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Tris(hydroxymethyl)phosphine (THP) was prepared by the addition of a stoichiometric amount of base to tetrakis(hydroxymethyl)phosphonium chloride (THPC). Freshly prepared THP was successfully immobilised onto wool through a Mannich-type condensation reaction between a hydroxymethyl group and an amine on the wool surface, forming stable gt;P-CH2-Nlt; coupling links. The immobilisation of THP to wool stabilised the THP, which resulted in the decreased oxidation of THP to tris(hydroxymethyl)phosphine oxide (THPO). The presence of immobilised phosphine groups was determined colorimetrically by reaction with Ni2+ ions, which produced a bright orange nickel-phosphine complex, as well as quantitatively, by measuring nickel uptake using ICP-MS. Immobilised THP-wool showed proportional binding for varying concentrations of metal solution. Decreasing or increasing the concentration of the metal solution resulted in a corresponding proportional response of metal binding. Following immobilisation onto wool, oxidation of the system by 6% H2O2 resulted in a reduced binding of 24% for Cu, 25% for Co, 27% for Ni, and 93% for Cd relative to unoxidised THP immobilised onto wool. Additional modification of the THP-wool systems via reaction with amino acids and other related compounds overall did not appear to enhance the metal binding capacity relative to the unmodified THP-wool system. The only modified THP-wool system that showed either retention or an increase in metal binding capacity for all metals analysed was that of 2-aminopyridine, followed by oxidation with H₂O₂.