2-Hydroxyethyl acrylate → HCID 21225502, compound

HRID 488481Notes

Reaction equation

HRID 488481 reaction equation
O=C=[N:3]C1CC(C)(C)CC(C)(CN=C=O)C1.[C:17]([O:21][CH2:22][CH2:23]O)(=[O:20])[CH:18]=[CH2:19].[N-]=C=O>>[NH2:3][C:17]([O:21][CH2:22][CH3:23])=[O:20].[C:17]([O-:21])(=[O:20])[CH:18]=[CH2:19]

Participants

4

Reactant 3

HCID 131652-Hydroxyethyl acrylate2×HCID 105034IsocyanateHCID 169132Isophorone diisocyanate

Product 1

HCID 21225502HCID 21225502, compoundYield 2,150.1%

Procedure

A 250 mL, 3 neck round bottom flask fitted with a mechanical stirrer and a thermometer was dried under nitrogen and charged with poly-7-FOX diol (polyfluorooxetane diol with heptafluoro group) (24.3 grams, 9.1 meq.) from Example 5. Isophorone diisocyanate (3.0 grams, 27.2 meq) and dibutyltindilaurate (12 mg) were added and the mixture was heated at 70 C for 14 hours. The reaction mixture was cooled to room temperature and washed with heptane (2 times 100 mL each). The isocyanate-terminated poly-7-FOX prepolymer was then dissolved in tetrahydrofuran (50 mL) and treated with dibutyltin dilaurate (12 mg). The resulting solution was reacted with 2-hydroxyethyl acrylate (HEA, 1.16 gram, 10 meq) at room temperature. No observable exotherm was observed on the addition of HEA. The progress of the reaction was monitored by following the disappearance of the isocyanate band in an infrared spectroscopic spectrum (IR) at 2270 cm−1. The mixture was heated at a temperature of 60 C for 4 hours. On completion, as indicated by the disappearance of the NCO band in the IR, the reaction mixture was precipitated into water (450 mL). The resulting solution was dried over magnesium sulfate, filtered and stripped of solvent under reduced pressure to produce 17.2 grams of a urethane-acrylate terminated poly-7-FOX.

Workup

  1. customA 250 mL, 3 neck round bottom flask fitted with a mechanical stirrer
  2. customa thermometer was dried under nitrogen
  3. additioncharged with poly-7-FOX diol (polyfluorooxetane diol with heptafluoro group) (24.3 grams, 9.1 meq.) from Example 5
  4. temperaturethe mixture was heated at 70 C for 14 hours
  5. washwashed with heptane (2 times 100 mL each)
  6. customThe isocyanate-terminated poly-7-FOX prepolymer
  7. dissolutionwas then dissolved in tetrahydrofuran (50 mL)
  8. additiontreated with dibutyltin dilaurate (12 mg)
  9. customthe reaction mixture was precipitated into water (450 mL)
  10. dry with materialThe resulting solution was dried over magnesium sulfate
  11. filtrationfiltered

Sources & evidence

ORD record
ord-73c6db57416b4f8b99f7375e16dc03ba
Source dataset
uspto-grants-2005_12
Patent number
US06972317B2

Reaction notes

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