Patent GB-497935-A (GB)
Title: Production of fast dyeings
IPC: C09B37/00
Filed: 1937-06-22
Abstract: Azo dyes, forming on the material; printing; regenerated cellulose, dyeing.-Fast dyeings are obtained by applying to the fibre a 5-hydroxy-7-sulpho-naphtho-oxazole, -thiazole or -imidazole, substituted at the carbon atom of the heterocyclic ring by an aromatic or araliphatic radicle which contains an amino-group capable of being diazotized and which may contain further substituents, diazotizing and coupling with itself or with another diazo-compound from an amine of the constitution above defined, which has been applied to the fibre in the same bath. The coupling may be performed or completed by neutralizing the diazo-solution or by passing the fibre through an alkaline bath. In the examples, the following components are specified: 31-amino-, 31-amino-41-methoxy-, 311- or 411-aminobenzoyl-31-amino-, 311-aminobenzoyl-41-amino-, 411- or 311-aminobenzoyl-31-amino-41-methoxy, 311-amino-411-methoxy benzoyl-31- or -41-amino-, 31-amino-41-ethyl- or -methylsulphonyl, 311 - amino - 411 - ethyl- or -methylsulphonyl-benzoyl-31-amino, 31-amino-41-chloro- and 31-amino-41-methyl-C-phenyl-1 : 2 - (N) - imidazolo - 5 - naphthol - 7 - sulphonic acid, 31 - amino- or 31 - amino - 41 - methoxy - C - phenyl - 1 : 2 - (N) - thiazolo - 5 - naphthol - 7 - sulphonic acid, 31 - amino - C - phenyl - 1 - (N) - 2 - oxazolo-5-naphthol-7-sulphonic acid and 31- or 41 - amino - C - cinnamyl - 1 : 2 - (N) - imidazolo - 5-naphthol-7-sulphonic acid and a mixture of 31-amino-C-phenyl-1 : 2-(N)-imidazolo-5-naphthol-7-sulphonic acid and 31-amino-41-methoxy-C-phenyl - 1 : 2-(N)-thiazolo-5-naphthol-7-sulphonic acid.  They are applied to the fibre in the form of their ammonium or sodium salts and diazotized and developed sometimes in the presence of the usual dyeing assistants.  Some of the dyeings are after-treated with copper sulphate.  In example (8) a fabric of viscose staple fibre or cotton is printed with a paste containing 31-amino-C-phenyl-1 : 2-(N)-imidazolo-5-naphthol-7-sulphonic acid, ammonia, wheat starch tragacanth thickening and sodium nitrite, dried, steamed in acid vapour, passed through a bath of sodium carbonate and finished as usual; the steaming may be replaced by an acid bath treatment; other modifications of the printing process are given including simultaneous use of vat dyestuffs.  In general, the process may be applied to animal fibres, wool and natural silk being specified, but compounds of the general formula <FORM:0497935/IV/1> (where X = 0, S or NH and R = an aromatic or araliphatic radical containing a diazotizable amino group and which may contain other substituents) are especially useful on cellulosic fibres or p  mixtures thereof with animal fibres.  Specifications 1675/05, [Class 2], and 347,609 are referred to.  311-And 411-aminobenzoyl-31-amino-C-phenyl-1 : 2 - (N) - imidazolo - 5 - naphthol - 7 - sulphonic acids (and their 41-methoxy derivatives) are obtained by the action of m- and p-nitrobenzoyl chlorides respectively on the 31-amino compounds (and their 41-methoxy derivatives) followed by reduction of the nitro group.  311-Aminobenzoyl-41-amino-C-phenyl- 1 : 2-(N) - imidazolo - 5 - naphthol - 7 - sulphonic acid and its 411-methoxy derivative are obtained by the action of 3-nitrobenzoyl chloride and its 4-methoxy derivative respectively on the 41-amino compound, followed by reduction of the nitro group.  Corresponding products are obtainable from the corresponding 31-amino compound.  31-Amino-41-methyl (or ethyl) sulphonyl-C-phenyl - 1 : 2 - (N) - imidazolo - 5 - naphthol - 7 - sulphonic acid is obtained by the action of 3-nitro-4-methyl (or ethyl) sulphonylbenzoyl chloride on 1 : 2 - diamino - 5 - naphthol - 7 - sulphonic acid, followed by reduction of the nitro group.  311 - Amino - 411 - methyl (or ethyl) sulphonylbenzoyl - 31 - amino - C - phenyl - 1 : 2 - (N)-imidazolo-5-naphthol-7-sulphonic acid is obtained by the action of 3-nitro-4-methyl (or ethyl) sulphonyl-benzoyl chloride on the 31-amino compound, followed by reduction of the nitro group,  31 - And 41-amino-C-cinnamyl-1 : 2-(N)-imidazolo - 5 - naphthol - 7 - sulphonic acids are obtained by the action of 3-nitro cinnamic acid chloride and 4-nitrocinnamic aldehyde respectively on 1 : 2-diamino-5-naphthol-7-sulphonic acid, followed by reduction of the nitro group.  31-Amino-41-chloro (or methyl) -C-phenyl-1 : 2-(N) - imidazolo - 5 - naphthol - 7 - sulphonic acid is obtained by the action of 4-chloro (or methyl) -3-nitrobenzoyl chloride or 4-chloro-3-nitrobenzaldehyde on 1 : 2 - diamino - 5 - naphthol - 7 - sulphonic acid, followed by reduction of the nitro group.