Facile Functionalization of Electrospun Poly(ethylene- co -vinyl alcohol) Nanofibers via the Benzoxaborole-Diol Interaction

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Abstract

A facile functionalization method of poly(ethylene- co-vinyl alcohol) (EVOH) nanofiber meshes was demonstrated by utilizing the benzoxaborole-diol interaction between EVOH and benzoxaborole-based copolymers (BOP). EVOH and BOP were firstly mixed to prepare the quasi-gel-state solution with enough viscosity for electro-spinning. The fiber morphology was controlled via changing the mixing ratio of EVOH and BOP. The prepared EVOH/BOP nanofiber mesh showed good stability in aqueous solution. Over 97% of the nanofibers remained after the immersion test for 24 h in acid or alkali aqueous solutions without changing their morphology. Temperature and pH-responsive moieties were copolymerized with BOP, and cationic dye was easily immobilized into the nanofiber mesh via an electrostatic interaction. Therefore, the proposed functionalization technique is possible to perform on multi-functionalized molecule-incorporated nanofibers that enable the fibers to show the environmental stimuli-responsive property for the further applications of the EVOH materials.

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An improved class of sugar-binding boronic acids, soluble and capable of complexing glycosides in neutral water.

Meenakshi Dowlut, Dennis G Hall (2006)

This study describes a new class of carbohydrate-binding boronic acids. ortho-Hydroxymethyl phenylboronic acid (boronophthalide) was shown to be superior to the well-established dialkylamino ("Wulff-type") analogues, and it is more soluble in aqueous solvents. The most significant finding in this work is the surprising ability of ortho-hydroxyalkyl arylboronic acids to complex model glycopyranosides under physiologically relevant conditions. These boronic acid units appear to complex hexopyranosides mainly using their 4,6-diol. This behavior is significant because a majority of cell-surface glycoconjugates present free 4,6-diols. Thus, conjugatable forms of these boronic acids could be used in the design of oligomeric receptors and sensors to exploit multivalency effects. Such receptors could dramatically expand the potential of boronic acids toward the selective recognition of cell-surface glycoconjugates.

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Electrospinning of poly(ethylene-co-vinyl alcohol) fibers.

El-Refaie Kenawy, John M Layman, Jessica Watkins … (2003)

Solutions of poly(ethylene-co-vinyl alcohol) or EVOH, ranging in composition from 56 to 71 wt% vinyl alcohol, can be readily electrospun at room temperature from solutions in 70% 2-propanol/water (rubbing alcohol). The solutions are prepared at 80 degrees C and allowed to cool to room temperature. Interestingly, the solutions are not stable at room temperature and eventually the polymer precipitates after several hours. However, prior to precipitation, electrospinning is extensive and rapid, allowing coverage of fibers on various substrates, including a grounded metal plate, dielectrics interposed between the charged jet and the metal ground, and on the human body. Fiber diameters of ca. 0.2-8.0 microm were obtained depending upon the solution concentration, an attractive range for tissue engineering, wound healing, and related applications. Electrospun EVOH mats have been shown to support the culturing of smooth muscle cells and fibroblasts.

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Universal (Switchable) RAFT Agents

San H Thang, Massimo Benaglia, Yen K. Chong … (2009)

The polymerization of most monomers that are polymerizable by radical polymerization can be controlled by the reversible addition-fragmentation chain transfer (RAFT) process. However, it is usually required that the RAFT agent be selected according to the types of monomer being polymerized. Thus, RAFT agents (dithioesters, trithiocarbonates) suitable for controlling polymerization of "more activated" monomers (MAMs; e.g., styrene, acrylates, methacrylates, etc.) tend to inhibit polymerization of "less activated" monomers (LAMs; e.g., vinyl acetate, N-vinylpyrrolidone, etc.). Similarly RAFT agents suitable for polymerizations of LAMs (xanthates, certain dithiocarbamates) tend to give little or poor control over polymerizations of MAMs. We now report a new class of "switchable" RAFT agents, N-(4-pyridinyl)-N-methyldithiocarbamates, that provide excellent control over polymerization of LAMs and, after addition of 1 equiv of a protic or Lewis acid, become effective in controlling polymerization of MAMs, allowing the synthesis of poly(MAM)-block-poly(LAM) with narrow molecular weight distributions.

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Author and article information

Contributors

Hatsuo Ishida: Role: Academic Editor

Journal

Journal ID (nlm-ta): Polymers (Basel)

Journal ID (iso-abbrev): Polymers (Basel)

Journal ID (publisher-id): polymers

Title: Polymers

Publisher: MDPI

ISSN (Electronic): 2073-4360

Publication date (Electronic): 05 February 2016

Publication date Collection: February 2016

Volume: 8

Issue: 2

Electronic Location Identifier: 41

Affiliations

[1 ]International Center for Young Scientists (ICYS) and International Center for Materials Nanoarchitectonics (WPI-MANA), National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan

[2 ]Biomaterials Unit, WPI-MANA, NIMS, 1-1 Namiki, Tsukuba, Ibaraki 305-0044, Japan; EBARA.Mitsuhiro@ 123456nims.go.jp

[3 ]Graduate School of Industrial Science and Technology, Tokyo University of Science, 6-3-1 Niijuku, Katsushika, Tokyo 125-8585, Japan

Author notes

[* ]Correspondence: KOTSUCHIBASHI.Yohei@ 123456nims.go.jp ; Tel.: +81-29-851-3354 (ext. 8918); Fax: +81-29-860-4762

Article

Publisher ID: polymers-08-00041

DOI: 10.3390/polym8020041

PMC ID: 6432579

SO-VID: 129ef1f2-90ae-44f6-99f6-aca67844cead

License:

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons by Attribution (CC-BY) license ( http://creativecommons.org/licenses/by/4.0/).

History

Date received : 01 December 2015

Date accepted : 29 January 2016

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Facile Functionalization of Electrospun Poly(ethylene- co-vinyl alcohol) Nanofibers via the Benzoxaborole-Diol Interaction

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Abstract

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Electrospinning for biomedical applications

Most cited references 38

An improved class of sugar-binding boronic acids, soluble and capable of complexing glycosides in neutral water.

Electrospinning of poly(ethylene-co-vinyl alcohol) fibers.

Universal (Switchable) RAFT Agents

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