Issue 2, 2010

Synthesis of well-defined primary amine-based homopolymers and block copolymers and their Michael addition reactions with acrylates and acrylamides

Abstract

A series of well-defined primary amine-based AB diblock copolymers were synthesised via atom transfer radical polymerisation (ATRP) using 2-aminoethyl methacrylate hydrochloride (AMA), with the other block comprising the following comonomers: 2-(diisopropylamino)ethyl methacrylate (DPA), 2-hydroxypropyl methacrylate (HPMA) and 2-(methacryloyloxy)ethyl phosphorylcholine (MPC). These copolymers were prepared with reasonably narrow polydispersities (Mw/Mn ≈ 1.1–1.4) in either 80 : 20 or 95 : 5 2-propanol–water mixtures at 50 °C using a 2-(N-morpholino)ethyl isobutyryl bromide initiator. The chain extension efficiency of PAMA was also investigated using a further charge of AMA. Unfortunately, such ‘self-blocking’ was problematic due to both catalyst deactivation and termination of the living chain ends. Nevertheless, low polydispersity all-methacrylic diblock copolymers were obtained in high yields via sequential monomer addition, provided that AMA was used as the second monomer in such syntheses. PAMA49 homopolymer and selected PAMA-based copolymers were reacted with various acrylates and acrylamides in aqueous solution at pH 9, with mean degrees of functionalisation being determined by 1H NMR spectroscopy. This facile Michael addition chemistry provides access to a library of novel functional water-soluble homopolymers and diblock copolymers.

Graphical abstract: Synthesis of well-defined primary amine-based homopolymers and block copolymers and their Michael addition reactions with acrylates and acrylamides

Article information

Article type
Paper
Submitted
27 Oct 2009
Accepted
06 Dec 2009
First published
08 Jan 2010

Polym. Chem., 2010,1, 221-230

Synthesis of well-defined primary amine-based homopolymers and block copolymers and their Michael addition reactions with acrylates and acrylamides

E. S. Read, K. L. Thompson and S. P. Armes, Polym. Chem., 2010, 1, 221 DOI: 10.1039/B9PY00320G

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