Effect of different additives on the phase separation behavior and thermodynamics of p-tert-alkylphenoxy poly (oxyethylene) ether in absence and presence of drug

doi:10.1016/j.cjche.2017.10.011

摘要/Abstract

摘要： Cloud point (CP) determinations of 4-(1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol (TX-100 (nonionic surfactant)) was carried out in aqueous as well as in the attendance of drug (ceftriaxone sodium trihydrate (CFT))/(CFT + different inorganic salts) and discussed thoroughly. Nonionic surfactants are employed extensively in different formulations. In aqueous solution, the values of CP of TX-100 are obtained to increase by means of enhancing of their concentration in the solution. The CP values of TX-100 solutions were found to decrease in the presence of drug and their values decrease more with rising concentrations of the drug. The values of CP of CFT and TX-100 mixtures were found to further decrease in the attendance of inorganic salts in comparison to their absence. The effect of different sodium salts in decreasing CP values of TX-100 was achieved in the following order:NaCO₃ > Na₂SO₄ > NaCl. However, in the case of potassium and ammonium salts, the decreasing order obtained is K₂SO₄ > KCO₃ > KCl and (NH₄)₂SO₄ > Na₂CO₃ > NH₄Cl respectively. Various thermodynamic parameters for example standard free energy (ΔG_c^Θ), standard enthalpy (ΔH_c^Θ) as well as standard entropy (ΔS_c^Θ) changes of phase separation were also evaluated and discussed in detail on the basis of their behavior.

关键词: Cloud point, TX-100, Ceftriaxone sodium trihydrate, Inorganic salts, Thermodynamic parameters

Abstract: Cloud point (CP) determinations of 4-(1,1,3,3-tetramethylbutyl)phenyl-polyethylene glycol (TX-100 (nonionic surfactant)) was carried out in aqueous as well as in the attendance of drug (ceftriaxone sodium trihydrate (CFT))/(CFT + different inorganic salts) and discussed thoroughly. Nonionic surfactants are employed extensively in different formulations. In aqueous solution, the values of CP of TX-100 are obtained to increase by means of enhancing of their concentration in the solution. The CP values of TX-100 solutions were found to decrease in the presence of drug and their values decrease more with rising concentrations of the drug. The values of CP of CFT and TX-100 mixtures were found to further decrease in the attendance of inorganic salts in comparison to their absence. The effect of different sodium salts in decreasing CP values of TX-100 was achieved in the following order:NaCO₃ > Na₂SO₄ > NaCl. However, in the case of potassium and ammonium salts, the decreasing order obtained is K₂SO₄ > KCO₃ > KCl and (NH₄)₂SO₄ > Na₂CO₃ > NH₄Cl respectively. Various thermodynamic parameters for example standard free energy (ΔG_c^Θ), standard enthalpy (ΔH_c^Θ) as well as standard entropy (ΔS_c^Θ) changes of phase separation were also evaluated and discussed in detail on the basis of their behavior.

Key words: Cloud point, TX-100, Ceftriaxone sodium trihydrate, Inorganic salts, Thermodynamic parameters

Marzia Rahman, Md. Anamul Hoque, Mohammed Abdullah Khan, Malik Abdul Rub, Abdullah M. Asiri. Effect of different additives on the phase separation behavior and thermodynamics of p-tert-alkylphenoxy poly (oxyethylene) ether in absence and presence of drug[J]. Chinese Journal of Chemical Engineering, 2018, 26(5): 1110-1118.

参考文献

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

[2] M.J. Rosen, Surfactants and Interfacial Phenomena, third ed. Wiley, New York, 2004.

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

[4] M.A. Rub, N. Azum, A.M. Asiri, 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(2016) 595-603.

[5] D. Kumar, M.A. Rub, Effect of sodium taurocholate on aggregation behavior of amphiphilic drug solution, Tenside Surf. Deterg. 52(2015) 464-472.

[6] M.A. Rub, N. Azum, A.M. Asiri, Binary Mixtures of Sodium Salt of Ibuprofen and Selected Bile Salts:Interface, Micellar, Thermodynamic, and Spectroscopic Study, J. Chem. Eng. Data 62(2017) 3216-3228.

[7] D. Kumar, M.A. Rub, Kinetic study of nickel-glycylglycine with ninhydrin in alkanediyl-α,ω-gemini (m-s-m type) surfactant system, J. Mol. Liq. 240(2017) 253-257.

[8] H. Siddiqui, M. Kamil, M. Panda, Kabir-ud-Din, Solubilization of phenanthrene and fluorene in equimolar binary mixtures of gemini/conventional surfactants, Chin. J. Chem. Eng. 22(2014) 1009-1015.

