Dicyclopentylmercapto hydrodiphenol antioxidant and preparation method and application thereof

Abstract

The application discloses a dicyclopentylmercapto hydrogenated bisphenol antioxidant and a preparation method and application thereof. The structural formula of the dicyclopentylmercapto hydrogenated bisphenol antioxidant is shown as formula I: wherein R1 and R2 are independently selected from one of hydrogen, an alkyl group, an amine group, a hydroxyl group and an ester group. The modifiability and replaceability of the side groups of the dicyclopentylmercapto hydrogenated bisphenol antioxidant greatly enrich the types of phenolic antioxidants, and provide a new idea for the design and preparation of high-efficiency phenolic antioxidants. Moreover, the dicyclopentylmercapto hydrogenated bisphenol antioxidant has long-acting antioxidant capacity and anti-aging property.

Description

Technical Field

[0001] This invention relates to the fields of organic synthesis and polymer materials technology, and in particular to a dicyclopentylthio-hydrogenated bisphenol antioxidant, its preparation method and application. Background Technology

[0002] Polymer materials, due to their high performance, ease of modification, and light weight, have become an indispensable class of materials in people's production and daily life. However, polymer materials undergo oxidative aging during processing, storage, and use. There are many methods to delay the oxidation of polymer materials, and adding antioxidants is one of the simplest and most effective methods.

[0003] Amine antioxidants are the earliest and fastest-growing class of antioxidants among polymeric material antioxidants. However, their application is limited due to issues such as color contamination of products and the high toxicity of some varieties. Consequently, they have been gradually replaced by light-colored, low-toxicity phenolic antioxidants. However, compared to amine antioxidants, phenolic antioxidants have poorer antioxidant properties, thus requiring further improvement in their antioxidant performance. Summary of the Invention

[0004] In view of the shortcomings of the prior art, the present invention provides a dicyclopentyl mercaptohydrogenated bisphenol antioxidant, its preparation method and application, thereby solving the problem that the antioxidant performance of existing phenolic antioxidants cannot meet the requirements.

[0005] The technical solution adopted by the present invention to solve the above-mentioned technical problems is as follows:

[0006] In a first aspect, the present invention provides a dicyclopentyl mercaptohydrogenated bisphenol antioxidant, wherein the structural formula of the dicyclopentyl mercaptohydrogenated bisphenol antioxidant is shown in Formula I:

[0007]

[0008] R1 and R2 are independently selected from one of hydrogen, alkyl, amino, hydroxyl, and ester groups.

[0009] A second aspect of the present invention provides a method for preparing the above-mentioned dicyclopentylthio-hydrogenated bisphenol antioxidant, the method comprising the following steps:

[0010] A nucleophilic addition reaction was carried out between hydrogenated bisphenol A as shown in Formula II and 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III, and the purified product was a dicyclopentyl mercaptohydrogenated bisphenol antioxidant as shown in Formula I; wherein R1 and R2 in Formula III are independently selected from one of hydrogen, alkyl, amino, hydroxyl, and ester groups.

[0011] The reaction pathway described above is shown below:

[0012]

[0013] Preferably, the step of performing a nucleophilic addition reaction between hydrogenated bisphenol A as shown in Formula II and 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III, followed by purification to obtain the dicyclopentylthio-hydrogenated bisphenol antioxidant as shown in Formula I, specifically includes:

[0014] Hydrogenated bisphenol A as shown in Formula II, 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III, a first solvent and a catalyst are mixed and reacted at 60-120°C for 2-12 hours.

[0015] After the reaction is completed, a second solvent is added to induce crystallization. After filtration, the resulting filter cake is washed with the second solvent. Finally, the washed filter cake is vacuum dried at a temperature of 60–100 °C to obtain the dicyclopentyl mercaptohydrobisphenol antioxidant as shown in Formula I.

[0016] Preferably, the equivalent ratio of the hydrogenated bisphenol A and the 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol is 1:(2-4).

