Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 10, 2020
Previous Article Next Article

Clean synthesis of linear and star amphiphilic poly(ε-caprolactone)-block-poly(ethyl ethylene phosphonate) block copolymers: assessing self-assembly and surface activity

Author affiliations

Abstract

Anionic ring-opening polymerization (AROP) of 2-ethyl-2-oxo-1,3,2-dioxaphospholane (EP) has been utilized to create alternative hydrophilic moieties for utilization in surfactants. The current “go-to” hydrophilic unit is poly(ethylene glycol) (PEG), but this is non-biodegradable and there is some evidence that its use can lead to accumulation of toxic by-products. We have created new approaches leading to water-dispersible, fully degradable amphiphilic block copolymers. Our approach utilized poly(ε-caprolactone)-based macroinitiators in a solvent free process with organocatalyst DBU. We have prepared a comprehensive set of novel amphiphilic PCL-b-PEP block copolymers including linear diblock, triblock and star diblock copolymers characterized by SEC, 1H and 31P NMR and MALDI-TOF analyses. Supercritical carbon dioxide (scCO2) was exploited to efficiently extract the residual EP monomer leading to significantly increased gravimetric yields of purified product compared to conventional techniques such as dialysis. The self-assembly of the amphiphilic copolymers in water was investigated by DLS and cryo-TEM and their surface-activity as a function of concentration was investigated by tensiometry showing behavior that matches or exceeds commercially available surfactants.

Graphical abstract: Clean synthesis of linear and star amphiphilic poly(ε-caprolactone)-block-poly(ethyl ethylene phosphonate) block copolymers: assessing self-assembly and surface activity

Back to tab navigation

Supplementary files

Article information


Submitted
06 Mar 2020
Accepted
24 Apr 2020
First published
24 Apr 2020

Green Chem., 2020,22, 3248-3261
Article type
Paper

Clean synthesis of linear and star amphiphilic poly(ε-caprolactone)-block-poly(ethyl ethylene phosphonate) block copolymers: assessing self-assembly and surface activity

P. Baheti, T. Rheinberger, O. Gimello, C. Bouilhac, F. R. Wurm, P. Lacroix-Desmazes and S. M. Howdle, Green Chem., 2020, 22, 3248
DOI: 10.1039/D0GC00819B

Social activity

Search articles by author

Spotlight

Advertisements