Issue 14, 2023

Effect of amino group modification at allyl position of methacrylamides on polymerization and polymer pH-/thermo-responsiveness

Abstract

With an interest in β-amino acid derivative polymers containing a carbon backbone, the polymerization of N-n-propyl α-(aminomethyl)acrylamide (4b) and N-isopropyl α-(aminomethyl)acrylamide (4b) were investigated. The synthesis of 4 was achieved within many fewer steps than reported by using selective acylation and subsequent conjugate substitution of α-(chloromethyl)acryloyl chloride. 4 hardly homopolymerized, but copolymerization with N-substituted acrylamides afforded polymers with various compositions. Surprisingly, substitution with amino groups increased the hydrophobicity of the polymers and lowered the cloud point (Tc). Nevertheless, polymers containing the amino monomers as major components exhibited significantly higher Tc in 1 M HCl aq than those in water. Thus, in order to give clear pH responsiveness, it is necessary to use 4 as a major monomer.

Graphical abstract: Effect of amino group modification at allyl position of methacrylamides on polymerization and polymer pH-/thermo-responsiveness

Supplementary files

Article information

Article type
Paper
Submitted
30 dic. 2022
Accepted
31 ene. 2023
First published
01 feb. 2023

Polym. Chem., 2023,14, 1585-1590

Effect of amino group modification at allyl position of methacrylamides on polymerization and polymer pH-/thermo-responsiveness

Y. Kohsaka, N. Chinbat, K. Ito and Y. Akae, Polym. Chem., 2023, 14, 1585 DOI: 10.1039/D2PY01611G

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