[0017] Preferably, the ratio of the volume of the first solvent to the mass of the hydrogenated bisphenol A and the 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol is (2-10) mL:1 g.

[0018] Preferably, the molar ratio of the catalyst to the hydrogenated bisphenol A is (1.3-5):1.

[0019] Preferably, the amount of the second solvent is 20% to 150% of the volume of the first solvent.

[0020] Preferably, the first solvent is selected from one or more of toluene, xylene, solvent oil, chlorobenzene, dimethyl sulfoxide, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, or 1,2-dichloroethane, and the second solvent is selected from one or more of isopropanol, tert-butanol, isobutanol, acetonitrile, dioxane, ethylene glycol dimethyl ether, or methyl tert-butyl ether.

[0021] Preferably, the catalyst is selected from one or more of potassium carbonate, cesium carbonate, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, and sodium bicarbonate.

[0022] Preferably, the above-mentioned dicyclopentyl mercaptohydrogenated bisphenol antioxidant or the dicyclopentyl mercaptohydrogenated bisphenol antioxidant prepared by the above preparation method is used in polymer materials.

[0023] Beneficial effects:

[0024] This invention discloses a dicyclopentylmercapto-hydrogenated bisphenol antioxidant, its preparation method, and its applications. The modifiability and substitutability of the side groups in the dicyclopentylmercapto-hydrogenated bisphenol antioxidant provided by this invention greatly enrich the types of phenolic antioxidants, offering new ideas for the design and preparation of high-performance phenolic antioxidants. Furthermore, the dicyclopentylmercapto-hydrogenated bisphenol antioxidant of this invention not only possesses long-lasting antioxidant capabilities but also anti-aging properties. In addition, the preparation method provided by this invention is simple, uses widely available and inexpensive raw materials, and achieves a high product yield. Detailed Implementation

[0025] This invention provides a dicyclopentylthio-mercapto-hydrogenated bisphenol antioxidant, its preparation method, and its application. To make the objectives, technical solutions, and effects of this invention clearer and more explicit, the invention is further described in detail below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.

[0026] This invention provides a dicyclopentyl mercaptohydrogenated bisphenol antioxidant, the structural formula of which is shown in Formula I:

[0027]

[0028] R1 and R2 are independently selected from one of hydrogen, alkyl, amino, hydroxyl, and ester groups.

[0029] The sulfur atoms in the dicyclopentyl mercaptohydrobisphenol antioxidants provided in this invention can more flexibly donate or accept electrons. This flexibility allows the dicyclopentyl mercaptohydrobisphenol antioxidants to adapt to various environmental conditions and better cope with different oxidation situations. Therefore, the dicyclopentyl mercaptohydrobisphenol antioxidants of this invention generally have a broader antioxidant spectrum, which enables them to exhibit good antioxidant effects under various environmental conditions. Furthermore, the dicyclopentyl mercaptohydrobisphenol antioxidants provided in this invention belong to sulfur-containing antioxidants. Sulfur-containing antioxidants have diverse mechanisms of action, which can more comprehensively address different oxidation situations. Specifically, sulfur-containing antioxidants can generally undergo multi-electron transfer reactions, meaning they can donate multiple electrons to reduce oxidants, thereby effectively neutralizing free radicals. In contrast, ordinary phenolic antioxidants generally undergo single-electron transfer. Therefore, to a certain extent, sulfur-containing antioxidants may be more effective at combating oxidation reactions.

[0030] In addition, while phenolic antioxidants may decompose or become ineffective at high temperatures, sulfur-containing antioxidants maintain good stability under these conditions, thus extending their service life. Furthermore, sulfur-containing antioxidants exhibit good stability in acidic or alkaline environments, making them more suitable for certain specialized industrial environments. Moreover, sulfur-containing antioxidants can form complexes with metal ions, preventing them from participating in oxidation reactions; this property effectively inhibits oxidation reactions initiated by some metal ions. Furthermore, sulfur-containing antioxidants can sometimes delay the steps of the oxidation chain reaction, preventing the rapid propagation of oxidation reactions and demonstrating a good effect on inhibiting the initial stages of oxidation reactions.

