CN114426901A - High-temperature antioxidant solution and preparation method thereof - Google Patents
High-temperature antioxidant solution and preparation method thereof Download PDFInfo
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- CN114426901A CN114426901A CN202210071352.0A CN202210071352A CN114426901A CN 114426901 A CN114426901 A CN 114426901A CN 202210071352 A CN202210071352 A CN 202210071352A CN 114426901 A CN114426901 A CN 114426901A
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- China
- Prior art keywords
- naphthylamine
- temperature
- diphenylamine
- antioxidant solution
- preparation
- 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.)
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- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 47
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 55
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000001412 amines Chemical class 0.000 claims abstract description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 13
- -1 alkyl diphenylamine Chemical compound 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 19
- WJUMWVJBOZKPPU-UHFFFAOYSA-N 2,3-bis(6-methylheptyl)-N-phenylaniline Chemical compound C(CCCCC(C)C)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCC(C)C WJUMWVJBOZKPPU-UHFFFAOYSA-N 0.000 claims description 8
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 claims description 6
- UWKOGRXWKGLXLY-UHFFFAOYSA-N n,n-diphenyl-2,3-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C(C)C UWKOGRXWKGLXLY-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 10
- 239000007789 gas Substances 0.000 abstract description 8
- 239000003921 oil Substances 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 7
- 239000010687 lubricating oil Substances 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002184 metal Substances 0.000 description 3
- 238000005691 oxidative coupling reaction Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000004886 process control Methods 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
- 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
- C10M141/06—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 nitrogen-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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- 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
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
Abstract
The invention provides a high-temperature antioxidant solution and a preparation method thereof; the preparation method comprises the following steps: adding an amine source into a solvent, and introducing an oxygen donor for reaction to obtain a high-temperature antioxidant solution; the amine source is selected from diphenylamine and/or naphthylamine. Compared with the prior art, the high-temperature antioxidant solution provided by the invention takes a specific amine source as a raw material, the amine source is selected from diphenylamine and/or naphthylamine, gas is taken as an oxygen supply agent, and a catalyst is not adopted to prepare the high-temperature antioxidant solution; the prepared product is used in lubricating oil, can obviously improve the high-temperature performance of oil products, can replace alkyl diphenylamine and naphthylamine antioxidants, has better high-temperature performance, is used in higher-temperature use environments, and has wide prospect; meanwhile, the preparation method provided by the invention has the advantages of simple process, mild and easily-controlled conditions, low production cost, easiness in industrial large-scale production and wide application prospect.
Description
Technical Field
The invention relates to the technical field of antioxidants, in particular to a high-temperature antioxidant solution and a preparation method thereof.
Background
Antioxidants are the most important additives in lubricating oils and are directly related to the lifetime of the lubricating oil. The literature reports that dialkyl diphenylamine and alkyl-N-phenyl-alpha-naphthylamine are subjected to oxidative coupling reaction to obtain an antioxidant with more outstanding high-temperature oxidation resistance, and the antioxidant has far better performance than a gas parent compound and a mixture thereof, and the reaction equation is as follows:
US20080045425A1 adopts acetylacetone metal catalyst and gas assistant to realize synthesis; but the purity of the synthesized product is relatively low, and the product performance and the process have problems. EP0799289B1 adopts an organic peroxide oxygen supply agent, and the product is synthesized by oxidative coupling reaction without metal residue; but the difficulty of process control is high, and the requirement on equipment is relatively high. US5489711 adopts peroxide as an oxygen donor, and adopts oxidative coupling reaction to synthesize a target product; however, the reaction temperature is relatively low and the product purity is limited. Domestic CN200780030182.5 adopts acetylacetone metal catalyst and gas auxiliary agent to realize synthesis; however, the reaction temperature is relatively low, and the purity and process of the synthesized product are problematic. CN201910291587.9 (a method for preparing oxidation coupling high-temperature antioxidant without solvent) adopts organic solvent as oxygen donor to complete oxidation coupling reaction under reduced pressure.
Disclosure of Invention
In view of the above, the present invention provides a high temperature antioxidant solution and a preparation method thereof, and the high temperature antioxidant solution provided by the present invention is used in lubricating oil, and can significantly improve the high temperature performance of oil products.
