Synthesis and properties of self-healing waterborne polyurethanes containing disulfide bonds in the main chain
Source abstract
Abstract
Materials with intrinsic self-healing ability have attracted tremendous interest in literature, especially coatings in anti-corrosion applications. In this work, environmentally friendly waterborne polyurethanes containing disulfide bonds in the main chain were synthesized. Poly (e-caprolactone) glycol with a molecular weight of 1000 was used as soft segment, and isophorone diisocyanate, 2-bis(hydroxymethyl) propionic acid, and 2-hydroxyethyl disulfide were used as hard segment. The influence of 2-hydroxyethyl disulfide/2-bis(hydroxymethyl) propionic acid molar ratios on stability of dispersions and the self-healing property of the waterborne polyurethane films was investigated. The self-healing system was triggered by the chain exchange reaction of disulfide bonds and assisted by the shape memory effect to bring the crack on the waterborne polyurethane surfaces in spatial proximity. The tensile strength of the scratched waterborne polyurethane film was recovered to 90.5 % in 10 min at a modest healing temperature of 65 °C. Meanwhile, the prepared waterborne polyurethanes exhibited excellent dispersion stability and improved thermal stability.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Polymer composites and self-healing · Corrosion Behavior and Inhibition · Antimicrobial agents and applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (36)
Show source-provided references
1. EI-Wahab HA, EI-Fattah MA, Ayman HA, Elhenawy AA, Alian NA (2015) Synthesis and characterization of some arylhydrazone ligand and its metal complexes and their potential application as flame retardant and antimicrobial additives in polyurethane for surface coating. J Organomet Chem 791:99–10610.1016/j.jorganchem.2015.05.024 ↗
2. Sheikhy H, Shahidzadeh M, Ramezanzadeh B, Noroozi F (2013) Studying the effects of chain extenders chemical structures on the adhesion and mechanical properties of a polyurethane adhesive. J Ind Eng Chem 19:1949–195510.1016/j.jiec.2013.03.008 ↗
3. Qu RJ, Gao JJ, Tang B, Ma QL, Qu BH, Sun CM (2014) Preparation and property of polyurethane/nanosilver complex fibers. Appl Surf Sci 294:81–8810.1016/j.apsusc.2013.11.116 ↗
4. Massalha N, Brenner A, Sheindorf C, Haimov Y, Sabban I (2015) Enriching composite hydrophilic polyurethane foams with PAC to enhance adsorption of phenol from aqueous solutions. Chem Eng J 280:283–29210.1016/j.cej.2015.06.015 ↗
5. Ljubic D, Srinivasan M, Szoszkiewicz R, Javni I, Petrovic ZS (2015) Surface modified graphene/single-pase polyurethane elastomers with improved thermo-mechanical and dielectric properties. Eur Polym J 70:55–6510.1016/j.eurpolymj.2015.07.008 ↗
6. Hu J, Lu P, Lou C, Lee M, Lin J (2016) Small-diameter vascular grafts composed of polyester/spandex fibers: manufacturing techniques and property evaluations. Mater Lett 171:42–4510.1016/j.matlet.2016.01.154 ↗
7. Nelson AM, Long TE (2014) Synthesis, properties, and applications of ion-containing polyurethane segmented copolymers. Macromol Chem Phys 215:2161–217410.1002/macp.201400373 ↗
8. Chattopadhyay DK, Raju K (2007) Structural engineering of polyurethane coatings for high performance applications. Prog Polym Sci 32:352–41810.1016/j.progpolymsci.2006.05.003 ↗
9. Kwak YS, Park SW, Lee YH, Kim HD (2003) Preparation and properties of waterborne polyurethanes for water-vapor-permeable coating materials. J Appl Polym Sci 89:123–12910.1002/app.12128 ↗
10. Zhao W, Li M, Peng HX (2010) Functionalized MWNT-doped thermoplastic polyurethane nanocomposites for aerospace coating applications. Macromol Mater Eng 295:838–84510.1002/mame.201000080 ↗
11. Du H, Zhao Y, Li Q, Wang J, Kang M, Wang X, Xiang H (2008) Synthesis and characterization of waterborne polyurethane adhesive from MDI and HDI. J Appl Polym Sci 110:1396–140210.1002/app.28805 ↗
12. Lu Y, Larock RC (2008) Soybean-oil-based waterborne polyurethane dispersions: effects of polyol functionality and hard segment content on properties. Biomacromolecules 9:3332–334010.1021/bm801030g ↗
13. Koh E, Kim NK, Shin J, Kim YM (2014) Polyurethane microcapsules for self-healing paint coatings. RSC Adv 4:16214–1622310.1039/C4RA00213J ↗
14. Yang Y, Urban MW (2013) Self-healing polymeric materials. Chem Soc Rev 42:7446–746710.1039/c3cs60109a ↗
