Acyclic Unsaturation Containing Patents (Class 570/128)
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Patent number: 6875895Abstract: Provided is a bis(diphenylvinyl)arene compound having a reactive functional group on phenyl group, represented by below formula (1), wherein, Ar is an arylene group and has one or more substituents; R1-R22 each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, etc., and at least one of R1-R20 is a halogen atom, etc. The arene compound has sufficient solubility in an organic solvent and excellent reactivity.Type: GrantFiled: August 20, 2002Date of Patent: April 5, 2005Assignee: Sumitomo Chemical Company, LimitedInventors: Takahiro Ueoka, Hideyuki Ikehira, Yoshiaki Tsubata
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Patent number: 6838017Abstract: New tolane and bis-tolane compounds: in which X is F (fluoro), CN (cyano), OCF3 (trifluoromethoxy), or NCS (isothiocyanate) at least one of the pairs Y1 and Y2, Z1 and Z2, and A1 and A2 are fluoro groups. T1 for the tolanes is a triple bond. For the bis-tolane T1 and T2 are either both triple bonds or one of the two groups is a double bond. Rn or Rm may be an alkyl group, and alkenyl group, and alkoxy group, or an alkenoxy group. For the tolane compounds, Rn may be a: dioxane substituent: ?in which Rx may be as Rn or Rm above. These compounds exhibit useful nematic ranges and melting points. Also disclosed are eutectic mixtures including these compounds.Type: GrantFiled: September 5, 2000Date of Patent: January 4, 2005Assignee: HRL Laboratories, LLCInventors: Shin-Tson Wu, Zheng Chai
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Patent number: 6812311Abstract: A method of producing a highly stable packaging substrate in which are provided a first precursor having a first backbone and a first ethynyl group, and a second precursor having a second backbone and a second ethynyl group. Furthermore provided is a crosslinker having a first and a second reactive group. The first precursor, the second precursor, the crosslinker, and a solvent are applied onto a surface to form an electrically insulating layer. The first ethynyl group is reacted with the first reactive group in a first carbon-carbon bond formation reaction and the second ethynyl group is reacted with the second reactive group in a second carbon-carbon bond formation reaction to crosslink the first backbone with the second backbone, thereby forming the packaging substrate. The solvent is removed in a further step.Type: GrantFiled: October 18, 2001Date of Patent: November 2, 2004Assignee: Honeywell International Inc.Inventors: Thomas McCarthy, Michael Wagaman, David Schwind
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Patent number: 6811832Abstract: Compounds of the formula (I): in which X1=H or F, X2=H or F, and Y=Cl, Br or I, are prepared by reacting, in a solvent or solvent mixture at a temperature below −60° C., a halobenzene of the formula (II) with an organic lithium compound and then with a formyl equivalent of the formula (III): and may be used as starting materials for preparing agrochemicals, electronic materials and pharmaceuticals.Type: GrantFiled: May 10, 2001Date of Patent: November 2, 2004Assignee: Clariant GmbHInventors: Rainer Wingen, Wolfgang Schmidt
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Patent number: 6770788Abstract: A two-step process for the preparation of fluoroolefin compounds of formula I wherein R is hydrogen or alkyl, and R1 is alkyl or cyclopropyl, or R and R1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group; Ar is phenyl or naphthyl both of which are optionally substituted; Ar1 is phenoxyphenyl, biphenyl, phenyl, benzylphenyl, or benzoylphenyl, all of which may be optionally substituted, comprising reacting fluorobromoolefin compounds of formula II with organozinc compounds of formula III or IV BrZnCH2Ar1 III Zn[CH2Ar1]2 IV in the presence of a palladium catalyst and a solvent, which compounds of formula II are obtained by reacting aldehyde compounds of formula V with (a) fluorotribromomethane, (b) a tri(substituted)phosphine or a hexaalkylphosphoramide or a mixture thereof, and (c) zinc, in the presence of a solvent, compounds of formula II.Type: GrantFiled: October 21, 2002Date of Patent: August 3, 2004Assignee: BASF AktiengesellschaftInventor: William Wakefield Wood
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Publication number: 20040147788Abstract: The invention relate to stilbene derivatives having formula I 1Type: ApplicationFiled: November 4, 2003Publication date: July 29, 2004Inventors: Jean-Francois Savouret, Marc Poirot, Philippe De Medina, Robert F. Casper
