Patent GB-295032-A (GB)
Title: Manufacture of strongly basic azo-dyestuffs
IPC: C09B44/02
Filed: 1928-08-01
Abstract: 295,032. Geigy Akt.-Ges., J. R. Aug. 6, 1927, [Convention date]. Samples furnished. Azo dyes.-Strongly basic azo dyestuffs containing the group in which A is hydrogen, alkyl, aryl, or substituted aryl, B is the residue of a strong base, and X is an acid residue, are obtained by either (1) treating an unsulphonated mono- or polyazo dyestuff which contains a primary or secondary amino-group successively with chloracetyl chloride and a tertiary or secondary aromatic base or a di- or tri-alkylamine of the aliphatic series, or (2) treating one or more of the components successively with the chloracetyl chloride and the base and subsequently coupling to produce the dyestuff. The products yield soluble hydrochlorides and give tannin-mordanted cotton-dyeings which are fast to light, washing, acids, and alkalies, and yield pure white reserves. Certain of the products are also suitable for dyeing weighted silk, leather, and jute. The following examples are specified :-(1) A solution in toluene of the dyestuff 4-aminobenzene-azo-#-naphthol is heated with chloracetylchloride and the separated chloracetylated dyestuff is boiled with pyridine; the product gives pure red dischargeable dyeings on tannin-mordanted cotton, vivid scarlet dyeings on weighted silk, and dyeings fast to light on leather. (2) A solution of p-nitraniline in toluene is heated with chloracetyl chloride, the resulting chloracetyl-p-nitraniline is boiled with pyridine, preferably in aqueous suspension, the nitro group in the product is reduced, and the, amine is diazotized and coupled in alkaline solution with 1- phenyl-3-methyl-5-pyra.zolone-; the product gives yellow dyeings on tannin-mordanted cotton and weighted silk. (3) m-Nitraniline is similarly converted into pyridoacetyl-m-nitraniline, the nitro group is reduced, and the amine is diazotized, coupled with m-toluidine, and the product is rediazotized and coupled with #-naphthol; the product gives on tannin-mordanted cotton and weighted silk fast pure red dyeings, dischargeable to a pure white. (4) Diazotized pyridoacetyl-m-phenylenediamine is coupled with pyridoacetyl-m-phenylenediamine, and the monoazo dyestuff is rediazotized and coupled with #- naphthol; the product gives bluish red dyeings on tannin-mordanted cotton and weighted silk. (5) 2: 7-Aminonaphthol is chloracetylated, the product is heated with pyridine, and the N- pyridoacetyl-2 : 7-aminonaphthol is coupled with diazotized a-naphthylamine; the product gives blue-red dyeings on tannin-mordanted cotton and weighted silk. (6) Chloracetyl-m-nitraniline is heated with dimethylamine, the nitro group of the hydrochloride of the resulting dimethylaminoacetyl-m-nitraniline is reduced, and the amine is diazotized and coupled with #-naphthol; the product gives orange-red dyeings on tannin-mordanted cotton and orange dyeings on weighted silk. (7) A solution in toluene of N-ethyl-pnitraniline is heated with chloracetyl chloride, the separated chloracetyl-ethyl-p-nitraniline is heated with pyridine, preferably in aqueous suspension, the nitro group in the, product is reduced, and the amine is diazotized and coupled with #-naphthol; the product gives orange dyeings on tannin-mordanted cotton and weighted silk. (8) A solution in toluene of p-nitrodiphenylamine is heated with chloracetyl chloride, the separated product is heated with pyridine, the nitro group is reduced, and the amine is diazotized and coupled with #-naphthol; the product gives orange-red dyeings on tannin-mordanted cotton and weighted silk. A table is also given showing the properties of the following dyestuffs and the shades of the dyeings on tanninmordanted cotton :-pyridoacetyl-p-phenylenediamine # acetoacetanilide, 1- pyridoacetyl-2- chloro-4-phenylenediamine --> #-naphthol, 1- pyridoacetyl-2-chloro-4-phenylenediamine # 1- phenyl - 3 - methyl-5-pyrazolone, 1-pyridoacetylamino-2-methoxy-5-aminobenzene # #-naphthol, 1-pyridoacetylamino 2-methoxy-5-aminobenbene # 2<1> : 5<1>-dichlorophenyl-3-methyl-5-pyrazolone, pyridoacetyl - 1 : 4-naphthylenediamine # #-naphthol, 1-pyridoacetylamino-2-methoxy- 4-aminobenzene # #-naphthol, pyridoacetyl-oamino-p-toluidine # 1-phenyl-3-methyl-5- pyrazolone, pyridoacetyl - p - phenylenediamine # pyridoacetyl-2 : 7-aminonaphthol, p-toluidine # pyridoacetyl-2:7 (or 1 : 4) -aminonaphthol, aniline # pyridoacetyl-2: 7 (or 1 : 4) - aminonaphthol, dimethylaminoacetyl-p-phenylenediamine # #-naphthol, pyridoacetyl-pphenylenediamine # pyridoacetyl-m-phenylenediamine, # pyridoacetyl-2 : 7-aminonaphthol (or 1-phenyl-3-methyl-5-pyrazolone). and pyridoacetyl - N - ethyl - m - toluylenediamine # #- naphthol.