CH452084A - Process for the preparation of water-soluble aminoanthraquinone dyes - Google Patents

Description

  

      Additional patent to main patent no. 430 006 Process for the production of water-soluble aminoanthraquinone dyes The invention relates to a process for the production of water-soluble aminoanthraquinone dyes of the formula
EMI0001.0013
    In this formula, R1 are identical or different low molecular weight alkyl radicals or

  Halogen atoms and R2 a hydrogen atom, a halogen atom or a low molecular weight alkyl radical. The nucleus A can be substituted by halogen atoms, the cyclohexyl radical B by low molecular weight alkyl radicals.



  In this case, an anthraquinone derivative of the formula is condensed with elimination of hydrogen halide
EMI0001.0029
    in which R3 is a hydrogen atom or the sulfonic acid group and R4 is a halogen atom or the primary amino group, with a compound of the formula
EMI0001.0035
    wherein R, represents the primary amino group when R4 represents a halogen atom, and represents a halogen atom,

    when R4 is the primary amino group, and the product obtained sulfonates when R3 is a hydrogen atom.



  The nucleus A in the anthraquinone derivative II is preferably unsubstituted, but can, especially in the 6 and / or 7 positions, be substituted by halogen atoms.

   The cyclohexyl radical B is also generally unsubstituted, but it is also possible to use compounds in which one or both positions ortho to the amino group are substituted by alkyl radicals, in particular by the methyl or ethyl radical.



  In the phenyl radical bonded to the Anührachinongerüst via a nitrogen atom, the positions 2, 4 and 6 or the positions 2 and 6 are preferably occupied by low molecular weight alkyl radicals, in particular by methyl and / or ethyl radicals.



  Chlorine and bromine atoms are preferred halogen atoms in all cases.



  The condensation reaction, which takes place with elimination of hydrogen halide between the compounds (II) and (III), is carried out under the usual conditions. In general, condensation will take place at an elevated temperature, preferably at temperatures above 100 ° C. and given. possibly in an inert solvent, e.g. B. in chlorinated or nitrated aromatic hydrocarbons.

   The condensation is expediently carried out in the presence of an acid-binding agent such as sodium carbonate, sodium acetate or pyridine, and a catalyst, for example in the presence of copper (1) chloride, other copper (1) compounds or copper (11 ) connections or made of metallic copper.

   The dye obtained is isolated, for example by filtration, preferably after the crystallization has been carried out by adding a crystallization accelerator, e.g. B. an alcohol was promoted.



  If the reaction product does not contain a sulfonic acid group, this is finally introduced in the usual way. A second sulfonic acid group already reduces the particularly good property of the new dyes of uniformly dyeing striped polyamide fabrics. It is preferably sulfonated with cooling, for example at temperatures between 0 and 25 C with concentrated sulfuric acid containing small amounts of free sulfur trioxide. The sulfonation product can be poured onto ice and isolated by filtration.



  The products obtained are blue compounds which are readily soluble in water. They are particularly suitable for dyeing textile materials, such as. B. fibers, threads, yarns, nonwovens, woven and knitted fabrics made of synthetic polyamides. These include in particular polycondensation products from adipic acid or other dicarboxylic acids and diamines, especially hexamethylenediamine, or from higher molecular weight aminocarboxylic acids, especially ci-aminoundecanoic acid, and also polylactams, e.g.

   B. poly -, - caprolactam or poly (o-capryl-lactam, understood.



  Fabrics made from these synthetic polyamides, which are often streaky, are dyed completely evenly. However, the new dyes are also suitable for dyeing wool. The dyeings obtained have excellent fastness properties, in particular very good fastness to water, washing, milling, perspiration and light.



  The parts mentioned in the example are parts by weight and the percentages are percentages by weight. The temperatures are given in degrees Celsius. <I> Example </I> 32 parts of 1-chloro-4-mesidino-anthraquinone, 160 parts of cyclohexylamine, 8 parts of sodium acetate and 1.6 parts of copper (1) chloride are heated to 140.degree. The 1-cyclohexyl-amino-4-mesidino-anthraquinone formed by the reaction is precipitated by adding methanol.

   Of this, 10 parts in 50 parts of oleum (10%) are sulfonated at 10-15. When the sulfonation has ended, the reaction mass is poured onto ice, filtered and washed with sodium chloride solution (10%) until the reaction is neutral.



  A blue dye powder is obtained which uniformly dyes wool and synthetic polyamides and particularly streaky polyamide fabrics in blue shades with good light and wet fastness properties.

 

Claims (1)

PATENT CLAIM Process for the preparation of water-soluble aminoanthraquinone dyes of the formula EMI0002.0068 where R1 is identical or different low molecular weight alkyl radicals or halogen atoms and R2 is a hydrogen atom, a halogen atom or a low molecular weight alkyl radical and the nucleus A can be substituted by halogen atoms and the cyclohexyl radical B by low molecular weight alkyl radicals, characterized in that that one is an anthraquinone derivative of the formula EMI0002.0081 in which R3 is a hydrogen atom or the sulfonic acid group and R4 is a halogen atom or the primary amino group, with a compound of the formula EMI0002.0088 wherein R, stands for the primary amino group when R4 is a halogen atom, and for a halogen atom when R4 is the primary amino group, condensed with elimination of hydrogen halide and the product obtained sulfonated when R3 stands for a hydrogen atom.