Patent GB-993162-A (GB)
Title: New water-insoluble monoazo dyestuffs
Inventor: BARKER PETER WILLIAM
IPC: C09B62/45
Filed: 1962-04-17
Abstract: m - Acrylamido - N:N - bis (b  - benzoyloxy ethyl) aniline is prepared by reacting acryloyl chloride with m-amino-N:N-bis(b -benzoyloxy-ethyl) aniline.  m - Acrylamido - N:N - bis-(b :g  - di - acryloyloxypropyl) aniline is prepared by reacting acryloyl chloride with the corresponding m-amino bis-(dihydroxy propyl) compound.  m - (b  - Acetoxypropionylamido) - N:N - bis-(b -acetoxyethyl) aniline is prepared by reacting b -acetoxypropionyl chloride and the corresponding m-amino compound.  m-Acetoacetamido - N:N - bis (b  - acetoxyethyl) aniline is prepared by reacting diketene with the corresponding m-amino compound.  m - [di - (ethoxycarbonyl) methyl carbonamido] N:N - bis - (b  - acetoxyethyl) aniline is obtained by reacting sodio malonic ester with the corresponding substituted phenylisocyanate.  m - Cyclohexyloxycarbonamido - N:N - bis-(b -acetoxy ethyl) aniline is prepared by reacting cyclohexanol with the corresponding substituted phenyl isocyanate.  m - b  - Ethoxyethoxycarbonamido - N:N - bis-(b  - phenyl carbamyloxyethyl) aniline is prepared by the reaction of phenyl isocyanate with 3-nitro-N:N-bis (b -hydroxyethyl) aniline, reduction of the nitro group to amino followed by phosgenation of the amino group to give the isocyanate which is then reacted with the monoethyl ether of ethylene glycol.  m - (Toluene sulphonamido) - N:N - bis (b -acetoxyethyl) aniline is obtained by reacting p-toluene sulphonyl chloride and the corresponding substituted aniline.ALSO:The invention comprises the water-insoluble monoazo dyestuffs which are devoid of sulphonic and carboxylic acid groups and are of the formula <FORM:0993162/C4-C5/1> wherein D represents the radical of a diazo component of the benzene, naphthalene or heterocylic series provided that D is not the 4 - cyano - 2 - trifluoromethyl radical; Y is hydrogen or a chlorine or bromine atom or an alkyl or alkoxy radical of not more than 4 carbon atoms; A is -CO-, -CO.O- or -SO2-; R represents a cyclohexyl radical, a substituted or unsubstituted lower alkenyl radical, an acyloxy lower alkyl radical, an alkoxycarbonyl lower alkyl radical, an acyl lower alkyl radical, an alkylsulphonyl lower alkyl radical a cyano-lower alkyl radical, or a radical of the benzene series; R1 and R2 each represent lower alkyl radical of at least 2 carbon atoms, each of R1 and R2 being substituted by at least one acyloxy radical; and the term "lower" indicates that the total number of carbon atoms in the radical is not greater than 8.  The dyes are prepared by conventional diazotization and coupling procedures or by acylating compounds of formula similar to that given above in which R1 and R2 are replaced by R3 and R4 which each represent lower alkyl radicals of at least 2 carbon atoms each of R3 and R4 being substituted by at least one hydroxyl radical by treatment with a functional derivative of an organic acid.  In examples: p-nitroaniline is diazotized and coupled -with N: N - bis - (b  - acetoxyethyl) - m - acryloyl amino aniline (1); 2-amino-6-methylsulphonyl-benzothiazole is diazotized and coupled with m-(b  - acetoxypropionamido) - N:N - bis - (b -acetoxyethyl) aniline (4); and 2-amino-5-nitrothiazole is diazotized and coupled with m [di - (ethoxycarbonyl) methyl - carbonamido]- N:N - bis - (b - acetoxyethyl) aniline (14). Many additional examples are furnished and starting materials listed. The dyes are employed for dyeing fibres of secondary cellulose acetate, polyamides such as polyhexamethylene adipamide, polycaprolactam and polyesters such as polyethyleneterephthalate. The dyes are preferably employed as fine dispersions in water.