# US 5,348,670 A · Phosphorous amine lubricant additives

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- Number: US 5,348,670 A
- Document ID: US5348670A
- Status: Granted
- Kind: A
- Application number: 08/013,510
- Filed: 1993-02-04
- Granted: 1994-09-20
- Earliest claimed: 1990-05-18
- Assignees: Elco Corporation
- Inventors: Randolph A. McDonald; Gerald D. Burt
- Web page: https://patentgrep.com/patent/US5348670A

## CPC

- C10M 173/00: Lubricating compositions containing more than 10% water
- C07F 9/091: {with hydroxyalkyl compounds with further substituents on alkyl}
- C10M 125/24: Compounds containing phosphorus, arsenic or antimony
- C10M 125/26: Compounds containing silicon or boron, e.g. silica, sand
- C10M 129/06: having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 129/28: having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 133/08: containing hydroxy groups
- C10M 137/02: having no phosphorus-to-carbon bond
- C10M 139/00: Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
- C10M 159/123: {obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds}
- C10M 2201/02: Water
- C10M 2201/085: Phosphorus oxides, acids or salts
- C10M 2201/087: Boron oxides, acids or salts
- C10M 2201/10: Compounds containing silicon
- C10M 2201/102: Silicates
- C10M 2201/105: Silica
- C10M 2207/021: having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 2207/12: having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof
- C10M 2219/024: of esters, e.g. fats
- C10M 2223/04: Phosphate esters
- C10M 2223/042: Metal salts thereof
- C10M 2223/12: obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
- C10M 2223/121: of alcohols or phenols
- C10M 2227/00: Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M 2227/06: Organic compounds derived from inorganic acids or metal salts
- C10M 2227/061: Esters derived from boron
- C10M 2227/062: Cyclic esters
- C10M 2227/063: Complexes of boron halides
- C10M 2227/065: derived from Ti or Zr
- C10M 2227/066: derived from Mo or W
- C10N 2040/00: Specified use or application for which the lubricating composition is intended
- C10N 2040/02: Bearings
- C10N 2040/20: Metal working
- C10N 2040/22: with essential removal of material {, e.g. cutting, grinding or drilling}
- C10N 2040/24: without essential removal of material {, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding}; Punching metal
- C10N 2040/241: {Manufacturing joint-less pipes}
- C10N 2040/242: {Hot working}
- C10N 2040/243: {Cold working}
- C10N 2040/244: {of specific metals}
- C10N 2040/245: {Soft metals, e.g. aluminum}
- C10N 2040/246: {Iron or steel}
- C10N 2040/247: {Stainless steel}
- C10N 2040/25: Internal-combustion engines
- C10N 2040/251: {Alcohol-fuelled engines}
- C10N 2040/255: {Gasoline engines}
- C10N 2040/28: Rotary {engines}
- C10N 2040/30: Refrigerators lubricants {or compressors lubricants}
- C10N 2040/32: Wires, ropes or cables lubricants
- C10N 2040/34: Lubricating-sealants
- C10N 2040/36: Release agents {or mold release agents}
- C10N 2040/38: {Conveyors or chain belts}
- C10N 2040/40: {Generators or electric motors in oil or gas winning field}
- C10N 2040/42: {Flashing oils or marking oils}
- C10N 2040/44: {Super vacuum or supercritical use}
- C10N 2040/50: {Medical uses}
- C10N 2050/01: {Emulsions, colloids, or micelles}
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

Lubricant additives are disclosed which are produced by reacting an alkanolamine, a carboxylic acid and phosphorous acid. The reaction product may also include a boron compound and/or a monofunctional alcohol. The additives are useful in combination with metalworking oils, particularly in extreme pressure applications, to replace currently used chlorinated paraffin additives.

## Claims

### Claim 1

A lubricant additive comprising the reaction product of:
(a) an alkanolamine of the formula: ##STR8## wherein each of R and R' are independently selected from the group consisting of hydrogen and a C.sub.1 to C.sub.6 alkyl group and x, y and z are each integers of from 0 to 10, at least one of which is not 0;
(b) an aliphatic carboxylic acid of the formula: ##STR9## wherein R.sup.3 is a C.sub.1 to C.sub.30 hydrocarbon group; and (c) phosphorous acid;
wherein said reaction is carried out at a temperature of about 50.degree. to about 250.degree. C. and the molar ratio of said alkanolamine to said phosphorous acid is about 0.1:1 to about 10:1.

### Claim 2 (depends on 1)

The product according to claim 1, wherein the molar ratio of said alkanolamine to said carboxylic acid is about 0.5:1 to about 2:1.

### Claim 3 (depends on 1)

The product according to claim 1, wherein said alkanolamine is diethanolamine.

### Claim 4 (depends on 1)

The product according to claim 1, wherein said alkanolamine is isopropanolamine.

### Claim 5 (depends on 1)

The product according to claim 1, wherein the aliphatic carboxylic acid is a long-chain aliphatic carboxylic acid and R.sup.3 is a C.sub.14 -C.sub.30 hydrocarbon group.

### Claim 6 (depends on 1)

The product according to claim 1, wherein the reaction is conducted at a temperature of about 150.degree. to about 160.degree. C.

### Claim 7 (depends on 1)

The product according to claim 1, wherein (a) and (b) are reacted to form an intermediate and then said intermediate is reacted with (c) to form said reaction product.

### Claim 8 (depends on 1)

The product according to claim 1, wherein the reaction of (a), (b) and (c) occurs essentially simultaneously.

### Claim 9 (depends on 1)

A lubricant composition comprising a major proportion of a lubricating oil and a friction reducing amount of the product of claim 1.

### Claim 10 (depends on 9)

A lubricant composition according to claim 9, wherein said lubricating oil is emulsifiable in water.

### Claim 11 (depends on 9)

A lubricant composition according to claim 9, wherein the pH of said product is about 5.5 to about 7.

### Claim 12 (depends on 9)

A composition according to claim 9, wherein said product is present in said oil in amount of about 0.1 to about 10 wt %.

### Claim 13 (depends on 1)

A method of lubricating a metalworking operation comprising performing said operation in the presence of a lubricating oil containing the product of claim 1.

### Claim 14 (depends on 13)

A method according to claim 13, wherein said operation is an extreme pressure operation.