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Polycycloacetals via polytransacetalization of diglycerol bisacetonide

(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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Chicago
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.
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.
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.
MLA
Hufendiek, Andrea et al. “Polycycloacetals via Polytransacetalization of Diglycerol Bisacetonide.” POLYMER CHEMISTRY 9.38 (2018): 4789–4797. Print.
@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 {\textrangle} 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},
  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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