Granted Patent B2

US 12,606,766 · App. 18/431,334 · Granted Apr 21, 2026

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

Assignee: INFINEUM INTERNATIONAL LIMITED

C10M133/40C10M101/00C10M163/00C10M2203/1085C10M2215/221C10N2010/12C10N2020/02C10N2030/12C10N2050/01

Abstract

Claims (65)

1 . A lubricant composition comprising:

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

a compound of structure (I):

wherein:

each A is individually an oxygen atom, a sulfur atom, an oxymethyl (—CH 2 —O—) moiety, or a methylthio (—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; or another compound of structure (I) connected as an ether or thioether at a meta position to the ring nitrogen 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; or a nitrile-containing linear, branched, and/or cyclic C 1 -C 20 moiety;

R 3 is hydrogen; a halogen; or a linear, branched, and/or cyclic C 6 -C 24 hydrocarbyl moiety;

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; or a nitrile-containing linear, branched, and/or cyclic C 1 -C 20 moiety; 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; or an R 1 -A-moiety;

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:

an optionally substituted triazole corrosion inhibitor, an optionally substituted benzotriazole corrosion inhibitor, an optionally substituted thiadiazole, 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; or

substantially none of the following: 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; and a tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor; and

at least one additional lubricant additive selected from the group consisting of a calcium- and/or magnesium-containing detergent, an ashless dispersant, an additional 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.

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

R 3 is a linear, branched, and/or cyclic C 8 -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; or a nitrile-containing linear, branched, and/or cyclic C 1 -C 12 moiety; and

R 5 is hydrogen; or an R 1 -A-moiety;

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

4 . A lubricant composition comprising the composition of claim 1 , 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 compound of structure (I) to a sum of the optionally substituted diaryl amine and hindered phenol antioxidants is from 10:1 to 1:10;

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

substantially no molybdenum-containing friction modifier;

an additional corrosion inhibitor comprising 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.

5 . The lubricant composition of claim 1 , wherein the at least one lubricant additive comprises a molybdenum-containing friction modifier.

6 . A method of inhibiting and/or mitigating copper and/or lead corrosion on a powertrain surface exposed to a composition, the method comprising incorporation of an amount of a 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 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 . A method to inhibit and/or mitigate copper and/or lead corrosion on a powertrain surface comprising exposing the powertrain surface to the non-aqueous composition of claim 1 , or a complex or reaction product thereof, wherein the composition comprises 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.

8 . A method of inhibiting and/or mitigating copper and/or lead corrosion on a powertrain surface exposed to a composition, the method comprising incorporation of an amount of a 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 none of the following: 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; and a tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor.

9 . A method to inhibit and/or mitigate copper and/or lead corrosion on a powertrain surface comprising exposing the powertrain surface to the non-aqueous composition of claim 1 , or a complex or reaction product thereof, wherein the composition comprises substantially none of the following: 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; and a tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor.

10 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the compound of structure (I) and a tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor (and optionally also comprising: a calcium-containing detergent and substantially no magnesium-containing detergent; and/or a calcium salicylate detergent), and when subject to a high temperature corrosion bench test (HTCBT) at ˜135° C. according to ASTM D6594, exhibits a dissolved copper level after 168 hours of no more than 25 ppm Cu and a dissolved lead level after 168 hours of no more than 100 ppm Pb.

11 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the compound of structure (I) and an optionally substituted triazole corrosion inhibitor and/or an optionally substituted benzotriazole corrosion inhibitor (and optionally also comprising: a calcium-containing detergent and substantially no magnesium-containing detergent; and/or a calcium salicylate detergent), and when subject to a high temperature corrosion bench test (HTCBT) at ˜135° C. according to ASTM D6594, exhibits a dissolved copper level after 168 hours of no more than 25 ppm Cu and a dissolved lead level after 168 hours of no more than 140 ppm Pb.

12 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the compound of structure (I) and one or more of an ashless dihydrocarbyl dithiocarbamate, a C 8 -C 18 acrylate, and a C 2 -C 6 dialkylene glycol diester (and optionally also comprising a calcium salicylate detergent), and when subject to a high temperature corrosion bench test (HTCBT) at ˜135° C. according to ASTM D6594, exhibits a dissolved copper level after 168 hours of no more than 25 ppm Cu and a dissolved lead level after 168 hours of no more than 140 ppm Pb.

13 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the compound of structure (I) and substantially none of 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, and a tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor (and optionally further comprising one or more of a calcium salicylate detergent, a combination of magnesium- and calcium-containing detergents, substantially no sulfonate detergents, substantially no molybdenum friction modifier, a zinc dihydrocarbyl dithiophosphate antiwear agent in which the hydrocarbyl groups are connected to the dithiophosphate moiety via secondary carbon atoms, and at least one boron-containing compound), and when subject to a high temperature corrosion bench test (HTCBT) at ˜135° C. according to ASTM D6594, exhibits a dissolved copper level after 168 hours of no more than 25 ppm Cu and a dissolved lead level after 168 hours of no more than 140 ppm Pb.

