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Pure Appl. Chem., 1980, Vol. 52, No. 7, pp. 1883-1905

http://dx.doi.org/10.1351/pac198052071883

Preparation and application of water-soluble polymer-metal complexes

K. Geckeler, G. Lange, H. Eberhardt and E. Bayer

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  • Berdous S., Berdous D., Saidi-Amroun N., Akretche D. E., Saidi M.: The Permeability of Polyester Film (PEN) to Copper Ions. International Journal of Polymer Analysis and Characterization 2013, 18, 358. <http://dx.doi.org/10.1080/1023666X.2013.785066>
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  • Rivas Bernabé L., Pereira Eduardo, Guzmán Catherine, Maureira Antonio: Complexes of Water-Soluble Polymers with Cu2+ and Ag+ as Antibacterial Agents. Macromol Symp 2011, 304, 46. <http://dx.doi.org/10.1002/masy.201150607>
  • Llanos J., Camarillo R., Pérez A., Cañizares P., Rodrigo M. A.: Costs estimation of an integrated process for the treatment of heavy-metal loaded aqueous effluents. electrochem 2011, 41, 1099. <http://dx.doi.org/10.1007/s10800-011-0278-z>
  • Lakshmipraba Jagadeesan, Arunachalam Sankaralingam, Gandi Devadas Avinash, Thirunalasundari Thyagarajan: Synthesis, nucleic acid binding and cytotoxicity of polyethyleneimine-copper(II) complexes containing 1,10-phenanthroline and l-valine. Eur J Med Chem 2011, 46, 3013. <http://dx.doi.org/10.1016/j.ejmech.2011.04.033>
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  • Rivas Bernabé L., Maureira N. Antonio, Guzmán S. Catherine: Water-Soluble Polymers and Their Polymer-Metal Ion-Complexes as Antibacterial Agents. Macromol Symp 2010, 287, 69. <http://dx.doi.org/10.1002/masy.201050110>
  • Rivas Bernabé L., Sánchez Julio, Pooley S. Amalia, Basaez Luis, Pereira Eduardo, Bucher Christophe, Royal Guy, Aman Eric Saint, Moutet Jean-Claude: Water-Soluble Polyelectrolytes with Ability to Remove Arsenic. Macromol Symp 2010, 296, 416. <http://dx.doi.org/10.1002/masy.201051057>
  • Kümmel Rolf, Schumann Gerald: Zur kinetischen Beschreibung der Membranfiltration wasserlöslicher Metall-Polychelatogen-Komplexe. Z Chem 2010, 24, 448. <http://dx.doi.org/10.1002/zfch.19840241217>
  • Rivas Bernabé L., Maureira Antonio, Guzmán Catherine, Mondaca M. Angélica: Poly(2-acrylamido glycolic acid-co-2-acrylamido-2-methyl-1-propane sulfonic acid): Synthesis, characterization, and retention properties for environmentally impacting metal ions. J Appl Polym Sci 2009, 111, 78. <http://dx.doi.org/10.1002/app.29019>
  • Rivas Bernabé L., Maureira Antonio, Pereira Eduardo D.: Water-Soluble Polyacids with Capability to Remove Metal Ions in Homogenous Phase by Using the Liquid Phase Polymer-Based Retention Technique. Macromol Symp 2009, 279, 228. <http://dx.doi.org/10.1002/masy.200950533>
  • Rivas Bernabé L, Pereira Eduardo, Maureira Antonio: Functional water-soluble polymers: polymer-metal ion removal and biocide properties. Polym Int 2009, 58, 1093. <http://dx.doi.org/10.1002/pi.2632>
  • Maureira Antonio, Rivas Bernabé L.: Metal ions recovery with alginic acid coupled to ultrafiltration membrane. Euro Poly J 2009, 45, 573. <http://dx.doi.org/10.1016/j.eurpolymj.2008.11.021>
