Polymeric viscosity modifiers for use in lubricants
A lubricating oil composition having greater than 50 wt % of a base oil and 0.1 wt % to 20 wt %, both based on the total weight of the lubricating oil composition, of a dispersant viscosity modifier obtainable by: A) reacting: a) at least one of a lactone of formula (I) or a derivative thereof: wherein X is oxygen, and R is an optionally substituted hydrocarbylene group having from 1 to 20 carbon atoms; and b) at least one compound selected from amines, alcohols and oxazolines; and B) reacting the reaction product of step A) onto an acylated olefin copolymer obtainable by acylating a copolymer of ethylene and one or more C 3 -C 10 alpha-olefins having a number average molecular weight of 5,000 to 200,000 g/mol as measured by GPC, with an acylating agent. Methods employing the lubricating oil compositions and uses of the lubricating compositions as engine oils are also described.
1. A lubricating oil composition comprising:
greater than 50 wt % of a base oil, based on the total weight of the lubricating oil composition, and
0.1 wt % to 20 wt %, based on the total weight of the lubricating oil composition, of a dispersant viscosity modifier obtainable by:
A) forming a reaction product by reacting components a) and b) in a molar ratio of about 1:1:
a) at least one of a lactone of formula (I) or a derivative thereof:
wherein X is oxygen, and R is an optionally substituted hydrocarbylene group having from 1 to 20 carbon atoms, wherein the hydrocarbylene group can be substituted with 1-3 substituents independently selected from halogen, hydroxyl, nitro, cyano, carboxy, and an alkyl or alkenyl group having 1 to 32 carbon atoms which may be linear or branched; and
b) at least one compound selected from:
a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group; and
a linear, branched cyclic or aromatic alcohol comprising at least one primary or secondary alcohol according to Formula (III), or a tertiary alkyl or alkenyl alcohol according to Formula (IV), wherein Forumla (III) and Formula (IV) are as follows:
wherein R 1 is selected from hydrogen and an optionally substituted linear or branched alkyl or alkenyl group, and R 2 is an optionally substituted linear or branched alkyl or alkenyl group and the number of carbon atoms of R 1 and R 2 add to a total of 7 to 31 carbon atoms, and
wherein R 3 , R 4 , and R 5 are each independently selected from an optionally substituted linear or branched alkyl or alkenyl group wherein the number of carbon atoms of R 3 , R 4 , and R 5 add to a total of 7 to 31 carbon atoms; and
B) reacting the reaction product of step A) onto an acylated olefin copolymer obtainable by acylating a copolymer of ethylene and one or more C 3 -C 10 alpha-olefins having a number average molecular weight (Mn) of 5,000 to 200,000 g/mol as measured by GPC, with an acylating agent.
2. The lubricating oil composition of claim 1 , wherein the dispersant viscosity modifier is present in an amount of from about 0.1 wt % to about 10 wt %, based on the total weight of the lubricating oil composition.
3. The lubricating oil composition of claim 1 , wherein the dispersant viscosity modifier is present in an amount of from about 0.5 wt % to about 8 wt %, based on the total weight of the lubricating oil composition.
4. The lubricating oil composition of claim 1 , wherein the dispersant viscosity modifier is present in an amount of 1 wt % to about 5 wt %, based on the total weight of the lubricating oil composition.
5. The lubricating oil composition of claim 1 , wherein the base oil is selected from a Group II base oil having at least 90 wt % saturates, a Group III base oil having at least 90 wt % saturates, a Group IV base oil, a Group V base oil and mixtures of two or more thereof.
6. The lubricating oil composition of claim 1 , wherein the copolymer is an ethylene-propylene copolymer.
7. The lubricating oil composition of claim 1 , wherein the copolymer is acylated with an ethylenically unsaturated acylating agent having at least one carboxylic acid or carboxylic anhydride group.
8. The lubricating oil composition of claim 7 , wherein the acylating agent is maleic anhydride.
9. The lubricating oil composition of claim 1 , wherein component b) is an N-arylphenylene diamine of the formula II:
wherein R 1 is hydrogen, —NH-aryl, —NH-arylalkyl, —NH-alkyl or a branched or straight chain radical having from 4 to 24 carbon atoms selected from an alkyl group, an alkenyl group, an alkoxyl group, an aralkyl group, an alkaryl group, a hydroxyalkyl group and an aminoalkyl group; R 2 is —NH 2 , CH 2 —(CH 2 ) n —NH 2 , or CH 2 -aryl-NH 2 , in which n has a value from 1 to 10; and R 3 is selected from a hydrogen, an alkyl group, an alkenyl group, an alkoxyl group, an aralkyl group, and an alkaryl group having from 4 to 24 carbon atoms.
