At present, the energy crisis is becoming increasingly outstanding, and the expanding market of pressure sensitive adhesives (PSAs) puts forward higher requirements for biomass materials. Vanillin comes from biomass raw materials, and it has been widely used in related research fields. So far, there are few reports on the preparation of novel monomers containing Schiff base structure from silicone and vanillin. In this work, vanillin reacts with methacrylic anhydride to prepare monomers with double bond structure, and furthermore a fresh type of silicone/vanillin monomer is prepared by aldehyde-amine condensation reaction. Finally, the novel monomer is introduced into polyurethane matrix, and a series of silicone/vanillin-based PSAs are prepared under UV conditions. The results show that the introduction of silicone/vanillin monomer can improve the residual carbon rate of PSAs, and the residual carbon rate of PUPG-C is as high as 12 wt%. Moreover, by comparison to the control group PUPG-0, the ball number, 180? peel strength and shear strength of PUPG-A are increased by 120.0 %, 215.0 % and 49.8 %, respectively. It is worth noting that the 180? peel strength of PSAs on functionalized glass has been strengthened, which greatly promotes the application of PSAs on functionalized glass. In short, this work provides a simple, versatile and extensible method for designing PSAs with silicone/vanillin structure in the future.