  • Rivas Bernabé L., Maureira Antonio: Water-soluble Polyelectrolytes Contaning Sulfonic Acid Groups with Metal Ion Binding Ability by Using the Liquid Phase Polymer Based Retention Technique. Macromol Symp 2008, 270, 143. <http://dx.doi.org/10.1002/masy.200851017>
  • Kumar Rajendran Senthil, Arunachalam Sankaralingam, Periasamy Vaiyapuri Subbarayan, Preethy Christo Paul, Riyasdeen Anvarbatcha, Akbarsha Mohammad Abdulkader: DNA binding and biological studies of some novel water-soluble polymer–copper(II)–phenanthroline complexes. Eur J Med Chem 2008, 43, 2082. <http://dx.doi.org/10.1016/j.ejmech.2007.09.017>
  • Rivas Bernabé L., Maureira Antonio: Poly(2-acrylamido glycolic acid-co-acryloyl morpholine) and poly(2-acrylamido glycolic acid-co-acrylamide): Synthesis, characterization, and retention properties for environmentally impacting metal ions. Euro Poly J 2008, 44, 523. <http://dx.doi.org/10.1016/j.eurpolymj.2007.11.024>
  • Rivas Bernabé L., Maureira Antonio E., Mondaca María A.: Aminodiacetic water-soluble polymer–metal ion interactions. Euro Poly J 2008, 44, 2330. <http://dx.doi.org/10.1016/j.eurpolymj.2008.05.001>
  • Senthil Kumar R., Sasikala K., Arunachalam S.: DNA interaction of some polymer–copper(II) complexes containing 2,2′-bipyridyl ligand and their antimicrobial activities. J  Inorg Biochem 2008, 102, 234. <http://dx.doi.org/10.1016/j.jinorgbio.2007.08.005>
  • Kumar R. Senthil, Arunachalam S., Periasamy V.S., Preethy C.P., Riyasdeen A., Akbarsha M.A.: Synthesis, DNA binding and antitumor activities of some novel polymer–cobalt(III) complexes containing 1,10-phenanthroline ligand. J Polyhedron 2008, 27, 1111. <http://dx.doi.org/10.1016/j.poly.2007.12.008>
  • Schulte-Bockholt Michael, Schuster Michael: Removal enrichment and recovery of Ni(II), Zn(II) and phosphate from phosphation rinsing waters with liquid-phase polymer-based retention technique. Separation Purification Technology 2008, 63, 172. <http://dx.doi.org/10.1016/j.seppur.2008.04.011>
  • Choi S. J., Geckeler K. E.: Synthesis and properties of hydrophilic polymers, part 11: Synthesis, biodegradability, and metal complexation of copolymers of ethylenediaminetetraacetic acid dianhydride and lactose. J Appl Polym Sci 2007, 103, 2932. <http://dx.doi.org/10.1002/app.25515>
  • Aguirre María del Carmen, Rivas Bernabé L.: Arsenite retention properties of water-soluble metal–polymers. J Appl Polym Sci 2007, 106, 1889. <http://dx.doi.org/10.1002/app.26737>
  • Gökçeören A., Erbil C., Sezer E.: Voltammetric investigation of polyelectrolyte-Cu(II) complexes. J Appl Electrochem 2007, 37, 941. <http://dx.doi.org/10.1007/s10800-007-9334-0>
  • Cañizares P., Pérez Á., Camarillo R., Llanos J., López M.L.: Selective separation of Pb from hard water by a semi-continuous polymer-enhanced ultrafiltration process (PEUF). Desalinisation 2007, 206, 602. <http://dx.doi.org/10.1016/j.desal.2006.04.066>
  • Soykan Cengiz, Coskun Ramazan, Kirbag Sevda: Poly(crotonic acid-co-2-acrylamido-2-methyl-1-propanesulfonic acid)–metal complexes with copper(II), cobalt(II), and nickel(II): Synthesis, characterization and antimicrobial activity. Euro Poly J 2007, 43, 4028. <http://dx.doi.org/10.1016/j.eurpolymj.2007.06.033>