The invention provides a preparation method of a high-temperature antioxidant solution, which comprises the following steps:
adding an amine source into a solvent, and introducing an oxygen donor for reaction to obtain a high-temperature antioxidant solution; the amine source is selected from diphenylamine and/or naphthylamine.
Preferably, the solvent is a pentaerythritol ester.
Preferably, the amine source is diphenylamine and naphthylamine; the molar ratio of diphenylamine to naphthylamine is 5: (1-25).
Preferably, the diphenylamine is selected from one or more of diisooctyldiphenylamine, octylbutyldiphenylamine and diisopropylphenyldiphenylamine.
Preferably, the naphthylamine is selected from one or more of N-phenyl-alpha-naphthylamine, N-phenyl-beta-naphthylamine, alkylated N-phenyl-alpha-naphthylamine and alkylated N-phenyl-beta-naphthylamine.
Preferably, the mass ratio of the solvent to the amine source is (0.5-4): 1.
preferably, the oxygen donor is air or oxygen.
Preferably, the reaction temperature is 170-210 ℃ and the reaction time is 20-30 h.
Preferably, the oligomer proportion after the reaction is more than 60% by weight.
The invention also provides a high-temperature antioxidant solution which is prepared by adopting the preparation method of the technical scheme.
The invention provides a high-temperature antioxidant solution and a preparation method thereof; the preparation method comprises the following steps: adding an amine source into a solvent, and introducing an oxygen donor for reaction to obtain a high-temperature antioxidant solution; the amine source is selected from diphenylamine and/or naphthylamine. Compared with the prior art, the high-temperature antioxidant solution provided by the invention takes a specific amine source as a raw material, the amine source is selected from diphenylamine and/or naphthylamine, gas is taken as an oxygen supply agent, and a catalyst is not adopted to prepare the high-temperature antioxidant solution; the prepared product is used in lubricating oil, can obviously improve the high-temperature performance of oil products, can replace alkyl diphenylamine and naphthylamine antioxidants, has better high-temperature performance, is used in higher-temperature use environments, and has wide prospect; meanwhile, the preparation method provided by the invention has the advantages of simple process, mild and easily-controlled conditions, low production cost, easiness in industrial large-scale production and wide application prospect.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a preparation method of a high-temperature antioxidant solution, which comprises the following steps:
adding an amine source into a solvent, and introducing an oxygen donor for reaction to obtain a high-temperature antioxidant solution; the amine source is selected from diphenylamine and/or naphthylamine.
In the present invention, the solvent is preferably a pentaerythritol ester; the source of the pentaerythritol ester is not particularly limited in the present invention, and commercially available products or self-products known to those skilled in the art may be used.
In the present invention, the amine source is selected from diphenylamine and/or naphthylamine, preferably diphenylamine and naphthylamine; the source of the amine source is not particularly limited in the present invention, and commercially available or self-prepared products well known to those skilled in the art may be used.
In a preferred embodiment of the invention, the amine source is diphenylamine and naphthylamine; the molar ratio of diphenylamine to naphthylamine is preferably 5: (1-25).
In the present invention, the diphenylamine is preferably selected from one or more of diisooctyldiphenylamine, octylbutyldiphenylamine and diisopropylphenyldiphenylamine, more preferably diisooctyldiphenylamine; the naphthylamine is preferably selected from one or more of N-phenyl-alpha-naphthylamine, N-phenyl-beta-naphthylamine, alkylated N-phenyl-alpha-naphthylamine and alkylated N-phenyl-beta-naphthylamine, more preferably N-phenyl-alpha-naphthylamine. In a preferred embodiment of the invention, the diphenylamine is diisooctyldiphenylamine and the naphthylamine is N-phenyl-alpha-naphthylamine; the mass ratio of the diisooctyl diphenylamine to the N-phenyl-alpha-naphthylamine is preferably (1-4): 1, more preferably 1: 1.
in the invention, the mass ratio of the solvent to the amine source is preferably (0.5-4): 1, more preferably (0.9 to 1.1): 1.
in the present invention, the oxygen donor is preferably air or oxygen, more preferably air. The source of the oxygen donor is not particularly limited, and the continuous feeding in the reaction is ensured.
