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US 2010/0137173 A1Published application
Pyrrolidine-2,5-dione derivatives for use in friction modification
AssigneeAfton Chemical Corporation
InventorsRoger Sheets, Nubar Ozbalik
Life of this patent
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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.
Claims67
A compound as represented by formula I below:
- or a tribologically acceptable salt, solvate, hydrate, or proadditive thereof,
- wherein R1 is selected from the group consisting of:
- hydrogen, —(C1-C6)alkyl, —(C1-C6)alkenyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, and a radical having formula II below, where z may be from 1-10;
- wherein said —(C1-C6)alkyl, —(C1-C6)alkenyl, —(C3-C7)cycloalkyl, and —(C2-C8)heterocyclyl substituents are optionally substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxyl, —(C1-C16)alkyl, —(C1-C16)alkenyl, —CN, —NR8R9, —OR8, —(C3-C7)cycloalkyl, —(C2-C6)heterocyclyl, —CO2R15, —SO2NR8R9, NR15SO2R10, —SO2R10 and —CONR8R11;
- wherein R8 and R11 of said —CONR8R11 group may be taken together with the atoms to which they are attached to form a —(C2-C9)heterocyclyl;
- and wherein R2 may vary independently and has the following formula III:
- and wherein Ra and Rb are independently a (C3-C15) alkyl, cycloalkyl or cycloalkenyl;
- and wherein R4 is selected from the group consisting of hydrogen, (C1-C6)alkyl, (C1-C6)alkenyl, —(C3-C7)cycloalkyl, and —(C2-C9)heterocyclyl;
- wherein said (C1-C6)alkyl, (C1-C6)alkenyl, —(C3-C7)cycloalkyl, and —(C2-C9)heterocyclyl substituents may be optionally substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxyl, —(C1-C16)alkyl, (C1-C16)alkenyl, —CN, —NR8R9, —OR8, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R15, —SO2NR8R9, NR15SO2R10, —SO2R10 and —CONR8R11;
- wherein R8 and R11 of said —CONR8R11 group may be taken together with the atoms to which they are attached to form a —(C2-C9)heterocyclyl;
- and wherein R8 and R9 may each be substituents independently selected from the group consisting of hydrogen, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl and said —(C2C9)heterocyclyl group may optionally be interrupted by one to three elements independently selected from the group consisting of —(C═O), —SO2, —S—, —O—, —P—, —N—, —NH— and —NR15, —(C6-C10)aryl, —(C1-C9)heteroaryl, COR15 and —SO2R15;
- wherein said —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, —(C1-C9)heteroaryl, —COR18 and —SO2R15 R8 or R9 substituents may optionally be substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, -chalcogen, —CF3, —CN, —(C1-C6)alkyl, —NH(C1-C6)alkyl, —NH(C3-C7)cycloalkyl, —NH(C2-C9)heterocyclyl, —NH(C6-C10)aryl, —NH(C1-C9)heteroaryl, —N((C1-C6)alkyl)2, —N((C3-C7)cycloalkyl)2-, —N((C2-C9)heterocyclyl)2, —N((C6-C10)aryl)2, —N((C1-C9)heteroaryl)2, —O(C1-C6)alkyl, —O(C3-C2)cycloalkyl, —O(C2-C9)heterocyclyl, —O(C6-C10)aryl, —O(C1-C9)heteroaryl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R10, SO2NR8R9, NR15SO2R10, —SO2R10, —CONH2, —CONHR10, and —CONR10R11;
- wherein R10 and R11 of said —CONR10R11 group may be taken together with the nitrogen atom to which they are attached to form a —(C2-C9) heterocyclyl;