[0031] In some embodiments, the dicyclopentyl mercaptohydrobisphenol antioxidant may be one of the following structural formulas, but is not limited thereto:

[0032]

[0033] This invention provides a method for preparing the above-mentioned dicyclopentyl mercaptohydrobisphenol antioxidant, the method comprising the following steps:

[0034] A nucleophilic addition reaction was carried out between hydrogenated bisphenol A as shown in Formula II and 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III, and the purified product was a dicyclopentyl mercaptohydrogenated bisphenol antioxidant as shown in Formula I; wherein R1 and R2 in Formula III are independently selected from one of hydrogen, alkyl, amino, hydroxyl, and ester groups.

[0035] The reaction pathway described above is shown below:

[0036]

[0037] In some embodiments, Formula III may be one of the following structural formulas, but is not limited thereto:

[0038]

[0039] In some embodiments, when R1 and R2 in formula III are both hydrogen, the structural formula of formula III is: The structure of this dicyclopentyl mercaptohydrobisphenol antioxidant is as follows:

[0040] In some embodiments, when R1 and R2 in formula III are both hydrogen, the structural formula of formula III is: The reaction formula for preparing this dicyclopentylthio-hydrogenated bisphenol antioxidant is as follows:

[0041]

[0042] In some embodiments, when R1 in Formula III is a hydroxyl group and R2 is an isopropyl group, the structural formula of Formula III is as follows: The structure of this dicyclopentyl mercaptohydrobisphenol antioxidant is as follows:

[0043] In some embodiments, when R1 in Formula III is a hydroxyl group and R2 is an isopropyl group, the structural formula of Formula III is as follows: The reaction formula for preparing this dicyclopentylthio-hydrogenated bisphenol antioxidant is as follows:

[0044]

[0045] In some embodiments, the step of subjecting hydrogenated bisphenol A as shown in Formula II and 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III to a nucleophilic addition reaction, followed by purification to obtain a dicyclopentylthio-hydrogenated bisphenol antioxidant as shown in Formula I, specifically includes:

[0046] Hydrogenated bisphenol A as shown in Formula II, 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III, a first solvent and a catalyst are mixed and reacted at 60-120°C for 2-12 hours.

[0047] After the reaction is completed, a second solvent is added to induce crystallization. After filtration, the resulting filter cake is washed with the second solvent. Finally, the washed filter cake is vacuum dried at a temperature of 60–100 °C to obtain the dicyclopentyl mercaptohydrobisphenol antioxidant as shown in Formula I.

[0048] In some embodiments, the equivalent ratio of the hydrogenated bisphenol A to the 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol is 1:(2-4).

[0049] In the preparation method of this invention, 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol should participate in the reaction at a ratio of not less than 2 equivalents, because this dicyclopentyl mercaptohydrobisphenol antioxidant has a disubstituted structure. In addition, appropriately increasing the proportion of 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol can accelerate the reaction rate and shorten the reaction time. However, a feed ratio greater than 4 equivalents will result in an excessively high concentration of 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol, which will reduce the reaction rate and cause waste of raw materials.

[0050] In some preferred embodiments, the equivalent ratio of the hydrogenated bisphenol A and the 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol is 1:(2.2-4).

[0051] In some embodiments, the ratio of the volume of the first solvent to the mass of the hydrogenated bisphenol A and the 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol is (2-10) mL:1 g.

