Patent GB-824171-A (GB)
Title: New benzene monoazo-naphthylamine dyestuffs and their manufacture
IPC: C09B62/473
Filed: 1955-12-21
Abstract: Sulphones or sulphonamides of formula <FORM:0824171/IV (b)/1> where Z is an alkyl residue containing a halogen atom in the a - or o -position, and Y is a benzene residue or <FORM:0824171/IV (b)/2> where "aryl" is a benzene residue are made for use as diazo-components (see Group IV (c)), by acylating the corresponding diamine with a halide or an anhydride of an acid HOOC-Z.  Preferably sulphonamides are acylated with anhydrides and sulphones with acid chlorides.  Acylation is advantageously effected at - 10 DEG  to +10 DEG  C. at pH 3-6 with a small excess of acylating agent.  The reaction may be effected in an aqueous medium and/or in the presence of organic solvents.  Acid-binding agents may be present.  Specified acylating agents are chloracetyl and a - and b -chlorpropionyl chlorides and chlorand brom-propionic and chlor-acetic anhydrides. Groups specified for Y are methyl-, chloro- and methoxy-phenyl and N-ethylphenyl- and -methylchlorophenyl-amino groups.  Specified products are 2-amino-5-(a - and b -chloropropionylamino) - 41 - methoxy -, 2 - amino - 5 - chloracetylamino - and 2 - amino - 5 - chloracetylamino - 41 - methyl - 1,11 - diphenyl sulphones and 2-amino-5-chloracetylaminobenzene - 1 - sulphonic acid - N - ethylphenylamide.  Examples illustrate the preparation of 2-amino-5-chloracetylamino-41-methyl-1,11-diphenyl sulphone and 2-amino-5-chloracetylaminobenzene - 1 - sulphonic acid N-ethyl anilide and in addition to the above products 2 - amino - 5 - bromacetylamino and - b  - chlopropionylamino - 41 - methyl - 1,11 - diphenyl sulphones are described.  Specifications 341,397, [Group IV], and 632,699 are referred to.ALSO:The invention comprises dyestuffs of formula:  <FORM:0824171/IV(c)/1> where R is a 2-naphthylamine monosulphonic acid residue, in which the amino group in the 2-position is a primary or secondary one, bound in 1-position to the azo group, Y is a benzene residue or Aryl-N-Alkyl, where "Aryl" is a benzene residue, and Z is an p  alkyl residue containing a halogen atom in the a - or o -position. They are made by coupling in an acid medium appropriate diazobenzenes and naphthylamine sulphonic acids.  Specified coupling components are 2-naphthylamine-6-and -7-mono- and -3,6- and -5,7-disulphonic acids, 2-naphthylamine-3- and -5-oxy-7-, -7-oxy-4- and especially -8-oxy-6-sulphonic acids and 2 - methylamino - 8 - oxy - naphthalene - 6 - sulphonic acid. Groups specified for Y are methyl, chloro- and methoxy-phenyl and N-ethyl-phenylamino- and N-methyl-chlorophenylamino groups. Specified diazo components are 2-amino-5-(a - and b -chloropropionylamino) - 41 - methoxy -, 2 - amino - 5 - (chloracetylamino)- and especially 2-amino-5-(chloracetylamino) - 41 - methyl - 1,11 - diphenyl sulphones, and 2-amino-5-(chloracetylamino)-benzene-1-sulphonic acid-N-ethyl-phenylamide.  Diazotization is advantageously effected in the presence of wetting agents and solvents. Preferred dyestuffs are those of formula <FORM:0824171/IV(c)/2> where n is 1 or 2.  The dyestuffs dye materials of animal origin such as leather, silk and wool and synthetic fibres such as animalized artificial silk and superpoly-amides and -urethanes. Examples are provided of the preparation of the dyestuffs and their use in dyeing wool in bluish-red and orange shades, additional components used to certain of those already specified being 2-amino-5-bromacetyl- and -b -chloropropionyl-amino - 41 - methyl - 1,11 - diphenyl sulphones and 2 - N - ethylamino - 8 - oxynaphthalene - 6 - sulphonic acid. Specifications 341,397, [Group IV], and 632,699 are referred to.