Pentaerythritol triacrylate → Urethane acrylate

HRID 734955Notes

Reaction equation

HRID 734955 reaction equation
[C:1]([O:5][CH2:6][C:7](CO)(COC(=O)C=C)COC(=O)C=C)(=[O:4])[CH:2]=[CH2:3].O=C=[N:24]C1CC(C)(C)CC(C)(CN=C=O)C1>CC(CC(C)=O)C>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[NH2:24][C:1]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 19042Pentaerythritol triacrylateHCID 169132Isophorone diisocyanate

Product 1

HCID 21863578Urethane acrylateYield 499.5%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Procedure

A solution containing 50 ml of MIBK and 59.6 g (0.20 moles) of pentaerythritol triacrylate was added dropwisely to a solution containing 100 ml of MIBK and 22.2 g (0.1 moles) of isophorone diisocyanate included in a 500 ml flask at the temperature of 25° C., while air bubbling was conducted. After the dropwise addition was completed, 0.3 g of dibutyltin dilaurate was added to the mixture, and heating and stirring were conducted for 4 hours at the temperature of 70° C. After the reaction was completed, the obtained reaction solution was washed with 100 ml of 5% hydrochloric acid. Then, an organic layer was separated, and then solvent was removed under reduced pressure at the temperature of 40° C., or less to obtain 80.5 g of urethane acrylate which was a transparent and colorless viscous liquid.

Workup

  1. additionwas added dropwisely to a solution
  2. customincluded in a 500 ml flask at the temperature of 25° C., while air
  3. custombubbling
  4. additionAfter the dropwise addition
  5. addition0.3 g of dibutyltin dilaurate was added to the mixture
  6. temperatureheating
  7. customthe obtained reaction solution
  8. washwas washed with 100 ml of 5% hydrochloric acid
  9. customThen, an organic layer was separated
  10. customsolvent was removed under reduced pressure at the temperature of 40° C.

Sources & evidence

ORD record
ord-20ba0a20cdba43e3834e1c5d6af0cd46
Source dataset
uspto-grants-2009_09
Patent number
US07592405B2

Reaction notes

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