CN116574548B - Amide type organic friction improver, preparation method and application thereof - Google Patents
Amide type organic friction improver, preparation method and application thereof Download PDFInfo
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- CN116574548B CN116574548B CN202310517551.4A CN202310517551A CN116574548B CN 116574548 B CN116574548 B CN 116574548B CN 202310517551 A CN202310517551 A CN 202310517551A CN 116574548 B CN116574548 B CN 116574548B
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- organic friction
- friction modifier
- friction
- base oil
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- 150000001408 amides Chemical class 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 239000003607 modifier Substances 0.000 claims abstract description 43
- 239000002199 base oil Substances 0.000 claims abstract description 29
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims abstract description 11
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims abstract description 4
- 229920013639 polyalphaolefin Polymers 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 10
- 239000002184 metal Substances 0.000 abstract description 10
- 238000001179 sorption measurement Methods 0.000 abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 3
- -1 amide compound Chemical class 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 239000000446 fuel Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C10M133/22—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms containing a carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/0206—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers used as base material
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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 provides an amide type organic friction modifier, a preparation method and application thereof, wherein the structural formula is as follows: The organic friction modifier is an amide compound, diacetone acrylamide and oleylamine are used as reaction substrates, and the reaction is carried out for 24 hours at the temperature of 80 ℃ and the vacuum degree of 0.095MPa, so that the product is obtained. The nitrogen atoms and the oxygen atoms in the molecular structure of the organic friction improver have lone pair electrons, an ordered molecular adsorption film can be formed on the surface of metal, friction on the surface of a metal friction pair is reduced, and the organic friction improver has excellent antifriction performance in base oil.
Description
Technical Field
The invention relates to the technical field of lubricating oil additives, in particular to an amide type organic friction modifier, a preparation method and application thereof.
Background
At present, the combustion conversion efficiency of automobile fuel is about 38%, and 33% of energy converted into mechanical power is lost due to friction; in order to reduce fuel consumption and emissions, improving fuel economy, in addition to an effective way of improving combustion efficiency of an engine, reducing the friction coefficient of lubricating oil is considered as an effective way of improving fuel economy. Zinc dialkyldithiophosphates (ZDDP) have been used for over seventy years in engine oil formulations, but ZDDP results in exhaust emissions containing P, S and other elements, and also reduces the life of the automobile exhaust catalyst. With the continuous upgrading and development of emission regulations of various countries in the world, the requirements of increasingly strict energy conservation and emission reduction and fuel economy improvement of the automobile industry are met, and engine lubricating oil and additives are developing towards the trend of low sulfur, phosphorus and low ash; the amount of ZDDP used will then decrease gradually while still ensuring that the engine oil has stable lubricating properties, and therefore low sulfur phosphorous, ash-free organic friction modifiers (Organic Friction Modifier) have been widely studied and used. The organic friction modifier is a substance which can form a physical or chemical adsorption film on the friction surface so as to reduce the friction coefficient, improve the lubricating property and enhance the film forming capability; the friction modifier can improve the mixing and boundary lubrication of the engine and reduce friction loss, thereby achieving the purpose of energy saving.
Therefore, the development of efficient ashless organic friction modifiers that gradually reduce or replace the use of ZDDP would have significant application prospects.
Disclosure of Invention
The invention aims to provide an amide type organic friction modifier, a preparation method and application thereof, wherein the friction modifier has excellent antifriction performance in poly alpha-olefin base oil, and simultaneously has good synergistic effect when being used together with Zinc Dialkyl Dithiophosphate (ZDDP), so that the usage amount of the ZDDP in the base oil can be reduced, and a lower friction coefficient can be obtained.
The amide type organic friction modifier prepared by the invention has the advantages of simple preparation process, low preparation cost, high yield and excellent antifriction performance.
The invention is realized by the following technical scheme:
an amide-type organic friction modifier having the structure shown below:
(1)DAAMOA
A method of preparing an amide-type organic friction modifier as described above, comprising: diacetone acrylamide and oleylamine are used as reaction substrates, and react for 24 hours at the temperature of 80 ℃ and the vacuum degree of 0.095MPa to obtain the product.
Specifically, the preparation method of the organic friction modifier comprises the following steps:
Diacetone acrylamide and oleylamine with the molar ratio of 1:1 are taken as reaction substrates to react for 24 hours at the temperature of 80 ℃ and the vacuum degree of 0.095MPa, so as to obtain the target product.
The invention also provides application of the amide type organic friction modifier, which is used in the poly alpha-olefin base oil, and the using amount of the organic friction modifier in the base oil is 0.5-2 wt% based on the mass of the base oil. For example, the organic friction modifier is used in an amount of 0.5wt％、0.6wt％、、0.7wt％、0.8wt％、0.9wt％、1wt％、1.1wt％、1.2wt％、1.3wt％、1.4wt％、1.5wt％、1.6wt％、1.7wt％、1.8wt％、1.9wt％ or 2wt% in the base oil, based on the mass of the base oil.
