CN115975695A - Lubricating oil composition capable of realizing wide-temperature-range super-lubricity - Google Patents
Lubricating oil composition capable of realizing wide-temperature-range super-lubricity Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 44
- 238000010586 diagram Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 5
- 238000002425 crystallisation Methods 0.000 abstract description 3
- 230000008025 crystallization Effects 0.000 abstract description 3
- 125000005594 diketone group Chemical group 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract description 3
- 230000001276 controlling effect Effects 0.000 abstract description 2
- 239000000374 eutectic mixture Substances 0.000 abstract 1
- 229910000831 Steel Inorganic materials 0.000 description 19
- 239000010959 steel Substances 0.000 description 19
- 230000008018 melting Effects 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 4
- 150000002085 enols Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- LCQBWQKQSFBVSN-UHFFFAOYSA-N 1-(4-ethylphenyl)nonane-1,3-dione Chemical compound CCCCCCC(=O)CC(=O)C1=CC=C(CC)C=C1 LCQBWQKQSFBVSN-UHFFFAOYSA-N 0.000 description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 2
- 238000003512 Claisen condensation reaction Methods 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- ZNBVIYMIVFKTIW-UHFFFAOYSA-N 1-(4-propylphenyl)ethanone Chemical compound CCCC1=CC=C(C(C)=O)C=C1 ZNBVIYMIVFKTIW-UHFFFAOYSA-N 0.000 description 1
- LMOXYMSDLCVONT-UHFFFAOYSA-N 1-[4-(4-propylphenyl)phenyl]ethanone Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C(C)=O)C=C1 LMOXYMSDLCVONT-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
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Abstract
The invention discloses a beta-diketone lubricating oil composition, which designs a multi-component beta-diketone composition capable of being mutually dissolved in any proportion by regulating and controlling the number and position of benzene rings in a central structure and the length of a side chain on the premise of keeping a diketone core functional group, and realizes ultra-smoothness in a wide temperature range of-40 to +150 ℃; the invention changes the original beta-diketone lubricating oil from a single substance to a binary or ternary composition, and utilizes mutual interference of a plurality of components on crystallization to form a eutectic mixture, thereby ensuring the fluidity of the lubricating oil at low temperature; the proportion of the tautomers of the components is regulated and controlled by the number of benzene rings and the length of a side chain; when the working temperature is lower, the proportion of the high-reactivity component is increased, and the tribochemical reaction is ensured to be carried out; when the working temperature is higher, the proportion of the low-reaction active component is increased, and the self-stop of the tribochemical reaction is ensured; the molecular structure and proportion of the components are changed to adapt the components to different temperature working conditions.
Description
Technical Field
The invention belongs to the technical field of materials, and particularly relates to a lubricating oil composition capable of realizing wide-temperature-range super-lubricity.
Background
The friction and abrasion between each part structure of the mechanical equipment and parts in the unit can cause a great deal of energy loss, reduce the service life of the equipment and even cause serious mechanical accidents. Therefore, improving the wear conditions among the parts and reducing the friction coefficient as much as possible become necessary means for realizing energy conservation and emission reduction and improving the operation efficiency of the equipment.
The ultra-slip technology is one of the important means for solving the friction and wear of mechanical equipment at present. Ultra-smooth refers to a lubricated condition where the coefficient of friction of the two friction pair surfaces is less than 0.01. Academic papers such as Tribology Letters 2010,37 (2), 343-352, langmuir 2013,29 (17), 5207-5213 report a novel synthetic lubricant beta-diketone. Taking EPND (1- (4-ethylphenyl) nonane-1, 3-dione) which is the most widely researched at present as an example, the EPND has two tautomers of a ketone type and an enol type, and the two tautomers exist at the same time and act together to realize super-smoothness. The diketone functional group in the ketone formula can generate a tribochemical reaction with the steel surface under the action of frictional heat (namely the flash temperature when the microprotrusions on the solid surface are contacted), generate a chelate which can be dissolved in the beta-diketone, gradually eliminate the solid contact, and convert the mechanical friction (namely the external friction) between the solid surfaces into the collision and winding (namely the internal friction) between the lubricating oil beta-diketone molecules. On the other hand, a six-membered ring formed by intramolecular hydrogen bonds in the enol form and an ortho-position benzene ring can form a rod-shaped structure similar to biphenyl liquid crystal, have high intermolecular force and can form molecular orientation under the shearing action, so that the viscosity resistance of the lubricating oil beta-diketone is reduced. Finally, under the combined action of the two aspects, the beta-diketone can realize low friction performance of ultra-smooth magnitude.
