CH411183A - Process for the preparation of anthraquinone vat dye - Google Patents

Description

  

  Process for the preparation of anthraquinone vat dyes It has been found that valuable anthraquinone vat dyes are obtained if a 2- (f-oxynaphthyl-a) -4,6-lihalo-1,3,5-triazine is reacted with an amine which can be vetted.



  Dichlorotriazines of the formula are preferably used
EMI0001.0008
    wherein one X is a hydrogen atom and the other X is a hydrogen or halogen atom or an oxy group. One mole of the dichlorotriazine is expediently reacted with 2 moles of the vettable amine, preferably an aminoanthraquinone. Suitable aminoanthraquinones are in particular monoaminoanthraquinones, such as.

   B. the 1-amino anthraquinone and its simple substitution products mentioned such. B.



  the 1-amino-4-, -5- or -6-methoxy-anthraquinone, the 1-amino-3-, -6- or -7-chloroanthraquinone, the 1-amino-4-, -5- or -8 -acylamino-, in particular -benzoylaminoanthraquinones.



  The latter can be substituted in the benzoyl radicals, for example by halogen atoms, methoxy, alkyl, trifluoromethyl, sulfonamide or alkyl sulfone groups.

   In addition, 1,4-diamino-2-acetylanthraquinone or 1,4-diamino-2-benzoylanthraquinone should be mentioned, in which only the amino group in the 4-position can be acylated under normal conditions. There are also those aminoanthraquinones which still contain fused carbocyclic or heterocyclic rings,

   for example 4-aminoanthraquinone-2,1 (N) -benzacridone, 5-amino-1,94sothiazolanthrone, 4- or 5-aminoanthrapyrimidine, monoaminoacedianthrones, 4- or 5-amino-l, l'-dianthrimide carbazole, the 4- or 5-amino-5'-benzoylamino-dianthrimide carbazole or 4-amino-4'-benzoylamino-dianthrimide carbazole, 4 amino-anthrapyridones, aminodibenzanthrone, aminoisodibenzanthrone, aminodibenzpyrenquinone,

            Aminoanthanthrone, aminobenzanthrone or aminoflavanthrone. The reaction of the 2- (2'-oxynaphthyl1 ') - 4,6-dihalotriazines with the aminoanthraquinones is conveniently carried out in an inert organic solvent, for example nitrobenzene, chlorobenzene or o-dichlorobenzene at an elevated temperature.



  The dyes obtained are suitable for dyeing a wide variety of materials, for example as pigments, but in particular for dyeing or printing textile materials, in particular made from natural or regenerated cellulose, by the usual vat dyeing and printing processes. The dyeings obtained are characterized by very good light and wet fastness properties.



  In the following examples, unless otherwise stated, the parts are parts by weight, the percentages are percentages by weight, and the temperatures are given in degrees Celsius. <I> Example 1 </I>
EMI0002.0001
    A mixture of 9.2 parts of 1 aminoanthraquinone, 5.8 parts of 2- (2'-oxynaphthyl-1 ') - 4,6-dichloro-1,3,5-triazine and 150 parts by volume of nitrobenzene is used gradually heated to 170 and then stirred until the reaction is complete.

   The dye, which crystallizes in yellow prisms, is filtered off at 80, washed with alcohol and dried. It dyes cotton from a red-orange vat in yellow shades of excellent resistance to chlorine, washing, soda boiling and light.



  If the 1-aminoanthraquinone is replaced by the equivalent amounts of 1-amino-3-chloro-anthraquinone, 1-amino-3-bromo-anthraquinone, 1-amino-5-benzoylamino-anthraquinone, 1 amino-5- (o-fluorobenzoylamino) -anthraquinone, dyes of very true yellow tones are also obtained.



  A real red dye becomes with the appropriate reaction with 1-amino-4-benzoylamino-anthraquinone, and blue dyes with 4-amino-5'-chloro- and 4-amino-3 ', 5'-dichloro-anthraquinone -2.1 (N) 1 ', 2' (N) -benzaeridone were obtained. <I> Example 2 </I>
EMI0002.0025
    A mixture of 4 parts of 1-amino-5-benzoylaminoanthraquinone, 2 parts of the corresponding bromine-containing triazine derivative and 100 parts by volume of nitrobenzene is stirred for 20 hours at 170 to 175 '.

   The dye is filtered off at 90 °, washed with alcohol and dried. It contains a bromine atom in the molecule and colors from the reddish-brown vat in strong orange tones with excellent all-round fastness.



  If, in the example, the 1-aniino-5-benzoylaminoanthraquinone is replaced by the equivalent amount of 1 aminoanthraquinone, the result is a greenish yellow dye and 1-amino-4-benzoylaminoanthraquinone a red dye.

      <I> Example 3 </I>
EMI0002.0042
    In a mixture of 11.7 parts of 1-amino-4-benzoylamino-anthraquinone and 100 parts of N-methyl-pyrrolidone, 12 parts of 2 - (2 '- oxynaphthyl-1') - are added at 100 with stirring. 4,6-dichloro-1,3,5-triazine in 10 minutes and stirred for 3 hours.

    The reaction product crystallized in orange needles is filtered off at 90 °, washed with alcohol and water and dried. It represents 2- (2'-oxy-naphthyl-1 ') -4-chloro-6- (4 "-benzoyl amino-anthraquinonyl-1") -amino-1,3,5-triazine.



  6.7 parts of this intermediate are condensed with 5 parts of 1-amino-5-benzoylamino-anthraquinone in 120 parts of nitrobenzene at 190 to 195 hours for 15 hours. The dye obtained dyes cotton from a red vat in real red-tinged brown tones.

 

Claims (1)

PATENT CLAIM Process for the production of anthraquinone vat dyes, characterized in that a 2- (ss-oxynaphthalene-a) -4,6-dihalogeno-1,3,5-triazine is reacted with an amine which can be linked. SUBClaims 1. Process according to claim, characterized in that 2 moles of the connectable amine are used for one mole of the dihalotriazine. 2. Process according to patent claim, characterized in that 1 mol of dichlorotriazine of the formula EMI0003.0019 wherein one Y is a hydrogen atom, the other Y is a hydrogen or bromine atom, reacts with 2 mol of an a aminoanthraehinone.