CN113563324A - Environment-friendly multifunctional material containing ester group s-triazine, and preparation method and application thereof - Google Patents

Environment-friendly multifunctional material containing ester group s-triazine, and preparation method and application thereof Download PDF

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CN113563324A
CN113563324A CN202110832330.7A CN202110832330A CN113563324A CN 113563324 A CN113563324 A CN 113563324A CN 202110832330 A CN202110832330 A CN 202110832330A CN 113563324 A CN113563324 A CN 113563324A
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triazine
ester group
material containing
multifunctional material
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周文圣
周文忠
余磊
廖俊旭
赵鸿斌
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Dongguan Dosheng Environmental Protection Technology Co ltd
Dongguan University of Technology
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Dongguan University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
    • 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
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2030/40—Low content or no content compositions
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/42—Phosphor free or low phosphor content compositions
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/45—Ash-less or low ash content
    • 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
    • C10N2030/64—Environmental friendly compositions

Abstract

The invention discloses a green environment-friendly multifunctional material containing ester group s-triazine, and a preparation method and application thereof. The ester group-containing s-triazine derivative has a structure shown as a general formula I. The ester group-containing s-triazine derivative has the characteristics of simple preparation method, mild process conditions, easily obtained raw materials, low synthesis cost, high synthesis yield and the like; can be used as an extreme pressure, anti-wear, anti-friction and anti-corrosion additive, can obviously improve the bearing capacity of the base oil and improve the anti-wear and anti-friction performance of the base oil, and is an environment-friendly multifunctional additive;
Figure DDA0003175946440000011
wherein R is a straight chain or branched alkyl with 1-30C atoms.

Description

Environment-friendly multifunctional material containing ester group s-triazine, and preparation method and application thereof
Technical Field
The invention relates to a green environment-friendly multifunctional material containing ester group s-triazine, a preparation method and application thereof, and the derivative can be widely applied to the fields of machinery, energy, environment, materials, chemical industry and the like, and is particularly suitable for being used as a green environment-friendly lubricating oil (grease) additive.
Background
Lubricating oil additives are important substances determining the performance and service life of lubricating oil, and from the 20 th century and the 30 th century, a plurality of lubricating oil additives are developed and divided into five major categories such as cleaning agents, dispersing agents, antiwear agents, antioxidants and the like. With the continuous development of lubricating oil additives in China, the varieties of the lubricating oil additives are greatly increased, but certain gaps exist between the lubricating oil additives and developed countries in Europe and America in the aspects of technical level, product structures, production scale and the like, and a large number of high-end products are required to be imported. Therefore, the research on the lubricant additives is a hot topic, and particularly, the multifunctional lubricant additives which are environmentally friendly and have excellent comprehensive performance are provided.
Disclosure of Invention
In order to overcome the defects and shortcomings in the prior art, the invention aims to provide the green environment-friendly multifunctional material containing the ester group s-triazine, and the derivative does not contain elements harmful to the environment and human health, such as phosphorus, halogen, metal elements and the like, and has the characteristics of excellent performance and environmental friendliness.
The invention also aims to provide a preparation method of the environment-friendly multifunctional material containing the ester group s-triazine, which has the advantages of simple operation, convenient control, high production efficiency and low production cost and can be used for large-scale production.
The invention also aims to use the green environment-friendly multifunctional material containing the ester group s-triazine as a multifunctional additive of lubricating oil (grease) alone or in combination with other lubricating oil (grease) additives.
The purpose of the invention is realized by the following technical scheme: an environment-friendly multifunctional material containing ester group s-triazine has a chemical structure shown as a general formula I:
Figure BDA0003175946420000021
wherein R is a straight chain or branched alkyl with 1-30C atoms.
A large number of researches show that nitrogen element is helpful to form a high-performance protective film in the friction process and can effectively slow down the corrosion of active element sulfur on the metal surface, and heterocyclic derivatives containing nitrogen and sulfur heteroatoms are decomposed or partially decomposed in the friction process and chemically react with the metal surface to form a carbon and sulfur-rich reaction film, thereby playing the role of extreme pressure and abrasion resistance. From the perspective of molecular design, the invention designs and synthesizes a series of environment-friendly ester group-containing s-triazine derivatives, and the ester group-containing s-triazine derivatives are applied to the base oil of the lubricating oil to obtain a multifunctional lubricating oil additive with excellent comprehensive performance.
