Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Investigation of Fluorescent Shape Memory Polyurethanes Grafted with Various Dyes

  • Chung, Yong-Chan (Department of Chemistry, University of Suwon) ;
  • Choi, Jae-Won (Department of Polymer Engineering, University of Suwon) ;
  • Lee, Seung-Hwan (Department of Polymer Engineering, University of Suwon) ;
  • Chun, Byoung-Chul (School of Nano Engineering, Center for Nano Manufacturing, Institute of Basic Science, Inje University)
  • Received : 2011.02.08
  • Accepted : 2011.04.13
  • Published : 2011.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

Shape memory polyurethane (SMPU), grafted with a fluorescent dye (Rhodamine, Mehylene violet, or Fluorescein) through an allophanate linking, was tested for the fluorescence and the shape recovery effect. The main chain of SMPU was composed of 4,4'-methylenebis(phenylisocyanate) (MDI), poly(tetramethyleneglycol) (PTMG), and 1,4-butanediol (BD), and a fluorescent dye was connected through a second MDI linked to the carbamate moiety of the main chain. Three series of SMPU, differing according to their dye content, were prepared to compare their shape recovery and fluorescence properties. In tensile mechanical property, maximum stress increased up to 350% compared to the linear SMPU, and strain remained above 2000%. Shape recovery went to as high as 97%, and remained almost same after repetitive shape recovery test cycles. Finally, the fluorescence emission of SMPU was demonstrated in the luminescence spectrum and fluorescent light emission pictures. In addition, the response of SMPU to external stimuli such as metal ions was investigated.

