Metal‐ion‐retention properties of the poly(2‐acrylamido‐2‐methyl‐1‐propanosulfonic acid‐co‐4‐vinyl pyridine) resin

The water‐insoluble resin poly(2‐acrylamido‐2‐methyl‐1‐propanosulfonic acid‐co‐4‐vinyl pyridine), through a radical polymerization solution, was synthesized with ammonium persulfate as an initiator and N,N‐methylene bisacrylamide as a crosslinking reagent. The metal‐ion‐retention properties were studied by batch and column equilibrium procedures for the following metal ions: Hg(II), Cu(II), Cd(II), Zn(II), Pb(II), and Cr(III). These properties were investigated under competitive and noncompetitive conditions. The effects of the pH, maximum retention capacity, and regeneration capacity were studied. The resin showed a high retention ability for Hg(II) ions at pH 2.0. The retention of Hg(II) ions from a mixture of ions was greater than 90%. The resin showed a high selectivity for Hg(II) with respect to other metal ions. The Hg(II)‐loaded resin was able to be recovered with 4M HClO₄. The retention capacity was kept after four cycles of adsorption and desorption. The retention properties for Hg(II) were very similar with the batch and column methods. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 90: 3556–3562, 2003     

Heavy metal ions removal through poly(acrylamide-co-methacrylic acid) resin

The resin poly(acrylamide-co-methacrylic acid) P(AAm-co-MA) by radical polymerization was synthesized and its metal ion binding was studied using the batch and column equilibrium procedures for: Cd(II), Zn(II), Pb(II), Hg(II), Al(III), and Cr(III). Experiments were carried out at different pH, metal ion concentration, temperature, and contact time. The resin’s retention behavior was influenced by the pH. The highest retention 91% (0.248 mmol/g, 6.7 mg/g) was achieved at pH 5 for Al(III), and 87% (0.265 mmol/g, 54.9 mg/g) for Pb(II). For Hg(II), the yield was 85% (0.318 mmol/g, 63.7 mg/g) at pH 2. The metal-ion retention properties were dependent on the polymer/metal ion ratio. Under competitive conditions of Pb(II), Hg(II), and Al(III), the resin showed a higher retention of Hg(II), allowing the selective separation of this metal.     

Resins containing amino and carboxylic acid groups. Synthesis,characterization, and metal ion retention properties

The crosslinked poly[3‐(methacryloylamino)propyl]dimethyl(3‐sulfopropyl)ammonium hydroxide], P(MAPDSA), and poly[3‐(methacryloylamino)propyl]dimethyl(3‐sulfopropyl)ammonium hydroxide‐co‐acrylic acid], P(MAPDSA‐co‐AA), were synthesized by radical polymerization. The resins were completely insoluble in water. Due to the lower metal ion retention of P(MAPDSA), the metal ions investigated under competitive and noncompetitive conditions for Cu(II), Cd(II), Hg(II), Zn(II), Pb(II), and Cr(III) ions by batch and column equilibrium procedures were carried out only for P(MAPDA‐co‐AA), particularly for Hg(II). The resin–Hg(II) ion equilibrium was achieved before 15 min. The resin showed a maximum retention capacity value for Hg(II) at pH 2 of 1.89 meq/g. The resin showed a high selectivity to Hg(II) ions. The recovery of the resin was investigated at 25°C with different concentrations of HNO₃ and HClO₄. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 98: 525–530, 2005     

Water‐insoluble polymers with ability to remove metal ions

Crosslinked poly[3‐(methacryloylamino)propyl]dimethyl(3‐sulfopropyl)ammonium hydroxide‐co‐2‐acrylamido glycolic acid [P(MAAPDSA‐co‐AGCO)] was synthesized by radical polymerization and tested as an adsorbent under competitive and noncompetitive conditions for Cu(II), Cd(II), Hg(II), Zn(II), Pb(II), and Cr(III) by batch and column equilibrium procedures. The resin–metal ion equilibrium was achieved before 1 h. The resin showed a maximum retention capacity value for Hg(II) at pH 2 of 1.084 meq/g. The recovery of the resin was investigated at 20°C under different concentrations of HNO₃ and HClO₄. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 91: 3679–3685, 2004     

Preparation and adsorption properties of resins containing amine,sulfonic acid,and carboxylic acid moieties

