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Dye solubility in supercritical carbon dioxide. Effect of hydrogen bonding with cosolvents

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Abstract

The use of supercritical carbon dioxide is emerging as a potential method for achieving pollution-free dyeing. An important factor in supercritical fluid dyeing is the solubility of the dye in supercritical carbon dioxide. Our measurements show that the solubility of C. I. Disperse Red-60 dye in supercritical carbon dioxide is significantly enhanced upon addition of polar csolvents : ethanol and acetone. The solubility enhancement is attributed to the formation of hydrogen bonds between cosolvent and dye molecules. Observed solubility behavior is correlated using dilute-solution theory with lattice-fluid-hydrogen-bonding model. Needed physical and hydrogen-bonding molecular parameters are estimated using the experimental data.

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References

  • Bae, H. K. and Her, B. K., “Solubility of Disperse Dyes in Supercritical Carbon Dioxide”,HWAHAK KONGHAK,34, 379 (1996).

    CAS  Google Scholar 

  • Chang, K. H., Bae, H. K. and Shim, J. J., “Dyeing of PET Textile Fibers and Films in Supercritical Carbon Dioxide”,Korean J. Chem. Eng.,13, 310 (1996).

    CAS  Google Scholar 

  • Clifford, A. A. and Bartle, K. D., “Supercritical Fluid Dyeing”Textile and Tech. Int., 113 (1996).

  • Dobbs, J. M., Wong, J. M., Lahiere, R. J. and Johnston, K. P., “Modification of Supercritical Fluid Phase Behavior Using Polar Co-solvent”,Ind. Eng. Chem. Res.,26(1), 56 (1987).

    Article  CAS  Google Scholar 

  • Ewald, AH., Jepson, W.B. and Bowlinson, J.S., “The Solubility of Solids in Gases”,Disc. Farad. Soc.,15, 238 (1953).

    Article  Google Scholar 

  • Foster, N.R., Singh, H., Yun, S.L.J., Tomasko, D.L. and Macnaughton, S.J., “Polar and Nonpolar Co-solvent Effects on the Solubility of Cholesterol in Supercritical Fluids”,Ind. Eng. Chem. Res.,32, 2849 (1993).

    Article  CAS  Google Scholar 

  • Gerbert, B., Saus, W., Knittel, D., Buschmann, H.J. and Schollmeyer, E., “Dyeing Natural Fibers with Disperse Dyes in Supercritical Carbon Dioxide”,Textile Res. J.,64(7), 371 (1994).

    Article  Google Scholar 

  • Gupta, R.B., Combes, J.R. and Johnston, K.P., “Solvent Effect on Hydrogen Bonding in Supercritical Fluids”,J. Phys. Chem.,97, 707 (1993).

    Article  CAS  Google Scholar 

  • Gupta, R. B., Panayiotou, C, Sanchez, I. C. and Johnston, K. P., “Theory of Hydrogen Bonding in Supercritical Fluids”,AIChE J.,38(8), 1243 (1992).

    Article  CAS  Google Scholar 

  • Haarhaus, U., Swidersky, P. and Schneider, G. M., “High-Pressure Investigations on the Solubility of Dispersion Dyestuffs in Supercritical Gases by VIS/NIR-Spectroscopy. Part 1=1,4-Bis-(octadecylamino)-9,10-anthraquinone and Disperse Orange in CO2 and N2) up to 180 Mpa”,J. Supercrit. Fluids,8, 100 (1995).

    Article  CAS  Google Scholar 

  • Joung, S. N. and Yoo, K. P., “Solubility of Disperse Anthraquinone and Azo Dyes in Supercritical Carbon Dioxide at 313.15 to 393.15 K and from 10 to 25 MPa”,J. Chem. Eng. Data,43, 9 (1998).

    Article  CAS  Google Scholar 

  • Kazarian, S.G., Brantley, N.H., West, B.L., Vincent, M.F. and Eckert, C.A, “In Situ Spectroscopy of Polymers Subjected to Supercritical CO2: Plasticization and Dye Impregnation”,Appl. Spectroscopy,51(4), 491 (1997).

    Article  CAS  Google Scholar 

  • Ke, J., Jin, S., Han, B., Yan, H. and Shen, D., “Hydrogen Bonding of Some Organic Acid in Supercritical CO2 with Polar Co-solvents”,J. Supercrit. Fluids,11, 53 (1997).

    Article  CAS  Google Scholar 

  • Li, S., Varadarajan, G.S. and Hartland, S., “Solubility of Theobromine and Caffeine in Supercritical Carbon Dioxide: Correlation with Density-Based Models”,Fluid Phase Equilib.,68, 263 (1991).

    Article  CAS  Google Scholar 

  • Ozcan, A.S., Clifford, A.A., Bartle, K.D. and Lewis, D.M., “Dyeing of Cotton Fibres with Disperse Dyes in Supercritical Carbon Dioxide”,Dyes and Pigments,36(2), 103 (1998).

