CN110437909B - Lubricating oil base oil and preparation method thereof - Google Patents
Lubricating oil base oil and preparation method thereof Download PDFInfo
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- CN110437909B CN110437909B CN201910766990.2A CN201910766990A CN110437909B CN 110437909 B CN110437909 B CN 110437909B CN 201910766990 A CN201910766990 A CN 201910766990A CN 110437909 B CN110437909 B CN 110437909B
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- base oil
- lubricant base
- neopentyl glycol
- acrylate
- heptanoic acid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
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- 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
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/28—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
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- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
-
- 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
- C10N2030/02—Pour-point; Viscosity index
-
- 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
-
- 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
Abstract
The invention belongs to the technical field of compositions grafted to macromolecular compounds obtained by unsaturated carbon-carbon bond reaction, and particularly relates to lubricating oil base oil and a preparation method thereof. The lubricant base oil comprises a compound shown as a formula (I), a compound shown as a formula (II) and a compound shown as a formula (III);
Description
Technical Field
The invention belongs to the technical field of compositions grafted to macromolecular compounds obtained by unsaturated carbon-carbon bond reaction, and particularly relates to lubricating oil base oil and a preparation method thereof.
Background
Currently, lubricating oil is widely used in the industries of chemical industry, textile industry, machinery industry and the like. With the further popularization of the economic globalization, particularly the rapid development of the automobile industry, and the enhancement of the requirements of environmental protection and energy conservation, although the total supply of the lubricating oil is not greatly increased, the demand of high-grade lubricating oil is increasingly vigorous (the research on the structural composition and performance relationship of the lubricating oil base oil, wangxiwen and the like, applied to chemical engineering, 43 rd volume 3 rd, 539 page left column, 1 st to 5 th rows, published 2014 3 months and 31 days).
Generally, the lubricating oil consists of base oil and additives, and the lubricating oil base oil is used as the main body of the lubricating oil and accounts for 70-90% of the whole system. The base oil directly influences the quality of lubricating oil products, and along with the stricter environmental protection and energy conservation laws, the requirements on the quality and southwest of modern lubricating oil are higher and higher, and the effect of the base oil is increasingly obvious. The base oil can be classified into mineral oil (obtained by distilling crude oil under reduced pressure and performing different processes), animal and vegetable oil (such as rapeseed oil, sunflower seed oil, soybean oil, etc.) and synthetic lubricating oil according to the source. Among them, animal and vegetable lubricating oils, which were the first base oils used as lubricating oils, are gradually replaced with mineral oils because of their high oxidation rate and short service life. However, mineral oils have poor low temperature performance ("high temperature lube base oil research progress", lujun et al, industrial catalysis, vol 18, 9, 2010, page 15, left column, 1, lines 1-12, published, 9/30, 2010). The synthetic lubricating oil base oil is an oil product which is prepared by an organic synthesis method and has a certain chemical structure and special performance. The synthetic lubricating oil base oil has the characteristics of good lubricating property, long service life and the like (performance and application of the synthetic base oil in lubricating oil, Liqi and the like, petroleum commercial technology, No. 29 volume No. 2 in 2011, No. 7 page, No. 1 section No. 3 line in the left column, No. 2 section No. 1 line to 2 line in the left column, published 2011 12 months and 31 days).
However, the low temperature properties of the existing synthetic lubricating base oils are poor, especially the pour points of high viscosity lubricating oils are low, making it difficult to start up in cold regions in winter field operations.
Disclosure of Invention
In view of the above, the present invention aims to provide a lubricant base oil with good low temperature performance.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a lubricant base oil comprising a compound represented by formula (I), a compound represented by formula (II), and a compound represented by formula (III);
wherein n is more than or equal to 1.
In the present invention, the lubricating oil is used between two objects which move relative to each other, and is capable of reducing friction and wear caused by contact between the two objects.
In the present invention, the base oil is a substance that is a main component of the lubricating oil (70% to 90% in the lubricating oil system).
The lubricating base oil containing the compound represented by the formula (I), the compound represented by the formula (II) and the compound represented by the formula (III) is good in low-temperature performance, and the high-viscosity lubricating oil is high in pour point.
