Synthesis of 4-tert-butyldimethylsilyloxystyrene and its copolymerization with styrene using (eta(5)-indenyl)trichlorotitanium in the presence of methylaluminoxane

Abstract

Poly(styrene-co-4-tert-butyldimethylsilyloxystyrene) as a precursor of hydroxyl-functionalized syndiotactic polystyrene was successfully synthesized via (eta(15)-indenyl)trichlorotitanium (IndTiCl(3))-catalyzed copolymerization of styrene with 4-tert-butyldimethylsilyloxystyrene in toluene at 25 degrees C in the presence of methylaluminoxane (MAO) ([A1]/[Ti] = 2000). The amount of styrene derivative incorporated into the polymeric chain for a 20,7:1 mole feed ratio of styrene to 4-tert-butyldimethylsilyloxystyrene was found to be 1,8 mol-% from a H-1 NMR analysis. The styrene derivative was successfully prepared from 4-hydroxybenzaldehyde via first protecting the hydroxyl group using tert-butyldimethylchlorosilane followed by the 'Wittig-type' reaction with the 'Tebbe' reagent. The yield was about 82 wt.-% on the basis of the initial amount of 4-hydroxybenzaldehyde used.