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Synthesis of a furfural-based DOPO-containing co-curing agent for fire-safe epoxy resins.

ABSTRACT: A furfural-based DOPO-containing flame retardant, 6,6'-(((methylenebis(4,1-phenylene))bis(azanediyl))bis(furan-2-ylmethylene))bis(dibenzo[c,e][1,2]oxaphosphinine 6-oxide) (MBF-DOPO), was synthesized and utilized as a co-curing agent of 4,4'-diaminodiphenyl methane (DDM) for fire-safe epoxy thermosets. For the cured epoxy resin containing 4.0% MBF-DOPO, the limiting oxygen index (LOI) reached 32.9% (with the V-0 rating in UL-94 test), and the peak heat release rate and total smoke production values were respectively decreased by 29.3% and 33.6%, compared to pure epoxy resin. Scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR) results confirmed that the furfural-based flame retardant MBF-DOPO promoted the charring formation of the epoxy matrix, which effectively isolated the gas and heat transfer during combustion and thus enhanced the fire-safety performance of the epoxy thermosets. This work provides an effective route for synthesizing a furfural-based flame retardant, which possesses great potential for application in fire-safe epoxy thermosets.

SUBMITTER: Xie W

PROVIDER: S-EPMC9048244 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Synthesis of a furfural-based DOPO-containing co-curing agent for fire-safe epoxy resins.

Xie Weiqi W Huang Shiwen S Tang Donglin D Liu Shumei S Zhao Jianqing J

RSC advances 20200109 4

A furfural-based DOPO-containing flame retardant, 6,6'-(((methylenebis(4,1-phenylene))bis(azanediyl))bis(furan-2-ylmethylene))bis(dibenzo[<i>c</i>,<i>e</i>][1,2]oxaphosphinine 6-oxide) (MBF-DOPO), was synthesized and utilized as a co-curing agent of 4,4'-diaminodiphenyl methane (DDM) for fire-safe epoxy thermosets. For the cured epoxy resin containing 4.0% MBF-DOPO, the limiting oxygen index (LOI) reached 32.9% (with the V-0 rating in UL-94 test), and the peak heat release rate and total smoke p ...[more]

PMID: 35494575

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Project description:One-component epoxy resins (OCERs) with improved stability (shelf life) and controlled curing temperatures were prepared using epoxy resins and polyoxazoline-imidazole (POZ-Im) based thermal latent curing agents (TLCs). POZ homopolymers with molar masses of 1000, 2000, and 5000 g/mol were obtained via cationic ring-opening polymerization (CROP) of 2-ethyl-2-oxazoline, 2-propyl-2-oxazoline, 2-pentyl-2-oxazoline, and 2-phenyl-2-oxazoline. TLCs were prepared by physically entrapping imidazole, the curing agent, in the POZ matrix at the homopolymer/Im (HP/Im) ratios of 1:1 and 5:1 and characterized by FTIR and TGA. TLCs were then mixed with bisphenol A diglycidyl ether (DGEBA) to obtain OCERs with Im concentrations of 1, 3, and 5 wt %. Dynamic DSC tests were performed to determine the effect of the pendant group and molar mass of POZ, the POZ/Im ratio, and Im concentration on the curing behavior of the OCERs, whereas isothermal DSC tests were carried out to examine their thermal stability and optimal curing temperatures. Optical microscopy was performed to study the compatibility of the TLCs with DGEBA. This study showed that the dispersion quality of TLCs is highly associated with the compatibility of POZs and DGEBA, which affected the release of Im, thus left limit temperatures of curing. In addition, higher left limit temperatures were obtained when the POZ/Im ratio increased. Isothermal DSC results conformed to the improved stability and better thermal latency of the samples with a POZ/Im ratio of 5:1. Moreover, the higher left limit temperatures were obtained with the lowest molar mass of POZ due to the better interaction between the -OH end group of POZ and Im. The shelf life of PEOZ 1K-Im 5:1 1% OCER was predicted at -20, 0, and 20 °C, with an estimated 15.3 days at 20 °C using isothermal DSC and rheology at 50, 60, and 70 °C. Overall, this research contributes to the development of OCERs by introducing POZ-Im complexes as novel TLCs. The findings shed light on the importance of compatibility in achieving optimal dispersion and release of Im and the role of the POZ/Im ratio and POZ molar mass in controlling left limit temperatures, ultimately influencing the curing behavior of OCERs.

Dataset Information

Synthesis of a furfural-based DOPO-containing co-curing agent for fire-safe epoxy resins.

Publications

Synthesis of a furfural-based DOPO-containing co-curing agent for fire-safe epoxy resins.

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