Ethylene Glycol → Urea Urethane

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Reaction Steps

In an argon atmosphere, ethylene glycol (0.28 ml, 4.95 mmol) and triethylamine (0.5 ml) were dissolved in dry N-methylpyrrolidinone (5.0 ml) in a three-necked flask to give a solution. At room temperature, a solution of 4,4′-diphenylmethane diisocyanate (1.37 g, 5.50 mmol) in dry N-methylpyrrolidinone (5.0 ml) was slowly added dropwise to the solution. After the completion of the dropwise addition, the resultant solution was stirred for 1 hour at room temperature and was combined with a solution of the compound (4) (0.20 g, 0.55 mmol) prepared in Example 1 in dry N-methylpyrrolidinone (3.0 ml). The resultant mixture solution was stirred for 2 hours at room temperature. After the reaction, the reaction solution was poured into excess ethanol to precipitate the obtained polymer. The precipitated polymer was filtered off and dried under reduced pressure to give 1.34 g of a poly(urethane-urea) having a phosphorylcholine group represented by the above formula PUU-1 as light brown powder. The structure was identified by the 1H-NMR spectrum given below:

Provenance & Evidence