Benzothiazole derivative lubricating additive with antioxidant and wear-resistant properties as well as preparation method and application of benzothiazole derivative lubricating additive

Abstract

The invention provides a benzothiazole lubricating additive with antioxidant and wear-resistant performance and a preparation method and application thereof, the structural formula of the benzothiazole lubricating additive is shown as a formula I or a formula II, and R is independently selected from H atoms or straight-chain or branched-chain alkyl with 4-18 carbon atoms. Alkyl arylamine is introduced into the benzothiazole derivative, so that the antiwear performance of the benzothiazole derivative serving as a lubricating additive is improved, and meanwhile, the benzothiazole derivative has antioxidation performance. The benzothiazole derivative provided by the invention has good thermal stability, and has good solubility in base oil as a lubricating additive. The benzothiazole lubricating additive can greatly reduce the wear degree of lubricating oil and effectively improve the oxidation stability of the lubricating oil. The benzothiazole derivative disclosed by the invention is simple, convenient and efficient in synthetic route and easy to operate, provides convenience for large-scale production, and has application potential as a lubricating additive.

Description

Technical Field

[0001] The present invention belongs to the technical field of lubricating additives, and in particular relates to a benzothiazole derivative having both antioxidant and anti-wear properties, and a preparation method and application thereof. Background Art

[0002] As a functional material, lubricating oil is crucial for maintaining the normal operation of mechanical equipment and extending its service life. The reliability and stability of its performance directly affect the safe, efficient, and stable operation of modern mechanical systems. Additives play an indispensable role in lubricating oils, as they can optimize key lubricant properties such as anti-oxidation, friction reduction, anti-wear, and corrosion protection. The scientific and rational use of additives can effectively improve the stability of lubricants and thus extend the service life of mechanical equipment. However, under long-term high-temperature conditions, lubricating oils are prone to oxidation and deterioration, and their functional additives are also prone to decomposition and failure in high-temperature environments. This will reduce the overall performance of the lubricant and may ultimately lead to problems such as wear and corrosion in mechanical equipment.

[0003] Thiazole sulfur-containing additives have good thermal stability and antioxidant properties due to the thiazole ring functional group, which can significantly improve the thermal stability, antioxidant, anti-wear and corrosion resistance of lubricants, especially under high temperature and high load conditions. For example, quaternary phosphonium salt mercaptobenzothiazole ionic liquids can extend the oxidation induction period of ester base oils, reduce the friction coefficient and wear volume, and exhibit excellent antioxidant and friction-reducing and anti-wear properties. In addition, benzothiazole heterocyclic derivatives also show better thermal stability, copper corrosion resistance and lubricity, while benzothiazole borate derivatives have good oil solubility, corrosion resistance and thermal stability. Studies have found that thiazole derivatives and other additives have a synergistic effect in rapeseed oil, showing excellent extreme pressure and anti-wear properties. Despite this, thiazole-containing lubricating additives may still decompose and fail under extremely high temperatures, and their thermal stability and antioxidant properties still need to be further improved to adapt to complex working conditions. At the same time, due to the polarity of heterocyclic compounds, they may react adversely with base oils or other additives, leading to precipitation or instability, affecting the performance of lubricants. Therefore, their compatibility with other components of lubricants is also a research difficulty. Summary of the Invention

[0004] In view of the above-mentioned shortcomings of the prior art, the purpose of the present invention is to provide a benzothiazole derivative with both antioxidant and anti-wear properties, as well as a preparation method and application thereof, to solve the problem that thiazole derivatives in the prior art have poor anti-wear and antioxidant properties as lubricant additives.

[0005] To achieve the above objectives, the present invention is achieved through the following technical solutions.

[0006] In a first aspect, the present invention provides a benzothiazole lubricant additive having both antioxidant and anti-wear properties. The structural formula of the benzothiazole lubricant additive is shown in Formula I or Formula II:

[0007]

[0008] Wherein, the R is independently selected from a H atom or a linear or branched alkyl group having 4 to 18 carbon atoms.

