Coloration properties and clearability of phthalimide-derived monoazo disperse dyes containing ester groups

The coloration properties and clearability of disperse dyes prepared from phthalimide-derived diazo components and a coupling component containing two carboxylic acid ester groups have been investigated. Members of the series featured C₂-C₄ alkyl substituents on their phthalimidyl nitrogen atom. The nature of the N-alkyl group made no consistent difference to dye uptake on polyester. No correlation was found between percentage exhaustion and calculated solubility parameters. Wash fastness was extremely good. Comparison with analogues indicated that the diester motif was of significant extra benefit to wash fastness for phthalimide-derived dyes, but did not increase photostability above the lower range of commercial acceptability. Clearability was compared with that of dyes lacking one or both hydrolysable structural features, as well as with that of some industrial dyes. The novel dyes exhibited a greater tendency to be solubilised, consistent with hydrolysis of their ester and/or phthalimide functionalities.