Abstract
Three novel thiourea-based non-ionic surfactants, 3-decanoyl-1,1-diphenylthiourea, 3-dodecanoyl-1,1-diphenylthiourea and 1,1-diphenyl-3-tetradecanoylthiourea were synthesized from carbonyl chlorides, potassium thiocyanate and amines in high yield. The synthesized compounds were characterized by different techniques like 1H NMR, 13C NMR, FTIR and UV-Visible spectrophotometry. These surfactants are soluble in nonpolar and polar organic solvents and resist solubility in water due to the presence of thiourea group. Electronic absorption spectroscopy was used to evaluate their critical micelle concentration (CMC) in different solvents. The CMC was found to decrease with increase in hydrophobic carbon chain length as expected. Moreover, the effect of pH on their spectral transition was investigated and the two peaks were found to merge in highly alkaline conditions.
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References
Rosen MJ (1978) Surfactant and interfacial phenomena, John Willy and Sons New York
Rosen MJ (2004) Surfactants and interfacial phenomena, 3rd edn. Wiley, New Jersey
Qu G, Cheng J, Wei J, Yu T, Ding W, Luan H (2011) Synthesis, characterization and surface properties of series sulfobetaine surfactants. J Surf Deterg 14:31–35
Xu B, Han F, Shui J, Zhou Y (2009) Synthesis and characterization of lauryl trimethyl ammonium surfactants with new counteranion types. J Surf Deterg 12:351–354
Daoyong Y, Fang H, Hai X (2011) Determination of critical concentrations by synchronous fluorescence spectrometry. The Royal Society of Chemistry (S1–S18)
Jean LS (2002) Surfactants - types and uses, (FIRP Booklet #300A) Mérida-Venezuela Versión # 2
Seifert K, Domka F (2005) Inhibiting effect of surfactants and heavy metal ions on the denitrification process. Pol J Environ Stud 14:87–93
Aldrich C, Feng D (2000) Removal of heavy metals from wastewater effluents by biosorptive flotation. Minerals Eng 13:1129–1134
Holmberg K, Jönsson B, Kronberg B, Lindman B (2007) Surfactants and polymers in aqueous solution, 2nd edn. Wiley, Chichester
Negm NA, Kandile NG, Mohamad MA (2011) Synthesis, characterization and surface activity of new eco-friendly Schiff bases vanillin derived cationic surfactants. J Surf Deterg 14:325–331
Minggui C, **nqi H, Meilong F (2013) Novel synthesis of a new surfactant 4-((4-bromophenyl) (dodecyl)amino)-4-oxobutanoic acid containing a benzene ring using a copper catalyst cross-coupling reaction and its properties. J Surf Deterg 16:581–585
Péter S, László F, Zoltán S, István R, Péter B, Mohamed A, Antal T, Gabriella F (2002) Novel general procedure for the preparation of homogeneous nonionic surfactants. J Surf Deterg 5:353–357
Sujit KG, Pijus KK, Subhash CB (2003) Aggregation of non ionic surfactant igepal in aqueous solution: fluorescence and light scattering studies. Int J Mol Sci 4:562–571
Samik KH, Satya PM (2001) Determination of critical micelle concentration (CMC) of nonionic surfactants by donor–acceptor interaction with iodine and correlation of CMC with hydrophile–lipophile balance and other parameters of the surfactants. J Surf Deterg 4:303–309
Aguiar J, Carpena P, Molina BJA, Ruiz CC (2003) On the determination of the critical micelle concentration by the pyrene 1:3 ratio method. J Colloid Interface Sci 258:116–122
Maria VF, Epaminondas CV, Nikolaos S, Gill ME, George B, Dimitrios PT, Peter JH (2001) Critical micelle concentrations of nonionic surfactants in organic solvents: approximate prediction with UNIFAC. J Colloid Interface Sci 240:277–283
Anna M, Buzenna RR (2010) Prediction of critical micelle concentration of nonionic surfactants by a quantitative structure – property relationship. Comb Chem High Throughput Screen 13:39–44
Achouri ME, Alehyen S, Assioui A, Chami R, Bensajjay F, Prez L, Rosa M (2013) Synthesis and physico-chemical studies of ester-quat surfactants in the series of (dodecanoyloxy)propyl n-alkyl dimethyl ammonium bromide. J Surf Deterg 16:473–485
Chakraborty S, Shukla D, Jain A, Mishra B, Singh S (2009) Assessment of solubilization characteristics of different surfactants for carvedilol phosphate as a function of pH. J Colloid Interface Sci 335:242–249
Scramm LL, Stasiuk EN, Marangoni DG (2003) Surfactants and their applications. Annual Rep Prog Chem Sect 99:3–48
Chlebicki J, Wegrzynska J, Maliszewska I (2005) Preparation, surface-active properties, and antimicrobial activities of bisquaternary ammonium salts from amines and epichlorohydrin. J Surf Deterg 8:227–232
Negm NA, Aiad IA (2007) Synthesis and characterization of multifunctional surfactants in oil-field protection applications. J Surf Deterg 10:87–92
Acknowledgments
The authors gratefully acknowledge the financial support of Quaid-i-Azam University, Higher Education Commission Islamabad, Pakistan, and the Deanship of Scientific Research at King Saud University through the research group project no RGP-VPP-312. We also acknowledge the funding of Higher Education department Khyber Pakhtunkhwa, Pakistan.
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Ullah, I., Shah, A., Badshah, A. et al. Synthesis, Characterization and Investigation of Different Properties of Three Novel Thiourea-Based Non-ionic Surfactants. J Surfact Deterg 17, 1013–1019 (2014). https://doi.org/10.1007/s11743-014-1575-4
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DOI: https://doi.org/10.1007/s11743-014-1575-4