  • Rivas Bernabé L., Maureira Antonio: Poly(2-acrylamido glycolic acid): A water-soluble polymer with ability to interact with metal ions in homogenous phase. J Inorg Chem Commun 2007, 10, 151. <http://dx.doi.org/10.1016/j.inoche.2006.10.005>
  • Senthil Kumar R., Arunachalam S.: DNA binding and antimicrobial studies of some polyethyleneimine-copper(II) complex samples containing 1,10-phenanthroline and l-theronine as co-ligands. J Polyhedron 2007, 26, 3255. <http://dx.doi.org/10.1016/j.poly.2007.03.001>
  • Rivas Bernabé L., del Carmen Aguirre Marı´a: Nitrite removal from water using water-soluble polymers in conjunction with liquid-phase polymer-based retention technique. React & Funct Polym 2007, 67, 1487. <http://dx.doi.org/10.1016/j.reactfunctpolym.2007.07.041>
  • Kavlak Serap, Kaplan Can Hatice, Rzaev Zakir M. O., Güner Ali: Thermal properties of poly(maleic anhydride-alt-acrylic acid) in the presence of certain metal chlorides. J Appl Polym Sci 2006, 100, 3926. <http://dx.doi.org/10.1002/app.22780>
  • Rivas Bernabé L., Maureira Antonio, Geckeler Kurt E.: Novel water-soluble acryloylmorpholine copolymers: Synthesis, characterization, and metal ion binding properties. J Appl Polym Sci 2006, 101, 180. <http://dx.doi.org/10.1002/app.23163>
  • Rivas Bernabé L., Pooley S. Amalia, Pereira Eduardo, Montoya Erika, Cid Rocío: Poly(ethylene-alt-maleic acid) as complexing reagent to separate metal ions using membrane filtration. J Appl Polym Sci 2006, 101, 2057. <http://dx.doi.org/10.1002/app.23794>
  • Rivas Bernabé L., Aguirre María del Carmen, Pereira Eduardo: Retention properties of arsenate anions of water-soluble polymers by a liquid-phase polymer-based retention technique. J Appl Polym Sci 2006, 102, 2677. <http://dx.doi.org/10.1002/app.24093>
  • Rivas Bernabé L., Pereira Eduardo D., Robles Pamela, Cid Rocío: Metal Ion Removal from Aqueous Solution by Liquid Phase Polymer-Based Retention Technique. Macromol Symp 2006, 235, 152. <http://dx.doi.org/10.1002/masy.200650319>
  • Rivas Bernabé L., Pooley S. Amalia, Pereira Eduardo D., Maureira Antonio: Water-Soluble Polyelectrolytes with Metal Ion Removal Ability by Using the Liquid Phase Based Retention Technique. Macromol Symp 2006, 245-246, 116. <http://dx.doi.org/10.1002/masy.200651315>
  • Rivas Bernabé L., Pooley S. Amalia, Pereira Eduardo, Montoya Erika, Cid Rocío, Geckeler Kurt E.: Water-soluble polymer materials as complexing reagents for the separation of metal ions using membrane filtration. Polym Adv Technol 2006, 17, 865. <http://dx.doi.org/10.1002/pat.791>
  • Premkumar T., Geckeler K. E.: Nanosized CuO Particles via a Supramolecular Strategy. Small 2006, 2, 616. <http://dx.doi.org/10.1002/smll.200500454>
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  • Arthanareeswaran G., Latha C. S., Mohan D., Raajenthiren M., Srinivasan K.: Studies on Cellulose Acetate/Low Cyclic Dimmer Polysulfone Blend Ultrafiltration Membranes and their Applications. SEPARAT SCI 2006, 41, 2895. <http://dx.doi.org/10.1080/01496390600786192>
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  • Rivas Bernabé L., Pereira Eduardo, Cid Rocío, Geckeler Kurt E.: Polyelectrolyte-assisted removal of metal ions with ultrafiltration. J Appl Polym Sci 2005, 95, 1091. <http://dx.doi.org/10.1002/app.21424>
