Solubility and Phase Transfer of Insoluble Dyes in Organic Solvent by Polyurethane Reverse Micelle

Document Type : Research Paper

Authors

1 Department of Chemistry, Faculty of Science, University of Mohaghegh Ardabili, Ardabil, Iran

2 Department of Chemistry, Faculty of Science, University of Mohaghegh Ardabili, Postal Code 11367-56199, Ardabil, Iran

3 Department of Polymer, Faculty of Chemistry, Shahid Beheshti University, Postal Code 1983969411, Tehran, Iran

Abstract

Hypothesis: Amphiphilic systems present efficient ability in solublizing insoluble compounds by self-association to micellar structures. Polyurethanes with amphiphilic feature as polymeric assembling species illustrate specific characteristics such as H-bond assisting stability of arranged structures and functionalizing possibilty. In this respect, an amphiphilic random polyurethane (APU) synthesized from olive oil-based fatty acid was characterized for micellization in non-polar organic invironment along with its loading and transfering capability for insoluble dyes.
Methods: The solution of APU in non-polar organic solvent, toluene, at different concentrations was evaluated by turbidimetry and viscometry methods to realize the possibility of micelle formation and determine the aggregation point (RCMC). Morphology of the nanoparticles was investigated by field emision scanning electron microscopy (FE-SEM), atomic force microscopy (AFM) and dynamic light scattering (DLS). Capability of these polymeric micells as nano-carrier in encapsulating and solublizing of fushine hydrophilic dye in toluene as well as in phase transfering some hydrophilic cationic dyes from aqueous phase to toluene was investigated. Quantitative transferring capacity was spectroscopically evaluated by recording UV-Vis spectra of the dyes.
Findings: APU showed successful self-association into revers micelle at low critical concentration (0.02 mg/mL), expreesing efficent intermolecular interaction between hydrophilic segments of the polymer. Solvating capability of APU in the non-polar organic medium for hydrophilic dyes and phase transfer of this type of dyes from aqueous phase to organic phase illustrate the formation of assembled structures of APU with core-shell nature in the organic solvent and the embedding ability of APU. On the other hand, the reverse micelles formed in the organic phase were able to transfer cationic dyes from aqueous solution to organic medium. Based on the obtained results, APU can be utilized in removing cationic dyes from contaminated water and drug delivering process..

