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US4395350A Expired / Lapsed US ⏱️ 0.0 years remaining

Liquid crystal mixtures

Assignee: F Hoffmann La Roche AG
•
Filing: 1981-07-01
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Granted: 1983-07-26
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Expires: 2001-07-01
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Abstract

Abstract Liquid crystal mixtures containing a coloring substance which comprise about 5 to about 40 weight % of trans-p-[5-(4-alkylcyclohexyl)-2-pyrimidinyl]benzonitriles, about 10 to about 60 weight % of trans-4-alkylcyclohexane carboxylic acid phenyl esters and about 0.1 to about 15 weight % of one or more coloring substances of the formula ##STR1## wherein m stands for the number 1 and X is alkoxy and Y is nitro; or m stands for the number 1 or 2; and X is p-alkoxyphenyl and Y is nitro or dialkylamino, or X is alkoxy and Y is -p-nitrophenyl or -(dialkylamino)phenyl; or m stands for the number 2, and X is alkoxy and Y is alkoxy, nitro or dialkylamino, or both X and Y are dialkylamino; and wherein the alkoxy denotes a straight-chain group containing 1 to 12 carbon atoms and the alkyl groups in the dialkylamino each denote a straight-chain alkyl group containing 1 to 4 carbon atoms are described.

Inventors

  • 👤 Arthur Boller
  • 👤 Alfred Germann
  • 👤 Martin Schadt
  • 👤 Alois Villiger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 14:49
CPC Classifications
C; C09; C09B; C09B31/00; C09B31/02; C09B31/04; C09B31/043; C09B1/00; C09B1/50; C09B1/503; C09B29/00; C09B29/06; C09B29/08; C09B29/0805; C09B29/0807; C09B29/0809; C09B29/081; C09B29/10; C09B29/12; C09B31/06; C09B31/062; C09B43/00; C09B43/28; C09K; C09K19/00; C09K19/52; C09K19/60