The invention also aims to protect the preparation method of the lubricating oil base oil, which comprises the following steps:
A. preparing neopentyl glycol mono-heptanoate by taking neopentyl glycol and n-heptanoic acid as raw materials;
B. adding acrylic acid into the reacted system obtained in the step A, controlling the vacuum pressure of 7000Pa to 7500Pa and the temperature of 85 ℃ to 95 ℃, reacting for 10h to 12h, then increasing the vacuum degree until the vacuum pressure is less than or equal to 1000Pa, evaporating unreacted acrylic acid raw materials, washing the mixture in the reaction kettle with water until the pH value is 7, and dehydrating to obtain neopentyl glycol-heptanoic acid-acrylate;
C. neopentyl glycol-heptanoic acid-acrylate and 1-octene are used as raw materials to carry out polymerization reaction.
Further, in step B, acrylic acid is used in an amount of 2.5 to 3.5 times the amount of the neopentyl glycol substance in step A.
Further, in step a, the mass ratio of neopentyl glycol to n-heptanoic acid was 1: 1.
Further, in the step A, the reaction temperature is 110-120 ℃, the vacuum pressure is less than or equal to 1000Pa, and the reaction time is 8-10 h.
Further, in step A, the catalyst used is p-toluenesulfonic acid.
Further, in the step A, the dosage of the p-toluenesulfonic acid is 1% -2% of the mass sum of the neopentyl glycol and the n-heptanoic acid.
Further, in the step C, di-tert-butyl peroxide (DTBP) is used as an initiator, the reaction temperature is 110-120 ℃, the vacuum pressure is less than or equal to 1000Pa, and the reaction time is 8-10 h.
Further, the amount of the peroxy-di-tert-butyl as an initiator is 4 to 6 percent of the mass sum of the neopentyl glycol-heptanoic acid-acrylate and the 1-octene.
Further, in step C, the mass ratio of neopentyl glycol-heptanoic acid-acrylate to 1-octene was 1: 1.
Further, the preparation method of the lubricating oil base oil comprises the following steps:
A. mixing neopentyl glycol and n-heptanoic acid according to the mass ratio of 1:1, putting the mixture into a reaction kettle, adding p-toluenesulfonic acid accounting for 1-2% of the mass of neopentyl glycol and n-heptanoic acid, controlling the reaction temperature to be 110-120 ℃, vacuumizing and dehydrating, controlling the vacuum pressure to be less than or equal to 1000Pa, and performing esterification reaction for 8-10 h to generate neopentyl glycol mono-heptanoate;
B. adding 3 times of acrylic acid of neopentyl glycol substance into the reacted system obtained in the step A, controlling the vacuum pressure of 7000Pa-7500Pa, the temperature of 85-95 ℃, continuing to stir for 10-12 h, increasing the vacuum degree until the vacuum pressure is less than or equal to 1000Pa, evaporating unreacted acrylic acid raw materials, washing the mixture in the reaction kettle with water until the pH value is 7, and dehydrating to obtain neopentyl glycol-heptanoic acid-acrylate;
C. putting neopentyl glycol-heptanoic acid-acrylate and 1-octene into a reaction kettle according to the mass ratio of 1:1, adding 4-6% of peroxy di-tert-butyl of the sum of the mass of the neopentyl glycol-heptanoic acid-acrylate and the mass of the 1-octene as an initiator, controlling the polymerization temperature to be 110-120 ℃, controlling the vacuum pressure to be less than or equal to 1000Pa, and carrying out polymerization reaction for 8-10 h to obtain the neopentyl glycol-heptanoic acid-acrylate copolymer.
The invention has the beneficial effects that:
the lubricating base oil has higher viscosity and higher viscosity index.
The lubricating oil base oil has good low-temperature performance and high pour point of high-viscosity lubricating oil.
Detailed Description
The examples are provided for better illustration of the present invention, but the present invention is not limited to the examples. Therefore, those skilled in the art should make insubstantial modifications and adaptations to the embodiments of the present invention in light of the above teachings and remain within the scope of the invention.
