Patents by Inventor Kenneth J Toyne

Kenneth J Toyne has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5232625
    Abstract: Compounds suitable for use as constituents of ferroelectric smectic liquid crystal compositions, which are esters of formula (I), where R.sub.2 and R.sub.3 together represent the residue of an alicyclic hydrocarbon ring system where .degree.C. is an asymmetric carbon atom and X is a chain of up to three linked aromatic or alicyclic six-membered organic cyclic groups, laterally and/or terminally substituted. Preferred compounds have a formula (II), where R.sub.1 is alkyl or alkoxy, A, B, and D are phenyl, fluoro or chloro substituted phenyl or cyclohexyl, n is 0 or 1, Y is a bond or CH.sub.2 CH.sub.2 if n is 0, or a bond CH.sub.2 CH.sub.2 COO or COO if n is 1. Preferred groups C(CN)R.sub.2 R.sub.3 are formula (III) and (IV).
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: August 3, 1993
    Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: George W. Gray, Kenneth J. Toyne, David Lacey, David Holmes, Richard M. Scrowston
  • Patent number: 5204019
    Abstract: 4-Q.sup.1 -4'-Q.sup.2 -2,3-Difluorobiphenyls whereinQ.sup.1 and Q.sup.2 independently of one another are each R or R-A.sup.1 -A.sup.2 -Z in whichR (sic) alkyl having 1-15 C atoms or alkenyl having 3-15 C atoms each of which is unsubstituted or monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, and in which in each case one or two non-adjacent CH.sub.2 groups can also be replaced by --O--, --CO--, --O--CO, --CO--O-- or --O--COO--, (sic) --COO--, --O--CO--, --CH.sub.2 O, --O--CH.sub.2 --, --CH.sub.2 CH.sub.2 -- or a single bond, andA.sup.1 and A.sup.2 independently of one another . . (sic) each 1,4-phenylene which is unsubstituted or substituted by one or two fluorine atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups can also be replaced by --O--, and one of the two groups A.sup.1 and A.sup.2 can also be a single bond,subject to the proviso that Z is --CO--O, --O--CO--, --CH.sub.2 O--, --OCH.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: April 20, 1993
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller, David Coates, Ian C. Sage, Simon Greenfield, George W. Gray, Michael Hird, David Lacey, Kenneth J. Toyne
  • 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: 5156763
    Abstract: Laterally fluorinated 4-cyanophenyl and 4'-cyanobiphenyl benzoates are diosed of general formula I: ##STR1## in which R is R.sup.1 or R.sup.1 O, wherein R.sup.1 is C.sub.1 -C.sub.12 alkyl, m and n are 0 or 1 provided that (n+m) is 0 or 1, each of a, b, c and d are independently 0 or 1, provided (a+b+c+d) is not zero, but excluding the case where a and b are 0 and one of c and d is 0, being useful constituents of nematic liquid crystal materials.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: October 20, 1992
    Assignee: The Secretary of State for for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: George W. Gray, David Lacey, Kenneth J. Toyne, Michael Hird, Damien G. McDonnell
  • Patent number: 5147577
    Abstract: Compounds suitable for use as constituents of ferroelectric smectic liquid crystal compositions, which are ester of formula (I), where R.sub.2 and R.sub.3 together represent the residue of an alicyclic hydrocarbon ring system where *C is an asymmetric carbon atom and X is a chain of up to three linked aromatic or alicyclic six-membered organic cyclic groups, laterally and/or terminally substituted. Preferred compounds have a formula (II), where R.sub.1 is alkyl or alkoxy, A, B, and D are phenyl, fluoro or chloro substituted phenyl or cyclohexyl, n is 0 or 1, Y is a bond or CH.sub.2 CH.sub.2 if n is 0, or a bond CH.sub.2 CH.sub.2 COO or COO if n is 1. Preferred groups C(CN)R.sub.2 R.sub.3 are formula (III) and (IV).
