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Preparation of biocidal 4‐ethyl‐4‐(hydroxymethyl)oxazolidin‐2‐one‐based N ‐halamine polysiloxane for impregnation of polypropylene in supercritical CO 2
Author(s) -
Chen Yong,
He Qingkun,
Ren Guoyuan,
Feng Chunyan,
Li Na,
Yu Hao,
Han Qiuxia
Publication year - 2018
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.46624
Subject(s) - materials science , hydroxymethyl , solvent , polypropylene , polymer chemistry , supercritical fluid , reagent , supercritical carbon dioxide , chemical engineering , organic chemistry , nuclear chemistry , chemistry , composite material , engineering
ABSTRACT A cyclic N ‐halamine precursor, 4‐ethyl‐4‐(hydroxymethyl)oxazolidin‐2‐one (EHMO), was synthesized and attached to poly(methylhydrosiloxane) (PMHS) through silane alcoholysis between the OH of EHMO and SiH of PMHS. The alcoholysis product was chlorinated with tert ‐butyl hypochlorite to transfer the NH to NCl and obtain an EHMO‐based N ‐halamine polysiloxane. The N ‐halamine polysiloxane was impregnated into inert polypropylene (PP) fibers and formed a 72 nm coating layer using supercritical carbon dioxide (scCO 2 ) as solvent and swelling reagent at 28 MPa and 50 °C for biocidal application. The overall synthetic procedure and the impregnation process were characterized by FTIR, XPS, and SEM, respectively. The N‐halamine polysiloxane layer on PP imparted potent antibacterial abilities against both Staphylococcus aureus and Escherichia coli while pristine ones did not exhibit noticeable killing activities. Stability tests showed that the N ‐halamine polysiloxane layer was resistant to washing cycles, storage, and UV irradiation and the rechlorination of lost chlorines was good. The strategy of using CO 2 ‐philic PMHS as carrier polymer and scCO 2 as working solvent for impregnation presents a general and friendly procedure to functionalize inert substrates without the need of chemical linkage and organic solvent. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018 , 135 , 46624.