Novel biocidal polymers based on branched and linear poly(hydroxystyrene)

New biocidal polymers based on branched as well as linear poly(p-hydroxystyrene) were synthesized. Biocidal polymers were synthesized in two steps by creation of active centers via chloroacetylation of linear and branched poly(p-hydroxystyrene) using chloroacetyl chloride. The second step involves the immobilization of onium salts onto the chloroacetylated polymers. All the prepared polymers were characterized using elemental microanalysis, FT-IR, ¹H NMR spectra, and TGA. Antimicrobial activity of the prepared polymers was tested against various pathogenic microorganisms. The antimicrobial activity was found to be affected by the active group and the tested microorganism. The phosphonium salts showed higher activity than ammonium salts.     

Durable and regenerable antimicrobial textiles: Improving efficacy and durability of biocidal functions

2,2,5,5‐Tetramethylimidazolidinone (TMIO)‐modified cotton‐containing fabrics could provide excellent durable antimicrobial properties, but the biocidal speeds were low because of its amine halamine structures. To prepare biocidal fabrics that can inactivate microorganisms rapidly and survive repeated laundering and long duration of storage, 3‐methylol‐2,2,5,5‐tetramethylimidazolidinone and dimethylol‐5,5‐dimethylhydantoin were combined in different ratios in chemical modifications of cellulose fabrics. The mixtures of TMIO and hydantoin rings on the grafted cellulose provided a hybrid of imide, amide, and amine halamine structures in different ratios after chlorination, and led to varied efficacy and durability of biocidal properties on the finished fabrics. The effect of the combined halamine structures on biocidal efficacy and durability of the fabrics were discussed in this article. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 91: 2588‐2593, 2004     

丹皮酚及其席夫碱衍生物的抑菌性研究

以丹皮酚为先导,合成了丹皮酚缩1,3-丙二胺、丹皮酚缩2-羟基-1,3-丙二胺和丹皮酚缩糠胺3种丹皮酚席夫碱衍生物。琼脂扩散抑菌试验表明,丹皮酚及其衍生物对受试4种革兰氏阴性菌、阳性菌皆有明显的抑制作用。     

配位聚合物的合成及其性质

通过对配位聚合物的合成方法、影响因素、性质应用等内容的介绍,指出了配位聚合物作为新型功能性材料得到广泛关注的原因。并对配位聚合物的发展前景作了展望。     

两种二茂铁基席夫碱的合成及其抑菌活性

合成了两种标题化合物,产率分别为58.2%和81.3%;其结构通过元素分析、IR、1HNMR进行了表征;抑菌实验表明,两种席夫碱对大肠杆菌和金黄色葡萄球菌均有较好的抑菌活性.     

Synthesis,characterization, and thermal and antimicrobial studies of newly developed transition metal–polychelates derived from polymeric Schiff base

Monomeric Schiff base derived from salicylaldehyde and 1,3‐diaminopropane was subjected to polycondensation reaction with formaldehyde and piperazine in basic medium. The resin was found to form polychelates readily with Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) metal ions. The materials were characterized by elemental analysis, spectral studies (IR, ¹H‐NMR, ¹³C‐NMR, and UV–visible), magnetic moment measurements, and thermal analysis. The electronic spectra and magnetic moment measurements of the synthesized polychelates confirmed the geometry of the central metal ion. Metal–resin bonds were registered in the IR spectra of the polychelates. The thermogravimetric analysis data indicated that the polychelates were more stable than the corresponding polymeric Schiff base. All the synthesized metal–polychelates showed excellent antibacterial activities against the selected bacteria. The antimicrobial activities were determined by using the shaking flask method, where 25 mg/mL concentrations of each compound were tested against 10⁵ CFU/mL bacteria solutions. The number of viable bacteria was calculated by using the spread‐plate method, where 100 μL of the incubated antimicrobial agent in bacteria solutions were spread on agar plates, and the number of bacteria was counted after 24 h of incubation period at 37°C. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Biologically active polymers. IV. Synthesis and antimicrobial activity of polymers containing 8‐hydroxyquinoline moiety

Polymers containing 8‐hydroxyquinoline moiety were prepared. Modifications of the base polymer of glycidyl methacrylate were carried out in order to introduce chloromethyl groups, either by the hydrolysis of the poly(glycidyl methacrylate) and the chloroacetylation of the hydrolyzed polymer by the reaction with chloroacetyl chloride or by aminating the poly(glycidyl methacrylate) either with ethylenediamine or with hexamethylenediamine, followed by reacting the aminated polymers with chloroacetyl chloride. The polymers containing 8‐hydroxyquinoline moiety were prepared by reacting the chloromethyl groups containing polymers with potassium salt of 8‐hydroxy quinoline. The antimicrobial activity of the polymers obtained was examined against gram‐negative bacteria (Escherichia coli) and gram‐positive bacteria (Bacillus subtilus) as well as the fungus Trichophyton rubrum. Generally, all three polymers proved effective against the tested microorganisms, but growth inhibitory effects varied from one another. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 82: 1364–1374, 2001     

