A novel bio-based AB₂monomer for preparing hyperbranched polyamides derived from levulinic acid and furfurylamine

Abstract

A new AB2 type bio-based monomer (FDA-E) with two amino functional groups and one ester functional group was prepared from renewable levulinic acid and furfurylamine using a three-step reaction.

Recent development on bio‐based thermosetting resins

“…159 In addition, the condensation between two units of natural phenol can obtain bisphenol, while diol can be converted into diamine under certain conditions, both of which are feasible strategy for the preparation of di-unit bio-based benzoxazine. [161][162][163] Although there are fewer triphenols available in nature, in which the resveratrol and apigenin are successfully used to synthesize trifunctional benzoxazine. 163,164…”

“…[161][162][163] Although there are fewer triphenols available in nature, in which the resveratrol and apigenin are successfully used to synthesize trifunctional benzoxazine. 163,164…”

“…Daidzein is subject to flavonoids, the benzoxazine resin (Scheme 17) possess an unique benzopyranone structure, leading to the resin with not only intrinsic flame retardancy but also antibacterial potential 159 . In addition, the condensation between two units of natural phenol can obtain bisphenol, while diol can be converted into diamine under certain conditions, both of which are feasible strategy for the preparation of di‐unit bio‐based benzoxazine 161–163 . Although there are fewer triphenols available in nature, in which the resveratrol and apigenin are successfully used to synthesize trifunctional benzoxazine 163,164 …”

Recent advances on synthesis and biomaterials applications of hyperbranched polymers

“…Despite this, some special monomers have been designed to deviate this equal reactivity scenario, creating an accelerating reaction of the second B group than the first B group to vary the reaction kinetics, polymer molecular weight and to achieve higher DB than 0.5 (Segawa, Higashihara, & Ueda, 2013). A diverse range of monomers based on various organic reactions has been reported to achieve hyperbranched polymers through step‐growth mechanism, including polyesterfication (Hawker, Lee, & Frechet, 1991), polyetherification (Liu et al, 2014; Uhrich, Hawker, Frechet, & Turner, 1992), polyamidation (Uhrich, Boegeman, Fréchet, & Turner, 1991; Yamakawa, Ueda, Takeuchi, & Asai, 1999; Yang, Wu, Liu, Qiu, & Liu, 2019), palladium‐catalyzed Suzuki coupling (Monomer 3, Table 1; Xue et al, 2010), and copper‐catalyzed azide‐alkyne cycloaddition (CuAAC) reactions (Cao, Shi, Wang, Graff, & Gao, 2016; Gan, Cao, Shi, Zou, & Gao, 2018; Shi et al, 2015; Shi, Cao, Zou, et al, 2016), among many others. Recently, acid‐catalyzed Friedel‐Crafts substitution of aromatic AB 2 monomers, consisting of both an electron‐rich arene and a maleic functionality, resulted in hyperbranched polymers with DB = 100% made possible by accelerated rate of the intermediate species (Yang & Kong, 2016).…”

Base-Free Synthesis of Furfurylamines from Biomass Furans Using Ru Pincer Complexes

“…One of the most powerful and robust methods for effective C-N bond formation of amines is the reductive amination of carbonyl compounds. [4,[18][19][20][21][22][23][24][25][26][27][28][29][30]. This transformation features compelling advantages, such as simple operating setups, mild reaction conditions, direct use of available substrates, and inexpensive reagents [31].…”