Polyester and use of polyester in lubricants

Patent metadata

Field	Value
Publication number	US-10150928-B2
Application number	US-201415022286-A
Country	US
Kind code	B2
Filing date	Sep 3, 2014
Priority date	Sep 16, 2013
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

The presently claimed invention is directed to novel polyesters which are obtainable by reacting a mixture comprising at least one C8-C20 Guerbet alcohol, at least one aliphatic or cycloaliphatic dicarboxylic acid and at least one polyol with a hydroxyl functionality in the range of ≥2 to ≤6 and the use of these polyesters as a component of lubricating oil compositions.

First claim

The invention claimed is:

1. A polyester which is obtainable by reacting a mixture comprising
a) at least one acid selected from the group consisting of aliphatic dicarboxylic acids having 5 to 20 carbon atoms and cycloaliphatic dicarboxylic acid having 4 to 36 carbon atoms,
b) at least one monoalcohol of the formula I,

wherein p is 2;

and
c) at least one polyol with a hydroxyl functional in the range of ≥2 to ≤6 and wherein
≥25 to ≤50% by weight of component a),
≥40 to ≤70% by weight of component b) and
≥0.1 to ≤20% by weight of component c),
whereby and the sum of the weight of all components a), b) and c) adds up to 100%.

2. The polyester according to claim 1 , wherein the at least one aliphatic dicarboxylic acid having 5 to 20 carbon atoms is selected from the group consisting of
glutaric acid, azelaic acid, sebacic acid, adipic acid, pimelic acid, suberic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid and octadecanedioic acid.

3. The polyester according to claim 1 , wherein the at least one cycloaliphatic dicarboxylic acid having 4 to 36 carbon atoms is selected from the group consisting of
1,4-cyclohexanedicarboxylic acid, 2,6-decahydronaphthalenedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid and 2,5-norbornanedicarboxylic acid.

4. The polyester according to claim 1 , wherein the at least one polyol with a hydroxyl functionality in the range of ≥2 to ≤6 is selected from the group consisting of
ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, dipropylene glycol ,tripropylene glycol, 1,4-butanediol, 1,6-hexanediol, bisphenol A, trimethylolpropane, glycerol, castor oil, pentaerythritol, sorbitol, dipentaerythritol and sucrose.

5. The polyester according to claim 1 , wherein the at least one polyol with a hydroxyl functionality in the range of ≥2 to ≤6 is selected from the group consisting of
ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, dipropylene glycol, tripropylene glycol, 1 ,4-butanediol, 1 ,6-hexanediol, bisphenol A, trimethylolpropane glycerol, castor oil, pentaerythritol, sorbitol, dipentaerythritol and sucrose.

6. The polyester according to claim 5 , wherein the at least one aliphatic dicarboxylic acid having 5 to 20 carbon atoms is selected from the group consisting of
glutaric acid, azelaic acid, sebacic acid, adipic acid, pimelic acid, suberic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid and octadecanedioic acid.

7. The polyester according to claim 5 , wherein the at least one cycloaliphatic dicarboxylic acid having 4 to 36 carbon atoms is selected from the group consisting of
1,4-cyclohexanedicarboxylic acid, 2,6-decahydronaphthalenedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid and 2,5-norbornanedicarboxylic acid.

8. The polyester according to claim 1 , wherein the polyester has a viscosity in the range from ≥10 to ≤500 mm 2 /s at 40° C. determined according to DIN 51562-1.

9. The polyester according to claim 1 , wherein the polyester has a viscosity index in the range of ≥3 to ≤50 mm 2 /s at 100° C. determined according to DIN 51562-1.

10. The polyester according to claim 1 , wherein the polyester has a viscosity index in the range of ≥110 to ≤190 determined according to ASTM D 2270.

11. The polyester according to claim 1 , wherein the polyester has a density in the range from ≥0.91 to ≤1.10 g/cm 3 at 15° C. determined according to DIN 51757.