    Type: Grant
    Filed: June 1, 1989
    Date of Patent: September 15, 1992
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: George W. Gray, Kenneth J. Toyne, David Lacey, David Holmes, Richard M. Scroston
  • Patent number: 5037576
    Abstract: Compounds for use in ferroelectric smectic liquid crystal mixtures of general formula (I), where R.sub.1 is alkyl, Y is COO or OOC, m, n and p are 0 or 1 provided m+n is 2 or less and when Y is OOC, p is 0, X is a mesogenic group, especially 4.sup.1 -alkyl- or alkyl-biphenyl or bicyclohexyl. Methods for preparation of these compounds are given, and ferroelectric smectic liquid crystal mixtures containing them are described.
    Type: Grant
    Filed: May 3, 1989
    Date of Patent: August 6, 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: George W. Gray, David Lacey, Kenneth J. Toyne, Richard M. Scrowston, Adam Jackson
  • Patent number: 5002692
    Abstract: Amides having the following structure: ##STR1## used in ferroelectric smectic liquid crystal mixtures, especially as pitch compensators and liquid crystal compositions containing them.
    Type: Grant
    Filed: December 1, 1988
    Date of Patent: March 26, 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: George W. Gray, David Lacey, Kenneth J. Toyne, Richard M. Scrowston, Lawrence K. M. Chan, Madeline J. Bradshaw, Victoria Brimmell
  • Patent number: 4941992
    Abstract: Novel compounds suitable for use as chiral dopants in ferroelectric smectic liquid crystal materials comprising an optically active derivative of an .alpha.-amino acid of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of C.sub.1-20 alkyl or alkoxy, R is C.sub.1-20 n-alkyl and Y is C.sub.1-20 alkyl. A liquid crystal mixture and a device using these compounds are also described.
    Type: Grant
    Filed: July 17, 1987
    Date of Patent: July 17, 1990
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Adam Jackson, Richard M. Scrowston, George W. Gray, David Lacey, Kenneth J. Toyne
  • Patent number: 4923633
    Abstract: A compound suitable for use in a ferroelectric smectic liquid crystal composition having a structure which contains two chiral centers derived from alpha hydroxy carboxylic acid groups and having the formula: ##STR1## wherein R.sub.1 is n-alkoxy containing 1-12 carbo atoms and R.sub.2 is n-alkyl containing 1-12 carbon atoms. Methods of preparation and details of liquid crystal mixtures containing these compounds are described.
    Type: Grant
    Filed: November 30, 1987
    Date of Patent: May 8, 1990
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: George W. Gray, David Lacey, Kenneth J. Toyne, David Coates, Adam Jackson, Richard M. Scrowston
  • Patent number: 4913837
    Abstract: Heterocyclic compounds of the formula IR.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.n -R.sup.2Iwherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are defined in claim 1, can be used as components of liquid-crystalline phases.
    Type: Grant
    Filed: September 1, 1987
    Date of Patent: April 3, 1990
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: George W. Gray, Kenneth J. Toyne, David Lacey, Michael P. Burrow, Rudolf Eidenschink, Andreas Wachtler, Georg Weber
  • Patent number: 4868341
    Abstract: New bicyclohexyls of the formula IR.sup.1 --Cy--Cy--R.sup.2wherein R.sup.1 and R.sup.2 are each alkyl which has 1-10 C atoms and in which one or two CH.sub.2 group(s) can be replaced by 0 atoms, and Cy is 1,4-cyclohexylene,are suitable for use as the coponents of liquid-crystal dielectrics.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: September 19, 1989
    Assignees: Merck Patent Gesellschaft Mit Beschrankter Haftung, The Secretary of State for Defence in Her Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Rudolf Eidenschink, Michael Romer, Georg Weber, George W. Gray, Kenneth J. Toyne
  • Patent number: 4852977
    Abstract: Novel lactic acid derivatives which may be used as a component of a ferroelectric smectic liquid crystal mixture, which derivatives have the general formula: ##STR1## in which R.sub.1 is alkyl or alkoxy and R.sub.2 is alkyl. Liquid crystalline compositions containing these compounds are also described.
