CH478201A - Process for the production of azo dyes that are sparingly soluble in water - Google Patents

Description

  

  Process for the preparation of azo dyes of the formula which are sparingly soluble in water The invention relates to a process for the preparation of azo dyes of the formula which are sparingly soluble in water
EMI0001.0006
    wherein R1 is a hydrogen, chlorine or bromine atom, R2 is. Halogen atom, an alkyl or alkoxy group, R3 an optionally further substituted, low molecular weight alkyl radical,

       R4 and R5 are hydrocarbon radicals and Y is -C00-, -S-, -SO- or -SO2.



  The hydrocarbon radicals R4 and R5 are preferably identical or different, unsubstituted alkyl radicals having 1 to 4 carbon atoms.



  The process is characterized in that an amine of the formula
EMI0001.0025
         diazotized and with a compound of the formula
EMI0001.0027
    preferably in acidic, optionally buffered, medium. The new dyes pull from aqueous suspension sion on molded bodies, eg. B. fibers or threads, made of synthetic polyamides, e.g. B. nylon or Perlon (registered trademark), cellulose esters, e.g.

   B. acetate rayon or triacetate rayon, polyvinyl plastics, polyolefins, acrylonitrile polymers or polyterephthalic acid glycol esters, z. B. Terylene or Dacron (registered trademarks), in brilliant greenish to reddish blue tones.



  In combination with small amounts of red dyes, cheap light-, wash-, sweat-, chlorine-, sublimation-, pleating- and heat-setting, as well as etchable navy blue dyes and, together with red and yellow dyes, real black dyes can be produced. The wool reserve is very good.



  The dyes are particularly suitable for the so-called thermosol process. They diffuse very quickly into the fiber in the particularly favorable fixing range of 180 to 200 C and do not sublime again if these high temperatures are allowed to act for a long time. This avoids annoying soiling of the dyeing equipment.



  Because of: the excellent light fastness even in the lightest shades, the new dyes are very suitable as mixing components for the production of pastel-colored fashion shades.



  Dyeing is carried out according to processes known per se, that is to say preferably at temperatures between about 80 and 220.degree. C. Polyester fibers can be processed in the presence of carriers at temperatures between about 80 and 125.degree. C. or in the absence of carriers under pressure at about 100 to 140 C colored by the exhaust process or padded or printed at about 140 to 220 C in the presence of thickening agents.



  The processing of the monoazo dyes on dye preparations can be done in various ways. For example, the dried dye is ground with a suitable dispersant, optionally in the presence of fillers, or kneaded in paste form with a dispersant and then dried in vacuo or by atomization.



  In the following example, parts are parts by weight. The temperatures are given in degrees Celsius.



  <I> Example 1 </I> 6.9 parts of powdered sodium nitrite are slowly added to 150 parts of concentrated sulfuric acid at 60-70 = 'with stirring. The mixture is stirred for a further 10 minutes at 60, then cooled to 0 'and 19.7 parts of 2-amino-3-chloro-5-nitro-benzonitrile are added at 0.

   The mixture is stirred for 2 hours and the resulting diazonium salt solution is poured into a cold mixture of 26.6 parts of 3-diethylamino-4-ethoxy-1-methoxycarbonylaminobenzene, 20 parts of concentrated hydrochloric acid, 20 parts of ice and 10 parts of aminosulfonic acid.



  The coupling reaction is carried out in acidic, if necessary buffered, medium at 0 <B> '</B>. The dye obtained is filtered off, washed free of acid and dried. Dyeing instructions 7 parts of the 2-cyano-4-nitro-6-chloro-2'-methoxycarbonylamino-4 'N, N- (diethyl) -amino-5'-ethoxy-1,1'-azobenzene obtained according to Example 1 are mixed with 4 parts of sodium dinaphthylmethanedisulphonic acid,

   4 parts of sodium cetyl sulfate and 5 parts of anhydrous sodium sulfate were ground to a fine powder in a ball mill for 48 hours.



  With the dye preparation obtained in this way, a polyester fiber fabric (Dacron, registered trademark), e.g. B. with the addition of lauryl sulfonate and the emulsion of a chlorinated benzene in water at 80-100 or in the absence of a dye accelerator can be colored under pressure at 110-140.



  The dye preparation is also suitable for printing, padding and the thermal process.



  The blue dyeings obtained are light, dye, wash, water, sea water, sweat, smoke, gas, sublimation, thermosetting and pleating. They can also be white-etched. The dye builds up well and reserves acetate silk, wool and cotton.
EMI0002.0049
  


 

Claims (1)

PATENT CLAIM Process for the production of azo dyes of the formula that are sparingly soluble in water EMI0002.0052 wherein R; a hydrogen, chlorine or bromine atom, R2 halogen, alkyl or alkoxy, R :; an optionally further substituted, low molecular weight alkyl radical, R., and R ;; Hydrocarbon radicals and Y mean -C00-, -S-, -SO- or <B> -SO- "</B>, characterized in that a diazotized amine of the formula EMI0002.0064 with a compound of the formula EMI0002.0065 is coupled. Comment from <I> of the </I> Federal <I> Office for Intellectual Property: </I> If parts of the description are not in accordance with the definition of the invention given in the claim, it should be remembered that according to Art. 51 of the Patent Act, the patent claim is authoritative for the material scope of the patent.