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US4731095A
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Nitrogen containing copolymers useful as additives for lowering the cloud point of hydrocarbon middle distillates and compositions containing them
Assignee: Elf Antar France
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Filing: 1985-09-16
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Granted: 1988-03-15
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Expires: 2005-09-16
Abstract
Abstract Copolymers with nitrogen groups are used as additives to lower the cloud point and improve the filterability limit temperature and the pour point of middle distillates such as gas oils. They are obtained by reacting a compound having a primary amine group with a copolymer comprising 15 to 40% of recurrent units form a linear alpha -olefin, 20 to 70% of recurrent units form and alpha , beta -unsaturated dicarboxylic compound and 15 to 45% of recurrent units form an alkyl ester of unsaturated monocarboxylic acid.
Inventors
- 👤 Jacques Garapon
- 👤 Bernard Sillion
- 👤 Bernard Damin
- 👤 Robert Leger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:01
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/30; C08F8/32; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/234; C10L1/236; C10L1/2364; C10L1/2366
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
193 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 being a copolymer consisting essentially of: 15-40% mole of recurrent units (A) from at least one unbranched α-olefin of at least 16 carbon atoms; 20-70% by mole of imidized recurrent units (B) from condensation, prior or subsequent to copolymerization, of at least one unsaturated α,β-dicarboxylic compound, in the form of a diacid, a lower alkyl diester or an anhydride, with at least one compound having a single primary amine group, having the formula: ##STR5## 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; and 1- 40% by mole of recurrent units (C) from at least one alkyl ester of an unsaturated monocarboxylic acid.
Claim 2
Dependent Claim
193 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 being a copolymer consisting essentially of: 15-40% mole of recurrent units (A) from at least one unbranched α-olefin of at least 16 carbon atoms; 20-70% by mole of imidized recurrent units (B) from condensation, prior or subsequent to copolymerization, of at least one unsaturated α,β-dicarboxylic compound, in the form of a diacid, a lower alkyl diester or an anhydride, with at least one compound having a single primary amine group, having the formula: ##STR5## 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; and 1- 40% by mole of recurrent units (C) from at least one alkyl ester of an unsaturated monocarboxylic acid.
Claim 3
Dependent Claim
21 words
A composition according to claim 1, wherein said linear α-olefin providing the recurrent units (A) contains 16 to 30 carbon atoms.
Claim 4
Dependent Claim
40 words
A composition according to claim 1, wherein said unsaturated α,β-dicarboxylic compound condensed to provide the imidized recurrent units (B) is at least one maleic or alkylmaleic acid, a methyl, ethyl or propyl diester thereof or a maleic or alkylmaleic anhydride.
Claim 5
Dependent Claim
36 words
A composition according to claim 1, wherein said alkyl ester of an unsaturated monocarboxylic acid providing the recurrent units (C) is at least one alkyl acrylate or methacrylate having 4-30 carbon atoms in the alkyl group.
Claim 6
Dependent Claim
25 words
A composition according to claim 1, wherein said compound having an amine group (I) is at least one linear primary amine having 12-24 carbon atoms.
Claim 7
Dependent Claim
19 words
A composition according to claim 5, wherein the linear primary amine is: dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, eiscosylamine or docosylamine.
Claim 8
Dependent Claim
39 words
A composition according to claim 1, wherein said compound having 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 to 18 carbon atoms.
Claim 9
Dependent Claim
102 words
A composition according to claim 1, which is obtained by the steps of: (a) effecting a radical-promoted copolymerization of appropriate proportions of said at least one linear α-olefin, said at least one unsaturated α,β-dicarboxylic compound in the form of a diacid, a lower alkyl diester or an anhydride, and said at least one alkyl ester of an unsaturated monocarboxylic acid; and (b) condensing resultant copolymer with said at least one compound having 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 10
Dependent Claim
39 words
A composition according to claim 8, wherein the proportion of said compound having a primary amine group having the formula (I) or (II) ranges from 0.9 to 1.1 mole per mole of α,β-unsaturated dicarboxylic compound in said resultant copolymer.
Claim 11
Dependent Claim
98 words
A composition according to claim 1, which is obtained by the step of effecting a radical-promoted copolymerization of appropriate proportions of said at least one linear α-olefin, said at least one imidized α,β-unsaturated dicarboxylic compound and said at least one alkyl ester of an unsaturated monocarboxylic acid, said imidized 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 said at least one compound having a primary amine group and having said formula (I) or (II).
Claim 12
Dependent Claim
51 words
A composition according to claim 1, wherein said compound having an amine group (I) is at least one polyamine having the formula: ##STR6## 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 13
Dependent Claim
43 words
A composition according to claim 11, wherein said polyamine having formula (I) is N-dodecyl 1,3-diamino propane, N-tetradecyl 1,3-diamino propane, N-hexadecyl 1,3-diamino propane, N-octadecyl 1,3-diamino propane, N-eicosyl 1,3-diamino propane, N-docosyl 1,3-diamino propane, N-hexadecyldipropylene triamine, N-octadecyl dipropylene triamine, N-eicosyl dipropylene triamine or N-docosyl dipropylene triamine.