In the invention, the reaction temperature is preferably 170-210 ℃, and more preferably 180-200 ℃; the reaction time is preferably 20 to 30 hours, more preferably 24 hours. Therefore, the invention synthesizes the oligomer high-temperature antioxidant solution in the pentaerythritol ester solvent at high temperature by using gas as an oxygen donor and diphenylamine and/or naphthylamine as raw materials without adopting a catalyst.
In the present invention, the oligomer proportion after the reaction is preferably more than 60% by weight.
The preparation method provided by the invention has the advantages of simple process, mild condition, easiness in control, low production cost, easiness in industrial large-scale production and wide application prospect.
The invention also provides a high-temperature antioxidant solution which is prepared by adopting the preparation method of the technical scheme. The high-temperature antioxidant solution provided by the invention takes a specific amine source as a raw material, the amine source is selected from diphenylamine and/or naphthylamine, gas is taken as an oxygen donor, and a catalyst is not adopted to prepare the high-temperature antioxidant solution; the prepared product is used in lubricating oil, can obviously improve the high-temperature performance of oil products, can replace alkyl diphenylamine and naphthylamine antioxidants, has better high-temperature performance, is used in higher-temperature use environments, and has wide prospect.
The invention provides a high-temperature antioxidant solution and a preparation method thereof; the preparation method comprises the following steps: adding an amine source into a solvent, and introducing an oxygen donor for reaction to obtain a high-temperature antioxidant solution; the amine source is selected from diphenylamine and/or naphthylamine. Compared with the prior art, the high-temperature antioxidant solution provided by the invention takes a specific amine source as a raw material, the amine source is selected from diphenylamine and/or naphthylamine, gas is taken as an oxygen supply agent, and a catalyst is not adopted to prepare the high-temperature antioxidant solution; the prepared product is used in lubricating oil, can obviously improve the high-temperature performance of oil products, can replace alkyl diphenylamine and naphthylamine antioxidants, has better high-temperature performance, is used in higher-temperature use environments, and has wide prospect; meanwhile, the preparation method provided by the invention has the advantages of simple process, mild and easily-controlled conditions, low production cost, easiness in industrial large-scale production and wide application prospect.
To further illustrate the present invention, the following examples are provided for illustration. The raw materials used in the following examples of the present invention are all commercially available products.
Examples 1 to 6
Adding diphenylamine and naphthylamine serving as raw materials into pentaerythritol ester, and introducing an oxygen supply agent for reaction to obtain a high-temperature antioxidant solution; the raw materials and the amounts, the reaction conditions and the parameters are shown in Table 1.
Data sheets of raw materials and amounts, reaction conditions, and parameters in the preparation methods provided in examples 1 to 6
And (3) performance testing:
taking example 6 as an example, the performance data of the high-temperature antioxidant solution provided in comparative example 6, and equivalent amounts of diisooctyldiphenylamine, N-phenyl-alpha-naphthylamine and their compounded products used as oil antioxidants are shown in Table 2.
TABLE 2 data of various properties of the high temperature antioxidant solution provided in example 6, equivalent amounts of diisooctyl diphenylamine, N-phenyl-alpha-naphthylamine and their combination in oil antioxidants
Table continuation: each performance data of the high-temperature antioxidant solution provided in the embodiment 1-5 after being used as an antioxidant of an oil product
As shown in Table 2, the high-temperature antioxidant solution provided by the invention has the advantages of corrosion and oxidation stability and thermal stability due to the combination of the raw materials aniline and naphthylamine which are equivalent, can replace alkyl diphenylamine and naphthylamine antioxidants, has better high-temperature performance, is used in higher-temperature use environments, and has wide prospects.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. A preparation method of a high-temperature antioxidant solution comprises the following steps:
adding an amine source into a solvent, and introducing an oxygen donor for reaction to obtain a high-temperature antioxidant solution; the amine source is selected from diphenylamine and/or naphthylamine.
2. The method of claim 1, wherein the solvent is pentaerythritol ester.
3. The production method according to claim 1, wherein the amine source is diphenylamine and naphthylamine; the molar ratio of diphenylamine to naphthylamine is 5: (1-25).
