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Issue 1, 2010
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Self-healing polymers prepared via living radical polymerisation

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Abstract

Diels–Alder chemistry has been used to synthesise polymerisation initiators and a dimethacrylic cross-linker that leads to efficient cleavage and reformation; self-healing. The initiators were prepared using 1-(2-hydroxyethyl)-1H-pyrrole-2,5-dione (3) as an intermediate, and reacting this with furfuryl alcohol to afford 2-bromo-2-methyl-propionic acid 2-[1-(2-bromo-2-methyl-propionyloxymethyl)-3,5-dioxo-10-oxa-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl]-ethyl ester (7) and 9-anthracenemethanol to yield initiator (8). The former exhibited polymers with excellent cleavage properties (Mn 12 000 g mol−1 to 6500 g mol−1) with reformation at efficiency of 50% (Mn 8900 g mol−1). The initiator from the anthracene derivative initially indicated that retro-Diels–Alder was not occurring with no change in the NMR or GPC data. An excess of a rhodamine-based dienophile was added to capture any cleaved anthracene-terminated polymer, with results indicating that the polymer is cleaving and reforming upon the cooling cycle. Similar results were observed with arm first stars, made using a Diels–Alder based dimethacrylate cross-linker. Little cleavage was observed initially, however, addition of the tag gave a significant reduction in Mw (7080 g mol−1 to 5300 g mol−1) and Mw/Mn (1.78 to 1.26).

Graphical abstract: Self-healing polymers prepared via living radical polymerisation

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Article information


Submitted
23 Oct 2009
Accepted
15 Dec 2009
First published
15 Jan 2010

Polym. Chem., 2010,1, 102-106
Article type
Paper

Self-healing polymers prepared via living radical polymerisation

J. A. Syrett, G. Mantovani, W. R. S. Barton, D. Price and D. M. Haddleton, Polym. Chem., 2010, 1, 102
DOI: 10.1039/B9PY00316A

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