Patent GB-993259-A (GB)
Title: New azo dyestuffs
Inventor: HICKMOTT PETER WILLIAM
IPC: C09B/
Filed: 1962-03-08
Abstract: 2 - Hydroxy - 3 - naptho - N - (41 - dodecylphenyl) amide is obtained by reacting 2-hydroxy-3-naphthoic acid with 4-dodecyl aniline in toluene in the presence of phosphorus oxychloride. Additional amides are prepared by reacting 2 - (21 - methyl - phenoxy) -, 4 - (benzyloxy) - and 3 - (41 - methylphenylsulphonylamino) aniline instead of 4-dodecyl aniline in similar processes.  3 - [N - (b  - (41 - methylphenoxy)ethyl) - N - methylsulphamyl] - aniline is obtained by reacting m-nitrobenzene sulphochloride with N - [b  - (41 - methylphenoxy)ethyl] - N - methylamine and reducing the nitro group to an amino' group.  4 - [N - (b  - (41 - chlorophenoxy)ethyl) - N - ethylsulphamyl] aniline is obtained by reacting p-acetylamino benzene sulphochloride with N - [b  - (4 - chlorophenoxy)ethyl] - N - ethylamine and hydrolysing the acetylamino group to an amino group. 5 - [N - b  - phenylethyl - N - phenylsulphamyl] - 2 - methoxy aniline is obtained by reacting 3-acetylamino-4-methoxy benzene sulphochloride with N - b  - phenyl - ethyl - N - phenylamine and hydrolysing the acetylamino group to an amino group.  Specifications 858,183, 862,318 and 885,814 are referred to.ALSO:The invention comprises azo dyes which are represented by the formula <FORM:0993259/C4-C5/1> wherein one of the symbols V represents a group of the formula <FORM:0993259/C4-C5/2> and the other symbol V represents a group of the formula -X2-(A-X1)m-Q, wherein Y1, Y2 and Y3 each independently represent a hydrogen, chlorine or bromine atom, R represents a hydrogen atom or an alkyl radical containing from 1 to 5 carbon atoms, X1 and X2 each independently represent a direct link or a -O-, -S-, <FORM:0993259/C4-C5/3> group, A represents a divalent aliphatic or aromatic radical, m represents 0 or 1, Q represents an aliphatic, cycloaliphatic or aromatic radical containing 5 or more carbon atoms, R1 represents a hydrogen atom, or an alkyl, aralkyl or aryl, E represents the residue of a coupling component, Z represents a hydrogen atom, or a chlorine or bromine atom or a nitro, cyano, trifluoromethyl, methyl, methoxy, sulphonic acid, carboxylic acid, -SO2NR2R2 or -CONR2R2 group, wherein R2 represents an alkyl radical containing from 1 to 5 carbon atoms, provided that the dyestuffs contain at least one sulphonic or carboxylic acid group. The dyes are prepared by conventional diazotization and coupling and acylation procedures. E is preferably the residue of a coupling component which couples in ortho or vicinal position to an hydroxy or enolizable keto group and especially of the acylacetarylamide, naphthol or 1 - aryl - 5 - pyrazolone series.  In examples: 4 - dodecylaniline - 2 - sulphonic acid is diazotized and coupled with 2-acryloylamino-5-naphthol-7-sulphonic acid to obtain an orange dye (1) and the trisodium salt of 7-(41-dodecyl-21 - sulphophenylazo) - 1 - amino - 8 - naphthol-3: 6-disulphonic acid is reacted with acryloyl chloride to obtain a red dye (37). Many additional examples are furnished and starting materials listed.  The dyes are suitable for dyeing cellulose textile materials and nitrogen containing textile materials e.g. polyamides and in particular wool.  Specifications 858,183, 862,318 and 885,814 are referred to.