Synthesis of colorant-modified polystyrene copolymers with tailored structures for toner applications

Abstract

This article demonstrates an efficient method to combine nitroxide mediated radical polymerization (NMRP) with click chemistry for the synthesis of colorant modified polystyrene based functional copolymers. The chemistry involves (i) a living radical copolymerization of styrene (St)/butyl acrylate (BA)/4-chloromethylstyrene (CMS), (ii) a azide-functionalization of benzyl chloride of the copolymer P(St-BA-CMS), and (iii) an azide–alkyne click reaction between the azide-functionalized copolymer and the propargylized colorant molecule oil orange, by which the polymer structure and composition can be facilely controlled, and the material can be endowed with permanent color due to the covalent bonding between colorant and polymer. The ternary copolymerization was studied in detail and the functionalization efficiency was monitored through the whole transformation process using GPC, ¹H-NMR and FTIR as well as DSC. The polystyrene based copolymer exhibited absorption at 400–600 nm in UV-visible spectroscopy, confirming the high reactivity of the clickable moiety of the terpolymer and the effectiveness of azide–alkyne click reaction in constructing new polystyrene architecture.