Lubricant and fuel additives derived from treated amines

• US 7,645,728 B2
• Filed: 02/17/2004
• Issued: 01/12/2010
• Est. Priority Date: 02/17/2004
• Status: Active Grant

• Current Assignee: Afton Chemical Corporation (Newmarket Corporation)
• Original Assignee: Afton Chemical Corporation (Newmarket Corporation)
• Inventors: Esche, Carl K. Jr., Loper, John T.
• Primary Examiner(s): Caldarola; Glenn
• Assistant Examiner(s): GOLOBOY, JAMES C
• Application Number:
  US10/779,970
• Publication Number:
  US 20050181959A1
• Time in Patent Office: 2,156 Days
• Field of Search: 508/291, 508/542
• US Class Current: 508/542
• CPC Class Codes: C10L 1/2364 homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups C10L1/221 takes precedence
• CPC Class Codes: C10L 1/2366 homo- or copolymers derived from unsaturated compounds containing amine groups C10L1/221 takes precedence
• CPC Class Codes: C10L 1/238 obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds C10L1/221 takes precedence
• CPC Class Codes: C10L 1/2383 Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) C10L1/221 takes precedence
• CPC Class Codes: C10L 1/2387 Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C) C10L1/221 takes precedence
• CPC Class Codes: C10L 10/04 for minimising corrosion or incrustation
• CPC Class Codes: C10L 10/08 for improving lubricity; for reducing wear
• CPC Class Codes: C10M 133/16 Amides; Imides
• CPC Class Codes: C10M 133/56 Amides; Imides
• CPC Class Codes: C10M 149/06 containing monomers having an unsaturated radical bound to an amido or imido group
• CPC Class Codes: C10M 159/12 Reaction products
• CPC Class Codes: C10M 159/16 obtained by Mannich reactions
• CPC Class Codes: C10M 2215/08 Amides
• CPC Class Codes: C10M 2215/086 Imides
• CPC Class Codes: C10M 2217/024 containing monomers having an unsaturated radical bound to an amido or imido group
• CPC Class Codes: C10M 2217/043 Mannich bases
• CPC Class Codes: C10N 2020/04 Molecular weight; Molecular weight distribution
• CPC Class Codes: C10N 2030/04 Detergent property or dispersant property
• CPC Class Codes: C10N 2030/06 Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
• CPC Class Codes: C10N 2040/042 for automatic transmissions
• CPC Class Codes: C10N 2040/045 : for continuous variable transmission [CVT]
• CPC Class Codes: C10N 2040/08 : Hydraulic fluids, e.g. brake-fluids
• CPC Class Codes: C10N 2040/252 : Diesel engines
• CPC Class Codes: C10N 2040/255 : Gasoline engines

Abstract

A composition for use as an additive for fuels or lubricants. The composition includes a reaction product of a treated amine and a compound selected from the group consisting of hydrocarbyl succinic anhydrides, Mannich adducts derived from hydrocarbyl-substituted phenols reacted with formaldehydes, ethylene-propylene copolymers grafted with ethylenically unsaturated carboxylic groups, copolymers of unsaturated acids and polyolefins, and acid or ester functionalized hydrocarbon polymers. The reaction product is oil soluble and has a number average molecular weight ranging from about 900 to about 50,000 as determined by gel permeation chromatography. The treated amine includes an aliphatic or aromatic amine containing at least one primary or secondary amino group reacted with an aliphatic or aromatic nitrile and hydrogen.

Claims

1. A composition for use as an additive for fuels or lubricants comprising a reaction product comprising Mannich adducts derived from hydrocarbyl-substituted phenols, formaldehydes and treated amines, wherein the reaction product is oil soluble and has a number average molecular weight ranging from about 900 to about 50,000 as determined by gel permeation chromatography, and wherein the treated amine comprises an aliphatic or aromatic amine containing at least one primary or secondary amino group reacted with acrylonitrile or at least one homologue thereof followed by reduction to the primary amine,

with the proviso that the aliphatic amine is chosen from aminoguanidine bicarbonate;

a mixture of amines comprising tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine, and compounds having the structure H₂NCH₂CH₂(NHCH₂CH₂)_xNH₂, wherein x is 3 or higher;

heavy polyamines; and

hydroxyamines,

with the proviso that the aromatic amine is chosen from N-arylphenylenediamines; and

with the further proviso that if the aliphatic amine is a hydroxyamine, the hydroxyamine is chosen from oligomers, polymers, aminoethylethanolamine, aminopropyldiethanolamine, partially propoxylated hexamethylene diamine, 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.

