journal article·2020-04

Bio-based self-healing Eucommia ulmoides ester elastomer with damping and oil resistance

Xin Qi, Jichuan Zhang, Liqun Zhang, Dongmei Yue

Journal of Materials Science· Volume 55· Issue 11
Publisher page

Abstract

Eucommia ulmoides gum (EUG) is an essential bio-based material with a similar chemical structure to natural rubber, but it is rigid plastic at room temperature due to crystallization, which limits its wide application. Herein, we report a new method for synthesis of functional Eucommia ulmoides ester (EUET) elastomer by chemical modification of EUG. First, EUG was epoxidized by performic acid formed from hydrogen peroxide and formic acid in situ in toluene solution and then subjected to ring-opening reaction with acetic acid. It was found that EUET contained both α-hydroxyl ester and β-hydroxyl ester in the molecular chain. Unlike EUG, EUET was no longer crystallized due to the reduction of regularity, and it has been successfully converted into elastomer, which was confirmed by the elastic strain recovery experiment. Furthermore, because of the presence of polar groups and the hydrogen bond between them, EUET could self-heal under the condition of 50 °C, and their vulcanizates possessed excellent mechanical properties, resilience, oil resistance and damping properties. This study may promote the application of EUG in the field of bio-based functional elastomers.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Polymer composites and self-healing · Synthetic Organic Chemistry Methods · biodegradable polymer synthesis and properties

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (33)

