CN101787322A - Extreme pressure antiwear agent containing ester-based thiadiazole derivative and preparation method thereof - Google Patents
Extreme pressure antiwear agent containing ester-based thiadiazole derivative and preparation method thereof Download PDFInfo
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Abstract
The invention discloses an extreme pressure antiwear agent containing an ester-based thiadiazole derivative shown as a following formula and a preparation method thereof. The is prepared from 2,5-dimercapto-1,3,4-thiadiazoles and an alpha, beta-unsaturated carbonyl compound by an addition reaction. The obtained extreme pressure antiwear agent containing the ester-based thiadiazole derivative can be used singly as additives of lubricating oil to make lubricating agents have excellent antiwear capability and extreme pressure resistance capability, can increase a PB value by about 73% in mineral oil, can decrease a wear scar diameter by 25-40%, and can increase the PB value by about 82% in colza oil. The obtained extreme pressure antiwear agent containing the ester-based thiadiazole derivative can be also compounded with other lubricant oil additives. In the formula, R is FORMULA, wherein R<1> is selected from the straight chains, branched chains or naphthenic bases of C1-C30, and R<2> and R<3> are independently selected from the straight chains, branched chains or naphthenic bases of C1-C30 respectively.
Description
Technical field: the present invention relates to a kind of organic compound and preparation method thereof, particularly a kind of extreme pressure antiwear agent containing ester-based thiadiazole derivative and preparation method thereof.
Background technology: environment and resource are the 21 century two large problems that face of human society, and tribology is closely related with it.Along with environmental protection and the energy-conservation harshness and complicated day by day that mechanical property is required, lubricating oil also is faced with various new requirements and challenge.Recent two decades comes the development of environmental friendly lubricant very rapid, has become a megatrend of lubricant development.
Existing studies show that, the nitrogen heterocyclic ring class additive of containing metal element is not the good multifunctional type lubricating oil additive of a class, it meets the environment protection requirement of " ashless ", " without phosphorus ", expects that it will have a good application prospect in green lubricating oil.In heterogeneous ring compound, thiadiazoles has higher cloud density and abundant active element S, N.Therefore when the design additive, can reduce the requirement that active element is introduced.Thiadiazoles derivative and vegetable seed wet goods environmental friendliness base oil have good synergistic.Its many derivatives, as carboxylic acid derivative, dimercapto derivative except that having outstanding antiwear and friction reduction property, also have very excellent metal system passivity energy, be developed to multi-functional lubricating oil additive and be widely used in the severe rugged environment such as Seatask unit.CN00801801.4 and CN00802316.6 disclose the thiadiazoles dimer and have been used as extreme-pressure additive with reaction product of gathering (ether) glycol and adducts, CN200480029627.4 discloses the lubricating composition of molybdate compound and thiadiazoles, on the thiadiazoles parent, introduced oxyalkyl chain, has good wear-resistant and anti-extreme pressure energy, but its oil soluble is poor, can only be used in the lubricating grease, and its preparation also uses halohydrocarbon, do not met environmental protection requirement.Therefore be necessary to develop a kind of oil soluble thiadiazoles derivative of preparation technology's environmental protection as extreme pressure anti-wear additives.
Summary of the invention: the object of the present invention is to provide a kind of ashless without phosphorus ester-based thiadiazole derivative that contains, it has good wear-resistant and anti-extreme pressure energy as lubricating oil additive.
Another object of the present invention provides a kind of preparation method of above-mentioned extreme pressure antiwear agent containing ester-based thiadiazole derivative, and it is simple to have technology, reaction conditions gentleness, the cheap characteristics that are easy to get and meet Atom economy of the raw material of use.
