Sulfo containing monoazo dyestuffs containing a benzthiazole diazo moiety and an N-benzylamino anilino coupling component

Abstract

Azo dyestuffs of formula ##STR1## wherein R.sub.1 denotes hydrogen, C.sub.1 --C.sub.4 alkyl, Cl, Br, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2, --CN, --SCN, --SO.sub.2 CH.sub.3, --SO.sub.2 C.sub.2 H.sub.5, --SO.sub.3 H, --SO.sub.2 NX.sub.2 (X=H or C.sub.m H.sub.2m.sub.+1 with m = 1-4) or --COOC.sub.n H.sub.2n.sub.+1 (n = 0-4);R.sub.2 represents hydrogen, CH.sub.3, C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, Cl, Br, or the grouping --NHCOC.sub.n H.sub.2n.sub.+1 (n = 0-4);R.sub.3 denotes hydrogen, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.3 or C.sub.2 H.sub.5 ;R.sub.4 represents C.sub.n H.sub.2n.sub.+1 (n = o-4), or CH.sub.2 CH.sub.2 SO.sub.3 H;R.sub.5 represents hydrogen or a sulphonic acid group, and p is 1 or 2,With only one of the residues R.sub.1, R.sub.4 and R.sub.5 representing or containing a sulphonic acid group. The dyestuffs are suitable for dyeing nitrogen-containing materials especially for dyeing synthetic polyamide and polyurethane fibers. The dyestuffs are very well absorbed on the polyamide fibers both from an acid dyebath and from a neutral dyebath. In one example synthetic polyamide fibers are dyed in clear shades having good to very good fastness properties.

Description

The subject of the invention is new monoazo dyestuffs containing sulphonic acid groups, of formula ##STR2## as well as processes for their manufacture and their use for dyeing nitrogen-containing fibre materials.

In formula (I),

R.sub.1 denotes hydrogen, C.sub.1 -C.sub.4 alkyl, Cl, Br, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2, --CN, --SCN, --SO.sub.2 CH.sub.3, --SO.sub.2 C.sub.2 H.sub.5, --SO.sub.3 H, --SO.sub.2 NX.sub.2 (X = H or C.sub.m H.sub.2m.sub.+1 with m = 1-4) or --COOC.sub.n H.sub.2n.sub.+1 (n = 0-4); R.sub.2 represents hydrogen, CH.sub.3, C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, Cl, Br or the grouping --NHCOC.sub.n H.sub.2n.sub.+1 (n = 0-4); R.sub.3 denotes hydrogen, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.3 or C.sub.2 H.sub.5 ; R.sub.4 represents C.sub.n H.sub.2n.sub.+1 (n = 0-4), CH.sub.2 CH.sub.2 CN, CH.sub.2 CH.sub.2 OH or CH.sub.2 CH.sub.2 SO.sub.3 H; R.sub.5 represents hydrogen or a sulphonic acid group, and p is 1 or 2. with only one of the residues R.sub.1, R.sub.4 and R.sub.5 representing or containing a sulphonic acid group.

The substituent R.sub.1 can be located in the 4-, 5-, 6- or 7-position of the benzthiazole ring. According to the definition, the new dyestuffs (I) only contain one sulphonic acid group in the molecule. Thus either R.sub.1 or R.sub.5 can represent SO.sub.3 H, or (only) R.sub.4 contains a sulphonic acid group.

The dyestuffs of formula (I) are manufactured by diazotising amines of formula ##STR3## wherein R.sub.1 and p possess the abovementioned significance, combining the product with compounds of formula ##STR4## wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the abovementioned significance, and in each case so choosing the amines of formula (II) and coupling components of formula (III) that only one sulphonic acid group is contained in the finished dyestuff (I).

