Solvent- and catalyst-free synthesis of fully biobased nonisocyanate polyurethanes with different macromolecular architectures

Carré, C.; Bonnet, Lara; Avérous, Luc

doi:10.1039/c5ra17638g

Cited by 56 publications

(56 citation statements)

References 37 publications

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“…[137] ChemSusChem 2019, 12,724 -754 www.chemsuschem.org 2019 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim Dimers of fatty acids (DFA) can be generatedb yD iels-Alder reactiont oo btain renewable dicarboxylica cids. [156] 4v was reacted with renewable diamines for the synthesis of PHU networks with high renewable content. Polymeric compounds are also generally present (the structures in Figure 4a re representativeso ft he dimericc ompounds).…”

Section: Terminal Biscarbonatesmentioning

confidence: 99%

“…[155] 4v was obtained by Averous and co-workers from the reaction of the bisacyl halide of aD FA (Radiacid 0970) with two equivalents of GC. [156] 4v was reacted with renewable diamines for the synthesis of PHU networks with high renewable content. Similarly, 4w was prepared by the esterification of commercially availableP ripol 1009 (hydrogenated dimerized linoleic acid) with GC, by using nonrenewable coupling reagents such as 1,3-dicyclohexylcarbodiimide (DCC, 2equiv) and employed for the synthesis PHUs in bulk and miniemulsion processes.…”

Section: Terminal Biscarbonatesmentioning

confidence: 99%

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Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

et al. 2019

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Given the large amount of anthropogenic CO2 emissions, it is advantageous to use CO2 as feedstock for the fabrication of everyday products, such as fuels and materials. An attractive way to use CO2 in the synthesis of polymers is by the formation of five‐membered cyclic organic carbonate monomers (5CCs). The sustainability of this synthetic approach is increased by using scaffolds prepared from renewable resources. Indeed, recent years have seen the rise of various types of carbonate syntheses and applications. 5CC monomers are often polymerized with diamines to yield polyhydroxyurethanes (PHU). Foams are developed from this type of polymers; moreover, the additional hydroxyl groups in PHU, absent in classical polyurethanes, lead to coatings with excellent adhesive properties. Furthermore, carbonate groups in polymers offer the possibility of post‐functionalization, such as curing reactions under mild conditions. Finally, the polarity of carbonate groups is remarkably high, so polymers with carbonates side‐chains can be used as polymer electrolytes in batteries or as conductive membranes. The target of this Review is to highlight the multiple opportunities offered by polymers prepared from and/or containing 5CCs. Firstly, the preparation of several classes of 5CCs is discussed with special focus on the sustainability of the synthetic routes. Thereafter, specific classes of polymers are discussed for which the use and/or presence of carbonate moieties is crucial to impart the targeted properties (foams, adhesives, polymers for energy applications, and other functional materials).

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Section: Terminal Biscarbonatesmentioning

confidence: 99%

Section: Terminal Biscarbonatesmentioning

confidence: 99%

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

et al. 2019

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“…Although the use of 1,4-butanediamine led to thermoset material, a material with properties of a partially cross-linked elastomer was obtained with aminated oligomers [116]. Fully fatty-acid derived NIPU were synthesized by Averous et al [117]. Bis(cyclic carbonate)s were synthesized from dimerized fatty acid by halogenation employing toxic and corrosive thionyl chloride, followed by esterification with glycerol carbonate.…”

Section: Polyurethane Resinsmentioning

confidence: 99%

Sustainable Synthetic Approaches for the Preparation of Plant Oil‐Based Thermosets

Llevot

2016

J Americ Oil Chem Soc

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a more sustainable future. Due to an ever-increasing population on our planet and industrial developments, a major focus is on energy and fuel supply, as well as chemical and polymer production. In search for alternatives to the finite fossil feedstocks, the renewability and structural diversity of biomass makes it an excellent candidate [1][2][3][4][5][6]. Especially in polymer science, the use of renewable resources has been intensively investigated and discussed in several reviews over the last years [7][8][9][10][11]. Amongst biomass, vegetable oils constitute a platform of aliphatic hydrocarbons, particularly studied as polymer precursors due to their good availability, low price, inherent biodegradability and potential for chemical modifications [12][13][14][15][16]. Vegetable oils are composed of triglycerides, which consist of three fatty acid chains esterified with glycerol. Fatty acids vary in their chain length, as well as degree and location of their unsaturations. The fatty acid structures of the plant oils discussed in this review are shown in Scheme 1 and the composition of these oils displayed in Table 1. The fatty acid composition of the triglycerides, depending on the plant origin, influences their properties significantly [14]. Well-defined fatty acids can be recovered after hydrolysis of triglycerides and further separation and purification [17]. The latter can be transformed into difunctional monomers for the synthesis of a broad range of thermoplastic polymers [18]. However, this additional step decreases the sustainability of the synthesis. Thus, the direct polymerization of poly-functional vegetable oils into thermoset polymers represents a "greener" approach towards polymeric materials.Thermosets are cross-linked polymeric materials known for their good thermomechanical properties and chemical resistance. The production of these polymers represents ~20% of the total annual polymer production [19]. Thermosets can be synthesized in different chemical ways and the production of biobased thermosets has been recently Abstract The good availability and high degree of functionalization possibilities of plant oils entitles them to be one of the most intensively studied renewable resources, especially in polymer science. However, in line with the principles of green chemistry, the use of renewable resources should be accompanied with catalytic procedures, comparably less or non-toxic chemicals, as well as reduction of waste and energy consumption to achieve an overall sustainable process. In this review, these aspects are addressed using the example of plant oil-based thermoset materials, which bear the advantage, in terms of sustainability, of not requiring a separation or purification step prior to polymerization. The direct homopolymerization of plant oils, as well as copolymerization, exclusively with other renewable resources, are highlighted. The sustainability of the synthesis of a broad range of thermosets including epoxy resins, polyurethane networks, polybenzoxazines and unsaturated poly...

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“…In 2015, Rokicki et al [27] and Maisonneuve et al [28] were published two reviews on NIPUs on their of synthesis, properties and applications. Moreover, recently Carré et al [29] describes the syntheses of novel and fully biobased NIPU via a green chemistry process, without solvent and catalysts from vegetable oils.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of epoxyurethane polymers from isocyanate free oligo-polyhydroxyurethane

Cornille¹,

Serres²,

Michaud³

et al. 2016

European Polymer Journal

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Solvent- and catalyst-free synthesis of fully biobased nonisocyanate polyurethanes with different macromolecular architectures

Abstract: A bis(cyclic carbonate) based on a dimeric fatty acid was successfully synthesized.

Cited by 56 publications

References 37 publications

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

Sustainable Synthetic Approaches for the Preparation of Plant Oil‐Based Thermosets

Syntheses of epoxyurethane polymers from isocyanate free oligo-polyhydroxyurethane

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Solvent- and catalyst-free synthesis of fully biobased nonisocyanate polyurethanes with different macromolecular architectures

Abstract: A bis(cyclic carbonate) based on a dimeric fatty acid was successfully synthesized.

Cited by 56 publications

References 37 publications

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

Sustainable Synthetic Approaches for the Preparation of Plant Oil‐Based Thermosets

Syntheses of epoxyurethane polymers from isocyanate free oligo-polyhydroxyurethane

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Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization