Multipurpose oxypyridinones and their functional use-2
A composition is provided to comprise a non-aqueous medium and a 3,4-oxypyridinone compound of structure (I): with each A being oxygen and/or sulfur, and with a variety of substituents at R 1 -R 5 to enable a solution or an at least semi-stable emulsion to be formed in the non-aqueous medium. Methods of use are included herein, which may be focused on situations where the composition can be used as a lubricant and/or coolant.
1 . A composition comprising a non-aqueous medium and a 3,4-oxypyridinone compound of structure (I):
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 an oligomeric and/or polymeric moiety containing repeat units comprising reacted pendant to one or more repeat units, optionally olefins, hydrogenated conjugated dienes, or combinations thereof, at least one of which repeat units is attached to the ring nitrogen, optionally with a spacer, a number average molecular weight of which oligomeric and/or polymeric moiety is from 700 g/mol to 30000 g/mol;
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 may together comprise from 3 to 12 carbons and form a (hetero)cyclic ring structure,
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 an oligomeric and/or polymeric moiety containing repeat units comprising reacted pendant to one or more repeat units, optionally olefins, hydrogenated conjugated dienes, or combinations thereof, at least one of which repeat units is attached to the ring nitrogen, optionally with a spacer, a number average molecular weight of which oligomeric and/or polymeric moiety is from 700 g/mol to 30000 g/mol;
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 may together comprise from 3 to 12 carbons and form a (hetero)cyclic ring structure.
2 . The composition of claim 1 , wherein the non-aqueous medium comprises a Group I, Group II, Group III, Group IV, and/or Group V lubricating oil basestock.
3 . The 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) (based on 3,4-oxypyridinone ring(s) plus optional spacer only, not including connected oligomer and/or polymer portion(s)) to a sum of the optionally substituted diaryl amine and hindered phenol antioxidants is from 10:1 to 1:10 or from 5:1 to 1:5.
6 . The composition of claim 3 , wherein the at least one lubricant additive comprises:
a zinc dialkyldithiophosphate antiwear agent;
an organic friction modifier, a molybdenum-containing friction modifier, or a combination thereof;
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.
7 . The composition of claim 4 , wherein the at least one lubricant additive comprises:
a zinc dialkyldithiophosphate antiwear agent;
an organic friction modifier, a molybdenum-containing friction modifier, or a combination thereof;
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.
8 . The composition of claim 3 , wherein the at least one lubricant additive comprises substantially no molybdenum-containing friction modifier.
9 . The composition of claim 4 , wherein the at least one lubricant additive comprises substantially no molybdenum-containing friction modifier.
10 . A lubricant composition comprising the composition of claim 1 .
11 . A lubricant composition comprising the composition of claim 3 .
12 . A lubricant composition comprising the composition of claim 4 .
13 . A lubricant composition comprising the composition of claim 5 .
14 . A lubricant composition comprising the composition of claim 6 .
15 . A lubricant composition comprising the composition of claim 7 .
16 . A lubricant composition comprising the composition of claim 8 .
17 . A lubricant composition comprising the composition of claim 9 .
18 . 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.
19 . 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 a lubricant composition.
20 . 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.
21 . A method of improving oxidative degradation of and/or mitigating impact of oxidative degradation of a lubricant composition 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.
22 . 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 (and optionally also a magnesium detergent and/or a salicylate 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 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 comprises only either or both of the optionally substituted diaryl amine and hindered phenol antioxidants and not the 3,4-oxypyridinone of structure (I).