The results of the application of a new hydrophobization agent based on a triethoxymethylsilane and standard starch aqueous mixture for mass-produced cellulosic materials—printing paper, paperboard, and sack paper—have been evaluated to examine whether such a mixture can be used in industrial practice. The application of this agent on laboratory sheets prepared in a repetitive recycling process was performed to investigate its influence on the formation and properties of the products, as well as the contamination of circulating water. Measurements of the water contact angle, Cobb tests, and water penetration dynamics (PDA) were performed to test the barrier properties of the resulting materials. The effects of the applied coatings and recycling process on the paper’s tensile strength, tear index, roughness, air permeance, and ISO brightness were studied. Studies have proven that this formulation imparts relatively high surface hydrophobicity to all materials tested (contact angles above 100°) and a significant improvement in barrier properties while maintaining good mechanical and optical performance. The agent also does not interfere with the pulping and re-forming processes during recycling and increases circulation water contamination to an acceptable degree. Attenuated total reflectance Fourier-transform infrared (FT-IR) spectra of the paper samples revealed the presence of a polysiloxane network on the surface.