CN104927972A - Antirust oil composition - Google Patents
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- CN104927972A CN104927972A CN201410106175.0A CN201410106175A CN104927972A CN 104927972 A CN104927972 A CN 104927972A CN 201410106175 A CN201410106175 A CN 201410106175A CN 104927972 A CN104927972 A CN 104927972A
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Abstract
The invention provides an antirust oil composition, a method for improving the damping and noise-reducing performance of antirust oil, and a method for improving the antirust property of antirust oil. The provided antirust oil composition comprises Mannich base, an antirust agent, and lubricant base oil accounting for the most weight; wherein the Mannich base is prepared by the following steps: (1) in the presence of an alkylation reaction catalyst, reacting phenol and/or mono-o-alkyl phenol with polyolefin, and collecting the alkylation products; (2) carrying out Mannich reactions among the alkylation products obtained in the step (1), polyethylene-polyamine, and aldehyde to obtain an intermediate; (3) carrying out secondary Mannich reactions among the intermediate obtained in the step (2), p-hydroxyl diphenylamine derivatives and aldehyde, and collecting the finally-obtained Mannich base. The obtained antirust oil composition has an excellent damping, noise-reducing, and antirust performance, and can fully meet the application requirements of low-noise bearing.
Description
Technical field
The present invention relates to a kind of anticorrosive oil composition, particularly relate to a kind of low noise anticorrosive oil composition with vibration and noise reducing performance.
Background technology
In recent years, the development of the bearing industry such as China's automobile bearing, precision machine tool bearing, railway bearing, household electrical appliances bearing fast.Bearing is widely used in the standardized component of all kinds of machinery, is generally made up of lasso (inner ring, outer ring) rolling body (as steel ball) and retainer.Except the bearing of some special purposes is made up of non-metallic material rolling body and retainer, most bearing is all made up of metallic substance.It is ubiquitous problem that metallic substance produces corrosion in atmospheric environment.Bearing rust then can affect its class of precision, reduces its work-ing life, even scraps, or in use accidents caused.
Along with the development of household electrical appliance and universal, household electrical appliances main frame manufacturer proposes more and more stricter requirement to bear vibration and noise objective.The micro precision bearing that household electric appliances generally use not only requires that vibration values is low, sound without exception, and requires that bearing has certain vibration life and noise lifetime.Therefore, require that bearing slushing oil has good vibration and noise reducing performance.
Numerous reports and patent documentation is had both at home and abroad about water-base cutting fluid composition.Patent CN1136075A reports a kind of high purity, vibration-absorbing and rustproof oil.This slushing oil is a kind of high cleanliness factor vibration damping slushing oil of bearing, patent determines the rational formula of oil product, and has carried out the art breading such as refining, filtration to related components, and the cleanliness factor of oil product is greatly improved.Patent CN102344848A reports a kind of bearing anti-corrosive oil composition, comprises sulfonate and tetrahydroglyoxaline succinic acid swallow, said composition oil molten good stability, place for a long time not skinning, do not produce precipitation.
US5725612 reports a kind of Mannich base and manufacture method thereof.The alkyl ortho-cresol that this Mannich base is replaced by alkyl and aldehyde, amine react manufacture and obtain, effective in the generation of suppression engine deposits as purification agent.A kind of Mannich base and manufacture method thereof is reported in US20040168364.This Mannich base reacts manufacture by phenolic compound and aldehyde, amine and obtains, and can suppress the generation of engine deposits as purification agent.
The effect of slushing oil more and more tends to diversification.Bearing slushing oil, except having good rust inhibition, also should have certain vibration damping, Noise Reduction, meets the particular requirement that the protection of the metal bearing be under multiple envrionment conditions and bearing use to make product.
Summary of the invention
The invention provides a kind of method of anticorrosive oil composition and raising slushing oil vibration and noise reducing performance, improve the method for slushing oil rustless property.