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 207 words
A coloring substance-containing liquid crystal mixture which comprises about 5 to about 40 weight % of one or more trans-p-[5-(4-alkylcyclohexyl)-2-pyrimidinyl]benzonitriles of the formula ##STR18## wherein R 1 is a straight-chain alkyl group containing 2 to 7 carbon atoms, about 10 to about 60 weight % of one or more trans-4-alkylcyclohexane carboxylic acid phenyl ester of the formula ##STR19## wherein R 2 is a straight-chain alkyl group containing 2 to 6 carbon atoms and R 3 is cyano or a straight-chain alkoxy group containing 1 to 6 carbon atoms, and about 0.1 to about 15 weight % of one or more coloring substances of the formula ##STR20## wherein m is the integer 1 and X is alkoxy and Y is nitro, or m is the integer 1 or 2, and X is p-alkoxyphenyl and Y is nitro or dialkylamino, or X is alkoxy and Y is p-nitrophenyl or p-(dialkylamino)phenyl; or m is the integer 2, and X is alkoxy and Y is alkoxy, nitro or dialkylamino, or both X and Y are dialkylamino groups; and wherein the alkoxy denotes a straight-chain alkoxy group containing 1 to 12 carbon atoms and the alkyl groups in the dialkylamino each denote a straight-chain alkyl group containing 1 to 4 carbon atoms.
Claim 2
Dependent Claim 207 words
A coloring substance-containing liquid crystal mixture which comprises about 5 to about 40 weight % of one or more trans-p-[5-(4-alkylcyclohexyl)-2-pyrimidinyl]benzonitriles of the formula ##STR18## wherein R 1 is a straight-chain alkyl group containing 2 to 7 carbon atoms, about 10 to about 60 weight % of one or more trans-4-alkylcyclohexane carboxylic acid phenyl ester of the formula ##STR19## wherein R 2 is a straight-chain alkyl group containing 2 to 6 carbon atoms and R 3 is cyano or a straight-chain alkoxy group containing 1 to 6 carbon atoms, and about 0.1 to about 15 weight % of one or more coloring substances of the formula ##STR20## wherein m is the integer 1 and X is alkoxy and Y is nitro, or m is the integer 1 or 2, and X is p-alkoxyphenyl and Y is nitro or dialkylamino, or X is alkoxy and Y is p-nitrophenyl or p-(dialkylamino)phenyl; or m is the integer 2, and X is alkoxy and Y is alkoxy, nitro or dialkylamino, or both X and Y are dialkylamino groups; and wherein the alkoxy denotes a straight-chain alkoxy group containing 1 to 12 carbon atoms and the alkyl groups in the dialkylamino each denote a straight-chain alkyl group containing 1 to 4 carbon atoms.
Claim 3
Dependent Claim 126 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 1, which contains about 0.1 to about 10 weight % of one or more coloring substances of the formula ##STR21## wherein m 1 is the integer 1, and X 1 is alkoxy and Y 1 is nitro, p-nitrophenyl or p-(dialkylamino)phenyl, or X 1 is p-alkoxyphenyl and Y 1 is nitro or dialkylamino; or m 1 is the integer 2, and X 1 is p-alkoxyphenyl and Y 1 is nitro, or X 1 is alkoxy and Y 1 is p-nitrophenyl, alkoxy or nitro; and wherein the alkoxy denotes a straight-chain alkoxy group containing 1 to 12 carbon atoms and the alkyl groups in the dialkylamino each denote a straight-chain alkyl group containing 1 to 4 carbon atoms.
Claim 4
Dependent Claim 109 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 1, wherein the coloring substance is present from about 0.1 to about 5 weight % and comprises one or more coloring substances of the formula ##STR22## wherein m 2 is the integer 2, and X 2 is p-alkoxyphenyl and Y 2 is dialkylamino, or X 2 is alkoxy and Y 2 is p-(dialkylamino)phenyl or dialkylamino, or both X 2 and Y 2 are dialkylamino groups; and wherein the alkoxy denotes a straight-chain alkoxy group containing 1 to 12 carbon atoms and the alkyl groups in the dialkylamino each denote a straight-chain alkyl group containing 1 to 4 carbon atoms.
Claim 5
Dependent Claim 49 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 1, which contains in addition one or more coloring substances of the formula ##STR23## wherein R 7 is a straight-chain alkyl group containing 5 to 8 carbon atoms, in an amount of about 0.1 to about 5 weight %.
Claim 6
Dependent Claim 31 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 4, which contains one or more coloring substances of formula VI in an amount of up to about 3 weight %.
Claim 7
Dependent Claim 56 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 1, which also contains one or more optically active compounds of the formula ##STR24## wherein Z is the group --CH 2 -- or --CH 2 O-- and n is the integer 1, 2, 3 or 4, in an amount of up to about 4 weight %.
Claim 8
Dependent Claim 24 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 6, wherein the optically active additive is (+)- or (-)-4'-(2-methylbutyl)-4-cyanobiphenyl or (+)- or (-)-4'-(2-methylbutyloxy)-4-cyanobiphenyl.
Claim 9
Dependent Claim 45 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 1 or 6, wherein, in the compound of formula XII, the alkoxy group is a straight-chain alkoxy group containing 3 to 9 carbon atms, and the alkyl group in the dialkylamino is methyl or ethyl.
Claim 10
Dependent Claim 127 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 1 or 6, wherein the coloring substance comprises one or more compounds selected from the group consisting of compounds of the formulas ##STR25## wherein R 4 is a straight-chain alkyl group containing 1 to 9 carbon atoms, and ##STR26## wherein R 5 is a straight-chain alkyl group containing 1 to 9 carbon atoms, and wherein one or more of the compounds of formula III are present in an amount of 0 to about 3 weight % and the compounds of formula IV are present in an amount of 0 to about 10 weight %, provided that the sum of the amounts of coloring substances of formulas III and/or IV present is at least about 0.3 weight %.
Claim 11