The other purpose of the invention is realized by the following technical scheme: the preparation method of the green environment-friendly multifunctional material containing the ester group s-triazine comprises the following steps:
(1) under the action of alkali, cyanuric chloride reacts with dialkyl amine to prepare an intermediate I, and the structural general formula of the intermediate I is as follows:
Figure BDA0003175946420000022
wherein R is a straight chain or branched alkyl with 1-30C atoms;
(2) under the action of alkali, 2-mercaptobenzothiazole reacts with the intermediate I to prepare an intermediate II, and the structural general formula of the intermediate II is as follows:
Figure BDA0003175946420000023
(3) under the action of alkali, the intermediate II reacts with 2- (methylamino) ethanol to prepare an intermediate III, and the structural general formula of the intermediate III is as follows:
Figure BDA0003175946420000031
(4) under the action of alkali, the intermediate III reacts with dodecanoyl chloride to prepare the green environment-friendly multifunctional material containing the ester group s-triazine.
Preferably, the reaction medium for the reactions in the steps (1) to (4) is one or more of chloroform, dichloromethane, water, ethanol, tetrahydrofuran and acetone.
Preferably, the reaction temperature of the reactions in the steps (1) to (4) is-5 to 80 ℃.
Preferably, the reaction time of the reactions in the steps (1) to (4) is 0.5 to 12.0 hours.
The invention also aims to realize the following technical scheme: the green environment-friendly multifunctional material containing the ester group s-triazine is used as a lubricating oil (grease) additive to be used alone or compounded with other lubricating oil (grease) additives.
Preferably, the green environment-friendly multifunctional material containing the ester-based s-triazine is added into base oil as a lubricating oil (grease) additive, and the addition amount of the green environment-friendly multifunctional material is 0.1-10 wt% of the base oil.
The invention has the beneficial effects that: the multifunctional lubricating oil additive containing the ester group s-triazine derivative has excellent thermal stability, corrosion resistance, extreme pressure performance, wear resistance and friction reduction performance, and is a lubricating oil additive with excellent comprehensive performance.
The preparation process is simple, the reaction conditions are mild, the used raw materials are cheap and easy to obtain, and the synthesis yield is high; the derivative is phosphorus-free, halogen-free and ashless, and is an environment-friendly lubricating oil additive.
Drawings
FIG. 1 is a NMR chart of example 1;
FIG. 2 is a NMR chart of example 2;
FIG. 3 is a NMR chart of example 3;
FIG. 4 is a mass spectrum of example 1;
FIG. 5 is a mass spectrum of example 2;
FIG. 6 is a mass spectrum of example 3;
FIG. 7 is a scanning electron microscope image of the surface topography of the plaque using vegetable oil base oil (a), (b), (c), (d) oil samples with 1.0% by weight of ZDDP additive (the same applies hereinafter), (e), (f) oil samples with 1.0% by weight of the additive of example 1, (g), (h) oil samples with 1.0% of the additive of example 2, and (i), (j) oil samples with 1.0% of the additive of example 3.
Detailed Description
For the understanding of those skilled in the art, the present invention will be further described with reference to the following examples and drawings, which are not intended to limit the present invention.
Example 1
0.05mol (9.25g) of cyanuric chloride, 0.06mol (8.30g) of K2CO3And 80mL of acetone were sequentially added to a 250mL three-necked flask, and 0.05mol (6.46g) of di-n-butylamine was added dropwise in an ice bath to conduct reaction for 2.0 hours. After the reaction is finished, the reaction solution is extracted by diethyl ether in a separating funnel, washed by saturated saline, dried by anhydrous magnesium sulfate, filtered, and the filtrate is rotated and evaporated to remove the solvent, so that the 2-di-n-butylamino-4, 6-dichloro-1, 3, 5-s-triazine is obtained.
