CH238627A - Process for the production of a vat dye. - Google Patents

Description

  

      Additional patent to the main patent No. 23623.1. Process for the production of a vat dye. It has been found that a vat dye can be produced by adding 1 mol of diphenylenedioxydicarboxylic acid or one of its functional derivatives,

   the respectively the carboxyl group. Contains carboxyl derivative groups bound to the same positions in the diphenylene dioxide molecule that the bromine atoms occupy in dibromodiphenylene dioxide, which is obtained by bromination of diphenylene dioxide in nitrobenzene,

    with 2 moles of 1-amino-5-benzoylamin.oanthraquinOn reacts.



       The new dye is a brown-red powder that blends with violet-brown color and dyes cotton in real, pure, yellow tones.



  To carry out the reaction, diphenylenedioxydicarboxylic acid can bezw. one of their reactive derivatives, for example the acid chloride, can be used.

    The reaction is preferably carried out in an inert distribution or solvent, in particular those with a higher boiling point such as chlorobenzal, nitrobenzene or dichlorobenzene, and at elevated temperature, in the presence or absence of acid-binding and catalytically active agents.



  The diphenylenedioxydicarboxylic acid used as starting material according to 4 @ em process can! in the following way he will keep: 36.8 parts of diphenylene dioxide: of the formula
EMI0001.0054
    are distributed in 120 parts of nitrobenzene.

         67 parts of bromine are slowly added dropwise at room temperature, the mixture is stirred until the initially violent evolution of hydrogen bromide has ceased, filtered off, washed first with nitrobenzene, then with alcohol and dried. One receives a. Product that crystallizes from chlorobenzene in colorless needles and melts at 145-150.

   The analysis shows that a dibromodiphenylene dioxide is present. 20 parts of the dibromodiphenylenedioxide described in the preceding paragraph who distributed the together with 11 parts of cuprocyanide in 100 parts of anhydrous pyridine and heated under pressure to ± 250-255 for 6 hours. After cooling, it is filtered off, washed first with pyridine, then with alcohol and dried.

   To remove copper compounds, the raw product is briefly boiled with 30% nitric acid, then filtered off and washed out with water. A brownish product is obtained which, recrystallized from nitrobenzene, melts at 285-290. According to the analysis, a diphenylenedioxyddinitrile is present.



  7.7 parts of the diphenylenedioxyddinitrile described in the preceding paragraph who distributed the together with 4 parts of caustic potash in 500 parts of 96% alcohol and heated to 180-185 for 8 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 acid reaction occurs.

   After cooling, the diphenydenedioxy dicarboxylic acid precipitated in this way is filtered off, washed with water and dried. A yellowish-white, very poorly soluble powder is obtained.

      <I> Example: </I> 2 parts of finely powdered diphenylenedioxydicarboxylic acid (see above) are divided into <B> 100 </B> parts of o-dichlorobenzene and after adding 10 parts of thionyl chloride to 140 -180 heated until the conversion into the Diphenylendioxy.ddicarbonsäuredichlorid is completely completed. The excess thionyl chloride is distilled off, a boiling solution of 5,

  5 parts of 1-amino-5-benzoyla.minoanthraquinone in 100 parts of o-dichlorobenzene are added and the mixture is heated et-, va. 1 hour to simmer. After cooling, it is filtered off, washed first with o-dichlorobenzene, then with alcohol and dried.

 

Claims (1)

PATENT CLAIM: A process for the production of a vat dye, characterized in that 1 mol of diphenylenedioxydicarboxylic acid or one of its functional derivatives that contain the carboxyl groups or. Contains approx. Rboxyl derivative groups bound at the same points in the diphenylenedioxy dmolecule, which take the bromine atoms in dibromodiphenylenedioxide, which is obtained by brominating diphenylenedioxide in nitrobenzene, with 2 moles of 1-amino-5-benzoylaminoanthraquinone i- I mset. The new dye is a brown-red powder, that associate with violet-brown color; and dyes cotton in real, pure, yellow tones. <B> SUBClaims: </B> 1. Process according to patent claim, characterized by the use of dipheny lendioxyddiearbonsäurecMorids. 2. The method according to claim, characterized by carrying out the reaction in a high-boiling indifferent solvent.