Enhancement of mechanical property of modified polyurethane with bis-butyl succinate

Year 2021, Volume: 8 Issue: 2, 519 - 526, 31.05.2021

Thi Sinh Vo , Tran Thi Bich Chau Vo , Tran Trung Tien Nguyen Truong Sinh

https://doi.org/10.18596/jotcsa.878515

Cited By: 7

Abstract

In this study, we explore an a new crosslinker (bis-butyl succinate, BBS) with terminal alkyne group to react with glycidyl azide polymer-based polyurethane (original PU) via “azide-alkyne” click reaction, which has supported enhancing mechanical properties and cross-link densities of modified PUs with BBS. Besides, this crosslinker has been designed and synthesized successfully via an esterification reaction to can incorporate with the original PU through the formation of 1,2,3-triazole groups. Moreover, the mechanical properties of resultant modified PUs are investigated to indicate a relationship of mole ratio of [C≡C]/[N3] and cross-link density. Specifically, the stress and Young’s modulus of the modified PUs increase, whereas their strain decrease on increasing the synthesized BBS content regarding to the increased rigid 1,2,3-triazole networks, as well as the cross-link densities of the modified PUs increase with the BBS content through the Mooney-Rivlin equation. As such, there is an enhancement in the mechanical behaviors of the original PU cross-linked with BBS.

Keywords

Polyurethane, Cross-linker, Glycidyl azide polymer, Azide-alkyne click

Supporting Institution

No

Project Number

No

Thanks

The authors thank the support of Can Tho University.

References

• 1. Acik G, Karabulut HRF, Altinkok C, Karatavuk AO. Synthesis and characterization of biodegradable polyurethanes made from cholic acid and L-lysine diisocyanate ethyl ester. Polymer Degradation and Stability. 2019; 165: 43-8.
• 2. Caraculacu AA, Coseri S. Isocyanates in polyaddition processes. Structure and reaction mechanisms. Prog Polym Sci. 2001; 26: 799-851.
• 3. Acik B, Acik G, Erdemi H. Synthesis and characterization of bile acid, poly (ε-caprolactone) and ʟ-lysine diisocyanate ethyl ester based polyurethanes and investigation of their biodegradability properties. Eur Polym J. 2021; 146: 110247.
• 4. Binder WH, Sachsenhofer R. 'Click' chemistry in polymer and material science: An update. Macromol Rapid Comm. 2008; 29: 952-81.
• 5. Diaz DD, Punna S, Holzer P, Mcpherson AK, Sharpless KB, Fokin VV, Finn MG. Click chemistry in materials synthesis. 1. Adhesive polymers from copper-catalyzed azide-alkyne cycloaddition. J Polym Sci Pol Chem. 2004; 42: 4392-403.
• 6. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed. 2002; 41: 2596-9.
• 7. Vo TS, Vo TTBC. Preparation and Characterization of Bis-Propargyl-Succinate, and its Application in Preliminary Healing Ability of Crosslinked Polyurethane using" Azide-Alkyne" Click. Journal of Engineering Science & Technology Review. 2020; 13.
• 8. Wool RP. Mechanisms of frequency shifting in the infrared spectrum of stressed polymer. Journal of Polymer Science, Polymer Physics Edition. 1975; 13: 1795-808.
• 9. Wool RP. Infrared studies of deformation in semicrystalline polymers. Polymer Engineering and Science. 1980; 20: 805-15.
• 10. Cifre JGH, de la Torre JG. Orientation of polymer chains in dilute solution under shear: Effect of chain model and excluded volume. Macromol Theor Simul. 2004; 13: 273-9.
• 11. Ward IM, Hadley DW. An introduction to the mechanical properties of solid polymers. John Wiley & Sons, Chichester,. 2004; ISBN: 0-471-93887-4.
• 12. Keicher T, Kuglstatter W, Eisele S, Wetzel T, Krause H. Isocyanate-Free Curing of Glycidyl Azide Polymer (GAP) with Bis-Propargyl-Succinate (II). Propellants, Explosives, Pyrotechnics. 2009; 34: 210-7.
• 13. Flory PJ. Statistical mechanics of swelling of network structures. J Chem Phys. 1950; 18: 108 – 11.
• 14. Mullins L. Determination of degree of crosslinking in natural rubber vulcanizates (Part 3). Journal of Applied Polymer Science. 1959; 1: 1 – 7.
• 15. Hagen R, Salmen L, Stenberg B. Effects of the type of crosslink on viscoelastic properties of natural rubber. J Polym Sci Polym Phys. 1996; 34: 1997-2006.