Synthesis and antimicrobial activity of some polymers derived from modified amino polyacrylamide by reacting it with benzoate esters and benzaldehyde derivatives

Functionalized polymers have gained much interest in the last decades. This is due to their functional groups and their polymer nature, which give them unique properties and more advantages than the corresponding small molecules. In this trend, we modified polyacrylamide by introducing an amino group in the side chain of the polymer by reacting it with ethylenediamine. The amine‐modified polymer was reacted with two classes of active compounds. The first group is aromatic aldehydes containing active groups such as p‐hydroxybenzaldehyde, vanillin, p‐chlorobenzaldehyde, and anisaldehyde. The second group is phenolic ester derivatives such as p‐hydroxymethylbenzoate, 2,4‐dihydroxymethylbenzoate, 2‐hydroxymethylbenzoate and 3,4,5‐trihydroxypropylbenzoate. The antimicrobial activity of these two classes were explored by cut plug method against Candida albicans SC5314, Aspergillus flavus, and Fusarium oxysporium as fungal organisms and Bacillus subtilis, Escherichia coli, and Staphylococcus aureus as bacterial organisms. It was found that the diameter of inhibition zone varied according to the active group in the modified polymer and the examined microorganism. In general, the modified polymers showed antimicrobial activity against the tested microorganisms. However, the polymer derivative of p‐chlorobenzaldehyde being the most effective on bacteria and fungi species. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci, 2006     

Development of Green Dual Polymers for Antibacterial Applications

In this article, we report on the antibacterial properties of a novel antimicrobial poly(citric acid-co-curcumin) polymer system that was prepared by a catalyst–free polyesterification process. The dual polymer of poly(citric acid-co-curcumin) was synthesized by varying the weight ratio of citric acid and curcumin monomers. Details of the synthesis, spectral (Fourier transform infrared, ultraviolet), thermal stability (Thermogravimetric analyses), and the morphological (Scanning electron microscopy/energy dispersive spectroscopy) characterization of dual polymers are presented in this scientific article. The UV–visible spectrometry was used to confirm the copolymerization of curcumin dispersion in the dual polymer systems. The presence of functional groups of copolymers was confirmed by Fourier transform infrared spectroscopy. The thermogravimetric analysis results indicated that poly(citric acid-co-curcumin) have a thermal stability up to 225°C. The ratios used were 1:0.25, 1:0.5, 1:0.75, and 1:1 and their antibacterial properties were studied with respect to their activity on gram-positive and gram-negative bacteria. This dual polymer was inoculated onto a Petri dish and its ability to inhibit the growth of Escherichia coli, Staphylococcus, Bacillus subtilis, Candida albicans (fungus), and Micrococcus luteus was evaluated using the bacterial disc method. Results indicated inhibition properties to increase with increasing curcumin content and the dual polymer with highest curcumin content showed excellent antimicrobial activities against both gram-negative and gram-positive microorganisms. Hence, it was clear that the developed dual polymers may be effectively used for antibacterial applications such as wound dressing.     

Facile Fabrication of Povidone Iodine-Embedded Polytetrafluoroethylene Superhydrophobic Films with Improved Antiadhesive and Bactericidal Properties in Bacterial Environments

It remains a challenge to maintain the antiadhesion properties of superhydrophobic films after exposure to bacterial environments. In this work, superhydrophobic bactericidal polymer films via the simple incorporation of polyvinylpyrrolidone-iodine (PVP-I) or iodine into polytetrafluoroethylene (PTFE) are fabricated to improve their antiadhesive and antibacterial capability. Superhydrophobic iodine-embedded films, polytetrafluoroethylene/polyvinylpyrrolidone-iodine and polytetrafluoroethylene-iodine (PTFE/PVP-I and PTFE-I), show excellent antiadhesive and bactericidal performances even post exposure to bacterial solutions as compared to iodine-free counterparts by controlling the release of iodine. Especially, superhydrophobic PTFE/PVP-I films display a more sustained iodine release profile and significant antibacterial properties against gram-positive (S. aureus, methicillin-resistant S. aureus (MRSA)) and gram-negative (E. coli) bacteria. Such a facile combination of antiseptic agents and superhydrophobic surface could be widely used for antiseptic biomedical applications.     