[0052] When the proportion of the first solvent is less than 2, the solubility of the reactants decreases, reducing the probability of collisions between them and thus slowing down the reaction rate. When the proportion of the first solvent is greater than 10, the concentration of the reactants is too low, which also leads to a slowdown in the reaction rate and wastes solvent. Therefore, this invention limits the ratio of the volume of the first solvent to the total mass of the hydrogenated bisphenol A and 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol to (2-10) mL:1 g.

[0053] In some preferred embodiments, the ratio of the volume of the first solvent to the mass of the hydrogenated bisphenol A and the 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol is (2-8) mL:1 g.

[0054] In some embodiments, the molar ratio of the catalyst to the hydrogenated bisphenol A is (1.3 to 5):1.

[0055] The main function of the catalyst is to remove hydrogen atoms from the hydrogenated bisphenol A, facilitating nucleophilic attack. When the catalyst ratio is less than 1.3, the hydrogen removal efficiency is low; when the catalyst ratio is greater than 5, the solution becomes too alkaline, which interferes with the nucleophilic substitution reaction and wastes catalyst.

[0056] In some preferred embodiments, the molar ratio of the catalyst to the hydrogenated bisphenol A is (2-4):1.

[0057] In some embodiments, the amount of the second solvent is 20% to 150% of the volume of the first solvent.

[0058] The main function of the second solvent is to wash away unreacted raw materials or impurities. If too little is used, it will not be able to wash them thoroughly; if too much is used, it will cause some product loss and waste solvent.

[0059] In some preferred embodiments, the amount of the second solvent is 80% to 120% of the volume of the first solvent.

[0060] In some embodiments, the first solvent is selected from one or more of toluene, xylene, solvent oil, chlorobenzene, dimethyl sulfoxide, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, or 1,2-dichloroethane, and the second solvent is selected from one or more of isopropanol, tert-butanol, isobutanol, acetonitrile, dioxane, ethylene glycol dimethyl ether, or methyl tert-butyl ether.

[0061] In some preferred embodiments, the first solvent is selected from xylene or solvent oil, and the second solvent is selected from isopropanol or ethylene glycol dimethyl ether.

[0062] In some embodiments, the catalyst is selected from one or more of potassium carbonate, cesium carbonate, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, and sodium bicarbonate.

[0063] In some preferred embodiments, the catalyst is potassium carbonate.

[0064] In some embodiments, the above-described dicyclopentyl mercaptohydrobisphenol antioxidant or the dicyclopentyl mercaptohydrobisphenol antioxidant prepared by the above preparation method is provided for use in polymer materials.

[0065] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are merely some embodiments of the present invention, not all embodiments, and are intended only to illustrate the present invention and not to limit it. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0066] Example 1

[0067] The preparation of a dicyclopentyl mercaptohydrogenated bisphenol antioxidant includes the following steps:

[0068] Acetonitrile (160 mL), hydrogenated bisphenol A (12.01 g, 0.05 mol), 3-(2-bromoethyl)cyclopentane-1-thiol (24.95 g, 0.12 mol), and potassium carbonate (13.82 g, 0.10 mol) were added sequentially to a reactor. The reaction was carried out at 100 °C for 11 h, and the reaction progress was monitored by TLC. When the reaction point of hydrogenated bisphenol A disappeared, ethylene glycol dimethyl ether (95 mL) was added to induce crystallization. The mixture was filtered, and the resulting filter cake was washed three times with 60 mL of ethylene glycol dimethyl ether. Finally, it was dried under vacuum at 80 °C to obtain the final product. The yield was 89.2%.

[0069] The reaction pathway described above is shown below:

[0070]

[0071] Example 2

[0072] The preparation of a dicyclopentyl mercaptohydrogenated bisphenol antioxidant includes the following steps:

[0073] Acetonitrile (150 mL), hydrogenated bisphenol A (12.01 g, 0.05 mol), 4-(2-bromoethyl)-2-methylcyclopentane-1-thiol (26.64 g, 0.12 mol), and potassium carbonate (13.82 g, 0.10 mol) were added sequentially to a reactor. The reaction was carried out at 90 °C for 11 h, and the reaction progress was monitored by TLC. When the reaction point of hydrogenated bisphenol A disappeared, ethylene glycol dimethyl ether (95 mL) was added to induce crystallization. The mixture was filtered, and the resulting filter cake was washed three times with 60 mL of ethylene glycol dimethyl ether. Finally, it was dried under vacuum at 70 °C to obtain the desired product. The yield was 99.5%.

