Modified high molecular weight succinimides

• US 5,334,321 A
• Filed: 03/09/1993
• Issued: 08/02/1994
• Est. Priority Date: 03/09/1993
• Status: Expired due to Term

• Current Assignee: Chevron Research And Technology Company (Chevron Corp.)
• Original Assignee: Chevron Research And Technology Company (Chevron Corp.)
• Inventors: Harrison, James J., Ruhe, William R. Jr.
• Primary Examiner(s): Howard, Jacqueline V.
• Application Number:
  US08/028,433
• Time in Patent Office: 511 Days
• Field of Search: 252/51.5 A, 252/51.5 R, 548/545, 548/546, 549/228, 549/229
• US Class Current: 508/291
• 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 10/04 for minimising corrosion or incrustation
• CPC Class Codes: C10L 10/18 use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
• CPC Class Codes: C10M 133/56 Amides; Imides
• CPC Class Codes: C10M 2205/028 containing aliphatic monomers having more than four carbon atoms
• CPC Class Codes: C10M 2207/028 Overbased salts thereof
• CPC Class Codes: C10M 2207/262 derived from hydroxy substituted aromatic acids, e.g. salicylates
• CPC Class Codes: C10M 2207/281 of (cyclo)aliphatic monocarboxylic acids
• CPC Class Codes: C10M 2207/282 of (cyclo)aliphatic oolycarboxylic acids
• CPC Class Codes: C10M 2207/283 of polyhydroxy compounds
• CPC Class Codes: C10M 2207/286 of polymerised unsaturated acids
• CPC Class Codes: C10M 2207/287 Partial esters
• CPC Class Codes: C10M 2207/302 derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
• CPC Class Codes: C10M 2207/304 derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
• CPC Class Codes: C10M 2207/34 Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
• CPC Class Codes: C10M 2215/04 having amino groups bound to acyclic or cycloaliphatic carbon atoms
• CPC Class Codes: C10M 2215/26 Amines
• CPC Class Codes: C10M 2215/28 Amides; Imides
• CPC Class Codes: C10M 2217/046 Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
• CPC Class Codes: C10M 2217/06 Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
• CPC Class Codes: C10M 2219/046 : Overbasedsulfonic acid salts
• CPC Class Codes: C10M 2219/087 : containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
• CPC Class Codes: C10M 2219/088 : Neutral salts
• CPC Class Codes: C10M 2219/089 : Overbased salts
• CPC Class Codes: C10M 2223/045 : Metal containing thio derivatives
• CPC Class Codes: C10N 2010/04 : Groups 2 or 12
• CPC Class Codes: C10N 2040/08 : Hydraulic fluids, e.g. brake-fluids
• CPC Class Codes: C10N 2040/25 : Internal-combustion engines
• CPC Class Codes: C10N 2040/251 : Alcohol-fuelled engines
• CPC Class Codes: C10N 2040/252 : Diesel engines
• CPC Class Codes: C10N 2040/253 : Small diesel engines
• CPC Class Codes: C10N 2040/255 : Gasoline engines
• CPC Class Codes: C10N 2040/28 : Rotary engines
• CPC Class Codes: C10N 2070/02 : Concentrating of additives

Abstract

Alkenyl or alkyl succinimide additives which are the reaction product of a high molecular weight alkenyl- or alkyl-substituted succinic anhydride and a polyalkylene polyamine having an average of greater than 4 nitrogen atoms per mole, wherein the reaction product is post-treated with a cyclic carbonate, are compatible with fluorocarbon engine seals and, for concentration levels at which fluorocarbon seal compatibility is achieved, possess improved dispersancy and/or detergency properties when employed in lubricating oils and fuels,

Claims

1. A modified polyamino alkenyl or alkyl succinimide comprising the succinimide reaction product of:

(i) an alkenyl- or alkyl-substituted succinic anhydride derived from a polyolefin having a Mn of about 2000 to about 2700 and a Mw/Mn ratio of about 1 to about 5; and

(ii) a polyalkylene polyamine having greater than 4 nitrogen atoms per mole;

wherein the succinimide reaction product is post-treated with a cyclic carbonate.

2. A modified polyamino alkenyl or alkyl succinimide according to claim 1 wherein the charge mole ratio of (ii) to (i) is from about 0.35:

1 to about 0.6;

1; and

the charge mole ratio of cyclic carbonate to basic amine nitrogen in the succinimide reaction product is from about 1.5;

1 to about 4;

1.

