Methine dyes

Patent metadata

Field	Value
Publication number	US-10808129-B2
Application number	US-201816155111-A
Country	US
Kind code	B2
Filing date	Oct 9, 2018
Priority date	Oct 13, 2017
Publication date	Oct 20, 2020
Grant date	Oct 20, 2020

Abstract

The present invention relates to novel methine dyes, methods for the preparation thereof and use thereof for dyeing plastics, especially polyamides, so as to obtain yellow to orange colourings with improved light fastness and improved thermal stability. Methine dyes for example accord to the formula (I)

in which
R 1 is hydrogen, halogen, alkyl, COOH or COOR 9 ,
R 2 is oxygen or sulfur,
R 3 is hydrogen, halogen, COOH, COOR 10 or CN,
R 4 is alkyl or phenyl,
R 5 and R 6 are each independently alkyl,
R 7 and R 8 are each independently hydrogen, halogen, alkyl or COOR 11 , and
R 9 , R 10 and R 11 are each independently alkyl.

First claim

What is claimed is:

1. A dye of the formula (I)

in which
R 1 is hydrogen, halogen, C 1 -C 4 -alkyl, which is optionally mono- to trisubstituted, identically or differently, by halogen, COOH or COOR 9 ,
R 2 is oxygen,
R 3 is hydrogen, halogen, COOR 10 or CN,
R 4 is C 1 -C 4 -alkyl or phenyl,
R 5 and R 6 are each independently C 1 -C 4 -alkyl,
R 7 and R 8 are each independently hydrogen, halogen, C 1 -C 4 -alkyl, which is optionally mono- to trisubstituted, identically or differently, by methoxy or ethoxy, or COOR 11 , and
R 9 , R 10 and R 11 are each independently C 1 -C 4 -alkyl, and

where R 1 and R 3 are not both hydrogen.

2. The dye of claim 1 , wherein in formula (I)
R 1 is hydrogen, fluorine, chlorine, CF 3 or COOR 9 ,
R 2 is oxygen,
R 3 is hydrogen, fluorine, chlorine or CN,
R 4 , R 5 and R 6 are each independently methyl or ethyl,
R 7 and R 8 are each independently hydrogen, each independently unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl; or methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl in each case mono- or disubstituted, identically or differently, by methoxy or ethoxy, and
R 9 is methyl or ethyl.

3. The dye of claim 1 , wherein in formula (I)
R 1 is fluorine, chlorine, CF 3 or COOR 9 ,
R 2 is oxygen,
R 3 is hydrogen,
R 4 , R 5 and R 6 are each methyl,
R 7 and R 8 are each independently hydrogen, each independently unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl or 1-methyl-2-methoxyethyl, and
R 9 is methyl.

4. A method for producing a dye of claim 1 , the method comprising contacting an aldehyde of the formula (II)

in which R 1 , R 3 , R 4 , R 5 , R 6 , have the definitions specified in claim 1 ,
with a barbituric acid derivative of the formula (III)

in which R 2 , R 7 , and R 8 have the definitions specified in claim 1 .

Assignees

• Lanxess Deutschland Gmbh

Inventors

• Borst Hans-Ulrich
• Michaelis Stephan
• Linke Frank

Classifications

• C08L77/02

  Polyamides derived from omega-amino carboxylic acids or from lactams thereof (C08L77/10 takes precedence) · CPC title

• C09B23/00 Primary

  Methine or polymethine dyes, e.g. cyanine dyes · CPC title

• C08F2/44

  Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers · CPC title

• C08K5/3465

  condensed with carbocyclic rings · CPC title

• C08L77/06

  Polyamides derived from polyamines and polycarboxylic acids (C08L77/10 takes precedence) · CPC title