Acrylic Acid → Phenoxyethyl acrylate methyl methacrylate acrylic acid

HRID 2191169Notes

Reaction equation

HRID 2191169 reaction equation
[C:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:4])[CH:2]=[CH2:3].[C:15]([O:20][CH3:21])(=[O:19])[C:16]([CH3:18])=[CH2:17].[C:22]([OH:26])(=[O:25])[CH:23]=[CH2:24].N(C(C)(C)C(OC)=O)=NC(C)(C)C(OC)=O>C(C(C)=O)C.C(O)(C)C>[C:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:4])[CH:2]=[CH2:3].[C:15]([O:20][CH3:21])(=[O:19])[C:16]([CH3:18])=[CH2:17].[C:22]([OH:26])(=[O:25])[CH:23]=[CH2:24]

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 6658Methyl MethacrylateHCID 39485Phenoxyethyl acrylateHCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)3×

Product 1

HCID 86634647Phenoxyethyl acrylate methyl methacrylate acrylic acid

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6569Methyl Ethyl KetoneSolvent3×

Conditions

Temperature
75 °C

Procedure

360.0 g of methyl ethyl ketone was placed in a 2 L three-necked flask equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas introduction tube, and was heated to 75° C. Thereafter, while the temperature inside the flask was maintained at 75° C., a mixture solution of 180.0 g of phenoxyethyl acrylate (PhOEA), 158.4 g of methyl methacrylate (MMA), 21.6 g of acrylic acid (AA), 72 g of methyl ethyl ketone, and 1.44 g of V-601 (trade name, manufactured by Wako Pure Chemical Industries Ltd.) was added drop-wise into the flask at a constant rate such that the drop-wise addition was completed in 2 hours. After the drop-wise addition was completed, a solution of 0.72 g of V-601 in 36.0 g of methyl ethyl ketone was added into the flask, stirred at 75° C. for 2 hours, and a solution of 0.72 g of V-601 in 36.0 g of isopropanol was further added, and the contents of the flask were stirred at 75° C. for 2 hours. Then, the temperature inside the flask was increased to 85° C., and stirring was continued for another 2 hours. As a result, a resin solution of a copolymer of phenoxyethyl acrylate/methyl methacrylate/acrylic acid (in a ratio of 50/45/6 by mass) was obtained.

Workup

  1. customequipped with a stirrer
  2. temperatureThereafter, while the temperature inside the flask was maintained at 75° C.
  3. additionsuch that the drop-wise addition
  4. additionAfter the drop-wise addition
  5. stirringthe contents of the flask were stirred at 75° C. for 2 hours
  6. temperatureThen, the temperature inside the flask was increased to 85° C.
  7. stirringstirring
  8. waitwas continued for another 2 hours

Sources & evidence

ORD record
ord-ef7848f87b6e4d2d937b41046241d885
Source dataset
uspto-grants-2012_12
Patent number
US08328342B2

Reaction notes

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