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 dec 2022
Accepted
31 jan 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements