Furfuryl-containing tertiary phosphine oxides and polymers based on some of them

The syntheses of dimethyl(furfuryloxymethyl)phosphine oxide (DPO), methylbis(furfuryloxymethyl)phosphine oxide (MPO), tris(furfuryloxymethyl)phosphine oxide (TPO), dimethyl(tetrahydrofurfuryloxymethyl)phosphine oxide (DTPO), methyl-bis(tetrahydrofurfuryloxymethyl)phosphine oxide (MTPO) and tris(tetrahydrofurfuryloxymethyl)phosphine oxide (TTPO) from dimethyl(chloromethyl)phosphine oxide, methyl-bis(chloromethyl)phosphine oxide, tris(chloromethyl)phosphine oxide and the furfuryl and tetrahydrofurfuryl sodium alkoxides via the Williamson reaction are reported. Phosphorus-containing furan polymers with reduced flammability are prepared by polymerizing MPO and TPO using p-toluenesulphonic acid as catalyst. The oxygen indexes of these polymers, as determined by ASTM D-2863, are 35.1 and 33.1% O₂, respectively; for the phosphorus-free polymer from difurfurylidene acetone, it is 23.0% O₂. It is shown that DPO can be used as an efficient fire-retardant for reducing the flammability of a polymer from difurfurylidenacetone.