GB952892A - New reactive anthraquinone dyestuffs - Google Patents

Abstract

The invention comprises anthraquinone dyes of formula <FORM:0952892/C3/1> wherein m is an integer, A and B may be the same or different and each represents a mono- or di-cyclic radical of the benzene series, at least one of A and B carrying a substituent of formula -N(R)Z, wherein R is a hydrogen atom or an alkyl radical having up to 4 carbon atoms and Z is a halogen-containing heterocyclic radical which contains 2 or 3 nitrogen atoms in the heterocyclic ring and the ring X in the anthraquinone nucleus may contain a hydroxy or sulphonic acid group. The dyes are prepared by reacting an anthraquinone dye of the above formula which contains in at least one of A and B an amino group of formula -NHR, with a heterocyclic compound having 2 or 3 nitrogen atoms in the ring and at least two halogen atoms in ortho positions to the nitrogen atoms. In a modified process the products wherein Z is a triazine residue containing 2 chlorine or bromine atoms are further reacted with an equimolar amount of ammonia, an organic mercaptan, hydroxyl or amino compound to replace one halogen atom by the corresponding group. Specified heterocyclic compounds include 2,4,6-tri-bromo- and -chloropyrimidines, 2,4,5,6-tetra-chloropyrimidine, 5-methyl- or -nitro- or -cyano-2,4,6-trichloropyrimidine, 2,4 - dichloro - 5 - nitro - pyrimidine or -6-methylpyrimidine, 2,4-dichloro-5-nitro- or -carboxy- or -carboethoxy-pyrimidine, cyanuric chloride or bromide and their primary condensation products with ammonia or mercapto-, hydroxyl- or amino compounds. The dyes may be used to colour wool, silk, polyamides and polyacrylonitrile fibres, but are preferably used to dye cellulose fibres in the presence of an acid-binding agent in green shades. Examples describe the preparation of the dyes. Trisodium 1 - anilino - 4 - [41 - (411 - aminophenyl)anilino] - anthraquinone trisulphonate is obtained by condensation of benzidine with 1 - anilino - 4 - hydroxy - anthraquinone in the presence of boric acid, followed by sulphonation with oleum; disodium 1,4-bis-(31-aminoanilino)-anthraquinone disulphonate and disodium 1-amino - 4 - (41 - aminoanilino) - anthraquinone disulphonate are similarly prepared. Specifications 822,047, 838,337, 842,933, 885,059, 885,547, 887,723 and 891,601 are referred to.