The following iodine value is measured according to GB/T5532-2008 animal and vegetable oil iodine value measurement;
the following kinematic viscosities were measured according to GB/T265 and 1998 kinematic viscosity measurements and kinetic viscosity calculations of petroleum products;
the following viscosity index calculations were performed according to GB/T1995-1998 viscosity index calculation method for petroleum products;
the following pour points were measured according to GB/T3535-2006 Petroleum products pour Point determination.
Example 1
The lubricating oil base oil is prepared from the following raw materials in the following steps:
A. putting 104.0g of neopentyl glycol and 130.2g of n-heptanoic acid into a 1000ml reaction kettle, adding 4.7g of p-toluenesulfonic acid as a catalyst, controlling the reaction temperature at 110 ℃, vacuumizing and dehydrating, controlling the vacuum pressure at 900Pa, and carrying out esterification reaction for 8h to obtain neopentyl glycol mono-heptanoate.
B. Adding 180.0g of fresh acrylic acid into the system after the reaction in the step A, controlling the pressure to be 7500Pa and the temperature to be 95 ℃, continuing stirring for esterification reaction for 10 hours, stopping the reaction, controlling the vacuum pressure to be 900Pa, evaporating excessive acrylic acid, washing a reaction substrate for 5 times to be neutral, and dehydrating to obtain neopentyl glycol-monoacid-acrylic ester for later use;
C. and (2) accurately weighing 135.0g of neopentyl glycol-monoacid-acrylate and 56.1g of 1-octene obtained by the reaction, putting the neopentyl glycol-monoacid-acrylate and the 1-octene in a 250ml reaction kettle, adding 7.68g of di-tert-butyl peroxide initiator, vacuumizing, heating, stirring and reacting, controlling the reaction temperature to be 110 ℃, the vacuum pressure to be 900Pa, and reacting for 8 hours to obtain the neopentyl glycol-monoacid-acrylate copolymer.
Example 2
The lubricating oil base oil is prepared from the following raw materials in the following steps:
A. putting 104.0g of neopentyl glycol and 130.2g of n-heptanoic acid into a 1000ml reaction kettle, adding 2.35g of p-toluenesulfonic acid as a catalyst, controlling the reaction temperature at 120 ℃, vacuumizing and dehydrating, controlling the vacuum pressure at 800Pa, and performing esterification reaction for 10 hours to generate neopentyl glycol mono-heptanoate;
B. adding 216.0g of fresh acrylic acid into the system after the reaction in the step A, controlling the pressure to be 7000Pa and the temperature to be 85 ℃, continuing stirring for esterification reaction for 12h, stopping the reaction, controlling the vacuum pressure to be 800Pa, evaporating excess acrylic acid, washing a reaction substrate for 5 times to be neutral, and dehydrating to obtain neopentyl glycol-more acid-acrylate for later use;
C. and (2) accurately weighing 135.0g of neopentyl glycol-monoacid-acrylate and 56.1g of 1-octene obtained by the reaction, putting the neopentyl glycol-monoacid-acrylate and the 1-octene in a 250ml reaction kettle, adding 9.6g of di-tert-butyl peroxide initiator, vacuumizing, heating, stirring and reacting, controlling the reaction temperature to be 120 ℃, the vacuum pressure to be 800Pa, and the reaction time to be 10 hours.
Example 3
The lubricating oil base oil is prepared from the following raw materials in the following steps:
A. putting 104.0g of neopentyl glycol and 130.2g of n-heptanoic acid into a 1000ml reaction kettle, adding 4.7g of p-toluenesulfonic acid serving as a catalyst, controlling the reaction temperature to be 115 ℃, vacuumizing and dehydrating, controlling the vacuum pressure to be 600Pa, and performing esterification reaction for 9 hours to obtain neopentyl glycol mono-heptanoate.
B. Adding 252.0g of fresh acrylic acid into the system after the reaction in the step A, controlling the pressure to be 7200Pa and the temperature to be 90 ℃, continuing stirring for esterification reaction for 12 hours, stopping the reaction, controlling the vacuum pressure to be 800Pa, evaporating excessive acrylic acid, washing a reaction substrate for 5 times to be neutral, and dehydrating to obtain neopentyl glycol-monoacid-acrylate for later use;
C. and (2) accurately weighing 135.0g of neopentyl glycol-monoacid-acrylate and 56.1g of 1-octene obtained by the reaction, putting the neopentyl glycol-monoacid-acrylate and the 1-octene in a 250ml reaction kettle, adding 11.5g of di-tert-butyl peroxide initiator, vacuumizing, heating, stirring and reacting, controlling the reaction temperature to be 120 ℃, the vacuum pressure to be 800Pa, and the reaction time to be 8 hours.
