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US4198130A Expired / Lapsed US ⏱️ 0.0 years remaining

Liquid crystal mixtures

Assignee: Merck Patent GmbH
•
Filing: 1978-05-22
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Granted: 1980-04-15
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Expires: 1998-05-22
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Abstract

Abstract Liquid crystal mixtures having positive anisotropy of the dielectric constants comprising a nematogenic material having a clearing point above 60° C., one or more compounds of the formula ##STR1## wherein R 1 and R 2 are hydrogen or straight-chain alkyl, provided that at least one of R 1 and R 2 is other than hydrogen and that R 1 and R 2 together contain no more than 9 carbon atoms, and, if desired, one or more additional doping agents, are described.

Inventors

  • 👤 Arthur Boller
  • 👤 Alfred Germann
  • 👤 Martin Schadt
  • 👤 Hanspeter Scherrer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 23:29
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07C; C07C1/00; C07C1/20; C07C1/22; C07C45/00; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/782; C07C49/792; C09; C09K; C09K19/00; C09K19/04; C09K19/42; C09K19/48; C09K19/52; C09K19/58; C07C2521/00; C07C2521/18; C07C2523/00; C07C2523/38; C07C2523/40; C07C2523/44; C07C2601/00; C07C2601/12; C07C2601/14

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 79 words
A nematic liquid crystal mixture having positive anisotropy of the dielectric constants comprising a nematogenic material having a clearing point above 60° C. and one or more compounds of the formula ##STR18## wherein R 1 and R 2 are hydrogen or straight-chain alkyl, provided that at least one of R 1 and R 2 is other than hydrogen and that the sum of the number of carbon atoms present in R 1 and R 2 is at most 9.
Claim 2
Dependent Claim 79 words
A nematic liquid crystal mixture having positive anisotropy of the dielectric constants comprising a nematogenic material having a clearing point above 60° C. and one or more compounds of the formula ##STR18## wherein R 1 and R 2 are hydrogen or straight-chain alkyl, provided that at least one of R 1 and R 2 is other than hydrogen and that the sum of the number of carbon atoms present in R 1 and R 2 is at most 9.
Claim 3
Dependent Claim 132 words
A nematic liquid crystal mixture in accordance with claim 1, further comprising as an additional doping agent a compound of the formula ##STR19## wherein R 3 and R 4 are straight-chain alkyl containing a total of at most 14 carbon atoms or R 3 is straight-chain alkyl and R 4 is straight-chain alkoxy containing together a total of at most 8 carbon atoms, and/or a compound of the formula ##STR20## wherein R 5 and R 6 are straight-chain alkyl containing together a total of at most 6 carbon atoms, and/or a compound of the formula ##STR21## wherein R 7 and R 8 are the same as R 5 and R 6 described above, and/or any other organic solvent or solvent mixture having a specific resistance of at least 10 7 ohm cm.
Claim 4
Dependent Claim 33 words
A nematic liquid crystal mixture in accordance with claim 2, wherein the compound of formula I is present in an amount in the range of from about 1 wt.% to about 20 wt.%.
Claim 5
Dependent Claim 33 words
A nematic liquid crystal mixture in accordance with claim 3, wherein the compound of formula I is present in an amount in the range of from about 5 wt.% to about 15 wt.%.
Claim 6
Dependent Claim 33 words
A nematic liquid crystal mixture in accordance with claim 4, wherein the number of carbon atoms present in each of R 1 and R 2 in the compound of formula I is 2-6.
Claim 7
Dependent Claim 25 words
A nematic liquid crystal mixture in accordance with claim 5, wherein the compound of formula I is 1-n-hexyl-4-cyclohexyl-benzene, 1-n-butyl-4-cyclohexyl-benzene, 1-methyl-4-(4-n-butyl-cyclohexyl)-benzene, 1-ethyl-4-(4-n-butyl-cyclohexyl)-benzene, 1-n-propyl-(4-n-propyl-cyclohexyl)-benzene, 1-ethyl-4-(4-n-propyl-cyclohexyl)-benzene or (4-n-butyl-cyclohexyl)-benzene.
Claim 8
Dependent Claim 406 words