12. A process for the preparation of the polyester according to claim 1 comprising the steps of
i) reacting a mixture comprising component a), component b) and component c), each case defined as in claim 1 , in the presence of at least one catalyst selected from the group consisting of titanium-containing compounds, zirconium-containing compounds and tin-containing compounds,
ii) heating the mixture obtained according to step i) to a temperature in the range of 80° C. to 160° C. in a first step and subsequently to a temperature in the range of 190° C. to 240° C. in a second step,
iii) applying vacuum to the reaction mixture obtained according to step ii),
iv) cooling of the reaction mixture obtained according to step iii) to a temperature in the range of 20° C. to 90° C. and adding water to the reaction mixture and
v) drying and purification of the reaction mixture obtained according to step iv).

13. A lubricating oil composition comprising
a) ≥1% to ≤99.9% by weight of at least one polyester according to claim 1 ,
b) ≥0% to ≤99% by weight of at least one base stock selected from the group consisting of mineral oils (Group I, II or III oils), polyalphaolefins (Group IV oils), polymerized and interpolymerized olefins, alkyl naphthalenes, alkylene oxide polymers, silicone oils, phosphate esters and carboxylic acid esters (Group V oils),
and
c) ≥0.1 to ≤25 by weight of one or more performance additives, whereby the by weight of the components a), b) and c) is in each case related to the overall weight of the lubricating oil composition and the sum of the weight of all components a), b) and c) adds up to 100%.

14. A light, medium and heavy duty engine oil, industrial engine oil, marine engine oil, automotive engine oil, crankshaft oil, compressor oil, refrigerator oil, hydrocarbon compressor oil, very low-temperature lubricating oil and flits, high temperature lubricating oil and fats, wire rope lubricant, textile machine oil, refrigerator oil, aviation and aerospace lubricant, aviation turbine oil, transmission oil, gas turbine oil, spindle oil, spin oil, traction fluid, transmission oil, plastic transmission oil, passenger car transmission oil, truck transmission oil, industrial transmission oil, industrial gear oil, insulating oil, instrument oil, brake fluid, transmission liquid, shock absorber oil, heat distribution medium oil, transformer oil, flit, chain oil, minimum quantity lubricant for metalworking operations, oil to the warm and cold working, oil for water-based metalworking liquid, oil for neat oil metalworking fluid, oil for semi-synthetic metalworking fluids, oil for synthetic metalworking fluids, drilling detergent for the soil exploration, hydraulic oil, in a biodegradable lubricant or lubricating grease or wax, chain saw oil, release agent, moulding fluid, gun, pistol and rifle lubricant or watch lubricant or food grade approved lubricant which comprises the lubricating composition according to claim 13 .

15. A method for reducing the friction coefficient of a lubricating oil composition
in the lubrication of a mechanical device comprising formulating said lubricating oil composition with at least one polyester according to claim 1 .

16. The method according to claim 15 , wherein the friction coefficient is measured at 0-25% slide roll ratio (SRR), mean speed 4mm/s, using mini-traction machine (MTM) measurements at 70° C. and 1GPa loading.

17. The polyester according to claim 1 , wherein said at least one acid is at least one cycloaliphatic dicarboxylic acid having 4 to 36 carbon atoms and is selected from the group consisting of
1,4-cyclohexanedicarboxylic acid, 2,6-decahydronaphthalenedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid and 2,5-norbarnanedicarboxylic acid.

Assignees

• Basf Se

Inventors

• Scherer Markus
• Rinklieb Ronny

Classifications

• C10N2030/06

  Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure · CPC title

• C10N2040/06

  Instruments or other precision apparatus, e.g. damping fluids · CPC title

• C10N2040/16

  Dielectric; Insulating oil {or insulators} · CPC title

• C10N2040/08

  Hydraulic fluids, e.g. brake-fluids · CPC title

• C10N2040/46

  Textile oils · CPC title