Diphenylmethane diisocyanate → Urea Urethane

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In an argon atmosphere, 1,4-butanediol (0.120 g, 1.33 mmol) and dibutyltin dilaurate (0.2 ml) were dissolved in N-methylpyrrolidinone (6.50 ml) in a three-necked flask. A solution of 4,4′-diphenylmethane diisocyanate (2.00 g, 7.99 mmol) in N-methylpyrrolidinone (6.50 ml) was slowly added dropwise to the solution at room temperature. After the completion of the dropwise addition, the solution was reacted at 50° C. for 2 hours. Thereafter, a solution of the compound (6) from Example 1 (2.53 g, 4.00 mmol) in N-methylpyrrolidinone (4.00 ml) was slowly added dropwise to the reaction solution at 0° C., followed by reaction at 0° C. for 0.5 hour. After the completion of the reaction, a solution of polytetramethylene glycol (2.66 g, 2.66 mmol) in N-methylpyrrolidinone (3.00 ml) was slowly added dropwise to the reaction solution at 0° C., followed by reaction at 50° C. overnight. The resultant reaction solution was poured into an excess of a solvent mixture (methanol:diethyl ether=1:1 (by volume)) The precipitate caused was suction filtered and dried under reduced pressure to give a segmented poly(urethane-urea) with a phosphorylcholine group represented by Formula SPUU-3 above as a brown solid (weight: 4.72 g, yield: 64.6%). The structure of the polymer was determined from the IR spectrum given below. From the 1H-NMR spectrum, the phosphorylcholine group content in the polymer SPUU-3 was found to be 38.7 mol %.

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