The chemical structural formula of extreme pressure antiwear agent containing ester-based thiadiazole derivative of the present invention is as follows:
R is in the formula
R wherein
1Be selected from C
1～C
30Straight chain, side chain or cycloalkyl; R
2, R
3Independently be selected from C respectively
1～C
30Straight chain, side chain or cycloalkyl.2 Methylpropionic acid methyl esters alkylthio-5-sulfydryl-1,3 is wherein arranged, the 4-thiadiazoles, 2 Methylpropionic acid ethyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid propyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid isopropyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid butyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid isobutyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid pentyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid isopentyl ester alkylthio-5-sulfydryl-1,3,4-thiadiazoles, 2 Methylpropionic acid peopentyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, the own ester alkylthio of 2 Methylpropionic acid-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid cyclohexyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid heptyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid monooctyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, the different monooctyl ester alkylthio of 2 Methylpropionic acid-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid ester in ninth of the ten Heavenly Stems alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid ester in last of the ten Heavenly stems alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid dodecyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid cetyl ester alkylthio-5-sulfydryl-1,3,4 thiadiazoles, 2 Methylpropionic acid stearyl alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid docosyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid ceryl ester alkylthio-5 sulfydryl-1,3, the 4-thiadiazoles, 2 Methylpropionic acid octacosyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-methyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-ethyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-propyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-isopropyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-butyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2 isobutyl propionates alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-amyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-isoamyl propionate alkylthio-5-sulfydryl-1,3,4-thiadiazoles, 2-propionic acid peopentyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-n-hexyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-propionic acid cyclohexyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-heptyl propionate alkylthio-5-sulfydryl-1,3,4 thiadiazoles, 2-n-octyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, the different monooctyl ester alkylthio-5 of 2-propionic acid sulfydryl-1,3, the 4-thiadiazoles, 2-nonyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-n-decyl propionate alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-propionic acid dodecyl ester alkylthio-5-sulfydryl-1,3,4 thiadiazoles, 2-propionic acid cetyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-propionic acid stearyl alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-propionic acid docosyl ester alkylthio-5-sulfydryl-1,3,4 thiadiazoles, 2-propionic acid ceryl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2-propionic acid octacosyl ester alkylthio-5-sulfydryl-1,3, the 4-thiadiazoles, 2,5-two (dimethyl succinate alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (diethyl succinate alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (dipropyl succinate alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (diisopropyl ester amber acid alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (dibutyl succinate alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid diisobutyl ester alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (diamyl succinate alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid diisoamyl ester alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid peopentyl ester alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid dihexyl alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid dicyclohexyl ester alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid two heptyl ester alkylthios)-1,3, the 4-thiadiazoles, 2,5-two (dioctyl succinate alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid di-isooctyl alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid ester alkylthio in two ninth of the ten Heavenly Stems)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid didecyl ester alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid two (dodecyl ester alkylthio))-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid two (cetyl ester alkylthio))-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid two (stearyl alkylthio))-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid two (docosyl ester alkylthio))-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid two (ceryl ester alkylthio))-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid two (octacosyl ester alkylthio))-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid methylethyl ester alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid methyl butyl ester alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid propyl group butyl ester alkylthio)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid butyl polyhexamethylene alkylthio)-1,3, the 4-thiadiazoles, 2,5 two (Succinic Acid hexyl octyl group ester alkylthios)-1,3, the 4-thiadiazoles, 2,5-two (Succinic Acid octyl group dodecyl ester alkylthio)-1,3,4-thiadiazoles and 2,5-two (Succinic Acid iso-octyl cetyl ester alkylthio)-1,3, the 4-thiadiazoles.
The preparation method of extreme pressure antiwear agent containing ester-based thiadiazole derivative of the present invention is as follows:
With 1.0 mole 2,5-dimercapto-1,3, the 4-thiadiazoles joins in 300～1600 milliliters the organic solvent, stir and add 0.01～0.5 mol catalyst and 0.5～3.0 mole of methacrylic ester down successively, acrylate or maleic acid diester, reacted 0.5～12 hour down at 20～200 ℃, be cooled to 20 ℃ then, filter, the a small amount of organic solvent washing of filter residue, the organic solvent after the washing is incorporated filtrate into, and filtrate water is washed till neutral back anhydrous magnesium sulfate drying, filter, filtrate obtains extreme pressure antiwear agent containing ester-based thiadiazole derivative after steaming and removing organic solvent under normal pressure.
