IP Library Granted Patent US 7,045,177
Granted Patent B2
US 7,045,177 · App. 10/992,245 · Granted May 16, 2006

Sulfoderivatives of acenaphtho[1,2-

Assignee: Nitto Denko Corporation
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Quick Facts
Patent No.
US 7,045,177
App. No.
10/992,245
Granted
May 16, 2006
Kind
B2
Abstract

The present invention provides a series of new chemical compounds, lyotropic liquid crystal systems, materials, blends, mixtures, namely acenaphtho[1,2-b]quinoxaline sulfoderivatives of the general structural formula: wherein n is an integer in the range of 1 to 4; m is an integer in the range of 0 to 4; z is an integer in the range of 0 to 6, and m+z+n≦10; X and Y are individually selected from the group consisting of CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , Cl, Br, OH, OCOCH 3 NH 2 , NHCOCH 3 , NO 2 , F, CF 3 , CN, OCN, SCN, COOH, and CONH 2 ; M is a counterion; and j is the number of counterions in the molecule.

Claims (117)

1. An acenaphtho[1,2-b]quinoxaline sulfoderivative of the general structural formula:

wherein:

n is an integer in the range of 1 to 4;

m is an integer in the range of 0 to 4;

z is an integer in the range of 0 to 6 and m+z+n≦10; X and Y are individually selected from the group consisting of CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , Cl, Br, OH, OCOCH 3 , NH 2 , NHCOCH 3 , NO 2 , F, CF 3 , CN, OCN, SCN, COOH, and CONH 2 ;

M is a counterion; and

j is the number of counterions in the molecule,

with the proviso that when n=1 and SO 3 — occupies position 1, then m ≠0 or z ≠0.

2. The acenaphtho[1,2-b]quinoxaline sulfoderivative of claim 1 wherein the structural formula is chosen from the group consisting of structures I, IIA–VIII:

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 6;

wherein:

m is an integer in the range of 0 to 4, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 6;

wherein:

m is an integer in the range of 0 to 4, and z is an integer in the range of 0 to 4;

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 4;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 4; and

wherein for each structures I, IIA–VIII:

X and Y are individually selected from the group consisting of CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , Cl, Br, OH, OCOCH 3 , NH 2 , NHCOCH 3 , NO 2 , F, CF 3 , CN, OCN, SCN, COOH, and CONH 2 ;

M is a counterion; and

j is the number of counterions in the molecule.

3. The acenaphtho[1,2-b]quinoxaline sulfoderivative of claim 1 wherein said derivative is capable of forming a lyotropic liquid crystal system.

4. The acenaphtho[1,2-b]quinoxaline sulfoderivative of claim 1 wherein said derivative is capable of forming an optically isotropic or anisotropic film.

5. A lyotropic liquid crystal system comprising at least one acenaphtho[1,2-b]quinoxaline sulfoderivative of the general structural formula:

wherein:

n is an integer in the range of 1 to 4;

m is an integer in the range of 0 to 4;

z is an integer in the range of 0 to 6 and m+z+n≦10; X and Y are individually selected from the group consisting of CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , Cl, Br, OH, OCOCH 3 , NH 2 , NHCOCH 3 , NO 2 , F, CF 3 , CN, OCN, SCN, COOH, and CONH 2 ;

M is a counterion; and

j is the number of counterions in the molecule.

6. The lyotropic liquid crystal system of claim 5 comprising a mixture of said acenaphtho [1,2-b]quinoxaline sulfoderivatives.

7. The lyotropic liquid crystal system of claim 6 comprising a mixture of acenaphtho[1,2-b]quinoxaline sulfoderivatives wherein:

monosulfoderivatives of structures of claim 5 at n=1 are present in a concentration range of approximately 0% to 99% by mass;

disulfoderivatives of structures of claim 5 at n=2 are present in a concentration range of approximately 0% to 99% by mass;

trisulfoderivatives of structures of claim 5 at n=3 are present in a concentration range of approximately 0% to 30% by mass; and

tetrasulfoderivatives of structure of claim 5 at n=4 are present in a concentration range of approximately 0% to 20%;

wherein the total amount of the mono-, di-, tri-, and tetra-sulfoderivatives is 100% by mass.

8. The lyotropic liquid crystal system of claim 5 wherein said lyotropic liquid crystal system is based on a mixture of water and an organic solvent miscible with water.

9. The lyotropic liquid crystal system of claim 5 wherein the content of acenaphtho[1,2-b]quinoxaline sulfoderivatives is in the range of approximately 3% to 60% by mass.

10. The lyotropic liquid crystal system of claim 9 wherein the content of acenaphtho[1,2-b]quinoxaline sulfoderivatives is in the range of approximately 7% to 30% by mass.

