1,6-Hexanediol → HCID 131716352, compound

In a 100 mL reaction flask fitted with mechanical stirrer and argon inlet were combined trimethylene carbonate (51.45 g, 504 mmol), l-lactide (8.07 g, 56 mmol), and 1,6-hexanediol (47 mg, 0.40 mmol). The flask was evacuated and filled with argon several times, immersed in an oil bath at 160° C. and stirring was initiated. After 10 mins., the polymerization catalyst, 25 μL of 0.02M solution of tin(II) octoate in toluene, was added via syringe. The mixture was stirred at 160° C. for 4 hrs., then the polymer was removed from the flask, dissolved in tetrahydrofuran (450 mL), and precipitated into methanol (1200 mL) in a blender. The precipitated polymer was stirred with additional methanol (400 mL) in the blender, filtered, and dried in the vacuum oven at 50° C. Yield: 43.8 g (74%). Weight average molecular weight=120,000 (polydispersity 1.5). Proton NMR (400 MHz) shows a final composition of 80% trimethylene carbonate units and 20% lactic acid units (theoretical 82% and 18%, respectively). This polymer is especially useful as a coating polymer.

1. customIn a 100 mL reaction flask
2. customfitted with mechanical stirrer and argon inlet
3. customThe flask was evacuated
4. additionfilled with argon several times
5. customimmersed in an oil bath at 160° C.
6. addition, the polymerization catalyst, 25 μL of 0.02M solution of tin(II) octoate in toluene, was added via syringe
7. stirringThe mixture was stirred at 160° C. for 4 hrs
8. custom, then the polymer was removed from the flask
9. dissolutiondissolved in tetrahydrofuran (450 mL)
10. customprecipitated into methanol (1200 mL) in a blender
11. stirringThe precipitated polymer was stirred with additional methanol (400 mL) in the blender
12. filtrationfiltered
13. customdried in the vacuum oven at 50° C

ORD record

ord-0ae803d131b048cb98ff2c4e6d97545d

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05185408