Pyrrolidine-2,5-dione derivatives for use in friction modification

A technology of tribology and alkyl, applied in the direction of lubricating composition, organic chemistry, additives, etc., can solve problems such as no public or recognized suggestions, no solution to low-temperature viscosity problems, etc.

Inactive Publication Date: 2010-07-07
AFTON CHEMICAL +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A further disadvantage is that this formula is solid at room temperature and requires additional heating for transfer and mixing
[0007] There is no apparent disclosure or awareness suggestion in EP 0020037A1, aware of the low temperature performance problems of its preferred friction modifiers, nor any suggestion of a commercially viable solution to this low temperature viscosity problem

Method used

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  • Pyrrolidine-2,5-dione derivatives for use in friction modification
  • Pyrrolidine-2,5-dione derivatives for use in friction modification
  • Pyrrolidine-2,5-dione derivatives for use in friction modification

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Embodiment 1

[0124] 339.4 grams of C containing about forty (40) wt.% inner vinylidene 20 -C 24 Olefin (1.1 mol), 112.8 grams (1.2 mol) of molten maleic anhydride, 2.42 grams of p-toluenesulfonic acid (TsOH) and 1.64 grams of synthetic antioxidant (a hindered phenol antioxidant) were charged into a 1.0 L autoclave. The stirred mixture was subjected to vacuum (28 in. Hg), nitrogen purge, and vacuum cycles while stirring with heating. After about 5 hours at a temperature of about 225°C, the formed alkylsuccinic anhydride is transferred to a separate reactor where unreacted maleic anhydride is removed by distillation. Ammonia gas (16.95 grams) was bubbled into the stirred mixture at about 160°C for about 2 to about 3 hours. The hot mixture was vacuum filtered to give a clear product containing 2.29% N. The infrared spectrum of this transparent product shows that the carbonyl bond is at 1771, 1709cm -1 (imide). The amount of acid groups titratable by a strong base is 2.07 milliequivalents...

Embodiment 2

[0125] 450.0 g linear αC 20 -C 24 Olefin (1.5 mol), 149.6 g (1.5 mol) of molten maleic anhydride, 3.21 g of p-toluenesulfonic acid (TsOH) and 2.20 g of synthetic antioxidant (a hindered phenol antioxidant) were charged into a 2.0 L autoclave. The stirred mixture, sealed under vacuum, was stirred and heated at 225°C for approximately 5 hours. The resulting alkylsuccinic anhydride is transferred to a separate reactor where unreacted maleic anhydride is removed by distillation. A portion of the intermediate product (99.0 g) was neutralized with ammonia gas (4.21 g) at 160°C to yield 98.8 g of succinimide containing 2.94% N. Representative isomerized linear C 20 Succinimide structures include (E)-3-(eicosyl-8-en-8-yl)pyrrolidine-2,5-dione, shown above. Example 3

Embodiment 3

[0126] 344.9 grams of C containing about forty (40) wt.% inner vinylidene 20 -C 24 Olefin (1.1 mol), 114.6 g (1.2 mol) of molten maleic anhydride, 2.46 g of p-toluenesulfonic acid (TsOH) and 1.67 g of synthetic antioxidant (a hindered phenol antioxidant) were charged into a 1.0 L autoclave. The stirred mixture was subjected to vacuum (28 in. Hg), nitrogen purge, and vacuum cycles while stirring with heating. After about 5 hours at about 225°C, the formed alkylsuccinic anhydride is transferred to a separate reactor where unreacted maleic anhydride is removed by distillation. The product was diluted with 45.0 g of process oil. 43.9 grams of commercial tetraethylenepentamine (TEPA) was added dropwise under temperature-controlled conditions, resulting in a mixture stirred at 160°C under vacuum for 3 hours. The product (258.5 g) contained 6.09% N and had a total base number (TBN) of 146.5 mg KOH / g. Representative vinylidene C 20 Bis-succinimide structures include (2,2'-azanedi...

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Abstract

The present disclosure relates to a compound of the formula I or a tribologically acceptable salt, solvate, hydrate, or proadditive thereof, wherein R1, R2 and R4 are as defined herein. Such novel pyrrolidine, or succinimide, derivatives may be useful as friction modifiers in lubricant compositions. This disclosure also relates to a method of using such friction modifier compounds in lubricating fluid formulations to lubricate machine parts, including gear, axle, engine, and transmission parts, and to lubricant compositions containing such friction modifier compounds.

Description

technical field [0001] The present disclosure relates to lubricant additives useful in lubricating fluids that have satisfactory friction characteristics without compromising low temperature viscosity. The present disclosure also relates to the preparation of such lubricant additives, and concentrates containing such lubricant additives, as well as devices lubricated with lubricating fluids containing such lubricant additives. Background technique [0002] Friction modifier compounds used in lubricant formulations may generally have a formula that includes polar functional groups attached to a hydrophobic hydrocarbon chain that preferably has a suitable formula and number of carbon atoms to render it oil soluble. Molecules of this nature can typically be used in amounts of about 0.01 wt.% to about 0.5 wt.%, based on the weight of the fully formulated lubricant, and can provide a suitable degree of Fresh oil shudder protection; however, they may fail stability tests due to t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C10M133/44C07D207/412C10N60/14C10N60/12C10N40/26C10N40/12C10N40/28C10N40/25C10N40/04C10N30/02
CPCC10N2230/04C10N2240/044C10M133/56C10M2215/04C10M2215/08C10N2240/105C10N2220/022C10M2207/122C10M2223/12C10M2219/044C10M2217/024C10N2260/14C10N2240/04C10M149/06C07D207/412C10N2240/042C10M133/44C10N2240/12C10M2207/34C10N2230/06C10M2215/28C10M2219/042C10N2240/106C10N2240/045C10M2207/282C10N2260/12C10M2207/129C10M2201/18C10M133/16C10N2230/02C10M2217/043C10M2215/02C10N2230/45C10M2203/024C10N2240/10C10M2215/086C10N2230/76C10M2215/223C10N2030/02C10N2030/76C10N2040/045C10N2040/044C10N2040/042C10N2040/04C10N2040/26C10N2040/28C10N2040/12C10N2040/25C10N2020/02C10N2030/04C10N2030/06C10N2030/45C10N2060/12C10N2060/14
Inventor 罗杰·希茨纽巴·奥兹巴里克
Owner AFTON CHEMICAL
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