    Type: Grant
    Filed: August 19, 1986
    Date of Patent: August 1, 1989
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Lawrence K. M. Chan, David Coates, Peter A. Gemmell, George W. Gray, David Lacey, Kenneth J. Toyne, Daniel J. S. Young
  • Patent number: 4824217
    Type: Grant
    Filed: August 19, 1986
    Date of Patent: April 25, 1989
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Lawrence K. M. Chan, David Coates, Peter A. Gemmell, George W. Gray, David Lacey, Kenneth J. Toyne, Daniel J. S. Young, Matthew F. Bone, Adam Jackson, Richard M. Scrowston
  • Patent number: 4784793
    Abstract: Novel derivatives of cyclic and acyclic terpenoid alcohols, having general formula (I) X--(CO).sub.n --O--T.sub.1, where n=O or l, T.sub.1 is a terpenoid group and X is a combination of cyclic groups, e.g. phenyl, cyclohexyl and pyrimidyl, X preferably contains up to three cyclic groups. Preferred derivatives are esters of cyclic terpenoid alcohols, e.g. menthol, borneol and isopineocampheol, e.g. formula (II) (-)-menthol. Ferroelectric smectic liquid crystal mixtures and devices containing these derivatives as chiral dopants in a tilted smectic host are also described. The properties of various other derivatives of terpenoid alcohols of formula (I) are also described, e.g. those of neomenthol, isolongifolol, fenchol, carveol, myrthenol, nopol, citronellol, perilla alcohol and dihydrocitronellol.
    Type: Grant
    Filed: September 22, 1986
    Date of Patent: November 15, 1988
    Assignees: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland, STC PLC
    Inventors: David Coates, George W. Gray, David Lacey, Daniel J. S. Young, Kenneth J. Toyne, Matthew F. Bone
  • Patent number: 4696549
    Abstract: Novel terphenyls having a relatively high clearing point and which are suitable for use in liquid crystal materials or in the preparation of compounds for use in such material are characterized by a formula: ##STR1## wherein: R.sub.1 is selected from H, alkyl, alkoxy, alkylcarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy;R.sub.2 is selected from H, alkyl, alkoxy;X.sub.1 is selected from H and fluorine;X.sub.2 is selected from H and fluorine; and ##STR2## provided that one of X.sub.1 and X.sub.2 is fluorine. Compounds wherein ##STR3## are generally useful as liquid crystal compounds.
    Type: Grant
    Filed: December 5, 1985
    Date of Patent: September 29, 1987
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Lawrence Kam Ming Chan, George W. Gray, Kenneth J. Toyne, David Lacey, Rudolf Eidenschink, Michael Romer
  • Patent number: 4695131
    Abstract: A fluorinated compound having a formula: ##STR1## R.sub.1 is hydrogen or alkyl having up to 12 carbon atoms; R.sub.2 is selected from hydrogen, alkyl having up to 12 carbon atoms, alkoxy having up to 12 carbon atoms, ##STR2## wherein R.sub.3 is hydrogen or alkyl having up to 12 carbon atoms, and wherein R.sub.4 is hydrogen, alkyl having up to 12 carbon atoms or alkoxy having up to 12 carbon atoms; ##STR3## represents a cyclohexane ring which is in the trans configuration if 1, 4-disubstituted; ##STR4## represents a benzene ring; each of X, Y and Z independently represents hydrogen or fluorine in one or more of the lateral benzene ring positions, provided that at least one of X, Y and Z is present representing fluorine;n=0 or 1 provided that when n=0 ##STR5## and R.sub.1 is alkyl; with the proviso that in Formula I when n is 1 and ##STR6## where R.sub.1 is n-alkyl and R.sub.2 is n-alkyl or n-alkoxy the total number of carbon plus oxygen atoms in the two groups R.sub.1 and R.sub.2 is less than 10.
