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US4168242A
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Novel alkenyl-substituted oxa-amines and their use as additives for lubricating oils and fuels
Assignee: Orogil SA
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Filing: 1978-01-27
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Granted: 1979-09-18
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Expires: 1998-01-27
Abstract
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.
Inventors
- 👤 Gerard Soula
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 18:40
CPC Classifications
C; C10; C10M; C10M133/00; C10M133/52; C10M133/54; C08; C08F; C08F8/00; C08F8/30; C08F8/32; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/222; C10L1/2222; C10L1/2225; C10L1/234; C10L1/238; C10M133/02; C10M133/04; C10M133/06; C10M133/08; C10M2203/00; C10M2203/06; C10M2205/00; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/028; C10M2207/28; C10M2207/282; C10M2207/34; C10M2209/00; C10M2209/10; C10M2209/103; C10M2209/108; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/24; C10M2215/26; C10M2217/00; C10M2217/04; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/044; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/042; C10M2223/045; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05; C10N; C10N2010/00; C10N2010/04
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
150 words
A composition of matter comprising at least one compound of the formula: ##STR9## in which formula: R represents a C 20 -C 350 alkenyl group, R' represents a member selected from a hydrogen atom and the radical R, R 1 and R 2 represent a member selected from a hydrogen atom and a methyl radical, R" represents a radical of the formula: ##STR10## in which R' 1 and R' 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' 3 and R' 4 represent a member selected from a hydrogen atom, the radical R, a radical of the formulae: ##STR13## a C 1 -C 4 alkyl group and a phenyl group, in which R' 5 and R' 6 represent a member selected from a hydrogen atom and the radical R.
Claim 2
Dependent Claim
150 words
A composition of matter comprising at least one compound of the formula: ##STR9## in which formula: R represents a C 20 -C 350 alkenyl group, R' represents a member selected from a hydrogen atom and the radical R, R 1 and R 2 represent a member selected from a hydrogen atom and a methyl radical, R" represents a radical of the formula: ##STR10## in which R' 1 and R' 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' 3 and R' 4 represent a member selected from a hydrogen atom, the radical R, a radical of the formulae: ##STR13## a C 1 -C 4 alkyl group and a phenyl group, in which R' 5 and R' 6 represent a member selected from a hydrogen atom and the radical R.
Claim 3
Dependent Claim
35 words
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 50 -C 300 alkenyl group.
Claim 4
Dependent Claim
120 words
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 1 and R 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 1 -C 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 20 -C 350 alkenyl group and X represents a halogen selected from chlorine and bromine.
Claim 5
Dependent Claim
32 words
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 6
Dependent Claim
26 words
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 7
Dependent Claim
17 words
A composition of matter in accordance with claim 3 wherein the halogenated polyolefin is a halogenated polyisobutylene.
Claim 8
Dependent Claim
147 words
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 1 and R 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 1 -C 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 20 -C 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° and 200° C.
Claim 9
Dependent Claim
35 words
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 10
Dependent Claim
24 words
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 11
Dependent Claim
22 words
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 12
Dependent Claim
33 words
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° and 180° C.
Claim 13
Dependent Claim
21 words
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 14
Dependent Claim
34 words
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 15
Dependent Claim
34 words
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 16
Dependent Claim
34 words
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 17
Dependent Claim
34 words
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 18
Dependent Claim
37 words
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 19
Dependent Claim
37 words
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 20
Dependent Claim
37 words
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 21
Dependent Claim
37 words
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.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-09-17 | 1983-03-19 | 1983-09-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-09-17 | 1987-03-19 | 1987-09-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-09-17 | 1991-03-19 | 1991-09-18 | $7700.00 | Window Closed / Lapsed |