METHOD OF MODULATING STABILITY OF SULFONATED DYE

• US 20090199352A1
• Filed: 02/10/2009
• Published: 08/13/2009
• Est. Priority Date: 02/11/2008
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Hall, Lachlan Everett, Silverbrook, Kia, Indusegaram, Sutharsiny, Vonwiller, Simone Charlotte, Starling, Scott Matthew, Ridley, Damon Donald, Gonzaga, Graciel
• Granted Patent: US 8,038,737 B2
• Time in Patent Office: Days
• US Class Current: 8/568
• CPC Class Codes: C09B 47/24 Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
• CPC Class Codes: C09B 69/04 of anionic dyes with nitrogen containing compounds
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: Y10S 8/919 Paper
• CPC Class Codes: Y10T 428/24934 including paper layer

Abstract

A method of modulating a stability of a sulfonated dye, particularly its ozonefastness. The method comprises providing a salt of the dye, wherein the salt comprises at least one organic cation selected from the group consisting of:

• • a first organic cation having a positive charge delocalized between a nitrogen atom and at least one other heteroatom;
  • a second organic cation having a positive charge delocalized between a nitrogen atom and at least two other atoms; and
  • a third organic cation of formula (A):

wherein:

• • R^p, R^q and R^r are each independently selected from a C_1-6 alkyl group;
  • s is 0, 1, 2 or 3; and
  • Ar is a C_6-12 aryl group or C_3-12 heteroaryl group.

Claims

1. A method of modulating a stability of a sulfonated dye, said method comprising providing a salt of said dye, wherein said salt comprises at least one organic cation selected from the group consisting of:

a first organic cation having a positive charge delocalized between a nitrogen atom and at least one other heteroatom;

a second organic cation having a positive charge delocalized between a nitrogen atom and at least two other atoms; and

a third organic cation of formula (A);

2. The method of claim 1, wherein said at least one other heteroatom is selected from the group consisting of:

N, S and P

3. The method of claim 1, wherein said first and second organic cations lack any alkyl groups having a length of more than 6 atoms.

4. The method of claim 1, wherein said first or second organic cation is selected from the group consisting of:

imidazole cations;

benzimidazole cations;

thiazole cations;

thiabendazole cations;

guanidine cations;

phosphazene cations;

hexidine cations and di(C_1-6 alkyl)aminopyridine cations.

5. The method of claim 1, wherein said first or second organic cation is selected from the group consisting of:

imidazole cations and phosphazene cations.

6. The method of claim 5, wherein said first or second organic cation is an imidazole cation of the formula (B):

7. The method of claim 6, wherein R¹⁰, R¹¹, R¹², R¹³ and R¹⁴ are each independently selected from H and C_1-6 alkyl.

8. The method of claim 6, wherein at least one of R¹⁰, R¹¹, R¹², R¹³ and R¹⁴ is not H.

9. The method of claim 5, wherein said first or second organic cation is a phosphazene cation of formula (C):

10. The method of claim 1, wherein said salt modulates an ozonefastness of said dye.

11. The method of claim 1, wherein said dye is a phthalocyanine dye.

12. The method of claim 1, wherein said dye is an IR-absorbing dye.

13. The method of claim 1, wherein said salt is of formula (I):

14. The method of claim 1, wherein said salt is of formula (II):

15. The method of claim 14, wherein M is Ga(OH).

16. The method of claim 1, wherein said dye is disposed on or in a substrate.

17. The method of claim 1, wherein said dye is printed onto a print medium.

18. The method of claim 1, wherein said print medium is paper.