CH214907A - Process for the production of a vat dye of the anthraquinone series. - Google Patents

Description

  

  Process for the production of a vat dye of the anthraquinone series. It was found that anthraquinone-2 .1- (N) -1 '. 2 '- (N) -6'-aroylaminobenzolakridone or anthraquinone-2. 1- (S) -1'.2 '- (S) -6'-aroyl-aminothioxanthones of the following type
EMI0001.0009
    X = NH or S R = aryl radical with linking groups represent clear red to blue vat dyes with excellent fastness properties.



  The following methods have been found to form the above dyes. The same thing consists in having anthraquinone 2.1- (N) -1 '. 2 '- (N) -6'-aminobenzolakridone or anthraquinone-2.1- (S) -1'. 2 '- (S) -6'-aminobenzol- thioxanthones, conveniently in a suitable solvent, eg. B. in nitrobenzene, aroylated in the heat with acylating agents that contain coupling groups.

   Examples of these are: the halides of anthraquinone carboxylic acids, nitroanthraquinone carboxylic acids or aminoanthraquinone carboxylic acids, 2-phenylanthraquinone-Bz-4-carboxylic acid, pyrazole anthrone-2-carboxylic acid and 8-oxy-1.

       2-naphthophenazine-Bz-carboxylic acid. By substitution, preferably in the Bz remainder of the Akridon- respectively. Thioxanthone ring by non-solubilizing groups, e.g. B. halogens, OCH3 or OCoH5 groups or in the acyl radical, e.g. B. through the amino or acylamino groups, the nuances can be strongly influenced.



  The dyestuffs obtained form dark colored crystals which are not very soluble in organic solvents, which dissolve easily in the hydrosulphite vat and color the vegetable fibers in real clear red to blue tones; In Rongalit potash printing, they give extensive prints with very good fastness properties on cotton and artificial silk.



  The Antlirachinon - 2. 1- (N) -1 '. 2'- (N) - 6'-aminobenzolakridones respectively. 2. 1- (S) -1 '. 2 '- (S) - 6'-Aminobenzoltliioxanthones can easily be prepared from the corresponding nitro derivatives by reduction or from the 6'-halogen derivatives by exchanging the halogen for the amino group or for acid amide residues and saponifying the latter.



  The subject matter of the present patent is a process for the production of a vat fabric which dyes in blue-tinged Bordo tones. The method is characterized in that one anthracliinon-2.1- (N) -1 '. 2'- (N) -3'-chloro-6'-aminobenzolak pidone with a 1-aminoanthraquinone-2-c @ irbonsäureli <ilogen id.

   The reaction is advantageously carried out at elevated temperatures in the presence of an inert solvent such as. B. nitrobenzene. The pulp formed is deposited in violet needles, which are sparingly soluble in organic solvents and from the dull violet Hydi-osrilfitlz-iipe the fibers in chlorine-, boil- and lightfast, clear,

   stain bluish bordeaux. In the Ronga.lit potash print, the finely distributed dye on cotton and rayon gives deep, clear bordeaux tones of very good eclipse. <I> Example 1: </I>
EMI0002.0038
  
    80 <SEP> parts by weight <SEP> Antlirachinon-2.1- (N) 1 '. <SEP> 2 '- (N) -3'. <SEP> 6'-diclilor benzolalridone,
<tb> 70 <SEP> <B><I>31</I> </B> <SEP> p-toluenesulfamide,
<tb> 20 <SEP> dehydrated <SEP> potassium acetate,
<tb> 700 <SEP> nitrobenzene <SEP> and
<tb> 2 <SEP> copper acetate.

         are heated with thorough stirring for 3 hours at 205 while distilling off the acetic acid formed. The deposited crystals are filtered off with suction at 55 11 C, washed with chlorobenzene, alcohol and water and dried. The sulfamide forms purple needles. To saponify the same, 100 parts by weight are dissolved in 600 parts by weight of concentrated sulfuric acid and heated to 60 to 70 C per hour; then it is poured into water, stirred for 1 hour, filtered off with suction, weighted and dried.

   The antlirachinone- 2. 1- (N) -1 '. 2'- (N) - 3'- chloro - 6'- amiriobenzol- akridon forms blue needles.



  <I> Example 2: </I>
EMI0002.0053
  
    35 <SEP> parts by weight <SEP> of this <SEP> aminoacridone,
<tb> 30 <SEP> 1.-Amirioantbracliinon-2 carboxylic acid chloride <SEP> and
<tb> 800 <SEP> ,, <SEP> nitrobenzene are heated to 160 to 170 ° C for 1 hour while stirring. The dyestuff separated out in an excellent yield is sucked off while still hot, washed with w: ii-no chlorobenzene and with alcohol and dried.

   It forms violet needles, which are not very thin in organic solvents and which color the fibers from the dull violet 11y-drosullitkiipe in clear blue-tinged bordo shades that are chlorine-, boil- and lightfast. In the Rongalit pottery print, the finely distributed dye on cotton and artificial silk gives deep, clear Bordo tones of very good fastness.

 

Claims (1)

PATENT CLAIM: Process for the production of a vat dye of the anthraquinone series, characterized in that one anthraquinone 2.1- (N) -1 '. 2'- (N) - 3'-chloro-6'-aminobenzolakridon with a 1- Aniirioantliracliinori -2 -carbonsäureha.logenid implemented. The dye that can be obtained in this way forms violet needles that are not very soluble in organic solvents and dye the fibers from the dull violet drosulfite vat in clear blue-tinged Bordeaux tones that are chlorine-, boil- and lightfast.