Dithiolene metal complex colorless IR absorbers

Patent metadata

Field	Value
Publication number	US-9920087-B2
Application number	US-201715623699-A
Country	US
Kind code	B2
Filing date	Jun 15, 2017
Priority date	Jan 17, 2007
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

The invention relates to the use of compounds of formulae (I) and/or (II) as colorless IR absorbers wherein M is Ni, Pd, Pt, Au, Ir, Fe, Zn, W, Cu, Mo, In, Mn, Co, Mg, V, Cr or Ti, X 1 , X 2 and X 3 are each independently of the others sulfur or oxygen, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently of the others hydrogen, NR 7 R 8 , unsubstituted or substituted C 1 -C 18 alkyl, C 1 -C 18 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C 1 -C 18 alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, R 7 and R 8 , each independently of the other, being unsubstituted or substituted C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, a further IR absorber optionally being added to the compounds of formulae (I) and (II). The invention relates also to novel dithiolene compounds of formulae (I) and (II) wherein X 1 is oxygen and X 2 and X 3 are oxygen or sulfur. The invention relates furthermore to novel dithiolene compounds of formulae (I) and (II) wherein R 1 to R 6 are NR 7 R 8 .

First claim

The invention claimed is:

1. A method of using colorless IR absorbers comprising
a) treating a material with a compound of formula I and/or II

wherein
M is Ni, Pd, Pt,
X 1 is oxygen,
X 2 and X 3 are each independently of the other sulfur or oxygen,
R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each independently of the others hydrogen, NR 7 R 8 , unsubstituted or substituted C 1 -C 18 alkyl, C 1 -C 18 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted or substituted C 1 -C 18 alkenyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl, R 7 and R 8 , each independently of the other, being unsubstituted or substituted C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl,
wherein the material is a security print, an invisible and IR readable bar code, a laser-welded plastic, a dried print, a fixed toner on paper, a laser marked plastic, or a heated preform,
optionally a further IR absorber; and
b) using the treated material of a) for security printing, invisible and IR readable bar codes, laser-welding of plastics, drying of print, fixing of toners on paper, laser marking, and heating of plastics preforms.

2. The method of claim 1 , wherein for formulae I and II
R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are NR 7 R 8 , wherein R 7 and R 8 are each independently of the other unsubstituted or substituted C 1 -C 18 alkyl, unsubstituted or substituted aryl, unsubstituted or substituted arylalkyl or unsubstituted or substituted heteroarylalkyl.

3. The method according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 are each independently of the others —N(C 1 -C 6 alkyl) 2 , unsubstituted C 1 -C 8 alkyl, —(CH 2 )n-[O—(CH 2 ) m ] k —OCH 3 with n=2-6, m=2 or 3, k=1-6; vinyl or allyl, —(CH 2 )q-phenyl with q=1-6.

4. The method of claim 1 , wherein the compound of formulae I is

5. The method of claim 1 , wherein the material is treated with a compound of formula I

wherein
M is Ni, Pd, or Pt,
X 1 is oxygen,
X 2 is sulfur or oxygen,
R 1 , R 2 , R 3 , and R 4 , are each independently of the others hydrogen, NR 7 R 8 , unsubstituted C 1 -C 18 alkyl, C 1 -C 18 alkyl wherein the alkylene chain is interrupted with oxygen, unsubstituted C 1 -C 18 alkenyl,
R 7 and R 8 , each independently of the other, being unsubstituted C 1 -C 18 alkyl.

6. The method of claim 1 wherein the material is treated with a compound of formula I

wherein
M is Ni, Pd, or Pt,
X 1 is oygen,
X 2 is sulfur or oxygen,
R 1 , R 2 , R 3 , and R 4 , are NR 7 R 8 , wherein R 7 and R 8 are each independently of the other unsubstituted C 1 -C 18 alkyl.

7. The method of claim 6 , wherein R 7 and R 8 are each independently of the other unsubstituted C 1 -C 6 alkyl.

8. The method according to claim 1 , wherein step b) is using the treated material for laser-welding of plastics.

9. The method according to claim 1 , wherein step b) is using the treated material for security printing or producing invisible and IR readable bar codes.

10. The method according to claim 1 , wherein the further IR absorbers are polymethines.

Assignees

• Basf Se

Inventors

• Lehmann Urs
• Heizler Daniel

Classifications

• B29K2027/16

  PVDF, i.e. polyvinylidene fluoride · CPC title

• C07D233/86

  Oxygen and sulfur atoms, e.g. thiohydantoin · CPC title

• B29C65/1674

  making use of laser diodes (B29C65/167 takes precedence) · CPC title

• C07D239/22

  with hetero atoms directly attached to ring carbon atoms · CPC title

• B29K2995/0027

  for light outside the visible spectrum · CPC title