CN111019736B - Sulfur-phosphorus-free organic friction modifier and preparation method thereof - Google Patents
Sulfur-phosphorus-free organic friction modifier and preparation method thereof Download PDFInfo
- Publication number
- CN111019736B CN111019736B CN201911122256.9A CN201911122256A CN111019736B CN 111019736 B CN111019736 B CN 111019736B CN 201911122256 A CN201911122256 A CN 201911122256A CN 111019736 B CN111019736 B CN 111019736B
- Authority
- CN
- China
- Prior art keywords
- friction
- friction modifier
- phosphorus
- sulfur
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/09—Diamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Abstract
The invention belongs to the technical field of lubricating oil additives, and particularly relates to a sulfur-phosphorus-free organic friction modifier and a preparation method thereof, wherein the friction modifier is an amine compound which is obtained by reacting long-chain fatty acyl chloride with organic amine to form amide under the action of triethylamine by taking the organic amine as a reaction substrate and dichloromethane as a solvent, and then further reducing the amide by using lithium aluminum hydride; the nitrogen atom in the structure of the organic friction modifier has lone pair electrons, and an ordered molecular adsorption film is formed on the surface of the metal, so that the friction and the abrasion on the surface of a metal friction pair are reduced; improves the anti-friction performance of the lubricating oil, is an environment-friendly additive which does not contain sulfur and phosphorus and is ashless, and has simple synthetic route, considerable yield and obvious antifriction effect.
Description
Technical Field
The invention relates to the technical field of lubricating oil additives, in particular to a sulfur-phosphorus-free organic friction modifier and a preparation method thereof.
Background
Lubricating oil additives have become a major component of lubricating oils, and with the increasing demands on the properties of lubricating oil products, research and development of new component additives have been driven. With the increasing strictness of energy-saving and environment-friendly laws and regulations, engine lubricating oil not only needs to improve the lubricating protection effect required by the operation of machinery, but also needs to consider the fuel economy.
Increasingly stringent requirements are placed on vehicle fuel economy by increasingly advanced vehicle engine technology and increasingly stringent environmental regulations. Improving fuel economy through low viscosity engine oils is an important area of current engine oil development, and low viscosity lubricants have become an irresistible trend with increasing machine precision and upgrading of lubricant processes. The low viscosity of the engine oil needs effective antifriction agent to match, the antifriction agent is an additive capable of reducing the friction coefficient of the lubricating oil under the condition of boundary lubrication, and the function of the antifriction agent is mainly to form a layer of physical or chemical adsorption film on the metal surface, avoid the direct contact of the surfaces of friction pairs, effectively improve the lubricating performance, increase the oil film strength, reduce the friction coefficient under the states of mixed lubrication and boundary lubrication, reduce the friction force and abrasion and achieve the purpose of energy conservation.
Therefore, it is of great importance to the development of energy-saving engine oils to investigate the use of friction reducers in engine oils and their contribution to engine oil passage through energy-saving stands.
Disclosure of Invention
The invention overcomes the defects of the prior art and provides a sulfur-phosphorus-free organic friction modifier and a preparation method thereof. Aims to solve the problems that the existing friction modifier has low friction reduction coefficient and poor effect in low-viscosity base oil and simultaneously causes influence on the environment.
The invention is realized by the following technical scheme.
The sulfur-phosphorus-free organic friction modifier is an amine compound, and the amine compound comprises any one of the following structural formulas I-VIII:
wherein R in the structural formula is selected from hydrogen atom or C8、C10、C12、C18Any of the linear alkyl groups of (a);
preferably, the friction modifier is added in an amount of 0.2 to 3% by weight based on the base oil.
More preferably, the friction modifier is added in an amount of 0.5 to 1.5% by weight based on the weight of the base oil.
Preferably, the base oil is a low viscosity PAO or a synthetic ester or a mixture of both.
A preparation method of a sulfur-free phosphorus type organic friction modifier is characterized in that the friction modifier is an amine compound which is obtained by reacting long-chain fatty acyl chloride with organic amine to form amide under the action of triethylamine by taking the organic amine as a reaction substrate and dichloromethane as a solvent and then further reducing the amide compound by lithium aluminum hydride.
