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Phosphorus-based α-amino acid mimetic for enhanced flame-retardant properties in an epoxy resin

Version 3 2025-06-02, 01:34
Version 2 2024-06-04, 09:12
Version 1 2019-02-18, 14:25
journal contribution
posted on 2025-06-02, 01:34 authored by MK Stanfield, F Stojcevski, A Hendlmeier, RJ Varley, J Carrascal, AF Osorio, DJ Eyckens, Luke HendersonLuke Henderson
This work demonstrates the introduction of a phosphonate moiety into a commonly used curing agent, 4,4′-diaminodiphenylmethane (DDM), via an α-aminophosphonate. This compound (DDMP) can be prepared and isolated in analytical purity in under 1h and in good yield (71%). Thermoset polymer (epoxy-derived) samples were prepared using a room-temperature standard cure (SC) and a post-cured (PC) protocol to encourage incorporation of the α-aminophosphonate into the polymer network, with improved flammability properties observed for the latter. Thermogravimetric analysis under a nitrogen atmosphere showed increased char yield at 600°C, and similar observations were made when analysis was conducted in air. Significant reductions in flammability are observed at very low phosphorus content (P%=0.16–0.49%), demonstrated by higher char yields (25.5 from 14.0% in air), decreased burn time from ignition (60 to 24s), and decreased mass loss after ignition (87.6 to 58.5%). Limiting Oxygen Index for the neat polymer (P%=0%, 20.3±0.8%) increased with increasing α-aminophosphonate additive (P%=0.16%, 20.8±0.6%; P%=0.32%, 21.4±0.4%; P%=0.49%, 22.6±0.8%).

History

Journal

Australian Journal of Chemistry

Volume

72

Pagination

226-232

Location

Clayton, Vic.

ISSN

0004-9425

eISSN

1445-0038

Language

English

Publication classification

C1 Refereed article in a scholarly journal

Copyright notice

2019, CSIRO

Issue

3

Publisher

CSIRO PUBLISHING

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