Skip to main content
SpringerLink
Log in

Effect of Sodium Dodecylbenzenesulfonate on the Association Behavior of Promethazine Hydrochloride in Aqueous/Electrolyte Solutions at Different Temperatures

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

The interaction between the amphiphilic phenothiazine drug promethazine hydrochloride (PMT) and an anionic surfactant sodium dodecylbenzenesulfonate has been investigated using the conductometric technique in the absence and presence of an inorganic salt (50 mmol·kg−1 NaCl) at five different compositions and temperatures. PMT is employed for the cure of allergic symptoms. Different physicochemical parameters such as critical micellar concentration (cmc), thermodynamic, and micellar composition are evaluated and discussed in detail using regular solution theory (RST). The addition of salt decreased the surface charge of micelles, lowering the cmc values of the amphiphile. The interaction parameter (β) is negative at all temperatures and compositions indicating attractive interactions. Due to the presence of NaCl in mixed systems the attractive interaction (β) was further increased (β values more negative). The negative values of Gibbs energy (\( \Delta G^{0}_{\text{m}} \)) of mixing revealed the stability of the solution. Owing to the presence of NaCl, the \( \Delta G^{0}_{\text{m}} \) values are found to be more negative suggesting that the driving force for interaction was significantly increased and micellization more thermodynamically favorable.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Attwood, D., Florence, A.T.: Surfactant Systems. Their Chemistry, Pharmacy and Biology. Chapman and Hall, New York (1983)

    Google Scholar 

  2. Rosen, M.J.: Surfactants and Interfacial Phenomena, 3rd edn. Wiley, New York (2004)

    Book  Google Scholar 

  3. Khan, F., Siddiqui, U.S., Rub, M.A., Khan, I.A., Khan, I.A., Kabir-ud-Din: Micellization and interfacial properties of cationic gemini surfactant (12–4–12) in the presence of additives in aqueous electrolyte solution: a tensiometric study. J. Mol. Liq. 191, 29–36 (2014)

    Article  CAS  Google Scholar 

  4. Khan, F., Siddiqui, U.S., Rub, M.A., Khan, I.A., Kabir-ud-Din: Micellization behavior of butanediyl-1, 4-bis(dimethyldodecylammonium bromide) gemini surfactant in presence of organic additives. J. Dispers. Sci. Technol. 36, 83–93 (2015)

    Article  CAS  Google Scholar 

  5. Savaroglua, G., Genc, L.: Determination of micelle formation of ketorolac tromethamine in aqueous media by acoustic measurements. Thermochim. Acta 552, 5–9 (2013)

    Article  Google Scholar 

  6. Tadros, T.F.: Applied Surfactants: Principles and Applications. Wiley, New York (2005)

    Book  Google Scholar 

  7. Akbaş, H., Işcan, M., Sidim, T.: Composition of mixed anionic/nonionic surfactant micelles. J. Surfactants Deterg. 3, 77–80 (2000)

    Article  Google Scholar 

  8. Rub, M.A., Azum, N., Asiri, A.M.: Interaction of cationic amphiphilic drug nortriptyline hydrochloride with TX-100 in aqueous and urea solutions and the studies of physicochemical parameters of the mixed micelles. J. Mol. Liq. 218, 595–603 (2016)

    Article  Google Scholar 

  9. Al-Muhanna, M.K., Rub, M.A., Azum, N., Khan, S.B., Asiri, A.M.: Effect of gelatin on micellization and microstructural behavior of amphiphilic amitriptyline hydrochloride drug solution: a detailed study. J. Chem. Thermodyn. 89, 112–122 (2015)

    Article  CAS  Google Scholar 

  10. Rub, M.A., Azum, N., Asiri, A.M.: Self-association behavior of an amphiphilic drug nortriptyline hydrochloride under the influence of inorganic salts. Russ. J. Phys. Chem. B 10, 1007–1013 (2016)

