US4422856A
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N-Substituted succinimides, their preparation and use as motor fuel additives
Assignee: Elf Antar France
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Filing: 1981-02-13
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Granted: 1983-12-27
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Expires: 2001-02-13
Abstract
Abstract N-substituted succinimides are obtained by reacting in a first stage, maleic anhydride with an oxyalkylated or polyoxyalkylated monoalcohol of formula R.sup.1 --O--A.sub.n OH wherein R 1 is an aliphatic radical having from 12 to 25 carbon atoms, A is an alkylene radical having 2 to 4 carbon atoms and n is an integer from 1 to 50, and by further reacting the reaction product of the first stage either with a monoprimary amine of formula R.sup.2 --X--Z.sub.m NH.sub.2 or a bi-primary amine of the formula H.sub.2 N--Z--NH.sub.p H, wherein R 2 is an aliphatic radical having from 8 to 25 carbon atoms, Z is an alkylene radical having from 2 to 4 carbon atoms, X is --NH-- or --O--, m is an integer from 0 to 4 and p an integer from 2 to 6. The resultant succinimides are useful as anti-rust and detergent additives for motor fuels.
Inventors
- 👤 Paul Maldonado
- 👤 Choua Cohen
- 👤 Bernard Sillion
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 09:22
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/34; C07D207/36; C07D207/40; C07D207/416; C08; C08G; C08G65/00; C08G65/02; C08G65/32; C08G65/329; C08G65/331; C08G65/332; C08G65/3324; C08G65/333; C08G65/33303; C08G65/33306; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/222; C10L1/224
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
138 words
The N-substituted succinimide obtained by reacting maleic anhydride with at least one oxyalkylated or polyoxyalkylated monoalcohol of the general formula R.sup.1 --O--A--.sub.n OH wherein R 1 is a linear or branched, saturated or unsaturated C 12-25 aliphatic radical; A is a linear or branched C 2-4 alkylene radical, at least two carbon atoms of which are in a straight chain; and n is an integer from 1 to 50; and reacting the resulting succinic anhydride oxyether with a monoprimary amine of the general formula R.sup.2 --X--Z--.sub.m NH.sub.2 wherein R 2 is a linear or branched, saturated or unsaturated, C 8-25 aliphatic radical; Z is a linear or branched C 2-4 alkylene radical at least two carbon atoms of which are in a straight chain; X is --NH-- or --O--; and m is an integer from 0 to 4.
Claim 2
Dependent Claim
138 words
The N-substituted succinimide obtained by reacting maleic anhydride with at least one oxyalkylated or polyoxyalkylated monoalcohol of the general formula R.sup.1 --O--A--.sub.n OH wherein R 1 is a linear or branched, saturated or unsaturated C 12-25 aliphatic radical; A is a linear or branched C 2-4 alkylene radical, at least two carbon atoms of which are in a straight chain; and n is an integer from 1 to 50; and reacting the resulting succinic anhydride oxyether with a monoprimary amine of the general formula R.sup.2 --X--Z--.sub.m NH.sub.2 wherein R 2 is a linear or branched, saturated or unsaturated, C 8-25 aliphatic radical; Z is a linear or branched C 2-4 alkylene radical at least two carbon atoms of which are in a straight chain; X is --NH-- or --O--; and m is an integer from 0 to 4.
Claim 3
Dependent Claim
28 words
An N-substituted succinimide according to claim 1, wherein in said oxyalkylated or polyoxyalkylated monoalcohol, the radical R 1 is a linear C 12 or C 13 alkyl radical.
Claim 4
Dependent Claim
45 words
An N-substituted succinimide according to claim 2, wherein said oxyalkylated or polyoxyalkylated monoalcohol is polyoxypropylated lauric alcohol, trioxypropylated tridecyl alcohol, tridecyl alcohol with sequential recurrent units of ethylene oxide and propylene oxide or tridecyl alcohol with sequential recurrent units of ethylene oxide and isobutylene oxide.
