Use of carboxylic acid esters as lubricants

Patent metadata

Field	Value
Publication number	US-9708564-B2
Application number	US-201314411670-A
Country	US
Kind code	B2
Filing date	Jun 27, 2013
Priority date	Jul 6, 2012
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

The presently claimed invention is directed to the use of carboxylic acid esters which are obtained by reacting aliphatic dicarboxylic acids and a mixture of structurally different monoalcohols having 10 carbon atoms as lubricants and a process for their preparation.

First claim

The invention claimed is:

1. A lubricant composition comprising one or more carboxylic acid esters that are obtainable by reacting a mixture comprising:
a) at least one acid selected from the group consisting of aliphatic dicarboxylic acids and aliphatic dicarboxylic acid anhydrides,
b1) a monoalcohol having 10 carbon atoms and a structure of the general formula I,

wherein
R 1 is selected from the group consisting of pentyl, iso-pentyl, 2-methyl-butyl, 3-methyl-butyl and 2,2-dimethyl-propyl,
R 2 is H or methyl,
R 3 is selected from the group consisting of ethyl, propyl and iso-propyl, and
b2) a monoalcohol having 10 carbon atoms and a structure of the general formula II,

wherein
R 4 is selected from the group consisting of pentyl, iso-pentyl, 2-methyl-butyl, 3-methyl-butyl and 2,2-dimethyl-propyl,
R 5 is H or methyl,
R 6 is selected from the group consisting of ethyl, propyl and iso-propyl,
with the proviso that the monoalcohol b1) and the monoalcohol b2) have a different structure and the monoalcohols b1) and b2) are present in a molar ratio in the range of 1.05:1 to 2.0:1 in relation to the acid a) and a weight ratio of monoalcohol b1) to monoalcohol b2) is in the range of 5:1 to 95:1.

2. The lubricant composition of claim 1 , wherein the aliphatic dicarboxylic acid is selected from the group consisting of glutaric acid, diglycolic acid, succinic acid, azelaic acid, sebacic acid, 1,4-cyclohexanedicarboxylic acid, adipic acid, 2,6-decahydronaphthalenedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, and 2,5-norbornanedicarboxylic acid.

3. The lubricant composition of claim 1 , wherein the aliphatic dicarboxylic acid is adipic acid.

4. The lubricant composition of claim 1 , wherein R 1 is pentyl, R 2 is H, and R 3 is propyl.

5. The lubricant composition of claim 1 , wherein R 4 is 2-methyl-butyl, R 5 is H, and R 6 is propyl.

6. The lubricant composition of claim 1 , wherein the mixture further comprises a monoalcohol b3) having 10 carbon atoms and a structure of the general formula III,

wherein
R 7 is selected from the group consisting of pentyl, iso-pentyl, 2-methyl-butyl, 3-methyl-butyl and 2,2-dimethyl-propyl,
R 8 is H or methyl,
R 9 is selected from the group consisting of ethyl, propyl and iso-propyl,
with the proviso that monoalcohol b3) has a different structure from both the monoalcohol b1) and the monoalcohol b2).

7. The lubricant composition of claim 1 obtainable by reacting a mixture comprising adipic acid, 2-propyl-heptanol, 2-propyl-4-methyl-hexanol and 2-propyl-5-methyl-hexanol.

8. A method for improving the hydrolysis stability of lubricants comprising obtaining as lubricants one or more carboxylic acid esters obtainable by reacting a mixture comprising:
a) at least one acid selected from the group consisting of aliphatic dicarboxylic acids and aliphatic dicarboxylic acid anhydrides, b1) a monoalcohol having 10 carbon atoms and a structure of the general formula I,

wherein
R 1 is selected from the group consisting of pentyl, iso-pentyl, 2-methyl-butyl, 3-methyl-butyl and 2,2-dimethyl-propyl,
R 2 is H or methyl,
R 3 is selected from the group consisting of ethyl, propyl and iso-propyl, and
b2) a monoalcohol having 10 carbon atoms and a structure of the general formula II,

wherein
R 4 is selected from the group consisting of pentyl, iso-pentyl, 2-methyl-butyl, 3-methyl-butyl and 2,2-dimethyl-propyl,
R 5 is H or methyl,
R 6 is selected from the group consisting of ethyl, propyl and iso-propyl,
with the proviso that the monoalcohol b1) and the monoalcohol b2) have a different structure and the monoalcohols b1) and b2) are present in a molar ratio in the range of 1.05:1 to 2.0:1 in relation to the acid a) and a weight ratio of monoalcohol b 1) to monoalcohol b2) is in the range of 5:1 to 95:1.

9. The lubricant composition of claim 1 further comprising one or more additives selected from the group consisting of polymer thickeners, viscosity index (VI) improvers, antioxidants, corrosion inhibitors, detergents, dispersants, demulsifiers, defoamers, dyes, wear protection additives, EP (extreme pressure) additives, AW (antiwear) additives, and friction modifiers.

10. The lubricant composition of claim 1 that is effective as an industrial oil.

11. The lubricant composition of claim 1 , comprising a diester (1) of an acid selected from the group consisting of aliphatic dicarboxylic acids and aliphatic dicarboxylic acid anhydrides and b1) a monoalcohol having 10 carbon atoms and a structure of the general formula I,

wherein
R 1 is selected from the group consisting of pentyl, iso-pentyl, 2-methyl-butyl, 3-methyl-butyl and 2,2-dimethyl-propyl,
R 2 is H or methyl,
R 3 is selected from the group consisting of ethyl, propyl and iso-propyl, and
a diester (2) of an acid selected from the group consisting of aliphatic dicarboxylic acids and aliphatic dicarboxylic acid anhydrides and b2) a monoalcohol having 10 carbon atoms and a structure of the general formula II,

wherein
R 4 is selected from the group consisting of pentyl, iso-pentyl, 2-methyl-butyl, 3-methyl-butyl and 2,2-dimethyl-propyl,
R 5 is H or methyl,
R 6 is selected from the group consisting of ethyl, propyl and iso-propyl, as lubricants.

12. The method of claim 8 further comprising adding one or more additives selected from the group consisting of polymer thickeners, viscosity index (VI) improvers, antioxidants, corrosion inhibitors, detergents, dispersants, demulsifiers, defoamers, dyes, wear protection additives, EP (extreme pressure) additives, AW (antiwear) additives, and friction modifiers to the one or more carboxylic acid esters.

13. A metalworking fluid which comprises the lubricant composition of claim 1 .

14. A transformer oil which comprises the lubricant composition of claim 1 .

15. A coating composition which comprises the lubricant composition of claim 1 .

16. A plasticizing agent which comprises the lubricant composition of claim 1 .

17. The lubricant composition of claim 1 , wherein the weight ratio of monoalcohol b1) to monoalcohol b2) is in the range of 6:1 to 50:1.

18. The lubricant composition of claim 1 , wherein the weight ratio of monoalcohol b1) to monoalcohol b2) is in the range of 10:1 to 40:1.

19. The lubricant composition of claim 1 , wherein the weight ratio of monoalcohol b1) to monoalcohol b2) is in the range of 20:1 to 35:1.

Assignees

• Basf Se

Inventors

• Scherer Markus
• Breitscheidel Boris

Classifications

• C10N2040/16

  Dielectric; Insulating oil {or insulators} · CPC title

• C10N2020/02

  Viscosity; Viscosity index · CPC title

• C10M105/36 Primary

  of polycarboxylic acids · CPC title

• C10M2207/2825

  used as base material · CPC title

• C10N2040/20

  Metal working · CPC title