Patent GB-959816-A (GB)
Title: Process for the coloration of aromatic polyester textile materials and monoazo dyestuffs used therein
Inventor: BERRIE ALISTAIR HOWARD
IPC: C09B31/147
Filed: 1961-08-28
Abstract: The invention comprises the monoazo dyes of formula <FORM:0959816/C3/1> wherein X is a halogen atom or a lower carboalkoxy or carbo-(substituted alkoxy) radical, Y is a hydrogen or halogen atom, Z is a hydrogen atom or a lower alkoxy or substituted alkoxy radical and the term "lower" indicates a radical of not more than 5 carbon atoms. The preparation of dyes of formula <FORM:0959816/C3/2> wherein A is an aromatic radical of the carbocyclic or heterocyclic series, R1 is hydrogen or a substituted or unsubstituted alkyl, aralkyl or aryl radical, and R2 and R3 may independently be hydrogen or substituted or unsubstituted alkyl, aralkyl or aryl radicals or may together represent the atoms necessary to form with the adjacent nitrogen atom, a heterocyclic ring, provided that the dye is free of sulphonic acid and acylsulphonamide groups and salts thereof and provided also that R2 and R3 are not both hydrogen when A and R1 are both phenyl or substituted phenyl radicals, which are used in dyeing polyester materials in yellow and orange shades (see Division D1) is also described.  The dyes are prepared by coupling a diazotized aromatic amine with a coupling component of formula <FORM:0959816/C3/3> Specified amines include 2-methoxy-4-nitroaniline, 1- and 2-naphthylamine, methyl p-aminobenzoate, mono- and di-chloroanilines, 2 - aminobenzonitrile, 2 - amino - 6 - thiocyanobenzothiazole, 4 - aminoazobenzene, 2-amino - 5 - nitro - thiazole, 2 - aminobenzoic acid, diethylamide, 4 - aminophenyl - methylsulphone, 4 - aminobenzenesulphonamide and 2 - naphthylamine - 6 - diethylsulphonamide. Many dyes are specified in examples.ALSO:Aromatic polyester textile materials are coloured in yellow and orange shades by applying thereto a water-insoluble dye of formula :-  <FORM:0959816/D1-D2/1> wherein A is an aromatic radical of the carbocyclic or heterocyclic series, R1 is hydrogen or a substituted or unsubstituted alkyl, aralkyl or aryl radical, and R2 and R3 may independently be hydrogen or substituted or unsubstituted alkyl, aryl or aralkyl radicals or may together with the adjacent nitrogen atom form a heterocyclic ring, provided that the dye is free of sulphonic acid and acylated sulphonamide groups and salts thereof and provided also that R2 and R3 are not both hydrogen when A and R1 are both phenyl or substituted phenyl radicals.  The aromatic polyester materials are dyed in the customary manner in the presence of the usual adjuvants.  In examples: (1) 3-carbamoyl-4-(21-methoxy-41-nitrophenylazo) -5-pyrazolone is milled in the presence of water and the sodium salt of a formaldehyde-naphthalene sulphonic acid condensate, the dispersion is added to water containing oleyl sodium sulphate, polyethylene terephthalate is placed in the bath which is heated in a closed vessel and dyed polyester is rinsed in an aqueous alkaline solution of sodium hydrosulphite and cetyl trimethylammonium bromide; (117) a padding liquor is prepared by milling 1-phenyl-3-N-(41-methoxyphenyl) -carbamoyl-4-(211-chlorophenylazo)-5-pyrazolone in water containing the sodium salt of a formaldehyde-naphthalene sulphonic acid condensate and an octylphenolethylene oxide condensate and mixing the resultant dispersion with sodium alginate, padding polyethylene terephthalate fabric with this liquor, drying the fabric and heating at 200 DEG C. for 2 minutes and finally rinsing as in (1).