Patent GB-786663-A (GB)
Title: Improvements in or relating to copperable disazo dyestuffs of the triazine series
IPC: C09B43/16
Filed: 1955-05-20
Abstract: The invention comprises copperable dyestuffs of formula <FORM:0786663/IV (b)/1> where X is Cl, OH or a primary, secondary or tertiary amino group, HOR1 is a residue of a phenol, the OH group being o to the -N=N-group, which contains as a nuclear substituent a lower alkylsulphonyl group or a sulphonic acid amide group which may be substituted on the N atom by lower alkyl, substituted lower alkyl, cycloalkyl, aryl-alkyl or mononuclear aryl groups, HO-R2 is a phenolic residue, the OH group being o to the -N=N- group and m and n are 1 or 2.  The term "lower" relates to groups with up to 6 carbon atoms.  They may be made either by condensing, preferably in an aqueous medium and in the presence of an acidbinding agent, 1 mol. of a six-membered triazine containing 3 replaceable chlorine atoms attached to C atoms with 2 mols. of a compound of formula <FORM:0786663/IV (b)/2> where n is 1 or 2 coupling in an alkaline medium, optionally in the presence of an organic tertiary base, at the 6-position of each naphthalene nucleus of the condensation product thus obtained 1 mol. of appropriate diazotized aminophenols, or by coupling in an alkaline medium appropriate diazotized aminophenols in the 6 position of the above naphthalene compounds and condensing the monoazo dyestuffs thus obtained with the substituted triazine. Mixed dyestuffs may be obtained by using a mixture of the two naphthalenic components instead of one of them.  Dyestuffs where n and/or m are 2 may also be made by coupling appropriate diazo compounds with a 2-(41-nitro)-benzoylamino-5-naphthol-7-sulphonic acid, reducing to the corresponding amine and condensing with the triazine.  The remaining C1 atom in the triazine ring of the above products may be replaced by OH or an appropriate amino group by treatment with an aqueous solution of an alkali metal hydroxide or carbonate, or with ammonia or a primary or secondary amine. Preferred are symmetrical dyestuffs where R1OH and R2OH are residues of 2-amino-4-methylsulphonyl-, -sulphonamido- and N-methylsulphonamido-phenol, X is phenylamino and m and n are 1. Other specified components corresponding to R1OH are 2-amino-4-ethylsulphonyl- and -5- and -6-sulphonamidophenol.  The R1OH components may contain substituents such as halogens and lower alkyl groups.  As N-substituted sulphonamides ethyl-, 21 - hydroxyethyl-, 31 - methoxypropyl-, cyclohexyl-, benzyl- and phenyl-amides are also mentioned.  Components corresponding to R2OH may contain substituents such as SO3H, NO2, lower alkyl, acylamino, alkylsulphonyl and sulphonamido groups which may be substituted on the N atom, and halogen atoms.  Cyanuric chloride is a specified triazine.  The dyestuffs in the form of their alkali metal salts dye cotton and regenerated cellulose in bluish red shades when coppered. Coppering may be effected by the single bath or after-coppering processes.  Examples are provided illustrating the preparation of the dyestuffs from certain of the reactants indicated above and their use in dyeing cotton and regenerated cellulose by aftercoppering processes, components used corresponding to R2OH additional to those already mentioned are 2 - amino - 4 - chloro-, -nitro-, -methyl- and -4,6-di-chloro-phenols, 2-amino-6-chloro-phenol-4-sulphonic acid and 2-amino-phenol-4-carboxylic acid phenylamide, the values of X when an amine residue being phenyl-, 4 - methoxy- and -methyl - phenyl-, cyclohexyl-, methyl- and hydroxyethyl-amino.