US4171273A
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US
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Fatty alkyl succinate ester and succinimide modified copolymers of ethylene and an alpha olefin
Assignee: Afton Chemical Additives Corp
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Filing: 1977-03-14
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Granted: 1979-10-16
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Expires: 1997-03-14
Abstract
Abstract Fatty alkyl succinate ester and succinimide modified copolymers of ethylene and an alpha-olefin, such as an ethylene-propylene copolymer, are useful as shear stable viscosity index (VI) improvers, dispersants and pour point depressants in lubricating oils. Especially useful is the succinate ester of mixtures of primary n-alkanols containing about 12 to about 18 carbon atoms and the N-(3-dimethylaminopropyl) succinimide derivative of the copolymer of ethylene and an alpha-olefin, such as an ethylene-propylene copolymer. This succinate ester-succinimide derivative is prepared by reacting the copolymer in an aromatic solvent with maleic anhydride in the presence of a free radical initiator, then esterifying the anhydride with a fatty alcohol or mixtures thereof in the presence of an acidic catalyst and finally converting any unreacted anhydride and half esters to the succinimide by reaction with a polyamine containing a primary amine. Additive concentrates containing 5 to 30 wt. % of the copolymer derivative in a solvent facilitate the introduction of the additive into a lubricating oil blend.
Inventors
- 👤 James O. Waldbillig
- 👤 Isaac D. Rubin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 19:10
CPC Classifications
C; C10; C10M; C10M149/00; C10M149/02; C10M149/06; C08; C08F; C08F8/00; C08F8/14; C08F8/30; C08F8/32; C10M2215/00; C10M2215/086; C10M2215/12; C10M2215/22; C10M2215/221; C10M2215/223; C10M2215/224; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/04; C10N; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 67
Claim 1
Independent Claim
253 words
A method of preparing a fatty alkyl succinate ester and succinimide modified copolymer of ethylene and an alpha olefin comprising: (a) reacting said ethylene-alpha-olefin copolymer with maleic anhydride in the presence of a free radical initiator and a solvent for the reaction mixture to produce a resulting succinic anhydride derivative of said ethylene-alpha-olefin copolymer, (b) adding an inert liquid diluent to the resulting reaction mixture containing said succinic anhydride derivative, (c) removing remaining maleic anhydride and solvent from the resulting reaction mixture, (d) reacting the succinic anhydride derivative with a n--C 4 to n--C 22 alcohol or mixtures thereof in the presence of an acidic catalyst to produce the corresponding succinate ester, (e) reacting unesterified carboxylic acid or anhydride groups of said copolymer derivative with a polyamine having the formula: ##STR3## wherein R 1 and R 2 are the same or different and are alkyl radicals having 1 to 4 carbon atoms; R 3 is a methylene radical having 1 to 4 carbon atoms; R 4 and R 5 are the same or different and are methylene or methine radicals having 1 to 4 carbon atoms; X 1 is O, S, NH, N--R 1 , or CH 2 (if R 4 and R 5 are methylene radicals) or N or CH (if R 4 and R 5 are methine radicals); X 2 is N or NH and Y is NH 2 or R 3 --NH 2 to produce the corresponding fatty alkyl succinate ester and succinimide modified copolymers of ethylene and alpha olefin.
Claim 2
Independent Claim
253 words
A method of preparing a fatty alkyl succinate ester and succinimide modified copolymer of ethylene and an alpha olefin comprising: (a) reacting said ethylene-alpha-olefin copolymer with maleic anhydride in the presence of a free radical initiator and a solvent for the reaction mixture to produce a resulting succinic anhydride derivative of said ethylene-alpha-olefin copolymer, (b) adding an inert liquid diluent to the resulting reaction mixture containing said succinic anhydride derivative, (c) removing remaining maleic anhydride and solvent from the resulting reaction mixture, (d) reacting the succinic anhydride derivative with a n--C 4 to n--C 22 alcohol or mixtures thereof in the presence of an acidic catalyst to produce the corresponding succinate ester, (e) reacting unesterified carboxylic acid or anhydride groups of said copolymer derivative with a polyamine having the formula: ##STR3## wherein R 1 and R 2 are the same or different and are alkyl radicals having 1 to 4 carbon atoms; R 3 is a methylene radical having 1 to 4 carbon atoms; R 4 and R 5 are the same or different and are methylene or methine radicals having 1 to 4 carbon atoms; X 1 is O, S, NH, N--R 1 , or CH 2 (if R 4 and R 5 are methylene radicals) or N or CH (if R 4 and R 5 are methine radicals); X 2 is N or NH and Y is NH 2 or R 3 --NH 2 to produce the corresponding fatty alkyl succinate ester and succinimide modified copolymers of ethylene and alpha olefin.
Claim 3
Dependent Claim
20 words
A method according to claim 1 wherein the solvent of step (a) is an aromatic solvent containing no benzylic hydrogen.
Claim 4
Dependent Claim
14 words
A method according to claim 1 wherein the aromatic solvent is benzene or chlorobenzene.
Claim 5
Dependent Claim
12 words
A method according to claim 1 wherein the alpha olefin is propylene.
Claim 6
Dependent Claim
47 words
A method according to claim 1 wherein the ethylene-alpha-olefin is an ethylene-propylene copolymer having an amorphous structure, a number average molecular weight between about 10,000 and 100,000, a propylene content of 20 to 70 mole percent and a M w /M n of less than about 5.
Claim 7
Dependent Claim
26 words
A method according to claim 1 wherein the reactions of steps (a), (d) and (e) are carried out at temperatures in the range of 80°-200° C.