[0009] Wherein, the compound of formula I includes:

[0010]

[0011] Compounds of formula II include:

[0012]

[0013] In its structure, n=3-17.

[0014] A second aspect of the present invention provides a method for preparing a benzothiazole derivative having both antioxidant and anti-wear properties. The preparation of the compound of formula I comprises the following steps: using 2-chlorobenzothiazole and alkylaniline as reaction raw materials, DMSO, DMF, etc. as an organic solvent, and a base as a catalyst, and performing a substitution reaction by heating to obtain a benzothiazole lubricating additive of formula I;

[0015] The preparation of the compound of formula II comprises the following steps: either using 2-chlorobenzothiazole and naphthylamine as reaction raw materials, using DMSO, DMF or the like as an organic solvent, and using a base as a catalyst; the obtained product is directly used as a lubricating additive or further subjected to an alkylation reaction with an α-olefin to prepare a benzothiazole lubricating additive of formula II.

[0016] The alkylaniline is selected from linear / branched 4-alkylaniline or naphthylamine having 4 to 18 carbon atoms, preferably linear 4-alkylaniline having 8 to 12 carbon atoms; the α-olefin is selected from long-chain α-olefin having 4 to 18 carbon atoms, preferably α-olefin having 8 to 12 carbon atoms;

[0017] The base catalyst is any one of triethylamine, potassium carbonate, sodium carbonate, and pyridine;

[0018] A third aspect of the present invention provides a use of a benzothiazole derivative having both anti-oxidation and anti-wear properties as a lubricating additive having both anti-wear and anti-oxidation properties in the field of lubricating oil and / or grease.

[0019] Preferably, the benzothiazole derivative is used in a lubricating additive for reducing the diameter of wear spots in lubricating oil.

[0020] Preferably, the benzothiazole derivative is used in a lubricating additive for improving the oxidation stability of lubricating oil.

[0021] A fourth aspect of the present invention provides a lubricating oil and / or grease containing a benzothiazole derivative having both antioxidant and anti-wear properties as an additive, wherein the amount of the benzothiazole derivative added is 0.1-5.0 wt%, preferably 0.5-2.0 wt%, based on the weight of the base oil and / or base grease.

[0022] Preferably, based on the weight of the base oil and / or base fat, the added amount of the benzothiazole derivative is 0.1-1.0 wt%, 1.0-2.0 wt%, 2.0-3.0 wt%, 3.0-4.0 wt% or 4.0-5.0 wt%.

[0023] More preferably, based on the weight of the base oil and / or base fat, the added amount of the benzothiazole derivative is 0.5-2.0 wt%, more preferably 0.5-1.0 wt%.

[0024] Preferably, the base oil is a low-viscosity base oil.

[0025] Further preferably, the low viscosity base oil is a low viscosity III+ hydrocarbon base oil, polyalphaolefin or synthetic ester.

[0026] Compared with the prior art, the present invention has the following beneficial effects:

[0027] 1. The benzothiazole derivatives provided by the present invention contain sulfur-nitrogen heterocycles, which can increase the adsorption of the compound as a lubricating additive on metal surfaces, thereby improving its friction-reducing and anti-wear properties. In addition, the introduction of an aromatic secondary amine structure with an antioxidant effect into its structure improves the oxidative stability of the oil product. The long-chain alkyl group in the structure can ensure its solubility in base oil.

[0028] 2. The benzothiazole derivatives of the present invention introduce functional group structures such as aromatic secondary amines on the basis of the benzothiazole ring. Compared with the prior art, the benzothiazole derivatives in the present application have significant advantages in anti-wear and antioxidant properties.

[0029] 3. The benzothiazole derivatives of the present invention have a simple synthesis route and do not require tedious post-processing. As an additive, they have good solubility in base oil and can significantly reduce the wear spot diameter of the base oil while improving the oxidation stability.