Antibacterial Properties of Ester—Cross-Linked Cellulose–Containing Fabrics Post-Treated with Metal Salts

To improve the performance properties of cellulose-containing fabric, ester was cross-linked with polycarboxylic acid in the presence of specific catalysts. Its pendant carboxyl groups were exploited in binding some heavy metals (by reacting with some salts, such as zinc acetate, zinc chloride, zinc sulfate, cupric acetate, cupric chloride, cupric sulfate, and nickel sulfate) capable of imparting their antibacterial activity toward some gram-positive bacteria (viz., B. subtilis, B. mycoides, Sta. aureus) and a gram-negative bacteria (E. coli). Zinc salts impart to the fabric the highest antibacterial activity, followed by cupric acetate. Zinc chloride proved to be the metal salt that yielded the maximum antibacterial activity.     

Multicomponent Petasis‐borono Mannich Preparation of Alkylaminophenols and Antimicrobial Activity Studies

In this work we report the antibacterial activity of alkylaminophenols. A series of such compounds was prepared by a multicomponent Petasis‐borono Mannich reaction starting from salicylaldehyde and its derivatives. The obtained compounds were tested against a large panel of microorganisms, Gram‐positive and Gram‐negative bacteria, and a yeast. Among the several tertiary amine derivatives tested, indoline‐derived aminophenols containing a nitro group at the para‐phenol position showed considerable activity against bacteria tested with minimal inhibitory concentrations as low as 1.36 μm against Staphyloccocus aureus and Mycobacterium smegmatis. Cytotoxicity of the new para‐nitrophenol derivatives was observed only at concentrations much higher than those required for antibacterial activity.     

Cationic starch iodophores

Cross‐linked cationic starches N‐(2‐hydroxyl)propyl‐3‐trimethyl ammonium starch chloride (CQS chloride), N‐(2‐hydroxyl)propyl‐3‐trimethyl ammonium starch iodide (CQS iodide), and N‐(2‐hydroxyl)propyl‐3‐trimethyl ammonium starch iodide–iodine (CQS triiodide) with the degree of substitution (DS) according to cationic groups from 0.04 to 0.62, as well as cross‐linked starch–iodine complexes were synthesized and tested as potential antibacterial agents. Cationic starch iodine derivatives were obtained during ion exchange reaction between CQS chloride and iodide or iodide–iodine anions in aqueous solutions. CQS_DS≤0.3 chloride can form several types of iodine complexes, such as the blue amylose–iodine inclusion complex and ionic CQS⁺I^?·(I₂)_m complex (m ≥ 1). The antibacterial activity of modified starches–iodine samples against different pathogenic bacterial cultures and contaminated water microorganisms was evaluated. CQS chloride and CQS iodide were found to be bacteriostatic. A strong antibacterial activity was characteristic of CQS triiodides in which molecular iodine is present in both ionic and inclusion complexes. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Polymerized ionic liquids-based hydrogels with intrinsic antibacterial activity: Modern weapons against antibiotic-resistant infections

In this study, the inherent antibacterial activity of 11 different polymerized ionic liquids (PILs)-based hydrogels as well as their corresponding monomers was examined in an extensive screening. The methicillin-resistant Staphylococcus aureus Xen 30 (MRSA Xen 30) and Pseudomonas aeruginosa Xen 5 (P. aeruginosa Xen 5) were chosen as test microorganisms. Both are typical representatives of gram-positive and gram-negative bacteria, respectively. Six of the 11 tested monomers were able to eradicate more than 80% of P. aeruginosa Xen 5 cells in suspension. Unfortunately, the anionic, neutral and zwitterionic representatives lost their function after polymerization. However, the cationic gels retained their antibacterial activity with nearly 100% eradication of selected microorganisms - even at the smallest amount tested. Bactericidal activity against gram-positive MRSA Xen 30 was high when the bacteria were treated with the imidazolium-based monomers. Five of the tested compounds showed rather limited bactericidal activity <50% killed bacteria. The weak antibacterial activities could be significantly increased by crosslinking them to three-dimensional networks. As a result, all the hydrogels possessed strong killing efficiencies of at least 68% and were able to maintain this activity even at low hydrogel volume fractions. These findings are very promising for the development of new antibacterial materials for medical applications, for example, stent coatings.     

