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Atom transfer radical polymerization of monomers containing amide and ester moieties monitored by dilatometric method

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Abstract

The kinetics of atom transfer radical polymerization of N-(S)-α-methylbenzylmethacryloylamine (S-(-)-α-MBMA) and α-methylbenzylmethacrylate (α-MBM) monomers, as assessed by % conversion, were determined at 48 °C in a toluene/ethanol mixture (60:40) by a dilatometry method. The effect of the presence of — CONH- or — COOR- moieties on the ATRP polymerization of such monomers was investigated. Controlled polymerizations were performed with the catalyst system \( \left[ {\hbox{M}} \right]/\left[ {{\hbox{R}} - {\hbox{X}}} \right]/\left[ {{\hbox{M}}{{\hbox{t}}^{\rm{n}}} - {\hbox{Y}}} \right]/\left[ {\hbox{L}} \right] \) at molar ratios of 100:15:15:15; 200:15:15:15; 300:15:15:15; and 400:15:15:15, where R-X was EBIB or MCP, M nt -Y(CuBr or CuCl) and L (Me6TREN). Also with N-S-(-)-α-MBMA, some studies used ATCA and ABPA as R-X. Plots of the ln[M]0/[M] vs t as well as from the log Rp vs log [M] showed that the ATRP processes followed a pseudo first-order kinetics with respect to the monomer concentration and that the molecular weight of the resulting polymers increased with the conversion. The ATRP results for both monomers showed a similar trend and revealed that the presence of N-S-(-)-α-MBMA (amide group) affects the polymerization, i.e. it did not react when the EBIB/CuBr/Me6TREN catalyst system was used. The Mn and Mw were determined by 1H-NMR and GPC. PDI values fell between 1.19 and 1.5, and indicated that the majority of the systems showed good control of polymerization.

