2-Hydroxyethyl Methacrylate → Urethane methacrylate

HRID 724229Notes

Reaction equation

HRID 724229 reaction equation
[C:1]([O-])(=[O:13])[CH2:2]CCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.CC(CCCCN=C=O)C(N=C=O)(C)C.[N-:53]=[C:54]=[O:55].[C:56]([O:61]CCO)(=[O:60])[C:57]([CH3:59])=[CH2:58]>CC(C)=O>[C:56]([OH:61])(=[O:60])[C:57]([CH3:59])=[CH2:58].[NH2:53][C:54]([O:13][CH2:1][CH3:2])=[O:55]

Participants

6

Reactant 4

HCID 133602-Hydroxyethyl MethacrylateHCID 105034Isocyanate2×HCID 3033881Trimethylhexa-1,6-diyl diisocyanateHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 10012418Urethane methacrylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

212 g (approx. 0.2 mol) Tego-Diol BD-1000, 140 g acetone and 0.1 g dibutyltin dilaurate are introduced first into a 2I 3-neck flask equipped with thermometer, reflux cooler, mechanical stirrer and drying tube, and 84 g (0.4 mol) trimethyl-hexamethylene diisocyanate added in measured does, 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 3.7%. 53 g hydroxyethyl methacrylate is added, accompanied by cooling. After 72 hours at room temperature, an isocyanate value of 0.1 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-7ab601e93d5e4815945cb69d344fe0a0
Source dataset
uspto-grants-2006_11
Patent number
US07141616B2

Reaction notes

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