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US4116643A
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Amine salts of carboxylate half esters of 1-aza-3,7-dioxabicyclo [3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for gasoline and middle distillate fuels
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1977-07-11
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Granted: 1978-09-26
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Expires: 1997-07-11
Abstract
Abstract Amine salts of carboxylate half esters 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 [hydroxymethyl]aminomethane (THAM) adducts or mixtures are anti-rust additives for hydrocarbon fuels, such as gasoline and middle distillates.
Inventors
- 👤 Jack Ryer
- 👤 Stanley J. Brois
- 👤 Esther D. Winans
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 00:54
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/232; C10L1/233; C10M; C10M2205/00; C10M2205/02; C10M2205/026; C10M2205/06; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/10; C10M2207/14; C10M2207/144; C10M2207/146; C10M2207/16; C10M2207/26; C10M2207/262; C10M2207/28; C10M2207/287; C10M2207/289; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/086; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/022; C10M2217/023; C10M2217/024; C10M2217/028; C10M2217/04; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2219/10; C10M2219/104; C10M2219/108; C10M2225/00; C10M2225/04; C10M2225/041; C10N; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
130 words
A fuel composition comprising a major amount of liquid hydrocarbon fuel and in the range of about 0.001 to 0.5 wt.% of a fuel soluble amine salt-ester wherein said amine contains from 1 to 3 nitrogens and from 2 to 12 carbons and said ester is the half ester reaction product of: (a) about 1 molar proportion of a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid or anhydride having about 2 to about 50 carbon atoms per hydrocarbyl group partly 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 half ester reaction product having a 1-aza-3,7-dioxabicyclo[3.3.0] octyl ring.
Claim 2
Dependent Claim
130 words
A fuel composition comprising a major amount of liquid hydrocarbon fuel and in the range of about 0.001 to 0.5 wt.% of a fuel soluble amine salt-ester wherein said amine contains from 1 to 3 nitrogens and from 2 to 12 carbons and said ester is the half ester reaction product of: (a) about 1 molar proportion of a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid or anhydride having about 2 to about 50 carbon atoms per hydrocarbyl group partly 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 half ester reaction product having a 1-aza-3,7-dioxabicyclo[3.3.0] octyl ring.
Claim 3
Dependent Claim
17 words
A composition according to claim 1, wherein said hydrocarbyl substituted acid or anhydride 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
76 words
A composition according to claim 1 wherein said amine salt is the equimolar reaction product of a hydroxy amine having the formula HO--(CH.sub.2).sub.n -- N R.sub.1 R.sub.2 wherein n represents the whole number 2, 3 or 4, R 1 and R 2 may be the same or different and each represents hydrogen, a hydroxyl alkyl group having 2 to 4 carbons or an alkyl group having 2 to 4 carbons and said half ester reaction product.
Claim 6
Dependent Claim
12 words
A composition according to claim 4 wherein said hydroxy amine is ethanolamine.
Claim 7
Dependent Claim
35 words
A composition according to claim 1 wherein said amine salt is the equivalent reaction product of an alkylene polyamine of the class consisting of ethylene diamine and diethylene triamine and said half ester reaction product.
Claim 8
Dependent Claim
17 words
A composition according to claim 1, wherein said hydrocarbyl group contains about 12 to 24 carbon atoms.
Claim 9
Dependent Claim
17 words
A composition according to claim 6, wherein said hydrocarbyl substituted acid or anhydride is octadecenyl succinic anhydride.
Claim 10
Dependent Claim
17 words
A composition according to claim 6, wherein said hydrocarbyl substituted acid or anhydride is tetrapropenyl succinic anhydride.
Claim 11
Dependent Claim
110 words
A fuel composition comprising a major amount of liquid hydrocarbon fuel and in the range of about 0.001 to 0.5 wt.% of a fuel soluble ethoxylated half ester which is the reaction product of: (a) about 1 molar proportion of a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid or anhydride having about 6 to about 50 carbon atoms per hydrocarbyl group partly 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 reaction product having a 1-aza-3,7-dioxabicyclo[3.3.0] octyl ring.
Claim 12
Dependent Claim
110 words
A fuel composition comprising a major amount of liquid hydrocarbon fuel and in the range of about 0.001 to 0.5 wt.% of a fuel soluble ethoxylated half ester which is the reaction product of: (a) about 1 molar proportion of a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid or anhydride having about 6 to about 50 carbon atoms per hydrocarbyl group partly 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 reaction product having a 1-aza-3,7-dioxabicyclo[3.3.0] octyl ring.
Claim 13
Dependent Claim
30 words
A composition according to claim 10 wherein said ethoxylated half ester is the reaction product of one to three moles of ethylene oxide to one mole of said reaction product.
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) | 1981-09-25 | 1982-03-27 | 1982-09-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-25 | 1986-03-27 | 1986-09-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-25 | 1990-03-27 | 1990-09-26 | $7700.00 | Window Closed / Lapsed |