Aliphatic–aromatic polyester–polyaniline composites: preparation,characterization, antibacterial activity and conducting properties

Poly(butylene adipate‐co‐terephthalate) (PBAT) composites containing polyaniline (PANI) were prepared using a melt blending process. Acrylic‐acid‐grafted PBAT (PBAT‐g‐AA) and PANI were used to improve the compatibility and dispersibility of PANI within the PBAT matrix. The composites were characterised morphologically using scanning electron microscopy, chemically using Fourier transform IR spectrometry and ¹³C solid‐state nuclear magnetic resonance, and optically using UV‐visible spectroscopy. The electrical conductivity of the composites was also evaluated with a resistance tester and a cyclic voltameter. Escherichia coli (BCRC 10239) was chosen as the standard bacterium for determining the antibacterial properties of the composite materials. The anti‐static properties of the composites were also evaluated. The PBAT‐g‐AA/PANI composite showed markedly enhanced antibacterial and anti‐static properties due to the formation of amide bonds by the condensation of the carboxylic acid groups of PBAT‐g‐AA with the amino groups of PANI. The optimal level of PANI was 9 wt%, as excess PANI led to separation of the two organic phases, lowering their compatibility. Copyright © 2012 Society of Chemical Industry     

A study on melt spinning of polyethylene terephthalate filament yarns containing various concentrations of synthesized CuO nanoparticles

In this research the CuO nanoparticles were synthesized with four different methods then used to produce polyethylene terephthalate (PET) fibers with antibacterial, antifungal, and photocatalytic properties during the melt spinning process. Nanoparticles were synthesized in different ways using copper acetate salt (Cu(CH₃COO)₂) and sodium hydroxide (NaOH). The synthesis of copper oxide (CuO) nanoparticles was confirmed by field-emission scanning electron microscopy (FE-SEM images), EDX patterns, TGA, FTIR, X-ray diffraction pattern XRD, and UV-vis absorption spectrum. The results showed that synthesized nanoparticles exhibited strong antibacterial activity against gram-positive and gram-negative bacteria. Finally, after examining the fibers with different percentages of nanoparticles), fibers containing 1% of nanoparticles were produced using a 20% nanocopper oxide masterbatch as the optimal sample. The presence of nanoparticles in the fiber structure was confirmed by FE-SEM images, EDX, XRD, and FTIR analysis. Furthermore, the tensile properties, thermal behavior, and photocatalytic properties of the fibers were investigated. Evaluation of the antibacterial and antifungal activity of the produced fibers against gram-positive bacteria Staphylococcus aureus and Candida albicans fungus showed about 90% death of bacteria and fungi.     

Electrochemical synthesis of poly(2‐iodoaniline) and poly(aniline‐co‐2‐iodoaniline) in acetonitrile

Poly(2‐iodoaniline) (PIANI) and poly(aniline‐co‐2‐iodoaniline) [P(An‐co‐2‐IAn)] were synthesized by electrochemical methods in acetonitrile solution containing tetrabutylammonium perchlorate (TBAP) and perchloric acid (HClO₄). The voltametry of the copolymer shows characteristics similar to those of conventional polyaniline (PANI), and it exhibits higher dry electrical conductivity than PIANI and lower than PANI. The observed decrease in the conductivity of the copolymer relative to PANI is attributed to the incorporation of the iodine moieties into the PANI chain. The structure and properties of these conducting films were characterized by FTIR and UV‐Vis spectroscopy and by an electrochemical method (cyclic voltametry). Conductivity values, FTIR and UV‐Vis spectra of the PIANI and copolymer were compared with those of PANI and the relative solubility of the PIANI and the copolymer powders was determined in various organic solvents. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 89: 1652–1658, 2003     