Although β -diketone ultra-slip materials have promising application prospects, the temperature range in which lubricity can be maintained is a factor that must be considered in practical industrial applications. Generally, lubricating oils are required to be usable in a temperature range of-20 to +120 ℃ or even wider. However, the currently studied beta-diketones, due to their own structural properties, have only ultra-smooth operating conditions ranging from room temperature to 100 ℃.
For low-temperature working conditions, beta-diketone has a molecular structure similar to liquid crystal, and the intermolecular interaction force is strong, so that crystallization is easy to occur. For example, the most widely studied beta-diketone, EPND (1- (4-ethylphenyl) nonane-1, 3-dione), solidifies at about 0.6 ℃ and loses its fluidity as a lubricant.
The chemical reactivity of the beta-diketone with the metal is increased under the high-temperature working condition. When the ambient temperature is too high, the chemical reaction continues until the beta-diketone reaction is exhausted, causing an ultra-slip failure or even a lubrication failure, even if the microprotrusion contact is completely eliminated after the ultra-slip is achieved (i.e., the flash temperature disappears).
In conclusion, how to realize the ultra-lubricity performance in a wider temperature range is a technical problem which needs to be solved urgently when the beta-diketone is pushed to practical industrial application.
Disclosure of Invention
The invention aims to provide a beta-diketone lubricating oil composition, which designs a multi-component beta-diketone composition capable of being mutually dissolved in any proportion by regulating and controlling the number and position of benzene rings in a central structure and the length of side chains on the premise of keeping a diketone core functional group, and realizes ultra-smoothness in a wide temperature range of-40 to +150 ℃.
In order to achieve the purpose, the technical scheme is as follows:
a can realize the ultra-slippery lubricating oil composition of wide temperature range, it is made up of two or three kinds of beta-diketone lubricating oil component according to the arbitrary proportion; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
wherein X and Y are integers, X is more than or equal to 0 and less than or equal to 2, Y is more than or equal to 0 and less than or equal to 2, X + Y is more than or equal to 1 and less than or equal to 2; r is 1 Is C m H 2m+1 、C m H 2m OCH 3 Or C m H 2m OOCH 3 ，R 2 Is C n H 2n+1 、C n H 2n OCH 3 Or C n H 2n OOCH 3 Wherein m is more than or equal to 1 and less than or equal to 10, n is more than or equal to 1 and less than or equal to 10, and the m and the n are integers.
According to the scheme, the mass ratio of any two beta-diketone lubricating oil components is not more than ten times.
A lubricating oil composition capable of realizing wide-temperature-range super-lubricity is prepared from two beta-diketone lubricating oil components in a mass ratio of 1:1, preparing a composition; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
wherein, X =1, y =1; r 1 Is C m H 2m+1 ，R 2 Is C n H 2n+1 (ii) a M is more than or equal to 3 and less than or equal to 8, n is more than or equal to 3 and less than or equal to 8, and m and n are integers.
Compared with the prior art, the invention has the following beneficial effects:
the original beta-diketone lubricating oil is changed into a binary or ternary composition from a single substance, and a mixture with a eutectic point is formed by utilizing mutual interference of a plurality of components on crystallization, so that the fluidity of the lubricating oil at low temperature is ensured.
The ratio of the tautomers (i.e., chemical reactivity) of the constituent elements is controlled by the number of benzene rings and the length of side chains. The more benzene rings or the longer side chain, the higher the enol form ratio and the lower the chemical reaction activity; the fewer benzene rings or the shorter side chains, the higher the ketone formula ratio and the higher the chemical reactivity. When the working temperature is lower, the proportion of the high-reactivity component is increased, and the tribochemical reaction is ensured to be carried out; when the working temperature is higher, the proportion of the low-reaction active component is increased, and the self-stop of the tribochemical reaction is ensured. The molecular structure and proportion of the components are changed to adapt the components to different temperature working conditions.
Drawings
FIG. 1: melting points of the A component, the B component and the composition thereof in example 1.
FIG. 2: example 1 low temperature friction testing of the resulting beta-diketone composition.
FIG. 3: high temperature friction testing of component A, component B and combinations thereof in example 1.
Detailed Description
The following examples further illustrate the technical solutions of the present invention, but should not be construed as limiting the scope of the present invention.
The specific embodiment provides a lubricating oil composition capable of realizing wide-temperature-range super-lubricity, which consists of two or three beta-diketone lubricating oil components in any proportion; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
wherein X and Y are integers, X is more than or equal to 0 and less than or equal to 2, Y is more than or equal to 0 and less than or equal to 2, X + Y is more than or equal to 1 and less than or equal to 2; r 1 Is C m H 2m+1 、C m H 2m OCH 3 Or C m H 2m OOCH 3 ，R 2 Is C n H 2n+1 、C n H 2n OCH 3 Or C n H 2n OOCH 3 Wherein m is more than or equal to 1 and less than or equal to 10, n is more than or equal to 1 and less than or equal to 10, and the m and the n are integers.