[0030] 4. The benzothiazole derivatives of the present invention have excellent thermal stability, and the initial decomposition temperature is greater than 250°C. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1This is the hydrogen nuclear magnetic resonance spectrum of the benzothiazole derivative prepared in Example 1 of the present invention.

[0032] Figure 2 This is the infrared spectrum of the benzothiazole derivative prepared in Example 1 of the present invention.

[0033] Figure 3 This is a comparison of the wear spot morphologies of the CTL4 blank sample used in Example 2 of the present invention and the CTL4 sample added with the benzothiazole derivative I-1 (0.5 wt %) prepared in Example 1 on a four-ball friction tester.

[0034] Figure 4 This is a comparison of the wear spot morphologies of the CTL4 blank sample and the CTL4 sample with the benzothiazole derivative I-1 (2.0 wt %) prepared in Example 1 added thereto on a four-ball friction tester in Example 3 of the present invention.

[0035] Figure 5 This is the hydrogen nuclear magnetic resonance spectrum of the benzothiazole derivative prepared in Example 4 of the present invention.

[0036] Figure 6 This is the infrared spectrum of the benzothiazole derivative prepared in Example 4 of the present invention.

[0037] Figure 7 This is a comparison of the wear spot morphologies of the CTL4 blank sample and the CTL4 sample with the benzothiazole derivative I-2 (0.5 wt %) prepared in Example 4 added thereto on a four-ball friction tester in Example 5 of the present invention.

[0038] Figure 8 This is the hydrogen nuclear magnetic resonance spectrum of the benzothiazole derivative prepared in Example 6 of the present invention.

[0039] Figure 9 This is the infrared spectrum of the benzothiazole derivative prepared in Example 6 of the present invention.

[0040] Figure 10 This is a comparison of the wear spot morphologies of the CTL4 blank sample and the CTL4 sample with the benzothiazole derivative I-3 (0.5 wt %) prepared in Example 6 added thereto on a four-ball friction tester in Example 7 of the present invention.

[0041] Figure 11 This is the hydrogen nuclear magnetic resonance spectrum of the benzothiazole derivative prepared in Example 8 of the present invention.

[0042] Figure 12 This is the infrared spectrum of the benzothiazole derivative prepared in Example 8 of the present invention.

[0043] Figure 13This is a comparison of the wear spot morphologies of the CTL4 blank sample and the CTL4 sample with the benzothiazole derivative II-1 (0.5 wt %) prepared in Example 8 added thereto on a four-ball friction tester in Example 9 of the present invention.

[0044] Figure 14 This is a comparison of the wear spot morphologies of the CTL4 blank sample used in Comparative Example 1 of the present invention, the benzothiazole derivative I-1 prepared in Example 1, and the commercial lubricating additive thiadiazole derivative of the comparative example on a four-ball friction tester.

[0045] Figure 15 This is a comparison of the wear spot morphologies of the CTL4 blank sample used in Comparative Example 2 of the present invention, the benzothiazole derivative I-1 prepared in Example 1, and the comparative example 2-dodecyldisulfide benzothiazole on a four-ball friction tester. DETAILED DESCRIPTION

[0046] The following describes the implementation of the present invention through specific embodiments. People skilled in the art can easily understand other advantages and effects of the present invention from the contents disclosed in this specification.

[0047] Before further describing the specific embodiments of the present invention, it should be understood that the scope of the present invention is not limited to the specific embodiments described below. It should also be understood that the terminology used in the examples is intended to describe specific embodiments and is not intended to limit the scope of the present invention. The experimental procedures in the following examples, where specific conditions are not specified, were generally performed under conventional conditions or according to the conditions recommended by the respective manufacturers.

