Rosin side chain type catalyst-free vitrimers with high cross-link density, mechanical strength, and thermal stability

Abstract

The emergence of vitrimer, a new class of polymer materials can address the problem of recyclability, reprocess ability and recyclability of thermosetting plastics. Rosin, a natural product, is an ideal raw material for the preparation of polymers in a more sustainable way. Nevertheless, due to the huge steric hindrance caused by the hydrogenated phenanthrene ring structure, the cross-link density of materials is frequently lowered. In this study, hydrogenated rosin was adopted for preparing hydrogenated rosin side-chain type diacids, which were reacted with mixed epoxy to obtain rosin side-chain type vitrimers. It was completely characterized by differential scanning calorimetry test, thermogravimetric analysis, shape memory test and self-healing test. The prepared vitrimers exhibited good self-healing properties, excellent heat resistance (T_d = 352 °C) as well as high mechanical properties (tensile strength of 46.75 MPa). The tricyclic diterpene structure of rosin was introduced into the side chain in order to avoid the reduction of cross-link density resulting from the huge steric hindrance of the rigid tricyclic hydrophenylene skeleton. Vitrimers can undergo dynamic transesterification reaction without external catalysts due to the autocatalytic effect of tertiary amines from epoxy. Moreover, our work expanded the application field of rosin, increased the added value of rosin, and provided a novel method for preparing rosin-based vitrimers with ideal properties.

Graphical abstract

Keywords

vitrimers / rosin / catalyst-free / high mechanical properties / dynamic transesterification reaction

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Acknowledgements

This research was supported by the National Natural Science Foundation of China (Grant No. 32171734) and the Scientific Research Funds of Huaqiao University (Grant No. 20BS201).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-022-2291-7 and is accessible for authorized users.

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