# US 4,168,242 A · Novel alkenyl-substituted oxa-amines and their use as additives for lubricating oils and fuels

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- Number: US 4,168,242 A
- Document ID: US4168242A
- Status: Granted
- Kind: A
- Application number: 05/872,941
- Filed: 1978-01-27
- Granted: 1979-09-18
- Earliest claimed: 1977-02-22
- Assignees: Orogil
- Inventors: Gerard Soula
- Web page: https://patentgrep.com/patent/US4168242A

## CPC

- C10M 133/54: Amines
- C08F 8/32: by reaction with amines
- C10L 1/2225: {hydroxy containing (C10L1/221 takes precedence)}
- C10L 1/238: obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)}
- C10M 133/08: containing hydroxy groups
- C10M 2203/06: Well-defined aromatic compounds
- C10M 2205/00: Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M 2207/028: Overbased salts thereof
- C10M 2207/282: of (cyclo)aliphatic oolycarboxylic acids
- C10M 2207/34: Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
- C10M 2209/103: Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M 2209/108: etherified
- C10M 2215/04: having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof
- C10M 2215/26: Amines
- C10M 2217/046: Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
- C10M 2217/06: Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
- C10M 2219/044: Sulfonic acids, Derivatives thereof, e.g. neutral salts
- C10M 2223/04: Phosphate esters
- C10M 2223/042: Metal salts thereof
- C10M 2223/045: Metal containing thio derivatives
- C10M 2229/02: Unspecified siloxanes; Silicones
- C10M 2229/05: containing atoms other than silicon, hydrogen, oxygen or carbon
- C10N 2010/04: Groups 2 or 12
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

Novel compositions of matter comprising alkenyl amines are provided. They are prepared by the reaction of a halogenated polyolefin with at least one polyamine having an ether group, such as tris(6-amino-3-oxa-hexyl)amine, N,N-bis(6-amino-3-oxa-hexyl)ethanol amine, N-ethyl-N,N-bis(6-amino-3-oxa-hexyl)amine, etc. The novel compositions of matter provide detergent-dispersant additives for use in lubricating oils and fuels.

## Claims

### Claim 1

A composition of matter comprising at least one compound of the formula: ##STR9## in which formula: R represents a C.sub.20 -C.sub.350 alkenyl group,
R' represents a member selected from a hydrogen atom and the radical R,
R.sub.1 and R.sub.2 represent a member selected from a hydrogen atom and a methyl radical,
R" represents a radical of the formula: ##STR10## in which R'.sub.1 and R'.sub.2 represent a member selected from a hydrogen atom, the radical R and a radical of the formula: ##STR11## R"' represents a radical of the formula: ##STR12## in which R'.sub.3 and R'.sub.4 represent a member selected from a hydrogen atom, the radical R, a radical of the formulae: ##STR13## a C.sub.1 -C.sub.4 alkyl group and a phenyl group, in which R'.sub.5 and R'.sub.6 represent a member selected from a hydrogen atom and the radical R.

### Claim 2 (depends on 1)

A composition of matter in accordance with claim 1, characterized by the fact that it contains at least one alkenyl amine of formula (I) in which R represents a C.sub.50 -C.sub.300 alkenyl group.

### Claim 3 (depends on 1)

A composition of matter in accordance with claim 1, comprising the reaction product of at least one polyamine of the formula ##STR14## in which formula R.sub.1 and R.sub.2 represent a member selected from a hydrogen atom and a methyl radical,
r represents a member selected from a radical of the formula: ##STR15## a C.sub.1 -C.sub.4 alkyl radical, and a phenyl radical, m is a whole number from 1 to 3
n is a number selected from 0, 1 and 2
m+n being equal to 2 or 3
with a halogenated polyolefin of the formula RX in which R represents a C.sub.20 -C.sub.350 alkenyl group and X represents a halogen selected from chlorine and bromine.

