Currently, there is little literature data about the production of colored siloxanes with covalently bound dyes. However, the demand for such products remains very high. Colored siloxanes are needed in various fields: microfluidic devices, sensors, photosensitive materials. In this work, two azo dyes based on commercially available natural phenol, eugenol, were obtained: phenylazoeugenol (AE) and bis(phenylazo)eugenol (BAE). The dyes were introduced into the hydrosilylation reaction with siloxanes of different chain lengths (trisiloxane, pentasiloxane, and polysiloxanes). The siloxanes functionalized with dyes were characterized by NMR spectroscopy, GPC, TGA, and DSC. The optical properties of the resulting compounds were investigated. It has been shown that high-molecular colored siloxanes mix perfectly with organosilicon liquids and have an intense color even with the addition of small amounts of dye (1 wt. %), which makes these products very promising for producing colored damping fluids that will make it possible to detect the leakage of PMS in the machines and eliminate the problem in time.