Biopolymer blended films of poly(butylene succinate)/cyclic olefin copolymer with enhanced mechanical strength for packaging applications

The demand for biodegradable materials is on the rise because humanity is now more concerned about a sustainable lifestyle than ever before. In this regard, we present solution casting synthesized novel biopolymer blended films of poly(butylene succinate)/cyclic olefin copolymer (PBS/COC) for packaging applications. These films were characterized by X-ray diffraction (XRD), Fourier transform infrared microscopy (FTIR), scanning electron microscopy (SEM), universal tensile testing (ASTM D882 standard), and antibacterial Disc diffusion tests using gram-negative Escherichia coli (E.coli) and gram-positive Staphylococcus aureus (S.aureus) bacteria. The XRD and FTIR revealed the type of bonding to be physical in-between the constituent polymers; ensuring the biodegradable nature of their blends, while the thickness of films was found to be <100 μm. The SEM, tensile, and antibacterial testing concluded that 30%PBS with 70%COC by weight blending is the best composition; showing a compact/pin-holes free morphology, the highest strength of 91 MPa, and contact inhibition with E.coli and S.aureus bacteria.     

Antimicrobial activity of some new 4‐arylazo‐3‐methylthiophene disperse dyes on polyester fabrics

A series of novel 4‐arylazo‐3‐methylthiophenes was synthesized by the heterocyclization of 2‐arylhydrazono‐2‐acetyl thioacetanilide derivatives with a variety of α‐halogenated reagents, such as chloroacetone, phenacyl bromide, ethyl chloroacetate, and chloroacetonitrile. The structures of the synthesized thiophene derivatives were confirmed by ultraviolet–visible, IR, and ¹H‐NMR spectroscopic techniques and elemental analysis. The synthesized dyes were applied to polyester fabrics as disperse dyes, and their fastness properties were evaluated. The dyed polyester fabrics displayed antibacterial efficacy against Gram‐positive (Staphylococcus aureus) and Gram‐negative (Escherichia coli) bacteria. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

Synthesis and antibacterial activity of copolymers having a quaternary ammonium salt side group

Copolymers with a quaternary ammonium salt side group have been prepared from vinylbenzyl–cetyldimethylammonium chloride and acrylonitrile and their antibacterial activity has been examined with Bacillus subtilis, Staphylococcus aureus, and Escherichia coli. Growth inhibitory effect has been found to increase with the increase in the quaternary ammonium salt concentration in the copolymer. The effect is small on gram-negative bacteria and large on gram-positive bacteria.     

Electrical and structural properties of polyaniline/cellulose triacetate blend films

Polyaniline (PANI) has been blended with cellulose triacetate (CTA) to obtain both good mechanical properties and good electrical properties. The effects of PANI weight percentage on the optical, structural, morphological and electrical properties in the blend films of polyaniline and cellulose triacetate (PANI/CTA) have been investigated. The phenomenon of percolation was observed in these blend films. It is found that the electrical conductivity of the blend films increases with the increase of polyaniline content up to a value of 10⁻⁴ S cm⁻¹ at 84 weight percentage of PANI. The experimental percolation threshold of the dried blend films is obtained at 9.5 wt% of polyaniline. The values of Mott’s temperature, density of states at the Fermi level [N (E _f)], hopping distance (R _hop), and barrier height (W _hop) for PANI/CTA blend films are calculated. By applying Mott’s theory, it is found that the PANI/CTA blend films obey the three dimensional variable range hopping mechanism.     

