Self-Immolative, Adaptable, Oleic-Acid-Based Thermosets: Modular Design, Degradability, and Light-Driven Reprocessability

Self-Immolative, Adaptable, Oleic-Acid-Based Thermosets: Modular Design, Degradability, and Light-Driven Reprocessability | Authorea try { document.documentElement.classList.add('js'); } catch (e) { } var _gaq = _gaq || []; _gaq.push(['_setAccount', 'G-8VDV14Y67G']); _gaq.push(['_trackPageview']); (function() { var ga = document.createElement('script'); ga.type = 'text/javascript'; ga.async = true; ga.src = ('https:' == document.location.protocol ? 'https://ssl' : 'http://www') + '.google-analytics.com/ga.js'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(ga, s); })(); Skip to main content Preprints Collections Wiley Open Research IET Open Research Ecological Society of Japan All Collections About About Authorea FAQs Contact Us Quick Search anywhere Search for preprint articles, keywords, etc. Search Search ADVANCED SEARCH SCROLL This is a preprint and has not been peer reviewed. Data may be preliminary. 3 April 2026 V1 Latest version Share on Self-Immolative, Adaptable, Oleic-Acid-Based Thermosets: Modular Design, Degradability, and Light-Driven Reprocessability Authors : Sumin Kang , Songah Jeong , Seoyeon Choi , Van Nguyen , Eunpyo Choi , Jinsoo Park , and Hyungwoo Kim 0000-0003-1958-3587 [email protected] Authors Info & Affiliations https://doi.org/10.22541/au.177522718.87118622/v1 116 views 70 downloads Contents Abstract Information & Authors Metrics & Citations View Options References Figures Tables Media Share Abstract This paper presents a rational molecular design for sustainable thermosets that utilizes biomass feedstocks and provides molecular-level control over both the malleability and degradability of the thermosets. For this design, we deliberately synthesized an oleic-acid-based degradable core monomer via a one-pot process, which was then used to copolymerize with a polycaprolactone-based functional macromonomer to form a robust transparent network containing active sites for programmable degradation in response to a specific stimulus, thus releasing the predesigned products. With the addition of trace alcohols, the renewable networks became recyclable through covalent bond exchange while maintaining site-specific degradability. Furthermore, incorporating polydopamine-coated ZrO2 nanoparticles reinforced the network, imparting enhanced modulus, radiopacity, and light-driven spatiotemporal control. As a result, the composite demonstrated rapid underwater healing, shape-preserving reconfiguration capabilities, and an adhesive performance that was recyclable yet disposable. This design concept could be extended by incorporating other biomass-derived units or synergistic additives, thereby offering a feasible molecular strategy for the development of sustainable thermosets, which ultimately highlights the significance of the molecular engineering of abundant fatty acids for the production of functional polymeric materials for use in practical applications. Article category: Full Paper Subcategory: Sustainable Materials Self-Immolative, Adaptable, Oleic-Acid-Based Thermosets: Modular Design, Degradability, and Light-Driven Reprocessability Sumin Kang, Songah Jeong, Seoyeon Choi, Van Du Nguyen, Eunpyo Choi, Jinsoo Park, and Hyungwoo Kim* S. Kang, Dr. S. Jeong, S. Choi, Prof. H. Kim School of Polymer Science and Engineering, Chonnam National University, 77 Yongbong-ro, Buk-gu, Gwangju 61186, Korea E-mail: [email protected] Dr. V. D. Nguyen Korea Institute of Medical Microrobotics, 43-26, Cheomdangwagi-ro 208-beon-gil, Buk-gu, Gwangju 61011, Korea Prof. E. Choi Department of Mechanical Engineering, Sogang University, 35, Baekbeom-ro, Mapo-gu, Seoul 04107, Korea Prof. J. Park Department of Mechanical Engineering, Chonnam National University, 77 Yongbong-ro, Buk-gu, Gwangju 61186, Korea Keywords: oleic acid, thermosets, recycling , near-infrared, depolymerization Abstract This paper presents a rational molecular design for sustainable thermosets that utilizes biomass feedstocks and provides molecular-level control over both the malleability and degradability of the thermosets. For this design, we deliberately synthesized an oleic-acid-based degradable core monomer via a one-pot process, which was then used to copolymerize with a polycaprolactone-based functional macromonomer to form a robust transparent network containing active sites for programmable degradation in response to a specific stimulus, thus releasing the predesigned products. With the addition of trace alcohols, the renewable networks became recyclable through covalent bond exchange while maintaining site-specific degradability. Furthermore, incorporating polydopamine-coated ZrO 2 nanoparticles reinforced the network, imparting enhanced modulus, radiopacity, and light-driven spatiotemporal control. As a result, the composite demonstrated rapid underwater healing, shape-preserving reconfiguration capabilities, and an adhesive performance that was recyclable yet disposable. This design concept could be extended by incorporating other biomass-derived units or synergistic additives, thereby offering a feasible molecular strategy for the development of sustainable thermosets, which ultimately highlights the significance of the molecular engineering of abundant fatty acids for the production of functional polymeric materials for use in practical applications. 