3. A modified polyamino alkenyl or alkyl succinimide according to claim 1 wherein the polyolefin has a Mn value of about 2100 to about 2400.

4. A modified polyamino alkenyl or alkyl succinimide according to claim 3 wherein the polyolefin has a Mn value of about 2200.

5. A modified polyamino alkenyl or alkyl succinimide according to claim 1 wherein the polyolefin is polybutene.

6. A modified polyamino alkenyl or alkyl succinimide according to claim 5 wherein the polybutene is polyisobutene.

7. A modified polyamino alkenyl or alkyl succinimide according to claim 1 wherein the polyalkylene polyamine has greater than 4 to about 12 nitrogen atoms per mole.

8. A modified polyamino alkenyl or alkyl succinimide according to claim 7 wherein the polyalkylene polyamine has from about 5 to about 7 nitrogen atoms per mole.

9. A modified polyamino alkenyl or alkyl succinimide according to claim 8 wherein the polyalkylene polyamine is Union Carbide HPA-X heavy polyamine.

10. A modified polyamino alkenyl or alkyl succinimide according to claim 8 wherein the polyalkylene polyamine comprises 20% by weight diethylene triamine and 80% by weight heavy polyamine.

11. A modified polyamino alkenyl or alkyl succinimide according to claim 1 wherein the succinic anhydride has a succinic ratio from about 1 to less than about 2.

14. A modified polyamino alkenyl succinimide according to claim 1 wherein the cyclic carbonate is ethylene carbonate.

15. A modified polyamino alkenyl or alkyl succinimide according to claim 1 wherein the polyolefin is polyisobutene having a Mn of about 2200, the succinic anhydride has a succinic ratio from about 1 to about 1.7, the polyalkylene polyamine comprises heavy polyamine having a Mn of 275, the charge mole ratio of (ii) to (i) is from about 0.4:

1 to about 0.5;

1, the cyclic carbonate is ethylene carbonate, and the charge mole ratio of cyclic carbonate to basic amine nitrogen in the succinimide reaction product is from about 2;

1 to about 3;

1.

16. A modified polyamino alkenyl or alkyl succinimide according to claim 1 wherein the polyolefin is polyisobutene having a Ma of about 2200, the succinic anhydride has a succinic ratio from about 1 to about 1.7, the polyalkylene polyamine comprises 20% by weight diethylene triamine and 80% by weight heavy polyamine having a Mn of 275, the charge mole ratio of (ii) to (i) is from about 0.4:

1 to about 0.5;

1, the cyclic carbonate is ethylene carbonate, and the charge mole ratio of cyclic carbonate to basic amine nitrogen in the succinimide reaction product is from about 2;

1 to about 3;

1.

12. A modified polyamino alkenyl or alkyl succinimide according to claim wherein the succinic anhydride has a succinic ratio from about 1 to less than about 1.3.

13. A modified polyamino alkenyl or alkyl succinimide according to claim wherein the succinic anhydride has a succinic ratio from about 1.3 to about 1.7.

17. A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and an effective amount of a modified polyamino alkenyl or alkyl succinimide sufficient to be compatible with fluorocarbon seals and simultaneously control engine sludge and varnish, wherein the modified succinimide comprises the succinimide reaction product of:

(i) an alkenyl- or alkyl-substituted succinic anhydride derived from a polyolefin having a Mn of about 2000 to about 2700 and a Mw/Mn ratio of about 1 to about 5; and

(ii) a polyalkylene polyamine having greater than 4 nitrogen atoms per mole;

wherein the succinimide reaction product is post-treated with a cyclic carbonate.

18. A lubricating oil composition according to claim 17 wherein the charge mole ratio of (ii) to (i) is from about 0.35:

1 to about 0.6;

1; and

the charge mole ratio of cyclic carbonate to basic amine nitrogen in the succinimide reaction product is from about 1.5;

1 to about 4;

1.

19. A lubricating oil composition according to claim 17 wherein the polyolefin has a Mn of about 2100 to about 2400.

20. A lubricating oil composition according to claim 19 wherein the polyolefin has a Mn of about 2200.

21. A lubricating oil composition according to claim 17 wherein the polyolefin is polybutene.

22. A lubricating oil composition according to claim 21 wherein the polybutene is polyisobutene.

23. A lubricating oil composition according to claim 17 wherein the polyalkylene polyamine has greater than 4 to about 12 nitrogen atoms per mole.