[0048] When the embodiments provide numerical ranges, it should be understood that, unless otherwise specified in the present invention, both endpoints of each numerical range and any numerical value between the two endpoints may be selected. Unless otherwise defined, all technical and scientific terms used in the present invention have the same meaning as those generally understood by those skilled in the art. In addition to the specific methods, equipment, and materials used in the embodiments, according to the understanding of the prior art by those skilled in the art and the description of the present invention, any methods, equipment, and materials of the prior art similar or equivalent to the methods, equipment, and materials described in the embodiments of the present invention may also be used to implement the present invention.

[0049] Example 1

[0050] This embodiment provides a specific benzothiazole derivative I-1. The structure of the benzothiazole derivative I-1 is

[0051] The formula is

[0052] The preparation method is as follows:

[0053] 1) Preparation of benzothiazole derivative I-1: To a 100 mL round-bottom flask, 1.0 eq of 2-chlorobenzothiazole, 20 mL of dimethyl sulfoxide, and 2.0 eq of anhydrous potassium carbonate were added. 1.1 eq of 4-dodecylaniline was then added at room temperature to form a mixture. The mixture was stirred at 100°C for 12 hours. After the reaction, 50 mL of deionized water was added, and the mixture was extracted with ethyl acetate. The resulting organic phase was concentrated by rotary evaporation and further recrystallized from petroleum ether to obtain an off-white solid in an 88% yield. The specific synthetic route is shown below:

[0054]

[0055] The structure of the prepared benzothiazole derivative I-1 was characterized:

[0056] 1 H-NMR (500MHz, Chloroform-d): δ9.06(s,1H),7.60(d,J=5.0Hz,1H),7.53(d,J=5.0Hz,1H),7.39(d,J=5.0Hz,2H),7.30(t,J=5.0Hz,1H) ,7.21(d,J=5.0Hz,2H),7.12(t,J=5.0Hz,1H),2.61(t,J=5.0Hz,2H),1.65-1.60(m,2H),1.33-1.27(m,10H),0.88(t,J=10.0Hz,9H)ppm.

[0057] IR(ATR):3180.28,3034.18,2920.49,1622.15,1567.84,1514.08,1453.98,1329.19,1314.74,1 273.61,1247.93,1225.32,1178.89,1017.51,920.62,844.56,823.35,788.11,746.40,721.96cm -1 .

[0058] The H NMR spectrum and IR spectrum of the benzothiazole derivative I-1 are shown as follows: Figure 1 and Figure 2 shown.

[0059] Example 2

[0060] In this example, the benzothiazole derivative I-1 prepared in the above Example 1 was added to the base oil as a lubricating additive to conduct anti-wear and antioxidant performance tests.

[0061] The benzothiazole derivative I-1 prepared in Example 1 was added to 200 mL of III+ base oil CTL4 in an amount of 0.5 wt %, heated to 60° C., and stirred for 30 min.

[0062] The wear spot diameters of the CTL4 blank sample without any lubricating additives and the CTL4 sample with the benzothiazole derivative I-1 added were tested using a four-ball friction tester. The test conditions were: load 196N, speed 1200rpm, oil temperature 75℃, 60min, and the wear spot morphology is compared. Figure 3 The oxidation stability of a CTL4 blank sample without any lubricant additives and a CTL4 sample with the benzothiazole derivative I-1 added were tested using a rotating oxygen bomb method. Comparative data on wear spot diameters and the time required for the rotating oxygen bomb pressure to drop by 175 kPa are shown in Table 1.

[0063] Table 1

[0064] Wear spot diameter / mm Rotating oxygen bomb time / min Blank 0.655 25 Benzothiazole derivative I-1 0.382 536

[0065] Example 3

[0066] In this example, the benzothiazole derivative I-1 prepared in the above Example 1 was added to the base oil as a lubricating additive to conduct anti-wear and antioxidant performance tests.

[0067] The benzothiazole derivative I-1 prepared in Example 5 was added to 200 mL of III+ base oil CTL4 in an amount of 2 wt %, heated to 60° C., and stirred for 30 min.

