4,4"-(1,4-phenylenebis(nitrilomethylidyne))-bis(2-methoxyphenol) (VPP), an aromatic imine compound, was synthesized from vanillin and p-phenylenediamine via a Schiff base reaction. Using VPP and bis(2-aminophenyl) disulfide (APD) as chain extenders, dynamic covalent bonds including aromatic imine bonds (Ar—C==N—Ar) and disulfide bonds (S—S) were introduced into polyurethane (PU) elastomers to prepare PU elastomer materials with sunlight-induced self-healing capabilities, denoted as PU-VPP-x [where x represents the molar amount of VPP (mmol), and the molar amount of APD is (8-x) mmol, the same below]. The chemical structures of VPP and PU-VPP-x were characterized by FTIR, 1HNMR, 13CNMR, and XRD. The visible light absorption of VPP was tested using UV-Vis. The effects of n(VPP):n(APD) on the thermal properties, mechanical properties, and self-healing performance of the synthesized PU-VPP-x were investigated based on TGA, DSC, a universal testing machine, and self-healing experiments. The results indicated that VPP exhibited a significant absorption peak at 388 nm in the visible light region, confirming its visible light absorption capability. PU-VPP-x was found to be an amorphous material. The PU-VPP-2 prepared by n(VPP):n(APD)=1:3, had a glass transition temperature of 5.58 °C, a tensile strength of 4.80 MPa, and an elongation at break of 582.34%. The self-healing efficiency under sunlight irradiation for 8 hours was 100.41%.