CH329379A - Process for the production of a new vat dye - Google Patents

Description

  

  Process for the preparation of a new vat dye It is known from British Patent No. 339396 that 9-, 11- or 14-amino-benz-anthronanthraquinonylacridines by acylation, for example with acetyl or Ben7o @ rl chloride or the corresponding anhydrides, can be converted into olive dyes.

   It has now been found that by treating 11-amino-benzanthrone-anthraquinone-aeridin with an acylating Dn, -ivnt of 1-nitr-a-a.nthraquinone-2-carbon-
EMI0001.0018
  
     The system used for the numbering of the benzanthrone anthraehinone acridine ring in this description is that in The Ring Index by Patterson and Capell (publisher:

   Reinhold Publishing Corporation), 1940, on page 571 under no. 3888. Drisch an amino group is replaced, very usable dark brown vat dyes he can keep, which deliver rich shades when dyeing and which are particularly useful in modern continuous dyeing processes because of their resistance to the conditions of vatting at high temperatures.



  The new vat dye has the fol lowing formula: This acylation is conveniently carried out by heating the reactants in a suitable diluent, eg. B. in o-dichlorobenzene or nitrobenzene carried out.



  The reduction is carried out before the vatting, for example by treating the nitro compound with ammonia or one of the customary reducing agents. The 11-amino-benzanthrone-anthraquinone-acridine used for the present process can be obtained by condensation of equimolecular amounts of 3-bromobenzanthrone with 1,5-diamino-anthraehinone or an acylamino-1-amino-anthraquinone,

      Fusion of the condensation product with potassium hydroxide, ring closure and, if necessary, separation of the acrylic residue by hydrolysis.



  The new dye provides brown shades on cellulose fibers that have good fastness properties to washing and light. It is superior to previously known brown vat dyes in that it is very resistant to the conditions of vatting at high temperature, so that it is particularly useful in modern vat dyeing processes, at which temperatures of around 85-100 C occur.



  In the following example, parts mean weighted parts.



  <I> Example </I> 29 parts of 11-amino-benzanthrone-anthraquinone-acridine in a very finely divided state and 24 parts of 1-nitro-anthraquinone-2-carboxylic acid chloride are dissolved in 500 parts of o-dichloro benzene registered. The mixture is stirred and slowly heated to 175 C and then stirred at 1.75-180 C. until the development of product is filtered off and added to 500 parts of fresh o-diehlorbenzols.

   The mixture is heated to 180 ° C. and ammonia is passed through it in order to replace the nitro group with an amino group. The o-diehlobenzene is removed by steam distillation, whereupon the dye is filtered off and dried.



  The dye is a brown, dark-black substance that dissolves in concentrated sulfuric acid to form a green solution and dyes cellulose fibers from a dull corinth-red-colored alkaline hydrosulfite vat in shades which, depending on the amount of dye applied, fluctuate between chocolate, char-brown and brownish-black .



  Instead of the o - diehlorbenzene used as diluent for the reaction of the nitro compound with ammonia, an equal amount by weight of nitrobenzene can be used. The nitro compound can also be reduced to the amino compound by heating in an autoclave with a 25% solution of ammonia in water, similarly for 15 hours at 125 ° C.

 

Claims (1)

PATENT CLAIM Process for the production of a new vat dye with the following formula: EMI0002.0063 characterized in that 11-amino-benzanthrone-anthraquinone-acridine is reacted with 1-nitro-anthraquinone-2-carbonyl chloride and then the nitro group is converted into an amino group.