Backbone-Degradable Acrylate Latex: Toward Overcoming Hydrolysis Limitations of Cyclic Ketene Acetal Monomers,Macromolecules

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Backbone-Degradable Acrylate Latex: Toward Overcoming Hydrolysis Limitations of Cyclic Ketene Acetal Monomers
Macromolecules ( IF 5.1 ) Pub Date : 2024-03-15 , DOI: 10.1021/acs.macromol.3c02474
Srinivasa Reddy Mothe ₁ , Wenguang Zhao ₁ , Alexander M. van Herk ₂ , Praveen Thoniyot _{1,

3}

Affiliation

Latex particles made with radical emulsion polymerization contain all carbon-backbone polymer chains, which are nonhydrolyzable and nonbiodegradable in the environment and hence pose a huge challenge as persistent pollutants. Radical ring-opening copolymerization (rROP) of cyclic ketene acetals (CKAs) such as 2-methylene-1,3-dioxepane (MDO) with vinyl monomers is an interesting approach being explored intensely for introducing degradable ester groups in the polymer backbones, opening up the potential of synthesizing biodegradable copolymers. However, carrying out such reactions in an aqueous medium to obtain biodegradable dispersions is very challenging due to the hydrolytic instability of CKAs. There are conflicting reports on preparing degradable lattices via rROP of MDO with vinyl acetate (VAc) monomers, but subsequent detailed reaction parameters were published, which show that under the right conditions, successful copolymerizations can be performed. We report that the use of neutral surfactants, high pH, and stabilizing comonomers play a crucial role in the successful incorporation of degradability in the polymer backbone during emulsion copolymerization. This is the first report on the synthesis of acrylate copolymers with the incorporation of hydrolytic degradability (utilizing MDO) under potentially more industrially feasible emulsion polymerization conditions. The findings underscore the potential for further improvement in this area. The results in the current study provide further insight into the breadth of parameters that must be carefully considered to produce biodegradable lattices via the rROP of CKAs.

中文翻译：

主链可降解丙烯酸酯乳胶：克服环状乙烯酮缩醛单体的水解限制

采用自由基乳液聚合制备的乳胶颗粒全部含有碳主链聚合物链，在环境中不可水解且不可生物降解，因此作为持久性污染物构成了巨大的挑战。环状烯酮缩醛（CKA）如 2-亚甲基-1,3-二氧杂环己烷（MDO）与乙烯基单体的自由基开环共聚（rROP）是一种正在深入探索的有趣方法，用于在聚合物主链中引入可降解的酯基团，提高合成可生物降解共聚物的潜力。然而，由于 CKA 的水解不稳定性，在水介质中进行此类反应以获得可生物降解的分散体非常具有挑战性。关于通过 MDO 与醋酸乙烯酯 (VAc) 单体的 rROP 制备可降解晶格的报道相互矛盾，但随后公布的详细反应参数表明，在正确的条件下，可以成功进行共聚。我们报告说，在乳液共聚过程中，使用中性表面活性剂、高 pH 值和稳定共聚单体对于成功地将可降解性纳入聚合物主链中起着至关重要的作用。这是第一份关于在工业上更可行的乳液聚合条件下合成丙烯酸酯共聚物并结合水解降解性（利用 MDO）的报告。研究结果强调了该领域进一步改进的潜力。当前研究的结果进一步深入了解了通过 CKA 的 rROP 生产可生物降解晶格时必须仔细考虑的参数范围。

更新日期：2024-03-15

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