Patents Examined by Richard Treanor
  • Patent number: 5167862
    Abstract: Compounds which may be used as a dopant or host in a ferroelectric chiral smectic liquid crystal mixture. The compounds are characterized in that they are derivates of an X-hydroxy carboxylic acid and contain the chiral unit (I), in which Ro may be alkyl, alkoxy, halogen, formula (II), where b may be 0 to 3 and the phenyl ring may be substituted, and a is 0 or 1. The chiral unit is combined with a range of mesogenic combinations of groups. Lactic acid derivatives are described in detail (i.e. Ro.dbd.methyl) together with various preparative routes, for example the compound formula (III), which has dopant properties in a range of hosts.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: December 1, 1992
    Inventors: Lawrence K. M. Chan, David Coates, Peter A. Gemmell, George W. Gray, David Lacey, Kenneth J. Toyne, Daniel J. S. Young
  • Patent number: 5093471
    Abstract: Novel mesogenic amine curing agent for reactive monomers, such as epoxy resins and diisocyanates, comprises a mesogenic moiety, a primary amine, and a flexible alkyl spacer connected between the mesogenic moiety and the primary amine and wherein the alkyl spacer is a saturated, linear alkyl group having from about one to about twenty carbon atoms. Novel mesogenic amine has the formula: ##STR1## where M is --O--, ##STR2## or --CH.sub.2 --, where R is --NO.sub.2 or --CN, andwhere x is 1 to 20.Novel mesogenic amine has a labile group subject to cross-linking and the formula: ##STR3## where K is ##STR4## where L is ##STR5## where M is --o--, ##STR6## or --CH.sub.2 --, where Z is cinnamate, an alkene having from one to ten carbons, an isocyanate, an alkoxy, or an alcohol having from one to ten carbons,where T is a cyano, a nitro or an alkyl group having from about one to ten carbons, andwhere X is 1 to 20.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: March 3, 1992
    Assignee: Kent State University
    Inventor: John L. West
  • Patent number: 5087387
    Abstract: An improved light modulating material for use in electro-optic and thermo-optic display devices is produced by forming a homogeneous solution comprising an acrylic resin containing active hydrogen groups, a liquid crystal material, a diisocyanate or epoxide, and a solvent. The homogeneous solution is preferably applied to a conductive substrate and the solvent is then evaporated, causing phase separation resulting in formation of a liquid crystal phase dispersed within a solid polymer matrix. Application of an electric field to the substrate causes the liquid crystal material to align, which in turn causes the coating to switch from substantially translucent to substantially transparent. If the electric field is removed the light modulating material again becomes substantially translucent. Switching times can be improved by incorporating a titanate or zirconate organometallic material into the light modulating material.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: February 11, 1992
    Assignee: Kent Research Corporation
    Inventors: Patrick W. Mullen, Frederick E. Nobile
  • Patent number: 5084204
    Abstract: Naphthylacetylenes of the formula IR.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --C.tbd.C--A.sup.3 --(Z.sup.2 --A.sup.4).sub.n --R.sup.2 Iin which R.sup.1, A.sup.1, Z.sup.1, m, A.sup.2, A.sup.3, Z.sup.2, A.sup.4, n and R.sup.2 have the meanings described herein, are suitable as components of liquid crystal phases.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: January 28, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Georg Weber
  • Patent number: 5084203
    Abstract: In one embodiment this invention provides an optical medium which consists of a microdispersion of liquid crystal droplets in a synthetic resin matrix. A preferred invention optical medium exhibits a Kerr effect, and can transmit propagating light waves with low scattering loss under waveguiding conditions.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: January 28, 1992
    Assignee: Hoechst Celanese Corp.
    Inventors: Michael J. Sansone, Mark S. Kwiatek
  • Patent number: 5080832
    Abstract: Optically nonlinear aromatic carboxylic acid cocrystals are provided of the formula: ##STR1## wherein each R is CN or NO.sub.2, n is 1-4, m is 1-3 and X and Y are individually (C.sub.1 -C.sub.3)alkyl, (C.sub.1 -C.sub.3)-alkanolyl, (C.sub.1 -C.sub.3)alkoxycarbonyl, ar(C.sub.1 -C.sub.5)alkyl, aryl, (C.sub.1 -C.sub.3)alkoxy, hydroxy, halo or mixtures thereof.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: January 14, 1992
    Assignee: Regents of the University of Minnesota
    Inventors: Margaret C. Etter, Gayle M. Frankenbach
  • Patent number: 5080827
    Abstract: An optically active compound particularly useful as a component of liquid crystal compositions having a high response rate and a chiral liquid crystal composition containing the same are provided, which optically active compound is expressed by the formula (I) ##STR1## wherein R.sup.1 represents alkyl or alkoxy each of 1-20 C, H, halogen or CN; ##STR2## and ##STR3## each represent a specified six-membered ring; R.sup.2 represents alkyl of 1-20 C; the asterisk designates an asymmetric carbon atom; and m and n each represents 0 or 1.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: January 14, 1992
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Shinichi Saito, Kouji Ohno, Hiromichi Inoue, Makoto Ushioda
  • Patent number: 5081221
    Abstract: Provided is a novel chiral smectic C liquid crystalline polyester consisting essentially of structural units (A), (B) and (C) of the following formulae: ##STR1## which is optically active and wherein R represents an alkyl group having 1 to 3 carbon atoms, and ##STR2## wherein n represents an integer of 2 to 10.