0.05mol (8.362g) of 2-mercaptobenzothiazole and 0.06mol (3.366g) of KOH are dissolved in a mixed solution of 20mL of acetone and 20mL of water to prepare a potassium salt solution of 2-mercaptobenzothiazole for later use. 0.04mol (11.04g) of 2-di-n-butylamino-4, 6-dichloro-1, 3, 5-s-triazine and 20mL of acetone are added into a 250mL three-necked bottle, the temperature is raised to 42 ℃, a potassium salt solution of 2-mercaptobenzothiazole is added dropwise, and the constant temperature reaction is carried out for 12 hours. After the reaction is finished, pouring the reaction liquid into a separating funnel, extracting with ethyl acetate, washing with saturated saline solution, drying with anhydrous magnesium sulfate, filtering, removing the solvent from the filtrate to obtain a crude product, and performing silica gel column chromatography to obtain 2-di-n-butylamino-4- (benzothiazole-2-yl-sulfenyl) -6-chloro-1, 3, 5-s-triazine.
0.04mol (3.00g) of 2- (methylamino) ethanol, 0.04mol (4.24g) of anhydrous sodium carbonate and 50mL of ethanol were added to a 250mL three-necked flask, and 0.03mol (12.21g) of 2-di-n-butylamino-4- (benzothiazol-2-yl-thio) -6-chloro-1, 3, 5-s-triazine was added dropwise at room temperature, followed by reaction for 0.5h and then reflux reaction for 12 h. After the reaction, insoluble matter was removed by suction filtration, the solvent was removed by rotary evaporation, the residue was dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate to obtain intermediate 3. And reacting the intermediate 3 with the dodecanoyl chloride for 3 hours under ice bath to obtain a crude product. The crude product was purified by silica gel column chromatography to give 15.70g of a white solid in 83.3% yield. The analysis results are shown in figures 1 and 4,1H NMR(400MHz,CDCl3)δ8.00(d,J＝8.1Hz,1H),7.83(d,J＝7.8Hz,1H),7.45(t,J＝7.5Hz,1H),7.36(t,J＝7.5Hz,1H),4.26(dt,J＝10.8,5.3Hz,2H),3.80(dd,J＝12.8,6.8Hz,2H),3.56–3.37(m,4H),3.18(d,J＝34.1Hz,3H),2.28(t,J＝7.5Hz,2H),1.65–1.50(m,6H),1.34–1.18(m,20H),0.97–0.82(m,9H).MALDI-TOF-MS,m/z:calcd for C33H52N6O2S2[M+1]+:628.32,found:629.214。
example 2
0.05mol (9.25g) of cyanuric chloride, 0.06mol (8.30g) of K2CO3And 80mL of acetone were sequentially added to a 250mL three-necked flask, and 0.05mol (12.07g) of diisooctylamine was added dropwise in an ice bath to react for 2.0 hours. After the reaction is finished, extracting the reaction solution by using ethyl ether in a separating funnel, washing the reaction solution by using saturated saline solution, drying the reaction solution by using anhydrous magnesium sulfate, filtering the reaction solution, and removing the solvent by rotary evaporation of the filtrate to obtain the 2-diisooctylamino-4, 6-dichloro-1, 3, 5-s-triazine.
0.05mol (8.362g) of 2-mercaptobenzothiazole and 0.06mol (3.366g) of KOH are dissolved in a mixed solution of 20mL of acetone and 20mL of water to prepare a potassium salt solution of 2-mercaptobenzothiazole for later use. 0.04mol (15.53g) of 2-diisooctylamino-4, 6-dichloro-1, 3, 5-s-triazine and 20mL of acetone are added into a 250mL three-necked bottle, the temperature is raised to 42 ℃, a potassium salt solution of 2-mercaptobenzothiazole is added dropwise, and the constant temperature reaction is carried out for 12 hours. After the reaction is finished, pouring the reaction liquid into a separating funnel, extracting with ethyl acetate, washing with saturated saline solution, drying with anhydrous magnesium sulfate, filtering, removing the solvent from the filtrate to obtain a crude product, and performing silica gel column chromatography to obtain the 2-diisooctylamino-4- (benzothiazole-2-yl-sulfenyl) -6-chloro-1, 3, 5-s-triazine.