Synthesis and antimicrobial activities of new water‐soluble bis‐quaternary ammonium methacrylate polymers

New methacrylate monomers containing pendant quaternary ammonium moieties based on 1,4‐diazabicyclo‐[2.2.2]‐octane (DABCO) were synthesized. The DABCO group contains either a butyl or a hexyl pendant group comprising the hydrophobic segment of the monomers and one tether group to the methacrylate moiety. The monomers were homopolymerized in water by using 2,2′‐azobis(2‐methylpropionamide) dihydrochloride (V‐50) as an initiator. The monomers and polymers were characterized by elemental analysis, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), FTIR, and ¹³C‐NMR. The antimicrobial activities of the corresponding small molecules (bis‐quaternary ammonium monocarboxylates) and polymers were investigated against Staphylococcus aureus and Escherichia coli. Although the small molecules did not show any antimicrobial activity, the polymers were moderately effective against both Gram‐positive and Gram‐negative bacteria. The minimum inhibitory concentration (MIC) values of the polymers with butyl and hexyl hydrocarbon chains against S. aureus and E. coli were found to be 250 and 62.5 μg/mL, respectively. The minimum bactericidal concentration (MBC) value for the polymer with the butyl group was higher than 1 mg/mL, whereas the MBC value for the polymer with hexyl group was found to be 62.5 μg/mL. Thus, an increase of the alkyl chain length from 4 to 6 significantly increased the antimicrobial activity of the polymer. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 94: 635–642, 2004     

Biologically active polymers. IV. Synthesis and antimicrobial activity of tartaric acid polyamides

New bactericidal polyamides with quaternary ammonium or phosphonium salts were prepared, and their antimicrobial activities were explored. The polyamides were synthesized by the polycondensation of diethyl‐l‐tartrate or chloromethylated diethyl‐l‐tartrate with ethylenediamine in dry absolute ethanol. The polyamides were modified to yield polymers with either quaternary ammonium or phosphonium salts. The polymers were characterized with elemental microanalysis and ¹H‐NMR and IR spectra. The antimicrobial activity of the polymers bearing onium salts was studied against Gram‐negative bacteria (Escherichia coli, Pseudomones aeruginosa, Shigella sp., and Salmonella typhae), Gram‐positive bacteria (Bacillus subtilis and Bacillus cereus), and a fungus (Trichophytum rubrum) by the cut‐plug and viable‐cell‐count methods. Although all the polymers showed high antibacterial activity, some had no antifungal activity. The tributyl phosphonium salt of the polyamide was more effective against both Gram‐negative and Gram‐positive bacteria than the triethyl ammonium and triphenyl phosphonium salts of the polyamide. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102: 4780–4790, 2006     

Synthesis and antimicrobial activity of Schiff base of chitosan and acylated chitosan

Chitosan, a biocompatible, biodegradable, nontoxic polymer, is prepared from chitin, which is the second most naturally occurring biopolymer after cellulose. Schiff base of chitosan, sorbyl chitosan, and p‐aminobenzoyl chitosan were synthesized working under high‐intensity ultrasound and their antimicrobial properties were analyzed against Escherichia coli, Staphylococcus aureus, and Aspergillus niger. The structures of the derivatives were characterized by FTIR spectroscopy and elemental analysis. The results of antimicrobial activities indicated that the antimicrobial activities of the derivatives increased with increasing the concentration. The antibacterial activity of schiff base of chitosan against E. coli was stronger, while acylated chitosan had better inhiting effect on S. aureus than others. It was also found that the antifungal activities of the derivatives were stronger than that of chitosan, and schiff base of chitosan was obviously superior to acylated chitosan. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Microbial susceptibility of various polymers and evaluation of thermoplastic elastomers with antimicrobial additives

