Note: Descriptions are shown in the official language in which they were submitted.
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The inventioD relates to DematOgeDeOuS mixtures
which contain N-(4-methoxybenzylideDe)-4'-D-butylaniline
aod N-(4-ethoxybenzylideDe)-4'-n-butylaniline and N-(4-
methoxybenzylidene)-4'-0-D-~utyrylamiDopheDol and at least
one member of the group ¢onsistiDg of 4-oaproyloxybeDzoi¢-
acid-4'-ethoxyphenole4ter aDd 4-oaproyloxybenzoic-acid-4~-
butoxyphenolester.
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Nematogeneous compounds and nematogeneous mixtures
possess special electro-optical properties, which allow the
construction of light-diifusing component parts, e.g., o$
liquid crystal iDdicators. In the practical operation of
such light-diffusing compoDent parts, the nematic phase used
should show the greatest possible liquid crystalline nematic
ra~ge (persistaDoe range).
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~5 While such substaD¢es have been known ~or some time
~ for high temperature ranges, it has beeD ODly iD the last
,- few years that Dematoge~eous co~pounds have bee~ found for
the range
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between room temperature and below. ~or working at temperature~
at and below 0C., no pure nematogeneou~ substances have so far
been found. For these temperatureq, nematogeneous mlxtures are
employed. Nematogeneous mixtures with melting points below 0~.
are already known. For example, for a mixture Or 70.2 mol %
N-(4-methoxybenzylidene)-4'-n-butylaniline and 29.8 mol %
N-(4-ethoxybenzylidene)-4'-n-butylaniline, a melting point
below -40C. (German Published Application 2,~21,085) is
reported. In an experimental retesting, however, a melting point
Or 14.5C. was measured ~or a mlxture of the given composition,
whlch was prepared ~rom an N-(4-methoxybenzylidene)-4'-n-butyl-
aniline havlng a melting point Or 21C., a clearing point
Or 44-45C. and a purity determlned by gas chromatography Or abov~
99~ and an N-(4-ethoxybenzylldene)-4'-n-butylaniline having a
meltlng point Or 35C., a clearlng point Or 79C. and a purity
determined by gas-chromatography o~ above 99%. With 810w
cooling, the solldiricatlon point iq between -2C. and -8C.,
~ub~ect to the undercoollng errects.
In addition, nematogeneous mixtures are known wlth
melting points down to -3C. (German Published Application
2,032,~66), which consi3t o~ a mlxture of N-(4-methoxybenzylidene _
4'-n-butylaniline or N-(4-ethoxybenzylidene)-4'-n-butylaniline
and N-(4-methoxybenzylidene)-4'-0-n-butyrylamlnophenol and
4-caproyloxybenzoic acld-4-ethoxyphenolester or 4-caproyloxy-
benzoic-acid-4-butoxyphenolester. For these compositions, it is
stated that by the substitution Or N-(4-ethylbenzylidene)-4'-n-
butylani~ne ~or N-(4-methoxybenzylidene)-4'-n-butylaniline~ the
melting polnts Or the compositions would o~ cour~e be higher.
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Unexpectedly, it has now been ~ound that nematogeneous
mixtures, which contain N-(4-methoxybenzylidene)-4'-n-butylanilin
and N-(4-ethoxybenzylidene)-4'-n-butylaniline and N-(4-methoxy-
benzylidene)-4'-0-n-butyrylaminophenol and at least one member
Or the group consisting of 4-caproyloxybenzoic-acid-4'-ethoxy-
phenolester and 4-caproyloxybénzoic-acid-4'-butoxyphenolester,
exhibit solidification pointq Or partially below -30C. with larg
persistence areas. Both with day-long standing as well as with
mechanical stirring at low temperatures, these mixtures do not
æol~ as crystals to some degree. If they are cooled below
their solidlfication points, their viscosity increases and they
~- ~ finally become solidified like glass. These mixtures
exhiblt a marked "dynamic scattering" e~ect and are well
suited as solvent~ for nuclear resonance spectroscopy.
The solidification points depend on the percentage
compositlon Or the mixtures. In the following Table 1 mixtures
- are given with solidlfication points above 0C. and in Table 2
mlxtures with solidlfication points below 0C.
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~ TABLE 1
Composition in % Clearing
bY weight Solidirication Point
No. I II III IV Point in C. in C.
1 5 5 45 45 i6 95
2 13 7 28 52 6 87
Z5 3 45 45 5 5 9 66
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TABLE 2
Solidi~ica- Clearing
Composition in % by weight tion Point Point
l No. I _II III IV V in G. in C.
4 18 18 32 32 0 -5 84
~ 5 22.75 12.75 32.5 32.5 0 _24 73
: 6 30 30 20 0 20 -34 72
~. 7 30 30 20 10 10 -34 73
.. . 8 32.5 17.5 17.532.5 -15 60
9 36 36 14 14 0 _24 69 .
In the tables, numbers I through V were applied to .
the components a~ follows: .
: \ I: N-(4-methoxybenzylidene)-4'-n-butylaniline
II: N-(4-ethoxybenzylidene)-4'-n-butylaniline ~ .
15III: N-(4-methoxybenzylldene)-4'-0-n-butyrylaminophenol
~A;- IV: 4-caproyloxybenzoic-acid-4'-ethoxyphenolester
.~ V: 4-caproyloxybenzoic-acid-4'-butoxyphenolester ,,'. .=' ' .
. Mixtures o~ the following compositions have
~; solidification points below 0C.: 15 to 38% by weight of
; 20 component I, 10 to 38~ by weight of component II; 10 to 35~
by weight of component III and at least one member of the group
:, consisting of 10 to 35% by weight of component IV and 10 to 35
by weight o omponent V.
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The nematogeneous mixtures of the present invention may
be used like those indicated in related art. They are
especially suited as active phase in electro-optical display
units. The production o~ such electro-optical display units,
USiDg nematogeneous mixtures,is known. The nematogeneous
mixtures of the preseDt inveDtion are easy to iorm
homotropic textures. Moreover, from the chemical point of
view they are remarkably stable.
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