Metal-cyanine dye having axial ligands which reduce visible absorption

• US 7,367,665 B2
• Filed: 08/09/2004
• Issued: 05/06/2008
• 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): Shah; Manish S.
• Application Number:
  US10/913,372
• Publication Number:
  US 20060028520A1
• Time in Patent Office: 1,366 Days
• Field of Search: 347/100, 347/95, 347/96, 347/101, 106/31.13, 106/31.27, 106/31.6, 540/122, 540/145, 514/185, 514/410, 523/160
• US Class Current: 347/100
• CPC Class Codes: C09B 47/085 substituting the central metal atom
• CPC Class Codes: C09D 11/32 characterised by colouring agents
• 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

The present invention provides an IR-absorbing metal-cyanine dye, said metal having at least one axial ligand bound thereto, wherein said axial ligand comprises a moiety suitable for reducing intermolecular interactions between adjacent dye molecules, thereby minimizing absorption of visible light.

Dyes of this type are especially suitable for use in netpage and Hyperlabel systems.

Claims

1. An IR-absorbing metal-cyanine dye, said metal having at least one axial ligand bound thereto, wherein said axial ligand comprises a moiety suitable for reducing intermolecular interactions between adjacent dye molecules, thereby minimixing absorption of visible light,

wherein said 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_3-20arylene group or a C_3-20 heteroarylene group;

M is selected from Ga(A³), Al(A¹), Mn(A¹), Fe(A¹) or Pb(A¹)(A²);

A¹and/or A² is of formula (III);

wherein

C¹ represents a core unit having two or more branching poisons;

each P¹ is independently selected from H or a hydrophilic 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.

2. The dye of claim 1, wherein said axial ligand reduces intermolecular interactions by steric repulsion.

3. The dye of claim 1, wherein said axial ligand comprises a polymeric chain.

4. The dye of claim 1, wherein said axial ligand comprises a dendrimer.

5. The dye of claim 1, wherein said axial ligand includes a PEG chain.

6. The dye of claim 1, wherein Q¹, Q², Q³ and Q⁴ are the same.

7. The dye of claim 1, wherein C¹ is a atom, an N atom, a Si atom, a C_1-8alkyl residue, a C_3-8cycloalkyl residue, or a phenyl residue.

8. The dye of claim 1, wherein P¹ is a hydrophilic moiety comprising an acid group (including salts thereof), a sulfonamide group, a hydrophilic polymer chain or an ammonium group.

9. The dye of claim 1, wherein P¹ is of formula:

(CH₂CH₂O)_vR⁶, wherein v is an integer from 2 to 5000 and R⁶ is H, C_3-6alkyl or C(O)C_1-8alkyl.

10. The dye of claim 1, wherein P¹ is of formula:

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

11. The dye of claim 1, wherein P¹ is of formula:

C_1-12-alkyl-N⁺(R^a)(R^b)(R^c) or C_1-12alkyl-U, wherein R^a, R^b, R^c may be the same or different and are independently selected front H, C_3-8alkyl, C_6-12arylalkyl or C_6-12aryl, and U is pyridinium, imidazolinium or pyrroliniumn.

12. The dye of claim 1, wherein g is 2, 3 or 4.

13. The dye 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):

wherein is P¹ is as defined in claim 1.

14. The dye of claim 1, wherein Q¹,Q²,Q³ and Q⁴ are selected from an arylene or heteroaylene group of the formula:

wherein

R¹ and R² may be the same or different and are selected from hydrogen, hydroxyl, C_1-12alkyl, C_1-12alkyl bearing a hydrophilic or hydrophilizable group, C_1-12alkoxy, C_1-12alkoxy bearing a hydrophilic or hydrophilizable, group, amino, C_1-12alkylamino, di(C_1-12alkyl)amino, halogen, cyano, thiol, C_1-12alkylthio, nitro, carboxy, C_1-12alkylcarbonyl, C_1-12alkoxycarbonyl, C_1-12alkylcarbonyloxy or C_1-12alkylcarbonylamino;

T is selected from a substituent comprising a polymeric chain or a C_3-30hydrocarbyl group;

W is hydrophilic group;

E is selected from —

OH, —

O, C_3-6alkyl, carboxy-C_1-6alkyl, sulfo-C_1-6alkyl, C_1-6alkoxy, C_5-12arylalkyl, C_1-6alkylcarbonyl, C_5-12arylalkylcarbonyl, C_1-6alkoxycarbonyl or C_5-12arylalkoxycarbonyl;

m is 0, 1 or 2;

n is 0, 1 or 2; and

p is 0, 1 or 2.

15. The dye of claim 14, wherein R¹ and R² are selected from hydrogen or C_1-8alkoxy.

16. The dye of claim 14, wherein W is selected from a substituent comprising a PEG chain;

a substituent comprising an ammonium group;

a substituent comprising an acid group, including salts thereof;

a substituent comprising a sulfonamide group.

17. An ink comprising a dye according to claim 1.

18. An inkjet ink comprising a dye according to claim 1 and a singlet oxygen quencher.

19. An inkjet ink comprising a dye according to claim 1, said dye being preselected to minimize visible absorption by reducing intermolecular interactions between adjacent dye molecules.