Skip to main content

Synthesis, characterization and ring opening activity of barium mercaptoacetate towards ε-caprolactone

Abstract

A novel alkaline earth metal salt such as barium mercaptoacetate (Ba-MA) was successfully synthesized and characterized by various analytical techniques such as FTIR spectroscopy, UV–visible spectroscopy, XRD, particle size analysis and SEM. Further, its application towards the ring opening polymerization of ε-caprolactone (CL) as a novel initiator was tested at two different experimental conditions such as monomer to initiator ratio [M/I] variation and temperature variation under nitrogen atmosphere with mild stirring condition. The poly(caprolactone) (PCL) formation in the presence of Ba-MA was confirmed by measuring the melting temperature (Tm), degradation temperature (Td), XRD and GPC of PCL. The Tm of PCL varied between 68.4 and 71.6 °C while increasing the [M/I]. The chemical structure and functional groups of PCL were confirmed by NMR spectroscopy and FTIR spectroscopy, respectively. The band gap (Eg) value increased with the increase in [M/I] ratio due to the decrease in Ba content.

This is a preview of subscription content, access via your institution.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

References

  1. Sharma P, Virk HS (2009) Fabrication of nanoparticles of Ba carbonate/oxalate using reverse micelle techniques. Open Surf Sci J 1:34–39

    Article  CAS  Google Scholar 

  2. Ramaswamy V, Vimalathithan M, Ponnusamy V (2010) Synthesis of well dispersed, elliptical shaped BaSO4 nanoparticles via water-chloroform mixed solvent. Arch Phys Res 1:217–226

    CAS  Google Scholar 

  3. Raju S, Muralidharan R, Sonila H (2014) Synthesis, spectral and antibacterial studies of semi-organic single crystal: barium thiourea chloride. Res J Pharm Biol Chem Sci 5:1440–1445

    CAS  Google Scholar 

  4. Zelati A, Amirabadizadch A, Kompany A (2011) Preparation and characterization of barium carbonate nanoparticles. Int J Chem Eng Appl 2:299–303

    CAS  Google Scholar 

  5. Ramaswamy V, Vimalathithan M, Ponnusamy V (2012) Synthesis of monodispersed barium sulphate nanoparticles using water-benzene mixed solvent. Adv Mater Lett 3:29–33

    Article  CAS  Google Scholar 

  6. Bauer S, Muller H, Bein T, Srock N (2005) Synthesis and characterization of the open-framework barium bisphosphonate [Ba3(O3PCH2NH2CH2PO3)2(H2O)4]·3H2O. Inorg Chem 44:9464–9470

    Article  CAS  PubMed  Google Scholar 

  7. Hopwood JD, Marn S (1997) Synthesis of BaSO4 nanoparticle and nano filaments in reverse micelles and microemulsion. Chem Mater 9:1819–1828

    Article  CAS  Google Scholar 

  8. Damavarapu R, Klapotke TM, Stierstorfer J, Tarantik KR (2010) Barium salts of tetrazole derivatives—synthesis and characterization. Propellants Explos Pyrotech 35:395–406

    Article  CAS  Google Scholar 

  9. Zhang C, Shen E, Wang E, Kang Z, Gao L, Hu C, Xu L (2006) One-step solvothermal synthesis of high ordered BaWO4 and BaMoO4 nanostructures. Mater Chem Phys 96:240–243

    Article  CAS  Google Scholar 

  10. Errandonea D (2009) Comment on molten salt synthesis of barium molybdate and tungstate microcrystals. Mater Lett 63:160–161

    Article  CAS  Google Scholar 

  11. Zelati A, Amirabadizadeh A, Kompany A (2011) Preparation and characterization of barium carbonate nanoparticles. Int J Chem Eng Appl 2:299–303

    CAS  Google Scholar 

  12. Jacobo SE, Pascual CD, Clemente RR, Blesa MA (1997) Synthesis of ultrafine particles of barium ferrite by chemical co-precipitation. J Mater Sci 32:1025–1028

    Article  CAS  Google Scholar 

  13. Hu MZC, Miller GA, Payzant EA, Rawn CJ (2000) Homogeneous (co)precipitation of inorganic salts for synthesis of monodispersed barium titanate particles. J Mater Sci 35:2927–2936

    Article  CAS  Google Scholar 

  14. Luo Z, Li H, Xia J, Zhu W, Guo J, Zhang B (2007) Microwave assisted synthesis of barium tungstate nanosheets and nanobelts by using polymer PVP micelle as templates. Mater Lett 1:1845–1848

