US4062786A
Expired / Lapsed
US
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Lactone oxazolines as oleaginous additives
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1976-09-24
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Granted: 1977-12-13
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Expires: 1996-09-24
Abstract
Abstract Lactone oxazoline reaction products of hydrocarbon substituted lactone carboxylic acids, for example, polybutyl lactone carboxylic acid, with 2,2-disubstituted-2-amino-1-alkanols, such as tris-(hydroxymethyl)aminomethane (THAM), and their derivatives are useful additives in oleaginous compositions, such as sludge dispersants for lubricating oil, or anti-rust agents for gasoline.
Inventors
- 👤 Stanley J. Brois
- 👤 Antonio Gutierrez
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 20:33
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/26; C07D307/30; C07D307/32; C07D307/33; C07D307/34; C07D307/56; C07D307/60; C07D309/00; C07D309/16; C07D309/28; C07D309/30; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/232; C10L1/233; C10L1/24; C10L1/2493; C10M; C10M133/00; C10M133/02; C10M133/38; C10M133/44; C10M133/48; C10M133/52; C10M133/58; C10M135/00; C10M135/32; C10M2205/00; C10M2205/02; C10M2205/022; C10M2205/026; C10M2205/14; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2209/086; C10M2209/10; C10M2209/11; C10M2209/112; 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; C10M2219/085; C10M2219/087; C10M2219/088; C10M2219/089; C10M2219/09; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/045; C10M2223/047; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05; C10N; C10N2010/00; C10N2010/06; C10N2040/00; C10N2040/08; C10N2040/25; C10N2040/251; C10N2040/255; C10N2040/28; C10N2070/00; C10N2070/02; F; F02; F02B; F02B3/00; F02B3/06
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
66 words
A lactone oxazoline reaction product obtained from heating together an equimolar mixture of a hydrocarbon-substituted lactone acid material selected from the group consisting of acids, amides and esters, and a 2,2-disubstituted-2-amino-1-alkanol having 1 to 3 hydroxy groups and containing a total of 4 to 8 carbons at a temperature of from 100°-240° C. until infra-red absorption for oxazoline is maximal indicating completion of the oxazoline reaction.
Claim 2
Dependent Claim
66 words
A lactone oxazoline reaction product obtained from heating together an equimolar mixture of a hydrocarbon-substituted lactone acid material selected from the group consisting of acids, amides and esters, and a 2,2-disubstituted-2-amino-1-alkanol having 1 to 3 hydroxy groups and containing a total of 4 to 8 carbons at a temperature of from 100°-240° C. until infra-red absorption for oxazoline is maximal indicating completion of the oxazoline reaction.
Claim 3
Dependent Claim
56 words
A reaction product according to claim 1 wherein said amino-alkanol has the formula ##STR24## 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.
Claim 4
Dependent Claim
38 words
An oil-soluble reaction product according to claim 2 wherein said hydrocarbon-substituted lactone acid material is polyisobutyl lactone carboxylic acid, said amino-alkanol is tris-(hydroxymethyl) aminomethane and said heating is continued until about 2 molar equivalents of water have evolved.
Claim 5
Dependent Claim
92 words
A lubricating oil composition comprising: a major amount of lubricating oil and 0.01 to 20 wt. % of an oil-soluble, lactone oxazoline reaction product obtained from heating together a molar proportion of a C 4 -C 400 hydrocarbon substituted lactone acid material selected from the group consisting of acids, amides and esters; and one molar proportion of a 2,2-disubstituted-2-amino-1-alkanol having 1 to 3 hydroxy groups and containing a total of 4 to 8 carbons at a temperature of from 100°-240° C. untiil cessation of water evolution indicating completion of the oxazoline reaction.
Claim 6
Dependent Claim
92 words
A lubricating oil composition comprising: a major amount of lubricating oil and 0.01 to 20 wt. % of an oil-soluble, lactone oxazoline reaction product obtained from heating together a molar proportion of a C 4 -C 400 hydrocarbon substituted lactone acid material selected from the group consisting of acids, amides and esters; and one molar proportion of a 2,2-disubstituted-2-amino-1-alkanol having 1 to 3 hydroxy groups and containing a total of 4 to 8 carbons at a temperature of from 100°-240° C. untiil cessation of water evolution indicating completion of the oxazoline reaction.
Claim 7
Dependent Claim
12 words
A composition according to claim 4 wherein said amino-1-alkanol is tris-(hydroxymethyl) aminomethane.
Claim 8
Dependent Claim
161 words
An additive concentrate comprising: an amount of mineral lubricating oil in the range of 10 to 80 parts by weight, 20 to 90 parts by weight of a lactone oxazoline of one molar proportion of a hydrocarbon substituted C 4 -C 10 mono-unsaturated lactone acid material selected from the group consisting of carboxylic acid, ester and amide thereof, having more than 8 carbon atoms in said hydrocarbon substituent; reacted with about one molar proportion of a 2,2-disubstituted-2-amino-1-alkanol having 1 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula: ##STR25## 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 100° to 240° C. until cessation of water evolution indicating completion of the oxazoline reaction.
Claim 9
Dependent Claim
161 words
An additive concentrate comprising: an amount of mineral lubricating oil in the range of 10 to 80 parts by weight, 20 to 90 parts by weight of a lactone oxazoline of one molar proportion of a hydrocarbon substituted C 4 -C 10 mono-unsaturated lactone acid material selected from the group consisting of carboxylic acid, ester and amide thereof, having more than 8 carbon atoms in said hydrocarbon substituent; reacted with about one molar proportion of a 2,2-disubstituted-2-amino-1-alkanol having 1 to 3 hydroxy groups and containing a total of 4 to 8 carbons of the formula: ##STR25## 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 100° to 240° C. until cessation of water evolution indicating completion of the oxazoline reaction.
Claim 10
Dependent Claim
2 words
Polyisobutyl lactone-[5,5-bis-(hydroxymethyl)oxazoline-2].
Claim 11
Dependent Claim
2 words
Polyisobutyl lactone-[5,5-bis-(hydroxymethyl)oxazoline-2].
Claim 12
Dependent Claim
117 words
A process for preparing lactone oxazolines comprising the step of heating together equimolar amounts of an alkyl lactone acid material selected from the group consisting of acids, amides and esters and 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: ##STR26## 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 100° to 240° C. until cessation of water evolution indicating completion of the oxazoline reaction.
Claim 13
Dependent Claim
117 words
A process for preparing lactone oxazolines comprising the step of heating together equimolar amounts of an alkyl lactone acid material selected from the group consisting of acids, amides and esters and 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: ##STR26## 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 100° to 240° C. until cessation of water evolution indicating completion of the oxazoline reaction.
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) | 1980-12-12 | 1981-06-13 | 1981-12-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-12 | 1985-06-13 | 1985-12-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-12 | 1989-06-13 | 1989-12-13 | $7700.00 | Window Closed / Lapsed |