Thermally resistant and strong remoldable triple-shape memory thermosets based on bismaleimide with transesterification
Source abstract
Abstract
It is still a great challenge to endow remoldable triple-shape memory thermosets (Rtri-SMTs) with high glass transition temperature (Tg) and high mechanical properties. Herein, two Rtri-SMTs with high Tg and high tensile properties, coded as BA1 and BA2, were developed through building unique dynamic crosslinked networks based on bismaleimide and novel bisallyl compounds with dynamic ester bonds (AEG1 and AEG2). The Tg values of BA1 and BA2 resins are 143 °C and 203 °C, respectively, much higher than those of Rtri-SMTs reported so far (10–110 °C); meanwhile, BA resins exhibit high tensile strengths (BA1: 81 MPa; BA2: 84 MPa) and moduli (BA1: 2165 MPa; BA2: 3233 MPa), which are severally at least about 1.3–1.4 and 3.2–4.7 times of those Rtri-SMTs in the literature, respectively. Besides the superiorly high thermal and tensile properties, both BA resins are able to be remolded and reconfigured through the re-arrangement of crosslinked networks induced by dynamic exchange reaction of ester bonds. The mechanism behind these attractive properties of BA1 and BA2 resins is discussed. Remoldable triple-shape memory thermosets with high glass transition temperature, high mechanical properties and good reconfigurability were developed.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Polymer composites and self-healing · Photochromic and Fluorescence Chemistry · Lignin and Wood Chemistry
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (51)
Show source-provided references
1. Sellinger AT, Wang DH, Tan LS, Vaia RA (2010) Electrothermal polymer nanocomposite actuators. Adv Mater 22:3430–3435. https://doi.org/10.1002/adma.20090410710.1002/adma.200904107 ↗
2. Xiao X, Kong D, Qiu X, Zhang W, Zhang F, Liu L, Liu Y, Zhang S, Hu Y, Leng J (2015) Shape-memory polymers with adjustable high glass transition temperatures. Macromolecules 48:3582–3589. https://doi.org/10.1021/acs.macromol.5b0065410.1021/acs.macromol.5b00654 ↗
3. Wie JJ, Chatterjee S, Wang DH, Tan L-S, Ravi Shankar M, White TJ (2014) Azobenzene-functionalized polyimides as wireless actuators. Polymer 55:5915–5923. https://doi.org/10.1016/j.polymer.2014.06.08410.1016/j.polymer.2014.06.084 ↗
4. Melly SK, Liu L, Liu Y, Leng J (2020) Active composites based on shape memory polymers: Overview, fabrication methods, applications, and future prospects. J Mater Sci 55:10975–11051. https://doi.org/10.1007/s10853-020-04761-w10.1007/s10853-020-04761-w ↗
5. Chen B, Yuan L, Guan Q, Liang G, Gu A (2018) Preparation and mechanism of shape memory bismaleimide resins with high transition temperature, high toughness and good processability. J Mater Sci 53:10798–10811. https://doi.org/10.1007/s10853-018-2367-410.1007/s10853-018-2367-4 ↗
6. Sokolowski WM, Tan SC (2007) Advanced self-deployable structures for space applications. J Spacecraft Rockets 44:750–754. https://doi.org/10.2514/1.2285410.2514/1.22854 ↗
7. Lan X, Liu Y, Lv H, Wang X, Leng J, Du S (2009) Fiber reinforced shape-memory polymer composite and its application in a deployable hinge. Smart Mater Struct 18:024002. https://doi.org/10.1088/0964-1726/18/2/02400210.1088/0964-1726/18/2/024002 ↗
8. Liu Y, Du H, Liu L, Leng J (2014) Shape memory polymers and their composites in aerospace applications: a review. Smart Mater Struct 23:023001. https://doi.org/10.1088/0964-1726/23/2/02300110.1088/0964-1726/23/2/023001 ↗