10. The lubricating oil composition of claim 9 , wherein component b) is selected from the group consisting of 1-(2-amino-ethyl)imidazolidin-2-one, 4-(3-aminopropyl) morpholine, 3-(dimethylamino)-1-propylamine, N-phenyl-p-phenylenedi amine, N-(3-aminopropyl)-2-pyrrolidinone, aminoethyl-acetamide, β-alanine methyl ester, 1-(3-aminopropyl)imidazole, branched β-amines, arylamines, polyetheramines, and poly(arylamines).
11. The lubricating oil composition of claim 9 , wherein component b) is selected from the group consisting of N-phenyl-1,4-phenylenediamine, N-phenyl-1,3-phenylendiamine, and N-phenyl-1,2-phenylenediamine.
12. The lubricating oil composition of claim 9 , wherein the amine is N-phenyl-1,4-phenylenediamine.
13. The lubricating oil composition of claim 1 , wherein in step A) the lactone is employed and the lactone is selected from acetolactone, propiolactone, butyrolactone, valerolactone, caprolactone, δ-valerolactone, methyl-δ-valero-lactone, ε-caprolactone, methyl-ε-caprolactone, dimethyl-ε-caprolactone, methoxy-ε-caprolactone, cyclohexyl-ε-caprolactone, methylbenzyl-ε-caprolactone, caprylolactone, and methyl-caprylolactone.
14. The lubricating oil composition of claim 1 , wherein the lactone is c-caprolactone.
15. The lubricating oil composition of claim 1 , wherein the composition further comprises one or more of antioxidants, friction modifiers, anti-wear agents, detergents, antifoam agents, process oil, and dispersants.
16. The lubricating oil composition of claim 1 , wherein the dispersant viscosity modifier is further reacted with a component c), wherein component c) is at least one compound selected from:
a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group; a linear, branched cyclic or aromatic alcohol comprising at least one primary, secondary, or tertiary alkyl or alkenyl alcohols; and an oxazoline.
17. The lubricating oil composition of claim 16 , wherein component c) is selected from, N-phenyl-1,4-phenylenediamine, N-phenyl-1,3-phenylendiamine, N-phenyl-1,2-phenylenediamine, and dioctyl amine.
18. The lubricating oil composition of claim 16 , wherein component c) is selected from the group consisting of 2-ethylhexanol, 2-butyloctanol, isomyristyl alcohol, 2-hexyldecanol, isostearyl alcohol, 2-octyldodecanol, 2-decyltetradecanol, 2-dodecylhexadecanol, 2-tetradecyloctadecanol 2-dodecylhexadecanol, 2-hexyloctanol 2-ethylhexanol, 2-hydroxy-2,3-dimethylhexane, 2-butylhexanol, 2-propylhexan-1-ol, 3-Propyl-1-hexanol, 3-methyl-1-heptanol, 3-ethylheptan-1-ol, 2-ethyl-4-methylhexan-1-ol, 2,4-diethylhexan-1-ol, 2-naphthol, benzyl alcohol, 3-phenoxybenzyl alcohol, 2-naphthylmethanol, 9-anthracenemethanol, 1-pyrenemethanol, 2-(9-anthracenylmethoxy)ethanol, 2-(9-anthracenyloxyethanol), and 1-naphthalene methanol.
19. The lubricating oil composition of claim 16 , wherein component c) is 2-phenyl-2-oxazoline; 2-ethyl-2 oxazoline; 2-methyl-2-oxazoline; 2-benzyl-4,4-dimethyl-2-oxazoline; 2-ethyl-4,4-dimethyl-2 oxazoline; 2,4,4-trimethyl-2-oxazoline; 4,4-dimethyl-2-oxazoline; 2,4,5-trimethyl-3-oxazoline; 2-(2,6-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline; 2-[1-(hydroxymethyl)ethyl] oxazoline; mixtures thereof, and derivatives thereof. In yet other approaches, the oxazoline or derivative thereof includes pendant groups in positions 2, 4, and 5 or combinations thereof wherein the pendant groups are selected from heterocyclic, aromatics, hydrocarbyl groups of C 1 to C 32 , and mixtures thereof.
20. A method of improving the soot or sludge handling capability of an engine oil, comprising a step of lubricating an engine with the lubricating oil composition as claimed in claim 1 .
21. The method of claim 20 , wherein the improvement in soot or sludge handling is measured relative to a same lubricating oil composition that does not contain the dispersant viscosity modifier.
22. A method of improving thin film and boundary layer friction in an engine comprising the step of lubricating the engine with the lubricating oil composition as claimed in claim 1 .
23. The method as claimed in claim 22 , wherein the improved thin film and boundary layer friction is determined relative to a same composition that does not contain the dispersant viscosity modifier.
24. A method for improving boundary layer friction in an engine, comprising the step of lubricating the engine with the lubricating oil composition as claimed in claim 1 .
25. The method as claimed in claim 24 , wherein the improved boundary layer friction is determined relative to a same composition that does not contain the dispersant viscosity modifier.
26. A method for improving thin film friction in an engine, comprising the step of lubricating the engine with the lubricating oil composition as claimed in claim 1 .
