Isosorbide-based Polymethacrylates
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Implication
Chemical synthesis study demonstrates controlled polymerization of bio-derived isosorbide methacrylates, highlighting viable routes to thermally stable and microphase-separated block copolymers.
Key Points
- To synthesize a novel bio-derived monomer from isosorbide and evaluate its free-radical and controlled reversible addition–fragmentation chain transfer (RAFT) polymerization behavior.
- Synthesized acetylated methacrylic isosorbide (AMI) via a two-step tandem esterification using a scandium(III) triflate catalyst with acetic anhydride and methacrylic anhydride.
- Polymerized AMI regioisomers via free-radical polymerization and RAFT polymerization utilizing a hydroxyethyl 4-cyano-4-(phenylcarbonothioylthio)pentanoate (HO-CPAD) chain transfer agent, followed by chain extension with n-butyl acrylate.
- Acetylation occurred preferentially at the endo hydroxyl group of isosorbide with an endo-acetate to exo-acetate ratio of 4.2:1.
- Radical polymerization yielded Poly(AMI) with a glass transition temperature (Tg) of approximately 130 °C and thermal decomposition (5% weight loss) at 251 °C under nitrogen and 217 °C in air.
- RAFT polymerization achieved narrow molar mass distributions (Đ ≤ 1.09), and subsequent chain extension produced PAMI-b-PnBA block copolymers (17–36 wt % PAMI) exhibiting microphase separation with dual Tg values at approximately −45 °C and +120 °C.
Cite This Study
Gallagher et al. (2015) studied this question.