9. Keller P, Lake M, Codell D, Barrett R, Taylor R, Schultz M (2006) Development of elastic memory composite stiffeners for a flexible precision reflector. 47th AIAA/ASME/ASCE/AHS/ASC Struct, Struct. Dyn. Mater. Conf. Doi:https://doi.org/10.2514/6.2006-217910.2514/6.2006-2179 ↗
10. Ding Z, Yuan L, Huang T, Liang G, Gu A (2019) High-temperature triple-shape memory polymer with full recovery through cross-linking all-aromatic liquid crystalline poly(ester imide) under reduced molding temperature. Ind Eng Chem Res 58:8734–8742. https://doi.org/10.1021/acs.iecr.9b0066210.1021/acs.iecr.9b00662 ↗
11. Pilate F, Toncheva A, Dubois P, Raquez JM (2016) Shape-memory polymers for multiple applications in the materials world. Eur Polym J 80:268–294. https://doi.org/10.1016/j.eurpolymj.2016.05.00410.1016/j.eurpolymj.2016.05.004 ↗
12. Kong D, Li J, Guo A, Zhang X, Xiao X (2019) Self-healing high temperature shape memory polymer. Eur Polym J. https://doi.org/10.1016/j.eurpolymj.2019.10927910.1016/j.eurpolymj.2019.109279 ↗
13. Shi Y, Yoonessi M, Weiss RA (2013) High temperature shape memory polymers. Macromolecules 46:4160–4167. https://doi.org/10.1021/ma302670p10.1021/ma302670p ↗
14. Hager MD, Bode S, Weber C, Schubert US (2015) Shape memory polymers: past, present and future developments. Prog Polym Sci 49–50:3–33. https://doi.org/10.1016/j.progpolymsci.2015.04.00210.1016/j.progpolymsci.2015.04.002 ↗
15. Yang Z, Chen Y, Wang Q, Wang T (2016) High performance multiple-shape memory behaviors of poly(benzoxazole-co-imide)s. Polymer 88:19–28. https://doi.org/10.1016/j.polymer.2016.02.00110.1016/j.polymer.2016.02.001 ↗
16. McBride MK, Podgorski M, Chatani S, Worrell BT, Bowman CN (2018) Thermoreversible folding as a route to the unique shape-memory character in ductile polymer networks. ACS Appl Mater Interfaces 10:22739–22745. https://doi.org/10.1021/acsami.8b0600410.1021/acsami.8b06004 ↗
17. Sabzi M, Babaahmadi M, Rahnama M (2017) Thermally and electrically triggered triple-shape memory behavior of poly(vinyl acetate)/poly(lactic acid) due to graphene-induced phase separation. ACS Appl Mater Interfaces 9:24061–24070. https://doi.org/10.1021/acsami.7b0225910.1021/acsami.7b02259 ↗
18. Zheng N, Fang G, Cao Z, Zhao Q, Xie T (2015) High strain epoxy shape memory polymer. Polym Chem 6:3046–3053. https://doi.org/10.1039/c5py00172b10.1039/c5py00172b ↗
19. Capiel G, Marcovich NE, Mosiewicki MA (2019) Shape memory polymer networks based on methacrylated fatty acids. Eur Polym J 116:321–329. https://doi.org/10.1016/j.eurpolymj.2019.04.02310.1016/j.eurpolymj.2019.04.023 ↗
20. Chen X, Li L, Wei T, Venerus DC, Torkelson JM (2019) Reprocessable polyhydroxyurethane network composites: effect of filler surface functionality on cross-link density recovery and stress relaxation. ACS Appl Mater Interfaces 11:2398–2407. https://doi.org/10.1021/acsami.8b1910010.1021/acsami.8b19100 ↗
21. Montarnal D, Capelot M, Tournilhac F, Leibler L (2011) Silica-like malleable materials from permanent organic networks. Science 334:965–968. https://doi.org/10.1126/science.121264810.1126/science.1212648 ↗
22. Feng X, Fan J, Li A, Li G (2019) Multireusable thermoset with anomalous flame-triggered shape memory effect. ACS Appl Mater Interfaces 11:16075–16086. https://doi.org/10.1021/acsami.9b0309210.1021/acsami.9b03092 ↗
