METHOD OF PRINTING AN IR-ABSORBING DYE ONTO A SUBSTRATE

• US 20090061094A1
• Filed: 11/03/2008
• Published: 03/05/2009
• 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 7,825,108 B2
• Time in Patent Office: Days
• US Class Current: 427/288
• CPC Class Codes: C09D 11/32 characterised by colouring agents

Abstract

A method of printing an IR-absorbing dye onto a substrate whilst minimizing visible coloration of the substrate. The method comprises: (i) preselecting the dye from a metal-cyanine of formula (I):

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 Si(A¹)(A²), Ge(A¹)(A²), Ga(A¹), Al(A¹), Mn(A¹), Fe(A¹), Sn(A¹)(A²), Pb(A¹)(A²);
A¹ and A² may be the same or different and are axial ligands comprising a group for reducing {tilde over (□)}□ interactions between adjacent dye molecules; and (ii) printing the dye onto the substrate.

Claims

1. A method of printing an IR-absorbing dye onto a substrate whilst minimizing visible coloration of the substrate, said method comprising:

(i) preselecting said dye from a metal-cyanine of formula (I);

2. The method of claim 1, wherein said axial ligand reduces {tilde over (□

)}□

interactions by steric repulsion.

3. The method of claim 1, wherein said axial ligand comprises a dendrimer

4. The method of claim 1, wherein said axial ligand is hydrophilic

5. The method of claim 1, wherein said metal is selected from the group consisting of Si, Ge, Ga, Al, Mn, Fe, Sn or Pb.

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

7. The method of claim 1, wherein A¹ and/or A² comprise a dendrimer.

8. The method of claim 1, wherein A¹ and/or A² is of formula (III)

9. The method of claim 8, 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.

10. The method of claim 8, 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.

11. The method of claim 8, 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.

12. The method of claim 8, 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.

13. The method of claim 8, wherein g is 2, 3 or 4.

14. The method 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):

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

17. The method of claim 15, wherein W is —

SO₃H or a water-soluble salt thereof.

18. The method of claim 1, wherein said dye is printed in the form of coded data.

19. The method of claim 18, wherein said substrate comprises an interface surface and wherein the coded data is printed over a substantial portion of said interface surface.

20. The method claim 1, wherein said substrate is a paper sheet, a label, a tag, a packaging material or a product item.

16. The method of 15, wherein R¹ and R² are selected from hydrogen or C_1-8 alkoxy.