2-Hydroxyethyl acrylate → Urethane acrylate

HRID 2232662Notes

Reaction equation

HRID 2232662 reaction equation
[N-:1]=[C:2]=[O:3].[N-]=C=O.[O:7]=[C:8]1CC(C)(C)CC(C)=[CH:9]1.FC(F)(F)C(C1CCC(O)CC1)(C1CCC(O)CC1)C(F)(F)F.[C:40]([O:44]CCO)(=[O:43])[CH:41]=[CH2:42]>CC(C)=O.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.COC1C=CC(O)=CC=1>[C:40]([OH:44])(=[O:43])[CH:41]=[CH2:42].[NH2:1][C:2]([O:7][CH2:8][CH3:9])=[O:3]

Participants

7

Reactant 3

HCID 131652-Hydroxyethyl acrylateHCID 27822244-[1,1,1,3,3,3-Hexafluoro-2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-olHCID 21298402Isophorone DI-isocyanate

Product 1

HCID 21863578Urethane acrylateYield 821.4%

Reagents, catalysts & solvents 3

HCID 90154-MethoxyphenolCatalystHCID 9809426Di-n-butyldilauryltinCatalyst2×HCID 180AcetoneSolvent

Procedure

In 300 g of acetone were dissolved 46.2 g of isophoronediisocyanate, 70.3 g of 4,4'-(perfluoroisopropylidene)dicyclohexanol and 0.8 g of di-n-butyltin dilaurate. The mixture was reacted at 54° to 56° C. for 15 hours with stirring while introducing dry nitrogen. To the mixture were added 10 g of 2-hydroxyethyl acrylate, 0.4 g of di-n-butyltin dilaurate and 0.1 g of hydroquinone monomethyl ether and the mixture was reacted at 54° to 56° C. for 16 hours. A few drops of the reaction mixture were placed on KBr plate. The plate was dried and subjected to infrared absorption spectrum analysis to find an absorption based on isocyanate group (2250 cm-1) disappeared. The reaction mixture was poured into a large excess amount of hexane and the resulting precipitates were filtered, dried and pulverized to obtain 114 g of urethane acrylate in the form of white powder.

Workup

  1. customThe mixture was reacted at 54° to 56° C. for 15 hours
  2. additionwhile introducing dry nitrogen
  3. customthe mixture was reacted at 54° to 56° C. for 16 hours
  4. customThe plate was dried
  5. customan absorption
  6. additionThe reaction mixture was poured into a large excess amount of hexane
  7. customthe resulting precipitates
  8. filtrationwere filtered
  9. customdried

Sources & evidence

ORD record
ord-e0176e71a351451480f0d2f604d40f58
Source dataset
uspto-grants-1988_11
Patent number
US04788327

Reaction notes

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