Organoboron compounds, processes for their preparation, uses thereof

Abstract

The application provides a sulfur-free and phosphorus-free organic boron compound, a preparation method and application thereof.The organic boron compound has excellent antioxidant performance and anti-wear and friction-reducing performance.

Description

TECHNICAL FIELD

[0001] The present application relates to an organic boron compound, in particular to a sulfur-free and phosphorus-free organic boron compound and a preparation method and application thereof. BACKGROUND

[0002] With the rapid development of industrial technology, lubricating oil and its additives also develop rapidly. For lubricating oil additives, only high-temperature-resistant, environmentally friendly, high-efficiency and multi-effect development can meet the requirements of higher lubricating oil. Boron-containing lubricating materials have the characteristics of extreme pressure and wear resistance, corrosion and rust prevention, sealing and environmental adaptability, non-toxicity and odorlessness; nitrogen-containing lubricating materials have the characteristics of ash-free, high electronegativity, small atomic radius, and easy to form hydrogen bonds between molecules adsorbed on the metal surface to improve the oil film strength; and both types of lubricating materials have the advantages of multifunctionality, designable molecular structure and combinable active elements. Therefore, the research on nitrogen-containing organic boron lubricating materials has attracted widespread attention in the field of modern friction and lubrication.

[0003] CN106366106A discloses a nitrogen-containing borate ester lubricating oil additive prepared by the reaction of boric acid, fatty alcohol and ethanolamine, which has strong hydrolysis resistance and good wear resistance and friction reduction. CN102936527A discloses an organic boron friction reducer prepared by the reaction of boric acid, natural oil and fat and organic alcohol amine, which has good thermal stability, good oil solubility and good wear resistance and friction reduction. CN112410096A discloses a nitrogen-containing borate ester lubricating oil additive prepared by the reaction of boric acid, sulfur-nitrogen alcohol and aromatic diethanolamide, which can protect equipment and machinery, increase the anti-friction performance of lubricating oil and reduce energy consumption. CN101735255A discloses a boron-nitrogen compound prepared by the reaction of oleic acid, triethanolamine, boric acid tributyl ester, butanol or ethanolamine, which has good wear resistance and friction reduction effect when added to liquid paraffin or other base oil.

[0004] At present, the sulfur-free and phosphorus-free organic boron has good wear resistance and friction reduction performance, but its oxidation resistance still has a large room for improvement. In addition, the trend of additive technology development is multifunctionalization, and the development of multifunctional additives can improve the performance of additives, reduce the variety and amount of additives in the formula system, improve the formula applicability, and meet the requirements of energy saving and environmental protection. SUMMARY

[0005] The present application provides a sulfur-free and phosphorus-free organic boron compound and a preparation method and application thereof, which has excellent oxidation resistance and wear resistance and friction reduction performance.

[0006] The organic boron compound of the present application has the structure shown in formula (I):

[0007]

[0008] In formula (I), there are a number of L groups and b number of boron-containing groups, a is an integer between 1 and 10 (preferably an integer between 1 and 5), b is an integer between 1 and 5 (preferably an integer between 1 and 3), the a number of L groups are identical to or different from each other and are each independently selected from the group represented by formula (II);

[0009]

[0010] In formula (II), HO is bonded to the benzene ring (HO is preferably located at the meta position of the chain where R1 is located on the benzene ring); y number of R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); the R groups are each independently selected from H and C 1-20 linear or branched alkyl (preferably each independently selected from H and C 1-4 linear or branched alkyl, more preferably tert-butyl); n is an integer between 1 and 10 (preferably an integer between 1 and 3); R1 is each independently selected from a single bond and C 1-20 linear or branched alkylene (preferably selected from a single bond and C 1-4 linear or branched alkylene); R2 in the n number of repeating units are identical to or different from each other and are each independently selected from a single bond and C 1-20 linear or branched alkylene (preferably each independently selected from a single bond and C 1-4 linear or branched alkylene); R3 is selected from H and C 1-20 linear or branched alkyl (preferably selected from H and C 1-4 linear or branched alkyl); the A groups in the n number of repeating units are identical to or different from each other and are each independently selected from a single bond, a group represented by formula (III) and a group represented by formula (IV),

[0011]

[0012] the R4 groups are each independently selected from H and C 1-20 linear or branched alkyl (preferably selected from H and C 1-4 linear or branched alkyl);

