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).
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Patent number: 7462427Abstract: The use of a mesogenic compound having a terminal end chain comprising carbon, oxygen, or sulphur, which has at least one pendent C1-4alkyl, C1-4alkoxy or a cycloalkyl ring, arranged no more than 6 atoms from the end of the chain either decreasing the melting point, increasing the clearing point, increasing the speed of switching and/or increasing the tilt angle of a liquid crystal mixture. Examples of such compounds are of formula (I) where M is a mesogenic core group, and X and Y are terminal groups, provided that at least one group X or Y is a group of sub-formula (i) where Z1, Z2, R1, R2, R3, R4, R5, R6, R7, s, q, m and n are as defined in the specification. Novel compounds of formula (I) are also described and claimed.Type: GrantFiled: September 12, 2002Date of Patent: December 9, 2008Assignee: Qinetiq LimitedInventors: John W Goodby, Michael Hird, Kenneth J Toyne, Guirec Y Cosquer, Stephen J Cowling, Neil Gough
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Patent number: 7351452Abstract: A compound of formula (I) or a dimer thereof; where R1 and R2 are independently selected from optionally substituted alkyl, optionally substitituted alkenyl, optionally substituted alkynyl, a functional group or a group of sub-formula (i) —(O)m—(CH2)p—R7??(i) where m is 0 or 1; p is an integer of from 1 to 12; R7 is a group of formula —CqX2q+1 where q is an integer of from 1 to 12 and X is halogen such as fluoro, or R7 a group of sub-formula (ii) where k is an integer of from 1 to 10, R8, R10, and R12 and each R9 and R11 are independently selected from alkyl, alkenyl or aryl, such as lower alkyl and in particular methyl; provided that at least one of R1 or R2 is a group of sub-formula (i); R3, R4, R5 and R6 are independently selected from hydrogen or halogen, and in particular fluorine, n is 0 or 1, and A is a ring structure as specified. Compounds of formula (I) may have liquid crystal properties and/or be useful in liquid crystal devices.Type: GrantFiled: November 7, 2002Date of Patent: April 1, 2008Assignee: Qinetiq LimitedInventors: John W Goodby, Michael Hird, Kenneth J Toyne, Chu C Dong, Robert D. C Richards
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Publication number: 20040206933Abstract: The use of a mesogenic compound having a terminal end chain comprising carbon, oxygen, or sulphur, which has at least one pendent C1-4alkyl, C1-4alkoxy or a cycloalkyl ring, arranged no more than 6 atoms from the end of the chain either decreasing the melting point, increasing the clearing point, increasing the speed of switching and/or increasing the tilt angle of a liquid crystal mixture. Examples of such compounds are of formula (I) where M is a mesogenic core group, and X and Y are terminal groups, provided that at least one group X or Y is a group of sub-formula (i) where Z1, Z2, R1, R2, R3, R4, R5, R6, R7, s, q, m and n are as defined in the specification. Novel compounds of formula (I) are also described and claimed.Type: ApplicationFiled: April 29, 2004Publication date: October 21, 2004Inventors: John W Goodby, Michael Hird, Kenneth J Toyne, Guirec Y Cosquer, Stephen J Cowling, Neil Gough
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Patent number: 6666989Abstract: Polymeric compounds of general formula (I) where X, X1, X2 are independently straight or branched chain C1-16 alkyl, halogen and H; (a) is a suitable mesogenic group; Z=single covalent bond, oxygen CO2, OCO; n=1-20; Y=oxygen, CO2, OCO, CH2, CHOH, CH2O; m=3-10,000. The compounds are liquid crystal polymers useful in liquid crystal devices, sensors, and in non-linear optical devices. The compounds are prepared by polymerization of the oxitane monomer to obtain the side-chain liquid crystalline polyoxitane compound. In this way the mesogenic groups are spaced on every fourth carbon atom in the polymer chain allowing greater mobility for the mesogenic group.Type: GrantFiled: August 15, 2000Date of Patent: December 23, 2003Assignee: Qinetiq LimitedInventors: Kenneth J Toyne, Stephen J Cowling, John W Goodby
