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Journal of Materials Science

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12-03-2020 | Chemical routes to materials

Imidazole-loaded microcapsules as latent curing agent with superior solvent stability and shelf life

Authors: Ying Xue, Chunmei Li, Jiaojun Tan, Zhengzhou Su, Yumin Yang, Guoxian Zhang, Qiuyu Zhang

Published in: Journal of Materials Science | Issue 17/2020

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Abstract

A novel microcapsule-type thermal latent curing agent with a double-shell structure was successfully fabricated. 1-Benzyl-2-methylimidazole (1B2MZ) was encapsulated by poly(methyl methacrylate-n-butyl acrylate) (PMMA/BA) using the solvent evaporation method, which served as the primary microcapsules (PMCs) to be deposited by polydopamine (PDA). Various glass transition temperatures (T_g, from 116.7 to 57.2 °C) and thermal properties of shell material PMMA/BA were obtained by tuning the mass ratio of BA to MMA monomer. PMMA/BA with 20 wt% of BA ratio was selected as the shell of PMCs for its appropriate T_g (92.33 °C) and relatively good thermal resistance. (Decomposition temperature was 222.83 °C.) The obtained PMCs and the double-shell microcapsules (DMCs) had good spherical shape, and the chemical structure of DMCs was confirmed by Fourier transform infrared spectra. Thermogravimetric analysis indicated that the core contents of PMCs and DMCs were 11.95 and 11.37%, respectively. After being coated by PDA, the solvent resistances of microcapsules in weak-polar (toluene) and high-polar (dichloromethane, DCM and acetone) solvents were significantly improved. When storing at room temperature for more than 4 months, the mixture of DMCs and the diluted epoxy could be cured at 120 °C for 1 h.

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Jin F-L, Li X, Park S-J (2015) Synthesis and application of epoxy resins: a review. J Ind Eng Chem 29:1–11

Vietri U, Guadagno L, Raimondo M, Vertuccio L, Lafdi K (2014) Nanofilled epoxy adhesive for structural aeronautic materials. Compos Part B 61:73–83

Jin H, Miller GM, Pety SJ et al (2013) Fracture behavior of a self-healing, toughened epoxy adhesive. Int J Adhes Adhes 44:157–165

Saldanha D, Canto C, Da Silva L, Carbas R, Chaves F, Nomura K, Ueda T (2013) Mechanical characterization of a high elongation and high toughness epoxy adhesive. Int J Adhes Adhes 47:91–98

Ahmadi Z (2019) Nanostructured epoxy adhesives: a review. Prog Org Coat 135:449–453

Ke L, Li C, He J, Dong S, Chen C, Jiao Y (2020) Effects of elevated temperatures on mechanical behavior of epoxy adhesives and CFRP-steel hybrid joints. Compos Struct 235:111789

Aliakbari M, Jazani OM, Sohrabian M, Jouyandeh M (2019) Multi-nationality epoxy adhesives on trial for future nanocomposite developments. Prog Org Coat 133:376–386

Ferdosian F, Ebrahimi M, Jannesari A (2013) Curing kinetics of solid epoxy/DDM/nanoclay: isoconversional models versus fitting model. Thermochim Acta 568:67–73

Jin H, Mangun CL, Stradley DS, Moore JS, Sottos NR, White SR (2012) Self-healing thermoset using encapsulated epoxy-amine healing chemistry. Polymer 53:581–587

10.

Hsu Y-G, Lin K-H, Lin T-Y, Fang Y-L, Chen S-C, Sung Y-C (2012) Properties of epoxy-amine networks containing nanostructured ether-crosslinked domains. Mater Chem Phys 132:688–702

11.

Parildar RA, Ibik AAB (2013) Characterization of tertiary amine and epoxy functional all-acrylic coating system. Prog Org Coat 76:955–958

12.

Fan M, Liu J, Li X, Cheng J, Zhang J (2013) Curing behaviors and properties of an extrinsic toughened epoxy/anhydride system and an intrinsic toughened epoxy/anhydride system. Thermochim Acta 554:39–47

13.

Foix D, Rodriguez MT, Ferrando F, Ramis X, Serra A (2012) Combined use of sepiolite and a hyperbranched polyester in the modification of epoxy/anhydride coatings: a study of the curing process and the final properties. Prog Org Coat 75:364–372

14.

Flores M, Fernandez-Francos X, Ferrando F, Ramis X, Serra A (2012) Efficient impact resistance improvement of epoxy/anhydride thermosets by adding hyperbranched polyesters partially modified with undecenoyl chains. Polymer 53:5232–5241

15.

Park SJ, Jin FL (2004) Thermal stabilities and dynamic mechanical properties of sulfone-containing epoxy resin cured with anhydride. Polym Degrad Stab 86:515–520

16.

Park SJ, Jin FL, Lee JR, Shin JS (2005) Cationic polymerization and physicochemical properties of a biobased epoxy resin initiated by thermally latent catalysts. Eur Polym J 41:231–237

17.

Jin F-L, Park S-J (2007) Thermal and rheological properties of vegetable oil-based epoxy resins cured with thermally latent initiator. J Ind Eng Chem 13:808–814

18.

Park SJ, Kim HC, Lee HI, Suh DH (2001) Thermal stability of imidized epoxy blends initiated by N-benzylpyrazinium hexafluoroantimonate salt. Macromolecules 34:7573–7575

19.

Jin F-L, Park S-J (2008) Fracture toughness of difunctional epoxy resin/thermally latent initiator system modified with polyesters. J Ind Eng Chem 14:564–567

20.