Diazo components of formula (II) are, for example: 2-amino-(1,3)-benzthiazole, 4-chlor-2-amino-(1,3)-benzthiazole, 5-chlor-2-amino-(1,3)-benzthiazole, 6-chlor-2-amino-(1,3)-benthiazole, 7-chlor-2-amino-(1,3)-benzthiazole, 4-brom-2-amino-(1,3)-benzthiazole, 5-brom-2-amino-(1,3)-benzthiazole, 6-brom-2-amino-(1,3)-benzthiazole, 4,6-dichlor-2-amino-(1,3)-benzthiazole, 4,7-dichlor-2-amino-(1,3)-benzthiazole, 4,6-dibrom-2-amino-(1,3)-benzthiazole, 4-methyl-2-amino-(1,3)-benzthiazole, 6-methyl-2-amino-(1,3)-benzthiazole, 4,7-dimethyl-2-amino-(1,3)-benzthiazole, 6-ethyl-2-amino-(1,3)-benzthiazole, 4-methoxy-2-amino-(1,3)-benzthiazole, 4-ethoxy-2-amino-(1,3)-benzthiazole, 6-methoxy-2-amino-(1,3)-benzthiazole, 6-ethoxy-2-amino-(1,3)-benzthiazole, 6-nitro-2-amino-(1,3)-benzthiazole, 6-cyan-2-amino-(1,3)-benzthiazole, 6-thiocyanato-2-amino-(1,3)-benzthiazole, 6-methylsulphonyl-2-amino-(1,3)-benzthiazole, 6-ethylsulphonyl-2-amino-(1,3)-benzthiazole, 2-amino-(1,3)-benzthiazole-(6)-sulphonic acid, 2-amino-(1,3)-benzthiazole-(6)-sulphonic acid amide, 2-amino-(1,3)-benzthiazole-(6)-sulphonic acid dimethylamide, 2-amino-(1,3)-benzthiazole-(6)-sulphonic acid diethylamide, 2-amino-(1,3)-benzthiazole-(6)-sulphonic acid dibutylamide, 2-amino-(1,3)-benzthiazole-(6)-carboxylic acid, 2-amino-(1,3)-benzthiazole-(6)-carboxylic acid methyl ester, 2-amino-(1,3)-benzthiazole-(6)-carboxylic acid ethyl ester, and 2-amino-(1,3)-benzthiazole-(6)-carboxylic acid butyl ester.

