CN101724492B - Extreme pressure antiwear agent and preparation method thereof and lubricating oil combination - Google Patents
Extreme pressure antiwear agent and preparation method thereof and lubricating oil combination Download PDFInfo
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- CN101724492B CN101724492B CN 200810224384 CN200810224384A CN101724492B CN 101724492 B CN101724492 B CN 101724492B CN 200810224384 CN200810224384 CN 200810224384 CN 200810224384 A CN200810224384 A CN 200810224384A CN 101724492 B CN101724492 B CN 101724492B
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Abstract
The invention relates to an extreme pressure antiwear agent which is characterized by being a product by the joint sulphidation of thio-phosphate zinc and alkene; and the thio-phosphate zinc is compound denoted by a formula (1). The invention further provides a preparation method of the extreme pressure antiwear agent, comprising the following steps of: reacting fatty glyceride with phosphorus pentasulfite to obtain a thio-phosphate product; reacting the obtained thio-phosphate product with zinc oxide and/or zinc hydroxide to obtain the thio-phosphate zinc; and jointly sulphidizing the obtained thio-phosphate zinc and the alkene in the presence of sulfur. The invention further provides a lubricating oil combination containing the extreme pressure antiwear agent.
Description
Technical field
The lubricating oil composition that the present invention relates to a kind of extreme pressure anti-wear additives and preparation method thereof and contain this extreme pressure anti-wear additives.
Background technology
Lubricating oil works between two mechanical parts that have relative movement and come in contact, and protects moving parts not receive or few damaged through forming thin film.Lubricating oil is made up of base oil and additive two portions.Extreme pressure anti-wear additives and friction improver all are the oil dopes of using always.When two types of additives of adding are used between the moving parts in the common base oil; Can significantly reduce the frictional coefficient of surface in contact from the physicals friction improver; Extreme pressure anti-wear additives then can only perhaps not reduce the frictional coefficient of surface in contact on a small quantity; This frictional coefficient is under lower exercise intensity, to obtain, and basically do not have chemical reaction between the moving parts this moment, and to parts generation provide protection is oil film.When the exercise intensity between parts, when the load continuation increases, because parts surface friction aggravation, at the high temperature and the pressure of the microcell instantaneous generation of possibility of friction surface; Complicated friction chemical reaction can take place in this microcell; The metal of microcell also maybe be inter-adhesive, produces scratch greatly, at this moment; Extreme pressure anti-wear additives can reduce wearing and tearing better than friction improver; Guard block is injury-free, and this is because extreme pressure anti-wear additives generates friction chemical reaction product film in the metallic surface, has prevented the further damage of parts.That is to say that when as oil dope, friction improver is protected friction surface when underload, reduce frictional coefficient; Extreme pressure anti-wear additives is protected friction surface when middle high loading, form protective membrane, reduces wearing and tearing.
The sulfuration haco oil is the broad-spectrum extreme pressure anti-wear additives and the friction improver of twentieth century early development, is widely used in gear oil, steam cylinder oil, petrol engine running in oil and the railway grease.Along with the minimizing of cetacean number with to the protection of ecotope, gradually adopt non-haco oil to substitute production as raw material, developed a series of surrogate.Surrogate mainly adopts three kinds of methods synthetic: (1) will react with Fatty Alcohol(C12-C14 and C12-C18) from the mixed fatty acid (comprising saturated and unsaturated fatty acids) that vegetable and animals oils makes; Generate fatty ester; Vulcanize then, the structure of this product is the most approaching with the sulfuration haco oil, but cost is higher; (2) animal-plant oil is mixed with certain proportion with alhpa olefin, then sulfuration; (3) animal-plant oil is mixed with certain proportion with fatty ester, then sulfuration.
The sulfurized olefin cotton oil that adopts second kind of scheme to make is sold as commodity agent T405 at home.Such additive can effectively reduce the frictional coefficient of lubricating oil, is applied to machining oil, hydraulic guide rail oil, slide rail oil, industrial gear wet goods.
Usually, in additive, introduce the extreme pressure property that sulphur can increase additive, sulphur content is high more, and extreme pressure property is good more.But; With sulphur vegetables oil is vulcanized, after sulphur content acquires a certain degree, (be generally 10%), product is crosslinked serious; Become gelatin material or heavy-gravity product extremely; Oil soluble is poor, can't be used for oil dope and use, and therefore commercially available T404, T405 agent sulphur content all is controlled at below 8%.In addition, adopt sulphur directly to vulcanize as vulcanizing agent, the oil colours pool that obtains is very dark, influences the exterior quality of lubricating oil, has therefore limited the application of such anti-wear agent.
