Influence of spacer group on the structure and thermal properties of copolymers based on acrylonitrile and methacrylic 1,3-thiazole and 1,2,3-triazole derivatives

Tejero, Rubén; López, Daniel

doi:10.1016/j.eurpolymj.2015.08.014

Cited by 6 publications

(8 citation statements)

References 30 publications

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“…Therefore, the P(AN-co-MTZ-BuI) copolymers present much lower glass transition temperatures than P(AN-co-MTZ-MeI) copolymers. The introduction of carbonate group as spacer gives similar characteristics to previously described homopolymer bearing succinate group [24,26]. Therefore, it has been demonstrated that the thermal properties of the cationic copolymers can be modulated by varying the composition and the alkylating agent.…”

Section: Resultsmentioning

confidence: 57%

Influence of side chain structure on the thermal and antimicrobial properties of cationic methacrylic polymers

Cuervo-Rodríguez

Muñoz‐Bonilla

Araujo

et al. 2019

European Polymer Journal

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A novel methacrylic monomer, 2-(((2-(4-methylthiazol-5-yl)ethoxy)carbonyl)oxy)ethyl methacrylate (MTZ), containing in the lateral chain both hydrolytically sensitive carbonate and thiazole groups has been firstly described. Posterior, it was free-radical polymerized and copolymerized with acrylonitrile in anhydrous solution of dimethylsulfoxide, with the purpose of investigate the influence of its chemical and structural characteristics on the antimicrobial activity. Cationic antimicrobial polymers were subsequently obtained by alkylation reaction with methyl and butyl iodide agents. Their thermal behavior was analyzed in all series, modified and unmodified copolymers in terms of glass transition temperature and thermal stability. The antimicrobial activity in solution was tested against Gram-positive Staphylococcus aureus and Staphylococcus epidermidis, Gram-negative Escherichia coli and Pseudomonas aeruginosa bacteria, and Candida parapsilosis yeast and further correlated with their zeta potential. Then, blends of these cationic polymers with commercial polyacrylonitrile as matrix material were prepared and their effectiveness as antimicrobial coating was determined against Gram-negative Escherichia coli bacteria. In addition and due to the presence of the carbonate groups in the copolymer structures, these systems could be further used as antimicrobial releasing coatings in alkaline conditions.

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Section: Resultsmentioning

confidence: 57%

Influence of side chain structure on the thermal and antimicrobial properties of cationic methacrylic polymers

Cuervo-Rodríguez

Muñoz‐Bonilla

Araujo

et al. 2019

European Polymer Journal

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“…The resulting copolymers were not water soluble, due to the shorter PTTBM segment with respect to the hydrophobic PS block. In addition, TTBM monomer presents a longer spacer in comparison with others monomers with analogous structures previously used for the synthesis of antimicrobial polymers, thus its water solubility is reduced . This fact is important as these copolymers will be used in surfaces to introduce antimicrobial activity, therefore we can avoid or reduce diffusion problems to the aqueous media.…”

Section: Resultsmentioning

confidence: 99%

“…In that work, the copolymer also consisted of PS segment and a methacrylic block containing triazole and thiazole groups, which were quaternized with butyl iodide. This quaternized block had more rigid side chain than the PTTBM block used in the current study. Chain mobility is also an important factor for successful membrane disruption, as the cationic charge along flexible chain could better interact simultaneously with the bacterial membrane through multiple interactions …”

Section: Resultsmentioning

confidence: 99%

“…In the current work, block copolymers based on styrene and 4‐(1‐(2‐(4‐methylthiazol‐5‐yl)ethyl)‐1H‐1,2,3‐triazol‐4‐yl)butyl methacrylate (TTBM) were synthesized by simultaneous “click chemistry” and controlled atom transfer radical polymerization (ATRP), and further the thiazole and triazole groups were quaternized with either methyl or butyl iodide. The copolymers were designed to have a flexible side chain with a butyl spacer to enhance the contact with the bacterial membrane. Additionally, the hydrophobic/hydrophilic balance was adjusted by the presence of a long polystyrene block to maintain the copolymer water insoluble, and avoid any possible leaching out of the film.…”

