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Inexpensive and Recyclable Thermosets Jacob J pubs.acs.org/acsapm Letter Polystyrene-Based Vitrimers: Inexpensive and Recyclable Thermosets Jacob J. Lessard, Georg M. Scheutz, Rhys W. Hughes, and Brent S. Sumerlin* Cite This: ACS Appl. Polym. Mater. 2020, 2, 3044−3048 Read Online ACCESS Metrics & More Article Recommendations *sı Supporting Information ABSTRACT: We report a straightforward and scalable method for the generation of polystyrene-based vinylogous urethane vitrimers using conventional radical polymerization. The copoly- merization of the commercially available and inexpensive monomers styrene and (2-acetoacetoxy)ethyl methacrylate pro- duced β-ketoester-functional network precursors on a multigram scale, which could be cross-linked with diamines to yield thermally robust vitrimer materials. Vitrimers were (re)processed over three destruction/compression cycles with acid catalysis to overcome the effects of backbone entanglements. Lastly, the viscoelastic properties were investigated, revealing a higher activation energy fl for viscous ow (Ea) compared with previously prepared methacrylate-based analogs. KEYWORDS: covalent adaptable network, vitrimer, reprocessable thermosets, dynamic cross-links, recyclable networks he cross-linked structure of a thermoset endows the effective tool for investigating the fundamental relationships T material with mechanical durability and chemical between network structure and flow behavior,14,27 the broader resistance. However, these benefits come at the cost of utility of simplified conventional radical polymerization for dramatically impeded reprocessability via conventional ther- industrial applications is undeniable.28 Despite this, in the field momechanical methods.1 To circumvent the static nature of of vitrimers, there are very few reports that take advantage of thermosets without entirely compromising their stability, the simplicity of conventional radical polymerization of vinyl network structures containing dynamic linkages have been monomers to generate vitrimer materials.8,29,30 Nishimura et developed to permit cross-link exchange and macroscopic al. synthesized vitrimers via silyl ether cross-linking of linear 2,3 flow. In particular, vitrimers have shown great promise in copolymers from styrene and 2-(4-vinyl-benzyloxy)-ethanol 2,4 terms of material properties and reprocessability. Thus far, prepared by conventional radical polymerization.8 However, Downloaded via UNIV OF FLORIDA on June 2, 2021 at 21:48:55 (UTC). most research has focused on the exploration of different cross- both the cross-linker and the reactive comonomer in this 5−9 10−13 link exchange chemistries, catalyst systems, and report required additional synthetic steps, potentially limiting 14−17 network structures. However, a critical hurdle for the scalability and cost efficiency. application of vitrimers lies in the translation from the See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles. Herein, we report a straightforward protocol for the scalable academic laboratory to industrially relevant materials and 2,18−20 synthesis of polystyrene-based vitrimers (VitPS) from commer- procedures. For example, vitrimer materials have been cially available and inexpensive reagents using conventional developed using readily available, inexpensive monomers or radical polymerization (Figure 1). Styrene and (2- postpolymerization modification from commercially available 7,8,21−26 acetoacetoxy)ethyl methacrylate (AAEMA) were copolymer- polymers. Our group recently prepared vitrimeric ized at 70 °C, yielding linear vitrimer precursors. The poly(methyl methacrylate) mimetics that exhibited superior incorporation of the β-ketoester-bearing AAEMA monomer thermal and solvent stability while maintaining reprocessability allowed for facile network formation with xylylene diamine via through amine exchange of vinylogous urethane (VU) cross- 31 26 VU formation. The polymerization of the network precursors links. Moreover, we reported that the phase separation and the vitrimer formation were scalable (>15 g of polymer present in vitrimers derived from block copolymers leads to enhanced resistance to macroscopic deformation as compared with networks prepared from statistical copolymers of identical Received: May 18, 2020 compositions.14 The polymers in these two previous studies Accepted: June 29, 2020 were synthesized using reversible addition−fragmentation Published: July 9, 2020 chain transfer (RAFT) polymerization to limit the molecular weight and allow block copolymer formation, respectively. Although the control afforded by RAFT polymerization is an © 2020 American Chemical Society https://dx.doi.org/10.1021/acsapm.0c00523 3044 ACS Appl. Polym. Mater. 