Synthesis Of Amine-Terminating Agents N-Benzylidene-3-Tris (Methoxyethoxyethoxy) Silane-1-Propanamine And Its Application In The SSBR

With the rapid development of automobile industry,energy conservation and environmental protection have been the focus of vehicle manufacturers,the requirements for high-performance tires with high speed,safety and energy-saving properties have been more universal,especially the synthetic rubber SSBR.among these methods,the synthesis of chain-end functionalized SSBR using reaction of the living polymer chain ends with a variety of electrophiles(terminator)has become the most effective way to prepare SSBR with low rolling and received considerable attention.Up to now with this method the benzophenone,aldimines,silane,and alkoxysilane-functionalized SSBR have been synthesized.The studies have shown that schiff base(imine compounds,containing-C=N-group in molecule)can react with polymeric organolithiums stoichiometrically and has high reaction activity without side reactions.Therefore we has designed a new kind of terminator to be applied to end-functionalize SSBR.In this paper,the N-benzylidene-3-tris(methoxyethoxyethoxy)silane-1-propanamine(Imine-GLYME)was synthesized and designed by the 3-aminopropyltris(methoxyethoxyethoxy)silane and benzaldehyde using the toluene as solvent which molecular structure is characterized by FT-IR spectrum and NMR spectrum.The results showed that the ideal terminator Imine-GLYME was synthesized.N-benzylidene-3-tris(methoxyethoxyethoxy)silane-1-propanamine(Imine-GLYME)functionalized PS has been synthesized using the styrene as monomers,Imine-GLYME as terminator,n-BuLi as initiator,cyclohexane as solvent by living anionic polymerization.The molecular structure of PS-GLYME is characterized by NMR spectrum(1H-NMR,13C-NMR)and GPC spectrum.The results of 1H-NMR,13C-NMR and GPC clearly indicated that the reaction of polybutadienyllithium with Imine-GLYME has been carried out and Imine-GLYME functionalized PS was successful obtained.GPC chromatograms showed that Imine-GLYME incorporation into the end of PS caused side reactions and unfunctionalized products:dimers and trimers were observed.However,only put addition of 1,1-diphenyl ethylene(DPE)before functionalizing could eliminate the side reaction,prevent the formation of side products and increase functionalization efficiency.At the same time,the functionalization reaction mechanism was also discussed,then we use the terminator to end-functionalize polybutadiene to investigate the efficiency of different structural modifiers on PB-GLYME.Finally,the terminator is applied to end-functionalize SSBR,the goal of this study is to provide theoretical and experimental basis for the preparation of end functionalized SSBR.