Phenyl isocyanate → Carbamate

HRID 1890205Notes

Reaction equation

HRID 1890205 reaction equation
[CH3:1][C:2]([CH3:21])=[C:3]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4]1.C1(=[O:28])CCCCC1.C1([N:35]=[C:36]=[O:37])C=CC=CC=1>C(N(CC)CC)C>[CH3:1][C:2]([CH3:21])=[C:3]1[CH:8]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])=[CH:13][CH:14]=2)[CH:7]=[CH:6][CH:5]=[CH:4]1.[C:36](=[O:37])([O-:28])[NH2:35]

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 7967CyclohexanoneHCID 85771059HCID 85771059, compound

Product 2

HCID 276CarbamateHCID 85771059HCID 85771059, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

100 g of phenoxy resin (YP-50, hydroxyl group equivalent=284, Toto Kasei Inc., trade name) and 330 g of cyclohexanone were introduced into a 1 L separable flask fitted with a reflux condenser, thermometer and stirrer, and the mixture heated with stirring to dissolve the resin. Subsequently, 41.9 g phenyl isocyanate and 0.3 g triethylamine were added, and reacted at 130° C. for 3 hours. Next, the product was reprecipitated in ethanol, and dried to give a phenoxy resin to which carbamate had been added. This resin was then dissolved in dimethylformamide (DMF) to give a concentration of 30 mass %, and the resin primer of Example 4 was thus obtained.

Workup

  1. customfitted with a reflux condenser
  2. temperaturethermometer and stirrer, and the mixture heated
  3. dissolutionto dissolve the resin
  4. customreacted at 130° C. for 3 hours
  5. customNext, the product was reprecipitated in ethanol
  6. customdried

Sources & evidence

ORD record
ord-95d9c4f1456c4c04aed4a89c1860fe03
Source dataset
uspto-grants-2013_08
Patent number
US08507100B2

Reaction notes

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