Acetone → 2-Methylprop-2-enoic acid--prop-2-enimidic acid (1/1)

HRID 1581460Notes

Reaction equation

HRID 1581460 reaction equation
[C:1]([O:6]CC1OC1)(=[O:5])[C:2]([CH3:4])=[CH2:3].C[N:12](CCCCCCCCCCCC)C.C1(C=CC(O)=CC=1)O.CC(C)=O>CS(C)=O>[C:1]([NH2:12])(=[O:6])[CH:2]=[CH2:3].[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 180AcetoneHCID 785HydroquinoneHCID 7837Glycidyl methacrylateHCID 8168Lauryldimethylamine

Product 1

HCID 1614772-Methylprop-2-enoic acid--prop-2-enimidic acid (1/1)Yield 6,304.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

After 20 g of the obtained prepolymers were dissolved in 62 g of dimethyl sulfoxide, 6.71 g of glycidyl methacrylate, 504 mg of N,N-dimethyldodecylamine (catalyst), and 62.4 mg of hydroquinone (polymerization inhibitor) were added. The obtained solution was allowed to react for 7 hours at 140° C. in a nitrogen atmosphere. Acetone was added to the resultant solution to precipitate a polymer. The polymer was sufficiently washed to obtain 23.4 g of terminal methacrylate acrylamide macromonomer (weight average molecular weight: 1,400). It was confirmed that a polymerizable group was introduced into the terminal because H1-NMR(D20) 6.12, 5.70 ppm methacryloyl group olefin peak, and the acid value (0.057meq/g) decreased.

Workup

  1. customto react for 7 hours at 140° C. in a nitrogen atmosphere
  2. customto precipitate a polymer
  3. washThe polymer was sufficiently washed

Sources & evidence

ORD record
ord-30cab33dc24544618487b3d3d5608fed
Source dataset
uspto-grants-2004_05
Patent number
US06730456B2

Reaction notes

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