Monoazo dyes based on 4-methyl-4-(4'-aminobenzoyl)aminoantipyrine
Abstract Generated abstract
This study reports the synthesis of pyrazolone monoazo dyes using 4-methyl-4-(4'-aminobenzoyl)-aminoantipyrine as the diazo component. The compound was diazotized with sodium nitrite in hydrochloric acid at low temperature and coupled with various azo components under acidic, alkaline, or acetic-acidic conditions. Eleven previously undescribed dyes were obtained, producing shades from yellow to violet, and their coloristic properties and resistance to washing were evaluated. Because the dyes are insoluble in water, dyeings were formed directly on the fiber and generally showed good fastness to wet treatments.
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PROCEEDINGS
OF THE TOMSK POLYTECHNIC INSTITUTE
OF THE ORDER OF THE OCTOBER REVOLUTION AND THE ORDER OF THE RED BANNER OF LABOR
named after S. M. KIROV
Volume 198 1974
MONOAZO DYES BASED ON
4-METHYL-4-(4′-AMINOBENZOYL)-AMINOANTIPYRINE
L. F. SADOVSKAYA, G. M. STEPNOVA, L. A. SHABROVA
(Presented by the scientific-methodological seminar of the Faculty of Chemical Technology)
In order to study anti-inflammatory activity, we obtained 4-methyl-4-(4′-aminobenzoyl)-aminoantipyrine by reduction of 4-methyl-4-(4′-nitrobenzoyl)-aminoantipyrine [1]. It was of interest to synthesize pyrazolone monoazo dyes on the basis of this compound. In the synthesis of these dyes, 4-methyl-4-(4′-aminobenzoyl)-aminoantipyrine was used by us as the diazo component.
\[ \mathrm{ \begin{array}{c} \text{[[unclear: structural formula of 4-methyl-4-(4′-aminobenzoyl)-aminoantipyrine diazonium salt]]} \end{array} \ \xrightarrow[\mathrm{HCl}]{\mathrm{NaNO_2}}\ \begin{array}{c} \text{[[unclear: structural formula of monoazo dye, with }{-}\mathrm{N{=}N{-}ArX}\text{ substituent]]} \end{array} } \]
To prepare the solution of the diazo component, 4-methyl-4-(4′-aminobenzoyl)-aminoantipyrine was dissolved in the calculated amount of hydrochloric acid. The solution was cooled to 0–5°C; then, with continuous stirring and cooling, a solution of sodium nitrite was slowly added to it. The presence of hydrochloric acid during diazotization was determined with Congo paper, and that of nitrous acid with iodine-starch paper. The solutions of azo components were prepared in the usual manner [2]. Coupling was carried out with cooling and mechanical stirring. The presence of the diazo component during coupling was determined by a spot test with an alkaline solution of R-salt, and that of the azo component by a spot test with diazotized 4-nitroaniline.
After completion of coupling, the dye was filtered off, washed with water, treated with solvent, and dried.
The dyes obtained are insoluble in water; dyeings with them were produced by synthesizing the dyes on the fiber from the components. Owing to their insolubility in water, the dyes give dyeings fast to wet treatments. The characteristics of the dyes obtained are given in the table.
Table
| No. | Azo component | Conditions for dissolving the azo component | Coupling medium | Dye color | Fastness of dyeings to washing |
|---|---|---|---|---|---|
| 1 | Salicylic acid | Cold, with soda | Alkaline | Yellow | 5/5 |
| 2 | Phenol | Cold, with alkali | Alkaline | Yellow-brown | 5/5 |
| 3 | 4-Nitroaniline | Cold, with hydrochloric acid | Acidic | Bright yellow | 5/5 |
| 4 | Resorcinol | Cold, with soda | Alkaline | Yellow | 3/4 |
| 5 | 1-Naphthol | With heating, with alkali | Alkaline | Bordeaux | 4/5 |
| 6 | 2-Naphthol | With heating, with alkali | Alkaline | Orange | 4/5 |
| 7 | 1-Naphthylamine | With heating, with hydrochloric acid | Acidic | Bright orange | 4/4 |
| 8 | 2-Naphthylamine | With heating, with hydrochloric acid | Acidic | Bordeaux | 4/4 |
| 9 | R-acid | Cold, with soda | Alkaline | Pink | 4/4 |
| 10 | Ash acid | Cold, with soda | Alkaline | Violet | 4/5 |
| 11 | Chromotropic acid | Cold, with sodium acetate | Acetic-acidic | Red-violet | 3/5 |
Conclusions
Eleven pyrazolone monoazo dyes not described in the literature have been synthesized; their coloristic properties have been studied, and the fastness of the dyeings to wet treatments has been determined.
Literature
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A. S. Saratnikov, G. M. Stepnova, E. V. Shmidt, L. A. Shabrova, L. N. Lavrent’eva, T. P. Prishchep. Synthesis and pharmacological study of antipyramides of substituted aromatic acids. Izv. Sib. otd. AN SSSR, 12, issue 3, 84, 1965.
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M. A. Chekalin, F. F. Eremin. Production of azo dyes, Goskhimizdat, 417, 1952.