GB856452A - Protective agents against textile pests, mould and bacteria - Google Patents

Abstract

Haloalkyl-, haloaralkyl- and-or haloarylsulphonamides of aminodiphenylamines or Niminosubstituted aminodiphenylamines, halogenated in one or both of the aromatic nuclei, are obtained by reacting the corresponding aminodiphenylamines, which may be substituted, with haloalkyl-, haloaralkyl- or haloarylsulphonic acid chlorides. Alternatively the halogen may be introduced in other ways, e.g. by chlorination or bromination with free halogens or sulphuryl chloride or bromide, by the reaction of diazonium chlorides to give fluorine or chlorine compounds, or by the exchange of moveable groups for fluorine. In an example, 2-aminodiphenylamine is dissolved in anhydrous pyridine and chloromethane-sulphonic acid added dropwise while stirring and cooling in a mixture of ice and salt. After stirring for several hours, the mixture is poured into water, the separated reaction product is dissolved in water with the aid of sodium hydroxide, treated with carbon and fuller's earth, filtered, reprecipitated with acid, filtered off, washed with water and dissolved in ether. This solution is filtered through carbon and distilled, and the residue recrystallised from aqueous methanol. The resulting chloromethanesulphonyl-2-aminodiphenyl-amine is dissolved in orthodichlorbenzene, a little ferric chloride added, and chlorine introduced until analysis shows approx. six atoms of chlorine per molecule. The solvent is then distilled off and the residue worked up as above. Numerous examples are given in the specification of starting materials for and products obtained by the above condensation, with or without the after-chlorination. Specification 738,758 is referred to.