[0074] The reaction pathway described above is shown below:

[0075]

[0076] Example 3

[0077] The preparation of a dicyclopentyl mercaptohydrogenated bisphenol antioxidant includes the following steps:

[0078] Acetonitrile (230 mL), hydrogenated bisphenol A (12.01 g, 0.05 mol), 3-(2-bromoethyl)-2,5-dimethylcyclopentane-1-thiol (23.60 g, 0.10 mol), and potassium carbonate (13.82 g, 0.10 mol) were added sequentially to a reactor. The reaction was carried out at 100 °C for 8 h, and the reaction progress was monitored by TLC. When the reaction point of hydrogenated bisphenol A disappeared, ethylene glycol dimethyl ether (160 mL) was added to induce crystallization. The mixture was filtered, and the resulting filter cake was washed three times with 60 mL of ethylene glycol dimethyl ether. Finally, it was dried under vacuum at 70 °C to obtain the final product. The yield was 94.2%.

[0079] The reaction pathway described above is shown below:

[0080]

[0081] Example 4

[0082] The preparation of a dicyclopentyl mercaptohydrogenated bisphenol antioxidant includes the following steps:

[0083] Xylene (160 mL), hydrogenated bisphenol A (12.01 g, 0.05 mol), 2-amino-4-(2-bromoethyl)cyclopentane-1-thiol (22.30 g, 0.10 mol), and potassium carbonate (13.82 g, 0.10 mol) were added sequentially to a reactor. The reaction was carried out at 110 °C for 10 h, and the reaction progress was monitored by TLC. When the reaction point of hydrogenated bisphenol A disappeared, isopropanol (120 mL) was added to induce crystallization. The mixture was filtered, and the resulting filter cake was washed three times with 60 mL of isopropanol. Finally, it was dried under vacuum at 100 °C to obtain the final product. The yield was 93.4%.

[0084] The reaction pathway described above is shown below:

[0085]

[0086] Example 5

[0087] The preparation of a dicyclopentyl mercaptohydrogenated bisphenol antioxidant includes the following steps:

[0088] Toluene (210 mL), hydrogenated bisphenol A (12.01 g, 0.05 mol), 4-(2-bromoethyl)-2-mercaptocyclopentan-1-ol (22.39 g, 0.10 mol), and potassium carbonate (13.82 g, 0.10 mol) were added sequentially to a reactor. The reaction was carried out at 65 °C for 12 h, and the reaction progress was monitored by TLC. When the reaction point of hydrogenated bisphenol A disappeared, isopropanol (100 mL) was added to induce crystallization. The mixture was filtered, and the resulting filter cake was washed three times with 60 mL of isopropanol. Finally, it was dried under vacuum at 80 °C to obtain the desired product. The yield was 99.1%.

[0089] The reaction pathway described above is shown below:

[0090]

[0091] Example 6

[0092] The preparation of a dicyclopentyl mercaptohydrogenated bisphenol antioxidant includes the following steps:

[0093] N,N-dimethylformamide (180 mL), hydrogenated bisphenol A (12.01 g, 0.05 mol), 5-(2-bromoethyl)-3-isopropyl-2-mercaptocyclopentan-1-ol (26.60 g, 0.10 mol), and potassium carbonate (13.82 g, 0.10 mol) were added sequentially to a reactor. The reaction was carried out at 80 °C for 10 h, and the reaction progress was monitored by TLC. When the reaction point of hydrogenated bisphenol A disappeared, isopropanol (180 mL) was added to induce crystallization. The mixture was filtered, and the resulting filter cake was washed three times with 60 mL of isopropanol. Finally, it was dried under vacuum at 70 °C to obtain the final product. The yield was 97.3%.

