CH220109A - Process for the production of a new copper-containing azo dye. - Google Patents

Description

  

  <B> Additional patent </B> to main patent no. 197582. Process for the production of a new copper-containing azo dye. It has been found that a new copper-containing azo dye is obtained if 1 mole of 1-phenyl- (4'-phenyl-4 "-amino) -3-methyl-5-pyrazolone of the formula
EMI0001.0006
    1 mole of cyanuric chloride, 1 mole of 4-amino-4'-oxy-azobenzene-3'-carboxylic acid,

      1 mol of aniline and 1 mol of diazotized l.-amino-3-sulfobenzene-6-carboxylic acid can act on one another in such a way that the cyanuric chloride gives rise to the pyrazolone derivative, the 4-amino-3'-oxyazobenzene -4'-carboxylic acid and the aniline are linked and the diazo compound engages in the 4-position of the pyrazolone nucleus,

   and the dye obtained in this way is treated with copper-releasing lubricants.



  The copper-containing dye thus obtained forms a brown powder which dyes cotton in yellow, lightfast shades. The 1-phenyl- (4'-pheriyl-4 "-aDiino) -3-methyl-5-pyrazolone can be prepared as follows 22.6 parts of finely ground monoacetylbenzidine are mixed in 50 parts of water and a little ice, 30 parts of hydrochloric acid d --- 1.15 are added, a solution of 7 parts of sodium nitrite in about 20 parts of water is slowly added dropwise at 0-15 and, when the addition of the nitrite is complete, the mixture is stirred for about 1 hour and filtered.



  The filtered diazo solution is left with thorough stirring into an externally cooled mixture of 100 parts of tin chloride for about; 63% and 50 parts of hydrochloric acid d = 1.15 run in at 0-5.



  The hydrazine formed is difficult to solve. The mixture is stirred for about 12 hours, suction filtered, washed with dilute hydrochloric acid and then with water.



  The hydrazine chlorohydrate of the formula thus prepared
EMI0001.0044
    is boiled in 500 parts of water and 100 parts of hydrochloric acid d --- 1.15 for about 2-3 hours. The hydrochloride of aminodiphenyis goes into solution. If necessary, it is tinned with hydrogen sulfide, filtered and allowed to cool.

   A large part of the Clilorhvdrate fails. Further oil can be salted out from the mother liquor or the base can be set free with alkalis.



  The latter forms, uni-crystallized from alcohol, white crystals of F. <B> 179 ', </B> which adhere to. to tan the air.



  <B> 27.2 </B> parts of the chlorohydrate of Ilvdrrazine are poured into hot water; inunt. It is condensed with 14 parts - #, eetessig-> ester at about 60, slowly blunting the acid released during the condensation.

       After the condensation has ended, it is allowed to cool, and with alkali metal plie- noIplitliiiiein-alli: aliscli, stirs for 12 hours, egg, - warms until everything is dissolved and the 1-Plieny1 - (- I'-phenyl-d "_amirio) - e-nietlry1-5.py razoli> ii by k eutralization.



  The production of the pyrazolone can also be based on the hydrazine produced by the sulfite method.



  The new product is because: 'It powder from F. 19-1', soluble in dilute caustic soda and dilute mineral acids. Example:

         6.5 parts of 1-phenyl- (4'-p1) eiiy-1-4 "-amino) - methyl-5-pyrazo @ one of the formula are dissolved.
EMI0002.0069
    in about 5–10 parts of water, containing 10 parts of sodium hydroxide solution in front of 36 "Be and 15 parts of potassium carbonate.



  The filtered reading is mixed inan langsani with the diazo compound from 21.7 parts of 1-amino-3-sulfobenzene-6-carboxylic acid. Once the coupling is complete, the dye solution is neutralized with acetic acid. <B> -Man </B> cools finite ice and slowly gives a suspension of 18,

  4 parts of cyanuric chloride irr ice water zii. lfan stirs, blunting the acid that is released. 25.7 parts of 4- @ lmino-4'-oYazobenzene-3'-aarboxylic acid are then added at regular temperature. The mixture is stirred for a few hours and warmed up to about <B> 50 '</B>.

   The condensation product is extracted, suction filtered, suspended in about 200 parts of water and boiled after adding 18.6 g of aniline for about 1 hour. It is made weakly alhaliscli with soda, the excess aniline is driven off with waterdanipf, filtered and the dye is removed, put on and dried.



  The dye is sucked off, the color cup then finite about. 500 parts of water are grooved and mixed with dilute ammonia until an ammoniacal reaction is achieved.

   One then gives a solution of copper oxide, made from 60 parts of crystalline. Copper sulfate, to and. stirs, if necessary after heating to about 60 ", until the complex formation is complete. -_N-oh, because it cools, the copper-containing dye is removed and dried as usual.

 

Claims (1)

PATENT CLAIM: experienced for the production of a new azo dye, thereby gekenrizeiclinet, da.ss one on 1 31.o1 1-Pheny-1- (4'-phenyl-4 "-amino) -3_metliyl-5-pyrazolone of the formula EMI0002.0136 1 mol of CYaiini-cliloi # id, 1 111o1 4-amino-4'-oxy-azobenzene-3'-carboxylic acid, 1 -Hol aniline and 13l01 dia, zotierte 1-A.mino-3-sulfobenzene-6-carbonic acid allow one another to act in such a way that the vanuric chloride causes the pvrazolone derivative, the 4-aniirio-3'- oxyazabenzene-4'-car- lions <i, The acid and the aniline are linked and the diazo compound intervenes in the 4-position of the pyrazolon nucleus, and the dye thus obtained is treated with copper-releasing agents. The copper-containing dye thus obtained forms a brown powder which dyes cotton in yellow, lightfast tunes.