Keywords

References

  1. Takahashi, T.; Hayashi, N.; Hayashi, S. J. Appl. Polym. Sci. 1996, 60, 1061. https://doi.org/10.1002/(SICI)1097-4628(19960516)60:7<1061::AID-APP18>3.0.CO;2-3
  2. Chen, L. W.; Lin, J. R. J. Appl. Polym. Sci. 1998, 69, 1575. https://doi.org/10.1002/(SICI)1097-4628(19980822)69:8<1575::AID-APP12>3.0.CO;2-U
  3. Cho, J. W.; Lee, S. H. Eur. Polym. J. 2004, 40, 1343. https://doi.org/10.1016/j.eurpolymj.2004.01.041
  4. Rabani, G.; Luftmann, H.; Kraft, A. Polymer 2006, 47, 4251. https://doi.org/10.1016/j.polymer.2006.03.106
  5. Wang, W.; Ping, P.; Chen, X.; Jing, X. Eur. Polym. J. 2006, 42, 1240. https://doi.org/10.1016/j.eurpolymj.2005.11.029
  6. Xu, J.; Shi, W.; Pang, W. Polymer 2006, 47, 457. https://doi.org/10.1016/j.polymer.2005.11.035
  7. Razzaq, M. Y.; Anhalt, M.; Frormann, L.; Weidenfeller, B. Mater. Sci. Eng. A 2007, 471, 57. https://doi.org/10.1016/j.msea.2007.03.059
  8. Hu, J.; Yang, Z.; Yeung, L.; Ji, F.; Liu, Y. Polym. Int. 2005, 54, 854. https://doi.org/10.1002/pi.1785
  9. Yang, Z.; Hu, J.; Liu, Y.; Yeung, L. Mater. Chem. Phys. 2006, 98, 368. https://doi.org/10.1016/j.matchemphys.2005.09.065
  10. Chun, B. C.; Chong, M. H.; Chung, Y. C. J. Mat. Sci. 2007, 42, 6524. https://doi.org/10.1007/s10853-007-1568-z
  11. Chun, B. C.; Cho, T. K.; Chong, M. H.; Chung, Y. C. J. Mat. Sci. 2007, 42, 9045. https://doi.org/10.1007/s10853-007-1824-2
  12. Chung, Y. C.; Cho, T. K.; Chun, B. C. J. Appl. Polym. Sci. 2009, 112, 2800. https://doi.org/10.1002/app.29538
  13. Chung, Y. C.; Lim, N. K.; Choi, J. W.; Chun, B. C. J. Intell. Mater. Sys. Struct. 2009, 20, 1163. https://doi.org/10.1177/1045389X09103659
  14. Cho, J. W.; Kim, J. W.; Jung, Y. C.; Goo, N. S. Macro. Rapid. Com. 2005, 26, 412. https://doi.org/10.1002/marc.200400492
  15. Paik, I. H.; Goo, N. S.; Jung, Y. C.; Cho, J. W. Smart. Mater. Struct. 2006, 15, 1476. https://doi.org/10.1088/0964-1726/15/5/037
  16. Leng, J. S.; Lv, H. B.; Liu, Y. J.; Du, S. Y. Appl. Phys. Lett. 2007, 91, 144105. https://doi.org/10.1063/1.2790497
  17. Schmidt, A. M. Macro. Rapid. Com. 2006, 27, 1168. https://doi.org/10.1002/marc.200600225
  18. Leng, J. S.; Lan, X.; Liu, Y. J.; Du, S. Y.; Huang, W. M.; Liu, N.; Phee, S. J.; Yuan, Q. Appl. Phys. Lett. 2008, 92, 014104. https://doi.org/10.1063/1.2829388
  19. Leng, J. S.; Huang, W. M.; Lan, X.; Liu, Y. J.; Du, S. Y. Appl. Phys. Lett. 2008, 92, 204101. https://doi.org/10.1063/1.2931049
  20. Huo, F. J.; Su, J.; Sun, Y. Q.; Yin, C. X.; Tong, H. B.; Nie, Z. X. Dyes and Pigments 2010, 86, 50. https://doi.org/10.1016/j.dyepig.2009.11.007
  21. Dong, M.; Ma, T. H.; Zhang, A. J.; Dong, Y. M.; Wang, Y. W.; Peng, Y. Dyes and Pigments 2010, 87, 164. https://doi.org/10.1016/j.dyepig.2010.03.015
  22. Andreia, S.; Renato, E. F.; Reda, M. E.; Paulo, A. Eur. Polym. J. 2006, 42, 2270. https://doi.org/10.1016/j.eurpolymj.2006.07.004
  23. Nagao, D.; Anzai, N.; Kobayashi, Y.; Gu, S.; Konno, M. J. Coll. Inter. Sci. 2006, 298, 232. https://doi.org/10.1016/j.jcis.2005.10.052
  24. Yang, S.; Meng, F.; Tian, He.; Chen, K. Eur. Polym. J. 2002, 38, 911. https://doi.org/10.1016/S0014-3057(01)00265-8
  25. Seckin, T.; Gultek, A.; Kartac, S. Dyes and Pigments 2003, 56, 51. https://doi.org/10.1016/S0143-7208(02)00116-X
  26. Makovec, D.; Campelj, S.; Bele, M.; Maver, U.; Zorko, M.; Drofenik, M.; Jamnik, J.; Gaberscek, M. Coll. Surf. A: Physicochem. Eng. Aspects 2009, 334, 74. https://doi.org/10.1016/j.colsurfa.2008.10.006
  27. Chuan, D.; Wei, Y. X.; Wei, Y. L. J. Photochem. Photobio. A: Chem. 2005, 174, 15. https://doi.org/10.1016/j.jphotochem.2005.02.007
  28. Mohammad, T.; Morrison, H. J. Chrom. B 1997, 704, 265. https://doi.org/10.1016/S0378-4347(97)00475-1
  29. Kim, H. J.; Park, J. E.; Choi, M. G.; Ahn, S.; Chang, S. K. Dyes and Pigments 2010, 84, 54. https://doi.org/10.1016/j.dyepig.2009.06.009
  30. Nolan, E. M.; Ryu, J. W.; Jaworski, J.; Feazell, R. P.; Sheng, M.; Lippard, S. J. J. Am. Chem. Soc. 2006, 128, 15517. https://doi.org/10.1021/ja065759a
  31. Jang, Y. J.; Jun, E. J.; Lee, Y. J.; Kim, Y. S.; Kim, J. S.; Yoon, J. J. Org. Chem. 2005, 70, 9603. https://doi.org/10.1021/jo0509657
  32. Swamy, K. M. K.; Lee, Y. J.; Lee, H. N.; Chun, J.; Kim, Y.; Kim, S. J. J. Org. Chem. 2006, 71, 8626. https://doi.org/10.1021/jo061429x
  33. Shamansky, L. M.; Yang, M.; Olteanu, M.; Chronister, E. L. Mat. Lett. 1996, 26, 113. https://doi.org/10.1016/0167-577X(95)00214-6
  34. Guan, X.; Liu, X.; Su, Z.; Liu, P. React. Funct. Polym. 2006, 66, 1227. https://doi.org/10.1016/j.reactfunctpolym.2006.03.005
  35. Cho, H. K.; Lone, S.; Kim, D. D.; Choi, J. H.; Choi, S. W.; Cho, J. H.; Kim, J. H.; Cheong, I. W. Polymer 2009, 50, 2357. (F polyester) https://doi.org/10.1016/j.polymer.2009.03.032
  36. Uthirakumar, P.; Suh, E. K.; Hong, C. H.; Lee, Y. S. Polymer 2005, 46, 4640. https://doi.org/10.1016/j.polymer.2005.03.063
  37. Nagasaka, M.; Yoshida, K.; Sato, K.; Hoshi, T.; Anzai, J. I. J. Coll. Inter. Sci. 2010, 348, 441. https://doi.org/10.1016/j.jcis.2010.05.013
  38. Freij-Larsson, C.; Wesslen, B. J. Appl. Polym. Sci. 1993, 50, 345. https://doi.org/10.1002/app.1993.070500215
  39. Tan, K.; Obendorf, S. K. J. Mem. Sci. 2006, 274, 150. https://doi.org/10.1016/j.memsci.2005.08.004
  40. Archambault, J. G.; John, L. Coll. Surf. B: Biointer. 2004, 39, 9. https://doi.org/10.1016/j.colsurfb.2004.08.009
  41. Hur, M. K.; Kwak, J. M.; Hur, T. A. Polymer (Korea) 1996, 20, 392.
  42. Petrovic, Z. S.; Javni, I.; Divjakovic, V. J. J. Polym. Sci. Part B: Polym. Phys. 1998, 36, 221. https://doi.org/10.1002/(SICI)1099-0488(19980130)36:2<221::AID-POLB3>3.0.CO;2-U
  43. Sekkar, V.; Gopalakrishnan, S.; Devi, K. A. Eur. Polym. J. 2003, 39, 1281. https://doi.org/10.1016/S0014-3057(02)00364-6
  44. Jane, S. R.; Sekkar, V.; Krishinamurthy, V. N. J. Appl. Polym. Sci. 1996, 62, 2317. https://doi.org/10.1002/(SICI)1097-4628(19961226)62:13<2317::AID-APP17>3.0.CO;2-#

