Patent GB-399097-A (GB)
Title: Manufacture of intermediate products and dyestuffs therefrom
IPC: C09B29/30
Filed: 1933-02-27
Abstract: N.N<1> - diacyl - 1.4 - diamino - 8 - oxynaphthalene - 6-sulphonic acids are prepared by treating the corresponding diamino compound with an acylating agent.  In an example 1-amino-5-oxynaphthalene-7-sulphonic acid is acetylated and diazotized aniline run in.  The resulting monazo dye is reduced by means of stannous chloride to give 1.4-diamino-8-oxynaphthalene-6-sulphonic acid.  The acetylation of this by means of acetic anhydride and 3- and 4-nitrobenzoyl chlorides is described, in the latter two cases reduction of the nitro group to amino by iron and acetic acid also being exemplified.  Azo dyes are formed in substance or on the fibre by treating the above N.N<1>-diacyl compounds with a diazo compound.  In the case of the aliphatic acyl compounds subsequent coupling with simple diazo compounds yields acid dyes; using aromatic acyl compounds the dyes obtained have affinity for vegetable fibres such as cotton, or artificial silk from regenerated cellulose such as viscose silk, and such dyestuffs may be further developed on the fibre.  The dinitro compounds obtained by using nitroarylacyl bodies may be coupled directly or first reduced and coupled (cf. Specification 13778/02, [Class 2, Acids and salts, Organic &c.].) In examples (1) diacetyl - 1.4 - diamino - 8 - oxynaphthalene - 6 - sulphonic acid is coupled (alkaline) with diazotized aniline or o-anisidine (dyes wool red to violet shades in an acid bath); instead of the diacetyl derivative, the diformyl-, dipropionyl, dicarbethoxy, or dibenzoyl compounds may be used; (2) 2-naphthylamine-4.8-disulphonic acid is diazotized, coupled with a -naphthylamine, further diazotized and coupled with 3<1>.3<11>- or 4<1>.4<11>-diaminodibenzoyl - 1.4 - diamino - 8 - oxynaphthalene-6-sulphonic acid; blue direct-dyeing cotton dyes are obtained which can be converted into green tints by development on the fibre with "yellow components," for instance pyrazole derivatives, acetoacetic arylides, benzoylacetone; thus development on the fibre with 1-phenyl-3-methyl-5-pyrazolone yields a pure green shade.  Instead of 2-naphthylamine-4.8-disulphonic acid 1-amino-8-toluenesulphoxynaphthalene-3.6-disulphonic acid may be used and the disazo dye saponified to remove the ester radicle; similar shades are obtained which may be further developed to fast green dyeings by diazotizing on the fibre and coupling with the above yellow components.  Also 1-amino-4.7-disulphonic acid, 1-amino-4- or 5-sulphonic acids, an amino benzene sulphonic acid may be used as first components, and 1-aminonaphthalene-6- or 7-sulphonic, an ether of 1-amino-2- or 7-oxynaphthalene, or benzene derivatives such as cresidine may replace a -naphthylamine as middle component; a benzene derivative in either position leads to dyes of redder or bluer shades, whereas an aminonaphthol ether as middle component yields dyes giving greener shades; thus the diazo compound of aminoazobenzene sulphonic acid leads to a violet dye; (3) the dye 1-amino-5 - acetoxynaphthalene - 7 - sulphonic acid \sM 2-naphthylamine-5-sulphonic acid is diazotized and coupled with 3<1>-3<11>- or 4<1>.4<11>-diamino dibenzoyl - 1.4 - diamino - 8 - oxynaphthalene - 6 - sulphonic acid; on saponifying off the acetyl group blue direct-dyeing dyes are obtained which can be further developed on the fibre; (4) 1 - amino - 8 - toluenesulphoxynaphthalene-3.6-disulphonic acid (or any of the first components in (2) ) is diazotized, coupled with a -naphthylamine, and the product further diazotized and coupled with a mixture of 1 - naphthylamine - 6 - or 7 - sulphonic acids; further diazotization and coupling with 3<1>.3<11>-or 4<1>.4<11> - diaminodibenzoyl - 1.4 - diamino - 8 - oxynaphthalene-6-sulphonic acid followed by saponification of the ester radicle yields blue trisazo cotton dyes which can be further developed on the fibre; (5) cotton impregnated with 3<1>.3<11>- (or 4<1>.4<11>-) dinitrodibenzoyl-1.4-diamino-8-oxynaphthalene-6-sulphonic acid is developed with diazotized m-nitro-p-toluidine to give a lilac shade; using a diazotized 4-amino-4<1>-ethoxydiphenylamine a blueish-grey dye is obtained, and other suitable diazo components derived from unsulphonated benzene, naphthalene, diphenyl or anthraquinone compounds or aminoazo or diaminoazo compounds may be used.