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A biobased Schiff base from protocatechualdehyde and its application in flame-retardant, low-smoke epoxy resin systems.

ABSTRACT: Herein, a new renewable Schiff base flame retardant 4,4'-((1E,1'E)-((oxybis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(benzene-1,2-diol) (PH-ODA) was prepared by the reaction of protocatechualdehyde with 4,4'-diaminodiphenyl ether (ODA). PH-ODA (acting as a carbonization agent) combined with ammonium polyphosphate (APP) were used as intumescent flame retardants for commercial bisphenol A epoxy resin (DGEBA). For the cured epoxy resin containing 7.5% APP and 2.5% PH-ODA, the limiting oxygen index (LOI) reached 29.9% (with the V-0 rating in UL-94 test), and the peak heat release rate and total smoke production were respectively decreased by 88.1% and 68.3%, compared with pure epoxy resin. The enhancement of fire-safety performance was due to PH-ODA/APP promoting the formation of a compact intumescent char structure. It was also found that the synergism between PH-ODA and APP was helpful to enhance the fire resistance of the epoxy matrix. This work provides a facile and sustainable route for synthesizing Schiff base compounds from biomass-derived resources, possessing great potential for application in highly-effective intumescent flame retardants.

SUBMITTER: Xie W

PROVIDER: S-EPMC9072551 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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A biobased Schiff base from protocatechualdehyde and its application in flame-retardant, low-smoke epoxy resin systems.

Xie Weiqi W Huang Shiwen S Liu Shumei S Zhao Jianqing J

RSC advances 20190930 53

Herein, a new renewable Schiff base flame retardant 4,4'-((1<i>E</i>,1'<i>E</i>)-((oxybis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis(benzene-1,2-diol) (PH-ODA) was prepared by the reaction of protocatechualdehyde with 4,4'-diaminodiphenyl ether (ODA). PH-ODA (acting as a carbonization agent) combined with ammonium polyphosphate (APP) were used as intumescent flame retardants for commercial bisphenol A epoxy resin (DGEBA). For the cured epoxy resin containing 7.5% APP and 2.5% PH- ...[more]

PMID: 35529374

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Project description:In this work, ammonium polyphosphate (APP) was surface-modified by bio-based arginine (Arg) for the first time to enhance its flame retardance for fire-safety epoxy resin (EP). The structure of Arg modified APP (Arg-APP) was characterized by Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS), 1H nuclear magnetic resonance (1H-NMR), and scanning electron microscopy (SEM). The results illustrated that Arg was attached on the surface of APP through a cation exchange reaction. With Arg acting as the efficient carbon source, the char-forming ability of Arg-APP was significantly improved as illustrated by thermogravimetric analysis (TGA). The flame retardance of EP/APP and EP/Arg-APP composites was evaluated using the limit oxygen index (LOI), vertical burning tests (UL-94), and cone calorimeter tests (CCT). The results showed that at the same weight loading (15 wt%), Arg-APP had better flame retardance and smoke suppression performance compared with pristine APP, which can be attributed to Arg-APP constituting an integrated intumescent flame retardant (IFR) and facilitating formation of char residues with significantly expanded structures and higher carbonization degrees. When the weight loading of Arg-APP reached 25 wt%, the EP/Arg-APP composite could achieve an LOI value as high as 34.7%, pass V-0 requirements in UL-94 tests, and decrease the peak heat release rate and total smoke production by 83.5% and 61.1% compared with neat EP in CCT, respectively, indicating the superior flame retardance performance of Arg-APP. Finally, the effects of the flame retardant additives on the mechanical properties of EP were evaluated by the differential scanning calorimetry (DSC) tests and tensile-strain tests. At the same additive weight loading (15 wt%), the EP/Arg-APP composite showed higher glass-transition temperature and better tensile-strain properties compared with EP/APP composite, which can be attributed to the Arg shell structure improving the compatibility between APP and the organic substrate. In conclusion, this work presents a convenient and environmentally friendly method to improve the practical performance of APP.

Dataset Information

A biobased Schiff base from protocatechualdehyde and its application in flame-retardant, low-smoke epoxy resin systems.

Publications

A biobased Schiff base from protocatechualdehyde and its application in flame-retardant, low-smoke epoxy resin systems.

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