The preparation method of the sulfur-free phosphorus type organic friction modifier is characterized in that the organic amine is preferably any one of diethylenetriamine, triethylene tetramine, tetraethylene pentamine and tri (2-aminoethyl) amine.
The preparation method of the sulfur-free phosphorus-type organic friction modifier is characterized in that the long-chain fatty acyl chloride is preferably caprylyl chloride.
Compared with the prior art, the invention has the beneficial effects that.
The organic friction modifier has lone pair electrons on nitrogen atoms in the structure, can provide electrons for electron-deficient tracks of metal, has strong adsorption effect on the metal, further forms an ordered molecular adsorption film on the surface of the metal, and reduces the friction and the abrasion on the surface of a metal friction pair. The organic friction modifier can obviously reduce the friction coefficient and the abrasion of the low-viscosity base oil, and effectively improve the anti-friction performance of the lubricating oil. The organic friction modifier is an environment-friendly additive which does not contain sulfur and phosphorus and is ashless, and has the advantages of simple synthetic route, considerable yield and obvious friction reducing effect.
A sulfur-free phosphorus-containing organic friction modifier is synthesized through a two-step method, and the friction reduction and wear resistance of the compound in low-viscosity base oil is evaluated through a four-ball friction wear tester. The sulfur-phosphorus-free nitrogen-containing compound has a simple synthetic route, does not need a complicated post-treatment process, has good solubility in base oil as an additive, can obviously reduce the friction coefficient, the wear scar diameter and the wear rate of the base oil, improves the bearing capacity of lubricating oil, and is a novel ash-free environment-friendly organic friction reducer.
Drawings
Fig. 1 is a synthetic route of N, N', N ″ -tri-N-octyl-diethylenetriamine generated in example 1 of the present invention.
FIG. 2 is a graph comparing the coefficient of friction at room temperature against the coefficient of friction at TE77 friction tester prepared in example 1 of the present invention.
FIG. 3 is a graph showing a comparison of the coefficient of friction at 100 ℃ in a TE77 friction tester prepared in example 1 of the present invention.
FIG. 4 is a comparison of the surface microscopic topography of the friction modifier prepared in example 1 of the present invention in a TE77 friction tester friction-back friction wear at room temperature.
FIG. 5 is a comparison of the surface microscopic topography of the friction modifier prepared in example 1 of the present invention at 100 ℃ in a reciprocating friction wear surface of a TE77 friction tester.
FIG. 6 is a synthetic route to N, N', N "-tri-N-octyl-tris (2-aminoethyl) amine of example 2 of this invention.
FIG. 7 is a graph comparing the coefficient of friction at room temperature against the coefficient of friction at TE77 friction tester prepared in example 2 of the present invention.
FIG. 8 is a graph showing a comparison of the coefficient of friction at 100 ℃ in a TE77 friction tester prepared in example 2 of the present invention.
FIG. 9 is a comparison of the surface microscopic topography of the friction modifier prepared in example 2 of the present invention in a TE77 friction tester friction-back friction wear at room temperature.
FIG. 10 is a comparison of the surface microscopic topography of the friction modifier prepared in example 2 of the present invention at 100 ℃ in a TE77 friction tester of reciprocating friction wear.
FIG. 11 shows the synthesis route of N, N' -triethylenetetramine generated in example 3 of the present invention.
FIG. 12 is a graph comparing the coefficient of friction at room temperature against the coefficient of friction at TE77 friction tester prepared in example 3 of the present invention.
FIG. 13 is a graph showing a comparison of the coefficient of friction at 100 ℃ in a TE77 friction tester prepared in example 3 of the present invention.
FIG. 14 is a comparison of the surface microscopic topography of the friction modifier prepared in example 3 of the present invention in a TE77 friction tester friction-back friction wear at room temperature.