[0068] The wear spot diameters of the CTL4 blank sample without any lubricating additives and the CTL4 sample with the benzothiazole derivative I-1 added were tested using a four-ball friction tester. The test conditions were: load 196N, speed 1200rpm, oil temperature 75℃, 60min, and the wear spot morphology is compared. Figure 4 The oxidation stability of a CTL4 blank sample without any lubricant additives and a CTL4 sample containing the benzothiazole derivative I-1 were tested using a rotating oxygen bomb method. Comparative data on wear spot diameters and the time required for the rotating oxygen bomb pressure to drop by 175 kPa are shown in Table 2.

[0069] Table 2

[0070] Wear spot diameter / mm Rotating oxygen bomb time / min Blank 0.655 25 Benzothiazole derivative I-1 0.327 292

[0071] Example 4

[0072] This embodiment provides a specific benzothiazole derivative I-2, the structural formula of the benzothiazole derivative I-2 is

[0073] The preparation method is as follows:

[0074] 1) Preparation of benzothiazole derivative I-2: To a 100 mL round-bottom flask, 1.0 eq of 2-chlorobenzothiazole, 30 mL of dimethyl sulfoxide, and 2.2 eq of triethylamine were added. 1.1 eq of 4-tert-butylaniline was then added at room temperature to form a mixture. The mixture was stirred at 100°C for 12 hours. After the reaction, 80 mL of deionized water was added, and the mixture was extracted with ethyl acetate. The resulting organic phase was concentrated by rotary evaporation and further recrystallized from petroleum ether to give a white solid in a 90% yield. The specific synthetic route is shown below:

[0075]

[0076] The structure of the prepared benzothiazole derivative I-2 was characterized:

[0077] 1 H-NMR (500MHz, Chloroform-d): δ7.60(d,J=10.0Hz,1H),7.55(d,J=5.0Hz,1H),7.41(s,4H),7.32-7.29(m,1H),7.14-7.11(m,1H),1.34(s,9H)ppm.

[0078] IR(ATR):2963.51,1611.69,1557.37,1513.58,1446.81,1363.00,1327.96,1311.04,1270.28,1248.34,1192.48, 1127.70,1109.69,1067.80,1018.99,922.49,831.21,747.64,723.77,689.80,621.82,598.09,583.41,539.51cm -1 .

[0079] The H NMR spectrum and IR spectrum of the benzothiazole derivative I-2 are shown as follows: Figure 5 and Figure 6 shown.

[0080] Example 5

[0081] In this example, the benzothiazole derivative I-2 prepared in the above Example 4 was added to the base oil as a lubricating additive to conduct anti-wear and antioxidant performance tests.

[0082] The benzothiazole derivative I-2 prepared in Example 4 was added to 200 mL of III+ base oil CTL4 in an amount of 0.5 wt %, heated to 60° C., and stirred for 30 min.

[0083] The wear spot diameters of the CTL4 blank sample without any lubricating additives and the CTL4 sample with the benzothiazole derivative I-2 added were tested using a four-ball friction tester. The test conditions were: load 196N, speed 1200rpm, oil temperature 75℃, 60min, and the wear spot morphology is compared. Figure 7 The oxidation stability of a CTL4 blank sample without any lubricant additives and a CTL4 sample containing the benzothiazole derivative I-2 were tested using a rotating oxygen bomb method. Comparative data on wear spot diameters and the time required for the rotating oxygen bomb pressure to drop by 175 kPa are shown in Table 3.

[0084] Table 3

[0085] Wear spot diameter / mm Rotating oxygen bomb time / min Blank 0.655 25 Benzothiazole derivative I-2 0.322 546

[0086] Example 6

[0087] This embodiment provides a specific benzothiazole derivative I-3, the structural formula of the benzothiazole derivative I-3 is

[0088] The preparation method is as follows:

[0089] 1) Preparation of benzothiazole derivative I-3: To a 100 mL round-bottom flask, 1.0 eq of 2-chlorobenzothiazole, 20 mL of dimethyl sulfoxide, and 2.2 eq of triethylamine were added. 1.1 eq of 4-isobutylaniline was added at room temperature to form a mixture, which was stirred at 110°C for 12 hours. After the reaction, 50 mL of deionized water was added, and the mixture was extracted with ethyl acetate. The resulting organic phase was concentrated by rotary evaporation and further recrystallized from petroleum ether to obtain a white solid in an 85% yield. The specific synthetic route is shown below:

[0090]

[0091] The structure of the prepared benzothiazole derivative I-3 was characterized:

[0092] 1 H-NMR (500MHz, Chloroform-d): δ9.67(s,1H),7.59(d,J=5.0Hz,1H),7.50(d,J=5.0Hz,1H),7.38(d,J=10.0Hz,2H),7.28(t,J=5.0Hz,1H ),7.21(d,J=5.0Hz,2H),7.10(t,J=10.0Hz,1H),2.61(t,J=5.0Hz,2H),1.65-1.60(m,2H),1.37-1.31(m,6H),0.89(t,J=5.0Hz,3H)ppm.

[0093] IR(ATR):2924.58,2852.52,1621.72,1566.28,1514.94,1453.45,1328.77,1273.28,1247.69,1225.65,1118.3 8,1017.43,920.09,844.19,824.64,790.80,746.26,722.32,693.59,661.92,595.97,581.60,536.77,502.54cm -1 .

[0094] The H NMR spectrum and IR spectrum of the benzothiazole derivative I-3 are shown as follows: Figure 8 and Figure 9 shown.

[0095] Example 7

[0096] In this example, the benzothiazole derivative I-3 prepared in the above Example 6 was added to the base oil as a lubricating additive to conduct anti-wear and antioxidant performance tests.

[0097] The benzothiazole derivative I-3 prepared in Example 6 was added to 200 mL of III+ base oil CTL4 in an amount of 0.5 wt %, heated to 60° C., and stirred for 30 min.

[0098] The wear spot diameters of the CTL4 blank sample without any lubricating additives and the CTL4 sample with the benzothiazole derivative I-3 added were tested using a four-ball friction tester. The test conditions were: load 196N, speed 1200rpm, oil temperature 75℃, 60min, and the wear spot morphology is compared. Figure 10 The oxidation stability of a CTL4 blank sample without any lubricant additives and a CTL4 sample containing the benzothiazole derivative I-2 were tested using a rotating oxygen bomb method. Comparative data on wear spot diameters and the time required for the rotating oxygen bomb pressure to drop by 175 kPa are shown in Table 4.

[0099] Table 4

[0100] Wear spot diameter / mm Rotating oxygen bomb time / min Blank 0.655 25 Benzothiazole derivative I-3 0.319 413

[0101] Example 8

[0102] This embodiment provides a specific benzothiazole derivative II-1, the structural formula of the benzothiazole derivative II-1 is

[0103] The preparation method is as follows:

[0104] 1) Preparation of benzothiazole derivative II-1: To a 100 mL round-bottom flask, 1.0 eq of 2-chlorobenzothiazole, 20 mL of dimethyl sulfoxide, and 2.2 eq of sodium carbonate were added. 1.1 eq of naphthylamine was added at room temperature to form a mixture, which was stirred at 100°C for 12 hours. After the reaction, 50 mL of deionized water was added, and the mixture was extracted with ethyl acetate. The resulting organic phase was concentrated by rotary evaporation and further recrystallized from petroleum ether to obtain an off-white solid in a 70% yield. The specific synthetic route is shown below:

[0105]

[0106] The structure of the prepared benzothiazole derivative II-1 was characterized:

[0107] 1 H-NMR (500MHz, Chloroform-d): δ10.41(s,1H),8.28(d,J=5.0Hz,1H),8.21(d,J=5.0Hz,1H),7.98(d, J=5.0Hz,1H),7.79-7.75(m,2H),7.60-7.53(m,4H),7.31(t,J=5.0Hz,1H),7.31(t,J=10.0Hz,1H)ppm.

