Synthesis of a silane coupling agent containing a 4-(perfluoroalkyl)phenyl group and its application to the surface modification of glass

Abstract

Eight silane coupling agents, CF 3(C 6H 4)C 2H 4Si(CH 3)(OCH 3) 2 (C 6H 4= p-phenylene) ( 1), C 4F 9(C 6H 4)C 2H 4Si(CH 3)(OCH 3) 2 ( 2), C 6F 13(C 6H 4)C 2H 4Si(CH 3)(OCH 3) 2 ( 3), C 8F 17(C 6H 4)C 2H 4Si(CH 3)(OCH 3) 2 ( 4), CF 3(C 6H 4)C 2H 4Si(OCH 3) 3 ( 5), C 4F 9(C 6H 4)C 2H 4Si(OCH 3) 3 ( 6), C 6F 13(C 6H 4)C 2H 4Si(OCH 3) 3 ( 7) and C 8F 17(C 6H 4)C 2H 4Si(OCH 3) 3 ( 8) have been prepared by the hydrosilylation reaction of dichloro(methyl)silane or trichlorosilane with the corresponding 4-perfluoroalkylstyrene in the presence of hydrogen hexachloroplatinate(IV), followed by reaction with sodium methoxide. These new coupling agents were freely soluble in hydrocarbon solvents. Their application for the surface modification of glass has been attempted. From measurements of the contact angles θ (°) of water and oleic acid on a modified glass plate surface, it was found that the silane coupling agents show a high degree of surface modification. The oxidation resistance of the modified glass surface has also been investigated.