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Publication number: 20040138467Abstract: Aromatic and aromatic/heteroaromatic molecular structures with controllable electron conducting properties are derived from the incorporation of electron active substituents in selective positions.Type: ApplicationFiled: November 25, 2003Publication date: July 15, 2004Inventors: Roger Harquail French, Ross Getty, Simona Percec
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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: 6733883Abstract: This invention relates to novel fluorinated dendrons and to a universal strategy for producing functional fluorinated dendrons programmed to self-assemble into supramolecular nanocylinder compositions containing p-stacks of high electron or hole mobility donors (D), acceptors (A), or D-A complexes in the core. Such nanocylinder compositions are uniquely applicable to devices spanning from single supramolecule to nanoscopic and to macroscopic scales including transistors, photovoltaics, photoconductors, photorefractives, light emissives, and optoelectronics.Type: GrantFiled: November 12, 2002Date of Patent: May 11, 2004Assignee: The Trustees of the University of PennsylvaniaInventor: Virgil Percec
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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: 6696111Abstract: 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 IA and/or IB in which Ra, Rb, Ya, Yb, Za, Zb, La, Lb, c and d are as defined herein, is suitable for use in MLC, TN and STN displays.Type: GrantFiled: October 11, 2001Date of Patent: February 24, 2004Assignee: Merck Patent GmbHInventors: Michael Heckmeier, Matthias Bremer
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Patent number: 6693223Abstract: A novel liquid crystal compound, a nematic liquid crystal composition, and a liquid crystal display system using the composition are disclosed herein. The liquid crystal compound is represented by the general formula (I): wherein R represents a hydrogen atom or a straight chain alkyl group having 1 to 7 carbon atoms and each of X, Y and Z independently represents hydrogen atom or fluorine atom. The nematic liquid crystal composition of the present invention can provide liquid crystal materials in response to desired purposes even by its addition in a small amount without spoiling other characteristics.Type: GrantFiled: February 27, 2003Date of Patent: February 17, 2004Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Kiyofumi Takeuchi, Haruyoshi Takatsu, Sadao Takehara, Masashi Osawa
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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: 6682661Abstract: 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 electroptical system. The electroptical system comprises a PDLC film comprising a liquid crystal mixture forming micro-droplets in an optically isotropic, transparent polymer matrix between 2 electrode layers. 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: March 18, 2002Date of Patent: January 27, 2004Assignee: Merck Patent GesellschaftInventors: David Coates, Owain Llyr Parri, Simon Greenfield, Martin David Tillin, Mark John Goulding, Patrick Nolan
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Patent number: 6670511Abstract: A fluorine-containing diene represented by the formula 1: CF2═CF(CF2)nCXYOCF═CF2 Formula 1 wherein each of X and Y which are independent of each other, is an atom selected from a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, provided that X and Y are not simultaneously hydrogen atoms or fluorine atoms, and n is an integer of from 1 to 3.Type: GrantFiled: May 15, 2002Date of Patent: December 30, 2003Assignee: Asahi Glass Company LimitedInventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
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Patent number: 6653515Abstract: &agr;,&bgr;,&bgr;-Trifluorostyrene and derivatives thereof synthesized in two steps from 1,1,1,2-tetrafluoroethylene. In the first step, 1,1,1,2-tetrafluoroethylene is reacted with a base, a metal salt such as zinc chloride and an optionally amine to form a trifluorovinyl metal complex. In the second step, the trifluorostyrene or derivative is obtained by reacting the trifluorovinyl metal complex with an aryl transfer agent such as, for example, an aryl triflate or an aryl halide, in the presence of a metal catalyst and optionally a coordinating ligand. Both steps may be carried out in one reactor.Type: GrantFiled: December 14, 2001Date of Patent: November 25, 2003Assignee: Ballard Power Systems Inc.Inventors: Charles Stone, Timothy J. Peckham, Donald J. Burton, Anilkumar Raghavanpillai