[0013] m is an integer between 0 and 10 (preferably an integer between 1 and 5);

[0014] the R5 groups are each independently selected from a trivalent C 1-20 linear or branched alkyl (preferably each independently selected from a trivalent C 1-4 linear or branched alkyl);

[0015] each G2 group is each independently selected from a binding end bonded to a G4 group present in another L group other than the L group it is present in, C 1-10straight or branched alkyl, -R6G3, H; each G3group is independently selected from -OG1, C 1-10 straight or branched alkyl, H (preferably each independently selected from -OG1, C 1-4 straight or branched alkyl, OH, H);

[0016] said R6group is selected from a single bond, C 1-20 straight or branched alkylene (preferably each independently selected from a single bond, C 1-4 straight or branched alkylene);

[0017] G1group is selected from a binding end to a boron atom in the boron-containing group, H;

[0018] G4group is selected from a binding end to a G2group present in another L group other than the L group it is in, H;

[0019] in the a L groups, at least one A group is selected from a group represented by formula (III) and at least one G1group is selected from a binding end to a boron atom in the boron-containing group;

[0020] each A' group in the b boron-containing groups is independently selected from a binding end to a G1group present in an L group, a group represented by formula (V), -OR', said R' group being H or C 1-20 straight or branched alkyl (preferably each independently selected from H or C 1-4 straight or branched alkyl);

[0021]

[0022] in formula (V), m is an integer between 0 and 10 (preferably an integer between 1 and 5);

[0023] each R0group is independently selected from C 1-10 straight or branched alkyl, -R6G5, H (preferably each independently selected from C 1-4 straight or branched alkyl, -R6G5, H);

[0024] each R5group is independently selected from a trivalent C 1-20 straight or branched alkyl (preferably each independently selected from a trivalent C 1-4 straight or branched alkyl);

[0025] G6group is selected from -R6G5, C 1-4 straight or branched alkyl, H;

[0026] said R6group is selected from a single bond, C 1-20 straight or branched alkylene (preferably each independently selected from a single bond, C1-4 linear or branched alkyl group, OH, H, wherein the G1groups are each independently selected from a binding end to a boron atom in the boron-containing group, C

[0027] each G5group is independently selected from -OG1, C 1-4 linear or branched alkyl group, OH, H, wherein the G1groups are each independently selected from a binding end to a boron atom in the boron-containing group, C 1-4 linear or branched alkyl group, H;

[0028] In the group of formula (V), at least one G1group is selected from a binding end to a boron atom in the boron-containing group;

[0029] In b boron-containing groups, at least one A' group is selected from a binding end to a G1group present in the L group;

[0030] Each group in the organic boron compound complies with the bonding rules.

[0031] According to the present application, the two binding ends of formula (III) or formula (IV) to formula (II) can be bonded to the groups of formula (II) in any manner, for example, in one direction to formula (II) or in the opposite direction to formula (II).

[0032] According to the present application, examples of the organic boron compound that can be cited include one or more of the following structurally compounds:

[0033]

[0034]

[0035] wherein the R groups are H or C1-C 20 linear or branched alkyl group.

[0036] According to the present application, the method for preparing the organic boron compound comprises the following steps:

[0037] (1) reacting a compound of formula (X) with a peroxide;

[0038]

[0039] In formula (X), HO is bonded to the benzene ring (HO is preferably located in the meta position of the chain where R1is located on the benzene ring); y R groups are bonded to the benzene ring; y is selected from an integer between 0 and 4 (preferably an integer between 1 and 3); the R groups are each independently selected from H and C 1-20 linear or branched alkyl group (preferably each independently selected from H and C 1-4 linear or branched alkyl group, more preferably selected from tert-butyl); n is an integer between 1 and 10 (preferably an integer between 1 and 3); R1is each independently selected from a single bond and C1-20 linear or branched alkylene (preferably selected from the group consisting of a single bond and C 1-4 linear or branched alkylene); R2in the n repeating units are the same as or different from each other, and each is independently selected from the group consisting of a single bond and C 1-20 linear or branched alkylene (preferably each is independently selected from the group consisting of a single bond and C 1-4 linear or branched alkylene); R3is selected from the group consisting of H and C 1-20 linear or branched alkyl (preferably selected from the group consisting of H and C 1-4 linear or branched alkyl); A" in the n repeating units are the same as or different from each other, and each is independently selected from the group consisting of a single bond, wherein each of the R4groups is independently selected from the group consisting of H and C 1-20 linear or branched alkyl (preferably selected from the group consisting of H and C 1-4 linear or branched alkyl); at least one A" in formula (X) is