The incursion of microbial growth on polymeric products can deteriorate their performance and lead to the development of undesirable staining and odors. A growing trend in the industry has aimed to reduce microbial populations on high-touch surfaces via the use of antimicrobials to protect material aesthetics and durability or to prevent the spread of pathogenic microorganisms. In this study, a variety of plastic substrates (30 unique polymer compounds), including poly(acrylonitrile-co-butadiene-co-styrene), poly(butylene terephthalate), poly(etherimide), various thermoplastic elastomers (TPEs), poly(carbonates), and poly(amides), were screened for susceptibility to microbial attack using American Society for Testing and Materials (ASTM) G21 (fungi susceptibility), Japanese Industrial Standard (JIS) Z2801, and modified ASTM E1428-15a (bacterial susceptibility) test standards. TPEs were determined to be most susceptible to microbial attack under the appropriate environmental conditions. Subsequent studies assessed the use of an antimicrobial additive, zinc pyrithione (ZPT), for potential efficacy in a variety of TPE blends for diverse target market applications. ZPT proved to be very effective in protecting TPEs, reducing Staphylococcus aureus and Escherichia coli populations by 99.9% or more in JIS Z2801 testing and inhibiting fungal growth (rating = 0) according to the ASTM G21 standard.     

Biocidal polymers: Synthesis,antimicrobial activity,and possible toxicity of poly (hydroxystyrene‐co‐methylmethacrylate) derivatives

Functionalized polymers have gained much interest in the last decades. This is due to their functional group and their polymer nature that give them unique properties and more advantages than the corresponding small molecules. In this trend, polyhydroxystyrene‐co‐MMA was modified to introduce amino group in the side chain of the polymer. The amine modified polymer was reacted with two classes of active compounds. The first class is aldehydes such as vanilline, p‐hydroxybenzaldehyde, p‐chlorobenzaldehyde, and anisaldehyde. The second class is phenolic esters such as p‐hydroxymethylbenzoate, 2,4‐dihydroxymethyl benzoate, and methyl salicylate. The antimicrobial activities of the polymer and modified polymer with these two classes were explored with Gram‐negative bacteria (Escherichia coli), Gram‐positive bacteria (Bacillus subtilus), fugus like yeast (Candida albicans SC5314), and pathogenic molds (Aspergillus flavus, Trycophyton rubrum, and F. oxysporium). In vitro studies indicated that the start polymer did not affect on the test microorganisms, in contrary to its derivatives. The diameter of inhibition zone varied according to the active group in the modified polymer, polymer microstructure, and the test microorganism. Derivatives I, II, and III were selected among the most effective antimicrobial compounds. Their inhibitory effects on the ratio of surviving cell number (M/C) increased by increasing derivatives concentrations. Derivatives I and II were inhibitorier to C. albicans and molds than to bacteria while derivative III was only antibacterial. These derivatives seemed toxic to Brine shrimp by increasing their concentrations above 10 ppm, with derivative III being the less toxic, compared to others. To clarify this toxic effect and to decrease the toxicity of these derivatives, more detailed studies are necessary, and this will be focused in the nearest future. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011     

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     

Recent progress in thermal analysis of polymers: experimental techniques and a new aspect of temperature in measurement of material properties

Thermal analysis has been utilized in polymer research for a long time and its usefulness is widely recognized. High‐performance commercial instruments have driven significant progress in the thermal studies of polymers. On the other hand, new experimental instruments have been developed in laboratories as well. In this paper attention is paid to the latter category. The laboratory‐made instrument focused on the target material and/or phenomena provides data that are not available from other techniques. Experiments using the temperature modulation technique, which has been successfully utilized in laboratory‐made instruments, are introduced in this paper. The temperature modulation technique reveals a new aspect of temperature useful for studies of material properties. © 2016 Society of Chemical Industry     

1-D and 2-D lanthanide coordination polymers constructed from 4-sulfobenzoate and 1,10-phenanthroline

Two complexes {[Dy₂(4-SBA)₃(phen)₂(H₂O)₄] · 2H₂O}_n (1) and {[Eu₂(4-SBA)₃(phen)₂(H₂O)₂]}_n (2) (4-SBA = 4-sulfobenzoate, phen = 1,10-phenanthroline) were synthesized and their structures were determined by X-ray crystallography. The 1 has a 1-D chain structure by bidentate and tridentate 4-SBA ligands as linkages and 3-D network was formed by strong hydrogen bonds. The 2 has a 2-D network structure by tridentate and tetradentate 4-SBA ligands as linkages. The luminescence properties and thermal stability of the two complexes were investigated.     

Ion imprinted polymers for selective recognition and separation of lanthanum and cerium ions from other lanthanide

The lanthanide-ion-imprinted polymers (L-IIPs) were synthesized from La³⁺ or Ce³⁺ ion and complexing agents either Schiff base or azobenzene with ethylene glycol-dimethylacrylate as cross-linking agent, 4-vinylpyridine monomer and 2,2-azobisisobutyronitrile initiator. After polymerization, cavities in the polymer particles corresponding to the La³⁺/Ce³⁺ ions were created by leaching in 20 mL of HCl solution (2.0 mol L^?1). The maximum sorption capacity is found to be 25.0, 24.3, 24.5 and 24.7 mg g^?1 of La-IIP-Schiff, La-IIP-Azo, Ce-IIP-Schiff, Ce-IIP-Azo polymers, respectively at pH 6. The L-IIPs gave good selectivity to La or Ce ions in the presence of other selected lanthanide cations with close atomic radius. The L-IIPs were reused and regenerated for ten times without a significant decrease in binding affinity.     