  • Rivas Bernabé L., Pooley S. Amalia, Pereira Eduardo D., Cid Rocío, Luna Maribel, Jara M. Antonieta, Geckeler Kurt E.: Water-soluble amine and imine polymers with the ability to bind metal ions in conjunction with membrane filtration. J Appl Polym Sci 2005, 96, 222. <http://dx.doi.org/10.1002/app.21425>
  • Sajitha C. J., Mohan D.: Studies on cellulose acetate-carboxylated polysulfone blend ultrafiltration membranes. III. J Appl Polym Sci 2005, 97, 976. <http://dx.doi.org/10.1002/app.21799>
  • Moreno-Villoslada Ignacio, Oyarzún Felipe, Miranda Víctor, Hess Susan, Rivas Bernabé L.: Binding of chlorpheniramine maleate to pharmacologically important alginic acid, carboxymethylcellulose, κ-carageenan, and ι-carrageenan as studied by diafiltration. J Appl Polym Sci 2005, 98, 598. <http://dx.doi.org/10.1002/app.22056>
  • Moreno-Villoslada Ignacio, González Felipe, Jofré Marlen, Chandía Patricio, Hess Susan, Rivas Bernabé L.: Complexation Behavior of Cu2+ in the Presence of Iminodiacetic Acid and Poly(ethyleneimine). Macromol Chem Phys 2005, 206, 1541. <http://dx.doi.org/10.1002/macp.200500127>
  • Bell R.R., Saunders G.C.: Cadmium adsorption on hydrous aluminium (III) oxide: effect of adsorbed polyelectrolyte. Appl Geoch 2005, 20, 529. <http://dx.doi.org/10.1016/j.apgeochem.2004.10.004>
  • Şolpan Dilek, Torun Murat: Investigation of complex formation between (sodium alginate/acrylamide) semi-interpenetrating polymer networks and lead, cadmium, nickel ions. Colloid Surf A Phys Eng Aspects 2005, 268, 12. <http://dx.doi.org/10.1016/j.colsurfa.2005.04.035>
  • Cañizares Pablo, Lucas Antonio de, Pérez Ángel, Camarillo Rafael: Effect of polymer nature and hydrodynamic conditions on a process of polymer enhanced ultrafiltration. J Membr Sci 2005, 253, 149. <http://dx.doi.org/10.1016/j.memsci.2004.12.042>
  • Moreno-Villoslada Ignacio, Oyarzún Felipe, Miranda Víctor, Hess Susan, Rivas Bernabé L.: Comparison between the binding of chlorpheniramine maleate to poly(sodium 4-styrenesulfonate) and the binding to other polyelectrolytes. Polymer 2005, 46, 7240. <http://dx.doi.org/10.1016/j.polymer.2005.06.033>
  • Rivas Bernabé L., Pereira Eduardo, Gallegos Paola, Homper Daniela, Geckeler Kurt E.: Metal ion binding capability of the water-soluble poly(vinyl phosphonic acid) for mono-, di-, and trivalent cations. J Appl Polym Sci 2004, 92, 2917. <http://dx.doi.org/10.1002/app.20246>
  • Rivas Bernabé L., Pooley S. Amalia, Maureira Antonio: Removal of metal ions by water-soluble polymacromonomers in conjunction with ultrafiltration membrane. J Appl Polym Sci 2004, 92, 2955. <http://dx.doi.org/10.1002/app.20267>
  • Kavlak Serap, Kaplan Can Hatice, Güner Ali: Interaction of poly(maleic anhydride-alt-acrylic acid) with transition metal cations, Ni2+, Cu2+, and Cd2+: A study by UV-Vis spectroscopy and viscosimetry. J Appl Polym Sci 2004, 92, 2698. <http://dx.doi.org/10.1002/app.20271>
  • Rivas Bernabé L., Pereira Eduardo D., Horta Arturo, Renamayor Carmen S.: Macromolecular size of polyelectrolytes containing ammonium and sulfonic acid groups, as determined by light scattering. Euro Poly J 2004, 40, 203. <http://dx.doi.org/10.1016/j.eurpolymj.2003.04.001>
