US4222882A
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Polymers bearing groups derived from N-substituted lactams and their use as lubricating oil additives
Assignee: Rhone Poulenc Industries SA
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Filing: 1979-01-26
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Granted: 1980-09-16
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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 Mn of between about 20,000 and 300,000; (2) by functionalizing the said polymer by means of an N-substituted lactam of the type of N-alkylcaprolactam, N-binylcaprolactam, and particularly of the type of N-alkylpyrrolidione and N-vinylpyrrolidone; and (3) by hydrogenating the said functionalized polymer. A variant method of preparing the said polymers comprises subjecting the living polymer to a metalation operation before functionalization; the hydrogenation operation is carried out before metalation or after functionalization. The said polymers may be used as additives which improve the viscosity index and the dispersing power of lubricating oils. The amount of additive added is between about 0.1 and 10 percent by weight.
Inventors
- 👤 Daniel Brulet
- 👤 Robert Pocheville
- 👤 Bernard Chauvel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 09:58
CPC Classifications
C; C08; C08C; C08C19/00; C08C19/30; C08C19/42; C08C19/44; C08C19/02; C10; C10M; C10M133/00; C10M133/02; C10M133/38; C10M143/00; C10M143/10; C10M143/12; C10M2215/00; C10M2215/08; C10M2215/082; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/028; C10M2217/06
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
117 words
A lubricating oil polymer additive produced in accordance with the process which comprises: subjecting a living polymer of number average molecular weight (Mn) of between about 20,000 and 300,000, said living polymer being 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 an N-substituted lactam of the formula: ##STR12## in which Z represents a member selected from a C 1 -C 20 alkyl radical, a C 2 -C 10 alkenyl radical, a phenyl radical, and n represents a whole number from about 2 to 11; and to a hydrogenation.
Claim 2
Dependent Claim
117 words
A lubricating oil polymer additive produced in accordance with the process which comprises: subjecting a living polymer of number average molecular weight (Mn) of between about 20,000 and 300,000, said living polymer being 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 an N-substituted lactam of the formula: ##STR12## in which Z represents a member selected from a C 1 -C 20 alkyl radical, a C 2 -C 10 alkenyl radical, a phenyl radical, and n represents a whole number from about 2 to 11; and to a hydrogenation.
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
24 words
A lubricating oil polymer additive according to claim 1, wherein the phenyl radical is also substituted by a C 1 -C 10 alkyl group.
Claim 5
Dependent Claim
25 words
A lubricating oil polymer additive according to claim 1, wherein the functionalization operation is preceded by an operation of metalation of the said living polymer.
Claim 6
Dependent Claim
20 words
A lubricating oil polymer additive according to claim 4, wherein the hydrogenation operation is carried out before the metalation operation.
Claim 7
Dependent Claim
30 words
A lubricating oil polymer additive according to any of claims 1 to 3, wherein the said living polymer has a number average molecular weight Mn of between 30,000 and 150,000.
Claim 8
Dependent Claim
38 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the living polymer employed is a random or block polymer or copolymer of at least one diene selected from among butadiene, isoprene, and dimethylbutadiene.
Claim 9
Dependent Claim
48 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the living polymer employed 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 10
Dependent Claim
50 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the living polymer employed 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 among styrene and α-methylstyrene, and from divinylbenzene.
Claim 11
Dependent Claim
42 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the said living polymers employed are obtained by anionic polymerization in the presence of organometallic catalysts at a temperature of between about minus 80° and plus 150° C.
Claim 12
Dependent Claim
38 words
A lubricating oil polymer additive according to claim 1, wherein the said living polymer employed is obtained in the presence of a member selected from n-butyllithium and 1,4-dilithio-1,1,4,4-tetraphenylbutane, at a temperature of between about 0° and 100° C.
Claim 13
Dependent Claim
46 words
A lubricating oil polymer additive according to claim 4, wherein the metalation operation is carried out at a temperature of between about minus 80° and plus 150° C., in the presence of a complex consisting of a diamine and an organic compound of an alkali metal.
