Perspective ArticleSynthesis and antibacterial activities of quaternary ammonium salts with different alkyl chain lengths grafted on polyvinyl alcohol-formaldehyde sponges
Graphical abstract
Introduction
Medical dressings are an important class of medical materials used to cover sores, wound dressings can replace damaged skin and act as a temporary barrier to avoid wound infections and provide a beneficial environment for wound healing [1]. Traditional cotton dressings including cotton balls, cotton gauze and cotton bandages which have the characteristics of water absorption and heat preservation are still widely used in various types of wounds [2]. However, these products have no antibacterial effects and are prone to cause wound infection during used. In addition, the traditional cotton dressings are easy to stick to the wound when they are removed, so there are great defects for cotton dressings used as medical dressings [3]. With new requirements of medical dressings, such as antibacterial effect, anti-adhesion and high liquid absorption, some medical dressings with special functions have been developed in recent years [[4], [5], [6]]. At present, according to the type of antibacterial dressing materials, it can be roughly divided into sponge dressings [7], film dressings [8] and hydrogel dressings [9].
The sponge antibacterial dressings have the advantages of excellent exudate absorption capacity, good oxygen transmission rate and outstanding biocompatibility [[10], [11], [12]] which are beneficial for wound healing and can also be used as a drug carrier. Chen et al. [13] reported a chitosan/poly(vinyl alcohol) (PVA) composite sponge and demonstrated the antibacterial and hemostatic activities, the chitosan/PVA sponge with high liquid absorption and antibacterial properties can effectively promote the wound healing. Liang et al. [14] reported a novel silver nanoparticles (AgNPs)/chitosan composite dressing and tested the antimicrobial activity. The AgNPs/chitosan dressing with excellent absorption capacity promoted wound healing and accelerated the reepithelialization and collagen deposition.
Because of its low toxicity, low price, excellent antibacterial spectrum and other outstanding features, the quaternary ammonium salt is currently the most widely used organic antibacterial agent. Shao et al [15] reported a quaternary ammonium salt containing perfluoroalkyl and tested the antimicrobial activity. The results showed that the quaternary ammonium salt had an excellent antibacterial effect on both E. coli and S. aureus, the minimum inhibitory concentration (MIC) was 7.8 μg/mL. Zhang et al. [16] synthesized twelve quaternary ammonium compounds and tested their antimicrobial activities and vitro cytotoxicity. The minimum inhibitory concentration (MIC) of E. coli and S. aureus ranges from 2.8–167.7 μg/mL. Compared with small molecular compounds, polymeric quaternary ammonium salt antibacterial agent has a higher charge density and stronger antibacterial ability. In addition, it has the characteristics of high chemical stability, low residual toxicity, easy processing and so on. Kim et al. [17] introduced quaternary ammonium salts grafted chitosan and studied their antimicrobial activities against S. aureus. The results showed that the antimicrobial activity of chitosan modified by quaternary ammonium salt was significantly higher than that of quaternary ammonium salt small molecules. Tang et al. [18] synthesized an antimicrobial biopolymer dye with chitosan modified by quaternary ammonium salt. The results showed that the antimicrobial effect of this polymer on E. coli and S. aureus was excellent. The antibacterial rates were greater than 99%.
Polyvinyl alcohol–formaldehyde (PVF) sponges with open-cell structure exhibit remarkable absorption capacity, excellent mechanical properties and good biocompatibility [19,20]. Because of the hydroxyl groups in the PVF sponges, it has been widely used as cleaning materials and biomedical materials. Meanwhile, a large amount of hydroxyl groups in PVF sponges provide a chance to modify the surface property to obtain grafting PVF sponges [21,22]. In this study, antibacterial PVF sponges are successfully prepared via grafting quaternary ammonium salts with different alkyl chain lengths (n = 4, 6, 8, 10, 12, 14, 16, 18) onto the PVF network under alkaline condition and the antibacterial activities of the PVF-g-QA sponges are investigated extensively.
