IP Library › Granted Patent US 10,385,215
Granted Patent B2
US 10,385,215 · App. 15/308,504 · Granted Aug 20, 2019

Polymerizable dichroic dyes

Inventors: Cedric Klein (Herrlisheim-pres-Colmar, FR); Frederic Lincker (Schiltigheim, FR); Frederic Reveaud (Mulhouse, FR)
Assignee: ROLIC AG
C09B69/101C09B1/22C09B1/473C09B1/585C09K19/3809C09K19/3861C09K19/56C09K19/586C09K19/603C09K2019/0448C09K2219/03
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Quick Facts
Patent No.
US 10,385,215
App. No.
15/308,504
Granted
Aug 20, 2019
Kind
B2
Abstract

New dichroic dyes having a composition with slave materials. The dyes may be used for a dichroic polymer network, a dichroic liquid crystalline polymer film (LCP film) or a dichroic liquid crystalline polymer gel, which for instance find application as electro-optical or optical devices.

Claims (45)

1. A composition comprising at least a dichroic dye of formula (I) and at least one slave material which is selected from the group consisting of a liquid crystal and a polymerizable liquid crystal:

wherein

X 2 , X 1 are independently from each other NR,

R represents hydrogen, unbranched or branched lower alkyl radical,

Y 1 , Y 2 independently from each other are a single bond,

Z 1 is O,

Z 2 is a single bond,

n2 is 1,

n1, n3, n4, n5, n6 are 0,

W 1 , W 4 , W 5 , W 6 are hydrogen,

W 2 , W 3 independently from each other are unsubstituted or substituted, straight chain or branched C 1 -C 30 alkyl, in which one —CH— or —CH 2 — group may be replaced by one or more linking group consisting of —O—, —S—, —NR 1 —, —CH(OR 1 )—, —CO—NR 1 —, —NR 1 —CO—, —CO—O—, —O—CO—, —SO 2 — or an aromatic group which is unsubstituted or substituted by one or more straight chain or branched lower alkyl radical, —F, —Cl or —OR 1 , and wherein

R 1 represents hydrogen, straight chain or branched lower alkyl radical,

PG is a polymerizable group consisting of CH 2 ═CQ-COO—, wherein Q is hydrogen or methyl;

or

a dichroic dye of formula (I), wherein

X 1 is S

X 2 is single bond or NR,

R has the same meaning as mentioned above,

Y 1 is S,

Y 2 is a single bond or NR,

Z 1 , Z 2 are single bond,

n1, n6 are 1,

n2, n3, n4, n5, are 0,

W 2 , W 3 , W 4 , W 5 are hydrogen

W 1 , W 6 are independently from each other are unsubstituted or substituted, straight chain or branched C 1 -C 30 alkyl, in which one —CH— or —CH 2 — group may be replaced by one or more linking group consisting of —O—, —S—, —NR 1 —, —CH(OR 1 )—, —CO—NR 1 —, —NR 1 —CO—, —CO—O—, —O—CO—, —SO 2 — or an aromatic group which is unsubstituted or substituted by one or more straight chain or branched lower alkyl radical, —F, —Cl or —OR 1 , and wherein

R 1 having the same meaning as mentioned above,

PG is a polymerizable group consisting of CH 2 ═CQ-COO—, wherein Q is hydrogen or methyl;

or

a dichroic dye of formula (I), wherein

X 1 , X 2 are independently from each other NR

Y 1 , Y 2 are independently from each other NR,

R has the same meaning as mentioned above,

Z 1 , Z 2 are independently from each other a single bond or O

n2, n5 are 1,

n1, n3, n4, n6, are 0,

W 1 , W 6 are hydrogen

W 2 , W 3 W 4 , W 5 are independently from each other unsubstituted or substituted, straight chain or branched C 1 -C 30 alkyl, in which one —CH— or —CH 2 — group may be replaced by one or more linking group consisting of —O—, —S—, —NR 1 —, —CH(OR 1 )—, —CO—NR 1 —, —NR 1 —CO—, —CO—O—, —O—CO—, —SO 2 — or an aromatic group which is unsubstituted or substituted by one or more straight chain or branched lower alkyl radical, —F, —Cl or —OR 1 , and wherein

R 1 having the same meaning as mentioned above,

PG is a polymerizable group consisting of CH 2 ═CQ-COO—, wherein Q is hydrogen or methyl.

2. A composition according to claim 1 , wherein said composition additionally comprises at least one chiral polymerizable liquid crystalline compound or at least one chiral component.

3. A process for the preparation of a dichroic polymer network, a dichroic liquid crystalline polymer film (LCP film) or a dichroic liquid crystalline polymer gel, which process comprises polymerizing a composition according to claim 1 .

4. A dichroic polymer network, a dichroic liquid crystalline polymer film (LCP film) or a dichroic liquid crystalline polymer gel comprising a composition according to claim 1 .

5. An electro-optical or optical device, comprising a dichroic polymer network, a dichroic liquid crystalline polymer film (LCP film) or a dichroic liquid crystalline polymer gel according to claim 4 .

6. An electro-optical or optical device according to claim 5 , which is represented by a polarizer, an optical film, a security or an authentication device.

7. A dichroic polymer network, a dichroic liquid crystalline polymer film (LCP film) or a dichroic liquid crystalline polymer gel comprising a composition according to claim 2 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2016
From: KLEIN, CEDRIC; LINCKER, FREDERIC; REVEAUD, FREDERIC
To: ROLIC AG
Reel/Frame 040199/0389 →
Priority Claims (1)
EP 14169195 · May 21, 2014 · regional
Continuity (1)
Related Publication 20170058126A1 · Mar 2, 2017