Reaction #417902

ord-fc827500438e447a9fbd537c7d9446a6

Reaction equation

C=Cc1ccc(OC(C)(C)C)cc1
p-tert-Butoxystyrene
C=CC(=O)OC1CCCCC1
cyclohexyl acrylate
CC(C)(C#N)N=NC(C)(C)C#N
2,2′-azobisisobutyronitrile
C=CC(=O)OC1CCCCC1.C=Cc1ccc(OC(C)(C)C)cc1
p-tert-butoxystyrene cyclohexyl acrylate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Othera polymerization reaction at 75° C. for 6 hours
  2. 2
    TemperatureThe reaction solution was cooled
  3. 3
    FiltrationThe precipitated crystal was collected by filtration
  4. 4
    Washwashed with methanol
  5. 5
    Otherdried under reduced pressure

Procedure

p-tert-Butoxystyrene (176.3 g (1.0 mol)) and 16.2 g (0.105 mol) of cyclohexyl acrylate were dissolved in 250 ml of isopropanol, and in a nitrogen stream, 2,2′-azobisisobutyronitrile was added. The mixture was allowed to undergo a polymerization reaction at 75° C. for 6 hours. The reaction solution was cooled and then poured in 5,000 ml of methanol for crystallization. The precipitated crystal was collected by filtration, washed with methanol and dried under reduced pressure to obtain 172.5 g of poly(p-tert-butoxystyrene/cyclohexyl acrylate) as white powder crystal. The component ratio between p-tert-butoxystyrene unit and cyclohexyl acrylate unit in the obtained resin was found to be about 90:10 from 1HNMR and 13CNMR measurements. Also, the results of GPC measurement using polystyrene as a standard were Mw of about 20,600 and Mw/Mn of 1.55.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08877423B2uspto-grants-2014_11