[9] M.A. Rub, F. Khan, M.S. Sheikh, N. Azum, A.M. Asiri, 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(2016) 196-207.

[10] D. Bhatt, K.C. Maheria, J. Parikh, Studies on surfactant-ionic liquid interaction on clouding behavior and evaluation of thermodynamic parameters, J. Surfactant Deterg. 16(2013) 547-557.

[11] D. Kumar, K.-E. Neo, M.A. Rub, Dipeptide glycyl-glycine (Gly-Gly)-ninhydrin reaction:Effect of alkanediyl α,ω-bis(dimethylcetylammonium bromide) (16-s-16, s=4, 5, 6) gemini surfactants on the reaction rate, Tenside Surf. Deterg. 53(2016) 168-175.

[12] M.A. Hoque, M.M. Alam, M.R. Molla, S. Rana, M.A. Rub, M.A. Halim, M.A. Khan, F. Akhtar, Interaction of cetyltrimethylammonium bromide with drug in aqueous/electrolyte solution:A combined conductometric and molecular dynamics method study, Chinese J. Chem. Eng. (2017), https://doi.org/10.1016/j.cjche.2017.06.016.

[13] D. Myers, Surfactant Science and Technology, second ed. VCH, New York, 1992.

[14] S.A. Buckingham, C.J. Garvey, G.G. Warr, Effect of head-group size on micellization and phase behavior in quaternary ammonium surfactant systems, J. Phys. Chem. 97(1993) 10236-10244.

[15] T. Inoue, T. Misono, Cloud point phenomena for POE-type nonionic surfactants in imidazolium-based ionic liquids:Effect of anion species of ionic liquids on the cloud point, J. Colloid Interface Sci. 337(2009) 247-253.

[16] H. Arai, M. Murata, K. Shinoda, Interaction between polar and surfactant. Composition of the complex between poly(vinylpyrrolidinone) and sodium alkyl sulfate as revealed by surface tension, dialysis, and solubilization, J. Colloid Interface Sci. 37(1971) 223-227.

[17] S. Chauhan, K. Sharma, K. Kumar, G. Kumar, A comparative study of micellization behavior of an ethoxylated alkylphenol in aqueous solutions of glycine and leucine, J. Surfactant Deterg. 17(2014) 161-168.

[18] C. Batigoc, H. Akbas, Spectrophotometric determination of cloud point of Brij 35 nonionic surfactant, Fluid Phase Equilib. 303(2011) 91-95.

[19] H. Schott, Effect of inorganic additives on solutions of nonionic surfactants-XVI. Limiting cloud points of highly polyoxyethylated surfactants, Colloids Surf. A Physicochem. Eng. Asp. 186(2001) 129-136.

[20] Z. Huang, T. Gu, The effect of mixed cationic-anionic surfactants on the cloud point of non-ionic surfactant, J. Colloid Interface Sci. 138(1990) 580-582.

[21] R.K. Mahajan, J. Chawla, M.S. Bakshi, Depression of the cloud point of Tween in presence of glycol additives and triblock polymers, Colloid Polym. Sci. 282(2004) 1165-1168.

[22] M.B. Khan, M.A. Hoque, D.M.S. Islam, Physicochemical investigation of the clouding behavior and thermodynamics of p-tert-alkylphenoxy poly(oxyethylene) ether micelles in aqueous environment and in the presence of dios, J. Chem. Thermodyn. 89(2015) 177-182.

[23] A.D. Mudawadkar, G.H. Sonawane, T.J. Patil, Thermodynamics of micellization of nonionic surfactant Triton X-100 in presence of additive Poly-N-vinyl-pyrrolidone using clouding phenomenon, Orient. J. Chem. 29(1) (2013) 227-233.

[24] K. Shinoda, T. Makagawa, B. Tanamushi, T. Ishemushi, Colloidal Surfactants, Academic Press, New York, 1963.

[25] M. Alauddin, T. Parvin, T. Begum, Effect of organic additives on the cloud point of Triton X-100 micelles, J. Appl. Sci. 9(12) (2009) 2301-2306.

[26] R.K. Mahajan, K.K. Vohra, N. Kaur, V.K. Aswal, Organic additives and electrolytes as cloud point modifiers in octylphenol ethoxylate solutions, J. Surfactant Deterg. 11(2008) 243-250.

[27] K.S. Sharma, S.R. Patil, A.K. Rakshit, Study of the cloud point of C₁₂E_n nonionic surfactants:Effect of additives, Colloids Surf. A 219(2003) 67-74.

