Patent GB-476493-A (GB)
Title: Improvements in the manufacture and production of azo dyestuffs
IPC: C09B29/20
Filed: 1936-06-06
Abstract: Azo dyes are made in substance or on the fibre by coupling o-hydroxycarboxylic acid amides in which one hydrogen atom of the amide group is replaced by the radicle of a mono-azaphenanthrene with diazo compounds of cyclic amines.  Since the amides are in some cases soluble in acid the treatment on the fibre may be carried out in acid solution.  In examples (1)-(3) the following dyes are formed on cotton according to the usual method, (1) and (2) 1-omega-trifluoromethyl-3-aminophenyl-4-ethylsulphone --> 2<1>.3<1>-hydroxynaphthoyl - 9 - or 10 - amino - 4-azaphenanthrene (scarlet-red); other diazo components specified are 4-chloro-3-aminobenzotrifluoride, o- or p-nitroaniline, 2 : 5-dichloraniline, 1-amino-2-methoxy-5-ethyl- or benzylsulphonebenzene, 1-methyl-2-amino-5-chlor- or 5-nitrobenzene, 1-amino-3-methyl-4-nitrilo-6-chlorobenzene, m-chloraniline, 2-aminodiphenyl sulphone 1-methyl-3-nitro-4-aminobenzene; the corresponding amides from o-hydroxycarboxyazanaphthalenes and o-hydroxycarboxyazaphenanthrenes may also be used; (3) 1-amino-3-methyl-4-cyano-6-chlorobenzene --> 2<1> : 3<1>-hydroxynaphthoyl-8-amino-4-azaphenanthrene (brick red); additional diazo components specified are 1-amino-2-trifluormethyl-4-chlorbenzene, 4-amino-4<1>-methoxydiphenylamine, 4-aminodiphenylamine, 1-methoxy-2-amino-5-nitrobenzene, 1-methoxy-3-nitro-4-aminobenzene; 4-benzoylamino-2 : 5-diethoxy-1 - aminobenzene or 4 - amino - 3 - methoxydiphenylamine --> 2<1> : 3<1>-hydroxyanthracenoyl-9- or 10-amino-4-azaphenanthrene; 4-benzoylamino - 2 : 5 - dimethoxy - 1 - aminobenzene, dianisidine, 4-amino-4<1>-methoxydiphenylamine or 3 - amino - 4 - methoxy - 6 - benzoylamino - 1-methylbenzene --> 2<1> : 3<1> - hydroxyanthracenoyl - 10 - amino - 4 - azaphenanthrene; the amides from benzofurane-o-hydroxycarboxylic acids or o-hydroxyphenanthrene carboxylic acids and aminoazaphenanthrenes are also specified; (4) a mixed fabric of staple fibre (Zellwolle) and wool is impregnated with a solution containing 2<1> : 3<1>-hydroxynaphthoyl-10-amino-4-azaphenanthrene, ammonia, ethanol and a dispersing agent and developed with diazotized o-phenetidine --> a -naphthylamine (black); additional components include o-chloraniline, 2 - chlor - 4 - nitroaniline, 6 - chlor-2-toluidine, 4 : 4<1> - dichlor - 2 - aminodiphenylether, 4-amino-2 : 5-dimethoxy-2<1> : 6<1>-dichlor-4<1>-nitroazobenzene and 4-aminodiphenylamine.  Other arylides specified are those from 2 : 3-oxynaphthoic acid and monoamino-2- or 3-azaphenanthrenes. Those derived from other carboxylic acids, e.g. 2 : 3-hydroxycarbazolecarboxylic acid, 2 : 3-hydroxydiphenylene carboxylic acids or from 2 : 3-hydroxycarboxylic acids of azaphenanthrenes, azanaphthalenes, anthracene or phenanthrene may also be used as well as those from 2 : 3-oxynaphthoic acid and diaminoazaphenanthrenes and substituted aminoazaphenanthrenes. Specification 463,456 is referred to.  The amides from o-hydroxyazanaphthalene and o-hydroxyazaphenanthrene carboxylic acids (obtained by action of carbon dioxide on the alkali salts of hydroxyazanaphthalenes and hydroxyazaphenanthrenes) are made by converting the acids into their acetoxy derivatives by means of acetic anhydride, reacting with thionyl chloride to form the corresponding chlorides, condensing the latter with aminoazaphenanthrenes and splitting off the acetyl group.