Completely water‐insoluble resins containing amine, carboxylic acid, and sulfonic acid as ligand groups were synthesized by radical polymerization in solution. The yield was higher than 97%. The resins were characterized by FTIR spectroscopy and thermal analysis. The metal ion retention properties at different pH values were investigated by a batch method. Metal ions studied were: Cu(II), Cd(II), Zn(II), Hg(II), Pb(II), and Cr(III). The metal ion binding ability depended strongly on the pH. The retention properties were also tested under competitive conditions. Elution of the metal ion was investigated in acid medium at different concentrations. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 90: 700–705, 2003     

Poly(N-hydroxymethyl acrylamide-co-acrylic acid) and poly(N-hydroxymethyl acrylamide-co-acrylamidoglycolic acid): synthesis, characterization, and metal ion removal properties

Macroreticular chelating resins containing carboxylic groups, poly(N-hydroxymethyl acrylamide-co-acrylic acid) P(HMA-co-AA) and poly(N-hydroxymethyl acrylamide-co-2-acrylamido glycolic acid) P(HMA-co-AGA) were synthesized by solution radical polymerization with ammonium persulfate as initiator and N,N′-methylene-bis-acrylamide as cross-linking reagent. The polymerization yield was 98.9 and 91.9% for P(HMA-co-AA) and P(HMA-co-AGA), respectively. The retention properties were studied under competitive and noncompetitive conditions by batch equilibrium procedure for the following metal ions: Cd(II), Cr(III), Zn(II), Pb(II), and Hg(II). The effects of pH, time, temperature, and initial ion concentration on adsorption were investigated. The resins showed a significant ability to retain Pb(II), greater than 79%, at pH 5.     

Separation of metal ions by water‐insoluble polymers containing sulfonic/sulfonate groups

A water‐insoluble polymer, poly(sodium 4‐styrene sulfonate), was synthesized by radical polymerization at different amounts (2, 4, 6, and 8 mol %) of crosslinking reagent (CR). At the lowest CR level (2 mol %), only a water‐soluble polymer is obtained, and consequently it could not be studied as resin. The polymerization yield ranged from 82.6 to 91.6%. The resin is characterized by FTIR spectroscopy, thermal analysis, and scanning electron microscopy. The metal ion affinity is studied for the cations: Hg(II), Cd(II), Zn(II), Pb(II), Cr(III), and Al(III) with a batch equilibrium procedure under different experimental conditions. The metal ion affinity increased as the pH increased. At pH 5, the resin showed an affinity greater than 97% for all metal ions. Hg(II) showed the highest retention value at pH 2. The maximum retention capacity is determined at optimum pH for Hg(II), Cd(II), Pb(II), and Zn(II). © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 4328–4333, 2006     

Resin. III. Synthesis,characterization, and ion-exchange properties of a 2,2′-dihydroxybiphenyl–formaldehyde copolymer resin

A 2,2′-dihydroxybiphenyl–formaldehyde copolymer, synthesized by the condensation of 2,2′-dihydroxybiphenyl with CH₂O in the presence of an acid catalyst, proved to be a selective chelating ion-exchange copolymer for certain metals. The chelating ion-exchange properties of this copolymer were studied for Fe(III), Cu(II), Ni(II), Zn(II), Cd(II), and Pb(II) ions. A batch equilibrium method was employed in the study of the selectivity of metal ion uptake, involving the measurements of the distribution of a given metal ion between the copolymer sample and the solution containing the metal ion. The study was carried out over a wide pH range and in media of various ionic strengths. The copolymer showed a higher selectivity for Fe(III), Cu(II), and Ni(II) ions than for Co(II), Zn(II), Cd(II), and Pb(II) ions. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Adsorption properties of poly(acrylaminophosphonic-carboxyl-hydrazide)type chelating fiber for heavy metal ions

In this article, the adsorption properties of poly(acrylaminophosphonic-carboxyl-hydrazide) chelating fibers for Cu(II), Cd(II), Co(II), Mn(II), Pb(II), Zn(II), Ni(II), and Cr(III) are investigated by a batch technique. Based on the research results of binding capacity, adsorption isotherm, effect of pH value on sorption, and adsorption kinetics experiments, it is shown that the poly(acrylaminophosphonic-carboxyl-hydrazide) chelating fibers have higher binding capacities and good adsorption kinetic properties for heavy metal ions. The sorption of the metal ions on the chelating fibers is strongly dependent on the equilibrium pH value of the solution. The adsorption isotherms of Cu(II) and Cd(II) on the chelating fiber exhibit a Langmuir-type equation. The adsorbed Cu(II), Cd(II), Zn(II), and Pb(II) could be eluted by diluted nitric acid. © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 70: 7–14, 1998     

