A curing agent for epoxy resin based on microencapsulation of 1-butylimidazole
Source abstract
Abstract
An efficient and economical strategy for rapid microencapsulation of 1-butylimidazole (1-BMI) was developed. The strategy is based on the thiol-yne click reaction of trimethylolpropane tris(3-mercaptopropionate) and 1,7-octadiyne in oil-in-water emulsion. The thiol-yne click reaction is not only green and efficient, but also improves the cross-linking density of shell. Thus, the obtained shell prevents the leakage of curing agent and prolongs the storage period of EP/MCs system. The whole process of preparing 1BMI-MCs only took 40 min. Moreover, the effects of stirring speed and the ratio of 1BMI on the size and core content of microcapsules (MCs) were investigated. Results demonstrated that the optimal particle size was about 10.8 μm, and the maximum content of 1BMI in MCs was 33% corresponding to 60% 1BMI in oil phase. Afterward, the 1BMI MCs were used as latent curing agent (LCA) for epoxy resin (EP). In the curing reaction of the epoxy resin, the 1BMI-MCs exhibited a delayed kinetic behavior compared to pure 1BMI. Furthermore, the E-51/MCs system had a storage term of 16 weeks. The shell material not only had no effect on curing effect of E-51, but also toughen the cured EP systems. This paper provided a promising method for long-term storage of LCA.
Source: expertdata · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Epoxy Resin Curing Processes · Photopolymerization techniques and applications · Synthesis and properties of polymers
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (49)
Show source-provided references
1. Unruh D, Pastine S, Moreton J, Fréchet J (2011) Thermally activated, single component epoxy systems. Macromolecules 44:6318–632510.1021/ma200673v ↗
2. Zhu J, Peng H, Rodriguez-Macias F, Margrave J, Barrera E (2010) Reinforcing epoxy polymer composites through covalent integration of functionalized nanotubes. Adv Func Mater 14:643–64810.1002/adfm.200305162 ↗
3. Yang X, Guo L, Xu X, Shang S, Liu H (2020) A fully bio-based epoxy vitrimer: Self-healing, triple-shape memory and reprocessing triggered by dynamic covalent bond exchange. Materials 186:108248
4. Ning K, Zhou L, Zhao B (2021) A novel aminothiazole-based cyclotriphosphazene derivate towards epoxy resins for high flame retardancy and smoke suppression. Polym Degrad Stab 190:10965110.1016/j.polymdegradstab.2021.109651 ↗
5. Ruan K, Zhong X, Shi X, Dang J, Gu J (2021) Liquid crystal epoxy resins with high intrinsic thermal conductivities and their composites: a mini-review. Materials Today Physics 20:10045610.1016/j.mtphys.2021.100456 ↗
6. Goncalves F, Santos M, Cernadas T, Ferreira P, Alves P (2022) Advances in the development of biobased epoxy resins: insight into more sustainable materials and future applications. Int Mater Rev 67:119–14910.1080/09506608.2021.1915936 ↗
7. Zhang Q, Wang J, Yang S, Cheng J (2019) Facile construction of one-component intrinsic flame-retardant epoxy resin system with fast curing ability using imidazole-blocked bismaleimide. Compos B Eng 177:10738010.1016/j.compositesb.2019.107380 ↗
8. Suzuki K, Sugita Y, Sanda F, Endo T (2010) One-component epoxy resin with imine as water-initiated latent hardener: improvement of the mechanical and adhesive properties by the addition of methacrylate copolymer. J Appl Polym Sci 96:1943–194910.1002/app.21651 ↗
9. Zhang B, Zhao Y, Sun X, Fei X, Wei W, Li X, Liu X (2020) Microcapsules derived from Pickering emulsions as thermal latent curing accelerator for epoxy resins. J Ind Eng Chem 83:224–23410.1016/j.jiec.2019.11.032 ↗
10. Ham Y, Dong H, Sun H, Shin Y, Yang M, Shin J (2010) Microencapsulation of imidazole curing agent for epoxy resin. J Ind Eng Chem 16:728–73310.1016/j.jiec.2010.07.011 ↗