FIG. 15 is a comparison of the surface microscopic topography of the friction modifier prepared in example 3 of the present invention at 100 ℃ in a reciprocating friction wear surface of a TE77 friction tester.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects to be solved by the present invention more clearly apparent, the present invention is further described in detail with reference to the embodiments and the accompanying drawings. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. The technical solutions of the present invention are described in detail below with reference to the embodiments and the drawings, but the scope of protection is not limited thereto.
Example 1
And (3) synthesis and antifriction performance of N, N' -tri-N-octyl-diethylenetriamine. The reaction equation is shown in FIG. 1.
The specific reaction process is as follows:
6.0g of diethylenetriamine and 19.5g of triethylamine are dissolved in 200mL of dichloromethane, 28.3g of octanoyl chloride is dropwise added in an ice bath, the ice bath is removed after the dropwise addition is finished, and the reaction is carried out for 12 hours at room temperature. Adding 200ml of water into a reaction bottle, separating out an organic phase, washing the organic phase with 100ml of water for three times, drying the organic phase with anhydrous sodium sulfate, evaporating the solvent under reduced pressure to obtain a crude product, recrystallizing the crude product with dichloromethane and petroleum ether to obtain 25.8g of octanamide derivative of diethylenetriamine, dissolving 4.0g of octanamide derivative in 150ml of anhydrous tetrahydrofuran, adding 2.0g of lithium aluminum hydride in batches under ice bath, heating to reflux under the protection of nitrogen, continuing to react for 48 hours, adding 6ml of water into the reaction solution when the reaction solution is cooled to room temperature, stirring until bubbles are completely released, adding 150ml of dichloromethane and a proper amount of anhydrous sodium sulfate, stirring to be clear, filtering, evaporating the solvent from the filtrate to obtain 3.3g of a target product N, N' -tri-N-octyl-diethylenetriamine,1H-NMR(400MHz,CDCl3)δ2.64(t,4H),2.59(t,4H),2.55(t,4H),2.40(t,2H),1.47(m,4H),1.42(t,2H),1.27(m,30H),0.88(t,9H)ppm；MS(EI):m/z calcd[M+H+]C28H62N3 +:440.5；Found:440.5.
adding the prepared N, N' -tri-N-octyl-diethylenetriamine into PAO4 in an addition amount of 0.5%, heating to 60 ℃, and stirring for 30 min. The blank sample and the test sample of example 1 were tested for four-ball wear spot diameter and coefficient of friction under the following test conditions: load 196N, main shaft rotation speed 1200r/min, oil temperature 75 ℃, 30min, the detection results are shown in Table 1.
Table 1 four ball machine test scrub spot diameter, average coefficient of friction.
| Abrasion Spot diameter (mm) | Average coefficient of friction | |
| Blank sample | 0.545 | 0.072 |
| Example 1 | 0.429 | 0.051 |
In addition, the coefficient of friction at room temperature (see FIG. 2) and at 100 deg.C (FIG. 3), the load was 160N, the frequency of reciprocal vibration was 2Hz, and the stroke was 10mm, respectively, evaluated on a TE77 friction tester, and the topography of the wear surface was observed with a three-dimensional profiler (FIGS. 4 and 5).
Example 2
The synthesis and antifriction performance of N, N' -tri-N-octyl-tri (2-aminoethyl) amine. The reaction equation is shown in FIG. 6.
