Patent GB-706427-A (GB)
Title: New disazo dyestuffs
Inventor: KNIGHT ARTHUR HOWARD
IPC: C09B35/28
Filed: 1951-05-25
Abstract: N-substituted diaminobenzanilides of the general formula <FORM:0706427/IV (b)/1> (wherein R represents a b -phenoxyethyl group the phenyl group of which carries at least one substituent selected from halogen, alkyl of 1-6 carbon atoms and cycloalkyl, the primary amino groups are in meta- or paraposition to the -CO.NR- bridge, and the nuclei X and Y may carry a further substituent or substituents, e.g. an alkyl or alkoxy group) are prepared by condensing an appropriate m- or p-mononitro-N-(b -phenoxyethyl)-aniline with an appropriate mononitrobenzoyl halide and then reducing the nitro groups.  The products, of which many examples are listed, are intermediates for disazo dyestuffs (see Group IV (c)). Specifications 645,594 and 706,426 are referred to.ALSO:The invention comprises the manufacture of disazo dyestuffs by tetrazotizing N-substituted diaminobenzanilides of the general formula <FORM:0706427/IV(c)/1> (wherein R represents a b -phenoxyethyl group the phenyl group of which carries at least one substituent selected from halogen, alkyl of 1-6 carbon atoms and cycloalkyl, the primary amino groups are in meta- or para-position to the -CO.NR-bridge, and the nuclei X and Y may carry a further substituent or substituents, e.g. an alkyl or alkoxy radical) and coupling with two molecular proportions of one or more 1-phenyl-3-methyl-5-pyrazolone-monosulphonic acids, and the products so obtainable (which dye animal fibres such as wool and silk yellow shades from a neutral or weakly acid dyebath, e.g. one containing ammonium acetate).  Examples describe the production of the following dyestuffs: (1) 3 : 3\sv-diamino-1\sv-N-b -4"-chlorophenoxyethylbenzanilide \sQ 1 - (4\sv - sulphophenyl)-3-methyl-5-pyrazolone (2 mols); (2) 3 : 3\sv-diamino-6\sv-methyl-1\sv-N-b -2" : 4"-dichlorophenoxyethylbenzanilide \sQ 1 - (2\sv : 5\sv-dichloro-4\sv-sulphophenyl)-3-methyl-5-pyrazolone (2 mols); (3) 3 : 4-diamino-1\sv-N-b -2":4"-dichlorophenoxyethylbenzanilide \sQ the coupling component of (1); (4) and (5) the tetrazo component of (2) 2 mols of 1-(2\sv : 5\sv-dichloro-4\sv-sulphophenyl)- or 1-(3\sv- or 4\sv-sulphophenyl)-3-methyl-5-pyrazolone; (6) 3 : 3\sv-diamino-6\sv-methyl-1\sv-N-b -4"-tert. -butylphenoxyethylbenzanilide \sQ the coupling component of (2); (7) the coupling component of (2) \sM the tetrazo component of (2) --> the coupling component of (1); (8) the tetrazo component of (6) \sQ the coupling component of (1); (9) 3 : 3\sv-diamino-4 : 6\sv-dimethyl-1\sv-N-b -4"-chlorophenoxyethylbenzanilide \sQ 1-(2\sv-chloro-5\sv-sulphophenyl)-3-methyl-5-pyrazolone (2 mols); (10) 3 : 3\sv-diamino-6\sv-methyl-1\sv-N-b -4"-cyclohexylphenoxy ethylbenzanilide \sQ 1-(2\sv-chloro-4\sv-methyl-5\sv-sulphophenyl) -3-methyl-5-pyrazolone (2 mols); (11) 3 : 3\sv-diamino-4 : 6\sv-dimethyl-1\sv-N-b -2\sv : 4"-dichlorophenoxyethylbenzanilide \sQ 1 - (3\sv - sulphophenyl) - 3 - methyl-5-pyrazolone (2 mols); (12) 3 : 4\sv-diamino-1\sv-N-b -4"-cyclohexylphenoxyethylbenzanilide \sQ 1-(4\sv-chloro-2\sv-sulphophenyl) - 3 - methyl - 5 - pyrazolone (2 mols).  A table gives the properties of further dyestuffs, the following additional tetrazo components being specified: 3 : 4\sv-diamino-4-methyl-1\sv-N-b -4"-chloro- and -2"-methyl-phenoxyethylbenzanilide, 4:4\sv-and 3:4\sv-diamino-1\sv-N-b -4"-tert.-butylphenoxyethylbenzanilide, 3 : 3\sv-diamino-1\sv-N-b -2": 4"-dichlorophenoxyethylbenzanilide, 4 : 3\sv-diamino-6\sv - methoxy-1\sv-N-b -4"-chlorophenoxyethylbenzanilide and 4 : 4\sv-diamino-1\sv-N-b -4"-chlorophenoxyethylbenzanilide.  Lists of still further tetrazo components and further coupling components are given.  Specifications 645,594 and 706,426, [Group IV(b)], are referred to.