Section: Introductionmentioning

confidence: 99%

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Contact Active Antimicrobial Coatings Prepared by Polymer Blending

Cuervo-Rodríguez

López-Fabal

Gómez-Garcés

et al. 2017

Macromolecular Bioscience

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Herein, contact active antimicrobial films are prepared by simply blending cationic amphiphilic block copolymers with commercial polystyrene (PS). The copolymers are prepared by combining atom transfer radical polymerization and "click chemistry." A variety of copolymers are synthesized, and composed of a PS segment and an antimicrobial block bearing flexible side chain with thiazole and triazole groups, 4-(1-(2-(4-methylthiazol-5-yl)ethyl)-1H-1,2,3-triazol-4-yl) butyl methacrylate (TTBM). The length of the TTBM block is varied as well as the alkylating agent. Different films are prepared from N,N-dimethylformamide solution, containing variable PS-b-PTTBM/PS ratio: from 0 to 100 wt%. Remarkably, the blend films, especially those with 30 and 50 wt% of copolymers, exhibit excellent antimicrobial activities against Gram-positive, Gram-negative bacteria and fungi, even higher than films prepared exclusively from the cationic copolymers. Blends composed of 50 wt% of the copolymers present a more than 99.999% killing efficiency against the studied microorganisms. The better activity found in blends can be due to the higher roughness, which increases the surface area and consequently the contact with the microorganisms. These results demonstrate that the use of blends implies a reduction of the content of antimicrobial agent and also enhances the antimicrobial activity, providing new insights for the better designing of antimicrobial coatings.

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“…As above mentioned, in addition to the charge density and the hydrophobic/hydrophilic balance, the flexibility of the side chain, the length of the side chain was varied; MTA2 with a long side chain of ethyl succinate, showed higher flexibility than MTA1 leading polymers with lower glass transition temperature (T g ). 21 The flexibility of the side chain was also varied in polymers bearing both functional groups, MTA3, MTA4, MTA5 and MTA6 in which the length of the lateral chain was also systematically changed. In the copolymers MTA3, MTA4 and MTA5 the side chain incorporates alkyl group, methyl, butyl and nonyl, respectively; whereas the MTA6 contains a methyl succinate group, which is a more polar group.…”

Section: Antimicrobial Copolymer Design and Film Preparationmentioning

confidence: 99%

Tailoring Macromolecular Structure of Cationic Polymers towards Efficient Contact Active Antimicrobial Surfaces

Tejero¹,

Gutiérrez²,

López³

et al. 2018

Preprint

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The aim of this work is the preparation of contact active antimicrobial films by blending copolymers with quaternary ammonium salts and polyacrylonitrile as matrix material. A series of copolymers based on acrylonitrile and methacrylic monomers with quaternizable groups were designed with the purpose of investigating the influence of their chemical and structural characteristics on the antimicrobial activity of these surfaces. The biocide activity of these systems was studied against different microorganisms, such as the Gram-positive bacteria Staphylococcus aureus and the Gram-negative bacteria Pseudomona aeruginosa and the yeast Candida parapsilosis. The results confirmed that parameters such as flexibility and polarity of the antimicrobial polymers immobilized on the surfaces strongly affect the efficiency against microorganisms. In contrast to the behavior of copolymers in water solutions, when they are tethered to the surface, the active cationic groups are less accessible and then the mobility of the side chain is critical for a good contact with the microorganism. Blend films composed of copolymers with high positive charge density and chain mobility present up to a more than 99.999% killing efficiency against the studied microorganisms.Preprints (www.preprints.org) | NOT PEER-REVIEWED | Posted:

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Influence of spacer group on the structure and thermal properties of copolymers based on acrylonitrile and methacrylic 1,3-thiazole and 1,2,3-triazole derivatives

Cited by 6 publications

References 30 publications

Influence of side chain structure on the thermal and antimicrobial properties of cationic methacrylic polymers

Influence of side chain structure on the thermal and antimicrobial properties of cationic methacrylic polymers

Contact Active Antimicrobial Coatings Prepared by Polymer Blending

Tailoring Macromolecular Structure of Cationic Polymers towards Efficient Contact Active Antimicrobial Surfaces

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