Thioglycolic Acid → Methyl 2-methylprop-2-enoate;styrene

HRID 2231888Notes

Reaction equation

HRID 2231888 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)CS.N(C(C)(C)C#N)=NC(C)(C)C#N>>[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 1133Thioglycolic AcidHCID 6547AzobisisobutyronitrileHCID 6658Methyl MethacrylateHCID 7501Styrene

Product 1

HCID 159984Methyl 2-methylprop-2-enoate;styrene

Procedure

A monomeric mixture of 45 parts of methyl methacrylate and 55 parts of styrene added with thioglycolic acid as a chain transfer agent was bulk polymerized in the presence of azobisisobutyronitrile as an initiator to obtain an oligomer having a molecular weight of about 2,000 after purification by reprecipitation. The resulting oligomer was dissolved in xylene and added with glycidyl methacrylate in an amount of 1.3 times equivalent of carboxyl groups contained in the oligomer, a catalytic amount of N,N-dimethyldodecylamine and a trace amount of a radical polymerization inhibitor. Then, the mixture was reacted at 120° C. for 5 hours and purified by reprecipitation to obtain a methyl methacrylate/styrene copolymer having vinyl groups at chain ends.

Workup

  1. customto obtain an oligomer
  2. customafter purification
  3. customby reprecipitation
  4. dissolutionThe resulting oligomer was dissolved in xylene
  5. additionadded with glycidyl methacrylate in an amount of 1.3 times equivalent of carboxyl groups
  6. customThen, the mixture was reacted at 120° C. for 5 hours
  7. custompurified by reprecipitation

Sources & evidence

ORD record
ord-0cd23e4100964eb8857a232dc3f96642
Source dataset
uspto-grants-1988_11
Patent number
US04785053

Reaction notes

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