Journal of Polymers and the Environment

, Volume 26, Issue 5, pp 1940–1949 | Cite as

Novel Bio-based Bisfuranic Polyesters by Interchange Reactions Between Bisfuranic Diester Bearing Pendent Carboxylic Acid Group and Bio-based Dihydroxy Compounds

Original Paper

Abstract

Five new polyesters fully based on renewable organic compounds were synthesized by melt polycondensation of a new bisfuranic monomer prepared from methyl 2-furoate and levulinic acid with bio-based aliphatic dihydroxy compounds. The polymerization process consisted of a precondensation step under a stream of dry argon at atmospheric pressure involving elimination of methanol, followed with a melt polycondensation step at 180 °C under vacuum. The polyesters were characterized by infrared spectroscopy (FTIR) and elemental analysis. The thermal behavior of the polyesters was studied by differential scanning calorimetry (DSC) and thermogravimetric analysis. All polyesters synthesized showed good thermal stabilities, they experience only 1% mass loss at temperatures higher than 270 °C. The glass transition temperatures (Tg) of the polyesters, measured by DSC, were in the range from 37 to 119 °C. The swelling capacity was measured by beaker test method; the capacity range observed was from 112 to 232%. Based on this percentage range the polyesters are generally considered hydrophilic.

Graphical Abstract

Keywords

Bio-based polyester Melt polycondensation Bisfuran Aliphatic dihydroxy compounds Interchange reactions 

Notes

Acknowledgements

This work was performed in The University of Jordan. The authors gratefully acknowledge The University of Jordan for the financial support of this project (Recommendation number 2/2014–2015) and for providing facilities and chemicals. The authors thank Ms. Fatima Mustafa and Ms. Rula Hassouneh for NMR measurements and Ms. Ruba Zalloum and Mrs. Abeer Malhis for FTIR and thermal analyses measurements.