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Patent number: 6649227Abstract: Provided are liquid crystalline compounds having a wide liquid crystal phase temperature range, low viscosity, a large elastic constant ratio K33/K11 and excellent solubility at low temperature, a liquid crystal composition using the same and a liquid crystal display.Type: GrantFiled: July 6, 2001Date of Patent: November 18, 2003Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Takashi Kato, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
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Patent number: 6635318Abstract: Disclosed is a tetracyclic compound of the formula I in which R1, R2 are each, independently of one another, an alkyl or alkenyl radical having up to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF3, or monosubstituted by halogen. One or more CH2 groups in these radicals may also, in each case independently of one another be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— such that the O atoms are not linked directly to one another. Z is —OCF2—, —CF2O— or a single bond. L1, L2, L3, and L4 are each, independently of one another, H or F. m is 1 or 2. Similar compounds, as well as liquid-crystalline media having these compounds, are also disclosed.Type: GrantFiled: August 13, 2001Date of Patent: October 21, 2003Assignee: Merck Patent Gesellschaft mit beschränkter HaftungInventors: Peer Kirsch, Joachim Krause, Georg Lüssem, Dagmar Klement
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Patent number: 6623810Abstract: The present invention provides novel phenylacetylene compounds, liquid crystal compositions having a large refractive index anisotropy (&Dgr;n), and liquid crystal elements produced with the same.Type: GrantFiled: April 25, 2001Date of Patent: September 23, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Chizu Sekine, Koichi Fujisawa, Kazunori Iwakura, Masayoshi Minai
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Publication number: 20030171628Abstract: The present invention provides a perfluoroolefin-hydrocarbon hybrid compound represented by the following general formula (1):Type: ApplicationFiled: February 26, 2003Publication date: September 11, 2003Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGYInventors: Masakazu Nishida, Taizo Ono
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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: 6599590Abstract: The invention relates to a fluoro-substituted alkenyl compound represented by formula (1) wherein Y1, Y2, Y3 and Y4 are each independently H or F, provided that at least one of Y1 and Y2 is F; Q1 is a single bond or an alkylene group of 1-20 carbon atoms, at least one —CH2— being optionally substituted by —O—, provided that two or more —O— are not adjacent to each other; Q2 is a single bond or —C≡C—; Rings A1, A2 and A3 are each independently a cyclohexane ring, a dioxane ring, a cyclohexene ring, a pyrimidine ring, a pyridine ring, or a benzene ring, or a benzene ring having at least one hydrogen atom substituted by F; Z1, Z2 and Z3 are each independently a single bond, —CH2CH2—, —CH2O—, —OCH2—, —COO—, —OCO—, —CH═CH—, —C≡C—, —CF2O—, or —OCF2; and m and n are each independently 0 or 1; provided that Y3 is F when Ring A3 is a cyType: GrantFiled: May 22, 2001Date of Patent: July 29, 2003Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Yasuhiro Haseba, Shuichi Matsui, Hiroyuki Takeuchi, Yasuhiro Kubo, Etsuo Nakagawa
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Patent number: 6552228Abstract: The present invention relates to a process for the treatment of an aryl carbamoyl fluoride comprising in its molecule at least one perhalogenated aliphatic carbon, which carbon carries at least one halogen atom to be exchanged with fluorine. This process comprises the stage of bringing the said carbamoyl fluoride into contact with hydrofluoric acid, the ratio of hydrofluoric [lacuna] to carbamoyl fluoride being maintained during the reaction at a value at least equal to 4, preferably to 5, and characterized in that the said ratio is at most equal to 11. Application to organic synthesis.Type: GrantFiled: July 5, 2000Date of Patent: April 22, 2003Assignee: Rhodia ChimieInventors: Gilbert Guidot, Christophe Rochin, Laurent Saint-Jalmes
