Patent GB-862269-A (GB)
Title: New azo dyestuffs
Inventor: BOOTH GERALD
IPC: C09B62/53
Filed: 1957-10-04
Abstract: 2 - Anisidine - 4 - N - (beta - chloroethyl) amide, 2 - amino - 5 - nitrobenzenesulphon - N - (betachloroethyl) amide and 2-naphthylamine-6-sulphon - N - (beta - chloroethyl) amide are made by reacting beta-chloroethylamine with p acetyl-2-anisidine-4-sulphochloride (prepared by heating acetyl-2-anisidine with chlorosulphonic acid), acetyl-2-anisidine with chlorosulphonic acid), 4 - nitroacetanilide - 2 - sulphonyl chloride (prepared by reacting 4-nitroacetanilide-2-sulphonic acid with a mixture of phosphorus oxychloride and phosphorus pentachloride) and 2-acetylaminonaphthalene-6-sulphonyl chloride respectively and hydrolysing the acetylated amino groups with hydrochloric acid.  3 - N:N - Diethylaminobenzenesulphon - N - (beta - chloroethyl) amide and 3 - (21 - chloroethyl) aminosulphonylbenzoylchloride are made by reacting beta-chloroethylamine with 3-N:N-diethylaminobenzenesulphonyl chloride (prepared by treating sodium diethyl metanilate with chlorsulphonic acid) and benzoic acid-3-sulphonyl chloride respectively.  2 - Naphthol - 6 - sulphon - N - (beta - chloroethyl) amide is made by reacting beta-chloroethylamine with 2-hydroxy-1-naphthoic acid 6-sulphonyl chloride and decarboxylating the amide formed with hydrochloric acid.  3 - Acetoacetylaminobenzenesulphon - N - beta-chloroethyl) amide is made by reacting diketene with 3-aminobenzene sulphon-N-(betachlorethyl) amide.  2 - Amino - 4 - trifluoromethylbenzenesulphonN-(beta-chloroethyl) amide is made by reacting 2 - nitro - 4 - trifluoromethylchlorobenzene with sodium disulphide, passing chlorine into the 2:21 - dinitro - 4:41 - di - (trifluoromethyl) diphenyldisulphide so obtained to give 2-nitro-4-trifluoromethylbenzenesulphonyl chloride and reacting the latter with beta-chloroethylamine to obtain 2-nitro-4-trifluoromethylbenzene-sulphon-N-(beta-chloroethyl) amide which is then reduced.ALSO:The invention comprises water-insoluble azo dyestuffs which are free from sulphonic acid, carboxylic acid and acylsulphonamide groups and which contain not more than one phenolic hydroxyl or enolizable carbonyl group and at least one group of the formula -SO2NRR1, each of which is directly attached to a different aryl nucleus present in the azo dyestuff, wherein R represents a chloro- or bromo-alkyl or chloroor bromo-cycloalkyl radical, R1 is hydrogen or a substituted or unsubstituted hydrocarbon radical or a chloro- or bromo-alkyl or chloro- or bromo-cycloalkyl radical or R and R1 are joined to form with the nitrogen atom a heterocyclic ring containing a chlorine or bromine atom.  The dyestuffs are made by diazotization and coupling or by converting the appropriate azo compound containing one or more sulphonic acid groups to the sulphonyl chloride and treating the latter with an amine of the formula HNRR1. Lists of aromatic amines, coupling components and azo compounds which may be used are given.  The dyestuffs of the invention include those of the formulae:-  <FORM:0862269/IV(c)/1> where B is a substituted or unsubstituted benzene or naphthalene nucleus, D is a substituted or unsubstituted amino group, X is a hydrogen or halogen atom and Y is chlorine or bromine, <FORM:0862269/IV(c)/2> where P is a substituted or unsubstituted aryl or heterocyclic nucleus, Y is chlorine or bromine and Z and Z1 are substituted or unsubstituted alkyl radicals and may be the same or different, and  <FORM:0862269/IV(c)/3> and <FORM:0862269/IV(c)/4> where Y is a chlorine or bromine atom and the benzene rings may be substituted.  Many examples are given.  The dyestuffs colour animal fibres such as wool, silk and regenerated protein fibres and artificial fibres such as cellulose ester fibres, polyamide, polyurethane, polyester, polyacrylonitrile and modified polyacrylonitrile fibres from aqueous dispersions by known methods. The dyestuffs may be used singly or in mixtures and may be applied to artificial textile materials in conjunction with a prior, simultaneous or subsequent treatment with an amine, phenol or thiophenol.  The dyestuffs may be formed on the textile material by treating the latter separately or simultaneously with aqueous solutions or dispersions of appropriate coupling components and of aromatic or heterocyclic amines in conjunction with nitrous acid. The dyestuffs may also be applied to textile materials in the form of printing pastes containing the usual thickeners and adjuvants.  In Examples (1) polyamide textile material, (92) silk and (93) modified polyacrylonitrile fibre are dyed with an aqueous dispersion of dyestuff followed by an alkaline treatment; and (94) a polyamide textile material and (95) a cellulose acetate rayon fibre are dyed by treatment with an amine and nitrous acid followed by a coupling component. Specification 548,903 is referred to.