Methyl p-toluenesulfonate → Urethane acrylate

HRID 532094Notes

Reaction equation

HRID 532094 reaction equation
C(N=C=O)CCCCC[N:7]=[C:8]=[O:9].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=CC=CC=1.C1(C)C=CC(S(OC)(=O)=O)=CC=1>>[C:13]([OH:20])(=[O:9])[CH:14]=[CH2:19].[NH2:7][C:8]([O:20][CH2:13][CH3:14])=[O:9]

Participants

4

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 7412Benzoyl chlorideHCID 13192Hexamethylene diisocyanate

Product 1

HCID 21863578Urethane acrylate

Procedure

1300 g of HDI (hexamethylene diisocyanate), 1.3 g of benzoyl chloride and 1.3 g of methyl para-toluenesulfonate are initially charged in a 41 four-neck flask while stirring. Within 3 hours, 1456 g of a difunctional polypropylene glycol polyether having a number-average molecular weight of 2000 g/mol are added at 80° C., and the mixture is stirred at the same temperature for a further 1 hour. Subsequently, the excess HDI was distilled off by thin-film distillation at 130° C. and 0.1 torr. The resulting prepolymer has an NCO content of 3.23% and a viscosity of 1650 mPas (25° C.).

Workup

  1. stirringthe mixture is stirred at the same temperature for a further 1 hour
  2. distillationSubsequently, the excess HDI was distilled off by thin-film distillation at 130° C.
  3. customa viscosity of 1650 mPas (25° C.)

Sources & evidence

ORD record
ord-ef763fcd9b3640449450bd06b778138b
Source dataset
uspto-grants-2014_10
Patent number
US08852829B2

Reaction notes

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