Patent US4153566A successfully refreshed from Google Patents.
US4153566A
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Oxazoline additives useful in oleaginous compositions
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1976-07-30
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Granted: 1979-05-08
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Expires: 1996-07-30
Abstract
Abstract Oxazoline reaction products of hydrocarbon substituted dicarboxylic acid, ester, or anhydride, for example octadecenylsuccinic anhydride, with 2,2-disubstituted-2-amino-1-alkanols, such as tris-hydroxymethylaminomethane (THAM), and their derivatives are useful additives in oleaginous compositions, such as sludge dispersants for lubricating oil, or anti-rust agents for gasoline.
Inventors
- 👤 Jack Ryer
- 👤 Harold N. Miller
- 👤 James Zielinski
- 👤 Stanley J. Brois
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 20:37
CPC Classifications
C; C10; C10M; C10M1/00; C10M1/08; C07; C07D; C07D263/00; C07D263/02; C07D263/08; C07D263/10; C07D263/12; C07D263/14; C07F; C07F5/00; C07F5/02; C07F5/04; C07F9/00; C07F9/02; C07F9/547; C07F9/6527; C07F9/653; C08; C08F; C08F8/00; C08F8/30; C08F8/32; C08G; C08G63/00; C08G63/68; C08G63/685; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/221; C10L1/232; C10L1/233; C10L1/234; C10L1/238; C10L1/26; C10L1/2691; C10L1/30; C10L1/301; C10L1/303; C10M2205/00; C10M2205/02; C10M2205/022; C10M2205/026; C10M2205/14; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/027; C10M2207/028; C10M2207/10; C10M2207/12; C10M2207/121; C10M2207/122; C10M2207/28; C10M2207/282; C10M2207/32; C10M2207/34; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2209/086; C10M2209/10; C10M2209/103; C10M2209/109; C10M2209/11; C10M2209/112; C10M2211/00; C10M2211/02; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/086; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042; C10M2223/045; C10M2223/06; C10M2223/061; C10M2223/065; C10M2223/08; C10M2223/12; C10M2225/00; C10M2225/04; C10M2225/041; C10M2227/00; C10M2227/06; C10M2227/061; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05; C10N; C10N2010/00; C10N2010/04; C10N2040/00; C10N2040/02; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/08; C10N2040/25; C10N2040/252; C10N2040/253; C10N2050/00; C10N2050/10; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
178 words
A lubricating oil composition comprising: a major amount of lubricating oil and 0.1 to 10 wt. % of bis-oxazoline of a molar proportion of a hydrocarbon-substituted C 4 -C 10 mono unsaturated dicarboxylic acid material selected from the group consisting of dicarboxylic acid, ester and anhydrides thereof, having from about 8 to 49 carbon atoms in said hyrocarbon substituent; reacted with about two molar proportions of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula: ##STR4## wherein X is alkyl or hydroxy alkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH 2 ) n OH where n is 1 to 3; at a temperature in the range of about 140 to 240° C. for about 1/2 to 24 hours with the removal of about three molar proportions of water to thereby produce said bis-oxazoline having the structure ##STR5## wherein R is said hydrocarbon substituent and X is as defined above.
Claim 2
Dependent Claim
178 words
A lubricating oil composition comprising: a major amount of lubricating oil and 0.1 to 10 wt. % of bis-oxazoline of a molar proportion of a hydrocarbon-substituted C 4 -C 10 mono unsaturated dicarboxylic acid material selected from the group consisting of dicarboxylic acid, ester and anhydrides thereof, having from about 8 to 49 carbon atoms in said hyrocarbon substituent; reacted with about two molar proportions of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula: ##STR4## wherein X is alkyl or hydroxy alkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH 2 ) n OH where n is 1 to 3; at a temperature in the range of about 140 to 240° C. for about 1/2 to 24 hours with the removal of about three molar proportions of water to thereby produce said bis-oxazoline having the structure ##STR5## wherein R is said hydrocarbon substituent and X is as defined above.
Claim 3
Dependent Claim
16 words
A composition according to claim 1, wherein said hydrocarbon-substituted dicarboxylic acid material is alkenyl succinic anhydride.
Claim 4
Dependent Claim
11 words
A composition according to claim 2, wherein said amino-1-alkanol is 2-amino-2-methyl-1propanol.
Claim 5
Dependent Claim
11 words
A composition according to claim 2, wherein said amino-1-alkanol is tris-hydroxy-methylaminomethane.
Claim 6
Dependent Claim
15 words
A composition according to claim 1, wherein said time is about 2 to 8 hours.
Claim 7
Dependent Claim
188 words
An additive concentrate comprising: a major amount of mineral lubricating oil in the range of 98 to 45 parts by weight, 2 to 45 parts by weight of bisoxazoline of a molar proportion of a hydrocarbon-substituted C 4 -C 10 mono unsaturated dicarboxylic acid material selected from the group consisting of dicarboxylic acid, ester and anhyrides thereof; having from about 8 to 49 carbon atoms in said hydrocarbon substituent; reacted with about two molar proportions of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula: ##STR6## wherein X is alkyl or hydroxy alkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH 2 ) n OH where n is 1 to 3; at a temperature in the range of about 140° to 240° C. for about 1/2 to 24 hours with the removal of about three molar proportions of water to thereby produce said bis-oxazoline having the structure ##STR7## wherein R is said hydrocarbon substituent and X is as defined above.
Claim 8
Dependent Claim
188 words
An additive concentrate comprising: a major amount of mineral lubricating oil in the range of 98 to 45 parts by weight, 2 to 45 parts by weight of bisoxazoline of a molar proportion of a hydrocarbon-substituted C 4 -C 10 mono unsaturated dicarboxylic acid material selected from the group consisting of dicarboxylic acid, ester and anhyrides thereof; having from about 8 to 49 carbon atoms in said hydrocarbon substituent; reacted with about two molar proportions of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula: ##STR6## wherein X is alkyl or hydroxy alkyl, said alkyl groups having 1 to 3 carbon atoms, and at least one of said X is a hydroxy alkyl group of the structure --(CH 2 ) n OH where n is 1 to 3; at a temperature in the range of about 140° to 240° C. for about 1/2 to 24 hours with the removal of about three molar proportions of water to thereby produce said bis-oxazoline having the structure ##STR7## wherein R is said hydrocarbon substituent and X is as defined above.
Claim 9
Dependent Claim
16 words
A concentrate according to claim 6, wherein said hydrocarbon substituted dicarboxylic acid is alkenyl succinic anhyride.
Claim 10
Dependent Claim
12 words
A concentrate according to claim 7, wherein said amino alcohol is 2-amino-2-methyl-1-propanol.
Claim 11
Dependent Claim
12 words
A composition according to claim 7, wherein said amino alcohol is tris-hydroxy-methylaminomethane.
Claim 12
Dependent Claim
24 words
A composition according to claim 6, wherein said temperature is about 170° to 220° C. and said time is about 2 to 8 hours.
References Cited (Backward Citations)
US2569428A
Cited
US2831858A
Cited
US2905644A
Cited
US3219666A
Cited
US3235557A
Cited
DE1444904A1
Cited
US3248397A
Cited
US4049564A
Cited
US4035309A
Cited
US3966620A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-07 | 1982-11-06 | 1983-05-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-07 | 1986-11-06 | 1987-05-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-07 | 1990-11-06 | 1991-05-08 | $7700.00 | Window Closed / Lapsed |