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Rigid polyurethanes, polyesters, and polycarbonates from renewable ketal monomers

Sophie Lingier (UGent) , Yann Spiesschaert (UGent) , Bastiaan Dhanis (UGent) , Stefaan De Wildeman (UGent) and Filip Du Prez (UGent)
(2017) MACROMOLECULES. 50(14). p.5346-5352
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Abstract
Two novel biobased diols containing rigid cyclic ketal functionalities have been synthesized on a relatively large scale from glycerol and two diketones, i.e., 1,4-cyclohexanedione and 4,4'-bicyclohexanone. The diols have been used in several types of step growth reactions, resulting in polycarbonates, polyesters, and polyurethanes. While molecular weights (M-n) of up to 50 kg mol(-1) are obtained for the polyurethanes, they also exhibit high glass transition (T-g = 95-150 degrees C) and degradation temperatures (T-d = 260-320 degrees C), are transparent, and show a high mechanical strength (E = 1.10-1.35 GPa) but brittle behavior. For the polycarbonates, M-n values higher than 24 kg mol(-1) and T-g's in the range of 70-100 degrees C have been obtained. Moreover, the polycarbonates show good mechanical properties like ductility and are transparent. Finally, a new generation of fully renewable polyesters have been synthesized with dimethyl succinate and dimethyl furan dicarboxylate. While moderate molecular weight values are obtained, the polyesters show T-g's of up to 96 degrees C as well as high T-d's (+/- 315 degrees C).
Keywords
ACETALIZED GALACTARIC ACID, ALIPHATIC POLYESTERS, AROMATIC COPOLYESTERS, THERMAL-PROPERTIES, BIOBASED POLYMERS, BICYCLIC MONOMERS, MOLECULAR-WEIGHT, CO-POLYESTERS, BISPHENOL-A, D-MANNITOL

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Chicago
Lingier, Sophie, Yann Spiesschaert, Bastiaan Dhanis, Stefaan De Wildeman, and Filip Du Prez. 2017. “Rigid Polyurethanes, Polyesters, and Polycarbonates from Renewable Ketal Monomers.” Macromolecules 50 (14): 5346–5352.
APA
Lingier, S., Spiesschaert, Y., Dhanis, B., De Wildeman, S., & Du Prez, F. (2017). Rigid polyurethanes, polyesters, and polycarbonates from renewable ketal monomers. MACROMOLECULES, 50(14), 5346–5352.
Vancouver
1.
Lingier S, Spiesschaert Y, Dhanis B, De Wildeman S, Du Prez F. Rigid polyurethanes, polyesters, and polycarbonates from renewable ketal monomers. MACROMOLECULES. 2017;50(14):5346–52.
MLA
Lingier, Sophie et al. “Rigid Polyurethanes, Polyesters, and Polycarbonates from Renewable Ketal Monomers.” MACROMOLECULES 50.14 (2017): 5346–5352. Print.
@article{8547557,
  abstract     = {Two novel biobased diols containing rigid cyclic ketal functionalities have been synthesized on a relatively large scale from glycerol and two diketones, i.e., 1,4-cyclohexanedione and 4,4'-bicyclohexanone. The diols have been used in several types of step growth reactions, resulting in polycarbonates, polyesters, and polyurethanes. While molecular weights (M-n) of up to 50 kg mol(-1) are obtained for the polyurethanes, they also exhibit high glass transition (T-g = 95-150 degrees C) and degradation temperatures (T-d = 260-320 degrees C), are transparent, and show a high mechanical strength (E = 1.10-1.35 GPa) but brittle behavior. For the polycarbonates, M-n values higher than 24 kg mol(-1) and T-g's in the range of 70-100 degrees C have been obtained. Moreover, the polycarbonates show good mechanical properties like ductility and are transparent. Finally, a new generation of fully renewable polyesters have been synthesized with dimethyl succinate and dimethyl furan dicarboxylate. While moderate molecular weight values are obtained, the polyesters show T-g's of up to 96 degrees C as well as high T-d's (+/- 315 degrees C).},
  author       = {Lingier, Sophie and Spiesschaert, Yann and Dhanis, Bastiaan and De Wildeman, Stefaan and Du Prez, Filip},
  issn         = {0024-9297},
  journal      = {MACROMOLECULES},
  keywords     = {ACETALIZED GALACTARIC ACID,ALIPHATIC POLYESTERS,AROMATIC COPOLYESTERS,THERMAL-PROPERTIES,BIOBASED POLYMERS,BICYCLIC MONOMERS,MOLECULAR-WEIGHT,CO-POLYESTERS,BISPHENOL-A,D-MANNITOL},
  language     = {eng},
  number       = {14},
  pages        = {5346--5352},
  title        = {Rigid polyurethanes, polyesters, and polycarbonates from renewable ketal monomers},
  url          = {http://dx.doi.org/10.1021/acs.macromol.7b00899},
  volume       = {50},
  year         = {2017},
}

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