Radical Copolymerization of Thionoglycolide and Derivatives for Preparation of Degradable Vinyl Polymers,Macromolecules

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Radical Copolymerization of Thionoglycolide and Derivatives for Preparation of Degradable Vinyl Polymers
Macromolecules ( IF 5.1 ) Pub Date : 2024-08-19 , DOI: 10.1021/acs.macromol.4c01259
Oleksandr Ivanchenko ₁ , Stéphane Mazières ₁ , Sonia Mallet-Ladeira ₂ , Simon Harrisson ₃ , Mathias Destarac ₁

Affiliation

This study explores the copolymerization behavior of thionated glycolide derivatives with a focus on thionoglycolide (TGD). It was found that TGD exhibits a nuanced reactivity profile, showing the highest compatibility with styrene and tert-butyl acrylate (tBA). Kinetic analysis of the TGD/tBA system conducted at 100 °C in bulk demonstrated comparable incorporation rates for both monomers. Furthermore, RAFT copolymerization mediated by a trithiocarbonate RAFT agent resulted in a well-defined copolymer with M_n = 13.4 kg mol^–1 and Đ = 1.2. 2D-NMR microstructural analysis revealed that TGD was exclusively incorporated in its ring-closed S,O-thioketal form, suggesting a selective 1,2-vinyl propagation mechanism. The degradability of the resulting copolymers was also investigated, with NaOCl, NaOMe, and benzoyl peroxide effectively cleaving S,O-thioketal linkages.

中文翻译：

硫代乙交酯及其衍生物的自由基共聚制备可降解乙烯基聚合物

本研究探讨了硫代乙交酯衍生物的共聚行为，重点是硫代乙交酯 (TGD)。研究发现，TGD 表现出微妙的反应性特征，与苯乙烯和丙烯酸叔丁酯 ( t BA) 具有最高的相容性。在 100 °C 下批量进行的 TGD/ t BA 系统动力学分析表明，两种单体的掺入率相当。此外，由三硫代碳酸酯 RAFT 试剂介导的 RAFT 共聚产生了结构明确的共聚物，其M _n = 13.4 kg mol ^–1和Đ = 1.2。 2D-NMR 微观结构分析表明，TGD 仅以其闭环 S,O-硫缩酮形式结合，表明选择性 1,2-乙烯基增长机制。还研究了所得共聚物的降解性，NaOCl、NaOMe 和过氧化苯甲酰可有效裂解 S,O-硫缩酮键。

更新日期：2024-08-19

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