Journal of Polymer Science Part A: Polymer Chemistry, Vol.34, No.5, 801-809, 1996
Zwitterionic Polymerization of 1-(4-((4-Hydroxy-1-Naphthyl)Thio)Butyl)Quinuclidinium Hydroxide Inner Salt
The zwitterion, 1-[4-[(4-hydroxy-1-naphthyl)thio]butyl]quinuclidinium hydroxide inner salt, was synthesized from tetrahydro-1-(4-hydroxy-1-naphthyl)thiophenium hydrochloride and quinuclidine and characterized by NMR and IR spectroscopy. Polymerization of the zwitterion was studied over the temperature range 175-225 degrees C. The polymer was identified as poly(1,4-piperidinediylethyleneoxy-1,4-naphthylenethiotetramethylene) based on NMR and IR spectroscopy. The polymer was found to contain 3-butenylthio and 4-hydroxy-1-naphthyl end groups. Based on the signal area of the olefinic end group, the polymer (M) over bar(n) varied between 8500 and 13,000. The highest molecular weight was achieved at the lowest temperature, indicating that termination became more favored at higher temperature. A mechanism is proposed to describe the polymerization.