GB1039928A - Reactive monoazo dyestuffs containing a benzene sulphonanilide group - Google Patents

Abstract

The invention comprises monoazo dyes of the formula <FORM:1039928/C4-C5/1> wherein R1 represents H or C1-C4 alkyl, E represents the residue of a coupling component which contains a single sulphonic acid group; and V represents a chloroacetyl or b -chloropropionyl group or a group of the formula <FORM:1039928/C4-C5/2> wherein Y1, Y2 and Y3 each independently represent a H or a Cl atom; R2 represents a C1-4 alkyl radical, and the benzene rings A1 and A11 may be substituted by Cl, NO2, CH3 or -OCH3 groups. The residue of the coupling component may be any of the known series of coupling components which contain a sulphonic group. The dyes may be obtained either by treating a monoazo compound of the formula <FORM:1039928/C4-C5/3> with chloroacetyl chloride, b -chloropropionyl chloride, a 2:4-dichloro-6-(C1-C4) aloxy- 1:3:5-triazine, acryloyl chloride or mono-, dior trichloroacryloyl chloride or by diazotizing an amine of the formula <FORM:1039928/C4-C5/4> (see Division C2 for preparation) and coupling with a coupling component which contains a single sulphonic group. The dyestuffs are suitable for colouring natural and artificial textile materials for example cotton, viscose rayon, regenerated cellulose, wool, silk polyamides and modified polyarylonitrile fibres. These dyes give yellowish red to bluish-red, orange, greenish-yellow, or yellow shades (see also Division D1). The monoazo compounds of Formula I may be prepared by diazotizing an amine of the formula <FORM:1039928/C4-C5/5> wherein T represents NO2 or acylamino, coupline with a coupling component containing a single SO3H group, and subsequently converting the nitro or acylamino group to a primary NH2 group (see Division C2 for preparation of starting material).ALSO:Amines of the formula <FORM:1039928/C2/1> wherein R1 represents H or C1-C4 alkyl, T represents NO2 or acylamino and the benzene rings A1 and A11 may be substituted by Cl, NO2, CH3, or -OCH3 groups, are prepared (1) by reacting a sulphonylchloride of the formula <FORM:1039928/C2/2> with a nitroamine of the formula <FORM:1039928/C2/3> and subsequently hydrolysing the acetylamino group to an amino group to give compounds of Formula II wherein T is NO2; (2) by reacting a sulphonyl chloride of the formula <FORM:1039928/C2/4> and an amine of the formula <FORM:1039928/C2/5> wherein T1 represents an acylamino group, and reducing the nitro group to an amino group to give compounds of Formula II wherein T is acylamino. These compounds are useful as intermediates in the preparation of dyestuffs (see Division C4). Also amines of the formula <FORM:1039928/C2/6> wherein V represents a chloroacetyl, or b -chloropropionyl group or a group of the formula <FORM:1039928/C2/7> wherein Y1, Y2 and Y3 each independently represent H or Cl; R2 represents a C1-C4 alkyl; are obtained either by reacting an amine of the formula <FORM:1039928/C2/8> with chloroacetyl chloride, b -chloropropionyl chloride, a 2:4-dichloro-6-(C1-C4) alkoxy-1:3:5-triazine, acryloyl chloride or a mono-, di- or trichloroacryloyl chloride, and then reducing the nitro group to an amino group, or by condensing a sulphonyl chloride of the formula <FORM:1039928/C2/9> with an amine of the formula <FORM:1039928/C2/100> and then reducing the nitro group to an amino group. These compounds are useful as dyestuff intermediates (see Division C4).ALSO:Reactive monoazo dyes of the formula <FORM:1039928/D1-D2/1> wherein R1 represents H or C1-C4 alkyl, E represents the residue of a coupling component which contains a single sulphonic acid group; and V represents a chloroacetyl or b -chloro-propionyl group or a group of the formula <FORM:1039928/D1-D2/2> wherein Y1, Y2 and Y3 each independently represent a H or a atom; R2 represents a C1-C4 alkyl radical; and the benzene rings A1 and A11 may be substituted by a, NO2, CH3, or-OCH3 groups (see Division C4); are applied to textile materials by dyeing, padding or printing processes. Specified textile materials are cotton, viscose rayon, regenerated cellulose, wool, silk, polyamides and modified polyacrylonitrile fibres. The dyes may be applied to nitrogen-containing textile materials from a mildly alkaline, neutral or acid dyebath.