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Patent number: 6180024Abstract: Methods, based on the Wittig-Horner reaction, are provided for the synthesis of compounds of formula (I) where m is from 5-150, X and Y are independently selected from: CN, H, OH, COCH3, CO2H, CO2H, CO2R1, where R1 is C1-12 alkyl, NCS, SCN, CF3, CH2X where X is F, Cl, Br, OH, CHF2 and formula (IB), where J for each X and Y group is independently selected from: CH2, single covalent bond, OOC, CO2, O, CH2O, OCH2, CH2CO2, CH2OOC; p=1-20; L for each X and Y group is independently selected from: O, CH2OCO, CO2, S, NH; (a) is defined by formula (IC), where rings A, B and C are independently selected from phenyl, cyclohexyl, pyridine and pyrimidine and may be independently of each other substituted with at least one of Cl or F; linking groups A and B may be selected from single bond, CO2, OOC, CH2O, OCH2, CH2CH2, C≡C; Z is selected from CN, F, Cl, NO2, R, OR, CO2R, CF3, OOCR, NCS, SCN, where R=straight chain or branched chain alkyl and may include from 1-16 carbon atoms and inclType: GrantFiled: February 26, 1999Date of Patent: January 30, 2001Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Keith M Blackwood, Michelle Jones, David Lacey, Alan W Hall, Kenneth J Toyne, Steven Pringle
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Patent number: 6051639Abstract: A material of general formula I: ##STR1## where E=0 indicates a non-cyclic system, and E=1 indicates a cyclic system;G is R.sub.3 SiR.sub.1 R.sub.2 (O).sub.kR.sub.1, R.sub.2, R.sub.3 are independently selected from C.sub.1-16 alkyl which may be partly or fully halogenated, H and formula IA: ##STR2## wherein Y is a propylene group which may be partially halogenated with fluorine or chlorine and Y.sub.1 is independently selected from COO, OCO, O, S, CHOH, CHF, CO or CH.sub.2 ;Q and Q.sub.1 are independently selected from (CH.sub.2).sub.n wherein one or more non-adjacent methylenes may be replaced by O andn=0-20;Z and Z.sub.1 are independently selected from O, S, single covalent bond, COO or OCO; ##STR3## represents a mesogenic group and is given by the general structure II ##STR4## A, B, D are selected from the following rings: ##STR5## the above rings may be substituted with one or more of the following substituents in at least one of the available substitution positions: F, Cl, Br, CH.sub.Type: GrantFiled: August 25, 1998Date of Patent: April 18, 2000Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Georg H Mehl, John W Goodby, Rachel P Tuffin, Kenneth J Toyne
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Patent number: 5595682Abstract: Liquid crystal compounds having the formula (I) ##STR1## in which A.sub.1 is alkyl, alkoxy or alkenyl; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are independently halogens, m, n, p and q are independently 0, 1, 2, 3 or 4 such that m+n+p+q.noteq.0; Y is O or COO; and A.sub.2 is an end group of the formula (II), ##STR2## where Z is halogen, CH.sub.3, CN, CF.sub.3 or, CHF.sub.2 ; R is a linear or branched alkyl group or H; and R.sub.1 is a linear or branched alkyl group or H.Type: GrantFiled: April 18, 1995Date of Patent: January 21, 1997Assignees: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain And Northern Ireland, Defence Research AgencyInventors: John W. Goodby, Kenneth J. Toyne, Christopher J. Booth
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Patent number: 5578242Abstract: Liquid crystal compounds of the formula:R.sup.1 --Z.sup.1).sub.m --(Z.sup.2)--X--(Z.sup.3)--(Z.sup.4).sub.n --R.sup.2These compounds may be mixed with other liquid crystal compounds to give liquid crystal mixtures which may then be used in liquid crystal devices. In the formula X is COS, CSS and CSO; each of Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are independently phenyl, substituted phenyl, where substitution is lateral substitution selected from F, Cl, Br, NO.sub.2, CN, NCS; naphthalene, substituted naphthalene, where substitution is lateral substitution selected from F, Cl, Br, NO.sub.2, CN, NCS, CH.sub.3 ; thiophene, pyridine and pyrimidine; each of A.sup.1 and A.sup.2 is independently selected from single bond, C.tbd.C, CH.dbd.CH; A.sup.3 is selected from C.tbd.C and single bond; each of R.sup.1 and R.sup.2 are independently selected from CN, NCS, CH.dbd.C(CN).sub.2, C.tbd.C--CN, C.tbd.C--CF.sub.Type: GrantFiled: April 12, 1995Date of Patent: November 26, 1996Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland of Defence Research AgencyInventors: John W. Goodby, Michael Hird, Kenneth J. Toyne, Alexander J. Seed, Damien G. McDonnell, Amarjit K. Samra
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Patent number: 5498366Type: GrantFiled: June 14, 1994Date of Patent: March 12, 1996Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Damien G. McDonnell, Sally E. Day, David Coates, John A. Jenner, Michael Hird, Kenneth J. Toyne
