Structural features of crumb rubber (CR) particles obtained by grinding on rollers and ultra-disperse powder elastomeric modifiers (PEM) obtained by high-temperature shear-induced grinding (HTSG) of CR or co-grinding with butadiene styrene thermoplastic elastomer (SBS) have been studied by electron and optical microscopy methods. Samples of modified bitumen were obtained at different mixing times (1–40 min) in a wide temperature range (120–180 °C). The products of interaction of PEM with hot bitumen precipitated on filters when washed with solvent from modified bitumen (MB) were studied by scanning electron microscopy (SEM). The self-similarity PEM particles and PEM breakdown fragments in bitumen up to the size of 100–200 nm were noted. The rapid (for 1 min) decomposition of PEM particles into fragments is shown, which is due to the specific structure formed as a result of HTSG. It has been suggested that this fragmentation may be caused by bitumen penetrating deep into the porous particle and breaking it, due to differently directed swelling pressure and precede the classical swelling associated with the penetration of solvent between rubber macromolecules, or occur concurrently with it.