Synthesis of ${\beta}-Cyclodextrin$ Derivative Containing Cyanuric Chloride Moiety and Its Application to Fragrant Finish of Textiles

Cyanuric Chloride 잔기를 갖는 ${\beta}-Cyclodextrin$ 유도체의 합성과 섬유 방향가공에의 응용

  • Ko, Jae-Hoon (Digital Dyeing and Finishing Technology Team, Korea Institute of Industrial Technology) ;
  • Park, Yoon-Cheol (Digital Dyeing and Finishing Technology Team, Korea Institute of Industrial Technology) ;
  • Kim, Jin-Woo (Division of Chemical and Bio Engineering, Hanyang University) ;
  • Kim, Young-Ho (Department of Organic Materials and Fiber Engineering, Soongsil University)
  • 고재훈 (한국생산기술연구원 디지털가공팀) ;
  • 박윤철 (한국생산기술연구원 디지털가공팀) ;
  • 김진우 (한양대학교 응용화공생명공학부) ;
  • 김영호 (숭실대학교 유기신소재.파이버공학과)
  • Published : 2007.08.30

Abstract

[ ${\beta}$ ]-Cyclodextrin derivative containing cyanuric chloride moiety (${\beta}CD-CC$) was synthesized by a reaction of ${\beta}-cyclodextrin\;({\beta}CD-CC)$ with cyanuric chloride in alkaline condition. FT-IR and UV spectra along with the results of elemental analysis indicated that cyanuric chloride was bound to ${\beta}CD$. Remaining monochlorotriazine group in ${\beta}CD-CC$ was expected to be used as a reactive site for cellulosic fibers. The ${\beta}CD-CC$ could be used as a host material for inclusion complex of various guest molecules. As an example, vanillin, a flavoring agent in foods and others, was included in the ${\beta}CD-CC$ to make a perfume inclusion complex. UV analysis showed that the vanillin-included complex of ${\beta}CD-CC$ released vanillin more slowly than vanillin itself, which reveals that it can be used as a feasible fragrant finishing agent for textiles.

Keywords

References

  1. M. L. Bender and M. Komiyama, 'Cyclodextrin Chemistry', Springer-Verlag, New York, 1978, pp.3-9
  2. P. C. Manor and W. Saenger, 'Topography of Cyclodextrin Inclusion Complexes. III. Crystal and Molecular Structure of Cyclohexaamylose Hexahydrate, the Water Dimer Inclusion Complex', J Am Chern Soc, 1974,96,3630-3639 https://doi.org/10.1021/ja00818a042
  3. J. M. Lehn, Ed., 'Comprehensive Supramolecular Chemistry', Vol. 3, Cyclodextrins, Pergamon, New York, 1996, pp.190-191
  4. M. H. Lee, K. J. Yoon, and S.-W. Ko, 'Grafting onto Cotton Fiber with Acrylamidomethylated $\beta$-Cyclodextrin and Its Application', J Appl Polym Sci, 2000, 78, 1986-1991 https://doi.org/10.1002/1097-4628(20001209)78:11<1986::AID-APP190>3.0.CO;2-7
  5. J. Szejtli, 'Cyclodextrins in the Textile Industry', Starch/Starke, 2003, 55, 191-196
  6. M. H. Lee, K. J. Yoon, and S.-W. Ko, 'Synthesis of a Vinyl Monomer Containing $\beta$-Cyclodextrin and Grafting onto Cotton Fiber', J Appl Polym Sci, 2001, 80,438-446 https://doi.org/10.1002/1097-4628(20010418)80:3<438::AID-APP1117>3.0.CO;2-2
  7. A. Cireli and B. Yurdakul, 'Application of Cyclodextrin to the Textile Dyeing and Washing Processes', J Appl Polym Sci, 2006, 100, 208-218 https://doi.org/10.1002/app.22863
  8. E. P. A. Kumbasar, R. Atav, and A. Yurdakul, 'Equalizing Effect of $\beta$-Cyclodextrin on Dyeing of Polyamide 6,6 Woven Fabrics with Acid Dyes', J Appl Polym Sci, 2007, 103, 2660-2668 https://doi.org/10.1002/app.25416
  9. H. Reuscher and R. Hirsenkorn, 'Beta W7 MCT-New Ways in Surface Modification', J Incl Phenom, 1996,25, 191-196 https://doi.org/10.1007/BF01041567
  10. S. H. Hong, C. N. Choi, and S. Y. Kim, 'Synthesis of Bifunctional Reactive Dyes and Its Dyeability', J Korean Fiber Soc, 1996,33, 134-139
  11. D. J. Kim, K. C. Nam, and S. W. Park, 'A Study on the Reactive Dyes -Synthesis and Application of Bifunctional Reactive Dyes Containing Monochlorotriazinyl and Phosphonic Acid Group-', J Korean Soc of Text Eng Chern, 21, 1984, 17-24
  12. J. Shugar and J. T. Ballinger, 'Chemical Technicians' Ready Reference Handbook', McGraw-Hill Inc., NY, 1990, p.299
  13. S. Divakar and M. M. Maheswaram, 'Structural Studies on Inclusion Compounds of $\beta$-Cyclodextrin with Some Substituted Phenols', J Incl Phenom, 1997, 27, 113-126 https://doi.org/10.1023/A:1007949215051