11. Ma A, Zhang Q, Zhang H, Shi Y, Liu Y (2013) A novel single component epoxy resin adhesive with microcapsule latent curing agent of 2-phenylimidazole/polymethyl acrylic glycidyl ester. J Elastomers Plast 47:440–448
12. Zhang P, Shah S, Gao F, Sun H, Cui Z, Cheng J, Zhang J (2019) Latent curing epoxy systems with reduced curing temperature and improved stability. Thermochim Acta 676:130–13810.1016/j.tca.2019.03.022 ↗
13. Yang B, Mao Y, Zhang Y, Bian G, Zhang L, Wei Y, Jiang Q, Qiu Y, Liu W (2019) A novel liquid imidazole-copper (II) complex as a thermal latent curing agent for epoxy resins. Polymer 178:12158610.1016/j.polymer.2019.121586 ↗
14. Zhen Y, Ma S, Tang Z, Liu Y, Xu X, Li Q, Zhang K, Wang B, Wang S, Zhu J (2021) Amino acids as latent curing agents and their application in fully bio-based epoxy resins. Green Chem 23:6566–657510.1039/D1GC02126E ↗
15. Fan J, Zheng Y, Xie Y, Sun Y, Luan Y, Jiang W, Wang C, Liu S, Liu X (2017) Effect of solvent evaporation technique on the characteristics of curing agent microcapsules and the curing process. Compos Sci Technol 138:80–9010.1016/j.compscitech.2016.11.014 ↗
16. Yan Y, Guo X, Li J, Zhang J, Li A, Ren L, Yu H (2020) Preparation and curing behavior of latent 2-Phlm-PS microcapsule curing agent for epoxy resin. Appl Polym Sci 138:5037910.1002/app.50379 ↗
17. Gu J, Yang X, Li C, Kou C (2016) Synthesis of cyanate ester microcapsules via solvent evaporation technique and its application in epoxy resins as a healing agent. Ind Eng Chem Res 55:10941–1094610.1021/acs.iecr.6b03093 ↗
18. Tao Y, Tao Y, Sun M, Wang B (2017) Synthesis and characterization of polythiol@melamine -formaldehyde resin for epoxy based hardener. Acta Mater Compos Sin 34:298–307
19. Mozaffari S, Beheshty M (2019) Thermally-latent curing agents for epoxy resins: a review. Iran J Polym Sci Technol 31:409–426
20. Mozaffari S, Beheshty M (2021) Nanoclay-modified microcapsules as a latent curing agent in epoxy. Polym Bull 78:3103–311510.1007/s00289-020-03247-8 ↗
21. Li Q, Kim S, Hui N, Lee J (2013) Effects of dual component microcapsules of resin and curing agent on the self-healing efficiency of epoxy. Compos B Eng 55:79–8510.1016/j.compositesb.2013.06.006 ↗
22. Tan X, Zhang J, Guo D, Sun G, Zhou Y, Zhang W, Guan Y (2020) Preparation, characterization and repeated repair ability evaluation of asphalt-based crack sealant containing microencapsulated epoxy resin and curing agent. Constr Build Mater 256:11943310.1016/j.conbuildmat.2020.119433 ↗
23. Nascimento D, Avendaño J, Mehl A, Moura M, Carvalho M, Duncanson W (2017) Flow of tunable elastic microcapsules through constrictions. Sci Rep 7:11898–1190410.1038/s41598-017-11950-2 ↗
24. Xing S, Yang J, Huang Y, Zheng Q, Zeng J (2015) Preparation and characterization of a novel microcapsule-type latent curing agent for epoxy resin. Mater Des 85:661–67010.1016/j.matdes.2015.07.098 ↗
25. Shin M, Kim J, Shin J (2012) Microencapsulation of imidazole curing agents by spray-drying method using W/O emulsion. J Appl Polym Sci 126:108–11510.1002/app.35490 ↗
26. Yan C, Min Z, Ming Q (2008) Preparation and characterization of microencapsulated polythiol. Polymer 49:2531–254110.1016/j.polymer.2008.03.044 ↗
27. Zhao L, Yang X, Li Q, Ma L (2019) Latent curing agent DDM-PMMA microcapsule for epoxy resin. Appl Polym Sci 136:4775710.1002/app.47757 ↗
28. Zhao L, Yang X, Ma L, Li Q (2020) Preparation of imidazole embedded polyurea microcapsule for latent curing agent. Appl Polym Sci 137:4934010.1002/app.49340 ↗
29. Zhang J, Zhang Z, Wang J, Zang Q, Sun J, Tang B (2021) Recent progress in the applications of amino–yne click chemistry. Polym Chem 12:2978–298610.1039/D1PY00113B ↗
30. Hong Y, Lee D, Lim D, Koo H, Kim K (2022) Copper-free click chemistry: applications in drug delivery. Cell Track Tissue Eng Adv Mater 34:2107192
