Non-isocyanate polyurethane foams based on six-membered cyclic carbonates

Coste, Guilhem; Berne, Dimitri; Ladmiral, Vincent; Négrell, Claire; Caillol, Sylvain

doi:10.1016/j.eurpolymj.2022.111392

Cited by 19 publications

(17 citation statements)

References 41 publications

(51 reference statements)

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“…Literature summarized the reactivity of 5-, 6-, and 7-membered cyclic carbonates and identified their reactivity in the following order: CC5 < CC6 < CC7 < CC8. [60,61] Therefore, CC5 received a great deal of attention despite having lower reactivity than CC6, CC7, and CC8 because the synthesis of higher-order cyclic carbonates requires the use of hazardous precursors such as phosgene, ethyl chloroformate, or CS 2 . [62] It was observed that the six-and seven-membered cyclic carbonates are more reactive with amines and polymerize at a faster rate than the five-membered cyclic carbonates.…”

Section: Selection Of the CCmentioning

confidence: 99%

Innovations in applications and prospects of non‐isocyanate polyurethane bioplastics

Mangal,

H.,

Bose

et al. 2023

Biopolymers

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Currently, conventional plastics are necessary for a variety of aspects of modern daily life, including applications in the fields of healthcare, technology, and construction. However, they could also contain potentially hazardous compounds like isocyanates, whose degradation has a negative impact on both the environment and human health. Therefore, researchers are exploring alternatives to plastic which is sustainable and environmentally friendly without compromising its mechanical and physical features. This review study highlights the production of highly eco‐friendly bioplastic as an efficient alternative to non‐biodegradable conventional plastic. Bioplastics are produced from various renewable biomass sources such as plant debris, fatty acids, and oils. Poly‐addition of di‐isocyanates and polyols is a technique employed over decades to produce polyurethanes (PUs) bioplastics from renewable biomass feedstock. The toxicity of isocyanates is a major concern with the above‐mentioned approach. Novel green synthetic approaches for polyurethanes without using isocyanates have been attracting greater interest in recent years to overcome the toxicity of isocyanate‐containing raw materials. The polyaddition of cyclic carbonates (CCs) and polyfunctional amines appears to be the most promising method to obtain non‐isocyanate polyurethanes (NIPUs). This method results in the creation of polymeric materials with distinctive and adaptable features with the elimination of harmful compounds. Consequently, non‐isocyanate polyurethanes represent a new class of green polymeric materials. In this review study, we have discussed the possibility of creating novel NIPUs from renewable feedstocks in the context of the growing demand for efficient and ecologically friendly plastic products.

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Section: Selection Of the CCmentioning

confidence: 99%

Innovations in applications and prospects of non‐isocyanate polyurethane bioplastics

Mangal,

H.,

Bose

et al. 2023

Biopolymers

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“…[ 54 ] Various authors have thus taken advantage of this reaction to synthesize bis‐cyclic carbonates by grafting cyclic carbonates on polythiols backbones of different structures. [ 18,55–63 ]…”

Section: Synthesis Of Multifunctional Monomersmentioning

confidence: 99%

“…More recently, Coste et al synthesized a 6CC tetrafunctional monomer by reacting TMPAE with a tetrathiol, the pentaerythritol tetrakis(3‐mercaptopropionate), using similar conditions and achieving 87% yield. [ 63 ]…”

Section: Synthesis Of Multifunctional Monomersmentioning

confidence: 99%

“…synthesized catalyst‐free PHU foams in mild temperature conditions, by using a liquid 6CC tetrafunctional monomer, which is known for being more reactive than 5CC monomers ( Figure ). [ 63 ] The tetracarbonate, synthesized by thiol‐ene reaction beforehand, is manually mixed with PMHS, the same foaming agent as the one used by Cornille et al [ 107 ] The amine is then added to the mixture before injection in a silicone mold. Particular attention was paid to the selection of liquid diamines, in particular IPDA, mxDA, and 5DA, in order to ensure the homogeneity of the medium.…”

