# US 5,346,637 A · Antiwear additives

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- Number: US 5,346,637 A
- Document ID: US5346637A
- Status: Granted
- Kind: A
- Application number: 07/991,614
- Filed: 1992-12-16
- Granted: 1994-09-13
- Earliest claimed: 1992-12-16
- Assignees: Mobil Oil Corporation
- Inventors: Andrew G. Horodysky; Shi-Ming Wu
- Web page: https://patentgrep.com/patent/US5346637A

## CPC

- C10M 159/123: {obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds}
- C10M 125/22: Compounds containing sulfur, selenium or tellurium
- C10M 125/24: Compounds containing phosphorus, arsenic or antimony
- C10M 129/72: of polycarboxylic acids
- C10M 129/95: Esters
- C10M 133/08: containing hydroxy groups
- C10M 133/12: having amino groups bound to a carbon atom of a six-membered aromatic ring
- C10M 137/02: having no phosphorus-to-carbon bond
- C10M 2201/065: Sulfides; Selenides; Tellurides
- C10M 2201/066: Molybdenum sulfide
- C10M 2201/084: containing sulfur, selenium or tellurium
- C10M 2201/085: Phosphorus oxides, acids or salts
- C10M 2207/282: of (cyclo)aliphatic oolycarboxylic acids
- C10M 2207/285: of aromatic polycarboxylic acids
- C10M 2207/286: of polymerised unsaturated acids
- C10M 2207/34: Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
- C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof
- C10M 2215/06: having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M 2215/064: Di- and triaryl amines
- C10M 2215/065: Phenyl-Naphthyl amines
- C10M 2215/066: Arylene diamines
- C10M 2215/067: Polyaryl amine alkanes
- C10M 2215/068: having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
- C10M 2223/02: having no phosphorus-to-carbon bonds
- C10M 2223/04: Phosphate esters
- C10M 2223/042: Metal salts thereof
- C10M 2223/049: Phosphite
- C10M 2223/10: Phosphatides, e.g. lecithin, cephalin
- C10M 2223/12: obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
- C10M 2223/121: of alcohols or phenols
- C10N 2040/00: Specified use or application for which the lubricating composition is intended
- C10N 2040/02: Bearings
- C10N 2040/08: Hydraulic fluids, e.g. brake-fluids
- C10N 2040/135: {Steam engines or turbines}
- C10N 2040/20: Metal working
- C10N 2040/25: Internal-combustion engines
- C10N 2040/251: {Alcohol-fuelled engines}
- C10N 2040/252: {Diesel engines}
- C10N 2040/253: {Small diesel 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}
- 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)
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

A multifunctional antiwear and antioxidant lubricant additive is the reaction product of a diacyl halide, a source of phosphorus or a source of phosphorus and an aryl amine. The diacyl halide is derived from a hydrocarbon-substituted succinic anhydride, suitably dodecenyl succinic anhydride, an alkoxylated amine and an inorganic acid halide, suitably thionyl chloride. A suitable source of phosphorus is dibutyl phosphite or bis(nonylphenyl)phosphite. A suitable aryl amine is N-octylphenyl-1-naphthylamine.

## Claims

### Claim 1

A lubricant composition comprising a major proportion of lubricant and a minor multifunctional antioxidant and antiwear amount of an additive product comprising the reaction product of a hydrocarbon-substituted diacyl halide, derived from a hydrocarbon-substituted succinic ester-carboxylic acid and a halogenating agent, a source of phosphorus or a source of phosphorus and an aryl or alkaryl amine, the hydrocarbon group of the hydrocarbon-substituted succinic ester-acid contains from about 1 to about 300 carbon atoms.

### Claim 2 (depends on 1)

The composition of claim 1 in which the hydrocarbon-substituted succinic ester-carboxylic acid is derived from a reaction product of an alkoxylated amine and a hydrocarbon-substituted succinic anhydride, the hydrocarbon-substitued succinic anhydride is represented by the structural formula: ##STR4## where R is a hydrocarbon group containing from about 1 to 300 carbon atoms.

### Claim 3 (depends on 2)

The composition of claim 2 in which the hydrocarbon-substituted succinic anhydride is derived from a condensation reaction between dodecene and maleic anhydride.

### Claim 4 (depends on 2)

The composition of claim 2 in which the alkoxylated amine is free of active amino-hydrogen atoms.

### Claim 5 (depends on 2)

The composition of claim 2 in which the alkoxylated amine is represented by the structural formula: ##STR5## where R.sub.2 is a hydrocarbon group containing from about 1 to 100 carbon atoms, R.sub.3 is a hydrocarbon group containing 3 to 25 carbon atoms, R.sub.4, R.sub.5 and R.sub.6 are hydrogen or the same or different hydrocarbon group containing about 1 to 60 carbon atoms, x is an integer ranging from about 0 to 20, y is an integer ranging from about 0 to 20, z is an integer ranging from about 0 to 20, and x+y+z equals at least 1.

### Claim 6 (depends on 2)

The composition of claim 2 in which the alkoxylated amine is represented by the structural formula: ##STR6## where R.sub.2 is a hydrocarbon group containing from about 1 to 100 carbon atoms, R.sub.4 and R.sub.5 are hydrogen, or the same or different hydrocarbon group containing about 1 to 60 carbon atoms, x is an integer ranging from about 0 to 20, y is an integer ranging from about 0 to 20, and x+y equals at least 1.

### Claim 7 (depends on 5)

The composition of claim 5 in which the groups, represented by R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different hydrocarbon groups selected from the group consisting of methyl, ethyl, propyl, butyl, isobutyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, polymers and copolymers made therefrom.

### Claim 8 (depends on 6)

The composition of claim 6 in which the groups, represented by R.sub.2, R.sub.4 and R.sub.5 are the same or different hydrocarbon groups selected from the group consisting of methyl, ethyl, propyl, butyl, isobutyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, polymers and copolymers made therefrom.

### Claim 9 (depends on 1)

The composition of claim 1 in which the halogenating agent is an inorganic acid halide.

### Claim 10 (depends on 9)

The composition of claim 9 in which the inorganic acid halide is thionyl chloride.

### Claim 11 (depends on 1)

The composition of claim 1 in which the source of phosphorus is an organophosphite.

### Claim 12 (depends on 11)

The composition of claim 11 in which the organophosphite is a diorgano or triorgano phosphite in which the organo group contains from 3 to 100 carbon atoms.

### Claim 13 (depends on 12)

The composition of claim 12 in which the organo phosphite is dibutyl phosphite, tributyl phosphite, diphenyl phosphite, triphenyl phosphite or bis(nonylphenyl) phosphite.

### Claim 14 (depends on 13)

The composition of claim 13 in which the alkaryl amine is N-octylphenyl-1-naphthylamine.

### Claim 15 (depends on 1)

The composition of claim 1 in which the lubricant is a mineral or synthetic oil or a mixture thereof.

### Claim 16 (depends on 1)

The composition of claim 1 in which the amount of the additive product ranges from 0.001 to 10 wt. % based on the entire weight of the composition.

### Claim 17 (depends on 15)

The composition of claim 15 in which the lubricant is a grease made from a mineral oil or synthetic oil or mixture thereof and a grease thickener.

### Claim 18

A process for making a product of reaction suitable for use as a lubricant additive comprising (1) reacting a hydrocarbon-substituted succinic anhydride with an alkoxylated amine which is free of an active amino-hydrogen to produce a hydrocarbon-substituted ester-carboxylic acid; (2) reacting the hydrocarbon-substituted ester-carboxylic acid with an inorganic acid halide to produce a diacyl halide; and (3) reacting the diacyl halide with a source of phosphorus or a source of phosphorus and an aryl amine or an alkaryl amine.

### Claim 19 (depends on 18)

The process of claim 18 in which the hydrocarbon substituted succinic anhydride is dodecenyl succinic anhydride.

### Claim 20 (depends on 18)

The process of claim 18 in which the inorganic acid halide is thionyl chloride.

### Claim 21 (depends on 18)

The process of claim 18 in which the source of phosphorus is bis(nonylphenyl) phosphite or dibutyl phosphite.

### Claim 22 (depends on 21)

The process of claim 21 in which the amine is N-octylphenyl-1-naphthylamine.

### Claim 23

A method of reducing wear between relatively moving surfaces comprising contacting the relatively moving surfaces with a reaction product of a hydrocarbon-substituted diacyl halide, derived from a hydrocarbon-substituted succinic ester-carboxylic acid and a halogenating agent, a source of phosphorus or a source of phosphorus and an aryl or alkaryl amine, the hydrocarbon group of the hydrocarbon-substituted succinic ester-acid contains from about 1 to about 300 carbon atoms.

### Claim 24 (depends on 23)

The method of claim 23 in which the hydrocarbon-substituted succinic ester-carboxylic acid is derived from a reaction product of an alkoxylated amine and a hydrocarbon-substituted succinic anhydride.

### Claim 25

A lubricating additive product prepared by a process comprising (1) reacting a hydrocarbon-substituted succinic anhydride with an alkoxylated amine which is free of an active amino-hydrogen to produce a hydrocarbon-substituted ester-carboxylic acid; (2) reacting the hydrocarbon-substituted ester-carboxylic acid with an inorganic acid halide to produce a diacyl halide; and (3) reacting the diacyl halide with a source of phosphorus or a source of phosphorus and an aryl amine or alkaryl amine.