31. Borbora A, Manna U (2021) Impact of chemistry on the preparation and post-modification of multilayered hollow microcapsules. Chem Commun 57:2110–212310.1039/D0CC06917E ↗
32. Hoyle C, Bowman C (2010) Thiol-ene click chemistry. J German Chem Soc 49:1540–1573
33. Li C, Tan J, Gu J, Qiao L, Zhang B, Zhang Q (2016) Rapid and efficient synthesis of isocyanate microcapsules via thiol-ene photopolymerization in Pickering emulsion and its application in self-healing coating. Compos Sci Technol 123:250–25810.1016/j.compscitech.2016.01.001 ↗
34. Liu D, Yu B, Jiang X, Yin J (2013) Responsive hybrid microcapsules by the one-step interfacial thiol-ene photopolymerization. Langmuir 29:5307–531410.1021/la400098c ↗
35. Li C, Tan J, Gu J, Xue Y, Qiao L, Zhang Q (2017) Facile synthesis of imidazole microcapsules via thiol-click chemistry and their application as thermally latent curing agent for epoxy resins. Compos Sci Technol 142:198–20610.1016/j.compscitech.2017.02.014 ↗
36. Geng Z, Jaeman J, Xi Y, Hawker C (2021) Click chemistry strategies for the accelerated synthesis of functional macromolecules. J Polym Sci 59:963–104210.1002/pol.20210126 ↗
37. Tan J, Li C, Dan S, Li H, Gu J, Zhang B, Zhang H, Zhang Q (2016) One-step thiol-isocyanate dispersion polymerization: preparation of uniform, cross-linked and functional particles. Chem Eng J 304:461–46810.1016/j.cej.2016.06.118 ↗
38. Chan J, Zhou H, Hoyle C, Lowe A (2009) Photopolymerization of thiol-alkynes: polysulfide networks. Chem Mater 21:1579–158510.1021/cm803262p ↗
39. Qin A, Lam J, Tang B (2010) Click polymerization. Chem Soc Rev 39:2522–254410.1039/b909064a ↗
40. Durham O, Norton H, Shipp D (2015) Functional polymer particles via thiol-ene and thiol-yne suspension “click” polymerization. RSC Adv 5:66757–6676610.1039/C5RA12553G ↗
41. Mavila S, Sinha J, Hu Y, Podgorski M, Bowman C (2021) High refractive index photopolymers by thiol-yne “click” polymerization. ACS Appl Mater Interfaces 13:15647–1565810.1021/acsami.1c00831 ↗
42. Fairbanks B, Scott T, Kloxin C, Anseth K, Bowman C (2009) Thiol-yne photopolymerizations: novel mmechanism, kinetics, and step-growth formation of highly cross-linked networks. Macromolecules 42:211–21710.1021/ma801903w ↗
43. Chan J, Shin J, Hoyle C, Bowman C, Lowe A (2010) Synthesis, Thiol-yne “click” photopolymerization, and physical properties of networks derived from novel multifunctional alkynes. Macromolecules 43:4937–494210.1021/ma1004452 ↗
44. Rajalingam K, Hallmann L, Strunskus T, Bashir A, Wöll C, Tuczek F (2010) Self-assembled monolayers of benzylmercaptan and para-cyanobenzylmercaptan on gold: surface infrared spectroscopic characterization. Phys Chem Chem Phys 12:4390–439910.1039/b923628g ↗
45. Zhang H, Yang L, Li Y, Tang Z, Zheng Z, Zhang L (2017) Preparation and properties of soybean oil-based curing agents for epoxy resin. J Appl Polym Sci 134:4475410.1002/app.44754 ↗
46. Özdemir N, Dayan O, Demirmen S (2016) Synthesis, structural, and spectroscopic (FT-IR, NMR, and UV) characterization of 1-(Cyclohexylmethyl)-2-(pyridin-2-yl)-1H-benzo[d]imidazole by experimental techniques and quantum chemical calculations. Opt Spectrosc 120:706–72010.1134/S0030400X16050209 ↗
47. Rialdi G (2007) Handbook of thermal analysis and calorimetry. Donghua University Press, Shanghai, China, pp 33–104
48. Hickey C, Bickerton S (2013) Cure kinetics and rheology characterisation and modelling of ambient temperature curing epoxy resins for resin infusion/varmt and wet layup applications. J Mater Sci 48:690–701https://doi.org/10.1007/s10853-012-6781-810.1007/s10853-012-6781-8 ↗
49. Isarn I, Ramis X, Ferrando F, Serra A (2018) Thermoconductive thermosetting composites based on boron nitride fillers and thiol-epoxy matrices. Polymers 10:277–29310.3390/polym10030277 ↗