[0040] (2) reacting the reaction product of step (1) with a compound represented by formula (Y);

[0041]

[0042] in formula (Y), m is an integer between 0 and 10 (preferably an integer between 1 and 5); each of the R0' groups is independently selected from the group consisting of C 1-10 linear or branched alkyl, -R6OH, H (preferably each is independently selected from the group consisting of C 1-4 linear or branched alkyl, -R6OH, H); each of the R5groups is independently selected from the group consisting of trivalent C 1-20 linear or branched alkyl (preferably each is independently selected from the group consisting of trivalent C 1-4 linear or branched alkyl); each G5' group is independently selected from the group consisting of C 1-4 linear or branched alkyl, OH, H; G6' group is selected from the group consisting of C 1-10 linear or branched alkyl, -R6OH, H; each of the R6groups is independently selected from the group consisting of a single bond, C 1-20 linear or branched alkylene (preferably each is independently selected from the group consisting of a single bond, C 1-4 linear or branched alkylene);

[0043] in formula (Y), at least one G5' group is selected from OH or at least one G6' group or R0' group is selected from -R6OH, and at least one R0' group or G6' group is H;

[0044] (3) reacting the reaction product of step (2) with an inorganic boron compound, a compound represented by formula (Y), and optionally a C 10-20 alcohol, and collecting the product.

[0045] According to the present application, in step (1), the compound represented by formula (X) can be selected from cardanol, alkylated cardanol, which can be obtained by reacting cardanol with an alkylating agent, for example, t-butylated cardanol can be obtained by reacting cardanol with t-butyl chloride.

[0046] According to the present application, in step (1), the peroxide is preferably one or more of hydrogen peroxide, peroxyformic acid, peroxyacetic acid, peroxy sulfonic acid, meta-chloro peroxy benzoic acid, t-butyl hydroperoxide, t-butyl peroxy acetate, methyl ethyl ketone peroxide, dibenzoyl peroxide and cyclohexanone peroxide, more preferably one or more of hydrogen peroxide, peroxyformic acid, peroxyacetic acid and peroxy sulfonic acid.

[0047] According to the present application, in steps (2), (3), the compound represented by formula (Y) can be selected from one or more of aliphatic amines, polyene polyamines, one or more hydroxyl-substituted aliphatic amines, one or more hydroxyl-substituted polyene polyamines, for example, one or more of ethanolamine, diethanolamine, hydroxyethyl ethylenediamine (i.e., N-(2-hydroxyethyl)ethylenediamine), diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine and pentaethylenehexaamine.

[0048] According to the present application, in step (3), the inorganic boron compound is preferably selected from one or more of boric acid, boric oxide and boric acid half-ester, which can be selected from monoalkyl boric acid ester, dialkyl boric acid ester, wherein the alkyl group is a C1-C 20 alkyl group. The C 10-20 alcohol can be selected from one or more of dodecanol, tetradecanol, hexadecanol and octadecanol.

[0049] According to the present application, the equivalent ratio between the compound represented by formula (X), the peroxide, the compound represented by formula (Y) in step (2), the inorganic boron compound, the compound represented by formula (Y) in step (3), and the optional C 10-20 alcohol is preferably 1:0.5-30:0.5-10:0.5-10:0.5-20:0-10, more preferably 1:2-30:1-5:1-8:2-6:0-3 or 1:2-30:1-5:1-8:2-6:0.1-3.

[0050] According to the present application, the reaction temperature of step (1) is preferably 0-100°C, more preferably 20-80°C; the reaction temperature of step (2) is preferably 50-150°C, more preferably 60-100°C; and the reaction temperature of step (3) is preferably 80-200°C, more preferably 110-150°C.

[0051] According to the present application, the reaction time of step (1), step (2), and step (3) is generally longer, and in general, the reaction time of step (1) is preferably 1 to 10 hours, more preferably 3 to 5 hours; the reaction time of step (2) is preferably 1 to 10 hours, more preferably 2 to 4 hours; and the reaction time of step (3) is preferably 1 to 10 hours, more preferably 3 to 5 hours.

[0052] According to the present application, the reaction steps (1), (2), or (3) can be carried out in the presence of a diluent and / or a solvent, or can be carried out without using a diluent and / or a solvent.

[0053] According to the present application, the diluent can be selected from one or more of API I, II, III, IV, and V group base oils, and common commercial products or grades include 150SN, 200SN, 350SN, 500SN, 650SN, 150BS, HVI-100, HVI-150, HVI-200, HVI-350, HVI-400, HVI-500, HVI-150BS, PAO4, PAO6, PAO8, PAO10, alkylbenzene, alkylnaphthalene, and the like.

[0054] According to the present application, the solvent can be selected from C 6-20 aromatic hydrocarbons (such as benzene, toluene, xylene, and cumene), C 6-10 alkanes (such as n-hexane, cyclohexane, and petroleum ether), solvent naphtha, and the like. These solvents can be used singly, or two or more in combination. The solvent can be removed after the reaction is completed, using a method known to those skilled in the art, for example, by distilling off the solvent under normal or reduced pressure.

[0055] According to a particular embodiment of the present application, the diluent and / or solvent can be added at any stage of the reaction steps, in a conventional amount in the art, and is not particularly limited.

[0056] According to the present application, it is apparent that the reaction steps are generally carried out under the protection of an inert gas atmosphere. As the inert gas, for example, nitrogen and argon, and the like, can be mentioned, and is not particularly limited.

[0057] According to the present application, in step (3), a promoter that promotes the completion of the reaction can be added, and common promoters include water, ethanol, propanol, butanol, aqueous ammonia, and the like. If a promoter is added, it can be removed after the reaction is completed, using a method known to those skilled in the art, for example, by distilling off under normal or reduced pressure.

[0058] According to the present application, by the aforementioned production method of the organic boron compound, as a reaction product, a single kind of organic boron compound can be produced, a mixture of a plurality of kinds of organic boron compounds can be produced, or a mixture of one or more kinds of the aforementioned organic boron compounds and the aforementioned diluent (if used) can be produced. These reaction products are all intended by the present application, and the difference in the form of existence thereof does not affect the realization of the effect of the present application. Therefore, these reaction products are collectively referred to as organic boron compounds without distinction in the context of the present specification. In view of this, according to the present application, there is no absolute necessity for further purification of the reaction product, or for further separation of a specific structure of the organic boron compound from the reaction product. Of course, the purification or separation is preferred for further enhancement of the intended effect of the present application, but is not essential to the present application. Nevertheless, as the method of the purification or separation, for example, the purification or separation of the reaction product by column chromatography or preparative chromatography, and the like, can be mentioned.

[0059] The organic boron compound of the present application has both excellent antioxidation performance and excellent antiwear and friction-reducing performance. The organic boron compound of the present application can be used as an antioxidant, an antiwear agent, and a friction-reducing agent for lubricating oil. The production method of the organic boron compound of the present application is simple in steps and high in conversion rate in the reaction process. BRIEF DESCRIPTION OF DRAWINGS

[0060] Figure 1 Infrared spectrum of the product of Example 2. DETAILED DESCRIPTION

[0061] In the present specification, the term "single bond" is sometimes used in the definition of a group. By "single bond", it is meant that the group is absent. For example, assuming the structural formula -CH2-A-CH3, wherein the group A is defined as being selected from a single bond and a methyl group. In view of this, if A is a single bond, it means that the group A is absent, and in this case, the structural formula is correspondingly simplified to -CH2-CH3.

[0062] In the context of the present specification, the expression "number + valence + group" or the like means a group obtained by removing the number of hydrogen atoms from the base structure (such as a chain, a ring, or a combination thereof) to which the group corresponds, and preferably means a group obtained by removing the number of hydrogen atoms from the carbon atoms (preferably saturated carbon atoms and / or non-identical carbon atoms) contained in the structure. For example, "3-valent straight-chain or branched alkyl group" means a group obtained by removing 3 hydrogen atoms from a straight-chain or branched alkane (i.e., the base chain to which the straight-chain or branched alkyl group corresponds).

[0063] The present application is further illustrated by the following examples, but is not limited thereto.

