Renewable Aromatic–Aliphatic Copolyesters Derived from Rapeseed

Abstract

Novel (co)polyesters are synthesized from rapeseed-derived renewable starting materials. Aliphatic monomers are obtained from oleic and erucic acid via thiol-ene addition, whereas ferulic acid is used for the synthesis of aromatic monomers. Copolyesters with different ratios of these monomers are prepared via base-catalyzed transesterifi cation reactions under neat conditions. Both monomer and polymer synthesis are optimized to achieve a high yield using environmentally benign synthetic procedures. A focus is put on applying less-toxic reagents (i.e., avoiding halogenated compounds) and on minimizing the produced waste, in order to meet the requirements of green chemistry. The resulting thioether-bearing (co)polyester series is analyzed, and fi nally oxidized to sulfone analogues. The thermal properties before and after oxidation are then compared. and thermal properties of the new (co)polyesters was performed.

Chemo-enzymatic Synthesis, Derivatizations, and Polymerizations of Renewable Phenolic Monomers Derived from Ferulic Acid and Biobased Polyols: An Access to Sustainable Copolyesters, Poly(ester-urethane)s, and Poly(ester-alkenamer)s

“…However, they are often hard to process because of a too high melting temperature (T m ). To lower the T m , p-hydroxycinnamic acids were copolymerized with aliphatic monomer to increase the structural flexibility of the resulting polymers (38)(39)(40). Another approach, recently applied for the synthesis of bisphenols from vanillin (41), is to prepare A 2 -type bisphenols from these p-hydroxycinnamic acids and aliphatic moieties then polymerize them with B 2 -type monomers for the preparation of alternating copolymers.…”

Bio-based Polymer from Ferulic Acid by Electropolymerization

“…Bio-based polymers using ferulic acid have been reported, including polyester (Mialon et al 2010;Kreye et al 2013;Pion et al 2013Pion et al , 2014Oulame et al 2015;Barbara et al 2015;Nguyen et al 2015;Maiorana et al 2016;Reano et al 2016), copolymer with methacrylic acid (Iemma et al 2010), and liquid-crystalline forms (Wang et al 2012). Ferulic acid has many physiological functions including antimicrobial, anti-oxidant, anti-thrombotic, and carcinostatic activities; it has been studied for its applications in the food, cosmetic, and pharmaceutical fields (Ou and Kwok 2004;Pei et al 2015;Takahashi et al 2015).…”

Polyethylene ferulate (PEF) and congeners: polystyrene mimics derived from biorenewable aromatics

“…Hydroxyethylcoumaric methylester has been investigated as a comonomer for photocrosslinkable polymers. 20 Meier et al 21 discovered polycondensation of hydroxyethyldihydroferulic methylester to form polyethylene dihydroferulate (cf., Table 1, entry 2) using triazabicyclodecene (TBD) as an organocatalyst. 20 Meier et al 21 discovered polycondensation of hydroxyethyldihydroferulic methylester to form polyethylene dihydroferulate (cf., Table 1, entry 2) using triazabicyclodecene (TBD) as an organocatalyst.…”