The specific reaction process is as follows:
5.0g of tris (2-aminoethyl) amine and 13.8g of triethylamine were dissolved in 200mL of dichloromethane and subjected to ice-bath16.8g of octanoyl chloride is added dropwise, the ice bath is removed after the dropwise addition, and the reaction is carried out for 12 hours at room temperature. Adding 200ml of water into a reaction bottle, separating out an organic phase, washing the organic phase with 100ml of water for three times, drying the organic phase with anhydrous sodium sulfate, evaporating the solvent under reduced pressure to obtain a crude product, recrystallizing the crude product with dichloromethane and petroleum ether to obtain 17.1g of the caprylamide derivative of tris (2-aminoethyl) amine, dissolving 4.0g of the caprylamide derivative of tris (2-aminoethyl) amine in 150ml of anhydrous tetrahydrofuran, adding 1.2g of lithium aluminum hydride in batches under ice bath, heating to reflux under the protection of nitrogen, continuing to react for 48 hours, adding 6ml of water into the reaction solution when the reaction solution is at room temperature, stirring until bubbles are completely released, adding 150ml of dichloromethane and a proper amount of anhydrous sodium sulfate, stirring until the solution is clear, filtering, evaporating the solvent from the filtrate to obtain 3.2g of the target product N, N' -tri-N-octyl-tris (2-aminoethyl) amine,1H-NMR(400MHz,CDCl3)δ2.64(t,4H),2.59(t,4H),2.55(t,4H),2.40(t,2H),1.47(m,4H),1.42(t,2H),1.27(m,30H),0.88(t,9H)ppm；MS(EI):m/z calcd[M+H+]C28H62N3 +:440.5；Found:440.5.
the prepared N, N' -tri-N-octyl-tri (2-aminoethyl) amine was added to PAO4 in an amount of 0.5%, heated to 60 ℃ and stirred for 30 min. The blank sample and the test sample of example 2 were tested for four-ball wear spot diameter and coefficient of friction under the following test conditions: the load is 196N, the rotating speed of the main shaft is 1200r/min, the oil temperature is 75 ℃, and the detection results are shown in table 2.
Table 2 four ball machine test scrub spot diameter, average coefficient of friction.
| Abrasion Spot diameter (mm) | Average coefficient of friction | |
| Blank sample | 0.545 | 0.072 |
| Example 2 | 0.401 | 0.044 |
In addition, the coefficient of friction at room temperature (FIG. 7) and at 100 deg.C (FIG. 8) was evaluated at room temperature (FIG. 7) and at 100 deg.C (FIG. 8), respectively, under a load of 160N, at a frequency of 2Hz of reciprocating vibration, at a stroke of 10mm, and the topography of the wear surface was observed with a three-dimensional profilometer (FIGS. 9 and 10).
Example 3
The synthesis and antifriction performance of N, N' -triethylene tetramine. The reaction equation is shown in FIG. 11.
The specific reaction process is as follows:
10.0g of triethylene tetramine and 27.6g of triethylamine are dissolved in 200mL of dichloromethane, 33.6g of octanoyl chloride is dropwise added in an ice bath, the ice bath is removed after the dropwise addition, and the reaction is carried out for 12 hours at room temperature. Adding 200ml of water into a reaction bottle, separating out an organic phase, washing the organic phase with 100ml of water for three times, drying the organic phase with anhydrous sodium sulfate, evaporating the solvent under reduced pressure to obtain a crude product, recrystallizing the crude product with dichloromethane and petroleum ether to obtain 25g N, N '-octylamide derivatives of triethylene tetramine, dissolving 5.0g of the octylamide derivatives in 150ml of anhydrous tetrahydrofuran, adding 1.5g of lithium aluminum hydride in batches under ice bath, heating to reflux under the protection of nitrogen, continuing to react for 48 hours, adding 6ml of water into the reaction solution when the reaction solution is at room temperature, stirring until bubbles are completely released, adding 150ml of dichloromethane and a proper amount of anhydrous sodium sulfate, stirring to be clear, filtering, evaporating the solvent from the filtrate to obtain 4.2g of a target product N, N' -triethylene tetramine,1H-NMR(400MHz,CDCl3)δ2.64(t,4H),2.59(t,4H),2.55(t,4H),2.40(t,2H),1.47(m,4H),1.42(t,2H),1.27(m,30H),0.88(t,9H)ppm；MS(EI):m/z calcd[M+H+]C28H62N3 +:440.5；Found:440.5.
adding the prepared N, N' -triethylene tetramine into PAO4 in an addition amount of 0.5%, heating to 60 ℃, and stirring for 30 min. The blank sample and the test sample of example 2 were tested for four-ball wear spot diameter and coefficient of friction under the following test conditions: the load is 196N, the rotating speed of the main shaft is 1200r/min, the oil temperature is 75 ℃, and the detection results are shown in table 3.
