Synthesis and characterization of poly(norbornene) substituted with phthalimide and ammonium groups via living ring-opening metathesis polymerization

2-Norbornene-5-methylphthalimide (NBEPI) was prepared to synthesize an amino group containing poly(norbornene) via living ring-opening metathesis polymerization (ROMP) using a well-defined catalyst {Cl2Ru(CHPh)[P(C6H11)(3)](2)}. The resulting poly(NBEPI) was of high molecular weight and had a reasonably narrow molecular weight distribution (Mn = 298,900 and PDI = 1.22). The glass transition temperature (T-g) of poly(NBEPI) is 140 degrees C. The 10% decomposition temperature of poly(NBEPI) is 410 degrees C. Hydrazinolysis of poly(NBEPI) gave poly(2-norbornene-5-methylamine), poly(NBEMA), Though insoluble in almost all organic solvents, poly(NBEMA) becomes soluble in water after quaternization of the amine groups by gaseous HCl. Because of the living nature of the polymerization of NBEPI, poly(NBEMA) is reasonably linear and has a well-controlled molecular weight. The hydrogenation of poly(NBEPI) by diimide generated in situ from p-toluenesulfonylhydrazide decreased the T-g but increased thermal stability. (C) 1999 Elsevier Science B.V. All rights reserved.