Lubricating compositions and methods for the use thereof

Patent metadata

Field	Value
Publication number	US-2017107440-A1
Application number	US-201615294342-A
Country	US
Kind code	A1
Filing date	Oct 14, 2016
Priority date	Oct 15, 2015
Publication date	Apr 20, 2017
Grant date	—

Abstract

Disclosed herein are lubricating compositions and methods of use of the same, including for, e.g., use in metalworking operations.

First claim

1 . A lubricating composition comprising a partial or half-ester of a compound derived from the Diels-Alder reaction of a conjugated fatty acid and an acid precursor dienophile.

2 . The lubricating composition of claim 1 , wherein the acid precursor dienophile is an acrylic acid or acrylic acid ester.

3 . The lubricating composition of claim 1 , wherein the acid precursor dienophile is at least one of methacrylic acid, maleic anhydride, fumaric acid, a fumaric acid mono or diester or a combination thereof.

4 . The lubricating composition of claim 1 , wherein the conjuaged fatty acid is derived from tall oil fatty acid.

5 . The lubricating composition of claim 1 , wherein the conjugated fatty acid is linoleic acid.

6 . The lubricating composition of claim 1 , wherein the compound derived from the Diels-Alder reaction of a conjugated fatty acid and acrylic acid is DIACID 1550, and the partial ester is a DIACID 1550 partial ester.

7 . The lubricating composition of claim 6 , wherein the DIACID 1550 partial ester is derived from an esterification reaction comprising an alcohol and DIACID 1550, and wherein the reaction comprises a molar excess of carboxyl moieties.

8 . The lubricating composition of claim 7 , wherein the alcohol is selected from the group consisting of n-pentanol, 1-docecanol, 2-ethyl-1-hexanol, and combinations thereof.

9 . The lubricating composition of claim 7 , wherein the reaction further comprises a catalyst.

10 . The lubricating composition of claim 8 , wherein the catalyst is hypophosphourous acid.

11 . The lubricating composition of claim 6 , wherein the composition comprises an effective amount of the DIACID 1550 partial ester to reduce or inhibit foaming as compared to DIACID 1550 or DIACID 1550 bis-ester alone.

12 . The lubricating composition of claim 6 , wherein the composition comprises a semi-synthetic metalworking fluid or a full-synthetic metalworking fluid.

13 . An aqueous metalworking composition comprising an effective amount of a DIACID 1550 partial ester.

14 . The metalworking composition of claim 13 , wherein the DIACID 1550 partial ester is derived from a reaction comprising an alcohol and DIACID 1550, and wherein the reaction comprises a molar excess of carboxyl moieties.

15 . The metalworking fluid of claim 14 , wherein the alcohol is selected from the group consisting of n-pentanol, 1-docecanol, or 2-ethyl-1-hexanol.

16 . The metalworking composition of claim 14 , wherein the reaction further comprises a catalyst.

17 . The metalworking composition of claim 16 , wherein the catalyst is an acid.

18 . The metalworking composition of claim 12 , wherein the acid is hypophosphourous acid.

19 . The metalworking composition of claim 16 , wherein the reaction is neutralized with a base.

20 . The metalworking composition of claim 13 , wherein the metalworking composition comprises a semi-synthetic metal working fluid or a synthetic metal working fluid.

21 . The metalworking composition of claim 13 , wherein the metalworking composition is a semi-synthetic metalworking fluid and further includes a coupling solvent.

22 . The metalworking composition of claim 21 , wherein the coupling solvent is a glycol ether.

23 . The metalworking composition of claim 22 , wherein the glycol ether is tripropylene glycol methyl ether or diethylene glycol monobutyl ether.

24 . The metalworking composition of claim 13 , wherein the metalworking composition is a synthetic metalworking fluid and further includes a nonionic surfactant.

25 . The metalworking composition of claim 24 , wherein the nonionic surfactant is at least one of a alkylphenol ethoxylate, a linear alcohol ethoxylate, or a DIACID 1550 ethoxylate.

26 . The metalworking composition of claim 25 , wherein the alkylphenol ethoxylate is at least one of nonyl phenol ethoxylate and octylphenol ethoxylate.

27 . The metalworking composition of claim 25 , wherein the linear alcohol ethoxylate is at least one of: tall oil fatty acid ethoxylate, TERGITOL™ NP-4, TERGITOL™ NP-7, and TERGITOL™ NP-9.

28 . The metalworking composition of claim 25 , wherein the DIACID 1550 ethoxylate is at least one of: OCD-383 and OCD-384.

29 . The metalworking composition of claim 13 , further comprising at least one of a biocide and a fungicide.

30 . A method of lubricating a metal workpiece by applying the aqueous metalworking composition of claim 13 to the metal workpiece.

31 . A metalworking process comprising performing a metalworking operation by flushing, spraying, high pressure spraying, brushing, flowing, fluting, roll coating, immersion, or any combination thereof with the aqueous metalworking composition of claim 13 .

32 . A compound having the structure:

wherein R 1 and R 2 are independently selected from the group comprising H, alkyl, alkenyl, cycloalkyl, chloroalkyl, chlorocycloalky, polyoxyethylene, polyoxypropylene, or a mixture thereof, and wherein at least one of R 1 or R 2 but not both is H and the other is not.

33 . The compound of claim 32 , wherein at least one of R 1 or R 2 but not both is at least one of alkyl, alkenyl, cycloalkyl, chloroalkyl, chlorocycloalky, polyoxyethylene and polyoxypropylene.

34 . The compound of claim 33 , wherein the compound has the structure:

35 . A composition comprising the compound of claim 32 , wherein at least 10 mol % of R 1 and R 2 is H.

36 . The composition of claim 35 , wherein up to 90 mol % of R 1 and R 2 are at least one of alkyl, alkenyl, cycloalkyl, chloroalkyl, chlorocycloalky, polyoxyethylene and polyoxypropylene.

Assignees

• Ingevity South Carolina Llc

Inventors

• Cuff Thomas J
• Bowers James L
• Olivier Eric J
• Yao Kejian

Classifications

• C10M105/40

  containing free hydroxy or carboxyl groups · CPC title

• B05D1/28

  performed by transfer from the surfaces of elements carrying the liquid or other fluent material, e.g. brushes, pads, rollers · CPC title

• C10N2040/20

  Metal working · CPC title

• C10M173/02

  not containing mineral or fatty oils · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title