Rapid and Controlled Organocatalyzed Ring-Opening Polymerization of 3S-(Isobutyl)morpholine-2,5-dione and Copolymerization with Lactide,Macromolecules

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Rapid and Controlled Organocatalyzed Ring-Opening Polymerization of 3S-(Isobutyl)morpholine-2,5-dione and Copolymerization with Lactide
Macromolecules ( IF 5.1 ) Pub Date : 2020-07-27 , DOI: 10.1021/acs.macromol.0c00940
Tobias F. Burton ₁ , Julien Pinaud ₁ , Olivia Giani ₁

Affiliation

Morpholine-2,5-diones are increasingly attractive monomers derived from amino-acids whose copolymerization with other monomers produces interesting biodegradable materials. In this study, the rapid and controlled organocatalyzed ring-opening polymerization of 3S-(isobutyl)morpholine-2,5-dione (MD) and its copolymerization with lactide (LA) was accomplished using 1,8-diazabicyclo(5,4,0)undec-7-ene and a thiourea (TU) cocatalyst. The amount of TU used for the polymerization was found to be fundamental for achieving good control. A range of polymers with molecular weights between 8.1 and 25.2 kg mol^–1 was thus produced with narrow chain distributions (Đ = 1.13–1.18) in short periods (5 to 10 min). Secondly, copolymers with varying compositions (MD:LA = 25:75;50:50; 75:25) were prepared (11.2 to 12.7 kg mol^–1;Đ = 1.09–1.26). The kinetics of these polymerizations suggest that concurrent thioimidate and cyclic imidate mechanisms are occurring and that these are governed by the quantity of TU in respect to MD.

中文翻译：

3S-（异丁基）吗啉-2,5-二酮的快速可控的有机催化开环聚合和丙交酯共聚合

吗啉-2,5-二酮是越来越有吸引力的氨基酸衍生单体，其与其他单体的共聚可产生有趣的可生物降解材料。在这项研究中，使用1,8-二氮杂双环（5,4,3,5-二氮杂双环（5,4,3,5-二氮杂双环戊二烯），可实现3S-（异丁基）吗啉-2,5-二酮（MD）的快速可控的有机催化开环聚合及其与丙交酯的共聚反应。 0）十一碳7-烯和硫脲（TU）助催化剂。发现用于聚合的TU的量是实现良好控制的基础。甲范围与8.1之间分子量的聚合物的和25.2公斤摩尔^-1因此产生具有窄分布的链（Đ= 5到10分钟（1.13–1.18）。其次，制备具有不同组成的共聚物（MD：LA = 25：75; 50：50; 75:25）（11.2至12.7 kg摩尔^–1；Đ = 1.09–1.26）。这些聚合反应的动力学表明同时存在硫代亚氨酸酯和环状亚氨酸酯的机理，并且这些机理受TU相对于MD的数量的控制。

更新日期：2020-08-11

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