Use of aryl or heteroaryl substituted dithiolene metal complexes as IR absorbers

Patent metadata

Field	Value
Publication number	US-9260614-B2
Application number	US-201113885792-A
Country	US
Kind code	B2
Filing date	Nov 23, 2011
Priority date	Nov 24, 2010
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

Abstract

The present invention relates to the use of specific metal complexes of dithiolenes with aryl or heteroarylsubstituted imidazolidine-2-chalcogenone-4,5-dithione ligands as colorless IR absorbers.

First claim

The invention claimed is:

1. A security printing method comprising contacting a printing ink formulation comprising a colorless IR absorber with a substrate to produce a printed security document,
wherein said colorless IR absorber is a compound of formula (I)

wherein
M is Ni, Pd, or Pt,
X 1 and X 2 are each independently sulfur or oxygen,
R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, and substituted heteroaryl.

2. The method according to claim 1 , wherein M is Ni.

3. The method according to claim 1 , wherein the compound is of formula (1) is at least one compound selected from the group consisting of compounds of formulae (1) to (37):

4. The method according to claim 1 , wherein the compound is in a form of a mixture, the mixture comprising the compound of formula (I) and a further IR absorber different from a compound of formula (I).

5. The method according to claim 1 , wherein the printed security document is a bank note.

6. The method according to claim 1 , wherein the contacting improves fastness properties of the printed security document.

7. A printing ink formulation, comprising
a) a compound of formula (I):

wherein
M is Ni, Pd, or Pt,
X 1 and X 2 are each independently sulfur or oxygen,
R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, and substituted heteroaryl, and wherein the compound is a colourless IR absorber,
a polymeric binder,
a solvent,
optionally a colorant, and
optionally a further additive.

8. The printing ink formulation according to claim 7 , comprising
0.0001 to 25% by weight of the compound of formula (I),
5 to 74% by weight of the polymeric binder,
1 to 94.9999% by weight of the solvent,
0 to 25% by weight of the colorant, and
0 to 25% by weight of the additive,
wherein a sum of the weights of the compound, the polymeric binder, the solvent, the colorant, and the additive is 100%.

9. A security document, wherein the security document is obtained by a printing method, according to claim 1 .

10. The security document according to claim 9 , wherein the security document is at least one selected from the group consisting of a bank note, a passport, a check, a voucher, an ID-card, a transaction card, a stamp and a tax label.

11. The method according to claim 1 , wherein X 1 is oxygen.

12. The method according to claim 3 , wherein said compound is at least one compound selected from the group consisting of formula (1) and (37).

13. A printing ink formulation, comprising:
at least one compound selected from the group consisting of formula (1) to (37) according to claim 3 ,
a polymeric binder,
a solvent,
optionally a colorant, and
optionally a further additive.

14. The printing ink formulation according to claim 13 , comprising
0.0001 to 25% by weight of at least one compound selected from the group consisting of formula (1) to (37),
5 to 74% by weight of the polymeric binder,
1 to 94.9999% by weight of the solvent,
0 to 25% by weight of the colorant, and
0 to 25% by weight of the additive,
wherein a sum of the weights of the compound, the polymeric binder, the solvent, the colorant, and the additive is 100%.

Assignees

• Reichelt Helmut
• Gessner Thomas
• Heizler Daniel
• Lehmann Urs
• Basf Se

Inventors

• Reichelt Helmut
• Gessner Thomas
• Heizler Daniel
• Lehmann Urs

Classifications

• B42D15/00

  Printed matter of special format or style not otherwise provided for · CPC title

• C09D11/02

  Printing inks (C09D11/30 takes precedence) · CPC title

• B41M5/26

  Thermography (B41M5/20, B41M5/24 take precedence); {Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used (B23K takes precedence; thermographic or photothermographic systems using noble metal compounds G03C1/494)} · CPC title

• C07D233/96

  having three double bonds between ring members or between ring members and non-ring members · CPC title

• C09D11/03 Primary

  characterised by features other than the chemical nature of the binder · CPC title