Section snippets
Materials
Polyvinyl alcohol (PVA 17–99) and Triton X-100 were purchased from Aladdin. Epichlorohydrin and N,N-dimethylalkylamine (n = 4, 6, 8, 10, 12, 14, 16, 18) were obtained from Energy Chemical. Yeast extract (LP0021), Tryptone (LP0042) and Nutrient Agar (CM1160) were purchased from Sigma-Aldrich. E. coli ATCC 25922 and S. aureus ATCC 6538 were obtained from Huankai Microbial Technology Co., Ltd., China. LIVE/DEAD™ BacLight™ Bacterial Viability Kit was purchased from Thermo Fisher Scientific Company,
Characterization of chemical structure of as-prepared PVF-g-QA sponges with different alkyl chain lengths
The FTIR spectra of as-prepared PVF-g-QA sponges (n = 4, 6, 8, 10, 12, 14, 16, 18) are exhibited in Fig. 1. The peaks of 3200–3600 cm−1, 2843–2943 cm−1 and 1012 cm−1 for original PVF are attributed to the OH, CH and C-O-C stretching vibration in the network. After the grafting reaction, because of the low grafting percentage of PVF-g-QA sponges, the absorption peak intensity of 3200–3600 cm−1 corresponding to the hydroxyl groups (OH) has no significant reduction and the strong characteristic
Conclusions
Antibacterial PVF-g-QA sponges with different alkyl chain lengths (n = 4, 6, 8, 10, 12, 14, 16, 18) are successfully synthesized through a facile grafting reaction of quaternary ammonium salts (QA) to the PVF network. The grafting percentages of PVF-g-QA sponges are from 1.1% to 1.6%. As-prepared PVF-g-QA sponges display interconnected pore structure, high porosity and broad distribution from a few microns to 200 μm and reach absorption equilibrium only within 1 min in both saline solution and
Data availability
The raw/processed data required to reproduce these findings cannot be shared at this time due to technical or time limitations.
Declaration of Competing Interest
The authors declare no conflict of interest.
Acknowledgements
This work was supported by the National Key Laboratory of Human Factors Engineering of China (Grant Nos. SYFD061906K).
References (39)
- et al.
Medical applications of poly-4-hydroxybutyrate: a strong flexible absorbable biomaterial
Biochem. Eng. J.
(2003) - et al.
EGF containing gelatin-based wound dressings
Biomaterials.
(2001) - et al.
Acceleration of wound healing in diabetic rats by layered hydrogel dressin
Carbohydr. Polym.
(2012) - et al.
Characterization of cellulose based sponges for wound dressings
Colloids Surf. A: Physicochem. Eng. Aspects.
(2015) - et al.
Construction of silver sulfadiazine loaded chitosan composite sponges as potential wound dressings
Carbohydr. Polym.
(2017) - et al.
Bubble template fabrication of chitosan/poly(vinyl alcohol) sponges for wound dressing applications
Int. J. Biol. Macromol.
(2013) - et al.
Synthesis and antimicrobial activity of a perfluoroalkyl-containing quaternary ammonium salt
J. Fluor. Chem.
(2003) - et al.
Synthesis and characterization of chitosan based dye containing quaternary ammonium group
Carbohydr. Polym.
(2016) - et al.
Facile fabrication of poly(vinyl alcohol) gels and derivative aerogels
Polymer.
(2014) - et al.
Antibacterial and biocompatible cross-linked waterborne polyurethanes containing Gemini quaternary ammonium salts
Biomacromolecules.
(2018)
Enhanced antibacterial and wound healing activities of microporous chitosan-Ag/ZnO composite dressing
Carbohydr. Polym.
Surface modification and antibacterial activity of electrospun polyurethane fibrous membranes with quaternary ammonium moieties
J. Membr. Sci.
Synthesis and characterization of antibacterial polyurethane coatings from quaternary ammonium salts functionalized soybean oil based polyols
Mat. Sci. Eng. C-Mater.
Antifungal activity of gemini quaternary ammonium salts
Microbiol. Res.
Wound dressing from polyvinyl alcohol/chitosan electrospunfiber membrane loaded with OH-CATH30 nanoparticles
Carbohydr. Polym.
Evaluation of chitosan nano dressing for wound healing: characterization, in vitro and in vivo studies
Int. J. Biol. Macromol.
Modified cotton gauze dressings that selectively absorb neutrophil elastase activity in solution
Wound Repair Regen.
Antibacterial hemostatic dressings with nanoporous bioglass containing silver
Int. J. Nanomedicine
Development and characterization of composite chitosan/active carbon hydrogels for a medical application
J. Appl. Polym. Sci.
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