The chemical structural formula of methacrylic ester, acrylate and maleic acid diester that the present invention uses is as follows:
R wherein
1Be selected from C
1～C
30Straight chain, side chain or cycloalkyl; R
2, R
3Independently be selected from C respectively
1～C
30Straight chain, side chain or cycloalkyl.Methyl methacrylate is wherein arranged, Jia Jibingxisuanyizhi, propyl methacrylate, isopropyl methacrylate, butyl methacrylate, Propenoic acid, 2-methyl, isobutyl ester, the methacrylic acid pentyl ester, the methacrylic isoamyl valerate, the methacrylic acid peopentyl ester, N-Hexyl methacrylate, cyclohexyl methacrylate, the methacrylic heptyl heptylate, Octyl methacrylate, Isooctyl methacrylate, nonyl methacrylate, decyl-octyl methacrylate, lauryl methacrylate, the methacrylic acid cetyl ester, the methacrylic acid stearyl, methacrylic acid docosyl ester, methacrylic acid ceryl ester, methacrylic acid octacosyl ester, methyl acrylate, ethyl propenoate, propyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, the vinylformic acid pentyl ester, the vinylformic acid isopentyl ester, the vinylformic acid peopentyl ester, Ethyl acrylate, cyclohexyl acrylate, the vinylformic acid heptyl ester, Octyl acrylate, Isooctyl acrylate monomer, vinylformic acid ester in the ninth of the ten Heavenly Stems, decyl acrylate, dodecylacrylate, the vinylformic acid cetyl ester, the vinylformic acid stearyl, vinylformic acid docosyl ester, vinylformic acid ceryl ester, vinylformic acid octacosyl ester, dimethyl maleate, ethyl maleate, dipropyl maleate, isopropyl maleate, dibutyl maleinate, diisobutyl maleate, dipentyl maleate, the toxilic acid diisoamyl ester, toxilic acid two peopentyl esters, the toxilic acid dihexyl, dicyclohexyl maleate, toxilic acid two heptyl esters, dioctyl maleate, diisooctyl maleate, dinonyl maleate, toxilic acid didecyl ester, toxilic acid two (dodecyl) ester, toxilic acid two (hexadecyl) ester, toxilic acid two (octadecyl) ester, toxilic acid two (docosyl) ester, toxilic acid two (ceryl) ester, toxilic acid two (octacosyl) ester, toxilic acid methylethyl ester, toxilic acid methyl butyl ester, toxilic acid propyl group butyl ester, toxilic acid butyl polyhexamethylene, toxilic acid hexyl octyl group ester, toxilic acid octyl group dodecyl ester and toxilic acid iso-octyl cetyl ester.
The organic solvent that the present invention uses is acetone, benzene, toluene, chloroform, ethyl acetate, N, dinethylformamide, tetrahydrofuran (THF), dioxane, dimethyl sulfoxide (DMSO) or C
1-C
4Fatty Alcohol(C12-C14 and C12-C18).
The catalyzer that the present invention uses is triethylamine, pyridine, 2,4,6-collidine, 4-Dimethylamino pyridine, N, accelerine, N, N-Diethyl Aniline, yellow soda ash, sodium bicarbonate, sodium hydroxide or potassium hydroxide.
The synthetic method of extreme pressure antiwear agent containing ester-based thiadiazole derivative of the present invention can be represented with following chemical equation:
Extreme pressure antiwear agent containing ester-based thiadiazole derivative of the present invention is owing to introduced the oil soluble carbochain that contains ester group, make this extreme pressure antiwear agent containing ester-based thiadiazole derivative can be dissolved in the lubricating oil, and ester group can be adsorbed in the metallic surface effectively, strengthens the extreme-pressure anti-wear effect.
Extreme pressure antiwear agent containing ester-based thiadiazole derivative of the present invention can use separately and add in the lubricating oil, can obtain the lubricating system of good wear-resistant and anti-extreme pressure energy, and it can improve P in mineral oil
BValue about 73% reduces wear scar diameter 25%～40%, can improve P in rapeseed oil
BValue about 82%; Also can with the compound use of other lubricating oil additive, can reach synergy synergy.
