Development of a bio-based adhesive by polymerization of Boc-protected vinyl catechol derived from caffeic acid†

Abstract

Catechol is a functional group that is versatile and abundant in nature, exhibiting various functions. In this report, a tert-butoxycarbonyl (Boc)-protected vinyl catechol (VC) monomer was synthesized from caffeic acid, which is a bio-abundant molecule found generally in coffee beans, in order to develop a bio-based adhesive. Reversible addition–fragmentation chain transfer (RAFT) polymerization of the Boc-protected VC afforded well-defined, bio-based catechol-containing polymers with controlled molecular weights and narrow molecular weight distributions. Specifically, it was facile to deprotect the pendent Boc groups quantitatively under acidic or thermal conditions to provide the desired P(VC) without requiring further purification. Consequently, the catechol-containing polymer as a primer showed highly strong adhesion against aluminum when coupled with a commercially available polyurethane adhesive.