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Though hindered phenol/polymer-based hybrid damping materials, with an excellent loss factor, attract more and more attention, the significantly decreased mechanical property and the narrow damping temperature range limit the application of such promising materials. To solve the problems, a polyurethane (hindered phenol)/polyvinyl acetate multilayer system with varied layer numbers was prepared in this study. The multilayer microstructures were first verified through the scanning electron microscopy. A subsequent molecular dynamics simulation revealed the promoted diffusion of polyurethane (hindered phenol) and polyvinyl acetate layers, the compact chain packing of the polyurethane (hindered phenol) layer, the extended chain packing of the polyvinyl acetate layer, the intermolecular hydrogen bonds among the three components and the enhanced interface interactions between the two layers in a quantitative manner. Further the mechanical and dynamic mechanical analysis detected the successful preparation of the multilayer hybrids with simultaneously improved mechanical and damping properties. Then, by a combination of molecular dynamics simulation and experiment, the relationship between the structure evolution and the properties of the multilayer hybrids was established, which was expected to have some guiding significance for industrial production.