4-Methoxyphenol → Urethane acrylate

HRID 1892101Notes

Reaction equation

HRID 1892101 reaction equation
[CH2:1]([OH:23])[CH2:2][CH2:3]CCCCCCCCCCCCCCCCCCC.C(N=C=O)CCCCCN=C=[O:32].C1C=C(C[N:43]=[C:44]=[O:45])C=C(CN=C=O)C=1.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C([O-])(=O)CCCCCCCCCCC.C(OCCO)(=O)C=C.COC1C=CC(O)=CC=1>C1(C)C=CC=CC=1>[C:1]([OH:23])(=[O:32])[CH:2]=[CH2:3].[NH2:43][C:44]([O:23][CH2:1][CH3:2])=[O:45]

Participants

8

Reactant 6

HCID 90154-MethoxyphenolHCID 12620Behenyl Alcohol2×HCID 131652-Hydroxyethyl acrylateHCID 13192Hexamethylene diisocyanateHCID 192621,3-Bis(isocyanatomethyl)benzeneHCID 9809426Di-n-butyldilauryltin2×

Product 1

HCID 21863578Urethane acrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

Into 50 parts of toluene, 5.8 parts of behenyl alcohol (“NAA-422”, trade name, produced by NOF Corporation, hydroxyl value: 180) was added and the mixture was heated up to 40° C. After thorough dissolution of the behenyl alcohol, 50 parts of hexamethylene diisocyanate subjected to isocyanurate modification (“TAKENATE D-170N”) was added and the mixture was maintained at 70° C. for 30 minutes. Subsequently, 0.02 parts of dibutyltin laurate was added and the mixture was maintained at 70° C. for 3 hours. Further, 2.8 parts of 2-hydroxyethyl acrylate (Light Ester HOA), 36.1 parts of polycaprolactone-modified hydroxyethyl acrylate (“PLACCEL FA1”), 48.1 parts of polycaprolactone-modified hydroxyethyl acrylate (“PLACCEL FA5”), 0.02 parts of dibutyltin laurate and 0.02 parts of hydroquinone monomethyl ether were added and the mixture was maintained at 70° C. for 5 hours. Thereafter, 92.8 parts of toluene was added to obtain a urethane acrylate having a solid content of 50% by weight. The average number of repetitions per one molecule of the urethane acrylate relative to the number of repetitions of a caprolactone unit per one residue of an acrylate monomer is 2. Further, the maximum difference in the number of repetitions between two kinds of the urethane acrylates is 5.

Workup

  1. additionwas added
  2. temperaturethe mixture was maintained at 70° C. for 30 minutes
  3. temperaturethe mixture was maintained at 70° C. for 3 hours
  4. temperaturethe mixture was maintained at 70° C. for 5 hours

Sources & evidence

ORD record
ord-73b59f5c0d8d4b209e69e6431085ac34
Source dataset
uspto-grants-2013_08
Patent number
US08507632B2

Reaction notes

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