CH236231A - Process for the production of a vat dye. - Google Patents

Description

  

      Learn about the production of a nfipen dye. It has been found that a vat dye can be produced if 1 112o1 thianthrene dicarboxylic acid or one of its functional derivatives, which contain the carboxyl groups, respectively. Contains carboxyl derivative groups in the same places in the thianthrene molecule,

   which the bromine atoms in the dibromothianthene occupy, which is obtained by bromination of thianthrene in nitrobenzene, with 2 moles of 1-amino-5-benzoylaminoanthraquino: i.



  The new dye is a brown-red powder that vents with a green-violet color and dyes cotton in very real, especially light yellow tones.



  To carry out, Thia.nthrendicarboxylic acid can bezw. one of their functional derivatives, for example the acid chloride, can be used. The reaction is preferably carried out in an inert distribution or solvent, especially those with a higher boiling point, such as chlorobenzene, nitrobenzene or dichlorobenzene, and at elevated temperature, in the presence or absence of acid-binding and catalytically active agents.



  The thianthrendicarboxylic acid used as starting material in the present process can be obtained in the following manner: 216 parts of thianthrene are distributed in 800 parts of nitrobenzene.

   A mixture of 336 parts of bromine and 100 parts of nitrobenzene is slowly added dropwise at room temperature. After several days of stirring at room temperature, the evolution of hydrogen bromide has decreased. One sucks off sharply, rinsed thoroughly with alcohol and dried. The product thus obtained is a white powder which dissolves in concentrated sulfuric acid with a blue color. The analysis shows that it is a dibromothianthrene.



  30 parts of the dibromothianthrene described in the preceding paragraph are distributed together with 16 parts of cuprocyanide in 100 parts of anhydrous pyridine and heated to 250-255 for 6 hours in an autoclave. After cooling, it is filtered, the residue is washed out with alcohol, then stirred for a short time with 30% nitric acid at room temperature, filtered, washed and dried. A brownish, crystalline powder is obtained. According to the analysis, a thianthrendinitrile is present.



  23.4 parts of the thianthrendinitrile described in the preceding paragraph are distributed together with 10 parts of caustic potash in 600 parts of 96% alcohol and heated to 180-185 for 12 hours in an autoclave. The alcohol is then distilled off as completely as possible, the residue is dissolved in water, boiled with a little animal charcoal and filtered. The clear solution is then heated to the boil and hydrochloric acid is added until the congo acidic reaction occurs. The thianthrendicarboxylic acid precipitated in this way is filtered, washed with water and dried.

   He holds a yellowish white, very poorly soluble powder, which dissolves in concentrated sulfuric acid with a red color. Example <I> 1: </I> 1 part of finely powdered thianthrendicarboxylic acid (see above) is distributed in 75 parts of o-dichlorobenzene and the mixture, after adding 6 parts of thionyl chloride, is heated to 140-180 until the Conversion into the thianthrendicarboxylic acid dichloride is completely complete.

   It is distilled off, the excess thionyl chloride is added, a boiling solution of 2.3 parts of 1-amino-5-benzoylaminoanthraquinone in 90 parts of dichlorobenzene is added and the mixture is heated to the boil for about 1 hour. After cooling, it is filtered off, washed first with o-dichlorobenzene, then with alcohol and dried.



  <I> Example 2: </I> 30 parts of finely powdered thianthrene diearonic acid (see above) are distributed in 2000 parts of o-dichlorobenzene and, after adding 50 parts of thionyl chloride, the mixture is heated to 140-180 until the conversion into the thianthrendicarboxylic acid dichloride is completely complete.

   The excess thionyl chloride is completely distilled off, a solution of 70 parts of 1-amino-5-benzoylaminoanthraquinone and 30 parts of anhydrous pyridine in 1,000 parts of o-dichlorobenzene are added and the mixture is heated about. Simmer for 1 hour.

       After cooling, it is filtered off, washed first with o-dichlorobenzene, then with alcohol and finally with water and dried. The dye thus obtained is identical to that described in Example 1.



       Other acid-binding substances, such as pieoline, quinoline, dimethylaniline, etc., can also be used instead of pvridine.

 

Claims (1)

PATENT CLAIM: Process for the production of a vat dye, characterized in that 1 '.Hol thianthrene dicarboxylic acid or one of its functional derivatives which contain the carboxyl groups or. Contains carboxyl derivative groups in the same places in the thia.nthrene molecule that the bro, matome occupy in the dibromothianthrene, obtained by brominating thianthrene in nitrobenzene, with? Mol 1- amino-5-benzo @ # 1- aminoanthraquinone converts :. The new dye is a brownish-red powder that vests with a green-violet color, and cotton in a very real color. especially lightfast yellow tones. SUBCLAIMS: 1. Method according to claim, characterized by the use of Thianthrendica.rbonsii, ureehlorids. 2. The method according to the patent claim, characterized by the implementation of the implementation in a high-boiling indifferent solution.