Gallium naphthalocyanine dye

• US 7,750,147 B2
• Filed: 08/01/2007
• Issued: 07/06/2010
• Est. Priority Date: 08/09/2004
• Status: Expired due to Fees

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Hall, Lachlan Everett, Silverbrook, Kia, Indusegaram, Sutharsiny, Vonwiller, Simone Charlotte, Starling, Scott Matthew, Fielder, Simon, Lapstun, Paul, Ridley, Damon Donald
• Primary Examiner(s): KLEMANSKI, HELENE G
• Application Number:
  US11/832,637
• Publication Number:
  US 20070299257A1
• Time in Patent Office: 1,070 Days
• Field of Search: 540/140, 106/31.49
• US Class Current: 540/140
• CPC Class Codes: C09B 47/045 Special non-pigmentary uses, e.g. catalyst, photosensitisers of phthalocyanine dyes or pigments
• CPC Class Codes: C09B 47/0678 having-COOH or -SO3H radicals or derivatives thereof directly linked to the skeleton
• 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 67/0086 anionic dispersing agents
• CPC Class Codes: C09B 67/009 polymeric dispersing agent
• CPC Class Codes: C09D 11/32 characterised by colouring agents
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: G06F 3/03545 Pens or stylus

Abstract

An IR-absorbing naphthalocyanine dye of formula (I) is described:

• wherein
• M is Ga(A¹);
• A¹ is an axial ligand selected from —OH halogen, —OR³, —OC(O)R⁴;
• R¹ and R² may be the same or different and are selected from hydrogen or C_1-12 alkoxy;
• R³ is selected from C_1-12 alkyl, C_5-12 aryl, C_5-12 arylalkyl or Si(R^x)(R^y)(R^z); and
• 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
• W is a sulfonic acid group, including salts thereof.

Claims

1. An IR-absorbing naphthalocyanine dye of formula (I):

2. The dye of claim 1, wherein each W is a cationic nitrogen salt of a sulfonic acid group.

3. The dye of claim 2, wherein each W is —

SO₃Z, wherein Z is N⁺(R^m)(Rⁿ)(R^s)(R^t), and wherein 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.

4. The dye of claim 1, wherein R¹ and R² are both H.

5. The dye of claim 1, wherein M is Ga(OH).

6. A substrate having a dye according to claim 1 disposed thereon.