Tetraphenylethylene-based protic organic ionic compound, preparation method thereof and application of tetraphenylethylene-based protic organic ionic compound as water-based lubricating additive

Abstract

The invention provides a tetraphenylethylene-based protic organic ionic compound, a preparation method thereof and application of the tetraphenylethylene-based protic organic ionic compound as a water-based lubricating additive, and belongs to the technical field of lubricating materials. According to the invention, carboxyl-functionalized tetraphenyl ethylene is taken as an anion, an alcohol amine compound is taken as a cation, and when the obtained proton-type organic ionic compound is taken as a water-based lubricating additive, the lubricating property of a water-based basic lubricating liquid can be effectively improved, and the proton-type organic ionic compound has the functions of leakage detection and wear sensing. The tetraphenyl ethylene-based proton type organic ionic compound structurally comprises a tetraphenyl ethylene functional group, and can emit fluorescence under ultraviolet excitation, so that leakage monitoring of a lubricating device can be realized; alcohol amine cations can provide good water solubility and stable lubricating effect, and can provide good corrosion resistance. The tetraphenyl ethylene-based proton type organic ionic compound has relatively high polarity, is easily adsorbed on an interface, and can improve the lubricating property of the water-based basic lubricating liquid.

Description

Technical Field

[0001] The invention relates to the technical field of lubricating materials, and in particular to a proton-type organic ion compound based on tetraphenylethylene, a preparation method thereof, and an application thereof as a water-based lubricating additive. Background Art

[0002] Lubricating materials with excellent performance are of great significance for reducing the failure of mechanical industrial equipment and increasing the service life of equipment. Oil-based lubricants are widely used in the transportation industry and industrial production due to their excellent lubricating properties, which significantly reduce friction and extend the service life of equipment. However, the large-scale use of oil-based lubricants relying on petroleum resources will lead to resource shortages and environmental pollution. Since the early 1990s, water-based lubricants have been used in mechanical processing, metal cutting and other fields. However, the disadvantage of weak lubrication performance of water-based lubricants limits their widespread use. Therefore, it is particularly important to develop water-based lubricating additives with excellent lubrication performance and multiple functions. Summary of the invention

[0003] In view of this, the object of the present invention is to provide a proton type organic ionic compound based on tetraphenylethylene and a preparation method thereof and an application thereof as a water-based lubricating additive. The proton type organic ionic compound based on tetraphenylethylene provided by the present invention can effectively improve the lubrication performance of a water-based base lubricating fluid.

[0004] In order to achieve the above-mentioned object of the invention, the present invention provides the following technical solutions:

[0005] The present invention provides a proton-type organic ion compound based on tetraphenylethylene, comprising an organic anion and an organic cation;

[0006] The organic anion has a structure shown in any one of Formula I to Formula IV:

[0007]

[0008] The organic cation has one or two structures shown in Formula V to Formula VII:

[0009]

[0010] In formula VII, n is a positive integer from 1 to 7;

[0011] The amount of the organic cation is such that the charge of the compound is conserved.

[0012] The present invention provides a method for preparing the above-mentioned proton-type organic ionic compound based on tetraphenylethylene, comprising the following steps:

[0013] A tetraphenylethylene compound, an alcohol amine compound and an alcohol solvent are mixed to perform an acid-base neutralization reaction based on proton transfer between the alcohol amine and the carboxylic acid to obtain a proton-type organic ion compound based on tetraphenylethylene;

[0014] The tetraphenylethylene compound is one of 4-(1,2,2-triphenylvinyl)benzoic acid, 4,4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid, 4,4-(1,2-diphenylethylene-1,2-diyl)dibenzoic acid and 4,4,4,4,4-(ethylene-1,1,2,2-tetrayl)tetrabenzoic acid;

[0015] The alcoholamine compound is one or two of diethanolamine, triethanolamine and N-alkyldiethanolamine, and the N-alkyldiethanolamine has a structure shown in Formula VIII:

[0016]

[0017] In Formula VIII, n is a positive integer of 1-7.