Anticorrosive oil composition of the present invention comprises the lubricant base of Mannich base, rust-preventive agent and primary amount, and wherein said Mannich base is prepared by following methods:
(1) under catalyst for alkylation reaction exists, phenol and/or single ortho alkyl phenol and polyolefine are reacted, collect alkylate;
(2) alkylate step (1) obtained and polyamines polyene, aldehyde generation Mannich reaction, obtain intermediate product;
(3) intermediate product of step (2) and p-hydroxydiphenylamine derivative, aldehyde be there is second time Mannich reaction, collect and obtain final Mannich base.
In step (1), described polyolefine is by ethene, propylene, C
4-C
10alpha-olefin is polymerized separately or copolymerization and the polyolefine obtained, described C
4-C
10alpha-olefin can select in n-butene, iso-butylene, positive amylene, n-hexylene, positive octene and positive decene one or more, preferred polyisobutene, described polyolefinic number-average molecular weight is 300-3000, preferred 500-2000, more preferably 500-1500.
Described single ortho alkyl phenol preferred alkyl carbonatoms is single ortho alkyl phenol of 1-6, most preferably ortho-cresol.
Described catalyst for alkylation reaction is selected from Lewis acid catalyst, one or more of preferred aluminum chloride, boron trifluoride, tin tetrachloride, titanium tetrabromide, boron trifluoride phenol, boron trifluoride alcohol complex and boron trifluoride ether complex, most preferably boron trifluoride ethyl ether complex and/or boron trifluoride methanol.
Mol ratio between described polyolefine, phenol and/or single ortho alkyl phenol, catalyzer is 1:1-3:0.1-0.5, preferred 1:1.5-3:0.1-0.4, most preferably 1:1.5-3:0.2-0.4.
Reaction times is 0.5h-10h, preferred 1h-8h, most preferably 3h-5h.
Temperature of reaction is 0 DEG C-200 DEG C, preferably 10 DEG C-150 DEG C, most preferably 20 DEG C-100 DEG C.
Need to add solvent in the reaction of step (1), also can add solvent.Described solvent is selected from the hydro carbons of boiling point between 60 DEG C-120 DEG C, such as normal hexane, normal heptane, 60-90 sherwood oil, 90-120 sherwood oil.Described solvent and described polyolefinic mass ratio are 0.5:1-2:1, preferred 0.7:1-1.5:1, most preferably 0.9:1-1.3:1.After step (1) adds solvent participation reaction, by distil process except desolventizing.
In step (2), described polyamines polyene has following general formula:
H
2N(CH
2)
y[(NH(CH
2)
y]
xNH
2
Wherein x is the integer of 0-10, and y is integer 2 or 3.One or more in the preferred diethylenetriamine of described polyamines polyene, triethylene tetramine, tetraethylene pentamine, five ethene hexamines, six ethene seven amine, seven ethene eight amine, eight ethene nine amine, nine ethene ten amine and ten ethene undecylamines, most preferably tetraethylene pentamine.Polyamines polyene can react preparation by ammonia and alkylene dihalide such as dichloro alkanes.
The preferred formaldehyde of described aldehyde, acetaldehyde, C
3-C
7alkanoic, one or more most preferably in paraformaldehyde, paraformaldehyde and formaldehyde.
The alkylate that described step (1) obtains, the mol ratio between described polyamines polyene and described aldehyde are 1:0.3-3:0.1-3.5, preferred 1:0.4-2:0.2-2.5, most preferably 1:0.5-1.5:0.3-2.
The temperature of described Mannich reaction is 50 DEG C-200 DEG C, preferably 60 DEG C-150 DEG C, most preferably 80 DEG C-130 DEG C.
The time of described Mannich reaction is 1h-10h, preferred 2h-8h, most preferably 3h-6h.