Summary of the invention
The objective of the invention is to overcome in the prior art vegetables oil sulfidation sulphur content improves and causes poor, the saturate shortcoming of polarization anti-wear agent oil soluble; Provide a kind of oil soluble good, and have the extreme pressure anti-wear additives and preparation method thereof of good extreme pressure property, abrasion resistance and antioxidant property and the lubricating oil composition that contains this extreme pressure anti-wear additives.
The invention provides a kind of extreme pressure anti-wear additives, wherein, this anti-wear agent is the common sulfurized product of sulphur phosphoric acid zinc salt and alkene; Said sulphur phosphoric acid zinc salt is the compound by formula (1) expression:
Formula (1)
Wherein, X
1, X
2, X
3And X
4Be by the group shown in formula (2), formula (3), formula (4), formula (5) or the formula (6) independently of one another:
Formula (2) formula (3)
Formula (4) formula (5) formula (6)
R wherein
1, R
2, R
3, R
4, R
5, r
6And R
13Be respectively the alkyl or alkenyl that carbonatoms is 8-24.
The present invention also provides a kind of preparation method of extreme pressure anti-wear additives, and wherein, this method comprises glycerin fatty acid ester and thiophosphoric anhydride reaction, obtains the sulphur phosphoric acid product; Phosphorus sulfuric acid product and zinc oxide and/or zinc hydroxide reaction with gained obtain the sulphur phosphoric acid zinc salt; Then in the presence of sulphur, the sulphur phosphoric acid zinc salt and the alkene of gained is vulcanized jointly, wherein, said glycerin fatty acid ester is one or more in the compound shown in formula (7), formula (8), formula (9) and the formula (10):
Formula (7) formula (8)
Formula (9) formula (10)
R wherein
7, R
8, R
9, R
10, R
11And R
12Be respectively the alkyl or alkenyl that carbonatoms is 8-24.
The present invention also provides a kind of lubricating oil composition, and said composition contains base oil and anti-wear agent, and wherein, said anti-wear agent is an extreme pressure anti-wear additives provided by the invention.
For obtaining the vegetable oil derivatives additive of high extreme pressure property, the present invention adopts the sulphur phosphatization to vegetables oil elder generation, and the scheme of revulcanization further increases sulphur content.The phosphoric of introducing in the product has simultaneously also played good wear-resistant effect.The sulfide aliphatic acid ester sulphur phosphoric acid acid zinc salt that the present invention obtains, T405 is shallow for color when compared commodity sulfurized olefin cotton oil.Sulphur content is higher than general sulfurized olefin cotton oil product, and extreme pressure property improves, and the phosphoric of introducing has also improved abrasion resistance and antioxygen property.Be applicable to each class lubricating oil such as engine oil, gear oil, the chain saw wet goods is applicable to that also with the vegetables oil or derivatives thereof be in the lubricating oil of base oil.
Embodiment
Extreme pressure anti-wear additives provided by the invention is the common sulfurized product of sulphur phosphoric acid zinc salt and alkene; Said sulphur phosphoric acid zinc salt is the compound by formula (1) expression:
Formula (1)
Wherein, X
1, X
2, X
3And X
4Can be the group shown in formula (2), formula (3), formula (4), formula (5) or the formula (6) independently of one another:
Formula (2) formula (3)
Formula (4) formula (5) formula (6)
R wherein
1, R
2, R
3, R
4, R
5, R
6And R
13Can be respectively the alkyl or alkenyl that carbonatoms is 8-24.
Said alkene can be selected from one or more in the terminal olefin that carbonatoms is 8-30, and under the preferable case, said alkene is selected from one or more in the terminal olefin that carbonatoms is 14-18.
According to anti-wear agent provided by the invention, wherein, said sulfurized condition comprises that curing temperature can be 100-160 ℃, and curing time can be 2-8 hour, is preferably 3.5-4.5 hour.
According to anti-wear agent provided by the invention, wherein, be benchmark with the total amount of this anti-wear agent; The content of element sulphur can be 10-20 weight %; The content of phosphoric can be 1-5 weight %, and the content of zinc element can be 1-5 weight %, and surplus is carbon, protium and oxygen element.
