Integration of graft copolymerization and ring-opening reaction: A mild and effective preparation strategy for "clickable" cellulose fibers

Lijian Sun; Xueren Qian; Chunyue Ding; XianHui An

doi:10.1016/j.carbpol.2018.06.054

Integration of graft copolymerization and ring-opening reaction: A mild and effective preparation strategy for "clickable" cellulose fibers

Carbohydr Polym. 2018 Oct 15:198:41-50. doi: 10.1016/j.carbpol.2018.06.054. Epub 2018 Jun 13.

Authors

Lijian Sun¹, Xueren Qian², Chunyue Ding³, XianHui An¹

Affiliations

¹ Key Laboratory of Bio-based Materials Science and Technology of Ministry of Education, Northeast Forestry University, Harbin, 150040 Heilongjiang Province, China.
² Key Laboratory of Bio-based Materials Science and Technology of Ministry of Education, Northeast Forestry University, Harbin, 150040 Heilongjiang Province, China. Electronic address: qianxueren@aliyun.com.
³ Key Laboratory of Bio-based Materials Science and Technology of Ministry of Education, Northeast Forestry University, Harbin, 150040 Heilongjiang Province, China; Institute of Papermaking Science and Technology, Bioengineering College, Sichuan University of Science and Engineering, Zigong, 643000 Sichuan Province, China.

PMID: 30093017
DOI: 10.1016/j.carbpol.2018.06.054

Abstract

A mild and effective strategy to prepare alkynyl-functionalized cellulose fibers (A-CFs) and azido-functionalized cellulose fibers (N₃-CFs) was presented. Epoxy-cellulose fibers (Epoxy-CFs), graft copolymerization products of cellulose fibers (CFs) and glycidyl methacrylate (GMA), were prepared using cerium ammonium nitrate (CAN) as initiator. Epoxy groups content of Epoxy-CFs were as high as 2.5 mmol/g. Introduction of alkynyl/azido groups into Epoxy-CFs were achieved through ring-opening reactions of epoxy groups with propargylamine (PgAm) and sodium azide (NaN₃), respectively. Under appropriate conditions, A-CFs with alkynyl groups of 0.57 mmol/g and N₃-CFs with azido groups of 0.35 mmol/g were obtained. Click reactivities of A-CFs, N₃-CFs and Epoxy-CFs were verified by Cu(I) catalyzed alkyne-azido cycloaddition (CuAAC) and thiol-epoxy click reactions. A-CFs, N₃-CFs, Epoxy-CFs and their clicked products were characterized by attenuated total reflectance Fourier-transform infrared spectroscopy (ATR-FTIR) and X-ray photoelectron spectroscopy (XPS).

Keywords: Alkynyl/azido functionalized cellulose; Cellulose fibers; Click chemistry; Graft copolymerization; Ring-opening reaction.