Coupling components of formula (III) are, for example: N-ethyl-N-benzyl-aniline, 3-(N-ethyl-N-benzyl-amino)-toluene, N-methyl-N-benzyl-aniline, 3-(N-methyl-N-benzylamino)-toluene, N-butyl-N-benzyl-aniline, 3-(N-butyl-N-benzyl-amino)-toluene, 3-(N-ethyl-N-benzyl-amino)-chlorobenzene, 3-(N-ethyl-N-benzyl-amino)-bromobenzene, 3-(N-ethyl-N-benzyl-amino)-acetanilide, 3-(N-ethyl-N-benzylamino)-propionic acid anilide, 3-(N-ethyl-N-benzylamino)-anisole, 3-(N-ethyl-N-benzylamino)-ethoxybenzene, 3-(N-butyl-N-benzylamino)-methoxybenzene, 2-(N-benzyl-amino)-toluene, 2-(N-benzyl-amino)-anisole, 4-methyl-2-(N-ethyl-N-benzyl-amino)-anisole, 4-methyl-2-(N-methyl-N-benzyl-amino)-anisole, 4-methyl-2-(N-butyl-N-benzyl-amino)-anisole, 4-methyl-2-(N-methyl-N-benzylamino)-ethoxybenzene, 4-methyl-2-(N-ethyl-N-benzyl-amino)-ethoxybenzene, 4-methyl-2-(N-butyl-N-benzyl-amino)-ethoxybenzene, 4-acetylamino-2-(N-methyl-N-benzyl-amino)-anisole, 4-acetylamino-2-(N-ethyl-N-benzylamino)-anisole, 4-acetylamino-2-(N-butyl-N-benzylamino)-anisole, 4-acetyl-amino-2-(N-ethyl-N-benzyl-amino)-ethoxybenzene, 4-formyl-amino-2-(N-ethyl-N-benzylamino)-anisole, 4-formylamino-2-(N-ethyl-N-benzylamino)-ethoxybenzene, 2-(N-methyl-N-benzylamino)-1,4-dimethoxybenzene, 2-(N-ethyl-N-benzylamino-)1,4-dimethoxybenzene, 2-(N-butyl-N-benzyl-amino)-1,4-dimethoxy-benzene, 2-(N-ethyl-N-benzyl-amino)-1,4-diethoxy-benzene, 3-(N-.beta.-cyanethyl-N-benzyl-amino)-toluene, 3-(N-.beta.-hydroxyethyl-N-benzyl-amino)-toluene, 3-(N-.beta.-cyanethyl-N-benzyl-amino)-anisole, 3-(N-.beta.-hydroxyethyl-N-benzylamino)-anisole, 3-[N-(3-sulphobenzyl)-amino]-toluene, 3-[N-methyl-N-(3-sulphobenzyl)-amino]-toluene, 3-[N-ethyl-N-(3-sulphobenzyl)-amino]-toluene, 3-[N-butyl-N-(3-sulphobenzyl)-amino]-toluene, 3-[N-methyl-N-(3-sulphobenzyl)-amino]-chlorobenzene, 3-[N-ethyl-N-(3-sulphobenzyl)-amino]-chlorobenzene, 3-[N-butyl-N-(3-sulphobenzyl)-amino]-chlorobenzene, 3-[N-ethyl-N-(3-sulphobenzyl)-amino]-bromobenzene, 3-[N-methyl-N-(3-sulphobenzyl)-amino]-acetanilide, 3-[N-ethyl-N-(3-sulphobenzyl)-amino]-acetanilide, 3-[N-butyl-N-(3-sulphobenzyl)-amino]-acetanilide, 3-[N-ethyl-N-(3-sulphobenzyl)-amino]-formanilide, 3-[N-ethyl-N-(3-sulphobenzyl)-amino]-propionic acid anilide, 3-[N-methyl-N-(3-sulphobenzyl)-amino]-anisole, 3-[N-ethyl-N-(3-sulphobenzyl)-amino]-anisole, 3-[N-butyl-N-(.beta.-sulphobenzyl)-amino]-anisole, 3-[N-ethyl-N-(3-sulphobenzyl)-amino]-ethoxybenzene, 2-[N-(3-sulphobenzyl)-amino]-toluene, 2-[N-(3-sulphobenzyl)-amino]-anisole, 4-methyl-2-[N-methyl-N-(3-sulphobenzyl)-amino]-anisole, 4-methyl-2-[N-ethyl-N-(3-sulphobenzyl)-amino]-anisole, 4-methyl-2-[N-butyl-N-(3-sulphobenzyl)-amino]-anisole, 4-methyl-2-[N-methyl-N-(3-sulphobenzyl)-amino]-ethoxybenzene, 4-methyl-2-[N-ethyl-N-(3-sulphobenzyl)-amino]-ethoxybenzene, 4-acetylamino-2-[N-methyl-N-(3-sulphobenzyl)-amino]-anisole, 4-acetylamino-2-[N-ethyl-N-(3-sulphobenzyl)-amino]-anisole, 4-acetylamino-2-[N-butyl-N-(3-sulphobenzyl)-amino]-anisole, 4-acetylamino-2-[N-ethyl-(3-sulphobenzyl)-amino]-ethoxybenzene, 4-formylamino-2-[N-ethyl-N-(3-sulphobenzyl)-amino]-anisole, 4-propionylamino-2 -[N-ethyl-N-(3-sulphobenzyl)-amino]-anisole, 2-[N-methyl-N-(3-sulphobenzyl)-amino]-1,4-dimethoxybenzene, 2-[N-ethyl-N-(3-sulphobenzyl)-amino]-1,4-dimethoxybenzene, 2-[N-butyl-N-(3-sulphobenzyl)-amino]-1,4-dimethoxybenzene, 2-[N-ethyl-N-(3-sulphobenzyl)-amino]-1,4-diethoxybenzene, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-toluene, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-ethylbenzene, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-chlorobenzene, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-bromobenzene, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-anisole, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-ethoxybenzene, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-formanilide, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-acetanilide, 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-propionic acid anilide, 4-acetylamino-2-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-toluene, 4-acetylamino-2-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-anisole, 4-acetylamino-2-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-ethoxybenzene, 4-formylamino-2-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-anisole, 4-propionylamino-2-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-anisole, 2-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-1,4-dimethoxybenzene, and 2[N-benzyl-N-(.beta.-sulphoethyl)-amino]-1,4-diethoxybenzene.