A nematic liquid crystal mixture in accordance with any one of claims 1, 2, 3, 4, 5 or 6, wherein the nematogenic material comprises one or more compounds of the formula ##STR22## wherein R 9 is straight-chain alkyl of 2 to 8 carbon atoms, straight-chain alkoxy of 4 to 7 carbon atoms, straight-chain alkanoyloxy of 2 to 8 carbon atoms or straight-chain alkylcarbonate of 2 to 11 carbon atoms, and/or one or more compounds of the formula ##STR23## wherein R 10 is straight-chain alkyl of 4 to 7 carbon atoms or straight-chain alkylcarbonate of 2 to 11 carbon atoms, and/or one or more compounds of the formula ##STR24## wherein R 11 is straight-chain alkyl of 4 to 8 carbon atoms, straight-chain alkoxy of 5 to 8 carbon atoms, straight-chain alkanoyloxy of 2 to 8 carbon atoms or straight-chain alkylcarbonate of 3 to 11 carbon atoms, and/or one or more compounds of the formula ##STR25## wherein R 12 is straight-chain alkyl of 4 to 8 carbon atoms, straight-chain alkoxy of 4 to 8 carbon atoms, straight-chain alkanoyloxy of 4 to 9 carbon atoms or straight-chain alkylcarbonate of 4 to 11 carbon atoms, and/or one or more trans-cinnamic acid esters of the formula ##STR26## wherein R 13 is straight-chain alkyl of 1 to 8 carbon atoms, and/or one or more compounds of the formula ##STR27## wherein one of R 14 and R 15 are cyano and the other is straight-chain alkyl of 3 to 9 carbon atoms, straight-chain alkoxy of 2 to 9 carbon atoms or straight-chain alkanoyloxy of 2 to 9 carbon atoms, and/or one or more compounds of the formula ##STR28## wherein one of R 16 and R 17 is hydrogen, straight-chain alkyl of 1 to 7 carbon atoms, straight-chain alkoxy of 1 to 7 carbon atoms or straight-chain alkanoyloxy of 2 to 7 carbon atoms and the other is cyano and one of X, Y and Z is nitrogen and the two others are a CH group, and/or one or more compounds of the formula ##STR29## wherein R 18 and R 19 are straight-chain alkyl of 1 to 10 carbon atoms, straight-chain alkoxy of 1 to 10 carbon atoms, straight-chain alkanoyloxy of 2 to 11 carbon atoms or straight-chain alkylcarbonate of 2 to 11 carbon atoms and R 20 is chlorine, bromine or methyl, and/or one or more compounds of the formula ##STR30## wherein R 21 is straight-chain alkyl of 3 to 8 carbon atoms.
Claim 9
Dependent Claim 34 words
A nematic liquid crystal mixture in accordance with claim 1 which contains p-n-butylbenzoic acid p'-cyanophenyl ester, p-n-pentylbenzoic acid p'-cyanophenyl ester, p-n-hexylbenzoic acid p'-cyanophenyl ester, p-n-heptylbenzoic acid p'-cyanophenyl ester, 5-n-pentyl-2-(4-cyanophenyl)-pyrimidine, 5-n-heptyl-2-(4-cyanophenyl)-pyrimidine, 2-(4-cyanophenyl)-5-(4-n-butylphenyl)-pyrimidine, 1-n-hexyl-4-cyclohexyl-benzene and 4-methyl-4'-n-pentyl-biphenyl.
Claim 10
Dependent Claim 52 words
A nematic liquid crystal mixture in accordance with claim 8 which contains 8.7 wt.% p-n-butylbenzoic acid p'-cyanophenyl ester, 9.84 wt.% p-n-pentylbenzoic acid p'-cyanophenyl ester, 13.35 wt.% p-n-hexylbenzoic acid p'-cyanophenyl ester, 15.02 wt.% p-n-heptylbenzoic acid p'-cyanophenyl ester, 8.35 wt.% 5-n-pentyl-2-(4-cyanophenyl)-pyrimidine, 17.91 wt.% 5-n-heptyl-2-(4-cyanophenyl)-pyrimidine, 15.8 wt.% 2-(4-cyanophenyl)-5-(4-n-butylphenyl)-pyrimidine, 5 wt.% 1-n-hexyl-4-cyclohexyl-benzene and 7 wt.% 4-methyl-4'-n-pentyl-biphenyl.
Claim 11
Dependent Claim 20 words
A nematic liquid crystal mixture in accordance with claim 1 which contains 4'-n-pentyl-4-cyanobiphenyl, 4'-n-pentyloxy-4-cyanobiphenyl, 5-n-pentyl-2-(4-cyanophenyl)-pyrimidine, 5-n-heptyl-2-(4-cyanophenyl)-pyrimidine, 2-(4-cyanophenyl)-5-(4-n-butylphenyl)-pyrimidine, 4-cyano-4"-n-pentyl-p-terphenyl and 1-n-hexyl-4-cyclohexyl-benzene.
Claim 12
Dependent Claim 34 words
A nematic liquid crystal mixture in accordance with claim 10 which contains 37.44 wt.% 4'-n-pentyl-4-cyanobiphenyl, 22.65 wt.% 4'-n-pentyloxy-4-cyanobiphenyl, 5.16 wt.% 5-n-pentyl-2-(4-cyanophenyl)-pyrimidine, 10.49 wt.% 5-n-heptyl-2-(4-cyanophenyl)-pyrimidine, 11.31 wt.% 2-(4-cyanophenyl)-5-(4-n-butylphenyl)-pyrimidine, 7.95 wt.% 4-cyano-4"-n-pentyl-p-terphenyl and 5 wt.% 1-n-hexyl-4-cyclohexyl-benzene.
Claim 13
Dependent Claim 52 words
A nematic liquid crystal mixture in accordance with claim 8 which contains 8.7 wt.% p-n-butylbenzoic acid p'-cyanophenyl ester, 9.84 wt.% p-n-pentylbenzoic acid p'-cyanophenyl ester, 13.35 wt.% p-n-hexylbenzoic acid p'-cyanophenyl ester, 15.02 wt.% p-n-heptylbenzoic acid p'-cyanophenyl ester, 8.35 wt.% 5-n-pentyl-2-(4-cyanophenyl)-pyrimidine, 17.91 wt.% 5-n-heptyl-2-(4-cyanophenyl)-pyrimidine, 15.8 wt.% 2-(4-cyanophenyl)-5-(4-n-butylphenyl)-pyrimidine, 8 wt.% 1-n-hexyl-4-cyclohexyl-benzene and 6 wt.% 4-methyl-4'-n-pentyl-biphenyl.