The preparation method of the extreme pressure anti-wear additives that the present invention also provides comprises glycerin fatty acid ester and thiophosphoric anhydride reaction, obtains the sulphur phosphoric acid product; Phosphorus sulfuric acid product and zinc oxide and/or zinc hydroxide reaction with gained obtain the sulphur phosphoric acid zinc salt; Then in the presence of sulphur, the sulphur phosphoric acid zinc salt and the alkene of gained is vulcanized jointly, wherein, said glycerin fatty acid ester is one or more in the compound shown in formula (7), formula (8), formula (9) and the formula (10):
Formula (7) formula (8)
Formula (9) formula (10)
R wherein
7, R
8, R
9, R
10, R
11And R
12Be respectively the alkyl or alkenyl that carbonatoms is 8-24.
The temperature of said glycerin fatty acid ester and thiophosphoric anhydride reaction can be 20-120 ℃; Be preferably 60-90 ℃, the reaction times can be 1-8 hour, is preferably 1.5-3 hour; The weight ratio of thiophosphoric anhydride and glycerin fatty acid ester can be 2-60: 100, be preferably 10-30: 100.
Following formula schematically shows the reaction process of monoglyceride and bis-fatty acid glyceryl ester and thiophosphoric anhydride respectively:
Wherein, said glycerin fatty acid ester can be in the compound shown in formula (7), formula (8), formula (9) and the formula (10) one or more, can be commercially available, and also can be made by vegetables oil and glycerine reaction.Because therefore vegetables oil wide material sources and cheap can practice thrift cost with vegetables oil and glycerine reaction obtain fatty acid glyceryl ester.Said vegetables oil can be the vegetables oil of triglyceride structure for various staples, for example, can be in Oleum Gossypii semen, VT 18, Uni Ace R, plam oil, Oleum Cocois and the peanut oil one or more.
The temperature of said vegetables oil and glycerine reaction can be 150-300 ℃, is preferably 175-250 ℃, and more preferably 220-230 ℃, the reaction times can be 0.5-12 hour, is preferably 2-8 hour, more preferably 3-5 hour.The weight ratio of glycerine and vegetables oil can be 5-75: 100, be preferably 10-50: 100.More preferably under the situation, make glycerine excessive, for example, the weight ratio that makes glycerine and vegetables oil is 30-50: 100, and after reaction finishes, separate and remove settled glycerine.
In order to improve speed of response, the reaction of vegetables oil and glycerine can be used catalyzer.This catalyzer can be used for the catalyzer of transesterification reaction for routine; For example; Can be in alkalimetal oxide, alkaline earth metal oxide, alkali metal hydroxide, alkaline earth metal hydroxides, tin compound, aluminum alkoxide and the phenoxy aluminium one or more, be preferably in alkalimetal oxide, alkaline earth metal oxide, alkali metal hydroxide and the alkaline earth metal hydroxides one or more.Vegetables oil with 100 weight parts is a benchmark, and this catalyst consumption can restrain for 0.1-3, is preferably the 0.5-1.5 gram.
Mainly contain triglyceride in the vegetables oil, following formula schematically shows the transesterification reaction of vegetables oil (that is triglyceride) and glycerine:
Final product is the mixture for the compound shown in formula (7), formula (8), formula (9) and the formula (10).
The temperature of said sulphur phosphoric acid product and zinc oxide and/or zinc hydroxide reaction can be 50-120 ℃; Be preferably 70-90 ℃; Reaction times can be 1-8 hour, is preferably 2-4 hour, and the weight ratio of zinc oxide and/or zinc hydroxide and sulphur phosphoric acid product can be 5-50: 100.
This reaction can be represented with following equation:
2(XO)
2PSSH+ZnO→[(XO)
2PSS]
2Zn+H
2O
Wherein, product [(XO)
2PSS]
2Zn is the compound shown in the formula (1).
Said common sulfurized temperature can be 100-160 ℃, and curing time can be 2-8 hour, is preferably 3-5 hour; With respect to the sulphur phosphoric acid zinc salt of 100 weight parts, the consumption of alkene can be the 15-50 weight part, is preferably the 25-35 weight part, and the consumption of sulphur can be the 15-50 weight part, is preferably the 20-30 weight part.
Wherein, said alkene is selected from one or more in the terminal olefin that carbonatoms is 8-30, and under the preferable case, said alkene is selected from one or more in the terminal olefin that carbonatoms is 14-18.