The addition of ester-based thiadiazole derivative extreme-pressure anti-friction additive in lubricating oil that contain of the present invention is 0.1wt%～15wt%.
Description of drawings:
Fig. 1 is the different monooctyl ester alkylthio of 2-propionic acid-5-sulfydryl-1,3 that embodiment 1 obtains, the infrared spectra spectrogram of 4-thiadiazoles.
Fig. 2 be embodiment 2 obtain 2,5-two (dibutyl succinate alkylthio)-1,3, the infrared spectra spectrogram of 4-thiadiazoles.
Fig. 3 is the different monooctyl ester alkylthio of 2-propionic acid-5-sulfydryl-1,3 that embodiment 1 obtains, the thermogravimetric analysis figure (TGA) of 4-thiadiazoles.
Fig. 4 be embodiment 2 obtain 2,5-two (dibutyl succinate alkylthio)-1,3, the thermogravimetric analysis figure (TGA) of 4-thiadiazoles.
Embodiment: for a better understanding of the present invention, describe by the following examples.
With 2,5-dimercapto-1,3,4-thiadiazoles 30.0g (0.2 mole) joins in the 300ml toluene, stir and to add 4.0g (0.1 mole) sodium hydroxide and 36.8g (0.2 mole) isopropyl acrylate down successively, 70 ℃ of following isothermal reactions 4 hours are cooled to 20 ℃, filter, filter residue washs with small amount of toluene, and the toluene after the washing is incorporated filtrate into, and filtrate water is washed till neutral back anhydrous magnesium sulfate drying, filter, obtain yellow opaque thickness oily product after filtrate is steamed and desolventized under normal pressure.The different monooctyl ester alkylthio of product 2-propionic acid-5-sulfydryl-1,3,4-thiadiazoles quality is 48.4g, productive rate is 72.4%.Fig. 1 is the Infrared spectroscopy of product, and analytical results is as follows: IR (cm
-1): 3067.2 (N-H), 2959.2,2928.1,2865.1 (CH
2-,-CH
3), 1732.0 (C=O), 1043.4 (heterocycle skeletons), 588.8 (C-S).
Embodiment 2
With 2,5-dimercapto-1,3,4-thiadiazoles 30.0g (0.2 mole) joins in the 300ml chloroform, stir and slowly to add 10.1g (0.1 mole) triethylamine and 91.2g (0.4 mole) dibutyl maleinate down successively, 70 ℃ of following isothermal reactions 6 hours are cooled to 20 ℃, filter, filter residue washs with minimum of chloroform, and the chloroform after the washing is incorporated filtrate into, and filtrate water is washed till neutral back anhydrous magnesium sulfate drying, filter, obtain red opaque thickness oily product after filtrate is steamed and desolventized under normal pressure.Product 2,5-two (dibutyl succinate alkylthio)-1,3,4-thiadiazoles quality is 93.7g, productive rate is 77.3%.Fig. 2 is the Infrared spectroscopy of product, and analytical results is as follows: IR (cm
-1): 3064.6 (N-H), 2958.4,2928.2,2872.7 (CH
2-,-CH
3), 1735.2 (C=O), 1041.1 (heterocycle skeletons), 600.9 (C-S).
Embodiment 3
Present embodiment is the ultimate analysis of sample.Table 1 has been listed the results of elemental analyses of embodiment 1～2, results of elemental analyses as can be known from table 1, the measured value of the C of all target compounds, H, N, S element and the theoretical value of calculating by molecular formula meet the requirement of lubricating oil additive basically, and absolute error is in allowed band.Can determine that the gained compound is a target compound.
Table 1 results of elemental analyses
Embodiment 4
Present embodiment is extreme pressure and antiwear behavior test and the heat stability testing to sample
According to the GB3142-82 standard, carried out measuring (addition is 1.0wt%) to base oil with by the last non seizure load (PB value) that ester-based thiadiazole derivative is added in commercially available refining rapeseed oil (RSO) and the hydrogenation mineral oil (5CST) that contains of example 1,2 preparation.The MS-10JB type four-ball tester that the four-ball tester that experiment is used produces as Xiamen trier factory, used steel ball is a secondary GCr15 standard steel ball (AISI-52100), and its diameter is 12.7mm, and hardness is 59～61HRC.At room temperature carry out, rotating speed is 1450rpm.The results are shown in table 2.