[0108] IR(ATR):3172.81,3132.89,3059.99,2847.65,1925.73,1627.39,1605.50,1562 .06,1509.90,1448.14,1448.14,1395.84,1309.61,1270.73,1261.11,1238.15,1 157.88,1131.91,1087.42,1066.88,1019.18,964.27,950.71,912.72,869.49,84 8.74,778.77,750.31,721.26,681.80,673.20,636.02,599.80,585.44,562.04cm -1 .

[0109] The H NMR spectrum and IR spectrum of benzothiazole derivative II-1 are shown as follows: Figure 11 and Figure 12 shown.

[0110] Example 9

[0111] In this example, the benzothiazole derivative II-1 prepared in the above Example 8 was added to the base oil as a lubricating additive to conduct anti-wear and antioxidant performance tests.

[0112] The benzothiazole derivative II-1 prepared in Example 8 was added to 200 mL of III+ base oil CTL4 in an amount of 0.5 wt %, heated to 90° C., and stirred for 30 min.

[0113] The wear spot diameters of the CTL4 blank sample without any lubricating additives and the CTL4 sample with benzothiazole derivative II-1 were tested using a four-ball friction tester. The test conditions were: load 196N, speed 1200rpm, oil temperature 75℃, 60min, and the wear spot morphology is compared in Table 1. Figure 13 The oxidation stability of a CTL4 blank sample without any lubricant additives and a CTL4 sample with the benzothiazole derivative II-1 added were tested using a rotating oxygen bomb method. Comparative data on wear spot diameters and the time required for the rotating oxygen bomb pressure to drop by 175 kPa are shown in Table 5.

[0114] Table 5

[0115] Wear spot diameter / mm Rotating oxygen bomb time / min Blank 0.655 25 Benzothiazole derivative II-1 0.422 320

[0116] Comparative Example 1

[0117] This comparative example compares the anti-wear and antioxidant properties of the prior art benzothiazole derivatives with those of commercial thiadiazole derivatives, the structures of which are as follows:

[0118]

[0119] The commercial thiadiazole derivative and benzothiazole derivative I-1 were added to 100 ml of CTL4 base oil at an addition amount of 0.5 wt %, heated to 60° C., and stirred for 30 min.

[0120] The wear spot diameter and oxidation stability of a blank sample of CTL4 base oil without any modifier, a sample with commercial thiadiazole derivatives, and a sample with benzothiazole derivative I-1 were tested using a four-ball friction tester and a rotating oxygen bomb. Figure 14 The comparative data of wear spot diameter and the time taken for the rotating oxygen bomb pressure to drop by 175 kPa are shown in Table 6.

[0121] Table 6

[0122] Wear spot diameter / mm Rotating oxygen bomb time / min Blank 0.655 25 Comparative Example 1 0.794 103 Benzothiazole derivative I-1 0.327 536

[0123] The results show that compared with the thiadiazole lubricating additives in the prior art, the benzothiazole derivative I-1 prepared in Example 1 of the present application has a smaller wear spot diameter and a longer rotating oxygen bomb time, indicating that it exhibits better anti-wear and antioxidant properties.

[0124] Comparative Example 2

[0125] This comparative example compares the anti-wear and antioxidant properties of the benzothiazole derivatives in the prior art with those of the benzothiazole derivatives (2-dodecyldithiobenzothiazole) reported in the literature, and its structure is as follows:

[0126]

[0127] The above-mentioned 2-dodecyldithiobenzothiazole and benzothiazole derivative I-1 were added to 100 ml of CTL4 base oil at an addition amount of 0.5 wt %, heated to 60° C., and stirred for 30 minutes.