    Article  CAS  Google Scholar 

  • Ozcan, S.A., Clifford, A.A. and Bartle, K.D., “Solubility of Disperse Dyes in Supercritical Carbon Dioxide”,J. Chem. Eng. Data,42, 590 (1997).

    Article  Google Scholar 

  • Panayiotou, C. and Sanchez, I. C, “Hydrogen Bonding in Fluids: An Equation of State Approach”,J. Phys. Chem.,95, 10090 (1991).

    Article  CAS  Google Scholar 

  • Prausnitz, J. M., Lichlenthater, R. N. and Azevedo, E. G., “Molecular Thermodynamics of Fluid Phase Equilibria”, 2nd ed. ; Prentice-Hall Inc., Englewood Cliffs, NJ, Chapter 5 (1986).

    Google Scholar 

  • Sanchez, I. C. and Lacombe, R. H., “Elementary Molecular Theory of Classical Fluids 2. Statistical Thermodynamics of Fluid Mixtures”,J. Phys. Chem.,80, 2352 (1976) ; also “Elementary Molecular Theory of Classical Fluids. Pure Fluids”,ibid.,80, 2568 (1976).

    Article  CAS  Google Scholar 

  • Saus, W., Knittel, D. and Schollmeyer, E., “Farben aus uberkritischem Kohlendioxid-eine Alternative zur HT-Farbung von Polyester”Textile Praxis International,47, 1052 (1992).

    CAS  Google Scholar 

  • Saus, W., Knittel, D. and Schollmeyer, E., “Dyeing of Textiles in Supercritical Carbon Dioxide”Textile Res. J.,63(3), 135 (1993).

    CAS  Google Scholar 

  • Schmitt, W. J. and Reid, R. C, “The Influence of the Solvent Gas on the Solubility and Selectivity in Supercritical Extraction”, In Supercritical Fluid Technology ; Penninger, J. M., et al., Eds.; Elsevier; New York, 123 (1985).

    Google Scholar 

  • Shim, J. J. and Johnston, K. P., “Adjustable Solute Distribution between Polymers and Supercritical Fluids”,AIChE J.,35(7), 1097 (1989).

    Article  CAS  Google Scholar 

  • Sung, H. D. and Shim, J.J., “Dye Solubility in Supercritical Carbon Dioxide”, submitted toJ. Supercrit. Fluids, (1999).

  • Swidersky, P., Tuma, D. and Schneider, G.M., “High-Pressure Investigations on the Solubility of Dispersion Dyestuffs in Supercritical Gases by VIS-Spectroscopy. Part II 1,4-Bis-(n-alkylamino)-9,10-anthraquinones and Disperse Red 11 in CO2 N2O and CHF3 up to 180 MPa”,J. Supercrit. Fluids,9, 12 (1996).

    Article  CAS  Google Scholar 

  • Ting, S.S.T., Macnaughton, S.J., Tomasko, D.I. and Foster, N. R., “Solubility of Naproxen in Supercritical Carbon Dioxide with and without Co-solvents”,Ind. Eng. Chem. Res.,32, 1471 (1993).

    Article  CAS  Google Scholar 

  • Ting, S. S. T., Tomasko, D. L., Macnaughton, S. J. and Foster, N. R., “Chemical-Physical Interpretation of Co-solvent Effects in Supercritical Fluids”,Ind. Eng. Chem Res.,32, 1482 (1993).

    Article  CAS  Google Scholar 

  • Tsekhanskaya, Y.T., Iomtev, M.B. and Mushkina, E.V., “Solubility of Naphthalene in Ethylene and Carbon Dioxide Under Pressure”,Russian J. Phys. Chem,38(9), 1173 (1964).

    Google Scholar 

  • Wang, X. and Tavlarides, L. L., “Solubility of Solutes in Compressed Gases: Dilute Solution Theory”,Ind. Eng. Chem. Res.,33, 724 (1994).

    Article  CAS  Google Scholar 

  • Zhong, M., Han, B., Yan, H. and Peng, D. Y., “Effect of Ethanol and n-Octane on the Solubility of Stearic Acid in the Supercritical CO2”,Fluid Phase Equilib.,134, 175 (1997a).

    Article  CAS  Google Scholar 

  • Zhong, M., Han, B. and Yan, H., “Solubility of Stearic Acid in Supercritical CO2 with Co-solvents”,J. Supercrit Fluids,10, 113 (1997b).

    Article  CAS  Google Scholar 

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Correspondence to Ram B. Gupta.

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Muthukumaran, P., Gupta, R.B., Sung, HD. et al. Dye solubility in supercritical carbon dioxide. Effect of hydrogen bonding with cosolvents. Korean J. Chem. Eng. 16, 111–117 (1999). https://doi.org/10.1007/BF02699013

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