Nitrogen-substituted water-dispersible phthalocyanine dyes

• US 7,572,327 B2
• Filed: 07/05/2005
• Issued: 08/11/2009
• Est. Priority Date: 07/05/2005
• Status: Expired due to Fees

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Silverbrook, Kia, Indusegaram, Sutharsiny, Vonwiller, Simone Charlotte, Starling, Scott Matthew, Ridley, Damon Donald, Gonzaga, Graciel
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US11/172,814
• Publication Number:
  US 20070008392A1
• Time in Patent Office: 1,498 Days
• Field of Search: 106/31.49, 106/31.47, 540/123, 540/124, 540/125, 540/127
• US Class Current: 106/31.49
• CPC Class Codes: C09B 47/0676 having nitrogen atom(s) linked directly to the skeleton
• CPC Class Codes: C09B 47/30 Metal-free phthalocyanines
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: Y10T 428/24802 Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]

Abstract

A phthalocyanine dye of formula (I) is provided:

wherein:

• M is a metal group or is absent;
• n is 1 or 2;
• X is selected from —CHR³—, —NR³—, —O— or —S—;
• R¹, R² and R³ are independently selected from hydrogen, C^1-8 alkyl, C^1-8 alkoxy, carboxy, carboxy-C^1-8 alkyl, hydroxyl, hydroxy-C^1-8 alkyl; or
• R¹ and R², or R² and R³ together are joined to form a C^4-12 aryl or C^3-12 heteroaryl group, optionally substituted with 1, 2, 3 or 4 substituent groups, the or each substituent group being independently selected from C^1-12 alkyl, C^1-12 alkoxy, phenyl-C^1-8 alkyl, phenyl-C^1-8 alkoxy, —(OCH₂CH₂)_dOR^d, cyano, halogen, amino, hydroxyl, thiol, —SR^v, —NR^uR^v, nitro, phenyl, phenoxy, —CO₂R^v, —C(O)R^v, —OCOR^v, —SO₂R^v, OSO₂R^v, —NHC(O)R^v, —CONR^uR^v, —CONR^uR^v, sulfonic acid, sulfonic acid salt and sulfonamide;
• d is an integer from 2 to 5000;
• R^d is H, C_1-8 alkyl or C(O)C_1-8 alkyl and
• R^u and R^v are independently selected from hydrogen, C_1-12 alkyl, phenyl or phenyl-C_1-8 alkyl.

Claims

1. A phthalocyanine dye of formula (IV) or (V):

2. The dye of claim 1, wherein at least one W is a sulfonic acid or sulfonic acid salt of formula —

SO₃Z, wherein;

Z is H, Li, Na, K or N⁺(R^m)(Rⁿ)(R^S)(R^t); and

R^m, Rⁿ, R^s, R^t may be the same or different and are independently selected from the group consisting of;

H, C^1-8 alkyl, C^6-12 arylalkyl and C^6-12 aryl.

3. The dye of claim 1, wherein M is SnCl², V═

O or Ga(OH).

4. An inkjet ink comprising a dye according to claim 1.