    Article  Google Scholar 

  11. Schreier, S., Malheiros, S.V., de Paula, E.: Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochim. Biophys. Acta 1508, 210–234 (2000)

    Article  CAS  Google Scholar 

  12. Azum, N., Rub, M.A., Asiri, A.M.: Self-association and micro-environmental properties of sodium salt of ibuprofen with BRIJ-56 under the influence of aqueous/urea solution. J. Dispers. Sci. Technol. 38, 96–104 (2017)

    Article  CAS  Google Scholar 

  13. Azum, N., Rub, M.A., Asiri, A.M.: Micellization and interfacial behavior of the sodium salt of ibuprofen–BRIJ-58 in aqueous/brine solutions. J. Solution Chem. 45, 791–803 (2016)

    Article  CAS  Google Scholar 

  14. Kumar, D., Rub, M.A., Akram, M., Kabir-ud-Din: Role of gemini surfactants (m–s–m type; m = 16, s = 4–6) on the reaction of [Zn(II)–Gly–Phe] + with ninhydrin. J. Phys. Org. Chem. 27, 729–734 (2014)

    Article  CAS  Google Scholar 

  15. Rub, M.A., Azum, N., Asiri, A.M., Alfaifi, S.Y.M., Alharthi, S.S.: Interaction between antidepressant drug and anionic surfactant in low concentration range in aqueous/salt/urea solution: a conductometric and fluorometric study. J. Mol. Liq. 227, 1–14 (2017)

    Article  CAS  Google Scholar 

  16. Naqvi, A.Z., Rub, M.A., Kabir-ud-Din: Study of phospholipid induced phase separation in amphiphilic drugs. Colloid J. 77, 525–531 (2015)

    Article  CAS  Google Scholar 

  17. Azum, N., Rub, M.A., Asiri, A.M.: Energetics of clouding phenomenon in amphiphilic drug imipramine hydrochloride with pharmaceutical excipients. Pharmaceut. Chem. J. 48, 201–208 (2014)

    Article  CAS  Google Scholar 

  18. Rub, M.A., Azum, N., Khan, F., Asiri, A.M.: Surface, micellar, and thermodynamic properties of antidepressant drug nortriptyline hydrochloride with TX-114 in aqueous/urea solutions. J. Phys. Org. Chem. (2016). doi:10.1002/poc.3676

    Google Scholar 

  19. Kumar, D., Neo, K.-E., Rub, M.A.: Effect of alkanediyl-a, x-type cationic dimeric (gemini) surfactants on the reaction rate of ninhydrin with [Cu(II)–Gly–Tyr] + complex. J. Surfactant Deterg. 19, 101–109 (2016)

    Article  CAS  Google Scholar 

  20. Menger, F.M., Littau, C.A.: Gemini-surfactants: synthesis and properties. J. Am. Chem. Soc. 113, 1451–1452 (1991)

    Article  CAS  Google Scholar 

  21. Kumar, D., Rub, M.A., Akram, M., Kabir-ud-Din: Interaction of chromium(III) complex of glycylphenylalanine with ninhydrin in aqueous and cetyltrimethylammonium bromide (CTAB) micellar media. Tenside Surfactants Deterg. 51, 157–163 (2014)

    Article  CAS  Google Scholar 

  22. Kumar, D., Rub, M.A., Akram, M., Kabir-ud-Din: Effect of gemini (alkanediyl-a, x-bis(dimethylcetylammonium bromide)) (16–s–16, s = 4, 5, 6) surfactants on the interaction of ninhydrin with chromium-glycylphenylalanine. Spectrochim. Acta, Part A 132, 288–294 (2014)

    Article  CAS  Google Scholar 

  23. Bahadur, P., Chand, M.: Studies on sodium dodecyl benzene sulfonate in the presence of additives. Tenside, Surfactants, Deterg. 35, 134–141 (1998)

