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US4011173A Expired / Lapsed US ⏱️ 0.0 years remaining

Modified nematic mixtures with positive dielectric anisotropy

Assignee: Merck Patent GmbH
•
Filing: 1974-04-17
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Granted: 1977-03-08
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Expires: 1994-04-17
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Abstract

Abstract Nematic mixtures on the basis of derivatives of azoxybenzene and/or the phenyl ester of benzoic acid, containing at least one compound of the general formula X -- R -- Y wherein X represents straight-chain alkyl of 4-9 carbon atoms or dialkylamino of 2-4 carbon atoms, Y represents cyano, nitro, or trifluoromethyl, and R represents a divalent group of the Formula 2a, 2b, 2c, or 2d: ##STR1## AND OPTIONALLY ADDITIONALLY ONE OR MORE COMPOUNDS OF Formula 3 ##STR2## wherein R 1 and R 2 represent alkyl or alkoxy of 1-8 carbon atoms, possess a positive dielectric anisotropy and are advantageously utilized as dielectrics in liquid/crystal cells with homogeneous orientation.

Inventors

  • 👤 Ralf Steinstrasser

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 20:18
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/42

Claims Analysis

Total Claims: 36
Claim 1
Independent Claim 134 words
A modified liquid crystal nematic mixture having positive dielectric anisotropy and an enantiotropic nematic mesophase of about 20° to 80° C. extending over temperatures from 0° to 30° C., comprising an admixture of: a. at least one nematic compound of the formula ##STR6## wherein A is azoxy or carbonyloxy and R 1 and R 2 are each straight-chain alkyl or alkoxy of 1-8 carbon atoms; and b. at least one compound of the formula X - R - Y wherein X is dialkylamino of 2-4 carbon atoms; Y is cyano, nitro or trifluoromethyl; and R is selected from the group consisting of divalent radicals of the formulae ##STR7## characterized in that component (b) is present in an amount sufficient to increase the dielectric anisotropy of the admixture to a value of at least +2.
Claim 2
Dependent Claim 134 words
A modified liquid crystal nematic mixture having positive dielectric anisotropy and an enantiotropic nematic mesophase of about 20° to 80° C. extending over temperatures from 0° to 30° C., comprising an admixture of: a. at least one nematic compound of the formula ##STR6## wherein A is azoxy or carbonyloxy and R 1 and R 2 are each straight-chain alkyl or alkoxy of 1-8 carbon atoms; and b. at least one compound of the formula X - R - Y wherein X is dialkylamino of 2-4 carbon atoms; Y is cyano, nitro or trifluoromethyl; and R is selected from the group consisting of divalent radicals of the formulae ##STR7## characterized in that component (b) is present in an amount sufficient to increase the dielectric anisotropy of the admixture to a value of at least +2.
Claim 3
Dependent Claim 21 words
A modified nematic mixture according to claim 1, comprising 65-99% by weight of (a) and correspondingly 35-1% by weight of (b).
Claim 4
Dependent Claim 21 words
A modified nematic mixture according to claim 2, comprising 70-95% by weight of (a) and correspondingly 30-5% by weight of (b).
Claim 5
Dependent Claim 20 words
A modified nematic mixture according to claim 1, wherein R has the structure 2c or 2d and Y is cyano.
Claim 6
Dependent Claim 20 words
A modified nematic mixture according to claim 1, wherein R has the structure 2a or 2b and Y is cyano.
Claim 7
Dependent Claim 12 words
A modified nematic mixture according to claim 5, wherein X is dimethylamino.
Claim 8
Dependent Claim 13 words
A modified nematic mixture according to claim 1, wherein component (b) is 4-dimethylaminobenzonitrile.
Claim 9
Dependent Claim 27 words
A modified nematic mixture according to claim 1, wherein component (a) is one in which at least one of R 1 and R 2 is straight-chain alkyl.
Claim 10
Dependent Claim 23 words
A modified nematic mixture according to claim 8, wherein component (a) is selected from the group consisting of 4-n-buty-4'-methoxy-azoxybenzene, 4-ethyl-4'-methoxyazoxybenzene and mixtures thereof.
Claim 11
Dependent Claim 33 words
A modified nematic mixture according to claim 8, wherein component (a) is selected from the group consisting of the 4-n-pentylphenyl ester of anisic acid, the 4'-pentylphenyl ester of 4-n-hexoxybenzoic acid and mixtures thereof.
Claim 12
Dependent Claim 222 words