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References

  1. Weng Z., Zheng Y., Tang A., and Gao C., Synthesis, Dye Encapsulation, and Highly Efficient Colouring Application of Amphiphilic Hyperbranched Polymers, J. Chem., 67, 103-111, 2014.
  2. Ghosh S.K., Kawaguchi S., Jinbo Y., Izumi Y., Yamaguchi K., Taniguchi T., Nagai K., and Koyama K., Nanoscale Solution Structure and Transfer Capacity of Amphiphilic Poly(amidoamine) Dendrimers Having Water and Polar Guest Molecules Inside, Macromolecules, 36, 9162-9169, 2003.
  3. Gao H., Jones M.C., Chen J., Prud’homme R.E., and Leroux J.C., Core Cross-linked Reverse Micelles from Star-Shaped Polymers, Mater., 20, 3063-3067, 2008.
  4. Cestari A.R., Vieira E.F., Vieira G.S., and Almeida L.E., The Removal of Anionic Dyes from Aqueous Solutions in the Presence of Anionic Surfactant Using Aminopropylsilica-A Kinetic Study, Hazard. Mater., 138, 133-141, 2006.
  5. Hu J., Xu Y., and Zhang Y., Amphiphilic Random Polycarbonate Self-assemble into GSH/pH Dual Responsive Micelle-Like Aggregates in Water, Chinese Chem. Lett., 30, 2039-2042, 2019.
  6. Nguyen T.B.T., Li S., and Deratani A., Reverse Micelles Prepared from Amphiphilic Polylactide-b-Poly(ethylene glycol) Block Copolymers for Controlled Release of Hydrophilic Drugs, J. Pharm., 495, 154-161, 2015.
  7. Li L., Raghupathi K., Song C., Prasad P., and Thayumanavan S., Self-assembly of Random Copolymers, ChemComm., 50, 13417-13432, 2014.
  8. He , Design, Synthesis and Study of Functional Amphiphilic Polymers and Their Applications, PhD Thesis, Department of Chemistry, University of Massachusetts, Amherst, USA, 2019.
  9. Vrignaud S., Anton N., Gayet P., Benoit J.-P., and Saulnier P., Reverse Micelle-Loaded Lipid Nanocarriers: A Novel Drug Delivery System for the Sustained Release of Doxorubicin Hydrochloride, Eur. J. Pharm. Biopharm., 79, 197-204, 2011.
  10. Orellano M.S., Longo G.S., Porporatto C., Correa N.M., and Falcone R.D., Role of Micellar Interface in the Synthesis of Chitosan Nanoparticles Formulated by Reverse Micellar Method, Colloids Surf. A: Physicochem. Eng. Asp., 599, 124876-124888, 2020.
  11. Sun X. and Bandara N., Applications of Reverse Micelles Technique in Food Science: A Comprehensive Review, Food. Sci. Technol., 91, 106-115, 2019.
  12. Caracciolo P., Sanz Pita C., and Abel Abraham G., Synthesis, Characterization and Applications of Amphiphilic Elastomeric Polyurethane Networks in Drug Delivery, J., 45, 331-338, 2013.
  13. Hevus I., Kohut A., and Voronov A., Micellar Assemblies from Amphiphilic Polyurethanes for Size-Controlled Synthesis of Silver Nanoparticles Dispersible Both in Polar and Nonpolar Media, Nanopart. Res.,14, 2012.
  14. Ma Ch., Bi X., Ngai T., and Zhang G., Polyurethane-Based Nanoparticles as Stabilizers for Oil-in-Water or Water-in-Oil Pickering Emulsions, Mater. Chem. A., 1, 5353-5360, 2013.
  15. Zhang , Zhang D., Bai H., and Ming W., ZnO Nanoparticles Coated with Amphiphilic Polyurethane for Transparent Polyurethane Nanocomposites with Enhanced Mechanical and UV-Shielding Performance, ACS Appl. Nano Mater., 3, 56-67, 2020.
  16. Chen X., Zhang G., Zhang Q., Zhan X., and Chen F., Preparation and Performance of Amphiphilic Polyurethane Copolymers with Capsaicin-Mimic and PEG Moieties for Protein Resistance and Antibacteria, Eng. Chem. Res., 54, 3813-3820, 2015.
  17. Zhou L., Yu L., Ding M., Li J., Tan H., Wang Z., and Fu Q., Synthesis and Characterization of pH-Sensitive Biodegradable Polyurethane for Potential Drug Delivery Applications, Macromolecules, 44, 857-864, 2011.
  18. Liu C., Gao C., and Yan D., Synergistic Supramolecular Encapsulation of Amphiphilic Hyperbranched Polymer to Dyes, Macromolecules, 39, 8102-8111, 2006.
  19. Adeyi A.A., Jamil S.N.A. M., Abdullah C., Choong T.S. Y., Lau K.L., and Abdullah M., Simultaneous Adsorption of Cationic Dyes from Binary Solutions by Thiourea-Modified Poly(acrylonitrile-co-acrylic acid): Detailed Isotherm and Kinetic Studies, Materials, 12, 2903, 2019.
  20. Aghaghafari E., Zamanloo M.R., Omrani I., and Salarvand E., A Novel Olive Oil Fatty Acid-Based Amphiphilic Random Polyurethane: Micellization and Phase Transfer Application, Surface. A., 583, 123951, 2019.
  21. Wu J., Liu C., and Gao Ch., Competitive Supramolecular Encapsulation of Amphiphilic Hyperbranched Polymers Made from A2 and BB’2 Type Monomers. 1. Polyaddition of 1-(2-aminoethyl)piperazine to Divinyl Sulfone., Open Macromol. J., 3, 12-26, 2009.
  22. Jungmann N., Schmidt M., Ebenhoch J., Weis J., and Maskos M., Dye Loading of Amphiphilic Poly(organosiloxane) Nanoparticles., Chemie Int. Ed., 42, 1714-1717, 2003.