Table 3 four ball machine test scrub spot diameter, average coefficient of friction.
| Abrasion Spot diameter (mm) | Average coefficient of friction | |
| Blank sample | 0.545 | 0.072 |
| Example 3 | 0.456 | 0.061 |
In addition, the coefficient of friction at room temperature (FIG. 12) and at 100 deg.C (FIG. 13), the load was 160N, the frequency of reciprocal vibration was 2Hz, and the stroke was 10mm, respectively, were evaluated on a TE77 friction tester, and the topography of the wear surface was observed with a three-dimensional profiler (FIGS. 14 and 15).
While the invention has been described in further detail with reference to specific preferred embodiments thereof, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (7)
1. The sulfur-phosphorus-free organic friction modifier is characterized in that the friction modifier is an amine compound, and the amine compound comprises any one of the following structural formulas I-VIII:
wherein R in the structural formula is selected from hydrogen atom or C8、C10、C12、C18Any of the linear alkyl groups of (1).
2. The sulfur-phosphorus-free organic friction modifier according to claim 1, wherein the friction modifier is added in an amount of 0.2 to 3% by weight based on the base oil.
3. The sulfur-phosphorus-free organic friction modifier according to claim 2, wherein the friction modifier is added in an amount of 0.5 to 1.5% by weight based on the weight of the base oil.
4. A sulfur-phosphorus-free organic friction modifier according to claim 2 or claim 3, wherein the base oil is a low viscosity PAO or a synthetic ester or a mixture of both.
5. The preparation method of the sulfur-phosphorus-free organic friction modifier according to claim 1, wherein the friction modifier is an amine compound obtained by using organic amine as a reaction substrate, using methylene chloride as a solvent, reacting long-chain fatty acyl chloride with the organic amine to form amide under the action of triethylamine, and further reducing the amide with lithium aluminum hydride.
6. The method of claim 5, wherein the organic amine is one of diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and tris (2-aminoethyl) amine.
7. The method of claim 5, wherein the long chain fatty acid chloride is caprylyl chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911122256.9A CN111019736B (en) | 2019-11-15 | 2019-11-15 | Sulfur-phosphorus-free organic friction modifier and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911122256.9A CN111019736B (en) | 2019-11-15 | 2019-11-15 | Sulfur-phosphorus-free organic friction modifier and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111019736A CN111019736A (en) | 2020-04-17 |
| CN111019736B true CN111019736B (en) | 2022-04-15 |
Family
ID=70200261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911122256.9A Active CN111019736B (en) | 2019-11-15 | 2019-11-15 | Sulfur-phosphorus-free organic friction modifier and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111019736B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111454761B (en) * | 2020-04-23 | 2022-02-08 | 中国科学院上海高等研究院 | Organic liquid crystal friction modifier with alkyl terminal chain and preparation method thereof |
| CN115246797B (en) * | 2021-04-27 | 2023-07-21 | 中国科学院上海高等研究院 | Azacrown ether compound, and preparation method and application thereof |
| JP2024069163A (en) * | 2022-11-09 | 2024-05-21 | ダイキン工業株式会社 | Repellent agent |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4549885A (en) * | 1984-10-30 | 1985-10-29 | Ethyl Corporation | Fuel compositions |
| CN101343591A (en) * | 2007-06-29 | 2009-01-14 | 英菲诺姆国际有限公司 | Lubricating oils having improved friction stability |
| JP2011001406A (en) * | 2009-06-16 | 2011-01-06 | Chevron Japan Ltd | Lubricating oil composition |
| CN104232244A (en) * | 2013-06-07 | 2014-12-24 | 中国石油化工股份有限公司 | Application of imidazole ionic liquid in lubricating oil additive |
| CN105779085A (en) * | 2016-02-26 | 2016-07-20 | 北京雅士科莱恩石油化工有限公司 | Diesel oil clearing agent containing friction modifier and saving fuel oil and preparing method thereof |
-
2019
