INKJET INK COMPRISING METAL-CYANINE DYE WITH IMPROVED WATER-SOLUBILITY

• US 20090054664A1
• Filed: 10/12/2008
• Published: 02/26/2009
• Est. Priority Date: 08/09/2004
• Status: Active Grant

• 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, Sintic, Maxine
• Granted Patent: US 7,737,271 B2
• Time in Patent Office: Days
• US Class Current: 548/416
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C09D 11/32 characterised by colouring agents
• CPC Class Codes: Y10T 428/31993 Of paper

Abstract

An inkjet ink comprising an IR-absorbing dye. The dye is a metal-cyanine complex of formula (I):

wherein
Q¹, Q², Q³ and Q⁴ are the same or different and are independently selected from a C_3-20 arylene group or a C_3-20 heteroarylene group;
M is selected from Ti(A¹)(A²), Zr(A¹)(A²), V(A¹)(A²), Si(A¹)(A²), Ge(A¹)(A²), Ga(A¹), Al(A¹), Mn(A¹), Fe(A¹), Sn(A¹)(A²), or Pb(A¹)(A²); and
A¹ and A² may be the same or different and are axial ligands of formula (IIIa)

wherein:
C¹ represents a core unit having two or more branching positions;
each P¹ is independently selected from H, a hydrophilic moiety or a branched moiety;
g¹ is an integer from 2 to 8;
q¹ is 0 or an integer from 1 to 6; and
each p¹ is independently selected from 0 or an integer from 1 to 6.

Claims

1. An inkjet ink comprising an IR-absorbing dye which is a metal-cyanine complex of formula (1):

2. The inkjet ink of claim 1, wherein Q¹, Q², Q³ and Q⁴ are the same.

3. The inkjet ink of claim 1, wherein C¹ is a C atom, an N atom, a Si atom, a C_1-8 alkyl residue, a C_3-8 cycloalkyl residue, or a phenyl residue.

4. The inkjet ink of claim 1, wherein P¹ is of formula:

(CH₂CH₂O)_vR⁶, wherein v is an integer from 2 to 5000 and R⁶ is H, C_1-6 alkyl or C(O)C_1-8 alkyl.

5. The inkjet ink of claim 1, wherein P¹ is of formula:

SO₃Z, PO₃Z₂, C_1-12 alkyl-CO₂Z, C_1-12 alkyl-SO₃Z, C_1-12-alkyl-PO₃Z₂, C_1-12 alkyl-OSO₃Z or C_1-12-alkyl-OPO₃Z₂, wherein Z is H or a water-soluble cation.

6. The inkjet ink of claim 1, wherein P¹ is of formula:

C_1-12-alkyl-N⁺(R^a)(R^b)(R^c) or C_1-12 alkyl-U, wherein R^a, R^b, R^c may be the same or different and are independently selected from H, C_1-8 alkyl, C_6-12 arylalkyl or C_6-12 aryl, and U is pyridinium, imidazolinium or pyrrolinium.

7. The inkjet ink of claim 1, wherein g is 2, 3 or 4.

8. The inkjet ink of claim 1, wherein A¹ and/or A² is a pentaerythritol derivative (A), a triethanolamine derivative (B), a phloroglucinol derivative (C), or a 3,5-dihydroxybenzyl alcohol derivative (D):

9. The inkjet ink of claim 1, wherein Q¹, Q², Q³ and Q⁴ are selected from an arylene or heteroarylene group of the formula:

10. The inkjet ink of claim 9, wherein R¹ and R² are selected from hydrogen or C_1-8 alkoxy.

11. The inkjet ink of claim 9, wherein W is selected from a substituent comprising a PEG chain;

a substituent comprising an ammonium group;

a substituent comprising a sulfonic acid group, including salts thereof, a substituent comprising a sulfonamide group.