Self-immolative Polymers as a Degradable and Triggerable Class of Surfactants
Abstract
Self-immolative polymers (SIPs) are degradable polymers that undergo end-to-end depolymerization upon triggering. They have potential for the development of degradable surfactants addressing human and environmental toxicity concerns associated with non-degradable surfactants, but they have not yet been investigated as surfactants. Herein, polyglyoxylamide SIPs with different pendent groups and end-caps were synthesized, envisioning they could serve as depolymerizable analogues of poly(vinyl alcohol) and its derivatives. Polyglyoxylamides with pendent hydroxyls stabilized both PEA and PLA particle suspensions. They showed the potential to undergo triggered degradation, resulting in destabilization of the suspensions. However, untriggered suspensions exhibited poor long-term stability, so further structural tuning will be needed to optimize their properties for applications. Additionally, poly(ethylene glycol)-poly(ethyl glyoxylate) block copolymers were synthesized as potential emulsifiers of oil-in-water emulsions. Triggering depolymerization of the SIPs led to loss of emulsion stability, showing the promise of SIP block copolymers as a degradable and triggerable class of surfactants.