1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions

A method for improving the anti-wear properties of a lubricating fluid while lubricating an automotive component requiring lubrication, comprising:

• 1) adding a lubricating fluid to an automotive component requiring lubrication, said fluid comprising (a) a base oil, and (b) one or more compounds of formula I,
• or a tribologically acceptable salt or solvate thereof;
• and
• 2) operating the automotive component that contains the fluid,
• wherein the anti-wear performance of the fluid is improved relative to the performance of a lubricating fluid free of the compound of 1) (b);
• and
• wherein R1, R2, R3, R4, R5, R6, and R7 are substituents independently 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, —(C3-C7)cycloalkyl, and —(C2-C9)heterocyclyl;
• 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;
• wherein R8 and R9 are each substituents independently selected from the group consisting of hydrogen, —(C1-C6)alkyl, —(C3-C7)cycloalkyl, —(C2-C9)heterocyclyl and said —(C2-C9)heterocyclyl group is optionally interrupted by one to three elements independently selected from the group consisting of —(C═O), —SO2, —S—, —O—, —P—, —N—, —NH—, —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 —SO2R15R8 or R9 substituents are optionally 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;
• 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 is optionally 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 is optionally interrupted by one to three elements independently selected from the group consisting of —(C═O), —SO2, —S—, —O—, —P—, —N—, —NH—, and —NR15;
• 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 are optionally 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;
• 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 are optionally substituted by one to three moieties independently selected from the group consisting of hydrogen, halogen, hydroxy, —CN, —(C1-C6)alkyl, —NH2, —NHR12, —NR122, 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;
• wherein R12 and R13 are each independently, hydrogen, or —(C1-C6)alkyl;
• wherein R14 is hydrogen or —(C1-C6)alkyl;
• and
• wherein R15 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 R15 substituent is optionally 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-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;
• 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.