  23. Smith G.N., Brown P., Rogers S.E., and Eastoe J., Evidence for a Critical Micelle Concentration of Surfactants in Hydrocarbon Solvents, Langmuir, 29, 3252-3258, 2013.
  24. Chang C., Wang S., Liu I., and Chiu Y., A Simple Method for Determining the Critical Micellar Concentration of a Surfactant, Chin. Chem. Soc., 34, 243-246, 1987.
  25. Froehner S., Sanez J., Dombroski L.F., and Gracioto M.P., Critical Aggregates Concentration of Fatty Esters Present in Biodiesel Determined by Turbidity and Fluorescence, Sci. Pollut. Res, 24, 20747-20758, 2017.
  26. Jones M.C., Gao H., and Leroux J.C., Reverse Polymeric Micelles for Pharmaceutical Applications, Control. Release, 132, 208-215, 2008.
  27. Hevus I., Modgil A., Daniels , Kohut  A., Sun  C., Stafslien S., and Voronov A., Invertible Micellar Polymer Assemblies for Delivery of Poorly Water-Soluble Drugs, Biomacromolecules, 13, 2537-2545, 2012.
  28. Zepon K.M ., Otsuka I., Bouilhac C., Muniz E.C., Sun C., Stafslien S., and Voronov A., Glyco-Nanoparticles Made from Self-Assembly of Maltoheptaose-block-Poly(methyl methacrylate): Micelle, Reverse Micelle, and Encapsulation, Biomacromolecules, 16, 2012-2024, 2015.
  29. Wu C., Li N.J., Chen K.C., and Hsu H.F., Determination of Critical Micelle Concentrations of Ionic and Nonionic Surfactants Based on Relative Viscosity Measurements by Capillary Electrophoresis, Chem. Intermed., 40, 2371-2379, 2014.
  30. Jha K., Bhattarai A., and Chatterjee S.K., Determination of Critical Micelle Concentration of Cetyltrimethylammonium Bromide in Presence and Absence of KCl and NaCl in Aqueous Media at Room Temperature by Viscosity Measurement, Bibechana, 11, 131-135, 2014.
  31. Smith G.L. and McCormick C.L., Water-Soluble Polymers. 78. Viscosity and NRET Fluorescence Studies of pH-Responsive Twin-Tailed Associative Terpolymers Based on Acrylic Acid and Methacrylamide, Macromolecules, 34, 918-924, 2001.
  32. Li Y. and Kwak J.C., pH-Dependent Viscosity Enhancement in Aqueous Systems of Hydrophobically Modified Acrylamide and Acrylic Acid Copolymers, Langmuir, 18, 10049-10051, 2002.
  33. Alexandridis P. and Andersson K., Effect of Solvent Quality on Reverse Micelle Formation and Water Solubilization by Poly(ethylene oxide)/Poly(propylene oxide) and Poly(ethylene oxide)/Poly (butylene oxide) Block Copolymers in Xylene, Colloid Interface Sci., 194, 166-173, 1997.
  34. Santhanalakshmi J. and Maya S., In Solvent Effects on Reverse Micellisation of Tween 80 and Span 80 in Pure and Mixed Organic Solvents, Proceedings of the Indian Academy of Sciences-Chemical Sciences, Indian Acad. Sci. (Chem. Sci.), 109, 27-38.1997.
  35. Jones M.C. and Leroux J.C., Polymeric Micelles–A New Generation of Colloidal Drug Carriers, J. Pharm. Biopharm., 48, 101-111, 1999.
  36. Van Horn W.D., Ogilvie M.E., and Flynn P.F., Reverse Micelle Encapsulation as a Model for Intracellular Crowding, Am. Chem. Soc., 131, 8030-8039, 2009.
  37. Jungmann N., Schmidt M., Ebenhoch J., Weis J., and Maskos M., Dye Loading of Amphiphilic Poly(Organosiloxane) Nanoparticles, Chem. Int. Ed., 42, 1714-1717, 2003.
  38. Li C., Guo S., Lin Z., Wang J., and Ge T., Surface Activity of Branched Alkylamino-Compounds and Their Influence on Phase Transfer Behavior in Water Solutions of Dyes, J. Phys. Chem., 90, 360-367, 2016.
  39. Li C., Weng S., Jin M., and Wan D., Dendritic Macrosurfactant Assembly for Physical Functionalization of HIPE-Templated Polymers, Polymers, 12, 779-790, 2020.
  40. Mahato P., Saha S., Choudhury S., and Das A., Solvent-Dependent Aggregation Behavior of a New Ru (II)-Polypyridyl Based Metallosurfactant, Comm., 47, 11074-11076, 2011.
  41. Savariar E.N., Aathimanikandan S.V., and Thayumanavan S., Supramolecular Assemblies from Amphiphilic Homopolymers: Testing the Scope, Am. Chem. Soc., 128, 16224-16230, 2006.
  42. Nazarzadeh Zare E., Mansour-Lakouraj M., and Alizadeh Feremi J., Rhodamine B Dye Removal from Aqueous Solutions Using Poly(N-vinylpyrrolidone-co-maleic anhydride)/Rice Husk Biocompatible Nanocomposite: Isothermal, Kinetics and Thermodynamic Studies, J. Polym. Sci. Technol. (Persian), 31, 81-92, 2018.
  43. Zhao H., Yu Y., Li Z., Luo B., Wang X., Wang Y., and Xia Y., Linear Polymeric Ionic Liquids as Phase-Transporters for Both Cationic and Anionic Dyes with Synergic Effects., Chem., 6, 7060-7068, 2015.
Iranian Journal of Polymer Science and Technology
Volume 34, Issue 5 - Serial Number 175
January and February 2022
Pages 443-455

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