Further, the organic friction modifier and ZDDP are added to the base oil simultaneously, the ZDDP being added in an amount of 0.5% to 2.0% by weight of the base oil. For example, the ZDDP is added to the base oil in an amount of 0.5wt％、0.6wt％、、0.7wt％、0.8wt％、0.9wt％、1wt％、1.1wt％、1.2wt％、1.3wt％、1.4wt％、1.5wt％、1.6wt％、1.7wt％、1.8wt％、1.9wt％ or 2wt% based on the mass of the base oil.
The invention has the technical characteristics and beneficial effects that:
The amide type organic friction modifier, the preparation method and the application thereof have the advantages that the preparation flow of the organic friction modifier is simple, the preparation cost is low, the yield is high, and the organic friction modifier can be dissolved in poly alpha-olefin base oil; the nitrogen atoms and the oxygen atoms in the molecular structure of the organic friction modifier are provided with lone pair electrons, electrons can be provided for electron-deficient orbits of metals, the organic friction modifier has a strong adsorption effect on the metals, further an ordered molecular adsorption film is formed on the surfaces of the metals, friction on the surfaces of friction pairs of the metals is reduced, and the organic friction modifier has good antifriction performance; when used together with ZDDP, the composition has good synergistic effect, can reduce the use amount of ZDDP in base oil, and can obtain lower friction coefficient.
Drawings
FIG. 1 is a synthetic route diagram of example 1 of the present invention.
FIG. 2 is an infrared spectrum of the friction modifier prepared in example 1 of the present invention.
FIG. 3 is a mass spectrum of the friction modifier prepared in example 1 of the present invention.
FIG. 4 is a graph showing the comparison of friction coefficients at different temperatures for the friction modifier prepared in example 1 of the present invention.
FIG. 5 is a graph showing the comparison of friction coefficients of the friction modifier prepared in example 1 of the present invention at various addition amounts.
FIG. 6 is a graph of friction coefficient comparisons for friction modifiers prepared in example 1 of the present invention used with ZDDP.
Detailed Description
The invention is further illustrated and described below in connection with specific examples.
Example 1
3.38G (0.02 mol) of diacetone acrylamide and 5.35g (0.02 mol) of oleylamine are weighed and added into a 25ml single-neck flask, and the mixture is reacted for 24 hours at the temperature of 80 ℃ and the vacuum degree of 0.095MPa to obtain 8.29g (yield 99.1 wt%) of a target product, which is recorded as DAAMOA, and the reaction process is shown in FIG. 1.
And (3) infrared spectrum analysis:
The infrared spectrum containing the target product DAAMOA obtained in the above example 1 is shown in fig. 2, and the characteristic absorption peak of the N-H bond of 3500-3400cm -1 in the infrared spectrum of the product DAAMOA disappears, which indicates that the N-H bond in oleylamine reacts; the absorption peak of C=O stretching vibration at 1710cm -1 in the infrared spectrogram of the product DAAMOA disappears, and the absorption peak of C=N stretching vibration at 1662cm -1 appears, which indicates that the ketone-C=O in diacetone acrylamide reacts with-NH 2 in oleylamine molecules to generate-C=N bond. Further, it was demonstrated that the ketoamine condensation reaction occurred between oleylamine and diacetone acrylamide.
Mass spectrometry:
the mass spectrum of the product DAAMOA is shown in figure 3, and a peak is obvious at a mass-to-charge ratio of 419.4005, and the product is a product obtained by carrying out ketoamine condensation reaction on diacetone acrylamide and oleylamine and removing one molecule of water. As can be seen by combining an infrared spectrogram and a mass spectrogram analysis, diacetone acrylamide and oleylamine undergo a ketoamine condensation reaction to generate a product DAAMOA.
Friction performance test:
The test instrument is a TE-77 long-range reciprocating friction test machine, and the upper friction pair is The cylindrical pins, the lower friction pair is a 38mm multiplied by 58mm multiplied by 3.9mm plate, the materials are GCr15 steel, and the contact mode is line contact.
The product DAAMOA obtained in example 1 was dissolved in poly-alpha-olefin base oil (PAO 6, exxonMobil) at an addition amount of 1wt% (based on the mass of the base oil) with stirring, and a reciprocating friction test was performed at 25℃and 80℃and 135℃respectively under the following test conditions: load 100N, stroke 10mm, frequency 10Hz, time 3600s.
TABLE 1 average coefficient of friction for products of example 1 subjected to reciprocating friction tests at different temperatures
As can be seen from the data presented in table 1 and the friction coefficient curves presented in fig. 4, the samples added to the product DAAMOA of example 1 all had a reduction in friction coefficient at different temperatures, with a reduction in the range of 11.3% to 27.5% compared to the base oil PAO 6.
Further examining the tribological properties of the product DAAMOA of example 1 added (the following mass percentages are based on the mass of the base oil PAO 6) in an amount of 0.5wt%, 1wt% and 2wt% respectively to the base oil PAO6, the test conditions were: the load is 100N, the stroke is 10mm, the frequency is 10Hz, the temperature is 80 ℃, and the time is 3600s.
TABLE 2 average coefficient of friction for the products of example 1 tested for reciprocating friction at various addition levels
As can be seen by combining the data presented in table 2 and the friction coefficient curves presented in fig. 5, the friction coefficient of the samples added with different amounts of the product DAAMOA of example 1 was reduced by 21.1% to 27.5% compared to the base oil PAO 6.
Tribological property evaluations were performed on the product DAAMOA of example 1 compounded with ZDDP. The samples were oil samples obtained by adding 1wt% DAAMOA, 1wt% ZDDP, 0.5wt% DAAMOA+0.5wt% ZDDP to base oil PAO6 (the following mass percentages are based on the mass of PAO6, respectively). The test conditions were: the load is 100N, the stroke is 10mm, the frequency is 10Hz, the temperature is 135 ℃, and the time is 3600s.
TABLE 3 average coefficient of friction for the products of example 1 and ZDDP used alone and after compounding
As can be seen from the data presented in table 3 and the coefficient of friction curves presented in fig. 6, the coefficient of friction of the product DAAMOA of example 1 after compounding with ZDDP was significantly lower than DAAMOA and ZDDP alone, with a drop of over 20.5%, indicating a synergistic effect.
The invention has the beneficial effects that:
The amide type organic friction modifier, the preparation method and the application thereof have the advantages that the preparation flow of the organic friction modifier is simple, the preparation cost is low, the yield is high, and the organic friction modifier can be dissolved in base oil PAO 6; the organic friction modifier has lone pair electrons on nitrogen atoms and oxygen atoms in a molecular structure, can provide electrons for electron-deficient orbits of metals, has strong adsorption effect on the metals, further forms an ordered molecular adsorption film on the surfaces of the metals, reduces friction on the surfaces of friction pairs of the metals, and has good antifriction performance; the organic friction modifier has good synergistic effect when used together with ZDDP, can reduce the use amount of ZDDP in base oil, and obtains lower friction coefficient.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (6)
1. An amide-type organic friction modifier characterized in that the organic friction modifier has a structural formula of formula (1):
2. A method of preparing the amide type organic friction modifier of claim 1, comprising: diacetone acrylamide and oleylamine are used as reaction substrates, and react for 24 hours at the temperature of 80 ℃ and the vacuum degree of 0.095MPa to obtain the product.
3. The method for preparing an amide type organic friction modifier according to claim 2, wherein the molar ratio of diacetone acrylamide to oleylamine is 1:1.
4. Use of an amide type organic friction modifier according to claim 1, wherein the organic friction modifier is added to a base oil in an amount of 0.5 to 2.0wt% of the base oil based on the mass of the base oil.
5. The use of an amide type organic friction modifier according to claim 4 wherein the base oil is a polyalphaolefin.
6. The use of an amide type organic friction modifier according to claim 4 wherein the organic friction modifier and zinc dialkyldithiophosphate are added simultaneously to the base oil in an amount of 0.5wt% to 2.0wt% of the base oil.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310517551.4A CN116574548B (en) | 2023-05-09 | 2023-05-09 | Amide type organic friction improver, preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310517551.4A CN116574548B (en) | 2023-05-09 | 2023-05-09 | Amide type organic friction improver, preparation method and application thereof |
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| CN116574548A CN116574548A (en) | 2023-08-11 |
| CN116574548B true CN116574548B (en) | 2024-04-30 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3479271A (en) * | 1970-10-27 | 1973-05-03 | Lubrizol Corporation, The | Thickened aqueous compositions containing crylamidoalkanesulfonate polymers |
| CN108753479A (en) * | 2018-06-05 | 2018-11-06 | 深圳市艾德化学品科技有限公司 | A kind of direct fuel-injection engine gas handling system decarbonizer |
| CN115197767A (en) * | 2022-06-24 | 2022-10-18 | 一汽解放汽车有限公司 | Gear lubricating oil composition |
-
2023
- 2023-05-09 CN CN202310517551.4A patent/CN116574548B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3479271A (en) * | 1970-10-27 | 1973-05-03 | Lubrizol Corporation, The | Thickened aqueous compositions containing crylamidoalkanesulfonate polymers |
| CN108753479A (en) * | 2018-06-05 | 2018-11-06 | 深圳市艾德化学品科技有限公司 | A kind of direct fuel-injection engine gas handling system decarbonizer |
| CN115197767A (en) * | 2022-06-24 | 2022-10-18 | 一汽解放汽车有限公司 | Gear lubricating oil composition |
Non-Patent Citations (1)
| Title |
|---|
| 有机摩擦改进剂研究进展;夏垒;辽宁科技大学学报;20211015;第44卷(第05期);393-400 * |
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