[0018] Preferably, the molar ratio of the carboxyl group in the tetraphenylethylene compound to the amine group in the alcoholamine compound is 1:1 to 1.1.

[0019] Preferably, when the alcoholamine compounds are two of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of different alcoholamine compounds is 1:1.

[0020] Preferably, the alcohol solvent is anhydrous methanol or anhydrous ethanol.

[0021] Preferably, the acid-base neutralization reaction based on proton transfer between alcohol amine and carboxylic acid is carried out at a temperature of 40 to 64.7° C. and for a time of 6 to 12 hours.

[0022] The present invention provides the use of the proton-type organic ion compound based on tetraphenylethylene as a water-based lubricating additive.

[0023] Preferably, the water-based lubricant additive is a leakage monitoring lubricant additive and / or a wear sensing lubricant additive.

[0024] The present invention provides a water-based lubricant, comprising a water-based base lubricant and the above-mentioned proton-type organic ion compound based on tetraphenylethylene.

[0025] Preferably, the water-based lubricant comprises one of water, ethylene glycol, polyethylene glycol, a water-ethylene glycol mixture and a water-polyethylene glycol mixture;

[0026] The mass content of the tetraphenylethylene-based proton organic ion compound in the water-based lubricant is 0.1-5%.

[0027] The present invention provides a proton-type organic ion compound based on tetraphenylethylene, comprising an organic anion and an organic cation, wherein the organic anion has a structure shown in any one of formulas I to IV, and the organic cation has one or two structures shown in formulas V to VII; the present invention uses carboxyl-functionalized tetraphenylethylene as anion and an alcoholamine compound as a cation, and the obtained proton-type organic ion compound can effectively improve the lubrication performance of a water-based base lubricating fluid when used as a water-based lubricating additive, and has the functions of leakage detection and wear perception. The proton-type organic ion compound based on tetraphenylethylene of the present invention has a tetraphenylethylene functional group in its structure, and can emit fluorescence under ultraviolet excitation, so that it can realize leakage monitoring of lubricating devices; the alcoholamine cation can provide good water solubility and stable lubrication effect, and can provide good corrosion resistance. The proton-type organic ion compound based on tetraphenylethylene in the present invention has a large polarity and is easily adsorbed on a metal interface (such as iron, etc.) to construct a tribochemical reaction film, which can improve the lubrication performance of a water-based lubricant. At the same time, the metal ions (such as iron ions) generated by wear will complex with the carboxylate radicals in the proton-type organic ion compound, thereby quenching the fluorescence of the tetraphenylethylene. The wear perception at this location is achieved by quenching the fluorescence.

[0028] The present invention provides a method for preparing the above-mentioned proton-type organic ionic compound based on tetraphenylethylene. The preparation method provided by the present invention is simple, does not require complex steps such as ion exchange, separation, and purification, has low preparation cost, and is easy to achieve industrial mass production. The ionic liquid prepared by the present invention using the above-mentioned method has excellent lubrication performance and luminescence under ultraviolet light for leakage monitoring. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 The fluorescence excitation spectra of B1 and B2 added to deionized water at 1 wt% mass fraction as multifunctional water-based lubricants;

[0030] Figure 2 The fluorescence emission spectra of B1 and B2 added to deionized water at 1 wt% mass fraction as multifunctional water-based lubricants;

[0031] Figure 3 The fluorescence emission spectra of B1 added to deionized water at a mass fraction of 1 wt% as a multifunctional water-based lubricant after adding different doses of iron ion solution. DETAILED DESCRIPTION

[0032] The present invention provides a proton-type organic ion compound based on tetraphenylethylene, comprising an organic anion and an organic cation;

[0033] The organic anion has a structure shown in any one of Formula I to Formula IV:

[0034]

[0035] The organic cation has one or two structures shown in Formula V to Formula VII:

[0036]

[0037] In Formula VII, n is a positive integer of 1 to 7, specifically 1, 2, 3, 4, 5, 6 or 7;

[0038] The amount of the organic cation is such that the charge of the compound is conserved.

