1,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate) → p-Hydroxystyrene p-tert-butoxystyrene

Participants

Reaction Steps

In 400 mL of isopropanol, 56.7 g of p-acetoxystyrene and 26.4 g of p-tert-butoxystyrene were dissolved, then 8.3 g of 2,2′-azobis(methyl 2-methylpropionate) (V-601: trade name of a product from Wako Pure Chemicals Ind., Ltd.) was added, followed by reacting at 80° C. for 6 hours under nitrogen gas flow. After the reaction, said reaction solution obtained was poured into 10 L of water for precipitation, followed by filtering off deposited crystal. The thus obtained crystal was added to 450 mL of methanol, followed by charging 234 g of a 15% aqueous tetramethylammonium hydroxide solution and reacting under reflux for 4 hours while stirring. The thus obtained solution was cooled to room temperature, then neutralized by adding drop-wise 12.9 g of glacial acetic acid. The neutral solution was poured into 10 L of water for precipitation, followed by filtering off deposited crystal and drying under reduced pressure, to obtain 42.6 g of poly(p-hydroxystyrene/p-tert-butoxystyrene) as a white powder crystal. The thus obtained crystal was named polymer A1. A composition ratio of p-hydroxystyrene unit and p-tert-butoxystyrene unit in polymer A1 was found to be about 7:3 from the measurement results by 13CNMR. Weight average molecular weight (Mw) of polymer A1 was about 9,500 and distribution (Mw/Mn) thereof was about 1.75 from the measurement results by gel permeation chromatography using polystyrene as a standard.

Provenance & Evidence