High Performance, Reprocessable, and Degradable Biobased Polyhydroxyurethane Vitrimers from an Imine-Containing Vanillin Dicyclocarbonate.

IF 5.2 Q1 POLYMER SCIENCE

ACS Macro Letters Pub Date : 2025-07-09 DOI:10.1021/acsmacrolett.5c00308

Yuanmeng Wang,Min Fan,Jingbo Zhao

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引用次数: 0

Abstract

Polyhydroxyurethane (PHU) is an emerging type of nonisocyanate polyurethane that is accessible by the aminolysis of cyclocarbonates (CCs) with amines. Biobased PHUs additionally conform to green, environmentally friendly, and sustainable development. Here, a five-membered vanillin di-CC with an imine group (VAI-5CC) was prepared through a cyclocarbonation of an imine-containing vanillin-tetraol with dimethyl carbonate under normal pressure, and the aminolysis of VAI-5CC with a triamine and hexanediamine or poly(propylene glycol) bis(2-aminopropyl ether) was explored. Several new biobased vanillin PHU vitrimers (CC-PHUs) with hydroxyurethane and imine (HU-IM) dual dynamic bonds were prepared successfully through this sustainable and green strategy. Aromatic vanillin units provide the CC-PHUs with excellent mechanical properties (storage modulus of 3.6-4.2 GPa and tensile strength of 74-106 MPa). HU-IM dual dynamic covalent bonds make the CC-PHUs easily reprocessed at a low temperature (110 °C). CC-PHUs were easily degraded under acidic conditions due to the presence of imine bonds.

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高性能，可再加工，可降解的生物基聚羟基聚氨酯聚合物，从含亚胺的香草醛二环碳酸盐。

聚羟基聚氨酯（PHU）是一种新兴的非异氰酸酯聚氨酯，可通过胺对环碳酸盐（cc）的氨解而获得。此外，生物基phu符合绿色、环保和可持续发展的要求。本文以含亚胺的香草素四醇为原料，在常压下与碳酸二甲酯进行环碳酸化反应，制备了带亚胺基的五元香兰素二烷基醇（VAI-5CC），并探讨了VAI-5CC与三胺-己二胺或聚（丙二醇）双（2-氨基丙醚）的氨解反应。通过这种可持续和绿色的策略，成功地制备了几种具有羟基和亚胺双动态键的生物基香兰素PHU vitrimers （CC-PHUs）。芳香香兰素单元使CC-PHUs具有优异的力学性能（储存模量为3.6-4.2 GPa，拉伸强度为74-106 MPa）。HU-IM双动态共价键使cc - phu在低温（110℃）下易于再加工。由于亚胺键的存在，CC-PHUs在酸性条件下容易降解。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Macro Letters 化学-

CiteScore

10.40

自引率

3.40%

发文量

209

审稿时长

1 months

期刊介绍： ACS Macro Letters publishes research in all areas of contemporary soft matter science in which macromolecules play a key role, including nanotechnology, self-assembly, supramolecular chemistry, biomaterials, energy generation and storage, and renewable/sustainable materials. Submissions to ACS Macro Letters should justify clearly the rapid disclosure of the key elements of the study. The scope of the journal includes high-impact research of broad interest in all areas of polymer science and engineering, including cross-disciplinary research that interfaces with polymer science. With the launch of ACS Macro Letters, all Communications that were formerly published in Macromolecules and Biomacromolecules will be published as Letters in ACS Macro Letters.