A modified liquid crystal nematic mixture having positive dielectric anisotropy and an enantiotropic nematic mesophase of about 20° to 80° C. extending over temperatures from 0° to 30° C., comprising an admixture of: a. 20-95% by weight of at least one nematic compound of the formula ##STR8## wherein A is azoxy or carbonyloxy and R 1 and R 2 are each straight-chain alkyl or alkoxy of 1-8 carbon atoms; b. 3-65% by weight of at least one compound of the formula X -- R -- Y wherein X is straight-chain alkyl of 4-9 carbon atoms or dialkylamino of 2-4 carbon atoms; Y is cyano, nitro or trifluoromethyl when X is dialkylamino, and Y is nitro or trifluoromethyl when X is straight-chain alkyl; and R is selected from the group consisting of divalent radicals of the formulae ##STR9## characterized in that component (b) is present in an amount sufficient to increase the dielectric anisotropy of the admixture to a value of at least +2; and c. 2-27% by weight based on the total composition of at least one compound of the formula ##STR10## wherein R 1 and R 2 are each alkyl or alkoxy of 1-8 carbon atoms, said component (c) being present in an amount sufficient to compensate the clearing-point-lowering effect of the addition of component (b) to the nematic component (a).
Claim 13
Dependent Claim 222 words
A modified liquid crystal nematic mixture having positive dielectric anisotropy and an enantiotropic nematic mesophase of about 20° to 80° C. extending over temperatures from 0° to 30° C., comprising an admixture of: a. 20-95% by weight of at least one nematic compound of the formula ##STR8## wherein A is azoxy or carbonyloxy and R 1 and R 2 are each straight-chain alkyl or alkoxy of 1-8 carbon atoms; b. 3-65% by weight of at least one compound of the formula X -- R -- Y wherein X is straight-chain alkyl of 4-9 carbon atoms or dialkylamino of 2-4 carbon atoms; Y is cyano, nitro or trifluoromethyl when X is dialkylamino, and Y is nitro or trifluoromethyl when X is straight-chain alkyl; and R is selected from the group consisting of divalent radicals of the formulae ##STR9## characterized in that component (b) is present in an amount sufficient to increase the dielectric anisotropy of the admixture to a value of at least +2; and c. 2-27% by weight based on the total composition of at least one compound of the formula ##STR10## wherein R 1 and R 2 are each alkyl or alkoxy of 1-8 carbon atoms, said component (c) being present in an amount sufficient to compensate the clearing-point-lowering effect of the addition of component (b) to the nematic component (a).
Claim 14
Dependent Claim 25 words
A modified nematic mixture according to claim 11 comprising 45-80% by weight of (a); 10-45% by weight of (b); and 10-25% by weight of (c).
Claim 15
Dependent Claim 28 words
A modified nematic mixture according to claim 11, wherein at least one of R 1 and R 2 of component (c) is straight-chain alkyl of 4-8 carbon atoms.
Claim 16
Dependent Claim 39 words
A modified nematic mixture according to claim 13, wherein component (c) is selected from the group consisting of the 4'-n-butylphenyl ester of 4-anisoyloxybenzoic acid, the 4'-n-butylphenyl ester of 4-(4-n-hexoxybenzoyloxy)-benzoic acid, the 4'-n-butylphenyl ester of 4-(4-n-butylbenzoyloxy)benzoic acid and mixtures thereof.
Claim 17
Dependent Claim 34 words
In a liquid crystal electrooptical cell comprising transparent or translucent electrodes surrounding a dielectric nematic composition having a homogeneous orientation, the improvement wherein said nematic composition is the modified nematic mixture of claim 1.
Claim 18
Dependent Claim 34 words
In a liquid crystal electrooptical cell comprising transparent or translucent electrodes surrounding a dielectric nematic composition having a homogenous orientation, the improvement wherein said nematic composition is the modified nematic mixture of claim 11.
Claim 19
Dependent Claim 104 words
A process for increasing the dielectric anistropy of a nematic substance consisting of at least one compound of the formula ##STR11## wherein A is azoxy or carbonyloxy and R 1 and R 2 are each straight-chain alkyl or alkoxy of 1-8 carbon atoms, which comprises admixing therewith at least one compound of the formula X -- R -- Y wherein X is dialkylamino of 2-4 carbon atoms; Y is cyano, nitro or trifluoromethyl; and R is selected from the group consisting of divalent radicals of the formulae ##STR12## in an amount sufficient to increase the dielectric anisotropy to a value of at least +2.
Claim 20
Dependent Claim 104 words
