Patent GB-532708-A (GB)
Title: New disazo dyestuffs
IPC: C09B35/28
Filed: 1939-07-27
Abstract: 532,708. Dyes. CLIFFE, W. H., KERSHAW, A., KNIGHT, A. H., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. July 27, 1939, No. 21883. [Class 2 (iii)] Disazo dyes are obtained by coupling a tetrazotized di-(amino-N-substituted) anilide of a dicarboxylic acid of the benzene series with an arylpyrazolone (1 mol.) and with the same or a different arylpyrazolone or salicylic acid (1 mol.), the product containing at least one sulphonic acid group. The products dye wool and silk yellow shades, fast to washing, milling, perspiration, sulphur storing and light, from an acid bath or from a neutral bath, e.g. one containing ammonium acetate. The N-substituent may be alkyl with not more than 8 carbon atoms, phenylalkyl, cycloalkyl or phenyl and the various phenyl groups in the dyestuff may be substituted, e.g. by Cl. Br. CH 3  3 or OCH  3 . Specified pyrazolone components are the 1- phenyl-, 1-(21-chloro) phenyl-, 1-(4<SP>1</SP>-methyl) phenyl-, 1-(31- or 4<SP>1</SP>-sulpho)phenyl-, 1-(2<SP>1</SP>- chloro-5<SP>1</SP>-sulpbo)phenyl-, 1-(4<SP>1</SP>-chloro-2<SP>1</SP>-sulpho)phenyl-, 1-(2<SP>1</SP>:5<SP>1</SP>-dichloro-4<SP>1</SP>-sulpho)phenyl-, 1-(3<SP>1</SP>-carboxy)phenyl-, 1-(2<SP>1</SP>-methyl-5<SP>1</SP>- sulpho)phenyl-, 1-(2<SP>1</SP>-chloro-4<SP>1</SP>-methyl-5<SP>1</SP>-sulpho)phenyl-, 1-(2<SP>1</SP>-chloro-4<SP>1</SP>-methyl-5<SP>1</SP>-sulpho) phenyl-, 1-(6<SP>1</SP>-chloro-3<SP>1</SP>-methyl-4<SP>1</SP>-sulpho) phenyl-, 1-(41-methoxy- or ethoxy-2<SP>1</SP>-sulpho) phenyl- and 1-(4<SP>1</SP>-sulpho)naphthylderivatives of 3-methyl-5-pyrazolone and 1-(4<SP>1</SP>-sulpho) phenyl-5-pyrazolone-3-carboxylic acid and its alkyl esters. Specified di-carboxylic acids of the benzene series are phthalic, isophthalic, terephthalic, 4-chlorophthalic and 3:6-di-chloropbthalic acids. Examples are given of the production of the dyestuffs (1) and (2) terephthalicdi-(4-amino-2-N-benzyl-toluidide) <SP>#</SP> #  (1) 1- (4<SP>1</SP>-sulpho)phenyl-3-methyl-5-pyrazolone, (2) 1- (2<SP>1</SP>:5<SP>1</SP>-dichloro-4<SP>1</SP>-sulpho)phenyl-3-methyl-5- pyrazolone (2 mols.), (3) phthalic-di-(4-amino-2- N -benzyl-toluidide) <SP>#</SP> #  1-(2<SP>1</SP>:5<SP>1</SP>-dichloro-4<SP>1</SP>-sulpho)phenyl-3-methyl-5-pyrazolone (2 mols.) (4) and (5) terephthalic-di-(4-amino-1-N-ethyl-anilide) <SP>#</SP> #  1-(2<SP>1</SP>:5<SP>1</SP>-dichloro-4<SP>1</SP>-sulpho)phenyl-3- methyl-5-pyrazolone (1 mol.) and (4) 1-phenyl-3- methyl-5-pyrazolone or (5) salicylic acid (1 mol.). A table is also given showing the shades obtainable on wool with the dyestuffs from various components, additional tetrazo components being terepbthalic-di-(4-amino-1-N-n-butyl-anilide), phthalic-di-(4-amino-2-N-benzyl-anisidide), phthalic-di-(4-amino-1-N-ethyl or 1-N- phenyl-anilide), terephthalic-di-(4-amino-1-N- cyclohexyl-anilide), terephthalic-di-(4-amino- 2-N-ethyl-toluidide) and phtbalic-di-(4-amino- 2-N-ethyltoluidide). Di-anilides as above defined are obtained by reaction of the di-carboxylic acid chloride (1 mol.) with the appropriate nitro-N-alkyl-, phenylalkyl-, -cycloalkyl- or phenyl-amine, followed by reduction of the nitro group.