Alternative phthalocyanine dyes suitable for use in offset inks

• US 7,566,363 B2
• Filed: 05/13/2008
• Issued: 07/28/2009
• Est. Priority Date: 07/24/2007
• Status: Expired due to Fees

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Silverbrook, Kia, Vonwiller, Simone Charlotte, Starling, Scott Matthew, Ridley, Damon Donald
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US12/119,497
• Publication Number:
  US 20090035533A1
• Time in Patent Office: 441 Days
• Field of Search: 106/31.49, 106/31.78, 540/123, 540/128, 540/135, 540/139, 540/140, 347/100, 235/375
• US Class Current: 106/31.49
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C09B 47/0678 having-COOH or -SO3H radicals or derivatives thereof directly linked to the skeleton
• CPC Class Codes: C09B 69/04 of anionic dyes with nitrogen containing compounds
• CPC Class Codes: C09D 11/36 based on non-aqueous solvents
• CPC Class Codes: Y10T 428/24802 Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]

Abstract

A phthalocyanine phthalocyanine salt suitable for formulation in a solvent-based or oil-based ink vehicle is disclosed. The phthalocyanine comprises one or more sulfonate groups and a counterion of at least one sulfonate group is an ammonium cation comprising at least 15 carbon atoms. Ammonium salts of sulfonated gallium naphthalocyanines exemplify such phthalocyanine salts.

Claims

1. A phthalocyanine salt comprising one or more sulfonate groups, wherein a counterion of at least one sulfonate group is an ammonium cation comprising at least 20 carbon atoms.

2. The phthalocyanine salt of claim 1, wherein said ammonium cation comprises at least one group C_6-30 alkyl group or at least one C_6-30 benzylalkyl group.

3. The phthalocyanine salt of claim 1 comprising a plurality of sulfonate groups.

4. The phthalocyanine salt of claim 1, which is an IR-absorbing phthalocyanine salt.

5. The phthalocyanine salt of claim 1, which is a naphthalocyanine.

6. The phthalocyanine salt of claim 1, wherein said ammonium cation is of formula:

N⁺(R^m)(Rⁿ)(R^s)(R^t), wherein;

each of R^m, Rⁿ, R^s and R^t is independently selected from the group consisting of;

C_1-30 alkyl, C_5-12 aryl and C_5-30 arylalkyl;

or

R^m and Rⁿ are together joined to form a C_5-10 heterocycloalkyl group, with R^s and R^t being independently selected from the group consisting of;

C_1-30 alkyl, C_5-12 aryl and C_5-30 arylalkyl;

or

R^m, Rⁿ and R^s are together joined to form a C_5-10 heteroaryl group, with R^t being independently selected from the group consisting of;

C_1-30 alkyl, C_5-12 aryl and C_5-30 arylalkyl.

7. The phthalocyanine salt of claim 6, wherein at least one of R^m, Rⁿ, R^s and R^t comprises 10 or more carbon atoms.

8. The phthalocyanine salt of claim 6, wherein at least two of R^m, Rⁿ, R^s and R^t comprise 6 or more carbon atoms.

9. The phthalocyanine salt of claim 6, wherein at least three of R^m, Rⁿ, R^s and R^t comprise 6 or more carbon atoms.

10. The phthalocyanine salt of claim 6, wherein each of R^m, Rⁿ, R^s and R^t is independently selected from C_1-30 alkyl.

11. The phthalocyanine salt of claim 6, wherein said ammonium cation is of formula:

12. The phthalocyanine salt of claim 1, wherein said salt is of formula (Ia):

13. The phthalocyanine salt of claim 1, which is of formula (I):

14. A solvent-based or oil-based ink comprising a phthalocyanine salt according to claim 1.

15. An analog printer, or a module thereof, comprising an ink supply, a printing plate and means for disposing ink from said ink supply onto said plate, wherein said ink comprises a phthalocyanine salt according to claim 1.

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

17. The substrate of claim 1, which is a label, packaging or surface of a product item.

18. A system for interacting with a coded substrate, said system comprising:

a substrate having human-readable information and machine-readable coded data disposed thereon or therein; and

a sensing device for reading the machine-readable coded data,

wherein said coded data comprises a phthalocyanine salt according to claim 1.