Isocyanate-Free Fully Biobased Star Polyester-Urethanes: Synthesis and Thermal Properties

Quienne, Baptiste; Kasmi, Nejib; Dieden, Reiner; Caillol, Sylvain; Habibi, Youssef

doi:10.1021/acs.biomac.0c00156

Cited by 43 publications

(20 citation statements)

References 36 publications

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“…Hydroxyurethane moieties have also been incorporated as side-groups in fluorinated, alternating copolymers 22 and polyester-graft-poly(ethylene glycol) brush copolymers, 23 and recently biobased ester-urethane star polymers based on glycerol and dimethyl-2,5furan dicarboxylate were reported. 24 Hence, PHUs with diverse microstructures can be achieved and hydroxyurethane functionalities can be used to decorate various polymer backbones, but copolymers with a PHU block or more complex architectures are lacking, especially when considering synthesis conditions devoid of solvents and hazardous reagents.…”

Section: Introductionmentioning

confidence: 99%

Solubility-governed architectural design of polyhydroxyurethane-graft-poly(ε-caprolactone) copolymers

2021

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Section: Introductionmentioning

confidence: 99%

Solubility-governed architectural design of polyhydroxyurethane-graft-poly(ε-caprolactone) copolymers

2021

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“…Varying the stoichiometric ratio of the reactive functional groups in a crosslinking polymerization results in changes in the thermophysical and thermomechanical properties of the formed network, as reported in literature for irreversible network polymerizations, such as epoxy-amine reactions [ 19 , 20 , 21 ] and polyester formation [ 22 ]. Moreover, changing the (ratio between the) concentrations of the functional groups results in important changes in the kinetics of the polymerization reactions.…”

Section: Resultsmentioning

confidence: 99%

The Influence of the Furan and Maleimide Stoichiometry on the Thermoreversible Diels–Alder Network Polymerization

et al. 2021

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In recent work, the thermoreversible Diels–Alder reaction between furan and maleimide functional groups has been studied extensively in the context of self-healing elastomers and thermosets. To elaborate the influence of the stoichiometric ratio between the maleimide and furan reactive groups on the thermomechanical properties and viscoelastic behavior of formed reversible covalent polymer networks, a series of Diels–Alder-based networks with different stoichiometric ratios was synthesized. Differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA) and dynamic rheology measurements were performed on the reversible polymer networks, to relate the reversible network structure to the material properties and reactivity. Such knowledge allows the design and optimization of the thermomechanical behavior of the reversible networks for intended applications. Lowering the maleimide-to-furan ratio creates a deficit of maleimide functional groups, resulting in a decrease in the crosslink density of the system, and a consequent decrease in the glass transition temperature, Young’s modulus, and gel transition temperature. The excess of unreacted furan in the system results in faster reaction and healing kinetics and a shift of the reaction equilibrium.

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“…The TGA curves under pure nitrogen flow show three stages of decomposition (Figure a). The first stage of decomposition in the range of 150–200 °C was mainly due to the breakage of ester linkages . BPE-B1 and BPE-B2 displayed much higher thermal stability with higher T d5 s (200 and 207 °C) and higher residues (30.5 and 31.0%).…”

Section: Resultsmentioning

confidence: 99%

Novel “Rigid to Flexible” Biobased Polyesters Fully Derived from 5-Hydroxymethylfurfural: Promising as Sustainable UV Shielding and Gas Barrier Materials

Jing

et al. 2022

ACS Sustainable Chem. Eng.

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A series of novel biobased polyesters are synthes i z e d b y i n t r o d u c i n g d i f u r a n y l m o n o m e r s -b i s -(hydroxymethylfurfuryl)amines (BHMFAs) and 2,5-furandicarboxylate (FDCA) for the first time under mild condensation conditions, in which both FDCA and BHMFAs are derived from the biomass platform chemical 5-hydroxymethylfurfural. The special structure of the polyesters, in which the structural repeating unit contains three furan rings and alterable side chains (ethyl, heptyl, dodecyl, benzyl, and phenethyl groups), endows their controllable performance, conformation, and free volume. The results showed that all of the polyesters are amorphous, confirmed by the results of DSC, XRD, and density functional theory. Different side chains of the polyesters result in T g s varying from 3.5 to 51.6 °C, tensile moduli from 3 to 551 MPa, and elongations at break from 13 to 1100%. Significantly, the polyester with phenethyl as the side chain shields ∼100% UV light. The polyester with benzyl as the side chain reduces gas permeability coefficients (PCO 2 and PO 2 ) by approximately three times compared with poly (ethylene terephthalate) (PET), which can be well explained by fractional free volume calculation results from molecular dynamics simulation. In addition, the polyesters show high dielectric constants (ε = 4.01−4.58) and maintain relatively low dielectric loss (tanδ = 0.023−0.043). This work provides strategies for designing and synthesizing biopolyesters with rigid to flexible structures, excellent UV shielding, gas barriers, and dielectric properties by varying the structure of the side chains and by introducing the difuran ring group.

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Isocyanate-Free Fully Biobased Star Polyester-Urethanes: Synthesis and Thermal Properties

Abstract: Fully biobased isocyanate free polyester-urethanes with interesting properties were prepared by combination of biobased diamine, carbon dioxide and sugar-derived diacids.

Cited by 43 publications

References 36 publications

Solubility-governed architectural design of polyhydroxyurethane-graft-poly(ε-caprolactone) copolymers

Solubility-governed architectural design of polyhydroxyurethane-graft-poly(ε-caprolactone) copolymers

The Influence of the Furan and Maleimide Stoichiometry on the Thermoreversible Diels–Alder Network Polymerization

Novel “Rigid to Flexible” Biobased Polyesters Fully Derived from 5-Hydroxymethylfurfural: Promising as Sustainable UV Shielding and Gas Barrier Materials

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