Propylene Oxide → Urethane acrylate

HRID 850683Notes

Reaction equation

HRID 850683 reaction equation
[C:1]([O:5][CH2:6][CH2:7]O)(=[O:4])[CH:2]=[CH2:3].C1OC1C.COC1C=CC(O)=CC=1.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.O=C=[N:61]C1CC(C)(C)CC(C)(CN=C=O)C1>>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[NH2:61][C:1]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 5

HCID 6378Propylene OxideHCID 90154-MethoxyphenolHCID 131652-Hydroxyethyl acrylateHCID 169132Isophorone diisocyanateHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 21863578Urethane acrylate

Procedure

14.92 Grams of an addition product of 2-hydroxyethyl acrylate with propylene oxide [BLENMAR 10APE-550B of Nippon Oil and Fats Co. Ltd.; a compound of the formula (vi) wherein R2 is H, R3 is CH3, e is 1 and f is 9], 0.63 g of hydroquinone monomethyl ether, 0.51 g of di-n-butyltin dilaurate and 222 g of isophorone diisocyanate were charged to a 4-liter four-necked flask equipped with a stirrer, a thermoregulator, a thermometer and a condenser, allowed to react with one another at 40 to 50° C. for 30 minutes and then the reaction was further continued at 80 to 90° C. to produce the second urethane acrylate [a compound of the formula (2) wherein R2 is H, R3 is CH3, A2 is an isophorone group, e is 1, f is 9 and g is 2].

Workup

  1. additionwere charged to a 4-liter four-necked flask
  2. customequipped with a stirrer
  3. customto react with one another at 40 to 50° C. for 30 minutes
  4. customwas further continued at 80 to 90° C.

Sources & evidence

ORD record
ord-fd37c4baabd44a9ca150470b8468b4df
Source dataset
uspto-grants-2000_01
Patent number
US06017973

Reaction notes

Loading…