4. A method of preparation according to claim 3, characterized in that the diphenylamine is selected from one or more of diisooctyldiphenylamine, octylbutyldiphenylamine and diisopropylphenyldiphenylamine.
5. The method of claim 3, wherein the naphthylamine is selected from one or more of N-phenyl-alpha-naphthylamine, N-phenyl-beta-naphthylamine, alkylated N-phenyl-alpha-naphthylamine, and alkylated N-phenyl-beta-naphthylamine.
6. The method according to claim 1, wherein the mass ratio of the solvent to the amine source is (0.5-4): 1.
7. the method of claim 1, wherein the oxygen donor is air or oxygen.
8. The preparation method according to claim 1, wherein the reaction temperature is 170-210 ℃ and the reaction time is 20-30 h.
9. The method according to claim 1, wherein the oligomer content after the reaction is more than 60 wt%.
10. A high-temperature antioxidant solution, which is prepared by the preparation method of any one of claims 1 to 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210071352.0A CN114426901A (en) | 2022-01-21 | 2022-01-21 | High-temperature antioxidant solution and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210071352.0A CN114426901A (en) | 2022-01-21 | 2022-01-21 | High-temperature antioxidant solution and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114426901A true CN114426901A (en) | 2022-05-03 |
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| CN202210071352.0A Pending CN114426901A (en) | 2022-01-21 | 2022-01-21 | High-temperature antioxidant solution and preparation method thereof |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1117714A (en) * | 1966-03-28 | 1968-06-19 | Mobil Oil Corp | Stabilized organic compositions |
| US3666716A (en) * | 1966-04-07 | 1972-05-30 | Uniroyal Inc | Derivatives of diphenylamine and the phenylnaphthylamines as antioxidants and as synergists with dialkyl 3,3{40 -thiodipropionates |
| WO1995017488A2 (en) * | 1993-12-15 | 1995-06-29 | Exxon Research & Engineering Company | Lubricant composition containing a polymeric antioxidant |
| US6426324B1 (en) * | 1993-12-15 | 2002-07-30 | Noveon Ip Holdings Corp. | Lubricant composition |
| CN105733740A (en) * | 2014-12-08 | 2016-07-06 | 中国石油天然气股份有限公司 | Amine oligomer anti-oxidant and preparation method thereof |
| CN107573983A (en) * | 2017-10-23 | 2018-01-12 | 中国石油化工股份有限公司 | A kind of high temperature resistant antioxidant and its preparation method and application |
| CN109942435A (en) * | 2019-04-12 | 2019-06-28 | 江苏飞亚化学工业有限责任公司 | A kind of oxidation coupling high-temperature antioxidant non-solvent preparation |
-
2022
- 2022-01-21 CN CN202210071352.0A patent/CN114426901A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1117714A (en) * | 1966-03-28 | 1968-06-19 | Mobil Oil Corp | Stabilized organic compositions |
| US3666716A (en) * | 1966-04-07 | 1972-05-30 | Uniroyal Inc | Derivatives of diphenylamine and the phenylnaphthylamines as antioxidants and as synergists with dialkyl 3,3{40 -thiodipropionates |
| WO1995017488A2 (en) * | 1993-12-15 | 1995-06-29 | Exxon Research & Engineering Company | Lubricant composition containing a polymeric antioxidant |
| US6426324B1 (en) * | 1993-12-15 | 2002-07-30 | Noveon Ip Holdings Corp. | Lubricant composition |
| CN105733740A (en) * | 2014-12-08 | 2016-07-06 | 中国石油天然气股份有限公司 | Amine oligomer anti-oxidant and preparation method thereof |
| CN107573983A (en) * | 2017-10-23 | 2018-01-12 | 中国石油化工股份有限公司 | A kind of high temperature resistant antioxidant and its preparation method and application |
| CN109942435A (en) * | 2019-04-12 | 2019-06-28 | 江苏飞亚化学工业有限责任公司 | A kind of oxidation coupling high-temperature antioxidant non-solvent preparation |
Non-Patent Citations (1)
| Title |
|---|
| SUMITTRA DUANGKAEWMANEE等: "Synergistic and antagonistic effects on oxidation stability of antioxidants in a synthetic ester based oil", 《TRIBOLOGY INTERNATIONAL》 * |
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