Solvent and/or thinner can also be added in the reaction of step (2), described solvent is selected from the hydro carbons of boiling point between 100 DEG C-160 DEG C, such as toluene, dimethylbenzene, No. 150 industrial napthas, the add-on of described solvent is about the 2%-80% of alkylate quality in step (1), preferred 5%-60%, most preferably 5%-30%; Described thinner comprise in mineral lubricating oils, polyolefine, polyethers one or more, the add-on of described thinner is about the 5%-80% of alkylate quality in step (1), preferred 10%-70%, most preferably 10%-60%.
Wherein said mineral lubricating oils can select API I, II, III class mineral lubricant oil base oil, preferably 40 DEG C of viscosity are 20-120 centistoke (cSt), viscosity index at least mineral lubricant oil base oil more than 50, and more preferably 40 DEG C of viscosity are 28-110 centistoke (cSt), the viscosity index mineral lubricant oil base oil at least more than 80.
Described polyolefine is polymerized separately by ethene, propylene, alpha-olefin or copolymerization and the polyolefine obtained, described alpha-olefin comprise in n-butene, iso-butylene, positive amylene, n-hexylene, positive octene and positive decene one or more, preferably 100 DEG C of viscosity is the poly-alpha olefins (PAO) of 2-25 centistoke (cSt), and most preferably 100 DEG C of viscosity are 6-10 centistoke (cSt).Described polyolefinic number-average molecular weight is 500-3000, preferred 700-2500, most preferably 1000-2000.
Described polyethers is the polymkeric substance generated by alcohol and epoxide reaction, and described alcohol is ethylene glycol and/or 1,3-PD, described epoxide is oxyethane and/or propylene oxide, the number-average molecular weight of described polyethers is 500-3000, preferred 700-3000, most preferably 1000-2500.
In step (3), the structure of described p-hydroxydiphenylamine derivative is:
Wherein R
1for H, C1-C8 alkyl, hydroxyl or nitro, preferred H, C1-C4 alkyl or hydroxyl, most preferably H.
In step (3), the preferred formaldehyde of described aldehyde, acetaldehyde, C
3-C
7alkanoic, one or more most preferably in paraformaldehyde, paraformaldehyde and formaldehyde.
The mol ratio of the intermediate product of described step (2), p-hydroxydiphenylamine derivative and described aldehyde is 1:0.3-3:0.1-2, preferred 1:0.3-2:0.1-2, most preferably 1:0.5-1.5:0.3-1.5.
The temperature of described Mannich reaction is 40 DEG C-200 DEG C, preferably 60 DEG C-150 DEG C, most preferably 80 DEG C-130 DEG C.
The time of described Mannich reaction is 1h-10h, preferred 2h-8h, most preferably 3h-6h.
In the compositions of the present invention, described Mannich base accounts for 0.1% ~ 15% of composition total mass, and preferably 0.5% ~ 10%, most preferably 1% ~ 5%.
The rust-preventive agent used in the present composition be selected from sulfonate, alkenyl succinic acid, alkenyl succinate and oxidized petrolatum soap one or more.
Described sulfonate can select in sulfonated petro-leum, sulfonated alkyl naphathalene and alkylbenzene sulfonate one or more.Described sulfonated petro-leum can select in petroleum sodium sulfonate, petrolic magnesium sulfonate, calcium mahogany sulfonate and barium mahogany sulfonate one or more, preferred barium mahogany sulfonate.Described sulfonated alkyl naphathalene can select C6-C12 sulfonated alkyl naphathalene, such as, can select alkaline dinonyl naphthalene sulfonate barium (T705), neutral dinonyl naphthalene sulfonate barium, dinonylnaphthalene sulfonic acid calcium.Described alkylbenzene sulfonate can select C6-C12 alkylbenzene sulfonate, such as, can select Sodium dodecylbenzene sulfonate.
Described alkenyl succinic acid or its salt can select in dodecenylsuccinic acid, 17 alkenyl imidazoline alkenyl succinates (T703), dialkyl succinylsuccinate 17 alkenyl imidazoline salt (HY-10002), amine ethyl 17 alkenyl imidazoline dodecenylsuccinic acid salt and 2-amine ethylenyl tetrahydroglyoxaline alkenyl succinic acid one or more.