Part 8. Preparation,characterization and metal complexing of poly[(2‐hydroxyethyl)‐DL‐aspartamide] in aqueous solution

Poly[(2‐hydroxyethyl)‐DL ‐aspartamide] was synthesized by polyreaction of aspartic acid and subsequent polymer‐analogous functionalization with ethanolamine. The water‐soluble polymer was characterized by FTIR, NMR, TGA and light‐scattering measurements. The metal complexing properties of the polymer were studied for Cr(III), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Sr(II), Cd(II) and Pb(II) ions in aqueous solution using the liquid‐phase polymer‐based retention (LPR) method. According to the retention profiles of LPR, Cr(III), Fe(III), Cu(II) and Pb(II) showed a strong interaction with this polymer under these conditions, indicated by retention values of about 100 %. In contrast, Co(II), Ni(II), Zn(II), Sr(II) and Cd(II) exhibited retention values of only 50–60 % in dilute solution at pH 5. © 2000 Society of Chemical Industry     

Preparation and adsorption properties of the chelating resins containing carboxylic,sulfonic, and imidazole groups

The crosslinked poly(1‐vinylimidazole‐co‐acrylic acid), P(VIm‐co‐AA), and poly(1‐vinylimidazole‐co‐2‐acrylamido‐2‐methyl‐1‐propane sulfonic acid) P(VIm‐co‐APSA) were synthesized by radical polymerization and tested as adsorbents under competitive and noncompetitive conditions for Cu(II), Cd(II), Hg(II), Zn(II), Pb(II), and Cr(III) by batch equilibrium procedure. The resin–metal ion equilibrium was achieved before 1 h. The resin P(VIm‐co‐AA) showed a maximum retention capacity (MRC) value for Pb(II) at pH 3 and Hg(II) at pH 1 of 1.1 and 1.2 mEq/g, respectively, and the resin P(VIm‐co‐AA) showed at pH 3 the following MRC values: Hg(II) (1.5 mEq/g), Cd(II) (1.9 mEq/g), Zn(II) (2.7 mEq/g), and Cr(III) (2.8 mEq/g). The recovery of the resin was investigated at 25°C with 1 M and 4 M HNO₃ and 1 M and 4 M HClO₄. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 89: 2852–2856, 2003     

Water‐insoluble polymers containing amine,sulfonic acid,and carboxylic acid groups: Synthesis,characterization, and metal‐ion‐retention properties

Crosslinked poly(acryloylmorpholine) and its copolymers poly(acryloyl morpholine‐co‐acrylic acid) and poly(acryloylmorpholine‐co‐2‐acrylamide‐2‐methyl‐1‐propane sulfonic acid) were synthesized by radical polymerization. The resins were completely insoluble in water and were characterized with Fourier transform infrared spectroscopy and thermal analysis. The metal ions Ag(I), Cu(II), Cd(II), Hg(II), Zn(II), Pb(II), Al(III), and Cr(III) were investigated under competitive and noncompetitive conditions by a batch equilibrium procedure. The resin‐metal‐ion equilibrium was achieved before 5 min. The recovery of the resin was investigated at 20°C with different concentrations of HNO₃ and HClO₄. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 99: 3266–3274, 2006     

Polyelectrolyte‐assisted removal of metal ions with ultrafiltration

The water‐soluble polymers poly(styrene sulfonic acid‐co‐maleic acid) and poly(acrylic acid‐co‐maleic acid) were investigated with respect to their metal‐ion‐binding ability with ultrafiltration. The studied metal ions included Ag(I), Cu(II), Ni(II), Co(II), Ca(II), Mg(II), Pb(II), Cd(II), Zn(II), Al(III), and Cr(III) ions. The retention properties of the polyelectrolytes for the metal ions depended strongly on the ligand type. As for the carboxylate ligands, with increasing concentration and pH, the metal‐binding affinity increased. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 95: 1091–1099, 2005     

