Methacrylic Acid → 2-Methylprop-2-enoic acid--ethyl prop-2-enoate (1/1)

HRID 904764

Reaction equation

HRID 904764 reaction equation
C([O-])(=O)C=C.[C:6]([O:10][CH2:11][CH3:12])(=[O:9])[CH:7]=[CH2:8].[C:13]([OH:18])(=[O:17])[C:14]([CH3:16])=[CH2:15]>>[C:6]([O:10][CH2:11][CH3:12])(=[O:9])[CH:7]=[CH2:8].[C:13]([OH:18])(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

4

Reactant 3

HCID 4093Methacrylic AcidHCID 8821Ethyl AcrylateHCID 25188Acrylate

Product 1

HCID 1076652-Methylprop-2-enoic acid--ethyl prop-2-enoate (1/1)

Conditions

Temperature
65 °C

Procedure

Into an agitated reactor outfitted for nitrogen blanketing of the contents there are charged: 1,009 parts of a 35% solids polybutadiene latex having an average particle size of 1,000 A; 360 parts water; 1 part acetic acid to give the reaction mass a pH of 4; 0.085 part of the bisodium salt of ethylenediaminetetracetic acid (herein referred to as "EDTA.2Na+ " or just "EDTA") and 1.05 parts of K2S2O8. Heat is applied until the charged contents reach 65° C. At this point, two continuous addition streams are started and feed into the reactor. One is an aqueous stream which is charged over a 11/4 hour period and contains 68 parts of a water solution of 0.125% K2S2O8 and 2.5% sodium dodecylbenzene sulfonate. The other is a monomer stream which is charged over a one-hour period and consists of 85 parts of a 92:8 weight ratio mixture of ethyl acrylate (EA) and methacrylic acid (MAA) calculated to give a 20% shell in the resulting graft copolymer (based on wt. polybutadiene plus wt. interpolymerized EA and MAA contents). After the addition is completed, the reaction mass is maintained at 65° C. with continued stirring for 3 additional hours. Analysis of the resulting AgAg graft copolymer latex material shows that approximately 100% interpolymerization of the acid and acrylate monomers has been achieved to yield particles consisting of 20% shell, the shell consisting of about 92% EA and 8% MAA. Extraction with methyl ethyl ketone (MEK) of the resultant AgAg material demonstrates that 79% of the EA/MAA monomeric mixture has actually been grafted to the 1,000 A polybutadiene (PBD) particles and 21% exists in the shell as non-grafted EA/MAA copolymer.

Workup

  1. additionAfter the addition
  2. customto yield particles
  3. extractionExtraction with methyl ethyl ketone (MEK) of the resultant AgAg material

Sources & evidence

ORD record
ord-b95da32c27294277b1aaf4becdb35d95
Source dataset
uspto-grants-1983_12
Patent number
US04419496

Linked notes

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