Patent GB-420775-A (GB)
Title: The manufacture of new monoazodyestuffs
IPC: C09B29/30
Filed: 1934-01-23
Abstract: Azo dyes are prepared by coupling a diazo component of the benzene series with a coupling component of the naphthalene or pyrazolone series, at least one of the components containing an amino group substituted by an alkoxyfatty acid group.  The same dyes are obtainable by acting with an alkoxyfatty acid halide or anhydride on azo dyes prepared from a diazo component of the benzene series and a coupling component of the naphthalene or pyrazolone series, at least one of the components containing a primary or secondary amino group. Suitable diazo components containing an alkoxyfatty acid group are obtainable from alkoxyalkacylamino-aminobenzenes, which may be substituted on the nitrogen atom of the alkoxyalkacylamino group by an alkyl, aralkyl, cycloalkyl or aryl group and may be substituted in the nucleus by methyl, methoxy or sulphonic groups.  Suitable coupling components containing an alkoxyfatty acid group are alkoxyalkacylaminonaphtholsulphonic acids, which may be substituted on the nitrogen atom with an alkyl group.  In the examples: (1) diazotized 1 - methoxyacetyl-ethylamino-4-aminobenzene is coupled with 2-(4<1>-methoxyphenylamino)-8-naphthol-6-sulphonic acid or 2-phenylamino-8-naphthol-6-sulphonic acid; diazo components from 1-methoxyacetylamino-4-aminobenzene, 1 - methoxyacetylamino - 4 - aminobenzene - 3 - sulphonic acid, 1-ethoxyacetylamino-4-aminobenzene-3-sulphonic acid, or 1-b -methoxybutyrylamino - 3 - aminobenzene may also be used; (2) diazotized aniline is coupled with 1-methoxyacetylamino-8-naphthol-4 : 6-disulphonic acid; the same dye is obtainable by treating with methoxyacetic anhydride in an aqueous medium the dye from diazotized aniline and 1 - amino - 8 - naphthol - 4 : 6 - disulphonic acid. Dyes containing an alkoxyacylamino group in the diazo component are obtainable also from diazotized 1-methoxyacetylamino-4-aminobenzene, 1 - methoxyacetylamino - 4 - aminobenzene - 3 - sulphonic acid, 1 - methoxyacetyl-ethylamino-4-aminobenzene, or 1-methoxy - acetyl - cyclohexylamino - 4 - aminobenzene and the following components : 1-(2<1>-chloro-5<1>-sulphophenyl) - 3 - methyl - 5 - pyrazolone, 2 - naphthol-6 : 8-disulphonic acid, 1-acetylamino-8 - naphthol - 4 : 6 - disulphonic acid, 1 - acetylamino - 8 - naphthol - 3 : 6 - disulphonic acid, 1 - naphthol - 4 - sulphonic acid, 1 - naphthol-3 : 6-disulphonic acid, 2-amino-8-naphthol-6-sulphonic acid, 2-(2<1>-methoxyphenylamino)-8-naphthol - 6 - sulphonic acid, and 1 - toluene - sulphamino-8-naphthol-3 : 6-disulphonic acid. Dyes containing an alkoxyacylamino group in the coupling component are obtainable also by coupling 1-methoxyacetylamino-8-naphthol-3 : 6-disulphonic acid, 1-methoxyacetylamino-8-naphthol-4 : 6-disulphonic acid, 2-methoxyacetylamino - 5 - naphthol - 7 - sulphonic acid, or 2 - methoxyacetylamino - 8 - naphthol - 6 - sulphonic acid with the diazo compounds from aniline, o- and p-toluidine, 2-chloro-4-aminotoluene, 4-chloro-2-aminotoluene, anthranilic acid, p-xylidine, 2-chloro-5-aminobenzoic acid, 4 - chloro - 2 - aminoanisole, 2- (or 4-)aminodiphenyl ether, 4-aminodiphenylether-2 (or 3)-sulphonic acid, 1 - ethylacetylamino - 4 - aminobenzene, 1 - ethylbenzoylamino - 4 - amino - benzene, 4 - aminotoluene - 3 - sulphanilide, aniline - 3 - sulphanilide, o - aminodiphenyl - sulphone, 1 - methoxyacetyl - ethylamino - 4 - aminobenzene, and 1-cyclohexylacetylamino-4-aminobenzene.  The dyes give yellow, orange, red, violet or brown shades on animal fibres. Alkoxyacylamino compounds.--1 - Methoxy - acetyl - ethylamino - 4 - aminobenzene is preby treating 1-ethylamino-4-nitrobenzene with methoxyacetic anhydride in an aqueous medium, and reducing the product.  1-Methoxyacetylamino - 4 - aminobenzene, 1 - methoxy - acetylamino - 4 - aminobenzene - 3 - sulphonic acid, 1 - ethoxyacetylamino - 4 - aminobenzene-3-sulphonic acid, 1-b -methoxybutyrylamino-3-aminobenzene, and 1-methoxyacetylcyclohexylamino-4-aminobenzene are similarly obtainable.  The methoxyacetylaminonaphtholsulphonic acids mentioned above are obtainable by treating the corresponding aminonaphtholsulphonic acids with methoxyacetic anhydride in an aqueous medium.