Patent GB-462715-A (GB)
Title: Improvements in the manufacture and production of azo dyestuffs
IPC: C09B29/32
Filed: 1935-07-09
Abstract: Azo dyes; azo dyes, forming upon the material; printing.--Azo dyestuffs are manufactured by coupling diazo compounds of cyclic amines in substance or on the fibre with enolizable ketocarboxylic acid amides containing at least one radicle of a polynuclear aza compound having the aza nitrogen in a 6-membered ring and no other hetero atom besides nitrogen in the molecule, e.g. compounds of the types <FORM:0462715/IV/1> or <FORM:0462715/IV/2> where R is an alkyl or aryl group, R<1> is the radicle of an aza compound of the said kind and R<11> is an aromatic radicle, whilst when R, R<1> or R<11> is present more than once, the radicles must belong to the same class but need not be the same members of the class, and in which a hydrogen atom of the methylene groups or the imido groups or both may be replaced by an alkyl group.  In examples: (1) cotton yarn is impregnated with 9-(terephthaloyl-bis-acetyl)-amino-4-azaphenanthrene and a greenish yellow dyeing is developed with diazotized o-chloraniline, yellow dyeings with diazotized 5-trifluoromethyl-2-chloraniline, 2-aminodiphenyl sulphone or 1-amino-2-methoxy-5-sulphodiethylaminobenzene, or a golden orange with diazotized 4-chloro-2-nitraniline; if the coupling component is coupled in substance with diazotized metanilic acid, there is obtained a dyestuff which dyes silk and wool yellow shades; (2) cotton material is slop-padded with the coupling component of (1) and printed with a paste containing diazotized 1-methyl-2-amino-4-chlorobenzene, yielding a greenish yellow print; (3) cotton yarn is impregnated as in (1) and a greenish yellow dyeing is developed with diazotized 1-methyl-2-amino-4-chlorobenzene or a yellow with diazotized 1 - amino - 2 - methoxy - 5 -sulphodiethylaminobenzene; (4) cotton yarn is impregnated with 9-acetoacetylamino-4-azaphenanthrene and a greenish yellow dyeing is developed with diazotized o-chloraniline or a yellow with diazotized 1-amino-5-trifluoromethylphenyl-2-ethylsulphone.  There may similarly be used other amides, e.g. those from 6-, 7- or 8-amino-4-azaphenanthrenes, amino-1-, 8- and 9-azaphenanthrenes and amino-1 : 8-diazaphenanthrenes, with diazotized amines of the isocylic or heterocyclic series, e.g. amino derivatives of napthalene, triphenylene, anthrapyrimidines, diphenylene oxides or sulphides, benzothiazoles, pyrene, chrysene, benzperylene, diphenyl, dimethyldiphenyls, dimethoxydiphenyls, pyridine, quinoline, alkylazaphenanthrenes and azanthracenes.  A table gives the shades of further dyestuffs, the following additional components being specified: diazo components: 4-nitro-2-toluidine, 5-chloro-2-toluidine, 5-nitro-2 - amino - 1 - methoxybenzene, a -aminoanthraquinone, 4 - benzoylamino - 2 : 5 - dimethoxyaniline, p-nitraniline, 2 : 5-dichloraniline, and 4 - chloro - 3 - aminobenzotrifluoride; coupling components: 9- and 10-benzoylacetylamino-4-azaphenanthrene and 10 - terephthaloyl - bis-acetylamino-4-azaphenanthrene.  Specifications 361,097, 391,468, 404,794, 461,425, and 462,650 are referred to.  Samples have been furnished under Sect. 2 (5) of dyestuffs produced by coupling diazotized 1-amino-2-methyl-5-chlorobenzene in substance and on the fibre with: (A) the acid amide from benzoylacetic ester and amino-1-azacarbazole; (B) the acid amide from terephthaloyl-bis-acetic ester and 2-methyl-8-amino-1-azanaphthalene; (C) the acid amide from 6-quinoloylacetic ester and 1-aminonaphthalene; (D) the acid amide from terephthaloyl-bis-acetic ester and 3-amino-1-azanaphthalene.  The Provisional Specification comprises the use, as coupling components, of enolizable ketocarboxylic acid amides of aza-compounds in general.  The following additional types, in which R, R<1> and R<11> have the meanings given above, are specified: <FORM:0462715/IV/3> and <FORM:0462715/IV/4>