CH421343A - Process for the preparation of azo compounds - Google Patents

Description

  

  Process for the preparation of azo compounds It has been found that new valuable azo compounds are obtained if an organic compound having one or more diazotized amino groups in the molecule is combined with a compound of the formula
EMI0001.0009
    reacted, in which X1 and X2 are hydrogen or alkyl, cycloalkyl, aralkyl or aryl radicals.

   These hydrocarbon radicals can be substituted, e.g. B. by alkyl, alkoxy, hydroxyalkyl, hydroxyalkoxy, haloalkyl, alkyl or arylsulfonyl or optionally N-substituted sulfonamide groups, carbonamide, nitro or cyano groups or by acylamino groups, also by halogen atoms or by phenyl ,

          Alkoxyphenyl, halophenyl or nitrophenyl groups. If both X1 and X are such hydrocarbon radicals, these can be the same or different. Finally, it is also possible to use compounds of the formula (I) in which there is a non-negative substituent on the carbon atom 4 instead of a hydrogen atom.



  The organic compounds with at least one diazotized amino group in the molecule include all azo components commonly used in the chemistry of azo compounds. They can be substituted by one or more water-solubilizing or preferably by non-water-solubilizing atoms and groups of atoms, e.g.

   B. by at least one halogen atom or an alkoxy, nitro, sulfonyl, sulfonamide, carbon amide, acylamino, haloalkyl or cyano group or a tertiary nitrogen atom. If the components contain hydroxyl, alkoxy or carboxyl groups in the ortho position to azo groups,

      the azo compounds obtained can be converted into the metal complex compounds with the help of metal compounds.



  When using tetrazotized diamines, 1 mole of tetrazonium compound can be coupled with 2 moles of the same compound (I) or a mixture of various such compounds or of one or more compounds (I) and one or more other coupling components.



  The coupling reaction is carried out under the usual conditions, in a neutral, acidic or alkaline medium and preferably in the cold. But you can also heat the reaction mixture.



  The azo compounds obtained are vorzügli che pigments for plastic compounds, resins and varnish raw materials of all kinds and disperse dyes, eg. B. for dyeing hydrophobic fibers, threads and products made from them, e.g. B. from linear, aromatic polyesters' rule. The dyeings obtained have very good fastness properties.



  The parts mentioned in the examples are parts by weight and the percentages are percentages by weight. The temperatures are given in degrees Celsius.



  <I> Example 1 </I> 17.2 parts of 1-amino-2-chloro-4-nitrobenzene are diazotized in the customary manner with 6.9 parts of sodium nitrite. The resulting solution of the diazo compound is slowly added, with stirring, to a solution, cooled to 0, of 24 parts: 1,2-diphenylpyrazolidine 3- imino-5-one in 250 parts of water and 11 parts of 30% sodium hydroxide solution.

   The pH of the reaction mixture is maintained at B by adding sodium hydroxide solution. The azo compound obtained is filtered off and washed neutral.



  By grinding the dyestuff with dispersants and, if appropriate, adjusting agents and additives customary in dyeing, it is possible to produce dyeing preparations. These can be used to produce aqueous dyestuff dispersions that dye polyester fibers made from terephthalic acid and ethylene glycol in a reddish yellow.

   The dyeings obtained are exceptionally fast to light, wash, water, perspiration, pleating and thermal fusing. The dye's resistance to catalytic fading is excellent. Co-treated wool remains undyed, especially if it has been treated in the dye bath with an alkaline reducing agent, e.g. B. a dithionite, be treated.

   The dye can also be converted in a known manner by adding thickeners. make a printing paste.



  The dye obtained can also be used as a mixture with red or blue disperse dyes.



  Further dyes of the general formula can be used in the manner indicated above
EMI0002.0046
    by using the equivalent amount of a diazo component which has the following radical R: 2-chlorophenyl, 2,4-dichlorophenyl, 2-nitro-4-chlorophenyl, 2,6-dichloro-4-nitrophenyl, 2,5-dichloro -4-nitrophenyl, 2-chloro-4-methylsulfonylphenyl, 2-chlorophenyl-4-sulfonic acid amide, 2-chlorophenyl-4-sulfonic acid methylamide, 2-chlorophenyl-4-sulfonic acid dimethylamide,

            2,5-dichlorophenyl-4-sulfonic acid amide, 2,5-dichlorophenyl-4-sulfonic acid methylamide, 2,5-dichlorophenyl-4-sulfonic acid dimethylamide, 2-cyano-4-nitrophenyl, 2-trifluoromethylphenyl, 2-trifluoro-methyl-4- nitrophenyl or 2,5-dichloro-4-methyl-sulfonylphenyl.



  Instead of 1,2 Di @ phenylpyrazolidin-3-imino-5-one can, for. B. Connections are used in which. X1 and / or X, methyl, ethyl, hydroxyethyl, methoxyphenyl, chloro- or bromophenyl or 2-methoxy-4-nitrophenyl are.

 

Claims (1)

PATENT CLAIM Process for the production of azo compounds, characterized in that an organic compound with at least one diazotized amino group in the molecule with a compound of the formula EMI0002.0082 converts, in which X1 and X2 are hydrogen or an optionally substituted hydrocarbon radical.