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However, the pKa of the boronic acid can be tuned by the addition of various substituents, so that this reversible covalent bond can be applied over a large range of pH values. Jay et al. reported a pH-responsive polymeric network crosslinked through boronate–diol complexes with self-healing properties . For this purpose, a 10 mol% phenyl boronic acid (PBA)-functionalized poly(2-hydroxypropylmethacrylamide) [poly(HPMAm)] and a 1 mol% salicylhydroxamic acid (SHA)functionalized poly(HPMAm) were synthesized and mixed with each other, resulting in a covalent crosslinked network across the entire pH range.
After 24 h the two cut pieces were reconnected and this process could be repeated three times. A new biocompatible polysaccharide-based self-healing hydrogel was reported by Wei et al. . The reversible imine and acylhydrazone bonds were introduced into the hydrogel networks by the reaction of N-carboxyethyl chitosan and adipic acid dihydrazide with oxidized sodium alignate. The self-healing ability was investigated by rheological recovery tests, macroscopic self-healing experiments, and beam-shaped strain compression measurements.
27 Repeated self-healing of crossed ruptured specimen of a polyurethane with reversible alkoxyamine units (Reproduced from . Copyright 2015 Elsevier) 46 N. Kuhl et al. NCO HO N OH O O HO n NCO PEG2000 N IPDI H CTPO H N O O n O H N O O N O O N ICPEG2000 Scheme 17 Synthesis of the reversible polyurethane ICPEG2000 (see text for details). Adopted from  Zhang et al. reported an alkoxyamine-crosslinked polyurethane that was capable of autonomous healing at ambient temperatures . Therefore, an alkoxyamine derivative, 5-hydroxy-2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-methyl pentane-nitrile (CTPO), was synthesized.