Compounds and methods of making the compounds

a technology of compounds and compounds, applied in the field of antioxidants and processes for making antioxidants, can solve the problems of lubricating oils used in automobiles or trucks that are subjected to a demanding environment during use, and achieve the effect of reducing the amount of oxidation of oil and reducing the oxidation of lubricating oil

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

AI Technical Summary

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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  • Compounds and methods of making the compounds
  • Compounds and methods of making the compounds
  • Compounds and methods of making the compounds

Examples

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example 1

[0052]A 2-liter 4-neck flask was equipped with a nitrogen atmosphere and reflux condenser. The flask was charged with 950 g of (polyisobutenyl)phenol and a few drops of a defoamer. With agitation, the contents in the flask were heated to 80° C. and 138 g of N-phenyl-phenylenediamine (NPPDA) was added in portions, followed by dropwise addition of 60.8 g of 37% aqueous solution of formaldehyde over approximately 90 min. The reaction was then held at 80° C. for 4 hrs and then at reflux for 4 hrs. The reaction mixture was vacuum stripped at 110° C. The product was diluted with 336 g of process oil and then filtered over Celite. A total of approx. 1307 g of product thus obtained had TAN (total acid number) of 28.6 and % N=1.52.

[0053]552.6 g of the above product and 61.8 g of 2,6-ditertbutylphenol were charged to a 1-liter flask equipped with nitrogen atmosphere and reflux condenser. With agitation, the contents in the flask were heated to 60° C. and 1.5 g of dimethylaminopropylamine (DMA...

example 2

[0054]A 1-liter 4-neck flask was charged with 314.4 g of 4-dodecylphenol and 247.2 g of 2,6-ditertbutylphenol and equipped with nitrogen atmosphere and reflux condenser. With agitation, the contents in the flask were heated to 60° C. and 6 g of DMAPA catalyst was added followed by dropwise addition of 97.2 g of 37% aqueous solution of formaldehyde over approximately 20 min. The reaction was then held at 60° C. for 1 hr. Reflux condenser was replaced with a distillation condenser and the temperature then gradually raised to 150° C. A total of approximately 558 g of product thus obtained had TAN (total acid number) of 122.4.

[0055]344 g of the above product, 321.7 g of process oil and few drops of a defoamer were charged to a 1-liter flask equipped with nitrogen atmosphere and reflux condenser. With agitation, the contents in the flask were heated to 80° C. and 128.8 g of N-phenyl-phenylenediamine (NPPDA) was added in portions, followed by dropwise addition of 60.8 g of 37% aqueous sol...

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Abstract

The present application is directed to compounds that are the reaction product of (i) a hydrocarbyl phenol, (ii) a hindered phenol; (iii) an diaryldiamine and (iv) an aldehyde. Methods of making and using the compounds of the present application are disclosed.

Description

DESCRIPTION OF THE DISCLOSURE[0001]1. Field of the Disclosure[0002]The present application is directed to novel antioxidants, processes for making the antioxidants, and compositions that comprise the antioxidants.[0003]2. Background of the Disclosure[0004]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.[0005]The oxidation of lubricating oils during use is often controlled to some extend 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.[0006]A combination of antioxidants is often employed in lubricants. One such combination includes both ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C10M159/16
CPCC08G14/06C10M159/16C10M2207/023C10M2217/043C10N2230/10C10N2240/10C10N2270/02C10M2207/026C10M2207/08C10M2215/04C10N2030/10C10N2040/25C10N2070/02C07C213/08C07C215/74C09K15/24
Inventor MATHUR, NARESH C.
Owner AFTON CHEMICAL
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