CH370511A - Process for the preparation of dyes of the anthraquinone series - Google Patents

Description

  

      Process for the preparation of dyes of the anthraquinone series It has been found that new dyes of the anthraquinone series are obtained if the hydroxyl groups of the hydroxyalkylamine radicals are carried out with the aid of halogenating agents in arylamino anthraquinone compounds containing β-hydroxyalkylsulfonic acid amide groups Replaced halogen atoms.



  The arylaminoanthraquinones containing ss- or γ-hydroxyalkylsulfonic acid amide groups are treated with halogenating agents, eg. B. with thionyl chloride, optionally with the addition of inert solvents or diluents, expediently at elevated temperature, for example the temperature of the boiling thionyl chloride.

   The arylaminoanthraquinones containing ss- or γ-hydroxyalkylsulfonic acid amide groups used here can, for. B. from the corresponding arylamino-anthraquinone sulfonic acid chloride compounds by reacting with β- or γ-hydroxyalkylamino compounds, such as ß-hydroxyethylamine, 1-hydroxy-2-amnopropylamine or γ-hydroxypropylamine, or from anthraquinone compounds,

      which contain an exchangeable group, such as 1-amino-4 = bromanthraquinone-2-sulphonic acid, by condensation with arylamino-ss or -y -hydroxyalkylsulfonic acid amides, such as. B. Anüin- 3- or -4-sulfonic acid-ss-hydroxyäthylamid obtained.



  The products of the process are new, valuable dyes that dye animal fibers such as wool, natural silk or casein fibers or fibers made of linear polyamides and linear polyurethanes in strong shades with very good fastness properties.



  The parts given in the examples are parts by weight and the percentages given are percentages by weight. <I> Example 1 </I> 38 parts of 1-amino-4- (anlino-p-sulfonic acid-ß-hydroxyethylamide) -anthraquinone-2-sulfonic acid sodium are introduced into 600 parts of thionyl chloride. 12 parts of anhydrous pyridine are added added and stirred for 40 hours at ordinary temperature.

    It is then filtered, adhering thionyl chloride is washed out with cyclohexane and the filter material is treated with 15% aqueous potassium chloride solution. It is filtered again and washed with aqueous potassium chloride solution. A dye in which the hydroxyl group is replaced by chlorine and dyes the wool in blue tones with good fastness properties is obtained with good yield.

      <I> Example 2 </I> 25 parts of the anhrachinone compound which can be obtained from 1,4-di- (p-phenylanilino) anthraquinone by introducing four sulfonic acid chloride groups using chlorosulfonic acid,

      Reaction of about two sulfonic acid chloride groups with β-hydroxyethylamine to sulfonic acid-β-hydroxyethyl amide groups and hydrolysis of the remaining sulfonic acid chloride groups to sulfonic acid groups are added to 150 parts of N-dimethylformamide and slowly treated with 30 parts of thionyl chloride while stirring and cooling.

   Stirring is continued for about 5 hours at the usual temperature, the reaction material is poured onto a mixture of ice and water, filtered and washed with aqueous sodium chloride solution until the washing solution reacts neutral. After drying at ordinary temperature, a dye is obtained which dyes wool in green shades of good fastness properties.

 

Claims (1)

PATENT CLAIM Process for the preparation of dyes of the anthraquinone series, characterized in that the hydroxyl groups of the hydroxyalkylamine radicals are replaced by halogen atoms with the aid of halogenating agents in arylaminoanthraquinone compounds containing B- or γ-hydroxyalkylsulfonic acid amide groups.