Patent GB-489014-A (GB)
Title: Improvements in or relating to the printing and colouring of textile and like materials
IPC: D06P3/68
Filed: 1936-10-12
Abstract: Azo dyes, forming on the material; printing.-A composition for use in the production of azo dyes upon the material comprises an aryldiazoimino compound, soluble in alkali, derived from a primary arylamine which may carry up to five substituents selected from halogen, alkyl, aryl, aralkyl, alkoxy, aryloxy, aralkoxy, hydroaryloxy and trifluoroalkyl and a coupling component of the general formula <FORM:0489014/IV/1> wherein Ar represents an aryl residue which may carry one or more substituents as above, x and y are integers each less than 4, preferably 2, 1 or 0 and x + y is not less than 2.  The diazoimino compounds may be replaced by nitrosamines or azo-sulphonates.  The materials dyed or printed may be of cotton, regenerated cellulose, cellulose esters or ethers, wool, silk or leather.  Specified primary arylamines are aniline, 2-chloraniline, 2 : 5-dichloraniline, 4-chloro - 2 - aminoanisole, 4 - chloro - 2 - aminophenetole, 2-anisidine, 4-chloro-2 : 5-dimethylaniline, 4 - chloro - 2 - aminotoluene, 4 - benzoylamino-2 : 5-dimethoxyaniline, 5-nitro-2-aminoanisole, 1-methoxy-2-naphthylamine, 4-chloro-2 - aminodiphenyl ether, m - aminobenzotrifluoride, o-aminoazotoluene, dianisidine, 4 : 41-diaminodiphenylmethane and 3-aminocarbazole.  Specified stabilizing agents for use in preparing the diazoimino compounds are piperidine-a -carboxylic acid, methylglucamine, sarcosin, 1 - methylaminoethane - 2 - sulphonic acid, proline, nipecotinic acid, benzyleneimine-p-sulphonic acid, 1-naphthylamine-2 : 4 : 8-trisulphonic acid and 2-ethylamino-4-sulphobenzoic acid. Specified coupling components are pyrocatechol, resorcinol, m-aminophenol, pyrogallol, 2 : 4-diaminophenol, 2-amino-4-hydroxytoluene, 4-aminoresorcinol, 2-hydroxy-4-aminoanisole, 3 : 5-diaminophenol, 1 : 5- and 1 : 7-aminonaphthols, 2 : 4- and 4 : 8-dihydroxy-1-naphthylamines, 3 - amino - 6 - hydroxycarbazole, phloroglucinol, 1 : 5-, 2 : 6- and 2 : 7-dihydroxynaphthalenes, 1 : 5-dihydroxyanthracene, m-toluylenediamine, 1 : 5 - diaminonaphthalene, 1 : 3 : 5-triaminobenzene and similar compounds in which Ar in the above formula is an anthracene, diphenyl, phenanthrene, chrysene or pyrene residue.  The following examples are specified: (1) resorcinol is ground with the diazoimino compound from diazotized 4-chloro-2-aminoanisole and piperidine-a -carboxylic acid and the mixture is incorporated in an aqueous paste containing ethylene glycol monoethyl ether, caustic soda and starch-gum tragacanth thickener; cotton piece goods, printed with this paste and dried, are subjected for 2 minutes to vapours from a boiling acetic acid solution, rinsed, soaped, rinsed and dried to obtain a brown print; (2) m-aminophenol is mixed with the same diazoimino compound and sugar and the mixture similarly used to obtain a reddish brown print; (3) pyrogallol is mixed with the diazoimino compound from 4-chloro-2-aminotoluene and piperidine-a -carboxylic acid and the mixture similarly used to obtain a tan print; (4) 1 : 5-dihydroxynaphthalene is ground with the diazoimino compound of (1) and the mixture similarly used to obtain a brown print; (5) resorcinol is ground with the diazoimino compound from tetrazotized dianisidine and methylglucamine and the mixture similarly used to obtain a dark brown print; (6) 1 : 7-aminonaphthol is mixed with the diazoimino compound of (3) and the mixture similarly used to obtain a brown print; (7) 1 : 5-aminonaphthol is mixed with the diazoimino compound of (1) and sugar and the mixture similarly used to obtain a brown print.  A table is also given showing the shades obtainable with various combinations of components.