Ammonia → Styrene methylol maleimide

HRID 1193470Notes

Reaction equation

HRID 1193470 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:9]([C:11]1[C:12]([NH:14][C:15](=[O:17])[CH:16]=1)=[O:13])[OH:10].[OH-].C[N+](C)(C)C.N.C=CC1C=CC=CC=1.C1(=O)NC(=O)C=C1>C1(=O)CCCCC1.O.CN(C=O)C.CO>[CH2:9]([C:11]1[C:12]([NH:14][C:15](=[O:17])[CH:16]=1)=[O:13])[OH:10].[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

10

Reactant 5

HCID 222AmmoniaHCID 7501StyreneHCID 60966Tetramethylammonium hydroxideHCID 219817513-(Hydroxymethyl)-1H-pyrrole-2,5-dioneHCID 66643759Maleimide styrene

Product 1

HCID 86742784Styrene methylol maleimide

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 7967CyclohexanoneSolvent

Procedure

Styrene methylol maleimide copolymer was prepared by copolymerizing styrene (0.9 g) with methylol maleimide (1.0 g) in 10 ml cyclohexanone at 70° C. using azobisisobutylronitrile as an initiator for a period of 3 hours. The polymer was isolated by trituration of the solid, cooled reaction mixture with methanol. A sample of the polymer was examined by 1H/NMR (proton nuclear magnetic resonance) and found to have a spectrum consistent with the assigned composition. An IR spectrum of a film prepared from DMF solution showed a band in the region where OH stretching is expected. The polymer was found to be insoluble in water, but soluble in dilute tetramethyl ammonium hydroxide solution. A film treated with ammonia vapor gave an IR spectrum which no longer had the band associated with the --CH2OH group but which conformed to the spectrum of maleimide styrene copolymer.

Workup

  1. customThe polymer was isolated by trituration of the solid
  2. temperaturecooled
  3. customgave an IR spectrum which

Sources & evidence

ORD record
ord-19bfcb862fad456b9e524e6a7e2e59b0
Source dataset
uspto-grants-1989_03
Patent number
US04810613

Reaction notes

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