Cited by

  1. Characterisation and application of polyurethane copolymers grafted with photoluminescent dyes vol.130, pp.4, 2014, https://doi.org/10.1111/cote.12097
  2. Preparation of water-compatible antifungal polyurethane with grafted benzimidazole as the antifungal agent vol.132, pp.14, 2014, https://doi.org/10.1002/app.41676
  3. Characterization and proof testing of the halochromic shape memory polyurethane vol.71, pp.5, 2014, https://doi.org/10.1007/s00289-014-1116-3
  4. Lateral sol–gel cross-linking of polyurethane using the a grafted triethoxysilyl group vol.72, pp.3, 2014, https://doi.org/10.1007/s10971-014-3471-9
  5. Modification of polyurethane by graft polymerization of poly(acrylic acid) for the control of molecular interaction and water compatibility vol.72, pp.10, 2015, https://doi.org/10.1007/s00289-015-1429-x
  6. Synthesis and characterization of fluorescein-grafted polyurethane for potential application in biomedical tracing vol.31, pp.6, 2017, https://doi.org/10.1177/0885328216681893
  7. Effect of the ionized carboxyl group on the water compatibility and the antifungal activity of the benzimidazole-grafted polyurethane vol.74, pp.9, 2017, https://doi.org/10.1007/s00289-017-1916-3
  8. The grafting of phthalic acid onto polyurethane copolymer and its impact on the surface hydrophilicity, tensile stress, and shape recovery properties vol.56, pp.6, 2011, https://doi.org/10.1080/10601325.2019.1590124
  9. Ultrafast hybrid nanocomposite scintillators: A review vol.242, pp.None, 2011, https://doi.org/10.1016/j.jlumin.2021.118534