Patent GB-740862-A (GB)
Title: Improvements relating to monoazo dyestuffs and their use
IPC: C09B29/30
Filed: 1953-10-15
Abstract: Amines, used as diazo components in the preparation of azo dyes (see Group IV (c)), of general formula <FORM:0740862/IV(a)/1> where X represents hydrogen, chlorine, a methyl, methoxy or sulphonic acid group, Y represents hydrogen or a methyl group, and n1 and n2 represent 0 or 1, are prepared from 5 - amino - 2 - hydroxybenzene - 1 - carboxylic acids which may be substituted in the 3-position as defined, by reaction with p-nitrobenzoyl chloride or p-nitrophenyl isocyanate, reducing the nitro group to the amino group, again reacting with p-nitrobenzoyl chloride or p-nitrophenylisocyanate and reducing the nitro group to the amino group.  The acylating agents may contain methyl group ortho- or metato the nitro group.  Several compounds corresponding to the general formula are specified.ALSO:The invention comprises monoazo dye stuffs corresponding to the general formula: <FORM:0740862/IV(c)/1> wherein X represents hydrogen, chlorine, a methyl, methoxy or sulphonic acid group, Y represents hydrogen or a methyl group, n1 and n2 are 0 or 1, and A represents the radical of a 2-(31- or 41-aminobenzoylamino) - 5 - hydroxynapthalene-7-sulphonic acid or a 2-[31 or41- (311-or 411-aminobenzoylamino)-benzoylamino] -5-hydroxynapthalene-7-sulphonic acid or a derivative thereof in which the -N-C-bridging members, between the benzene and napthalene nucleus, are members of a thiazole or imidazole ring fused to the napthalene ring in the 1:2- positions, the benzene nuclei of A containing, if desired, further substituents, preferably non-ionogenic (i.e. which do not form salts).  The dyestuffs are prepared by diazotising the corresponding amine (see Group IV(b)) and coupling with component A.  The dyestuffs may be used as direct cellulose dyestuffs and dye in red shades but are preferably diazotized on the fibre and developed with coupling components not containing sulphonic acid groups.  Unsulphonated phenolic and enolic azo components are suitable developers, but naphthols coupling ortho to the hydroxy group are preferred, particularly 2-naphthol which yields red shades.  As diazo components, 5-[41-(411 -aminobenzoylamino)-benzoylamino] -, 5-[41-(311-methyl-411 - aminobenzoylamino)-benzoylamino]-, 5-[41-(311-methyl-411-aminobenzoylamino) -31 - methylbenzoylamino]-, 5-[41- (411-aminobenzoylamino)-31 methylbenzoylamino]-, 5-[41-(211:511-dimethyl-411 -aminobenthoylamino) - benzoylamino]-, 5-[41-(211-methyl-411 - aminobenzoylamino)-benzoylamino]-, 5-[41-(411-aminobenzoylamino)-21 -methylbenzoylamino]- and 5-[41 -(411-aminophenylureido) - benzoylamino]-2-hydroxybenzene -1-carboxylic acid, 5-[41 -(311-methyl-411-aminobenzoylamino) - benzoylamino]- and 5-[41-(411-aminobenzoylamino) - benzoylamino]-3-sulpho-2-hydroxy-benzene-1-carboxylic acid, 5-[41-(411 aminobenzoylamino)-benzoylamino] -3-methyl-, 5-[41 - (411-aminobenzoylamino) - benzoyl - amino]-3-chloro- and 5-[41-(411-aminobenzoylamino) - benzoylamino]-3-methoxy-2-hydroxybenzene-1-carboxylic acid, 41-(411-aminophenylureido)- and 41(311-methyl-411-aminobenzoylamino) - 3 - carboxy - 4 - hydroxydiphenylurea, and 41-(311-methyl-411 aminobenzoylamino)-5-sulpho - 3 - carboxy-4-hydroxydiphenyl urea are specified.  As azo components, 2-(41-aminobenzoylamino)-, 2-(31-aminobenzoylamino)-, 2-(41-methyl-31 -aminobenzoylamino)-, 2-(41-methoxy-31 -aminobenzoylamino)-, 2-(31-methyl-41 -aminobenzoylamino)-, 2-(41-chloro-31 -aminobenzoylamino)-, 2-[31 or 41-(411 -aminobenzoylamino) - benzoylamino]-, 2-[41-(411-amino-311-methyl-benzoylamino)] -2-[31-(411-aminobenzoylamino)-41 - methylbenzoylamino]- and 2-[41-(311-amino-411-methyl-benzoylamino) -benzoylamino]-, 5-hydroxynapthalene-7-sulphonic acid, 2-(411 or 311-aminophenyl)- and 2-[411- or 311- (4111- or 3111-aminobenzoylamino)-phenyl]-naphtho - 11.21:4.5-imidazole-51-hydroxy-71 -sulphonic acid, 2-(411 or 311-aminophenyl)-, and 2-[411- or 311- (4111- or 3111 -aminobenzoylamino)-phenyl]- naphtho-11.21 :4.5 -thiazole-51-hydroxy-71-sulphonic acid are specified. Examples describe the preparation of monoazo-dyes using the components described above and also the diazotization of the dyes on the fibres and development with 2-naphthol.