Chromophores with perfluoroalkyl substituents

Patent metadata

Field	Value
Publication number	US-9388206-B2
Application number	US-201214115878-A
Country	US
Kind code	B2
Filing date	Apr 25, 2012
Priority date	May 6, 2011
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

The present invention relates to specific metal complexes of dithiolenes with perfluoroalkyl substituted imidazolidine-2-chalcogenone-4,5-dithione ligands, a process for their preparation and their use as colourless IR absorbers, for optical filters application; especially for plasma display panels, or for laser welding of plastics. The compounds may be used in compositions for inks, paints and plastics, especially in a wide variety of printing systems and are particularly well-suited for security applications.

First claim

The invention claimed is:

1. A metal dithiolene complex of formula (I)

wherein
M is Ni, Pd, or Pt;
X 1 and X 2 are each independently sulfur or oxygen;
at least one of the substituents R 1 , R 2 , R 3 and R 4 is a group R f having a formula— —(CH 2 ) n —(CF 2 ) m —F,
the substituents R 1 , R 2 , R 3 and R 4 are each independently the group R f , an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group,

m+n is an integer of 4 to 10,
n is an integer of 1 or 2, and
m is an integer of 3 to 8.

2. The metal dithiolene complex of claim 1 , having a formula (Ia), (Ib), (Ic) or (Id)

3. The metal dithiolene complex of claim 1 , wherein two of the substituents R 1 , R 2 , R 3 and R 4 are the group Rand the other two of the substituents R 1 , R 2 , R 3 and R 4 are substituted or unsubstituted straight-chain, branched or cyclic C 1 -C 18 alkyl radicals; or all of the substituents R 1 , R 2 , R 3 and R 4 are the group R f .

4. The metal dithiolene complex of claim 1 , wherein M is Ni.

5. The metal dithiolene complex of claim 1 , having a formula selected from the group consisting of (A-1) to (A-57)

6. A method of printing, comprising contacting the metal dithiolene complex of claim 1 with a substrate, to obtain a printed document.

7. The method of claim 6 , wherein the metal dithiolene complex is present in a printing ink formulation that improves a fastness property of a printed security document.

8. A printing ink formulation, comprising
a) the metal dithiolene complex of claim 1 ,
b) a polymeric binder,
c) a solvent,
d) optionally a colorant, and
e) optionally a further additive.

9. The printing ink formulation of claim 8 , comprising
a) 0.0001 to 25% by weight of the metal dithiolene complex of claims 1 ,
b) 5 to 74% by weight of the polymeric binder,
c) 1 to 94.9999% by weight of the solvent,
d) 0 to 25% by weight of the colorant, and
e) 0 to 25 % by weight of the further additive,
wherein the sum of components a) to e) adds up to 100%.

10. A security document, comprising a substrate and the metal dithiolene complex of claim 1 .

11. A security document, comprising the printing ink formulation of claim 8 .

12. The security document of claim 10 , which is selected from the group consisting of a bank note, a passport, a cheek, a voucher, an ID card, a transaction card, a stamp and a tax label.

13. A colorless IR absorber comprising the metal dithiolene complex of claim 1 .

14. A cosmetic preparation, comprising the metal dithiolene complex of claim 1 .

15. A process for preparing the metal dithiolene complex of claim 2 having the formula (Ib)

the process comprising reacting a compound of formula (II)

with metallic nickel and a Lawesson's reagent

in a solvent.

16. The metal dithiolene complex of claim 1 , wherein M is Pd.

17. The metal dithiolene complex of claim 1 , wherein M is Pt.

Assignees

• Lehmann Urs
• Heizler Daniel
• Basf Se

Inventors

• Lehmann Urs
• Heizler Daniel

Classifications

• C09D11/10

  based on artificial resins · CPC title

• C07F15/0066

  without a metal-carbon linkage · CPC title

• A61K2800/524

  Preservatives · CPC title

• B42D25/29

  Securities; Bank notes · CPC title

• C07F9/005

  Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages · CPC title