[0039] In the present invention, the proton-type organic ionic compound based on tetraphenylethylene preferably has the following structure:

[0040]

[0041]

[0042] The present invention provides a method for preparing the above-mentioned proton-type organic ionic compound based on tetraphenylethylene, comprising the following steps:

[0043] A tetraphenylethylene compound, an alcohol amine compound and an alcohol solvent are mixed to perform an acid-base neutralization reaction based on proton transfer between the alcohol amine and the carboxylic acid to obtain a proton-type organic ion compound based on tetraphenylethylene;

[0044] The tetraphenylethylene compound is one of 4-(1,2,2-triphenylvinyl)benzoic acid, 4,4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid, 4,4-(1,2-diphenylethylene-1,2-diyl)dibenzoic acid and 4,4,4,4,4-(ethylene-1,1,2,2-tetrayl)tetrabenzoic acid;

[0045] The alcoholamine compound is one or two of diethanolamine, triethanolamine and N-alkyldiethanolamine, and the N-alkyldiethanolamine has a structure shown in Formula VIII:

[0046]

[0047] In Formula VIII, n is a positive integer of 1-7.

[0048] In the present invention, the N-alkyldiethanolamine is preferably N-butyldiethanolamine and N-ethyldiethanolamine.

[0049] In the present invention, the molar ratio of the carboxyl group in the tetraphenylethylene compound to the amine group in the alcoholamine compound is preferably 1:1 to 1.1. When the alcoholamine compound is two of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of different alcoholamine compounds is preferably 1:1.

[0050] Specifically, when the tetraphenylethylene compound is 4-(1,2,2-triphenylvinyl)benzoic acid, the alcoholamine compound is one of diethanolamine, triethanolamine and N-alkyldiethanolamine; the molar ratio of the 4-(1,2,2-triphenylvinyl)benzoic acid to the alcoholamine compound is preferably 1:1 to 1.1.

[0051] When the tetraphenylethylene compound is 4,4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid, the alcoholamine compound is one or two of diethanolamine, triethanolamine and N-alkyldiethanolamine; when the alcoholamine compound is one of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of 4,4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid to the alcoholamine compound is preferably 1:2. When the alcoholamine compound is two of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of 4,4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid to the first alcoholamine and the second alcoholamine is preferably 1:1:1.

[0052] When the tetraphenylethylene compound is 4,4-(1,2-diphenylethylene-1,2-diyl)dibenzoic acid, the alcoholamine compound is one or two of diethanolamine, triethanolamine and N-alkyldiethanolamine; when the alcoholamine compound is one of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of 4,4-(1,2-diphenylethylene-1,2-diyl)dibenzoic acid to the alcoholamine compound is preferably 1:2. When the alcoholamine compound is two of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of 4,4-(1,2-diphenylethylene-1,2-diyl)dibenzoic acid to the first alcoholamine and the second alcoholamine is preferably 1:1:1.

[0053] When the tetraphenylethylene compound is 4,4,4,4,4-(ethylene-1,1,2,2-tetrayl)tetrabenzoic acid, the alcoholamine compound is one or two of diethanolamine, triethanolamine and N-alkyldiethanolamine; when the alcoholamine compound is one of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of 4,4,4,4,4-(ethylene-1,1,2,2-tetrayl)tetrabenzoic acid to the alcoholamine compound is preferably 1:4. When the alcoholamine compound is two of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of 4,4,4,4,4-(ethylene-1,1,2,2-tetrayl)tetrabenzoic acid to the first alcoholamine and the second alcoholamine is preferably 1:2:2.

[0054] In the present invention, the alcohol solvent is preferably anhydrous methanol or anhydrous ethanol. In the present invention, the molar amount of the tetraphenylethylene compound and the volume ratio of the alcohol solvent are preferably 0.01 mol: 100-200 mL. The alcohol solvent used in the present invention can increase the solubility of the tetraphenylethylene compound.

[0055] In the present invention, the mixing is preferably heated mixing, and the heating temperature is preferably 50°C. The present invention has no special requirements for the mixing method, and the mixing method well known in the art can be used. In the present invention, the temperature of the acid-base neutralization reaction based on the proton transfer of the alcoholamine and the carboxylic acid is preferably 40 to 64.7°C, more preferably 50 to 60°C; the time is preferably 6 to 12 hours, and more preferably 8 to 10 hours.

[0056] In the present invention, after the acid-base neutralization reaction based on proton transfer of alcoholamine and carboxylic acid, the present invention preferably removes the alcohol solvent in the obtained acid-base neutralization reaction solution and dries the obtained product. In the present invention, the method of removing the alcohol solvent is preferably rotary evaporation. In the present invention, the drying is preferably vacuum drying, the drying temperature is preferably 60° C., and the drying time is preferably 12 hours.

[0057] The present invention provides the use of the above-mentioned proton-type organic ionic compound based on tetraphenylethylene as a water-based lubricant additive. In the present invention, the water-based lubricant additive is preferably a leakage monitoring lubricant additive and / or a wear sensing lubricant additive. The proton-type organic ionic compound based on tetraphenylethylene of the present invention has a tetraphenylethylene functional group in its structure and can emit fluorescence under ultraviolet excitation, so that it can realize leakage monitoring of lubricating devices.

[0058] The present invention provides a water-based lubricant, comprising a water-based base lubricant and the above-mentioned proton-type organic ion compound based on tetraphenylethylene.

[0059] In the present invention, the water-based lubricant preferably includes one of water, ethylene glycol, polyethylene glycol, a water-ethylene glycol mixture and a water-polyethylene glycol mixture. In the present invention, the polyethylene glycol is preferably polyethylene glycol 200. In the present invention, in the water-ethylene glycol mixture, the volume ratio of water to ethylene glycol is preferably 4:1 to 1:4, more preferably 1:1; in the water-polyethylene glycol mixture, the volume ratio of water to polyethylene glycol is preferably 1:1.

[0060] In the present invention, the mass content of the tetraphenylethylene-based protic organic ion compound in the water-based lubricant is preferably 0.1 to 5%, more preferably 0.5 to 4%, and further preferably 1 to 2%.

[0061] The following is a detailed description of a proton-type organic ionic compound based on tetraphenylethylene provided by the present invention, its preparation method and its application as a water-based lubricating additive in conjunction with the embodiments, but they should not be construed as limiting the scope of protection of the present invention.

[0062] Example 1

[0063] 0.01 mol of 4-(1,2,2-triphenylvinyl)benzoic acid was dissolved in 100 mL of anhydrous methanol, and the mixture was heated at 50°C until dissolved. Then, 0.01 mol of diethanolamine was added and the mixture was reacted at 50°C for 6 h. After the solvent was removed by rotary evaporation, the mixture was vacuum dried at 60°C for 12 h to obtain a proton-type organic ionic compound with diethanolamine as a cation and monocarboxyl-functionalized tetraphenylethylene as an anion, which was recorded as A1.

[0064] Example 2

[0065] 0.01 mol of 4,4-(1,2,2-triphenylvinyl)benzoic acid was dissolved in 100 mL of anhydrous ethanol, and the mixture was heated at 50°C until dissolved. Then, 0.01 mol of triethanolamine was added, and the mixture was reacted at 70°C for 12 h. After the solvent was removed by rotary evaporation, the mixture was vacuum dried at 60°C for 12 h to obtain an organic ionic compound with triethanolamine as a cation and monocarboxyl-functionalized tetraphenylethylene as an anion, which was recorded as A2.

[0066] Example 3

[0067] 0.01 mol of 4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid was dissolved in 100 mL of anhydrous methanol, and 0.02 mol of diethanolamine was added after heating at 50°C to dissolve, and the mixture was reacted at 50°C for 6 h. After rotary evaporation to remove the solvent, the mixture was vacuum dried at 60°C for 12 h to obtain an organic ionic compound with triethanolamine as a cation and dicarboxyl-functionalized tetraphenylethylene as anion, which was recorded as B1.

[0068] Example 4

[0069] 0.01 mol of 4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid was dissolved in 100 mL of anhydrous ethanol, and 0.02 mol of triethanolamine was added after heating at 50°C to dissolve. The mixture was reacted at 70°C for 12 h, and the solvent was removed by rotary evaporation. The mixture was then vacuum dried at 60°C for 12 h to obtain an organic ionic compound with triethanolamine as a cation and dicarboxyl-functionalized tetraphenylethylene as anion, which was recorded as B2.

[0070] Example 5

[0071] 0.01 mol of 4,4,4,4,4-(ethylene-1,1,2,2-tetrayl)tetrabenzoic acid was dissolved in 100 mL of anhydrous methanol, and 0.04 mol of diethanolamine was added after heating at 50°C to dissolve. The mixture was reacted at 50°C for 10 h, and the solvent was removed by rotary evaporation. The mixture was then vacuum dried at 60°C for 12 h to obtain an organic ionic compound with diethanolamine as a cation and tetracarboxyl-functionalized tetraphenylethylene as an anion, which was recorded as C1.

[0072] Example 6

[0073] 0.01 mol of 4,4,4,4,4-(ethylene-1,1,2,2-tetrayl)tetrabenzoic acid was dissolved in 100 mL of anhydrous ethanol, and the mixture was heated at 50°C until dissolved. Then, 0.04 mol of triethanolamine was added, and the mixture was reacted at 70°C for 12 h. After the solvent was removed by rotary evaporation, the mixture was vacuum dried at 60°C for 12 h to obtain an organic ionic compound with triethanolamine as a cation and tetracarboxyl-functionalized tetraphenylethylene as anion, which was recorded as C2.

[0074] Example 7

[0075] 0.01 mol of 4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid was dissolved in 100 mL of anhydrous methanol, and the mixture was heated at 50°C until dissolved. Then, 0.02 mol of N-ethyldiethanolamine was added, and the mixture was reacted at 50°C for 12 h. After the solvent was removed in vacuo, the mixture was dried in vacuo at 60°C for 12 h to obtain an organic ionic compound with N-ethyldiethanolamine as a cation and dicarboxyl-functionalized tetraphenylethylene as an anion, which was recorded as D1.

[0076] Example 8

[0077] 0.01 mol of 4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid was dissolved in 100 mL of anhydrous methanol, and 0.02 mol of N-butyldiethanolamine was added after heating at 50°C to dissolve, and the mixture was reacted at 50°C for 12 h. After the solvent was removed in vacuo, the mixture was dried in vacuo at 60°C for 12 h to obtain an organic ionic compound with N-butyldiethanolamine as a cation and dicarboxyl-functionalized tetraphenylethylene as an anion, which was recorded as D2.

[0078] Performance Testing

[0079] 1. Friction performance test

[0080] The tribological properties of proton-type organic ionic compounds based on tetraphenylethylene as water-based lubricant additives were evaluated using the SRV-IV micro-vibration friction and wear tester produced by Optimol Grease Company of Germany, and compared with water-based lubricant base fluids. The friction pair of the SRV-IV micro-vibration friction and wear tester is a bearing steel ball and a bearing steel disk, and the test conditions are: temperature 25°C, frequency 25Hz, amplitude 1mm, load 100~300N, and test time 30min.

[0081] Test Example 1

[0082] A1-C2 prepared in Examples 1-6 were added to deionized water at 1 wt% mass fraction to obtain 1 wt.% mass fraction of different proton-type organic ionic compound water-based lubricants. Water was selected as a reference sample, and its tribological properties were tested under a load of 100N. Its average friction coefficient is as follows. The test results are shown in Table 1:

[0083] Table 1 Average friction coefficient of 1wt.% water-based lubricants with different proton-type organic ionic compounds

[0084] Sample No. water A1 A2 B1 B2 C1 C2 Average friction coefficient 0.4020 0.2462 0.1526 0.1445 0.1586 0.1728 0.1714

[0085] It can be seen from Table 1 that the proton-type organic ionic compounds based on tetraphenylethylene prepared in Examples 1 to 6 of the present invention can reduce the average friction coefficient of the aqueous solution as a water-based lubricating additive.

