Inkjet ink comprising metal-cyanine dye with improved water-solubility

• US 7,737,271 B2
• Filed: 10/12/2008
• Issued: 06/15/2010
• 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, Sintic, Maxine
• Primary Examiner(s): Wilson; James O.
• Assistant Examiner(s): Ward; Paul V.
• Application Number:
  US12/249,950
• Publication Number:
  US 20090054664A1
• Time in Patent Office: 611 Days
• Field of Search: 540/145, 106/31.13
• US Class Current: 540/145
• 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 (I):

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

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

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

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

7. The inkjet ink of claim 6, wherein R¹ and R² are selected from the group consisting of:

hydrogen and C_1-8 alkoxy.