Ammonia → Styrene methylol maleimide

HRID 1589913Notes

Reaction equation

HRID 1589913 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 azobis-isobutylronitrile 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. customof 3 hours
  2. customThe polymer was isolated by trituration of the solid
  3. temperaturecooled
  4. customgave an IR spectrum which

Sources & evidence

ORD record
ord-8567c306b7114bcbb35476de2490f7f3
Source dataset
uspto-grants-1993_04
Patent number
US05200529

Reaction notes

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