AbstractFractionation of softwood and hardwood LignoBoost kraft lignins, using sequential extraction with organic solvents of increasing hydrogen-bonding ability (dichloromethane, n-propanol, and methanol), was carried out. Using SEC, analytical pyrolysis, FTIR and UV/VIS spectroscopy, and chemical analytical methods, four fractions were obtained and characterized in terms of their yield, composition, functionality, lignin structural features, and antioxidant properties. In tests with free radicals (ABTS . +, DPPH . , O2 . -) and the ORAC (oxygen radical absorbance capacity) assay, the high radical scavenging capacity of the lignin’s soluble fractions was demonstrated. The antioxidant activity of the fractions was tested by their influence on thermo-oxidative destruction of model polyurethane elastomers. The TGA data clearly revealed the antioxidant effect of the three fractions, with the most prominent activity for the propanol-soluble fraction. The dichloromethane fraction has potential as an antioxidant for non-polar products. Novel correlations between lignin’s structural features and its radical scavenging activity were found that can be used for tuning lignin’s antioxidant properties.