Synthesis of new biobased linear poly(ester amide)s

Abstract

In the present work, we investigated the synthesis of new biobased linear aliphatic PEAs with a controlled regicity, in a two steps procedure. First, dioldiamide derivatives were successfully synthesized, then polycondensation reaction using the usual alcohol plus acid reaction was performed. NMR analyses demonstrate that dioldiamide can be synthesized in one step from diacid and ethanolamine condensation with high conversion. A new library of polymers was then synthesized, and characterized. Overall, the reactivity of amine or alcohol or acid functions is investigated by in-depth 1 H and 13 C NMR versus HSQC NMR analysis. These results can be used to follow the complex evolution of monoesterification or diesterification reactions, monoamidation or diamidation reactions when dicarboxylic acids versus alcohol or amine are reacted. Thermal degradation was examined, and a good stability of all the polymers was evidenced. The thermal properties of the polymers were also analyzed, and high melting temperatures were measured, thanks to the control of the regicity. Comparing the melting and crystallization temperature revealed a fast rate of crystallization, an important feature for polymer melt processing. The solubility behavior of these polymers was found to be close to the one of polyamides, suggesting the use of this new polymers library to replace polyamides in applications where biodegradability of the materials is required.

Synthesis, Properties, and Biodegradation of Sequential Poly(Ester Amide)s Containing γ-Aminobutyric Acid

“…The poly(ester amide)s showed two stage decomposition behavior in TG. Similar two step thermal degradation behaviors were observed for some reported poly(ester amide)s, where the first degradation step was assigned to the ester bond cleavage [34,49,50]. All the poly(ester amide)s showed higher T d5 values than that of PA4 [24] as indicated in Table 2.…”

“…Poly(ester amide)s are polymers having both ester and amide bonds in their polymer main chains [25][26][27][28][29][30][31][32][33][34]. Poly(ester amide)s with aliphatic ester moieties can possess both biodegradability for aliphatic ester bonds and excellent physical properties due to the amide bonds.…”

“…As PA4 has been reported to be biodegradable in seawater [22,37], we expected that the poly(ester amide)s containing GABA units could also be the polymers biodegradable in seawater. In addition [38], the copolymers with regular sequences such as alternating and periodic copolymers could have some specific properties such as higher melting temperature (T m ) and/or glass-transition temperature (T g ) not expected from those of the corresponding homopolymers [39], in comparison with the corresponding random copolymers [12,25,34,38]. In this study, we synthesized a series of new sequential poly(ester amide)s containing GABA unit and investigated their thermal properties and biodegradabilities in seawater and in activated sludge.…”

Hybrid alkyds, the glowing route to reach cutting-edge properties?

“…Polyamide are characterized by -CONH groups that lead to hydrogen bonds between them, conferring high strength and mechanical properties to the polymer, despite low molecular weight. [118][119][120] Polyamides have been introduced into alkyds in order to improve the thixotropy, a rheological property of the resin. Thixotropy is defined as the continuous decrease of viscosity with time when flow is applied to a sample that has been previously at rest and the subsequent recovery of viscosity in time when the flow is discontinued.…”

Synthesis and Characterization of Partially Renewable Oleic Acid-Based Ionomers for Proton Exchange Membranes

“…Thus, affording materials in an environmentally friendly way and, consequently, reducing the use of non-renewable resources, is the main reason why the chemical industry is constantly pursuing alternatives for the synthesis of new polymers using precursors obtained from natural resources such as vegetable oils, saccharides, and biomass, among others that are available on a large scale and can be effectively used as monomers [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. These renewable polymers have to be produced at low cost, with few steps for their synthesis and should also have properties comparable with their counterparts obtained from petrochemical compounds in order to be used on a commercial scale [ 11 , 12 ]. In this regard, vegetable oils containing unsaturated fatty acids are promising, cheap, and renewable sources to generate a huge number of oleochemicals that can be employed for the synthesis of high-value compounds in a sustainable manner [ 13 , 14 ].…”