27. The method as claimed in claim 26 , wherein the improved thin film friction is determined relative to a same composition in the absence of the dispersant viscosity modifier.
28. A process for making a polymeric composition comprising the steps of:
A) forming a reaction product by reacting components a) and b) in a molar ratio of about 1:1:
a) a lactone of formula (I) or a derivative thereof:
wherein X is oxygen, and R is an optionally substituted hydrocarbylene group having from 1 to 20 carbon atoms, wherein the hydrocarbylene group can be substituted with 1-3 substituents independently selected from halogen, hydroxyl, nitro, cyano, carboxy, and an alkyl or alkenyl group having 1 to 32 carbon atoms which may be linear or branched; and
b) at least one compound selected from:
a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group;
a linear, branched cyclic or aromatic alcohol comprising at least one primary, or secondary alcohol according to Formula (III), or a tertiary alkyl or alkenyl alcohol according to Formula (IV), wherein Formula (III) and Formula (IV) are as follows:
wherein R 1 is selected from hydrogen and an optionally substituted linear or branched alkyl or alkenyl group, and R 2 is an optionally substituted linear or branched alkyl or alkenyl group and the number of carbon atoms of R 1 and R 2 add to a total of 7 to 31 carbon atoms, and
wherein R 3 , R 4 , and R 5 are each independently selected from an optionally substituted linear or branched alkyl or alkenyl group wherein the number of carbon atoms of R 3 , R 4 , and R 5 add to a total of 7 to 31 carbon atoms; and
B) reacting the reaction product of step A) to an acylated olefin copolymer obtainable by acylating a copolymer of ethylene and one or more C 3 -C 10 alpha-olefins having a number average molecular weight Mn of 5,000 to 200,000 g/mol as measured by GPC.
29. The method of claim 28 , wherein the acylated olefin copolymer is reacted with a component c) prior to reacting with the reaction product of step A), wherein component c) is at least one compound selected from:
a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group;
a linear, branched cyclic or aromatic alcohol comprising at least one primary, secondary, or tertiary alkyl or alkenyl alcohols; and
an oxazoline.
30. The method of claim 28 , wherein step B) is carried out at a temperature range of from 115° C. to 250° C.
31. The method of claim 29 , wherein the reaction of the acylated olefin copolymer and component c) is carried out at a temperature of from 115° C. to 250° C. for 1 to 5 hours and step B) is carried out at a temperature of from 115° C. to 250° C.
32. A lubricating oil composition comprising:
greater than 50 wt % of a base oil, based on the total weight of the lubricating oil composition, and
0.1 wt % to 20 wt %, based on the total weight of the lubricating oil composition, of a dispersant viscosity modifier obtainable by:
A) forming a first reaction product by reacting components a) and b) in a molar ratio of about 1:1:
a) at least one of a lactone of formula (I) or a derivative thereof:
wherein X is oxygen, and R is an optionally substituted hydrocarbylene group having from 1 to 20 carbon atoms, wherein the hydrocarbylene group can be substituted with 1-3 substituents independently selected from halogen, hydroxyl, nitro, cyano, carboxy, and an alkyl or alkenyl group having 1 to 32 carbon atoms which may be linear or branched; and
b) at least one compound selected from:
a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group;
a linear, branched cyclic or aromatic alcohol comprising at least one primary or secondary alcohol according to Formula (III), or a tertiary alkyl or alkenyl alcohol according to Formula (IV), wherein Formula (III) and Formula (IV) are as follows:
wherein R 1 is selected from hydrogen and an optionally substituted linear or branched alkyl or alkenyl group, and R 2 is an optionally substituted linear or branched alkyl or alkenyl group and the number of carbon atoms of R 1 and R 2 add to a total of 7 to 31 carbon atoms, and
wherein R 3 , R 4 , and R 5 are each independently selected from an optionally substituted linear or branched alkyl or alkenyl group wherein the number of carbon atoms of R 3 , R 4 , and R 5 add to a total of 7 to 31 carbon atoms; and
B) forming a second reaction product by reacting:
c) at least one compound selected from:
a linear, branched cyclic or aromatic amine comprising at least one primary or secondary amino group;
a linear, branched cyclic or aromatic alcohol comprising at least one primary, secondary, or tertiary alkyl or alkenyl alcohols; and
an oxazoline; and
d) an acylated olefin copolymer obtainable by acylating a copolymer of ethylene and one or more C 3 -C 10 alpha-olefins having a number average molecular weight (Mn) of 5,000 to 200,000 g/mol as measured by GPC, with an acylating agent;
C) reacting the first and the second reaction product of steps A) and B).
33. The lubricating oil composition of claim 32 , wherein component b) is an amine, and component c) is an amine.
34. The lubricating oil composition of claim 33 , wherein the amine of components b) and c) is N-phenyl-1,4-phenylenediamine.