A lubricating oil additive suitable as an extreme pressure/anti-wear additive comprises the product obtainable by reacting at elevated temperature a mixture comprising (i) sulphur, (ii) at least one C.sub.10 to C.sub.100 unsaturated carboxylic acid, and (iii) at least one hydrocarbyl-substituted phenol, the amount of (iii) in the mixture being 15 to 65% w/w based on the combined weight of (i) (ii) and (iii). The reaction mixture can further comprise an olefin and/or, a mercaptan and/or a lubricating oil as a diluent. The additive is also useful as an anti-oxidant. Additive concentrates and lubricating oil compositions comprise a lubricating oil and the additives of the present invention.