Gallium naphthalocyanine salts for use as improved infrared dyes

• US 7,658,792 B2
• Filed: 07/10/2006
• Issued: 02/09/2010
• Est. Priority Date: 07/10/2006
• 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, Ridley, Damon Donald, Gonzaga, Graciel
• Primary Examiner(s): Klemanski; Helene
• Application Number:
  US11/482,990
• Publication Number:
  US 20080005855A1
• Time in Patent Office: 1,310 Days
• Field of Search: 106/31.49, 540/131, 540/132, 540/133
• US Class Current: 106/31.49
• CPC Class Codes: C09B 47/0673 having alkyl radicals linked directly to the Pc skeleton; having carbocyclic groups linked directly to the skeleton
• CPC Class Codes: C09B 47/0678 having-COOH or -SO3H radicals or derivatives thereof directly linked to the skeleton
• CPC Class Codes: C09B 47/26 Amide radicals
• 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: Y10T 428/24802 Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
• CPC Class Codes: Y10T 428/24934 including paper layer

Abstract

There is provided an IR-absorbing naphthalocyanine dye of formula (I):

wherein

• M is Ga(A¹);
• 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;
• 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);
• 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
• each B is independently selected from a base, wherein BH⁺ has a pK_a of between 4 and 9. The dye is suitable for use in IR-absorbing inkjet inks, providing compatibility with known CMYK inks together with an optimally red-shifted λ_max.

Claims

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

2. The dye of claim 1, wherein BH⁺ has a pK_a of between 4.5 and 8.

3. The dye of claim 1, wherein each B is independently selected from the group consisting of a nitrogen base and an oxyanion base.

4. The dye of claim 3, wherein said nitrogen base is a nitrogen-containing C_5-12 heteroaryl base.

5. The dye of claim 4, said nitrogen base is imidazole or pyridine.

6. The dye of claim 3, wherein said oxyanion base is a carboxylate base.

7. The dye of claim 6, wherein said carboxylate base is of formula R⁵C(O)O^—

, wherein R⁵ is selected from the group consisting of;

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

8. The dye of claim 1, wherein each B is the same.

9. The dye of claim 1, wherein each B is imidazole.

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

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

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

13. An inkjet ink comprising a dye according to claim 1, wherein said ink has a pH in the range of 4 to 7.