Azo compound and salts thereof, as well as dye-based polarization films and polarizing plates comprising the same

• US 8,477,268 B2
• Filed: 05/19/2009
• Issued: 07/02/2013
• Est. Priority Date: 06/17/2008
• Status: Active Grant

• Current Assignee: Nippon Kayaku Company Limited, Polatechno Co.,Ltd.
• Original Assignee: Nippon Kayaku Company Limited, Polatechno Co.,Ltd.
• Inventors: Nishiguchi, Takuto, Ohno, Hiroaki, Higeta, Takahiro, Sadamitsu, Yuichi
• Primary Examiner(s): KOSACK, JOSEPH R
• Application Number:
  US12/999,447
• Publication Number:
  US 20110164208A1
• Time in Patent Office: 1,505 Days
• Field of Search: 349/96, 252/299.62, 534/797, 534/806, 534/811, 534/812, 534/815, 534/829, 534/836
• US Class Current: 349/96
• CPC Class Codes: C09B 29/0014 from diazotized aminonaphthalene
• CPC Class Codes: C09B 29/0808 unsubstituted amino group
• CPC Class Codes: C09B 31/047 containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
• CPC Class Codes: C09B 31/072 containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
• CPC Class Codes: C09B 31/08 from a coupling component "C" containing directive hydroxyl and amino groups
• CPC Class Codes: C09B 31/20 from a coupling component"D" containing a directive hydroxyl group
• CPC Class Codes: C09B 31/22 from a coupling component "D" containing directive hydroxyl and amino groups
• CPC Class Codes: C09B 31/30 Other polyazo dyes
• CPC Class Codes: G02B 5/3033 in the form of a thin sheet or foil, e.g. Polaroid

Abstract

Azo compounds represented by formula (1) (In the formula, R₁ represents a lower alkoxy group with a sulfone group. R₂-R₅ each independently represents a hydrogen atom, lower alkyl group or lower alkoxy group. X is an optionally substituted amino group, optionally substituted benzoylamino group, optionally substituted phenylamino group, optionally substituted phenyl azo group or optionally substituted naphthotriazole group. m represents 1 or 2 and n represents 0 or 1.) and salts thereof.

Claims

1. An azo compound represented by Formula (1) and a salt thereof

2. The azo compound and a salt thereof according to claim 1, wherein X is a benzoylamino group that may have a substituent, a phenylamino group that may have a substituent, a phenylazo group that may have a substituent or a naphthotriazole group that may have a substituent, and these substituents are a hydrogen atom, a lower alkyl group, a lower alkoxyl group, a hydroxyl group, a carboxyl group, a sulfone group, an amino group or a substituted amino group.

3. The azo compound and a salt thereof according to claim 1 or 2, wherein X is a phenylamino group represented by Formula (2)

4. The azo compound and a salt thereof according to claim 1 or 2, wherein X is a benzoylamino group represents by Formula (3)

5. The azo compound and a salt thereof according to claim 1 or 2, wherein X is a naphthotriazole group represents by Formula (4)

6. The azo compound and a salt thereof according to claim 1 or 2, wherein X is a phenylazo group represented by Formula (5)

7. The azo compound and a salt thereof according to claim 1, wherein R₁ is a straight chain lower alkoxyl group having a sulfone group.

8. The azo compound and a salt thereof according to claim 1, wherein R₁ is a sulfopropoxy group.

9. The azo compound and a salt thereof according to claim 1, wherein R₂ to R₅ are each independently a hydrogen atom, a methyl group or a methoxy group.

10. A dye-based polarizing film comprising a polarizing film base containing an azo compound and/or a salt thereof according to claim 1.

11. A dye-based polarizing film comprising a polarizing film base containing an azo compound and/or a salt thereof according to claim 1, and at least one organic dye other than the azo compound and/or a salt thereof.

12. A dye-based polarizing film comprising a polarizing film base containing two or more azo compounds and/or salts thereof according to claim 1 and at least one organic dye other than the azo compound and/or a salt thereof.

13. The dye-based polarizing film according to any one of claims 10 to 12, wherein the polarizing film base is a film comprising a polyvinyl alcohol resin or a derivative thereof.

14. A dye-based polarizing plate obtainable by attaching a transparent protecting layer to at least one of surfaces of a dye-based polarizing film according to any one of claims 10 to 12.

15. A polarizing plate for a liquid crystal display comprising a dye-based polarizing film according to claim 13.

16. A polarizing plate for a liquid crystal display comprising a dye-based polarizing plate according to claim 14.

17. A color polarizing film for a liquid crystal projector comprising a dye-based polarizing film according to claim 13.

18. A color polarizing plate for a liquid crystal projector comprising a dye-based polarizing plate according to claim 14.

19. A liquid crystal display device comprising a polarizing film according to claim 15.

20. A liquid crystal display device comprising a polarizing plate according to claim 16.

21. A liquid crystal display device comprising a color polarizing film for a liquid crystal projector according to claim 17.

22. A liquid crystal display device comprising a color polarizing plate for a liquid crystal projector according to claim 18.