SULFONATED DYE SALTS HAVING IMPROVED STABILITY

• US 20090202799A1
• 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 8,292,995 B2
• Time in Patent Office: Days
• US Class Current: 428/211.100
• 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 salt of a sulfonated dye modulates a stability of the dye, particularly its ozonefastness. The salt comprises an 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 salt of a sulfonated dye, said salt modulating a stability 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);

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.

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

N, S and P

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

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

imidazole cations and phosphazene cations.

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

wherein;

R¹⁰, R¹¹, R¹², R¹³ and R¹⁴ are each independently selected from H, C_1-16 alkyl, C_6-12 aryl, C_5-12 heteroaryl, C_7-16 arylalkyl and C_6-16 heteroarylalkyl;

and wherein R¹² and R¹³ may together be joined to form a C_5-12 cycloalkylene, C_6-12 arylene or C_5-12 heteroarylene group.

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

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

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

wherein;

R¹⁵, R¹⁶ and R¹⁷ are each independently selected from C_6-12 aryl, C_5-12 heteroaryl;

N(R²⁰)(R²¹) and —

N═

P[N(R²²)₂]₃;

R¹⁸ and R¹⁹ are each independently selected from H and C_1-8 alkyl;

or R¹⁸ and R¹⁹ are together;

═

P(Ph)₃;

R²⁰ and R²¹ are each independently selected from H and C_1-8 alkyl;

or R²⁰ and R²¹ are together joined to form a nitrogen-containing C_5-10 heterocycloalkyl group; and

R²² is C_1-6 alkyl.

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

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

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

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

wherein;

Q¹, Q², Q³ and Q⁴ are the same or different and are independently selected from a C_3-20 arylene group or a C_3-20 heteroarylene group;

M is (H₂) or a metal selected from the group comprising;

Si(A¹)(A²), Ge(A¹)(A²), Ga(A¹), Mg, Al(A¹), TiO, Ti(A¹)(A²), ZrO, Zr(A¹)(A²), VO, V(A¹)(A²), Mn, Mn(A¹), Fe, Fe(A¹), Co, Ni, Cu, Zn, Sn, Sn(A¹)(A²), Pb, Pb(A¹)(A²), Pd and Pt;

A¹ and A² are axial ligands, which may be the same or different, and are selected from the group comprising;

—

OH, halogen, —

OR³, —

OC(O)R⁴ and —

O(CH₂CH₂O)_eR^e wherein e is an integer from 2 to 10 and R^e is H, C_1-8 alkyl or C(O)C_1-8 alkyl;

R³ is C_1-20 alkyl, C_5-12 aryl, C_5-20 arylalkyl or Si(R^x)(R^y)(R^z);

R⁴ is C_1-20 alkyl, C_5-12 aryl or C_5-20 arylalkyl;

R^x, R^y and R^z are the same or different and are selected from C_1-12 alkyl, C_5-12 aryl, C_5-12 arylalkyl, C_1-12 alkoxy, C_5-12 aryloxy or C_5-12 arylalkoxy; and

Z₁⁺, Z₂⁺, Z₃⁺ and Z₄⁺ may be the same or different and are each an organic cation as defined in claim 1.

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

wherein

M is (H₂) or a metal selected from the group comprising;

Si(A¹)(A²), Ge(A¹)(A²), Ga(A¹), Mg, Al(A¹), TiO, Ti(A¹)(A²), ZrO, Zr(A¹)(A²), VO, V(A¹)(A²), Mn, Mn(A¹), Fe, Fe(A¹), Co, Ni, Cu, Zn, Sn, Sn(A¹)(A²), Pb, Pb(A¹)(A²), Pd and Pt;

A¹ is an axial ligand selected from —

OH, halogen, —

OR³, —

OC(O)R⁴ or O(CH₂CH₂O)_eR^e wherein e is an integer from 2 to 10 and R^e is H, C_1-8 alkyl or C(O)C_1-8 alkyl;

R³ is selected from C_1-12 alkyl, C_5-12 aryl, C_5-12 arylalkyl or Si(R^x)(R^y)(R^z);

R⁴ is selected from C_1-12 alkyl, C_5-12 aryl or C_5-12 arylalkyl;

R^x, R^y and R^z may be the same or different and are selected from C_1-12 alkyl, C_5-12 aryl, C_5-12 arylalkyl, C_1-12 alkoxy, C_5-12 aryloxy or C_5-12 arylalkoxy; and

Z₁⁺, Z₂⁺, Z₃⁺ and Z₄⁺ may be the same or different and are each an organic cation as defined in claim 1.

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

16. A substrate having the salt according to claim 1 disposed thereon or therein.

17. The substrate of claim 16, wherein said substrate is paper.

18. A printing ink comprising the salt according to claim 1.