Synthesis of polystyrene with cyclic anhydride end-group

K. A. Wolske, C. W. Macosko, M. Tirrell

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Abstract

The synthesis of polymers with functional end-groups is a subject of intense activity and has been extensively reviewed recently. Neither mentions a route to cyclic anhydride end-functionality. Cyclic anhydride is an electrophilic group found in styrene-(maleic anhydride) copolymer whose reactions with amine end-functional polymers has been studied in our laboratory. A simple procedure is presented to transform a primary amine end-functional polystyrene into a cyclic anhydride end-functional polystyrene. SEC analyses of a nominal 10,000 number-average molar mass (M̄n) run primary amine end-functional polystyrene reveals relatively narrow molecular weight distribution (polydispersity = 1.1), but the average value of M̄n obtained from triplicate analyses (13,314) lacks sufficient precision to provide anything but a rough estimate of functionalization yield. For the same run, amine end-group titrimetric analyses gives a value of M̄n = 14,759. The resulting primary amine functionalization yield estimate is 90%-close to the result of Hirao et.al. SEC analyses of cyclic anhydride end-functional polystyrene synthesized from the above run of primary amine end-functional polystyrene shows negligable effect on the SEC peak shape or location. Anhydride end-group titrimetric analysis gives a value of M̄n = 15,244, which would correspond to a 97% anhydride functionalization yield estimate. The corresponding overall anhydride functionalization yield estimate is 87%.

Original languageEnglish (US)
Number of pages1
JournalAmerican Chemical Society, Polymer Preprints, Division of Polymer Chemistry
Volume31
Issue number2
StatePublished - Aug 1 1990
EventPapers presented at the Washington, DC Meeting 1990 of the ACS, Division of Polymer Chemistry - Washington, DC, USA
Duration: Aug 26 1990Aug 31 1990

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