    CAS  Google Scholar 

  24. Ray, G.B., Chakraborty, I., Ghosh, S., Moulik, S.P.: A critical and comprehensive assessment of interfacial and bulk properties of aqueous binary mixtures of anionic surfactants, sodium dodecylsulfate, and sodium dodecylbenzenesulfonate. Colloid Polym. Sci. 285, 457–469 (2007)

    Google Scholar 

  25. Allen, T.M., Hansen, C.B., Menenez, D.E.L.: Pharmacokinetics of long-circulating liposomes. Adv. Drug Deliv. Rev. 16, 267–284 (1995)

    Article  CAS  Google Scholar 

  26. Paria, S.: The mixing behavior of n-alkylpyridinium bromide–NP-9 mixed surfactant systems. Colloids Surf. A 281, 113–118 (2006)

    Article  CAS  Google Scholar 

  27. Clint, J.H.: Micellization of mixed nonionic surface active agents. J. Chem. Soc., Faraday Trans. 1(71), 1327–1334 (1975)

    Article  Google Scholar 

  28. Holland, P.M., Rubingh, D.N.: Nonideal multicomponent mixed micelle model. J. Phys. Chem. 87, 1984–1990 (1983)

    Article  CAS  Google Scholar 

  29. Joshi, T., Bharatiya, B., Kuperkar, K.: Micellization and interaction properties of aqueous solutions of mixed cationic and nonionic surfactants. J. Dispers. Sci. Technol. 29, 1–7 (2008)

    Article  Google Scholar 

  30. Motomura, K., Yamanaka, M., Aratono, M.: Thermodynamic consideration of the mixed micelle of surfactants. Colloid Polym. Sci. 262, 948–955 (1984)

    Article  CAS  Google Scholar 

  31. Rodenas, V., Valiente, M., Villafruela, M.S.: Different theoretical approaches for the study of the mixed tetraethylene glycol mono-n-dodecyl ether/hexadecyltrimethylammonium bromide micelles. J. Phys. Chem. B 103, 4549–4554 (1999)

    Article  CAS  Google Scholar 

  32. Lange, H., Beck, K.H.: Zur Mizellbildung in mischlo¨sungen homologer und nichthomologer Tenside. Kolloid Z. Z. Polym. 251, 424–431 (1973)

    Article  CAS  Google Scholar 

  33. Hall, D.G.: Electrostatic effects in dilute solutions containing charged colloidal entities. J. Chem. Soc., Faraday Trans. 87, 3529–3535 (1991)

    Article  CAS  Google Scholar 

  34. Kabir-ud-Din, Rub, M.A., Naqvi, A.Z.: Mixed micellization between an antidepressant drug imipramine hydrochloride and surfactants (conventional/gemini) at different temperatures and compositions. J. Solution Chem. 44, 2448–2469 (2015)

    Article  CAS  Google Scholar 

  35. Azum, N., Rub, M.A., Asiri, A.M.: Experimental and theoretical approach to mixed surfactant system of cationic gemini surfactant with nonionic surfactant in aqueous medium. J. Mol. Liq. 196, 14–20 (2014)

    Article  CAS  Google Scholar 

  36. Azum, N., Rub, M.A., Asiri, A.M.: Analysis of surface and bulk properties of amphiphilic drug ibuprofen and surfactant mixture in the absence and presence of electrolyte. Colloids Surf. B 121, 158–164 (2014)

    Article  CAS  Google Scholar 

  37. Rub, M.A., Khan, F., Sheikh, M.S., Azum, N., Asiri, A.M.: Tensiometric, fluorescence and 1H NMR study of mixed micellization of non-steroidal anti-inflammatory drug sodium salt of ibuprofen in the presence of non-ionic surfactant in aqueous/urea solutions. J. Chem. Thermodyn. 96, 196–207 (2016)

