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Anionic synthesis of amine ω-terminated β-myrcene polymers

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Abstract

Well-defined amine ω-terminated β-myrcene polymers were synthetized via anionic living polymerization under an inert atmosphere with dropwise addition of equimolar amounts of N-benzylidenetrimethylsilylamine to β-myrcene polymer living chain ends in benzene at 25 °C. Chain coupling and acetophenone polymers were not detected as side products. End-group titration with perchloric acid showed a polymer amination yield of up to 85 % of ω-terminated β-myrcene polymers. The amine ω-terminated β-myrcene polymers were synthesized with a narrow molecular weight distribution (\( \overset{-}{M_w}/\overset{-}{M_n} \) ≈ 1.1) as calculated by GPC analysis using polystyrene standards. Functionalization of the amine group in the polymer chain was corroborated with FTIR, 1H-NMR, and 13C-RMN spectra. A higher yield of the amine ω-terminated β-myrcene polymer was not achieved due to differences in isomer conformation in the β-myrcene polymer.

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References

  1. Wilbon PA, Chu F, Tang C (2013) Macromol Rapid Commun 34:8–37

    Article  CAS  Google Scholar 

  2. Holmberg AL, Reno KH, Wool RP, Epps TH (2014) Soft Matter 10:7405–7424

    Article  CAS  Google Scholar 

  3. Lligadas G, Ronda JC, Galià M, Cádiz V (2013) J Polym Sci A Polym Chem 51:2111–2124

    Article  CAS  Google Scholar 

  4. Zhang J, Li L, Boonkerd K, Zhang Z, Kim JK (2014) J Polym Res 21:404–415

    Article  Google Scholar 

  5. Gopalakrishnan P, Narayan-Sarathy S, Ghosh T, Mahajan K, Belgacem MN (2013) J Polym Res 21:340–349

    Article  Google Scholar 

  6. Xin Y, Uyama H (2012) J Polym Res 19:15–22

    Article  Google Scholar 

  7. Trumbo DL (1993) Polym Bull 31:629–636

    Article  CAS  Google Scholar 

  8. Newmark RA, Majumdar RN (1988) J Polym Sci A Polym Chem 26:71–77

    Article  CAS  Google Scholar 

  9. Loughmari S, Hafid A, Bouazza A, Bouadili AE, Zinck P, Visseaux M (2012) J Polym Sci A Polym Chem 52:2898–2905

    Article  Google Scholar 

  10. Pérez-Perrino M, Navarro R, Prucker O, Rühe J (2014) Macromolecules 47:2695–2702

    Article  Google Scholar 

  11. Kubo M, Takeuchi H, Ohara T, Itoh T, Nagahata R (1999) J Polym Sci A Polym Chem 37:2027–2033

    Article  CAS  Google Scholar 

  12. O’Brien CP, Rice JK, Dadmun MD (2004) Eur Polym J 40:1515–1523

    Article  Google Scholar 

  13. Orr CA, Cernohous JJ, Guegan P, Hirao A, Jeon HK, Macosko CW (2001) Polymer 42:8171–8178

    Article  CAS  Google Scholar 

  14. Aliferis T, Iatrou H, Hadjichristidis N (2004) Biomacromolecules 5:1653–1656

    Article  CAS  Google Scholar 

  15. Schlaad H, Antonietti M (2003) Eur Phys J E 10:17–23

    Article  CAS  Google Scholar 

  16. Zhu MQ, Xiang L, Yang K, Shen LJ, Long F, Fan JB, Yi HQ, Xiang J, Aldred M (2012) J Polym Res 19:9808–9819

    Article  Google Scholar 

  17. Hong K, Uhrig D, Mays JW (1999) Curr Opin Solid State Mater Sci 4:531–538

    Article  CAS  Google Scholar 

  18. Hadjichristidis N, Pitsikalis M, Pispas S, Iatrou H (2001) Chem Rev 101:3747–3792

    Article  CAS  Google Scholar 

  19. Hirao A, Hayashi M (1999) Acta Polym 50:219–231

    Article  CAS  Google Scholar 

  20. Hsieh HL, Quirk RP (1996) Anionic polymerization principles and practical application. Marcel Dekker, New York

    Google Scholar 

  21. Quirk RP, Chavan V, Janoski J, Yol A, Wesdemiotis C (2013) Macromol Symp 323:51–57

    Article  CAS  Google Scholar 

  22. Hirao A, Loykulnant S, Ishizone T (2002) Prog Polym Sci 27:1399–1471

    Article  CAS  Google Scholar 

  23. Pispas S (2006) J Polym Sci A Polym Chem. 44:606–613

    Article  CAS  Google Scholar 

  24. Anderson BC, Andrews GD, Arthur Jr P, Jacobson HW, Melby LR, Playtis AJ, Sharkey WH (1981) Macromolecules 14:1599–1601

    Article  CAS  Google Scholar 

  25. Higginson WC, Wooding NS (1952) J Chem Soc 760–774

  26. Quirk RP, Cheng PL (1986) Macromolecules 19:1291–1294

    Article  CAS  Google Scholar 

  27. Cernohous JJ, Macosko CW, Hoye TR (1998) Macromolecules 31:3759–3763

    Article  CAS  Google Scholar 

  28. Nakahama S, Hirao A (1990) Prog Polym Sci 15:299–335

    Article  CAS  Google Scholar 

  29. Nakahama S, Hirao A (1992) Prog Polym Sci 17:283–317

    Article  Google Scholar 

  30. Green TW, Wuts PGM (1999) Protective groups in organic synthesis, 3rd edn. Wiley, New York

    Book  Google Scholar 

  31. Hattori I, Hirao A, Yamaguchi K, Nakahama S, Yamazaki N (1983) Makromol Chem 184:1355–1362

    Article  CAS  Google Scholar 

  32. Hirao A, Hattori I, Sasagawa T, Yamaguchi K, Nakahama S (1982) Makromol Chem Rapid Commun 3:59–63

    Article  CAS  Google Scholar 

  33. Quirk RP, Summers GJ (1990) Br Polym J 22:249–254

    Article  CAS  Google Scholar 

  34. Quirk RP, Tae-Hee C, Taejun Y (2002) Macromol Chem Phys 203:1178–1187

    Article  CAS  Google Scholar 

  35. Sen MY (2005) Synthesis of middle-chain carboxyl- and primary amine-functionalized polystyrene using anionic polymerization techniques. M.S. Thesis, The University of Akron, Akron, Ohio

  36. Corcia AD, Liberti A, Sambucini C, Samperi R (1978) J Chromatogr 152:63–67

    Article  Google Scholar 

  37. Quirk RP, Gomochak DL, Bhatia RS, Wesdemiotis C, Arnould MA, Wollyung K (2003) Macromol Chem Phys 204:2183–2196

    Article  CAS  Google Scholar 

  38. Wehrli FW, Wirrhlin T (1978) Interpretation of carbon-13 NMR spectra. Heydon, London

    Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge financial support from Consejo Nacional de Ciencia y Tecnología (CONACYT 82698) of México and the scholarship awarded to Mónica Campos Covarrubias.

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Authors and Affiliations

  1. Facultad de Ingeniería Química, Campus de Ingenierías y Ciencias Exactas, Periférico Norte Kilómetro 33.5, Tablaje Catastral 13615, Col. Chuburná de Hidalgo Inn, C.P. 97203, Mérida, Yucatán, México

    A. Ávila-Ortega, Cristian Carrera-Figueiras & M. Campos-Covarrubias

  2. Unidad de Materiales, Laboratorio de Membranas, Centro de Investigación Científica de Yucatán, A.C. Calle 43 No. 130, Colonia chuburná de hidalgo, CP 97200, Mérida, Yucatán, México

    Manuel Aguilar-Vega & Maria I. Loría Bastarrachea

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  1. A. Ávila-Ortega
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  2. Manuel Aguilar-Vega
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  3. Maria I. Loría Bastarrachea
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  4. Cristian Carrera-Figueiras
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  5. M. Campos-Covarrubias
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Correspondence to A. Ávila-Ortega.

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Ávila-Ortega, A., Aguilar-Vega, M., Loría Bastarrachea, M.I. et al. Anionic synthesis of amine ω-terminated β-myrcene polymers. J Polym Res 22, 226 (2015). https://doi.org/10.1007/s10965-015-0856-6

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  • DOI: https://doi.org/10.1007/s10965-015-0856-6

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