Last non seizure load (the P of table 2 base oil and various additives
BValue)
| Additive | Concentration (wt%) | ??P BValue (N) | Additive | Concentration (wt%) | ??P BValue (N) |
| ??RSO | ??100 | ??588 | ??5CST | ??100 | ??510 |
| |
??1.0 | ??1069 | |
??1.0 | ??882 |
| Embodiment 2 | ??1.0 | ??588 | Embodiment 2 | ??1.0 | ??559 |
The result shows that such hydroxyl pyrrolotriazine derivatives adds to and has certain extreme pressure property in the lubricating oil.
With the vertical omnipotent friction wear testing machine of MMW-1 that trier factory in Jinan produces the ester-based thiadiazole derivative that contains of commodity ZDDP and embodiment 1,2 preparations has been measured the 392N load down, experimental period is 30 minutes, additive level is 5.0wt%, and rotating speed is the wear scar diameter (WSD) of 1450rpm.Used steel ball is a secondary GCr15 standard steel ball (AISI-52100), and its diameter is 12.7mm, and hardness is 59～61HRC; Testing used base oil is hydrogenation mineral oil (5CST).Experiment is at room temperature carried out.The results are shown in table 3.
Table 3 four ball commentary valency results (wear scar diameter, WSD)
| Additive | Concentration (%) | Wear scar diameter (mm) |
| Base oil | ??100 | ??0.684 |
| ??ZDDP | ??2.0 | ??0.406 |
| |
??2.0 | ??0.461 |
| Embodiment 2 | ??2.0 | ??0.514 |
The result shows that the synthetic compound can effectively reduce the WSD value among the embodiment, and effect is near ZDDP.
Fig. 3 and Fig. 4 represent to contain among the embodiment 1,2 the thermogravimetric analysis figure (TGA) of ester-based thiadiazole derivative extreme-pressure anti-friction additive respectively, and as can be seen from the figure decomposition temperature all more than 200 ℃, has higher thermostability, is suitable as lubricating oil additive.
Claims (6)
1. extreme pressure antiwear agent containing ester-based thiadiazole derivative is characterized in that its chemical structural formula is as follows:
R is in the formula
R wherein
1Be selected from C
1～C
30Straight chain, side chain or cycloalkyl; R
2, R
3Independently be selected from C respectively
1～C
30Straight chain, side chain or cycloalkyl.
2. extreme pressure antiwear agent containing ester-based thiadiazole derivative as claimed in claim 1, it is characterized in that can be used as lubricated oil additives uses separately or and the compound use of other lubricating oil additive, its addition is 0.1wt%～15wt%.
3. a kind of preparation method of extreme pressure antiwear agent containing ester-based thiadiazole derivative according to claim 1 is characterized in that the preparation method is as follows:
With 1.0 mole 2,5-dimercapto-1,3, the 4-thiadiazoles joins in 300～1600 milliliters the organic solvent, stir and add 0.01～0.5 mol catalyst and 0.5～3.0 mole of methacrylic ester down successively, acrylate or maleic acid diester, reacted 0.5～12 hour down at 20～200 ℃, be cooled to 20 ℃ then, filter, the a small amount of organic solvent washing of filter residue, the organic solvent after the washing is incorporated filtrate into, and filtrate water is washed till neutral back anhydrous magnesium sulfate drying, filter, filtrate obtains extreme pressure antiwear agent containing ester-based thiadiazole derivative after steaming and removing organic solvent under normal pressure.
4. the preparation method of extreme pressure antiwear agent containing ester-based thiadiazole derivative according to claim 3 is characterized in that the chemical structural formula of methacrylic ester, acrylate and maleic acid diester is as follows:
R wherein
1Be selected from C
1～C
30Straight chain, side chain or cycloalkyl; R
2, R
3Independently be selected from C respectively
1～C
30Straight chain, side chain or cycloalkyl.
