Patent GB-806938-A (GB)
Title: Monoazo dyestuffs of the benzene-azo-naphthalene series
IPC: C09B29/30
Filed: 1956-08-17
Abstract: 2 - Aminophenyl - phenyl - disulphimides of formula <FORM:0806938/IV (b)/1> wherein R1, R2, R3 and R4 are hydrogen or non-solubilizing radicals, are used as diazo components in the preparation of azo dyes (see Group IV (c)) and are prepared by reacting a benzene sulphonamide with a benzene sulphonyl chloride, either reactant having in the 2-position a nitro or acylamino group and treating the product by reduction of the nitro group or hydrolysis of the acylamino group.  In an example, o-nitrobenzene sulphochloride is reacted with benzene sulphonamide in an aqueous solution made alkaline to phenolphthalein, the resultant solution is made neutral and hydrogenated in the presence of Raney nickel and 2-aminophenyl-phenyl-disulphimide is precipitated by adding a mineral acid.  Further compounds specified are 2-aminophenyl-41-chloro- or -methyl- or -benzoylamino-phenyldisulphimide, 2 - aminophenyl - 31 - or - 41 - acetylaminophenyl- or -31 : 41-dichlorophenylor -21 : 41-dimethylphenyl- or -41-methyl-31-chlorophenyl or -21-methyl-51-chlorophenyl-disulphimide, 2 - amino - 4 - chlorophenyl - phenyl- or -31 : 41-dichlorophenyl- or -41-methyl-31-chlorophenyl- or -41-acetylamino - phenyl - disulphimide, 2 - amino - 3 : 4 - dichlorophenyl - phenyl - disulphimide and 2 - amino-5-nitrophenyl-phenyl-disulphimide.ALSO:The invention comprises monoazo dyes of formula <FORM:0806938/IV (c)/1> wherein R1, R2, R3 and R4 are hydrogen or non-solubilizing radicals, R5 is hydrogen or an amino, alkylamino, cycloalkylamino, aralkylamino, arylamino or acylamino group and R6 is hydrogen, or if R5 is hydrogen, is an acylamino group.  The dyes are prepared by coupling in known manner a diazotized aminophenylphenyl-disulphimide (see Group IV (b)) with a suitable aminonaphthol sulphonic acid.  When the coupling component contains an acylamino group the coupling is in neutral or alkaline medium and is ortho to the hydroxy group, but when the coupling component contains an amino, alkylamino, cycloalkylamino, aralkylamino or arylamino group the coupling is in acid medium and is ortho to the amino group.  Specified diazo components are 2-aminophenyl-41 - chloro - or methyl - or benzoylaminophenyl - disulphimide, 2 - aminophenyl - 21 : 41-dimethylphenyl - or 41 - methyl - 31 - chlorophenyl - or 31 - methyl - 51 - chlorophenyl - or disulphimide, 2 - amino - 4 - chlorophenylphenyl - or 31 : 41 - dichlorophenyl - or 41-methyl - 31 - chlorophenyldisulphimide and 2-amino - 3 : 4 - dichlorophenyl - phenyldisulphimide.  Specified coupling components are 2-substituted - 5 - hydroxynaphthalene - 7 - sulphonic acids the 2-substituents being chloroacetylamino, propionylamino, hexahydrobenzoylamino, butyroylamino, toluylamino, 41-phenylbenzoylamino 21 - chlorobenzoylamino, 21 : 51 - dichlorobenzoylamino, carbomethoxyamino, carboethoxyamino, carbopropoxyamino, carboisopropoxyamino, carbobutoxyamino and carboisobutoxyamino; and 2-substituted-8-hydroxynaphthalene-6-sulphonic acids the 2-substituents being acetylamino, chloroacetylamino, dichloroacetylamino, ethoxyacetylamino, propionylamino, b  - chloropropionylamino, benzoylamino, toluylamino, 41 - phenylbenzylamino, carbomethoxyamino, carbopropoxyamino, carbomethoxyethoxyamino, cyclohexylamino and benzylamino.  The dyes colour wool and polyamide or polyurethane fibres in yellowish orange to yellowish red shades.  In examples monoazo dyes of the above formula are prepared from the following components: diazo: 2-aminophenyl-phenyl- or 31- or 41-acetylaminophenyl - or 31 : 41 - dichlorophenyldisulphimide, 2 - amino - 4 - chlorophenyl - 41-acetylaminophenyl - disulphimide and 2-amino - 5 - nitrophenyl - phenyl - disulphimide; coupling: 2 - acetylamino - or b  - chloropropionylamino - or benzoylamino - or methoxyacetylamino - or carbomethoxyethoxyamino-5 - hydroxynaphthalene - 7 - sulphonic acid and 2 - carboethoxyamino - or (21 : 51 - dichlorobenzoylamino) or amino - or methylamino - or phenylamino - 8 - hydroxynaphthalene - 6 - sulphonic acid.