    Type: Grant
    Filed: September 6, 1988
    Date of Patent: January 14, 1992
    Assignee: Nippon Oil Company, Limited
    Inventor: Junji Watanabe
  • Patent number: 5073303
    Abstract: A photochromic material adapted for coating light transmissive materials. The photochromic material contains photosensitive silver halide crystals having dimensions in the range of approximately 50 Angstroms to 800 Angstroms. The silver halide crystals are surface doped with copper ions and another sensitizer selected from mild reducing agents or sulfur-bearing ions. The crystals are dispersed in a protective polymer that does not irreversibly bind halogen.
    Type: Grant
    Filed: July 2, 1990
    Date of Patent: December 17, 1991
    Assignee: BSG, Inc.
    Inventor: Jerome L. Reid
  • Patent number: 5071589
    Abstract: The novel liquid-crystalline mixtures (in the case of ferroelectric behavior they additionally contain an optically active compound as dope) are constructed from at least 2 mixture components of the general formula (I): ##STR1## wherein n=6 to 14 and x=2 to 14. In addition, the mixtures may also contain cyclohexanecarboxylates of the general formula (II) ##STR2## where R.sup.1 =(C.sub.10 -C.sub.16) or (C.sub.8 -C.sub.14)alkoxy and R.sup.2 =(C.sub.2 -C.sub.9)alkyl, alkenyloxyphenylpyrimidine derivatives of the general formula (III) ##STR3## where R.sup.3 =(C.sub.7 -C.sub.16)alkyl or (C.sub.6 -C.sub.14)alkoxy and y=4-14, and/or alkoxyphenyl derivatives of alkylpyrimidine, of the general formula (IV) ##STR4## where m and p=6 to 14.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: December 10, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Rolf Dubal, Claus Escher, Wolfgang Hemmerling, Ingrid Muller, Dieter Ohlendorf, Rainer Wingen
  • Patent number: 5072021
    Abstract: The present invention is directed to optically active compounds each containing a naphthalene skeleton, and to liquid crystal compositions which contain the aforesaid optical active compounds, these compositions being suitable for ferroelectric liquid crystal devices having excellent photostability and chemical stability and having a rapid responsivity.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: December 10, 1991
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Masakatsu Nakatsuka, Tsutomu Nishizawa
  • Patent number: 5068054
    Abstract: Disclosed are compounds of the general formula:R--O--Ar--COS--Ph--COO--R'characterized by the presence of the thioester (--COS--) core and wherein R is an alkyl group with typically 8 to 16 carbon atoms, Ar is a substituted aromatic core group such as 1,4-benzene, 2,6-naphthalene, 4,4'-biphenyl, or 4,4'-diphenylethane, and R' is a chiral branched alkyl group such as the 1-substituted cases 1-methylpropyl through 1-methyloctyl or 2-substituted case such as 2-methylbutyl. These materials or their mixtures possess ferroelectric phases and as such are of interest for electro-optical applications. In certain cases specific materials are of particular interest due to the existence of stable ferroelectric phases near room temperature with large polarization density and fast electro-optic response.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: November 26, 1991
    Assignee: International Business Machines Corporation
    Inventors: Kathleen M. Betterton, William D. Hinsberg, Huu T. Nguyen, Wing T. Tang, Robert J. Twieg
  • Patent number: 5068389
    Abstract: The invention relates to tertiary alcohols of the formula I ##STR1## wherein R.sup.1, A.sup.1, Z.sup.1, m, A.sup.2, Y, Q.sup.1, Q.sup.2, Q.sup.3 and Z.sup.2 have the meanings indicated in claim 1, and also to a process for the preparation of these compounds.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: November 26, 1991
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Rudolf Eidenschink, Joachim Krause, Hans-Adolf Kurmeier
  • Patent number: 5068052
    Abstract: A resin composition comprises a thermoplastic polymer and a smectic liquid crystal compound and is useful for fibers and film having been improved in mechanical properties.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: November 26, 1991
    Assignee: Polyplastics Co., Ltd.
    Inventors: Junji Watanabe, Michiro Naka, Kenji Hijikata
  • Patent number: 5064566
    Abstract: Compounds of the formula IR.sup.1 -A.sup.1 -A.sup.2 -R.sup.2 IwhereinR.sup.1 and R.sup.2 are each alkyl with 1-15 C atoms, and wherein one or two non-adjacent CH.sub.2 groups can also be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O--, --CO--S--, --S--CO--, --CHHalogen--, --CHCN-- and/or --CH.dbd.CH--,A.sup.1 is 1,4-phenylene, trans-1,4-cyclohexylene or a single bond andA.sup.2 is ##STR1## in which Z is --O--CO--, --CO--O--, --S--CO--, --CO--S--, CH.sub.2 O--, --OCH.sub.2 -- or --CH.sub.2 CH.sub.2 --, with the proviso that, if A.sup.1 is a single bond, A.sup.2 is ##STR2## are suitable as components of chirally tilted smectic liquid crystal phases.