    Article  Google Scholar 

  38. Azum, N., Rub, M.A., Asiri, A.M.: Micellization and interfacial behavior of binary and ternary mixtures in aqueous medium. J. Mol. Liq. 216, 94–98 (2016)

    Article  CAS  Google Scholar 

  39. Vethamuthu, M.S., Almgren, M., Karlsson, G., Bahadur, P.: Effect of sodium chloride and varied alkyl chain length on aqueous cationic surfactant—bile salt systems. Cryo-tem and fluorescence quenching studies. Langmuir 12, 2173–2185 (1996)

    Article  Google Scholar 

  40. Mandal, A.B., Moulik, S.P.: In: Mittal, K.L., Fendler, E.J. (eds.) Solution Behavior of Surfactants. Plenum Press, New York (1982)

    Google Scholar 

  41. Rub, M.A., Asiri, A.M., Naqvi, A.Z., Rahman, M.M., Khan, S.B., Kabir-ud-Din: Mixed micellization between amphiphilic drug promethazine hydrochloride and cationic surfactant (conventional as well as gemini). J. Mol. Liq. 177, 19–25 (2013)

    Article  CAS  Google Scholar 

  42. Rub, M.A., Khan, F., Kumar, D., Asiri, A.M.: Study of mixed micelles of promethazine hydrochloride (PMT) and nonionic surfactant (TX-100) mixtures at different temperatures and compositions. Tenside Surf. Deterg. 52, 236–244 (2015)

    Article  Google Scholar 

  43. Rub, M.A., Azum, N., Khan, S.B., Khan, F., Asiri, A.M.: Physicochemical properties of amphiphilic drug and anionic surfactant mixtures: experimental and theoretical approach. J. Disp. Sci. Technol. 36, 521–531 (2015)

    Article  CAS  Google Scholar 

  44. Hait, S.K., Majhi, P.R., Blume, A., Moulik, S.P.: A Critical assessment of micellization of sodium dodecyl benzene sulfonate (sdbs) and its interaction with poly(vinyl pyrrolidone) and hydrophobically modified polymers, JR 400 and LM 200. J. Phys. Chem. B 107, 3650–3658 (2003)

    Article  CAS  Google Scholar 

  45. Thakkar, K., Bharatiya, B., Shah, D.O., Bahadur, P.: Investigations on zwitterionic alkylsulfobetaines and nonionic Triton X-100 in mixed aqueous solutions: effect on size, phase separation and mixed micellar characteristics. J. Mol. Liq. 209, 569–577 (2015)

    Article  CAS  Google Scholar 

  46. Carale, T.R., Pham, Q.T., Blankschtein, D.: Salt effects on intramicellar interactions and micellization of nonionic surfactants in aqueous solutions. Langmuir 10, 109–121 (1994)

    Article  CAS  Google Scholar 

  47. Mukerjee, P., Korematsu, K., Okawauchi, M., Sugihara, G.: Effect of temperature on the electrical conductivity and the thermodynamics of micelle formation of sodium perfluorooctanoate. J. Phys. Chem. 89, 5308–5312 (1985)

    Article  CAS  Google Scholar 

  48. Schick, M.J.: Effect of temperature on the critical micelle concentration of nonionic detergents. Thermodynamics of micelle formation. J. Phys. Chem. 67, 1796–1799 (1963)

    Article  CAS  Google Scholar 

  49. Ray, A., Nemethy, G.: Micelle formation by nonionic detergents in water–ethylene glycol mixtures. J. Phys. Chem. 75, 809–815 (1971)

    Article  Google Scholar 

  50. Sharma, B., Rakshit, A.K.: Thermodynamics of micellization of a nonionic surfactant: Brij 35 in aquo–sucrose solution. J. Coll. Interface Sci. 129, 139–144 (1989)

    Article  CAS  Google Scholar 

  51. Mesa, C.L.: Dependence of critical micelle concentrations on intensive variables: a reduced variables analysis. J. Phys. Chem. 94, 323–326 (1990)

