Pyrolysis and flame retardant behavior of a novel compound with multiple phosphaphenanthrene groups in epoxy thermosets

- Novel flame retardant TDBA with multiple DOPO groups was synthesized.
- TDBA pyrolyzed along substituted DOPO and bisphenol-A routes.
- TDBA exerted quenching and charring effects on burning epoxy thermosets.
- TDBA endowed thermosets with excellent flame retardancy via bi-phase action.

A novel flame retardant compound (TDBA) with multiple phosphaphenanthrene groups was synthesized and confirmed by chemical structural and elemental characterization. Contrastive analysis on thermal decomposition behavior showed that the two kinds of bridge bonds linking phosphaphenanthrene groups in TDBA caused a wider decomposition temperature range, contributing to inhibiting combustion in relatively longer time. The application of TDBA in epoxy thermosets suggested that, TDBA capacitated the limited oxygen index of thermosets to surpass 35% and 4 wt.% or more loadings of TDBA made 4,4′-diamino-diphenyl methane curing thermosets pass UL94 V-0 rating especially. During combustion, the incorporated TDBA induced the matrix to decompose earlier, reduced the fuels production, reduced burning intensity and inhibited the combustion reaction of fuels in gaseous phase, and promoted the charring behavior of thermosets in condensed phase. The pyrolysis of TDBA proceeded along two main directions, namely substituted phosphaphenanthrene and bisphenol-A. Through releasing massive phenolic derivatives, PO free radicals and other certain phosphorus-containing substances, TDBA is capable to exert free radical quenching effect in gaseous phase, and to promote charring behavior to form compact residue with barrier effect on heat and fuels transportation in condensed phase. This bi-phase joint action mode from TDBA endowed epoxy thermosets with excellent flame retardancy.