Claim 14
Dependent Claim
62 words
A composition according to claim 1, wherein said compound having an amine group (I) is at least one polyamine having the formula: ##STR7## 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 15
Dependent Claim
38 words
A composition according to claim 13, wherein said polyamine having formula (I) is 1,3-diamino propane, N,N-dioctyl N,N-didecyl 1,3-diamino propane, N,N-didodecyl 1,3-diamino propane, N,N-ditetradecyl 1,3-diamino propane, N,N-dihexadecyl 1,3-diamino propane, N,N-dioctadecyl 1,3-diaminopropane, N,N-didodecyldipropylenetriamine, N,N-ditetradecyldipropylene triamine, N,N-dihexadecyldipropylene triamine or N,N-dioctadecyldipropylene triamine.
Claim 16
Dependent Claim
50 words
A composition according to claim 1, wherein said compound having an amine group (I) is at least one etheramine having the formula: ##STR8## 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 17
Dependent Claim
19 words
A composition according to claim 15, wherein said ether-amine is, 3-hexadecyloxy propylamine, 3-eicosyloxy propylamine, 3-docosyloxy propylamine, (2,4,6-trimethyldecyl)3-oxypropylamine or N-[(2,4,6-trimethyldecyl)-3-oxypropyl]1,3-diaminopropane.
Claim 18
Dependent Claim
41 words
A middle distillate composition, which comprises a major proportion of middle distillate having a distillation range from 150° to 450° C. and a minor proportion of at least one compound according to claim 1, sufficient to lower the cloud point thereof.
Claim 19
Dependent Claim
39 words
A middle distillate composition according to claim 17, wherein said middle distillate is a gas oil cut having a distillation range from an initial temperature of 160° to 190° C. to a final temperature of 350° to 390° C.
Claim 20
Dependent Claim
22 words
A middle distillate composition according to claim 17, wherein the proportion of said CO polymer is from 0.001 to 1% by weight.
Claim 21
Dependent Claim
22 words
A middle distillate composition according to claim 19, wherein the proportion of said CO polymer is from 0.01 to 0.2% by weight.
Claim 22
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 23
Dependent Claim
14 words
A method according to claim 21, wherein said effective amount is 0.001-1% by weight.
Claim 24
Dependent Claim
13 words
A method according to claim 22, wherein said amount is 0.01-0.2% by weight.
Claim 25
Dependent Claim
143 words
A compound, useful as an additive for decreasing the cloud point of middle distillates, having a number-average molecular weight of 1,000-10,000 and being a copolymer consisting essentially of: 15-40% by mole of recurrent units (A) from at least one linear α-olefin of at least 16 carbon atoms; 20-70% by mole of imidized recurrent units (B) from condensation, prior or subsequent to copolymerization, of at least one maleic or alkylmaleic acid, a methyl, ethyl or propyl diester thereof or a maleic or alkylmaleic anhydride with at least one compound having a single primary amine group; and 15-40% by mole of recurrent units (C) from at least one alkyl ester of ann unsaturated monocarboxylic acid, wherein said alkyl ester of an unsaturated monocarboxylic acid providing the recurrent units (C) is at least one alkyl acrylate or methalcrylate having 4-30 carbon atoms in the alkyl group.
Claim 26
Dependent Claim
143 words
A compound, useful as an additive for decreasing the cloud point of middle distillates, having a number-average molecular weight of 1,000-10,000 and being a copolymer consisting essentially of: 15-40% by mole of recurrent units (A) from at least one linear α-olefin of at least 16 carbon atoms; 20-70% by mole of imidized recurrent units (B) from condensation, prior or subsequent to copolymerization, of at least one maleic or alkylmaleic acid, a methyl, ethyl or propyl diester thereof or a maleic or alkylmaleic anhydride with at least one compound having a single primary amine group; and 15-40% by mole of recurrent units (C) from at least one alkyl ester of ann unsaturated monocarboxylic acid, wherein said alkyl ester of an unsaturated monocarboxylic acid providing the recurrent units (C) is at least one alkyl acrylate or methalcrylate having 4-30 carbon atoms in the alkyl group.
Claim 27
Dependent Claim
21 words
A compound according to claim 24, wherein said linear α-olefin providing the recurrent units (A) contains 16 to 30 carbon atoms.
Claim 28
Dependent Claim
185 words
A compound according to claim 24, wherein said at least one compound having a single primary amine group is: at least one primary amine having the formula R--NH 2 wherein R is a linear alkyl radical of 12-24 carbon atoms; at least one polyamine having the formula: ##STR9## 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; or at least one polyamine having the formula: ##STR10## 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; or at least one etheramine having the formula: ##STR11## 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; or 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 to 18 carbon atoms.
Claim 29
Dependent Claim
21 words
A compound according to claim 26, wherein said linear α-olefin providing the recurrent units (A) contains 16 to 30 carbon atoms.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-03-15 | 1991-09-14 | 1992-03-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-03-15 | 1995-09-14 | 1996-03-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-03-15 | 1999-09-14 | 2000-03-15 | $7700.00 | Window Closed / Lapsed |