Granted Patent B2

US 12,606,765 · App. 18/431,222 · Granted Apr 21, 2026

Inventors: David R. Coultas (Oxford, GB); Joanne Tory (Didcot, GB); Abby Casey (Oxford, GB)

Assignee: INFINEUM INTERNATIONAL LIMITED

C10M133/40C10M2215/221C10N2020/02C10N2030/10

Abstract

Claims (50)

1 . A composition comprising a non-aqueous medium and 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

wherein the non-aqueous medium comprises a Group I, Group II, Group III, Group IV, and/or Group V lubricating oil basestock.

2 . 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.

3 . A composition of claim 1 , further comprising at least one lubricant additive selected from the group consisting of a calcium- and/or magnesium-containing detergent, an ashless dispersant, a corrosion inhibitor, an antioxidant, a friction modifier, an 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.

4 . The composition of claim 3 , wherein the at least one lubricant additive comprises an optionally substituted diaryl amine antioxidant, a hindered phenol antioxidant, or both.

5 . The composition of claim 4 , wherein 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.

6 . The composition of claim 3 , wherein the at least one lubricant additive comprises one or more of: a zinc dialkyldithiophosphate antiwear agent; an organic friction modifier, a molybdenum-containing friction modifier, or a combination thereof; and 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.

7 . The composition according of claim 3 , wherein the at least one lubricant additive comprises 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 such as poly(vinyl acetate), or a combination or copolymer thereof.

8 . A lubricant composition comprising the composition of claim 1 .

9 . A method of inhibiting and/or mitigating viscosity increase in a composition comprising a non-aqueous medium by addition of the 3,4-oxypyridinone composition of claim 1 , or via formation of a complex or reaction product thereof, in an amount that is effective in disrupting oxidation catalysis through iron chelation.

10 . A method to inhibit and/or mitigate viscosity increase in a lubricant composition through effective disruption of oxidation catalysis through iron chelation comprising combining the non-aqueous 3,4-oxypyridinone-containing composition of claim 1 , or a complex or reaction product thereof, with the lubricant composition.

11 . A method of improving oxidative stability and/or mitigating impact of oxidative degradation of a composition comprising a non-aqueous medium comprising addition of the 3,4-oxypyridinone composition of claim 1 , or via formation of a complex or reaction product thereof, in an amount that is effective in disrupting oxidation catalysis through iron chelation.

12 . A method to improve improve oxidative degradation of and/or to mitigate viscosity increase in a lubricant composition comprising addition of the non-aqueous 3,4-oxypyridinone-containing composition of claim 1 , or a complex or reaction product thereof, to the lubricant composition in an amount effective to disrupt oxidation catalysis through iron chelation.

13 . A lubricant composition comprising the composition of claim 4 , wherein the lubricant composition comprising the 3,4-oxypyridinone of structure (I) and either or both of the optionally substituted diaryl amine and hindered phenol antioxidants, when subject to a CEC L-109 oxidation test for at least 200 hours at ˜150° C., exhibits an increase in a value of kinematic viscosity at ˜100° C. (KV100) that is:

at most 40% above a KV100 value from the same lubricant composition immediately before the CEC L-109 oxidation test began (0 hours); and

at least 30% below a KV100 value from a comparative composition that was subject to the CEC L-109 oxidation test for an identical time period,

wherein the comparative composition:

(a) comprises only either or both of the optionally substituted diaryl amine and hindered phenol antioxidants and not the 3,4-oxypyridinone of structure (I); and

(b) comprises the optionally substituted diaryl amine and hindered phenol antioxidants in an identical weight ratio to the lubricant composition, and comprises a collective amount of the optionally substituted diaryl amine and hindered phenol antioxidants that is identical to the sum of the amounts of optionally substituted diaryl amine antioxidant, hindered phenol antioxidant, and 3,4-oxypyridinone of structure (I) in the lubricant composition.

14 . The lubricant composition according of claim 4 , wherein the lubricant composition comprising the 3,4-oxypyridinone of structure (I) and either or both of the optionally substituted diaryl amine and hindered phenol antioxidants (and optionally also a magnesium detergent), when subject to a CEC L-109 oxidation test for at least 200 hours at ˜150° C., exhibits an increase in a value of kinematic viscosity at ˜100° C. (KV100) that is:

at most 30% above a KV100 value from the same lubricant composition immediately before the CEC L-109 oxidation test began (0 hours); and

at least 12% below a KV100 value from a comparative composition that was subject to the CEC L-109 oxidation test for an identical time period,

wherein the comparative composition:

(a) comprises only either or both of the optionally substituted diaryl amine and hindered phenol antioxidants and not the 3,4-oxypyridinone of structure (I); and

(b) comprises the optionally substituted diaryl amine and hindered phenol antioxidants in an identical weight ratio to the lubricant composition, and comprises a collective amount of the optionally substituted diaryl amine and hindered phenol antioxidants that is identical to the sum of the amounts of optionally substituted diaryl amine antioxidant, hindered phenol antioxidant, and 3,4-oxypyridinone of structure (I) in the lubricant composition.

15 . The lubricant composition according of claim 4 , wherein the lubricant composition comprising the 3,4-oxypyridinone of structure (I) (optionally in an amount from 0.25 wt % to 1.3 wt %, based on the weight of the lubricant composition) and either or both of the optionally substituted diaryl amine and hindered phenol antioxidants, when subject to an oxidation test in a heavy exhaust gas recycle (EGR) diesel engine with variable geometry turbocharging (VGT) for up to 420 hours, exhibits an increase in a value of kinematic viscosity at ˜40° C. (KV40) that is:

after ˜360 hours, at most 20 cSt above a KV40 value from the same lubricant composition immediately before the diesel engine oxidation test began (0 hours); and

after at least 324 hours, at least 15% below a KV40 value from a comparative composition that was subject to the diesel engine oxidation test for an identical time period,

wherein the comparative composition comprises only both the optionally substituted diaryl amine and hindered phenol antioxidants and not the 3,4-oxypyridinone of structure (I).

16 . The method of claim 15 , wherein the lubricant composition comprising the 3,4-oxypyridinone of structure (I) and either or both of the optionally substituted diaryl amine and hindered phenol antioxidants, when subject to an oxidation test in a heavy exhaust gas recycle (EGR) diesel engine with variable geometry turbocharging (VGT) for up to 420 hours, further exhibits an increase in a value of kinematic viscosity at ˜40° C. (KV40) that is:

after ˜360 hours, at most 1.5 cSt above a KV40 value from the same lubricant composition immediately before the diesel engine oxidation test began (0 hours); and

after at least 336 hours, at least 10% below a KV40 value from a comparative composition that was subject to the diesel engine oxidation test for an identical time period,

wherein the comparative composition comprises only both the optionally substituted diaryl amine and hindered phenol antioxidants and not the 3,4-oxypyridinone of structure (I).

17 . A method of improving oxidative degradation of and mitigating impact of oxidative degradation of a lubricant composition comprising a non-aqueous medium comprising addition of the 3,4-oxypyridinone containing composition of claim 1 , or via formation of a complex or reaction product thereof, in an amount that is effective in disrupting oxidation catalysis through iron chelation.

Assignments (1)

Continuity (1)

References Cited (75)