Synthesis of reactive phosphorus-based carbonate for flame retardant polyhydroxyurethane foams

Coste, Guilhem; Denis, Maxinne; Sonnier, Rodolphe; Caillol, Sylvain; Négrell, Claire

doi:10.1016/j.polymdegradstab.2022.110031

Cited by 14 publications

(8 citation statements)

References 47 publications

(65 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…MBDA has been chosen for its structure that contains aromatic rings, which would provide char formation during combustion. Moreover, in a previous study, MBDAC exhibited better results than other epoxies due to its two aromatic rings [ 45 ]. Different phosphorus contents were introduced in the PHUs, from 0 to 2 wt% phosphorus.…”

Section: Resultsmentioning

confidence: 99%

“…Different phosphorus compounds, with a P-H bond, and MBDA were added in a stoichiometric ratio 1:1. The synthesis mechanism of MBDA-DOPO was described in a previous work [ 45 ]. This reaction was based on a nucleophilic attack of P − , obtained at a high temperature (155 °C), which enabled the epoxide group to open and form a P-C bond as well as a hydroxy group.…”

Section: Resultsmentioning

confidence: 99%

“…The MBDAC-DOPO was synthetized according to the method used by Coste et al [ 45 ]. 4,4′-Methylenebis(N,N-diglycidylaniline) ( Figure S3 ) (100 g, 0.236 mol) and tetrabutylammonium bromide (2.29 g, 0.007 mmol) were solubilized in 150 mL of dichloromethane (DCM) and added to a 300 mL sealed reactor.…”

Section: Methodsmentioning

confidence: 99%

“…The MBDA-DOPO was synthetized according to the method used by Coste et al [ 45 ]. In a 500 mL three-necked round-bottom flask equipped with a condenser and a mechanical stirrer, 100 g (0.237 mol, 1 eq.)…”

Section: Methodsmentioning

confidence: 99%

“…A previous study focused on different structures of cyclic carbonates functionalized with DOPO in order to obtain PHU foams with FR properties [ 45 ]. The best results were obtained with the foam containing 2 wt% of phosphorus and a cyclic carbonate containing two aromatic rings.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Influence of Phosphorus Structures and Their Oxidation States on Flame-Retardant Properties of Polyhydroxyurethanes

Denis

Coste

Sonnier³

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

This article focuses on the synthesis of polyhydroxyurethane (PHU) materials containing novel phosphorus flame retardants (FR). Four different phosphorus compounds were grafted onto cyclic carbonate: 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), diethyl phosphite (DEP), diphenyl phosphite (DPP) and dibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide (BPPO). Thus, three novel phosphorus reactive cyclic carbonates which have never been reported so far were synthetized. Phosphorus FR containing PHU materials were characterized by FTIR to evidence the total conversion of the cyclic carbonate. Moreover, the gel contents up to 80% confirmed the formation of the polymer network. Then, the thermal stability and the flame-retardant properties were investigated by thermogravimetric analyses, cone calorimeter and pyrolysis combustion flow calorimeter. The mode of action of phosphorus compounds, depending on the oxidation state, was especially highlighted. Phosphonate (+III) provided better action in a condensed phase than phosphinate thanks to a more efficient char formation. Among phosphonates, differences were observed in terms of char-formation rate and expansion. DEP provided the best flame-retardant properties, with a reduction of 76% of pHRR with 2 wt% of phosphorus in cone calorimeter analysis. Therefore, this article highlighted the different modes of action of phosphorus flame retardants, depending on the oxidation state of phosphorus, in PHU materials.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Influence of Phosphorus Structures and Their Oxidation States on Flame-Retardant Properties of Polyhydroxyurethanes

Denis

Coste

Sonnier³

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

Water‐Induced Self‐Blown Non‐Isocyanate Polyurethane Foams

2022

View full text Add to dashboard Cite

For 80 years, polyisocyanates and polyols were central building blocks for the industrial fabrication of polyurethane (PU) foams. By their partial hydrolysis, isocyanates release CO 2 that expands the PU network. Substituting this toxic isocyanate-based chemistry by a more sustainable variant-that in situ forms CO 2 by hydrolysis of a comonomer-is urgently needed for producing greener cellular materials. Herein, we report a facile, up-scalable process, potentially compatible to existing infrastructures, to rapidly prepare water-induced self-blown non-isocyanate polyurethane (NIPU) foams. We show that formulations composed of poly(cyclic carbonate)s and polyamines furnish rigid or flexible NIPU foams by partial hydrolysis of cyclic carbonates in the presence of a catalyst. By utilizing readily available low cost starting materials, this simple but robust process gives access to greener PU foams, expectedly responding to the sustainability demands of many sectors.

show abstract

Water‐Induced Self‐Blown Non‐Isocyanate Polyurethane Foams

2022

View full text Add to dashboard Cite

For 80 years, polyisocyanates and polyols were central building blocks for the industrial fabrication of polyurethane (PU) foams. By their partial hydrolysis, isocyanates release CO2 that expands the PU network. Substituting this toxic isocyanate‐based chemistry by a more sustainable variant—that in situ forms CO2 by hydrolysis of a comonomer—is urgently needed for producing greener cellular materials. Herein, we report a facile, up‐scalable process, potentially compatible to existing infrastructures, to rapidly prepare water‐induced self‐blown non‐isocyanate polyurethane (NIPU) foams. We show that formulations composed of poly(cyclic carbonate)s and polyamines furnish rigid or flexible NIPU foams by partial hydrolysis of cyclic carbonates in the presence of a catalyst. By utilizing readily available low cost starting materials, this simple but robust process gives access to greener PU foams, expectedly responding to the sustainability demands of many sectors.

show abstract

Synthesis of reactive phosphorus-based carbonate for flame retardant polyhydroxyurethane foams

Cited by 14 publications

References 47 publications

Influence of Phosphorus Structures and Their Oxidation States on Flame-Retardant Properties of Polyhydroxyurethanes

Influence of Phosphorus Structures and Their Oxidation States on Flame-Retardant Properties of Polyhydroxyurethanes

Water‐Induced Self‐Blown Non‐Isocyanate Polyurethane Foams

Water‐Induced Self‐Blown Non‐Isocyanate Polyurethane Foams

Contact Info

Product

Resources

About