[28] K. Panchal, A. Desai, T. Nagar, Physicochemical behavior of mixed nonionic-ionic surfactants in water and aqueous salt solutions, J. Dispers. Sci. Technol. 27(2006) 33-38.

[29] M.A. Hoque, A. Mitu, M.O.F. Patory, D.M.S. Islam, Physicochemical studies of effect of additives on clouding behavior and thermodynamics of polyoxyethylene (20) sorbitan monooleate, Indian J. Chem. 55A (2016) 793-802.

[30] D.K. Rout, S. Chauhan, A. Agarwal, Cloud point and microemulsion phase behavior of sodium linear alkylbenzene sulfonate with tetrabutyl-and benzyltributylsubstituted ammonium halides, Ind. Eng. Chem. Res. 48(2009) 8842-8847.

[31] T. Inoue, H. Ohmura, D. Muratr, Cloud point temperature of polyoxyethylenetype nonionic surfactants and their mixtures, J. Colloid Interface Sci. 258(2003) 374-382.

[32] R.N. Brogden, A. Ward, Ceftriaxone. A reappraisal of its antibacterial activity and pharmacokinetic properties, and an update on its therapeutic use with particular reference to once-daily administration, Drugs 35(1988) 604-645.

[33] J.S. Joyal, N. Sitaras, F. Binet, J.C. Rivera, A. Stahl, K. Zaniolo, Z. Shao, A. Polosa, T. Zhu, D. Hamel, M. Djavari, D. Kunik, J.C. Honore, E. Picard, A. Zabeida, D.R. Varma, G. Hickson, J. Mancini, M. Klagsbrun, S. Costantino, C. Beausejour, P. Lachapelle, L.E.H. Smith, S. Chemtob, P. Sapieha, Ischemic neurons prevent vascular regeneration of neural tissue by secreting semaphorin 3A, Blood 117(2011) 6024-6035.

[34] C.J. Pendegrass, D. Gordon, C.A. Middleton, S.N.M. Sun, G.W. Blunn, Sealing the skin barrier around transcutaneous implants:In vitro study of keratinocyte proliferation and adhesion in response to surface modifications of titanium alloy, J. Bone Joint Surg. 90(2008) 114-121.

[35] M.A. Ferguson, N.L. Alderson, S.G. Trost, D.A. Essig, J.R. Burke, J.L. Durstine, Effects of four different single exercise sessions on lipids, lipoproteins, and lipoprotein lipase, J. Appl. Physiol. 85(1998) 1169-1174.

[36] N. Azum, M.A. Rub, A.M. Asiri, W.A. Bawazeer, Micellar and interfacial properties of amphiphilic drug-non-ionic surfactants mixed systems:Surface tension, fluorescence and UV-vis studies, Colloids Surf. A 522(2017) 183-192.

[37] J.L. Li, D.S. Bai, B.H. Chen, Effects of additives on the cloud points of selected nonionic linear ethoxylated alcohol surfactants, Colloids Surf. A Physicochem. Eng. Asp. 346(2009) 237-243.

[38] P. Parekh, R.U. Yerramilli, P. Bahadur, Cloud point and thermodynamic parameters of a non-ionic surfactant heptaoxyethylene dodecyl ether (C₁₂E₇) in presence of various organic and inorganic additives, Indian J. Chem. A 52(2013) 1284-1290.

[39] T. Gu, P.A. Galera-Gomez, The effect of different alcohols and other polar organic additives on the cloud point of Triton X-100 in water, Colloids Surf. A Physicochem. Eng. Asp. 147(1999) 365-370.

[40] D. Blankschtein, G.M. Thurston, G.B. Benedek, Phenomenological theory of equilibrium thermodynamic properties and phase separation of micellar solutions, J. Chem. Phys. 85(1986) 7268-7288.

[41] R.C. da Silva, W. Loh, Effect of additives on the cloud points of aqueous solutions of ethylene oxide-propylene oxide-ethylene oxide block copolymers, J. Colloid Interface Sci. 202(1998) 385-390.

[42] K. Shinoda, H. Takeda, The effect of added salts in water on the hydrophile-lipophile balance of nonionic surfactants:The effect of added salts on the phase inversion temperature of emulsions, J. Colloid Interface Sci. 32(1970) 642-646.

[43] R. Heusch, Structures in surfactant/water mixtures and their use in biotechnology, BTF-Biotech Forum 3(1986) 1-8.

[44] J. Parikh, J. Rathore, D. Bhatt, M. Desai, Clouding behavior and thermodynamic study of nonionic surfactants in presence of additives, J. Dispers. Sci. Technol. 34(2013) 1392-1398.