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 142:198–206

21.

Cao M, Xie P, Jin Z, Zhang Y, Zhang R, Chung TS, He C (2002) Novel microencapsulated curing accelerator for prolonging shelf life of epoxy resin composition. J Appl Polym Sci 85:873–878

22.

Arimitsu K, Fuse S, Kudo K, Furutani M (2015) Imidazole derivatives as latent curing agents for epoxy thermosetting resins. Mater Lett 161:408–410

23.

Fuensanta M, Grau A, Romero-Sánchez MD, Guillem C, López-Buendía ÁM (2013) Effect of the polymer shell in imidazole microencapsulation by solvent evaporation method. Polym Bull 70:3055–3074

24.

Matuszak C, Matuszak A (1976) Imidazole-versatile today, prominent tomorrow. J Chem Educ 53:280

25.

Yang B, Mao Y, Zhang Y et al (2019) A novel liquid imidazole-copper(II) complex as a thermal latent curing agent for epoxy resins. Polymer 178:121586

26.

Hamerton I, Howlin BJ, Jones JR, Liu S, Barton JM (1996) Effect of complexation with copper(II) on cured neat resin properties of a commercial epoxy resin using modified imidazole curing agents. J Mater Chem 6:305–310

27.

Kudo K, Furutani M, Arimitsu K (2016) Imidazobenzoxazin-5-ones as thermal latent curing agents for thermosetting epoxy resins. J Polym Sci Part A Polym Chem 54:3411–3414

28.

Barton JM, Buist GJ, Hamerton I, Howlin BJ, Jones JR, Liu S (1994) Preparation and characterization of imidazole-metal complexes and evaluation of cured epoxy networks. J Mater Chem 4:379–384

29.

Kaplan M, Wayda A, Lyons A (1990) Lanthanide-imidazole complexes as latent curing agents for epoxy resins. J Polym Sci Part A Polym Chem 28:731–740

30.

Ricciardi F, Romanchick WA, Joullié MM (1983) 1,3-Dialkylimidazolium salts as latent catalysts in the curing of epoxy resins. J Polym Sci Polym Lett Ed 21:633–638

31.

Lee DH, Yang M, Kim SH, Shin MJ, Shin JS (2011) Microencapsulation of Imidazole curing agents by spray-drying method. J Appl Polym Sci 122:782–788

32.

Mozaffari SM, Beheshty MH, Mirabedini SM (2017) Effect of processing conditions on the microencapsulation of 1-methylimidazole curing agent using solid epoxy resins. Iran Polym J 26:629–637

33.

Xu H, Fang Z, Tong L (2008) Effect of microencapsulated curing agents on the curing behavior for diglycidyl ether of bisphenol a epoxy resin systems. J Appl Polym Sci 107:1661–1669

34.

Shin MJ, Shin YJ, Shin JS (2018) Latent imidazole curing agents by microencapsulation with copolymers. Part Sci Technol 36:112–116

35.

Shin MJ, Shin YJ, Hwang SW, Shin JS (2013) Microencapsulation of imidazole curing agent by solvent evaporation method using W/O/W emulsion. J Appl Polym Sci 129:1036–1044

36.

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 85:661–670

37.

Ham YR, Lee DH, Kim SH, Shin YJ, Yang M, Shin JS (2010) Microencapsulation of imidazole curing agent for epoxy resin. J Ind Eng Chem 16:728–733

38.

Li Q, Mishra AK, Kim NH, Kuila T, Lau K-T, Lee JH (2013) Effects of processing conditions of poly(methylmethacrylate) encapsulated liquid curing agent on the properties of self-healing composites. Compos Part B 49:6–15

39.

Chuanjie F, Xiaodong Z (2009) Preparation and barrier properties of the microcapsules added nanoclays in the wall. Polym Adv Technol 20:934–939

40.

Wu G, An J, Sun D, Tang X, Xiang Y, Yang J (2014) Robust microcapsules with polyurea/silica hybrid shell for one-part self-healing anticorrosion coatings. J Mater Chem A 2:11614–11620

41.

Dreyer DR, Miller DJ, Freeman BD, Paul DR, Bielawski CW (2012) Elucidating the structure of poly(dopamine). Langmuir 28:6428–6435

42.

Kang S, Baginska M, White SR, Sottos NR (2015) Core–shell polymeric microcapsules with superior thermal and solvent stability. ACS Appl Mater Interfaces 7:10952–10956

43.

Zhang C, Ou Y, Lei WX, Wan LS, Ji J, Xu ZK (2016) CuSO₄/H₂O₂-induced rapid deposition of polydopamine coatings with high uniformity and enhanced stability. Angew Chem Int Ed 55:3054–3057

44.

Tian L, Li X, Zhao P et al (2015) Generalized approach for fabricating monodisperse anisotropic microparticles via single-hole swelling PGMA seed particles. Macromolecules 48:7592–7603

45.

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 123:250–258

Title: Imidazole-loaded microcapsules as latent curing agent with superior solvent stability and shelf life
Authors: Ying Xue
Chunmei Li
Jiaojun Tan
Zhengzhou Su
Yumin Yang
Guoxian Zhang
Qiuyu Zhang
Publication date: 12-03-2020
Publisher: Springer US
Published in: Journal of Materials Science / Issue 17/2020
Print ISSN: 0022-2461
Electronic ISSN: 1573-4803
DOI: https://doi.org/10.1007/s10853-020-04536-3

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