CH209347A - Process for the preparation of an azine series nitro dye. - Google Patents

Description

  

  Process for the preparation of an azine series nitro dye. It has been found that new valuable dyes can be obtained by using diphenylamine derivatives of the general formula:

    
EMI0001.0006
    wherein one Z is an amino group and the other Z is a sulfonic acid group, X is hydrogen or an alkyl or aralkyl radical and Y is an acyl radical, where X and Y together should contain at least five carbon atoms and the other subatituents in which the group
EMI0001.0015
   containing benzene nucleus, with substitution products of 1, 3, 5-trinitrobenzene,

      which contain an exchangeable substituent in the 2-position, condensed in such a way that azine ring closure occurs. The compounds obtained in this way correspond to the general formula:
EMI0001.0025
    where g, Y and Z have the meaning given above and the group
EMI0001.0027
    carrying benzene nucleus can contain further substituents.



  The condensation takes place in two stages, whereby a diphenylamine derivative is formed first, which then changes into the azine dye under suitable conditions with the escape of HNOs. _ For the first stage of the reaction, the use of weakly acid-binding agents, such as B. sodium acetate, calcium carbonate, magnesium carbonate and sodium carbonate are useful. The azine ring closure is then carried out with the use of more alkaline agents by heating to higher temperatures.

   However, it is also possible to carry out the formation of the diphenylamine derivative and the azine ring closure in one operation at the same time. In addition to good leveling properties, the new dyes show good fullness, seawater, perspiration and lightfastness of the dyeings obtained with them, which are also easy to iron. In the combination of these different fastness properties lies the special value of the new dyes produced by the process before the present invention, which in most cases also absorb well on the animal fiber from a neutral bath.



       The present patent now relates to a process for the preparation of a nitro dye of the azine series, characterized in that 1-N-benzoylethylamirro-4-aminobenzene is condensed with 1-chloro-2,4-dinitroberrzene-6-sulfonic acid which is formed Condensation product to 2 ', 4'-diamino-4- (N-benzoylethylamino) - diphenylamine-6'-sulfonic acid and this with 2, 4,

       6-trirritro anisole condensed.



  The dye obtained in this way is a readily water-soluble, brown-black powder and dyes wool and silk in well-leveling, full brown shades of good fastness to fulling, perspiration and seawater. The dyeings obtained are also lightfast and non-iron. <I> Example: </I> A mixture of. 24 parts of 1-N-benzoyl-ethylamino-4-amirrobenzene, 29 parts of 1-chloro-2,4-dinitrobenzene-6-sulforric acid, about 500 parts of water and 50 parts of chalk are refluxed until the reaction has ended is.

   Then the reaction mixture is made alkaline by adding sodium carbonate, and the solution is filtered boiling hot. The condensation product is separated off by adding sodium or potassium chloride, filtered off and washed with salt water.



  The paste of the 2 ', 4'-dinitro 4- (N-ber) zoylethylamino) -dipherrylamine-6'-sulphonic acid sodium obtained in this way is reduced by adding it to a heated mixture of water, acetic acid and iron filings. When the reduction is complete, the mixture is made alkaline with sodium carbonate, briefly boiled, the iron sludge is filtered off and the diamino compound formed is salted out by adding sodium chloride.



  From the paste of the 2 ', 4' diamirro-4- (N-berrzoyläthylamino) -diphenyl amirr-6'-sulfonic acid sodium, an amount corresponding to 47 parts of dry substance is dissolved in about 1000 parts of water with heating. About 70 parts of calcium carbonate and 24.3 parts of 2, 4, 6-trinitroanisole are then added and the mixture is heated to 70-800 ° C. for about 3 hours while stirring. An aqueous solution of 22.3 parts of sodium carbonate is then slowly added and the reaction mixture is stirred at 90 ° C. for a further 1-2 hours.

   The dye solution is diluted, filtered while boiling hot and cooled to around 30-40 ° C. The dye formed is separated out by the slow addition of sodium chloride, filtered off and, if necessary, treated with dilute sodium chloride solution to remove yellow-colored impurities.

 

Claims (1)

PATENT CLAIM: Process for the production of a nitro dye of the azine grater, characterized in that 1-N-benzoylethylamino-4-aminobenzene is condensed with 1-chloro-2,4-dinitrobenzene-6-sulfonic acid, the condensation product formed to 2 ' , 4'-Diamino-4- (N-benzoylätlrylami no) - diphenylami n - 6'-sulfonic acid reduced and this with 2, 4, 6-trinitroanisole condensed. The dye obtained in this way is a readily water-soluble, brown-black powder and dyes wool and silk in well-leveling, full brown shades of good fastness to fulling, perspiration and seawater. The dyeings obtained are also light and ironed.