15. Hager MD, Greil P, Leyens C, van der Zwaag S, Schubent US (2010) Self-healing materials. Adv Mater 22:5424–543010.1002/adma.201003036 ↗
16. Syrett JA, Becer CR, Haddleton DM (2010) Self-healing and self-mendable polymers. Polym Chem-UK 1:978–98710.1039/c0py00104j ↗
17. Zhang P, Li G (2016) Advances in healing-on-demand polymers and polymer composites. Prog Polym Sci 57:32–6310.1016/j.progpolymsci.2015.11.005 ↗
18. Stankiewicz A, Szczygieł I, Szczygieł B (2013) Self-healing coatings in anti-corrosion applications. J Mater Sci 48:8041–805110.1007/s10853-013-7616-y ↗
19. Yoon JA, Kamada J, Koynov K, Mohin J, Nicolay R, Zhang Y, Matyjaszewski K (2011) Self-healing polymer films based on thiol-disulfide exchange reactions and self-healing kinetics measured using atomic force microscopy. Macromolecules 45:142–14910.1021/ma2015134 ↗
20. Koh E, Lee S, Shin J, Kim YM (2013) Renewable polyurethane microcapsules with isosorbide derivatives for self-healing anticorrosion coatings. Ind Eng Chem Res 52:15541–1554810.1021/ie402505s ↗
21. Cho SH, White SR, Braun PV (2009) Self-healing polymer coatings. Adv Mater 21:645–64910.1002/adma.200802008 ↗
22. Wouters M, Craenmehr E, Tempelaars K, Fischer H, Stroeks N, van Zanten J (2009) Preparation and properties of a novel remendable coating concept. Prog Org Coat 64:156–16210.1016/j.porgcoat.2008.09.023 ↗
23. Luo X, Mather PT (2013) Shape memory assisted self-healing coating. ACS Macro Lett 2:152–15610.1021/mz400017x ↗
24. Amamoto Y, Otsuka H, Takahara A, Matyjaszewski K (2012) Self-healing of covalently cross-linked polymers by reshuffling thiuram disulfide moieties in air under visible light. Adv Mater 24:3975–398010.1002/adma.201201928 ↗
25. Rekondo A, Martin R, de Luzuriaga AR, Cabañero G, Grande HJ, Odriozola I (2014) Catalyst-free room-temperature self-healing elastomers based on aromatic disulfide metathesis. Mater Horiz 1:237–24010.1039/C3MH00061C ↗
26. Xu Y, Chen D (2016) A novel self-healing polyurethane based on disulfide bonds. Macromol Chem Phys. doi: 10.1002/m1cp.0001110.1002/m1cp.00011 ↗
27. Lafont U, van Zeijl H, van der Zwaag S (2012) Influence of cross-linkers on the cohesive and adhesive self-healing ability of polysulfide-based thermosets. ACS Appl Mater Inter 4:6280–628810.1021/am301879z ↗
28. Hernández B, Pflüger F, López-Tobar E, Kruglik SG, Garcia-Ramos JV, Sanchez-Cortes S, Ghomi M (2014) Disulfide linkage Raman markers: a reconsideration attempt. J Raman Spectrosc 45:657–66410.1002/jrs.4521 ↗
29. Santamaria-Echart A, Arbelaiz A, Saralegi A, Fernández-d’Arlas B, Eceiza A, Corcuera MA (2015) Relationship between reagents molar ratio and dispersion stability and film properties of waterborne polyurethanes. Colloid Surf A 482:554–56110.1016/j.colsurfa.2015.07.012 ↗
30. Asif A, Shi W, Shen X, Nie K (2005) Physical and thermal properties of UV curable waterborne polyurethane dispersions incorporating hyperbranched aliphatic polyester of varying generation number. Polymer 46:11066–1107810.1016/j.polymer.2005.09.046 ↗
31. Bohinc K, Kralj-Iglič V, Iglič A (2001) Thickness of electrical double layer. Effect of ion size. Electrochim Acta 46:3033–304010.1016/S0013-4686(01)00525-4 ↗
32. Nanda AK, Wicks DA (2006) The influence of the ionic concentration, concentration of the polymer, degree of neutralization and chain extension on aqueous polyurethane dispersions prepared by the acetone process. Polymer 47:1805–181110.1016/j.polymer.2006.01.074 ↗
33. Coutinho FM, Delpech MC, Alves TL, Ferreira AA (2003) Degradation profiles of cast films of polyurethane and poly (urethane-urea) aqueous dispersions based on hydroxy-terminated polybutadiene and different diisocyanates. Polym Degrad Stabil 81:19–2710.1016/S0141-3910(03)00058-2 ↗
34. Garcia-Pacios V, Iwata Y, Colera M, Martín-Martínez JM (2011) Influence of the solids content on the properties of waterborne polyurethane dispersions obtained with polycarbonate of hexanediol. Int J Adhes Adhes 31:787–79410.1016/j.ijadhadh.2011.05.010 ↗
35. Ding XM, Hu JL, Tao XM (2004) Effect of crystal melting on water vapor permeability of shape-memory polyurethane film. Text Res J 74:39–4310.1177/004051750407400107 ↗
36. Liu N, Zhao Y, Kang M, Wang J, Wang X, Feng Y, Li Q (2015) The effects of the molecular weight and structure of polycarbonatediols on the properties of waterborne polyurethanes. Prog Org Coat 82:46–5610.1016/j.porgcoat.2015.01.015 ↗