Quinone → Carbamic acid, ethyl ester

HRID 462021Notes

Reaction equation

HRID 462021 reaction equation
CC1C(N=C=O)=CC([N:8]=[C:9]=[O:10])=CC=1.C([C:16]([CH2:21][OH:22])(CO)CC)O.[C:23]([O:28][CH3:29])(=[O:27])[C:24]([CH3:26])=[CH2:25].C1(=O)C=CC(=O)C=C1.C(OCCO)(=O)C(C)=C>>[NH2:8][C:9]([O:22][CH2:21][CH3:16])=[O:10].[C:23]([O:28][CH3:29])(=[O:27])[C:24]([CH3:26])=[CH2:25]

Participants

7

Reactant 5

HCID 4650QuinoneHCID 6510TrimethylolpropaneHCID 6658Methyl Methacrylate2×HCID 11443Toluene 2,4-DiisocyanateHCID 133602-Hydroxyethyl Methacrylate

Product 2

HCID 5641Carbamic acid, ethyl esterHCID 6658Methyl Methacrylate

Conditions

Temperature
70 °C

Procedure

A U.V. curable urethane composition is prepared by heating 104.4 grams (0.6 moles) of tolylene diisocyanate to 70° C. and, while maintaining this temperature adding dropwise over 2 hours a homogeneous solution, also heated to 70° C., consisting of 26.8 grams of trimethylolpropane, 79.0 grams of methyl methacrylate and 0.02 grams p-benzoquinone. At the end of the reaction period, the product is maintained at 70° C. for an additional 6 hours. There is, thereafter, added dropwise 57.2 grams of 2-hydroxyethyl methacrylate over a period of one-half hour, after which the reaction is continued for an additional 10 hours, followed by the addition of 43 grams methyl methacrylate, to obtain a methyl methacrylate solution of a light yellow, transparent photopolymerizable prepolymer containing approximately 1.8% by weight of isocyanate groups.

Workup

  1. temperaturewhile maintaining this temperature
  2. additionadding dropwise over 2 hours a homogeneous solution
  3. customAt the end of the reaction period
  4. temperaturethe product is maintained at 70° C. for an additional 6 hours

Sources & evidence

ORD record
ord-c502d12013f7497d9c8654a11609f5d7
Source dataset
uspto-grants-1977_12
Patent number
US04065315

Reaction notes

Loading…