Performance detection
The lube base oils obtained in examples 1 to 3 were examined for the iodine value, kinematic viscosity at 100 ℃, viscosity index, pour point and other indicators, and the results are shown in Table 1.
Table 1 results of performance testing
| Detecting items | Example 1 | Example 2 | Example 3 |
| Iodine value/(g/100 g) | 0.15 | 0.08 | 0.11 |
| Kinematic viscosity at 100 deg.C/(mm)2/s) | 563.1 | 779.7 | 582.5 |
| Viscosity index | 327 | 358 | 344 |
| Pour point/. degree.C | -8 | -7 | -8 |
As can be seen from Table 1, the lubricant base oils produced in examples 1-3 have higher viscosities and viscosity indices, but also have relatively lower iodine numbers and lower pour points than base oil products of equivalent viscosities. Therefore, the base oil lubricating oil disclosed by the invention is good in low-temperature performance and high in viscosity.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (21)
1. A lubricant base oil characterized by comprising a compound represented by the formula (I), a compound represented by the formula (II) and a compound represented by the formula (III);
wherein n is more than or equal to 1;
the preparation method of the lubricating oil base oil comprises the following steps:
A. preparing neopentyl glycol mono-heptanoate by taking neopentyl glycol and n-heptanoic acid as raw materials;
B. adding acrylic acid into the reacted system obtained in the step A, controlling the vacuum pressure of 7000Pa to 7500Pa and the temperature of 85 ℃ to 95 ℃, reacting for 10h to 12h, then increasing the vacuum degree until the vacuum pressure is less than or equal to 1000Pa, evaporating unreacted acrylic acid raw materials, washing the mixture in the reaction kettle with water until the pH value is 7, and dehydrating to obtain neopentyl glycol-heptanoic acid-acrylate;
C. neopentyl glycol-heptanoic acid-acrylate and 1-octene are used as raw materials to carry out polymerization reaction.
2. The lubricant base oil of claim 1, wherein in step B, acrylic acid is used in an amount 2.5 times to 3.5 times the amount of neopentyl glycol material in step a.
3. The lubricant base oil according to claim 1 or 2, characterized in that in step a, the mass ratio of neopentyl glycol and n-heptanoic acid is 1: 1.
4. The lubricant base oil according to claim 1 or 2, wherein in the step A, the reaction temperature is 110-120 ℃, the vacuum pressure is less than or equal to 1000Pa, and the reaction time is 8-10 h.
5. The lubricant base oil as claimed in claim 3, wherein in the step A, the reaction temperature is 110-120 ℃, the vacuum pressure is less than or equal to 1000Pa, and the reaction time is 8-10 h.
6. The lubricant base oil of claim 1, 2 or 5, wherein in step A, the catalyst used is p-toluenesulfonic acid.
7. The lubricant base oil of claim 3, wherein in step A, the catalyst used is p-toluenesulfonic acid.
8. The lubricant base oil of claim 4, wherein in step A, the catalyst used is p-toluenesulfonic acid.
9. The lubricant base oil of claim 6, wherein in step A, the p-toluenesulfonic acid is used in an amount of 1% to 2% by mass of the sum of the neopentyl glycol and the n-heptanoic acid.
10. The lubricant base oil according to claim 1, 2, 5, 7, 8 or 9, wherein in step C, di-tert-butyl peroxide (DTBP) is used as an initiator, the reaction temperature is 110-120 ℃, the vacuum pressure is less than or equal to 1000Pa, and the reaction time is 8-12 h.
11. The lubricant base oil as claimed in claim 3, wherein in the step C, di-tert-butyl peroxide (DTBP) is used as an initiator, the reaction temperature is 110-120 ℃, the vacuum pressure is less than or equal to 1000Pa, and the reaction time is 8-12 h.
