Abstract
Bio-based polyureas (PUs) are prepared by the polyaddition of a multifunctional bio-photodimer 4,4'-diamino-α-truxillic acid having two amines and two carboxyls with an aromatic isocyanate comonomer. Weight average molecular weights of the PUs range from 2.4 × 105 to 2.5 × 105g mol−1 with a narrow distribution around 1.3. The 10% weight-loss temperature of the PUs ranges from 270 to 280 °C, whereas the softening temperature ranges between 180 and 210 °C. The PUs are well dissolved in polar organic solvents such as dimethylformamide and the cast film is prepared from these solutions. The films show high transparency and swell in the alkaline solution when the PU carboxyls are anionized. If metal nitrate salts are added to the films, mechanical properties are increased by the double interaction of the metal cation with carboxylate and nitrate with urea, which causes the films to change the color.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Mathers, R. T. & Meier, M. A. R . in Green Polymerization Methods: Renewable Starting Materials, Catalysis and Waste Reduction (eds Mathers, R. T. & Meier, M. A. R.) (Wiley-VCH Verlag GmbH & Co., Weinheim, Germany, 2011)
Zakzeski, J., Bruijnincx, P. C. A., Jongerius, A. L. & Weckhuysen, B. M. The catalytic valorization of lignin for the production of renewable chemicals. Chem. Rev. 110, 3552–3599 (2010).
Kaneko, T., Tran, H. T., Shi, D. J. & Akashi, M. Environmentally degradable, high-performance plastics from phenolic phytomonomers. Nature Mater 5, 966–970 (2006).
Miller, S. A. Sustainable polymers: opportunities for the next decade. ACS Macro Lett. 2, 550–554 (2013).
Megiatto, J. D., Cazeils, E. Jr ., Ham-Pichavant, F., Grelier, S., Gardrat, C. & Castellan, A. Styrene-spaced copolymers including anthraquinone and β-O-4 lignin model units: synthesis, characterization and reactivity under alkaline pulping conditions. Biomacromolecules 13, 1652–1662 (2012).
Suvannasara, P., Tateyama, S., Miyasato, A., Matsumura, K., Shimoda, T., Ito, T., Yamagata, Y., Fujita, T., Takaya, N. & Kaneko, T. Bio-based polyimides from 4-aminocinnamic acid photodimer. Macromelecules 47, 1586–1593 (2014).
Chopra, K. L., Major, S. & Pandya, D. K. Transparent conductors- a status review. Thin Solid Films 102, 1–46 (1983).
Ostroverkhova, O . in Handbook of Organic Materials for Optical and (Opto)- Electronic Devices (ed. Ostroverkhova, O.) (Woodhead Publishing Limited, Cambridge, UK, 2013)
Bondy, C. R., Gale, P. A. & Loeb, S. J. Metal organic analogs of Calix[4]arene based anion receptors. Arranging urea hydrogen-bond acceptors to selectively bind chloride and sulfate ions. J. Am. Chem. Soc. 126, 5030–5031 (2004).
Arman, B., Reddy, A. S. & Arya, G. Viscoelastic properties and shock response of coarse-grained models of multiblock versus diblock copolymers: insights into dissipative properties of polyurea. Macromolecules 45, 3247–3255 (2012).
Perez-Casas, C. & Yatsimirsky, A. K. Detailing hydrogen bonding and deprotonation equilibria between anions and urea/thiourea derivatives. J. Org. Chem. 73, 2275–2284 (2008).
Ferrer, A. S., Rogez, D. & Martinoty, P. Synthesis and characterization of new polyurea elastomers by sol-gel chemistry. Macromol. Chem. Phys. 211, 1712–1721 (2010).
Acknowledgements
This work was partially supported by Japan Science and Technology Agency, Advanced Low Carbon Technology Research and Development Program, No. 5170020, Tokyo, Japan.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Competing interests
The authors declare no conflict of interest.
Additional information
Supplementary Information accompanies the paper on Polymer Journal website
Supplementary information
Rights and permissions
About this article
Cite this article
Jin, X., Tateyama, S. & Kaneko, T. Salt-induced reinforcement of anionic bio-polyureas with high transparency. Polym J 47, 727–732 (2015). https://doi.org/10.1038/pj.2015.58
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/pj.2015.58
This article is cited by
-
Syntheses of Soluble Biopolyimides Using 4-Aminophenylalanine
Chinese Journal of Polymer Science (2020)