The lubricant compositions that the present invention also provides contains base oil and anti-wear agent, and wherein, said anti-wear agent is an extreme pressure anti-wear additives provided by the invention.Base oil with 100 weight parts is a benchmark, and the content of said anti-wear agent can be the 0.2-5 weight part, is preferably the 0.5-4 weight part.Wherein, said base oil can be various hydro carbons lubricant bases, for example can be in I. C. engine oil, precoating oil, gear oil, machinery oil, hydraulicefficiency oil, spindle oil, metal working oil and the railway grease one or more.
Below, will be explained in more detail the present invention through embodiment.
Embodiment 1
Present embodiment is used to explain the preparation of extreme pressure anti-wear additives of the present invention.
(1) 500 gram Oleum Gossypii semens, 300 gram glycerine, 4 are restrained in the there-necked flask of 1000 milliliters of CaO addings, open and stir, be warming up to 200 ℃, kept thermotonus 2 hours.Be cooled to 60 ℃ then, the glycerine of separate and subside, the hydrochloric acid that adds 1mol/L makes system be acid (pH value=4), washes 3 times (using 300 ml deionized water) at every turn, remove free water content with SODIUM SULPHATE ANHYDROUS 99PCT after, in 115 ℃ baking oven, be incubated 3 hours.Add 60 gram P then
2S
5, the unnecessary P of filtering after reacting 2 hours under 60 ℃
2S
5In filtrating, add 30 gram ZnO, be warming up to 80 ℃ of reactions 4 hours, filtering precipitate obtains the sulphur phosphoric acid zinc salt.
(2) the 100 sulphur phosphoric acid zinc salts that make of gram steps (1) and 30 gram 1-hexadecylenes and 25 gram sulphur are joined in 250 milliliters the there-necked flask,, filter then and obtain brown oily liquids, be product, remember and make A1 in 120 ℃ of nitrogen protections reaction 5 hours down.
Embodiment 2
Present embodiment is used to explain the preparation of extreme pressure anti-wear additives of the present invention.
(1) 500 gram VT 18s, 180 gram glycerine, 4 are restrained in the there-necked flask of 1000 milliliters of NaOH addings, open and stir, be warming up to 220 ℃, kept thermotonus 4 hours.Be cooled to 60 ℃ then, the glycerine of separate and subside, the hydrochloric acid that adds 1mol/L makes system be acid (pH value=4), washes 3 times (using 300 ml deionized water) at every turn, remove free water content with SODIUM SULPHATE ANHYDROUS 99PCT after, in 115 ℃ baking oven, be incubated 3 hours.Add 80 gram P then
2S
5, the unnecessary P of filtering after reacting 2 hours under 70 ℃
2S
5In filtrating, add 35 gram ZnO, be warming up to 80 ℃ of reactions 4 hours, filtering precipitate obtains the sulphur phosphoric acid zinc salt.
(2) the sulphur phosphoric acid zinc salt that 100 gram steps (1) is made restrains in the there-necked flask of 250 milliliters of sulphur addings with 25 gram 1-octadecylenes and 20, and reaction is 4 hours under 140 ℃ of nitrogen protections, filters then and obtains brown oily liquids, is product, remembers and makes A2.
Embodiment 3
Present embodiment is used to explain the preparation of extreme pressure anti-wear additives of the present invention.
(1) 100 gram glyceryl monostearates (CP, content＞98%) and 50 is restrained in the there-necked flask of 500 milliliters of hexanaphthenes addings, open and stir, be warming up to 60 ℃ it is dissolved fully.Add 30 gram P
2S
5, reacted 3 hours down at 60 ℃, then the unnecessary P of filtering
2S
5In filtrating, add 20 gram ZnO, be warming up to 70 ℃ of reactions 4 hours, filtering precipitate will be filtrated at 70 ℃, carry out underpressure distillation under the 1973Pa pressure, remove hexanaphthene, obtain the sulphur phosphoric acid zinc salt.
(2) the sulphur phosphoric acid zinc salt that 100 gram steps (1) is made restrains in the there-necked flask of 250 milliliters of sulphur addings with 35 gram 1-hexadecylenes and 30, and reaction is 3 hours under 150 ℃ of nitrogen protections, filters then and obtains brown oily liquids, is product, remembers and makes A3.
Embodiment 4-6
Embodiment 4-6 is used for the application as oil dope of extreme pressure anti-wear additives that illustrative embodiment 1,2 and 3 makes, lubricating oil composition promptly provided by the invention.