[45] M. El Nakaly, L.D. Ford, S.E. Friberg, D.W. Larsen, The structure of lamellar lyotropic liquid crystals from lecithin and alkanediols, J. Colloid Interface Sci. 84(1981) 228-234.

[46] M.S. Alam, Kabir-ud-Din, A.B. Mandal, Evaluation of thermodynamic parameters of some amphiphilic drugs in presence of sugars at the cloud point, Colloids Surf. B 105(2013) 236-245.

[47] C.K. Bahal, H.B. Kostenbauder, Interaction of preservatives with macromolecules V binding of chlorobutanol, benzyl alcohol, and phenylethyl alcohol by nonionic agents, J. Pharm. Sci. 53(1964) 1027-1029.

[48] J.M. Hierrezuelo, J.A. Molina-Bolivar, C.C. Ruiz, An energetic analysis of the phase separation in non-ionic surfactant mixtures:The role of the headgroup structure, Entropy 16(2014) 4375-4391.

[49] M.A. Rub, A.M. Asiri, A. Khan, A.A.P. Khan, N. Azum, S.B. Khan, Kabir-ud-Din, Investigation of micellar and phase separation phenomenon of the amphiphilic drug amitriptyline hydrochloride with cationic hydrotropes, J. Solut. Chem. 42(2013) 390-411.

[50] N. Azum, M.A. Rub, A.M. Asiri, Energetics of clouding phenomenon in amphiphilic drug imipramine hydrochloride with pharmaceutical excipients, Pharm. Chem. J. 48(2014) 201-208.

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

[52] Kabir-ud-Din, M.A. Rub, M.S. Sheikh, Cloud point modulation of an amphiphilic drug with pharmaceutical excipients, J. Chem. Eng. Data 55(2010) 5642-5652.

[53] D.C. Robins, I.L. Thomas, The effect of counterions on micellar properties of 2-dodecylaminoethanol salts:I. Surface tension and electrical conductance studies, J. Colloid Interface Sci. 26(1968) 407-414.

[54] M.A. Hoque, M.A. Khan, M.D. Hossain, Interaction of cefalexin monohydrate with cetyldimethylethylammonium bromide, J. Chem. Thermodyn. 60(2013) 71-75.

[55] Kabir-ud-Din, S. Khatoon, A.Z. Naqvi, Nonelectrolyte-induced CP variation of TX-114+TBAB system, Acta Phys. -Chim. Sin. 24(2008) 1180-1184.

[56] J.H. Clint, Surfactant Aggregation, Chapman and Hall, New York, 1992.

[57] G.C. Kresheck, in:F. Franks (Ed.), Water. A Comprehensive Treatise, Plenum, New York, 1995.

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

[59] M. Rahman, M.A. Khan, M.A. Rub, M.A. Hoque, Effect of temperature and salts on the interaction of cetyltrimethylammonium bromide with ceftriaxone sodium trihydrate drug, J. Mol. Liq. 223(2016) 716-724.

[60] M. Rahman, M.A. Khan, M.A. Rub, M.A. Hoque, A.M. Asiri, Investigation of the effect of various additives on the clouding behavior and thermodynamics of polyoxyethylene (20) sorbitan monooleate in absence and presence of ceftriaxone sodium trihydrate drug, J. Chem. Eng. Data 62(2017) 1464-1474.

[61] D. Kumar, M.A. Rub, Effect of anionic surfactant and temperature on micellization behavior of promethazine hydrochloride drug in absence and presence of urea, J. Mol. Liq. 238(2017) 389-396.

[62] M.R. Molla, M.A. Rub, A. Ahmed, A. Hoque, Interaction between tetradecyltrimethylammonium bromide and benzyldimethylhexadecylammonium chloride in aqueous/urea solution at various temperatures:An experimental and theoretical investigation, J. Mol. Liq. 238(2017) 62-70.

[63] S.K. Shivaji, A.K. Rakshit, Investigation of the properties decaoxyethylene n-dodecyl ether, C₁₂E₁₀, in the aqueous sugar-rich region, J. Surf. Deterg. 7(2004) 305-316.

[64] L.J. Chen, S.Y. Lin, C.C. Huang, Effect of hydrophobic chain length of surfactants on enthalpy-entropy compensation of micellization, J. Phys. Chem. 102(1998) 4350-4356.

[65] R. Lumry, S. Rajender, Enthalpy-entropy compensation phenomena in water solutions of proteins and small molecules:A ubiquitous property of water, Biopolymers 9(1970) 1125-1127.