DE849880C - Process for the production of new sulfonic acid group-free monoazo dyes of the pyrazolone series - Google Patents

Description

Process for the preparation of new sulfonic acid group-free monoazo dyes of the pyrazolone series It has been found that new, valuable sulfonic acid group-free monoazo dyes of the pyrazolone series are obtained if 4-nitro-6-chloro-2-amino-io-xybenzene with such i-phenyl-3-methyl-5-zolones combined, the phenyl radical of which is a sulfonic acid amide group of the composition contains, in which R 1 and R 1 are hydrogen or alkyl radicals. The i-phenyl-3-methY1-5-pyrazolones serving as starting materials in the present process can contain other substituents in the phenyl radical in addition to the sulfonic acid amide group, e.g. B. a methyl or methoxy group or i chlorine atom contain. The sulfonic acid amide group can preferably be an —SO, N 11, - group. However, sulfonic acid amide radicals also come into consideration in which the nitrogen atom of the sulfonic acid amide group contains two or preferably one alkyl radical. In particular, those sulfonic acid amides produce valuable dyes in which the total number of carbon atoms present in the sulfonic acid amide group is not higher than four. As examples of suitable azo components are to be mentioned: i-PhenY1-3-Metfiyl-5-pyrazolon-2'-sulfonic acid amide, i-PhenY1-3-methyl-5-pyrazolone-3'-sulfonic acid amide, i-PhenY1-3-methyl- 5-pyrazolone-4'-sulfonic acid amide, i- (2'-methyl) -phenY1-3-methY1-5-pyrazo-ion-5'-sulfonic acid amide, i- (2'-chloro) -phenY1-3-methyl- 5-pyrazolone-5'-sulfonic acid amide, i-PhenY1-3-methyl-5-pyrazolone-3'-sulfonic acid methylamide, i-PhenY1-3-methyl-5-pyra, zolone-3'-sulfonic acid dimethylamide, i-phenyl-3 -methY1-5-pyrazolone-3'-sulfonic acidoxy'ethylamide, i - phenyl - 3 - methyl - 5 - pyrazolone - 3 '- sulfonic acid -n - butylamide.

The coupling of the diazotized 4-nitro-6-chloro-2-amino-i-oxybenzene with the Pyrazolonsulfonsäureamiden of the specified type can according to the usual per se known methods take place, e.g. B. in acidic, preferably weakly acidic or in alkaline, preferably weakly alkaline agent.

The sulfonic acid group-free monoazo dyes obtainable by the present process are new and correspond to the general formula wherein R represents an aromatic radical of the benzene series which is a sulfonic acid amide group of the composition contains, wherein Ri and R, hydrogen or alkyl radicals.

These new products can be used to dye a wide variety of materials be used. Particularly valuable results are obtained when you use the dyes treated with metal donating agents. This treatment can be known in and of itself In substance, in the dye bath or on the fiber. So can the Metallization in substance z. B. with chromium donating agents in acidic, neutral or weakly alkaline medium, if desired in the presence of suitable additives, such as acids or bases or other acid-binding agents, organic solvents or other additives that promote complex formation, take place openly or under pressure.

The metallization on the fiber, preferably the chroming of the dyes dyed on wool, can be carried out, for example, by the known post-chroming process. However, the dyes are particularly suitable for dyeing by the single-bath chroming process, i. H. for dyeing: addition of alkali chromates and ammonium sulfate and dyed in this way produce dyeings with very good fastness properties.

The following examples serve to illustrate the invention. Unless otherwise stated, the parts mean parts by weight: le and the percentages mean percentages by weight. Example 25.3 parts of i'-PhenY1-3-methyl-5-pyrazolone-3'-sulfonic acid amide are dissolved in 100 parts of water and 8 parts of sodium hydroxide and, at o ', with the conventionally prepared diazo compound from 18.85 parts of 6- Chlorine-4-nitro-2-amino-i-oxybenzene coupled. The clutch starts immediately and is terminated after a short time. About 10 parts of sodium chloride are then added to each 100 parts by volume of the dye suspension thus obtained, the mixture is stirred for another hour, the dye is filtered off, washed with 50 % sodium chloride solution and dried. Nilan receives a dark red-brown powder that dissolves in hot water with red-brown color, and in concentrated sulfuric acid with yellow-brown color. The dye dyes wool in real shades of orange using the single-bath chrome plating process or the post-chrome plating process.

Dyestuffs which also dye wool in orange shades by the single bath chroming process are obtained if, in the above example, instead of 25.3 parts of i-phenyl-3-methY1-5-pyrazolone-3'-sulfonic acid amide, an equivalent amount of one of the following compounds used: i-PhenY1-3-methY1-5-pyrazolon-3'-sulfonic acid-N-methylamide, i-PhenY1-3-methyl-5-pyrazolone-3'-sulfonic acid-fl-oxyethylamide, i-phenyl-3- methyl-5-pyrazolone-4'-sulfonic acid amide, 1- (2'-methyl) -phenY1-3-methyl-5-pyrazolone-5'-sulfonic acid amide, i- (2'-chloro) -phenyl-3-methyl- 3-pyrazolone-5'-sulfonic acid amide.

Claims (1)

PATENT'S CLAIM: A process for the preparation of new sulfonic acid group-free monoazo dyes of the pyrazolone series, characterized in that diazotized 4-nitro-6-chloro-2-araino-i-oxybenzene is combined with such i-phenY1-3-methyl-5-pyrazolones, whose Phenyl radical is a sulfonic acid amide group of the composition contains, where R, and R2 are hydrogen or alkyl radicals, preferably alkyl radicals with a maximum of 4 carbon atoms, and the o, o'-dioxyazo dyes obtained are optionally converted into their metal complex compounds in substance or on the fiber in a manner known per se.