Non-aqueous lubricant and fuel compositions comprising fatty acid esters of hydroxy-carboxylic acids, and uses thereof

Patent metadata

Field	Value
Publication number	US-9828564-B2
Application number	US-201514813564-A
Country	US
Kind code	B2
Filing date	Jul 30, 2015
Priority date	Oct 26, 2010
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

The use as an anti-wear additive and/or friction modifier in a non-aqueous lubricant composition and/or in a fuel composition of at least one long chain fatty acid ester of a hydroxy carboxylic acid in which the long chain fatty acid has at least 4 carbon atoms and the ester is an oil-soluble ester of a mono- or poly-hydroxy carboxylic acid having 1 to 4 groups which are independently carboxylic acid groups or lower hydrocarbyl esters thereof and in which, when the hydroxy carboxylic acid is a mono-hydroxy carboxylic acid, the ester has a long chain fatty acid ester moiety of the hydroxy group of the hydroxy carboxylic acid and, when the hydroxy carboxylic acid is a poly-hydroxy carboxylic acid, the ester has independently long chain fatty acid ester moieties of one or two of the hydroxy groups of the poly-hydroxy carboxylic acid. Also, a non-aqueous lubricant composition and a fuel composition for an internal combustion engine which comprises at least one of said long chain fatty acid esters.

First claim

The invention claimed is:

1. A non-aqueous lubricant composition comprising a major amount of an oil of lubricating viscosity and a minor amount of at least one compound, each compound being an oil-soluble long chain fatty acid ester of a mono- or di-hydroxy carboxylic acid selected from citric acid, malic acid and tartaric acid, wherein:
(i) when the compound is an oil-soluble long chain fatty acid ester of a mono-hydroxy carboxylic acid,
the compound includes a long chain fatty acyl moiety substituted at the hydroxy group of the mono-hydroxy carboxylic acid, the long-chain fatty acyl moiety having 8 to 22 carbon atoms, and
each carboxylate of the mono-hydroxy carboxylic acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which independently has 1 to 3 carbon atoms;

(ii) when the compound is an oil-soluble long chain fatty acid mono-ester of a di-hydroxy carboxylic acid,
the compound includes a long chain fatty acyl moiety substituted at the hydroxy groups of the di-hydroxy carboxylic acid, the long-chain fatty acyl moiety having 8 to 22 carbon atoms, and
each carboxylate of the di-hydroxy carboxylic acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which independently has 1 to 3 carbon atoms; and

(iii) when the compound is an oil-soluble long chain fatty acid di-ester of a di-hydroxy carboxylic acid,
the compound includes two long chain fatty acyl moieties, each substituted at one of the hydroxy groups of the di-hydroxy carboxylic acid, each long-chain fatty acyl moiety independently having 8 to 22 carbon atoms, and
each carboxylate of the di-hydroxy carboxylic acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which independently has 1 to 3 carbon atoms.

2. The composition as claimed in claim 1 , wherein each compound is an oil-soluble long chain fatty acid ester of citric acid, wherein:
each compound includes a long chain fatty acyl moiety substituted at the hydroxy group of the citric acid, the long-chain fatty acyl moiety having 8 to 22 carbon atoms, and
each carboxylate of the citric acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which independently has 1 to 3 carbon atoms.

3. The composition as claimed in claim 1 in which each compound is a long chain fatty acid di-ester of tartaric acid, wherein
each compound includes two long chain fatty acyl moieties, each substituted at one of the hydroxy groups of the tartaric acid, each long-chain fatty acyl moiety independently having 8 to 22 carbon atoms, and
each carboxylate of the tartaric acid is independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which independently has 1 to 3 carbon atoms.

4. The composition as claimed in claim 1 in which each of the compounds is a long chain fatty acid mono-ester of tartaric acid, wherein
the compound includes a long chain fatty acyl moiety substituted at only one of the hydroxy groups of the tartaric acid, the long-chain fatty acyl moiety having 8 to 22 carbon atoms, and
each carboxylate of the tartaric acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which independently has 1 to 3 carbon atoms.

5. The composition as claimed in claim 1 in which each of the long chain fatty acyl moieties has 8 to 18 carbon atoms.

6. The composition as claimed in claim 2 in which each of the long chain fatty acyl moieties has 8 to 18 carbon atoms.

7. The composition as claimed in claim 3 in which each of the long chain fatty acyl moieties has 8 to 18 carbon atoms.

8. The composition as claimed in claim 1 in which each of the long chain fatty acyl moieties has 14 to 22 carbon atoms.

9. The composition as claimed in claim 2 in which each of the long chain fatty acyl moieties has 14 to 22 carbon atoms.

10. The composition as claimed in claim 3 in which each of the long chain fatty acyl moieties has 14 to 22 carbon atoms.

11. The composition as claimed in claim 1 in which each of the long chain fatty acyl moieties has 8, 14, 16, 18 or 22 carbon atoms.

12. The composition as claimed in claim 1 in which the long chain fatty acyl moieties is oleoyl.

13. The composition as claimed in claim 1 in which the long chain fatty acyl moieties is myristoyl.

14. The composition as claimed in claim 1 in which the alkyl moieties of the lower alkyl carboxylate esters are ethyl.

15. The composition as claimed in claim 2 in which the alkyl moieties of the lower alkyl carboxylate esters are ethyl.

16. The composition as claimed in claim 3 in which the alkyl moieties of the lower alkyl carboxylate esters are ethyl.

17. The composition as claimed in claim 1 , wherein each compound is derived from (a) reacting the mono- or di-hydroxy carboxylic acid and the long chain fatty acid or an acyl halide of the long chain fatty acid or (b) reacting a lower hydrocarbyl ester of the hydroxy carboxylic acid and the long chain fatty acid or an acyl halide of the long chain fatty acid.

18. The composition as claimed in claim 1 , wherein each compound is an oil-soluble long chain fatty acid ester of citric acid, wherein:
each compound includes a long chain fatty acyl moiety substituted at the hydroxy group of the citric acid, the long-chain fatty acyl moiety having 8 to 18 carbon atoms, and
each carboxylate of the citric acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which is ethyl.

19. The composition as claimed in claim 1 , wherein each compound is an oil-soluble long chain fatty acid ester of citric acid, wherein:
each compound includes a long chain fatty acyl moiety substituted at the hydroxy group of the citric acid, the long-chain fatty acyl moiety having 14 to 22 carbon atoms, and
each carboxylate of the citric acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which is ethyl.

20. The composition as claimed in claim 1 , wherein each compound is an oil-soluble long chain fatty acid mono- or di-ester of tartaric acid, wherein in which the oil soluble ester has the structural formula:
when the compound is an oil-soluble long chain fatty acid mono-ester of tartaric acid,
the compound includes a long chain fatty acyl moiety substituted at only one of the hydroxy groups of the tartaric acid, the long-chain fatty acyl moiety having 8 to 22 carbon atoms, and
each carboxylate of the tartaric acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which independently has 1 to 3 carbon atoms; and

when the compound is an oil-soluble long chain fatty acid di-ester of tartaric acid,
the compound includes two long chain fatty acyl moieties, each substituted at one of the hydroxy groups of the tartaric acid, each long-chain fatty acyl moiety independently having 8 to 22 carbon atoms, and
each carboxylate of the tartaric acid independently is a lower alkyl carboxylate ester, each lower alkyl carboxylate ester having an alkyl moiety which independently has 1 to 3 carbon atoms.

21. The composition as claimed in claim 20 , wherein each alkyl moiety of each lower alkyl carboxylate ester is ethyl.

22. The composition as claimed in claim 21 , wherein each long chain

Assignees

• Castrol Ltd

Inventors

• West Kevin Richard

Classifications

• C10L1/19 Primary

  Esters {ester radical containing compounds; ester ethers; carbonic acid esters (C10L1/1802, C10L1/1805, C10L1/1808, C10L1/1811, C10L1/1814, C10L1/1817 take precedence)} · CPC title

• C10M129/70

  of monocarboxylic acids · CPC title

• C10M2207/30

  Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids · CPC title

• C10M2207/288

  containing free carboxyl groups · CPC title

• C10M129/72 Primary

  of polycarboxylic acids · CPC title