Biomass-Derived Poly(ether-amide)s Incorporating Hydroxycinnamates

Abstract

Lignin-derived chemicals have great potential as feedstock to produce polymeric materials, due to the low cost and high abundance of lignin biomass. Lignin is one of the few nonpetroleum sources of aromatic carbon, a desirable moiety in high-performance polymers. Herein we describe the synthesis and characterization of a series of 21 poly­(ether-amide)­s that incorporate hydroxycinnamates derived from lignin. Three different hydroxycinnamates (coumaric acid, ferulic acid, sinapinic acid) were incorporated into dimers, and then copolymerized with a series of seven aliphatic and aromatic diamines via interfacial polymerization. The resultant polymers exhibited poor solubility in standard organic solvents (excluding DMF), but exhibited moderate glass transition temperatures and moderate thermal stabilities. Additionally, the polymers exhibit excellent resistance to hydrolysis. The modularity of this synthetic approach could be used to rapidly generate diverse polymers with a broad range of well-tuned properties.

Improving thermal and mechanical properties of biomass-based polymers using structurally ordered polyesters from ricinoleic acid and 4-hydroxycinnamic acids

“…In this case, the increase in T g was explained in terms of limited polymer-chain rotational exibility due to steric effect. 47 At present, the increase in T g through the introduction of methoxy groups in our study is believed to be due to the latter reason. Note that the crystallisation temperature (T c ) and the melting temperature (T m ) were observed only for P(CA-alt-RA) (Fig.…”

Influence of different amino functional groups on structural, optical, and morphological properties of PMMA and their nanocomposites

“…The protons of amide group (–CO–NH–) and carboxylic acid group (–COOH) were acidic in nature so there were good possibility to get exchange with deuterium of solvent, therefore their peak in NMR spectrum were not observed. [ 26,27 ] The absence of chemical shift for (–CO–NH–) confirms the formation of amide group which also support that PMMA was successfully attached with the amine moieties. The prominent peak for proton of β‐amine were observed at ~3.5 ppm [ 28 ] and the slight variation in the chemical shift may be due to the presence of different moieties attached with the amine group.…”

Substituent Effects on Thermal and Mechanical Properties of Resorcinol‐Based Semiaromatic Polyesters

“…This is because the introduction of methyl substituents into resorcinol caused the restriction in the rotational flexibility of polymer chains. [ 36,37 ] Besides, the T g of the polyesters with the same resorcinol unit except P(R‐Gl) declined as the dicarboxylic acid unit became longer (P(R‐Ad) > P(R‐Pi), P(2MR‐Gl) > P(2MR‐Ad) > P(2MR‐Pi), P(5MR‐Gl) > P(5MR‐Ad) > P(5MR‐Ad), P(25MR‐Gl) > P(25MR‐Ad) > P(25MR‐Pi)). This can be explained by the increase in their free volume due to the introduction of soft segments into the polymer backbone.…”