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US4229308A
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Polymer lubricating oil additives bearing nitrogen groups and their use as additives for lubricating oils
Assignee: Rhone Poulenc Industries SA
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Filing: 1979-01-26
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Granted: 1980-10-21
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Expires: 1999-01-26
Abstract
Abstract Novel lubricating oil polymer additives are obtained by the following: (1) by preparing, by anionic polymerization, a living diene polymer of an Mn of between about 20,000 and 300,000; (2) by functionalizing the said polymer by means of a non-polymerizable nitrogen compound having at least two <C-N=C> groups, such as the polypyridines, pyrimidine and its derivatives, pyrazine and its derivatives, 2,4,6-tri-(2-pyridyl)-1,3,5-triazine, dipyridyl sulfide, etc.; and (3) by hydrogenating the said functionalized polymer. A variant method of preparaing the said polymers comprises metalating the living polymer before functionalization; in accordance with this variant, the hydrogenation operation may take place before metalation or after functionalization. The said polymers can be used as additives which improve the viscosity index and the dispersing power of the lubricating oils. The amount of additive added is between about 0.1 and 10 percent by weight.
Inventors
- 👤 Daniel Brulet
- 👤 Bernard Chauvel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 17:21
CPC Classifications
C; C10; C10M; C10M143/00; C10M143/12; C08; C08C; C08C19/00; C08C19/30; C08C19/42; C08C19/44; C08F; C08F8/00; C10M2203/00; C10M2203/06; C10M2205/00; C10M2205/02; C10M2209/00; C10M2209/10; C10M2209/103; C10M2209/108; C10M2215/00; C10M2215/22; C10M2215/221; C10M2215/222; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/028; C10M2217/04; C10M2217/06; C10M2219/00; C10M2219/09; C10M2221/00; C10M2221/04; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
91 words
A lubricating oil polymer additive produced by subjecting a living polymer of a number average molecular weight Mn of between about 20,000 and 300,000, prepared by anionic polymerization of at least one C 4 -C 6 conjugated diene or a copolymer of a C 4 -C 6 conjugated diene with a vinyl aromatic compound to a functionalization operation by reaction with a nonpolymerizable heterocyclic nitrogen compound having at least two groups of the structure <C--N+C>; and to a hydrogenation to hydrogenate at least about 85 percent of the olefin double bonds.
Claim 2
Dependent Claim
91 words
A lubricating oil polymer additive produced by subjecting a living polymer of a number average molecular weight Mn of between about 20,000 and 300,000, prepared by anionic polymerization of at least one C 4 -C 6 conjugated diene or a copolymer of a C 4 -C 6 conjugated diene with a vinyl aromatic compound to a functionalization operation by reaction with a nonpolymerizable heterocyclic nitrogen compound having at least two groups of the structure <C--N+C>; and to a hydrogenation to hydrogenate at least about 85 percent of the olefin double bonds.
Claim 3
Dependent Claim
34 words
A lubricating oil polymer additive according to claim 1, wherein the anionic polymerization includes at least one C 4 -C 6 conjugated diene and at least one compound selected from among vinyl aromatic compounds.
Claim 4
Dependent Claim
23 words
A lubricating oil polymer additive according to claim 1, wherein the functionalization operation is preceded by a metalation of the said living polymer.
Claim 5
Dependent Claim
20 words
A lubricating oil polymer additive according to claim 3, wherein the hydrogenation operation is carried out before the metalation operation.
Claim 6
Dependent Claim
31 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the said living polymer has a number average molecular weight Mn of between about 30,000 and 150,000.
Claim 7
Dependent Claim
37 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the living polymer is a random or block polymer or copolymer of at least one diene, selected from among butadiene, isoprene, and dimethylbutadiene.
Claim 8
Dependent Claim
47 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the living polymer is a random or block copolymer of at least one diene selected from among butadiene, isoprene, and dimethylbutadiene, and of a vinyl aromatic compound selected from among styrene and α-methylstyrene.
Claim 9
Dependent Claim
50 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the living polymer is a "star" copolymer obtained from at least one diene selected from among butadiene, isoprene, and dimethylbutadiene, optimally mixed with a vinyl aromatic compound selected from among styrene and α-methylstyrene, and from divinylbenzene.
Claim 10
Dependent Claim
41 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the said living polymer is obtained by anionic polymerization in the presence of organometallic catalysts at a temperature of between about minus 80° and plus 150° C.
Claim 11
Dependent Claim
38 words
A lubricating oil polymer additive according to claim 9, wherein the said living polymer is obtained in the presence of a member selected from n-butyllithium or of 1,4-dilithio-1,1,4,4-tetraphenylbutane, at a temperature of between about 0° and 100° C.
