently represent a straight chain or branched alkyl group having 1 to 10 carbon atoms in which group any methylene group may be replaced by —O—, —CH═CH—, or —C≡C—, but there is not a case wherein —O— continues; ring A1 represents cyclohexane-1,4-diyl not adjacent any methylene group may be replaced by —O—; ring A2 represents 2,3-difluoro-1,4-phenylene in which phenylene hydrogen atoms at 5-position and 6-position mType: GrantFiled: April 24, 2000Date of Patent: February 19, 2002Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Hiroyuki Takeuchi, Yasuhiro Kubo, Fusayuki Takeshita, Etsuo Nakagawa
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Patent number: 6342572Abstract: The invention pertains to benzocyclobutene resins having flame retardant properties. Such resins have a high glass transition temperature (Tg>250° C.), low moisture absorption, low dielectric constant, good mechanical properties, flame retardancy (meets or exceeds UL94 V-O and/or VTM-O requirements), and can be cast onto a reinforcement to prepare a laminate for use as a substrate for electronic circuitry. The flame resistant compound is reaction product of a halogen containing compound of the formulae R&Parenopenst; DA)n or R&Parenopenst; DA&Parenclosest;n R2 wherein R is a halogen containing aromatic group, a halogen containing aliphatic group or a combination thereof; R2 is hydrogen, an aromatic group, an aliphatic group or an combination of an aromatic group and an aliphatic group which may contain halogen atoms; DA is a Diels-Alder reactive diene or a group that can act as a dienophile in a Diels-Alder reaction; and n is greater than or equal to 1; with a benzocyclobutene compound.Type: GrantFiled: December 28, 1999Date of Patent: January 29, 2002Assignee: Honeywell International Inc.Inventors: Michael W. Wagaman, Thomas F. McCarthy
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Patent number: 6329529Abstract: Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.Type: GrantFiled: July 31, 1998Date of Patent: December 11, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
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Patent number: 6309561Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one catenary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: December 24, 1997Date of Patent: October 30, 2001Assignee: 3M Innovative Properties CompanyInventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 6242645Abstract: Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating agents are disclosed.Type: GrantFiled: March 23, 2000Date of Patent: June 5, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Guido Peter Pez, Reno Joseph Pesaresi, Jr., Robert George Syvret
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Patent number: 6231934Abstract: The liquid crystalline compound is expressed by the general formula (1) Ra-A1-Z1-A2-Z2-A3-Z3-A4-Rb (1) wherein Ra represents an alkenyl group having 2 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms any methylene group (—CH2—) in the alkenylene or alkyl group may be replaced by —O—, —S—, —CO—, —CH═CH—, or —C≡C—, but in no case —O— and/or —S— continues, and any hydrogen atom in Ra may be replaced by a halogen atom; Rb represents Ra, a halogen atom, or cyano group provided that at least one of Ra and Rb represents a group having double bond; A1, A2, A3, and A4 independently represent trans-1,4-cyclohexylene group, 1,4-phenylene group any hydrogen atom on the ring may be replaced by fluorine atom or cyano group, cyclohexenediyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, or 1,3-dioxane-2,5-diyl group; and Z1, Z2, and Z3 independently represent an alkenylene groType: GrantFiled: September 28, 1998Date of Patent: May 15, 2001Assignee: Chisso CorporationInventors: Tomoyuki Kondo, Shuichi Matsui, Kazutoshi Miyazawa, Yasuko Sekiguchi, Etsuo Nakagawa
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Patent number: 6222064Abstract: A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.Type: GrantFiled: January 14, 2000Date of Patent: April 24, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Guido Peter Pez
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Patent number: 6200654Abstract: 1,4-disubstituted 2,6-difluorobenzene compound of formula I wherein R is an alkyl or alkenyl radical, A1 and A2, in each case independently of one another, are (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—, —CH2—O—, —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 proviso that at least one of the radicals A1 and A2 present in the molecule is are suitable as components of liquid-cType: GrantFiled: August 25, 1997Date of Patent: March 13, 2001Assignee: Merck Patent Gesellschaft mit beschrankter 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: 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: 6171664Abstract: 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: GrantFiled: June 17, 1999Date of Patent: January 9, 2001Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Matthias Bremer, Detlef Pauluth, Harald Hirschmann
