Diphenylmethane diisocyanate → Urethane acrylate

HRID 1253101Notes

Reaction equation

HRID 1253101 reaction equation
N(C1C=CC(CC2C=CC(N=C=O)=CC=2)=CC=1)=C=O.[C:20]([O-:33])(=[O:32])[CH2:21][CH2:22]CCCCCCCCC.[C:34]([O-])(=[O:46])[CH2:35]CCCCCCCCCC.C([Sn+2]CCCC)CCC.[N-:57]=[C:58]=[O:59]>C(C(C)=O)C>[C:20]([OH:33])(=[O:32])[CH:21]=[CH2:22].[NH2:57][C:58]([O:46][CH2:34][CH3:35])=[O:59]

Participants

5

Reactant 3

HCID 7570Diphenylmethane diisocyanateHCID 105034IsocyanateHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 21863578Urethane acrylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

Into a one liter 3-neck flask equipped with a mechanical stirrer, reflux condenser and drying tube, thermometer, and oil bath with temperature control, 130 g (0.1 mole) Sulfoester Polyol A (prepared as described below), was added to 50 g (0.2 mole) bis(4-isocyanatophenyl)methane, 0.03 g dibutyltin dilaurate, and 150 g methyl ethyl ketone. As stirring was initiated, the temperature began to rise. Additional heat was applied to raise the temperature of the contents of the flask to 60° C. and held at this temperature until analysis indicated the disappearance of hydroxyl and formation of isocyanate-terminated sulfopolyester (4 hours). There was then added 65 g pentaerythritol triacrylate and 500 ppm (with respect to the acrylate) of p-methoxy phenol. Stirring and heating was continued for an additional 4 hours at 60° C. The polymer was readily soluble in water from which it could be coated as a film and dried to a non-tacky coating that could be redissolved in water, sodium hydroxide solution, methanol, aqueous methanol, acetone, methylene chloride and other common organic solvents. The dried film had a calculated average molecular weight of 2400 and an acrylic group equivalent weight of about 400.

Workup

  1. customInto a one liter 3-neck flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. customdrying tube
  4. temperatureAdditional heat
  5. customterminated sulfopolyester (4 hours)
  6. additionThere was then added 65 g pentaerythritol triacrylate and 500 ppm (with respect to the acrylate) of p-methoxy phenol
  7. stirringStirring
  8. temperatureheating
  9. customdried to a non-tacky coating that
  10. dissolutioncould be redissolved in water

Sources & evidence

ORD record
ord-d2893c5e2daa47be8ceb316590264fe1
Source dataset
uspto-grants-1988_05
Patent number
US04746717

Reaction notes

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