Claim 12
Dependent Claim
46 words
A lubricating oil polymer additive according to claim 3 or claim 4, wherein the metalation operation is carried out at a temperature between about minus 80° and plus 150° C., in the presence of a complex consisting of diamine and organic compound of an alkali metal.
Claim 13
Dependent Claim
52 words
A lubricating oil polymer additive according to claim 11, wherein the metalation operation is carried out at a temperature of between about 0° and 80° C., in the presence of a complex formed of N,N,N',N'-tetramethyleneethylenediamine and a butyllithium, with a molar ratio of diamine to butyllithium of between about 0.5 and 1.2.
Claim 14
Dependent Claim
28 words
A lubricating oil polymer additive according to claim 12, wherein the butyllithium is sec-butyllithium and the molar ratio of diamine to sec-butyllithium is between about 0.7 and 1.
Claim 15
Dependent Claim
39 words
A lubricating oil polymer additive according to claim 12, wherein the amount of complex employed is such that the ratio of the number of mols of organometallic compound in said complex per mol of polymer is less than 50.
Claim 16
Dependent Claim
33 words
A lubricating oil polymer additive according to claim 14, wherein the ratio of the number of mols of organometallic compound in said complex per mol of polymer is between about 2 and 10.
Claim 17
Dependent Claim
46 words
A lubricating oil polymer additive according to claim 3 or claim 4, wherein the metalation step is followed by a grafting operation by addition of a monomer selected from among the C 4 -C 6 conjugated dienes, styrene, or their mixture, prior to the functionalization step.
Claim 18
Dependent Claim
28 words
A lubricating oil polymer additive according to claim 16, wherein the grafting operation is carried out at a temperature of between about minus 80° and plus 150° C.
Claim 19
Dependent Claim
26 words
A lubricating oil polymer additive according to claim 17, wherein the grafting operation is carried out at a temperature of between about 0° and 100° C.
Claim 20
Dependent Claim
44 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the nonpolymerizable nitrogen compound is a heterocyclic compound selected from among polypyridines having less than 20 pyridyl groups, pyrimidine and its derivatives, pyrazine and its derivatives, 2,4,6-tri(2-pyridyl)-1,3,5-triazine, and dipyridyl sulfide.
Claim 21
Dependent Claim
19 words
A lubricating oil polymer additive according to claim 19, wherein the polypyridines are selected from among 2,2'-dipyridine and tripyridine.
Claim 22
Dependent Claim
21 words
A lubricating oil polymer additive according to claim 19, wherein the derivatives of pyrimidine are selected from among quinazoline and naphtridine.
Claim 23
Dependent Claim
21 words
A lubricating oil polymer additive according to claim 19, wherein the derivatives of pyrazine are selected from among quinoxaline and pyridopyrazine.
Claim 24
Dependent Claim
41 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the amount of nonpolymerizable nitrogen compound is such that the ratio of mols of nitrogen compound to the number of functionalizable carbanion sites is at least 1.
Claim 25
Dependent Claim
38 words
A lubricating oil polymer additive according to claim 1, wherein the amount of nonpolymerizable nitrogen compound is such that the ratio of mols of nitrogen compound to number of functionalizable carbanion sites is equal to 1 or 2.
Claim 26
Dependent Claim
40 words
A lubricating oil polymer additive according to claim 3 or claim 4, wherein the amount of nonpolymerizable nitrogen compound is such that the ratio of mols of nitrogen compounds to number of functionalizable carbanion sites is between 1 and 2.
Claim 27
Dependent Claim
30 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the functionalization step is carried out at a temperature of between about 10° and 80° C.
Claim 28
Dependent Claim
26 words
A lubricating oil polymer additive according to claim 26, wherein the functionalization step is carried out at a temperature of between about 30° and 60° C.
Claim 29
Dependent Claim
38 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the hydrogenation step is conducted in the presence of a catalytic system obtained by reaction between a transition metal derivative and an organoreduction compound.
Claim 30
Dependent Claim
21 words
A lubricating oil polymer additive according to claim 28, wherein the catalytic system has a base of cobalt octoate and triethylaluminum.
Claim 31
Dependent Claim
27 words
A lubricating oil improved by the addition of 0.1 to 10 percent of its weight of a polymer additive according to any of claims 1 to 4.
Claim 32
Dependent Claim
32 words
A lubricating oil according to claim 30, improved by addition of 1 to 5 percent of its weight of one of the polymer additives according to any of claims 1 to 4.
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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) | 1983-10-21 | 1984-04-21 | 1984-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-21 | 1988-04-21 | 1988-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-21 | 1992-04-21 | 1992-10-21 | $7700.00 | Window Closed / Lapsed |