Recycling of Polydicyclopentadiene Enabled with N‐Coordinated Boronic Ester Bonds

Abstract

In this contribution, we reported the transformation of polydicyclopentadiene (PDCPD) from thermoset into vitrimer. First, two N‐coordinated diboronic diols were successfully synthesized via the reaction of N,N,N‐tri(2‐hydroxyethyl)amine and/or N,N,N“,N”‐tetrakis(2‐hydroxyethyl)ethylene diamine with 4‐(hydroxymethyl) phenylboronic acid and then they were transformed into two N‐coordinated cyclic boronic diacrylates. The latter two dienes carrying electron‐withdrawing substituents were used for the ring opening insertion metathesis copolymerization (ROIMP) of dicyclopentadiene to afford the crosslinked PDCPD. In the crosslinked PDCPD networks, N‐coordinated cyclic boronic bonds were integrated. It was found that the as‐obtained PDCPD networks displayed the excellent reprocessing properties. In the meantime, the fracture toughness was significantly improved. Owing to the inclusion of N‐coordinated cyclic boronic ester bonds, the modified PDCPDs had the thermal stability much superior to plain PDCPD. The results reported in this work demonstrated that PDCPD can successfully be transformed into the vitrimers via the introduction of N‐coordinated cyclic boronic ester bonds.This article is protected by copyright. All rights reserved

Toughened and Recyclable Epoxy Networks Featuring Nanostructures and Dynamic Covalent Bonds

“…To assess the antihydrolysis performance, the boronic ester-cross-linked epoxy networks were immersed into water and held at room temperature for 24 h. Notably, all of the networks remained intact (Figure S7), demonstrating that the epoxy networks had excellent hydrolysis resistance. It is proposed that the boronic ester bonds featuring boron–nitrogen (B–N) coordination are responsible for the excellent antihydrolysis performance. ,, …”

“…It is proposed that the boronic ester bonds featuring boron−nitrogen (B−N) coordination are responsible for the excellent antihydrolysis performance. 51,54,59 The cross-linked products derived from DGEBA, NH 2 -BO-BUDGE-BO-NH 2 , and/or NH 2 -BO-PCOE-BO-NH 2 were visually homogeneous and transparent, signifying that there was no macroscopic phase separation, in contrast to the blends cured under quiescent conditions (Figure S8). After extracting with a solvent (e.g., toluene), notably, no significant mass loss occurred, indicating that the PCOE chains fully participated in the formation of the cross-linked networks.…”