Methacrylic Acid → Methyl methacrylate isobornyl methacrylate methacrylic acid

HRID 2098230Notes

Reaction equation

HRID 2098230 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:8][C:9]([C:11]([O:13][CH:14]1[C@@:19]2([CH3:23])[C:20]([CH3:22])([CH3:21])[C@H:16]([CH2:17][CH2:18]2)[CH2:15]1)=[O:12])=[CH2:10].[C:24]([OH:29])(=[O:28])[C:25]([CH3:27])=[CH2:26].N(C(C)(C)C(OC)=O)=NC(C)(C)C(OC)=O>C(C(C)=O)C>[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:10][C:9]([C:11]([O:13][CH:14]1[C@@:19]2([CH3:23])[C:20]([CH3:22])([CH3:21])[C@H:16]([CH2:17][CH2:18]2)[CH2:15]1)=[O:12])=[CH2:8].[C:24]([OH:29])(=[O:28])[C:25]([CH3:27])=[CH2:26]

Participants

6

Reactant 4

HCID 4093Methacrylic AcidHCID 6658Methyl MethacrylateHCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)3×HCID 71311141Isobornylmethacrylate

Product 1

HCID 131730598Methyl methacrylate isobornyl methacrylate methacrylic acid

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent4×

Conditions

Temperature
75 °C

Procedure

In a 2 L three necked flask having a stirrer, a thermometer, a reflux condenser tube, and a nitrogen gas introducing pipe, 540.0 g of methyl ethyl ketone was charged, and the temperature was increased to 75° C. While maintaining the temperature in the reactor at 75° C., a mixed solution containing 108 g of methyl methacrylate, 388.8 g of isobornyl methacrylate, 43.2 g of methacrylic acid, 108 g of methyl ethyl ketone, and 2.16 g of “V-601” (trade name, manufactured by Wako Pure Chemical Inc., Ltd.) was added dropwise to the reactor at a constant speed so that the dropwise addition was completed in 2 hours. After the completion of the dropwise addition, a solution containing 1.08 g of “V-601” and 15.0 g of methyl ethyl ketone was added, and the resulting mixture was stirred at 75° C. for 2 hours. Thereafter, a solution containing 0.54 g of “V-601” and 15.0 g of methyl ethyl ketone was further added, and the resulting mixture was stirred at 75° C. for 2 hours. Thereafter, the temperature was increased to 85° C., and the mixture was continuously stirred for further 2 hours, thereby obtaining a resin solution of methyl methacrylate/isobornyl methacrylate/methacrylic acid (=20/72/8 [mass ratio]) copolymer.

Workup

  1. additionwas charged
  2. temperatureWhile maintaining the temperature in the reactor at 75° C.
  3. additionwas added dropwise to the reactor at a constant speed so that the dropwise addition
  4. additionAfter the completion of the dropwise addition
  5. additionwas added
  6. additionwas further added
  7. stirringthe resulting mixture was stirred at 75° C. for 2 hours
  8. temperatureThereafter, the temperature was increased to 85° C.
  9. stirringthe mixture was continuously stirred for further 2 hours

Sources & evidence

ORD record
ord-ee43bbf914054901b5bf65abeff33dce
Source dataset
uspto-grants-2013_05
Patent number
US08450394B2

Reaction notes

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