Preparation of some fatty glycolic acid derivatives and screening for antimicrobial activity

Nine glycolic acid derivatives were prepared and screened as primary plasticizers for polyvinyl chloride (PVC) and for antimicrobial activity. Two types of compounds were represented: (a) those with a methyl or ethyl ester grouping at the carboxyl function of glycolic acid and a fatty acyl group at the hydroxyl function; and (b) those with three acyl groups attached at the hydroxyl functions of the amide, resulting from the reaction of glycolic acid and diethanolamine. None of the compounds was compatible with PVC at the 35% level of incorporation, and the compounds were not further evaluated as plasticizers. They were screened for antimicrobial activity against a gram-positive bacterium,Staphylococcus aureus; a gram-negative bacterium,Escherichia coli; a yeast,Candida utilis; and a mold,Penicillium sp. Six of the compounds inhibited two or more of the test organisms suggesting some of these materials merit further testing as biostatic agents. A facility of the Southern Region, Science and Education Administration, U.S. Department of Agriculture.     

Preparation and properties of waterborne polyurethane/polyaniline codoped with dodecyl benzene sulfonic acid and hydrochloric acid blends

A conductive poly(aniline codoped with dodecyl benzene sulfonic acid and hydrochloric acid) [PANI‐D/H, yield: 32.2%, intrinsic viscosity ([η]): 1.39 dL/g, electrical conductivity: 7.3 S/cm] was synthesized by chemical oxidative polymerization from aniline‐dodecylbenzene sulfonic acid salt (A‐DS)/aniline‐hydrochloric acid salt (A‐HS) (6/4M ratio) in an aqueous system. Waterborne polyurethane (WBPU) dispersion obtained from isophorone diisocyanate/poly(tetramethylene oxide)glycol/dimethylol propionic acid/ethylene diamine/triethylene amine/water was used as a matrix polymer. The blend films of WBPU/PANI‐D/H with various weight ratios (99.9/0.1–25/75) were prepared by solution blending/casting. Effect of PANI‐D/H content on the mechanical property, dynamic mechanical property, hardness, electrical conductivity, and antistaticity of WBPU/PANI‐D/H blend films was investigated. The dynamic storage modulus and initial tensile modulus increased with increasing PANI‐D/H content up to 1 wt %, and then it was significantly decreased about the content. With increasing PANI‐D/H content, the glass transition temperature of soft segment (T_gs) and hard segment (T_gh) of WBPU/PANI‐D/H blend films were shifted a bit to lower the temperature. The tensile strength and hardness of WBPU/PANI‐D/H blend films increased a little with increasing PANI‐D/H content up to 0.5 wt %, and then it was dramatically decreased over the content. The elongation at break of WBPU/PANI‐D/H decreased with an increase in PANI‐D/H content. From these results, it was concluded that 0.5–1 wt % of PANI‐D/H was the critical concentration to reinforce those various properties of WBPU/PANI‐D/H blend films prepared in this study. The electrical conductivity of WBPU/ultrasonic treated PANI‐D/H (particle size: 0.7 μm) blend films prepared here increased from 4.0 × 10^?7 to 0.33 S/cm with increasing PANI‐D/H content from 0.1 to 75 wt %. The antistatic half‐life time (τ_1/2) of pure WBPU film was about 110 s. However, those of WBPU/ultrasonic treated PANI‐D/H blend films (τ_1/2: 8.2–0.1 s, and almost 0 s) were found to decrease exponentially with increasing PANI‐D/H content (0.1–9 wt %, and above 9 wt %). © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 93: 700–710, 2004     

Effectiveness of PANI/Cu/TiO2 ternary nanocomposite on antibacterial and antistatic behaviors in polyurethane coatings

