Patent GB-347120-A (GB)
Title: Improvements in and relating to the preparation and use of bodies as dyestuffs or dyestuff intermediates
IPC: C09B56/12
Filed: 1929-10-16
Abstract: Aminohydroxyanthrahydroquinone sulphuric esters; azo dyes; azo dyes, forming on the material; cellulose esters and regenerated celluloses, dyeing.-Aminohydroxyanthrahydroquinone sulphuric esters obtainable by acid or alkaline oxidation of 2-aminoanthrahydroquinone-9 : 10-disulphuric ester or its substitution products having the 1-position free (compare Specifications 333,146 and 334,902, [both in Class 2 (iii), Dyes &c.], are used as components of azo dyes, either by diazotization and coupling with the usual components, or by coupling with diazo compounds.  The monoazo dyes obtained by using the esters as diazo components may be further coupled with diazo compounds to produce disazo dyes.  The dyes containing amino groups may also be diazotized and coupled to yield disazo, trisazo or polyazo dyes, or if the disazo dyes obtained contain nitro groups these may be reduced, diazotized and further coupled.  In examples of the preparation of the parent material, (1) the sodium salt of 2-aminoanthrahydroquinone disulphuric ester is oxidized in caustic soda solution with sodium hypochlorite, and (2) 2-amino-3-chloranthrahydroquinone disulphuric ester is oxidized with ferric chloride in acetic acid.  In examples of the preparation of azo dyes, (3) the product of example (2) is diazotized and coupled with the o-anisidide of 2 : 3-oxynaphthoic acid, the product dyes in red-violet shades which change to red on treatment with acid oxidizing agents, (4) the dyestuff of the previous example is coupled with p-nitraniline; the product dyes a dull red, which becomes scarlet in an acid oxidizing bath, (5) the dyestuff of example (3) is coupled with diazotized p-nitraniline on the fibre, (6) the product of example (1) is diazotized and coupled with (a) 1-phenyl-3-methyl-5-pyrazolone; the product dyes wool and acetate silk a yellow shade which changes to greenish yellow on treatment with nitrous acid, the shades on wool become redder and stronger on chroming; (b) m-amino-p-cresol methyl ether; the product gives orange-yellow dyeings on wool and acetate silk, the shades on wool becoming brown when after-chromed, and (c) m-phenylenediamine; the product dyes wool and acetate silk in reddish brown shades, (7) the product of example (1) is diazotized, coupled with m-phenylenediamine and further coupled with diazotized p-nitraniline; the disazo dye obtained yields brownish shades on wool and acetate silk, (8) m-amino-p-cresol ether is diazotized, coupled with the product of example (1), further diazotized and coupled in alkaline solution with 1 : 5-aminonaphthol; the product dyes cotton and viscose silk in bluish shades, (9) the product of example (1) is coupled with diazotized aniline, diazotized and coupled with b -naphthol, to yield a disazo dye which dyes cotton a brownish shade becoming yellower and stronger when developed with nitrous acid, or with 1-phenyl-3-methyl-5-pyrazolone, to yield a product dyeing acetate silk in greenish yellow, and wool in khaki shades; the latter become brighter and redder when afterchromed or treated with nitrous acid, and (10) the product of example (2) is diazotized, coupled with b -naphthylamine, again diazotized and coupled (alkaline) with 1 : 8 : 4-aminonaphtholsulphonic acid to yield a product dyeing cotton in greenish blue and viscose silk in reddish blue shades or with 2-phenylamino-5-naphthol-7-sulphonic acid to yield a product dyeing in redder shades.  Specifications 333,506 and 333,507, [both in Class 2 (iii), Dyes &c.], also are referred to.