[0064] The main raw materials used are as follows:

[0065] Cardanol, Shanghai Wu Jing Chemical Technology Co., Ltd., technical grade

[0066] Zinc chloride, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0067] Concentrated sulfuric acid, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0068] Hydrogen peroxide (30%), National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0069] Formic acid, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0070] Boric acid, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0071] Diethanolamine, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0072] Diethylenetriamine, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0073] Ethanolamine, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0074] N-(2-hydroxyethyl)ethylenediamine, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0075] Tert-butyl chloride, National Pharmaceutical Group Chemical Reagent Co., Ltd., analytical pure

[0076] Antioxidant T501, Xingpu Company of Research Institute of Petroleum Refining and Petrochemical Industry, technical grade

[0077] Antioxidant T512, Xingpu Company of Research Institute of Petroleum Refining and Petrochemical Industry, technical grade

[0078] Cetyl alcohol, National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0079] Trimethylphenyl phosphate (TCP), National Pharmaceutical Group Chemical Reagent Co., Ltd., chemical pure

[0080] Diisooctyl sebacate, Beijing Chemical Three Factory, technical grade

[0081] Preparation of t-butylated epoxy cardanol

[0082] Take 100 g of cardanol, 8 g of formic acid, 0.3 g of sulfuric acid, 200 g of hydrogen peroxide, and add them to a three-necked flask with mechanical stirring, reflux condenser and temperature control. Start stirring and heating. Maintain the reaction temperature at 70°C for 3 hours. After the reaction is complete, cool it down and obtain a transparent brownish red liquid. Filter the reaction product, wash it with 5% KOH solution, then wash it with distilled water until it is neutral. Distill the organic phase under reduced pressure at 100 Pa and 150°C for 1 hour to remove water and unreacted raw materials, and obtain a transparent orange red liquid, epoxidized cardanol.

[0083] Dissolve 35 g of epoxidized cardanol in 100 ml of acetone, and then put it into a 250 ml three-necked flask. Add 0.9 g of zinc chloride catalyst, and start stirring and heating. Maintain the reaction temperature at 60°C, slowly add 9.5 g of t-butyl chloride dropwise into the flask, and continue the reaction for 3 hours after the addition is complete. After the reaction is complete, cool it down and obtain a transparent brownish red liquid. Filter the reaction product, wash it with 5% KOH solution, then wash it with distilled water until it is neutral. Distill it under reduced pressure at 1000 Pa and 120°C for 1 hour to remove the solvent, water and unreacted raw materials, and obtain a brownish red viscous liquid, t-butylated epoxidized cardanol.

[0084] The example reaction formula of the above reaction is shown below.

[0085]

[0086] Example 2

[0087] Put 22 g of t-butylated epoxidized cardanol prepared in Example 1, 5 g of N-(2-hydroxyethyl)ethylenediamine and 90 g of toluene into a 250 ml three-necked flask, and heat it with stirring at 90°C for 3 hours. After the reaction is complete, distill it under reduced pressure for 1 hour to remove the solvent and unreacted raw materials, and obtain a dark brownish red viscous liquid, t-butylated aminocardanol. Then add 3 g of boric acid, 10 g of N-(2-hydroxyethyl)ethylenediamine and 90 g of cyclohexane into the reaction vessel, stir and heat it to remove water, and react it at 120°C for 3 hours. Finally, filter it, and distill off the solvent and unreacted N-(2-hydroxyethyl)ethylenediamine to obtain an organic boron compound W-01.

[0088] The example reaction formula of the reaction is shown below, where R is H.

[0089]

[0090] Perform infrared spectrum analysis on the product prepared in Example 2, and the infrared spectrum is shown in Figure 1 , and the analysis results are shown in Table 1.

[0091] Table 1 Infrared analysis results of the product

[0092]

[0093] The characteristic peaks of C-OH stretching vibration, C-NH stretching vibration, benzene ring skeleton stretching vibration, N-C stretching vibration, O-C stretching vibration and B-O stretching vibration in the product indicate that the synthetic product is the target compound.

[0094] Example 3

[0095] Into a 250 mL three-necked flask, 36 g of the t-butylated epoxy cardanol prepared in Example 1, 10 g of diethanolamine and 90 g of toluene were added, heated under stirring, and reacted at 100°C for 4 h. After the reaction, the solvent and unreacted raw materials were removed by distillation under reduced pressure for 1 h to obtain a dark brownish red viscous liquid of t-butylated amino cardanol. Then, 6 g of boric acid, 20 g of diethanolamine and 90 g of cyclohexane were added to the reaction vessel, stirred and heated to remove water, and reacted at 150°C for 4 h. Finally, the solvent and unreacted diethanolamine were removed by filtration and distillation to prepare the organic boron compound W-02.

