Preparation, characterization and ion adsorption properties of functionalized polystyrene modified with 1,4-phenylene diisocyanate and diethylenetriamine
-
Mokhtar Dardouri
,
Abir ben Hadj Amor
Abstract
In the present work, linear polystyrene (PS) was functionalized by a sulfonation reaction providing sulfonated polystyrene (PSS). Then, the PSS polymer chains were cross-linked with the 1,4- phenylene diisocyanate (PPDI) group in tetrahydrofuran (THF), which led to a PSS-PPDI polymer. The PSS-PPDI was grafted by diethylenetriamine (DETA) in a solution of THF to obtain polymer PSS-PPDI-DETA. Their structures were characterized by infrared spectroscopy (ATR-FTIR), elemental analysis (EA), differential scanning calorimetry (DSC), thermogravemetric (TGA), thermodynamic (DTA) and differential thermogravimetric (DTG) analysis. Subsequently, the obtained polymers were tested for their ability to remove some metal ions from aqueous media such as Zn2+, Cd2+ and Co2+.
References
Bekri-Abess, I., Bayoudh, S., & Baklouti, M. (2008). The removal of hardness of water using sulfonated waste plastic. Desalination, 222, 81-86. DOI: 10.1016/j.desal.2007.01.121.10.1016/j.desal.2007.01.121Search in Google Scholar
Chandran, A., Varghese, H. T., Panicker, C. Y., Van Alsenoy, C., & Rajendran, G. (2011). FT-IR and computational study of (E)-N-carbamimidoyl-4-((2-formylbenzylidene)amino)benzene sulfonamide. Journal of Molecular Structure, 1001, 29-35. DOI: 10.1016/j.molstruc.2011.06.010.10.1016/j.molstruc.2011.06.010Search in Google Scholar
Chandran, A., Mary, S., Varghese, H. T., Panicker, C. Y., Manojkumar, T. K., Alsenoy, C. V., & Rajendran, G. (2012). Vibrational spectroscopic study of (E)-4-(benzylideneamino)- N-carbamimidoyl benzenesulfonamide. ISRN Analytical Chemistry, 2012, 1-11. DOI: 10.5402/2012/397026.10.5402/2012/397026Search in Google Scholar
Chohan, Z. H., Youssoufi, M. H., Jarrahpour, A., & Hadda, T. B. (2010). Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: Indolenyl sulfonamide derivatives. European Journal of Medicinal Chemistry, 45, 1189-1199. DOI: 10.1016/j.ejmech.2009.11.029.10.1016/j.ejmech.2009.11.029Search in Google Scholar
Hangan, A., Bodoki, A., Oprean, L., Alzuet, G., Liu-González, M., & Borrás, J. (2010). Synthesis, crystallographic and spectroscopic characterization and magnetic properties of dimer and monomer ternary copper(II) complexes with sulfonamide derivatives and 1,10-phenanthroline. Nuclease activity by the oxidative mechanism. Polyhedron, 29, 1305-1313. DOI: 10.1016/j.poly.2009.12.030.10.1016/j.poly.2009.12.030Search in Google Scholar
Hawkins, C. A., Sheppard, A. C., & Wood, T. G. (1997). Recent advances in aqueous two-component systems for heavy-duty metal protection. Progress in Organic Coatings, 32, 253-261. DOI: 10.1016/s0300-9440(97)00036-2.10.1016/S0300-9440(97)00036-2Search in Google Scholar
Kučera, F., & Jančař, J. (1996). Preliminary study of sulfonation of polystyrene by homogeneous and heterogeneous reaction. Chemical Papers, 50, 224-227.Search in Google Scholar
Kučera, F., & Jančař, J. (1998). Homogeneous and heterogeneous sulfonation of polymers: A review. Polymer Engineering & Science, 38, 783-792. DOI: 10.1002/pen.10244.10.1002/pen.10244Search in Google Scholar
Martins, C. R., Ruggeri, G., & De Paoli, M. A. (2003). Synthesis in pilot plant scale and physical properties of sulfonated polystyrene. Journal of the Brazilian Chemical Society, 14, 797-802. DOI: 10.1590/s0103-50532003000500015.10.1590/S0103-50532003000500015Search in Google Scholar
Matlock, M. M., Howerton, B. S., Henke, K. R., & Atwood, D. A. (2001). A pyridine-thiol ligand with multiple bonding sites for heavy metal precipitation. Journal of Hazardous Materials, 82, 55-63. DOI: 10.1016/s0304-3894(00)00353-8.10.1016/S0304-3894(00)00353-8Search in Google Scholar