The diazo components of formula (II) are diazotised in a known manner in concentrated sulphuric acid or in concentrated phosphoric acid or in a glacial acetic acid/propionic acid mixture by means of nitrosylsulphuric acid, and combined with the coupling components of formula (III) to give the dyestuffs of formula (I). The coupling reaction is carried out in aqueous solution in a neutral or acid medium. The choice of the diazo components of formula (II) and of the coupling components of formula (III) is always made in such a way that the resulting dyestuff of formula (I) only contains a single sulphonic acid group in the molecule. The dyestuffs of formula (I) are sparingly soluble in water in the cold and if the medium is acid, and can therefore be isolated in a simple manner by filtration. The dyestuffs of formula (I) however form very easily water-soluble sodium salts and can therefore easily be purified by recrystallisation. The sparingly water-soluble dyestuffs of formula (I) isolated under acid conditions can be rendered easily water-soluble by mixing them with suitable salts of strong bases and weak acids, for example sodium tetraborate, sodium carbonate, sodium hydrogen phosphate or tertiary sodium phosphate.

The dyestuffs of formula (I) are suitable for dyeing nitrogen-containing materials such as wool and silk, but preferably for dyeing synthetic polyamide and polyurethane fibres in clear color shades having very good wet fastness properties and good to very good light fastness properties. The dyestuffs are very well absorbed on the polyamide fibres both from an acid dyebath and from a neutral dyebath.

In the examples which follow, parts denote parts by weight:

EXAMPLE 1

150 parts of 2-amino-(1,3)-benzthiazole are introduced into 1000 parts of 85% strength orthophosphoric acid whilst stirring, and are subsequently diazotised by dropwise addition of 304 parts of 41.8% strength nitrosylsulphuric acid over the course of about 1 hour at 0.degree.-3.degree. C. The diazotisation is completed by stirring for a further 3 hours at 0.degree.-3.degree. C. Thereafter 10 parts of urea are added and the mixture is stirred for a further 30 minutes in order to destroy excess nitrosylsulphuric acid. The diazonium salt solution manufactured in this way is added, whilst stirring, to a mixture of 2000 parts of water, 3000 parts of ice and 310 parts of 3-[N-acetyl-N-(3'-sulphobenzyl)-amino]-toluene. The coupling starts immediately and goes to completion in the medium which is acid to Congo Red. After about 5 hours' stirring the resulting dyestuff suspension is heated to 70.degree. C. over the course of 2 hours and stirred at 70.degree. C. for 2 hours. The dyestuff, which is now in a coarse crystalline form, is suction-filtered and washed about 3 times on the filter with 2% strength sodium chloride solution. The wash water then has a pH-value of about 3-4. The dyestuff, of which about 465 parts are obtained after drying, has the constitution ##STR5##

The dyestuff forms an easily water-soluble sodium salt in the pH range of 4-10. It dyes synthetic polyamide fibres or fabrics both from a neutral dyebath and also from a weakly acid dyebath in clear red shades having good to very good fastness properties.

