Back
 JTST  Vol.8 No.2 , May 2022
Dyeing Thermodynamics and Supramolecular Structure of Lac Red on Protein Fibers
Abstract: The dyeing temperature of natural dye lac red on two kinds of natural protein fibers was studied, and the interaction between dyestuff and fiber was discussed through thermodynamic study and density functional theory (DFT) calculation. The optimum temperature for lac red dyed silk was 60˚C and wool showed a better response at 90˚C. The thermodynamics study revealed good Nernst isotherm and Freundlich adsorption models respectively, and the lac dye adsorption processes were both spontaneous and exothermic. The potential interaction of Laccaic acid A with the external environment by electrostatic potential and atomic charge distribution was first explored. With molecular simulation, Laccaic acid A and glycine composed 8 stable complexes. Then, typical hydrogen bonds, bond length, and binding energy, etc. were analyzed. The results revealed lac red on silk and wool fabric mainly depended on the weak hydrogen bonds and van der Waals force which determined the low dye fastness.
Cite this paper: Fu, K. , Li, J. , Qin, D. , Shi, L. , Ni, X. , Zhao, K. , Xu, D. , Yuan, A. and Zheng, C. (2022) Dyeing Thermodynamics and Supramolecular Structure of Lac Red on Protein Fibers. Journal of Textile Science and Technology, 8, 89-106. doi: 10.4236/jtst.2022.82008.
References

[1]   Gong, H., Zhou, H., Forrest, R.H., Li, S., Wang, J., Dyer, J.M. and Hickford, J.G. (2016) Wool Keratin-Associated Protein Genes in Sheep—A Review. Genes (Basel), 7, 24-40.
https://doi.org/10.3390/genes7060024

[2]   Sarker, P., Hosne Asif, A., Rahman, M., Islam, M. and Rahman, K. (2020) Green Dyeing of Silk Fabric with Turmeric Powder Using Tamarind Seed Coat as Mordant. Journal of Materials Science and Chemical Engineering, 8, 65-80.
https://doi.org/10.4236/msce.2020.82007

[3]   Vankar, P.S., Shanker, R. and Verma, A. (2007) Enzymatic Natural Dyeing of Cotton and Silk Fabrics without Metal Mordants. Journal of Cleaner Production, 15, 1441-1450.
https://doi.org/10.1016/j.jclepro.2006.05.004

[4]   Chairat, M., Rattanaphani, S., Bremner, J.B. and Rattanaphani, V. (2005) An Adsorption and Kinetic Study of Lac Dyeing on Silk. Dyes and Pigments, 64, 231-241.
https://doi.org/10.1016/j.dyepig.2004.06.009

[5]   Burwood, R., Read, G., Schofield, K. and Wright, D.E. (1967) The Pigments of Stick Lac. Part II: The Structure of Laccaic Acid A1. Journal of the Chemical Society C, 9, 842-851.
https://doi.org/10.1039/j39670000842

[6]   Pandhare, E.D., Rao, A.V.R., Shaikh, I.N. and Venkataraman, K. (1967) The Constitution of Laccaic Acid B. Wtrahedron Letters, 26, 2437-2440.
https://doi.org/10.1016/S0040-4039(00)90827-X

[7]   Santos, R., Hallett, J., Oliveira, M.C., Sousa, M.M., Sarraguça, J., Simmonds, M.S.J. and Nesbitt, M. (2015) HPLC-DAD-MS Analysis of Colorant and Resinous Components of Lac-Dye: A Comparison between Kerria and Paratachardina Genera. Dyes and Pigments, 118, 129-136.
https://doi.org/10.1016/j.dyepig.2015.02.024

[8]   Oka, H., Ito, Y., Yamada, S., Kagami, T., Hayakawa, J., Harada, K. and Ito, Y. (1998) Separation of Lac Dye Components by High-Speed Counter-Current Chromatography. Journal of Chromatography A, 813, 71-77.
https://doi.org/10.1016/S0021-9673(98)00311-2

[9]   Yamada, S., Noda, N., Mikami, E., Hayakawa, J. and Yamada, M. (1989) Analysis of Natural Coloring Matters in Food. III. Application of Methylation with Diazomethane for the Detection of Lac Color. Journal—Association of Official Analytical Chemists, 72, 48-51.
https://doi.org/10.1093/jaoac/72.1.48

[10]   Wu, C.H. (2007) Adsorption of Reactive Dye onto Carbon Nanotubes: Equilibrium, Kinetics and Thermodynamics. Journal of Hazardous Materials, 144, 93-100.
https://doi.org/10.1016/j.jhazmat.2006.09.083

[11]   Asif Tahir, M., Bhatti, H.N. and Iqbal, M. (2016) Solar Red and Brittle Blue Direct Dyes Adsorption onto Eucalyptus angophoroides Bark: Equilibrium, Kinetics and Thermodynamic Studies. Journal of Environmental Chemical Engineering, 4, 2431-2439.
https://doi.org/10.1016/j.jece.2016.04.020

[12]   Li, M., Song, K., Xie, K. and Hou, A. (2014) Crystal Morphology, Dispersing Stability and Dyeing Property of the Disperse Dye Based on Benzisothiazole. Pigment & Resin Technology, 43, 365-370.
https://doi.org/10.1108/PRT-10-2013-0099

[13]   Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Fox, D.J., et al. (2016) Gaussian 16. Revision B.01 Edition, Gaussian Inc., Wallingford.

