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US4511369A
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Copolymers with nitrogen groups, useful as additives for decreasing the cloud point of hydrocarbon middle distillates and compositions containing them
Assignee: Elf Antar France
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Filing: 1983-11-09
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Granted: 1985-04-16
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Expires: 2003-11-09
Abstract
Abstract Copolymers with nitrogen groups are used as additives to lower the cloud point of middle distillates such as gas oils. They are obtained by reacting a compound having a primary amine group with a copolymer comprising from 20 to 40% of recurrent units from a linear α-olefin, from 30 to 70% of recurrent units from an α,β-unsaturated dicarboxylic compound, from 5 to 30% of recurrent units from an alkyl ester of unsaturated monocarboxylic acid, and from 5 to 15% of recurrent units from styrene or a styrene derivative. These additives also improve the limit filterability temperature and the pour point of the middle distillates.
Inventors
- 👤 Jacques Denis
- 👤 Bernard Sillion
- 👤 Bernard Damin
- 👤 Robert Leger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 12:31
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/234; C10L1/236; C10L1/2364; C08; C08F; C08F8/00; C08F8/30; C08F8/32
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
217 words
A composition, useful as an additive for decreasing the cloud point of middle distillates, having a number-average molecular weight of 1,000-10,000, and consisting essentially of a copolymer comprising: 20-40% by mole of recurrent units (A) from at least one linear α-olefin; 30-70% by mole of recurrent units (B) from at least one unsaturated α,β-dicarboxylic compound, in the form of a diacid, a lower alkyl diester or an anhydride; 5-30% by mole of recurrent units (C) from at least one alkyl ester of an unsaturated monocarboxylic acid; and - 15% by mole of recurrent units (D) from styrene and/or at least one of its alkylated, halogenated or methoxlated derivatives, wherein the dicarboxylic units (B) of said copolymer are condensed with at least one compound having a single primary amine group, having the formula: R--Z[(CH.sub.2).sub.n NH].sub.m H (I) or HO--CH.sub.2 --R"--NH.sub.2 (II) wherein R is a monovalent saturated aliphatic radical having 1-30 carbon atoms, Z is 0, NH or NR', wherein R' is a monovalent saturated aliphatic radical having 1-30 carbon atoms; n is an integer from 2 to 4; m is zero or an integer from 1 to 4 when Z is NH, or an integer from 1 to 4 when Z is 0 or NR"; and R" is a divalent saturated aliphatic radical having 1-18 carbon atoms.
Claim 2
Dependent Claim
217 words
A composition, useful as an additive for decreasing the cloud point of middle distillates, having a number-average molecular weight of 1,000-10,000, and consisting essentially of a copolymer comprising: 20-40% by mole of recurrent units (A) from at least one linear α-olefin; 30-70% by mole of recurrent units (B) from at least one unsaturated α,β-dicarboxylic compound, in the form of a diacid, a lower alkyl diester or an anhydride; 5-30% by mole of recurrent units (C) from at least one alkyl ester of an unsaturated monocarboxylic acid; and - 15% by mole of recurrent units (D) from styrene and/or at least one of its alkylated, halogenated or methoxlated derivatives, wherein the dicarboxylic units (B) of said copolymer are condensed with at least one compound having a single primary amine group, having the formula: R--Z[(CH.sub.2).sub.n NH].sub.m H (I) or HO--CH.sub.2 --R"--NH.sub.2 (II) wherein R is a monovalent saturated aliphatic radical having 1-30 carbon atoms, Z is 0, NH or NR', wherein R' is a monovalent saturated aliphatic radical having 1-30 carbon atoms; n is an integer from 2 to 4; m is zero or an integer from 1 to 4 when Z is NH, or an integer from 1 to 4 when Z is 0 or NR"; and R" is a divalent saturated aliphatic radical having 1-18 carbon atoms.
Claim 3
Dependent Claim
21 words
A composition according to claim 1, wherein said linear α-olefin providing the recurrent units (A) comprises at least 16 carbon atoms.
Claim 4
Dependent Claim
93 words
A composition according to claim 1, wherein said linear α-olefin providing the recurrent units (A) comprises 16 to 30 carbon atoms; the unsaturated α,β- dicarboxylic compound providing the recurrent units (B) is at least one maleic or alkylmaleic acid, a methyl, ethyl or propyl diester thereof or a maleic or alkylmaleic anhydride; the alkyl ester of an unsaturated monocarboxylic acid providing the recurrent units (C) is at least one alkyl acrylate or methacrylate having 4 to 20 carbon atoms in the alkyl group; and the compound providing the recurrent units (D) is styrene.
Claim 5
Dependent Claim
25 words
A composition according to claim 1, wherein said compound providing an amine group (I) is at least one linear primary amine having 12-24 carbon atoms.
Claim 6
Dependent Claim
37 words
A composition according to claim 1, wherein said compound providing an amine group (II) is at least one amino-alcohol having the formula HO--CH.sub.2 --R"--NH.sub.2 wherein R" is a linear or branched alkylene radical having 1-18 carbon atoms.
Claim 7
Dependent Claim
106 words
A composition according to claim 1, which is obtained by the steps of: (a) effecting a radical-promoted copolymerization of appropriate proportions of at least one linear α-olefin, at least one unsaturated α,β-dicarboxylic compound in the form of a diacid, a lower alkyl diester or an anhydride, at least one alkyl ester of an unsaturated monocarboxylic acid and styrene and/or at least one styrene derivative; and (b) condensing the resultant copolymer with at least one compound providing a primary amine group and having the formula (I) or (II), in a proportion of at least about 0.5 mole per mole of α,β-unsaturated dicarboxylic compound in said resultant copolymer.