A process for increasing the dielectric anistropy of a nematic substance consisting of at least one compound of the formula ##STR11## wherein A is azoxy or carbonyloxy and R 1 and R 2 are each straight-chain alkyl or alkoxy of 1-8 carbon atoms, which comprises admixing therewith at least one compound of the formula X -- R -- Y wherein X is dialkylamino of 2-4 carbon atoms; Y is cyano, nitro or trifluoromethyl; and R is selected from the group consisting of divalent radicals of the formulae ##STR12## in an amount sufficient to increase the dielectric anisotropy to a value of at least +2.
Claim 21
Dependent Claim 55 words
A process according to claim 17, further comprising admixing at least one compound of the formula ##STR13## wherein R 1 and R 2 are each alkyl or alkoxy of 1-8 carbon atoms, in an amount sufficient to compensate the clearing-point-lowering effect of the admixture of the compound of the formula X -- R -- Y.
Claim 22
Dependent Claim 78 words
a modified nematic mixture according to claim 5, comprising 20-95% by weight of (a); 3-65% by weight of (b); and (c) 2-27% by weight based on the total composition of at least one compound of the formula ##STR14## wherein R 1 and R 2 are each alkyl or alkoxy of 1-8 carbon atoms, said component (c) being present in an amount sufficient to compensate the clearing-point-lowering effect of the addition of component (b) to the nematic component (a).
Claim 23
Dependent Claim 25 words
A modified nematic mixture according to claim 19, comprising 45-80% by weight of (a); 10-45% by weight of (b); and 10-25% by weight of (c).
Claim 24
Dependent Claim 28 words
A modified nematic mixture according to claim 19, wherein at least one of R 1 and R 2 of component (c) is straight-chain alkyl of 4-8 carbon atoms.
Claim 25
Dependent Claim 39 words
A modified nematic mixture according to claim 19, wherein component (c) is selected from the group consisting of the 4'-n-butylphenyl ester of 4-anisoyloxybenzoic acid, the 4'-n-butylphenyl ester of 4-(4-n-hexoxybenzoyloxy)-benzoic acid, the 4'-n-butylphenyl ester of 4-(4-n-butylbenzoyloxy)-benzoic acid and mixtures thereof.
Claim 26
Dependent Claim 15 words
A modified nematic mixture according to claim 19, wherein X in component (b) is dimethylamino.
Claim 27
Dependent Claim 23 words
A modified nematic mixture according to claim 19, wherein component (a) is selected from the group consisting of 4-n-butyl-4'-methoxy-azoxybenzene, 4-ethyl-4'-methoxy-azoxybenzene and mixtures thereof.
Claim 28
Dependent Claim 15 words
A modified nematic mixture according to claim 24, wherein X in component (b) is dimethylamino.
Claim 29
Dependent Claim 13 words
A modified nematic mixture according to claim 25, wherein component (b) is 4-dimethylaminobenzonitrile.
Claim 30
Dependent Claim 39 words
A modified nematic mixture according to claim 25, wherein component (c) is selected from the group consisting of the 4'-n-butylphenyl ester of 4-anisoyloxybenzoic acid, the 4'-n-butylphenyl ester of 4-(4-n-hexoxybenzoyloxy)benzoic acid, the 4'-n-butylphenyl ester of 4-(4-n-butylbenzoyloxy)benzoic acid and mixtures thereof.
Claim 31
Dependent Claim 24 words
A modified nematic mixture according to claim 24, wherein component (a) is a mixture of said compounds containing a major portion of said 4-n-butyl-4'-methoxyazoxybenzene.
Claim 32
Dependent Claim 15 words
A modified nematic mixture according to claim 28, wherein X in component (b) is dimethylamino.
Claim 33
Dependent Claim 13 words
A modified nematic mixture according to claim 29, wherein component (b) is 4-dimethylaminobenzonitrile.
Claim 34
Dependent Claim 39 words
A modified nematic mixture according to claim 29, wherein component (c) is selected from the group consisting of the 4'-n-butylphenyl ester of 4-anisoyloxybenzoic acid, the 4'-n-butylphenyl ester of 4-(4-n-hexoxybenzoyloxy)benzoic acid, the 4'-n-butylphenyl ester of 4-(4-n-butylbenzoyloxy)benzoic acid and mixtures thereof.
Claim 35
Dependent Claim 18 words
A modified nematic mixture according to claim 30, wherein component (c) is the 4'-n-butylphenyl ester of 4-(4-n-butylbenzoyloxy)-benzoic acid.
Claim 36
Dependent Claim 28 words
A modified nematic mixture according to claim 30, wherein component (c) is a mixture of the 4'-n-butylphenyl ester of 4-(4-n-butylbenzoyloxy)-benzoic acid and the 4'-n-butylphenyl ester of 4-(4-n-hexoxybenzoyloxy)-benzoic acid.

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Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-03-07 1980-09-06 1981-03-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-03-07 1984-09-06 1985-03-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-03-07 1988-09-06 1989-03-08 $7700.00 Window Closed / Lapsed

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