Studies of radical homopolymerization of N-(4-iodo-1,3-diphenylbutyl) acrylamide

Abstract

N-(4-iodo-1,3-diphenylbutyl) acrylamide (NIAM) is a potential hydrophobic monomer for preparation of hydrophobically modified polyacrylamide largely used for enhanced oil recovery. Moreover, it has an iodine group as substitute allowing further modification reactions. This monomer was synthesized via Ritter reaction as described in the literature and characterized by nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). DSC analysis of monomer showed two endothermic peaks referring to the melting points of a mixture of diastereoisomers. Conventional radical homopolymerization of NIAM was investigated, and the polymer was characterized by NMR, TGA, DSC and size-exclusion chromatography. The polymerization was successfully performed only in the presence of large amounts of radical initiator 2,2′-azobis(2-methylpropionitrile) (AIBN) suggesting an iodine transfer polymerization mechanism. The polymer showed low degree of polymerization, dispersity lower than 1.1 and glass transition temperature of 19.5 °C.

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Acknowledgements

The authors acknowledge the financial support by PETROBRAS S.A., Dr. Alexsandro Dallegrave for the UHPLC-QTOF-MS measurements, and Chun T-H. thanks the scholarship financial support given by Coordenação de Aperfeiçoamento de Pessoal de Nível Superior—Brasil (CAPES)—Finance Code 001.

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Correspondence to Cesar Liberato Petzhold.

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Huang, C.T., de Oliveira, L.A., de Carvalho Peres, A.C. et al. Studies of radical homopolymerization of N-(4-iodo-1,3-diphenylbutyl) acrylamide. Polym. Bull. 77, 4523–4535 (2020). https://doi.org/10.1007/s00289-019-02982-x

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Keywords

  • Polymer synthesis
  • Polyacrylamide
  • Functionalized polymer
  • Ritter reaction
  • Iodine transfer polymerization