- and wherein R8 and R9 may be taken together with the atom(s) to which they are attached to form a —(C2-C9)heterocyclyl, wherein said —(C2-C9)heterocyclyl group may optionally be substituted by one to three moieties selected from the group consisting of hydrogen, halogen, hydroxy, —CF3, —NO2, —CN, —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —C═N—OH, —C═N—O((C1-C6)-alkyl), —NR10R11, —OR11, —(C3-C7)cycloalkyl, —(C2C9)heterocyclyl, —CO2R15, —CONR10R11, —CONR8R11, —SR10, —SOR10, —SO2R10, —SO2NR10R11, —NHCOR15, —NR15CONR10R11, and —NR12SO2R10, wherein said —(C2-C6)alkenyl and —(C2-C8)alkynyl moieties of said —(C2-C9)heterocyclyl group may be optionally substituted by one to three R10 groups, and said —(C2-C9)heterocyclyl group may optionally be interrupted by one to three elements independently selected from the group consisting of —(C═O), —SO2, —S—, —O—, —P—, —N—, —NH— and —NR15;
- and wherein R10 is a substituent selected from the group consisting of —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9) heteroaryl;
- wherein said —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9) heteroaryl R10 substituents may optionally be substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —(C1-C6)alkyl, —NR15, and —O(C1-C6)alkyl;
- and wherein R11 is a substituent selected from the group consisting of hydrogen, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9)heteroaryl;
- wherein said —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9) heteroaryl R11, radicals may optionally be substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —(C1-C6)alkyl, —NH2, —NHR12, —N(R12)2, —OR12, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R13, —CONH2, —CONHR13, and —CONR13R14;
- wherein R13 and R14 of —CONR13R14 may be taken together with the nitrogen atom to which they are attached to form a —(C2-C9)heterocyclyl;
- and wherein R12 and R13 may each be independently selected from the group consisting of hydrogen and —(C1-C6)alkyl;
- and wherein R14 may be selected from the group consisting of hydrogen and —(C1-C6)alkyl;
- and wherein R15 may be a substituent selected from the group consisting of hydrogen, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9)heteroaryl;
- wherein said —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9)heteroaryl R15 substituent may optionally be substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, —CF3, —CN, —(C1-C6)alkyl, —NH(C1-C6)alkyl, —NH(C3-C7)cycloalkyl, —NH(C2-C9)heterocyclyl, —NH(C6-C10)aryl, —NH(C1-C9)heteroaryl, —N((C1-C6)alkyl)2, —N((C3-C7cycloalkyl)2-, —N((C2-C9)heterocyclyl)2, —N((C6-C10)aryl)2, —N((C1-C9)heteroaryl)2, —O(C1-C6)alkyl, —O(C3-C7)cycloalkyl, —O(C2-C9)heterocyclyl, —O(C6-C10)aryl, —O(C1-C9)heteroaryl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R10, —CONH2, —CONHR10, and —CONR10R11;
- and wherein R10 and R11 of said —CONR10R11 group may be taken together with the atoms which they are attached to form a —(C2-C9) heterocyclyl.
21 more elements
A lubricant additive comprising a reaction product obtained by the process of:
- a) combining a tri-substituted internal olefin, wherein each olefin comprises from about 12 to about 36 carbon atoms, and maleic anhydride at a sufficient elevated temperature for a sufficient amount of time to provide a maleated product;
- and
- (b) aminating and neutralizing the maleated product with an effective amount of a compound containing basic nitrogen at an elevated temperature.
A method of making a lubricant additive, comprising:
- a) combining a tri-substituted internal olefin, wherein each olefin comprises from about 12 to about 36 carbon atoms, and maleic anhydride at a sufficient elevated temperature for a sufficient amount of time to provide a maleated product;
- and
- (b) aminating and neutralizing the maleated product with an effective amount of a compound containing basic nitrogen at an elevated temperature.