Described oxidized petrolatum soap can select oxidized petrolatum barium soap, one or more in oxidized petrolatum magnesium soap and oxidized petrolatum calcium soap, and preferential oxidation petrolatum barium soap, trade names are T743.
The mixture of the preferred sulfonate of described rust-preventive agent and alkenyl succinate, mass ratio is therebetween 20 ~ 2:1, preferably 5 ~ 15:1.
Described rust-preventive agent accounts for 1% ~ 30% of present composition total mass, and preferably 3% ~ 25%, more preferably 5% ~ 20%.
Described lubricant base forms the main ingredient of the present composition, described lubricant base be selected from API I, II, III, IV, V class lubricating oil base oil one or more, one or more in preferred API I, II, III class lubricating oil base oil.
In anticorrosive oil composition of the present invention, preferably add oiliness improver, described oiliness improver can select in benzotriazole lipid acid amine salt, sulfuration haco oil, dimeracid, ethylene glycol fatty acid, sulfuration Oleum Gossypii semen, sulfurized olefin cotton oil, Triphenyl phosphate (TPP), triethyl phosphate, fatty acid butyl ester and ester one or more.
Described oiliness improver preferably accounts for 0.1% ~ 5% of composition total mass, and most preferably 0.2% ~ 3%.
Can also add oxidation inhibitor, viscosity index improver in anticorrosive oil composition of the present invention, and its consumption is from the conventional amount used of this area.
Present invention also offers a kind of method improving slushing oil vibration and noise reducing performance, the method is mixed by the lubricant base of above-mentioned Mannich base, rust-preventive agent and primary amount.
Present invention also offers a kind of method improving slushing oil rustless property, the method is mixed by the lubricant base of above-mentioned Mannich base, rust-preventive agent and primary amount.
Anticorrosive oil composition of the present invention has excellent vibration and noise reducing performance and rustless property, fully can meet the service requirements of low noise bearing, can be widely used in the various bearing industries such as automobile bearing, precision machine tool bearing, railway bearing, household electrical appliances bearing.
Embodiment
Table 1 gives the pharmaceutical chemicals used in embodiment of the present invention.
The specification of table 1 main chemical used and source
Embodiment 1 synthesizing polyisobutylene ortho-cresol
In the 500ml four-hole boiling flask that agitator, thermometer, prolong and dropping funnel are housed, add the polyisobutene (Mn=1000) of 34.93g (0.323mol) ortho-cresol, the boron trifluoride diethyl etherate catalyzer of 6.88g (0.048mol), 100ml normal hexane solvent and 161.61g (0.162mol) at 80 DEG C of reaction 2h.After reaction terminates, functional quality mark be the potassium hydroxide solution cleaning reaction mixture of 5% once, and be washed to neutral remove catalyzer with hot water, then underpressure distillation removes desolventizing and unreacted ortho-cresol.The hydroxyl valency of synthetic product polyisobutene ortho-cresol is 53.49mg/g.Hydroxy value measuring is with reference to the acetic anhydride method in GB/T7383-2007.