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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: 6541674Abstract: A process for condensing at least one carbonyl compound carrying at least one electron-withdrawing group with an aromatic derivative carrying at least one hydroxyl functional group, wherein the electron-withdrawing group present on the carbonyl compound is selected from fluoroalkyl derivatives, esters, including orthoesters, and nitriles and said condensation is carried out in a basic medium.Type: GrantFiled: November 29, 2000Date of Patent: April 1, 2003Assignee: Rhodia ChimieInventors: Roland Jacquot, Michel Spagnol
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Patent number: 6528676Abstract: The application discloses methods of treating mammalian diseases characterized by abnormal cell mitosis by administering estradiol derivatives including those comprising colchicine or combretastatin A-4 structural motifs of the general formulae found below in a dosage sufficient to inhibit cell mitosis. The application discloses novel compounds used in the methods.Type: GrantFiled: February 2, 1999Date of Patent: March 4, 2003Assignee: The Children's Medical Center CorporationInventors: Robert John D'Amato, Moses Judah Folkman
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Patent number: 6495728Abstract: A two-step process for the preparation of fluoroolefin compounds of formula I wherein R is hydrogen or alkyl, and R1 is alkyl or cyclopropyl, or R and R1 are taken together with the carbon atom to which they are attached to form a cyclopropyl group; Ar is phenyl or naphthyl both of which are optionally substituted; Ar1 is phenoxyphenyl, biphenyl, phenyl, benzylphenyl, or benzoylphenyl, all of which may be optionally substituted, comprising reacting fluorobromoolefin compounds of formula II with organozinc compounds of formula III or IV in the presence of a palladium catalyst and a solvent, which compounds of formula II are obtained by reacting aldehyde compounds of formula V with (a) fluorotribromomethane, (b) a tri(substituted)phosphine or a hexaalkylphosphoramide or a mixture thereof, and (c) zinc, in the presence of a solvent, compounds of formula II.Type: GrantFiled: September 12, 2001Date of Patent: December 17, 2002Assignee: BASF AktiengesellschaftInventor: William Wakefield Wood
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Patent number: 6448452Abstract: A polymer which contains monomer units formed by polymerization of a fluorine-containing diene of formula 1: CF2═CF(CF2)nCXYOCF═CF2 Wherein X and Y are hydrogen and chlorine, hydrogen and-bromine, hydrogen and iodine, fluorine and chlorine, fluorine and bromine, fluorine and iodine, chlorine and bromine, chlorine and iodine, bromine and bromine, bromine and iodine, or iodine and iodine and n is an integer from 1 to 3.Type: GrantFiled: April 25, 2001Date of Patent: September 10, 2002Assignee: Asahi Glass Company LimitedInventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
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Patent number: 6433231Abstract: A method for producing inexpensively in a high yield a halogen-containing aromatic compound, particularly a halogen-containing aromatic compound incorporating therein a bromodifluoroalkyl group, and a halogen-containing naphthalene compound useful as a raw material for a resin excelling in heat resistance, chemical resistance and water repellency, and having a low dielectric constant and a low refractivity are provided.Type: GrantFiled: June 21, 2001Date of Patent: August 13, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Seiichi Teshima, Masayoshi Konishi, Kozo Tajiri, Yoshinobu Asako, Sadao Miki
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Publication number: 20020066888Abstract: Liquid crystalline compounds are disclosed which have large dielectric anisotropy and relatively low viscosity, and which are represented by formula (1) 1Type: ApplicationFiled: April 26, 2001Publication date: June 6, 2002Inventors: Koichi Shibata, Shuichi Matsui, Hiroyuki Takeuchi, Katsuyuki Kawano, Yasuhiro Kubo, Etsuo Nakagawa
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Patent number: 6388146Abstract: The polymerizable compound of this invention is represented by general formula (I): where R is H, R′, R′O, R′COO, or R′OCO, R′ is a linear or branched alkyl group or alkenyl group having 1 to about 15 carbon atoms, A1 and A2 are independently a cyclohexane ring or a benzene ring which may include a substituent represented by formula (II) below; X is H or CH3; and Y1, Y2, Y3, and Y4 are independently H, F, Cl, CH3, CH3O, CF3, or CF3O wherein at least two of Y1, Y2, Y3, and Y4 are H and, if both A1 and A2 are cyclohexane rings, at least one of Y1, Y2, Y3, and Y4 is not H: where Y5, Y6, Y7, and Y8 are independently H, F, Cl, CH3, CH3O, CF3, or CF3O, at least two of Y5, Y6, Y7, and Y8 are H.Type: GrantFiled: January 27, 1999Date of Patent: May 14, 2002Assignees: Sharp Kabushiki Kaisha, Kanto Kagaku Kabushiki KaishaInventors: Noriaki Onishi, Aya Miyazaki, Hoyo Mizobe, Masahiko Yoshida, Kenji Suzuki
