High viscosity base fluids based on oil compatible polyesters

Patent metadata

Field	Value
Publication number	US-2023257673-A1
Application number	US-202118003938-A
Country	US
Kind code	A1
Filing date	Jul 1, 2021
Priority date	Jul 3, 2020
Publication date	Aug 17, 2023
Grant date	—

Abstract

A polyester is useful as a high viscosity base fluid. A method for its preparation involves isomerizing an alpha-olefin, epoxidizing an internal olefin, reacting an internal epoxide, and isolating the polyester. Lubricant compositions can contain such polyesters and the compositions are useful as automatic transmission fluids, manual transmission fluids, continuously variable transmission fluids, gear oil formulations, industrial gear oil formulations, axle fluid formulations, dual clutch transmission fluids, dedicated hybrid transmission fluids, or as hydraulic oils.

First claim

1 : A polyester, obtained from reaction of:
an internal epoxide derived from an internal olefin comprising 10 to 24 carbon atoms, or a diol derived from internal epoxide, with at least one saturated linear aliphatic dicarboxylic acid comprising 5 to 13 carbon atoms.

2 : The polyester according to claim 1 , wherein the internal olefin comprises not more than 30 mol % of double bonds being in the alpha-position.

3 : The polyester according to claim 1 , wherein the internal olefin comprises 12 to 20 carbon atoms.

4 : The polyester according to claim 1 , wherein the at least one saturated linear aliphatic dicarboxylic acid is selected from the group consisting of glutaric acid (pentanedioic acid), 2,2-dimethylglutaric acid (2,2-dimethylpentanedioic acid), adipic acid (hexanedioic acid), 2,4,4-trimethyladipic acid (2,4,4-trimethylhexanedioic acid), pimelic acid (heptanedioic acid), suberic acid (octanedioic acid), azelaic acid (nonanedioic acid), sebacic acid (decanedioic acid), undecanedioic acid, dodecanedioic acid, brassylic acid (tridecanedioic acid), and a mixture thereof.

5 : The polyester according to claim 1 , wherein the polyester has a melting point of equal to or below −15° C.

6 : The polyester according claim 1 , wherein the polyester has a glass transition temperature of equal to or below −50° C.

7 : The polyester according to claim 1 , having a number-average molecular weight M n in the range of 1,000 to 15,000 g/mol, determined by size exclusion chromatography (SEC) using polymethylmethacrylate standards.

8 : The polyester according to claim 1 , having a kinematic viscosity at 100° C. (KV100) in the range of 40 to 2000 cSt.

9 : The polyester according to claim 1 , wherein a molar ratio of carbon to oxygen, calculated by summing up the number of carbon atoms present in the diol and in diacid monomers and dividing the resulting numbers by four as being the number of oxygen atoms in a resulting diester unit, is in the range of 4:1 to 12:1.

10 : A method of lubricating an industrial gear, comprising:
preparing a lubricant formulation comprising the polyester according to claim 1 as a base oil, optionally, adding a further base oil selected from the group consisting of API Group II oils, API Group III oils, API Group IV oils, and a mixture thereof, to the lubricant formulation, and applying the lubricant formulation to the industrial gear.

11 : A lubricating composition, comprising:
(A) 20 to 60% by weight of at least one polyester prepared from an internal epoxide derived from an internal olefin comprising 10 to 24 carbon atoms, or from a diol derived from the internal epoxide, and at least one saturated linear aliphatic diacid comprising 5 to 13 carbon atoms; (B) 40 to 80% by weight of a base oil selected from the group consisting of API Group II oils, API Group III oils, API Group IV oils, and mixture thereof; and (C) 0 to 5% by weight of one or more additives,
based on a total weight of the lubricating composition.

12 : The lubricating composition according to claim 11 , wherein the internal olefin of component (A) comprises 12 to 20 carbon atoms.

13 : The lubricating composition according to claim 11 , wherein the one or more further additives (C) are selected from the group consisting of pour point depressants, dispersants, defoamers, detergents, demulsifiers, antioxidants, antiwear additives, extreme pressure additives, friction modifiers, anticorrosion additives, dyes, and a mixture thereof.

14 : A method for preparing the polyester according to claim 1 , the method comprising:
(a) isomerizing an alpha-olefin comprising 10 to 24 carbon atoms, to the internal olefin; (b) epoxidizing the internal olefin retrieved under (a); (c1) reacting the internal epoxide retrieved under (b) with the at least one saturated linear aliphatic dicarboxylic acid comprising 5 to 13 carbon atoms, or (c2) transferring the internal epoxide retrieved under (b) to the corresponding diol and reacting the diol with the at least one saturated linear aliphatic dicarboxylic acid comprising 5 to 13 carbon atoms; and (d) isolating the polyester.

15 : The polyester according to claim 2 , wherein the internal olefin comprises not more than 20 mol % of the double bonds in the alpha-position.

16 : The polyester according to claim 3 , wherein the internal olefin comprises 14 to 18 carbon atoms.

17 : The polyester according to claim 4 , wherein the at least one saturated linear aliphatic dicarboxylic acid is selected from the group consisting of azelaic acid (nonanedioic acid), sebacic acid (decanedioic acid), dodecanedioic acid, and a mixture thereof.

18 : The polyester according to claim 5 , wherein the polyester has a melting point of equal to or below −25° C.

19 : The polyester according to claim 8 , wherein the KV100 is in the range of 100 to 1,000 cSt.

20 : The method according to claim 10 , wherein the lubricant formulation is a gear oil formulation.

Assignees

• Evonik Operations Gmbh

Inventors

• Maier Stefan Karl
• Altenbuchner Peter
• Ziegler Fabian
• Zatocil Christiane
• Hilf Stefan
• Schweissinger Emily Clare
• Elsner Jens

Classifications

• C10M145/22 Primary

  Polyesters · CPC title

• C08G63/42

  Cyclic ethers (C08G59/00 takes precedence); Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters · CPC title

• C10M169/041

  the additives being macromolecular compounds only · CPC title

• C10M2203/003

  used as base material · CPC title

• C10M2209/102

  Polyesters · CPC title