Dependent Claim 191 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 1, 2, 3, 4 or 6, which contains in addition one or more of the following groups of liquid crystals: (a) up to about 50 weight % of one or more 4-cyanobiphenyls of the formula ##STR27## wherein R 8 is a straight-chain alkyl or alkoxy group containing 2 to 8 carbon atoms and R 9 is cyano; (b) up to about 30 weight % of one or more p-(5-alkyl-2-pyrimidinyl)benzonitriles of the formula ##STR28## wherein R 10 is a straight-chain alkyl group containing 2 to 7 carbon atoms; (c) up to about 10 weight % of one or more 4"-alkyl-4-cyano-p-terphenyls of the formula ##STR29## wherein R 11 is a straight-chain alkyl group containing 3 to 7 carbon atoms, (d) up to about 15 weight % of one or more p-alkylbenzoic acid p'-cyanophenyl esters of the formula ##STR30## wherein R 12 is a straight-chain alkyl group containing 2 to 7 carbon atoms; or (e) up to about 12 weight % of one or more 2-(4-cyanophenyl)-5-(4-alkylphenyl)pyrimidines of the formula ##STR31## wherein R 10 is a straight-chain alkyl group containing 2 to 7 carbon atoms.
Claim 12
Dependent Claim 35 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 9, wherein R 4 in the compound of formula III is heptyl, and R 5 in the compound of formula IV is methyl or heptyl.
Claim 13
Dependent Claim 31 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 4, wherein the total concentration of the compounds of formulas VI and XII is about 0.3 to about 10 weight %.
Claim 14
Dependent Claim 31 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 4, wherein the total concentration of the compounds of formulas VI and XII is about 0.3 to about 5 weight %.
Claim 15
Dependent Claim 31 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 2, wherein the amount of one or more coloring substances present comprises from about 0.3 to about 1.4 parts by weight.
Claim 16
Dependent Claim 43 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 2, wherein, in the compound of formula XIII, the alkoxy group is a straight-chain alkoxy group containing 3 to 9 carbon atoms, and the alkyl group in the dialkylamino is methyl or ethyl.
Claim 17
Dependent Claim 43 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 3, wherein, in the compound of formula XIV, the alkoxy group is a straight-chain alkoxy group containing 3 to 9 carbon atoms, and the alkyl group in the dialkylamino is methyl or ethyl.
Claim 18
Dependent Claim 31 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 3, wherein the amount of one or more coloring substances present comprises from about 0.4 to about 1.4 parts by weight.
Claim 19
Dependent Claim 31 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 4, wherein the amount of one or more coloring substances present comprises from about 1.0 to about 2.2 parts by weight.
Claim 20
Dependent Claim 123 words
A coloring substance-containing liquid crystal mixture comprising trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile, trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile, trans-p-[5-(4-heptylcyclohexyl)-2-pyrimidinyl]benzonitrile, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)-phenyl ester, 4'-pentyl-4-cyanobiphenyl, one or more coloring substances selected from the group consisting of compounds of the formulas ##STR32## wherein R 4 is a straight-chain alkyl group containing 1 to 9 carbon atoms, ##STR33## wherein R 5 is a straight-chain alkyl group containing 1 to 9 carbon atoms, and ##STR34## wherein R 7 is a straight-chain alkyl group containing 5 to 8 carbon atoms, optically active 4'-(2-methylbutyl)-4-cyanobiphenyl and optically active 4'-(2-methylbutyloxy)-4-cyanobiphenyl, with the proviso that at least one of the coloring substances is selected from the group consisting of compounds of formulas III and IV.
Claim 21
Dependent Claim 123 words
A coloring substance-containing liquid crystal mixture comprising trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile, trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile, trans-p-[5-(4-heptylcyclohexyl)-2-pyrimidinyl]benzonitrile, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)-phenyl ester, 4'-pentyl-4-cyanobiphenyl, one or more coloring substances selected from the group consisting of compounds of the formulas ##STR32## wherein R 4 is a straight-chain alkyl group containing 1 to 9 carbon atoms, ##STR33## wherein R 5 is a straight-chain alkyl group containing 1 to 9 carbon atoms, and ##STR34## wherein R 7 is a straight-chain alkyl group containing 5 to 8 carbon atoms, optically active 4'-(2-methylbutyl)-4-cyanobiphenyl and optically active 4'-(2-methylbutyloxy)-4-cyanobiphenyl, with the proviso that at least one of the coloring substances is selected from the group consisting of compounds of formulas III and IV.
Claim 22
Dependent Claim 158 words
A coloring substance-containing liquid crystal mixture, in accordance with claim 25, which contains about 7.73 parts by weight of trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile, about 5.52 parts by weight of trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile, about 14.38 parts by weight of trans-p-[5-(4-heptylcyclohexyl)-2-pyrimidinyl]benzonitrile, about 7.64 parts by weight of trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, about 6.95 parts by weight of trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, about 14.13 parts by weight of trans-4-butylcyclohexane carboxylic acid p-(ethoxy)-phenyl ester, about 12.62 parts by weight of trans-4-pentylcyclohexane carboxylic p-(methoxy)phenyl ester, about 27.28 parts by weight of 4'-pentyl-4-cyanobiphenyl, about 0.95 parts by weight of the compound of formula III wherein R 4 is heptyl, about 1 part by weight of the compound of formula IV wherein R 5 is methyl or heptyl, about 1.80 parts by weight of the compound of formula VI wherein R 7 is heptyl and up to about 4 parts by weight of a compound selected from the group consisting of optically active 4'-(2-methylbutyl)-4-cyanobiphenyl and optically active 4'-(2-methylbutyloxy)-4-cyanobiphenyl.

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Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-07-25 1987-01-24 1987-07-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-07-25 1991-01-24 1991-07-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-07-25 1995-01-24 1995-07-26 $7700.00 Window Closed / Lapsed

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