Multipurpose oxypyridinones and their functional use-3

1 . A lubricant composition comprising:

a Group I, Group II, Group III, Group IV, and/or Group V lubricating oil basestock;

a 3,4-oxypyridinone compound of structure (I):

wherein:

each A is individually an oxygen atom, a sulfur atom, an oxymethyl (—CH 2 —O—) moiety, or a thiomethyl (—CH 2 —S—) moiety;

R 1 is hydrogen; an ammonium ion; a C 1 -C 6 monoalkylammonium ion; a C 1 -C 6 dialkylammonium ion; a C 1 -C 6 trialkylammonium ion; a C 1 -C 6 tetraalkylammonium ion; a C 1 -C 6 monoalkylsilyl moiety; a C 1 -C 6 dialkylsilyl moiety; a C 1 -C 6 trialkylsilyl moiety; an optionally substituted aryl, alkyl, alkaryl, or aralkyl sulfonyl moiety; a linear, branched, and/or cyclic C 1 -C 20 hydrocarbyl sulfide; a linear, branched, and/or cyclic C 1 -C 20 hydrocarbyl moiety; an at least partially halogenated linear, branched, and/or cyclic C 1 -C 20 moiety; an ether-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a thioether-containing linear, branched, and/or cyclic C 1 -C 20 moiety; an ester-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a thioester-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a linear, branched, and/or cyclic C 1 -C 20 acyl moiety; a linear, branched, and/or cyclic C 1 -C 20 thioacyl moiety; a linear, branched, and/or cyclic C 1 -C 20 hydrocarbyloxyacyl moiety; a linear, branched, and/or cyclic C 1 -C 20 hydrocarbyloxythioacyl moiety; a linear, branched, and/or cyclic C 1 -C 20 hydrocarbylthiocarbonyl moiety; a linear, branched, and/or cyclic C 1 -C 20 hydrocarbylthio-thioacyl moiety; an amide-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a thioamide-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a ketone-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a thioketone-containing linear, branched, and/or cyclic C 1 -C 20 moiety; an aldehyde-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a thioaldehyde-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a mercaptan-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a hydroxyl-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a nonionic linear, branched, and/or (hetero) cyclic moiety containing 1 to 20 carbon atoms at least one nitrogen atom, and optionally at least one sulfur and/or oxygen atom; another 3,4-oxypyridinone connected as an ether or thioether at a meta position to the ring nitrogen thereof, or a combination thereof;

R 2 is hydrogen; a halogen; a linear, branched, and/or cyclic C 1 -C 12 hydrocarbyl moiety; an at least partially halogenated linear, branched, and/or cyclic C 1 -C 12 moiety; an amine-containing linear, branched, and/or cyclic C 1 -C 20 moiety; an ether-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a hydroxyl-containing linear, branched, and/or cyclic C 1 -C 12 moiety; an aldehyde-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a nitrile-containing linear, branched, and/or cyclic C 1 -C 20 moiety; or a combination thereof;

R 3 is hydrogen; a halogen; a linear, branched, and/or cyclic C 10 -C 24 hydrocarbyl moiety; or a combination thereof;

R 4 is hydrogen; a halogen; a linear, branched, and/or cyclic C 1 -C 12 hydrocarbyl moiety; an at least partially halogenated linear, branched, and/or cyclic C 1 -C 12 moiety; an amine-containing linear, branched, and/or cyclic C 1 -C 20 moiety; an ether-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a hydroxyl-containing linear, branched, and/or cyclic C 1 -C 12 moiety; an aldehyde-containing linear, branched, and/or cyclic C 1 -C 20 moiety; a nitrile-containing linear, branched, and/or cyclic C 1 -C 20 moiety; or a combination thereof; and

R 5 is hydrogen; a halogen; a linear, branched, and/or cyclic C 1 -C 12 hydrocarbyl moiety; an at least partially halogenated linear, branched, and/or cyclic C 1 -C 12 moiety; a hydroxylated linear, branched, and/or cyclic C 1 -C 6 moiety; an R 1 -A- moiety; or a combination thereof;

or alternatively one or more of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , and R 4 and R 5 may together form one or more (hetero)cyclic rings;

with the proviso that R 1 and R 3 are not both hydrogen; and

either:

a zinc dialkyldithiophosphate antiwear agent, an organic friction modifier, or both; or

substantially no organic friction modifier (and optionally substantially no friction modifier).

2 . The composition of claim 1 , wherein the lubricating oil basestock comprises a Group I, Group II, and/or Group III lubricating oil basestock.