Melchiors, M., Sonntag, M., Kobusch, C., & Jürgens, E. (2000). Recent developments in aqueous two-component polyurethane (2K-PUR) coatings. Progress in Organic Coatings, 40, 99-109. DOI: 10.1016/s0300-9440(00)00123-5.10.1016/S0300-9440(00)00123-5Search in Google Scholar
Nabuurs, T., Pears, D., & Overbeek, A. (1999). Defect free coatings from two-pack isocyanate curable acrylic dispersions. Progress in Organic Coatings, 35, 129-140. DOI: 10.1016/s0300-9440(99)00015-6.10.1016/S0300-9440(99)00015-6Search in Google Scholar
Ozer, O., Ince, A., Karagoz, B., & Bicak, N. (2013). Crosslinked PS-DVB microspheres with sulfonated polystyrene brushes as new generation of ion exchange resins. Desalination, 309, 141-147. DOI: 10.1016/j.desal.2012.09.024.10.1016/j.desal.2012.09.024Search in Google Scholar
Pan, H. Y., Zhang, Y. Y., Pu, H. T., & Chang, Z. H. (2014). Organic-inorganic hybrid proton exchange membrane based on polyhedral oligomeric silsesquioxanes and sulfonated polyimides containing benzimidazole. Journal of Power Sources, 263, 195-202. DOI: 10.1016/j.jpowsour.2014.04.055.10.1016/j.jpowsour.2014.04.055Search in Google Scholar
Prabhakaran, D., & Subramanian, M. S. (2003). Selective extraction and sequential separation of actinide and transition ions using AXAD-16-BTBED polymeric sorbent. Reactive and Functional Polymers, 57, 147-155. DOI: 10.1016/j. reactfunctpolym.2003.09.003.Search in Google Scholar
Reis Brandão, L., da Silva Meireles, C., de Assunção, R. M. N., & Rodrigues Filho, G. (2005). Diffusion of water through poly(styrenesulfonate) membranes produced from the sulfonation of wasted PS plastic cups. Polymer Bulletin, 55, 269-275. DOI: 10.1007/s00289-005-0430-1.10.1007/s00289-005-0430-1Search in Google Scholar
Roges, N. P. G. (1994). A guide to the complete interpretation of the infrared spectra of organic structures. New York, NY, USA: Wiley.Search in Google Scholar
Sasaki, K., & Crich, D. (2011). Facile amide bond formation from carboxylic acids and isocyanates. Organic Letters, 13, 2256-2259. DOI: 10.1021/ol200531k.10.1021/ol200531kSearch in Google Scholar
Senkal, B. F., & Senkal, E. (2007). Sulfonamide based polymeric sorbents for selective mercury extraction. Reactive and Functional Polymers, 67, 1465-1470. DOI: 10.1016/j. reactfunctpolym.2007.07.017.Search in Google Scholar
Senkal, B. F., & Yavuz, E. (2006). Ureasulfonamide polymeric sorbent for selective mercury extraction. Monatshefte f¨ur Chemie, 137, 929-934. DOI: 10.1007/s00706-006-0494-0.10.1007/s00706-006-0494-0Search in Google Scholar
Shah, R., & Devi, S. (1996). Preconcentration of mercury(II) on dithizone anchored poly(vinyl pyridine) support. Reactive and Functional Polymers, 31, 1-9. DOI: 10.1016/1381-5148(96)00029-6.10.1016/1381-5148(96)00029-6Search in Google Scholar
Song-Ping, H., Franz, K. J., Arnold, E. H., Devenyi, J., & Fish, R. H. (1996). Polymer pendant ligand chemistry-5. The selective and competitive removal of Ag+, Hg2+, Cu2+, Pb2+ and Cd2+ ions from aqueous solution utilizing a N-sulfonylethylenebis(dithiocarbamate) ligand anchored on macroporous polystyrene-divinylbenzene beads. Polyhedron, 15, 4241-4254. DOI: 10.1016/0277-5387(96)00171-4.10.1016/0277-5387(96)00171-4Search in Google Scholar
Sonmez, H. B., Senkal, B. F., & Bicak, N. (2003). Polymersupported iminodiacetamides for selective mercury extraction. Journal of Applied Polymer Science, 87, 1316-1321. DOI: 10.1002/app.11547.10.1002/app.11547Search in Google Scholar
Sugama, T. Kukacka, L. E., & Carciello, N. (1988). Failure mode of polyurethanes/aluminum oxide joint primed with hydrophilic macromolecules. International Journal of Adhesion and Adhesives, 8, 101-106. DOI: 10.1016/0143-7496(88)90030-9.10.1016/0143-7496(88)90030-9Search in Google Scholar
Tiravanti, G., Petruzzelli, D., & Passino, R. (1996). Low and non waste technologies for metals recovery by reactive polymers. Waste Management, 16, 597-605. DOI: 10.1016/s0956-053x(96)00109-2.10.1016/S0956-053X(96)00109-2Search in Google Scholar
