CN115975695B - Lubricating oil composition capable of realizing wide Wen Yuchao sliding - Google Patents
Lubricating oil composition capable of realizing wide Wen Yuchao sliding Download PDFInfo
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- CN115975695B CN115975695B CN202211671021.7A CN202211671021A CN115975695B CN 115975695 B CN115975695 B CN 115975695B CN 202211671021 A CN202211671021 A CN 202211671021A CN 115975695 B CN115975695 B CN 115975695B
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- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 45
- 238000010586 diagram Methods 0.000 claims description 6
- 238000005461 lubrication Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 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 6
- 230000001105 regulatory effect Effects 0.000 abstract description 4
- 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
- 230000005496 eutectics Effects 0.000 abstract description 2
- 229910000831 Steel Inorganic materials 0.000 description 19
- 239000010959 steel Substances 0.000 description 19
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 230000009257 reactivity Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000002085 enols Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000463 material Substances 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
- 238000005299 abrasion 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
- 230000001050 lubricating effect Effects 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
- 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process 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
- 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
- 230000000630 rising effect Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
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- Lubricants (AREA)
Abstract
The invention discloses a beta-diketone lubricating oil composition, which is designed into a multi-component beta-diketone composition which can be mutually dissolved in any proportion by regulating the number and the position of benzene rings and the length of side chains in a central structure on the premise of retaining core functional groups of diketones, and can realize ultra-slip in a wide temperature range of-40 to +150 ℃; the invention changes the original beta-diketone lubricating oil from a single substance into a binary or ternary composition, utilizes the mutual interference of a plurality of components on crystallization to form a mixture with a low eutectic point, and ensures the fluidity of the lubricating oil at low temperature; the tautomer ratio of the components is regulated and controlled by the number of benzene rings and the length of side chains; when the working temperature is lower, the proportion of the high-reactivity components is increased, so that the friction chemical reaction is ensured; when the working temperature is higher, the proportion of the low-reactivity components is increased, so that the self-stopping of the tribochemical reaction is ensured; the molecular structure and the proportion of the components are changed so as to be suitable for 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 Wen Yuchao sliding.
Background
The friction and wear between the parts of the structure of the mechanical device and the components of the unit can cause considerable energy losses, reducing the service life of the device and even causing serious mechanical accidents. Therefore, improving the abrasion condition among parts and reducing the friction coefficient as much as possible become necessary means for realizing energy conservation and emission reduction and improving the running efficiency of equipment.
The ultra-slip technology is one of the important means for solving the friction and abrasion of mechanical equipment at present. Super-slip refers to a lubrication state in which the friction coefficient of the two friction pair surfaces is less than 0.01. Tribology Letters 2010,37 (2), 343-352, langmuir 2013,29 (17), 5207-5213 et al academic papers report a novel synthetic lubricating material, β -diketone. Taking EPND (1- (4-ethylphenyl) nonane-1, 3-dione) as an example, which is the most widely studied at present, the compound has two tautomers of ketone type and enol type, and the two isomers simultaneously exist and jointly act to realize super-slip. The diketone functional group in the ketone formula can be subjected to tribochemical reaction with the steel surface under the action of frictional heat (namely, the flash temperature when the solid surface microprotrusions are contacted) to generate chelate which is soluble in beta-diketone, and the solid contact is gradually eliminated, so that the mechanical friction (namely, external friction) between the solid surfaces is converted into collision and entanglement (namely, internal friction) between lubricating oil beta-diketone molecules. On the other hand, the six-membered ring formed by the intramolecular hydrogen bond in the enol form and the ortho benzene ring can form a rod-shaped structure similar to biphenyl liquid crystal, have higher intermolecular acting force, and can form molecular orientation under the shearing action, thereby reducing the self viscous resistance of the lubricating oil beta-diketone. Finally, under the combined action of the two aspects, the beta-diketone can realize the low friction performance with super-slip magnitude.
Although the beta-diketone ultra-smooth material has good application prospect, the temperature range in which the lubricating performance can be maintained is a factor to be considered in practical industrial application. Generally, lubricating oils are required to be usable in a temperature range of-20 to +120 ℃ and even wider. However, the currently investigated β -diketones, due to their own structural characteristics, operate in a range of only room temperature to 100 ℃.
For the low-temperature working condition, the beta-diketone has a molecular structure similar to liquid crystal, so that the intermolecular interaction force is strong and crystallization is easy to occur. For example, the most widely studied β -diketone EPND (1- (4-ethylphenyl) nonane-1, 3-dione) solidifies at about 0.6 ℃ and loses fluidity as a lubricating oil.