Claim 8
Dependent Claim
21 words
A method according to claim 1 wherein the free radical initiator of step (a) is dibenzoyl peroxide, dicumyl peroxide or azobisisobutyronitrile.
Claim 9
Dependent Claim
17 words
A method according to claim 1 wherein the acidic catalyst of step (d) in p-toluene sulfonic acid.
Claim 10
Dependent Claim
22 words
A method according to claim 1 wherein the inert liquid diluent of step (b) is a high boiling point petroleum based oil.
Claim 11
Dependent Claim
26 words
A method according to claim 1 wherein the fatty alcohol of step (d) is a primary alcohol having 4 to 22 carbon atoms and mixtures thereof.
Claim 12
Dependent Claim
23 words
A method according to claim 10 wherein the fatty alcohol is a mixture of primary alcohols having about 12 to 18 carbon atoms.
Claim 13
Dependent Claim
14 words
A method according to claim 1 wherein the polyamine of step (e) is 3-(dimethylamino)-1-propylamine.
Claim 14
Dependent Claim
31 words
A method according to claim 1 wherein the fatty alkyl succinate ester-succinimide modified copolymer of ethylene and alpha olefin has a nitrogen content of about 0.01 to 1.0 weight percent nitrogen.
Claim 15
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 1.
Claim 16
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 2.
Claim 17
Dependent Claim
20 words
A succinate ester-sucinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 3.
Claim 18
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 4
Claim 19
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 5.
Claim 20
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 6.
Claim 21
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 7.
Claim 22
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 8.
Claim 23
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 9.
Claim 24
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 10.
Claim 25
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 11.
Claim 26
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 12.
Claim 27
Dependent Claim
20 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared by the method of claim 13.
Claim 28
Dependent Claim
13 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olephin.
Claim 29
Dependent Claim
13 words
A succinate ester-succinimide derivative of a copolymer of ethylene and an alpha olephin.
Claim 30
Dependent Claim
13 words
A copolymer derivative according to claim 27 wherein the alpha olefin is propylene.
Claim 31
Dependent Claim
18 words
A copolymer derivative according to claim 27 wherein the ester is a n--C 4 to n--C 22 ester.
Claim 32
Dependent Claim
18 words
A copolymer derivative according to claim 27 wherein the ester is a n--C 12 to n--C 18 ester.
Claim 33
Dependent Claim
123 words
A copolymer derivative according to claim 27 wherein the succinimide portion comprises a polyamine having the formula: ##STR4## wherein R 1 and R 2 are the same or different and are alkyl radicals having 1 to 4 carbon atoms; R 3 is a methylene radical having 1 to 4 carbon atoms; R 4 and R 5 are the same or different and are methylene or methine radicals having 1 to 4 carbon atoms; X 1 is O, S, NH, N--R 1 or CH 2 (if R 4 and R 5 are methylene radicals) or N or CH (if R 4 and R 5 are methine radicals); X 2 is N or NH and Y is NH 2 or R 3 --NH 2 .
Claim 34
Dependent Claim
16 words
A copolymer derivative according to claim 27 wherein nitrogen content is 0.01 to 1.0 weight percent.
Claim 35
Dependent Claim
24 words
A copolymer derivative according to claim 27 wherein the derivative is the n--C 4 to n--C 22 succinate ester-dimethylaminopropyl succinimide derivative of ethylenepropylene copolymer.
Claim 36
Dependent Claim
54 words
A lubricating oil composition comprising a major portion of a lubricating oil and a minor portion, sufficient to increase the viscosity index, depress the pour point and increase the dispersancy of said lubricating oil, of a fatty alkyl succinate ester-succinimide derivative of a copolymer of ethylene- and an alpha-olefin prepared according to claim 1.
Claim 37
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 16.
Claim 38
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 17.
Claim 39
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 18.
Claim 40
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 20.
Claim 41
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 21.
Claim 42
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 22.
Claim 43
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 23.
Claim 44
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 25.
Claim 45
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 26.
Claim 46
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 27.
Claim 47
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 28.
Claim 48
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 29.
Claim 49
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 31.
Claim 50
Dependent Claim
19 words
A lubricating oil composition according to claim 34 wherein the copolymer derivative is the copolymer derivative of claim 33.
Claim 51
Dependent Claim
18 words
A lubricating oil composition according to claim 34 wherein the minor amount is 0.10 to 5.0 weight percent.
Claim 52
Dependent Claim
40 words
A lubricating oil additive concentrate comprising a hydrocarbon solvent and about 5 to about 30 weight percent, based on solvent, of a fatty alkyl succinate-succinimide derivative of a copolymer of ethylene and an alpha olefin prepared according to claim 1.
Claim 53
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 16.
Claim 54
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 17.
Claim 55
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 18.
Claim 56
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 20.
Claim 57
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 21.
Claim 58
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 22.
Claim 59
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 23
Claim 60
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 25.
Claim 61
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 26.
Claim 62
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 27.
Claim 63
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 28.
Claim 64
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 29.
Claim 65
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 31.
Claim 66
Dependent Claim
20 words
A lubricating oil additive concentrate according to claim 50 wherein the copolymer derivative is the copolymer derivative of claim 33.
Claim 67
Dependent Claim
31 words
A lubricating oil additive concentrate according to claim 50 wherein the hydrocarbon solvent is a light lubricating oil having a viscosity of between about 75 and 300 SUS at 100° F.
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) | 1982-10-15 | 1983-04-16 | 1983-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-10-15 | 1987-04-16 | 1987-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-10-15 | 1991-04-16 | 1991-10-16 | $7700.00 | Window Closed / Lapsed |