    Type: Grant
    Filed: October 20, 1989
    Date of Patent: November 12, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Reinhard Hopf, Bernhard Scheuble, Reinhard Hittich, Joachim Krause, Volker Reiffenrath, Eike Poetsch, Thomas Geelhaar, Rudolf Eidenschink
  • Patent number: 5064569
    Abstract: Optically active compounds of the formula I can be used as components of chiral titled smectic liquid crystal phases:R.sup.1 --C*HX--Q--A.sup.4 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.n --X'--Q'--C*HY'--R.sup.5 (I)whereinR.sup.1 --C*HX--Q-- and --X'--Q'--C*HY--R.sup.5 are identical optically active radicals selected from the group --O--C*HCH.sub.3 --COO--n--alkyl, --O--C*HCH.sub.3 --CH.sub.2 --O--n--alkyl, --OCO--C*HC1--CHCH.sub.3 --CH.sub.3, --OCO--C*HCl--C*HCH.sub.3 --C.sub.2 H.sub.5, --OCO--C*HCl--CH.sub.2 --CHCH.sub.3 --CH.sub.3, --OCO--C*HCl--C(CH.sub.3).sub.3, --COO--C*HCH.sub.3 -COO--n--alkyl, --O--CO--C*HCH.sub.3 --o--n--alkyl, --OCH.sub.2 --C*HCH.sub.3 --O--n--alkyl, --COO--C*HCH.sub.3 CH.sub.2 --O--n--allyl, --OC*HCH.sub.3 --CH.sub.2 --COO--n--alkyl, --COO--C*HCH.sub.3 --CH.sub.2 --COO--n--alkyl, --OCH.sub.2 --C*HCH.sub.3 --COO--n--alkyl or --COO--CH.sub.2 --C*HCH.sub.3 --COO--n--alkyl, alkyl is of 1--12 c atoms,and --A.sup.4 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: November 12, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Thomas Geelhaar, Andreas Wachtler, Bernhard Scheuble
  • Patent number: 5062990
    Abstract: Octasubstituted tetraphyrazinotetraazaporphrazine and compositions forming an electron acceptable discotic liquid crystal phase are disclosed. Said compounds and the metal complexes are easily soluble in an organic solvent such as chloroform or dichloromethane etc and are insoluble in acetone and alcohols; and therefore a columnar phase by silica gel/dichloromethane, recrystallization from tetra-hydrofuran or refining through solid liquid extraction by acetone is possible. Furthermore, stability in a giant molecular can be expected and a functional membrane can be formed by a solution cast method etc., thereby employing as an electon or photoelectron material or an indication element.
    Type: Grant
    Filed: December 27, 1989
    Date of Patent: November 5, 1991
    Assignees: Eastern Co., Ltd., Iwawo Yamamoto
    Inventors: Iwawo Yamamoto, Kazuchika Ohta
  • Patent number: 5061399
    Abstract: Optically active naphthalene compounds having the formula: ##STR1## in which X and Y are selected from combinations (a), (b) and (c): (a) X is C.sub.1-10 alkyl or alkoxy and Y is C.sub.4-16 optically active alkyl, (b) X is C.sub.1-10 alkyl or alkoxy and Y is ##STR2## where R.sup.2 is C.sub.4-16 optically active alkyl, (c) X is ##STR3## where R.sup.1 is C.sub.1-10 alkyl or alkoxy and Y is C.sub.4-16 optically active alkyl. Ferroelectric smectic liquid crystal materials being compositions containing these compounds are also described.
    Type: Grant
    Filed: April 27, 1987
    Date of Patent: October 29, 1991
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: John A. Jenner, Ian C. Sage, Stephen J. Lewis
  • Patent number: 5059340
    Abstract: An optically active compound having a large spontaneous polarization value and capable of affording a composition exhibiting a suitable ferroelectric liquid crystal temperature range and a liquid crystal composition containing the same are provided, which compound is expressed by the formula ##STR1## wherein either one of R.sup.1 and R.sup.2 represents an alkyl group or an alkoxy group each of 1 to 20 carbon atoms and another thereof represents an optically active group.
    Type: Grant
    Filed: October 18, 1990
    Date of Patent: October 22, 1991
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Makoto Ushioda, Shinichi Saito, Hiromichi Inoue, Kouji Ohno
  • Patent number: 5059356
    Abstract: Disclosed is a polarizing film comprising a hydrophobic polymer containing a dichroic organic colorant in an oriented state which is characterized in that the dichroic organic colorant is substantially insoluble in water, organic solvents and liquid crystals and the dichroic ratio of the colorant is not less than 7 when it is measured with the film obtained by blending the colorant intimately with polyethylene terephthalate, melting the resulting blend and forming it into a film. This polarizing film has exceptionally excellent moisture resistance and thermal resistance.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: October 22, 1991
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Katsuji Nakamura, Junichi Fujio, Shin Hosonuma, Masakatsu Nakatsuka, Tsutomu Nishizawa