The aim of this study was the preparation of novel water repellent UV curable materials using acrylic modified melamine (AM) and poly-dimethylsiloxane (PDMS). UV curable acrylic melamines containing silicone segments (SiAMs) were synthesized by condensation of methylolmelamine, 2-hydroxyethyl acrylate, and carbinol-modified PDMS. The SiAM films with a 0.3 wt% PDMS segment that were cured by UV irradiation had higher transparency than that of a blended sample. Examination with a scanning electron microscope revealed that the blend sample has cohesion of the silicone segments, while such a phenomenon was not observed in the composite samples (SiAMs). From these results, it was confirmed that aggregation of the silicone segments was prevented by introducing the silicone segments into the acrylic melamine. By introducing 0.3 wt% of PDMS segments into AM, good watershedding properties were confirmed, while several of the most attractive features of AM, such as hardness, adhesion, and refractive index, were maintained.