Synthesis and characterization of elastomeric, biobased, nonisocyanate polyurethane from natural rubber
Ruedee Jaratrotkamjorn
Department of Materials Science and Technology, Faculty of Science, Prince of Songkla University, Songkhla, 90112 Thailand
Search for more papers by this authorArnaud Nourry
Unité Mixte de Recherche (France) Centre National de la Recherche Scientifique 6283, Institut des Molécules et Matériaux du Mans, Université du Maine, L’Université Nantes Angers Le Mans, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France
Search for more papers by this authorPamela Pasetto
Unité Mixte de Recherche (France) Centre National de la Recherche Scientifique 6283, Institut des Molécules et Matériaux du Mans, Université du Maine, L’Université Nantes Angers Le Mans, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France
Search for more papers by this authorEmilie Choppé
Unité Mixte de Recherche (France) Centre National de la Recherche Scientifique 6283, Institut des Molécules et Matériaux du Mans, Université du Maine, L’Université Nantes Angers Le Mans, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France
Search for more papers by this authorWannarat Panwiriyarat
Faculty of Science and Industrial Technology, Prince of Songkla University, Surat Thani Campus, Surat Thani, 84000 Thailand
Search for more papers by this authorCorresponding Author
Varaporn Tanrattanakul
Department of Materials Science and Technology, Faculty of Science, Prince of Songkla University, Songkhla, 90112 Thailand
Correspondence to: V. Tanrattanakul (E-mail: [email protected]) and J.-F. Pilard (E-mail: [email protected])Search for more papers by this authorCorresponding Author
Jean-François Pilard
Unité Mixte de Recherche (France) Centre National de la Recherche Scientifique 6283, Institut des Molécules et Matériaux du Mans, Université du Maine, L’Université Nantes Angers Le Mans, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France
Correspondence to: V. Tanrattanakul (E-mail: [email protected]) and J.-F. Pilard (E-mail: [email protected])Search for more papers by this authorRuedee Jaratrotkamjorn
Department of Materials Science and Technology, Faculty of Science, Prince of Songkla University, Songkhla, 90112 Thailand
Search for more papers by this authorArnaud Nourry
Unité Mixte de Recherche (France) Centre National de la Recherche Scientifique 6283, Institut des Molécules et Matériaux du Mans, Université du Maine, L’Université Nantes Angers Le Mans, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France
Search for more papers by this authorPamela Pasetto
Unité Mixte de Recherche (France) Centre National de la Recherche Scientifique 6283, Institut des Molécules et Matériaux du Mans, Université du Maine, L’Université Nantes Angers Le Mans, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France
Search for more papers by this authorEmilie Choppé
Unité Mixte de Recherche (France) Centre National de la Recherche Scientifique 6283, Institut des Molécules et Matériaux du Mans, Université du Maine, L’Université Nantes Angers Le Mans, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France
Search for more papers by this authorWannarat Panwiriyarat
Faculty of Science and Industrial Technology, Prince of Songkla University, Surat Thani Campus, Surat Thani, 84000 Thailand
Search for more papers by this authorCorresponding Author
Varaporn Tanrattanakul
Department of Materials Science and Technology, Faculty of Science, Prince of Songkla University, Songkhla, 90112 Thailand
Correspondence to: V. Tanrattanakul (E-mail: [email protected]) and J.-F. Pilard (E-mail: [email protected])Search for more papers by this authorCorresponding Author
Jean-François Pilard
Unité Mixte de Recherche (France) Centre National de la Recherche Scientifique 6283, Institut des Molécules et Matériaux du Mans, Université du Maine, L’Université Nantes Angers Le Mans, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France
Correspondence to: V. Tanrattanakul (E-mail: [email protected]) and J.-F. Pilard (E-mail: [email protected])Search for more papers by this authorABSTRACT
Linear and crosslinked polyhydroxyurethanes (PHUs) based on natural rubber (NR) were synthesized by a polyaddition reaction without a solvent or catalyst to exploit the reactivity of diamines or triamines with dicyclic carbonate groups. Oligo-isoprenes were obtained from the controlled oxidative degradation of NR and successive modifications of the chain ends. The syntheses of linear PHU were carried out with two approaches. The first one consisted of a reaction between amino telechelic oligo-isoprenes and aromatic or aliphatic dicyclic carbonates. The second approach proceeded through a reaction between oligo-isoprenes bearing cyclic carbonate chain ends and difunctional or trifunctional amines. The evolution of these reactions was studied by Fourier transform infrared spectrometry. The influence of the carbonate-to-amine molar ratio, the chain length of the oligo-isoprenes, and the reaction temperatures were investigated. The thermal properties of the PHUs were studied by differential scanning calorimetry and thermogravimetric analysis. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45427.
