Dyeing properties of novel azo disperse dyes derived from phthalimide and color fastness on poly(lactic acid) fiber

The coloration of poly(lactic acid) (PLA) fiber with 18 carbocyclic monoazo disperse dyes bearing a hydrolyzable phthalimide ring fused to the aromatic ring of their diazo components has been investigated. The phthalimidyl nitrogen atom was substituted with either a n-butyl, sec-butyl, or isopropyl group, while the adjoining phenyl ring bore a substitution pattern typical of commercial colorants. There was a broad correlation between percentage dye exhaustion onto PLA and that onto polyester (PET) fiber, although significant differences in certain instances were apparent with no clear trends regarding dye structure. Attempts to explain the observed percentage exhaustion values by mapping them to calculated partition coefficient or solubility parameter values were unsuccessful. Wash fastness was relatively good compared to that of some conventional disperse dyes applied to PLA. As was found to be the case with PET, the wash fastness of dyes on PLA tended to be highest when their diazo ring was substituted with electron acceptors.