0.04mol (3.00g) of 2- (methylamino) ethanol, 0.04mol (4.24g) of anhydrous sodium carbonate and 50mL of ethanol were added to a 250mL three-necked flask, and 0.03mol (15.58g) of 2-diisooctylamino-4- (benzothiazol-2-yl-thio) -6-chloro-1, 3, 5-s-triazine was added dropwise at room temperature for 0.5h, followed by reflux for 12 h. After the reaction, insoluble matter was removed by suction filtration, the solvent was removed by rotary evaporation, the residue was dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate to obtain intermediate 3. And reacting the intermediate 3 with the dodecanoyl chloride for 3 hours under ice bath to obtain a crude product. The crude product was purified by silica gel column chromatography to give 19.24g of a white solid in 86.67% yield. The analysis results are shown in FIGS. 2 and 5,1H NMR(400MHz,CDCl3)δ8.00(d,J＝8.0Hz,1H),7.84(d,J＝7.9Hz,1H),7.46(t,J＝7.5Hz,1H),7.37(t,J＝7.4Hz,1H),4.32–4.21(m,2H),3.82(d,J＝6.0Hz,2H),3.53–3.34(m,4H),3.19(d,J＝39.0Hz,3H),2.29(t,J＝7.4Hz,2H),1.68(dd,J＝75.0,23.7Hz,4H),1.20(d,J＝25.4Hz,32H),0.90–0.78(m,15H).MALDI-TOF-MS,m/z:calcd for C41H68N6O2S2[M+1]+:740.48,found:741.101。
example 3
0.05mol (9.25g) of cyanuric chloride, 0.06mol (8.30g) of K2CO3And 80mL of acetone were sequentially added to a 250mL three-necked flask, and 0.05mol (12.07g) of di-n-octylamine was added dropwise under ice bath to react for 2.0 hours. After the reaction is finished, extracting the reaction solution by using ethyl ether in a separating funnel, washing the reaction solution by using saturated saline solution, drying the reaction solution by using anhydrous magnesium sulfate, filtering the reaction solution, and removing the solvent by rotary evaporation of the filtrate to obtain the 2-di-n-octylamino-4, 6-dichloro-1, 3, 5-s-triazine.
0.05mol (8.362g) of 2-mercaptobenzothiazole and 0.06mol (3.366g) of KOH are dissolved in a mixed solution of 20mL of acetone and 20mL of water to prepare a potassium salt solution of 2-mercaptobenzothiazole for later use. 0.04mol (15.53g) of 2-di-n-octylamino-4, 6-dichloro-1, 3, 5-s-triazine and 20mL of acetone are added into a 250mL three-necked bottle, the temperature is raised to 42 ℃, a potassium salt solution of 2-mercaptobenzothiazole is added dropwise, and the constant temperature reaction is carried out for 12 hours. After the reaction is finished, pouring the reaction liquid into a separating funnel, extracting with ethyl acetate, washing with saturated saline solution, drying with anhydrous magnesium sulfate, filtering, removing the solvent from the filtrate to obtain a crude product, and performing silica gel column chromatography to obtain the 2-di-n-octylamino-4- (benzothiazole-2-yl-sulfenyl) -6-chloro-1, 3, 5-s-triazine.
0.04mol (3.00g) of 2- (methylamino) ethanol, 0.04mol (4.24g) of anhydrous sodium carbonate and 50mL of ethanol were added to a 250mL three-necked flask, and 0.03mol (15.58g) of 2-di-n-octylamino-4- (benzothiazol-2-yl-thio) -6-chloro-1, 3, 5-s-triazine was added dropwise at room temperature, followed by reaction for 0.5h and then reflux reaction for 12 h. After the reaction, insoluble matter was removed by suction filtration, the solvent was removed by rotary evaporation, the residue was dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate to obtain intermediate 3. And reacting the intermediate 3 with the dodecanoyl chloride for 3 hours under ice bath to obtain a crude product. The crude product was purified by silica gel column chromatography to give 19.24g of a white solid in 86.67% yield. The analysis results are shown in FIGS. 3 and 6,1H NMR(400MHz,CDCl3)δ7.92(d,J＝8.1Hz,1H),7.76(d,J＝7.7Hz,1H),7.38(t,J＝7.7Hz,1H),7.32–7.26(m,1H),4.22–4.16(m,2H),3.78–3.70(m,2H),3.39(d,J＝7.6Hz,2H),3.10(d,J＝33.8Hz,3H),2.21(t,J＝7.6Hz,2H),1.50(s,6H),1.16(s,38H),0.83–0.77(m,9H).MALDI-TOF-MS,m/z:calcd for C41H68N6O2S2[M+1]+:740.48,found:741.467。
example 4 Performance testing
The extreme pressure, wear resistance and friction reduction performance of the additive and the surface appearance of the ball-milled spots of the steel are as follows:
the ester-containing s-triazine derivatives prepared in examples 1 to 3 and commercially available ZDDP were added to vegetable oil in an amount of 1.0% by mass to prepare test oil samples. The maximum seizure-free load (P) of the lubricating oil was evaluated by a MS-10A type four-ball friction tester manufactured by Xiamen testing machine factory with reference to GB-3142-82BValue) and sintering load (P)DValue).The test conditions are room temperature (25 ℃), the rotating speed is 1450r/min, and the time is 10 s. The steel balls used in the test are standard grade II GCr15 steel balls produced by Shanghai Steel ball factories, the diameter is 12.7mm, and the hardness is 59-61 RC. PBValue sum PDThe results of the value tests are listed in table 1.