2. The composition of claim 1, wherein the aliphatic or aromatic amine is reacted with one to five equivalents of acrylonitrile or one of its homologues, followed by reduction of the primary amine per primary or secondary amino group in the amine.

3. The composition of claim 1, wherein the amine is a substantially linear aliphatic amine.

4. The composition of claim 1, wherein the amine is an aromatic amine.

5. The composition of claim 1, wherein the reaction product comprises a hydrocarbyl-substituted succinimide derived from the treated amine and a hydrocarbyl-substituted succinic acid having a mole ratio of succinic acid to treated amine ranging from about 0.3:

1.0 to about 12.0;

1.

6. The composition of claim 1, wherein the reaction product further comprises an untreated amine selected from the group consisting of aliphatic amines and aromatic amines.

7. A lubricant composition comprising an oil of lubricating viscosity and from about 0.1 to 10 wt. %, based on the total weight of the composition of the reaction product of claim 1.

8. A vehicle having moving parts and containing a lubricant for lubricating the moving parts, the lubricant comprising an oil of lubricating viscosity and from about 0.1 to 10 wt. %, based on the total weight of the lubricant composition, of the reaction product of claim 1.

9. An additive package for lubricants or fuels comprising a reaction product of claim 1 and a composition selected from the group consisting of hydrocarbyl succinic anhydrides reacted with an amine, Mannich adducts derived from hydrocarbyl-substituted phenols reacted with formaldehydes and amines, ethylene-propylene copolymers grafted with ethylenically unsaturated carboxylic groups reacted with amines, copolymers of unsaturated acids and polyolefins reacted with amines, and acid or ester functionalized hydrocarbon polymers reacted with amines, wherein the amines comprise untreated aliphatic or aromatic amines.

10. A lubricant composition comprising an oil of lubricating viscosity and from about 0.1 to 10 wt. %, based on the total weight of the lubricant composition, of the additive of claim 9.

11. A fuel composition comprising a hydrocarbyl fuel and from about 5 to about 200 pounds per thousand barrels of the composition of claim 1.

35. The lubricating composition of claim 7, wherein the composition has a sulfur content of less than 0.5 weight percent, a phosphorus content of less than 0.11 weight percent, and a sulfated ash content of less than 1.2 weight percent.

38. The composition of claim 1, wherein the reaction product comprises Mannich adducts derived from hydrocarbyl-substituted phenols, formaldehydes and treated amines.

12. A lubricant additive comprising a reaction product comprising Mannich adducts derived from hydrocarbyl-substituted phenols, formaldehydes and treated amines, wherein the reaction product is oil soluble and has a number average molecular weight ranging from about 900 to about 50,000 as determined by gel permeation chromatography, and wherein the treated amine comprises an aliphatic or aromatic amine containing at least one primary or secondary amino group reacted with acrylonitrile or one of its homologues, followed by reduction to the primary amine,

with the proviso that the aliphatic amine is chosen from aminoguanidine bicarbonate;

a mixture of amines comprising tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine, and compounds having the structure H₂NCH₂CH₂(NHCH₂CH₂)_xNH₂, wherein x is 3 or higher;

heavy polyamines; and

hydroxyamines,

with the proviso that the aromatic amine is chosen from N-arylphenylenediamines; and

with the further proviso that if the aliphatic or aromatic amine is a hydroxyamine, the hydroxyamine is chosen from oligomers, polymers, aminoethylethanolamine, aminopropyldiethanolamine, partially propoxylated hexamethylene diamine, 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.

13. The lubricant additive of claim 12, wherein the reaction product further comprises an untreated amine selected from the group consisting of aliphatic and aromatic amines.

14. The lubricant additive of claim 12, further comprising a composition selected from the group consisting of hydrocarbyl succinic anhydrides reacted with amines, Mannich adducts derived from hydrocarbyl-substituted phenols reacted with formaldehydes and amines, ethylene-propylene copolymers grafted with ethylenically unsaturated carboxylic groups reacted with amines, copolymers of unsaturated acids and polyolefins reacted with amines, and acid or ester functionalized hydrocarbon polymers reacted with amines, wherein the amines comprise untreated aliphatic or aromatic amines.

15. The lubricant additive of claim 12, wherein the reaction product is a post treated reaction product.

16. A lubricant composition comprising an oil of lubricating viscosity and from about 0.1 to 10 wt. %, based on the total weight of the lubricant composition, of the lubricant additive of claim 12.

