Abstract
Renewable vinyl compounds itaconic acid (IA) and its derivative 10-hydroxyhexylitaconic acid (10-HHIA) are naturally produced by fungi from biomass. This provides the opportunity to develop new biobased polyvinyls from IA and 10-HHIA monomers. In this study, we copolymerized these monomers at different ratios through free radical aqueous polymerization with potassium peroxodisulfate as an initiator, resulting in poly(IA-co-10-HHIA)s with different monomer compositions. We characterized the thermal properties of the polymers by thermogravimetric analysis (TGA) and Fourier-transform infrared spectroscopy (FT-IR). The nuclear magnetic resonance analysis and the gel permeation chromatography showed that the polymerization conversion, yield, and the molecular weights (weight-averaged Mw and number-averaged Mn) of the synthesized poly(IA-co-10-HHIA)s decreased with increasing 10-HHIA content. It is suggested that the hydroxyhexyl group of 10-HHIA inhibited the polymerization. The TGA results indicated that the poly(IA-co-10-HHIA)s continuously decomposed as temperature increased. The FT-IR analysis suggested that the formation of the hydrogen bonds between the carboxyl groups of IA and 10-HHIA in the polymer chains was promoted by heating and consequently the polymer dehydration occurred. To the best of our knowledge, this is the first time that biobased polyvinyls were synthesized using naturally occurring IA derivatives.
Highlights
Owing to the growing environmental interest, the development of renewable polymer materials derived from biomass is increasing in popularity [1,2,3,4]
The present study reports on the free radical polymerization of poly(IA-co-10-hydroxyhexylitaconic acid (10-HHIA))s with Itaconic acid (IA)
According to reported homo-polymerizations of IA [29,30,31,32,33,34], the poly(IA-co-10-HHIA) copolymers were synthesized by the free radical polymerization of IA and 10-HHIA in water with KPS as an initiator
Summary
Owing to the growing environmental interest, the development of renewable polymer materials derived from biomass is increasing in popularity [1,2,3,4]. Some renewable monomers that are produced by microbes from biomass consist of larger carbon numbers (higher than C5) [8]. These monomers are barely synthesized from petroleum resources and possess unique structural characteristics increasing their potential to be applied as new monomers. Itaconic acid (IA) is one of the most promising renewable vinyl compounds commercially produced using fungi, mostly Aspergillus terreus [9,10,11,12]. IA is a sustainable monomer because it is fermentatively produced from biomass.
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