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Patent number: 5496500Abstract: Liquid crystal compounds of formula (I) are described, where formula (I) is given as R.sub.1 --A--(X.sub.m --(B).sub.n --R.sub.2 where A is selected from nathyl, flourinated naphthyl, brominated naphthyl, B is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R.sub.1 and R.sub.2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, X is selected from C.tbd.C, COO and C.tbd.C, m is 0 or 1, n is 0 or 1 where m is 1 and n is 0 where m is 0; provided that where A is naphthyl, n is 1 and m is 0 then B is selected from methylated phenyl, brominated phenyl, thiophene, pyrimidine and pyridine; and further provided that where A is naphthyl, X is C.tbd.C, m is 1 and n is 1, then B is selected from thiophene, pyrimidine and pyridine.Type: GrantFiled: August 1, 1994Date of Patent: March 5, 1996Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain & Northern IrelandInventors: Kenneth J. Toyne, John W. Goodby, Alexander Seed, George W. Gray, Damien G. McDonnel, Edward P. Raynes, Sally E. Day, Kenneth J. Harrison, Michael Hird
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Patent number: 5486309Abstract: Optically active compounds of formula (I), where X has a structure (II) and B is C.sub.1-12 alkyl, a chiral group or a group having a general structure (III), where R and R' are H, C.sub.1-12 alkyl, alkoxy, alkylcarbonyloxy, or alkoxycarbonyl, each ring (IV) and (V) is the same or different, A and D are single bonds or bridging groups, each a and d is 0 or 1; Z, Z' are CN, Cl, F, Br or CF.sub.3 ; provided when Z is CN or Cl, then when B is alkyl X-Y is not (VI) or (VII). Ferroelectric smectic liquid crystal mixtures containing these compounds are also described.Type: GrantFiled: September 22, 1993Date of Patent: January 23, 1996Assignee: The Secretary of State for Defence in Her Majesty'3 s Government of the United Kingdom of Great Britain and Northern IrelandInventors: George W. Gray, David Lacey, Kenneth J. Toyne, Richard M. Scrowston, Ibrahim G. Shenouda, Lawrence K. M. Chan, Madeline J. Bradshaw, Victoria Brimmell, Jennifer Constant, Edward P. Raynes, Adam Jackson, Amarjit K. Samra
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Patent number: 5478496Abstract: The invention relates to the use of chiral and/or achiral compounds, containing at least one structural element from the group comprisingthiazole-2,4-diylthiazole-2,5-diyl1,2,4-thiadiazole-2,5-diyl1,2,4-thiadiazole-3,5-diylas components of media having a smectic liquid-crystalline phase.Type: GrantFiled: November 30, 1992Date of Patent: December 26, 1995Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: George W. Gray, Richard M. Scrowston, Kenneth J. Toyne, David Lacey, Adam Jackson, Joachim Krause, Eike Poetsch, Thomas Geelhaar, Georg Weber, Andreas Wachtler
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Patent number: 5456859Abstract: There is disclosed a cyanoalkane and cyanoalkene of general formula (I) which shows liquid crystalline properties: wherein R and R.sup.1 are independently C.sub.1-12 alkyl, alkoxy, perfluoroalkyl or perfluoroalkoxy; rings A, B, C and D are independently phenyl, which may carry one or two halogen substituents, trans-cyclohexyl, or (2, 2, 2) bicyclooctyl, each of a, b, c or d being independently 0 or 1 provided (a+b+c+d) is 2 or 3; links A and C are independently a single bond, CH.sub.2 CH.sub.2, COO, OOC, CH.sub.2 O or OCH.sub.2 ; n, m and p are independently 0 or an integer 1 to 4 provided (n+m+p) is not 0; W and Z are independently selected --CH.dbd.C(CN)-- and --C(CN).dbd.CH--; X and Y are independently selected from --CHCN-- and --C(CN).sub.2 --; w, x, y and z are 0 or 1, provided that w and z are 0 if x and/or y are 1, and further provided that at least one of w, x, y and z is 1.Type: GrantFiled: October 8, 1992Date of Patent: October 10, 1995Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: George W. Gray, David Lacey, Kenneth J. Toyne, Ibraham G. Shenouda, Abdul Luheshi
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Patent number: 5384071Abstract: This invention relates to novel chiral cyano-containing compounds suitable for use in ferroelectric smectic liquid crystal mixtures.Type: GrantFiled: January 8, 1993Date of Patent: January 24, 1995Assignee: Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Gt. Britian and Northern IrelandInventors: George W. Gray, David Lacey, Kenneth J. Toyne, Richard M. Scrowston, Ibrahim G. Shenouda, Lawrence K. M. Chan, Adam Jackson, Madeline J. Bradshaw, Victoria Brimmell, Jennifer Constant, Edward P. Raynes, Amarjit K. Samra