[0096] Example 4

[0097] Into a 250 mL three-necked flask, 36 g of the t-butylated epoxy cardanol prepared in Example 1, 10 g of diethanolamine and 90 g of toluene were added, heated under stirring, and reacted at 100°C for 4 h. After the reaction, the solvent and unreacted raw materials were removed by distillation under reduced pressure for 1 h to obtain a dark brownish red viscous liquid of t-butylated amino cardanol. Then, 6 g of boric acid, 20 g of diethanolamine and 90 g of cyclohexane were added to the reaction vessel, stirred and heated to remove water, and reacted at 150°C for 4 h. Finally, the solvent and unreacted diethanolamine were removed by filtration and distillation to prepare the organic boron compound W-02.

[0098] Comparative Example 1

[0099] Into a reaction vessel, 36.3 g of cetyl alcohol, 18.3 g of ethanolamine, 6.2 g of boric acid and 90 g of toluene were added, stirred and heated to react at 145°C for 6 h. Finally, the solvent and unreacted ethanolamine were removed by filtration and distillation to obtain the comparative organic boron compound V-01.

[0100] Example 5

[0101] W-01, W-02, W-03, V-01 were added into diisooctyl sebacate (diester) or TCP base oil (0.5% of the total mass of the oil product) at a dosage of 0.5%, and the anti-wear and friction-reducing performance was measured. The test conditions of the SRV anti-wear and friction-reducing evaluation experiment were: temperature 30℃, load 100N, stroke 1mm, test time 1 hour, frequency 50Hz. The SRV method is described in the national energy bureau standard NB / SH / T 0847-2010. The test results are shown in Table 2.

[0102] Table 2 SRV test results of the organic boron compounds of the present application and the comparative organic boron compounds

[0103]

[0104] As can be seen from Table 2, the organic boron compounds of the present application have better anti-wear and friction-reducing performance.

[0105] Example 6

[0106] W-01, W-02, W-03, V-01 and hindered phenol type antioxidants T501, T512 were added into diisooctyl sebacate or TCP base oil (0.5% of the total mass of the oil product) at a dosage of 0.5%, and the antioxidant performance was tested. The test results are shown in Table 3. The test instrument was a TA5000 model DSC instrument from TA Instruments, and the test conditions were: 190℃-240℃, oxygen pressure 0.5MPa, and heating rate 10℃ / min.

[0107] Table 3 Antioxidant test results

[0108]

[0109]

[0110] As can be seen by comparison, the organic boron compounds of the present application significantly improve the oxidation induction period relative to the comparative organic boron compounds, and in particular, the antioxidant performance in TCP base oil is extremely good, and is a kind of excellent antioxidant.

Claims

1. An organoboron compound, the structure of which is shown in formula (I): In formula (I), there are a L groups and b boron-containing groups, where a is an integer between 1 and 10, and b is an integer between 1 and 5. The a L groups may be the same as or different from each other, and each is independently selected from the groups shown in formula (II). In formula (II), HO is bonded to the benzene ring; y R groups are bonded to the benzene ring; y is selected from integers between 0 and 4; and each R group is independently selected from H and C. 1-20 Straight-chain or branched alkyl; n is an integer between 1 and 10; R1 is independently selected from single bonds and C bonds. 1-20 Straight-chain or branched alkylene groups; the R2s in the n repeating units may be the same or different from each other, and each is independently selected from single bonds and C bonds. 1-20 Straight-chain or branched alkylene groups; R3 is selected from H and C. 1-20 Straight-chain or branched alkyl; the A groups in the n repeating units may be the same or different from each other, and each is independently selected from single bonds, The groups shown in formula (III) and formula (IV), The R4 groups are each independently selected from H and C. 1-20 Straight-chain or branched alkyl groups; m is an integer between 0 and 10; Each of the R5 groups is independently selected from trivalent C. 1-20 Straight-chain or branched alkyl groups; Each G2 group is independently selected from the bonding end of a G4 group present in another L group besides the one it belongs to, and C. 1-10 Straight-chain or branched alkyl group, -R6G3, H; each G3 group is independently selected from -OG1, C 1-10 Straight-chain or branched alkyl groups, H; The R6 group is selected from single bonds, C 1-20 Straight-chain or branched alkylene groups; The G1 group is selected from the bonding end that is bonded to the boron atom in the boron-containing group, H; The G4 group is selected from the bonding end of the G2 group present in other L groups besides the L group it belongs to, and H; Among the a L groups, at least one A group is selected from the group shown in formula (III), and at least one G1 group is selected from the bonding end that is bonded to the boron atom in the boron-containing group; Each of the b boron-containing groups, specifically the A' group, is independently selected from the bonding end of the group bonded to the G1 group present in the L group, the group shown in formula (V), or -OR', wherein the R' group is H or C. 1-20 Straight-chain or branched alkyl groups; In equation (V), m is an integer between 0 and 10; Each of the R0 groups is independently selected from C 1-10 Straight-chain or branched alkyl groups, -R6G5, H; Each of the R5 groups is independently selected from trivalent C. 1-20 Straight-chain or branched alkyl groups; The G6 group is selected from -R6G5, C 1-4 Straight-chain or branched alkyl groups, H; The R6 group is selected from single bonds, C 1-20 Straight-chain or branched alkylene groups; Each G5 group is independently selected from -OG1, C 1-4 The alkyl, OH, or H groups, whether straight-chain or branched, wherein the G1 group is selected from the bonding end bonded to the boron atom in the boron-containing group, C 1-4 Straight-chain or branched alkyl groups, H; In the group shown in formula (V), at least one G1 group is selected from the bonding end that is bonded to the boron atom in the boron-containing group; In the b boron-containing groups, at least one A' group is selected from the binding end that is bonded to the G1 group present in the L group; The groups in the organoboron compound conform to the bonding rules.