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Patent number: 6117361Abstract: A compound represented by the following general formula (1) is provided. This has broader temperature range of nematic phase, lower viscosity and higher miscibility with other liquid crystal compounds at low temperature than those of conventional liquid crystal compounds, and the compounds have high chemical stability. ##STR1## wherein H.sub.1 to H.sub.8 represent independently a hydrogen atom or a halogen atom, provided that at least one of them is a halogen atom; R.sub.1 represents a moiety which is an alkyl group having 2 to 20 carbon atoms provided that one or more methylene groups (--CH.sub.2 --) which are not successive in the alkyl group are replaced with an oxygen atom (--O--) in the form of ether; Y.sub.1 represents an alkyl group having 1 to 20 carbon atoms, and one or more methylene groups in Y.sub.1 independently may be replaced with an oxygen atom, a sulfur atom, a dihydroxysilyl group, a dimethylsililene group, --CH.dbd.CH-- or --C.tbd.C--; X.sub.1 to X.sub.Type: GrantFiled: August 31, 1998Date of Patent: September 12, 2000Assignee: Chisso Corp.Inventors: Koichi Shibata, Tomoyuki Kondo, Shuichi Matsui, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 6030547Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one caternary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: December 24, 1997Date of Patent: February 29, 2000Assignee: 3M Innovative Properties CompanyInventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5981422Abstract: Stoichiometric and catalytic chemical transformations may be carried out in solution using novel fluorous multiphase systems (FMS). The term "fluorous" is defined as a carbon-fluorine bond rich organic molecule which is generated by replacing hydrogen atoms bonded to carbon atoms with fluorine. The novel complexes suitable for use as fluorous catalysts and reagents in the present invention contain sufficient number of fluorous moieties to render them preferentially soluble in the appropriate fluorous solvent without impairing the ability of the catalyst or reagent to be effective or participate in the corresponding reaction.Type: GrantFiled: August 26, 1997Date of Patent: November 9, 1999Assignee: Exxon Research and Engineering Co.Inventors: Istvan Tamas Horvath, Jozsef Rabai
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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: 5968410Abstract: The invention relates to fluorocyclohexane derivatives of the formula I ##STR1## in which R.sup.1, R.sup.2, y.sup.1, y.sup.2, X.sup.1, X.sup.2, A.sup.1, Z.sup.1, Z.sup.2, Z.sup.3, n, m, p and q are as defined above.Type: GrantFiled: July 29, 1998Date of Patent: October 19, 1999Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Peer Kirsch, Joachim Krause, Kazuaki Tarumi
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Patent number: 5858270Abstract: In order to provide novel compounds which are useful as liquid crystal materials for low voltages in several liquid crystal displays, have a large dielectric anisotropy, and are low in viscosity; and to improve characteristics of liquid crystal compositions, difluorooxymethane derivatives expressed by the following general formula (I) and liquid crystal compositions containing the compound are proposed ##STR1## wherein each of l, m, and n is 0 or 1, rings A.sub.1 to A.sub.3 independently represent six-membered rings such as trans-1,4-cyclohexylene and 1,4-phenylene, Z.sub.1 to Z.sub.3 independently represent a bonding group such as covalent bond and --CH.sub.2 CH.sub.2 --, L.sub.1 to L.sub.4 independently represent hydrogen atom or halogen atom, and X represents a group such as halogen atom and OCF3.They are useful as liquid crystal materials for low voltages in several modes such as active matrix mode and STN mode.Type: GrantFiled: January 30, 1997Date of Patent: January 12, 1999Assignee: Chisso CorporationInventors: Shuichi Matsui, Kazutoshi Miyazawa, Noriyuki Ohnishi, Yasuhiro Haseba, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5833879Abstract: A novel liquid crystalline compound having a sufficiently large .DELTA.n, a superior, low temperature compatibility with other liquid crystals and a chemical stability; a liquid crystal composition containing the above compound; and a display element using the above liquid crystal composition are provided,which liquid crystalline compound is expressed by the formula (1): ##STR1## wherein R.sub.1 is an alkyl group or alkoxy group of 1 to 10C, cyano group or a halogen atom; R.sub.2 is an alkyl group of 1 to 5C wherein one methylene group (--CH.sub.2 --) may be replaced by oxygen atom; X.sub.1 and X.sub.2 each independently are hydrogen atom or a halogen atom; A and B each independently are single bond, 1,4-phenylene ring or 1,4-cyclohexylene ring which may be substituted by halogen atom may be; and p is 1 to 5.Type: GrantFiled: February 12, 1996Date of Patent: November 10, 1998Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuko Sekiguchi, Etsuo Nakagawa
