Patent GB-894012-A (GB)
Title: New monoazo dyestuffs
Inventor: HUNTER JAMES STUART
IPC: C09B29/033
Filed: 1959-03-04
Abstract: N - b  - cyanoethyl - N - b  - phenoxyethyl - m - toluidine, N - b  - cyanoethyl - N - (g  - phenoxy - b  - hydroxypropyl) - m - toluidine, N - b  - cyanoethyl - N - b  - (a  - naphthoxyethyl) - aniline and N - b  - cyanoethyl - N - b  - 21 : 41 - dichlorophenyxyethyl - aniline are prepared by refluxing N-b -phenoxyethyl - m - toluidine, N - (g - phenoxy - b  - hydroxypropyl) - m - toluidine, N - b  - (a  - naphthoxyethyl)-aniline or N-b -21 : 41-dichlorophenoxyethyl-aniline with acrylonitrile in the presence of glacial acetic acid for several days, followed by fractional distillation.  N - b  - acetoxyethyl - N - b  - phenoxyethyl - aniline is prepared by heating N-b -hydroxyethyl-N-b -phenoxyethyl-aniline with acetic anhydride and fractionally distilling the mixture.  N - b  - carboethoxyethyl - N - b  - phenoxyethyl - aniline is prepared by heating N-b -phenoxyethyl-aniline with a mixture of glacial acetic acid, ethyl acrylate and cuprous chloride and fractionally distilling the mixture.  N - b  - acetamidoethyl - N - b  - phenoxyethyl - aniline is obtained by heating N-b -phenoxyethyl-aniline with b -chloroethylacetamide and fractionally distilling the mixture.  N - b - carbonamidoethyl - N - b  - phenoxyethyl - m-toluidine is prepared by partial hydrolysis of N - b  - cyanoethyl - N - b  - phenoxyethyl - m - toluidine with hydrochloric acid.  N - b  - cyanoethyl - N - b - p - chlorophenoxy - ethyl-m-chloroaniline is prepared by heating a mixture of p-chlorophenoxyethyl bromide, chalk, water and N-b -cyanoethyl-m-chloroaniline extracting the product with benzene and fractionally distilling the dried benzene extract.ALSO:The invention comprises water-insoluble monoazo dyes, which are free from sulphonic and carboxylic acid groups, of formula <FORM:0894012/IV (c)/1> wherein D is a mono- or bi-cyclic radical of the aromatic series which carries at least one electronegative substituent (i.e. a substituent having a positive value for the Hammett substitution constant when in the para position), A is an alkylene or hydroxyalkylene radical of 2 or 3 carbon atoms, R is a benzene or naphthalene radical, W is a radical of formula -CN, -CONH2, -OC(O)X, -COOY or -NHC(O)X wherein X is hydrogen or a substituted or unsubstituted alkyl radical of not more than 5 carbon atoms and Y is the same as X but excluding hydrogen and the nucleus B may carry a substituent.  The dyes give yellow to blue shades on polyester, polyamide, cellulose and polyacrylonitrile fibres.  In examples the dyes are prepared by normal diazotisation and coupling methods the components specified being: 2-chloro- or -cyano- or -trifluoromethyl-4-nitroaniline, 2 - trifluoromethyl - 4 - cyanoaniline, 4 - amino - 3 - chlorobenzenesulphon - N - (b  - chloroethyl) - amide, 4 - methylsulphonyl- or -nitro-aniline, 4-amino-3-chlorobenzene sulphonamide, 2 : 4-bis (methylsulphonly) - aniline, 2 - amino - 5 - nitrothiazole and 2 - amino - 6 - methylsulphonyl - or - thiocyano - benzthiazole; N - b  - cyanoethyl - N - b  - phenoxyethyl - or g  - phenoxy - b  - hydroxypropyl - m - toluidine, N - b  - acetoxy - or - carboethoxy - or - acetamido - ethyl - N - b  - phenoxyethyl - aniline, N - b  - cyanoethyl - N - b - (a  - naththoxyethyl) - or - 21 : 41 - dichlorophenoxyethyl - aniline, N - b  - cyanoethyl - N - b  - p - chlorophenoxyethyl - m - chloroaniline and N - b  - carbonamidoethyl - N - b  - phenoxyethyl - m - toluidine.