4-Methoxyphenol → Urethane acrylate

HRID 572816Notes

Reaction equation

HRID 572816 reaction equation
[O:1]=C=NC1CC(C)(C)CC(C)(CN=C=O)C1.C[O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=C[CH:20]=1.[N-:26]=[C:27]=[O:28]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.O>[C:22]([OH:25])(=[O:1])[CH:23]=[CH2:24].[NH2:26][C:27]([O:18][CH2:19][CH3:20])=[O:28]

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 105034IsocyanateHCID 169132Isophorone diisocyanate

Product 1

HCID 21863578Urethane acrylate

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 962WaterSolvent2×

Procedure

An amount of isophorone diisocyanate was added to a reaction vessel at room temperature. Heating jacket temperature was adjusted to 45° C. suspended in a room temperature water bath and stirred. When the reaction batch temperature was 45° C., dibutyltin dilaurate (DBTDL), as catalyst, and 4-methoxy phenol (MEHQ), as free-radical polymerization inhibitor, were also added. Pentaerytritol triacrylate was added incrementally to control exothermic activity. When the exothermic activity ceased, the result of Stage I was added and batch temperature was adjusted to 60° C. The batch was kept at 60° C. until no free isocyanate was detected by FTIR. Reaction scheme is given below. Viscosity of the product was 13,000 cP at 25° C. and it readily mixes with water. When the product was diluted with equal amount (by weight) of water viscosity was 50 cP at 25° C.

Workup

  1. temperatureHeating jacket temperature
  2. customwas adjusted to 45° C.
  3. customsuspended in a room temperature
  4. customwas 45° C.
  5. customthe result of Stage I
  6. additionwas added
  7. customwas adjusted to 60° C
  8. customReaction scheme
  9. customat 25° C.
  10. customat 25° C.

Sources & evidence

ORD record
ord-c94c71ab1cdb4bc5b54ce57a1a352ee6
Source dataset
uspto-grants-2015_05
Patent number
US09029489B2

Reaction notes

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