Supporting Information
Additional Supporting Information may be found in the online version of this article
Filename | Description |
---|---|
app45427-sup-0001-suppinfo_caption.docx14.4 KB | Supporting Information |
app45427-sup-0002-suppinfo.pdf1.4 MB | Supporting Information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
REFERENCES
- 1 Matsumura, S.; Soeda, Y.; Toshima, K. Appl. Microbiol. Biotechnol. 2006, 70, 12.
- 2 Cornille, A.; Auvergne, R.; Figovsky, O.; Boutevin, B.; Caillol, S. Eur. Polym. J. 2017, 87, 535.
- 3 Tomita, H.; Sanda, F.; Endo, T. J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 162.
- 4 Cornille, A.; Michaud, G.; Simon, F.; Fouquay, S.; Auvergne, R.; Boutevin, B.; Caillol, S. Eur. Polym. J. 2016, 84, 404.
- 5 Cornille, A.; Guillet, C.; Benyahya, S.; Negrell, C.; Boutevin, B.; Caillol, S. Eur. Polym. J. 2016, 84, 873.
- 6 Tryznowski, M.; Świderska, A.; Żołek-Tryznowska, Z.; Gołofit, T.; Parzuchowski, P. G. Polymer 2015, 80, 228.
- 7 Helou, M.; Carpentier, J.-F.; Guillaume, S. M. Green Chem. 2011, 13, 266.
- 8 Benyahya, S.; Desroches, M.; Auvergne, R.; Carlotti, S.; Caillol, S.; Boutevin, B. Polym. Chem. 2011, 2, 2661.
- 9 Kim, M.-R.; Kim, H.-S.; Ha, C.-S.; Park, D.-W.; Lee, J.-K. J. Appl. Polym. Sci. 2001, 81, 2735.
- 10 Ochiai, B.; Inoue, S.; Endo, T. J. Polym. Sci. Part A: Polym. Chem. 2005, 43, 6613.
- 11 Kihara, N.; Endo, T. J. Polym. Sci. Part A: Polym. Chem. 1993, 31, 2765.
- 12 Ochiai, B.; Kojima, H.; Endo, T. J. Polym. Sci. Part A: Polym. Chem. 2014, 52, 1113.
- 13 Tomita, H.; Sanda, F.; Endo, T. J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 3678.
- 14 Diakoumakos, C. D.; Kotzev, D. L. Macromol. Symp. 2004, 216, 37.
- 15 Annunziata, L.; Diallo, A. K.; Fouquay, S.; Michaud, G.; Simon, F.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume, S. M. Green Chem. 2014, 16, 1947.
- 16 Duval, C.; Kébir, N.; Jauseau, R.; Burel, F. J. Polym. Sci. Part A: Polym. Chem. 2016, 54, 758.
- 17 Blain, M.; Jean-Gérard, L.; Auvergne, R.; Benazet, D.; Caillol, S.; Andrioletti, B. Green Chem. 2014, 16, 4286.
- 18 Lambeth, R. H.; Henderson, T. J. Polymer 2013, 54, 5568.
- 19 Cornille, A.; Blain, M.; Auvergne, R.; Andrioletti, B.; Boutevin, B.; Caillol, S. Polym. Chem. 2017, 8, 592.
- 20 Sadaka, F.; Campistron, I.; Laguerre, A.; Pilard, J.-F. Polym. Degrad. Stab. 2012, 97, 816.
- 21 Panwiriyarat, W.; Tanrattanakul, V.; Pilard, J.-F.; Pasetto, P.; Khaokong, C. Mater. Sci. Forum 2011, 695, 316.