Example reaction formula is as follows:
Embodiment 2
Polyisobutene ortho-cresol 47.16g (0.045mol) obtained in embodiment 1 is added to 500ml to be under nitrogen protection equipped with in four mouthfuls of beakers of agitator, thermometer and skimmer; then the quadrol of 2.70g (0.045mol), 3.83g (0.047mol) formaldehyde is added; and the toluene adding 47ml is as reaction solvent; after 80 DEG C of reaction 1.5h; be cooled to room temperature; add the p-hydroxydiphenylamine of 4.17g (0.0225mol), 3.83g (0.047mol) formaldehyde, at 70 DEG C of reaction 1h.After question response terminates, underpressure distillation removes a small amount of water of desolventizing and generation, obtains final Mannich base purification agent.Example reaction formula is as follows:
Or it is a small amount of
Embodiment 3
Polyisobutene ortho-cresol 53.37g (0.051mol) obtained in embodiment 1 is added to 500ml to be under nitrogen protection equipped with in four mouthfuls of beakers of agitator, thermometer and skimmer; then the triethylene tetramine of 7.46g (0.051mol), 4.38g (0.054mol) formaldehyde is added; and the dimethylbenzene adding 54ml is as reaction solvent; after 100 DEG C of reaction 1.5h; be cooled to room temperature; add 5.87g (0.0255mol) 4-hydroxyl-2'-nitrodiphenylamine, 4.38g (0.054mol) formaldehyde, at 80 DEG C of reaction 1h.After question response terminates, underpressure distillation removes a small amount of water of desolventizing and generation, obtains final Mannich base purification agent.Example reaction formula reference example 2.
Embodiment 4
Polyisobutene ortho-cresol 58.80g (0.056mol) obtained in embodiment 1 is added to 500ml to be under nitrogen protection equipped with in four mouthfuls of beakers of agitator, thermometer and skimmer; then the diethylenetriamine of 2.89g (0.028mol), 4.78g (0.059mol) formaldehyde is added; and the toluene adding 53ml is as reaction solvent; after 100 DEG C of reaction 1.5h; be cooled to room temperature; add 2.59g (0.014mol) p-hydroxydiphenylamine, 2.39g (0.029mol) formaldehyde, at 80 DEG C of reaction 1h.After question response terminates, underpressure distillation removes a small amount of water of desolventizing and generation, obtains final Mannich base purification agent.
Embodiment 5
Polyisobutene ortho-cresol 40.01g (0.038mol) obtained in embodiment 1 is added to 500ml to be under nitrogen protection equipped with in four mouthfuls of beakers of agitator, thermometer and skimmer; then the tetraethylene pentamine of 3.61g (0.019mol), 3.25g (0.040mol) formaldehyde is added; and the dimethylbenzene adding 38ml is as reaction solvent; after 80 DEG C of reaction 1.5h; be cooled to room temperature; add 4 of 1.91g (0.0095mol); 4'-diamino biphenol, 1.63g (0.020mol) formaldehyde, at 70 DEG C of reaction 1h.After question response terminates, underpressure distillation removes a small amount of water of desolventizing and generation, obtains final Mannich base purification agent.
Embodiment 4,5 can see following example reaction formula:
Comparative example 1 synthesizing mannich alkali
Polyisobutene ortho-cresol 47.16g (0.045mol) obtained in embodiment 1 is added to 500ml to be under nitrogen protection equipped with in four mouthfuls of beakers of agitator, thermometer and skimmer; then the quadrol of 2.70g (0.045mol), 3.83g (0.047mol) formaldehyde is added; and the toluene adding 47ml is as reaction solvent, after 80 DEG C of reaction 1.5h.After reaction terminates, underpressure distillation removes a small amount of water of desolventizing and generation, obtains final Mannich base.
Some additives added in slushing oil or lubricant base as follows:
Contrast Mannich base, prepares by the embodiment 2 in CN103374085A, is labeled as DQJ-1;
Contrast Mannich base, prepares by the embodiment 4 in CN103374085A, is labeled as DQJ-2;
Contrast Mannich base, prepares by the embodiment 5 in CN103374085A, is labeled as DQJ-3;
Contrast Mannich base, prepares by the embodiment 6 in CN103374085A, is labeled as DQJ-4;
Rust-preventive agent, alkaline dinonyl naphthalene sulfonate barium, new capital, Chengdu petroleum additive factory, T705;
Rust-preventive agent, 17 alkenyl imidazoline alkenyl succinates, the emerging petroleum additive limited liability company in Jinzhou, T703;
Oiliness improver, 124 Triazole lipid acid amine salt, Ning Jiang chemical plant, Nanjing, T406;
Lubricant base, 100SN(40 DEG C of viscosity is 22.29mm
2/ s);
Lubricant base, 150SN(40 DEG C of viscosity is 29.40mm
2/ s).
