Rubber composites were prepared by mixing bromobutyl rubber (BIIR) with silica particles in the presence of 1-butylimidazole. In addition to pristine (precipitated) silica, silanized particles with aliphatic or imidazolium functional groups, respectively, were used as filler. The silanization was carried out either separately or in situ during compounding. The silanized particles were characterized by TGA, ¹H–²⁹Si cross polarization (CP)/MAS NMR, and Zeta potential measurements. During compounding, the bromine groups of BIIR were converted with 1-butylimidazole to ionic imidazolium groups which formed a dynamic network by ionic association. Based on DMA temperature and strain sweep measurements as well as cyclic tensile tests and stress–strain measurements it could be concluded that interactions between the ionic groups and interactions with the functional groups of the silica particles strongly influence the mechanical and viscoelastic behavior of the composites. A particularly pronounced reinforcing effect was observed for the composite with pristine silica, which was attributed to acid–base interactions between the silanol and imidazolium groups. In composites with alkyl or imidazolium functionalized silica particles, the interactions between the filler and the rubber matrix form dynamic networks with pronounced self-healing behavior and excellent tensile strength values of up to 19 MPa. This new approach in utilizing filler–matrix interactions in the formation of dynamic networks opens up new avenues in designing new kinds of particle-reinforced self-healing elastomeric materials with high technological relevance.