1. Introduction Thermosetting polymers are indispensable materials for structural, electronic, and biomedical applications due to their high dimensional stability, chemical resistance, and mechanical robustness. [1,2] However, their inherent irreversibility after curing means that they cannot be reshaped, repaired, or recycled, thus generating persistent waste streams with potentially negative environmental effects. As such, in the circular materials economy, chemical design and fabrication strategies for the production of sustainable polymer thermosets need to satisfy three key design principles: (i) the use of biomass to minimize dependence on fossil fuels, (ii) recycling/reuse through on-demand reversible and/or exchangeable covalent bonds, and (iii) controlled depolymerization for rapid, selective, and energy-efficient disposal, producing predetermined end-of-life products. [3–6] However, achieving these principles simultaneously within a single network system remains challenging. From the standpoint of molecular design, covalent adaptable networks (CANs), including vitrimers, have recently emerged as a transformative chemical design in the production of sustainable polymer thermosets. [7–10] In contrast to conventional thermosets, the network topology of these materials can be rearranged via associative and/or dissociative mechanisms to promote stress relaxation, reprocessing, and self-healing behavior. [11–15] Biobased CANs have gained particular attention because of their adaptability, sustainability, low cost, chemical accessibility, and structural versatility. In these terms, various biomass feedstocks, including plant oils, fatty acids, terpenes, lignin derivatives, and carbohydrates, have been employed to construct dynamic networks that require less petrochemical input. [16–22] Nevertheless, most previously reported biobased networks rely on disulfide, acetal, and imine linkages and typically require high temperatures to prompt bond exchange or strong acids or bases to cause random fragmentation for degradation. [22–25] Thus, they often suffer from low stability, require the use of toxic exogenous components, offer a less well-defined network structure, and further lack a chemical “exit pathway” via site-specific depolymerization under benign conditions at the end of their service life, leaving them still falling short of fulfilling the criteria for sustainable thermoset design. [24,26,27] For comparison, recent biobased CANs are summarized in Table S1, revealing biomass components, mechanical properties (tensile and adhesion strength), thermal behavior (glass transition and topology freezing), degradation conditions, and recycling mechanisms. Oleic acid (OA) is a highly accessible monounsaturated fatty acid that has been employed as a precursor in a wide range of polymeric materials such as elastomers, nanocomposites, gels, and delivery systems due to its heterogeneous functionalities (i.e., alkene and carboxylic acid groups) and intrinsic lipophilicity, most often serving as a hydrophobic or plasticizing component. [28–32] While OA has been widely utilized in organic and polymeric materials, it is typically incorporated in a relatively unmodified manner. Chemically precise modification of OA to encode programmable, site-specific network disassembly remains rare, and OA-based CANs reported to date generally do not enable controlled or on-demand degradation. In this paper, we present a molecular design strategy to address these challenges using an OA-derived adaptable and degradable network. We designed, for the first time, a chemically well-defined, self-immolative OA-based monomer via one-pot synthesis that is both stimulus-responsive and bearing polymerizable groups at both ends. This monomer was combined with a lipoic-acid-functionalized polycaprolactone (PCL) through thiol–ene click polymerization to fabricate a biocompatible network with programmable degradation capability, enabling site-specific molecular disassembly and oleylamine release. The addition of trace β-mercaptoethanol (BME) imparted malleability via thermally activated bond exchange without compromising thermomechanical properties. Furthermore, incorporation of polydopamine (PDA)-coated ZrO 2 nanoparticles (NPs) yielded reinforced renewable composites with enhanced modulus, radiopacity, and near-infrared (NIR)-triggered spatiotemporal control. Of note, the present system enables efficient bond exchange under low-intensity NIR irradiation compared to other light-controllable CANs and represents the first example of OA-based CANs operated by NIR light (Table S2). The resulting materials exhibit rapid underwater reprocessability, precise reconfiguration, and reusable yet disposable adhesive behavior, demonstrating a sustainable thermoset platform integrating biomass utilization, site-specific chemical recycling, and light-driven reprocessability. This design strategy provides a versatile molecular framework for transforming fatty acids into functional, high-performance polymer materials. 2. Results and discussion Figure 1 illustrates the synthetic route used to produce the proposed biobased, recyclable, degradable network derived from OA, which is abundant in nature in its ester form. The OA-based network (OAN) consists of three molecular components: (i) a degradable core monomer (dOA) synthesized from OA-derived isocyanate 1 and sacrificial diol 2 , (ii) a PCL-based telechelic macromonomer (PCL-LA), end-functionalized with DL-α-lipoic acid (LA), and (iii) BME. dOA is readily synthesized from OA via a one-pot reaction with an overall yield exceeding 70%, without intermediate purification. This process involves the azide formation of OA followed by Curtius rearrangement to produce 1 and subsequent urethane formation with two equivalents of 2 to yield dOA. PCL-LA is prepared from PCL-diol (2 kDa) through Steglich esterification with LA, with a high substitution yield of 85%, producing a biocompatible backbone bearing 1,2-dithiolane end groups that undergo a ring-opening reaction under photoirradiation. The subsequent combination of dOA and PCL-LA forms a network structure consisting of thioether and disulfide bonds generated via thiol-ene and ring-opening polymerization, respectively. This arises from the two alkene functionalities of dOA and the four latent thiols of PCL-LA that are generated due to homolytic photocleavage under 365-nm irradiation. Sub-stoichiometric amounts of BME are added during network formation, leading to the covalent incorporation of dangling alcohol functionalities into the network while maintaining the 1:1 stoichiometric balance between the alkene and thiol groups. Therefore, the resulting OAN exhibits both triggered degradation behavior due to the sacrificial xylenolic moieties from dOA and topological rearrangement via transesterification due to the residual hydroxyl functionalities. Figure 1. Overview of the design strategy for the proposed functional oleic-acid (OA)-based network (OAN): (i) synthesis of the degradable, OA-based monomer (dOA), (ii) polycaprolactone ( PCL) macromonomer functionalized with lipoate moieties (PCL-LA), and (iii) photo-cross-linking in the presence of β-mercaptoethanol (BME). The combination of these components produces an OAN that is degradable and recyclable. The triggered degradation behavior of dOA is schematically presented in Figure 2 a. The cleavage reaction of the tert -butyldimethylsilyl (TBS) group in dOA readily occurs following exposure to fluoride owing to the strong Si–F bond formation, [33,35,36] which concomitantly induces an electronic cascade leading to sequential 1,4-elimination toward both carbamate linkages. As a result, the two flanked oleylamine moieties in dOA fall apart and carbon dioxide is released. The process leading to two successive elimination events from a single triggering event includes both nucleophilic addition and rearomatization, as detailed in Figure S1. In the present study, the generation of oleylamine during the reaction was monitored using proton nuclear magnetic resonance ( 1 H NMR) spectroscopy (Figure 2b). After exposure to 2.0 equiv CsF, peak a for the methylene protons neighboring the amine in oleylamine gradually appeared at 2.85 ppm, while peak b at 3.11 ppm for the same protons near the carbamate disappeared. In contrast, peak c for the vinylic protons at 5.35 ppm for the internal alkenes did not change, thus we used it as a reference peak. A comparison of the full NMR spectra for dOA before and after the elimination events is presented in Figure S2. Figure 2c presents the changes in the normalized integration of peaks a and b (based on peak c ) during the elimination process. Two kinetic regions were observed when estimated using a pseudo-first-order kinetic model (Figure S3), representing each oleylamine elimination event, with a rate constant of 0.004 min –1 for k 1 and 0.002 min –1 for k 2 (both R 2 reports. [33,37,38] Collectively, these results indicate that triggered elimination reactions occurred in dOA. A series of OAN samples containing 0, 20, and 40 mol% BME relative to the total components (denoted as OAN 0 , OAN 20 , and OAN 40 , respectively) and a control network using only PCL-LA were fabricated. When the BME content exceeded 40%, network formation was inhibited because the excess BME interfered with the establishment of cross-linking points. In addition, X-ray photoelectron spectroscopy (XPS) analysis for S 2p 3/2 electrons revealed that, irrespective of the BME content, the OAN samples predominantly consisted of thioether bonds (>75%), with a minor fraction of disulfide bonds (Figure S4). The dominance of thioether linkages was attributed to the higher reactivity and irreversibility of thiol-ene polymerization compared to disulfide bond formation. [39–42] The thermal stability of the OAN samples was investigated using thermogravimetric analysis (TGA) (Figure 2d). Without dOA, the PCL-LA network alone exhibited good thermal stability with a 5% weight loss temperature ( T d5 ) of 360 °C. However, for OAN 0 , T d5 decreased to 262 °C due to the lower thermal stability of dOA ( T d5 , 248 °C) (Figure S5a). Increasing the BME content in the OAN led to a further decrease in T d5 , falling to 246 °C for OAN 20 and 218 °C for OAN 40 . This loss of thermal stability for the OAN due to the presence of dOA as well as BME that has the potential to reduce the overall cross-linking density. The thermal transition behavior of the OAN samples was also investigated using differential scanning calorimetry (DSC) (Figure 2e). The enantiotropic phase transition of the semi-crystalline PCL segments in PCL-LA was observed at 25–45 °C during heating, with a corresponding enthalpy of ~85 J g –1 . [43–45] This transition was also observed in the OAN samples, but their enthalpy was lower (42 to 45 J g –1 , increasing with a higher BME content) due to the formation of the thiol-ene-type network with dOA and enhanced network flexibility from incomplete cross-linking. Meanwhile, no transition was observed for dOA until thermal decomposition (Figure S5b). The thermal data for all samples are summarized in Table S3. The OAN samples were all fabricated in film form via solution casting followed by photopolymerization. UV–vis spectrometry revealed that the resulting transparent films had an optical transmittance of (Figure 2f). The absorption peak at 335 nm for PCL-LA, corresponding to the dithiolane moiety before ring opening, completely disappeared after irradiation, [46,47] indicating an increase in the transmittance of the network in the UVA region and highlighting the suitability of photopolymerization for network formation (Figure S6). The mechanical properties of the OAN films were evaluated using tensile testing (Figure 2g). The PCL-LA film was stiff and brittle, whereas OAN 0 was slightly tougher due to the incorporation of dOA. The addition of BME initially enhanced the overall toughness of OAN further, with OAN 20 exhibiting a toughness of those of OAN 0 ), despite a slight reduction in its elastic modulus (11 ± 3 MPa). This could be attributed to the additional hydrogen-bond-assisted inter-network interactions introduced by BME. However, the toughness of OAN 40 was almost 50% reduced due to the decrease in effective cross-linking points. Figure 2h presents a comparison of the elastic modulus and toughness values for the OAN and control samples. The swelling degree of the network samples was estimated in methanol (MeOH), water, and acetonitrile (MeCN) (Figure 2i). Because all of the samples were relatively hydrophobic, they did not swell in the protic solvents MeOH and water after 24 h of immersion at 25 °C. Although PCL-LA and OAN 0 exhibited appreciable swelling in MeCN, this swelling was suppressed in the BME-containing OAN samples, likely due to the intra-network interactions. However, all samples exhibited a high gel fraction after immersion, which was attributed to the formation of stable cross-linked structures. Figure 2. (a) Schematic description of the degradation mechanism for dOA when triggered by fluoride. (b) Change in the specific NMR peaks for dOA over time during the elimination process after exposure to fluoride. (c) Time-dependent normalized integration of the NMR peaks a and b during the elimination process. (d, e) Thermal properties of the network samples: (d) TGA thermograms, with the dotted line indicating 5% weight loss, and (e) DSC traces during the 2nd heating (dotted) and cooling (solid) cycles. (f) Optical transmittance spectra for the network samples (size: 3 cm × 6 cm × 0.1 mm). The inset shows a transparent OAN 20 film. (g) Representative tensile stress–strain curves and (h) corresponding average elastic moduli and toughness values for the samples. (i) (top) Swelling degree and (bottom) gel fractions of the samples measured in common media. Taking advantage of the dangling hydroxyl groups from BME and the ester linkages in the PCL backbone, both OAN 20 and OAN 40 exhibited thermally reversible bond exchange via transesterification. This was demonstrated by stress relaxation tests using a dynamic mechanical analyzer (DMA) under a 1% step strain. The applied stress in the strained samples relaxed over time in a temperature-dependent manner, while the change in their relaxation modulus ( G ) was monitored. The characteristic relaxation time (τ*), defined as the time required for G / G 0 to reach 1/ e , was found to decrease with an increase in the temperature. In particular, the relaxation rate for OAN 20 was sluggish at 40 °C, the temperature at which the DSC endothermic transition occurred, but significantly increased above 60 °C, providing evidence for the presence of associative bond exchange within the network ( Figure 3 a). OAN 40 exhibited a faster relaxation behavior than OAN 20 due to its higher hydroxyl content, which facilitated bond exchange (Figure 3b). Also, the exchange temperatures are relatively lower than those of other transesterification systems (Table S1), which can be attributed to the close proximity of reactive groups within the matrix—reducing entropic penalties—and to the favorable viscoelastic properties of the matrix. The activation energy ( E a ) for the topological rearrangement of each network sample was determined based on the linear correlation between τ* and the reciprocal temperature in an Arrhenius plot (Figure 3c). The E a for OAN 20 was 1.3 times higher than that for OAN 40 , which was consistent with their dynamic mechanical behavior and comparable to other vitrimer-type materials that undergo transesterification. [48–50] The thermal malleability of OAN 20 and OAN 40 was also confirmed via dilatometric creep analysis with a DMA (Figure 3d). The glass transition temperature ( T g ) for these samples was observed at around 30 °C due to the presence of the PCL segment, which was in accordance with the DSC data. The onset point for a separate plateau was defined as the topology freezing temperature ( T v ), which originates from thermally activated bond exchange and the rearrangement of the network topology, enhancing the viscoelastic fluid properties and volumetric expansion above T v . [51–53] OAN 20 had a T v of OAN 40 , which was consistent with the lowered E a resulting from the higher BME content. In addition, the cross-linking density of both networks was evaluated using DMA and determined to be 2044 and 449 mol cm –3 for OAN 20 and OAN 40 , respectively. This trend is consistent with the E a and T v values. Given that biocompatible components were employed in the proposed OAN design, the cytotoxicity of the network samples was tested against A549 and RAW264.7 cells at various network concentrations up to 10 mg mL –1 , and their relative viability was determined using colorimetric MTT assays (Figure 3e and 3f). After incubation, the epithelial A549 cells maintained high viability across all concentrations, while the viability of the macrophage cells decreased below 75% for the OAN samples only at concentrations exceeding 5 mg mL –1 . Even though a cytotoxic effect was observed at high concentrations, the proposed OAN can be regarded as biocompatible with minimal cytotoxicity, demonstrating its potential for use in sustainable practical applications. Figure 3. Stress relaxation tests for (a) OAN 20 and (b) OAN 40 at different temperatures. The dotted lines indicate the characteristic relaxation time (τ*). (c) Linear relationship between τ* and the reciprocal temperature based on the Arrhenius model for the estimation of the activation energy ( E a ) for the two networks. (d) Change in the thermal strain for (top) OAN 20 and (bottom) OAN 40 , during dilatometric creep tests with an applied axial force of 1.0 N. (d, e) Relative viability of (e) A549 and (f) RAW264.7 cells after culturing with the network samples at different concentrations. Based on the characterization results for the OAN samples, we selected OAN 20 for further testing due to its high mechanical strength, dimensional stability, and thermal reprocessability. This network was found to be self-healing, with scratches made on an OAN 20 film (thickness, 0.1 mm) with a razor blade completely restored within 80 min while stored at 60 °C ( Figure 4 a). The bulk-state recycling process for OAN 20 is also depicted in Figure 4b. After mechanical chopping, small pieces of OAN 20 were readily reprocessed into a smooth film by heating them at 80 °C for 1 h in an oven under light compression. The tensile stress–strain curve obtained for the recycled film was nearly identical to that for the pristine film (Figure 4c), with a similar elastic modulus and toughness (Figure 4d). These results demonstrate the remarkable chemical malleability of the proposed OAN, which is associated with thermally activated transesterification within the bulk phase and at the interface. As expected, the control films prepared using PCL-LA alone or OAN 0 were not recyclable under heating due to the absence of bond-exchange reactions (Figure S7a), whereas OAN 40 was recyclable in a manner similar to OAN 20 (Figure S7b). With the embedded dOA providing de-cross-linkable points within the network, the degradation of OAN 20 triggered by fluoride was investigated. Following exposure to 10 mM CsF in an EtOH/water mixture (1:1, v/v) at 25 °C, the integral area of the initial tensile curve decreased over time due to fluoride-induced de-cross-linking, leading to a gradual reduction in toughness. Consequently, the network became increasingly fragile during exposure and its toughness was unmeasurable after 10 d of immersion (Figure 4e). This degradation process was accelerated by increasing the fluoride concentration, with complete degradation achieved within 3 d using a concentration of 50 mM (Figure 4f). The degradation rate could be modulated not only by tuning trigger concentration, but also by adjusting surface accessibility and solvent or temperature conditions. In contrast, exposure to 50 mM chloride had only a limited effect, illustrating the selective degradation behavior of dOA. (The obtained tensile curves under other conditions are presented in Figure S8.) Fourier-transform infrared spectroscopy (FTIR) further corroborated the degradation behavior. The urethane-related N–H bending band at 1536 cm –1[54] progressively decreased upon triggering. In particular, the normalized N–H bending intensity followed a similar trend to the toughness reduction and almost disappeared within 1 h of exposure to CsF (50 mM), indicating that the mechanical deterioration is directly associated with urethane bond cleavage (Figure S9). This conceptual network employs fluoride-triggered degradation, but substituting the TBS group with other reactive units or employing polymer backbones other than PCL would allow flexibility in the choice of the triggering stimuli (e.g., metals, pH changes, enzymes or light) and in controlling the overall degradation behavior, thereby representing a versatile platform with a broad range for various applications. Figure 4. Representative photographs of OAN 20 films demonstrating (a) self-healing behavior following scratches and subsequent heating (scale bar, 0.2 mm) and (b) thermal recyclability after fracturing. (c) Tensile stress–strain curves of pristine and recycled OAN 20 samples. (d) Comparison of the elastic moduli and toughness values before and after recycling OAN 20 . (e) Overlaid tensile stress–strain curves for OAN 20 during degradation triggered by fluoride at 10 mM. (f) Change in the toughness values for OAN 20 over time after exposure to fluoride at different concentrations (violet) or 50 mM chloride (orange). We subsequently incorporated PDA-coated ZrO 2 NPs into OAN 20 as a proof of concept for a reinforced OA-based composite (OAC) with light-induced reprocessability. The PDA outer coating layer imparted photothermal properties on the chemically stable ZrO 2 core and improved the miscibility with the OAN 20 matrix during the formation of the OAC. Figure 5 a presents an illustration of the core–shell structure of the NPs, with corresponding TEM imaging confirming an average diameter of 22 ± 2 nm and shell thickness of ~3 nm, with a relatively uniform size distribution (Figure S10a). The zeta potential of ZrO 2 did not notably change when coated with PDA (Figure S10b). An aqueous dispersion of NPs (150 µg mL –1 in DI water) was also placed under NIR irradiation at 808 nm (3 W cm –2 ) and monitored using an IR thermal imaging camera, with the temperature increasing from in temperature due to the photothermal effect had a positive relationship with the NP concentration (Figure 5b), while DI water without NPs exhibited only a negligible increase. Figure 5c presents the changes in the temperature of the NP dispersion that was heated with NIR light and then cooled to near room temperature without NIR irradiation for five on/off cycles of 10 min each. These results support reliable and repeatable heating capabilities of the NPs. An illustration for the formation of the OAN 20 /NP composite is presented in Figure 5d. The NPs were added to a prepolymer formulation of OAN 20 to obtain the OAC, followed by UV curing. Though the NPs were well dispersed in the polymerizing mixture, without the prepolymer, the NPs aggregated in the matrix during the sequential curing process. The incorporation of the NPs dramatically stiffened the matrix (Figure 5e), with the elastic modulus of the OAC increasing proportionally with the NP content up to 2.5 wt% (Figure S11). As an example, the OAC sample containing 2.5 wt% NPs (OAC 2.5 ) had a modulus of 37 ± 3 MPa, which was 3.3 times higher than that of OAN 20 and comparable to that of general thermoplastic elastomers or polyurethanes. [55–58] However, a free-standing resilient composite did not form when the NP content exceeded 5 wt%, which likely compromised the overall integrity of the material. Accordingly, the 2.5 wt% NP content was selected as an optimal balance between mechanical reinforcement and network integrity, prioritizing sufficient robustness for light-controlled reprocessability rather than maximizing stiffness alone. The OAC samples exhibited photothermal behavior that was also dependent on the NP content. Following irradiation at 808 nm with a low intensity of 0.5 W cm –2 , the surface temperature of an OAC 2.5 film rapidly reached 60 °C within 30 s, whereas the matrix itself did not respond to NIR irradiation (Figure 5f). Here, the temperature rise and response time are sufficient to activate bond exchange, and higher temperatures or faster responses can be readily achieved by adjusting the PDA loading or irradiation intensity for specific target applications. Figure 5g compares the appearance of an OAC 2.5 disc with that of an OAN 20 sample produced without NPs. Unlike OAN 20 , the brown OAC 2.5 composite was visibly opaque and further radiopaque, which is attributed to the presence of NPs. This feature could be advantageous for potential biomedical or industrial applications, such as implantable devices, non-destructive testing, and real-time tracking. Figure 5. (a) (top) Illustration of a PDA-coated ZrO 2 nanoparticle (NP) with a corresponding TEM image. (bottom) Thermal infrared images of an NP dispersion in DI water under NIR irradiation for 10 min. (b) Change in the temperature of the NP dispersion according to the irradiation time at different NP concentrations. (c) Temperature profiles of the NP dispersion over five on–off NIR irradiation cycles (10 min per cycle). (d) Schematic depiction of the preparation of OA-based composite (OAC) samples composed of OAN 20 and NPs at varying concentrations. (e) Representative tensile stress–strain curves obtained from the OAC samples with different NP concentrations and (f) their corresponding change in temperature under NIR irradiation in air. (g) Comparison of photographs and radiographs of disc-shaped samples of OAN 20 and OAC 2.5 . Subsequent analysis revealed that OAC 2.5 could be recycled using both heat and NIR irradiation based on the synergistic properties of OAN 20 and the NPs ( Figure 6 a). Composite fractures were reformed to their initial film state (size: 1.5 cm × 1.5 cm × 0.2 mm) via transesterification activated either by direct heating at 60 °C for 1 h or by NIR irradiation (808 nm, 0.5 W cm –2 , 30 min), which raised the temperature to the same level. Of particular note, NIR irradiation could also restore the fractures in DI water (Figure 6a, right) via the rapid local heating of the exposed area. Figure 6b presents the results of stress relaxation tests for OAC 2.5 using DMA at various temperatures. An E a of 123.2 kJ mol –1 was observed, which was twice that of OAN 20 due to the greater energy required for bond exchange due to the presence of NPs in the matrix. A linear Arrhenius plot of τ* against the reciprocal temperature is presented in Figure S12. The photothermal behavior of OAC 2.5 was also investigated using on/off NIR irradiation tests (Figure 6c). Its temperature rapidly rose above 60 °C during the on state and then cooled to room temperature during the off state over five repeating cycles (30 s each). In contrast, the matrix alone did not increase in temperature under the same conditions. Furthermore, the change in temperature of OAC 2.5 using underwater NIR irradiation was examined in detail (Figure 6d). Despite the slower rate of increase, the temperature reached ~60 °C within 1 min due to the embedded NPs, whereas the surrounding medium did not experience significant heating, as evidenced by the thermal IR images (Figure 6d, inset). Similar elastic moduli were measured for OAC 2.5 when recycled by either heat or NIR irradiation, as estimated from the initial stages of tensile curves (Figure 6e). Surface scratches on the OAC 2.5 film were also thermally healed at 60 °C (Figure 6f); the same healing effect was achieved under NIR irradiation without external heating, while a scratched OAN 20 film was not healed by NIR irradiation due to the absence of NPs (Figure S13). The OAN 20 matrix still facilitated the triggerable degradation of the composite under the same aqueous conditions, regardless of the presence of the NPs. In particular, the initial toughness of OAC 2.5 rapidly decreased following exposure to 50 mM CsF and became unmeasurable after 2 d (Figure 6g). A comparison of tensile curves before and after 12 h of exposure confirmed the substantial loss of mechanical strength resulting from the triggered de-cross-linking induced by dOA (Figure 6g, inset). Other tensile curves at different time intervals during degradation are presented in Figure S14. Beyond mechanical reinforcement and photothermal heating, the incorporation of the nanoparticles enables localized and reversible activation of bond exchange with high spatial resolution, as well as a light-addressable adhesive system with practical bonding strength, offering a clear advantage over conventional thermal processing for controlled reprocessing and adhesion. Spatiotemporal control over OAC 2.5 using NIR irradiation was also investigated. Star-shaped OAC 2.5 samples were prepared using molding and cutting and then firmly integrated into an OAN 20 film under the same NIR irradiation conditions. Taking advantage of the light-induced selective heating of the star-shaped samples, we found that each star began to adhere to the substrate instantly at the onset of irradiation (~1 min) via covalent bond exchange at the interface, while maintaining sharp, unchanged vertices and edges. In contrast, notable deformation of the entire star pattern was observed when the star samples were attached to the substrate using thermal treatment, which required 1 h at 60 °C. This could be attributed to nonspecific heating, which increased the vertex angle from 57° to 125° (Figure 6h). To further demonstrate the light-addressable adhesive behavior, single-lap joint shear testing on a glass substrate revealed that OAC 2.5 had adhesive properties due to NP reinforcement, which were lacking in OAN 20 (Figure 6i). A significant enhancement in lap shear strength was found after NP reinforcement, accompanied by an increase in the toughness. Of particular note is that the shear strength rose from ~0.02 MPa for OAN 20 to ~0.72 MPa for OAC 2.5 , which was comparable to that of general silicone or hot-melt adhesives. Thus, when separated by force, the OAC 2.5 adhesive layer could be recycled under the same NIR or thermal conditions, enabling the rejoining of the adherends. Nevertheless, NIR-induced joint restoration offered advantages over thermal restoration, with a 20% higher shear strength after only 0.5 h of irradiation, compared to 1 h of heating. In addition, the shear strength measured after photothermal recycling was nearly identical to that of the pristine sample, likely due to an intrinsic deep penetration depth of NIR light, leading to effective heat transfer throughout the composite layer. Moreover, chemical detachment was only achieved following exposure to fluoride, resulting in permanent separation. After 12 h of immersion in an aqueous 50 mM CsF solution, the joint was practically de-bonded via triggered degradation, exhibiting only minimal strength (~0.03 MPa), while the adhesive layer was no longer recyclable. The load–displacement curves obtained during the shear tests are presented in Figure S15. Figure 6. (a) Schematic depiction of the thermal or NIR-induced recycling of an OAC 2.5 film in air and underwater. Photographs of underwater recycling are shown on the right. (b) Stress relaxation tests for OAC 2.5 at different temperatures. The dotted lines indicate the characteristic relaxation time (τ*) for each case, with an estimated E a of 123.2 kJ mol –1 . (c) Temperature profiles for OAC 2.5 over five NIR irradiation on–off cycles (30 s per cycle). (d) Temperature of OAC 2.5 under NIR irradiation underwater. (e) Comparison of the tensile stress–strain curves for pristine and recycled OAC 2.5 . (f) Thermal healing of scratches on an OAC 2.5 film. (g) Change in the toughness of OAC 2.5 over time after exposure to 50 mM CsF. The inset shows the initial tensile stress–strain curve and that after 12 h of degradation. (h) Light-induced attachment of star-shaped OAC 2.5 onto OAN 20 under NIR irradiation. Nonspecific thermal attachment is presented at the bottom for comparison. (i) (left) Schematics for the controlled adhesion properties of OAC 2.5 ; (right) change in its lap-shear strength when NPs are incorporated, when it is recycled by heat or light, and when it is de-bonded using fluoride. 3. Conclusion In this work, we demonstrated a sustainable molecular design concept for the OAN thermoset that combines recyclability, triggered degradability, and light-controllable reprocessability. Of note, dOA, synthesized via a facile one-pot process from OA, enabled specific de-cross-linking in response to fluoride exposure, while the telechelic PCL-LA macromonomer and BME co-monomer imparted tunable toughness, thermal malleability, and a bond-exchange capability. The optimized OAN 20 exhibited dimensional stability, self-healing, and bulk recyclability via thermally activated transesterification, while maintaining high transparency and biocompatibility. Furthermore, the PDA-coated ZrO 2 NPs were incorporated not as generic photothermal fillers, but as multifunctional components that simultaneously enable mechanical reinforcement, high-resolution reprocessability, and light-controlled adhesion. The resulting composites demonstrated rapid underwater healing, selective shape control, and recyclable adhesion under spatiotemporal NIR irradiation, delivering a mechanical performance comparable to conventional elastomers and adhesives but with the unique benefit of fluoride-triggered degradability. Overall, this study presents a versatile platform for the design of biobased, reprocessable, and degradable polymeric materials from abundant fatty acid feedstocks. Also, the self-immolative degradation pathway is inherently modular, allowing sustainable triggers beyond fluoride to be implemented via appropriate modification. Such systems enable (i) localized repair and stress relaxation in bulk thermoset materials, (ii) spatially programmable reprocessing, and (iii) on-demand debonding in multilayer or opaque assemblies. By integrating chemical adaptability with photothermal responsiveness, our approach provides new opportunities for the use of sustainable polymers in applications ranging from recyclable structural materials to bio-related device interfaces. 4. Experimental Section Synthesis of degradable oleic-acid-based monomer (dOA) : To a flame-dried round-bottom flask were added acetonitrile (2.5 mL), OA (750 mg, 2.65 mmol, 2.5 equiv), and triethylamine (537 mg, 5.31 mmol, 5.0 equiv) under a nitrogen atmosphere. Diphenylphosphoryl azide (876.9 mg, 3.19 mmol, 3.0 equiv) was then added sequentially, and the reaction mixture was stirred for 1 h at 25 °C. The solution was then heated to reflux at 80 °C for 4 h. After cooling to room temperature, a sacrificial diol ( 2 ) [33] (300 mg, 1.06 mmol, 1.0 equiv) dissolved in acetonitrile (1.5 mL) was added, followed by the addition of dibutyltin dilaurate (DBTL) (10 μL, 0.1 μmol, 0.0001 equiv). The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was then combined, dried over NaSO 4 , and concentrated under reduced pressure. Further purification using flash column chromatography (ethyl acetate/ n -hexane = 1:7, v/v) afforded dOA as a pale-yellow liquid (800 mg, 0.79 mmol, 72%). IR (cm –1 ): 3325, 2924, 2854, 1531, 1235; 1 H NMR (400 MHz, CDCl 3 ): δ 7.10 (s, 2 H), 5.37–5.32 (m, 4H), 5.07 (s, 4 H), 4.72 (m, 2 H), 3.23–3.17 (m, 4 H), 2.28 (s, 3 H), 2.03–1.99 (m, 8 H), 1.51–1.48 (m, 4 H), 1.33–1.30 (m, 40 H), 1.03 (s, 9 H), 0.88–0.86(m, 6 H), 0.19 (m, 6 H); 13 C NMR (100 MHz, CDCl 3 ): δ 160.17, 152.23, 134.83, 134.07, 133.75, 133.44, 131.07, 65.86, 44.86, 35.54, 33.74, 33.50, 33.44, 33.39, 33.05, 32.94, 30.95, 30.90, 30.46, 29.71, 26.42, 24.34, 22.40, 17.85; HRMS (TOF MS FD+): Calcd. for C 51 H 92 N 2 O 5 Si (M + ) 840.67824 m / z , found: 840.67700 m / z . Synthesis of polycaprolactone-based macro-monomer (PCL-LA) : Polycaprolactone diol (PCL-diol) ( M n , 2 kDa) (2.0 g, 1.00 mmol, 1.0 equiv) dissolved in DCM (10 mL) under a nitrogen atmosphere. DL-α-lipoic acid (515 mg, 2.50 mmol, 2.0 equiv), 4-dimethylaminopyridine (DMAP) (30.5 mg, 0.25 mmol, 0.25 equiv), and N -(3-dimethylaminopropyl)- N ′-ethylcarbodiimide (EDC) (427 mg, 2.75 equiv, 2.75 mmol) were then added sequentially. After stirring at 25 °C for 18 h, the mixture was washed with a saturated NaHCO₃ solution, brine, and water, and extracted using DCM. The organic layer was combined, dried over NaSO 4 , and concentrated under reduced pressure. The residue was precipitated from ethanol, filtered using aspiration, and dried under vacuum to afford the product as a yellow solid (2.1 g, 0.87 mmol, 87%). Substitution yield: 85%. M n , 2 kDa, Đ , 2.03; IR (cm –1 ): 2940, 2866, 1724, 1523, 1238, 1163; 1 H NMR (400 MHz, CDCl 3 ): δ 4.08–4.05 (m, 32 H), 3.88 (s, 4H), 3.57–3.56 (m, 2 H), 3.19–3.11 (m, 4 H), 2.48–2.45 (m, 2 H), 2.35–2.29 (m, 28 H), 1.93–1.89 (m, 2 H), 1.17–1.68 (m, 8 H), 1.67–1.62 (m, 56 H), 1.48–1.42 (m, 4H), 1.38–1.35 (m, 28 H), 0.97 (m, 4 H). Synthesis of degradable oleic-acid-based network (OAN 20 ) : To a mixture of PCL-LA (200 mg, 0.08 mmol, 2.0 equiv), dOA (43.2 mg, 0.21 mmol, 5.0 equiv), and BME (6.5 mg, 0.08 mmol, 2.0 equiv) were added 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) (1.2 mg, 0.008 mmol, 0.2 equiv), and 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure 2959) (total 3 wt%) as a photoinitiator. All components were dissolved in a small amount of DCM (2 mL), dropped onto a quartz plate, and allowed to stand at room temperature for 1 h to dry. The mixture was irradiated with UV light for 30 min to obtain the desired crosslinked film. Synthesis of degradable oleic-acid-based composite (OAC 2.5 ) : PCL-LA (200 mg, 0.08 mmol, 2.0 equiv), dOA (43.2 mg, 0.21 mmol, 5.0 equiv), BME (6.5 mg, 0.08 mmol, 2.0 equiv), TBD (1.2 mg, 0.008 mmol, 0.2 equiv), and Irgacure 2959 (3 wt%) were dissolved in a small amount of DCM (4 mL) and pre-polymerized under UV irradiation for 15 min at 25 °C. A dispersion of PDA-coated NPs (0.5, 1.5, or 2.5 wt% relative to the total solids) in MeOH (1 mL) was then added to the prepolymer mixture and stirred vigorously for 0.5 h. The resulting mixture was then transferred onto a quartz plate, air-dried at 25 °C for 1 h, and cured under UV irradiation for 45 min to produce the desired composite. Estimation of cross-linking density : The cross-linking density ( V e ) was estimated based on the rubber elasticity theory using equation 1, with the glass transition temperature ( T g ) defined from the tan δ curve, as reported previously. [34] \begin{equation} v_{e}=\frac{E^{\prime}}{3RT}\ \ \ \ \ \ \ (1)\nonumber \\ \end{equation} where E ′, R , and T indicate the storage modulus at T g + 30 °C, the gas constant, absolute temperature at T g + 30 °C, respectively. NIR-induced patterning of star-shaped samples : Star-shaped pieces of OAC 2.5 were cut and placed onto an OAN 20 film. The samples were selectively bonded using NIR irradiation (0.5 W cm –2 ) for <1 min. In contrast, thermal treatment at 60 °C under gentle pressure for 1 h resulted in nonspecific bonding of the star-shaped structures to the substrate. Lap shear tests : Glass slides were washed with acetone, treated with UV–ozone, and rinsed with DI water prior to use. Single-lap joint specimens were prepared via the in situ UV crosslinking of analyte samples between the glass slides, followed by thermal treatment at 80 °C for 30 min. The glued joints were directly subjected to lap shear tests using a universal tensile machine. The specimens were subsequently re-attached either by heating them at 60 °C for 1 h or via NIR irradiation (0.5 W cm –2 ) for 30 min and tested again under the same conditions. For the permanent debonding of the specimens via triggered degradation, the bonded joints were immersed in a 50 mM CsF solution for 12 h, rinsed, and dried under vacuum at 25 °C for 12 h before testing. Supporting Information Supporting Information is available from the Wiley Online Library or from the author. Acknowledgements This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (RS-2025-25404226) and the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (2020R1A5A8018367). This study was supported by the Korea Planning & Evaluation Institute of Industrial Technology (KEIT) grant funded by the Ministry of Trade, Industry and Energy (MOTIE) (No. RS-2024-00424466). Received: (will be filled in by the editorial staff) Revised: (will be filled in by the editorial staff) Published online: (will be filled in by the editorial staff) References [1] Y. Liu, Z. Yu, B. Wang, P. Li, J. Zhu, S. Ma, Green Chem. 2022 , 24 , 5691–5708; [2] S. Utekar, S. V. K, N. More, A. Rao, Compos. Pt. B-Eng. 2021 , 207 , 108596; [3] G. W. Coates, Y. D. Y. L. Getzler, Nat. Rev. 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Information & Authors Information Version history V1 Version 1 03 April 2026 Copyright This work is licensed under a Non Exclusive No Reuse License. Keywords depolymerization near-infrared oleic acid recycling thermosets Authors Affiliations Sumin Kang Chonnam National University View all articles by this author Songah Jeong Chonnam National University View all articles by this author Seoyeon Choi Chonnam National University View all articles by this author Van Nguyen Korea Institute of Medical Microrobotics View all articles by this author Eunpyo Choi Sogang University View all articles by this author Jinsoo Park Chonnam National University View all articles by this author Hyungwoo Kim 0000-0003-1958-3587 [email protected] Chonnam National University View all articles by this author Metrics & Citations Metrics Article Usage 116 views 70 downloads .FvxKWukQNSOunydq8rnd { width: 100px; } Citations Download citation Sumin Kang, Songah Jeong, Seoyeon Choi, et al. Self-Immolative, Adaptable, Oleic-Acid-Based Thermosets: Modular Design, Degradability, and Light-Driven Reprocessability. Authorea . 03 April 2026. DOI: https://doi.org/10.22541/au.177522718.87118622/v1 If you have the appropriate software installed, you can download article citation data to the citation manager of your choice. Simply select your manager software from the list below and click Download. For more information or tips please see 'Downloading to a citation manager' in the Help menu . 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