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Issue 38, 2018
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Polycycloacetals via polytransacetalization of diglycerol bisacetonide

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Abstract

Diglycerol bisacetonide was synthesized and isolated from acetone and diglycerol, which is renewable and available in large scale. DGA was directly used in polytransacetalization with 1,4-cyclohexanedione or 4,4′-bicyclohexanone as diketone monomers. Polycycloacetals were obtained with molecular weights (Mn) of up to 28 kg mol−1, broad dispersities (Đ = 1.5–4.0) and as semi-crystalline polymers with high melting points (Tm = 210–241 °C) and glass transition temperatures (Tg) of 48 °C or 65 °C. Introducing di(trimethylolpropane) (di-TMP) in the polymerization of DGA and 1,4-cyclohexanedione resulted in copolymers as confirmed by 1H-NMR and 13C-NMR spectroscopy. Increasing the di-TMP content from 10 to 50 mol% reduces the crystallinity of the polycycloacetals and increases the Tg, eventually yielding amorphous polymers (Tg = 60–71 °C). For the amorphous polycycloacetals, Young's moduli could be determined by tensile strength testing (E = 1.1–1.4 GPa). The polycycloacetals with renewable carbon contents in the range of 33–100% cover a wide range in material properties and are stable against hydrolysis at pH > 1–3, depending on the polycycloacetal composition.

Graphical abstract: Polycycloacetals via polytransacetalization of diglycerol bisacetonide

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Supplementary files

Article information


Submitted
12 Aug 2018
Accepted
27 Aug 2018
First published
27 Aug 2018

Polym. Chem., 2018,9, 4789-4797
Article type
Paper

Polycycloacetals via polytransacetalization of diglycerol bisacetonide

A. Hufendiek, S. Lingier, P. Espeel, S. De Wildeman and F. E. Du Prez, Polym. Chem., 2018, 9, 4789
DOI: 10.1039/C8PY01191E

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