Liquid-crystalline composition of matter

Details Liquid-crystalline composition of matter Liquid-crystalline composition of matter

2001-05-25

2004-03-30

Huff, Mark F. (Department: 1756)

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

C252S299640, C252S299610

Reexamination Certificate

active

06712992

ABSTRACT:

The present invention relates to a liquid-crystalline composition of matter comprising as components,
A) at least one compound of the formula I
Z
1
—Y
1
—A
1
—Y
3
—M—Y
4
—A
2
—Y
2
—Z
2
  I,
 where the variables, independently of one another, have the following meanings:
Z
1
and Z
2
are each a reactive group,
Y
1
to Y
4
are each a linking unit,
A
1
and A
2
are each a spacer, and
M is a mesogenic group,
B) at least one reactive compound selected from the group consisting of the subgroups
b1) vinyl or allyl ethers,
b2) vinyl or allyl esters of saturated or unsaturated carboxylic acids,
b3) methacrylic or acrylic esters of monofunctional or polyfunctional alcohols,
b4) polyester (meth)acrylates,
b5) vinylaromatics or vinylheteroaromatics, and
b6) compounds of the general formula II
CH
2
═CH—NR
2
—R
1
  II,
in which R
1
and R
2
are as defined in detail in the description, and
C) if desired, further additives.
The present invention further relates to the use of the compositions of matter of the invention for producing optical components, for printing or coating substrates, for producing dispersions and emulsions, films and pigments.
The present invention further relates to optical components, printed or coated substrates, dispersions and emulsions, films and pigments which have been produced using the compositions of matter according to the invention.
The preparation of cholesteric liquid-crystal mixtures usually involves using a liquid-crystalline (nematic) base material and one or more optically active dopants.
Despite process optimizations, including the selection of suitable and inexpensive raw materials, the preparation of liquid-crystalline base materials remains generally complicated and costly. The same applies, usually to a far greater extent, to the preparation of chiral dopants, typically involving the use of enantiomerically poor starting materials and possibly requiring a costly post-purification of the raw product obtained.
It is an object of the present invention to provide modified liquid-crystalline base materials, if desired in a mixture with chiral dopants, which base materials can be prepared more economically and whose optical properties are at least as good as or even better than the unmodified base materials.
We have found that, surprisingly, this object is achieved by liquid-crystalline compositions of matter obtained by mixing the liquid-crystalline (doped or undoped) base materials with the polymerizable compounds of the subgroups b1) to b6) mentioned at the beginning.
The present invention therefore provides a liquid-crystalline composition of matter comprising, as components,
A) at least one compound of the formula I
 Z
1
—Y
1
—A
1
—Y
3
—M—Y
4
—A
2
—Y
2
—Z
2
  I,
 where the variables, independently of one another, have the following meanings:
Z
1
and Z
2
are each a reactive group,
Y
1
to Y
4
are each a chemical single bond, oxygen, sulfur, —O—CO—, —CO—O—, —O—CO—O—, —CO—NR—, —NR—CO—, —O—CO—NR—, —NR—CO—O— or —NR—CO—NR—,
R is hydrogen or C
1
-C
4
-alkyl,
A
1
and A
2
are each a spacer having from 1 to 30 carbon atoms, in which the carbon chain may be monosubstituted or polysubstituted by methyl, fluorine, chlorine or bromine and/or interrupted by ether oxygen, thioether sulfur or non-adjacent imino or C
1
-C
4
-alkylimino groups, and
M is a mesogenic group,
B) at least one reactive compound selected from the group consisting of the subgroups
b1) vinyl or allyl ethers,
b2) vinyl or allyl esters of saturated or unsaturated carboxylic acids,
b3) methacrylic or acrylic esters of monofunctional or polyfunctional alcohols,
b4) polyester (meth)acrylates,
b5) vinylaromatics or vinylheteroaromatics, and
b6) compounds of the general formula II
CH
2
═CH—NR
2
—R
1
  II,
where:
R
2
is hydrogen, C
1
-C
4
-alkyl or, together R
3
, a saturated or unsaturated C
3
