Methine dyes

Patent metadata

Field	Value
Publication number	US-10487211-B2
Application number	US-201816154959-A
Country	US
Kind code	B2
Filing date	Oct 9, 2018
Priority date	Oct 13, 2017
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

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.

First claim

What is claimed is:

1. A dye of the formula (I)

wherein
R 1 is hydrogen, fluorine, chlorine, COOH or COOR 8 ,
R 2 is hydrogen, fluorine, chlorine, C 1 -C 4 -alkyl or CF 3 ,
R 3 is hydrogen, fluorine, chlorine, COOR 9 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 is hydrogen, fluorine, chlorine, C 1 -C 4 -alkyl or CF 3 ,
R 8 is C 1 -C 4 -alkyl, and
R 9 is C 1 -C 4 -alkyl,
wherein R 1 and R 3 are not both hydrogen.

2. The dye of claim 1 , wherein in formula (I)
R 1 is hydrogen, chlorine, COOH or COOCH 3 ,
R 2 is hydrogen, chlorine, methyl, ethyl, n-propyl, isopropyl or CF 3 ,
R 3 is hydrogen, fluorine, chlorine, COOCH 3 or CN,
R 4 is methyl or phenyl,
R 5 and R 6 are methyl, and
R 7 is hydrogen, chlorine, methyl, ethyl, n-propyl, isopropyl or CF 3 ,
wherein R 1 and R 3 are not both hydrogen.

3. The dye of claim 1 , wherein in formula (I)
R 1 is hydrogen, chlorine or COOCH 3 ,
R 2 is hydrogen or methyl,
R 3 is hydrogen, fluorine or chlorine,
R 4 is methyl,
R 5 and R 6 are methyl and
R 7 is hydrogen, chlorine or methyl,
wherein R 1 and R 3 are not both hydrogen.

4. A method for the bulk colouration of plastic, the method comprising adding one or more dyes of claim 1 into plastic as colorants for the plastic.

5. The method of claim 4 , wherein the plastic is one or more plastics selected from the group consisting of vinyl polymers, polyesters, polyolefins, polycarbonates, and polyamides.

6. The method of claim 4 , wherein the plastics are nylon-6 and/or nylon-6.6.

7. The method of claim 4 , wherein the method comprises adding to the plastic, an amount of 0.0001 to 1 percent by weight of the dyes, based on the amount of plastic.

8. The method of claim 4 , wherein the method comprises adding to the plastic, an amount of 0.01 to 0.5 percent by weight of the dyes, based on the amount of plastic.

9. A method for the bulk colouration of plastic, the method comprising mixing the one or more dyes of claim 1 in dry form with one or more plastics, or, grinding the one or more dyes in dry form with one or more plastics, to produce a mixture, and melting and homogenizing the mixture.

10. The method of claim 9 , wherein the one or more plastics are in the form of granules.

11. A method for the bulk colouration of plastics, the method comprising adding the one or more dyes of claim 1 to a molten plastic material comprising one or more plastics to form a mixture, and then homogenizing the mixture.

12. A method for the bulk colouration of plastics, the method comprising mixing the one or more dyes of claim 1 with monomeric starting components for producing one or more plastics, and subsequently polymerizing the monomeric components.

13. A method for the bulk colouration of polymethyl methacrylate (PMMA), the method comprising mixing the one or more dyes of claim 1 with one or more methyl methacrylate monomers to form a mixture, or dissolving the one or more dyes therein to form a solution, and polymerizing the monomers in the mixture or solution in the presence of one or more polymerization catalysts.

14. A plastic composition comprising the one or more dyes of claim 1 .

15. The plastic composition of claim 14 , wherein the plastic composition is a polyamide composition or a polymethyl methacrylate.

16. A moulding comprising one or more plastic compositions of claim 14 .

17. A method for producing a dye of claim 1 , the method comprising contacting one or more aldehydes of the formula (II)

in which R 1 , R 3 , R 4 , R 5 and R 6 have the definitions specified in claim 1 , with one or more benzothiazole derivatives of the formula (III)

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

Assignees

• Lanxess Deutschland Gmbh

Inventors

• Borst Hans-Ulrich
• Michaelis Stephan
• Linke Frank

Classifications

• C08J3/20

  Compounding polymers with additives, e.g. colouring · CPC title

• C07D417/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C08J2377/02

  Polyamides derived from omega-amino carboxylic acids or from lactams thereof (C08J2377/10 takes precedence) · CPC title

• C08K5/0041

  Optical brightening agents, organic pigments · CPC title

• C09B23/105 Primary

  two >CH- groups · CPC title