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Scalable synthesis of degradable copolymers containing α‑lipoic 2 acid via miniemulsion polymerization

Morris, Parker1; Watanabe, Kodai1; Albanese, Kaitlin1; Kent, Greggory2; Gupta, Rohini3; Gerst, Matthias4; Read de Alaniz, Javier1; Hawker, Craig1; Bates, Chris1

Published Nov 06, 2024 on Dryad. https://doi.org/10.5061/dryad.jh9w0vtmw

Data files

Nov 06, 2024 version files 8.90 MB

Abstract

A robust method is described to synthesize degradable copolymers under aqueous miniemulsion conditions using α-lipoic acid as a cheap and scalable building block. Simple formulations of α-lipoic acid (up to 10 mol%), n-butyl acrylate, surfactant, and costabilizer generate stable micelles in water with particle sizes <200 nm. The ready availability of these starting materials facilitated performing polymerization reactions at large scales (4 L), yielding 600 g of poly(n-butyl acrylate–stat–α-lipoic acid) latexes that degrade under reducing conditions (250 kg mol–1 → 8 kg mol–1). Substitution of α-lipoic acid with ethyl lipoate further improves the solubility of dithiolane in n-butyl acrylate, resulting in copolymers that degrade to even lower molecular weights after polymerization and reduction. In summary, this simple and scalable strategy provides access to large quantities of degradable copolymers and particles using cheap and commercially available starting materials.