Further valuable dyestuffs are obtained if the diazo components and coupling components listed in the table below are combined with one another in the manner indicated in Example 1. The dyestuffs dye polyamide in the shades indicated.

__________________________________________________________________________ Diazo Component Coupling Component Shade__________________________________________________________________________4-Chlor-2-amino-(1,3)-benzthiazole 3-[N-Ethyl-N-(3'-sulphobenzyl)- bluish-tinged red amino]-toluene5-Chlor-2-amino-(1,3)-benzthiazole " "6-Chlor-2-amino-(1,3)-benzthiazole " "6-Brom-2-amino-(1,3)-benzthiazole " "4,6-Dichloro-2-amino-(1,3)- " "benzthiazole4-Methyl-2-amino-(1,3)-benzthiazole " "6-Methyl-2-amino-(1,3)-benzthiazole) " "6-Ethyl-2-amino-(1,3)-benzthiazole " "6-Butyl-2-amino-(1,3)-benzthiazole " "4,6-Dimethyl-2-amino-(1,3)- " "benthiazole6-Methoxy-2-amino-(1,3)-benzthiazole " "6-Ethoxy-2-amino-(1,3)-benzthiazole " "6-Thiocyanato-2-amino-(1,3)- " strongly bluish-tinged redbenthiazole6-Methylsulphonyl-2-amino-(1,3)- " bluish-tinged redbenzthiazoleBenzosulphonyl-2-amino-(1,3)- " "benzthiazole2-Amino-(1,3)-benzthiazole-(6)- " rubysulphonic acid dimethylamide2-Amino-(1,3)-benzthiazole=(6)- " "carboxylic acid ethyl ester2-Amino-(1,3)-benzthiazole-(6)- " "carboxylic acid .beta.-methoxy-ethyl ester6-Nitro-2-amino-(1,3)-benzthiazole " red violet4-Methoxy-6-chlor-2-amino-:(1,3)- " strongly bluish-tinged redbenzthiazole4-Chloro-6-thiocyanate-2-amino- " bluish-tinged red(1,3)-benzthiazole2-Amino-(1,3)-benzthiazole 3-[N-n-Butyl-N-(3'-sulphobenzyl)- red amino]-toluene4-Chlor-2-amino-(1,3)-benzthiazole " bluish-tinged red6-Chlor-2-amino-(1,3)-benzthiazole " "2-Amino-(1,3)-benzthiazole-(6)- " rubycarboxylic acid ethyl ester2-Amino-(1,3)-benzthiazole 3-[N-Ethyl-N-(3'-sulphobenzyl)- bluish-tinged red amino]-anisole4-Chlor-2-amino-(1,3)-benzthiazole " strongly bluish-tinged red6-Chloro-2-amino-(1,3)-benzthiazole " "6-Thiocyanato-2-amino-(1,3)- " rubybenzthiazole2-Amino-(1,3)-benzthiazole-(6)- " bluish-tinged claretcarboxylic acid dimethylamide2-Amino-(1,3)-benzthiazole-(6)- " strongly bluish-tinged claretcarboxylic acid ethyl ester2-Amino-(1,3)-benzthiazole 3-[N-Ethyl-N-(3'-sulphobenzyl)- red amino]-chlorobenzene6-Chlor-2-amino-(1,3)-benzthiazole " bluish-tinged red6-Thiocyanato-2-amino-(1,3)- " strongly bluish-tinged redbenzthiazole2-Amino-benzthiazole-(6)- " rubycarboxylic acid ethyl ester2-Amino-(1,3)-benzthiazole 3-[N-Ethyl-N-(3'-sulphobenzyl)- bluish-tinged red amino]-acetanilide6-Chlor-2-amino-(1,3)-benzthiazole " strongly bluish-tinged red2-Amino-(1,3)-benzthiazole-(6)- " claretsulphonic acid dimethylamide2-Amino-(1,3)-benzthiazole-(6)- " bluish-tinged claretcarboxylic acid ethyl ester4,7-Dimethyl-2-amino-(1,3)-benzthiazole) " bluish-tinged red2-Amino-(1,3)-benzthiazole 4-Acetylamino-2-[N-ethyl-N- (3'-sulphobenzyl)-amino]-anisole red violet6-Chlor-2-amino-(1,3)-benzthiazole " reddish-tinged violet4,6-Dichlor-2-amino-(1,3)- " reddish-tinged violetbenzthiazole4-Methyl-2-amino-(1,3)- " "benzthiazole4,7-Dimethyl-2-amino-(1,3)- " "benzthiazole6-Thiocyanato-2-amino-(1,3)- " violetbenzthiazole2-Amino-(1,3)-benzthiazole-(6)- " slightly reddish-tingedcarboxylic acid ethyl ester violet6-Methoxy-2-amino-(1,3)- " "benzthiazole6-Methylsulphonyl-2-amino-(1,3)- " "benzthiazole__________________________________________________________________________