    Article  Google Scholar 

  52. Crook, E.H., Trebbi, G.F., Fordyce, D.B.: Thermodynamic properties of solutions of homogeneous p, t-octylphenoxyethoxyethanols (OPE1–10). J. Phys. Chem. 68, 3592–3599 (1964)

    Article  CAS  Google Scholar 

  53. Oda, H., Nagadome, S., Lee, S., Ohseto, F., Sasaki, Y., Sugihara, G.: Thermodynamic study on micelle formation in water and alcohols and on adsorption at air/water interface of n-nonyl-β-d-thiomaltoside (NTM) used as a membrane protein solubilizer by surface tension measurements. J. Oil Chem. Soc. Jpn. 46, 559–572 (1997)

    Article  CAS  Google Scholar 

  54. Islam, M.N., Kato, T.: Temperature dependence of surface phase behavior and micelle formation of some nonionic surfactants. J. Phys. Chem. B 107, 965–971 (2003)

    Article  CAS  Google Scholar 

  55. Lopez-Fontan, J.L., Costa, V., Ruso, J.M., Prieto, G., Sarmiento, F.: Electrical conductivities and critical micelle concentrations (determined by the local polynomial regression method) of imipramine and clomipramine hydrochlorides from (283 to 313) K. J. Chem. Eng. Data 49, 1008–1012 (2004)

    Article  CAS  Google Scholar 

  56. Rub, M.A., Azum, N., Asiri, A.M., Zayed, M.E.M., Al-Youbi, A.O.: Solution properties of phenothiazine drug promazine hydrochloride with cationic hydrotropes in aqueous/electrolyte solution at different temperature. J. Phys. Org. Chem. 29, 476–489 (2016)

    Article  Google Scholar 

  57. Kumar, D., Rub, M.A.: Aggregation behavior of amphiphilic drug promazine hydrochloride and sodium dodwecylbenzenesulfonate mixtures under the influence of NaCl/urea at various concentration and temperatures. J. Phys. Org. Chem. 29, 394–405 (2016)

    Article  CAS  Google Scholar 

  58. Al-Muhanna, M.K., Rub, M.A., Azum, N., Khan, S.B., Asiri, A.M.: Self-aggregation phenomenon of promazine hydrochloride under the influence of sodium cholate/sodium deoxycholate in aqueous medium. J. Dispers. Sci. Technol. 37, 450–463 (2016)

    Article  CAS  Google Scholar 

  59. Roy, G.B., Chakraborty, I., Ghosh, S., Moulik, S.P.: Studies on binary and ternary amphiphile combinations of tetrdecyltrimethyl ammonium bromide (C14TAB), tetrdecyl triphenyl phosphonium bromide (C14TPB), and tetradecyl pyridinium bromide (C14PB). A critical analysis of their interfacial and bulk behavior. J. Phys. Chem. B 111, 2828–2837 (2007)

    Article  Google Scholar 

  60. Asakawa, T., Kitano, H., Ohta, A., Miyagishi, S.: Convenient estimation for counterion dissociation of cationic micelles using chloride-sensitive fluorescence probe. J. Coll. Interface Sci. 242, 284 (2001)

    Article  CAS  Google Scholar 

  61. Chauhan, M.S., Sharma, K., Kumar, G., Chauhan, S.: A conductometric study of dimethylsulfoxide effect on micellization of sodium dodecyl sulfate in dilute aqueous electrolyte solutions. Colloid Surf. A 221, 135–140 (2003)

    Article  CAS  Google Scholar 

  62. Singh, O.G., Ismail, K.: Effect of sodium chloride on the aggregation, adsorption and counterion binding behavior of mixtures of sodium dioctylsulfosuccinate and sodium dodecylsulfate in water. Colloids Surf. A 414, 209–215 (2012)

