Synthesis and characterization of nitro-functionalized hydroxyl-terminated polybutadiene using N-iodosuccinimide

A convenient, inexpensive and highly efficient one-pot procedure of synthesizing nitro-functionalized hydroxyl-terminated polybutadiene (Nitro-HTPB) is reported by the reaction of hydroxyl-terminated polybutadiene (HTPB) and sodium nitrite in the presence of N-iodosuccinimide in EG–EtOAc–H2O at 60 °C for 24 h. The investigation of the effective parameters on the synthesis of Nitro-HTPB such as amounts of reactants, temperature and reaction time indicated that in the optimum reaction conditions, the nitration HTPB backbone is restricted to 6.7% of double bonds until the outstanding physical and chemical properties of HTPB are retained. The Nitro-HTPB was characterized by FTIR, 1H NMR, 13C NMR, DSC and TGA. The polymer showed good thermal stability, yield of 93%, viscosity of 14.2 Pa.s−1, number average molecular weight of 2730 gmol−1 and hydroxyl value of 34 mg KOH per g.