23. de Luzuriaga AR, Martin R, Markaide N, Rekondo A, Cabañero G, Rodríguez J, Odriozola I (2016) Epoxy resin with exchangeable disulfide crosslinks to obtain reprocessable, repairable and recyclable fiber-reinforced thermoset composites. Mater Horiz 3:241–247. https://doi.org/10.1039/c6mh00029k10.1039/c6mh00029k ↗
24. Taynton P, Yu K, Shoemaker RK, Jin Y, Qi HJ, Zhang W (2014) Heat- or water-driven malleability in a highly recyclable covalent network polymer. Adv Mater 26:3938–3942. https://doi.org/10.1002/adma.20140031710.1002/adma.201400317 ↗
25. Wang Y, Pan Y, Zheng Z, Ding X (2018) Reconfigurable and reprocessable thermoset shape memory polymer with synergetic triple dynamic covalent bonds. Macromol Rapid Commun 39:1800128. https://doi.org/10.1002/marc.20180012810.1002/marc.201800128 ↗
26. Zhu J, Fang G, Cao Z, Meng X, Ren H (2018) A self-folding dynamic covalent shape memory epoxy and its continuous glass fiber composite. Ind Eng Chem Res 57:5276–5281. https://doi.org/10.1021/acs.iecr.8b0022210.1021/acs.iecr.8b00222 ↗
27. Ji S, Fan F, Sun C, Yu Y, Xu H (2017) Visible light-induced plasticity of shape memory polymers. ACS Appl Mater Interfaces 9:33169–33175. https://doi.org/10.1021/acsami.7b1118810.1021/acsami.7b11188 ↗
28. Van Herck N, Du Prez FE (2018) Fast healing of polyurethane thermosets using reversible triazolinedione chemistry and shape-memory. Macromolecules 51:3405–3414. https://doi.org/10.1021/acs.macromol.8b0036810.1021/acs.macromol.8b00368 ↗
29. Fang Z, Zheng N, Zhao Q, Xie T (2017) Healable, reconfigurable, reprocessable thermoset shape memory polymer with highly tunable topological rearrangement kinetics. ACS Appl Mater Interfaces 9:22077–22082. https://doi.org/10.1021/acsami.7b0571310.1021/acsami.7b05713 ↗
30. Lawton MI, Tillman KR, Mohammed HS, Kuang W, Shipp DA, Mather PT (2016) Anhydride-based reconfigurable shape memory elastomers. ACS Macro Lett 5:203–207. https://doi.org/10.1021/acsmacrolett.5b0085410.1021/acsmacrolett.5b00854 ↗
31. Zhang H, Wang D, Wu N, Li C, Zhu C, Zhao N, Xu J (2020) Recyclable, self-healing, thermadapt triple-shape memory polymers based on dual dynamic bonds. ACS Appl Mater Interfaces 12:9833–9841. https://doi.org/10.1021/acsami.9b2261310.1021/acsami.9b22613 ↗
32. 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. Mater Des 186:108248. https://doi.org/10.1016/j.matdes.2019.10824810.1016/j.matdes.2019.108248 ↗
33. Wang Y, Pan Y, Zheng Z, Ding X (2019) Reprocessable and multiple shape memory thermosets with reconfigurability. Macromol Rapid Commun 40:1900001. https://doi.org/10.1002/marc.20190000110.1002/marc.201900001 ↗
34. Wang W, Wang F, Zhang C, Wang Z, Tang J, Zeng X, Wan X (2020) Robust, reprocessable, reconfigurable cellulose-based multiple-shape memory polymer enabled by dynamic metal-ligand bonds. ACS Appl Mater Interfaces 12:25233–25242. https://doi.org/10.1021/acsami.9b1331610.1021/acsami.9b13316 ↗
35. Niu X, Wang F, Kui X, Zhang R, Wang X, Li X, Chen T, Sun P, Shi AC (2019) Dual cross-linked vinyl vitrimer with efficient self-catalysis achieving triple-shape-memory properties. Macromol Rapid Commun 40:1900313. https://doi.org/10.1002/marc.20190031310.1002/marc.201900313 ↗
36. Ji F, Liu X, Lin C, Zhou Y, Dong L, Xu S, Sheng D, Yang Y (2018) Reprocessable and recyclable crosslinked polyethylene with triple shape memory effect. Macromol Mater Eng 304:1800528. https://doi.org/10.1002/mame.20180052810.1002/mame.201800528 ↗