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Patent number: 5779936Abstract: A liquid crystalline compound expressed by the general formula (1) ##STR1## (wherein R.sub.1 is an alkyl group having 1 to 12 carbon atoms and one CH.sub.2 group in the alkyl group may be replaced by oxygen atom or --CH.dbd.CH--; X represents hydrogen atom or fluorine atom; Y represents hydrogen atom or alkoxy group having 1 to 5 carbon atoms; l and m independently represent 0 or 1, respectively; and n and p independently represent an integer of 0 to 10, respectively, and when p is 0, n is 1 or more, and when Y is an alkoxy group, X is a fluorine atom and p is 0.)Liquid crystal compositions which are suitable for use in liquid crystal display devices, have a high clearing point, and have a function of decreasing viscosity, and novel liquid crystalline compounds useful as a component of the liquid crystal compositions are provided.Type: GrantFiled: July 24, 1996Date of Patent: July 14, 1998Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Atsuko Fujita, Tomoyuki Kondo, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5776367Abstract: A novel liquid crystalline compound having a low viscosity and a high elastic constant ratio and at the same time, a superior compatibility with other known liquid crystalline compounds, and a liquid crystal composition and a liquid crystal display element containing the novel compound, are provided.The compound is an alkenylcyclohexane derivative expressed by the formula (1): ##STR1## wherein R.sup.1 and R.sup.2 represent a linear or branched alkyl group of 1 to 15 carbon atoms or alkenyl group of 2 to 15 carbon atoms; at least one of R.sup.1 and R.sup.2 represents an alkenyl group; in these groups, one or more non-adjacent CH.sub.2 groups may be replaced by oxygen atom, sulfur atom or --C.tbd.C-- group; ring A.sup.1, ring A.sup.2 and ring A.sup.3 each independently represent 1,4-cyclohexylene group wherein one or more CH.sub.2 groups on the ring may be replaced by oxygen atom or sulfur atom, or 1,4-phenylene group wherein one or more CH groups on the ring may be replaced by nitrogen atom; Z.sup.1 and Z.sup.Type: GrantFiled: June 19, 1996Date of Patent: July 7, 1998Assignee: Chisso CorporationInventors: Shuichi Matsui, Yasuyuki Koizumi, Takashi Kato, Kazutoshi Miyazawa, Norihisa Hachiya, Etsuo Nakagawa
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Patent number: 5714088Abstract: Liquid crystalline compounds are disclosed which are expressed by the following general formula (1) ##STR1## wherein R.sub.1 represents a branched alkyl group having 3 to 10 carbon atoms, ring A represents 1,4-phenylene group or 1,4-cyclohexylene group, Z.sub.1 and Z.sub.2 independently represent a single bond or 1,2-ethylene group, respectively, X.sub.1, X.sub.2, X.sub.3, and X.sub.4 independently represent fluorine atom or hydrogen atom, respectively, and Y.sub.1 represents oxygen atom or a single bond. The compounds are excellent in compatibility with other liquid crystalline compounds, and have a large positive value of dielectric anisotropy, extremely low viscosity, extremely high specific resistance (high voltage holding ratio), and excellent UV stability.Type: GrantFiled: March 22, 1996Date of Patent: February 3, 1998Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuko Sekiguchi, Etsuo Nakagawa
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Patent number: 5670085Abstract: A liquid crystalline compound expressed by the formula ##STR1## wherein R.sub.1 represents an alkyl group of 1 to 12 carbon atoms, and one or two not adjacent CH.sub.2 group excluding the terminal in this group may be replaced by --CO-- group, --OCO-- group, --COO-- group or --CH.dbd.CH group; X and Z each represents H, F or Cl; Y represents perfluoroalkyl group or perfluoroalkyloxy group of 1 to 4 carbon atoms, and one or two F atoms in this group may be replaced by H; one of A, B and C represents cyclohexene ring and the others thereof are chosen from among covalent bond or cyclohexane group and benzene ring and these rings may be substituted by F or Cl; and l, m and n each are 0 or 1, independently of each other, but when m=0, then l=0.EffectivenessIt is possible to provide a liquid crystal composition having a large .DELTA.n, a low viscosity and a high voltage-holding ratio, and exhibiting a nematic liquid crystal phase within a broad temperature range and having a very high .DELTA..epsilon.Type: GrantFiled: January 18, 1996Date of Patent: September 23, 1997Assignee: Chisso CorporationInventors: Kazutoshi Miyazawa, Shuichi Matsui, Yasuyuki Goto, Etsuo Nakagawa, Shinichi Sawada
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Patent number: 5621147Abstract: A 1,1,2-trifluoro-2-(trans-4-substituted cyclohexyl)ethylene of the formula (1):R--(A).sub.m --Cy--CF=CF.sub.2 (1)wherein R is a C.sub.1-10 alkyl group, a halogen atom or a cyano group, provided that in the case of the alkyl group, an oxygen atom may be interposed in a carbon-carbon bond of the alkyl group or in a carbon-carbon bond between this alkyl group and A, some of carbon-carbon bonds in the alkyl group may be triple bonds or double bonds, one --CH.sub.2 -- group in the alkyl group may be substituted by a carbonyl group, and some or all of hydrogen atoms in the alkyl group may be substituted by fluorine atoms;Cy is an unsubstituted trans-1,4-cyclohexylene group;A is a trans-1,4-cyclohexylene group, a 1,4-phenylene group or a 1,4-cyclohexenylene group, wherein each of such cyclic groups is unsubstituted or substituted by one or more halogen atoms or cyano groups, one or more =CH-- groups constituting rings of such cyclic groups may be substituted by nitrogen atoms, and one or more --CH.sub.Type: GrantFiled: May 4, 1995Date of Patent: April 15, 1997Assignee: Asahi Glass Company Ltd.Inventors: Osamu Yokokoji, Tamaki Simizu, Seisaku Kumai
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Patent number: 5589102Abstract: Benzene derivatives of the formula I ##STR1## in which R, A.sup.1, A.sup.2 X, L.sup.1, L.sup.2 m and n are as defined in claim are suitable as components of liquid-crystalline media.Type: GrantFiled: September 5, 1995Date of Patent: December 31, 1996Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Kazuaki Tarumi
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Patent number: 5565140Abstract: The invention relates to novel halogenated benzene derivatives of the formula I ##STR1## in which n is 1 to 7 [sic], the rings A and B are each trans-1,4-cyclohexylene, or one of the rings A and B is alternatively 1,4-phenylene or 3-fluoro-l,4-phenylene, X is F, C1, CHF.sub.2, --CF.sub.3, --CN, --OCF.sub.3 or --OCHF.sub.2, Y and Z are each, independently of one another, H or F, r=1 or, in the case where s=1, B=trans-1,4-cyclohexylene and simultaneously X=--CHF.sub.2, --CF.sub.3, --OCF.sub.3 or --OCHF.sub.2, r is alternatively 0, and s=1 or, in the case where B=1,4-phenylene or 3-fluoro-1,4-phenylene, s=0.Type: GrantFiled: June 5, 1995Date of Patent: October 15, 1996Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Reinhard Hittich, Eike Poetsch, Volker Reiffenrath, Bernhard Rieger, Andreas Wachtler, David Coates, Herbert Plach
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Patent number: 5560863Abstract: 2-Fluorocyclohexene derivatives of formula I ##STR1## where R, A.sup.1, Z.sup.1, X, L.sup.1, L.sup.2, m and n are as defined herein, and their use as components of liquid-crystalline media for electro-optical display elements, in particular for matrix liquid-crystal displays.Type: GrantFiled: April 5, 1995Date of Patent: October 1, 1996Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Herbert Plach
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Patent number: 5545769Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.Type: GrantFiled: September 29, 1994Date of Patent: August 13, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
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Patent number: 5242618Abstract: Di- and trifluorotolans of the formula I. ##STR1## in which R.sup.1 is alkyl having up to 9 carbon atoms, andL is H or Fare suitable as components of liquid-crystalline media.Type: GrantFiled: April 19, 1991Date of Patent: September 7, 1993Assignee: Merck Patent GesellschaftInventors: Joachim Krause, Volker Reiffenrath, Ulrich Finkenzeller
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Patent number: 5220082Abstract: This invention concerns a process for the production of polyfluoroolefins by the catalytic addition of polyfluoroallylic fluorides to fluoroethylenes. 1:1 and 1:2 Adducts such as F-pentene-2 and F-heptene-3 can be formed selectively and reduced further to dihydro- or trihydropolyfluoroalkanes, which are useful as HFC cleaning agents.Type: GrantFiled: June 25, 1992Date of Patent: June 15, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan