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Effect of tannic acid chelating treatment on thermo-oxidative aging property of natural rubber

  • Chuanyu Wei , Tingting Zheng , Yuhang Luo , Changjin Yang , Yanchan Wei and Shuangquan Liao EMAIL logo
Published/Copyright: September 5, 2024
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e-Polymers
From the journal e-Polymers Volume 24 Issue 1

Abstract

Metal ions are crucial in the production and preservation of fresh natural rubber latex. However, they also catalyze the thermo-oxidative aging of rubber products, leading to premature product degradation. This study investigates the use of tannic acid (TA) to chelate metal ions, thereby enhancing the thermo-oxidative aging resistance of natural rubber (NR). The findings indicate that NR treated with a 1.5 g·L−1 TA solution exhibits superior tensile strength, elongation at break, and crosslink density post-thermo-oxidative aging compared to untreated samples. Analysis of ultraviolet–visible absorption spectra, Fourier transform infrared spectra, and X-ray photoelectron spectroscopy confirms that TA’s resistance to thermo-oxidative aging stems from its ability to form stable chelates with metal ions, reducing their catalytic activity and mitigating oxidative degradation. Consequently, TA chelation treatment is proposed as an effective method to enhance the thermo-oxidative aging resistance of NR.

Graphical abstract

Keywords: natural rubber; tannic acid; metal ion; thermo-oxidative aging

1 Introduction

Annually, millions of tons of vulcanized natural rubber (NR) products are manufactured globally (1). NR is a cornerstone of the global economy, accounting for approximately half of the total elastomer demand for industrial development (2,3). NR’s excellent combination of properties, such as high elasticity, high abrasion resistance, and high impact resistance, makes it an irreplaceable presence in a wide variety of fields (4).

Fresh natural rubber (FNR) contains trace amounts of metal ions that enhance the biological activity of enzymes associated with latex particles (5,6,7), thereby improving the yield and quality of NR latex. Research has indicated that certain metal ions serve as inorganic antimicrobial agents, preventing latex spoilage (8). While these ions are advantageous for FNR latex production and preservation, their potential detrimental effects on NR should not be overlooked (9). The omnipresent thermo-oxidizing environment can degrade the properties of NR products, culminating in product failure (10), a phenomenon termed thermo-oxidative aging (11,12,13). During this aging process, oxidative degradation of NR generates oxygen-containing functional groups (14), leading to chain scission (15). Metal ions such as Cu2+ and Fe2+ present in FNR act as potent oxidizing agents, exacerbating the thermo-oxidative aging process (16,17,18).

Metal ions, capable of binding to proteins and phospholipids on NR particles, are difficult to eliminate entirely (19). The incorporation of metal ion chelators can effectively inhibit the catalytic activity of these ions, such as Cu2+, Fe2+, and Mn2+, thereby mitigating the accelerated aging they induce (20). Chelating agent functions by forming ligand-bonded complexes with metal ions or atoms through strong interactions with negatively charged groups or electrically neutral polar molecules (21,22). The development of chelate-based multifunctional materials has shown promise across various fields (23,24), and the creation of functional metal–phenol networks, composed of phenol ligands and diverse metals (25), introduces novel mechanistic functionalities in the realm of soft matter (26). Tannic acid (TA), a well-known polyphenolic compound (27), is rich in phenolic groups and possesses multiple binding sites (27,28,29,30), including hydrogen, ionic, and ligand bonds, enabling it to interact strongly with metal ions in FNR (31,32). Moreover, TA’s antioxidant properties, such as reducing and radical scavenging activities, further enhance the antioxidant aging performance of FNR against thermal and oxidative degradation (33).

In this study, TA is employed as a chelating agent to form metal ion–ligand complexes in NR (34), with the formation confirmed by ultraviolet–visible (UV–Vis) spectroscopy (35,36,37). The chelating-treated NR is then blended, vulcanized, and subjected to thermo-oxidative aging experiments. The impact of TA chelation on NR’s thermo-oxidative aging resistance is assessed by comparing the macroscopic mechanical properties of the samples, further substantiated by microstructural and molecular characterization. The study concludes the mechanism by which TA chelation confers resistance to thermo-oxidative aging. In the complexation reaction, metal ions are rendered catalytically inactive, forming stable chelates. Chelation modification is essential for practical applications (38,39). The objective of this research is to investigate the efficacy and mechanism of TA as a chelating agent in mitigating the accelerated thermo-oxidative aging of FNR caused by metal ions, thereby enhancing the potential applications of NR and metal ion preservatives and prolonging the service life of NR products.

2 Experiment section

2.1 Material

FNR (38% dry rubber content) was purchased from Institute of Rubber Research, Chinese Academy of Tropical Agricultural Sciences. Zinc oxide (ZnO, AR), stearic acid (C18H36O2, AR), sulfur (S8, AR), and 2-mercaptobenzothiazole (C7H5NS2, AR) were obtained from Shanghai Aladdin Bio-Chem Technology Co., Ltd, China. Methylbenzene (C6H5CH3, AR) was purchased from Xilong Chemical Co., Ltd. TA (C76H52O46, AR) was obtained from Shanghai Macklin Co., Ltd.

2.2 Chelating pretreatment of NR

Fresh natural latex to 30% was diluted, transferred to a glass plate, allowed for molding, and then incubated in oven at 50°C to dry until completely transparent to obtain FNR. About 0.5, 1, and 1.5 g·L−1 TA solution and glycolic acid solution were prepared; six parts of 100 g dried NR were taken and soaked in different solutions for 12 h; then NR was taken out and allowed to dry until completely transparent.

About 80 phr of FNR were plasticated via an open mill; 0.4 phr of stearic acid, 4.8 phr of zinc oxide, 0.4 phr of 2-mercaptobenzothiazole, and 2.8 phr of sulfur were added in order to obtain the NR compound. After the FNR compound was incubated for 8 h, the positive vulcanization time t 90 was measured by rotor-free vulcanization instrument. The vulcanized FNR was obtained by pressing the compound with a plate vulcanizer at 145°C and t 90 corresponding time.

2.3 Thermo-oxidative aging

The thermo-oxidative aging test was carried out in the 7017-EL1 thermo-oxidative aging test chamber. The vulcanized FNR was suspended in the thermo-oxidative aging test chamber and exposed at 100°C for 12, 24, 36, and 48 h, respectively. In order to obtain reliable results, the sample strips were simultaneously placed in the thermo-oxidative aging chamber, and seven sample strips were taken at 12 h intervals.

2.4 Characterizations

2.4.1 UV–Vis spectrophotometer

The Lambda-750 UV–Vis Spectrophotometer was used to detect coordination bond formed by the chelation of metal ions with TA in FNR. The instrument wavelength was from 400 to 800 nm.

2.4.2 Mechanical property measurements

In order to characterize the mechanical properties of the samples before and after thermo-oxidative aging, the samples were tested by Gotech AI-7000 microcomputer-controlled electronic universal testing machine. The test reference standard was ISO 37-2005, the sample was cut as dumbbell 2 type, and the tensile speed was 500 mm·min−1. At least five samples were tested in order to obtain a reliable result.

2.4.3 Crosslink density

The crosslink density of the samples was determined by the equilibrium dissolution method. About 0.2 g of the sample was taken, accurately weighed (m 1), placed in a closed glass jar containing 100 ml of toluene, soaked at room temperature for 7 days, and then removed; the solvent on the surface of the sample was quickly wiped with filter paper and weighed (m 2), and the crosslink density of the vulcanized NR was calculated using the Flory–Rehner formula (40). At least three samples were tested in order to obtain a reliable result.

(1) ∅ r = m 1 / ρ + m 2 / ρ s m 1 / ρ

(2) − ln ( 1 − ∅ r ) − ∅ r − χ r ϕ r 2 = n V 0 ϕ r 1 / 3 − 1 2 ϕ r

(3) M c = ρ n

where ϕ r is the volume fraction of polymer in the swollen network, ρ is the density of NR (ρ = 0.913 g·cm−3), ρ s is the density of toluene solvent (ρ s = 0.866 g·mL−1), V 0 is the molar volume of the toluene solvent (V 0 = 106.2 mL·mol−1), n is the average number of movable chain segments per unit volume (mol·mL−1), χ r is the interaction parameter of NR-toluene (χ r = 0.393), and M c is the average molecular mass between the crosslink points.

2.4.4 Field emission scanning electron microscopy (FESEM)

In order to characterize the microscopic surface morphological changes of the samples before and after thermo-oxidative aging, Verios G4 UC FESEM was used for imaging analysis of the samples after gold spraying. Parameter setting: the acceleration voltage was 5 kV, and the magnification was 50,000 × .

2.4.5 Fourier transform infrared spectroscopy

Attenuated total reflectance Fourier transform infrared spectrometer (ATR-FTIR) was used to characterize the changes in chemical structure of samples before and after thermo-oxidative aging. The instrument model was Nicolet Is 50. The scanning range was from 4,000 to 400 cm−1, and the scanning times were 16.

2.4.6 X-ray photoelectron spectroscopy

The binding energies of O 1s, C 1s and Cu 2p before and after thermo-oxidative aging were characterized by X-ray photoelectron spectroscopy (XPS). All spectral peaks were calibrated with the C 1s binding energy of 284.8 eV. O 1s and C 1s were used to characterize the effect of TA chelation on the thermo-oxidative aging properties, and the change of Cu 2p binding energy before and after aging was used to reveal the anti-thermo-oxidative aging mechanism of TA chelation.

3 Results and discussion

3.1 TA chelates metal ions to form coordination bonds

The chelation reaction between TA molecules and metal ions results in the formation of metal–polyphenol complexes, as depicted in Figure 1(a) (41,42). The formation of these coordination bonds was confirmed using a UV–Vis spectrophotometer. In Figure 1(b), the addition of 1.5 g·L−1 TA to 10 mg·L−1 of Fe2+ solution for chelation treatment led to a pronounced absorbance peak at 560 nm in the TA-Fe2+ spectrum, indicative of the metal–ion coordination bond. In contrast, neither the Fe2+ solution nor the TA solution alone exhibited this peak. Figure 1(c) further demonstrates that FNR treated with a 1.5 g·L−1 TA solution also displayed the absorbance peak at 560 nm (43). These findings confirm that metal ions, particularly Fe ions, can form new ligand bonds with TA. The intensity of the absorbance peak in Figure 1 increases with the concentration of TA, peaking at 1.5 g·L−1 (FNR-TA-1.5). Consequently, a TA solution at this concentration was chosen for the chelation of FNR, and its impact on the thermo-oxidative aging performance was subsequently evaluated.

Figure 1 (a) Chelation of TA with metal ions, (b) UV–Vis absorption spectra of different solutions, and (c) UV–Vis spectra of NR chelated with different concentrations of TA solution.
Figure 1

(a) Chelation of TA with metal ions, (b) UV–Vis absorption spectra of different solutions, and (c) UV–Vis spectra of NR chelated with different concentrations of TA solution.

3.2 Effect of TA chelation on mechanical properties of FNR after thermo-oxidative aging

The efficacy of TA chelation treatment in mitigating the thermo-oxidative aging of NR was demonstrated through mechanical property assessments at various aging durations. Figure 2 illustrates that after 24 h of thermo-oxidative aging at 100°C, the tensile strength and tensile strength retention rate of FNR were 13.3 MPa and 82.10%, respectively. In contrast, the treated FNR-TA-1.5 exhibited a tensile strength of 16.08 MPa and a retention rate of 98.65%. This indicates that TA chelation provides a protective effect on NR’s physical and mechanical properties during aging. Initially, the molecular network of NR strengthens, leading to a temporary increase in tensile strength. However, as aging progresses, the molecular chains begin to break, causing a sharp decline in mechanical strength. At equivalent aging times, FNR-TA-1.5 maintains higher mechanical strength, elongation at break, and retention rate compared to untreated FNR, suggesting that chelation treatment can reduce the catalytic activity of metal ions, thereby diminishing their contribution to the aging process.

Figure 2 (a) Tensile strength at various durations of thermo-oxidative aging, (b) elongation at break at various durations of thermo-oxidative aging, (c) tensile strength retention rate at various durations of thermo-oxidative aging, and (d) elongation at break retention rate at various durations of thermo-oxidative aging.
Figure 2

(a) Tensile strength at various durations of thermo-oxidative aging, (b) elongation at break at various durations of thermo-oxidative aging, (c) tensile strength retention rate at various durations of thermo-oxidative aging, and (d) elongation at break retention rate at various durations of thermo-oxidative aging.

3.3 Effect of metal chelation on the microstructure of FNR after thermo-oxidative aging

The micro- and macro-structural integrity of crosslinked elastomers is directly related to the crosslink density (44). The average molecular mass M c between crosslinking sites is inversely proportional to the crosslinking density, and Figure 3(a) depicts the change in M c during thermo-oxidative aging. The crosslink density of FNR-TA-1.5 consistently exceeds that of untreated FNR over the same aging periods. At 12 h of aging, FNR-TA-1.5 exhibits a transient increase in crosslink density, while both FNR and FNR-TA-1.5 display a sharp decline in crosslink density crosslink density as aging progresses. This pattern mirrors the mechanical strength trends observed in Figure 2(a), where strength initially increases before declining with extended aging. During thermo-oxidative aging, crosslinking and chain scission in NR molecules are competing processes. In the initial phase, polysulfide bonds transform into monosulfide or disulfide bonds, leading to an initial increase in crosslink density and mechanical strength, and the formation of a continuous molecular network. The consistently higher crosslink density of FNR-TA-1.5 suggests that TA chelation treatment positively influences crosslink density, resulting in less damage to the network structure during aging. SEM analysis characterizes the surface morphology of samples before and after thermo-oxidative aging. Figure 3(b) illustrates that as the duration of thermo-oxidative aging increases, the quantity of surface cracks on the samples also increases, with a corresponding expansion in the size and depth of these cracks (45). Notably, specimens subjected to TA chelation treatment exhibit a reduced number of surface cracks, and the extent of these cracks in terms of area and depth is less pronounced. These findings indicate that chelation treatment mitigates the surface damage inflicted by thermo-oxidative aging on NR.

Figure 3 (a) Average molecular mass between cross-linking sites M c, (b) SEM diagram of the FNR and FNR-TA-1.5 under different thermo-oxidative aging time, and (c) mechanisms of changes in NR molecular network structure during thermo-oxidative aging.
Figure 3

(a) Average molecular mass between cross-linking sites M c, (b) SEM diagram of the FNR and FNR-TA-1.5 under different thermo-oxidative aging time, and (c) mechanisms of changes in NR molecular network structure during thermo-oxidative aging.

In summary, the mechanism of structural changes in the NR molecular network during thermo-oxidative aging is elucidated in Figure 3(c). The chelation by TA diminishes the catalytic activity of metal ions, thereby inhibiting the reaction 2ROOH → RO˙ + ROO˙· + H2O catalyzed by these ions with variable valency (46). This reduction in the formation of free radicals and oxygen-containing groups consequently enhances the anti-thermo-oxidative aging properties of NR.

3.4 Effects of chelation treatment on molecular structure after thermo-oxidative aging

Figure 4(a) presents the ATR-FTIR spectra prior to thermo-oxidative aging. The C–H stretching vibration peak in the ═CH− group is discernible at 2,959 cm−1, while the absorption bands at 2,916 and 2,845 cm−1 correspond to the stretching vibration peak of C–H group in −CH3 and −CH2−, respectively. The characteristic amide Ⅱ absorption peak is located at 1,538 cm−1. Additionally, the absorption bands at 1,375 cm−1 and 1,455 cm−1 are attributed to the deformation vibrations of −CH3 and −CH2 groups, respectively. These absorption peaks are also evident in the infrared spectra of both FNR and FNR-TA-1.5, suggesting that the molecular structure of NR remains undamaged following treatment with a 1.5 g·L−1 TA solution.

Figure 4 (a) ATR-FTIR spectra of FNR and FNR-TA-1.5 before thermo-oxidative aging and (b) ATR-FTIR spectra of FNR and FNR-TA-1.5 after thermo-oxidative aging for 24 h.
Figure 4

(a) ATR-FTIR spectra of FNR and FNR-TA-1.5 before thermo-oxidative aging and (b) ATR-FTIR spectra of FNR and FNR-TA-1.5 after thermo-oxidative aging for 24 h.

Figure 4(b) reveals the emergence of new peaks following 24 h of thermo-oxidative aging. The O–H stretching vibration absorption band is observed at approximately 3,300 cm−1, and the C–O absorption band associated with peroxides is detected between 1,000 and 1,200 cm−1, indicative of the formation of oxygen-containing groups during the oxidation process. Concurrently, the intensities of the peaks at 2,959, 2,916, 2,845, and 836 cm−1 diminish, suggesting partial molecular chain degradation and bond breakage in NR. A comparative analysis of the ATR-FTIR spectra for FNR and FNR-TA-1.5 after 24 h of thermo-oxidative aging indicates that the intensity of oxygen-containing groups’ peaks in FNR-TA-1.5 is reduced, while the intensities of the peaks at 2,959, 2,916, 2,845, and 836 cm−1 are marginally enhanced. These findings suggest that the chelation treatment with TA mitigates the bond breakage and substitution reactions induced by thermo-oxidative aging in NR.

To confirm the efficacy of TA chelate treatment in enhancing the anti-aging property of NR, XPS was employed to analyze the alterations in oxygen-containing groups pre- and post-thermo-oxidative aging. Figure 5(a) and (b) illustrates the C 1s sub-peaks for both FNR and FNR-TA-1.5 before and after aging. An increase in C–O and O–C═O content in FNR after 24 h of aging is evident, as shown in Figure 5(c) and (d), where the O 1s peak value also increases significantly. This suggests that the oxidation of double bonds occurs during thermo-oxidative aging of FNR, leading to the formation of new oxygen-containing groups. In contrast, the C–O and O–C═O peaks for FNR-TA-1.5 remain relatively low after aging, indicating a reduced number of oxygen-containing groups.

Figure 5 (a) C 1s XPS spectra of FNR, FNR-TA-1.5 before thermal oxidative aging, (b) C 1s XPS spectra of FNR-TA-1.5 after 24 h of thermo-oxidative aging, (c) O 1s XPS spectra of FNR and FNR-TA-1.5 before thermal oxidative aging, (d) O 1s XPS spectra of FNR and FNR-TA-1.5 after 24 h of thermo-oxidative aging, (e) Cu 2p XPS spectra of FNR and FNR- TA-1.5 after 24 h of thermo-oxidative aging, and (f) O/C ratios for different thermo-oxidative aging times.
Figure 5

(a) C 1s XPS spectra of FNR, FNR-TA-1.5 before thermal oxidative aging, (b) C 1s XPS spectra of FNR-TA-1.5 after 24 h of thermo-oxidative aging, (c) O 1s XPS spectra of FNR and FNR-TA-1.5 before thermal oxidative aging, (d) O 1s XPS spectra of FNR and FNR-TA-1.5 after 24 h of thermo-oxidative aging, (e) Cu 2p XPS spectra of FNR and FNR- TA-1.5 after 24 h of thermo-oxidative aging, and (f) O/C ratios for different thermo-oxidative aging times.

The binding energy of the Cu 2p core level in FNR and FNR-TA-1.5 was analyzed following 24 h of thermo-oxidative aging to elucidate the mechanism by which TA chelation enhances the thermo-oxidative aging resistance of NR. As depicted in Figure 5(e), the Cu 2p peak is clearly discernible after 24 h of thermo-oxidative aging in FNR.

The O/C ratio of FNR-TA-1.5, calculated from peak area measurements, is consistently lower before and after thermo-oxidative aging compared to FNR. As depicted in Figure 5(f), the specific growth rate of oxygen-containing groups in FNR-TA-1.5 is significantly lower than in FNR. These findings suggest that TA chelation effectively mitigates the formation of oxygen-containing groups on the molecular chain post-aging, thereby enhancing the thermo-oxidative aging resistance of NR. It is plausible that metal ions, initially bound to protein phospholipids, are released during thermo-oxidative aging and contribute to the accelerated aging process by catalyzing the reaction, as illustrated in Scheme 1.

Scheme 1 Catalytic mechanism of metal ions on thermo-oxidative aging.
Scheme 1

Catalytic mechanism of metal ions on thermo-oxidative aging.

Upon the formation of chelating coordination bonds, the binding energy typically diminishes (47,48,49). Consequently, the Cu 2p binding energy peak in FNR-TA-1.5, after 24 h of thermo-oxidative aging, becomes diminished or undetectable. This suggests that TA effectively forms a stable chelates with metal ions, thereby inhibiting their catalytic role in the thermo-oxidative aging process of NR. As a result, the anti-thermo-oxidative aging properties of NR are enhanced.

The tensile strength retention of 1.5 g·L−1 TA solution-chelated and treated NR after 24 h of thermo-oxidative aging was 21.34% higher than that of the original sample. This enhancement rate is higher than most of the reported antioxidants. In order to highlight the comparison of the resistance of NR to thermo-oxidative aging, we supplemented Table 1 with information on the changes in the tensile strength retention rate of rubber after thermo-oxidative aging by some of the antioxidants reported in the literature. Due to the complexity of the rubber vulcanization system, the variability of the thermo-oxidative aging conditions, and the non-uniformity of the characterization methods regarding the thermo-oxidative aging properties, we have listed as many conditions as possible in the table, in addition to which we have uniformly used the change in tensile strength retention to characterize the thermo-oxidative aging properties of each antioxidant against the rubber matrix.

Table 1

Effect of different antioxidants on the thermo-oxidative aging properties of rubber, which has been reported in the literature

Matrix Antioxidant Dosage Aging temperature Aging time promotion rate References
EPDM vulcanized rubber N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine 1.0 phr 90°C 48 h 6.9% (50)
Nature rubber + micro ZnO Nano ZnO system 5 phr 80°C 48 h 1.23% (51)
Nature rubber + antioxidant 4020-1.5 phr 1,6-bis(N,N0-dibenzyl thiocarbamoyl dithio)-hexane 0.2 phr 100°C 48 h 2.03% (52)
NR + carbon black PM propolis 5 phr 70°C 24 h 19% (53)
Nature rubber TA 1.5 g·L−1 100°C 24 h 21.34% This work

4 Conclusion

In summary, this study presents a method to enhance the thermal-oxidative aging resistance of NR by chelating metal ions with a TA solution. The findings indicate that chelation treatment with TA leads to the formation of stable chelates through coordination complexation, resulting in improved mechanical properties, crosslink density, and microscopic morphology of NR post-thermo-oxidative aging. Analysis of the post-aging molecular structure reveals a reduced a number of oxygen-containing groups following chelation, which correlates with enhanced anti-thermo-oxidative aging performance. The observed resistance to aging is attributed to the inactivation of metal ions by chelation, preventing the conversion of ROOH to free radicals. Consequently, TA solvent immersion chelation treatment is proposed as an effective strategy to mitigate the acceleration of thermo-oxidative aging in NR products and to enhance their anti-thermo-oxidative aging properties.

  1. Funding information: This research was supported by Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDC06010100), the National Key R&D Program of China (2022YFD230120202), the Natural Science Foundation of Hainan Province (No. 521CXTD438), the National Natural Science Foundation of China (No. 52163010), and the Natural Science Foundation of Hainan Province (No. 323QN195).

  2. Author contributions: Ms. Wei was chiefly responsible for the study’s design, development of objectives, and data analysis. Dr. Zheng revised the manuscript. Mr. Luo oversaw some sample preparation, while Dr. Yang and Associate Professor Wei supervised the writing process. Professor Liao sponsored the financial aspects and managed the project. All authors have reviewed and endorsed the final manuscript.

  3. Conflict of interest: The authors declare that they have no known competing financial interests or personal relationships that could have influenced the work reported in this article.

  4. Data availability statement: All datasets generated during this study are available from the corresponding author upon reasonable request.

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Received: 2024-03-19
Revised: 2024-05-22
Accepted: 2024-06-21
Published Online: 2024-09-05

© 2024 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/epoly-2024-0036
Keywords for this article
natural rubber; tannic acid; metal ion; thermo-oxidative aging
Creative Commons
BY 4.0

Articles in the same Issue

  1. Research Articles
  2. Flame-retardant thermoelectric responsive coating based on poly(3,4-ethylenedioxythiphene) modified metal–organic frameworks
  3. Highly stretchable, durable, and reversibly thermochromic wrapped yarns induced by Joule heating: With an emphasis on parametric study of elastane drafts
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