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

Pion, Florian; Armando, Félix Reano; Mouandhoime, Zahahe; Barbara, Isabelle; Flourat, Amandine L.; Ducrot, Paul‐Henri; Allais, Florent

doi:10.1021/bk-2015-1192.ch004

Cited by 12 publications

(8 citation statements)

References 108 publications

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“…[32][33][34] Due to the fused rings structure, isosorbide has a relatively high thermostability and low segmental mobility, and can be used to improve the glass transition temperatures of polyesters. [35][36][37][38][39][40][41] Furthermore, the larger steric hindrance of isosorbide will remarkably affect the crystallization kinetics and melting behaviors.…”

Section: Introductionmentioning

confidence: 99%

Biobased copolyesters from renewable resources: synthesis and crystallization kinetics of poly(propylene sebacate-co-isosorbide sebacate)

Zhou

Wei

et al. 2015

RSC Adv.

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In this work, a series of novel biobased copolymers, poly(propylene sebacate-co-isosorbide sebacate) (P(PSe-co-IS)), were synthesized by melt-polycondensation from sebacic acid (SA) and isosorbide (IS) with 1,3-propanediol (PD). In order to analyze the effects of isosorbide on the relative properties of poly(propylene sebacate) (PPSe), the composition, crystal structure, crystallization behavior, multiple melting behavior, and spherulitic morphology of these copolymers were investigated by 1 H-NMR, WAXD, DSC, TMDSC and POM, respectively. Results of 1 H-NMR indicated that IS have been successfully introduced into the PPSe main chains with the designed molar ratio. DSC data showed that crystallization ability of P(PSe-co-IS) copolymers was retarded with the introduction of IS. With the increment of IS, the overall crystallization rate decreased gradually. Furthermore, crystallization temperature (T c ), crystallization enthalpy (DH c ), melting temperature (T m ), and equilibrium melting temperature (T o m ) of P(PSe-co-IS) copolymers also decreased apparently with the increase of IS content. WAXD suggested that crystal structure of PPSe was not affected by IS, and POM revealed that all spherulites possess the typical "Maltese Cross" image. Furthermore, no obvious ring-banded spherulites could be detected for P(PSe-co-IS) copolymers in the wide temperature range except neat PPSe due to the hindrance of IS. With the increment of IS and crystallization temperature, the number of spherulites decreased rapidly and the size of spherulites increased, respectively.

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Section: Introductionmentioning

confidence: 99%

Biobased copolyesters from renewable resources: synthesis and crystallization kinetics of poly(propylene sebacate-co-isosorbide sebacate)

Zhou

Wei

et al. 2015

RSC Adv.

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“…For example, it was employed as the starting material by Pion et al (34) and Nguyen et al (54). A large number of polycyanurates from phenolic structures from renewable resources were studied in the chapter by Guenthner et al (56).…”

Section: Biobased Feedstockmentioning

confidence: 99%

Green Polymer Chemistry: Some Recent Developments and Examples

Cheng

Gross

Smith

2015

ACS Symposium Series

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“…Thus, creating high-value molecules from lignin appears to be a promising field of research. In particular, phenolic monomers show miscellaneous applications in different fields: anti-oxidant [ 4 ], anti-UV [ 5 , 6 ], or polymers [ 7 ]. However, today, they remain mostly derived from fossil resources.…”

Section: Introductionmentioning

confidence: 99%

Inhibition of Phenolics Uptake by Ligninolytic Fungal Cells and Its Potential as a Tool for the Production of Lignin-Derived Aromatic Building Blocks

Leriche-Grandchamp

Flourat

Shen

et al. 2020

JoF

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Lignin is the principal natural source of phenolics but its structural complexity and variability make it difficult to valorize through chemical depolymerization approaches. White rots are one of the rare groups of organisms that are able to degrade lignin in ecosystems. This biodegradation starts through extracellular enzymes producing oxidizing agents to depolymerize lignin and continue with the uptake of the generated oligomers by fungal cells for further degradation. Phanerochaete chrysosporium is one of the most studied species for the elucidation of these biodegradation mechanisms. Although the extracellular depolymerization step appears interesting for phenolics production from lignin, the uptake and intracellular degradation of oligomers occurring in the course of the depolymerization limits its potential. In this study, we aimed at inhibiting the phenolics uptake mechanism through metabolic inhibitors to favor extracellular oligomers accumulation without preventing the ligninases production that is necessary for extracellular depolymerization. The use of sodium azide confirmed that an active transportation phenomenon is involved in the phenolics uptake in P. chrysosporium. A protocol based on carbonyl cyanide m-chlorophenyl hydrazone enabled reaching 85% inhibition for vanillin uptake. This protocol was shown not to inhibit, but on the contrary, to stimulate the depolymerization of both dehydrogenation polymers (DHPs) and industrial purified lignins.

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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

Cited by 12 publications

References 108 publications

Biobased copolyesters from renewable resources: synthesis and crystallization kinetics of poly(propylene sebacate-co-isosorbide sebacate)

Biobased copolyesters from renewable resources: synthesis and crystallization kinetics of poly(propylene sebacate-co-isosorbide sebacate)

Green Polymer Chemistry: Some Recent Developments and Examples

Inhibition of Phenolics Uptake by Ligninolytic Fungal Cells and Its Potential as a Tool for the Production of Lignin-Derived Aromatic Building Blocks

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