Bio-based comb-like copolymers derived from alkyl 10-undecenoates and maleic anhydride

5 years ago

Bio-based comb-like copolymers derived from alkyl 10-undecenoates and maleic anhydride

Maria Aparecida Ferreira César-Oliveira, Fernando Augusto Ferraz, Aline Silva Muniz, Angelo Roberto dos Santos Oliveira

In this article, 10-undecenoic acid, based on castor oil, was used a raw material for the synthesis of alternating copolymers. ω-Unsaturated fatty esters as alkyl 10-undecenoates were prepared by the esterification reaction of 10-undecenoic acid with alkyl alcohol. A series of comb-like copolymers were synthesized by free radical polymerization from maleic anhydride and alkyl 10-undecenoates copolymers with different length of alkyl side chains in a toluene solution. These copolymers were investigated by 1H and 13C nuclear magnetic resonance, Fourier transform infrared spectroscopy, gel permeation chromatography, thermogravimetric analysis, differential scanning calorimetry (DSC). The copolymers were obtained in a low molecular weight in a range 3370–12,240 g mol−1 and their structural characterization indicated the formation of alternating copolymers. DSC characterization revealed that these comb-like copolymers showed amorphous to semicrystalline behavior by increasing the length of side chains. The bio-based comb-like copolymers allow for the development of new polymeric materials for several applications. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018. Vegetable oils are considered as the most important renewable raw materials having great advantages, including worldwide availability and low cost. Alkyl 10-undecenoates monomers were obtained from castor oil, and a series of comb-like copolymers were synthesized from maleic anhydride and alkyl 10-undecenoates. 1H NMR analysis showed the formation of alternating copolymers and DSC analysis revealed that these copolymers showed amorphous to semicrystalline behavior with increasing the length of side chains.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/pola.28978