5. the preparation method of extreme pressure antiwear agent containing ester-based thiadiazole derivative according to claim 3, it is characterized in that organic solvent is acetone, benzene, toluene, chloroform, ethyl acetate, N, dinethylformamide, tetrahydrofuran (THF), dioxane, dimethyl sulfoxide (DMSO) or C
1-C
4Fatty Alcohol(C12-C14 and C12-C18).
6. the preparation method of extreme pressure antiwear agent containing ester-based thiadiazole derivative according to claim 3, it is characterized in that catalyzer is triethylamine, pyridine, 2,4,6-collidine, 4-Dimethylamino pyridine, N, N xylidine, N, N-Diethyl Aniline, yellow soda ash, sodium bicarbonate, sodium hydroxide or potassium hydroxide.
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| CN109942510A (en) * | 2019-03-25 | 2019-06-28 | 深圳市优宝新材料科技有限公司 | Thiazole derivative grafted olefin and its preparation method and application |
| CN110845419A (en) * | 2019-11-14 | 2020-02-28 | 安徽金德润滑科技有限公司 | Extreme pressure antiwear agent and road vehicle gear oil containing same |
| CN113121468A (en) * | 2021-04-22 | 2021-07-16 | 青岛中科润美润滑材料技术有限公司 | Thiadiazole castor oil derivative and application thereof |
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| JP2014500388A (en) * | 2010-12-21 | 2014-01-09 | ザ ルブリゾル コーポレイション | Functionalized copolymer and lubricating composition thereof |
| CN102060805A (en) * | 2010-12-29 | 2011-05-18 | 大连理工大学 | 2-thio-1, 3, 4-thiadiazole-3-yl compound and preparation method thereof |
| CN102060805B (en) * | 2010-12-29 | 2013-10-16 | 大连理工大学 | 2-thio-1, 3, 4-thiadiazole-3-yl compound and preparation method thereof |
| CN103965139B (en) * | 2013-01-30 | 2016-03-09 | 中国石油天然气股份有限公司 | A kind of thiadiazoles derivative containing thiocarbamate and Synthesis and applications thereof |
| CN103965139A (en) * | 2013-01-30 | 2014-08-06 | 中国石油天然气股份有限公司 | Thiocarbamate-containing thiadiazole derivative, and preparation method and use thereof |
| EP2816099A1 (en) * | 2013-06-20 | 2014-12-24 | Eurollubricants Tribologie GmbH | Chain saw lubricant |
| CN104017632A (en) * | 2014-05-14 | 2014-09-03 | 阿文能源科技（上海）有限公司 | Non-phosphorus sulfur-free chloride-free ashless lubricating oil |
| CN104017632B (en) * | 2014-05-14 | 2016-10-26 | 阿文能源科技（上海）有限公司 | Without phosphorus ashless lubricating oil without chlorine |
| CN105541757A (en) * | 2016-01-26 | 2016-05-04 | 大连理工大学 | [5-(o-hydroxy phenyl methylene imido)-1,3,4-thiadiazole-2-yl]ethyl thioacetate, preparation method and application of [5-(o-hydroxy phenyl methylene imido)-1,3,4-thiadiazole-2-yl]ethyl thioacetate |
| CN105601587A (en) * | 2016-03-18 | 2016-05-25 | 大连理工大学 | 1,3,4-thiadiazole derivative, synthesis method and application of 1,3,4-thiadiazole derivative |
| CN109942510A (en) * | 2019-03-25 | 2019-06-28 | 深圳市优宝新材料科技有限公司 | Thiazole derivative grafted olefin and its preparation method and application |
| CN110845419A (en) * | 2019-11-14 | 2020-02-28 | 安徽金德润滑科技有限公司 | Extreme pressure antiwear agent and road vehicle gear oil containing same |
| CN113121468A (en) * | 2021-04-22 | 2021-07-16 | 青岛中科润美润滑材料技术有限公司 | Thiadiazole castor oil derivative and application thereof |
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