Dual-initiator alkoxyamines with an N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl) nitroxide moiety for preparation of block co-polymers

Gérard Audran (1) , Elena Bagryanskaya (2) , Mariya Edeleva (2) , Sylvain R.A. Marque (1) , Toshihide Yamasaki (1)

1 ICR - Institut de Chimie Radicalaire
2 - N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry

Dual initiators for controlled radical/ionic polymerization reactions attract much attention in terms of preparation of new materials. We studied the potential of dual-initiator alkoxyamines 3 [based both on para-substituted aromatic ring for external triggering or initiation of orthogonal polymerization and on N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl) nitroxide (SG1)] for nitroxide-mediated polymerization (NMP) with various monomers such as styrene, styrene sulphonate, 2-vinyl pyridine or methylmethacrylate. Alkoxyamines 3 were found to be as efficient in the NMP process as N-(2-methylpropyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxylprop-2-yl)hydroxylamine (1). Furthermore, in sharp contrast to 1, alkoxyamines 3 were easier to functionalize.

Domaines: Polymères

Gérard Audran, Elena Bagryanskaya, Mariya Edeleva, Sylvain R.A. Marque, Toshihide Yamasaki. Dual-initiator alkoxyamines with an N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl) nitroxide moiety for preparation of block co-polymers. RSC Advances, 2017, 7 (9), pp.4993-5001. ⟨10.1039/c6ra27231b⟩. ⟨hal-01813814⟩