Synthesis and characterization of quaternized poly-alkyl α-chloroacetoxymethacrylates

Summary

The homopolymers of ethyl α-chloroacetoxymethacrylate (ECAM) and t-butyl α-chloroacetoxymethacrylate (TBCAM) were quaternized homogeneously with trimethylamine (TMA) and N,N-dimethyldodecylamine in N,N-dimethylformamide (DMF). The ¹H-NMR measurments were used for the determination of the degree of quaternization (DQ) values. The DQ value of poly-ECAM quaternized with TMA at room temperature after 1 h was found to be 84 %, while the DQ value for poly-ECAM quaternized with N,N-dimethyldodecylamine was 37 %. Reactivity of poly-TBCAM was lower than that of poly-ECAM. The lower DQ value of TMA quaternized poly-TBCAM (19 %) is caused by steric hindrance in the vicinity of - CH₂Cl group due to bulky t-butyl group. Increasing reaction time, polymer concentration and temperature above a certain value for each polymer, resulted in crosslinked polymers. Solubility of the quaternized polymers is controlled by the substituents. Thermogravimetric analysis showed distinct differences in thermal stabilities which is controlled by the quaternary amine groups and ester substituents.