US4069023A
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US
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Carboxylate esters of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for oleaginous compositions
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1976-12-20
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Granted: 1978-01-17
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Expires: 1996-12-20
Abstract
Abstract Ester derivatives of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl alcohols which are the reaction products of organic acid materials, preferably long chain dicarboxylic anhydrides such as octadecenyl and polyisobutenylsuccinic anhydrides and aldehyde/tris [hydroxy-methyl] aminomethane (THAM) adducts or mixtures are oleaginous compositions which feature activity in gasoline as rust inhibitors and carburetor detergents; in automatic transmission fluids as friction modifiers and rust inhibitors; and, in automotive, industrial and lubricating oils as sludge dispersants, rust-inhibitors, friction modifiers and copper alloy corrosion inhibitors, the particular use depending on the molecular weight of the ester.
Inventors
- 👤 Stanley J. Brois
- 👤 Jack Ryer
- 👤 Esther Winans
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 07:47
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/22; C07D498/00; C07D498/02; C07D498/04; C08; C08F; C08F8/00; C08F8/30; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/221; C10L10/00; C10L10/04; C10L10/08; C10M; C10M2205/00; C10M2205/02; C10M2205/022; C10M2205/026; C10M2205/14; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/28; C10M2207/282; C10M2207/32; C10M2207/34; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2209/086; C10M2209/10; C10M2209/103; C10M2209/11; C10M2209/112; C10M2211/00; C10M2211/02; C10M2215/00; C10M2215/02; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/30; C10M2219/00; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/042; C10M2223/045; C10M2223/12; C10M2225/00; C10M2225/04; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05; C10N; C10N2010/00; C10N2010/04; C10N2040/00; C10N2040/08; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
111 words
A petroleum fuel oil composition comprising a major amount of fuel oil and in the range of about 0.001 to 0.5 wt. % of an oil dispersible or soluble ester which is the ester reaction product of: (a) about 1 molar proportion of a mono or a dicarboxylic acid or anhydride, having an aliphatic hydrocarbyl chain of about 6 to about 300 carbon atoms esterified with the reaction product of (b) either about 1 or 2 molar proportions of an aldehyde, or one molar proportion of ketone and one molar proportion of aldehyde, reacted with about 1 molar proportion of tris(hydroxymethyl) aminomethane; said ester reaction product having a 1-aza-3,7-dioxabicyclo[3.3.0] octyl ring.
Claim 2
Dependent Claim
111 words
A petroleum fuel oil composition comprising a major amount of fuel oil and in the range of about 0.001 to 0.5 wt. % of an oil dispersible or soluble ester which is the ester reaction product of: (a) about 1 molar proportion of a mono or a dicarboxylic acid or anhydride, having an aliphatic hydrocarbyl chain of about 6 to about 300 carbon atoms esterified with the reaction product of (b) either about 1 or 2 molar proportions of an aldehyde, or one molar proportion of ketone and one molar proportion of aldehyde, reacted with about 1 molar proportion of tris(hydroxymethyl) aminomethane; said ester reaction product having a 1-aza-3,7-dioxabicyclo[3.3.0] octyl ring.
Claim 3
Dependent Claim
21 words
A composition according to claim 1, wherein said fuel is gasoline and said acid or anhydride material is alkenyl succinic anhydride.
Claim 4
Dependent Claim
21 words
A composition according to claim 2, wherein said alkenyl group is a polymer of a C 2 to C 5 monoolefin.
Claim 5
Dependent Claim
27 words
A composition according to claim 1, wherein said acid is a monocarboxylic acid selected from the group consisting of palmitic, stearic, phenylstearic, isostearic, oleic and linoleic acid.
Claim 6
Dependent Claim
17 words
A composition according to claim 1, wherein said hydrocarbyl chain contains about 12 to 24 carbon atoms.
Claim 7
Dependent Claim
15 words
A composition according to claim 5, wherein said acid or anhydride is octadecenyl succinic anhydride.
Claim 8
Dependent Claim
15 words
A composition according to claim 5, wherein said acid or anhydride is tetrapropenyl succinic anhydride.
Claim 9
Dependent Claim
52 words
A composition according to claim 1, wherein said acid or anhydride is a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid or anhydride, and wherein said aldehyde is selected from the group consisting of formaldehyde, glyoxal, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, 2-ethylhexanol, dodecyl aldehyde, benzaldeyde, tolualdehyde, anisaldehyde, piperonal, naphthaldehyde, phenylacetaldehyde and furfural.
Claim 10
Dependent Claim
11 words
A composition according to claim 8, wherein said aldehyde is formaldehyde.
Claim 11
Dependent Claim
11 words
A composition according to claim 8, wherein said aldehyde is glyoxal.
Claim 12
Dependent Claim
53 words
A composition according to claim 8, wherein said tris-(hydroxymethyl) aminomethane is reacted with one molar proportion of said ketone and then with one molar proportion of said aldeyde, and wherein said ketone is selected from the group consisting of acetone, butanone, pentanone, methyl isobutyl ketone, pinacolone, amyl methyl ketone, cyclopentanone, cyclohexanone and acetophenone.
Claim 13
Dependent Claim
42 words
A composition according to claim 1, wherein said fuel oil is gasoline and said ester is the half ester reaction product of octadecenyl succinic anhydride and the reaction product of two molar proportions of formaldehyde with one molar proportion of tris-(hydroxymethyl) aminomethane.
Claim 14
Dependent Claim
22 words
A gasoline containing in the range of about 0.001 to 0.5 wt. % of acid ester of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl polyisobutylenesuccinate.
Claim 15
Dependent Claim
22 words
A gasoline containing in the range of about 0.001 to 0.5 wt. % of acid ester of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl polyisobutylenesuccinate.
Claim 16
Dependent Claim
23 words
A gasoline containing in the range of about 0.001 to 0.5 wt. % of half acid ester of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl octadecenylsuccinate.
Claim 17
Dependent Claim
23 words
A gasoline containing in the range of about 0.001 to 0.5 wt. % of half acid ester of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl octadecenylsuccinate.
Claim 18
Dependent Claim
22 words
A gasoline containing in the range of about 0.001 to 0.5 wt. % of half acid ester of 1-aza-3,7-dioxa-2,8-di-n-propyl-bicyclo[3.3.0] oct-5-yl methyl octadecenylsuccinate.
Claim 19
Dependent Claim
22 words
A gasoline containing in the range of about 0.001 to 0.5 wt. % of half acid ester of 1-aza-3,7-dioxa-2,8-di-n-propyl-bicyclo[3.3.0] oct-5-yl methyl octadecenylsuccinate.
Claim 20
Dependent Claim
18 words
A gasoline containing in the range of about 0.001 to 0.5 wt. % of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl stearate.
Claim 21
Dependent Claim
18 words
A gasoline containing in the range of about 0.001 to 0.5 wt. % of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl stearate.
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) | 1981-01-16 | 1981-07-18 | 1982-01-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-16 | 1985-07-18 | 1986-01-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-16 | 1989-07-18 | 1990-01-17 | $7700.00 | Window Closed / Lapsed |