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Coupled dimercaptotriazine derivative, and preparation method and use thereof

A bismercaptotriazine and derivative technology, applied in the field of lubricating additives, can solve the problems of extreme pressure and anti-wear properties that need to be further improved, containing phosphorus elements, etc.

Active Publication Date: 2013-06-12
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] After searching the literature of the prior art, it was found that Chinese patents with patent application numbers CN03129696.3 and CN03129697.1 disclosed a monothiaphosphostriazine derivative and a dithiaphosphostriazine derivative as extreme pressure resistance Grinding additive, which has good extreme pressure and antiwear performance, but still contains phosphorus element; the Chinese patent application number is CN200610023444.2 discloses hydroxyl-containing triazine derivatives as extreme pressure and antiwear agents, but does not contain active sulfur element; European patent EP320450 introduces a sulfur-containing triazine derivative, which has good anti-oxidation and anti-corrosion properties, but its extreme pressure and anti-wear properties need to be further improved

Method used

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  • Coupled dimercaptotriazine derivative, and preparation method and use thereof
  • Coupled dimercaptotriazine derivative, and preparation method and use thereof
  • Coupled dimercaptotriazine derivative, and preparation method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] The synthesis of the coupled bismercaptotriazine derivative extreme pressure antiwear agent of the present embodiment is as follows: figure 1 As shown, the details are as follows:

[0030] 1) Add 18.45g of 2,4,6-trichloro-1,3,5-triazine into 150ml of organic solvent (acetone), and heat at 0°C (0-10°C is acceptable, 0°C is selected in this embodiment) Slowly add 12.9g of di-n-butylamine (feeding ratio 1:1) and 6.9g of acid-binding agent (potassium carbonate) under stirring, continue to react for 1.5 hours after the addition is completed, pour into ice water after the reaction, separate liquids, and use organic Diluted with solvent (ether), dried, filtered, and the filtrate was rotary evaporated to obtain 24.4 g of intermediate 1 (2-di-n-butylamino-4,6-dichloro-1,3,5-triazine), with a yield of 88.1%. The intermediate is a yellow oily liquid.

[0031] 2) Take 13g of sodium hydrosulfide and dissolve it in 300ml of organic solvent (ethanol), then slowly add 21g of intermedia...

Embodiment 2

[0037] The synthesis of the coupled bismercaptotriazine derivative extreme pressure antiwear agent of the present embodiment is as follows: figure 1 As shown, the details are as follows:

[0038] 1) Add 18.45g of 2,4,6-trichloro-1,3,5-triazine into 150ml of organic solvent (chloroform), slowly add 24.15g of diisooctylamine under stirring at 0°C (feeding ratio 1: 1) and 2g of acid-binding agent (sodium hydroxide), continue to react for 2.5 hours after the addition is complete, pour into ice water after the reaction, separate the liquids, dilute the organic phase with an organic solvent (ether), dry, filter, and the filtrate is rotary evaporated to obtain the intermediate Compound 1 (2-Diisooctylamino-4,6-dichloro-1,3,5-triazine) 34.0g, yield 87.3%, this intermediate is brown oily liquid.

[0039] 2) Dissolve 15g of sodium hydrosulfide in 350ml of organic solvent (ethanol), then slowly add 33.5g of intermediate 1 (feeding ratio is about 1:2.2), the reaction temperature is 70°C ...

Embodiment 3

[0044] Embodiment 3, extreme pressure and anti-wear performance test

[0045] The extreme pressure and antiwear properties of the two coupled bismercaptotriazine derivatives obtained in Example 1 and Example 2 are tested as follows:

[0046] 1. Extreme pressure performance test

[0047] According to the GB3142-82 standard, the bis-mercaptotriazine derivatives of lithium-based grease and two couplings prepared by example 1 and 2 were added in lithium-based grease and rapeseed oil and the coupled bis-mercapto group prepared by example 2 The maximum non-seizing load of triazine derivatives added in rapeseed oil (P B value) was measured. The four-ball machine used in the experiment is the MS-10JB four-ball machine produced by Xiamen Testing Machine Factory. The steel ball used is the second-grade GCr15 standard steel ball (AISI-52100), with a diameter of 12.7mm and a hardness of 59-61HRC. Carried out at room temperature with a rotation speed of 1760 rpm. The results are list...

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Abstract

The invention discloses a coupled dimercaptotriazine derivative, and a preparation method and a use thereof. 2,4,6-trichloro-1,3,5-triazine, amine and sodium bisulfide are adopted as raw materials and undergo substitution and coupling reactions to obtain the coupled dimercaptotriazine derivative. The coupled dimercaptotriazine derivative can be used through the combination with other lubricating greases and lubricating oil additives as an extreme-pressure anti-wear agent, and can also be individually used as a lubricating oil or a lubricating grease additive to make a lubricant have very good wear and extreme pressure resistances; the derivative in lithium-based grease can improve the PB value by 40-100% and reduce the wear scar diameter by 35-50%; and the derivative in rapeseed oil can improve the PB value by 45-65% and reduce the wear scar diameter by 25-45%.

Description

technical field [0001] The invention relates to the field of lubricating additives, in particular to a coupled bismercaptotriazine derivative and its preparation method and use. Background technique [0002] Nowadays, people pay more and more attention to energy and environmental issues, which are two major problems faced by the whole world. Therefore, it is imminent to develop efficient and environment-friendly extreme pressure and antiwear agents. Dialkyldithiophosphate (ZDDP) is a lubricating oil additive widely used in the field of lubrication, which has good anti-oxidation, anti-corrosion and anti-wear effects. However, the zinc element in it can cause electrochemical corrosion and generate ash, while the phosphorus element can easily poison the catalyst in the automobile exhaust device and cause problems such as toxicity, water treatment, filter blockage, and environmental pollution. [0003] Studies have shown that nitrogen-containing heterocyclic compounds have a co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/46C10M135/20C10N30/06
Inventor 蒋俊辉白雪峰李秀峰赵彩松陈立新任天辉
Owner SHANGHAI JIAO TONG UNIV
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