[0094] The reaction pathway described above is shown below:

[0095]

[0096] Example 7

[0097] The preparation of a dicyclopentyl mercaptohydrogenated bisphenol antioxidant includes the following steps:

[0098] N,N-dimethylformamide (200 mL), hydrogenated bisphenol A (12.01 g, 0.05 mol), methyl 4-(2-bromoethyl)-2-mercapto-3-methylcyclopentane-1-carboxylate (28.80 g, 0.10 mol), and potassium carbonate (13.82 g, 0.10 mol) were added sequentially to a reactor. The reaction was carried out at 100 °C for 8 h, and the reaction progress was monitored by TLC. When the reaction point of hydrogenated bisphenol A disappeared, isopropanol (120 mL) was added to induce crystallization. The mixture was filtered, and the resulting filter cake was washed three times with 60 mL of isopropanol. Finally, it was dried under vacuum at 60 °C to obtain the final product. The yield was 94.1%.

[0099] The reaction pathway described above is shown below:

[0100]

[0101] Example 8

[0102] The preparation of a dicyclopentyl mercaptohydrogenated bisphenol antioxidant includes the following steps:

[0103] Tetrahydrofuran (180 mL), hydrogenated bisphenol A (12.01 g, 0.05 mol), methyl 4-(2-bromoethyl)-3-hydroxy-2-mercaptocyclopentane-1-carboxylate (28.19 g, 0.10 mol), and potassium carbonate (13.82 g, 0.10 mol) were added sequentially to a reactor. The reaction was carried out at 90 °C for 10 h, and the reaction progress was monitored by TLC. When the reaction point of hydrogenated bisphenol A disappeared, isopropanol (100 mL) was added to induce crystallization. The mixture was filtered, and the resulting filter cake was washed three times with 60 mL of isopropanol. Finally, it was dried under vacuum at 100 °C to obtain the final product. The yield was 94.1%.

[0104] The reaction pathway described above is shown below:

[0105]

[0106] Performance testing experiment

[0107] 1. Antioxidant effect test

[0108] The antioxidants prepared in Examples 1-8, blended with polypropylene, and samples of commercial 1076 antioxidant blended with polypropylene were subjected to thermal decomposition tests under air conditions. The test results are shown in Table 1.

[0109] Table 1

[0110] sample Temperature at which thermal degradation begins in air / °C Antioxidant 1076 230 Example 1 368 Example 2 420 Example 3 322 Example 4 330 Example 5 289 Example 6 387 Example 7 356 Example 8 294

[0111] As can be seen from Table 1, compared with the commercial 1076 antioxidant, the addition of the antioxidant of the present invention significantly increases the starting temperature of thermal degradation of the composite material, indicating that the antioxidant prepared by the present invention has a better antioxidant effect than the widely used commercial antioxidant.

[0112] 2. Antioxidant long-lasting antioxidant effect test

[0113] The antioxidants prepared in Examples 1-8 and blended with polypropylene, as well as the commercial 1076 antioxidant blended with polypropylene, were subjected to long-term thermal aging tests at 200°C. The test results are shown in Table 2.

[0114] Table 2

[0115] sample Time to start thermal degradation at 200℃ / min Antioxidant 1076 96 Example 1 548 Example 2 679 Example 3 485 Example 4 537 Example 5 412 Example 6 573 Example 7 600 Example 8 430

[0116] As can be seen from Table 2, compared with the commercial 1076 antioxidant, the addition of the antioxidant of the present invention significantly increases the time for the composite material to begin thermal degradation, indicating that the antioxidant prepared by the present invention has better long-lasting effect than the widely used commercial antioxidant.