- 2019-11-15 CN CN201911122256.9A patent/CN111019736B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4549885A (en) * | 1984-10-30 | 1985-10-29 | Ethyl Corporation | Fuel compositions |
| CN101343591A (en) * | 2007-06-29 | 2009-01-14 | 英菲诺姆国际有限公司 | Lubricating oils having improved friction stability |
| JP2011001406A (en) * | 2009-06-16 | 2011-01-06 | Chevron Japan Ltd | Lubricating oil composition |
| CN104232244A (en) * | 2013-06-07 | 2014-12-24 | 中国石油化工股份有限公司 | Application of imidazole ionic liquid in lubricating oil additive |
| CN105779085A (en) * | 2016-02-26 | 2016-07-20 | 北京雅士科莱恩石油化工有限公司 | Diesel oil clearing agent containing friction modifier and saving fuel oil and preparing method thereof |
Non-Patent Citations (2)
| Title |
|---|
| Alkyl-Cyclens as Effective Sulfur- and Phosphorus-Free Friction Modifiers for Boundary Lubrication;Michael Desanker;《ACS Applied Materials & Interfaces》;20170221;9118-9125 * |
| Synthesis, Surface-Active Properties, and Emulsification;Manar El-Sayed Abdul-Raouf;《J Surfact Deterg》;20100804;185-193 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111019736A (en) | 2020-04-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111019736B (en) | Sulfur-phosphorus-free organic friction modifier and preparation method thereof | |
| Yu et al. | Novel N, P-containing oil-soluble ionic liquids with excellent tribological and anti-corrosion performance | |
| EP2688992B1 (en) | Ionic-liquid-based lubricants and lubrication additives comprising ions | |
| CN110845417A (en) | Amino acid ionic liquid water-based additive and preparation method and application thereof | |
| JP2010530447A (en) | Use of ionic liquids to improve the properties of lubricant compositions | |
| Zhu et al. | Investigation on three oil-miscible ionic liquids as antiwear additives for polyol esters at elevated temperature | |
| CN110862356B (en) | Benzotriazole functionalized quaternary ammonium salt ionic liquid and preparation method and application thereof | |
| CN109609244B (en) | Extreme pressure anti-wear agent of oil-soluble boric acid ester modified graphene oxide and preparation method thereof | |
| Khatri et al. | Halogen-free ammonium–organoborate ionic liquids as lubricating additives: the effect of alkyl chain lengths on the tribological performance | |
| CN112321624A (en) | Chelate boron ionic liquid containing thiadiazole structure and application thereof | |
| CN110845430B (en) | Benzotriazole functionalized quaternary ammonium salt and preparation method and application thereof | |
| Zhu et al. | A comprehensive study of amino acids based ionic liquids as green lubricants for various contacts | |
| CN103980981B (en) | A kind of anti-friction agent of nitrogenous sulfur molybdenum phosphate and preparation method thereof | |
| CN112062729A (en) | Functionalized quaternary ammonium salt ionic liquid and preparation method and application thereof | |
| CN107827926B (en) | Micromolecule functionalized surfactant and preparation method and application thereof | |
| CN111378516B (en) | Organic friction modifier with different isomeric alkyl end chains and preparation method thereof | |
| CN111321027B (en) | Environment-friendly lubricant for water-soluble metal working fluid and synthetic method thereof | |
| CN107541318B (en) | Wear-resistant anti-rust oil containing graphene and preparation method thereof | |
| Su et al. | Synthesis and investigation of phosphorus-free ionic liquids as multifunctional lubricating additives | |
| CN104893787B (en) | A kind of boron-containing additive and its preparation method and application of high hydrolytic stability | |
| Ding et al. | Tribological behavior of plant oil-based extreme pressure lubricant additive in water-ethylene glycol liquid | |
| CN111979011A (en) | Nitrogen-containing non-sulfur-phosphorus organic lubricating oil antiwear agent and preparation method and application thereof | |
| CN115246797B (en) | Azacrown ether compound, and preparation method and application thereof | |
| US2516844A (en) | Lubricant composition | |
| CN110951518B (en) | Organic friction modifier and method for reducing friction coefficient of low-viscosity lubricating oil |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |