Zwitterionic polymerization of 1-[4-[(4-hydroxy-1-naphthyl)thio]butyl]quinuclidinium hydroxide inner salt

✍ Scribed by D. L. Cangiano; G. Odian; D. L. Schmidt

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 689 KB
• Volume: 34
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19960415)34:5<801::aid-pola10>3.0.co;2-m

✦ Synopsis

The zwitterion, 1 -[ 4-[ (4-hydroxy -1 -naphthyl)thio]butyl]quinuclidinium hydroxide inner salt, was synthesized from tetrahydro-l-(4-hydroxy-l-naphthyl)thiophenium hydrochloride and quinuclidine and characterized by NMR and IR spectroscopy. Polymerization of the zwitterion was studied over the temperature range 175-225°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-lnaphthyl end groups. Based on the signal area of the olefinic end group, the polymer M,, varied between 8500 and 13,000. The highest molecular weight was achieved at the lowest temperature, indicating that termination became more favored a t higher temperature. A mechanism is proposed to describe the polymerization.