2020, 2, 3044−3048 ACS Applied Polymer Materials pubs.acs.org/acsapm Letter Figure 1. Polymerization scheme, vitrimer formation scheme, and reprocessing images for polystyrene-based vitrimers. fi and >6 g vitrimer generated), and the networks could be Figure 2. Synthesis of poly(styrene-co-AAEMA). (A) Pseudo- rst- order rate plot of the averaged monomer consumption with time reprocessed over three deconstruction/compression cycles, showing a constant radical concentration throughout the course of the showing the retention of the network structure. polymerization. (B) Pseudo-first-order rate plot of each monomer Finally, we probed the viscoelastic properties of the resulting consumption showing a faster incorporation of AAEMA. (C) Percent polystyrene-based vitrimers, revealing a higher activation of unreacted AAEMA monomer compared with unreacted styrene fl energy for viscous ow (Ea) compared with previously monomer. (D) Gel permeation chromatography traces of poly- prepared methacrylate-based analogs.14,26 (styrene-co-AAEMA) polymerization over time, normalized using the The copolymerization of styrene with AAEMA (2 M total reaction solvent as an internal standard, show an increase in polymer concentration at a relatively constant molecular weight. monomer concentration, [AAEMA]o/[Sty]o 40:60) was conducted at 70 °C in toluene using azobis(isobutyronitrile) as a radical initiator (Figure 1). The copolymer molecular weight remained relatively constant with monomer conversion, as expected for conventional radical polymerizations (Figure 2A−D). The averaged monomer consumption followed a pseudo-first-order rate law, suggesting a constant radical concentration throughout the polymerization (Figure 2A). Notably, we found that AAEMA was consumed at a slightly faster rate than styrene, which is reflected in the decreasing monomer ratio of AAEMA to styrene and the steeper slope of the linear pseudo-first-order rate plot of AAEMA (Figure 2B,C). The differing rates of incorporation of AAEMA and styrene are indicative of a slight compositional drift during the copolymerization. In early stages, copolymers slightly enriched in AAEMA are generated, shifting toward styrene-rich copolymers in later stages as the reaction mixture becomes depleted of AAEMA (Figure 2D). Poly(styrene-co-AAEMA) (72.2 kg/mol, Đ = 1.62, 43% overall AAEMA incorporation) was isolated in multigram quantities through precipitation into methanol, followed by drying under reduced pressure (Figures β Figure 3. Formation of vitrimers by solution-casting poly(styrene-co- S1 and S2). The preservation of the -ketoester on the AAEMA) with a xylylene diamine cross-linker and p-toluenesulfonic polymer backbone was verified by Fourier transform infrared acid (TsOH) catalyst. (A) Stacked and normalized ATR-FTIR (FTIR) and 1H NMR spectroscopy (Figure 3A and Figure S3). spectra of poly(styrene-co-AAEMA) (orange) and vitrimer (black) Network formation was achieved by cross-linking poly- with a β-ketoester (purple) and vinylogous urethane (red) small- (styrene-co-AAEMA) with xylylene diamine (XDA, 0.86 mol molecule analog. (B) Differential scanning calorimetry traces of the equiv of diamine to AAEMA) and p-toluenesulfonic acid (0.1 polymer (orange) and vitrimer (black) showing an increase in Tg after mol % to XDA) as a catalyst via a solution-cast procedure cross-linking. The inset image shows the vitrimer material before and (Figure 3 and Figure S4).12 The resulting film was cured at 80 after processing. °C and compression-molded at 160 °C under a vacuum environment to yield the processed vitrimer material. The Additionally, the increase in the glass-transition temperature ffi fi ° e cient formation of VU cross-links was con rmed through (Tg) from 40 to 100 C was consistent with the formation of a ATR-FTIR spectroscopy by comparing the characteristic VU covalently cross-linked network structure (Figure 3B). ∼ −1 signals at 1650 and 1600 cm with carbonyl peaks from To validate the reprocessability of the networks, VitPS was 1700 to 1750 cm−1 in small-molecule analogs (Figure 3A). subjected to two additional destruction/compression cycles, 3045 https://dx.doi.org/10.1021/acsapm.0c00523 ACS Appl. Polym. Mater. 2020, 2, 3044−3048 ACS Applied Polymer Materials pubs.acs.org/acsapm Letter Figure 4. Vitrimer reprocessing and analysis. (A) Image of the vitrimer material after reprocessed cycles (P, processed; R×1, first reprocess cycle; R×2, second reprocess cycle). (B) Storage (solid) and loss (dashed) modulus of (re)processing cycles showing a slight increase in the rubbery plateau modulus for R×2. (C) Tan(δ) for all three (re)processing cycles. (D) Differential scanning calorimetry traces of vitrimer materials after × (re)processing showing an increase in Tg for R 2 (heating, exotherm up). (E) Stacked and normalized ATR-FTIR spectra after (re)processing
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