Copolymerizations of propylene with functionalized long-chain α-olefins using group 4 organometallic catalysts and their membrane application

Introduction of functional groups into polyolefins has the potential of broadening their end use. An attractive method for preparing polyolefins containing functional groups is the copolymerization of the olefins with α-olefins containing a functional group. Copolymerizations of propylene with 10-undecen-1-ol, containing a hydroxyl group protected by either TIBA or TBDMSCl, 11-chloro-1-undecene, 5-bromopent-1-ene and N-allyl-2,2,2-trifluoroacetamide were performed using three organometallic catalysts: the metallocene rac-Et(Ind)2ZrCl2 and two new benzamidinate catalysts [3-C5H4NC(NSiCH3)2]2TiCl2 and [(m-OMe-C6H4NC(NSiCH3)2]2ZrCl2. 10-Undecene-1-ol protected “in situ” with TIBA and N-(dec-9-enyl)-2,2,2-trifluoroacetamide gave copolymers with similar polar monomer incorporation percentages and molecular weights 17%; 28,900 g/mol for the protected 10-undecene-1-ol, and 15%; 27,100 g/mol for N-(dec-9-enyl)-2,2,2-trifluoroacetamide. 11-Chloro-1-undecene gave copolymers with up to 22% incorporation for 0.12 M of the comonomer in the reaction feed. The obtained copolymers were characterized by NMR, DSC, and GPC. Membranes were prepared from two copolymers containing the hydroxyl groups (6 and 10%) and one copolymer containing chlorine groups (7%). The membranes prepared could be wetted in contrast to polypropylene membranes which do not contain functional groups. In addition, it was observed that for both type of membranes prepared from the different copolymers containing the hydroxyl groups, the flux was significantly greater than for the membrane prepared from the copolymer containing a chlorine groups. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011