# US 4,396,517 A · Phenolic-containing mannich bases and lubricants containing same

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- Number: US 4,396,517 A
- Document ID: US4396517A
- Status: Granted
- Kind: A
- Application number: 06/291,651
- Filed: 1981-08-10
- Granted: 1983-08-02
- Earliest claimed: 1981-08-10
- Assignees: Mobil Oil Corporation
- Inventors: Robert M. Gemmill, Jr.; Andrew G. Horodysky
- Web page: https://patentgrep.com/patent/US4396517A

## CPC

- C10L 10/08: for improving lubricity; for reducing wear
- C10L 1/2225: {hydroxy containing (C10L1/221 takes precedence)}
- C10L 10/04: for minimising corrosion or incrustation
- C10M 133/08: containing hydroxy groups
- C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- 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)

## Abstract

Reaction products from certain phenol, aldehydes and amines are effective friction reducing additives in lubricants and in liquid fuels, such as gasoline and alcohol fuels.

## Claims

### Claim 1

A product of reaction made by reacting an aldehyde, cocoamine and at least one phenol of the formula: ##STR6## wherein R is hydrogen or a C.sub.1 to C.sub.30 hydrocarbyl group and R.sup.1 is a tertiary hydrocarbyl containing 4 to 20 carbon atoms.

### Claim 2 (depends on 1)

The product of claim 1 wherein said hydrocarbyl is alkyl, alkenyl, aryl, alkaryl or aralkyl and said tertiary hydrocarbyl is a tertiary alkyl or alkenyl.

### Claim 3 (depends on 1)

The product of claim 1 wherein in preparing same the aldehyde is an aliphatic aldehyde.

### Claim 4 (depends on 3)

The product of claim 3 wherein the aldehyde has the formula
R.sup.3 CHO
in which R.sup.3 is a C.sub.1 to C.sub.6 alkyl.

### Claim 5 (depends on 3)

The product of claim 3 wherein the aldehyde is formaldehyde, paraformaldehyde, acetaldehyde, aldol, benzaldehyde, furfural or the substituted members thereof.

### Claim 6 (depends on 5)

The product of claim 5 wherein the aldehyde is paraformaldehyde.

### Claim 7 (depends on 1)

The product of claim 1 wherein the amine is cocoamine, the phenol is p-tert-butylphenol and the aldehyde is paraformaldehyde, in a mole ratio of 2:1:2, respectively.

### Claim 8 (depends on 1)

The product of claim 1 wherein the amine is cocoamine, the phenol is p-tert-octylphenol and the aldehyde is paraformaldehyde, in a mole ratio of 2:1:2, respectively.

### Claim 9 (depends on 1)

A lubricant or liquid fuel composition comprising a major proportion of a lubricant or fuel and an antifriction amount of the product of claim 1.

### Claim 10 (depends on 9)

The composition of claim 9 wherein in preparing said product said hydrocarbyl is alkenyl, alkyl, aryl, alkaryl or aralkyl and said tertiary hydrocarbyl is a tertiary alkyl or alkenyl.

### Claim 11 (depends on 9)

The composition of claim 9 wherein in preparing said product the aldehyde is an aliphatic aldehyde.

### Claim 12 (depends on 11)

The composition of claim 11 wherein the aldehyde has the formula
R.sup.3 CHO
in which R.sup.3 is a C.sub.1 to C.sub.6 alkyl.

### Claim 13 (depends on 11)

The composition of claim 11 wherein the aldehyde is formaldehyde, paraformaldehyde, acetaldehyde, aldo, benzaldehyde, furfural or the substituted members thereof.

### Claim 14 (depends on 9)

The composition of claim 9 wherein in preparing the product the amine is cocoamine, the phenol is p-tert-butylphenol and the aldehyde is paraformaldehyde, in a mole ratio of 2:1:2, respectively.

### Claim 15 (depends on 9)

The composition of claim 9 wherein in preparing the product the amine is cocoamine, the phenol is p-tert-octylphenol and the aldehyde is paraformaldehyde, in a mole ratio of 2:1:2, respectively.

### Claim 16 (depends on 9)

The composition of claim 9 wherein said lubricant is a lubricating oil or a grease therefrom.

### Claim 17 (depends on 9)

The composition of claim 9 wherein the lubricant is a mineral or synthetic lubricating oil or mixtures thereof.

### Claim 18 (depends on 17)

The composition of claim 17 wherein the lubricating oil is a mineral oil.

### Claim 19 (depends on 17)

The composition of claim 17 wherein the lubricating oil is a synthetic oil.

### Claim 20 (depends on 17)

The composition of claim 17 wherein the lubricating oil is a mixture of mineral and synthetic oils.

### Claim 21 (depends on 16)

The composition of claim 16 wherein the lubricant is a grease.

### Claim 22 (depends on 9)

The composition of claim 9 wherein said fuel is a liquid hydrocarbon fuel or an alcohol fuel.

### Claim 23 (depends on 22)

The composition of claim 22 wherein the liquid hydrocarbon fuel is gasoline.

### Claim 24 (depends on 22)

The composition of claim 22 wherein the liquid hydrocarbon fuel is a diesel fuel.

### Claim 25 (depends on 22)

The composition of claim 22 wherein the alcohol is methanol.

### Claim 26 (depends on 22)

The composition of claim 22 wherein the alcohol is ethanol.