Borated polyol ester of hindered phenol antioxidant/friction modifier with enhanced performance

A compound having the following formula (IV):

• wherein Q is an alkylene group of 2 to 6 carbon atoms;
• each m is independently 1, 2, or 3;
• each p is independently 0, 1, 2, or 3;
• each q is independently 0, 1, 2, or 3;
• x is 0, 1, or 2;
• R1 and R2 are each independently a C1-C12 alkyl group;
• R3 is absent or a C1-C12 alkoxy group;
• R4 is absent or a C1-C12 alkoxy group;
• R5 is H, a C1-C12 alkyl group, or a C1-C3 alkanol;
• and R6 is H, a C1-C12 alkyl group, or a C1-C3 alkanol.

A compound having the following formula (V):

• wherein Q is an alkylene group of 2 to 6 carbon atoms;
• each m is independently 1, 2, or 3;
• each p is independently 0, 1, 2, or 3;
• each q is independently 0, 1, 2, or 3;
• x is 0, 1, or 2;
• R1 and R2 are each independently a C1-C12 alkyl group;
• R5 is H, a C1-C12 alkyl group, or a C1-C3 alkanol;
• and R6 is H, a C1-C12 alkyl group, or a C1-C3 alkanol.

A compound comprising the reaction product of:

• a. a polyol,
• b. a boron containing compound, and
• c. a phenolic acid or ester, wherein the polyol has the following formula (III):
• wherein each m is independently 1, 2, or 3;
• each p is independently 0, 1, 2, or 3;
• each q is independently 0, 1, 2, or 3;
• x is 0, 1, or 2;
• R5 is H, a C1-C12 alkyl group, or a C1-C3 alkanol;
• and R6 is H, a C1-C12 alkyl group, or a C1-C3 alkanol;
• and the phenolic acid or ester has the following formula (II):
• wherein Q is an alkylene group of 2 to 6 carbon atoms;
• R is H or a moiety suitable to undergo transesterification;
• R1 and R2 are each independently a C1-C12 alkyl group.