Diphenylmethane diisocyanate → Urea Urethane

関与物質

反応手順

In an argon atmosphere, 1,4-butanediol (0.350 ml, 4.00 mmol) and dibutyltin dilaurate (DBTDL) (0.2 ml) were dissolved in N-methylpyrrolidinone (NMP) (8.00 ml) in a three-necked flask. A solution of 4,4′-diphenylmethane diisocyanate (2.00 g, 7.99 mmol) in N-methylpyrrolidinone (8.00 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 (0.844 g, 1.33 mmol) in N-methylpyrrolidinone (1.50 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-1 above as a white solid (weight: 4.81 g, yield: 82.1%). 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-1 was found to be 14.9 mol %.

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