11. The lyotropic liquid crystal system of claim 5 further comprising up to approximately 30% by mass of surfactants.

12. The lyotropic liquid crystal system of claim 5 further comprising up to approximately 30% by mass of plasticizers.

13. The lyotropic liquid crystal system of claim 5 further comprising at least one water-soluble organic compound capable of forming a common lyotropic liquid crystal system with said at least one acenaphtho[1,2-b]quinoxaline sulfoderivative of claim 5 .

14. The lyotropic liquid crystal system of claim 6 comprising at least two sulfoderivatives having at least two different substituents Xm and/or Yz or at least one kind of substituent at two different location.

15. An optically anisotropic film comprising at least one acenaphtho[1,2-b]quinoxaline sulfoderivative of the general structural formula:

wherein:

n is an integer in the range of 1 to 4;

m is an integer in the range of 0 to 4;

z is an integer in the range of 0 to 6 and m+z+n≦10; X and Y are individually selected from the group consisting of CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , Cl, Br, OH, OCOCH 3 , NH 2 , NHCOCH 3 , NO 2 , F, CF 3 , CN, OCN, SCN, COOH, and CONH 2 ;

M is a counterion; and

j is the number of counterions in the molecule.

16. The optically anisotropic film of claim 15 containing a mixture of said acenaphtho[1,2-b]quinoxaline sulfoderivatives.

17. The optically anisotropic film of claim 15 further comprising at least one additional organic compound.

18. A method of forming an anisotropic transparent film comprising the steps of:

dissolving an acenaphtho[1,2-b]quinoxaline sulfoderivatives of claim 5 in a suitable solvent for creating the lyotropic liquid crystal system of supramolecules;

applying (depositing) a layer of the lyotropic liquid crystal with supramolecules onto a substrate;

externally impacting the lyotropic liquid crystal system to lower the viscosity of the applied layer;

applying external orienting action on the lyotropic liquid crystal system to provide dominant orientation of supramolecular;

allowing the deposited lyotropic liquid crystal system with dominant orientation of the supramolecules to return to at least its initial value of viscosity, and

drying said lyotropic liquid crystal system.

19. The method of claim 18 , wherein the external orienting action is applied simultaneously with applying a layer of the liquid crystal.

20. The method of claim 18 wherein the dried lyotropic liquid crystal system is treated with solutions of bi- or tri-valent metal salts to make the transparent film water-insoluble.

21. The optically anisotropic film of claim 15 wherein said film is at least partially crystalline.

22. The optically anisotropic film of claim 15 wherein the interplanar spacing is in the range of approximately about 3.1–3.7 Å along one optical axis.

23. The anisotropic film of claim 15 comprising at least two said acenaphtho[1,2-b]quinoxaline sulfoderivatives having at least two different substituents.

24. The anisotropic film of claim 15 wherein said film is birefringent.

25. The anisotropic film of claim 15 wherein said film is polarizing.

26. A lyotropic liquid crystal system of claim 5 wherein the structural formula is chosen from the group consisting of structures I, IIA–VIII, and any combinations thereof:

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 6;

wherein:

m is an integer in the range of 0 to 4, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 6;

wherein:

m is an integer in the range of 0 to 4, and z is an integer in the range of 0 to 4;

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 4;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 4; and

wherein for each structures I, IIA–VIII:

X and Y are individually selected from the group consisting of CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , Cl, Br, OH, OCOCH 3 , NH 2 , NHCOCH 3 , NO 2 , F, CF 3 , CN, OCN, SCN, COOH, and CONH 2 ;

M is a counterion; and

j is the number of counterions in the molecule.

27. The optically anisotropic film of claim 15 wherein the structural formula is chosen from the group consisting of structures I, IIA–VIII, and any combinations thereof:

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 6;

wherein:

m is an integer in the range of 0 to 4, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 6;

wherein:

m is an integer in the range of 0 to 4, and z is an integer in the range of 0 to 4;

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 3, and z is an integer in the range of 0 to 4;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 5;

wherein:

m is an integer in the range of 0 to 2, and z is an integer in the range of 0 to 4; and

wherein for each structures I, IIA–VIII:

X and Y are individually selected from the group consisting of CH 3 , C 2 H 5 , OCH 3 , Cl, Br, OH, OCOCH 3 , NH 2 , NHCOCH 3 , NO 2 , F, CF 3 , CN, OCN, SCN, COOH, and CONH 2 ;

M is a counterion; and

j is the number of counterions in the molecule.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2005
From: OPTIVA, INC.
To: INSOLVENCY SERVICES GROUP, INC.
Reel/Frame 016891/0382 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2005
From: INSOLVENCY SERVICES GROUP, INC.
To: NITTO DENKO CORPORATION
Reel/Frame 016835/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2005
From: DUTOVA, TATYANA Y.; NOKEL, ALEXEY Y.; SIDORENKO, ELENA N.; TIMOFEEV, SERGEY V.
To: OPTIVA, INC.
Reel/Frame 016194/0846 →
Continuity (2)
Provisional Application 6052406800 · Nov 21, 2003
Related Publication 20050109986A1 · May 26, 2005