US4199463A
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Alkylene glycol esters 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 and lubricants
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1979-01-22
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Granted: 1980-04-22
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Expires: 1999-01-22
Abstract
Abstract Alkylene glycol esters 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 friction reducing additives for liquid hydrocarbons, such as gasoline middle distillates and lubricants.
Inventors
- 👤 Jack Ryer
- 👤 Stanley Brois
- 👤 Esther D. Winans
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 09:33
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/232; C10L1/233; C10L10/00; C10L10/08; C10M; C10M133/00; C10M133/02; C10M133/38; C10M133/48; C10M133/52; C10M133/58; 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
108 words
A composition comprising a major amount of liquid hydrocarbon lubricants and at least a friction-reducing amount of an alkylene glycol ester of an ester which is the reaction product of: (a) about 1 molar proportion of a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid, anhydride or ester having about 6 to about 150 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
108 words
A composition comprising a major amount of liquid hydrocarbon lubricants and at least a friction-reducing amount of an alkylene glycol ester of an ester which is the reaction product of: (a) about 1 molar proportion of a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid, anhydride or ester having about 6 to about 150 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
12 words
A composition according to claim 2 wherein said alkenyl group is octadecenyl.
Claim 5
Dependent Claim
113 words
A lubricating composition comprising a major amount of liquid lubricatng oil and in the range of about 0.1 to 20 wt.% of an alkylene glycol ester of a half ester which is the reaction product of: (a) about 1 molar proportion of a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid, anhydride or ester having about 6 to about 150 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 6
Dependent Claim
113 words
A lubricating composition comprising a major amount of liquid lubricatng oil and in the range of about 0.1 to 20 wt.% of an alkylene glycol ester of a half ester which is the reaction product of: (a) about 1 molar proportion of a hydrocarbyl substituted C 4 to C 10 dicarboxylic acid, anhydride or ester having about 6 to about 150 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 7
Dependent Claim
75 words
A composition according to claim 4 wherein said alkylene glycol ester is the reaction product of one to ten moles of an ethoxylating agent to one mole of said half ester reaction product, said ethoxylating agent being of the class consisting of a C 2 to C 3 alkylene oxide and a glycol of the formula ##STR7## wherein x is 1 to 10, R y is hydrogen or methyl and z is 0 or 1.
Claim 8
Dependent Claim
59 words
A composition according to claim 5 wherein said alkylene glycol ester is of the formula ##STR8## wherein X is 1 to 10, R 1 represents a hydrocarbyl group of 6 to 150 carbons, z is 0 or 1, R is H or C 1 to C 12 hydrocarbyl group and R y is H or a CH 3 group.
Claim 9
Dependent Claim
17 words
A composition according to claim 5 wherein said hydrocarbyl group contains about 12 to 24 carbon atoms.
Claim 10
Dependent Claim
24 words
A composition according to claim 7 wherein said hydrocarbyl substituted acid or anhydride is octadecenyl succinic anhydride and said ethoxylating agent is ethylene oxide.
Claim 11
Dependent Claim
11 words
A composition according to claim 7 wherein said aldehyde is formaldehyde.
Claim 12
Dependent Claim
60 words
An alkylene glycol ester of carboxylic half esters of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl alcohol having the formula ##STR9## wherein X is 1 to 10, R 1 represents a hydrocarbyl group of 6 to 150 carbons, Z is 0 or 1, R is H or C 1 to C 12 hydrocarbyl group and R y is H or a CH 3 group.
Claim 13
Dependent Claim
60 words
An alkylene glycol ester of carboxylic half esters of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl alcohol having the formula ##STR9## wherein X is 1 to 10, R 1 represents a hydrocarbyl group of 6 to 150 carbons, Z is 0 or 1, R is H or C 1 to C 12 hydrocarbyl group and R y is H or a CH 3 group.
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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) | 1983-04-22 | 1983-10-22 | 1984-04-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-22 | 1987-10-22 | 1988-04-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-22 | 1991-10-22 | 1992-04-22 | $7700.00 | Window Closed / Lapsed |