Dithiolene Metal Complex Colorless IR Absorbers

Patent metadata

Field	Value
Publication number	US-2017285232-A1
Application number	US-201715623699-A
Country	US
Kind code	A1
Filing date	Jun 15, 2017
Priority date	Jan 17, 2007
Publication date	Oct 5, 2017
Grant date	—

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 2 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 arc NR 7 R 8 .

First claim

1 .- 11 . (canceled)

12 . 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.

13 . The method of claim 12 , 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.

14 . The method according to claim 12 , 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.

15 . The method of claim 12 , wherein the compound of formulae I or II is selected from the group consisting of

16 . The method of claim 12 , 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 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.

17 . The method of claim 12 wherein the material is treated with a compound of formula I

wherein
M is Ni, Pd, or Pt,
X 1 and X 2 are each independently of the other 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.

18 . The method of claim 17 , wherein R 7 and R 8 are each independently of the other unsubstituted C 1 -C 6 alkyl.

19 . The method according to claim 12 , wherein step b) is using the treated material for laser-welding of plastics.

20 . The method according to claim 12 , wherein step b) is using the treated material for security printing or producing invisible and IR readable bar codes.

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

Assignees

• Basf Se

Inventors

• Lehmann Urs
• Heizler Daniel

Classifications

• B29K2081/04

  Polysulfides, e.g. PPS, i.e. polyphenylene sulfide or derivatives thereof · CPC title

• B29B13/024 Primary

  Hollow bodies, e.g. tubes or profiles · CPC title

• C07F15/0066

  without a metal-carbon linkage · CPC title

• G02B5/22 Primary

  Absorbing filters {(G02B5/201 - G02B5/208 take precedence)} · CPC title

• B29K2995/0026

  Transparent · CPC title