Claim 8
Dependent Claim
34 words
A composition according to claim 6, wherein the proportion of said compound with a primary amine group of formula (I) or (II) ranges from 0.9 to 1.1 per mole of said α,β-unsaturated dicarboxylic compound.
Claim 9
Dependent Claim
99 words
A composition according to claim 1, which is obtained by the step of effecting a radical-promoted copolymerization of appropriate proportions of at least one linear α-olefin, at least one α,β-unsaturated dicarboxylic compound, at least one alkyl ester of an unsaturated monocarboxylic acid and styrene and/or at least one styrene derivative, said α,β-unsaturated dicarboxylic compound being at least one N-substituted imide obtained by prior reaction of an α,β-unsaturated dicarboxylic compound, in the form of a diacid, a lower alkyl diester or an anhydride, with at least one compound providing a primary amine group and having said formula (I) or (II).
Claim 10
Dependent Claim
42 words
A middle distillate composition, which it comprises a major proportion of middle distillate having a distillation range from 150° to 450° C. and a minor proportion of at least one composition according to claim 1 sufficient to decrease the cloud point thereof.
Claim 11
Dependent Claim
53 words
A composition according to claim 1, wherein said compound providing an amine group (I) is at least one polyamine having the formula: R--NH[(CH.sub.2).sub.n NH].sub.m H wherein R is a linear alkyl radical having 12-24 carbon atoms, n is an integer from 2 to 4, and m is an integer from 1 to 4.
Claim 12
Dependent Claim
64 words
A composition according to claim 1 wherein said compound providing an amine group (I) is at least one polyamine having the formula: R--NR'--(CH.sub.2).sub.n NH].sub.m H wherein R and R' are each a linear alkyl radical having 8-24 carbon atoms, R and R' together having 16-32 carbon atoms, n is an integer from 2 to 4, and m is an integer from 1 to 4.
Claim 13
Dependent Claim
52 words
A composition according to claim 1, wherein said compound providing an amine group (I) is at least one ether-amine having the formula: R--O--(CH.sub.2).sub.n NH].sub.m H wherein R is an alkyl radical having 12-24 carbon atoms, n is an integer from 2 to 4, and m is an integer from 1 to 4.
Claim 14
Dependent Claim
24 words
A composition according to claim 10, wherein said polyamine having formula (I) is N-dodecyl1,3-diaminopropane, N-tetradecyl1,3-diaminopropane, N-hexadecyl1,3-diaminopropane, N-octadecyl1,3-diaminopropane, N-eicosyl1,3-diaminopropane, N-docosyl1,3-diaminopropane, N-hexadecyldipropylenetriamine, N-octadecyldipropylenetriamine, N-eicosyldipropylenetriamine or N-docosyldipropylenetriamine.
Claim 15
Dependent Claim
31 words
A composition according to claim 11, wherein said polyamine having formula (I) is N,N-diethyl1,2-diaminoethane, N,N-diisopropyl1,2-diaminoethane, N,N-dibutyl1,2-diaminoethane, N,N-diethyl1,4-diamino butane, N,N-dimethyl1,3-diaminopropane, N,N-diethyl1,3-diaminopropane, N,N-dioctyl1,3-diaminopropane, N,N-didecyl1,3-diaminopropane, N,N-didodecyl1,3-diaminopropane, N,N-ditetradecyl1,3-diaminopropane, N,N-dihexadecyl1,3-diaminopropane, N,N-dioctadecyl1,3-diaminopropane, N,N-didodecyldipropylenetriamine, N,N-ditetradecyldipropylenetriamine, N,N-dihexadecyldipropylenetriamine or N,N-dioctadecyldipropylenetriamine.
Claim 16
Dependent Claim
24 words
A composition according to claim 12, wherein said ether-amine is 2-methoxyethylamine, 3-methoxypropylamine, 4-methoxybutylamine, 3-ethoxypropylamine, 3-octyloxypropylamine, 3-decylocypropylamine, 3-hexadecyloxypropylamine, 3-eicosyloxypropylamine, 3-docosyloxypropylamine, N-(3-octyloxypropyl)1,3-diaminopropane, N-3(3-decyloxypropyl)1,3-diaminopropane, (2,4,6-trimethyldecyl)3-oxypropylamine or N-[(2,4,6-trimethyldecyl)-3-oxypropyl]1,3-diaminopropane.
Claim 17
Dependent Claim
32 words
A method of lowering the cloud point of a middle distillate composition, comprising incorporating in said middle distillate composition an effective cloud point depressant amount of a composition according to claim 1.
Claim 18
Dependent Claim
14 words
A method according to claim 16, wherein said effective amount is 0.001-1% by weight.
Claim 19
Dependent Claim
13 words
A method according to claim 17, wherein said amount is 0.01-0.2% by weight.
Claim 20
Dependent Claim
19 words
A composition according to claim 9, wherein said amount of said cloud point depressant composition is 0.01-0.2% by weight.
References Cited (Backward Citations)
US4160739A
Cited
US4359325A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-04-15 | 1988-10-15 | 1989-04-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-15 | 1992-10-15 | 1993-04-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-15 | 1996-10-15 | 1997-04-16 | $7700.00 | Window Closed / Lapsed |