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Patent number: 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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Patent number: 6350925Abstract: A synthesis is provided for &agr;,&bgr;-difluoro-&bgr;-halo-ethenyl aromatic compounds such as &agr;,&bgr;,&bgr;-trifluorostyrenes by a process of reacting CFX2CFXI, wherein each X is independently F or Cl, provided that at least one X is Cl and at least one X is F, with an aromatic compound Ar to form (CFX2CFX)n—Ar, wherein n is 1, 2 or 3, and subsequently dechlorohalogenating this product to form (CFX═CF)n—Ar. Novel synthetic intermediate compounds are provided.Type: GrantFiled: July 31, 1998Date of Patent: February 26, 2002Assignee: 3M Innovative Properties CompanyInventor: George Van Dyke Tiers
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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: 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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Publication number: 20010039361Abstract: The present invention provides novel aromatic diamines useful in preparing polyimides for optical alignment layers in liquid crystal displays.Type: ApplicationFiled: December 20, 2000Publication date: November 8, 2001Inventors: Wayne M. Gibbons, Patricia A. Rose, Paul J. Shannon, Hanxing Zheng
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Patent number: 6312618Abstract: A new class of asymmetric polar diphenyldiacetylene liquid crystal compounds and method for preparation are disclosed. The new class of liquid crystal compounds comprises the basic structure: Wherein R1 is an alkenyl group having the general formula (C2H2n−1), X is a cyano group, a fluoro group, CF3, OCF3, or a chloro group, Y1 is unsubstituted, a fluoro group, a chloro group or a methyl group, Y2 is unsubstituted, a fluoro group, a chloro group, or a methyl group, Z1 is unsubstituted, a fluoro group, or a methyl group, and Z2 is unsubstituted, a fluoro group, or a methyl group. The compounds disclosed exhibit high birefringence, low rotational viscosity, and have unexpectedly broad nematic ranges. Also disclosed are eutectic mixtures comprising at least one polar diphenyldiacetylene having the general structure described above. The eutectic mixtures also have unexpectedly broad nematic ranges.Type: GrantFiled: April 3, 2000Date of Patent: November 6, 2001Assignee: HRL LaboratoriesInventors: Shin-Tson Wu, Mary E. Neubert
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Patent number: 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: 6288011Abstract: Pesticidal 1,4-diaryl-2,3-difluoro-2-butene compounds having the structural formula I and compositions and methods comprising those compounds for the control of insect and acarid pests.Type: GrantFiled: November 11, 1998Date of Patent: September 11, 2001Assignee: American Cyanamid Co.Inventors: Terence James Bentley, Keith Douglas Barnes
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Patent number: 6262319Abstract: A process and intermediate compounds for the preparation of fluoroolefin compounds which are useful as pesticidal agents.Type: GrantFiled: December 21, 1998Date of Patent: July 17, 2001Assignee: American Cyanamid Co.Inventors: Keith Douglas Barnes, Yulin Hu, David Allen Hunt
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Patent number: 6252001Abstract: Compounds of ethynyl aromatic compounds form polymers which have high thermal stability. The monomers are useful for coating a wide variety of substances such as dielectric coatings where high thermal resistance is desirable including electronic components such as computer chips.Type: GrantFiled: January 13, 2000Date of Patent: June 26, 2001Assignee: The Dow Chemical CompanyInventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
