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This chapter will review silicone based adhesive technologies, applications and characterization, emphasizing those self-adhesive materials often used in skin contact applications including transdermal drug delivery and wound care device attachment. The silicone pressure sensitive adhesives used in transdermal applications today are thermoplastic and based on silicone polymer and silicate resin chemistries. Previous research has suggested that some drugs readily diffuse through silicone adhesives, prompting their use in transdermal patches. A recently developed silicone acrylate hybrid adhesive technology combines polyacrylate and silicone molecular structures to form a stable, semi-interpenetrated network. This technology provides ease in formulating transdermal drug delivery systems through improved physical stability over simple blends of acrylate and silicone adhesives. The ability of some silicone adhesives to affix bandages without disrupting the wound bed upon removal has led to the wide acceptance of a third type of silicone adhesive technology that unlike the aforementioned thermoplastic materials is thermoset. This adhesive form is based on a platinum catalyzed, cross-linking reaction between vinyl functional and silicon-hydride functional silicone polymers. The various silicone adhesive types have been characterized via classical measurements of physical performances. Rheological techniques elucidated herein provide further understanding of the structure-property relationships previously unavailable using classical characterization approaches.