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Patent number: 5358663Abstract: Laterally cyano-substituted terphenyls of formula (I), wherein R.sup.1 and R.sup.2 are independently selected from hydrogen or C.sub.1-15 alkyl, alkoxy, or alkyl or alkoxy in which one or more CH.sub.2 groups are replaced by O, COO, OOC, CHX, CX.sub.2, CH=CX, CX=CH, CX=CX, where X is fluorine or chlorine. CRCN where R is alkyl, or C.tbd.C or in which a terminal CH.sub.3 of the said alkyl or alkoxy chain is replaced by CF.sub.3, n is 0 or 1, and the CN and F (if present) substituent are independently located in any of the available substitution positions. Liquid crystal materials containing these terphenyls are also described.Type: GrantFiled: September 18, 1992Date of Patent: October 25, 1994Assignee: The Secretary of State for Defence in her Britannic Majesty'3 s Government of U.K. of Gt. Britain and N. IrelandInventors: George W. Gray, David Lacey, Michael Hird, Kenneth J. Toyne
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Patent number: 5352381Abstract: Compounds of formula (I) where R is C.sub.1-15 alkyl, X is hydrogen, fluorine or chlorine, m and n are independently selected 1 or 0, W is C.sub.1-15 alkyl or alkoxy, CN or halogen, rings A and B Are independently selected from phenyl, laterally fluoro- or chloro- substituted phenyl, transcyclohexyl pyridyl, pyrimidyl or dioxanyl. Preferred embodiments have R=C.sub.3-8 and where W is alkyl or alkoxy then it is also preferable that W=C.sub.3-8. Where m=0, then preferably W=CN and where m=1, then preferably W=alkyl.Type: GrantFiled: April 13, 1992Date of Patent: October 4, 1994Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Damien G. McDonnell, Sally E. Day, David Coates, John A. Jenner, Michael Hird, Kenneth J. Toyne
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Patent number: 5334327Abstract: Novel compounds of formula (I), in which R is R.sup.1, R.sup.1 O or R.sup.1 COO, where R.sup.1 is C.sub.1-12 alkyl, n and m 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 m is 0 and one of c or d is 0 are described, being useful constituents of nematic liquid crystal materials.Type: GrantFiled: May 12, 1992Date of Patent: August 2, 1994Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and North IrelandInventors: George W. Gray, David Lacey, Kenneth J. Toyne, Michael Hird, Damien G. McDonnell
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Patent number: 5312563Abstract: Fluorinated 4"-cyano substituted terphenyls of general formula (I), wherein R.sub.1 is selected from alkenyl, H, R, RO and RCO where R is alkyl or perfluoroalkyl containing up to 12 carbon atoms, n is 1, 2 or 3 and the lateral fluorosubstituent(s) may be in any of the available substitution positions are provided. These have liquid crystalline properties and may be used as components of liquid crystal materials.Type: GrantFiled: January 22, 1993Date of Patent: May 17, 1994Assignee: The Secretary of State for Defence in her Britannic Majesty's Government of the U.K. of Great Britain and Northern IrelandInventors: David Coates, Ian Sage, Simon Greenfield, George W. Gray, David Lacey, Kenneth J. Toyne, Lawrence K. Chan, Michael Hird
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Patent number: 5273680Abstract: This invention relates to fluorinated oligophenyls of formula (I), in which a is 0 or 1 and in which the terminal substituents R.sup.1, R.sup.2 and R.sup.3 are each independently an alkyl or alkenyl residue each with up to 15 C atoms, optionally substituted by CN or by at least one halogen atom, and wherein one or more non adjacent CH.sub.2 groups of these residues may be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O--, --O--CO--O-- or --C.tbd.C--, one of the residues R.sup.1 and R.sup.2 may also denote a group of formula (II), any one of the following pairs of lateral substituents are both fluorine: (A, B), (C, D), (D, E), (C, E), (B, C), (D, J), (D, K), (A, C), (C, J), (C', D'), (D', E), (D', A), (C', E), (C', A), (D', J'), (D', K'), (C', J'), (B, G), (A, G), all of the other lateral substituents being hydrogen or fluorine, and to their use as components of liquid crystalline compositions.Type: GrantFiled: March 9, 1992Date of Patent: December 28, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: George W. Gray, Michael Hird, David Lacey, Kenneth J. Toyne, Volker Reiffenrath, Andreas Wachtler, Joachim Krause, Ulrich Finkenzeller, Thomas Geelhaar
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Patent number: 5252253Type: GrantFiled: July 16, 1991Date of Patent: October 12, 1993Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: George W. Gray, Kenneth J. Toyne, David Lacey, Michael Hird