3 . The composition of claim 1 , wherein:

all A's are oxygen atoms;

R 1 is hydrogen; a linear, branched, and/or cyclic C 1 -C 12 hydrocarbyl moiety; an ether-containing linear, branched, and/or cyclic C 1 -C 12 moiety; another 3,4-oxypyridinone connected as an ether at a meta position to the ring nitrogen thereof; or a combination thereof;

R 2 is hydrogen; a linear, branched, and/or cyclic C 1 -C 12 hydrocarbyl moiety; an ether-containing linear, branched, and/or cyclic C 1 -C 12 moiety; an aldehyde-containing linear, branched, and/or cyclic C 1 -C 12 moiety; a nitrile-containing linear, branched, and/or cyclic C 1 -C 12 moiety; or a combination thereof;

R 3 is a linear, branched, and/or cyclic C 10 -C 20 hydrocarbyl moiety;

R 4 is hydrogen; a linear, branched, and/or cyclic C 1 -C 12 hydrocarbyl moiety; an ether-containing linear, branched, and/or cyclic C 1 -C 12 moiety; an aldehyde-containing linear, branched, and/or cyclic C 1 -C 12 moiety; a nitrile-containing linear, branched, and/or cyclic C 1 -C 12 moiety; or a combination thereof; and

R 5 is hydrogen; an R 1 -A- moiety; or a combination thereof;

or R 4 and R 5 together comprise from 3 to 12 carbons and form a (hetero) cyclic ring structure.

4 . The composition of claim 1 , further comprising at least one additional lubricant additive selected from the group consisting of a calcium- and/or magnesium-containing detergent, an ashless dispersant, a corrosion inhibitor, an antioxidant, an additional friction modifier, an additional antiwear agent, an antifoamant, a viscosity modifier, a pour point depressant, a tackifier, a demulsifier, an extreme pressure agent, a seal swell agent, and a combination thereof.

5 . A lubricant composition comprising the composition of claim 4 , wherein the at least one lubricant additive comprises:

an optionally substituted diaryl amine antioxidant, a hindered phenol antioxidant, or both, wherein, when both are present, a weight ratio of the 3,4-oxypyridinone of structure (I) to a sum of the optionally substituted diaryl amine and hindered phenol antioxidants is from 10:1 to 1:10;

substantially no molybdenum-containing friction modifier;

an optionally substituted triazole corrosion inhibitor, an optionally substituted benzotriazole corrosion inhibitor, an optionally substituted thiadiazole corrosion inhibitor, an ashless dihydrocarbyl dithiocarbamate, a C 8 -C 18 acrylate, a C 2 -C 6 dialkylene glycol diester, a tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor, or a combination thereof; and/or

a multi-arm star viscosity modifier, an olefin copolymer viscosity modifier, a hydrogenated diene block copolymer viscosity modifier, a polystyrene copolymer viscosity modifier, a poly(meth)acrylate viscosity modifier, a poly(dialkyl fumarate)-based viscosity modifier, a poly(vinyl acyl ester)-based viscosity modifier, or a combination or copolymer thereof.

6 . A method of reducing friction and/or wear on a powertrain surface exposed to a composition, the method comprising incorporation of an amount of a 3,4-oxypyridinone compound of structure (I), or via formation of an effective complex or reaction product thereof, to attain the composition of claim 1 and/or at the powertrain surface, wherein the composition comprises a zinc dialkyldithiophosphate antiwear agent, an organic friction modifier, or both.

7 . A method to reduce friction and/or wear on a powertrain surface comprising exposing the powertrain surface to the non-aqueous 3,4-oxypyridinone-containing composition of claim 1 , or a complex or reaction product thereof, wherein the composition comprises a zinc dialkyldithiophosphate antiwear agent, an organic friction modifier, or both.

8 . A method of improving fuel economy of a powertrain exposed to a composition, the method comprising incorporation of an amount of a 3,4-oxypyridinone compound of structure (I), or via formation of an effective complex or reaction product thereof, to attain the composition of claim 1 and/or at or near the powertrain surface, wherein the composition comprises an organic friction modifier, and optionally wherein the fuel economy, when measured according to a motored friction B48 test, shows at least a 0.5% fuel economy improvement over an identical composition comprising no 3,4-oxypyridinone compound of structure (I).

9 . A method to reduce friction and/or wear to improve fuel economy on a powertrain surface comprising exposing the powertrain surface to the non-aqueous 3,4-oxypyridinone-containing composition of claim 1 , or a complex or reaction product thereof, wherein the composition comprises an organic friction modifier, and optionally wherein the fuel economy, when measured according to a motored friction B48 test, shows at least a 0.5% fuel economy improvement over an identical composition comprising no 3,4-oxypyridinone compound of structure (I).

