4-Methoxyphenol → Urethane acrylate

HRID 1710320Notes

Reaction equation

HRID 1710320 reaction equation
[C:1]([O:5]CC[N:8]=[C:9]=[O:10])(=[O:4])[CH:2]=[CH2:3].COC1C=CC(O)=CC=1.C(C1C=CC(C)=[C:26]([OH:31])[C:25]=1C(C)(C)C)(C)(C)C.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[NH2:8][C:9]([O:31][CH2:26][CH3:25])=[O:10]

Participants

5

Reactant 4

HCID 90154-MethoxyphenolHCID 30147682-Propenoic acid, 2-isocyanatoethyl esterHCID 9809426Di-n-butyldilauryltinHCID 19351831HCID 19351831, compound

Product 1

HCID 21863578Urethane acrylate

Conditions

Temperature
60 °C

Procedure

625 g (0.5 mol) of polyester polyol in the form of polycaprolactone diol (Daicel Chemical Industries, PLACCEL212, molecular weight: 1,250) and 142 g (1.0 mol) of 2-acryloyloxyethylisocyanate and 1.0 g each of p-methoxyphenol and di-t-butyl-hydroxytoluene were placed in a reaction vessel equipped with a stirring device, thermometer and condenser. After heating to 60° C. while stirring, heating was discontinued followed by the addition of 0.2 g of dibutyl tin dilaurate. Heating was resumed when the temperature inside the reaction vessel began to drop and stirring was continued at 80° C. The reaction was completed by confirming that the absorption spectrum of the isocyanate group (2,280 cm−1) had disappeared based on the infrared absorption spectrum to obtain a urethane acrylate compound in the form of a viscous liquid. The average molecular weight of the resulting urethane acrylate (UA-1) was 1,600.

Workup

  1. customequipped with a stirring device
  2. temperatureheating
  3. temperatureHeating
  4. stirringstirring
  5. customwas continued at 80° C

Sources & evidence

ORD record
ord-90307c2a7020465ca5837fc1a0f88a30
Source dataset
uspto-grants-2010_09
Patent number
US07790354B2

Reaction notes

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