-, C
4
- or C
5
-alkylene bridge, in which up to two CH
2
groups may be replaced by NH, N(C
1
-C
4
-alkyl), N(C
6
-C
10
-aryl) or oxygen and up to two CH groups may be replaced by N, and
R
3
is hydrogen, C
1
-C
4
-alkyl or a radical which, together with R
2
, forms a saturated or unsaturated C
3
-, C
4
- or C
5
-alkylene bridge, in which up to two CH
2
groups may be replaced by NH, N(C
1
-C
4
-alkyl), N(C
6
-C
10
-aryl) or oxygen and up to two CH groups may be replaced by N, and
C) if desired, further additives.
Suitable spacers A
1
and A
2
are all groups known for this purpose to a person skilled in the art. The spacers usually contain one to 30, preferably one to 12, particularly preferably one to six, carbon atoms and consist in particular of linear aliphatic groups. The carbon chain may be monosubstituted or polysubstituted by methyl, fluorine, chlorine or bromine and/or interrupted by ether oxygen, thioeher sulfur or non-adjacent imino or C
1
-C
4
-alkylimino groups.
Examples of representative spacers are:
—(CH
2
)
u
—, —(CH
2
CH
2
O)
v
CH
2
CH
2
—,
—CH
2
CH
2
SCH
2
CH
2
,
—CH
2
CH
2
NHCH
2
CH
2
—,
where u is 1 to 30, preferably 1 to 12, v is 1 to 14, preferably 1 to 5, and w is 1 to 9, preferably 1 to 3.
Preferred spacers are ethylene, propylene, n-butylene, n-pentylene and n-hexylene.
Mesogenic groups M can be all suitable mesogenic groups known to a person skilled in the art.
Particularly suitable mesogenic groups are those of the formula Ia
(—T—Y
5
)
r
—T—  Ia
where
T at each occurrence is a divalent, saturated or unsaturated carbocyclic or heterocyclic radical
Y
5
is a chemical single bond, oxygen, sulfur, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —CO—NR—, —NR—CO—, —O—CO—NR—, —NR—CO—O— or —NR—CO—NR— and
r is 0, 1, 2 or 3, where, if r>0, both T and Y
5
can be identical or different at each occurrence.
The radicals T may be ring systems which are substituted by fluorine, chlorine, bromine, cyano, hydroxyl, formyl, nitro, C
1
-C
20
-alkyl, C
1
-C
20
-alkoxy, C
1
-C
20
-alkoxycarbonyl, C
1
-C
20
-monoalkylaminocarbonyl, C
1
-C
20
-alkylcarbonyl, C
1
-C
20
-alkylcarbonyloxy or C
1
-C
20
-alkylcarbonylamino. Preferred radicals T are:
Examples of mesogenic groups M are:
Further possible mesogenic groups M correspond to the following formulae:
In accordance with the above examples for possible radicals T, the (unsubstituted) mesogenic groups shown above may of course be substituted by fluorine, chlorine, bromine, cyano, hydroxyl, formyl, nitro, C
1
-C
20
-alkyl, C
1
-C
20
-alkoxy, C
1
—C
20
-alkoxycarbonyl, C
1
-C
20
-monoalkylcarbonyl, C
1
-C
20
-alkylcarbonyl, C
1
—C
20
-alkylcarbonyloxy or C
1
-C
20
-alkylcarbonylamino. Preferred substituents are in particular short-chain aliphatic radicals, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl and alkoxy, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, alkylcarbonylamino and monoalkylaminocarbonyl radicals which contain these alkyl groups.
Example of reactive groups Z
1
and Z
2
are:
where the radicals R
4
to R
6
can be identical or different and are each hydrogen or C
1
-C
4
-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl. In the case of the maleimido group and the groups —N═C═O, —N═C═S, —O—C≡N, —COOH, and —OH and —NH
2
, the linking units Y
1
and/or Y
2
represent a chemical single bond.
Of the reactive groups, the cyanates can spontaneously trimerize to cyanurates. The other groups mentioned require further compounds (of the formula I or other auxiliary compounds) containing complementary reactive groups for polymerization. Thus, for example, isocyanates can polymerize with alcohols to give urethanes and with amines to give urea derivatives. Thiiranes and aziridines behave similarly. Carboxyl groups can be condensed to give polyesters and polyamides. The maleimido group is particularly suitable for free-radical copolymerization with olefinic compounds, for example styrene, or compounds comprising styrene structural elements.
The reactive groups may, together with the corresponding complementary reactive groups, be present in a single compound of the formula

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