A lubricant composition comprising a mixture of:
- (a) a major amount of a lubricating oil;
- and
- (b) a Brookfield viscosity improving effective amount of a compound having the formula I:
- or a tribologically acceptable salt, solvate, hydrate, or proadditive thereof,
- wherein R1 is selected from the group consisting of:
- hydrogen, —(C1-C6)alkyl, —(C1-C6)alkenyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, and a radical having formula II below, where z may be from 1-10;
- wherein said —(C1-C6)alkyl, —(C1-C6)alkenyl, —(C3-C7)cycloalkyl, and —(C2-C9)heterocyclyl substituents are optionally substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxyl, —(C1-C16)alkyl, —(C1-C16)alkenyl, —CN, —NR8R9, —OR8, —(C3-C7)cycloalkyl, ——(C2-C9)heterocyclyl, —CO2R15, —SO2NR8R9, NR15SO2R10, —SO2R10 and —CONR8R11;
- wherein R8 and R11 of said —CONR8R11 group may be taken together with the atoms to which they are attached to form a —(C2-C9)heterocyclyl;
- and wherein R2 may vary independently and has the following formula III:
- and wherein Ra and Rb are independently a (C3-C15) alkyl, cycloalkyl or cycloalkenyl;
- and wherein R4 is selected from the group consisting of hydrogen, (C1-C6)alkyl, (C1-C6)alkenyl, —(C3-C7)cycloalkyl, and —(C2-C9)heterocyclyl;
- wherein said (C1-C6)alkyl, (C1-C6)alkenyl, —(C3-C7)cycloalkyl, and —(C2-C9)heterocyclyl substituents may be optionally substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxyl, —(C1-C16)alkyl, (C1-C16)alkenyl, —CN, —NR8R9, —OR8, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R15, —SO2NR8R9, NR15SO2R10, —SO2R10 and —CONR8R11;
- wherein R8 and R11 of said —CONR8R11 group may be taken together with the atoms to which they are attached to form a —(C2-C9)heterocyclyl;
- and wherein R8 and R9 may each be substituents independently selected from the group consisting of hydrogen, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl and said —(C2-C9)heterocyclyl group may optionally be interrupted by one to three elements independently selected from the group consisting of —(C═O), —SO2, —S—, —O—, —P—, —N—, —NH— and —NR15, —(C6-C10)aryl, —(C1-C9)heteroaryl, COR15 and —SO2R15;
- wherein said —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, —(C1-C9)heteroaryl, —COR15 and —SO2R15 R8 or R9 substituents may optionally be substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, -chalcogen, —CF3, —CN, —(C1-C6)alkyl, —NH(C1-C6)alkyl, —NH(C3-C7)cycloalkyl, —NH(C2-C9)heterocyclyl, —NH(C6-C10)aryl, —NH(C1-C9)heteroaryl, —N((C1-C6)alkyl)2, —N((C3-C7)cycloalkyl)2-, —N((C2-C9)heterocyclyl)2, —N((C6-C10)aryl)2, —N((C1-C9)heteroaryl)2, —O(C1-C6)alkyl, —O(C3-C7)cycloalkyl, —O(C2-C9)heterocyclyl, —O(C6-C10)aryl, —O(C1-C9)heteroaryl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R10, SO2NR8R9, NR15SO2R10, —SO2R10, —CONH2, —CONHR10, and —CONR10R11;
- wherein R10 and R11 of said —CONR10R11 group may be taken together with the nitrogen atom to which they are attached to form a —(C2-C9) heterocyclyl;
- and wherein R8 and R9 may be taken together with the atom(s) to which they are attached to form a —(C2-C9)heterocyclyl, wherein said —(C2-C9)heterocyclyl group may optionally be substituted by one to three moieties selected from the group consisting of hydrogen, halogen, hydroxy, —CF3, —NO2, —CN, —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —C═N—OH, —C═N—O((C1-C6)-alkyl), —NR10R11, —OR15, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R15, —CONR10R11, —CONR8R11, —SR10, —SOR10, —SO2R10, —SO2NR10R11, —NHCOR15, —NR15CONR10R11, and —NR12SO2R10, wherein said —(C2-C6)alkenyl and —(C2-C6)alkynyl moieties of said —(C2-C9)heterocyclyl group may be optionally substituted by one to three R10 groups, and said —(C2-C9)heterocyclyl group may optionally be interrupted by one to three elements independently selected from the group consisting of —(C═O), —SO2, —S—, —O—, —P—, —N—, —NH— and —NR15;