Claim 14
Dependent Claim 52 words
A nematic liquid crystal mixture in accordance with claim 8 which contains 8.7 wt.% p-n-butylbenzoic acid p'-cyanophenyl ester, 9.84 wt.% p-n-pentylbenzoic acid p'-cyanophenyl ester, 13.35 wt.% p-n-hexylbenzoic acid p'-cyanophenyl ester, 15.02 wt.% p-n-heptylbenzoic acid p'-cyanophenyl ester, 8.35 wt.% 5-n-pentyl-2-(4-cyanophenyl)-pyrimidine, 17.91 wt.% 5-n-heptyl-2-(4-cyanophenyl)-pyrimidine, 15.8 wt.% 2-(4-cyanophenyl)-5-(4-n-butylphenyl)-pyrimidine, 9 wt.% 1-n-hexyl-4-cyclohexyl-benzene and 4 wt.% 4-methyl-4'-n-pentyl-biphenyl.
Claim 15
Dependent Claim 133 words
An electro-optical apparatus comprising a nematic liquid crystal mixture having positive anisotropy of the dielectric constants comprising a nematogenic material having a clearing point above 60° C. and one or more compounds of the formula ##STR31## wherein R 1 and R 2 are hydrogen or straight-chain alkyl, provided that at least one of R 1 and R 2 is other than hydrogen and that the sum of the number of carbon atoms present in R 1 and R 2 is at most 9, disposed between two plate means at least one of which plate means is transparent; means for controlling the optical activity of the cell; and said liquid crystal means having a helical structure in the direction perpendicular to the plate means and the surfaces of the plate means being wall oriented.
Claim 16
Dependent Claim 133 words
An electro-optical apparatus comprising a nematic liquid crystal mixture having positive anisotropy of the dielectric constants comprising a nematogenic material having a clearing point above 60° C. and one or more compounds of the formula ##STR31## wherein R 1 and R 2 are hydrogen or straight-chain alkyl, provided that at least one of R 1 and R 2 is other than hydrogen and that the sum of the number of carbon atoms present in R 1 and R 2 is at most 9, disposed between two plate means at least one of which plate means is transparent; means for controlling the optical activity of the cell; and said liquid crystal means having a helical structure in the direction perpendicular to the plate means and the surfaces of the plate means being wall oriented.
Claim 17
Dependent Claim 133 words
A rotation cell comprising a nematic liquid crystal mixture having positive anisotropy of the dielectric constants comprising a nematogenic material having a clearing point above 60° C. and one or more compounds of the formula ##STR32## wherein R 1 and R 2 are hydrogen or straight-chain alkyl, provided that at least one of R 1 and R 2 is other than hydrogen and that the sum of the number of carbon atoms present in R 1 and R 2 is at most 9, disposed between two plate means at least one of which plate means is transparent; means for controlling the optical activity of the cell; and said liquid crystal means having a helical structure in the direction perpendicular to the plate means and the surfaces of the plate means being wall oriented.
Claim 18
Dependent Claim 133 words
A rotation cell comprising a nematic liquid crystal mixture having positive anisotropy of the dielectric constants comprising a nematogenic material having a clearing point above 60° C. and one or more compounds of the formula ##STR32## wherein R 1 and R 2 are hydrogen or straight-chain alkyl, provided that at least one of R 1 and R 2 is other than hydrogen and that the sum of the number of carbon atoms present in R 1 and R 2 is at most 9, disposed between two plate means at least one of which plate means is transparent; means for controlling the optical activity of the cell; and said liquid crystal means having a helical structure in the direction perpendicular to the plate means and the surfaces of the plate means being wall oriented.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-04-15 1983-10-15 1984-04-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-04-15 1987-10-15 1988-04-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-04-15 1991-10-15 1992-04-15 $7700.00 Window Closed / Lapsed

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