2-Hydroxyethyl acrylate → Urethane acrylate

HRID 724228Notes

Reaction equation

HRID 724228 reaction equation
[C:1]([O-:14])(=[O:13])[CH2:2][CH2:3]CCCCCCCCC.[C:15]([O-])(=[O:27])[CH2:16]CCCCCCCCCC.C([Sn+2]CCCC)CCC.CC(CCCCN=C=O)C(N=C=O)(C)C.[N-:53]=[C:54]=[O:55].OCCOC(=O)C=C>C(OCC)(=O)C>[C:1]([OH:14])(=[O:13])[CH:2]=[CH2:3].[NH2:53][C:54]([O:27][CH2:15][CH3:16])=[O:55]

Participants

6

Reactant 4

HCID 131652-Hydroxyethyl acrylateHCID 105034Isocyanate2×HCID 3033881Trimethylhexa-1,6-diyl diisocyanateHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 21863578Urethane acrylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

212 g (approx. 0.2 mol) Tego-Diol BD-1000, 70 g ethyl acetate and 0.1 g dibutyltin dilaurate are introduced into a 2 l 3-neck flask equipped with thermometer, reflux cooler, mechanical stirrer and drying tube, and 126 g (0.6 mol) trimethyl-hexamethylene diisocyanate added in measured doses, accompanied by cooling, over a period of 30 minutes. The reaction mixture is stirred for 20 hours at room temperature until the isocyanate content has fallen to 7.7%. 91 g hydroxyethylacrylate is added accompanied by cooling. After 72 hours at room temperature, an isocyanate value of 0 is recorded, at which the reaction is ended. The ethyl acetate can be distilled off in fine vacuum.

Workup

  1. customequipped with thermometer
  2. temperaturereflux cooler, mechanical stirrer
  3. customdrying tube
  4. temperatureby cooling, over a period of 30 minutes
  5. temperatureby cooling
  6. distillationThe ethyl acetate can be distilled off in fine vacuum

Sources & evidence

ORD record
ord-6f4b19c22f8f4ddab9b42fbe5708668d
Source dataset
uspto-grants-2006_11
Patent number
US07141616B2

Reaction notes

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