- and wherein R10 is a substituent selected from the group consisting of —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9) heteroaryl;
- wherein said —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9) heteroaryl R10 substituents may optionally be substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —(C1-C6)alkyl, —NR15, and —O(C1-C6)alkyl;
- and wherein R11 is a substituent selected from the group consisting of hydrogen, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9) heteroaryl;
- wherein said —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9) heteroaryl R11 radicals may optionally be substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —(C1-C6)alkyl, —NH2, —NHR12, —N(R12)2, —OR12, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R13, —CONH2, —CONHR13, and —CONR13R14;
- wherein R13 and R14 of —CONR13R14 may be taken together with the nitrogen atom to which they are attached to form a —(C2-C9)heterocyclyl;
- and wherein R12 and R13 may each be independently selected from the group consisting of hydrogen and —(C1-C6)alkyl;
- and wherein R14 may be selected from the group consisting of hydrogen and —(C1-C6)alkyl;
- and wherein R15 may be a substituent selected from the group consisting of hydrogen, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9)heteroaryl;
- wherein said —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —(C6-C10)aryl, and —(C1-C9)heteroaryl R15 substituent may optionally be substituted by one to three moieties Independently selected from the group consisting of hydrogen, halogen, —CF3, —CN, —(C1-C6)alkyl, —NH(C1-C8)alkyl, —NH(C3-C7)cycloalkyl, —NH(C2-C9)heterocyclyl, —NH(C6-C10)aryl, —NH(C1-C9)heteroaryl, —N((C1-C6)alkyl)2, —N((C3-C7)cycloalkyl)2-, —N((C2-C9)heterocyclyl)2, —N((C6-C10)aryl)2, —N((C1-C9)heteroaryl)2, —O(C1-C6)alkyl, —O(C3-C7)cycloalkyl, —O(C2-C9)heterocyclyl, —O(C6-C10)aryl, —O(C1-C9)heteroaryl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl, —CO2R10, —CONH2, —CONHR10, and —CONR10R11;
- and wherein R10 and R11 of said —CONR10R11 group may be taken together with the atoms which they are attached to form a —(C2-C9) heterocyclyl.
24 more elements
A reaction product, or a tribologically acceptable salt or solvate thereof, obtained by:
- a. reacting a C10-C35 vinylidene olefin with maleic acid, anhydride, or ester to provide a hydrocarbon-substituted succinic acid, anhydride or ester;
- and
- b. aminating the said hydrocarbon-substituted succinic acid, anhydride or ester with an effective amount of a compound containing basic nitrogen.
A lubricant additive comprising a reaction product obtained by the process of:
- a. reacting a C10-C36 vinylidene olefin with maleic acid, anhydride, or ester to provide a hydrocarbon-substituted succinic acid, anhydride or ester;
- b. aminating the said hydrocarbon-substituted succinic acid, anhydride or ester with an effective amount of a compound containing basic nitrogen.
A method of making a lubricant additive, comprising:
- a) reacting a C10-C36 vinylidene olefin with maleic acid, anhydride, or ester to provide a hydrocarbon-substituted succinic acid, anhydride or ester;
- and
- b) aminating the said hydrocarbon-substituted succinic acid, anhydride or ester with an effective amount of a compound containing basic nitrogen.
A lubricant composition comprising a mixture of:
- (a) a major amount of a lubricating oil;
- and
- (b) a Brookfield viscosity improving effective amount of a reaction product obtained by:
- i) reacting a C10-C36 vinylidene olefin with maleic acid, anhydride, or ester to provide a hydrocarbon-substituted succinic acid, anhydride or ester;
- and
- ii) aminating the said hydrocarbon-substituted succinic acid, anhydride or ester with an effective amount of a compound containing basic nitrogen;
- or a tribologically acceptable salt, solvate, hydrate, or proadditive thereof.
4 more elements
Dependencies are inferred from the claim text.