Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid
Authors
Panić, Vesna V.Seslija, Sanja I.
Popović, Ivanka G.
Spasojević, Vuk D.
Popović, Aleksandar R.
Nikolić, Vladimir
Spasojević, Pavle M.
Article (Accepted Version)
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For the preparation of fully biobased unsaturated polyester resins (UPRs), the replacement of styrene with alternate nonpetroleum-based monomers turned out to be one of the most challenging tasks. Its complexity lies in the fact that reactive diluents (RD) have to have low viscosity and volatility, good compatibility with prepolymer, and capability to homopolymerize and copolymerize with its unsaturations. In this context, we directed our efforts to develop fully biobased UPRs using the dialkyl itaconates as an alternative to styrene. Therefore, a series of 100% biobased UPRs were prepared from itaconic acid and 1,2-propandiol and diluted by dialkyl itaconates. The resins were characterized by Fourier transform infrared spectroscopy, NMR, volatility, and viscosity measurements, while the cured samples were characterized by dynamic mechanical properties, thermomechanical analysis, thermogravimetric analysis data, and tensile tests. The influence of RD structure on the properties of cure...d samples was discussed in detail. It was shown that the prepared resins had evaporation rates of dialkyl itaconates of several orders of magnitude less compared to styrene. The cured resins with dimethyl itaconate showed comparable or even better thermal and mechanical properties compared to the one with styrene. This investigation showed that itaconic acid and dialkyl itaconates are promising bioresources for the preparation of fully biobased UPRs for mass consumption.
Source:
Biomacromolecules, 2017, 18, 12, 3881-3891Publisher:
- Amer Chemical Soc, Washington
Funding / projects:
- Synthesis and characterization of novel functional polymers and polymeric nanocomposites (RS-MESTD-Basic Research (BR or ON)-172062)
Note:
- This is the peer-reviewed version of the following article: Panic, V. V.; Seslija, S. I.; Popovic, I. G.; Spasojevic, V. D.; Popovic, A. R.; Nikolic, V. B.; Spasojevic, P. M. Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid. Biomacromolecules 2017, 18 (12), 3881–3891. https://doi.org/10.1021/acs.biomac.7b00840
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3059
DOI: 10.1021/acs.biomac.7b00840
ISSN: 1525-7797
WoS: 000418109200002
Scopus: 2-s2.0-85038208092
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Panić, Vesna V. AU - Seslija, Sanja I. AU - Popović, Ivanka G. AU - Spasojević, Vuk D. AU - Popović, Aleksandar R. AU - Nikolić, Vladimir AU - Spasojević, Pavle M. PY - 2017 UR - https://cherry.chem.bg.ac.rs/handle/123456789/3058 AB - For the preparation of fully biobased unsaturated polyester resins (UPRs), the replacement of styrene with alternate nonpetroleum-based monomers turned out to be one of the most challenging tasks. Its complexity lies in the fact that reactive diluents (RD) have to have low viscosity and volatility, good compatibility with prepolymer, and capability to homopolymerize and copolymerize with its unsaturations. In this context, we directed our efforts to develop fully biobased UPRs using the dialkyl itaconates as an alternative to styrene. Therefore, a series of 100% biobased UPRs were prepared from itaconic acid and 1,2-propandiol and diluted by dialkyl itaconates. The resins were characterized by Fourier transform infrared spectroscopy, NMR, volatility, and viscosity measurements, while the cured samples were characterized by dynamic mechanical properties, thermomechanical analysis, thermogravimetric analysis data, and tensile tests. The influence of RD structure on the properties of cured samples was discussed in detail. It was shown that the prepared resins had evaporation rates of dialkyl itaconates of several orders of magnitude less compared to styrene. The cured resins with dimethyl itaconate showed comparable or even better thermal and mechanical properties compared to the one with styrene. This investigation showed that itaconic acid and dialkyl itaconates are promising bioresources for the preparation of fully biobased UPRs for mass consumption. PB - Amer Chemical Soc, Washington T2 - Biomacromolecules T1 - Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid VL - 18 IS - 12 SP - 3881 EP - 3891 DO - 10.1021/acs.biomac.7b00840 ER -
@article{ author = "Panić, Vesna V. and Seslija, Sanja I. and Popović, Ivanka G. and Spasojević, Vuk D. and Popović, Aleksandar R. and Nikolić, Vladimir and Spasojević, Pavle M.", year = "2017", abstract = "For the preparation of fully biobased unsaturated polyester resins (UPRs), the replacement of styrene with alternate nonpetroleum-based monomers turned out to be one of the most challenging tasks. Its complexity lies in the fact that reactive diluents (RD) have to have low viscosity and volatility, good compatibility with prepolymer, and capability to homopolymerize and copolymerize with its unsaturations. In this context, we directed our efforts to develop fully biobased UPRs using the dialkyl itaconates as an alternative to styrene. Therefore, a series of 100% biobased UPRs were prepared from itaconic acid and 1,2-propandiol and diluted by dialkyl itaconates. The resins were characterized by Fourier transform infrared spectroscopy, NMR, volatility, and viscosity measurements, while the cured samples were characterized by dynamic mechanical properties, thermomechanical analysis, thermogravimetric analysis data, and tensile tests. The influence of RD structure on the properties of cured samples was discussed in detail. It was shown that the prepared resins had evaporation rates of dialkyl itaconates of several orders of magnitude less compared to styrene. The cured resins with dimethyl itaconate showed comparable or even better thermal and mechanical properties compared to the one with styrene. This investigation showed that itaconic acid and dialkyl itaconates are promising bioresources for the preparation of fully biobased UPRs for mass consumption.", publisher = "Amer Chemical Soc, Washington", journal = "Biomacromolecules", title = "Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid", volume = "18", number = "12", pages = "3881-3891", doi = "10.1021/acs.biomac.7b00840" }
Panić, V. V., Seslija, S. I., Popović, I. G., Spasojević, V. D., Popović, A. R., Nikolić, V.,& Spasojević, P. M.. (2017). Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid. in Biomacromolecules Amer Chemical Soc, Washington., 18(12), 3881-3891. https://doi.org/10.1021/acs.biomac.7b00840
Panić VV, Seslija SI, Popović IG, Spasojević VD, Popović AR, Nikolić V, Spasojević PM. Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid. in Biomacromolecules. 2017;18(12):3881-3891. doi:10.1021/acs.biomac.7b00840 .
Panić, Vesna V., Seslija, Sanja I., Popović, Ivanka G., Spasojević, Vuk D., Popović, Aleksandar R., Nikolić, Vladimir, Spasojević, Pavle M., "Simple One-Pot Synthesis of Fully Biobased Unsaturated Polyester Resins Based on Itaconic Acid" in Biomacromolecules, 18, no. 12 (2017):3881-3891, https://doi.org/10.1021/acs.biomac.7b00840 . .