EXAMPLE 2

18.5 parts of 6-chlor-2-amino-(1,3)-benzthiazole in 100 parts of 85% strength orthophosphoric acid are diazotised with 30.4 parts of 41.8% strength nitrosylsulphuric acid according to the data in Example 1 and the diazonium salt solution is combined with an aqueous suspension of 31 parts of 3-[N-benzyl-N-(.beta.-sulphoethyl)-amino]-toluene. After the usual working up, 47.3 parts of an azo dyestuff of constitution. ##STR6## are obtained. This dyestuff dyes polyamide fibres or polyamide fabrics from a neutral dyebath or from a weakly acid dyebath in fast, clear, somewhat bluish-tinged red shades.

Further valuable dyestuffs are obtained if the diazo components and coupling components listed in the table which follows are combined with one another in the manner indicated in Example 1. The dyestuffs dye polyamide in the shades indicated.

__________________________________________________________________________ Diazo Component Coupling Component Shade__________________________________________________________________________2-Amino-(1,3)-benzthiazole 3-[N-Benzyl-N-(.beta.-sulphoethylamino)- yellowish-tinged red toluene4-Chlor-2-amino-(1,3)- " bluish-tinged redbenzthiazole4,6-Dichloro-2-amino-(1,3)- " bluish-tinged redbenzthiazole4-Methyl-2-amino-(1,3)- " redbenzthiazole4,7-Dimethyl-2-amino-(1,3)- " redbenzthiazole6-Thiocyanato-2-amino-(1,3)- " strongly bluish-tinged redbenzthiazole6-Nitro-2-amino-(1,3)-benzthiazole " ruby6-Methylsulphonyl-2-amino-(1,3)- " strongly bluish-tinged redbenzthiazole2-Amino-(1,3)-benzthiazole-(6)- " "carboxylic acid ethyl ester2-Amino-(1,3)-benzthiazole-(6)- " "sulphonic acid dimethylamide__________________________________________________________________________

EXAMPLE 3

150 parts of 2-amino-(1,3)-benzthiazole are diazotised in accordance with the data in Example 1 and coupled with 280 parts of 2-[N-(3'-sulphobenzyl)-amino]-toluene according to the data in Example 1. 428 parts of dyestuff of formula ##STR7## are obtained, which dyes polyamide fibres from neutral or weakly acid dyebaths in clear scarlet-coloured shades.

Further valuable dyestuffs are obtained if the diazo components and coupling components of the table below are combined in accordance with the manner indicated in Example 1. The dyestuffs dye polyamide fibres in the shades indicated.

