Addition–Fragmentation Ring‐Opening Polymerization of Bio‐Based Thiocarbonyl l‐Lactide for Dual Degradable Vinyl Copolymers

• Published in: Macromolecular rapid communications. Vol. 44; no. 2; pp. e2200537 - n/a
• Main Authors: Kamiki, Ryoya, Kubo, Tomohiro, Satoh, Kotaro
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 01.01.2023
• Subjects: Acrylates; Addition polymerization; Chain transfer; Chemical stimuli; Copolymerization; degradable polymer; Dioxanes; dual degradation; Fragmentation; lactide; Monomers; Polymerization; Polymers; Polymers - chemistry; radical copolymerization; Ring opening polymerization; Styrene; Sulfur; Vinyl copolymers; dual degradation; lactide; degradable polymer; radical copolymerization; ring-opening polymerization
• ISSN: 1022-1336; 1521-3927; 1521-3927
• DOI: 10.1002/marc.202200537

This study is designed to synthesize novel degradable polymers by radical addition–fragmentation ring‐opening copolymerization of bio‐based thiocarbonyl compounds with various vinyl monomers. Thiocarbonyl l‐lactide is capable of radical copolymerization with acrylates and styrene via radical addition to the carbon–sulfur double bonds followed by ring‐opening as well as controlled copolymerization in conjunction with the reversible addition–fragmentation chain transfer (RAFT) process. The obtained polymers possess ring‐opened thioester and ring‐retained thioacetal functionalities in the backbone, both of which could be cleaved under appropriate conditions with different chemical stimuli. Novel degradable vinyl polymer is attained by radical addition–fragmentation ring‐opening copolymerization of bio‐based thiocarbonyl l‐lactide, which could be copolymerized with acrylates and styrene as well as controlled reversible addition–fragmentation chain transfer (RAFT) copolymerization. The produced copolymers exhibit dual degradability by different chemical stimuli owing to the ring‐opened thioester and ring‐retained thioacetal functionalities in the backbone.