Optimally, the mass ratio of any two beta-diketone lubricating oil components is not more than ten times.
The more optimized scheme is that the lubricating oil composition comprises two beta-diketone lubricating oil components in a mass ratio of 1:1, preparing a composition; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
wherein, X =1, y =1; r 1 Is C m H 2m+1 ，R 2 Is C n H 2n+1 (ii) a M is more than or equal to 3 and less than or equal to 8, n is more than or equal to 3 and less than or equal to 8, and m and n are integers.
Example 1
The beta-diketone lubricating oil composition consists of two components A and B. Component A (X =1, Y =0, R) 1 、R 2 Are all C 3 H 7 ) And B component (X =2, Y =0 1 、R 2 Are all C 3 H 7 ) The mass ratio of (1): 1.
the molecular formula of the component A is as follows:
is prepared from 4-n-propyl acetophenone and ethyl butyrate through claisen condensation reaction.
The molecular formula of the component B is as follows:
prepared by the claisen condensation reaction of 1- [4- (4-propylphenyl) phenyl ] ethanone and ethyl butyrate.
The melting point of the composition is tested by a differential scanning calorimeter, the testing atmosphere is nitrogen, the testing temperature range is-60 to +60 ℃, and the heating rate is 5 ℃ for 5min. As shown in fig. 1, the melting point of the composition is lower, about-29 c, than that of the individual components.
The friction performance of the composition is tested by a steel ball-steel disc rotating friction test, and the load, the sliding speed and the test time are respectively set to be 16N, 300mm5s and 3h. At-18 ℃, the A component and the B component are both solid and cannot be used as lubricating oil for testing, and the friction performance of the composition of the A component and the B component is shown in figure 2, and after 1.25 hours of running-in, the ultra-smooth is realized.
At 122 ℃, the friction performance of the component A, the component B and the composition thereof is shown in figure 3, although all the components can realize the ultra-sliding, the friction chemical reaction of the component A cannot be stopped, and the ultra-sliding fails after 0.5 hour. It can be seen that the beta-diketone lubricating oil composition can realize stable super-lubricity at-18 to +122 ℃.
Example 2
The difference between the present embodiment and embodiment 1 is that the mass ratio of the component A to the component B in the beta-diketone lubricating oil composition is 3:2, other steps, reagents and parameters were the same as those in example 1.
The melting point of the composition was confirmed to be-34 ℃ by differential scanning calorimetry. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-lubricity at the temperature of between 24 ℃ below zero and 112 ℃.
Example 3
Unlike case 1, in this embodiment, X =1, y =0, r in the a component of the β -diketone lubricating oil composition 1 Is C 2 H 5 ,R 2 Is C 4 H 9 Other steps, reagents and parameters were the same as in example 1.
Melting point of the composition the melting point of the composition was-33 ℃ as confirmed by differential scanning calorimetry. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-lubricity at the temperature of between 23 ℃ below zero and 120 ℃.
Example 4
The difference between this embodiment and case 1 is that X =1,Y =1,R in B component in beta-diketone lubricating oil composition 1 Is C 6 H 13 ,R 2 Is C 6 H 13 Other steps, reagents and parameters were the same as in example 1.
Melting point of the composition the melting point of the composition was-22 ℃ as confirmed by differential scanning calorimetry. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-lubricity at the temperature of between 11 ℃ below zero and 141 ℃.
Example 6
The difference between the embodiment and the embodiment 1 is that the beta-diketone lubricating oil composition consists of three components A, B and C, wherein X =1, Y =0, R in the component C 1 Is C 2 H 5 ,R 2 Is C 2 H 5 The mass ratio of the A component to the B component to the C component is 1:1:3, other steps, reagents and parameters were the same as those in example 1.
Melting point of the composition the melting point of the composition was-51 ℃ as confirmed by differential scanning calorimetry testing. The friction performance of the composition is verified by a steel ball-steel disc rotating friction test, and the composition can realize stable super-lubricity at the temperature of between 35 ℃ below zero and 108 ℃.
Example 7
In contrast to example 1, the present example is a beta-diketone lubricating oil compositionIn the component B, X =1,Y =1,R 1 Is C 4 H 8 OOCH 3 ,R 2 Is C 4 H 8 OOCH 3 Other steps, reagents and parameters were the same as those in example 1.
Melting point of the composition the melting point of the composition was-30 ℃ as confirmed by differential scanning calorimetry. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-lubricity at the temperature of between 15 ℃ below zero and 130 ℃.