21. A fuel composition comprising a fuel and from about 5 to 200 pounds per thousand barrels of the lubricant additive of claim 12.

17. A fuel additive comprising a reaction product comprising Mannich adducts derived from hydrocarbyl-substituted phenols, formaldehydes and treated amines, wherein the reaction product is oil soluble and has a number average molecular weight ranging from about 900 to about 50,000 as determined by gel permeation chromatography, and wherein the treated amine comprises an aliphatic or aromatic amine containing at least one primary or secondary amino group reacted with acrylonitrile or at least one homologue thereof, followed by reduction to the primary amine

with the proviso that the aliphatic amine is chosen from aminoguanidine bicarbonate;

a mixture of amines comprising tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine, and compounds having the structure H₂NCH₂CH₂(NHCH₂CH₂)_xNH₂, wherein x is 3 or higher;

heavy polyamines; and

hydroxyamines,

with the proviso that the aromatic amine is chosen from N-arylphenylenediamines; and

with the further proviso that if the aliphatic or aromatic amine is a hydroxyamine, the hydroxyamine is chosen from oligomers, polymers, aminoethylethanolamine, aminopropyldiethanolamine, partially propoxylated hexamethylene diamine, 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.

18. The fuel additive of claim 17, wherein the reaction product further comprises an untreated amine selected from the group consisting of aliphatic and aromatic amines.

19. The fuel additive of claim 17, further comprising a composition selected from the group consisting of hydrocarbyl succinic anhydrides reacted with amines, Mannich adducts derived from hydrocarbyl-substituted phenols reacted with formaldehydes and amines, ethylene-propylene copolymers grafted with ethylenically unsaturated carboxylic groups reacted with amines, copolymers of unsaturated acids and polyolefins reacted with amines, and acid or ester functionalized hydrocarbon polymers reacted with amines, wherein the amines comprise untreated aliphatic or aromatic amines.

20. The fuel additive of claim 17, wherein the reaction product is a post treated reaction product.

22. A method of lubricating moving parts of a vehicle, the method comprising using as a lubricating oil for one or more moving parts of the vehicle a lubricant composition containing a lubricant and a lubricant additive, the lubricant additive including a reaction product comprising Mannich adducts derived from hydrocarbyl-substituted phenols, formaldehydes and treated amines, wherein the reaction product is oil soluble and has a number average molecular weight ranging from about 900 to about 50,000 as determined by gel permeation chromatography, and wherein the treated amine comprises an aliphatic or aromatic amine containing at least one primary or secondary amino group reacted with acrylonitrile or a homologue thereof, followed by reduction to the primary amine,

with the proviso that the aliphatic amine is chosen from aminoguanidine bicarbonate;

a mixture of amines comprising tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine, and compounds having the structure H₂NCH₂CH₂(NHCH₂CH₂)_xNH₂, wherein x is 3 or higher;

heavy polyamines; and

hydroxyamines,

with the proviso that the aromatic amine is chosen from N-arylphenylenediamines; and

with the further proviso that if the aliphatic or aromatic amine is a hydroxyamine, the hydroxyamine is chosen from oligomers, polymers, aminoethylethanolamine, aminopropyldiethanolamine, partially propoxylated hexamethylene diamine, 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.

23. The method of claim 22 wherein the vehicle includes an internal combustion engine having a crankcase and wherein the lubricant composition comprises a crankcase oil present in the crankcase of the vehicle.

24. The method of claim 22 wherein the lubricant composition comprises a drive train lubricant present in an automotive drive train of the vehicle.

25. The method of claim 22, wherein the reaction product includes an untreated amine selected from the group consisting of aliphatic and aromatic amines.

26. The method of claim 22, wherein the lubricant additive includes a composition selected from the group consisting of hydrocarbyl succinic anhydrides reacted with amines, Mannich adducts derived from hydrocarbyl-substituted phenols reacted with formaldehydes and amines, ethylene-propylene copolymers grafted with ethylenically unsaturated carboxylic groups reacted with amines, copolymers of unsaturated acids and polyolefins reacted with amines, and acid or ester functionalized hydrocarbon polymers reacted with amines, wherein the amines comprise untreated aliphatic or aromatic amines.