The embodiment 6 ~ 10 of low noise slushing oil and comparative example 2 ~ 6
The embodiment 6 ~ 10 of low noise slushing oil and the formula composition of comparative example 2 ~ 6 are in table 1.Component each in table joined and be in harmonious proportion in container, 40 DEG C ~ 90 DEG C heating, mixing time is generally 1h ~ 6h, and preparation obtains embodiment and the comparative example of anticorrosive oil composition respectively.
Respectively these low noise anticorrosive oil compositions are surveyed the copper corrosion (GB/T5096) of slushing oil, humid heat test (GB/T2361), salt-fog test (SH/T0081), lamination experiment (SH/T0692 appendix A) and vibration values (SO910 bear vibration tester) as test sample, its test result is in table 1.
Table 1
Claims (13)
1. an anticorrosive oil composition, comprise the lubricant base of Mannich base, rust-preventive agent and primary amount, wherein said Mannich base is prepared by following methods: (1) is under catalyst for alkylation reaction exists, phenol and/or single ortho alkyl phenol and polyolefine are reacted, collects alkylate; (2) alkylate step (1) obtained and polyamines polyene, aldehyde generation Mannich reaction, obtain intermediate product; (3) intermediate product of step (2) and p-hydroxydiphenylamine derivative, aldehyde be there is second time Mannich reaction, collect and obtain final Mannich base.
2. according to composition according to claim 1, it is characterized in that, in the step (1) of the described Mannich base of preparation, described polyolefine is by ethene, propylene, C
4-C
10alpha-olefin is polymerized separately or copolymerization and the polyolefine obtained, described polyolefinic number-average molecular weight is 300-3000, described single ortho alkyl phenol preferred alkyl carbonatoms is single ortho alkyl phenol of 1-6, described catalyst for alkylation reaction is selected from Lewis acid catalyst, and the mol ratio between described polyolefine, phenol and/or single ortho alkyl phenol, catalyzer is 1:1-3:0.1-0.5.
3. according to composition according to claim 1, it is characterized in that, in the step (2) of the described Mannich base of preparation, described polyamines polyene has following general formula:
H
2N(CH
2)
y[(NH(CH
2)
y]
xNH
2
Wherein x is the integer of 0-10, and y is integer 2 or 3, and described aldehyde is selected from formaldehyde, acetaldehyde, C
3-C
7alkanoic, the alkylate that described step (1) obtains, the mol ratio between described polyamines polyene and described aldehyde are 1:0.3-3:0.1-3.5.
4. according to composition according to claim 1, it is characterized in that, in the step (3) of the described Mannich base of preparation, the structure of described p-hydroxydiphenylamine derivative is:
Wherein R
1for H, C1-C8 alkyl, hydroxyl or nitro, described aldehyde is selected from formaldehyde, acetaldehyde, C
3-C
7alkanoic, the mol ratio of the intermediate product of described step (2), p-hydroxydiphenylamine derivative and described aldehyde is 1:0.3-3:0.1-2, and the temperature of described Mannich reaction is 40 DEG C-200 DEG C.
5. according to composition according to claim 1, it is characterized in that, described Mannich base accounts for 0.1% ~ 15% of composition total mass.
6., according to composition according to claim 1, it is characterized in that, described rust-preventive agent be selected from sulfonate, alkenyl succinic acid, alkenyl succinate and oxidized petrolatum soap one or more.
7., according to composition according to claim 6, it is characterized in that, described sulfonate be selected from sulfonated petro-leum, sulfonated alkyl naphathalene and alkylbenzene sulfonate one or more.