TABLE 1 maximum No-seize load (P)BValue) and sintering load (P)DValue)
Figure BDA0003175946420000071
Figure BDA0003175946420000081
The result shows that the ester group-containing s-triazine derivative is added into the vegetable oil, and the P of the vegetable oilBAnd PDThe values are greatly improved, which shows that the extreme pressure performance of the lubricating oil can be greatly improved by the additive in the embodiment 1-4, and the extreme pressure performance of the additive is superior to that of the traditional additive ZDDP.
A commercially available ZDDP obtained from the ester-containing s-triazine derivatives prepared in examples 1-3 was added to vegetable oil in an amount of 1.0% by mass to prepare a test oil sample. The ball Wear Scar Diameter (WSD) was measured at a load of 392N, at a speed of 1450r/min and for a period of 30min on a four-ball friction tester, and the results are shown in Table 2 and the corresponding average friction coefficients are shown in Table 3.
TABLE 2 Steel ball scrub spot diameter (WSD)
Oil sample WSD/mm
Vegetable oil 1.405
ZDDP 0.782
Example 1 0.712
Example 2 0.707
Example 3 0.701
The results show that when the ester group-containing s-triazine derivative is added into vegetable oil, the WSD value of the vegetable oil is obviously reduced. The additive of the embodiment 1-3 can obviously improve the wear resistance of the lubricating oil, and the wear resistance of the additive is superior to that of the traditional additive ZDDP.
TABLE 3 mean coefficient of friction
Figure BDA0003175946420000082
Figure BDA0003175946420000091
The result shows that when the ester group-containing s-triazine derivative is added into the vegetable oil, the average friction coefficient of the vegetable oil is obviously reduced. The additive of the embodiment 1-3 can improve the antifriction performance of the lubricating oil, and the antifriction performance is superior to that of the traditional additive ZDDP.
FIG. 7 is a scanning electron microscope image of the surface topography of the vegetable oil and oil samples with 1.0% of the 3 additives synthesized. The result shows that compared with the surface of the steel ball grinding spots lubricated by vegetable oil, the steel ball grinding spots lubricated by the vegetable oil containing the additive are shallow, the diameter of the grinding spots is small, the grinding marks are regular, and the number of the grinding marks is reduced, which indicates that the additive plays a role in wear resistance when being added into the vegetable oil.
Thermal stability of lubricating oil additives:
the thermal stability of the additives prepared in examples 1 to 3 was examined using a TG209 type thermogravimetric analyzer manufactured by Germany Steady instruments manufacturing Ltd. The test conditions were: the nitrogen atmosphere and the temperature rise rate were 20 ℃/min, and the test results are shown in Table 4.
TABLE 4 thermal decomposition temperatures of additives
Additive agent T1/℃ T2/℃
Example 1 199 350
Example 2 198 372
Example 3 229 392
ZDDP 161 300
The results show that the ester-containing s-triazine derivatives synthesized in the examples have initial thermal decomposition temperature of 169-209 ℃ and final thermal decomposition temperature of 350-392 ℃, have excellent thermal stability, and are suitable for common working conditions and high-temperature working conditions.
Corrosion resistance of the multifunctional lubricating oil additive:
the ester group-containing s-triazine derivatives prepared in examples 1 to 3 were added to vegetable oil in an amount of 1.0% by mass to prepare test oil samples. The corrosion test was carried out with reference to the method of GB/T5096-2017. The test results are shown in Table 5.