    Article  CAS  Google Scholar 

  63. Kabir-ud-Din, Khan, A.B., Naqvi, A.Z.: Mixed micellization and interfacial properties of nonionic surfactants with the phenothiazine drug promazine hydrochloride at 30 °C. J. Solution Chem. 41, 1587–1599 (2012)

    Article  CAS  Google Scholar 

  64. Rub, M.A., Asiri, A.M., Khan, J.M., Khan, R.H., Kabir-ud-Din: Interaction of gelatin with promethazine hydrochloride: conductimetry, tensiometry and circular dichroism studies. J. Mol. Struct. 1050, 35–42 (2013)

    Article  Google Scholar 

  65. Kumar, D., Rub, M.A.: Effect of sodium turocholate on aggregation behavior of amphiphilic drug solution. Tenside Surfactants Deterg. 52, 464–472 (2015)

    Article  CAS  Google Scholar 

  66. Rub, M.A., Azum, N., Khan, S.B., Marwani, H.M., Asiri, A.M.: Micellization behavior of amphiphilic drug promazine hydrochloride and sodium dodecyl sulfate mixtures at various temperatures: effect of electrolyte and urea. J. Mol. Liq. 212, 532–543 (2015)

    Article  Google Scholar 

  67. Chauhan, S., Sharma, K.: Effect of temperature and additives on the critical micelle concentration and thermodynamics of micelle formation of sodium dodecyl benzene sulfonate and dodecyltrimethylammonium bromide in aqueous solution: a conductometric study. J. Chem. Thermodyn. 71, 205–211 (2014)

    Article  CAS  Google Scholar 

  68. Clint, J.H., Walker, T.J.: Thermodynamics of micellization of homologous series of n-alkyl methyl sulphoxides and n-alkyl(dimethyl)phosphine oxides. J. Chem. Soc., Faraday Trans. 1(71), 946–954 (1975)

    Article  Google Scholar 

  69. Wagle, V.B., Kothari, P.S., Gaikar, V.G.: Effect of temperature on aggregation behavior of aqueous solutions of sodium cumene sulfonate. J. Mol. Liq. 133, 68–76 (2007)

    Article  CAS  Google Scholar 

  70. Javadian, S., Gharibi, H., Bromand, Z., Sohrabi, B.: Electrolyte effect on mixed micelle and interfacial properties of binary mixtures of cationic and nonionic surfactants. J. Coll. Interface Sci. 318, 449–456 (2008)

    Article  CAS  Google Scholar 

  71. Khan, F., Rub, M.A., Azum, N., Kumar, D., Asiri, A.M.: Interaction of an amphiphilic drug and sodium bis(2-ethylhexyl)sulfosuccinate at low concentrations in the absence and presence of sodium chloride. J. Solution Chem. 44, 1937–1961 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Centre of Excellence for Advanced Materials Research and Chemistry Department, King Abdulaziz University, Jeddah are highly acknowledged.

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Malik Abdul Rub, Naved Azum, Abdullah M. Asiri, Heba A. Kashmery & Sulaiman Y. M. Alfaifi

  2. Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Malik Abdul Rub, Naved Azum & Abdullah M. Asiri

  3. Chemistry Department, Faculty of Science, Taif University, Taif, 21944, Saudi Arabia

    Salman S. Alharthi

Authors
  1. Malik Abdul Rub
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Naved Azum
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abdullah M. Asiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Heba A. Kashmery
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sulaiman Y. M. Alfaifi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Salman S. Alharthi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Malik Abdul Rub.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rub, M.A., Azum, N., Asiri, A.M. et al. Effect of Sodium Dodecylbenzenesulfonate on the Association Behavior of Promethazine Hydrochloride in Aqueous/Electrolyte Solutions at Different Temperatures. J Solution Chem 46, 862–885 (2017). https://doi.org/10.1007/s10953-017-0614-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-017-0614-y

Keywords

Search

Navigation