Application scheme: copolymerization of phthalimidyl (meth)acrylate with acrylate, then CO2/phthalimide derivative step and post-polymerization modifications (H+, nitroxide-type reagent, photocatalytic phosphorus reagent) referenced to Ref. 1-4.

Acrylate Monomers for Converting Polymer Backbones to Ethylene or Propylene

N-Phthalimidyl Acrylate (P3351) and N-Phthalimidyl Methacrylate (P3350) are acrylate and methacrylate monomers useful for postpolymerization modification. In polymers containing units derived from these monomers, the phthalimide moiety undergoes reduction via single-electron transfer (SET) from a catalyst, followed by decarboxylation and hydrogenation with a hydrogen donor, converting into ethylene units from P3351 or propylene units from P3350.¹) ²) In addition, postpolymerization modifications such as alkene addition via decarboxylation, nitroxide radical coupling, and phosphonylation through radical–polar crossover (RPC) following decarboxylation have also been reported.³) ⁴) These reactions enable the synthesis of copolymers with structures that have been difficult to access using conventional methods. Copolymers of P3350 with methyl methacrylate have also been reported to depolymerize into methyl methacrylate through β-scission, attracting attention for polymer recycling.⁵) ⁶)

Application scheme: copolymerization of phthalimidyl (meth)acrylate with acrylate, then CO2/phthalimide derivative step and post-polymerization modifications (H+, nitroxide-type reagent, photocatalytic phosphorus reagent) referenced to Ref. 1-4.
Source: TCI brochure FF227

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References

  1. S. Frech, P. Theato, et al., Macromolecules 2021, 54, 9937. doi:https://doi.org/10.1021/acs.macromol.1c01257
  2. J. B. Garrison, B. S. Sumerlin, et al., Polym. Chem. 2022, 13, 982. doi:https://doi.org/10.1039/D1PY01643A
  3. S. Frech, P. Theato, et al., Macromol. Rapid Commun. 2022, 43, 2200068. doi:https://doi.org/10.1002/marc.202200068
  4. T. Tamano, S. Inagi, et al., Angew. Chem. Int. Ed. 2025, 64, e202507572. doi:https://doi.org/10.1002/anie.202507572

Download TCI brochure Phthalimidyl (Meth)Acrylate Monomers for Post-polymerization Modifications (PDF)

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