Phthalocyanine dyes suitable for use in offset inks

• US 7,559,983 B2
• Filed: 09/04/2007
• Issued: 07/14/2009
• Est. Priority Date: 10/16/2006
• 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:
  US11/849,360
• Publication Number:
  US 20080087192A1
• Time in Patent Office: 679 Days
• Field of Search: 106/31.49, 540/131
• 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 69/02 Dyestuff salts, e.g. salts of acid dyes with basic dyes for Na, K or NH4+ salts or for chlorides, sulfates or chlorozincates, see the relevant dye groups
• CPC Class Codes: C09D 11/037 characterised by the pigment

Abstract

An IR-absorbing phthalocyanine dye 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 a phosphonium cation. Phosphonium salts of sulfonated gallium naphthalocyanines exemplify such dyes.

Claims

1. An IR-absorbing phthalocyanine dye suitable for formulation in a solvent-based or oil-based ink vehicle, said phthalocyanine comprising one or more sulfonate groups, wherein a counterion of at least one sulfonate group is a phosphonium cation, wherein:

each phosphonium cation is of formula;

P⁺(R^m)(Rⁿ)(R^s)(R^t);

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; and

at least one of R^m, Rⁿ, R^s and R^t comprises more than 4 carbon atoms.

2. The dye of claim 1 comprising a plurality of sulfonate groups.

3. The dye of claim 2 comprising a corresponding plurality of phosphonium counterions.

4. The dye of claim 1, which is a naphthalocyanine.

5. The dye of claim 1, which is of formula (I):

6. The dye of claim 5, wherein at least three of R^m, Rⁿ, R^s and R^t comprise more than 4 carbon atoms.

7. The dye of claim 5, wherein at least three of R^m, Rⁿ, R^s and R^t are independently selected from a C_6-30 alkyl group.

8. The dye of claim 5, wherein R¹ and R² are both hydrogen.

9. The dye of claim 5, wherein M is Ga(OH).

10. A solvent-based or oil-based ink comprising a dye according to claim 1.

11. A substrate having a dye according to claim 1 disposed thereon or therein.

12. The substrate of claim 11, which is a label, packaging or surface of a product item.