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Polycycloacetals via polytransacetalization of diglycerol bisacetonide

Andrea Hufendiek (UGent) , Sophie Lingier (UGent) , Pieter Espeel (UGent) , Stefaan De Wildeman and Filip Du Prez (UGent)
(2018) POLYMER CHEMISTRY. 9(38). p.4789-4797
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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 (M-n) of up to 28 kg mol(-1), broad dispersities (D = 1.5-4.0) and as semi-crystalline polymers with high melting points (T-m = 210-241 degrees C) and glass transition temperatures (T-g) of 48 degrees C or 65 degrees C. Introducing di(trimethylolpropane) (di-TMP) in the polymerization of DGA and 1,4-cyclohexanedione resulted in copolymers as confirmed by H-1-NMR and C-13-NMR spectroscopy. Increasing the di-TMP content from 10 to 50 mol% reduces the crystallinity of the polycycloacetals and increases the T-g, eventually yielding amorphous polymers (T-g = 60-71 degrees 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.
Keywords
ACETAL METATHESIS POLYMERIZATION, DELIVERY VEHICLE, POLYKETAL, MICROPARTICLES, GLYCEROL, POLYACETALS, POLYMERS, POLYURETHANES, POLYESTERS, COPOLYMERS, MONOMERS

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MLA
Hufendiek, Andrea, et al. “Polycycloacetals via Polytransacetalization of Diglycerol Bisacetonide.” POLYMER CHEMISTRY, vol. 9, no. 38, 2018, pp. 4789–97, doi:10.1039/c8py01191e.
APA
Hufendiek, A., Lingier, S., Espeel, P., De Wildeman, S., & Du Prez, F. (2018). Polycycloacetals via polytransacetalization of diglycerol bisacetonide. POLYMER CHEMISTRY, 9(38), 4789–4797. https://doi.org/10.1039/c8py01191e
Chicago author-date
Hufendiek, Andrea, Sophie Lingier, Pieter Espeel, Stefaan De Wildeman, and Filip Du Prez. 2018. “Polycycloacetals via Polytransacetalization of Diglycerol Bisacetonide.” POLYMER CHEMISTRY 9 (38): 4789–97. https://doi.org/10.1039/c8py01191e.
Chicago author-date (all authors)
Hufendiek, Andrea, Sophie Lingier, Pieter Espeel, Stefaan De Wildeman, and Filip Du Prez. 2018. “Polycycloacetals via Polytransacetalization of Diglycerol Bisacetonide.” POLYMER CHEMISTRY 9 (38): 4789–4797. doi:10.1039/c8py01191e.
Vancouver
1.
Hufendiek A, Lingier S, Espeel P, De Wildeman S, Du Prez F. Polycycloacetals via polytransacetalization of diglycerol bisacetonide. POLYMER CHEMISTRY. 2018;9(38):4789–97.
IEEE
[1]
A. Hufendiek, S. Lingier, P. Espeel, S. De Wildeman, and F. Du Prez, “Polycycloacetals via polytransacetalization of diglycerol bisacetonide,” POLYMER CHEMISTRY, vol. 9, no. 38, pp. 4789–4797, 2018.
@article{8599643,
  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 (M-n) of up to 28 kg mol(-1), broad dispersities (D = 1.5-4.0) and as semi-crystalline polymers with high melting points (T-m = 210-241 degrees C) and glass transition temperatures (T-g) of 48 degrees C or 65 degrees C. Introducing di(trimethylolpropane) (di-TMP) in the polymerization of DGA and 1,4-cyclohexanedione resulted in copolymers as confirmed by H-1-NMR and C-13-NMR spectroscopy. Increasing the di-TMP content from 10 to 50 mol% reduces the crystallinity of the polycycloacetals and increases the T-g, eventually yielding amorphous polymers (T-g = 60-71 degrees 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.}},
  author       = {{Hufendiek, Andrea and Lingier, Sophie and Espeel, Pieter and De Wildeman, Stefaan and Du Prez, Filip}},
  issn         = {{1759-9954}},
  journal      = {{POLYMER CHEMISTRY}},
  keywords     = {{ACETAL METATHESIS POLYMERIZATION,DELIVERY VEHICLE,POLYKETAL,MICROPARTICLES,GLYCEROL,POLYACETALS,POLYMERS,POLYURETHANES,POLYESTERS,COPOLYMERS,MONOMERS}},
  language     = {{eng}},
  number       = {{38}},
  pages        = {{4789--4797}},
  title        = {{Polycycloacetals via polytransacetalization of diglycerol bisacetonide}},
  url          = {{http://dx.doi.org/10.1039/c8py01191e}},
  volume       = {{9}},
  year         = {{2018}},
}
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