10 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the 3,4-oxypyridinone of structure (I) and the zinc dialkyldithiophosphate antiwear agent (and optionally also a calcium detergent), and when subject to a high frequency reciprocating rig (HFRR) at temperatures from ˜40° C. to ˜140° C., exhibits a decrease in average friction coefficient value at high temperatures that are at least 0.012 below average friction coefficient values from comparative compositions that were subject to the HFRR at identical temperatures for an identical time period, wherein the comparative compositions: (a) comprise only the zinc dialkyldithiophosphate antiwear agent and not the 3,4-oxypyridinone of structure (I); and (b) comprise only the 3,4-oxypyridinone of structure (I) and no zinc dialkyldithiophosphate antiwear agent, and wherein high temperatures are from ˜90° C. to ˜140° C.

11 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the 3,4-oxypyridinone of structure (I) and the zinc dialkyldithiophosphate antiwear agent (and optionally also a calcium detergent), and when subject to a high frequency reciprocating rig (HFRR) at a temperatures of ˜140° C., exhibits:

a decrease in average wear scar void volume value of at least 15% below average wear scar void volume values from comparative compositions that were subject to the HFRR at an identical temperature for an identical time period; and/or

a decrease in average wear scar diameter value of at least 10% below average wear scar diameter values from comparative compositions that were subject to the HERR at an identical temperature for an identical time period,

wherein the comparative compositions:

(a) comprise only the zinc dialkyldithiophosphate antiwear agent and not the 3,4-oxypyridinone of structure (I); and

(b) comprise only the 3,4-oxypyridinone of structure (I) and no zinc dialkyldithiophosphate antiwear agent.

12 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the 3,4-oxypyridinone of structure (I) and the zinc dialkyldithiophosphate antiwear agent, and when subject to a Sequence X timing chain wear test for at least 216 hours according to ASTM D8279, exhibits:

for times from 72 hours to 216 hours, a decrease in average timing chain elongation value of at least 25% below an average timing chain elongation value from a comparative composition that was subject to the Sequence X timing chain wear test for an identical time period; and/or

at ˜120 hours, a decrease in average timing chain elongation value of at least 40% below an average timing chain elongation values from a comparative composition that was subject to the Sequence X timing chain wear test for an identical time period,

wherein the comparative composition comprises only the zinc dialkyldithiophosphate antiwear agent and not the 3,4-oxypyridinone of structure (I).

13 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the 3,4-oxypyridinone of structure (I) and the organic friction modifier (optionally a weight ratio of organic friction modifier to 3,4-oxypyridinone of structure (I) can be from 10:1 to 3:1), and when subject to a high frequency reciprocating rig (HFRR) at a temperature of ˜140° C., exhibits:

a decrease in average wear scar void volume value of at least 15% below average wear scar void volume values from comparative compositions that were subject to the HFRR at an identical temperature for an identical time period; and/or

a decrease in average wear scar diameter value of at least 3.5% below average wear scar diameter values from comparative compositions that were subject to the HFRR at an identical temperature for an identical time period,

wherein the comparative compositions:

(a) comprise only the organic friction modifier and not the 3,4-oxypyridinone of structure (I); and

(b) comprise only the 3,4-oxypyridinone of structure (I) and no organic friction modifier.

14 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the 3,4-oxypyridinone of structure (I) and the organic friction modifier (optionally a weight ratio of organic friction modifier to 3,4-oxypyridinone of structure (I) can be from 8:1 to 4:3), and when subject to a high frequency reciprocating rig (HFRR) temperatures from ˜40° C. to ˜140° C., exhibits an average friction coefficient value from 0.080 to 0.115 and lower than an average friction coefficient value from a comparative composition that was subject to the HFRR at identical temperatures for an identical time period, wherein the comparative composition comprises an amount of only organic friction modifier equal to the combined amount of organic friction modifier and 3,4-oxypyridinone of structure (I).

15 . A method of reducing friction and/or wear on a powertrain surface exposed to a composition, the method comprising incorporation of an amount of a 3,4-oxypyridinone compound of structure (I), or via formation of an effective complex or reaction product thereof, to attain the composition of claim 1 and/or at the powertrain surface, wherein the composition comprises substantially no organic friction modifier (or substantially no friction modifier), and optionally, and when subject to a high frequency reciprocating rig (HFRR) at temperatures from ˜40° C. to ˜140° C., the composition exhibits a decrease in average friction coefficient value:

at all temperatures that are at least 0.02 below an average friction coefficient value from a comparative composition that was subject to the HFRR at identical temperatures for an identical time period; and

at moderate-to-high temperatures that are at least 0.06 below an average friction coefficient value from a comparative composition that was subject to the HFRR at identical temperatures for an identical time period, wherein moderate-to-high temperatures are from ˜80° C. to ˜140° C.,

wherein the comparative composition comprises substantially no 3,4-oxypyridinone of structure (I) and also substantially no friction modifier.