For high temperature conditions, the chemical reactivity of the beta-diketone with the metal increases. When the ambient temperature is too high, even if the microprotrusion contact is completely eliminated (i.e., the flash temperature disappears) after the ultra-slip is achieved, the chemical reaction continues until the beta-diketone reaction is depleted, resulting in an ultra-slip failure or even a lubrication failure.
In summary, how to achieve the ultra-slip performance in a wider temperature range is a technical problem that β -diketones are pushed to be solved in the actual industrial application.
Disclosure of Invention
The invention aims to provide a beta-diketone lubricating oil composition, which is designed into a multicomponent beta-diketone composition which can be mutually dissolved in any proportion by regulating the number and the position of benzene rings and the length of side chains in a central structure on the premise of retaining core functional groups of diketones and realizes ultra-slip in a wide temperature range of-40 to +150 ℃.
In order to achieve the above purpose, the following technical scheme is adopted:
A lubricating oil composition capable of realizing a wide Wen Yuchao slip is composed 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, Y is an integer, 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, and X+Y is more than or equal to 1 and less than or equal to 2; r 1 is C mH2m+1、CmH2mOCH3 or C mH2mOOCH3,R2 is C nH2n+1、CnH2nOCH3 or C nH2nOOCH3, 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 two 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 a wide Wen Yuchao slip is prepared from two beta-diketone lubricating oil components in a mass ratio of 1:1, the composition is as follows; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
Wherein x=1, y=1; r 1 is C mH2m+1,R2 or C nH2n+1; 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 low eutectic point is formed by utilizing the mutual interference of a plurality of components on crystallization, so that the fluidity of the lubricating oil at a low temperature is ensured.
The tautomeric proportion (i.e., chemical reactivity) of the components is regulated by the number of benzene rings and the length of the side chains. The more benzene rings or the longer side chains are, the higher the enol ratio is, and the lower the chemical reactivity is; the fewer benzene rings or the shorter the side chains, the higher the ketone type ratio and the higher the chemical reactivity. When the working temperature is lower, the proportion of the high-reactivity components is increased, so that the friction chemical reaction is ensured; when the working temperature is higher, the proportion of the low-reactivity component is increased, and the self-stopping of the tribochemical reaction is ensured. The molecular structure and the proportion of the components are changed so as to be suitable for different temperature working conditions.
Drawings
Fig. 1: melting points of the A-component, B-component and compositions thereof in example 1.
Fig. 2: low temperature friction test of the beta-diketone composition obtained in example 1.
Fig. 3: high temperature rub test of the A, B and compositions thereof in example 1.
Detailed Description
The following examples further illustrate the technical aspects of the present invention, but are not intended to limit the scope of the present invention.
The specific embodiment provides a lubricating oil composition capable of realizing wide Wen Yuchao sliding, 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, Y is an integer, 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, and X+Y is more than or equal to 1 and less than or equal to 2; r 1 is C mH2m+1、CmH2mOCH3 or C mH2mOOCH3,R2 is C nH2n+1、CnH2nOCH3 or C nH2nOOCH3, 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 two 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 two beta-diketone lubricating oil components are mixed according to the mass ratio of 1:1, the composition is as follows; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
Wherein x=1, y=1; r 1 is C mH2m+1,R2 or C nH2n+1; 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. The mass ratio of the a component (x=1, y=0, r 1、R2 are C 3H7) and the B component (x=2, y=0, r 1、R2 are C 3H7) is 1:1.
The molecular formula of the A component is as follows:
from 4-n-propyl acetophenone and ethyl butyrate by a claisen condensation reaction.
The molecular formula of the B component is as follows:
from 1- [4- (4-propylphenyl) phenyl ] ethanone and ethyl butyrate by a claisen condensation reaction.
The melting point of the composition is tested by a differential scanning calorimeter, the test atmosphere is nitrogen, the test temperature ranges from minus 60 ℃ to +60 ℃, and the temperature rising rate is 5 ℃ for 5min. As shown in FIG. 1, the melting point of the composition is lower, about-29℃compared to the single component.
The friction performance of the composition was tested by steel ball-steel disc rotational friction test, and the load, sliding speed, and test time were set to 16N, 300mm5s, and 3h, respectively. At-18 ℃, both the A component and the B component are solid and can not be used as lubricating oil for testing, and the friction performance of the two compositions is shown in figure 2, and the ultra-slip is realized after a running-in period of 1.25 hours.
The tribological properties of the A-component, B-component and combinations thereof are shown in FIG. 3 at 122 ℃, and although all three can achieve ultra-slip, the tribochemical reaction of the A-component cannot be stopped and the ultra-slip fails after 0.5 hours. Thus, the beta-diketone lubricating oil composition can realize stable super-slip performance at the temperature of-18 to +122 ℃.
Example 2
This embodiment differs from case 1 in that the mass ratio of the a component and the B component in the beta-diketone lubricating oil composition is 3:2, other steps, reagents and parameters were the same as in example 1.