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References

  1. Coessens V, Pintauer T, Matyjaszewski K (2001) Prog Polym Sci 26:337–377

    Article  CAS  Google Scholar 

  2. Davis KA, Matyjaszewski K (2002) Adv Polym Sci 159:1–166

    Article  Google Scholar 

  3. Matyjaszewski K (2003) Polym Int 52:1559–1565

    Article  CAS  Google Scholar 

  4. Tsarevsky NV, Matyjaszewski K (2007) Chem Rev 107:2270–2299

    Article  CAS  Google Scholar 

  5. Oh JK, Drumright R, Siegwart DJ, Matyjaszewski K (2008) Prog Polym Sci 33:448–477

    Article  CAS  Google Scholar 

  6. Sheiko SS, Sumerlin BS, Matyjaszewski K (2008) Prog Polym Sci 33:759–785

    Article  CAS  Google Scholar 

  7. Gao H, Matyjaszewski K (2009) Prog Polym Sci 34:317–350

    Article  CAS  Google Scholar 

  8. Matyjaszewski K (1997) J Macromol Sci Pure Appl Chem A34:1785–1801

    CAS  Google Scholar 

  9. Goto A, Fukuda T (2004) Prog Polym Sci 29:329–385

    Article  CAS  Google Scholar 

  10. Matyjaszewski K (1995) J Phys Org Chem 8:197–207

    Article  CAS  Google Scholar 

  11. Matyjaszewski K, Gaynor S, Greszta D, Mardare D, Shigemoto T (1995) J Phys Org Chem 8:306–315

    Article  CAS  Google Scholar 

  12. Gaynor S, Qiu J, Matyjaszewski K (1998) Macromolecules 31:5951–5954

    Article  CAS  Google Scholar 

  13. Haddleton DM, Martin CC, Dana BH, Duncalf DJ, Heming AM, Kukulj D, Shooter AJ (1999) Macromolecules 32:2110–2119

    Article  CAS  Google Scholar 

  14. Percec V, Barboiu B, Kim H-J (1998) J Am Chem Soc 120:305–316

    Article  CAS  Google Scholar 

  15. Kotani Y, Kato M, Kamigaito M, Sawamoto M (1996) Macromolecules 29:6979–6982

    Article  CAS  Google Scholar 

  16. Zhang X, Xia J, Matyjaszewski K (1998) Macromolecules 31:5167–5169

    Article  CAS  Google Scholar 

  17. Beers KL, Boo S, Gaynor SG, Matyjaszewski K (1999) Macromolecules 32:5772–5776

    Article  CAS  Google Scholar 

  18. Beers KL, Gaynor SG, Matyjaszewski K, Sheiko SS, Moller M (1998) Macromolecules 31:9413–9415

    Article  CAS  Google Scholar 

  19. Zhang X, Xia J, Matyjaszewski K (1999) Polym Prep Am Chem Soc, Div Polym Chem 40:440–441

    CAS  Google Scholar 

  20. Xia J, Johnson T, Gaynor S, Matyjaszewski K, DeSimone J (1999) Macromolecules 32:4802–4805

    Article  CAS  Google Scholar 

  21. Betts D, Johnson T, Anderson C, DeSimone JM (1997) Polym Prep Am Chem Soc, Div Polym Chem 38:760–761

    CAS  Google Scholar 

  22. Zhang Z, Ying S, Shi Z (1999) Polymer 40:5439–5444

    Article  CAS  Google Scholar 

  23. Listigovers NA, Georges MK, Odell PG, Keoshkerian B (1996) Macromolecules 29:8992–8993

    Article  CAS  Google Scholar 

  24. Sawamoto M, Senno M, Kotani Y, Kamigaito M (1999) Macromolecules 32:8005–8009

    Article  Google Scholar 

  25. Xue H, Xu Y-A, Ding Y-Y, Gao L-X, Ding M-X (2003) Polym Int 52:1423–1427

    Article  CAS  Google Scholar 

  26. Angiolini L, Benelli T, Giorgini L, Salatelli E (2005) Polymer 46:2424–2432

    Article  CAS  Google Scholar 

  27. Tsuji M, Sakai R, Satoh T, Kaga H, Kakuchi T (2002) Macromolecules 35:8255–8257

    Article  CAS  Google Scholar 

  28. Dasgupta A, Klapper M, Müllen K (2008) Polym Bull 60:199–210

    Article  CAS  Google Scholar 

  29. Teodorescu M, Matyjaszewski K (1999) Macromolecules 32:4826–4831

    Article  CAS  Google Scholar 

  30. Teodorescu M, Matyjaszewski K (2000) Macromol Rapid Commun 21:190–194

    Article  CAS  Google Scholar 

  31. Yañéz-Martínez B, Percino J, Chapela V (2010) J Appl Polym Sci (in press)

  32. Hernández A (2006) B. Sc. Thesis, Universidad Autónoma de Puebla, México

  33. Santamaría J (2006) M. Sc. Thesis, Universidad Autónoma de Puebla, México

  34. Camacho A (2009) B. Sc. Thesis, Universidad Autónoma de Puebla, México

  35. Gutiérrez-Pérez R, Percino MJ, Chapela VM, Alvarez C (1999) Des Monomers Polym 2:103–107

    Article  Google Scholar 

  36. Okamoto Y, Urakawa K, Ohta K, Yuki H (1978) Macromolecules 11:719–723

    Article  CAS  Google Scholar 

  37. Zeng F, Shen Y, Zhu S, Pelton R (2000) Macromolecules 33:1628–1635

    Article  CAS  Google Scholar 

  38. Alcantarilla T (2006) B. Sc. Thesis, Universidad Autónoma de Puebla

  39. Ciampolini M, Nardi N (1966) Inorg Chem 5:41–44

    Article  CAS  Google Scholar 

  40. Percino MJ, Chapela VM, Jimenez A (2004) J Appl Polym Sci 94:1662–1669

    Article  CAS  Google Scholar 

  41. Ding S, Radosz M, Shen Y (2004) Macromol Rapid Commun 25:632–636

    Article  CAS  Google Scholar 

  42. Wang JS, Matyjaszewski K (1995) J Am Chem Soc 117:5614–5615

    Article  CAS  Google Scholar 

  43. Wang JS, Matyjaszewski K (1995) Macromolecules 28:7901–7910

    Article  CAS  Google Scholar 

  44. Kato M, Sawamoto M, Higashimura T (1995) Macromolecules 28:1721–1723

    Article  CAS  Google Scholar 

  45. Matyjaszewski K, Xia J (2001) Chem Rev 101:2921–2990

    Article  CAS  Google Scholar 

  46. Kamigaito M, Ando T, Sawamoto M (2001) Chem Rev 101:3689–3746

    Article  CAS  Google Scholar 

  47. Ando T, Kamigato M, Sawamoto M (1997) Tetrahedron 53:15445–15457

    Article  CAS  Google Scholar 

  48. Matyjaszewski K, Wang JL, Grimaud T, Shipp DA (1998) Macromolecules 31:1527–1534

    Article  Google Scholar 

  49. Bellamy LJ (1975) The infra-red Spectra of Complex Molecules, 3rd edn. Wiley, New York

    Google Scholar 

  50. Nakanishi K, Solomon PH (1977) Infrared absorption spectroscopy, 2nd edn. Holden-day, Inc., Oakland

    Google Scholar 

Download references

Acknowledgements

The authors acknowledge VIEP-BUAP for financial support Projects PEZM-NAT08-G and CHCV-NAT09-G

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Authors and Affiliations

  1. Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, Complejo de Ciencias, ICUAP, Edif. 103F, 22 Sur y San Claudio, C.P. 72570, Puebla, Puebla, Mexico

    M. Judith Percino, Víctor M. Chapela, Alicia Camacho, Guillermo Soriano-Moro & Margarita Cerón

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  1. M. Judith Percino
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  2. Víctor M. Chapela
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  3. Alicia Camacho
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  4. Guillermo Soriano-Moro
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  5. Margarita Cerón
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Correspondence to M. Judith Percino.

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Percino, M.J., Chapela, V.M., Camacho, A. et al. Atom transfer radical polymerization of monomers containing amide and ester moieties monitored by dilatometric method. J Polym Res 18, 559–568 (2011). https://doi.org/10.1007/s10965-010-9449-6

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  • DOI: https://doi.org/10.1007/s10965-010-9449-6

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