Patent GB-958899-A (GB)
Title: Azo and anthraquinone dyestuffs containing quaternary ammonium groups
Inventor: GAMLEN GEORGE ALBERT
IPC: C09B1/00
Filed: 1961-07-03
Abstract: N - [b  - (4 - aminophenylsulphonyl)ethyl] pyridinium chloride is prepared by refluxing 4-nitrophenyl b -chloroethylsulphone with pyridine in benzene and filtering N-[b -(4-nitrophenylsulphonyl)ethyl] pyridinium chloride from the cooled mixture. The nitro compound is dissolved in methanol and hydrogenated in the presence of Raney nickel.  The preparation of N-[b -(4-aminobenzylsulphonyl)ethyl] pyridinium chloride, N-[b -(4-aminobenzoylamino)ethyl] pyridinium chloride and N-[b -(4-aminobenzoyl-N-methylamino)ethyl] pyridinium chloride by similar methods is also specified.ALSO:The invention comprises water-soluble azo and anthraquinone dyes which contain at least one group of formula <FORM:0958899/C3/1> wherein A is a substituted or unsubstituted alkulene radical, n is 1 or 2, X is -SO2-, <FORM:0958899/C3/2> or -CONR, wherein R is a hydrogen atom or a substituted or unsubstituted alkyl radical and V1, V2 and V3 are hydrocarbon radicals and may be the same or different, or at least two of V1, V2 and V3 are joined or fused together, to form with the nitrogen atom N a heterocyclic ring or rings, wherein the nitrogen atom is linked to carbon atoms in the said ring or rings through either single bonds or a single bond and a double bond, provided that the dyes contain at least as many carboxylic acid and/or sulphonic acid groups as there are groups of the above formula.  The dyes are prepared by treating suitable water-soluble azo or anthraquinone dyes containing at least one group of formula <FORM:0958899/C3/3> wherein Y is a halogen atom or a sulphate ester group with a tertiary amine of formula <FORM:0958899/C3/4> Specified tertiary amines include trimethylamine, N,N - dimethyl - N - ethyl - or - alkylamine, pyrrolizidone, 1 - azabicyclo - (2 : 2 : 1)-heptane, quinuclidine, 1-isogranatamine, 1,5-diazobicyclo - (3 : 3 : 1) - nonane, julolidine, 1,4 - diazobicyclo - (2 : 2 : 2) - octane, methylpyridines, quinoline, ethyl nicotinate and preferably, pyridine.  Alternatively the azo dyes may be obtained by the usual coupling procedure using suitably substituted components. The dyes may be used to colour natural and artificial textile materials such as natural and regenerated cellulose, wool, silk, polyamides, polyacrylonitrile and aromatic polyester fibres. The dyes are particularly valuable as reactive dyes for cellulose fibres when used in conjunction with an acid-binding agent.  In examples: (1) the monoazo dye N-[b -(4-aminophenylsulphonyl)ethyl] - pyridinium chloride --> 1 - amino - 8 - naphthol - 3,6 - disulphonic acid is prepared; (3) 1,4-di-(41-phenylanilino)anthraquinone is treated with chlorosulphonic acid to form the tetrasulphonyl chloride which is reacted with 0.95 equivalents of b -chloroethylamine hydrochloride in the presence of sodium carbonate and finally quaternized with pyridine.  The preparation of further mono- and dis-azo, metallized azo and anthraquinone dyes is specified in examples.  The tri-potassium salt of 1-amino-4-[31-(b -sulphato - ethylsulphonyl)anilino] - anthraquinone-2,5-disulphonic acid is prepared by condensing 1 - amino - 4 - bromoanthraquinone-2,5-disulphonic acid with 3-(b -hydroxyethylsulphonyl)aniline, treating the product with 98% sulphuric acid and isolating the sulphate ester as the potassium salt.  Specifications 740,533, 796,330, 824,171, 845,567, 852,960, 868,492, 870,047, 882,750, 885,681, 887,137 and 913,517 are referred to.