TABLE 5 copper sheet Corrosion test results
Additive (1.0 wt%) Corrosion grade
Example 1 1a
Example 2 1a
Example 3 1a
The results show that the corrosion rating of the oil samples containing 3 additives is 1a, indicating that all 3 additives have excellent corrosion resistance.
The above-described embodiments are preferred implementations of the present invention, and the present invention may be implemented in other ways without departing from the spirit of the present invention.

Claims (7)

1. The green environment-friendly multifunctional material containing ester group s-triazine is characterized by having a chemical structure shown as a general formula I:
Figure FDA0003175946410000011
wherein R is a straight chain or branched alkyl with 1-30C atoms.
2. A method for preparing the green environment-friendly multifunctional material containing the ester group s-triazine as claimed in claim 1, which comprises the following steps:
(1) under the action of alkali, cyanuric chloride reacts with dialkyl amine to prepare an intermediate I, and the structural general formula of the intermediate I is as follows:
Figure FDA0003175946410000012
wherein R is a straight chain or branched alkyl with 1-30C atoms;
(2) under the action of alkali, 2-mercaptobenzothiazole reacts with the intermediate I to prepare an intermediate II, and the structural general formula of the intermediate II is as follows:
Figure FDA0003175946410000013
(3) under the action of alkali, the intermediate II reacts with 2- (methylamino) ethanol to prepare an intermediate III, and the structural general formula of the intermediate III is as follows:
Figure FDA0003175946410000014
Figure FDA0003175946410000021
(4) under the action of alkali, the intermediate III reacts with dodecanoyl chloride to prepare the green environment-friendly multifunctional material containing the ester group s-triazine.
3. The method for preparing the green environment-friendly multifunctional material containing the ester group s-triazine as claimed in claim 2, wherein the method comprises the following steps: in the steps (1) - (4), the reaction medium of the reaction is one or a mixture of more of chloroform, dichloromethane, water, ethanol, tetrahydrofuran and acetone.
4. The method for preparing the green environment-friendly multifunctional material containing the ester group s-triazine as claimed in claim 2, wherein the method comprises the following steps: in the steps (1) - (4), the reaction temperature of the reaction is-5-80 ℃.
5. The method for preparing the green environment-friendly multifunctional material containing the ester group s-triazine as claimed in claim 2, wherein the method comprises the following steps: in the steps (1) - (4), the reaction time of the reaction is 0.5-12.0 h.
6. The use of the green multifunctional material containing ester group s-triazine as claimed in claim 1, wherein: the green environment-friendly multifunctional material containing the ester group s-triazine is used as a lubricating oil (grease) additive independently or is used in a compound way with other lubricating oil (grease) additives.
7. The use of the green multifunctional material containing ester group s-triazine as claimed in claim 6, wherein: the green environment-friendly multifunctional material containing the ester group s-triazine is used as a lubricating oil (grease) additive to be added into base oil, and the addition amount of the green environment-friendly multifunctional material is 0.1-10 wt% of the base oil.
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Citations (5)

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CN1200680A (en) * 1995-09-20 1998-12-02 诺沃挪第克公司 Novel attinity ligands and their use
US20040266633A1 (en) * 2003-04-14 2004-12-30 Fuji Photo Film Co., Ltd. Lubricant composition and triazine-ring-containing compound
CN103145634A (en) * 2012-05-08 2013-06-12 上海交通大学 Coupled dimercaptotriazine derivative, and preparation method and use thereof
CN104529921A (en) * 2014-11-28 2015-04-22 华东交通大学 Water-soluble triazine xanthic acid derivative, and preparation method and application thereof
CN108191850A (en) * 2018-01-19 2018-06-22 东莞理工学院 A kind of Striazine derivative multifunctional additive for lubricating oil and preparation method and application

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1200680A (en) * 1995-09-20 1998-12-02 诺沃挪第克公司 Novel attinity ligands and their use
US20040266633A1 (en) * 2003-04-14 2004-12-30 Fuji Photo Film Co., Ltd. Lubricant composition and triazine-ring-containing compound
CN103145634A (en) * 2012-05-08 2013-06-12 上海交通大学 Coupled dimercaptotriazine derivative, and preparation method and use thereof
CN104529921A (en) * 2014-11-28 2015-04-22 华东交通大学 Water-soluble triazine xanthic acid derivative, and preparation method and application thereof
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