14 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the compound of structure (I), a tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor, and either an optionally substituted triazole corrosion inhibitor or an optionally substituted benzotriazole corrosion inhibitor, and when subject to a Sequence VIII engine test according to ASTM D6709, exhibits:

an adjusted bearing weight loss from-3% to +50% below an adjusted bearing weight loss from a comparative composition under identical test conditions; and

a stripped viscosity at ˜100° C. of no more than 2.5% above a stripped viscosity at ˜100° C. from a comparative composition under identical test conditions,

wherein the comparative composition comprises substantially none of the 3,4-oxypyridinone compound of structure (I), substantially none of the tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor, and substantially none of either the optionally substituted triazole corrosion inhibitor or the optionally substituted benzotriazole corrosion inhibitor.

15 . A method of inhibiting and/or mitigating total acid number (TAN) increase over a time period, with no more than 7% change in total base number (TBN) over the same time period, in a composition, the method comprising incorporation of an amount of a compound of structure (I) in claim 1 to the composition, or formation of an effective complex or reaction product thereof in the composition, wherein the composition comprises substantially none of the following: 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; and a tri-hydrocarbyl C 1 -C 8 borate corrosion inhibitor and wherein the oxypyridinone compound of structure (I) is represented by the structure:

wherein:

each A is individually an oxygen atom, a sulfur atom, an oxymethyl (—CH 2 —O—) moiety, or a methylthio (—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; or another compound of structure (I) connected as an ether or thioether at a meta position to the ring nitrogen 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; or a nitrile-containing linear, branched, and/or cyclic C 1 -C 20 moiety;

R 3 is hydrogen; a halogen; or a linear, branched, and/or cyclic C 6 -C 24 hydrocarbyl moiety;

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; or a nitrile-containing linear, branched, and/or cyclic C 1 -C 20 moiety; 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; or an R 1 -A-moiety;

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.

16 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the compound of structure (I) (and optionally also comprising a zinc dihydrocarbyl dithiophosphate antiwear agent, a molybdenum-containing friction modifier, and a salicylate detergent), and when subject to a Sequence X timing chain wear test for at least 216 hours according to ASTM D8279, exhibits:

for times from 120 hours to 216 hours, a decrease in TAN value, as measured according to ASTM D664, of at least 1.0 mg KOH/g below a TAN value from a comparative composition that was subject to the Sequence X timing chain wear test for an identical time period; and

(i) a difference in TBN value, as measured according to ASTM D4739, at end of test that is no more than 0.5 mg KOH/g above or below a TBN value from a comparative composition that was subject to the diesel engine oxidation test for an identical time period, and/or (ii) a difference in TBN value, as measured according to ASTM D4739, at any time during the test that is no more than 1.0 mg KOH/g above or below a TBN value 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 substantially none of the compound of structure (I) but is otherwise identical to the lubricant composition.

17 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the compound of structure (I) (and optionally also comprising a zinc dihydrocarbyl dithiophosphate antiwear agent, a molybdenum-containing friction modifier, and a salicylate detergent), and when subject to a Sequence IVB valve train wear test for ˜200 hours according to ASTM D8350, exhibits:

for times of at least 175 hours, a decrease in TAN value, as measured according to ASTM D664, of at least 1.2 mg KOH/g below a TAN value from a comparative composition that was subject to the Sequence IVB valve train wear test for an identical time period; and/or

(i) a difference in TBN value, as measured according to ASTM D4739, at end of test that is no more than 0.5 mg KOH/g above or below a TBN value from a comparative composition that was subject to the Sequence IVB valve train wear test for an identical time period, and/or (ii) a difference in TBN value, as measured according to ASTM D4739, at times of at least 25 hours that are each no more than 1.0 mg KOH/g above or below a TBN value from a comparative composition that was subject to the Sequence IVB valve train wear test for an identical time period,

wherein the comparative composition comprises substantially none of the compound of structure (I) but is otherwise identical to the lubricant composition.

18 . A lubricant composition comprising the composition of claim 1 , wherein the lubricant composition comprises the compound of structure (I), and when subject to one or more of (a) an oxidation test in a heavy exhaust gas recycle (EGR) diesel engine with variable geometry turbocharging (VGT) for at least 360 hours, (b) a Sequence X timing chain wear test for at least 216 hours according to ASTM D8279, and/or (c) a Sequence IVB valve train wear test for ˜200 hours according to ASTM D8350, exhibits, at some time after TAN-TBN crossover and until end of test, a decrease in TAN value, as measured according to ASTM D664, that is at least 10% and/or at least 0.7 mg KOH/g below a TAN value from a comparative composition that was subject to the one or more tests for an identical time period, wherein:

TAN-TBN crossover represents the time during the test at which TBN values of both lubricant composition and comparative composition, measured according to ASTM D4739, exceed TAN values of both lubricant composition and comparative composition, respectively, by at least 3%, whereas both TAN values exceeded both TBN values by at least 3% at start of test (0 hours); and

the comparative composition comprises substantially none of the compound of structure (I) but is otherwise identical to the lubricant composition.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (75)