epsilon-CAPROLACTONE → Urethane acrylate

HRID 861209Notes

Reaction equation

HRID 861209 reaction equation
[N-:1]=[C:2]=[O:3].[N-]=C=O.C1(CC2C=CC=CC=2)C=CC=CC=1.[OH-].[K+].[C:22]1(=[O:29])[O:28]CCC[CH2:24][CH2:23]1.C(O)CCC[CH2:34][CH2:35][OH:36].C(OCCO)(=O)C=C>>[C:22]([OH:29])(=[O:28])[CH:23]=[CH2:24].[NH2:1][C:2]([O:36][CH2:35][CH3:34])=[O:3]

Participants

6

Reactant 5

HCID 10401epsilon-CAPROLACTONEHCID 123741,6-HexanediolHCID 131652-Hydroxyethyl acrylateHCID 14797Potassium HydroxideHCID 19824838Benzylbenzene diisocyanate

Product 1

HCID 21863578Urethane acrylate

Conditions

Temperature
60 °C

Procedure

In a flask equipped with a thermometer, a stirrer and a condenser was charged 524 parts of diphenylmethane diisocyanate and heated to 60° C. with stirring. To the flask was added dropwise 520 parts of a ring opening reaction product (OH value: 215 KOH-mg/kg) between ε-caprolactone and 1,6-hexanediol over a period of 1 hour while giving care to heat generation. The reaction was carried on over 10 hours, and 232 parts of hydroxyethyl acrylate was added thereto, followed by further continuing the reaction for 10 hours. After confirming disappearance of the absorption of an isocyanate group in the infrared absorption spectrum, an urethane acrylate containing a hard segment and a soft segment was obtained as a comparative composition (designated RSH-1).

Workup

  1. customIn a flask equipped with a thermometer, a stirrer and a condenser
  2. additionTo the flask was added dropwise 520 parts of a ring
  3. customwhile giving care
  4. temperatureto heat generation
  5. additionwas added
  6. customthe reaction for 10 hours
  7. customdisappearance of the absorption of an isocyanate group in the infrared absorption spectrum

Sources & evidence

ORD record
ord-0c8b7b05f72c4fcb91b4a34bc79c5f07
Source dataset
uspto-grants-1998_02
Patent number
US05714218

Reaction notes

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