Using dilatometry in the reversible addition fragmentation transfer polymerization of N-(S)-(−)-α-methylbenzyl methacryloylamine

• Published in: Journal of polymer research 2011-11, Vol.18 (6), p.1821-1827
• Main Authors: Soriano-Moro, J. Guillermo, Percino, M. Judith, Chapela, Víctor M., Guerrero-Santos, Ramiro
• Format: Article
• Language: English
• Subjects: Addition polymerization; Chain transfer; Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Dilatometry; Ethanol; Ethyl alcohol; Industrial Chemistry/Chemical Engineering; Optical activity; Original Paper; Polymer Sciences; Polymerization; Rafts
• ISSN: 1022-9760; 1572-8935
• DOI: 10.1007/s10965-011-9589-3

Optically active polymers were prepared using reversible addition-fragmentation chain transfer polymerization (RAFT) of N-(S)-α-methylbenzylmethacryloylamine (N-(S)-α-MBMA), a functional optically active monomer. RAFT polymerizations were carried out at 70 °C in ethanol using AIBN as a thermal initiator and benzyl or (1-phenyl)ethyl dithiobenzoate (BDB and PEDB, respectively) as the RAFT agents. The kinetic study was performed by dilatometry. Plots of conversion vs time indicated that the polymerizations followed first order kinetics. 1 H NMR, IR, and UV–vis spectrophotometric studies confirmed the presence of thiocarbonylthio moieties (−SCS-) in the polymer chains. The molecular weight distributions (MWDs) were moderately narrow with polydispersity indices between 1.3 and 1.6, which indicated that the control of the reaction was not completely achievement using BDB or PEDB as RAFT agents. The optical activity [α] D 25 measurements of synthesized polymers by RAFT did not show a noticeably linear increase dependence with respect to molecular weight, as was previously reported for another controlled free radical polymerization (CRP) system.