Surfaces with antibacterial and antistatic functionalities are one of the new demands of todays' industry. Therefore, a facile method for the preparation of multifunctional polyaniline/copper/TiO₂ (PANI/Cu/TiO₂) ternary nanocomposite based on in situ polymerization is presented. This nanocomposite was characterized through the different techniques and was utilized for induction of antibacterial and antistatic properties in polyurethane coatings. Measurement of the conductivity of PANI/Cu/TiO₂ ternary nanocomposite indicated higher electrical conductivity of this nanocomposite compared to pure PANI. The antibacterial activity of the modified polyurethane coatings was tested against Gram-positive and Gram-negative bacteria which led to remarkable reduction in bacterial growth. Besides, it was observed that polyurethane coating with 2 wt % content of ternary nanocomposite has a surface electrical resistance equal 4 × 10⁸ Ω/sq which acquires surface electrical resistance of standard antistatic coatings. The final coatings were also characterized in terms of thermal and mechanical properties to investigate the effect of the ternary nanocomposite on improvement of these properties. © 2020 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020 , 137, 48825.     

Synthesis of (R)‐ and (S)‐Ricinoleic Acid Amides and Evaluation of Their Antimicrobial Activity

A series of fatty acid amides derived from (R)‐ and (S)‐ricinoleic acid and 4 cyclic and acyclic amines were synthesized in a proecological solvent‐free process with yields ranging from 43 to 88%. All S‐configured compounds and both enantiomers of amide with 2‐amino‐2‐methyl‐1‐propanol were obtained and studied in terms of biological activity for the first time. The evaluation of antimicrobial activity of (R)‐ and (S)‐ricinoleic acid derivatives against 13 different microorganisms representing Gram‐negative and Gram‐positive bacteria, yeast, and molds showed significant inhibitory activity against Gram‐positive bacteria, especially Micrococcus luteus and Bacillus subtilis, and against selected molds. Ethanolamine‐ and pyrrolidine‐derived amides showed the most promising antibacterial and antimold potential. Derivatives from ricinoleic acid and pyrrolidine were the most active against both selected molds, Aspergillus brasiliensis and Penicillium expansum. Moreover, the R‐configured analog was the most potent against B. subtilis. The amides of ricinoleic acid with ethanolamine exhibited significant potential to Staphylococcus aureus, which distinguished them from the rest of tested derivatives to which this bacterium was very resistant.     

Radiation-Induced Acrylamide/4-Vinyl Pyridine Biocidal Hydrogels: Synthesis,Characterization, and Antimicrobial Activities

Acrylamide/4-vinyl pyridine hydrogels were synthesized by radiation polymerization technique using a γ-irradiator. The prepared radiation-synthesized acrylamide/4-vinyl pyridine hydrogels were then treated using a modifying agent with aromatic functional group. The modifying agent used in the modification of acrylamide/4-vinyl pyridine hydrogels was the N-aromatic alkyl quaternizing agent of chloromethyl benzene. The functional group on the modified acrylamide/4-vinyl pyridine hydrogels was confirmed with Fourier transform infrared (FTIR) spectrometry. Thermal analysis, surface morphology investigation, and swelling of the modified and unmodified hydrogels were completed. The antibacterial and antifungal activities of the modified and unmodified hydrogels were also tested against gram-positive Staphylococcus aureus (ATCC 25923); two gram-negative Escherichia coli (ATCC 25922), and Pseudomonas aeruginosa (ATCC 27853) human pathogenic bacteria and a fungal strain—Candida albicans (ATCC 10231) for their MBC values. It was found that acrylamide/4-vinyl pyridine hydrogels do not possess biocidal properties, whereas the modified form of acrylamide/4-vinyl pyridine?chloromethyl benzene showed highly bactericidal characteristics.     

Antimicrobial properties of some erucic acid-glycolic acid derivatives

Twelve fatty acid derivatives of glycolic acid containing erucic acid, or other selected vegetable oil fatty acids, were synthesized. These were screened for antimicrobial activity against a gram-positive bacterium,Staphylococcus aureus; a gram-negative bacterium,Escherichia coli; a mold,Penicillium notatum, and a yeast,Candida utilis. All of the compounds inhibited at least one of these organisms. These compounds were derivatives of glycolic acid prepared by esterification of the carboxyl function of glycolic acid with a long-chain fatty alcohol and reaction of the hydroxyl function of glycolic acid with a long-chain fatty acyl group.