Maleimide Functionalized Siloxane Resins

Polyorganosiloxanes are a commercially important class of compounds. They exhibit many important properties, including very low glass transition temperatures, making them useful over a wide temperature range. In practice, the polysiloxane polymer is often mixed with a filler material to help improve its mechanical properties. An alternative method for increasing polymer mechanical strength is through the incorporation of certain substituents on the polymer backbone. Hard substituents such as carbonates and imides generally result in improved mechanical properties of polysiloxanes. In this paper, we present the preparation of novel polysiloxane resins modified with hard maleimide substituents. Protected ethoxysilyl-substituted propyl-maleimides were prepared. The maleimide substituent was protected with a furanyl group and the monomer polymerized under aqueous acidic conditions. At elevated temperatures (>120 C), the polymer undergoes retro Diels-Alder reaction with release of foran (Equation 1). The deprotected polymer can then be selectively crosslinked by a forward Diels-Alder reaction (in the presence of a co-reactant having two or more dime functionalities).