Example 8
The difference between this embodiment and case 1 is that X =1,Y =1,R in B component in beta-diketone lubricating oil composition 1 Is C 6 H 12 OCH 3 ,R 2 Is C 6 H 12 OCH 3 Other steps, reagents and parameters were the same as those in example 1.
Melting point of the composition the melting point of the composition was-25 ℃ as confirmed by differential scanning calorimetry. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-lubricity at the temperature of-19 to +125 ℃.
Example 9
The difference between this embodiment and case 1 is that X =1,Y =1,R in B component in beta-diketone lubricating oil composition 1 Is C 3 H 6 OCH 3 ,R 2 Is C 3 H 6 OCH 3 Other steps, reagents and parameters were the same as those in example 1.
Melting point of the composition the melting point of the composition was-29 ℃ as confirmed by differential scanning calorimetry. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-lubricity at the temperature of between 20 ℃ below zero and 120 ℃.
Example 10
In the component A of the embodiment, X =1,Y =1,R 1 、R 2 Are all C 3 H 7 And X =1,Y =1,R in the component B 1 Is C 7 H 15 ,R 2 Is C 7 H 13 Other steps, reagents and parameters were the same as those in example 1.
Melting point of the composition the melting point of the composition was-55 ℃ as confirmed by differential scanning calorimetry. The friction performance of the composition is verified by a steel ball-steel disc rotating friction test, and the composition can realize stable super-lubricity at the temperature of between 40 ℃ below zero and 140 ℃.
Claims (3)
1. A lubricating oil composition capable of realizing wide-temperature-range super-lubricity is characterized by consisting of two or three beta-diketone lubricating oil components in any proportion; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
wherein X and Y are integers, X is more than or equal to 0 and less than or equal to 2, Y is more than or equal to 0 and less than or equal to 2, X + Y is more than or equal to 1 and less than or equal to 2; r 1 Is C m H 2m+1 、C m H 2m OCH 3 Or C m H 2m OOCH 3 ，R 2 Is C n H 2n+1 、C n H 2n OCH 3 Or C n H 2n OOCH 3 Wherein m is more than or equal to 1 and less than or equal to 10, n is more than or equal to 1 and less than or equal to 10, and the m and the n are integers.
2. The wide temperature range ultra-smooth achievable lubricating oil composition of claim 1, wherein the mass ratio of any two β -diketone lubricating oil components is not more than ten times.
3. A lubricating oil composition capable of realizing wide-temperature-range super-lubricity is characterized in that two beta-diketone lubricating oil components are mixed according to the mass ratio of 1:1, preparing a composition; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
wherein, X =1, y =1; r 1 Is C m H 2m+1 ，R 2 Is C n H 2n+1 (ii) a M is more than or equal to 3 and less than or equal to 8, n is more than or equal to 3 and less than or equal to 8, and m and n are integers。
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2186285A1 (en) * | 1994-05-13 | 1995-11-23 | Stanley James Brois | Carbonyl containing compounds and their derivatives as multi-functional fuel and lube additives |
| US5475145A (en) * | 1992-11-06 | 1995-12-12 | Rhone-Poulenc | β-diketones, processes for making β-diketones and use of β-diketones as stabilizers for PVC |
| JP2005264148A (en) * | 2004-01-30 | 2005-09-29 | Idemitsu Kosan Co Ltd | LUBRICATING OIL ADDITIVE COMPOSED MAINLY OF beta-DIKETONE COMPOUND |
| US20090143262A1 (en) * | 2005-03-30 | 2009-06-04 | Fujifilm Corporation | Lubricant Composition |
| CN111909754A (en) * | 2020-08-26 | 2020-11-10 | 武汉理工大学 | Composite lubricating composition and lubricating material |
-
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- 2022-12-20 CN CN202211671021.7A patent/CN115975695B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5475145A (en) * | 1992-11-06 | 1995-12-12 | Rhone-Poulenc | β-diketones, processes for making β-diketones and use of β-diketones as stabilizers for PVC |
| CA2186285A1 (en) * | 1994-05-13 | 1995-11-23 | Stanley James Brois | Carbonyl containing compounds and their derivatives as multi-functional fuel and lube additives |
| JP2005264148A (en) * | 2004-01-30 | 2005-09-29 | Idemitsu Kosan Co Ltd | LUBRICATING OIL ADDITIVE COMPOSED MAINLY OF beta-DIKETONE COMPOUND |
| US20090143262A1 (en) * | 2005-03-30 | 2009-06-04 | Fujifilm Corporation | Lubricant Composition |
| CN111909754A (en) * | 2020-08-26 | 2020-11-10 | 武汉理工大学 | Composite lubricating composition and lubricating material |
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