CA1165772A

CA1165772A - Carboxylic acid derivatives of alkanol tertiary monoamines

Info

Publication number: CA1165772A
Application number: CA000335614A
Authority: CA
Inventors: John W. Forsberg
Original assignee: Lubrizol Corp
Current assignee: Lubrizol Corp
Priority date: 1978-09-27
Filing date: 1979-09-14
Publication date: 1984-04-17

Abstract

ABSTRACT OF THE DISCLOSURE
Nitrogen-containing phosphorus-free carboxylic acid derivatives made by reaction of an acylating agent with an alkanol tertiary monoamine are described. Typically the carboxylic acylating agent is an alkyl or alkenyl succinic anhydride containing about 20 to about 500 carbon atoms in the alkyl or alkenyl group. A typical amine is diethyl ethanol amine. These derivatives are useful in incorpora-ting oil-soluble, water-insoluble functional additives, such as metal salts of acid phosphate and thiophosphate hydro-carbyl esters, into water-based functional fluids such as water-based hydraulic fluids.

Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A nitrogen-containing, phosphorus-free carboxylic acid derivative made by reaction of (A) at least one carboxylic acid acylating agent with (B) at least one alkanol ter-tiary monoamine, said acylating agent having at least one hydrocarbyl-based substituent of about 20 to about 500 carbon atoms and said monoamine (B) having one hydroxyl group and a total of up to about 40 carbon atoms, the reaction between components (A) and (B) being conducted at a temperature in the range of about 30°C to about 150°C, at least a portion of said derivative being in the form of a salt, said salt being an internal salt wherein carboxyl groups of said acylating agent are ionically bonded to nitrogen atoms within the same molecule and/or an external salt wherein the ionic salt is formed with nitrogen atoms which are not part of the same molecule.

2. A derivative as claimed in claim 1 wherein said acy-lating agent (A) can be represented by the formula or wherein hyd is a substantially hydrocarbyl alkyl or alkenyl group of about 30 to about 500 carbon atoms and said amine (B) can be represented by the formula wherein each R is independently a hydrocarbyl group of one to about 20 carbon atoms and R' is an alkylene group of two to about eighteen carbon atoms.

3. A derivative as claimed in claim 2 wherein said mono-amine (B) is diethyl ethanol amine and said derivative (A) is an ester/salt.

4. A derivative as claimed in claim 1 wherein the equiva-lent ratio of acylating agent (A) to monoamine (B) used in the reaction is in the range of about 1:0.5 to about 1:3Ø

5. A derivative as claimed in claim 3 wherein the equivalent ratio of acylating agent (A) to monoamine (B) used in the reaction is in the range of about 1:0.5 to about 1:3Ø

6. A derivative as claimed in claim 2 where hyd is a poly(isobutene) group of about 50 to about 300 carbon atoms and (A) is the only acylating agent present in the reaction.

7. A derivative as claimed in claim 5 where hyd is a poly(isobutene) group of about 50 to about 300 carbon atoms and (A) is the only acylating agent present in the reaction.

8. A derivative as claimed in claim 1 where said monoamine (B) is the only amine present in the reaction and the equivalent ratio of acylating agent (A) to monoamine (B) in the reaction is in the range of about 1:1 to about 1:2.5.

9, A derivative as claimed in claim 1 wherein there is also present in the reaction (C) at least one supple-mental alkanol amine in addition to the alkanol tertiary monoamine (B).

10. A derivative as claimed in claim 3 wherein there is also present in the reaction (C) at least one supple-mental alkanol amine in addition to the alkanol tertiary monoamine (B).

11. A derivative as claimed in claim 5 wherein there is also present in the reaction (C) at least one supplemen-tal alkanol amine in addition to the alkanol tertiary mono-amine (B).

12. A derivative ac claimed in claim 1 wherein said alkanol tertiary monoamine (B) is the only amine present in the reaction.

13. A derivative as claimed in claim 3 wherein said alkanol tertiary monoamine (B) is the only amine present in the reaction.

14. A derivative as claimed in claim 5 wherein said alkanol tertiary monoamine (B) is the only amine present in the reaction.

15. A water-dilutable lubricant additive composition comprising 40 to 70% by weight of a derivative as claimed in claim 1, 5 to 20% by weight of a non-ionic hydrophilic surfactant or wetting agent, and 10 to 40% by weight of a water-insoluble oil-soluble functional additive.

16. A composition as claimed in claim 15 wherein the water-insoluble functional additive is selected from phosphorous and/or sulfur-containing anti-wear, extreme pressure and load-carrying agents.

17, A water-dilutable hydraulic fluid concentrate comprising 95 parts by weight water and 5 parts by weight of a composition as claimed in claim 15.

18. A lubricant additive concentrate comprising in admixture a hydrocarbyl oil and a composition as claimed in claim 15, said hydrocarbyl oil being present in an amount of up to 15% by weight based on the total weight of the concentrate.

19. The derivative of claim 1 wherein said acylating agent (A) is represented by the formula or wherein hyd is said hydrocarbyl-based substituent.

20. The derivative of claim 1 wherein said monoamine (B) is represented by the formula wherein each R is independently a hydrocarbyl group of one to about 20 carbon atoms and R' is an alkylene group of two to about 18 carbon atoms.

21. The derivative of claim 1 wherein said monoamine (B) is diethyl ethanol amine.

22. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substitutent is an alkyl or an alkenyl group.

23. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent has about 20 to about 300 carbon atoms.

24. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent is a poly(isobutene) group.

25. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent has about 20 to about 200 carbon atoms.

26. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent is an alkyl or an alkenyl group of about 30 to about 500 carbon atoms.

27. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent has about 30 to about 300 carbon atoms.

28. The derivative of claim 1 or composition of claim 15 wherein said hyarocarbyl-based substituent is a poly(isobutene) group of about 30 to about 500 carbon atoms.

29. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent has about 30 to about 200 carbon atoms.

30. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent is an alkyl or an alkenyl group of about 50 to about 500 carbon atoms.

31. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent has about 50 to about 300 carbon atoms.

32. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent is a poly(isobutene) group of about 50 to about 500 carbon atoms.

33. The derivative of claim 1 or composition of claim 15 wherein said hydrocarbyl-based substituent has about 50 to about 200 carbon atoms.

34. The derivative of claim 1 wherein at least one supplemental carboxylic acylating agent in addition to the acylating agent (A) is present in the reaction.

35. The derivative of claim 30 wherein said supplemental acylating agent is a fatty acid of 10 to 18 carbon atoms.

36. The derivative of claim 30 wherein said supplemental acylating agent is a low molecular weight alkyl or alkenyl succinic acid.

37. The derivative of claim 30 wherein said supplemental acylating agent is tetrapropenyl succinic anhydride.

38. The derivative of claim 9 wherein said supplemental alkanol amine (C) has up to about 26 carbon atoms.

39. The derivative of claim 9 wherein said supplemental alkanol amine (C) is a primary, secondary or tertiary alkanol amine.

40. The derivative of claim 9 wherein said supplemental alkanol amine (C) has the formula wherein R1 and R2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, hydroxy alkyl and hydroxy alkenyl and R3 is alkylene.

41. The derivative of claim 9 wherein said supplemental alkanol amine (C) is ethanolamine.

42. A composition comprising (a) at least one normally water-insoluble, oil-soluble functional additive and (b) a nitrogen-containing, phosphorus-free carboxylic acid derivative as claimed in claim 1.

43. A composition comprising (a) at least one normally water-insoluble, oil-soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load-carrying agents, and (b) a nitrogen-containing, phosphorus-free carboxylic acid derivative as claimed in claim 1.

44. A water-based system comprising about 40 to about 70% of water, from 0 up to about 15% hydrocarbyl oil and a mixture comprising (a) from about 10 to about 40% of at least one normally water-insoluble, oil-soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load-carrying agents, and (b) from about 40 to about 70% of a nitrogen-containing, phosphorus-free carboxylic acid derivative as claimed in claim 1.

45. A composition comprising (a) at least one normally water-insoluble, oil-soluble functional additive, (b) a nitrogen-containing, phosphorus-free carboxylic acid derivative as claimed in claim 1, and (c) a surfactant.

46. A composition comprising (a) at least one normally water-insoluble, oil-soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load-carrying agents, (b) a nitrogen-containing, phosphorus-free carboxylic acid derivative as claimed in claim 1, and (c) a surfactant.

47. A water-based system comprising about 40 to about 70% of water, from 0 up to about 15% hydrocarbyl oil and a mixture comprising (a) from about 10 to about 40% of at least one normally water-insoluble, oil-soluble functional additive selected from the group consisting of phosphorus and/or sulfur-containing anti-wear, extreme pressure, or load-carrying agents, (b) from about 40 to about 70% of a nitrogen-containing, phosphorus-free carboxylic acid derivative as claimed in claim 1, and (c) from about 5 to about 20% of a surfactant.