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Ammonia → Styrene methylol maleimide

HRID 1090052
Notes
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Reaction equation

HRID 1090052 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887MethanolSolvent
HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent
HCID 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-3fec899561d6471a93755d6693e38665
Source dataset
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05081001

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes