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Adv Mater. 2021 May;33(18):e2100068. doi: 10.1002/adma.202100068. Epub 2021 Mar 30.

Self-Diagnostic Polymers-Inline Detection of Thermal Degradation of Unsaturated Poly(ester imide)s.

Advanced materials (Deerfield Beach, Fla.)

Alexander Funtan, Philipp Michael, Simon Rost, Jürgen Omeis, Klaus Lienert, Wolfgang H Binder

Affiliations

  1. Macromolecular Chemistry, Institute of Chemistry, Faculty of Natural Science II, Martin Luther University Halle-Wittenberg, Von-Danckelmann-Platz 4, 06120, Halle (Saale), Germany.
  2. ELANTAS Europe GmbH, Großmannstraße 105, 20539, Hamburg, Germany.
  3. ALTANA AG, Abelstraße 43, 46483, Wesel, Germany.

PMID: 33783026 DOI: 10.1002/adma.202100068

Abstract

Monitoring polymer degradation is an important quest, particularly relevant for industry. Although many indirect methodologies for assessing polymer degradation exist, only few are applicable for an inline-monitoring via optic detection-systems. An inline-monitoring system is introduced for the thermal degradation of crosslinked poly(ester imide)s (PEIs) by embedding trifluoroacetyl functionalized stilbene molecules, serving as chemosensors to track the release of generated alcoholic byproducts. Nucleophilic addition of an alcohol to the sensors trifluoroacetyl functionality triggers hemiacetal formation which is accompanied by significant changes in optical properties, in turn allowing monitoring of sensor activation by direct spectroscopy. Fluorescence spectroscopy offers an easy detection tool for the inline thermal monitoring of PEI-degradation.

© 2021 The Authors. Advanced Materials published by Wiley-VCH GmbH.

Keywords: chemosensors; optical sensors; poly(ester imide)s; stilbenes; thermal polymer degradation

References

  1. A. Göpferich, Biomaterials 1996, 17, 103. - PubMed
  2. W. Guo, T.-H. Chuang, S.-T. Huang, W.-T. Leu, S.-H. Hsiao, J. Polym. Res. 2007, 14, 401. - PubMed
  3. N. C. Billingham, in Encyclopedia of Polymer Science and Technology, John Wiley & Sons, New York 2002, p. 1. - PubMed
  4. J. R. White, A. Turnbull, J. Mater. Sci. 1994, 29, 584. - PubMed
  5. I. C. McNeill, in Comprehensive Polymer Science and Supplements (Eds: G. Allen, J. C. Bevington), Pergamon, Amsterdam, The Netherlands 1989, p. 451. - PubMed
  6. M. Leclerc, Adv. Mater. 1999, 11, 1491. - PubMed
  7. W. J. Yoo, J. K. Seo, K. W. Jang, J. Y. Heo, J. S. Moon, J.-Y. Park, B. G. Park, B. Lee, Opt. Rev. 2011, 18, 144. - PubMed
  8. a) O. Rifaie-Graham, E. A. Apebende, L. K. Bast, N. Bruns, Adv. Mater. 2018, 30, 1705483; - PubMed
  9. b) C. Calvino, L. Neumann, C. Weder, S. Schrettl, J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 640. - PubMed
  10. a) C. Viets, S. Kaysser, K. Schulte, Composites, Part B 2014, 65, 80; - PubMed
  11. b) H. Zhao, M. Zhang, M. Zhu, S. Xu, Y. Cao, J.-H. Yin, Appl. Sci. 2019, 9, 2390. - PubMed
  12. J. W. Grate, Chem. Rev. 2008, 108, 726. - PubMed
  13. a) J.-i. Hahm, Sensors 2011, 11, 3327; - PubMed
  14. b) R. Yang, J. Zhao, Y. Liu, Polym. Degrad. Stab. 2013, 98, 2466. - PubMed
  15. a) J. J. BelBruno, Chem. Rev. 2019, 119, 94; - PubMed
  16. b) O. S. Ahmad, T. S. Bedwell, C. Esen, A. Garcia-Cruz, S. A. Piletsky, Trends Biotechnol. 2019, 37, 294; - PubMed
  17. c) M. P. Tiwari, A. Prasad, Anal. Chim. Acta 2015, 853, 1; - PubMed
  18. d) S. Suriyanarayanan, P. J. Cywinski, A. J. Moro, G. J. Mohr, W. Kutner, Top. Curr. Chem. 2012, 325, 165. - PubMed
  19. H. Kim, Y. Kim, J. Y. Chang, Macromol. Chem. Phys. 2014, 215, 1274. - PubMed
  20. S. Dadkhah, E. Ziaei, A. Mehdinia, T. Baradaran Kayyal, A. Jabbari, Microchim. Acta 2016, 183, 1933. - PubMed
  21. a) W.-R. Zhao, T.-F. Kang, L.-P. Lu, F.-X. Shen, S.-Y. Cheng, J. Electroanal. Chem. 2017, 786, 102; - PubMed
  22. b) D. Lakshmi, A. Bossi, M. J. Whitcombe, I. Chianella, S. A. Fowler, S. Subrahmanyam, E. V. Piletska, S. A. Piletsky, Anal. Chem. 2009, 81, 3576. - PubMed
  23. S. Subrahmanyam, S. A. Piletsky, E. V. Piletska, B. Chen, K. Karim, A. P. F. Turner, Biosens. Bioelectron. 2001, 16, 631. - PubMed
  24. D. Kriz, O. Ramstroem, A. Svensson, K. Mosbach, Anal. Chem. 1995, 67, 2142. - PubMed
  25. O. Y. F. Henry, D. C. Cullen, S. A. Piletsky, Anal. Bioanal. Chem. 2005, 382, 947. - PubMed
  26. G. J. Mohr, U. E. Spichiger-Keller, Anal. Chim. Acta 1997, 351, 189. - PubMed
  27. G. J. Mohr, N. Tirelli, C. Lohse, U. E. Spichiger-Keller, Adv. Mater. 1998, 10, 1353. - PubMed
  28. H. N. Kim, Z. Guo, W. Zhu, J. Yoon, H. Tian, Chem. Soc. Rev. 2011, 40, 79. - PubMed
  29. a) P. Michael, W. H. Binder, Angew. Chem., Int. Ed. 2015, 54, 13918; - PubMed
  30. b) T. A. Dickinson, J. White, J. S. Kauer, D. R. Walt, Nature 1996, 382, 697; - PubMed
  31. c) O. S. Wolfbeis, J. Mater. Chem. 2005, 15, 2657; - PubMed
  32. d) P. Anbukarasu, D. Sauvageau, A. L. Elias, Biotechnol. J. 2017, 12, 1700050. - PubMed
  33. M. Martinez-Abadia, R. Gimenez, M. B. Ros, Adv. Mater. 2018, 30, 1704161. - PubMed
  34. N. Jornet-Martínez, Y. Moliner-Martínez, R. Herráez-Hernández, C. Molins-Legua, J. Verdú-Andrés, P. Campíns-Falcó, Sens. Actuators, B 2016, 223, 333. - PubMed
  35. S. Rochat, T. M. Swager, ACS Appl. Mater. Interfaces 2013, 5, 4488. - PubMed
  36. X. Liu, Y. Xu, D. Jiang, J. Am. Chem. Soc. 2012, 134, 8738. - PubMed
  37. J.-S. Yang, T. M. Swager, J. Am. Chem. Soc. 1998, 120, 5321. - PubMed
  38. H.-A. Ho, M. Bera-Aberem, M. Leclerc, Chem. - Eur. J. 2005, 11, 1718. - PubMed
  39. S. Ghosh, R. Manna, ChemistrySelect 2016, 1, 6558. - PubMed
  40. K.-W. Lienert, in Progress in Polyimide Chemistry II (Ed: H. R. Kricheldorf), Springer, Berlin/Heidelberg, Germany 1999, p. 45. - PubMed
  41. A. Anton, K.-W. Lienert, G. Hegemann, Macromol. Mater. Eng. 2008, 293, 331. - PubMed
  42. a) L.-H. Perng, J. Polym. Res. 2000, 7, 185; - PubMed
  43. b) M. Nedjar, J. Appl. Polym. Sci. 2011, 121, 2886. - PubMed
  44. a) T. J. Murray, Macromol. Mater. Eng. 2008, 293, 350; - PubMed
  45. b) S. Maiti, S. Das, J. Appl. Polym. Sci. 1981, 26, 957. - PubMed
  46. G. J. Mohr, U.-W. Grummt, J. Fluoresc. 2006, 16, 185. - PubMed
  47. a) P. Xue, C. Zhang, K. Wang, M. Liang, T. Zhang, Dyes Pigm. 2019, 163, 516; - PubMed
  48. b) A. Pucci, F. Di Cuia, F. Signori, G. Ruggeri, J. Mater. Chem. 2007, 17, 783; - PubMed
  49. c) F. Cellini, S. Khapli, S. D. Peterson, M. Porfiri, Appl. Phys. Lett. 2014, 105, 061907. - PubMed
  50. M. Yang, L. Chen, C.-S. Zhao, H.-Z. Huang, J.-S. Wang, Y.-Z. Wang, Polym. Adv. Technol. 2009, 20, 378. - PubMed
  51. a) S. Marais, M. Metayer, T. Q. Nguyen, M. Labbe, J. M. Saiter, Eur. Polym. J. 2000, 36, 453; - PubMed
  52. b) J. Reichlin, E. Bormashenko, A. Sheshnev, R. Pogreb, Proc. SPIE 2000, 4129, 305. - PubMed
  53. F. Scheidt, M. Schäfer, J. C. Sarie, C. G. Daniliuc, J. J. Molloy, R. Gilmour, Angew. Chem., Int. Ed. 2018, 57, 16431. - PubMed
  54. G. J. Mohr, F. Lehmann, U.-W. Grummt, U. E. Spichiger-Keller, Anal. Chim. Acta 1997, 344, 215. - PubMed

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