    Type: Grant
    Filed: January 25, 1984
    Date of Patent: September 22, 1987
    Inventors: Peter H. Balkwill, David I. Bishop, Andrew D. Pearson, Ian C. Sage, George W. Gray, David Lacey, Kenneth J. Toyne, Damien G. McDonnell
  • Patent number: 4659502
    Abstract: Ethane derivatives of the formula IR.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --(A.sup.3).sub.n --R.sup.2 IwhereinR.sup.1 is H, an alkyl group with 1-12 C atoms, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms and/or CO groups and/or --O--CO-- groups and/or --CO--O groups, F, Cl, Br or R.sup.3 --A.sup.4 --Z.sup.1 --,R.sup.2 is --CN or --Z.sup.2 --A.sup.4 --CN,A.sup.1 is --A--, --A--A.sup.5 -- or --A.sup.5 --A--,A.sup.2 is an 1,4-phenylene group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms,A is a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms, or is a 1,3-dithiane-2,5-diyl group or 1,4-bicyclo(2,2,2)-octylene group,A.sup.3, A.sub.4 are each a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.
    Type: Grant
    Filed: January 17, 1985
    Date of Patent: April 21, 1987
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Julie E. Fearon, Wendy E. Smith, George W. Gray, David Lacey, Kenneth J. Toyne, Georg Weber
  • Patent number: 4622164
    Abstract: New bicyclohexyls of the formula IR.sup.1 --Cy--Cy--R.sup.2wherein R.sup.1 and R.sup.2 are each alkyl which has 1-10 C atoms and in which one or two CH.sub.2 group(s) can be replaced by O atoms, and Cy is 1,4-cyclohexylene,are suitable for use as the components of liquid-crystal dielectrics.
    Type: Grant
    Filed: June 14, 1984
    Date of Patent: November 11, 1986
    Assignees: Merck Patent Gesellschaft mit beschrankter Haftung, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Rudolf Eidenschink, Michael Romer, Georg Weber, George W. Gray, Kenneth J. Toyne
  • Patent number: 4594465
    Abstract: Novel terphenyls having a relatively high clearing point and which are suitable for use in liquid crystal materials or in the preparation of compounds for use in such material are characterised by a formula: ##STR1## wherein: R.sub.1 is selected from H, alkyl, alkoxy, alkylcarbonyl, alkylcarbonyloxy and alkoxycarbonyloxy;R.sub.2 is selected from H, alkyl, alkoxy;X.sub.1 is selected from H and fluorine;X.sub.2 is selected from H and fluorine; and ##STR2## is selected from ##STR3## and ##STR4## provided that one of X.sub.1 and X.sub.2 is fluroine. Compounds wherein ##STR5## is ##STR6## or ##STR7## are generally useful as liquid crystal compounds.
    Type: Grant
    Filed: July 19, 1984
    Date of Patent: June 10, 1986
    Assignees: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland, Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Lawrence Kam Ming Chan, George W. Gray, Kenneth J. Toyne, David Lacey, Rudolf Eidensschink, Michael Romer
  • Patent number: 4544497
    Abstract: Liquid crystal compositions are described which comprise a mixture of compounds and which includes at least one additive compound characterized in that the composition includes one or more additive compounds of Formula I as follows: ##STR1## wherein R.sub.1 represents an alkyl group, R.sub.2 represents an alkyl or alkoxy group or hydrogen and ##STR2## represents a 1,4-disubstituted bicyclo(2,2,2)octane ring. The preparation and properties of novel compounds of Formula I are also described. These liquid crystal compositions are useful in display devices such as digital calculators and word displays.
    Type: Grant
    Filed: January 25, 1984
    Date of Patent: October 1, 1985
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Hilal M. Abdullah, Jennifer Constant, George W. Gray, Damien G. McDonnell, Kenneth J. Toyne