Extreme pressure anti-wear additives A1, A2 and the A3 that embodiment 1-3 is made is made into test with the 100SN hydrogenated base oil respectively and uses lubricating oil.Base oil with 100 weight parts is a benchmark, and the add-on of extreme pressure anti-wear additives A1, A2 and A3 is respectively 1 weight part, 2 weight parts and 3 weight parts, and the lubricating oil sample that makes is remembered respectively and made B1, B2 and B3.
Comparative Examples 1
This Comparative Examples is used to explain the application of T405 as oil dope.
T405 and 100SN hydrogenated base oil are made into test use lubricating oil.Base oil with 100 weight parts is a benchmark, and the add-on of T405 is 1 weight part, and the lubricating oil sample note that makes is made C1.
Performance test
Colourity: measure according to GB/T 6540 petroleum products color measurenent methods.
Supporting capacity: the last non seizure load of the lubricating oil sample that embodiment 4-6 and Comparative Examples 1 is made according to GB/T 3142 lubricating oil supporting capacity assay methods (four ball methods) is tested.
Oxidation-resistance: the lubricating oil sample according to SH/T 0719-2002 oil ageing assay method inductive phase makes embodiment 4-6 and Comparative Examples 1 under 170 ℃ is carried out the oxidation-resistance test.
Abrasion resistance: decrease performance measurement method (four-ball tester method) according to SH/T 0189 lubrication oil antiwear and measure lubricating oil sample that embodiment 4-6 and Comparative Examples 1 make at experiment condition 1200r/min, 75 ℃, the long term wear wear scar diameter during 30min.
Test result is listed in table 1.
Table 1
| Numbering | Colourity | Last non seizure load/N | Oxidation induction period/min | Wear scar diameter/mm |
| B1 | 2 | 833 | 44.9 | 0.45 |
| B2 | 2 | 841 | 46.5 | 0.44 |
| B3 | 2.5 | 845 | 47.6 | 0.44 |
| C1 | 3 | 637 | 20.1 | 0.43 |
Data from table 1 can be found out, compare with the lubricating oil sample of preparing with T405 with the lubricating oil sample of extreme pressure anti-wear additives preparation of the present invention, have better supporting capacity, anti-oxidative stability and abrasion resistance.
Claims (19)
1. an extreme pressure anti-wear additives is characterized in that, this anti-wear agent is the common sulfurized product of sulphur phosphoric acid zinc salt and alkene; Said sulphur phosphoric acid zinc salt is the compound by formula (1) expression:
Wherein, X
1, X
2, X
3And X
4Be by the group shown in formula (2), formula (3), formula (4), formula (5) or the formula (6) independently of one another:
R wherein
1, R
2, R
3, R
4, R
5, R
6And R
13Be respectively the alkyl or alkenyl that carbonatoms is 8-24.
2. anti-wear agent according to claim 1, wherein, said alkene is selected from one or more in the terminal olefin that carbonatoms is 8-30.
3. anti-wear agent according to claim 1 and 2, wherein, said alkene is selected from one or more in the terminal olefin that carbonatoms is 14-18.
4. anti-wear agent according to claim 1, wherein, said sulfurized condition comprises that curing temperature is 100-160 ℃, curing time is 2-8 hour; With respect to the sulphur phosphoric acid zinc salt of 100 weight parts, the consumption of alkene is the 15-50 weight part, and the consumption of sulphur is the 15-50 weight part.
5. according to claim 1 or 4 described anti-wear agents, wherein, be benchmark with the total amount of this anti-wear agent; The content of element sulphur is 10-20 weight %; The content of phosphoric is 1-5 weight %, and the content of zinc element is 1-5 weight %, and surplus is carbon, protium and oxygen element.
6. the preparation method of the said anti-wear agent of claim 1 is characterized in that, this method comprises glycerin fatty acid ester and thiophosphoric anhydride reaction, obtains the sulphur phosphoric acid product; Phosphorus sulfuric acid product and zinc oxide and/or zinc hydroxide reaction with gained obtain the sulphur phosphoric acid zinc salt; Then in the presence of sulphur, the sulphur phosphoric acid zinc salt and the alkene of gained is vulcanized jointly, wherein, said glycerin fatty acid ester is one or more in the compound shown in formula (7), formula (8), formula (9) and the formula (10):
R wherein
7, R
8, R
9, R
10, R
11And R
12Be respectively the alkyl or alkenyl that carbonatoms is 8-24.