References

  1. 1.
    Binder J, Raines R (2009) Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J Am Chem Soc 131:1979–1985CrossRefGoogle Scholar
  2. 2.
    Román-Leshkov Y, Chheda J, Dumesic J (2006) Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312:1933–1937CrossRefGoogle Scholar
  3. 3.
    Zhao H, Holladay J, Brown H, Zhang Z (2007) Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 316:1597–1600CrossRefGoogle Scholar
  4. 4.
    Gupta N, Nishimura S, Takagaki A, Ebitani K (2011) Hydrotalcite-supported gold-nanoparticle-catalyzed highly efficient base-free aqueous oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under atmospheric oxygen pressure. Green Chem 13:824–827CrossRefGoogle Scholar
  5. 5.
    Lilga M, Hallen R, Gray M (2010) Production of oxidized derivatives of 5-hydroxymethylfurfural (HMF). Top Catal 53:1264–1269CrossRefGoogle Scholar
  6. 6.
    Wilsens C, Noordover B, Rastogi S (2014) Aromatic thermotropic polyesters based on 2,5-furandicarboxylic acid and vanillic acid. Polymer 55:2432–2439CrossRefGoogle Scholar
  7. 7.
    Okada M, Tachikawa K, Aoi K (1997) Biodegradable polymers based on renewable resources II. Synthesis and biodegradability of polyesters containing furan rings. J Polym Sci A 35:2729–2737CrossRefGoogle Scholar
  8. 8.
    Gandini A, Belgacem M (1997) Furans in poly(BFL-1,3- butylene ester) chemistry. Prog Polym Sci 22:1203–1379CrossRefGoogle Scholar
  9. 9.
    Burgess S, Leisen J, Kraftschik B, Mubarak C, Kriegel R, Koros W (2014) Chain mobility, thermal, and mechanical properties of poly(ethylene furanoate) compared to poly(ethylene terephthalate). Macromolecules 47:1383–1391CrossRefGoogle Scholar
  10. 10.
    Hui Z, Gandini A (1992) Polymeric Schiff bases bearing furan moieties. Eur Polym J 28:1461–1469CrossRefGoogle Scholar
  11. 11.
    Boufi S, Gandini A, Belgacem M (1995) Urethanes and polyurethanes bearing furan moieties: 5. Thermoplastic elastomers based on sequenced structures. Polymer 36:1689–1696CrossRefGoogle Scholar
  12. 12.
    Mitiakoudis A, Gandini A (1991) Synthesis and characterization of furanic polyamides. Macromolecules 24:830–835CrossRefGoogle Scholar
  13. 13.
    Gaitonde V, Lee K, Kirschbaum K, Sucheck S (2014) Bio-based bisfuran: Synthesis, crystal structure, and low molecular weight amorphous polyester. Tetrahedron Lett 55:4141–4145CrossRefGoogle Scholar
  14. 14.
    Ziach K, Jurczak J (2015) Chiral crystals from dynamic combinatorial libraries of achiral macrocyclic imines. Cryst Growth Des 15:4372–4376CrossRefGoogle Scholar
  15. 15.
    Skouta M, Lesimple A, Le Bigot Y, Delmas M (1994) New method for the synthesis of difuranic diamines and tetrafuranic tetraamines. Synth Commun 24:2571–2576CrossRefGoogle Scholar
  16. 16.
    Cawse J, Stanford J, Still R (1984) Polymers from renewable sources, 1. Diamines and diisocyanates containing difurylalkane moieties. Macromol Chem 185:697–707CrossRefGoogle Scholar
  17. 17.
    Khrouf A, Abid M, Boufi S, Gharbi R, Gandini A (1998) Polyesters bearing furan moieties, a detailed investigation of the polytransesterification of difuranic diesters with different diols. Macromol Chem Phys 199:2755–2765Google Scholar
  18. 18.
    Pennanen S, Nyman G (1972) Studies of furan series part I. The acidic condensation of aldehydes with methyl 2-furoate. Acta Chem Scand 26:1018–1022CrossRefGoogle Scholar
  19. 19.
    Khrouf A, Boufi S, El Gharbi R, Belgacem N, Gandini A (1996) Polyesters bearing furan moieties 1. Polytransesterification involving difuranic diestersand aliphatic diols. Polym Bull 37:589–596CrossRefGoogle Scholar
  20. 20.
    Kamoun W, Salhi S, Rousseau B, El Gharbi R, Fradet A (2006) Furanic-aromatic copolyesters by interchange reactions between poly(ethylene terephthalate) and poly[ethylene 5,5′-isopropylidenebis(2-furoate)]. Macromol. Chem Phys 207:2042–2049Google Scholar
  21. 21.
    Abid S, El Gharbi R, Gandini A (2004) Polyamides incorporating furan moieties. 5. Synthesis and characterisation of furan-aromatic homologues. Polymer 45:5793–5801CrossRefGoogle Scholar
  22. 22.
    Hbaieb S, Kammoun W, Delaite C, Abid S, El Gharbi R (2015) New Copolyesters containing aliphatic and bio-based furanic units by bulk copolycondensation. J Macromol Sci Pure Appl Chem 52:365–373CrossRefGoogle Scholar
  23. 23.
    Bougarech A, Abid M, DaCruz-Boisson F, Abid S, El Gharbi R, Fleury E (2014) Modulation of furanic-sulfonated isophthalic copolyesters properties through diols units control. Eur Polym J 58:207–217CrossRefGoogle Scholar
  24. 24.
    Bougarech A, Abid M, Gouanve F, Espuche E, El Gharbi R, Fleury E (2013) Synthesis, characterization and water sorption study of new bio-based (furanic-sulfonated) copolyesters. Polymer 54:5482–5489CrossRefGoogle Scholar
  25. 25.
    Abid M, Abid S, El Gharbi R (2012) Polyterephthalates bearing bio-based moieties. J Macromol Sci Pure Appl Chem 49:758–763CrossRefGoogle Scholar
  26. 26.
    Barbooti M, Baysal A, Alderzi (2015) Spectrochemical methods of analysis. In: Barbooti M (ed) Environmental applications of instrumental chemical analysis, Taylor & Francis, Boca RatonCrossRefGoogle Scholar
  27. 27.
    Ibrahim M, Nada A, Kamal D (2005) Density functional theory and FTIR spectroscopic study of carboxyl group. Indian J Pure Appl Phys 43:911–917Google Scholar
  28. 28.
    Gharbi S, Andreolety J, Gandini A (2000) Polyesters bearing furan moieties IV. Solution and interfacial polycondensation of 2,2′-bis(5-chloroformyl-2-furyl) propane with various diols and bisphenols. Eur Polym J 36:463–472CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  1. 1.Chemistry Department, School of ScienceThe University of JordanAmmanJordan

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