Yavuz, E., Barim, G., & Senkal, B. F. (2009). Thiol containing sulfonamide based polymeric sorbent for mercury extraction. Journal of Applied Polymer Science, 114, 1879-1883. DOI: 10.1002/app.30808.10.1002/app.30808Search in Google Scholar
Zuo, G. J., & Muhammed, M. (1995). Selective binding of mercury to thiourea-based coordinating resins. Reactive and Functional Polymers, 27, 187-198. DOI: 10.1016/1381-5148(95)00067-p. 10.1016/1381-5148(95)00067-PSearch in Google Scholar
Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Catalysis in glycerol: a survey of recent advances
- A rapid LC-MS/MS method for determination of urinary EtG and application to a cut-off limit study
- Validated chiral chromatographic methods for clopidogrel bisulphate and its related substances in bulk drug and pharmaceutical dosage forms
- Effect of SO2 on SCR activity of MnOx/PG catalysts at low temperature
- Preparation of Pd/Al2O3@silicalite-1 core–shell beads and their application to hydrogenation reactions
- Effect of rapid batch decompression on hydrolysate quality after hydrothermal pretreatment of wheat straw
- Anthocyanins profile, total phenolics and antioxidant activity of two Romanian red grape varieties: Feteascǎ neagrǎ and Bǎbeascǎ neagrǎ (Vitis vinifera)
- Polyphenols, radical scavenger activity, short-chain organic acids and heavy metals of several plants extracts from “Bucharest Delta”
- Reaction of anhydrous zinc chloride with 2,3-thiophenedicarbaldehyde bis(semicarbazone) (2,3BSTCH2) and bis(thiosemicarbazone) (2,3BTSTCH2): Crystal structure of {[C6H5N2S]+[ZnCl3(C6H4N2S)]−} complex
- Synthesis and evaluation of a novel hydrophobically associating polymer based on acrylamide for enhanced oil recovery
- Synthesis of cardanol-based photo-active SET-LRP initiator and its application to preparation of UV-cured resin
- Preparation, characterization and ion adsorption properties of functionalized polystyrene modified with 1,4-phenylene diisocyanate and diethylenetriamine
- Synthesis of lanthanide-based SBA-15 mesoporous hybrids by a novel route
- Comparative ESI FT-MS and MALDI-TOF structural analyses of representative human N-linked glycans
Articles in the same Issue
- Catalysis in glycerol: a survey of recent advances
- A rapid LC-MS/MS method for determination of urinary EtG and application to a cut-off limit study
- Validated chiral chromatographic methods for clopidogrel bisulphate and its related substances in bulk drug and pharmaceutical dosage forms
- Effect of SO2 on SCR activity of MnOx/PG catalysts at low temperature
- Preparation of Pd/Al2O3@silicalite-1 core–shell beads and their application to hydrogenation reactions
- Effect of rapid batch decompression on hydrolysate quality after hydrothermal pretreatment of wheat straw
- Anthocyanins profile, total phenolics and antioxidant activity of two Romanian red grape varieties: Feteascǎ neagrǎ and Bǎbeascǎ neagrǎ (Vitis vinifera)
- Polyphenols, radical scavenger activity, short-chain organic acids and heavy metals of several plants extracts from “Bucharest Delta”
- Reaction of anhydrous zinc chloride with 2,3-thiophenedicarbaldehyde bis(semicarbazone) (2,3BSTCH2) and bis(thiosemicarbazone) (2,3BTSTCH2): Crystal structure of {[C6H5N2S]+[ZnCl3(C6H4N2S)]−} complex
- Synthesis and evaluation of a novel hydrophobically associating polymer based on acrylamide for enhanced oil recovery
- Synthesis of cardanol-based photo-active SET-LRP initiator and its application to preparation of UV-cured resin
- Preparation, characterization and ion adsorption properties of functionalized polystyrene modified with 1,4-phenylene diisocyanate and diethylenetriamine
- Synthesis of lanthanide-based SBA-15 mesoporous hybrids by a novel route
- Comparative ESI FT-MS and MALDI-TOF structural analyses of representative human N-linked glycans
