4-Methoxyphenol → Urethane acrylate

HRID 1370151Notes

Reaction equation

HRID 1370151 reaction equation
OC[C:3]([CH3:7])([CH2:5][OH:6])C.[N-:8]=[C:9]=[O:10].[N-]=C=O.CCCCCC.COC1C=CC(O)=CC=1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C(OC(O)CCC)(=O)C=C>C(OCCCC)(=O)C>[C:5]([OH:10])(=[O:6])[CH:3]=[CH2:7].[NH2:8][C:9]([O:6][CH2:5][CH3:3])=[O:10]

Participants

7

Reactant 5

HCID 90154-MethoxyphenolHCID 31344Neopentyl glycolHCID 30166411-Hydroxybutyl 2-propenoateHCID 9809426Di-n-butyldilauryltinHCID 21863440HCID 21863440, compound

Product 1

HCID 21863578Urethane acrylate

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent2×

Conditions

Temperature
70 °C

Procedure

An 80 wt-% solution of a urethane acrylate in butyl acetate was prepared by initially dissolving 0.125 mole of neopentyl glycol at 65° C. in butyl acetate. 1 Mole of trimeric hexane diisocyanate was then added at 65° C. and the batch was heated to 70° C. After the exothermic reaction had ended, heating was continued at 80° C. until a constant NCO value was obtained. 4-Methoxyphenol (inhibitor) and dibutyltin dilaurate (catalyst) were then added in a quantity of 0.05 wt-% in each case, based on the total batch. 2.75 Moles of butane diol monoacrylate were added at 60° C. in such a way that a temperature of 80° C. was not exceeded. After an NCO value of <0.1 was obtained, the solids content was then adjusted with butyl acetate.

Workup

  1. customAfter the exothermic reaction
  2. temperatureheating
  3. customwas obtained

Sources & evidence

ORD record
ord-0e3f9842825545c59f9da9428dfa2dbd
Source dataset
uspto-grants-2003_06
Patent number
US06582770B2

Reaction notes

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