Synthesis of 1-propenyl ethers and their using as modifiers of UV-cured coatings in radical and cationic polymerization

The 1-propenyl ethers of diols and polyols have recently attracted increasing attention as monomers and comonomers because these compounds undergo UV-photoinitiated polymerization. The synthesis of 1-propenyl ethers via the isomerization of corresponding, readily available allyl ethers catalysed by homogenized transition metal complexes with recycling of catalyst has been described. The properties of UV-cured coatings have been investigated for various compositions containing: the model ether (i.e. 1,4-di(1-propenyloxy)-butane), the unsaturated polyester resin [Estromal 103] or epoxy resin [Epidian 6] and radical (i.e. Irgacure 184) or cationic (i.e. triarylsulfonium salts with metal halide anions: PF₆⁻, SbF₆⁻) initiators. The purified or unrefined (i.e. including 0.05 mol% homogenized ruthenium(II) complex [RuClH(CO)(PPh₃)₃]) 1,4-di(1-propenyloxy)butane were applied as modifiers. The effect of presence of homogenized [RuClH(CO)(PPh₃)₃] in the composition has been discussed.