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yellow methine dye

A methine dye, methyl technology, applied in the direction of methine/polymethine dyes, organic dyes, organic chemistry, etc., to achieve good heat resistance and light resistance, improve thermal stability, improve the effect of light resistance

Active Publication Date: 2019-07-19
LANXESS DEUTDCHLAND GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the properties of these yellow colorants known from the prior art are not sufficient to meet the current technical requirements and improvements are especially needed with regard to their fastness properties such as light fastness and heat resistance

Method used

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  • yellow methine dye
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Examples

Experimental program
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Effect test

example 1

[0116] Preparation of compounds according to the invention

[0117]

[0118] where R 1 =-COOCH 3 , R 2 and R 3 = Cl, R 4 =-CH3 and R 5 and R 6 =-CH 3

[0119] In a feed of 100 ml of methanol, 25.9 g (=0.1 mol) of aldehydes of formula (II) (wherein R 1 =-COOCH 3 , R 4 =-CH 3 and R 5 and R 6 =-CH 3 ), and 18.6 g (=0.1 mol) of 3,4-dichlorophenylacetonitrile. Subsequently, the pH was adjusted to about 10 with about 1 g of 50% aqueous potassium hydroxide solution, and the reactor contents were heated to 60° C. and then stirred for about 6 hours. The mixture was then cooled to 25° C. and the reaction product was separated on a Nutsche filter. The filter cake was washed with about 50 ml of methanol and about 500 ml of water at a temperature of 90°C. The wet product was dried in a vacuum oven at a temperature of 80° C. and a pressure of 200 mbar.

[0120] Yield: 32.5 g (corresponding to 76% of theory), melting point 241°C

example 2

[0122] Preparation of compounds according to the invention

[0123]

[0124] where R 1 =-COOCH 3 , R 2 = H, R 3 = Cl, R 4 =-CH 3 and R 5 and R 6 =-CH 3

[0125] In a feed of 100 ml of methanol, 25.9 g (=0.1 mol) of aldehydes of formula (II) (where R = -COOCH 3 , R 4 =-CH 3 and R 5 and R 6 =-CH 3 ), and 15.2 g (=0.1 mol) of 4-chlorophenylacetonitrile. Subsequently, the pH was adjusted to about 10 with about 1 g of 50% aqueous potassium hydroxide solution, and the reactor contents were heated to 60° C. and then stirred for about 6 hours. The mixture was then cooled to 25° C. and the reaction product was separated on a Nutsche filter. The filter cake was washed with about 50 ml of methanol and about 500 ml of water (T=90° C.). The wet product was dried in a vacuum oven at a temperature of 80° C. and a pressure of 200 mbar.

[0126] Yield: 31.0 g (corresponding to 79% of theory), melting point 199°C

example 3

[0128] Preparation of compositions according to the invention

[0129]

[0130] where R 1 =-COOCH 3 , R 2 = Cl, R 3 = H, R 4 =-CH 3 and R 5 and R 6 =-CH 3

[0131] In a feed of 100 ml of methanol, 25.9 g (=0.1 mol) of aldehydes of formula (II) (wherein R 1 =-COOCH 3 , R 4 =-CH 3 and R 5 and R 6 =-CH 3 ), and 15.2 g (=0.1 mol) of 3-chlorophenylacetonitrile. Subsequently, the pH was adjusted to about 10 with about 1 g of 50% aqueous potassium hydroxide solution, and the reactor contents were heated to 60° C. and then stirred for about 6 hours. The mixture was then cooled to 25° C. and the reaction product was separated on a Nutsche filter. The filter cake was washed with about 50 ml of methanol and about 500 ml of water (T=90° C.). The wet product was dried in a vacuum oven at a temperature of 80° C. and a pressure of 200 mbar.

[0132] Yield: 29.5 g (corresponding to 75% of theoretical value), melting point 130°C

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Abstract

The present invention relates to novel methine dyes, a process for their preparation and their use for the dyeing of plastics, especially polyamides, to obtain yellow colorants with improved lightfastness and improved thermal stability.

Description

technical field [0001] The present invention relates to novel methine dyes, a process for their preparation and their use for dyeing plastics. Background technique [0002] Although there are already many yellow dyes on the market for the coloring of plastics, there is still a need for novel dyes with improved properties. In particular, with regard to the two properties of color strength and thermal stability, there is still a need to improve the known dyes. This applies in particular when the dyes are used for mass coloring of polyamides. [0003] The bulk coloring of synthetic polyamides places higher demands on the colorants used than the bulk coloring of other plastics. The melting point of synthetic polyamides is significantly higher, and the chemical reactivity of molten polyamides, especially nylon-6.6, is also substantially higher, so that the thermal stability of the colorants used must be exceptionally good. Few pigments meet these high requirements, especially ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/10C07D209/12C08K5/3417C08L77/00C08L33/12
CPCC07D209/12C08K5/3417C09B23/0058C09B23/0091C09B23/105C08L77/00C08L33/12C09B23/143C08L77/02C08L77/06C08K5/0041C08J3/12C08J3/201C08J2333/12
Inventor 汉斯-乌尔里希·伯尔斯特弗兰克·林克斯特凡·米凯利斯
Owner LANXESS DEUTDCHLAND GMBH
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