[0086] Test Example 2

[0087] The C1 prepared in Example 5 was added to deionized water at different mass fractions to obtain proton-type organic ionic compound water-based lubricants with different mass fractions. Water was selected as a reference sample, and its tribological properties were tested under a load of 100N. Its average friction coefficient was as follows. The test results are shown in Table 2:

[0088] Table 2 Average friction coefficient of water-based lubricants with different mass fractions of C1 proton organic ionic compounds

[0089] Sample No. water 0.5wt% 1wt% 3wt% 5wt% Average friction coefficient 0.4020 0.1872 0.1728 0.1861 0.1801

[0090] As shown in Table 2, when there is no water-based lubricating additive, that is, pure water, the average friction coefficient is higher. The proton-type organic ionic compound based on tetraphenylethylene prepared in Example 5 of the present invention is used as a water-based lubricating additive to reduce the average friction coefficient of the aqueous solution. And 1wt% is the optimal concentration.

[0091] Test Example 3

[0092] The B1 prepared in Example 3 was added to deionized water at a mass fraction of 1 wt% to obtain a 1 wt% proton-type organic ionic compound water-based lubricant. Water was selected as a reference sample, and its tribological properties were tested under different loads. The average friction coefficient was as follows. The test results are shown in Table 3:

[0093] Table 3 Average friction coefficient of B1 proton-type organic ionic compound water-based lubricant under different loads

[0094] Sample No. 100N 200N 300N Average friction coefficient 0.1445 0.1481 0.1538

[0095] It can be seen from Table 3 that the water-based lubricating additive prepared in the present invention still performs well under higher loads.

[0096] Test Example 4

[0097] D1 and D2 prepared in Examples 7 and 8 were added to a water-based base liquid of deionized water and ethylene glycol (1:1) at a mass fraction of 1 wt% to obtain a 1 wt% proton-type organic ionic compound water-based lubricant. The water-based base liquid of ionized water and ethylene glycol (1:1) was selected as a reference sample, and its tribological properties were tested under a load of 100 N. Its average friction coefficient is as follows. The test results are shown in Table 4:

[0098] Table 4 Average friction coefficient of D1 and D2 proton-type organic ionic compound water-based lubricants under 100N load

[0099] Sample No. Deionized water and ethylene glycol (1:1) D1 D2 Average friction coefficient 0.1887 0.1663 0.1595

[0100] It can be seen from Table 4 that the proton-type organic ionic compounds based on tetraphenylethylene prepared in Examples 7 and 8 of the present invention can be used as water-based lubricating additives to reduce the average friction coefficient of the water-based base lubricant.

[0101] Test Example 5

[0102] D1 and D2 prepared in Examples 7 and 8 were added to a water-based base liquid of deionized water and polyethylene glycol 200 (1:1) at a mass fraction of 1 wt% to obtain a 1 wt% proton-type organic ionic compound water-based lubricant. The water-based base liquid of deionized water and polyethylene glycol 200 (1:1) was selected as a reference sample, and its tribological properties were tested under a load of 100 N. Its average friction coefficient is as follows. The test results are shown in Table 5:

[0103] Table 5 Average friction coefficient of D1 and D2 proton-type organic ionic compound water-based lubricants under 100N load

[0104] Sample No. Deionized water and polyethylene glycol 200 (1:1) D1 D2 Average friction coefficient 0.1845 0.1643 0.1509

[0105] It can be seen from Table 5 that the proton-type organic ionic compounds based on tetraphenylethylene prepared in Examples 7 and 8 of the present invention, as water-based lubricating additives, can reduce the average friction coefficient of the water-based base lubricant.

[0106] 2. Fluorescence performance test

[0107] The fluorescence properties of proton-type organic ionic compounds based on tetraphenylethylene as well as friction sensing lubricants were evaluated using the FLS1000 steady-state / transient fluorescence spectrometer from Edinburgh, UK.

[0108] Test Example 6

[0109] Figure 1 The fluorescence excitation spectra of B1 and B2 prepared in Examples 3 and 4 of the present invention added to deionized water at a mass fraction of 1 wt % as multifunctional water-based lubricants prove that they can emit fluorescence under the irradiation of a common ultraviolet flashlight (365 nm).

