Diphenylmethane diisocyanate → Urea Urethane

In an argon atmosphere, 1,4-butanediol (0.240 g, 2.66 mmol) and dibutyltin dilaurate (0.2 ml) were dissolved in N-methylpyrrolidinone (7.00 ml) in a three-necked flask. A solution of 4,4′-diphenylmethane diisocyanate (2.00 g, 7.99 mmol) in N-methylpyrrolidinone (7.00 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 (1.69 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 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-2 above as a brown solid (weight: 5.09 g, yield: 77.2%). 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-2 was found to be 19.7 mol %.

1. additionAfter the completion of the dropwise addition
2. customthe solution was reacted at 50° C. for 2 hours
3. customfollowed by reaction at 0° C. for 0.5 hour
4. customAfter the completion of the reaction
5. customfollowed by reaction at 50° C. overnight
6. customThe resultant reaction solution
7. filtrationfiltered
8. customdried under reduced pressure

ORDレコード

ord-63e90ffa79f94b35947b9f9175e32ac3

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08063238B2