# US 4,394,278 A · Friction reducing additives and compositions thereof

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- Number: US 4,394,278 A
- Document ID: US4394278A
- Status: Granted
- Kind: A
- Application number: 06/267,105
- Filed: 1981-05-26
- Granted: 1983-07-19
- Earliest claimed: 1981-05-26
- Assignees: Mobil Oil Corporation
- Inventors: Andrew G. Horodysky; Joan M. Kaminski
- Web page: https://patentgrep.com/patent/US4394278A

## CPC

- C07F 5/04: Esters of boric acids
- 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 159/12: Reaction products
- C10M 2207/08: Aldehydes; Ketones
- C10M 2215/08: Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M 2215/082: containing hydroxyl groups; Alkoxylated derivatives
- C10M 2215/086: Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M 2215/12: Partial amides of polycarboxylic acids
- C10M 2215/122: Phtalamic acid
- C10M 2215/224: Imidazoles
- C10M 2219/08: Thiols; Sulfides; Polysulfides; Mercaptals
- C10M 2223/041: Triaryl phosphates
- 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
- C10N 2050/10: semi-solid; greasy
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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

The invention provides (1) products of reaction formed by reacting a hydrolyzed imidazoline, a mercaptan and an aldehyde and (2) products of reaction of (1) and a boron compound, as well as lubricant compositions containing same.

## Claims

### Claim 1

A reaction product produced by (1) reacting a hydrolyzed imidazoline with a mercaptan and an aldehyde, followed by (2) reacting the product of (1) with a boron compound.

### Claim 2 (depends on 1)

The reaction product of claim 1 wherein the hydrolyzed imidazoline employed has one of the formulas ##STR6## wherein R is a hydrocarbyl group containing from 9 to 29 carbon atoms and R.sup.1 is hydrogen or a C.sub.1 to C.sub.6 alkyl group.

### Claim 3 (depends on 1, 2)

The reaction product of claims 1 or 2 wherein the mercaptan used has the formula
R.sup.3 SH
wherein R.sup.3 is a hydrocarbyl group containing from 1 to 18 carbon atoms.

### Claim 4 (depends on 3)

The reaction product of claim 3 wherein the aldehyde used has the formula
R.sup.2 CHO
wherein R.sup.2 is hydrogen or a C.sub.1 to C.sub.8 alkyl group.

### Claim 5 (depends on 4)

The reaction product of claim 4 wherein the hydrocarbyl group of R is alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl or cycloalkenyl.

### Claim 6 (depends on 5)

The reaction product of claim 5 wherein R.sup.3 is an alkyl group.

### Claim 7 (depends on 1)

The reaction product of claim 1 made by (1) reacting hydrolyzed 1-(2-hydroxyethyl)-2-heptadecenyl imidazoline, formaldehyde and n-dodecyl mercaptan, followed by (2) reacting the product of (1) with boric acid.

### Claim 8

A lubricant or liquid hydrocarbon fuel composition comprising a major proportion of a lubricant or fuel and an antifriction or antioxidant amount of a product produced by (1) reacting a hydrolyzed imidazoline with a mercaptan and an aldehyde, followed by (2) reacting the product of (1) with a boron compound.

### Claim 9 (depends on 8)

The composition of claim 8 wherein the hydrolyzed imidazoline employed has one of the formulas ##STR7## wherein R is a hydrocarbyl group containing from 9 to 29 carbon atoms and R.sup.1 is hydrogen or a C.sub.1 to C.sub.6 alkyl group.

### Claim 10 (depends on 8, 9)

The composition of claims 8 or 9 wherein the mercaptan used has the formula
R.sup.3 SH
wherein R.sup.3 is a hydrocarbyl group containing from 8 to 18 carbon atoms.

### Claim 11 (depends on 10)

The composition of claim 10 wherein the aldehyde used has the formula:
R.sup.2 CHO
wherein R.sup.2 is hydrogen or a C.sub.1 to C.sub.8 alkyl group.

### Claim 12 (depends on 11)

The composition of claim 11 wherein the hydrocarbyl group of R is alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl or cycloalkenyl.

### Claim 13 (depends on 2)

The composition of claim 2 wherein R.sup.3 is an alkyl group.

### Claim 14 (depends on 8)

The composition of claim 8 wherein the reaction product is produced by (1) reacting hydrolyzed 1-(2-hydroxyethyl)-2-heptadecenyl imidazoline, formaldehyde and n-dodecyl mercaptan, followed by (2) reacting the product of (1) with boric acid.

### Claim 15 (depends on 8)

The composition of claim 8 wherein the lubricant is a lubricating oil.

### Claim 16 (depends on 8)

The composition of claim 8 wherein the lubricant is a grease.

### Claim 17 (depends on 15)

The composition of claim 15 wherein the lubricating oil is a mineral oil.

### Claim 18 (depends on 15)

The composition of claim 15 wherein the lubricating oil is a synthetic oil.

### Claim 19 (depends on 15)

The composition of claim 15 wherein the lubricating oil is a mixture of mineral oil and synthetic oil.