  • Azhgozhinova Galiya S, Güven Olgun, Pekel Nursel, Dubolazov Artem V, Mun Grigoriy A, Nurkeeva Zauresh S: Complex formation of linear poly(methacrylic acid) with uranyl ions in aqueous solutions. Journal of Colloid and Interface Science 2004, 278, 155. <http://dx.doi.org/10.1016/j.jcis.2004.05.010>
  • Barron-Zambrano J, Laborie S, Viers Ph, Rakib M, Durand G: Mercury removal and recovery from aqueous solutions by coupled complexation–ultrafiltration and electrolysis. J Membr Sci 2004, 229, 179. <http://dx.doi.org/10.1016/j.memsci.2003.10.028>
  • Sauer Nancy N., Ehler Deborah S., Duran Brandy L.: Lead Extraction from Contaminated Soil Using Water-Soluble Polymers. J. Environ. Eng. 2004, 130, 585. <http://dx.doi.org/10.1061/(ASCE)0733-9372(2004)130:5(585)>
  • Rivas Bernabé L., Pereira Eduardo D., Gallegos Paola, Geckeler Kurt E.: Water-soluble acidic polyelectrolytes with metal-removing ability. Polym Adv Technol 2002, 13, 1000. <http://dx.doi.org/10.1002/pat.247>
  • Barron-Zambrano J., Laborie S., Viers Ph., Rakib M., Durand G.: Mercury removal from aqueous solutions by complexation—ultrafiltration. Desalinisation 2002, 144, 201. <http://dx.doi.org/10.1016/S0011-9164(02)00312-0>
  • Cañizares Pablo, Pérez Ángel, Camarillo Rafael: Recovery of heavy metals by means of ultrafiltration with water-soluble polymers: calculation of design parameters. Desalinisation 2002, 144, 279. <http://dx.doi.org/10.1016/S0011-9164(02)00328-4>
  • Mladenova Rosica, Ignatova Milena, Manolova Nevena, Petrova Tsvetanka, Rashkov Iliya: Preparation, characterization and biological activity of Schiff base compounds derived from 8-hydroxyquinoline-2-carboxaldehyde and Jeffamines ED®. Euro Poly J 2002, 38, 989. <http://dx.doi.org/10.1016/S0014-3057(01)00260-9>
  • Moreno-Villoslada Ignacio, Rivas Bernabé L: Metal ion enrichment of a water-soluble chelating polymer studied by ultrafiltration. J Membr Sci 2002, 208, 69. <http://dx.doi.org/10.1016/S0376-7388(02)00176-X>
  • Ghosh A. K., Ramachandhran V., Singh Shiv Pal, Hanra M. S., Trivedi M. K., Misra B. M.: PREPARATION AND CHARACTERIZATION OF POLYSULFONE AND POLYETHERSULFONE MEMBRANES FOR CALCIUM (Ca2+) AND MAGNESIUM (Mg2+) SEPARATION BY COMPLEXATION ULTRAFILTRATION. Journal of Macromolecular Science, Part A 2002, 39, 557. <http://dx.doi.org/10.1081/MA-120004247>
  • Rivas Bernabé L, Martínez Esteban, Pereira Eduardo, Geckeler Kurt E: Synthesis, characterization and polychelatogenic properties of poly[(2-acrylamido-2-methyl-1-propane sulfonic acid)-co-(methacrylic acid)]. Polym Int 2001, 50, 456. <http://dx.doi.org/10.1002/pi.657>
  • Rivas Bernabé L, Moreno-Villoslada Ignacio: Polyelectrolyte behavior of three copolymers of 2-acrylamido-2-methyl-propanesulfonic acid and N-acryloyl-N′-methylpiperazine studied by ultrafiltration. J Membr Sci 2001, 187, 271. <http://dx.doi.org/10.1016/S0376-7388(01)00354-4>
  • Gohdes Joel W., Duran Brandy L., Clark Noline C., Robison Thomas W., Smith Barbara F., Sauer Nancy N.: PREPARATION OF WATER-SOLUBLE POLYMERS MODIFIED WITH SULFUR DONORS FOR RECOVERY OF HEAVY METALS. SEPARAT SCI 2001, 36, 2647. <http://dx.doi.org/10.1081/SS-100107217>