2. The organoboron compound according to claim 1, characterized in that, In formula (I), a is an integer between 1 and 5, and b is an integer between 1 and 3; in formula (II), HO is located at the meta position on the chain containing R1 on the benzene ring; y is selected from integers between 1 and 3; and the R groups are each independently selected from H and C. 1-4 Straight-chain or branched alkyl; n is an integer between 1 and 3; R1 is independently selected from single bonds and C bonds. 1-4 Straight-chain or branched alkylene groups; R2 in each of the n repeating units is independently selected from single bonds and C bonds. 1-4 Straight-chain or branched alkylene groups; R3 is selected from H and C. 1-4 Straight-chain or branched alkyl groups; each of the R4 groups is independently selected from H and C. 1-4 Straight-chain or branched alkyl; m is an integer between 1 and 5; each of the R5 groups is independently selected from trivalent C 1-4 Straight-chain or branched alkyl groups; each G3 group is independently selected from -OG1, C 1-4 Straight-chain or branched alkyl groups, OH groups, and H groups; the R6 group is selected from single bonds, C groups, and H groups. 1-4 A straight-chain or branched alkylene group; wherein the R' group is H or C. 1-4 Straight-chain or branched alkyl groups; each of the R0 groups is independently selected from C10. 1-4 Straight-chain or branched alkyl groups, -R6G5, H.

3. The organoboron compound according to claim 1, characterized in that, The organoboron compound includes one or more of the following structural compounds: The R group is H or C1-C. 20 Straight-chain or branched alkyl groups.

4. A method for preparing organoboron compounds, comprising the following steps: (1) React the compound shown in formula (X) with a peroxide; In formula (X), HO is bonded to the benzene ring; y R groups are bonded to the benzene ring; y is selected from integers between 0 and 4; and each R group is independently selected from H and C. 1-20 Straight-chain or branched alkyl; n is an integer between 1 and 10; R1 is independently selected from single bonds and C bonds. 1-20 Straight-chain or branched alkylene groups; the R2s in the n repeating units may be the same or different from each other, and each is independently selected from single bonds and C bonds. 1-20 Straight-chain or branched alkylene groups; R3 is selected from H and C. 1-20 Straight-chain or branched alkyl; the A" in the n repeating units may be the same or different from each other, and each is independently selected from single bonds, The R4 groups therein are each independently selected from H and C. 1-20 Straight-chain or branched alkyl group; at least one A is present in formula (X). (2) React the reaction product of step (1) with the compound shown in formula (Y); In equation (Y), m is an integer between 0 and 10; Each of the R0' groups is independently selected from C 1-10 Straight-chain or branched alkyl groups, -R6OH, H; each of the R5 groups is independently selected from trivalent C. 1-20 Straight-chain or branched alkyl groups; each G5' group is independently selected from C 1-4 The G6' group is a straight-chain or branched alkyl group, OH, or H; the G6' group is selected from C 1-10 Straight-chain or branched alkyl groups, -R6OH, H; each of the R6 groups is independently selected from single bonds, C 1-20 Straight-chain or branched alkylene groups; In formula (Y), at least one G5' group is selected from OH or at least one G6' group or R0' group is selected from -R6OH, and at least one R0' group or G6' group is H; (3) React the reaction product of step (2) with an inorganic boron compound, a compound of formula (Y), and optional C. 10-20 The alcohol reaction was carried out, and the product was collected.

