OJOPM  Vol.2 No.4 , October 2012
Synthesis, Characterisation and Photoresponsive Studies of Lignin Functionalised with 2-(5-(4-dimethylamino-benzylidin)-4-oxo-2-thioxo- thiazolidin-3-yl)-acetic Acid
A chromophoric system 2-(5-(4-dimethylamino-benzylidin)-4-oxo-2-thioxo-thiazoli din-3-yl)acetic acid with push-pull electron modulation was synthesised and incorporated onto lignin core (technical lignin, lignin sulphonic acid M.W. 52,400) and the photo responsive behaviour was investigated. The product was characterised by UV-visible, fluores-cence, FT-IR, and NMR spectroscopic methods. The results of the studies show that the incorporation of the chromo-phoric system on to the lignin core enhanced the light absorption and light stabilization properties of the chromophoric system. The remarkable stability on irradiation provides a novel photo responsive system with excellent light fastening properties which would find application in coating materials, dyes, paints etc.

Cite this paper
A. Chandran, S. Kuriakose and T. Mathew, "Synthesis, Characterisation and Photoresponsive Studies of Lignin Functionalised with 2-(5-(4-dimethylamino-benzylidin)-4-oxo-2-thioxo- thiazolidin-3-yl)-acetic Acid," Open Journal of Organic Polymer Materials, Vol. 2 No. 4, 2012, pp. 63-68. doi: 10.4236/ojopm.2012.24009.

[1]   J. F. Matte and J. Doucet, “Recent Developments in Lignin Utilization as Wood Adhesive: A review,” Cellulose Chemistry and Technology, Vol. 22, No. 1, 1988, pp. 7185.

[2]   D. W. Sundstrom and H. E. Klei, “Uses of By-Product Lignins from Alcohol Fuel Processes,” Biotechnology and Bioengineering Symposium, Vol. 12, 1982, pp. 45-56.

[3]   J. Ralph, R. D. Hatfield, S. Quideau, R. F. Helm, J. H. Grabber and H.-J. G. Jung, “Pathway of P-Coumaric Acid Incorporation into Maize Lignin as Revealed by NMR”, Journal of the American Chemical Society, Vol. 116, No. 21, 1994, pp. 9448-9456. doi:10.1021/ja00100a006

[4]   J. Ralph, R. F. Helm, S. Quideau and R. D. Hatfield, “Lignin-Feruloyl Ester Cross-Links in Grasses. Part 1. Incorporation of Feruloyl Esters into Coniferyl Alcohol Dehydrogenation Polymers,” Journal of the Chemical Society, Perkin Transactions, Vol. 1, 1995, pp. 29612969.

[5]   J. Ralph and F. Lu, “The DFRC Method for Lignin Analysis. Part 6. A Modified Method to Determine Acetate Regiochemistry on Native and Isolated Lignins,” Journal of Agricultural and Food Chemistry, Vol. 46, No. 11, 1998, pp. 4616-4619. doi:10.1021/jf980680d

[6]   J. H. Grabber, J. Ralph and R. D. Hatfield, “Ferulate Cross-Links Limit the Enzymatic Degradation of Synthetically Lignified Primary Walls of Maize Digestibility,” American society of Agronomy Inc, Maidson, 1993.

[7]   S. Sarkanen, P. C. Teller, C. R. Stevens and J. L. Mccarthy, “Lignin. 20. Associative Interactions between Kraft Lignin Components,” Macromolecules, Vol. 17, No. 12, 1984, pp. 2588-2597. doi:10.1021/ma00142a022

[8]   K. V. Sarkanen and C. H. Ludwig, “Definition and Nomen Clature,” In: Lignins: Occurance, Formation, Structure and Reactions, Wiley-Interscience, NewYork, 1971, pp. 1-16.

[9]   W. Boerjan, J. Ralph and M. Baucher, “Lignin Biosynthesis,” Annual Review of Plant Biology, Vol. 54, No. 1, 2003, pp. 519-546. doi:10.1146/annurev.arplant.54.031902.134938

[10]   J. Ralph, K. Lundquist, G. Brunow, F. Lu, H. Kim, P. F. Schatz, J. M. Marita, R. D. Hatfield, S. A. Ralph, J. H. Christensen and W. Boerjan, “Lignins: Natural Polymers from Oxidative Coupling of 4-hydroxy Phenyl Propanoids,” Phytochemistry Reviews, Vol. 3, No. 1, 2004, pp. 29-60. doi:10.1023/B:PHYT.0000047809.65444.a4

[11]   D. C. C. Smith, “P-Hydroxy Benzoate Groups in the Lignin of Aspen (Populus Tremula) ,” Journal of the Chemical Society, 1995, pp. 2347-2351.

[12]   D. C. C. Smith, “Ester Groups in Lignin,” Nature, Vol. 176, No. 4475, 1955, pp. 267-268. doi:10.1038/176267a0

[13]   J. R. Dyer, “Applications of Absorption Spectroscopy of Organic Compounds,” Phi Learning, New Delhi, 2009.

[14]   W. Kemp, “Organic Spectroscopy,” Macmillan, London, 1975.