The Rapid Chain Extension of Anthracene-Functional Polyesters by the Diels-Alder Reaction with Bismaleimides
✍ Scribed by Robert M. Kriegel; Katie L. Saliba; Genay Jones; David A. Schiraldi; David M. Collard
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 155 KB
- Volume
- 206
- Category
- Article
- ISSN
- 1022-1352
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✦ Synopsis
Abstract
Summary: The chain extension of anthracene end‐capped oligoesters by reaction with bismaleimides constitutes a rapid route to high molecular weight polyesters. Polytransesterification of bis(2‐hydroxyethyl) terephthalate in the presence of a small amount of 2‐hydroxyethyl 2‐anthracenecarboxylate provides low molecular weight anthracene‐terminated macromers with anthracene end group functionality (f~AN~) of 1.66–1.85. These are subject to rapid chain extension with di(4‐maleimidophenyl)methane by Diels‐Alder cycloadditions resulting in consumption of the anthracene and maleimide end groups to generate polymers with $\overline M _{\rm n}$ > 2.0 × 10^4^ g · mol^−1^. Thus, generation of the polymeric structure is achieved rapidly by addition reactions rather than sluggish transesterification reactions in which a condensate must be removed from the viscous polymer melt.
Chain extension of low‐molecular weight 2‐anthracenecarboxylate terminated oligoesters.
magnified imageChain extension of low‐molecular weight 2‐anthracenecarboxylate terminated oligoesters.