  • Choi S J, Geckeler K E: Part 8. Preparation, characterization and metal complexing of poly[(2-hydroxyethyl)-DL-aspartamide] in aqueous solution. Polym Int 2000, 49, 1519. <http://dx.doi.org/10.1002/1097-0126(200011)49:11<1519::AID-PI562>3.0.CO;2-K>
  • Menoud P., Cavin L., Renken A.: New Regeneration Process of Heavy-Metal-Loaded Chelating Resins. Chem Eng Technol 2000, 23, 441. <http://dx.doi.org/10.1002/(SICI)1521-4125(200005)23:5<441::AID-CEAT441>3.0.CO;2-G>
  • Osipova E.A., Sladkov V.E., Kamenev A.I., Shkinev V.M., Geckeler K.E.: Determination of Ag(I), Hg(II), Cu(II), Pb(II), Cd(II) by stripping voltammetry in aqueous solutions using complexing polymers in conjunction with membrane filtration. Analytica Chimica Acta 2000, 404, 231. <http://dx.doi.org/10.1016/S0003-2670(99)00713-8>
  • Bhattacharya A: Radiation and industrial polymers. Prog Polym Sci 2000, 25, 371. <http://dx.doi.org/10.1016/S0079-6700(00)00009-5>
  • Marty J., Persin M., Sarrazin J.: Dialysis of NI(II) through an ultrafiltration membrane enhanced by polymer complexation. J Membr Sci 2000, 167, 291. <http://dx.doi.org/10.1016/S0376-7388(99)00290-2>
  • Baticle P., Kiefer C., Lakhchaf N., Leclerc O., Persin M., Sarrazin J.: Treatment of nickel containing industrial effluents with a hybrid process comprising of polymer complexation–ultrafiltration–electrolysis. Separation Purification Technology 2000, 18, 195. <http://dx.doi.org/10.1016/S1383-5866(99)00063-5>
  • Effect of the Polymer Concentration on the Interactions of Water-Soluble Polymers with Metal Ions. Chem Lett 2000, 166. <http://dx.doi.org/10.1246/cl.2000.166>
  • Rivas B. L., Pooley S. A., Soto M., Geckeler K. E.: Water-soluble copolymers of 1-vinyl-2-pyrrolidone and acrylamide derivatives: synthesis, characterization, and metal binding capability studied by liquid-phase polymer-based retention technique. J Appl Polym Sci 1999, 72, 741. <http://dx.doi.org/10.1002/(SICI)1097-4628(19990509)72:6<741::AID-APP2>3.0.CO;2-#>
  • Montembault Véronique, Soutif Jean-Claude, Brosse Jean-Claude, Grote Manfred: Synthesis and complexing properties of resins containing aminocarboxylic acid as functional groups from diethylenetriaminepentaacetic acid bisanhydride and polyvinyl alcohols. React & Funct Polym 1999, 39, 253. <http://dx.doi.org/10.1016/S1381-5148(98)00006-6>
  • ARAÚJO Alberto N., COSTA Rui Cerdeira C., LIMA José L. F. C.: Application of Sequential Injection Analysis to the Assay of Lead Retention Characteristics by Poly(vinylpyrrolidone). Trace Analysis of Lead in Waters. Anal Sci 1999, 15, 991. <http://dx.doi.org/10.2116/analsci.15.991>
  • Müslehiddinoğlu Jale, Uludağ Yusuf, Özbelge Hilmi Önder, Yilmaz Levent: Effect of operating parameters on selective separation of heavy metals from binary mixtures via polymer enhanced ultrafiltration. J  Membr Sci 1998, 140, 251. <http://dx.doi.org/10.1016/S0376-7388(97)00280-9>
  • Rivas Bernabé L., Moreno-Villoslada Ignacio: Analysis of the retention profiles of poly (acrylic acid) with Co(II) and Ni(II). Polym Bull 1997, 39, 653. <http://dx.doi.org/10.1007/s002890050199>
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