Section: Synthesis Of Thermosetting Phus: High‐ Versus Low‐temperatur...mentioning

confidence: 99%

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Design of Plurifunctional Cyclocarbonates and their Use as Precursors of Poly(hydroxyurethane) Thermosets: A Review

Helbling,

Hermant,

Petit

et al. 2023

Macro Chemistry & Physics

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Polyhydroxyurethanes (PHUs) are promising polymers to replace polyurethanes (PUs), classically obtained by the isocyanate‐alcohol route. Various application fields of PUs, e.g. foams or coatings, require the use of thermosetting polymers. Hence, a great deal of effort has been devoted to the development of PHU thermosets in the recent literature. This review highlights the different strategies developed through the years to synthesize plurifunctional cyclic carbonates, also called poly(cyclic carbonate)s, and whose functionality ≥ 3 is a prerequisite for the synthesis of thermosetting PHUs. A special emphasize is accorded to the safe and eco‐friendly synthetic approaches (e.g., phosgene‐free, use of renewable reactants). In addition, the curing strategies implemented to overcome the low reactivity of the monomers and the limitations related to the transitions of the growing networks (i.e., viscosification, gelation, vitrification) are described. In the end, the curing of PHUs under mild thermal conditions, down to room temperature, is described. Such curing conditions are uncommon for PHU thermosets and are paving the way to much anticipated applications such as coatings, adhesives or 3D‐printing.This article is protected by copyright. All rights reserved

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“…Cornille et al reported the first NIPU foam utilizing hydrogen gas (H 2 ) generated from poly(methylhydrogenosiloxane) (Momentive MH 15) . This approach was also used to prepare epoxy-based foams and other NIPU foams. − However, the generation of flammable gas is a significant concern during production. Physical blowing agents such as Solkane − (hydrofluorocarbon) and supercritical CO 2 , chemical blowing agents such as CO 2 generated from maleic acid/citric acid , and NaHCO 3 were also studied for preparing NIPU foams.…”

mentioning

confidence: 99%

CO₂-Blown Nonisocyanate Polyurethane Foams

2023

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Polyurethane (PU) foams are produced from toxic, petrochemical- and phosgene-derived isocyanates. Although nonisocyanate polyurethane (NIPU) has shown promise as a replacement for traditional PU, the synthesis of NIPU foams has not been widely studied due to the difficulties in replicating the foaming process of PU, in situ CO2 production through the hydrolysis of isocyanates. Hereby, we report the synthesis of amine-CO2 adducts and their CO2 adsorption–desorption characteristics under different conditions. The results show that the amine-CO2 adducts can exhibit up to 87% CO2 desorption at 60 °C after aminolysis with cyclic carbonate. The amine-CO2 adduct is used as both a foaming agent and a comonomer to obtain low-density foams (0.203–0.239 g·cm–3) after heating at 50–60 °C for 24–48 h. This marks the successful synthesis of in situ CO2-blown NIPU foams using an amine-CO2 adduct.

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Non-isocyanate polyurethane foams based on six-membered cyclic carbonates

Cited by 19 publications

References 41 publications

Innovations in applications and prospects of non‐isocyanate polyurethane bioplastics

Innovations in applications and prospects of non‐isocyanate polyurethane bioplastics

Design of Plurifunctional Cyclocarbonates and their Use as Precursors of Poly(hydroxyurethane) Thermosets: A Review

CO₂-Blown Nonisocyanate Polyurethane Foams

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Non-isocyanate polyurethane foams based on six-membered cyclic carbonates

Cited by 19 publications

References 41 publications

Innovations in applications and prospects of non‐isocyanate polyurethane bioplastics

Innovations in applications and prospects of non‐isocyanate polyurethane bioplastics

Design of Plurifunctional Cyclocarbonates and their Use as Precursors of Poly(hydroxyurethane) Thermosets: A Review

CO2-Blown Nonisocyanate Polyurethane Foams

Contact Info

Product

Resources

About

CO₂-Blown Nonisocyanate Polyurethane Foams