- 22 Panwiriyarat, W.; Tanrattanakul, V.; Pilard, J.-F.; Pasetto, P.; Khaokong, C. J. Appl. Polym. Sci. 2013, 130, 453.
- 23 Panwiriyarat, W.; Tanrattanakul, V.; Pilard, J.-P.; Pasetto, P.; Khaokong, C. J. Polym. Environ. 2013, 21, 807.
- 24 Chumeka, W.; Pasetto, P.; Pilard, J.-F.; Tanrattanakul, V. J. Appl. Polym. Sci. 2015, 132, DOI: 10.1002/app.41426.
- 25 Panwiriyarat, W.; Tanrattanakul, V.; Pilard, J.-P.; Burel, F.; Kébir, N. J. Appl. Polym. Sci. 2016, 133, DOI: 10.1002/app.42943.
- 26 Rattanapan, S.; Pasetto, P.; Pilard, J.-F.; Tanrattanakul, V. J. Polym. Res. 2016, 23, 182.
- 27 Thébault, M.; Pizzi, A.; Dumarçay, S.; Gerardin, P.; Fredon, E.; Delmotte, L. Eur. Polym. J. 2014, 59, 329.
- 28 Thébault, M.; Pizzi, A.; Essawy, H. A.; Barhoum, A. Ind. Crops. Prod. 2015, 65, 513.
- 29 Kathalewar, M.; Sabnis, A.; D’Mello, D. Eur. Polym. J. 2014, 57, 99.
- 30 Kathalewar, M.; Sabnis, A. J. Appl. Polym. Sci. 2015, 132, DOI: 10.1002/app.41391.
- 31 Besse, V.; Auvergne, R.; Carlotti, S.; Boutevin, G.; Otazaghine, B.; Caillol, S.; Pascault, J.-P.; Boutevin, B. React. Funct. Polym. 2013, 73, 588.
- 32 Tamami, B.; Sohn, S.; Wilkes, G. L. J. Appl. Polym. Sci. 2004, 92, 883.
- 33 Javni, I.; Hong, D. P.; Petrović, Z. S. J. Appl. Polym. Sci. 2008, 108, 3867.
- 34 Javni, I.; Hong, D. P.; Petrović, Z. S. J. Appl. Polym. Sci. 2012, 128, 566.
- 35 Kébir, N.; Morandi, G.; Campistron, I.; Laguerre, A.; Pilard, J.-F. Polymer 2005, 46, 6844.
- 36 Jaratrotkamjorn, R.; Khaokong, C.; Tanrattanakul, V. J. Appl. Polym. Sci. 2012, 124, 5027.
- 37 Kataoka, H. J. Chromatogr. A 1996, 733, 19.
- 38 Maisonneuve, L.; More, A. S.; Foltran, S.; Alfos, C.; Robert, F.; Landais, Y.; Thierry, T.; Grau, E.; Cramail, H. RSC. Adv. 2014, 4, 25795.
- 39 Boyer, A.; Cloulet, E.; Tassaing, T.; Gadenne, B.; Alfos, C.; Cramail, H. Green Chem. 2010, 12, 2205.
- 40 Lamarzelle, O.; Durand, P-L.; Wirotius, A-L.; Chollet, G.; Grau, E.; Cramail, H. Polym. Chem. 2016, 7, 1439.
- 41 Besse, V.; Camara, F.; Méchin, F.; Fleury, E.; Caillol, S.; Pascault, J-P.; Boutevin, B. Eur. Polym. J. 2015, 71, 1.
- 42 Carré, C.; Bonnet, L.; Avérous, L. RSC Adv. 2014, 4, 54018.
- 43 Velthoven, L. J.; Gootjes, L.; Es, D. S.; Noordover, B. A. J.; Meuldijk, J. Eur. Polym. J. 2015, 70, 125.
- 44 Wang, X.; Soucek, M. D. Prog. Org. Coat. 2013, 76, 1057.
- 45 Nanclare, J.; Petrović, Z. S.; Javni, I.; Lonescu, M.; Jaramillo, F. J. Appl. Polym. Sci. 2015, 132, DOI: 10.1002/app.42492.