Claim 5
Dependent Claim
27 words
An N-substituted succinimide according to claim 1, wherein said monoprimary amine is N-oleyl propanediamine, N-isotridecyl propanediamine, 3-isotridecyloxy 1-propylamine, 3-hendecyloxy 1-propylamine, 3-tridecyloxy 1-propylamine or 3-(2-ethyl hexyl) oxy 1-propylamine.
Claim 6
Dependent Claim
37 words
An N-substituted succinimide according to claim 1, wherein said monoprimary amine of the general formula R.sup.2 --X--Z--.sub.m NH.sub.2 is used in a proportion of from 1.02 mole to 1.2 mole per mole of said succinic anhydride oxyether.
Claim 7
Dependent Claim
32 words
A motor fuel composition, comprising a major proportion of at least one motor fuel and from 10 to 500 ppm by weight of at least one N-substituted succinimide according to claim 1.
Claim 8
Dependent Claim
23 words
A motor fuel composition according to claim 6, wherein the proportion of the N-substituted succinimide is from 20 to 200 ppm by weight.
Claim 9
Dependent Claim
103 words
An N-substituted succinimide having the formula ##STR7## wherein R 1 is a linear or branched, saturated or unsaturated C 12-25 aliphatic radical; R 2 is a linear or branched, saturated or unsaturated, C 8-25 aliphatic radical; A is a linear or branched C 2-4 alkylene radical, at least two carbon atoms of which are in a straight chain; Z is a linear or branched C 2-4 alkylene radical, at least two carbon atoms of which are in a straight chain; X is --NH-- or --O--; m is an integer from 0 to 4; and n is an integer of from 1 to 50.
Claim 10
Dependent Claim
103 words
An N-substituted succinimide having the formula ##STR7## wherein R 1 is a linear or branched, saturated or unsaturated C 12-25 aliphatic radical; R 2 is a linear or branched, saturated or unsaturated, C 8-25 aliphatic radical; A is a linear or branched C 2-4 alkylene radical, at least two carbon atoms of which are in a straight chain; Z is a linear or branched C 2-4 alkylene radical, at least two carbon atoms of which are in a straight chain; X is --NH-- or --O--; m is an integer from 0 to 4; and n is an integer of from 1 to 50.
Claim 11
Dependent Claim
19 words
An N-substituted succinimide according to claim 8, wherein R 1 is a linear C 12 or C 13 radical.
Claim 12
Dependent Claim
44 words
An N-substituted succinimide according to claim 9, wherein R 1 --OA-- n is polyoxpropylated lauric alcohol, trioxypropylated tridecyl alcohol, tridecyl alcohol with sequential recurrent units of ethylene oxide and propylene oxide or tridecyl alcohol with sequential recurrent units of ethylene oxide and isobutylene oxide.
Claim 13
Dependent Claim
60 words
An N-substituted succinimide according to claim 8, wherein the moiety >N--Z--X-- m R 2 corresponds to a monoprimary amine having the formula H 2 N--Z--X-- m R 2 , wherein Z, X, m and R 2 are as defined in claim 16, said monoprimary amine being N-oleyl propanediamine, N-isotridecyl propanediamine, 3-isotridecyloxy 1-propylamine, 3-hendecyloxy 1-propylamine, 3-tridecyloxy 1-propylamine or 3-(2-ethyl hexyl)-oxy 1-propylamine.
Claim 14
Dependent Claim
32 words
A motor fuel composition, comprising a major proportion of at least one motor fuel and from 10 to 500 ppm by weight of at least one N-substituted succinimide according to claim 16.
Claim 15
Dependent Claim
23 words
A motor fuel composition according to claim 12, wherein the proportion of the N-substituted succinimide is from 20 to 200 ppm by weight.
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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) | 1986-12-26 | 1987-06-27 | 1987-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-26 | 1991-06-27 | 1991-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-26 | 1995-06-27 | 1995-12-27 | $7700.00 | Window Closed / Lapsed |