Patent GB-901434-A (GB)
Title: Azo dyestuffs
Inventor: BARKER PETER WILLIAM
IPC: C09B62/006
Filed: 1959-03-04
Abstract: The invention comprises azo dyes which contain two or more reactive groups, at least two of the reactive groups being dissimilar. Reactive groups are groups which contain atoms or sub-groups which are capable of reacting with natural or artificial textile materials to produce chemical links. Dissimilar groups are reactive groups which have different heterocyclic nuclei or different non-homologous chains of non-metallic atoms each of which has a valency of 2. Indicated reactive groups are dihalo-triazinylamino and dihalo-pyrimidylamino, monohalo-pyrimidylamino, nitro-monohalo-pyrimidylamino, haloalkylamino, g -halo-b - hydroxypropylamino, haloalkoxy, epoxypropylamino, haloalkylaminosulphonyl, haloacyl, vinylsulphonylamino, vinylsulphonyl, haloethylsulphonyl, sulphato-b -hydroxyethylsulphonyl, thiocyano, N-(g -halo-b - hydroxy-propyl) aminocarbonyl, haloacylamino, alkyl- and aryl-sulphonyloxy-alkylsulphonyl, alkyl- and aryl-sulphonyloxy-alkylaminosulphonyl, alkyl- and aryl-sulphonyloxyalkylamino, alkyl- and aryl-sulphonyloxyalkoxy and alkyl- and aryl-sulphonyloxyalkylaminocarbonyl.  The halo atoms are chlorine or bromine.  The dyes may be made by conventional diazotisation and coupling processes or by treating a dye which has at least one reactive group and at least one hydroxy, mercapto, sulphinic acid, sulphamyl or primary or secondary amino group, with a compound of formula Hal Y, so that a different reactive group is formed.  Dyes which contain at least two alkyl- or aryl-sulphonyloxyalkyl groups linked to the dye molecule via different atoms or groups, or one is directly attached and the other via an atom or group, may be made by treating an azo dye containing at least two hydroxyalkyl groups with an alkyl- or aryl-sulphonhalide.  Indicated groups or atoms through which the hydroxyalkyl groups may be linked are O, S, NH, O-alkylene-O, SO2NH, SO2, NR1, CONH and CONR1, where R1 is a hydrocarbon group which may be substituted.  Dyes free from SO3H and COOH are water-insoluble and may be applied in a disperse state.  The water-insoluble dyes, which contain a dihalo-1,3,5-triazin-2-ylamino group, may be applied to polyamide, polyurethane, polyvinyl-alcohol or modified polyacrylonitrile textile materials as in Specification 825,912. The dyes colour natural and artificial textile materials such as cotton, viscose rayon, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitriles and modifications thereof, and aryl polyesters.  Water-soluble dyes are preferred for cellulosic materials especially when applied in conjunction with an acid-binding agent (see Specification 797,946).  The dyeings may be after-treated to improve their wash fastness.  Nitrogenous materials are coloured from a mildly alkaline, neutral or acid dyebath.  A preferred class are water-insoluble dyes free from SO3H or COOH groups and which are of formula A-N=N-B where A is an aryl residue and B is an aryl residue with an amino group o or p to the azo link indicated being dyes of formula P.C2H4HNO2S-A1-N= N-B1-N(R1)CH2CHOHCH2Q where A1 is a benzenic or naphthalenic residue, P and Q are Cl or Br, R1 is H or alkyl, which may be substituted, or CH2CHOHCH2Q and B1 is phenylene or naphthylene with the N(R) group o or p to N2.  A second preferred class of dyes are those of formula <FORM:0901434/IV (b)/1> where A is the residue of a water-soluble dye linked to the triazine via N, X is Cl or Br, n is 1-5, m 1 or 2, R1 is H or ZY, Z is a :b  lower alkylene and Y is a chlorine, sulphato, phosphato or acylated hydroxy group, indicative of values represented by A are aminoazobenzene, naphthylazoaniline, aminophenyl-azonaphthol, aminophenylazopyrazolone, their metal, e.g. Cu, Cr, Co and Ni complexes, and X-N=N-D-N=N-E-NH(Cn-1H2n-1) where D is a divalent aryl radical, X a coupling component residue and E NH(Cn-1H2n-1) a radical of a coupling component containing an amino or alkylamino group. Examples are provided of the preparation of the dyes and their use in colouring processes to yield a variety of colours.  Specifications 838,337, 842,933, 852,911 and 879,073 also are referred to.