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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: 6207846Abstract: The present invention provides an improved process and intermediate compounds for the preparation of di-fluorovinylsilane insecticidal and acaricidal agents of the formula I wherein Ar is phenyl, 1- or 2-napthyl or a 5- or 6-membered heteroaromatic ring, each of which may be optionally substituted by any combination of from one to three halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C(O)R2 or S(O)nR3 groups, R and R1 are each independently C1-C4 alkyl or C3-C5 cycloalkyl; Ar1 is phenoxyphenyl, phenyl, biphenyl; phenoxypyridyl, benzylpyridyl, benzylphenyl, 1- or 2- napthyl or a 5- or 6-membered heteroaromatic ring, each of which may be optionally substituted by any combination of from one to five halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy or C(O)R4 groups, n is an integer of 0, 1 or 2; R2 and R4 are each independently C1-C4alkyl, benzyl or phenyl; R3 is C114 C4alkyl or C1 -C4haloalkyl; and the fluorine atoms attached to the double bond are traType: GrantFiled: July 2, 1999Date of Patent: March 27, 2001Assignee: American Cyanamid Co.Inventors: Keith D. Barnes, Yulin Hu
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Patent number: 6194606Abstract: The present invention provides compounds having the formula: in which R is hydrogen or C1-C4alkyl, preferably hydrogen and Y is hydrogen, C1-C4alkyl, C1-C4alkoxy, CF3, halogen (F, Cl, Br or I) or SO3M in which M is H, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C1-C4alkylammonium, mono-, di- or tri-hydroxyalkylammonium or ammonium that is di- or tri-substituted with a mixture of C1-C4alkyl and C1-C4hydroxyalkyl groups; a process for their production; and their use as intermediates in the production of asymmetric or symmetric fluorescent whitening agents.Type: GrantFiled: September 22, 1998Date of Patent: February 27, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Bernd Siebenhaar, Bruno Casagrande, Victor Eliu
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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: 6159393Abstract: A liquid-crystalline medium based on a mixture of polar compounds of positive dielectric anisotropy, characterized in that it contains one or more compounds of the general formula I ##STR1## in which R, Y, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2, L.sup.1 and m are as defined herein.Type: GrantFiled: April 21, 1997Date of Patent: December 12, 2000Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Kazuaki Tarumi, Ekkehard Bartmann, Volker Reiffenrath, Sabine Schoen, Detlef Pauluth, Brigitte Schuler, Eike Poetsch
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Patent number: 6139771Abstract: This invention provides LC compositions useful as birefringent materials in electrooptic devices which exhibit zero or low negatively sloped birefringence dispersion (e.g., exhibiting positive birefringence dispersion significantly lower than that of currently available LC compositions) or more preferably positively sloped birefringence dispersion in which birefringence of the material increases with wavelength. The invention provides compounds useful as components of LC compositions which exhibit negative birefringence where n.sub.o is higher than n.sub.e. The compounds of this invention are dimers of LC-like compounds in which the monomers are linked to each other through a high birefringence moiety (dimerization linker). The LC monomers consist of an LC core and one or two tail groups. Preferred monomers for this invention have low birefringence in comparison to the birefrigence of the monomer linking moiety.Type: GrantFiled: April 4, 1997Date of Patent: October 31, 2000Assignee: Displaytech, Inc.Inventors: David M. Walba, Daniel J. Dyer, Uwe Muller, Peter Cobben, Xin Hua Chen, William Thurmes, Michael Wand
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Patent number: 6121495Abstract: Compounds of ethynyl aromatic compounds form polymers which have high thermal stability. The monomers are useful for coating a wide variety of substances such as dielectric coatings where high thermal resistance is desirable including electronic components such as computer chips.Type: GrantFiled: September 12, 1996Date of Patent: September 19, 2000Assignee: The Dow Chemical CompanyInventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
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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: RE37087Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I in which R1, R2, R3, R4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.Type: GrantFiled: June 20, 1991Date of Patent: March 6, 2001Assignee: Schering AktiengesellschaftInventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles