An isocyanate with trimethoxysilane groups at the side chains (IPDI-M) was synthesized via an addition between the mercaptopropyl trimethoxysilane groups (MPTMS) and IPDI tripolymer (IPDI-T). Then, silane grafted isocyanate as the functional hard segment, castor oil as the soft segment, poly (ethylene adipate) diol (PEA) as the chain extender, and MPTMS as an end-capping reagent were applied to form a series of organosilicon hybrid bio-based polyurethane (CPUSi). The effect of the IPDI-M contents on the thermal stability, mechanical properties, and surface properties of the resulting product was systematically investigated. Profit from the Si–O–Si crosslinked structures formed from MPTMS curing, the tensile strength, and Young’s modulus of the resulting products increased from 9.5 MPa to 22.3 Mpa and 4.05 Mpa to 81.59 Mpa, respectively, whereas the elongation at break decreased from 342% to 101%. The glass transition temperature, thermal stability, transparency, hydrophobicity, and chemical resistance were remarkably strengthened for the obtained organosilicon-modified polyurethane with the increasing MPTMS content. At the end of the work, the thermal insulation coating that was based on CPUSi and ATO can effectively block near-infrared rays, and the temperature difference between the inside and outside of the film reached 15.1 °C.