27. The method of claim 22, wherein the reaction product is a post treated reaction product.

28. A method for lubricating moving parts comprising contacting the moving parts with a lubricant composition containing a lubricant and a lubricant additive, the lubricant additive comprising a reaction product comprising Mannich adducts derived from hydrocarbyl-substituted phenols, formaldehydes and treated amines, wherein the reaction product is oil soluble and has a number average molecular weight ranging from about 900 to about 50,000 as determined by gel permeation chromatography, and wherein the treated amine comprises an aliphatic or aromatic amine containing at least one primary or secondary amino group reacted with acrylonitrile or homologue thereof, followed by reduction to the primary amine,

with the proviso that the aliphatic amine is chosen from aminoguanidine bicarbonate;

a mixture of amines comprising tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine, and compounds having the structure H₂NCH₂CH₂(NHCH₂CH₂)_xNH₂, wherein x is 3 or higher;

heavy polyamines; and

hydroxyamines,

with the proviso that the aromatic amine is chosen from N-arylphenylenediamines; and

with the further proviso that if the aliphatic or aromatic amine is a hydroxyamine, the hydroxyamine is chosen from oligomers, polymers, aminoethylethanolamine, aminopropyldiethanolamine, partially propoxylated hexamethylene diamine, 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.

29. The method of claim 28 wherein the lubricant composition comprises a gear lubricant present in a gear box.

30. The method of claim 28, wherein the reaction product includes an untreated amine selected from the group consisting of aliphatic and aromatic amines.

31. The method of claim 28, wherein the lubricant additive includes a composition selected from the group consisting of hydrocarbyl succinic anhydrides reacted with amines, Mannich adducts derived from hydrocarbyl-substituted phenols reacted with formaldehydes and amines, ethylene-propylene copolymers grafted with ethylenically unsaturated carboxylic groups reacted with amines, copolymers of unsaturated acids and polyolefins reacted with amines, and acid or ester functionalized hydrocarbon polymers reacted with amines, wherein the amines comprise untreated aliphatic or aromatic amines.

32. The method of claim 28, wherein the reaction product is a post treated reaction product.

33. A method for decreasing combustion chamber deposits and/or intake valve deposits in an engine comprising providing a fuel containing an additive comprising Mannich adducts derived from hydrocarbyl-substituted phenols reacted with formaldehydes and amines,

wherein the amines comprise treated aliphatic or aromatic amines,

wherein the treated amines comprise an aliphatic or aromatic amine containing at least one primary or secondary amino group reacted with acrylonitrile or homologue thereof, followed by reduction to the primary amine,

with the proviso that the aliphatic amine is chosen from aminoguanidine bicarbonate;

a mixture of amines comprising tetraethylene pentamine, and pentaethylene hexamine, hexaethylene heptamine, and compounds having the structure H₂NCH₂CH₂(NHCH₂CH₂)_xNH₂, wherein x is 3 or higher;

heavy polyamines; and

hydroxyamines,

with the proviso that the aromatic amine is chosen from N-arylphenylenediamines; and

with the further proviso that if the aliphatic or aromatic amine is a hydroxyamine, the hydroxyamine is chosen from oligomers, polymers, aminoethylethanolamine, aminopropyldiethanolamine, partially propoxylated hexamethylene diamine, 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.

34. The method of claim 33, wherein the reaction product is a post treated reaction product.

36. A composition for use as an additive for fuels or lubricants comprising a reaction product comprising Mannich adducts derived from hydrocarbyl-substituted phenols, formaldehydes and treated amines, wherein the reaction product is oil soluble and has a number average molecular weight ranging from about 900 to about 50,000 as determined by gel permeation chromatography, and wherein the treated amine comprises an aliphatic or aromatic amine containing at least one primary or secondary amino group reacted with acrylonitrile or at least one homologue thereof, followed by reduction to the primary amine,

with the proviso that the aliphatic amine is chosen from anioguanidine bicarbonate;

a mixture of amines comprising tetraethylene pentamine, pentaethylene hexamine, hexaethylene heptamine, and compounds having the structure H₂NCH₂CH₂(NHCH₂CH₂)_xNH₂, wherein x is 3 or higher;

heavy polyamines; and

hydroxyamines,

with the further proviso that if the aliphatic amine is a hydroxylamine, the hydroxylamine is chosen from oligomers, polymers, aminoethylethanolamine, aminopropyldiethanolamine, partially propoxylated hexamethylene diamine, 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.

37. The composition of claim 36, wherein the reaction product comprises a hydrocarbyl-substituted succinimide derived from the treated amine and a hydrocarbyl-substituted succinic acid having a mole ratio of succinic aid to treated amine ranging from about 0.3:

1.0 to about 12.0;

1.