Antibacterial poly{(4-vinyl phenylboronic acid)-co-[2-(dimethylamino)ethyl methacrylate]} copolymers and their application in water-based paints

被引:11
作者
Cicek, Huseyin [1 ]
Kocak, Gokhan [2 ,3 ]
Ceylan, Ozgur [4 ]
Kutluca, Emir Ahmet [1 ]
Dikmen, Zeynep [5 ]
Butun, Vural [2 ,5 ]
机构
[1] Mugla Sitki Kocman Univ, Dept Chem, Fac Sci, TR-48000 Mugla, Turkey
[2] Eskisehir Osmangazi Univ, Dept Chem, TR-26480 Eskisehir, Turkey
[3] Adiyaman Univ, Dept Chem, TR-02040 Adiyaman, Turkey
[4] Mugla Sitki Kocman Univ, Ula Ali Kocman Vocat Sch, Food Qual Control & Anal Program, TR-48147 Mugla, Turkey
[5] Eskisehir Osmangazi Univ, Dept Polymer Sci & Technol, TR-26480 Eskisehir, Turkey
关键词
biomedical applications; coatings; composites; copolymers; quorum sensing; surfaces and interfaces; TRANSFER RADICAL POLYMERIZATION; QUATERNARY AMMONIUM-SALTS; QUORUM-SENSING INHIBITORS; BORONIC ACIDS; VIBRIO-HARVEYI; N-HALAMINE; 2-(DIMETHYLAMINO)ETHYL METHACRYLATE; ANTIMICROBIAL POLYMERS; DIBLOCK COPOLYMERS; SURFACE;
D O I
10.1002/app.46245
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Herein, we report the synthesis of poly(4-vinylphenylboronic acid) (PVPBA) and poly[2-(dimethylamino)ethyl methacrylate] (PDMAEMA) homopolymers, copolymers, and their methyl, pentyl, and octyl quaternized forms as dopant in water-based permanent antibacterial paints. Both quaternized and nonquaternized forms of P(VPBA-co-DMAEMA) copolymers have reflected higher MIC values relative to PDMAEMA homopolymers. High molecular weight copolymers were more active against Escherichia coli ATCC 25922, contrarily, lower molecular weight copolymers showed higher antibacterial activity against Staphylococcus aureus ATCC 25923. The paint films prepared with quaternized PDMAEMA homopolymers with a weight of 10% showed better antibacterial activity in water and airborne tests than the copolymers. However, it has been shown that the inadequate anti-biofilm properties of homopolymer-containing paint films are overcome with the VPBA content of the copolymer structure and the most effective antibacterial and anti-biofilm properties have been obtained with paint films containing P(VPBA-co-5QDMAEMA) copolymers. These paint films, which can maintain antibacterial and anti-biofilm properties for at least 1 year, have the potential to be an alternative to Ag/Cl based solid surfaces which require the active substance to be regenerated. (c) 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46245.
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页数:13
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共 69 条
[1]  
Abdullayev E., 2011, ABSTR PAP AM CHEM S, V241, P4040
[2]   Biological activity of selected boronic acids and their derivatives [J].
Adamczyk-Wozniak, Agnieszka ;
Komarovska-Porokhnyavets, Olena ;
Misterkiewicz, Boguslaw ;
Novikov, Volodymyr P. ;
Sporzynski, Andrzej .
APPLIED ORGANOMETALLIC CHEMISTRY, 2012, 26 (07) :390-393
[3]   Dynamic-Covalent Macromolecular Stars with Boronic Ester Linkages [J].
Bapat, Abhijeet P. ;
Roy, Debashish ;
Ray, Jacob G. ;
Savin, Daniel A. ;
Sumerlin, Brent S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19832-19838
[4]   Synthesis and Applications of Boronic Acid-Containing Polymers: From Materials to Medicine [J].
Brooks, William L. A. ;
Sumerlin, Brent S. .
CHEMICAL REVIEWS, 2016, 116 (03) :1375-1397
[5]   Selective quaternization of 2-(dimethylamino)ethyl methacrylate residues in tertiary amine methacrylate diblock copolymers [J].
Bütun, V ;
Armes, SP ;
Billingham, NC .
MACROMOLECULES, 2001, 34 (05) :1148-1159
[6]   Synthesis and aqueous solution properties of near-monodisperse tertiary amine methacrylate homopolymers and diblock copolymers [J].
Bütün, V ;
Armes, SP ;
Billingham, NC .
POLYMER, 2001, 42 (14) :5993-6008
[7]   Polymeric N-Halamine Latex Emulsions for Use in Antimicrobial Paints [J].
Cao, Zhengbing ;
Sun, Yuyu .
ACS APPLIED MATERIALS & INTERFACES, 2009, 1 (02) :494-504
[8]   Reversibly Switching the Function of a Surface between Attacking and Defending against Bacteria [J].
Cao, Zhiqiang ;
Mi, Luo ;
Mendiola, Jose ;
Ella-Menye, Jean-Rene ;
Zhang, Lei ;
Xue, Hong ;
Jiang, Shaoyi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (11) :2602-2605
[9]   Synthese and characterization of boronic acid functionalized macroporous uniform poly(4-chloromethylstyrene-co-divinylbenzene) particles and its use in the isolation of antioxidant compounds from plant extracts [J].
Cetinkaya, Onur ;
Duru, Mehmet Emin ;
Cicek, Huseyin .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2012, 909 :51-60
[10]   P(VPBA-DMAEA) as a pH-sensitive nanovalve for mesoporous silica nanoparticles based controlled release [J].
Chang, Yu-Jie ;
Liu, Xi-Zhen ;
Zhao, Qing ;
Yang, Xiao-Hai ;
Wang, Ke-Min ;
Wang, Qing ;
Lin, Min ;
Yang, Meng .
CHINESE CHEMICAL LETTERS, 2015, 26 (10) :1203-1208