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Semicrystalline long-chain polyphosphoesters from polyesterification

Hanna Busch, Sumit Majumder, Guenter Reiter, Stefan Mecking. Macromolecules 50 (2017) 2706–2713

Semicrystalline aliphatic polyphosphoesters can be obtained in a one-step approach by polyesterification of readily available bio-based long-chain diols with dichlorophosphorus compounds. Nonadecane-1,19-diol and tricosane-1,23-diol with respectively methylphosphonic dichloride or phenyl dichlorophosphate yield polymers (PPE19Me, PPE23Me, PPE19(OPh), and PPE23(OPh)) with molecular weights Mn up to 3 × 104 g mol–1. DSC analysis of these polymers and a C12 analogue reveal significantly enhanced crystallinities and melting points (up to Tm = 87 °C) with increasing methylene sequence length. DMA on injection-molded samples shows glass transitions at −19 °C (PPE19Me) and −12 °C (PPE23Me). Single crystals of PPE19Me accommodate a single C19 repeat unit, as concluded from a lamella thickness of only 3 nm thick determined by AFM. Hydrolytic degradation of solid polymer samples under ambient conditions occurred only to a minimal extent over three months by hydrolysis of very small amounts of in-chain anhydride defects.

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