N-Isopropylacrylamide → HCID 131728324, compound

HRID 1713952Notes

Reaction equation

HRID 1713952 reaction equation
[CH3:1][CH:2]([NH:4][C:5]([CH:7]=[CH2:8])=[O:6])[CH3:3].[C:9]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:13])[C:10]([CH3:12])=[CH2:11].N(C(C)(CC)C#N)=NC(C)(CC)C#N>C(OCC)(=O)C>[CH3:1][CH:2]([NH:4][C:5]([CH:7]=[CH2:8])=[O:6])[CH3:3].[C:9]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:13])[C:10]([CH3:12])=[CH2:11]

Participants

5

Reactant 3

HCID 16637N-IsopropylacrylamideHCID 17234Tridecyl methacrylateHCID 930792,2'-Azobis(2-methylbutyronitrile)

Product 1

HCID 131728324HCID 131728324, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A 25 ml reaction vessel was charged with 12 g ethyl acetate, 2.85 g (0.007 mol) TRIS, 0.95 g (0.008 mol) NIPAM, 0.21 g (0.0008 mol) tridecyl methacrylate, and 0.078 g. 2,2′-azobis(2-methylbutanenitrile). After nitrogen flushing for 3 minutes, the vessel was closed and placed in an oil bath. The polymerization was run for 17.5 hours at 76° C. The polymer was precipitated into deionized water, dried at room temperature (20° C.), dissolved in acetone and precipitated into deionized water. The purified polymer was heated at 50° C. to remove bound water. Upon mixing the polymer with HMDS and casting a film, the film had an elongation of 10%. Upon addition of 2 wt % sucrose acetate isobutyrate to the polymer (10 wt %) in HMDS, the cast films had an elongation of greater than 250% without an increase in tack.

Workup

  1. customA 25 ml reaction vessel
  2. customthe vessel was closed
  3. customplaced in an oil bath
  4. waitThe polymerization was run for 17.5 hours at 76° C
  5. customThe polymer was precipitated into deionized water
  6. customdried at room temperature (20° C.)
  7. dissolutiondissolved in acetone
  8. customprecipitated into deionized water
  9. customto remove
  10. additionUpon mixing the polymer with HMDS
  11. additionUpon addition of 2 wt % sucrose acetate isobutyrate to the polymer (10 wt %) in HMDS
  12. temperaturean increase in tack

Sources & evidence

ORD record
ord-2b24e2f3aca645b899b6ce81cfd9b0fa
Source dataset
uspto-grants-2010_09
Patent number
US07795326B2

Reaction notes

Loading…