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Compound and method of making the compound

Inactive Publication Date: 2008-04-17
AFTON CHEMICAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0017]Another aspect of the present application is directed to a method for reducing the oxidation of a lubricating oil. The me

Problems solved by technology

Lubricating oils as used in the internal combustion engines and transmissions of automobiles or trucks are subjected to a demanding environment during use.

Method used

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  • Compound and method of making the compound
  • Compound and method of making the compound
  • Compound and method of making the compound

Examples

Experimental program
Comparison scheme
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example 1

Method of Making a Compound

[0054]An exemplary process for making an compound of the present application was carried out as follows:

[0055]Step 1: A 1-liter 4-neck flask equipped with nitrogen sub-surface was charged with 236.8 g of trimethylolpropane triacrylate (TMPTA), 300 g methanol, and 0.8 g of laural mercaptan. To this solution 192.8 g of bis(2-ethylhexylamine) was added dropwise over 4 hr period and then allowed to stir at room temperature for 3 hrs. The temperature was then raised to 65° C. to distill methanol and finally vacuum stripped and filtered over Celite. A total of approximately 424 g of product was isolated. % N=2.74%

[0056]Step 2: A 500 mL flask was charged with 149 g of process oil, 64 g of 2,6-di-tert butylphenol and 1 g of potassium hydroxide. The mixture was heated to about 120° C. and then mild vacuum was applied to remove about 1.3 ml of distillate. Vacuum was removed and the mixture was then heated to 140° C. 161 g of the product isolated from step 1 was then...

example 2

Method of Making an Compound

[0058]Another exemplary process for making a compound of the present application was carried out as follows.

[0059]A 500 ml flask was charged with 74 g of TMPTA and 240 g of butanol. The flask was equipped with nitrogen sub-surface and reflux condenser and heated to about 80° C. 46 g of NPPDA was added in portions over 30 min and the mixture was then heated to reflux for 8 hrs. 51.5 g of 2,6-di-tert butylphenol and 0.7 g potassium hydroxide were added and the mixture was again held at reflux for 7 hrs. The reflux condenser was replaced with a distillation apparatus and the mixture was heated to 145° C., during which almost 200 ml butanol was removed. The mixture was cooled to 65° C. and 60.3 g of bis(2-ethylhexyl)amine was added dropwise over a 2 hr period. The mixture was held at 65° C. for 3 hrs and then vacuum stripped. 7 g of talc was added and stirred for 30 minutes, followed by filteration through paper to remove solids. The filtered product had 4.22...

example 3

Evaluation of Engine Oils Containing the Compound of Example 1 in the Thermo-Oxidation Engine Oil Simulation Test (TEOST MHT-4)

[0060]The TEOST MHT-4 is a standard lubricant industry test for the evaluation of the oxidation and carbonaceous deposit-forming characteristics of engine oils. The test is designed to simulate high temperature deposit formation in the piston ring belt area of modern engines. The test utilizes a patented instrument (U.S. Pat. No. 5,401,661 and U.S. Pat. No. 5,287,731; the disclosure of each patent is hereby incorporated by reference in its entirety) with the MHT-4 protocol being a relatively new modification to the test. Details of the test operation and specific MHT-4 conditions have been published by Selby and Florkowski (Selby et al.) in a paper entitled, “The Development of the TEOST Protocol MHT as a Bench Test of Engine Oil Piston Deposit Tendency” presented at the 12th International Colloquium Technische Akademie Esslingen, Jan. 11-13, 2000. Wilfried ...

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Abstract

The present application is directed to compounds that are the reaction product of (i) a polyacrylate, (ii) a hindered phenol, (iii) a diaryldiamine and optionally (iv) an alkyl amine. Methods for making these compounds and formulations employing the compounds are also disclosed.

Description

FIELD OF THE DISCLOSURE[0001]The present application is directed to novel compounds, processes for making the compounds, and compositions that comprise the compounds.BACKGROUND OF THE DISCLOSURE[0002]Lubricating oils as used in the internal combustion engines and transmissions of automobiles or trucks are subjected to a demanding environment during use. This environment results in the oil suffering oxidation which is catalyzed by the presence of impurities in the oil, such as iron compounds, and is also promoted by the elevated temperatures of the oil during use.[0003]The oxidation of lubricating oils during use is often controlled to some extent by the use of antioxidant additives. Antioxidant additives can extend the useful life of the lubricating oil by, for example, reducing or preventing unacceptable viscosity increases.[0004]A combination of antioxidants are often employed in lubricants. One such combination includes both hindered phenol compounds and alkylated diphenylamines ...

Claims

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Application Information

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IPC IPC(8): C10M129/68C10M129/72
CPCC07C229/18C10L1/221C10L1/2235C10L10/04C10L10/10C10N2270/02C10M159/12C10M2215/064C10N2230/02C10N2240/10C10M133/14C10N2030/02C10N2040/25C10N2070/02C10M133/12C10N2030/10
Inventor MATHUR, NARESH C.
Owner AFTON CHEMICAL
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