Process for producing asymmetric hypomethyl dye

A kind of technology of alkyl group and nitro group, applied in the field of preparing asymmetric methine dyes

Inactive Publication Date: 2002-10-16
BAYER AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The method involves the disadvantage that at least one of the two reactant components, preferably the aldehyde, must first be prepared in a further step

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Under nitrogen, 46.2 g of methyl 1,3,3-trimethyl-2-methyleneindoline-5-carboxylate were dissolved in 100 ml of n-butanol. Add 34.8 g of 1-phenyl-3-methyl-5-pyrazolone and stir for about 10 minutes. After adding 22.0 g of trimethyl orthoformate and 1 ml of glacial acetic acid, the mixture was refluxed at (102-105° C.) for 5 hours. A further 3 g of trimethyl orthoformate were then added, after which a further 10 hours of reflux were performed. The batch was cooled with stirring, followed by stirring for 2 hours. It was then filtered by applying vacuum, and the filter cake was washed with 200 ml of methanol, then 500 ml of hot water, and dried at 80° C. under reduced pressure.

[0050] 78.8 g of dye was isolated, which was >98.5% asymmetric methine dye of formula 1 below. This dye gives plastics such as polystyrene a vivid orange finish dyeing. In the absence of the glacial acetic acid catalyst, the yield was reduced by about 4%.

[0051] Formula 1 ...

Embodiment 2

[0052] Example 2 Example 1 was repeated using 41.8 g of 1-phenyl-3-methyl-5-pyrrolidone and 31 g of methyl orthoformate. 85.9 g of a dye mixture containing about 92% of the asymmetric methine dye of formula 1 and about 8% of the symmetric methine dye of the formula below were isolated. When used for the spin dyeing of plastics such as polystyrene, this dye mixture gave a vivid orange coloration, however it was significantly yellower than that produced by the dye prepared according to Example 1.

Embodiment 3

[0054] Under a nitrogen atmosphere, 46.2 g of methyl 1,3,3-trimethyl-2-methyleneindoline-5-carboxylate was dissolved in 100 ml of n-butanol. Add 61.6 g of pyrazolone and stir for about 10 minutes.

[0055] After adding 22.0 g of trimethyl orthoformate, the mixture was refluxed at (102-105° C.) for 5 hours. A further 3 g of trimethyl orthoformate were then added, followed by a further 10 hours of reflux. The batch was cooled with stirring and then stirred for 2 hours. It was then filtered by applying a vacuum and the filter cake was washed with 200 ml methanol and then 500 ml hot water and dried at 80° C. under reduced pressure.

[0056] Recrystallization from butanol afforded 100.6 g of the dye of formula 2, ie 91.6% of theory.

[0057] Formula 2

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PUM

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Abstract

The reaction of pyrazolones and methyleneindolines with orthoformates is an ideal one-step method for the preparation of asymmetric methine dyes.

Description

technical field [0001] The present invention relates to a new process for the preparation of asymmetric methine dyes, methine dye mixtures, their preparation and their use for dope dyeing of organic polymer materials. Background technique [0002] Asymmetric methine dyes, such as that in Example 1 of the present application, are very useful for dope dyeing of plastics. Such dyes are prepared, for example, by condensation of the corresponding pyrazolone aldehydes with the corresponding 2-methyleneindolenines (cf. DE-B 1 154 894). [0003] In addition, they can also be prepared by condensation of the corresponding 2-methyleneindolenine-ω-aldehydes with pyrazolones (cf. DE-B 1 172 387 and EP-A 419 110). [0004] F. Würthner, R. Sens, K.-H. Etzbach and G. Seybold, Angew. Chemie, 1999, 111 No 11, pp. 1753-1757 utilize solvents such as acetic anhydride for the preparation of special merocyanines. [0005] C. Reidlinger, R. Dworczak, W.M.F. Fabian and H. Junck, Dyes and Pigments ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/00C08K5/3445C08L101/00C09B23/10C09B67/22
CPCC08K5/3445C09B23/105C09B67/0033
Inventor J·W·施塔维茨K·H·雷恩哈德特C·蒂贝斯
Owner BAYER AG
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