    Article  CAS  Google Scholar 

  15. Chew K, Bakar M, Abu Bakar N (2013) Synthesis of barium nickel titanium oxide stabilized by citric acid. Model Numer Simul Mater Sci 3:23–27

    Article  Google Scholar 

  16. Huang KC, Huang TC, Hsieh WFG (2009) Morphology controlled synthesis of barium titanate nanostructures. Inorg Chem 48:9180–9184

    Article  CAS  PubMed  Google Scholar 

  17. Shen Y, Li C, Zhu X, Xie A, Qiu L, Zhu J (2007) Study on the preparation and formation mechanism of barium sulphate nanoparticles modified by different organic acids. J Chem Sci 119:319–324

    Article  CAS  Google Scholar 

  18. Dutta PK, Asiaie R, Akbar SA, Zhu W (1994) Hydrothermal synthesis and dielectric properties of tetragonal BaTiO3. Chem Mater 6:1542–1548

    Article  CAS  Google Scholar 

  19. Wu D, Lv Y, Guo R, Liu B, Wang H, Wei Z (2017) Kinetics of stannous octoate catalyzed ring opening polymerization of caprolactone. Macromol Res 25:1070–1076

    Article  CAS  Google Scholar 

  20. Sawdon AJ, Peng CA (2013) Guanosine based antiviral acyclovir incorporated in ring opening polymerization of ε-caprolactone. Macromol Res 21:1–8

    Article  CAS  Google Scholar 

  21. Scrivanti A, Beroluzzi M, Gatto M (2016) New heteroscorpionate lanthanide complexes for ring-opening polymerisation of ε-caprolactone and rac-lactide. Chem Pap 70:53–61

    Article  CAS  Google Scholar 

  22. Ni X, Liang Z, Ling J, Li X, Shen Z (2011) Controlled ring-opening polymerization of ε-caprolactone initiated by in situ formed yttrium trisalicylaldimine complexes, and their study by density functional theory. Polym Int 60:1715–1722

    Article  CAS  Google Scholar 

  23. Liu J, Liu L (2004) Ring opening polymerization of ε-caprolactone initiated by natural amino acids. Macromolecules 37:2674–2676

    Article  CAS  Google Scholar 

  24. Anbarasan R, Jeyapriya M, Meenarathi B, Tung KL (2018) Low temperature splinting activity and catalytic behavior of nano Ag doped sulphamicacid bridged diblock copolymer. Polym Adv Technol 29:2025–2035

    Article  CAS  Google Scholar 

  25. Murugesan A, Palanikumar S, Anbarasan R (2016) Synthesis, characterization and humidity sensor application of poly(methylorange) based triblock copolymer. J Chem Pharm Res 8:71–81

    CAS  Google Scholar 

  26. Agathian K, Kannammal L, Meenarathi B, Kailash S, Anbarasan R (2018) Synthesis, characterization and adsorption behavior of cotton fiber based Schiff base. Int J Biol Macromol 107:1102–1112

    Article  CAS  PubMed  Google Scholar 

  27. Rajkumar B, Meenarathi B, Anbarasan R (2016) Synthesis and characterization of novel fluorescent amphilic diblock copolymers. Polym Bull 73:2147–2163

    Article  CAS  Google Scholar 

  28. Jeyapriya M, Meenarathi B, Anbarasan R (2016) Synthesis, characterization, catalytic and splinting activity of nano Ag end capped l-glutathione bridged amphiphilic diblock copolymer. J Appl Polym Sci 133:1–11

    Article  CAS  Google Scholar 

  29. Meenarathi B, Palanikumar S, Kannammal L, Anbarasan R (2015) Synthesis, characterization and catalytic activity of Ag-acidfuchsin nanohybrid system towards the ring opening polymerization of caprolactone. Spectrochim Acta Part A 135:93–100

    Article  CAS  Google Scholar 

  30. Meenarathi B, Chen HH, Chen PH, Anbarasan R (2013) Near infrared dye functionalized MWCNT as an effective initiator for the ring opening polymerization of ε-caprolactone. J Polym Res 20:118–128

    Article  CAS  Google Scholar 

  31. Kailash S, Meenarathi B, Palanikumar S, Anbarasan R (2015) Synthesis, characterization, drug delivery, and splinting activity of folic acid bridged poly(ɛ-caprolactone-co-tetrahydrofuran). Int J Polym Mater Polym Biomater 64:620–627

