The cycloaliphatic epoxy compounds have been widely used as the monomers in cationic photopolymerization and the fluorine-modified organosilicon materials combine the merits of both organosilicon and organofluorine. In this work, three trifluoromethyl organosilicon cycloaliphatic epoxy monomers with different chain length (CE-FSi n , n = 3, 6, 9) were designed and prepared by using a facile two-step synthesis and very competitive raw materials. CE-FSi n showed good ability to cationically photopolymerize. The final conversion of the alicyclic epoxy group of CE-FSi n systems reached up to 84.0% under the irradiation for 900 s. The addition of CE-FSi n enhanced the surface water repellency, heat resistance, elongation at break and glass transition temperature (T g ) of the cured film because of the presence of organosilicon chain and trifluoromethyl group of CE-FSi n . The cured film of CE-FSi 3 -0.5% had the largest water contact angle (105.0 ), while the cured film of CE-FSi 9 -0.5% had tensile strength of 0.49 MPa and elongation at break of 68.51% that was three folds as that of the blank control. The addition of CE-FSi n had no obvious influences on the adhesion forces of the cured films, but decreased the pencil hardness.
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