[14]   Yang, Y., Weaver, M.N. and Merz, K.M. (2009) Assessment of the “6-31+G** + LANL2DZ” Mixed Basis Set Coupled with Density Functional Theory Methods and the Effective Core Potential: Prediction of Heats of Formation and Ionization Potentials for First-Row-Transition-Metal Complexes. The Journal of Physical Chemistry A, 113, 9843-9851.
https://doi.org/10.1021/jp807643p

[15]   Chen, C. and Liu, W. (2017) Research of Dyeing Thermodynamics and Supramolecular Structure of Luteolin on Wool Fabric. World Journal of Enguneering and Technolgy, 5, 20-29.

[16]   Qin, M., Zhong, F., Sun, Y., Tan, X., Hu, K., Zhang, H., Zhuang, L., et al. (2020) Experimental and DFT Studies on Surface Properties of Sulfonate-Based Surface Active Ionic Liquids. Journal of Molecular Structure, 1215, Article ID: 128258.
https://doi.org/10.1016/j.molstruc.2020.128258

[17]   Lu, T. and Chen, F. (2012a) Multiwfn: A Multifunctional Wavefunction Analyzer. Journal of Computational Chemistry, 33, 580-592.
https://doi.org/10.1002/jcc.22885

[18]   Humphrey, W., Dalke, A. and Schulten, K. (1996) VMD: Visual Molecular Dynamics. Journal of Molecular Graphics, 14, 33-38.
https://doi.org/10.1016/0263-7855(96)00018-5

[19]   Bader, R.F.W., Carroll, M.T., Cheeseman, J.R. and Chang, C. (1987) Properties of Atoms in Molecules: Atomic Volumes. Journal of the American Chemical Society, 109, 7968-7979.
https://doi.org/10.1021/ja00260a006

[20]   Knyazkov, D.A., Slavinskaya, N.A., Dmitriev, A.M., Shmakov, A.G., Korobeinichev, O.P. and Riedel, U. (2016) Structure of an n-Heptane/Toluene Flame: Molecular Beam Mass Spectrometry and Computer Simulation Investigations. Combustion, Explosion, and Shock Waves, 52, 142-154.
https://doi.org/10.1134/S0010508216020039

[21]   Chairat, M. (2009) Thermodynamics Study of Lac Dyeing of Silk Yarn Coated with Chitosan. Journal of Science & Technology, 6, 93-107.

[22]   Chiou, M.S. and Li, H.Y. (2002) Equilibrium and Kinetic Modeling of Adsorption of Reactive Dye on Cross-Linked Chitosan Beads. Journal of Hazardous Materials, B93, 233-248.
https://doi.org/10.1016/S0304-3894(02)00030-4

[23]   Qian, H.F. and Song, X.Y. (2007) The Structure of Azo Disperse Dyes and Its Distribution on Polyurethane Fiber Blend with Polyester, or Polyamide Fiber. Dyes and Pigments, 74, 672-676.
https://doi.org/10.1016/j.dyepig.2006.04.011

[24]   Khan, M.I., Min, T.K., Azizli, K., Sufian, S., Ullah, H. and Man, Z. (2015) Effective Removal of Methylene Blue from Water Using Phosphoric Acid Based Geopolymers: Synthesis, Characterizations and Adsorption Studies. RSC Advances, 5, 61410-61420.
https://doi.org/10.1039/C5RA08255B

[25]   Ncibi, M.C., Mahjoub, B. and Seffen, M. (2007) Kinetic and Equilibrium Studies of Methylene Blue Biosorption by Posidonia oceanica (L.) Fibres. Journal of Hazardous Materials, 139, 280-285.
https://doi.org/10.1016/j.jhazmat.2006.06.029

[26]   Chimprasit, A., Bremner, J.B., Danworaphong, S., Sajomsang, W., Gonil, P. and Chairat, M. (2019) A Kinetic and Thermodynamic Study of Lac Dye Adsorption on Silk Yarn Coated with Microcrystalline Chitosan. Coloration Technology, 135, 224-233.
https://doi.org/10.1111/cote.12396

[27]   Lu, T. and Chen, F. (2012b) Quantitative Analysis of Molecular Surface Based on Improved Marching Tetrahedra Algorithm.Journal of Molecular Graphics and Modelling, 38, 314-323.
https://doi.org/10.1016/j.jmgm.2012.07.004

[28]   Manzetti, S. and Lu, T. (2013) The Geometry and Electronic Structure of Aristolochic Acid: Possible Implications for a Frozen Resonance. Journal of Physical Organic Chemistry, 26, 473-483.
https://doi.org/10.1002/poc.3111

[29]   Lu, T. and Chen, F. (2013) Revealing the Nature of Intermolecular Interaction and Configurational Preference of the Nonpolar Molecular Dimers (H(2))(2), (N(2))(2), and (H(2))(N(2)). Journal of Molecular Modeling, 19, 5387-5395.
https://doi.org/10.1007/s00894-013-2034-2

[30]   Lu, T. and Manzetti, S. (2014) Wavefunction and Reactivity Study of Benzo[a]pyrene Diol Epoxide and Its Enantiomeric Forms. Structural Chemistry, 25, 1521-1533.
https://doi.org/10.1007/s11224-014-0430-6

[31]   Johnson, E.R., Keinan, S., Mori-Sanchez, P., Contreras-Garcia, J., Cohen, A.J. and Yang, W. (2010) Revealing Noncovalent Interactions. Journal of the American Chemical Society, 132, 6498-6506.
https://doi.org/10.1021/ja100936w

[32]   Chairat, M., Rattanaphani, V., Bremner, J.B., Rattanaphani, S. and Perkins, D.F. (2004) An Absorption Spectroscopic Investigation of the Interaction of Lac Dyes with Metal Ions. Dyes and Pigments, 63, 141-150.
https://doi.org/10.1016/j.dyepig.2004.02.006

 
 
Top