The Rapid Chain Extension of Anthracene-Functional Polyesters by the Diels-Alder Reaction with Bismaleimides

• Published in: Macromolecular chemistry and physics Vol. 206; no. 15; pp. 1479 - 1487
• Main Authors: Kriegel, Robert M., Saliba, Katie L., Jones, Genay, Schiraldi, David A., Collard, David M.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 05.08.2005; WILEY‐VCH Verlag; Wiley
• Subjects: Applied sciences; chain extension; Exact sciences and technology; macromers; Organic polymers; Physical Sciences; Physicochemistry of polymers; Polycondensation; polyesters; Polymer Science; Preparation, kinetics, thermodynamics, mechanism and catalysts; Science & Technology; macromers; CROSS-LINKING; MALEIMIDES; chain extension; polyesters; Ethylene terephthalate polymer; End group; Cyclopolymerization; Chain elongation; Mechanical properties; Diels Alder addition; Esterimide copolymer; Experimental study; Diimide; Transformation temperature; Heat of transformation; Cyclopolymer; Preparation; Ethylene terephthalate copolymer
• ISSN: 1022-1352; 1521-3935
• DOI: 10.1002/macp.200500063

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 (fAN) 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 × 104 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.