Patent GB-493501-A (GB)
Title: Improvements in the manufacture and production of dyestuffs
IPC: C09B55/00
Filed: 1937-04-21
Abstract: Dyestuffs containing metals are prepared by reacting primary aromatic amines containing in at least one o-position to an amino group an OH, O-alkyl, SH, S-alkyl, NH2, -NH, COOH or O-CH2-COOH group, i.e. groups capable of combining with metal, with ketones or aldehydes which also contain a group of the said kind in o-position, the resulting products being treated simultaneously or subsequently with agents supplying metal, the starting materials being so chosen that at most one of them contains OH as metallizable group.  Amines specified are o-aminophenols, 1-amino-2 : 4-dihydroxybenzene, 1 : 5 - diamino - 2 : 4-dihydroxybenzene, o-aminohydroxycarbazoles, 3 : 31-dioxybenzidine, o-aminonaphthols, o-anisidines, o - aminothiophenols, o - aminohydroxyanthraquinones, o-arylenediamines, anthranilic acid, 4 : 41-diamino-3 : 31-dicarboxydiphenyl, o-aminophenoxyacetic acid and their sulphonic or carboxylic acids.  Suitable aldehydes and ketones are salicyl aldehyde, mono-or dichlorsalicyl aldehydes, 2-hydroxy-1-naphthaldehyde, 1-hydroxy-2-naphthaldehyde, o-methoxybenzaldehyde, o-aminobenzaldehyde, 1-aminoanthraquinone-2-aldehyde, o-hydroxyacetophenone, o-aminoacetophenone, carbazole-o - hydroxyaldehydes, anthracene o-hydroxy aldehydes and their derivatives which may already be dyestuffs.  The products which are azomethines containing metal may be used for dyeing wool, silk, leather, cotton, acetate artificial silk or for colouring lacquers or artificial compositions.  In examples: (1) 4-sulphoanthranilic acid is boiled with chromium formate, sodium acetate and salicyl aldehyde in aqueous medium; 2-hydroxynaphthaldehyde, o-aminobenzaldehyde and o-hydroxyacetophenone may also be used; (2) similar to (1) using 2-aminoanisole-4-sulphonic acid and salicyl aldehyde; 5 - nitro - 2 - anisidine - 4-sulphonic acid or 1-amino-2-methoxynaphthalene - 6 - sulphonic acid and 1 - hydroxy - 2-aldehyde - 4 - methylbenzene - 6 - carboxylic acid or o-methoxybenzaldehyde may also be used; (3) 4 : 41 - diaminodiphenyl - 3 : 31 - dicarboxylic acid and 2-hydroxybenzaldehyde-5-sulphonic acid are condensed as in (1); 4 : 41-diaminodiphenylurea-3 : 31-dicarboxylic acid or 4 : 41-diaminodiphenylmethane - 3 : 31 - dicarboxylic acid and 1 - hydroxy - 2 - naphthaldehyde - 5-sulphonic acid are also specified; (4) 1 : 2 diaminobenzene and 1-hydroxy-2-naphthaldehyde-5-sulphonic acid are condensed as in (1); 1 : 2 - diaminobenzene - 4 - sulphonic acid, 4-nitro-1 : 2-diaminobenzene, 1 : 2-diaminonaphthalene, 1 : 2-diaminonaphthalene-5- sulphonic acid or 1 : 2-diaminoanthraquinone are also specified; (5) 2 - aminothiophenol and 2-hydroxybenzaldehyde - 5 - sulphonic acid are boiled in water and then with a solution of chromium oxide in formic acid; 1-hydroxy-2-naphthaldehyde-5-sulphonic acid may also be used; (6) the dyestuff aniline --> anthranilic acid and 2-hydroxybenzaldehyde-5-sulphonic acid are condensed as in (1); (7) o-hydroxybenzaldehyde, o-anisidine and zinc acetate are heated in ethanol; (8) the zinc salt of o-amino-thiophenol, 2-hydroxy-1-naphthaldehyde and zinc acetate are heated in methanol; (9) 2 - hydroxy - 1 - naphthaldehyde and 2 - aminodiphenylamine hydrochloride are condensed as in (8); (10) the azomethine compound from 2-hydroxy-1-naphthaldehyde and 1-aminocarbazole is heated with zinc acetate in methanol.