[0117] It should be understood that the application of the present invention is not limited to the examples above. Those skilled in the art can make improvements or modifications based on the above description, and all such improvements and modifications should fall within the protection scope of the appended claims.

Claims

1. A dicyclopentyl mercaptohydrobisphenol antioxidant, characterized in that, The structural formula of the dicyclopentyl mercaptohydrobisphenol antioxidant is shown in Formula I: R1 and R2 are independently selected from one of hydrogen, alkyl, amino, hydroxyl, and ester groups.

2. A method for preparing the dicyclopentyl mercaptohydrogenated bisphenol antioxidant according to claim 1, characterized in that, The preparation method includes the following steps: A nucleophilic addition reaction was carried out between hydrogenated bisphenol A as shown in Formula II and 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III, and the purified product was a dicyclopentyl mercaptohydrogenated bisphenol antioxidant as shown in Formula I; wherein R1 and R2 in Formula III are independently selected from one of hydrogen, alkyl, amino, hydroxyl, and ester groups. The reaction pathway described above is shown below:

3. The method for preparing the dicyclopentyl mercaptohydrogenated bisphenol antioxidant according to claim 2, characterized in that, The steps involved in the nucleophilic addition reaction of hydrogenated bisphenol A as shown in Formula II and 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III, followed by purification, to obtain the dicyclopentylthio-hydrogenated bisphenol antioxidant as shown in Formula I, specifically including: Hydrogenated bisphenol A as shown in Formula II, 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol as shown in Formula III, a first solvent and a catalyst are mixed and reacted at 60-120°C for 2-12 hours. After the reaction is completed, a second solvent is added to induce crystallization. After filtration, the resulting filter cake is washed with the second solvent. Finally, the washed filter cake is vacuum dried at a temperature of 60–100 °C to obtain the dicyclopentyl mercaptohydrobisphenol antioxidant as shown in Formula I.

4. The method for preparing dicyclopentyl mercaptohydrogenated bisphenol antioxidants according to claim 2, characterized in that, The equivalent ratio of the hydrogenated bisphenol A and the 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol is 1:(2-4).

5. The method for preparing the dicyclopentyl mercaptohydrogenated bisphenol antioxidant according to claim 3, characterized in that, The ratio of the volume of the first solvent to the mass of the hydrogenated bisphenol A and 3-(2-bromoethyl)-2,5-disubstituted cyclopentane-1-thiol is (2-10) mL:1 g.

6. The method for preparing the dicyclopentyl mercaptohydrogenated bisphenol antioxidant according to claim 3, characterized in that, The molar ratio of the catalyst to the hydrogenated bisphenol A is (1.3–5):

1.

7. The method for preparing the dicyclopentyl mercaptohydrogenated bisphenol antioxidant according to claim 3, characterized in that, The amount of the second solvent used is 20% to 150% of the volume of the first solvent.

8. The method for preparing the dicyclopentyl mercaptohydrogenated bisphenol antioxidant according to claim 3, characterized in that, The first solvent is selected from one or more of toluene, xylene, solvent oil, chlorobenzene, dimethyl sulfoxide, N,N-dimethylformamide, acetonitrile, tetrahydrofuran, or 1,2-dichloroethane, and the second solvent is selected from one or more of isopropanol, tert-butanol, isobutanol, acetonitrile, dioxane, ethylene glycol dimethyl ether, or methyl tert-butyl ether.

9. The method for preparing the dicyclopentyl mercaptohydrogenated bisphenol antioxidant according to claim 3, characterized in that, The catalyst is selected from one or more of potassium carbonate, cesium carbonate, sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, and sodium bicarbonate.

10. The application of the dicyclopentyl mercaptohydrogenated bisphenol antioxidant of claim 1 or the dicyclopentyl mercaptohydrogenated bisphenol antioxidant prepared by any one of claims 2-9 in polymer materials.

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