__________________________________________________________________________ Diazo Component Coupling Component Shade__________________________________________________________________________4-Chlor-2-amino-(1,3)-benzthiazole 2-[N-(3-Sulphobenzyl)-amino]-toluene bluish-tinged red6-Chlor-2-amino-(1,3)-benzthiazole " bluish-tinged red6-Methyl-2-amino-(1,3)-benzthiazole " red6-Thiocyanato-2-amino-(1,3)- " bluish-tinged redbenzthiazole2-Amino-(1,3)-benzthiazole 2-[N-(3-Sulphobenzyl)-amino]-anisole red4-Chlor-2-amino-(1,3)-benzthiazole " bluish-tinged red6-Chlor-2-amino-(1,3)-benzthiazole " bluish-tinged red4,7-Dimethyl-2-amino-(1,3)- " redbenzthiazole6-Thiocyanato-2-amino-(1,3)- " strongly bluish-tinged redbenzthiazole__________________________________________________________________________

EXAMPLE 4

23 parts of 2-amino-(1,3)-benzthiazole-(6)-sulphonic acid in 85% strength orthophosphoric acid are diazotised with nitrosylsulphuric acid analogously to the data in Example 1 and coupled with 21.5 parts of N-ethyl-N-benzyl-aniline. 42.4 parts of the dyestuff of formula ##STR8## are obtained. This dyestuff dyes polyamide fibres from neutral or weakly acid dyebaths in clear red shades.

Further valuable dyestuffs are obtained if, in this example, the coupling components of the table below are used in place of N-ethyl-N-benzyl-aniline. The dyestuffs manufactured in this way dye polyamide fibres in the shades indicated.

__________________________________________________________________________Diazo Component Coupling Component Shade__________________________________________________________________________as in Example 4 N-n-Butyl-N-benzyl-aniline red" 3-(N-Methyl-N-benzyl-amino)-toluene bluish-tinged red" 3-(N-Ethyl-N-benzyl-amino)-toluene strongly bluish-tinged red" 3-(N-n-Butyl-N-benzyl-amino)-toluene strongly bluish-tinged red" 3-(N-Ethyl-N-benzyl-amino)-chlorobenzene bluish-tinged red" 3-(N-Ethyl-N-benzyl-amino)-acetanilide strongly bluish-tinged red" 3-(N-Ethyl-N-benzyl-amino)-anisole strongly bluish-tinged red" 2-(N-Benzyl-amino)-toluene red" 2-(N-Benzyl-amino)-anisole bluish-tinged red" 4-Acetylamino-2-(N-ethyl-N-benzyl-amino)-anisole violet" 3-(N-Benzyl-amino)-acetanilide bluish-tinged red" 4-Acetylamino-2-(N-benzyl-amino)-anisole violet__________________________________________________________________________

Claims

1. Azo dyestuff of the formula ##STR9## wherein R.sub.1 denotes hydrogen, C.sub.1 -C.sub.4 alkyl, Cl, Br, --OCH.sub.3, --OC.sub.2 H.sub.5, --NO.sub.2, --CN, --SCN, --SO.sub.2 CH.sub.3, --SO.sub.2 C.sub.2 H.sub.5, --SO.sub.3 H or --SO.sub.2 NX.sub.2 with X being H or C.sub.m H.sub.2m.sub.+1 and m representing a number from 1 to 4, or R.sub.1 represents --COOC.sub.n H.sub.2n.sub.+1, with n representing a number from 0 to 4,

R.sub.2 represents hydrogen, --CH.sub.3, --C.sub.2 H.sub.5, --OCH.sub.3, --OC.sub.2 H.sub.5, Cl, Br or --NHCOC.sub.n H.sub.2n.sub.+1, with n representing a number from 0 to 4,

R.sub.3 denotes hydrogen or --OCH.sub.3, --OC.sub.2 H.sub.5, CH.sub.3 or C.sub.2 H.sub.5,

R.sub.4 represents C.sub.n H.sub.2n.sub.+1, with n representing a number from 0 to 4, or R.sub.4 represents --CH.sub.2 CH.sub.2 --SO.sub.3 H,

R.sub.5 represents hydrogen or sulphonic acid and p is 1 or 2,

with the proviso that the dyestuff contains only one sulphonic acid radical and one of R.sub.1, R.sub.4 and R.sub.5 represents or contains the said sulphonic acid radical.