Patent GB-774819-A (GB)
Title: New monoazo-dyestuffs and process for making them
IPC: C09B62/45
Filed: 1954-12-28
Abstract: The invention comprises monoazo dyestuffs which contain an acid group imparting solubility in water but contain no N-acylated sulphonamide groups, and also contain a group of formula <FORM:0774819/IV(b)/1> where R is an alkylene residue, Z is the residue of an organic sulphonic acid bound through an oxygen atom of its functional group to R, and n is 1 or 2.  They are made by normal processes selecting the components so as to obtain the appropriate groupings in the products.  Z is advantageously present in the g - or preferably b -position of R which is bound to -SO2- in a -position either through the -NH- group or directly. Particularly preferred are dyestuffs containing the groups -SO-2-(NH)n-1-(CH2)m-O-SO2-Z where n is 1 or 2, m is 2 or 3 and Z is an aliphatic or aromatic residue and equally those of formula <FORM:0774819/IV(b)/2> where Pz is a 5-pyrazolone sulphonic acid residue bound in the 4-position to Nz, R and Z are benzene residues free of SO3H7 COOH and OH groups and n is 1 or 2. Indicated as acid groups are -SO2NH2, sulphone groups e.g. MeSO2-, COOH and preferably SO3H.  Preferably the group of formula (1) is in the diazo component, and the acid group in the coupling component. Substituents such as halogen atoms and nitro, acylamino, alkyl and alkoxy groups may also be present in the dyestuff components but advantageously the diazo compounds should not contain an OH group o to the N2 group.  Specified components containing a group of formula (3) are as azo components:-aniline-4-sulphonic acid-b -(ethanesulphonyloxy)-ethylamide and -g -(benzensulphonyloxy)- and -b -(p-toluene sulphonyloxy)-propylamides. aniline-3- and -4- sulphonic acid -b - (benzene- and p-toluene-sulphonyloxy) -ethylamides, aniline -3- sulphonic acid -N-methyl -N- and 4-methyl aniline -3- sulphonic acid -b - (p-toluene-sulphonyloxy)-ethylamides, 2, 5-dichloro-aniline-4-sulphonic acid- and 4-methylaniline -3- sulphonic acid -b - (benzenesulphonyloxy) -ethy-lamides and 2-methoxyaniline -5- and aniline -2-, -3- and -4- sulphonic acid -b -(p-toluenesulphonyloxy)- ethyl sulphones and as coupling components:-2-naphthylamine-6-, 1-naphthol -4- and -5-, 2-naphthol -6- and 1-phenyl -3- methyl -5- pyrazolone -21-, -31- and 41- sulphonic acid -b - (benzenesulphonyloxy)-ethylamides, 2-naphthol -6- -b - (benzenesulphonyloxy)- and 1-phenyl -3- methyl -5- pyrazolone -31- b -(p-toluene-sulphonyloxy)-ethyl sulphones, 1-phenyl -3- methyl -5- pyrazolone -31-sulphonic acid -g - (benzenesulphonyloxy)-propylamide and 1-phenyl -3- methyl -5-pyrazolone -31- b -(p-toluenesulphonyloxy)-ethylamide.  Specified components containing the acid group are as azo components:-aniline -3- and -4- sulphonamides, -2-3- and -4- methyl sulphones and sulphonic acids, 2-methyl- and -methoxy-aniline -4-and 5-sulphonic acids and 2-naphthylamine -6- sulphonic acid and as coupling components:- 1-naphthol -4- and -5- sulphonic acids, 2-naphthol -3-, -4-, -5- -6-, -7- and -8- sulphonic acids, 2, 8-dioxynaphthalene-1 2-naphthylamine- and 2-amino-8-naphthol -6- sulphonic acid.  1- phenyl -5-pyrazolone -3- carboxylic acid, 1-phenyl -3-methyl -5- pyrazolone -21-, -31- and -41-sulphonic acid and 1-(21, 51-dichlorophenyl) -3- methyl -5- pyrazolone -41 sulphonic acid.  The dyestuffs dye nitrogenous fibres such as leather, silk, wool, superpolyamides and superpolyurethanes from a weak acid or neutral bath.  In examples illustrating the preparation of the dyestuffs and their use in dyeing wool in yellow shades components used in addition to certain of those specified above are as azo components aniline -4-b -(p-toluenesulphonyloxy)- ethyl sulphone, 2-methoxyaniline -5- sulphonic acid -N-b -(p-toluene- and ethane-sulphonyloxy) ethyl- and -N-g -(ethanesulphonyl-oxy)-propyl-amides and as a coupling component, 2-naphthylamine -6-b -(p-toluene-sulphonyloxy)-ethylamide.