Alkylated heterocyclic reaction products useful as antioxidants

A macromolecular reaction product comprising (a) i) less than about 10 wt. % of one or more heterocyclic compounds substituted with one 3,5-di-hydrocarbyl-4-hydroxylbenzyl group;

• ii) less than about 25 wt. % of one or more heterocyclic compounds substituted with two 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups;
• iii) greater than about 15 wt. % of one or more heterocyclic compounds substituted with three 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups;
• greater than 40 wt. % of at least one of iv) one or more heterocyclic compounds substituted with four 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups, v) one or more heterocyclic compounds substituted with five 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups, or combinations of iv) and v);
• and (b) one or more methylene-bridged heterocyclic compounds substituted with one or more 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups, wherein the methylene-bridge is between two heterocyclic groups, wherein all wt. % are based on the total weight of the macromolecular reaction product, and said macromolecular reaction product is liquid at room temperature or solids that melt at less than about 100° C.

A composition comprising:

• a) one or more organic materials that are susceptible to oxidation in the presence of air or oxygen selected from at least one oil of lubricating viscosity selected from Group I, II, and III mineral oils, poly-alpha-olefins, synthetic esters, gas to liquid derived oils, bio-based oils, internal combustion engine oils, railroad and marine lubricants, natural gas engine oils, gas turbine oils, steam turbine oils, aviation turbine oils, rust and oxidation oils, hydraulic fluids, compressor fluids, slideway oils, quench oils, manual and automatic transmission fluids, gear oils, and greases;
• b) an antioxidant product containing:
• i) less than about 10 wt. %, of one or more heterocyclic compounds substituted with one 3,5-di-hydrocarbyl-4-hydroxylbenzyl group;
• ii) less than about 20 wt. %, of one or more heterocyclic compounds substituted with two 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups;
• iii) in the range of from about 15 wt. % to about 40 wt. % of one or more heterocyclic compounds substituted with three 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups;
• iv) in the range of from about 10 wt % to about 70 wt. % of one or more heterocyclic compounds substituted with four 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups;
• v) in the range of from about 5 wt % to about 45 wt. % of one or more heterocyclic compounds substituted with five 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups;
• vi) in the range of from about 1 wt % to about 15 wt. % of one or more methylene-bridged heterocyclic compounds substituted with one or more 3,5-di-hydrocarbyl-4-hydroxylbenzyl groups, wherein the methylene-bridge is between two heterocyclic groups,
• wherein all wt. % are based on the total weight of the macromolecular reaction product;
• and
• c) one or more dispersants, detergents, anti-wear additives, extreme pressure additives, corrosion inhibitors, rust inhibitors, friction modifiers, metal deactivators, lubricity agents, pour point depressants, antiknock agents, anti-icing agents, viscosity index modifiers, emulsifiers, demulsifiers, seal swell agents, solubilizing agents, antifoam agents, other antioxidants or stabilizers, diluents, solvents, carrier fluids, Zinc dialkyldithiophosphate, at least one conventional hindered phenolic antioxidant, at least one conventional alkylated diphenylamine antioxidant, at least one organomolybdenum compound, at least one alkylated diphenylamine and at least one organomolybdenum compound, at least one phosphorus-free anti-wear or extreme pressure additive, at least one molybdenum-containing or boron-containing dispersant, at least one organoboron compound, at least one organoboron compound and at least one conventional alkylated diphenylamine, at least one sulfurized antioxidant, EP (extreme pressure) additive or anti-wear additive, at least one conventional alkylated diphenylamine along with at least one (i) sulfurized antioxidant, (ii) EP additive, (iii) anti-wear additive, and (iv) organoboron compound.