Functionalization of polyhydromethylsiloxane with nitrogen-containing organic compounds

Abstract

Linear polyhydromethylsiloxane (PHMS) was functionalized with nitrogen-containing organic compounds: N-allylaniline (Naa), N-allylcyclohexylamine (Nach), N-allylpiperidine (Nap) and 4-vinylpyridine (4VP) via hydrosilylation reaction in the presence of Pt0 complex (Karstedt’s catalyst) under mild conditions. Reaction course was followed by FTIR spectroscopy and final hydrosilylation products were characterized by FTIR, 1H, 29Si NMR and 29Si MAS-NMR spectroscopies as well as by elemental analysis. Results showed that functionalization of PHMS with N-allyl amines took place but in none of the systems it was complete. Hydrosilylation of Naa, Nach and Nap with PHMS led both, to the β and α addition products. 29Si NMR spectroscopy showed unequivocally that the reaction of PHMS with 4VP did not occur and the only reactions in the systems were hydrolysis of Si–H groups of PHMS followed by condensation of the silanol groups resulting in cross-linking of the polymer. All the functionalized polymers studied in the work contained reactive amine moieties prone to further modifications, therefore exhibit a great potential for various applications.