The synthesis and spectroscopic properties of monoazo dye series, whose members consist of N‐alkylphthalimide diazo components combined with a coupling component containing two ester groups, are reported. Such colourants are potentially alkali‐clearable as a consequence not only of the presence of diester functionality on the coupler, but also through use of the base‐sensitive phthalimide system. Shortening the N‐alkyl group by removing one or two methylene units from a butyl chain made little difference to absorption properties, as would be expected given the relatively minor differences in inductive character produced. Shifts in the absorption maximum of the dyes associated with dibromination of the phthalimidylazo motif and its subsequent cyanodehalogenation were in agreement with theory and literature data for related series. Diester substitution on the coupling component brought about hypsochromism and hypochromism.

The coloration and fastness properties of 18 carbocyclic monoazo disperse dyes bearing a phthalimide ring fused to the aromatic ring of their diazo components have been investigated. In each case, the phthalimidyl nitrogen atom was substituted with either a butyl, sec‐butyl or isopropyl group, while the adjoined phenyl ring bore a substitution pattern typical of commercial colorants. Dye uptake and build‐up onto both conventional and microfibre polyester through exhaustion dyeing were examined: while the expected tendency of greater exhaustion on microfibre was noted, there were few clear trends with respect to dye structure. The nature of the N‐alkyl group made no consistent difference to dye uptake. Attempts to explain the observed percentage exhaustion values by mapping them to calculated partition coefficient or solubility parameter values were unsuccessful. Wash fastness tended to be best for blue dicyano‐substituted derivatives, which may be as a result in part of these substituents promoting hydrolysis of the adjacent phthalimide ring to give more soluble phthalate species. In contrast, the dicyano dyes had relatively poor photostability compared with their unsubstituted analogues.