Acrylic Acid → Phenoxyethyl acrylate methyl methacrylate acrylic acid

HRID 1950660Notes

Reaction equation

HRID 1950660 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(O)(C)C.C(C(C)=O)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 introduced in a 2 L three-necked flask equipped with a stirrer, a thermometer, a reflux cooling tube, and a nitrogen gas supply tube and was then heated to 75° C. Then, a mixed solution of 180.0 g of phenoxyethyl acrylate, 162.0 g of methyl methacrylate, 18.0 g of acrylic acid, 72 g of methyl ethyl ketone, and 1.44 g of “V-601” (trade name, manufactured by Wako Pure Chemical Industries, Ltd.) was added dropwise thereto at a constant speed such that the addition was completed in 2 hours, while the temperature of the flask was maintained at 75° C. After the addition was completed, a solution of 0.72 g of “V-601” and 36.0 g of methyl ethyl ketone was added thereto, followed by stirring at 75° C. for 2 hours. Further, a solution of 0.72 g of “V-601” and 36.0 g of isopropanol was added thereto, followed by stirring at 75° C. for 2 hours. Then, the resultant solution was heated to 85° C., and stirred for 2 hours, to obtain a resin solution of a phenoxyethyl acrylate/methyl methacrylate/acrylic acid (=50/45/5[ mass ratio]) copolymer.

Workup

  1. customequipped with a stirrer
  2. temperaturea thermometer, a reflux cooling tube
  3. additionat a constant speed such that the addition
  4. temperaturewas maintained at 75° C
  5. additionAfter the addition
  6. stirringby stirring at 75° C. for 2 hours
  7. stirringstirred for 2 hours

Sources & evidence

ORD record
ord-b16c44c0006549e68ce24729053984d6
Source dataset
uspto-grants-2013_03
Patent number
US08403472B2

Reaction notes

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