Hot‐wire parallel technique: A new method for simultaneous determination of thermal properties of polymers

The hot‐wire parallel technique standardized for determining the thermal conductivity of ceramic materials was employed in the determination of the thermal properties of polymers. For these materials, additional care must be taken considering the low melting point of polymers, when compared with that for ceramic materials. Samples can be prepared either in the shape of bricks or in the shape of half‐cylinders. The thermal conductivity and the specific heat were simultaneously determined from the same experimental thermal transient, and the thermal diffusivity is derived from these properties. Five different polymers with different structures at room temperature were selected, and measurements were carried out from room temperature to approximately the maximum service operating temperature. A nonlinear least‐squares fitting method was employed in the calculations, so that all the experimental points obtained are considered in the thermal properties' calculations. The apparatus used in this work is fully automatic. The reproducibility is very good with respect to the thermal conductivity, even with a defective experimental arrangement with respect to the theoretical model. However, deviations from the theoretical model have a severe influence on the specific heat values and, consequently, on the thermal diffusivity. Experimental results were compared with those available in the literature, showing the applicability of this technique for the determination of thermal properties of polymers. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 85: 1779–1786, 2002     

Synthesis and characterization of coordination polymers of polyesters with pendant amino groups

Oligomeric polyester, namely, poly(tetramethylene aspartate) (PTMA), was synthesized from D ,L -aspartic acid and 1,4-butanediol by a melt-condensation technique. Polyester–metal complexes were synthesized by the reaction of PTMA with hydrated acetates of Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II), Mg(II), Ca(II), Pb(II), and Ce(IV) in DMSO. The polyester–metal complexes were characterized by elemental analysis, IR spectral studies, magnetic susceptibility measurements, and thermogravimetry. The metal ions were found to be six-coordinated with two water molecules as additional ligands besides oxygen and nitrogen atoms of polyester repeating units. Thermogravimetric analysis (TGA) showed that coordination polymers are thermally more stable than is polyester. © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 69: 751–759, 1998     

Synthesis and characterization of liquid crystalline polymers containing aromatic ester mesogen and a nonmesogenic ferrocene unit in the spacer

A new series of liquid crystalline polymers containing aromatic triad ester mesogen and 1,1′‐disubstituted ferrocene as a nonmesogenic unit along with polymethylene spacer was synthesized. The polymer was synthesized by a room temperature polycondensation reaction between bis(4‐chloroformyl phenyloxy alkyl ferrocene dicarboxylate) and quinol. The alkyl groups have been varied by an even number of methylene groups with a range from two to ten groups. All the polymers were found to possess liquid crystalline properties. The identification of the mesophase is more transparent with an increase in the spacer. The thermal characteristics were studied using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The results reveal that the thermal stability of the polymers was decreased with increasing spacer length. The T_g, T_m, and T_i of the polymers decreased with increasing methylene groups. The incorporation of the ferrocene moiety also has a considerable effect on the glass transition temperature. The char yield of the polymer decreases with an increasing methylene chain length. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 86: 3494–3501, 2002     

Thermal, Spectroscopic, Cyclic Voltammetric, and Biological Activity Studies of Cobalt(II), Nickel(II), and Copper(II) Complexes of Dicarboxylic Amino Acids and 8-Hydroxyquinoline

Mixed ligand complexes of Co^II, Ni^II and Cu^II with dicarboxylic amino acids (aspartic, glutamic or H₂ADA) as primary ligands and 8-hydroxyquinoline as a secondary ligand were prepared and characterized by elemental analysis, conductivity measurements, thermal analysis, cyclic voltammetry, and electronic and infrared (IR) spectroscopy. Cyclic voltammetry reveals a reversibility of the Cu^II/Cu^I couple, while the reactions of the Co^II and Ni^II complexes are irreversible. All complexes have a metal-to-ligand ratios of 1:1:1 and octahedral structures are suggested to be attained by interactions among both of the amino acids and 8-hydroxyquinoline anions with the metal ions. The reaction orders and activation energies have been computed by means of the Coats–Redfern and Horowitz–Metzger equations. The biological activity of selected complexes as anti-fungal agents has been tested.