7. method according to claim 6, wherein, the condition of said glycerin fatty acid ester and thiophosphoric anhydride reaction comprises that temperature of reaction is 20-120 ℃, and the reaction times is 1-8 hour, and the weight ratio of thiophosphoric anhydride and glycerin fatty acid ester is 2-60: 100.
8. according to claim 6 or 7 described methods, wherein, said glycerin fatty acid ester is through making vegetables oil and glycerine reaction.
9. method according to claim 8, wherein, the condition of vegetables oil and glycerine reaction comprises that temperature of reaction is 150-300 ℃, and the reaction times is 0.5-12 hour, and the weight ratio of glycerine and vegetables oil is 5-75: 100.
10. method according to claim 9, wherein, the condition of vegetables oil and glycerine reaction comprises that temperature of reaction is 175-250 ℃, and the reaction times is 2-8 hour, and the weight ratio of glycerine and vegetables oil is 10-50: 100.
11. method according to claim 8, wherein, said vegetables oil is one or more in Oleum Gossypii semen, VT 18, Uni Ace R, plam oil, Oleum Cocois and the peanut oil.
12. method according to claim 6, wherein, the condition of said sulphur phosphoric acid product and zinc oxide reaction comprises that temperature of reaction is 50-120 ℃, and the reaction times is 1-8 hour, and the weight ratio of zinc oxide and/or zinc hydroxide and sulphur phosphoric acid product is 5-50: 100.
13. method according to claim 6, wherein, said cure conditions comprises that curing temperature is 100-160 ℃, and curing time is 2-8 hour; With respect to the sulphur phosphoric acid zinc salt of 100 weight parts, the consumption of alkene is the 15-50 weight part, and the consumption of sulphur is the 15-50 weight part.
14. according to claim 6 or 13 described methods, wherein, said alkene is selected from one or more in the terminal olefin that carbonatoms is 8-30.
15. according to claim 6 or 13 described methods, wherein, said alkene is selected from one or more in the terminal olefin that carbonatoms is 14-18.
16. a lubricating oil composition, said composition contains base oil and anti-wear agent, it is characterized in that, said anti-wear agent is any described anti-wear agent among the claim 1-5.
17. lubricating oil composition according to claim 16 wherein, is a benchmark with the base oil of 100 weight parts, the content of said anti-wear agent is the 0.2-5 weight part.
18. according to claim 16 or 17 described lubricating oil compositions, wherein, said base oil is selected from one or more in I. C. engine oil, precoating oil, gear oil, machinery oil, hydraulicefficiency oil, metal working oil and the railway grease.
19. lubricating oil composition according to claim 18, wherein, said machinery oil is a spindle oil.
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| CN107974326B (en) * | 2016-10-25 | 2021-06-11 | 中国石油化工股份有限公司 | Antioxidant antiwear agent, preparation method thereof and lubricating oil composition |
| CN111057102B (en) | 2018-10-16 | 2024-03-12 | 中国石油化工股份有限公司 | Organophosphorus compounds, preparation method and application thereof |
| CN114806677A (en) * | 2022-05-10 | 2022-07-29 | 新乡市瑞丰新材料股份有限公司 | Extreme pressure antiwear agent special for gear oil and preparation method thereof |
| CN115651748B (en) * | 2022-09-23 | 2023-05-26 | 东莞市颖兴金属表面处理材料有限公司 | Saponified lubricant and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1033834A (en) * | 1988-10-11 | 1989-07-12 | 淄博塑料助剂厂 | The preparation method of polyhydric alcohol fatty acid ester |
| US5013465A (en) * | 1987-12-23 | 1991-05-07 | Exxon Chemical Patents, Inc. | Dithiophosphates |
| CN1599787A (en) * | 2001-06-01 | 2005-03-23 | 克鲁普顿公司 | Oxadiazole additives for lubricants |
-
2008
- 2008-10-23 CN CN 200810224384 patent/CN101724492B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013465A (en) * | 1987-12-23 | 1991-05-07 | Exxon Chemical Patents, Inc. | Dithiophosphates |
| CN1033834A (en) * | 1988-10-11 | 1989-07-12 | 淄博塑料助剂厂 | The preparation method of polyhydric alcohol fatty acid ester |
| CN1599787A (en) * | 2001-06-01 | 2005-03-23 | 克鲁普顿公司 | Oxadiazole additives for lubricants |
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