The melting point of the composition was confirmed to be-34 ℃ by differential scanning calorimeter testing. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-slip performance at the temperature of-24 to +112 ℃.
Example 3
This example differs from case 1 in that in the a-component of the beta-diketone lubricating oil composition, x=1, y=0, r 1 is C 2H5,R2 and C 4H9, and other steps, reagents and parameters are the same as in example 1.
The melting point of the composition was confirmed by differential scanning calorimeter testing and was-33 ℃. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-slip performance at the temperature of-23 to +120 ℃.
Example 4
This example differs from case 1 in that in the B component of the beta-diketone lubricating oil composition, x=1, y=1, r 1 is C 6H13,R2 and C 6H13, and other steps, reagents and parameters are the same as in example 1.
The melting point of the composition was confirmed by differential scanning calorimeter testing to be-22 ℃. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-slip performance at the temperature of-11 to +141 ℃.
Example 6
The present embodiment differs from case 1 in that the β -diketone lubricating oil composition is composed of A, B, C three components, wherein x=1, y=0, r 1 is C 2H5,R2 and C 2H5, and the mass ratio of the three components is 1:1:3, other steps, reagents and parameters were the same as in example 1.
The melting point of the composition was confirmed by differential scanning calorimeter testing to be-51 ℃. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-slip performance at the temperature of minus 35 to +108 ℃.
Example 7
This example differs from case 1 in that in the B component of the beta-diketone lubricating oil composition, x=1, y=1, r 1 is C 4H8OOCH3,R2 and C 4H8OOCH3, and other steps, reagents and parameters are the same as in example 1.
The melting point of the composition was confirmed by differential scanning calorimeter testing to be-30 ℃. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-slip performance at the temperature of minus 15 to plus 130 ℃.
Example 8
This example differs from case 1 in that in the B component of the beta-diketone lubricating oil composition, x=1, y=1, r 1 is C 6H12OCH3,R2 and C 6H12OCH3, and other steps, reagents and parameters are the same as in example 1.
The melting point of the composition was confirmed by differential scanning calorimeter testing and was-25 ℃. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-slip performance at the temperature of-19 to +125 ℃.
Example 9
This example differs from case 1 in that in the B component of the beta-diketone lubricating oil composition, x=1, y=1, r 1 is C 3H6OCH3,R2 and C 3H6OCH3, and other steps, reagents and parameters are the same as in example 1.
The melting point of the composition was confirmed by differential scanning calorimeter testing to be-29 ℃. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-slip performance at the temperature of-20 to +120 ℃.
Example 10
In this embodiment, the components x=1, y=1, and r 1、R2 are C 3H7, the components x=1, y=1, and r 1 are C 7H15,R2 and C 7H13, and the other steps, reagents, and parameters are the same as those of embodiment 1.
The melting point of the composition was confirmed by differential scanning calorimeter testing to be-55 ℃. The friction performance of the composition is proved by a steel ball-steel disc rotating friction test, and the composition can realize stable super-slip performance at the temperature of-40 to +140 ℃.
Claims (2)
1. A lubricating oil composition capable of realizing a wide Wen Yuchao slip is characterized by comprising two or three beta-diketone lubricating oil components, wherein the mass ratio of any two beta-diketone lubricating oil components is not more than ten; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
Wherein X, Y is an integer, 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, and X+Y is more than or equal to 1 and less than or equal to 2; r 1 is C mH2m+1、CmH2mOCH3 or C mH2mOOCH3,R2 is C nH2n+1、CnH2nOCH3 or C nH2nOOCH3, 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 n is an integer; the lubricating oil composition achieves ultra-lubrication over a wide temperature range of up to-40 ℃ and up to 141 ℃.
2. A lubricating oil composition capable of realizing a wide Wen Yuchao slip, characterized by comprising two beta-diketone lubricating oil components in a mass ratio of 1:1, the composition is as follows; the molecular structure diagram of the single-component beta-diketone lubricating oil is as follows:
Wherein x=1, y=1; r 1 is C mH2m+1,R2 or C nH2n+1; 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; the lubricating oil composition achieves ultra-lubrication over a wide temperature range of up to-40 ℃ and up to 140 ℃.
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Citations (4)
| 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 |
| CN111909754A (en) * | 2020-08-26 | 2020-11-10 | 武汉理工大学 | Composite lubricating composition and lubricating material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070116672A (en) * | 2005-03-30 | 2007-12-10 | 후지필름 가부시키가이샤 | Lubricant composition |
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Patent Citations (4)
| 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 |
| CN111909754A (en) * | 2020-08-26 | 2020-11-10 | 武汉理工大学 | Composite lubricating composition and lubricating material |
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