Facile preparation of polycarbonates from bio-based eugenol and 2-methoxy-4-vinylphenol

Abstract

<p>Polymerization of α,ω-diene functionalized carbonate monomers prepared from bio-based eugenol and 2-methoxy-4-vinylphenol through thiol–ene click and ADMET polymerizations produced polycarbonates with moderate molecular weight satisfactory thermal properties.</p>

Eugenol‐derived Organic Liquids as an In‐Situ CO2 Capturing and Conversion System for Eugenol‐based Polycarbonate Synthesis

“…Furthermore, the enhancement of the polymer polarity will form a stronger dipole‐dipole interaction, which also leads to an increase in T g of a polymer. The phenomenon was also observed in similar polymers [9,28] . A similar tendency was also observed in terms of the effect of the length of the aliphatic segments in aliphatic α,ω‐diene chains on the T g , as the T g s of P2a and P2b are 20 °C and 12 °C, respectively (Figure 3f).…”

“…The phenomenon was also observed in similar polymers. [9,28] A similar tendency was also observed in terms of the effect of the length of the aliphatic segments in aliphatic α,ω-diene chains on the T g , as the T g s of P2a and P2b are 20 °C and 12 °C, respectively (Figure 3f). All the carbons in the aliphatic chain are sp3 carbon in PH2b, however, the carbons in the carbon-carbon double bonds in P2b are sp2 carbon.…”

“…The monomers 2a-b were featured by α,ω-diene functional groups, implying that they were applicable for ADMET and thiol-ene click chemistry polymerization, which have been proven to be efficient polymerization methods. [9,23,27,28] To our delight, series of novel polycarbonates were successfully achieved. For example, the metal-free thiol-ene polymerization of 2a with 1,2-ethanedithiol (3a) (Scheme 3) produced a poly(thioether carbonate) P2a3a with a Mw of 29.7 kDa and a polydispersity index (Đe) of 1.6 in 94% yield.…”

Bio-based poly(ester-alt-thioether)s synthesized by organo-catalyzed ring-opening copolymerizations of eugenol-based epoxides and N-acetyl homocysteine thiolactone

“…34 More generally, similar degradation temperatures have been observed for polymers containing thioether bonds in their backbone, suggesting that carbonsulfur bond is the weakest linkage in the structure. 26,40 The remaining residual weights of poly(NHTLalt-DEGE) and poly(NHTL-alt-EGE) at 600°C are equal to 8.0 and 11.9 %, respectively. Linear aliphatic sections are known to decompose almost completely compared to double bonds and aromatic sections under the same TGA conditions.…”

“…Several examples can be found where Eugenol derivatives have been used in step growth polymerizations, resulting in various polymer backbone natures, such as aromatic polyesters, 24 poly(ester-thioether)s, 25 polycarbonates, 26 or poly(anhydride)s. 27 However, polycondensation reactions only enable a limited control of the polymer structure with high dispersities and no control of the chain ends. Eugenol-based monomers have been scarcely used in chain-growth polymerization.…”