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Lignin-Based Graft Copolymers via ATRP and Click Chemistry

Chung, Hoyong and Al-Khouja, Amer and Washburn, Newell R. (2013) Lignin-Based Graft Copolymers via ATRP and Click Chemistry. In: Green Polymer Chemistry: Biocatalysis and Materials II. ACS Symposium Series. No.1144. American Chemical Society , Washington, DC, pp. 373-391. ISBN 978-0-8412-2895-5 . https://resolver.caltech.edu/CaltechAUTHORS:20140402-144042541

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Abstract

New lignin-based graft copolymers have been developed by atom transfer radical polymerization (ATRP) and click chemistry. These hybrid materials have a lignin center and poly(n-butyl acrylate) or polystyrene grafts. Poly(n-butyl acrylate) represents a typical elastomeric polymer, and polystyrene is used as a representative glassy polymer, and grafting these onto lignin was pursued as a method to integrate a renewable resource into polymers commonly used in a broad range of applications. Two different graft copolymerization methods were used: “graft from” and “graft onto”. The “graft from” method utilized ATRP to polymerize vinyl monomers from a lignin-based macroinitiator. Kinetic data showed that the ATRP graft copolymerization occurred in controlled manner for both polystyrene and poly(n-butyl acrylate) with a conversion up to 25%. In “graft onto” method, the backbone lignin was linked to polystyrene graft via click chemistry. In the “graft onto” method, a polystyrene homopolymer was prepared by ATRP followed by end-group functionalization to obtain azide functionality at polymer chain terminals. As a counterpart of azide group, lignin hydroxyl groups were functionalized to alkyne groups for the click reaction, copper-catalyzed Huisgen cycloaddition. The click chemistry was conducted with high efficiency to form lignin-graft-polystyrene under mild conditions. Grafting efficiency was monitored by ^1H NMR and GPC. The ^1H NMR data demonstrated a complete functionalization of polystyrene terminal groups and following successful click reaction without remaining lignin or polystyrene fragments. In these experiments, GPC characterization indicated that click coupling completed within 5 hours. Unlike fully crosslinked lignin-based network polymers such as lignin-based polyurethane, these lignin-based graft copolymers may show high flexibility in processing as a thermoplastic polymer.


Item Type:Book Section
Related URLs:
URLURL TypeDescription
http://pubs.acs.org/doi/abs/10.1021/bk-2013-1144.ch025PublisherUNSPECIFIED
Additional Information:© 2013 American Chemical Society. Publication Date (Web): November 22, 2013. The authors would like to thank Prof. Krzysztof Matyjaszewski for allowing use of GPC.
Subject Keywords:lignin; polystyrene; poly(n-butyl acrylate); ATRP; click chemistry; graft copolymerization
Series Name:ACS Symposium Series
Issue or Number:1144
Record Number:CaltechAUTHORS:20140402-144042541
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20140402-144042541
Official Citation: Lignin-Based Graft Copolymers via ATRP and Click Chemistry Hoyong Chung, Amer Al-Khouja, and Newell R. Washburn Green Polymer Chemistry: Biocatalysis and Materials II. January 1, 2013, 373-391
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:44614
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:03 Apr 2014 15:51
Last Modified:03 Oct 2019 06:20

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