12. The lubricant base oil as claimed in claim 4, wherein in the step C, di-tert-butyl peroxide (DTBP) is used as an initiator, the reaction temperature is 110-120 ℃, the vacuum pressure is less than or equal to 1000Pa, and the reaction time is 8-12 h.
13. The lubricant base oil as claimed in claim 6, wherein in the step C, di-tert-butyl peroxide (DTBP) is used as an initiator, the reaction temperature is 110-120 ℃, the vacuum pressure is less than or equal to 1000Pa, and the reaction time is 8-12 h.
14. The lubricant base oil of claim 10, wherein the di-t-butyl peroxide is used as an initiator in an amount of 4% to 6% by mass of the sum of neopentyl glycol-heptanoic acid-acrylate and 1-octene.
15. The lubricant base oil according to any one of claims 11 to 13, wherein the di-tert-butyl peroxide is used as an initiator in an amount of 4% to 6% by mass of the sum of neopentyl glycol-heptanoic acid-acrylate and 1-octene.
16. The lubricant base oil of claim 1, 2, 5, 7, 8, 9, 11, 12, 13, or 14, wherein the ratio of the amount of material of neopentyl glycol-heptanoic acid-acrylate to 1-octene in step C is 1: 1.
17. The lubricant base oil of claim 3, wherein in step C, the mass ratio of neopentyl glycol-heptanoic acid-acrylate to 1-octene is 1: 1.
18. The lubricant base oil of claim 4, wherein in step C, the mass ratio of neopentyl glycol-heptanoic acid-acrylate to 1-octene is 1: 1.
19. The lubricant base oil of claim 6, wherein in step C, the mass ratio of neopentyl glycol-heptanoic acid-acrylate to 1-octene is 1: 1.
20. The lubricant base oil of claim 10, wherein in step C, the mass ratio of neopentyl glycol-heptanoic acid-acrylate to 1-octene is 1: 1.
21. The lubricant base oil of claim 16, wherein in step C, the mass ratio of neopentyl glycol-heptanoic acid-acrylate to 1-octene is 1: 1.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1196750A (en) * | 1995-09-21 | 1998-10-21 | 埃克森化学专利公司 | Synthetic ester base stocks for low emission lubricants |
| CN1651555A (en) * | 2000-02-09 | 2005-08-10 | 西铁城钟表股份有限公司 | Lubricating oil compositions and watch containing the same |
| CN102300966A (en) * | 2008-12-05 | 2011-12-28 | 道达尔炼油与销售部 | polyol ester lubricating oil |
| CN107312598A (en) * | 2017-06-30 | 2017-11-03 | 北京雅士科莱恩石油化工有限公司 | A kind of overweight load synthetic gear oil of low temperature |
| JP2018080246A (en) * | 2016-11-15 | 2018-05-24 | コスモ石油ルブリカンツ株式会社 | Base oil for lubricant oil and lubricant oil |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10150928B2 (en) * | 2013-09-16 | 2018-12-11 | Basf Se | Polyester and use of polyester in lubricants |
| KR20160047771A (en) * | 2014-10-23 | 2016-05-03 | 에스케이이노베이션 주식회사 | Lube base oil and method for preparing the same |
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2019
- 2019-08-20 CN CN201910766990.2A patent/CN110437909B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1196750A (en) * | 1995-09-21 | 1998-10-21 | 埃克森化学专利公司 | Synthetic ester base stocks for low emission lubricants |
| CN1651555A (en) * | 2000-02-09 | 2005-08-10 | 西铁城钟表股份有限公司 | Lubricating oil compositions and watch containing the same |
| CN102300966A (en) * | 2008-12-05 | 2011-12-28 | 道达尔炼油与销售部 | polyol ester lubricating oil |
| JP2018080246A (en) * | 2016-11-15 | 2018-05-24 | コスモ石油ルブリカンツ株式会社 | Base oil for lubricant oil and lubricant oil |
| CN107312598A (en) * | 2017-06-30 | 2017-11-03 | 北京雅士科莱恩石油化工有限公司 | A kind of overweight load synthetic gear oil of low temperature |
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| CN110437909A (en) | 2019-11-12 |
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