8. according to composition according to claim 6, it is characterized in that, described alkenyl succinic acid or its salt be selected from dodecenylsuccinic acid, 17 alkenyl imidazoline alkenyl succinates (T703), dialkyl succinylsuccinate 17 alkenyl imidazoline salt (HY-10002), amine ethyl 17 alkenyl imidazoline dodecenylsuccinic acid salt and 2-amine ethylenyl tetrahydroglyoxaline alkenyl succinic acid one or more.
9. according to composition according to claim 1, it is characterized in that, described rust-preventive agent is selected from the mixture of sulfonate and alkenyl succinate, and mass ratio is therebetween 20 ~ 2:1.
10. according to composition according to claim 1, it is characterized in that, described rust-preventive agent accounts for 1% ~ 30% of present composition total mass.
11. according to the composition one of claim 1-10 Suo Shu, it is characterized in that, oiliness improver is added in described anticorrosive oil composition, described oiliness improver be selected from benzotriazole lipid acid amine salt, sulfuration haco oil, dimeracid, ethylene glycol fatty acid, sulfuration Oleum Gossypii semen, sulfurized olefin cotton oil, Triphenyl phosphate (TPP), triethyl phosphate, fatty acid butyl ester and ester one or more, described oiliness improver accounts for 0.1% ~ 5% of composition total mass.
12. 1 kinds of methods improving slushing oil vibration and noise reducing performance, the method is mixed by the lubricant base of the Mannich base described in one of claim 1-10, rust-preventive agent and primary amount.
13. 1 kinds of methods improving slushing oil rustless property, the method is mixed by the lubricant base of the Mannich base described in one of claim 1-10, rust-preventive agent and primary amount.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113072674A (en) * | 2020-01-03 | 2021-07-06 | 万华化学集团股份有限公司 | Heat-sensitive tertiary amine catalyst, quaternized derivative thereof, preparation and application |
| CN115322824A (en) * | 2022-03-31 | 2022-11-11 | 南京科润工业介质股份有限公司 | Anti-rust oil composition |
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|---|---|---|---|---|
| US5633326A (en) * | 1989-12-13 | 1997-05-27 | Exxon Chemical Patents Inc. | Polyolefin-substituted amines grafted with poly(aromatic-N-monomers) for oleaginous compositions |
| US5725612A (en) * | 1996-06-07 | 1998-03-10 | Ethyl Corporation | Additives for minimizing intake valve deposits, and their use |
| CN1260332C (en) * | 2000-12-08 | 2006-06-21 | 申保安 | Full loss mechanical lubricating oil |
| CN103374085A (en) * | 2012-04-26 | 2013-10-30 | 中国石油化工股份有限公司 | Mannich base and manufacturing method and application thereof |
-
2014
- 2014-03-20 CN CN201410106175.0A patent/CN104927972B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5633326A (en) * | 1989-12-13 | 1997-05-27 | Exxon Chemical Patents Inc. | Polyolefin-substituted amines grafted with poly(aromatic-N-monomers) for oleaginous compositions |
| US5725612A (en) * | 1996-06-07 | 1998-03-10 | Ethyl Corporation | Additives for minimizing intake valve deposits, and their use |
| CN1260332C (en) * | 2000-12-08 | 2006-06-21 | 申保安 | Full loss mechanical lubricating oil |
| CN103374085A (en) * | 2012-04-26 | 2013-10-30 | 中国石油化工股份有限公司 | Mannich base and manufacturing method and application thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113072674A (en) * | 2020-01-03 | 2021-07-06 | 万华化学集团股份有限公司 | Heat-sensitive tertiary amine catalyst, quaternized derivative thereof, preparation and application |
| CN113072674B (en) * | 2020-01-03 | 2022-07-12 | 万华化学集团股份有限公司 | Heat-sensitive tertiary amine catalyst, quaternized derivative thereof, preparation and application |
| CN115322824A (en) * | 2022-03-31 | 2022-11-11 | 南京科润工业介质股份有限公司 | Anti-rust oil composition |
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| Publication number | Publication date |
|---|---|
| CN104927972B (en) | 2017-11-03 |
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