37. Tang Z, Liu Y, Guo B, Zhang L (2017) Malleable, mechanically strong, and adaptive elastomers enabled by interfacial exchangeable bonds. Macromolecules 50:7584–7592. https://doi.org/10.1021/acs.macromol.7b0126110.1021/acs.macromol.7b01261 ↗
38. Ding Z, Yuan L, Liang G, Gu A (2019) Thermally resistant thermadapt shape memory crosslinked polymers based on silyl ether dynamic covalent linkages for self-folding and self-deployable smart 3D structures. J Mater Chem A 7:9736–9747. https://doi.org/10.1039/c9ta01147a10.1039/c9ta01147a ↗
39. Zhang Y, Yuan L, Liang G, Gu A (2018) Developing reversible self-healing and malleable epoxy resins with high performance and fast recycling through building cross-linked network with new disulfide-containing hardener. Ind Eng Chem Res 57:12397–12406. https://doi.org/10.1021/acs.iecr.8b0257210.1021/acs.iecr.8b02572 ↗
40. Xie T (2010) Tunable polymer multi-shape memory effect. Nature 464:267–270. https://doi.org/10.1038/nature0886310.1038/nature08863 ↗
41. Phelan J, Sung C (1997) Cure characterization in bis(maleimide)-diallylbisphenol a resin by fluorescence, FT-IR, and UV-reflection spectroscopy. Macromolecules 30:6845–6851. https://doi.org/10.1021/ma961887f10.1021/ma961887f ↗
42. Chen Y, Dai Q, Zhang X, Feng T (2014) Microstructure and properties of SCE-Al2O3/PES-MBAE composite. J Nanomater. https://doi.org/10.1155/2014/35627310.1155/2014/356273 ↗
43. Davy KW, Kalachandra S, Pandain MS, Braden M (1998) Relationship between composite matrix molecular structure and properties. Biomaterials 19:2007–2014. https://doi.org/10.1016/S0142-9612(98)00047-710.1016/S0142-9612(98)00047-7 ↗
44. Yang Z, Wang Q, Wang T (2016) Dual-triggered and thermally reconfigurable shape memory graphene-vitrimer composites. ACS Appl Mater Interfaces 8:21691–21699. https://doi.org/10.1021/acsami.6b0740310.1021/acsami.6b07403 ↗
45. Kuang X, Guo E, Chen K, Qi HJ (2019) Extraction of biolubricant via chemical recycling of thermosetting polymers. ACS Sustain Chem Eng 7:6880–6888. https://doi.org/10.1021/acssuschemeng.8b0640910.1021/acssuschemeng.8b06409 ↗
46. Ware TH, McConney ME, Wie JJ, Tondiglia VP, White TJ (2015) Voxelated liquid crystal elastomers. Science 347:982–984. https://doi.org/10.1126/science.126101910.1126/science.1261019 ↗
47. Erb RM, Libanori R, Rothfuchs N, Studart AR (2012) Composites reinforced in three dimensions by using low magnetic fields. Science 335:199–204. https://doi.org/10.1126/science.121082210.1126/science.1210822 ↗
48. Stuart MA, Huck WT, Genzer J, Muller M, Ober C, Stamm M, Sukhorukov GB, Szleifer I, Tsukruk VV, Urban M, Winnik F, Zauscher S, Luzinov I, Minko S (2010) Emerging applications of stimuli-responsive polymer materials. Nat Mater 9:101–113. https://doi.org/10.1038/nmat261410.1038/nmat2614 ↗
49. Zheng N, Hou J, Xu Y, Fang Z, Zou W, Zhao Q, Xie T (2017) Catalyst-free thermoset polyurethane with permanent shape reconfigurability and highly tunable triple-shape memory performance. ACS Macro Lett 6:326–330. https://doi.org/10.1021/acsmacrolett.7b0003710.1021/acsmacrolett.7b00037 ↗
50. Zhao Q, Zou W, Luo Y, Xie T (2016) Shape memory polymer network with thermally distinct elasticity and plasticity. Sci Adv 2:1501297. https://doi.org/10.1126/sciadv.150129710.1126/sciadv.1501297 ↗
51. Lendlein A, Kelch S (2002) Shape-memory polymers. Angew Chem Int Ed 41:2034–2057. https://doi.org/10.1002/1521-3773(20020617)41:12%3c2034:AID-ANIE2034%3e3.0.CO;2-M10.1002/1521-3773(20020617)41:12<2034:AID-ANIE2034>3.0.CO;2-M ↗