Synthesis of degradable and chemically recyclable polymers using 4,4-disubstituted five-membered cyclic ketene hemiacetal ester (CKHE) monomers

Abstract

Novel degradable and chemically recyclable polymers were synthesized using five-membered cyclic ketene hemiacetal ester (CKHE) monomers.

Diverse chemically recyclable polymers obtained by cationic vinyl and ring-opening polymerizations of the cyclic ketene acetal ester “dehydroaspirin”

“…Recently, Goto et al have reported the base degradation of a vinyl polymer of a CKAE to the monomer precursor. 32 Similarly, the base degradation of the vinyl polymer of MBDO was investigated. 10 M aqueous NaOH ([NaOH]/[MBDO units] = 3/1) was added to the solution of the vinyl polymer and the reaction mixture was heated at 70 °C.…”

Stimuli-cleavable moiety enabled vinyl polymer degradation and emerging applications

“…Furthermore, Goto's research team undertook the synthesis of novel CKHE monomers, DMDL and PHDL, which were subsequently co-polymerized with an array of diverse monomers (including vinyl, acrylate, styrene, and acrylonitrile). 56 These endeavors yielded a spectrum of polymer products, characterized by M n values spanning from 30 to 100 kDa (as elucidated in Fig. 13b).…”

Radical Ring Opening Polymerization of Cyclic Ketene Acetals Derived From d-Glucal

“…Building on previous studies surrounding the degradation of statistical copolymers between vinylic monomers and CKAs, ,− , the hydrolytic degradation of poly­( 1 - co -MMA) was investigated (Table ). Dissolved in THF, poly­( 1 - co -MMA) could be readily degraded via the addition of NaOH/KOH (1 mol L –1 in H 2 O or MeOH) at room temperature.…”