Synthesis of water‐insoluble functional copolymers containing amide,amine, and carboxylic acid groups and their metal‐ion‐uptake properties

The crosslinked poly[N‐(3‐dimethylamino)propylmethacrylamide] [P(NDAPA)] and poly[N‐(3‐dimethylamino)propylmethacrylamide‐co‐acrylic acid] [P(NDAPA‐co‐AA)] were synthesized by radical polymerization. The resins were completely insoluble in water. The metal‐ion‐uptake properties were studied by a batch equilibrium procedure for the following metal ions: silver(I), copper(II), cadmium(II), zinc(II), lead(II), mercury(II), chromium(III), and aluminum(III). The P(NDAPA‐co‐AA) resin showed a lower metal‐ion affinity than P(NDAPA), except for Hg(II), which was retained at 71% at pH 2. At pH 5, the resin showed a higher affinity for Pb(II) (80%) and Cu(II) (60%), but its affinity was very low for Zn(II) and Cr(III). The polymer ligand–metal‐ion equilibrium was achieved during the first 20 min. By changing the pH, we found it possible to remove between 60 and 70% of Cd(II) and Zn(II) ions with (1M, 4M) HClO₄ and (1M, 4M) HNO₃. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 102:5232–5239, 2006     

Synthesis and properties of hydrophilic polymers,part 11: Synthesis,biodegradability, and metal complexation of copolymers of ethylenediaminetetraacetic acid dianhydride and lactose

The synthesis and characterization of poly(ethylenediaminetetraacetic acid‐co‐lactose) of high molar mass (132 kg mol^?1) is described. The polycondensate with pendant carboxylic groups was shown to be hydrolytically and microbiologically degradable by using conventional microbiological methods. The metal complexing properties of the polyester were studied for Cr(III), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Sr(II), Cd(II), Pb(II), and Al(III) ions in aqueous solution using the liquid‐phase polymer‐based retention (LPR) method. In addition, the complexing capacity of the Cu(II)‐saturated copolymer was determined by TGA to be 182 mg g^?1 polymer. According to the retention profiles determined as a function of filtration factor by using LPR in conjunction with inductively coupled plasma spectrometry, Cr(III) and Fe(III) showed a strong interaction with this polymer under these conditions, indicated by retention values of 100% at pH 5. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 2932–2939, 2007     

Analytical applications of newly synthesized copolymer resin derived from p‐aminophenol,dithiooxamide, and formaldehyde

A copolymer resin (p‐APDF) has been synthesized using the monomers p‐aminophenol, dithiooxamide, formaldehyde in 1 : 1 : 2M proportions in the presence of 2M HCl as catalyst. The structure of p‐APDF copolymer has been elucidated on the basis of elemental analysis and various physicochemical techniques, i.e., UV‐visible, FTIR, and ¹H‐NMR spectroscopy. The number average molecular weight of copolymer resin was determined by nonaqueous conductometric titration in DMF. Viscosity measurement were carried out in DMF indicate normal behavior. The prepared resin proved to be a selective ion exchange resin for some metal ions. The chelating ion exchange properties of this resin was studied for Fe(III) and Cu(II), Ni(II), Co(II), Zn(II), Cd(II), Pb(II) ions. A batch equilibrium method was used to study selectivity of metal ion uptake over a wide pH range and in media of various ionic strength. The resin showed a higher selectivity for Fe(III), Ni(II), Cu(II) ions than for Co(II), Pb(II), Zn(II), and Cd(II) ions. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Synthesis and properties of hydrophilic polymers. IX. Synthesis,biodegradability, and metal complexation of copolymers of ethylenediaminetetraacetic acid dianhydride and lactose

The synthesis and characterization of poly(ethylenediaminetetraacetic acid‐co‐lactose) with pendant carboxylic groups of high molar mass (132 kg mol^?1) is described. The polycondensate was hydrolytically and microbiologically degradable with conventional microbiological methods. The metal‐complexing properties of the polyester were studied for Cr(III), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Sr(II), Cd(II), Pb(II), and Al(III) ions in aqueous solution with the liquid‐phase polymer‐based retention (LPR) method. In addition, the complexing capacity of the Cu(II)‐saturated copolymer was determined by thermogravimetric analysis to be 182 mg g^?1 of polymer. According to the retention profiles determined as a function of the filtration factor with LPR in conjunction with inductively coupled plasma spectrometry, Cr(III) and Fe(III) showed a strong interaction with this polymer under these conditions, as indicated by retention values of about 100% at pH 5. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 90: 650–657, 2003     

