Methyl Methacrylate → HCID 22259533, compound

HRID 1648942Notes

Reaction equation

HRID 1648942 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8]([O:13][CH2:14][CH:15]1[O:17][CH2:16]1)(=[O:12])[C:9]([CH3:11])=[CH2:10].O1CCOCC1>N(C(C)(C)C#N)=NC(C)(C)C#N.O>[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8]([O:13][CH2:14][CH:15]1[O:17][CH2:16]1)(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

6

Reactant 3

HCID 6658Methyl MethacrylateHCID 7837Glycidyl methacrylateHCID 312751,4-Dioxane2×

Product 1

HCID 22259533HCID 22259533, compoundYield 253.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 962WaterSolvent

Procedure

A 500 ml. four-necked flask equipped with a stirrer, a condenser, a thermometer and a nitrogen introducing tube was charged with 85 g of methyl methacrylate, 21.3 g of glycidyl methacrylate, 100 ml of dioxane and 0.70 g of azobisisobutyronitrile, and the monomers were polymerized at 60° C. for 6 hours. After the reaction, 300 ml of dioxane was added to dilute the reaction mixture. The diluted mixture was poured into 3 liters of water with stirring to re-precipitate it. The precipitate was separated by filtration and dipped in methanol. The precipitate was again separated by filtration, and dried under reduced pressure at 60° C. to give 92 g of a methyl methacrylate/glycidyl methacrylate copolymer. Furthermore, the copolymer was dissolved in 200 ml of dioxane, and 15.75 g of diethanolamine and 0.8 g of triethylbenzyl ammonium iodide were added, and the reaction was carried out at 60° C. for 3 hours. The reaction mixture was reprecipitated with water. The precipitate was washed with methanol, and dried under reduced pressure at 60° C. to form 100 g (yield 90%) of the captioned polymer. The polymer had a viscosity, ηsp/c measured at 25° C. in chloroform in a concentration of 0.5 g/dl, of 0.40 dl/g.

Workup

  1. customfour-necked flask equipped with a stirrer, a condenser
  2. customthe monomers were polymerized at 60° C. for 6 hours
  3. additionwas added
  4. additionto dilute the reaction mixture
  5. customThe precipitate was separated by filtration
  6. customThe precipitate was again separated by filtration
  7. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-0144f4c531b34bf4be077924611c5859
Source dataset
uspto-grants-1983_11
Patent number
US04414254

Reaction notes

Loading…