Claim 14
Dependent Claim
54 words
A lubricating oil polymer additive according to claim 12, 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'-tetramethylene ethylene diamine and a butyllithium, with a molar ratio of diamine to butyllithium of between about 0.5 and 1.2.
Claim 15
Dependent Claim
28 words
A lubricating oil polymer additive according to claim 13, wherein the butyllithium is s-butyllithium and the molar ratio of diamine to s-butyllithium is between about 0.7 and 1.
Claim 16
Dependent Claim
40 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 about 50.
Claim 17
Dependent Claim
33 words
A lubricating oil polymer additive according to claim 15, 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 18
Dependent Claim
44 words
A lubricating oil polymer additive according to claims 4 or 5, wherein the metalation step is followed by a grafting operation by addition of a monomer selected from among C 4 -C 6 conjugated dienes, styrene or their mixture, prior to the functionalization step.
Claim 19
Dependent Claim
27 words
A lubricating oil polymer additive according to claim 17, wherein the grafting operation is effected at a temperature of between about minus 80 and plus 150° C.
Claim 20
Dependent Claim
26 words
A lubricating oil polymer additive according to claim 18, wherein the grafting operation is carried out at a temperature of between about 0° and 100° C.
Claim 21
Dependent Claim
67 words
A lubricating oil polymer additive according to any of claims 1 to 5, wherein in the formula I of the N-substituted lactams, Z represents a member selected from a C 1 -C 10 alkyl radical, a C 2 -C 4 alkenyl radical, and a phenyl radical substituted by a C 1 -C 5 alkyl group, and n represents a whole number of from about 3 to 5.
Claim 22
Dependent Claim
19 words
A lubricating oil polymer additive according to claim 20, wherein in the formula I, n is equal to 3.
Claim 23
Dependent Claim
24 words
A lubricating oil polymer additive according to claim 21, wherein the lactam of the formula I is selected from among N-methylpyrrolidone, N-ethylpyrrolidone, and N-vinylpyrrolidone.
Claim 24
Dependent Claim
24 words
A lubricating oil polymer additive according to claim 20, wherein the lactam of the formula I is selected from among N-methylcaprolactam, N-ethylcaprolactam, and N-vinylcaprolactam.
Claim 25
Dependent Claim
39 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the amount of N-substituted lactam employed is such that the molar ratio of N-substituted lactam to number of functionalizable carbanion sites is at least 1.
Claim 26
Dependent Claim
37 words
A lubricating oil polymer additive according to claim 1, wherein the amount of N-substituted lactam employed is such that the molar ratio of N-substituted lactam per number of functionalizable carbanion sites is from about 1 to 3.
Claim 27
Dependent Claim
39 words
A lubricating oil polymer additive according to claims 4 or 5, wherein the amount of N-substituted lactam used is such that the molar ratio of N-substituted lactam to number of functionalizable carbanion mols is from about 1 to 2.
Claim 28
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 29
Dependent Claim
26 words
A lubricating oil polymer additive according to claim 27, wherein the functionalization step is carried out at a temperature of between about 30° and 60° C.
Claim 30
Dependent Claim
39 words
A lubricating oil polymer additive according to any of claims 1 to 4, wherein the hydrogenation step is carried out in the presence of a catalytic system obtained by reaction between a transition metal derivative and an organoreduction compound.
Claim 31
Dependent Claim
21 words
A lubricating oil polymer additive according to claim 29, wherein the catalytic system has a base of cobalt octoate and triethylaluminum.
Claim 32
Dependent Claim
28 words
A lubricating oil improved by the addition of about 0.1 to 10 percent of its weight of a polymer additive according to any of claims 1 to 4.
Claim 33
Dependent Claim
34 words
A lubricating oil according to claim 31, improved by the addition of about 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) | 1983-09-16 | 1984-03-17 | 1984-09-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-16 | 1988-03-17 | 1988-09-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-16 | 1992-03-17 | 1992-09-16 | $7700.00 | Window Closed / Lapsed |