Abstract: Epoxy resin is widely used as insulation material for power equipment due to its excellent physical and chemical properties as well as electrical properties. However, it is difficult to effectively recycle and degrade, which does not meet the development requirements of green power due to overall abandonment of power equipment after retirement. In order to explore the degradable epoxy insulating materials and the influencing factors of their related properties, vanillin based monoepoxides containing aldehyde groups were synthesized based on the etherification reaction of vanillin and epichlorohydrin in this paper. On this basis, the degradable epoxy insulating materials containing Schiff base were obtained by curing with diamine curing agent 4,4′−methylene bicyclohexylamine. The molecular structure of the epoxy resin was characterized by Fourier transform infrared spectroscopy and superconducting nuclear magnetic resonance spectroscopy. The infrared spectroscopy, nuclear magnetic resonance hydrogen spectroscopy (¹H-NMR) and nuclear magnetic resonance carbon spectroscopy (¹³C-NMR) all confirmed that the synthesized product was a degradable epoxy resin containing Schiff base, and the Schiff base content in the degradable epoxy resin first increased and then decreased with temperature. The test results of thermal weightlessness and dielectric properties show that the degradable epoxy resin has good thermal stability and is proportional to the curing temperature; the dielectric property is also good, with dielectric constant of 2.1~3.7 and dielectric loss of 0.004~0.008, which are equivalent to traditional epoxy resin. The results of breakdown experiments and mechanical properties show that the breakdown field strength of degradable epoxy resin can reach up to 45.34 kV/mm and the elastic modulus is 3.4~3.7 GPa, which are higher than that of traditional epoxy resin. By exploring different degradation conditions, it was found that the material could be completely degraded within 40 minutes under the weak acid environment at 80 ℃.