Show source-provided references
1. Sheldon RA (2014) Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chem 16:950–963. https://doi.org/10.1039/c3gc41935e10.1039/c3gc41935e ↗
2. Sun Z, Li F, Du H et al (2013) A novel silvicultural model for increasing biopolymer production from Eucommia ulmoides Oliver trees. Ind Crops Prod 42:216–222. https://doi.org/10.1016/j.indcrop.2012.06.00110.1016/j.indcrop.2012.06.001 ↗
3. Zhang X, Cheng C, Zhang M et al (2008) Effect of alkali and enzymatic pretreatments of Eucommia ulmoides leaves and barks on the extraction of gutta percha. J Agric Food Chem 56:8936–8943. https://doi.org/10.1021/jf800642y10.1021/jf800642y ↗
4. Sarina Zhang J, Zhang L (2012) Dynamic mechanical properties of Eucommia ulmoides gum with different degree of cross-linking. Polym Bull 68:2021–2032. https://doi.org/10.1007/s00289-012-0712-310.1007/s00289-012-0712-3 ↗
5. Wang Y, Xia L, Xin Z (2018) Triple shape memory effect of foamed natural Eucommia ulmoides gum/high-density polyethylene composites. Polym Adv Technol 29:190–197. https://doi.org/10.1002/pat.410210.1002/pat.4102 ↗
6. Xia L, Wang Y, Ma Z et al (2017) Preparation of epoxidized Eucommia ulmoides gum and its application in styrene-butadiene rubber (SBR)/silica composites. Polym Adv Technol 28:94–101. https://doi.org/10.1002/pat.386310.1002/pat.3863 ↗
7. Yang F, Liu Q, Li X et al (2017) Epoxidation of Eucommia ulmoides gum by emulsion process and the performance of its vulcanizates. Polym Bull 74:3657–3672. https://doi.org/10.1007/s00289-017-1912-710.1007/s00289-017-1912-7 ↗
8. Shao H, Yu Q, Xiao P et al (2012) Study on viscoelastic properties of epoxidized trans-1,4-polyisoprene by rubber process analyzer. Polym Sci Ser A 54:760–766. https://doi.org/10.1134/s0965545x1208010x10.1134/s0965545x1208010x ↗
9. Johnson T, Thomas S (1999) Nitrogen/oxygen permeability of natural rubber, epoxidised natural rubber and natural rubber/epoxidised natural rubber blends. Polymer (Guildf) 40:3223–3228. https://doi.org/10.1016/S0032-3861(98)00528-X10.1016/S0032-3861(98)00528-X ↗
10. Jeerupun J, Wootthikanokkhan J, Phinyocheep P (2004) Effects of epoxidation content of ENR on morphology and mechanical properties of natural rubber blended PVC. Macromol Symp 216:281–292. https://doi.org/10.1002/masy.20045122610.1002/masy.200451226 ↗
11. Pire M, Norvez S, Iliopoulos I et al (2010) Epoxidized natural rubber/dicarboxylic acid self-vulcanized blends. Polymer (Guildf) 51:5903–5909. https://doi.org/10.1016/j.polymer.2010.10.02310.1016/j.polymer.2010.10.023 ↗
12. Dahham OS, Hamzah R, Bakar MA et al (2017) NMR study of ring opening reaction of epoxidized natural rubber in presence of potassium hydroxide/isopropanol solution. Polym Test 59:55–66. https://doi.org/10.1016/j.polymertesting.2017.01.00610.1016/j.polymertesting.2017.01.006 ↗
13. Jayawardenab S, Reyx D, Durand D (1984) Synthesis of macromolecular antioxidants. Makromol Chem 185:2089–2097. https://doi.org/10.1002/macp.1984.02185100410.1002/macp.1984.021851004 ↗
14. Xu T, Jia Z, Wang S et al (2017) Self-crosslinkable epoxidized natural rubber–silica hybrids. J Appl Polym Sci 134:1–10. https://doi.org/10.1002/app.4460510.1002/app.44605 ↗
15. Kwak MJ, Kim DH, You JB et al (2018) A sub-minute curable nanoadhesive with high transparency, strong adhesion, and excellent flexibility. Macromolecules 51:992–1001. https://doi.org/10.1021/acs.macromol.7b0210210.1021/acs.macromol.7b02102 ↗
16. Li C, Liu Y, Cao P et al (2014) Quaternary phosphonium modified epoxidized natural rubber: effect of reaction time, reaction mechanism, thermal property and antimicrobial activity. Polym Bull 71:2543–2557. https://doi.org/10.1007/s00289-014-1206-210.1007/s00289-014-1206-2 ↗
17. Derouet D, Radhakrishnan N, Brosse JC, Boccaccio G (1994) Phosphorus modification of epoxidized liquid natural rubber to improve flame resistance of vulcanized rubbers. J Appl Polym Sci 52:1309–1316. https://doi.org/10.1002/app.1994.07052091510.1002/app.1994.070520915 ↗
18. Perera MCS (1990) Reaction of aromatic amines with epoxidized natural rubber latex. J Appl Polym Sci 39:749–758. https://doi.org/10.1002/app.1990.07039032310.1002/app.1990.070390323 ↗
19. Cheng B, Lu X, Zhou J et al (2019) Dual cross-linked self-healing and recyclable epoxidized natural rubber based on multiple reversible effects. ACS Sustain Chem Eng 7:4443–4455. https://doi.org/10.1021/acssuschemeng.8b0643710.1021/acssuschemeng.8b06437 ↗
20. Liu Y, Li Z, Liu R et al (2019) Design of self-healing rubber by introducing ionic interaction to construct a network composed of ionic and covalent cross-linking. Ind Eng Chem Res 58:14848–14858. https://doi.org/10.1021/acs.iecr.9b0297210.1021/acs.iecr.9b02972 ↗
21. Saramolee P, Lopattananon N, Sahakaro K (2014) Preparation and some properties of modified natural rubber bearing grafted poly(methyl methacrylate) and epoxide groups. Eur Polym J 56:1–10. https://doi.org/10.1016/j.eurpolymj.2014.04.00810.1016/j.eurpolymj.2014.04.008 ↗
22. Yang Z, Peng H, Wang W, Liu T (2010) Crystallization behavior of poly(ε-caprolactone)/layered double hydroxide nanocomposites. J Appl Polym Sci 116:2658–2667. https://doi.org/10.1002/app10.1002/app ↗
23. Meninno S, Lattanzi A (2016) Organocatalytic asymmetric reactions of epoxides: recent progress. Chem A Eur J 22:3632–3642. https://doi.org/10.1002/chem.20150422610.1002/chem.201504226 ↗
24. Hamzah R, Bakar MA, Dahham OS et al (2016) A structural study of epoxidized natural rubber (ENR-50) ring opening under mild acidic condition. J Appl Polym Sci. https://doi.org/10.1002/app.4412310.1002/app.44123 ↗
25. Chen X, Zhang K, Talley SJ et al (2019) Quadruple hydrogen bonding containing supramolecular thermoplastic elastomers: mechanical and morphological correlations. J Polym Sci, Part A: Polym Chem 57:13–23. https://doi.org/10.1002/pola.2927210.1002/pola.29272 ↗
26. Faghihnejad A, Feldman KE, Yu J et al (2014) Adhesion and surface interactions of a self-healing polymer with multiple hydrogen-bonding groups. Adv Funct Mater 24:2322–2333. https://doi.org/10.1002/adfm.20130301310.1002/adfm.201303013 ↗
27. Zhang A, Yang L, Lin Y et al (2013) Self-healing supramolecular elastomers based on the multi-hydrogen bonding of low-molecular polydimethylsiloxanes: synthesis and characterization. J Appl Polym Sci 129:2435–2442. https://doi.org/10.1002/app.3883210.1002/app.38832 ↗
28. Wu DY, Meure S, Solomon D (2008) Self-healing polymeric materials: a review of recent developments. Prog Polym Sci 33:479–522. https://doi.org/10.1016/j.progpolymsci.2008.02.00110.1016/j.progpolymsci.2008.02.001 ↗
29. Zhao J, Zhang H, Ma C et al (2019) Binary modification of Eucommia ulmoides gum toward elastomer with tunable mechanical properties and good compatibility. J Polym Sci, Part A: Polym Chem 57:1247–1255. https://doi.org/10.1002/pola.2938110.1002/pola.29381 ↗
30. Yang GW, Wu GP (2019) High-efficiency construction of CO2-based healable thermoplastic elastomers via a tandem synthetic strategy. ACS Sustain Chem Eng 7:1372–1380. https://doi.org/10.1021/acssuschemeng.8b0508410.1021/acssuschemeng.8b05084 ↗
31. Frick EM, Zalusky AS, Hillmyer MA (2003) Characterization of polylactide-b-polyisoprene-b-polylactide thermoplastic elastomers. Biomacromol 4:216–223. https://doi.org/10.1021/bm025628b10.1021/bm025628b ↗
32. Bolton JM, Hillmyer MA, Hoye TR (2014) Sustainable thermoplastic elastomers from terpene-derived monomers. ACS Macro Lett 3:717–720. https://doi.org/10.1021/mz500339h10.1021/mz500339h ↗
33. Liu B, Gao X, Zhao Y et al (2017) 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide-based oligosiloxane as a promising damping additive for methyl vinyl silicone rubber (VMQ). J Mater Sci 52:1–15. https://doi.org/10.1007/s10853-017-1085-710.1007/s10853-017-1085-7 ↗