Patent GB-811521-A (GB)
Title: Monoazo dyestuffs of the benzeno-azo-naphthalene series and metal complexes thereof
IPC: C09B45/14
Filed: 1956-07-19
Abstract: The preparation by conventional methods of 1 - acetylamino - 3,6 - di - (dimethyl - and hydroxyethyl) sulphamyl - and 1 - benzoylamino - 3,6 - di - sulphamyl - 8 - naphthols is described via the sulphochlorides from the corresponding sulphonic acids. 2-Aminophenol-4-sulphonmorpholide is made by converting 2-nitro-1-chlorobenzene to the 4-sulphochloride, the latter to the corresponding sulphonmorpholide, subsequent hydrolysis of the chloro-group, and final reduction to the amine. The products are dyestuff intermediate vide Group IV (c). Specification 326,226, [Class 2 (iii)], is referred to.ALSO:The invention comprises dyestuffs of formula: <FORM:0811521/IV (c)/1> where X is H or Hlg, R1 and R2 are H, alkyl or hydroxy- or cyano-alkyl or may be linked to form a heterocyclic ring and R3 is H, acyl or sulphonyl and their 1,2-metal complexes.  Listed values for R1 and R2 are methyl, ethyl, n- and iso-propyl-, n-butyl, hydroxy-ethyl, -propyl and -butyl, cyano-ethyl and -propyl and sulphon-morpholide and for R3 are acetyl, propionyl, butyryl, benzoyl and phenyl- and methyl-sulphonyl.  The dyestuffs may be made in conventional fashion from appropriate 2-aminophenols and aminophthols and metallized in the usual way to yield 1,2-complexes.  In the formation of the complexes the starting dyestuffs may comprise the o-alkoxy or -acyl-o1-hydroxy-dyestuffs corresponding to those of the above formula.  Specified 2-aminophenols are 2 - aminophenol - 4 - N,N - dimethyl -, -diethyl-, -di-isopropyl-, -bis-hydroxy- and -cyano-ethyl, bis-hydroxypropyl-, N-cyano- and -hydroxy - ethyl -, 2 - amino - 6 - bromophenol-4 - N - ethyl, - N,N - dimethyl - and - diethyl-, 2 - amino - - 8 chlorophenol - 4 - N - hydroxyethyl-, -methyl-, -N,N-dimethyl-, -diethyl-, -diisopropyl-and -bis-hydroxy- and -cyano-ethyl-sulphonamides and 2-amino-6-chlorophenol-4-sulphonamide. Specified coupling components are 1 - benzenesulphonylamino - 3,6 - dimorpholino- and -diethyl-sulphamyl- and -bis-(diethylsulphamyl)-, 1-methylsulphonylamino-3,6-di - (diethylsulphamyl)-, 1 - acetylamino - 3,6-bis - (dimethyl -, - di - (cyanoethyl) -, and -hydroxy- and -cyano-ethyl-sulphamyl)-, 1-propionylamino - 3,6 - diethylsulphamyl -, 1 - benzoylamino - 3,6 - dimorpholino - and - disulphamyl- and -bis-(dihydroxyethyl-, -cyanoethyl-and -diethyl-sulphamyl)- and 1-amino-3,6 - bis - dimethylsulphamyl - 8 - naphthols.  Indicated metals for complex formation are those of atomic weights 52-66, e.g. copper, nickel and iron and especially chromium and cobalt. Dyeing may be effected with the metal dyestuffs in substance, on a substratum or in situ organic fibrous materials being dyed in violet to blue shades.  Dyeing is preferably carried out with the dyestuffs in a dispersed form.  Listed materials for dyeing include nitrogenous and cellulosic materials.  Synthetic resins, organic solvents, stains, varnishes and lacquers may be coloured. Examples are provided of the preparation of the dyestuffs and the use of their chromium and cobalt complexes in dyeing processes the dyestuff components used being selected from those listed above with the addition of 2-aminophenol-4 - sulphonamide, - 4 - N - ethylsulphonamide and -4-sulphonmorpholide and finished chromium dyestuffs derived from 1-acetylamino-3,6 - bis - dimethyl and N - hydroxyethyl - sulphonamido - 8 - naphitols are hydrolysed to the corresponding 1-amino-dyestuffs.  Specification 326,226, [Class 2 (iii)], is referred to.