[0110] Test Example 7

[0111] Figure 2 The fluorescence emission spectra of B1 and B2 prepared in Examples 3 and 4 of the present invention, when added to deionized water at a mass fraction of 1 wt%, as a multifunctional water-based lubricant, prove that they can emit blue fluorescence under the irradiation of a common ultraviolet flashlight (365 nm). Once a leak occurs, they can be illuminated by an ultraviolet flashlight to emit light, and have the potential for lubricant leakage monitoring and sensing.

[0112] Test Case 8

[0113] Figure 3 The B1 prepared in Example 3 of the present invention was added to deionized water at a mass fraction of 1 wt% as a multifunctional water-based lubricant. The fluorescence emission spectra after adding different doses of iron ion solution proved that it could complex the iron ions generated by friction and wear, and fluorescence quenching occurred. It has the potential for application in wear sensing under steel friction conditions.

[0114] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the scope of protection of the present invention.

Claims

1. A proton-type organic ionic compound based on tetraphenylethylene, characterized in that: including organic anions and organic cations; The organic anion has a structure shown in any one of Formula I to Formula IV: The organic cation has one or two structures shown in Formula V to Formula VII: In formula VII, n is a positive integer from 1 to 7; The amount of the organic cation is such that the charge of the compound is conserved.

2. The method for preparing the proton-type organic ionic compound based on tetraphenylethylene according to claim 1, comprising the following steps: A tetraphenylethylene compound, an alcohol amine compound and an alcohol solvent are mixed to perform an acid-base neutralization reaction based on proton transfer between the alcohol amine and the carboxylic acid to obtain a proton-type organic ion compound based on tetraphenylethylene; The tetraphenylethylene compound is one of 4-(1,2,2-triphenylvinyl)benzoic acid, 4,4-(2,2-diphenylethylene-1,1-diyl)dibenzoic acid, 4,4-(1,2-diphenylethylene-1,2-diyl)dibenzoic acid and 4,4,4,4,4-(ethylene-1,1,2,2-tetrayl)tetrabenzoic acid; The alcoholamine compound is one or two of diethanolamine, triethanolamine and N-alkyldiethanolamine, and the N-alkyldiethanolamine has a structure shown in Formula VIII: In Formula VIII, n is a positive integer of 1-7.

3. The preparation method according to claim 2, characterized in that: The molar ratio of the carboxyl group in the tetraphenylethylene compound to the amine group in the alcoholamine compound is 1:

1.

4. The preparation method according to claim 2 or 3, characterized in that: When the alcoholamine compounds are two of diethanolamine, triethanolamine and N-alkyldiethanolamine, the molar ratio of different alcoholamine compounds is 1:

1.

5. The preparation method according to claim 2, characterized in that: The alcohol solvent is anhydrous methanol or anhydrous ethanol.

6. The preparation method according to claim 2, characterized in that: The temperature of the acid-base neutralization reaction based on the proton transfer of the alcohol amine and the carboxylic acid is 40 to 64.7° C. and the time is 12 to 18 hours.

7. Use of the proton-type organic ionic compound based on tetraphenylethylene according to claim 1 or the proton-type organic ionic compound based on tetraphenylethylene prepared by the preparation method according to any one of claims 2 to 6 as a water-based lubricating additive.

8. The use according to claim 7, characterized in that: The water-based lubricant additive is a leakage monitoring lubricant additive and / or a wear sensing lubricant additive.

9. A water-based lubricant, characterized in that: The invention comprises a water-based base lubricant and the proton type organic ion compound based on tetraphenylethylene as claimed in claim 1 or the proton type organic ion compound based on tetraphenylethylene prepared by the preparation method as claimed in any one of claims 2 to 6.

10. The water-based lubricant according to claim 9, characterized in that The water-based lubricant comprises one of water, ethylene glycol, polyethylene glycol, a water-ethylene glycol mixture and a water-polyethylene glycol mixture; The mass content of the tetraphenylethylene-based proton organic ion compound in the water-based lubricant is 0.1-5%.

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