Resin I: Synthesis,characterization, and ion‐exchange properties of terpolymer resins derived from 2,4‐dihydroxypropiophenone,biuret, and formaldehyde

Terpolymers (2,4‐DHPBF) were synthesized by the condensation of 2,4‐dihydro‐xypropiophenone, biuret, and formaldehyde in the presence of acid catalyst with varying the molar ratio of reacting monomers. Terpolymer composition has been determined on the basis of their elemental analysis and their number–average molecular weight of these resin were determined by conductometric titration in nonaqueous medium. The viscosity measurements were carried out in N,N‐dimethyl formamide which indicate normal behavior. IR spectra were studied to elucidate the structure. The terpolymer resin has been further characterized by UV–visible and ¹H‐NMR spectra. The newly synthesized terpolymers proved to be selective chelating ion‐exchange terpolymers for certain metals. The chelating ion‐exchange properties of this terpolymer was studied for Fe (III), Cu (II), Hg (II), Cd (II), Co (II), Zn (II), Ni (II), and Pb (II) ions. A batch equilibrium method was employed in the study of the selectivity of metal ion uptake involving the measurement of the distribution of a given metal ion between the terpolymer sample and a solution containing the metal ion. The study was carried out over a wide pH range and in media of various ionic strengths. The terpolymer showed a higher selectivity for Fe (III), Hg (II), Cd (II), and Pb (II) ions than for Cu (II), Co (II), Zn (II), and Ni (II) ions. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008     

Poly(sodium 4-styrenesulfonate)–metal ion interactions

The metal ion-binding properties of poly(sodium 4-styrenesulfonate) in conjunction with membrane filtration were investigated for Cu(II), Cd(II), Co(II), Cr(III), Hg(II), Ni(II), Pb(II), Zn(II), and Fe(II). Different experiments were carried out at different pH's, metal ion concentrations, polymer concentrations, and molecular weight fractions. Only Fe(II) and Cr(III) were retained at pH 1, which allows a selective separation of these metals from all the other metal ions. At pH 3 the retention ability of this polymer increased for all the metal ions. On the other hand, the metal ion-retention properties are dependent on the polymer/metal ratio. © 1998 John Wiley & Sons, Inc. J. Appl. Polym. Sci. 70: 219–225, 1998     

Metal ion retention using the ultrafiltration technique: Preparation,characterization of the water-soluble poly(1-vinyl-2-pyrrolidone-co-itaconic acid) and its metal complexes in aqueous solutions

Radical copolymerization of 1-vinyl-2-pyrrolidone with itaconic acid at different feed monomer ratios (75–25 mol %) were investigated. The copolymers were characterized by elemental analysis, Fourier transform infrared (FTIR), ¹H and ¹³C NMR spectroscopy. The copolymer composition was determined from elemental analysis and found to be statistical copolymers. Additionally, viscosimetric measurements, molecular weight, and polydispersity have been determined. The metal complexation of poly(1-vinyl-2-pyrrolidone-co-itaconic acid) for the metal ions such as Cr(III), Co (II), Zn(II), Ni(II), Cu(II), Cd(II), and Fe(III) were investigated at pH 3, 5, and 7 in aqueous solution. The metal ion interaction with hydrophilic polymers was determined as a function of the pH and filtration factor. Poly(1-vinyl-2-pyrrolidone-co-itaconic acid) showed a high affinity for the metal ions at pH 5 and 7. The poly(NVP-co-IA), with a copolymer composition of 29 : 71 mol % (PVA-3), presented the highest metal ion retention values, particularly at higher pHs, at which the carboxylic acid groups are nonprotonated and could easily coordinate with the metal ions. According to the interaction pattern obtained, Cr(II), Zn(II), Pb(II), and Ni(II) formed the most stable complexes at pH 7. The thermal behaviors of the copolymer and polymer metal complex were characterized using differential scanning calorimetry (DSC) and thermogravimetry techniques under nitrogen atmosphere. The copolymers present high thermal stability and do not present glass transition in DSC curves between 25 and 500°C. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci 2008