5. The method according to claim 4, characterized in that, In formula (X), HO is located at the meta position on the chain containing R1 on the benzene ring; y is selected from integers between 1 and 3; and the R groups are each independently selected from H and C. 1-4 Straight-chain or branched alkyl; n is an integer between 1 and 3; R1 is independently selected from single bonds and C bonds. 1-4 Straight-chain or branched alkylene groups; R2 in each of the n repeating units is independently selected from single bonds and C bonds. 1-4 Straight-chain or branched alkylene groups; R3 is selected from H and C. 1-4 Straight-chain or branched alkyl; the R4 groups are each independently selected from H and C. 1-4 Straight-chain or branched alkyl groups; in formula (Y), m is an integer between 1 and 5; each of the R0' groups is independently selected from C 1-4 Straight-chain or branched alkyl groups, -R6OH, H; each of the R5 groups is independently selected from trivalent C. 1-4 Straight-chain or branched alkyl groups; each of the R6 groups is independently selected from single bonds, C... 1-4 Straight-chain or branched alkylene groups.

6. The method according to claim 4, characterized in that, In step (1), the compound represented by formula (X) is selected from cashew phenol, alkylated cashew phenol; and / or, the peroxide is selected from one or more of hydrogen peroxide, peroxyformic acid, peracetic acid, peroxysulfonic acid, m-chloroperoxybenzoic acid, tert-butyl hydroperoxide, tert-butyl peracetic acid, methyl ethyl ketone peroxide, benzoyl peroxide and cyclohexanone peroxide. And / or, in step (2), the compound represented by formula (Y) is selected from one or more of aliphatic amines, polyene polyamines, one or more hydroxyl-substituted aliphatic amines, and one or more hydroxyl-substituted polyene polyamines; And / or, in step (3), the inorganic boron compound is selected from one or more of boric acid, boron oxide and borate half esters.

7. The method according to claim 4, characterized in that, The compound shown in formula (X) and peroxides, the compound shown in formula (Y) in step (2), inorganic boron compounds, the compound shown in formula (Y) in step (3), and optional C 10-20 The equivalence ratio between the alcohols is 1:0.5~30:0.5~10:0.5~10:0.5~20:0~10.

8. The method according to claim 4, characterized in that, The compound shown in formula (X) and peroxides, the compound shown in formula (Y) in step (2), inorganic boron compounds, the compound shown in formula (Y) in step (3), and optional C 10-20 The equivalence ratio between alcohols is 1:2-30:1-5:1-8:2-6:0-3 or 1:2-30:1-5:1-8:2-6:0.1-3.

9. The method according to claim 4, characterized in that, The reaction temperature for step (1) is 0–100℃; the reaction temperature for step (2) is 50–150℃; and the reaction temperature for step (3) is 80–200℃.

10. The method according to claim 4, characterized in that, The reaction temperature for step (1) is 20–80℃; the reaction temperature for step (2) is 60–100℃; and the reaction temperature for step (3) is 110–150℃.

11. The method according to claim 4, characterized in that, The reaction time for step (1) is 1 to 10 hours; The reaction time for step (2) is 1 to 10 hours; the reaction time for step (3) is 1 to 10 hours.

12. The method according to claim 4, characterized in that, The reaction time for step (1) is 3 to 5 hours; The reaction time for step (2) is 2 to 4 hours; the reaction time for step (3) is 3 to 5 hours.

13. The method according to claim 4, characterized in that, The reaction steps (1), (2) or (3) are carried out in the presence of a diluent and / or a solvent.

14. The method according to claim 4, characterized in that, The reaction steps (1), (2) or (3) are carried out under the protection of an inert gas atmosphere.

15. Use of the organoboron compound according to any one of claims 1-3 or the organoboron compound prepared according to any one of claims 4-14 as an antioxidant, anti-wear agent or friction reducer for lubricating oils.

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