[0128] The wear spot diameter and oxidation stability of the blank sample of CTL4 base oil without any modifier, the sample with 2-dodecyldithiobenzothiazole, and the sample with benzothiazole derivative I-1 were tested using a four-ball friction tester and a rotating oxygen bomb. Figure 15 The comparative data of wear spot diameter and the time taken for the rotating oxygen bomb pressure to drop by 175 kPa are shown in Table 6.

[0129] Table 7

[0130] Wear spot diameter / mm Rotating oxygen bomb time / min Blank 0.655 25 Comparative Example 2 0.486 36 Benzothiazole derivative I-1 0.327 536

[0131] The results show that compared with 2-dodecyldisulfide benzothiazole in the prior art, the benzothiazole derivative I-1 prepared in Example 1 of the present application has a smaller wear spot diameter and a longer rotating oxygen bomb time, indicating that it exhibits better anti-wear and antioxidant properties.

[0132] The above embodiments are merely illustrative of the principles and effects of the present invention and are not intended to limit the present invention. Anyone skilled in the art may modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all equivalent modifications or alterations made by one of ordinary skill in the art without departing from the spirit and technical principles disclosed herein are intended to be covered by the claims of the present invention.

Claims

1. A benzothiazole lubricating additive having both antioxidant and anti-wear properties, characterized in that: The structural formula of the benzothiazole lubricating additive is shown in Formula I or Formula II:

2. The benzothiazole lubricating additive having both antioxidant and anti-wear properties according to claim 1, characterized in that: The R is independently selected from a hydrogen atom or a linear or branched alkyl group having 4 to 18 carbon atoms.

3. The benzothiazole lubricating additive having both antioxidant and anti-wear properties according to claim 1, characterized in that: Compounds of formula I include: Compounds of formula II include:

4. A benzothiazole lubricating additive having both antioxidant and anti-wear properties as claimed in claim 3, characterized in that: In its structure, n=3-17.

5. A method for preparing the benzothiazole lubricating additive having both antioxidant and anti-wear properties according to any one of claims 1 to 4, characterized in that: The preparation of the compound of formula I comprises the following steps: using 2-chlorobenzothiazole and alkylaniline as reaction raw materials, DMSO, DMF or the like as organic solvent, and a base as catalyst, and heating and substituting to obtain the benzothiazole lubricating additive of formula I; The preparation of the compound of formula II comprises the following steps: either using 2-chlorobenzothiazole and naphthylamine as reaction raw materials, using DMSO, DMF or the like as an organic solvent, and using a base as a catalyst; the obtained product is directly used as a lubricating additive or further subjected to an alkylation reaction with an α-olefin to prepare a benzothiazole lubricating additive of formula II.

6. The preparation method according to claim 5, characterized in that The alkylaniline is selected from linear / branched 4-alkylaniline or naphthylamine having 4 to 18 carbon atoms; the α-olefin is selected from long-chain α-olefin having 4 to 18 carbon atoms; The base catalyst is any one of triethylamine, potassium carbonate, sodium carbonate, and pyridine; The heating substitution reaction temperature is 80-110°C, preferably 90-100°C.

7. Use of the benzothiazole derivative having both antioxidant and antiwear properties as claimed in any one of claims 1 to 4 as a lubricating additive having both antiwear and antioxidant properties in the field of lubricating oils and / or greases.

8. The use according to claim 7, characterized in that The invention relates to an application of the benzothiazole derivative in a lubricating additive for reducing the diameter of wear spots in lubricating oil.

9. The use according to claim 7, characterized in that The benzothiazole derivative is used as a lubricating additive for improving the oxidation stability of lubricating oil.

10. A lubricating oil and / or grease containing the benzothiazole derivative having both antioxidant and antiwear properties according to any one of claims 1 to 4 as an additive, wherein the amount of the benzothiazole derivative added is 0.1-5.0 wt% based on the weight of the base oil and / or base grease.

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