### Claim 4 (depends on 1)

A composition of matter in accordance with claim 1, comprising the reaction product of a halogenated polyolefin with at least one polyamine selected from the class consisting of tris(6-amino-3-oxa-hexyl)amine, N,N-bis(6-amino-3-oxa-hexyl)ethanolamine, and N-ethyl-N,N-bis(6-amino-3-oxa-hexyl)amine.

### Claim 5 (depends on 3)

A composition of matter in accordance with claim 3 wherein the halogenated polyolefin is a member selected from the class consisting of chlorinated and brominated polyolefins.

### Claim 6 (depends on 3)

A composition of matter in accordance with claim 3 wherein the halogenated polyolefin is a halogenated polyisobutylene.

### Claim 7 (depends on 1)

A process for preparing a composition of matter in accordance with claim 1, which process comprises reacting at least one amine of the formula ##STR16## in which formula R.sub.1 and R.sub.2 represent a member selected from a hydrogen atom and a methyl radical,
r represents a member selected from a radical of the formula: ##STR17## a C.sub.1 -C.sub.4 alkyl radical, and a phenyl radical, m is a whole number from 1 to 3
n is a number selected from 0, 1 and 2
m+n being equal to 2 or 3
with a halogenated polyolefin of the formula RX in which R represents a C.sub.20 -C.sub.350 alkenyl group and X represents a halogen selected from chlorine and bromine, in a molar ratio of amine to halogenated polyolefin of between about 2:1 and 1:6, at a temperature between about 120.degree. and 200.degree. C.

### Claim 8 (depends on 7)

A process in accordance with claim 7, wherein the halogenated polyolefin contains from about 50 to 300 carbon atoms and from about 1 to 1.5 gram atom of halogen per gram molecule of halogenated polyolefin.

### Claim 9 (depends on 7)

A process in accordance with claim 7, wherein the halogenated polyolefin is a member selected from polypropylene, a halogenated polybutylene, and a halogenated polyisobutylene.

### Claim 10 (depends on 7)

A process in accordance with claim 7, wherein the molar ratio of amine to halogenated polyolefin is between about 2:1 and 1:4.

### Claim 11 (depends on 7)

A process in accordance with claim 7, wherein the reaction of the amine of formula II with the halogenated polyolefin RX is carried out at a temperature between about 130.degree. and 180.degree. C.

### Claim 12 (depends on 7)

A process in accordance with claim 7, wherein the amine of formula II is selected from among tris(6-amino-3-oxa-hexyl)amine, N,N-bis(6-amino-3-oxa-hexyl)ethanolamine, and N-ethyl-N,N-bis(6-amino-3-oxa-hexyl)amine.

### Claim 13 (depends on 1)

A novel lubricating composition comprising a major proportion of at least one lubricating oil and between about 1 and 10% by weight of at least one composition of matter in accordance with claim 1.

### Claim 14 (depends on 2)

A novel lubricating composition comprising a major proportion of at least one lubricating oil and between about 1 and 10% by weight of at least one composition of matter in accordance with claim 2.

### Claim 15 (depends on 1)

A novel lubricating composition comprising a major proportion of at least one lubricating oil and between about 4 and 10% by weight of at least one composition of matter in accordance with claim 1.

### Claim 16 (depends on 2)

A novel lubricating composition comprising a major proportion of at least one lubricating oil and between about 4 and 10% by weight of at least one composition of matter in accordance with claim 2.

### Claim 17 (depends on 1)

A fuel oil composition comprising a major proportion of at least one fuel oil and between about 5 and 6,000 parts per million by weight of at least one composition of matter in accordance with claim 1.

### Claim 18 (depends on 2)

A fuel oil composition comprising a major proportion of at least one fuel oil and between about 5 and 6,000 parts per million by weight of at least one composition of matter in accordance with claim 2.

### Claim 19 (depends on 1)

A fuel oil composition comprising a major proportion of at least one fuel oil and between about 40 and 2,000 parts per million by weight of at least one composition of matter in accordance with claim 1.

### Claim 20 (depends on 2)

A fuel oil composition comprising a major proportion of at least one fuel oil and between about 40 and 2,000 parts per million by weight of at least one composition of matter in accordance with claim 2.