Rigid biobased polycarbonates with good processability based on a spirocyclic diol derived from citric acid
Bonjour, O., Liblikas, I., Pehk, T., Khai-Nghi, T., Rissanen, K., Vares, L., & Jannasch, P. (2020). Rigid biobased polycarbonates with good processability based on a spirocyclic diol derived from citric acid. Green Chemistry, 22(12), 3940-3951. https://doi.org/10.1039/d0gc00849d
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Green ChemistryAuthors
Date
2020Copyright
© 2020 The Royal Society of Chemistry
Introducing biobased polymers from renewable sources for use as high-performance thermoplastics with high demands on mechanical rigidity, transparency, thermal stability, as well as good processability, is a significant challenge. In the present work we have designed and prepared a rigid biobased bis-spirocylic diol by di-cycloketalization of a bicyclic diketone (cis-bicyclo[3.3.0]octane-3,7-dione, obtained from citric acid) using trimethylolpropane. This spiro-diol monomer has two reactive primary hydroxyl groups and the synthesis from inexpensive biobased starting materials is straightforward and readily upscalable, involving no chromatographic purification. In order to explore the usefulness of the new monomer, it was employed in melt polycondensations with diphenylcarbonate at up to 280 °C to form rigid fully amorphous polycarbonates (PCs). Molecular weights (MWs) up to Mn = 28 kg mol−1 were achieved, and thermal and dynamic mechanical measurements showed glass transitions up to Tg = 100 °C, with no thermal decomposition until Td ∼350 °C. Solvent cast films had excellent mechanical flexibility and strength, as well as a high transparency with only slight coloration. Results by dynamic melt rheology implied that the high-MW PCs had a good processability at 170 °C, with a stable shear modulus over time, but started to degrade via chain scission reactions when the temperature approached 200 °C. In conclusion, the present work demonstrates the straightforward preparation of the citric acid-based spiro-diol, and indicates that it is an efficient building block for the preparation of rigid biobased PCs and other condensation polymers.
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Royal Society of ChemistryISSN Search the Publication Forum
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This work was supported by the European Regional Development Fund (project no. MOBTT21) and the Estonia-Russia Cross Border Cooperation Programme (ER30). O. B. is grateful to the Swedish Research Council Formas for financial support (diarienr 2016-00468), and P. J. acknowledges funding by the Swedish Foundation for Strategic Environmental Research through the “STEPS” project (no. 2016/1489). T. P. thanks The Estonian Ministry of Education and Research (grant no. IUT23-7) and the European Regional Development Fund (grant no. TK134). We are grateful to Jevgenija Martõnova and Prof. Riina Aav for obtaining single crystals for X-ray and this was supported by the Estonian Research Council (grant PRG339). ...License
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