    Article  CAS  Google Scholar 

  32. Grobelny Z, Golba S, Suliga JJ (2018) Mechanism of ε-caprolactone polymerization in the presence of alkali metal salts: investigation of initiation course and determining polymers structure by MALTI-TOF mass spectrometry. Polym Bull. https://doi.org/10.1007/s00289-018-2554-0

    Article  Google Scholar 

  33. Mahalakshmi S, Alagesan T, Parthasarathi V, Tung KL, Anbarasan R (2018) Non-isothermal crystallization kinetics and degradation kinetics studies on barium thioglycolate end capped poly(ε-caprolactone). J Therm Anal Calorim. https://doi.org/10.1007/s10973-018-7514-2

    Article  Google Scholar 

  34. Mahalakshmi S, Alagesan T, Parthasarathi V, Anbarasan R (2018) Non-isothermal crystallization and degradation kinetics studies of synthesized Mo-thioglycolate end capped poly(ε-caprolactone). Macromol Res. https://doi.org/10.1007/s13233-018

    Article  Google Scholar 

  35. Mahalakshmi S, Alagesan T, Parthasarathi V, Anbarasan R (2018) Non-isothermal crystallization and degradation kinetics studies on Mn-thioglycolate end capped poly(ε-caprolactone). Polym Eng Sci. https://doi.org/10.1002/pen.24979

    Article  Google Scholar 

  36. Jeyapriya M, Meenarathi B, Anbarasan R (2015) Synthesis and characterization of nano Ag end capped l-cysteine bridged diblock copolymer. Chin J Polym Sci 33:1404–1420

    Article  CAS  Google Scholar 

  37. Palanikumar S, Meenarathi B, Kannammal L, Siva P, Anabarasan R (2014) Effect of Fe3O4 on the sedimentation and structure–property relationship of starch under different pHs. Int J Biol Macromol 67:91–98

    Article  CAS  PubMed  Google Scholar 

  38. Yang X, Wang Y, Chen Y, Yan H (2016) The structural and electronic properties of BaO under epitaxial strains: first principles calculations. Acta Phys Polon A 129:64–68

    Article  CAS  Google Scholar 

  39. Jancirani A, Kohila V, Meenarathi B, Anbarasan R (2016) Synthesis, characterisation and non-isothermal degradation kinetics of novel poly(mono ethylene glycol dimethacrylate-co-4-aminobenzoate). Bull Mater Sci 39:1725–1733

    Article  CAS  Google Scholar 

  40. Oshimura M, Tang T, Takasu A (2011) Ring opening polymerization of caprolactone using perfluoroalkanesulfonates and perfluoroalkanesulfonimides as organic catalysts. J Polym Sci Part A Polym Chem 49:1210–1218

    Article  CAS  Google Scholar 

  41. Oshimura M, Takasu A (2010) Controlled ring opening polymerization of ε-caprolactone catalyzed by rare earth perfluoroalkanesulfonates and perfluoroalkanesulfonimides. Macromolecules 43:2283–2290

    Article  CAS  Google Scholar 

  42. Fan L, Zhang L, Shen Z (2004) Characteristics and kinetics of ring opening polymerization of ε-caprolactone initiated by Lanthanide tris(2,4,6-trimethylphenolate)s. Polym J 36:91–95

    Article  CAS  Google Scholar 

  43. Chen HH, Anbarasan R, Guo LS, Chen PH (2011) A novel report on Eosin Y functionalized MWCNT as an initiator for ring opening polymerization of caprolactone. Mater Chem Phys 126:584–590

    Article  CAS  Google Scholar 

  44. Zhou B, Zai Z, Huang TJ, Xu JT, Fan ZQ (2013) Synthesis and thermal behavior of poly(ε-caprolactone) grafted on multiwalled carbon nanotubes with high grafting degrees. Mater Chem Phys 137:1053–1061

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Dr. N. Sundararajan, Associate Professor, Department of English, KCET, Virudhunagar is gratefully acknowledged for his valuable help during the preparation of this manuscript.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to R. Anbarasan or Kuo-Lun Tung.

Ethics declarations

Conflict of interest

There is no conflict of interest among the authors.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Anbarasan, R., Kannammal, L., Meenarathi, B. et al. Synthesis, characterization and ring opening activity of barium mercaptoacetate towards ε-caprolactone. Polym. Bull. 76, 5381–5397 (2019). https://doi.org/10.1007/s00289-018-2658-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-018-2658-6

Keywords

  • Ba-mercaptoacetate
  • Ring opening polymerization
  • Degradation temperature
  • Band gap energy