24. A lubricating oil composition according to claim 23 wherein the polyalkylene polyamine has from about 5 to about 7 nitrogen atoms per mole.

25. A lubricating oil composition according to claim 24 wherein the heavy polyamine is Union Carbide HPA-X heavy polyamine.

26. A lubricating oil composition according to claim 24 wherein the polyalkylene polyamine comprises 20% by weight diethylene triamine and 80% by weight heavy polyamine.

27. A lubricating oil composition according to claim 17 wherein the succinic anhydride has a succinic ratio from about 1 to less than about 2.

28. A lubricating oil composition according to claim 27 wherein the succinic anhydride has a succinic ratio from about 1 to less than about 1.3.

29. A lubricating oil composition according to claim 27 wherein the succinic anhydride has a succinic ratio from about 1.3 to about 1.7.

30. A lubricating oil composition according to claim 17 wherein the cyclic carbonate is ethylene carbonate.

31. A lubricating oil composition according to claim 17 wherein the amount of the modified polyamino alkenyl or alkyl succinimide is from about 1 to about 5 weight percent on a dry polymer basis.

32. A lubricating oil composition according to claim 31 wherein the amount of the modified polyamino alkenyl or alkyl succinimide is lees than about 3 weight percent on a dry polymer basis.

33. A lubricating oil composition according to claim 17 wherein the amount of the modified polyamino alkenyl or alkyl succinimide is less than about 3 weight percent on a dry polymer basis and wherein the polyolefin is polyisobutene having a Mn of about 2200, the succinic anhydride has a succinic ratio from about 1 to about 1.7, the polyalkylene polyamine comprises heavy polyamine having a Mn of 275, the charge mole ratio of (ii) to (i) is from about 0.4:

1 to about 0.5;

1, the cyclic carbonate is ethylene carbonate, and the charge mole ratio of cyclic carbonate to basic amine nitrogen in the succinimide reaction product is from about 2;

1 to about 3;

1.

34. A lubricating oil composition according to claim 17 wherein The amount of the modified polyamino alkenyl or alkyl succinimide is less than about 3 weight percent on a dry polymer basis and wherein the polyolefin is polyisobutene having a Mn of about 2200, the succinic anhydride has a succinic ratio from about 1 to about 1.7, the polyalkylene polyamine comprises 20% by weight diethylene triamine and 80% by weight heavy polyamine having Mn of 275, the charge mole ratio of (ii) to (i) is from about 0.4:

1 to about 0.5;

1, the cyclic carbonate is ethylene carbonate, and the charge mole ratio of cyclic carbonate to basic amine nitrogen in the succinimide reaction product is from about 2;

1 to about 3;

1.

35. A lubricating oil concentrate comprising from about 90 to about 10 weight percent of an oil of lubricating viscosity and from about 10 to about 90 weight percent on a dry polymer basis of a modified polyamino alkenyl or alkyl succinimide comprising the succinimide reaction product of:

(i) an alkenyl- or alkyl-substituted succinic anhydride derived from a polyolefin having a Mn of about 2000 to about 2700 and a Mw/Mn ratio of about 1 to about 5; and

(ii) a polyalkylene polyamine having greater than 4 nitrogen atoms per mole;

wherein the succinimide reaction product is post-treated with a cyclic carbonate.

36. A lubricating oil concentrate according to claim 35 wherein the polyolefin is polyisobutene having a Mn of about 2200, the succinic anhydride has a succinic ratio from about 1 to about 1.7, the polyalkylene polyamine comprises having a Mn of 275, polyamine, the charge mole ratio of (ii) to (i) is from about 0.4:

1 to about 0.5;

1, the cyclic carbonate is ethylene carbonate, and the charge mole ratio of cyclic carbonate to basic amine nitrogen in the succinimide reaction product is from about 2;

1 to about 3;

1.

37. A lubricating oil concentrate according to claim 35 wherein the polyolefin is polyisobutene having a Mn of about 2200,the succinic anhydride has a succinic ratio from about 1 to about 1.7, the polyalkylene polyamine comprises 20% by weight diethylene triamine and 80% by weight heavy polyamine having a Mn of 275, the charge mole ratio of (ii) to (i) is from about 0.4:

1 to about the cyclic carbonate is ethylene carbonate, and the charge mole ratio of cyclic carbonate to basic amine nitrogen in the succinimide reaction product is from about 2;

1 to about 3;

1.