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US4035309A
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Metal-containing oxazoline additives and lubricating oils containing said additives
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1975-03-24
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Granted: 1977-07-12
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Expires: 1995-03-24
Abstract
Abstract Metal-containing oxazoline products from the metal salt (e.g. zinc acetate) promoted reaction of hydrocarbon substituted dicarboxylic acid material, for example, polyisobutenyl-succinic anhydride, with a 2,2-disubstituted-2-amino-1-alkanol, such as tris-hydroxymethylaminomethane (THAM) are useful additives in oleaginous compositions, such as sludge dispersants for lubricating oil or gasoline.
Inventors
- 👤 Stanley J. Brois
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 15:35
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/232; C10L1/233; C10M; C10M159/00; C10M159/12; C10M159/18; C10M2215/00; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/30; C10N; C10N2010/00; C10N2010/04; C10N2040/00; C10N2040/08; C10N2040/135
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
167 words
In a process for preparing oxazoline compounds wherein one molar equivalent of an alkenyl substituted succinic acid or alkenyl substituted succinic acid anhydride is reacted with one to two molar equivalents of a 2,2-di-substituted -2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbon atoms and represented by the formula: ##STR3## wherein X is an alkyl or hydroxy alkyl group and one of the X substituents being a hydroxyalkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3 at a temperature of from 140° to 240° C., the improvement which comprises conducting said reaction in the presence of from 0.01 to 10 wt. % based on the combined total weight of said reactants of a metal salt promotor of the class of a metal salt of a C 1-8 hydrocarbyl carboxylic acid or metal oxide whereby said reaction time is shortened, said metal being of the class consisting of zinc, manganese, iron, cobalt and nickel.
Claim 2
Dependent Claim
167 words
In a process for preparing oxazoline compounds wherein one molar equivalent of an alkenyl substituted succinic acid or alkenyl substituted succinic acid anhydride is reacted with one to two molar equivalents of a 2,2-di-substituted -2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbon atoms and represented by the formula: ##STR3## wherein X is an alkyl or hydroxy alkyl group and one of the X substituents being a hydroxyalkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3 at a temperature of from 140° to 240° C., the improvement which comprises conducting said reaction in the presence of from 0.01 to 10 wt. % based on the combined total weight of said reactants of a metal salt promotor of the class of a metal salt of a C 1-8 hydrocarbyl carboxylic acid or metal oxide whereby said reaction time is shortened, said metal being of the class consisting of zinc, manganese, iron, cobalt and nickel.
Claim 3
Dependent Claim
33 words
The process according to claim 1 wherein said metal carboxylate salt consists of metal salts of C 1 to C 8 fatty acids and said amino-alkanol is present in about two molar equivalents.
Claim 4
Dependent Claim
27 words
The process according to claim 2 wherein said salt is zinc acetate or zinc oxide, said amino alkanol is trishydroxy-aminomethane and said temperature is from 170-210° C.
Claim 5
Dependent Claim
148 words
An oil soluble reaction product having a weight average molecular weight of from about 200 to 5000 obtained from the reaction of one molar equivalent of an alkenyl substituted succinic acid or alkenyl substituted succinic acid anhydride with from one to two molar equivalents of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbon atoms and represented by the formula: ##STR4## wherein X is an alkyl or hydroxy alkyl group and one of the X substituents being a hydroxyalkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3 at a temperature of from 140° to 240° C., said reaction product containing from about 0.01 to 6 wt. % metal of the class consisting of zinc, manganese, iron, cobalt and nickel, said metal present as a metal salt of a C 1-8 hydrocarbyl carboxylic acid.
Claim 6
Dependent Claim
148 words
An oil soluble reaction product having a weight average molecular weight of from about 200 to 5000 obtained from the reaction of one molar equivalent of an alkenyl substituted succinic acid or alkenyl substituted succinic acid anhydride with from one to two molar equivalents of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbon atoms and represented by the formula: ##STR4## wherein X is an alkyl or hydroxy alkyl group and one of the X substituents being a hydroxyalkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3 at a temperature of from 140° to 240° C., said reaction product containing from about 0.01 to 6 wt. % metal of the class consisting of zinc, manganese, iron, cobalt and nickel, said metal present as a metal salt of a C 1-8 hydrocarbyl carboxylic acid.
Claim 7
Dependent Claim
25 words
The reaction product of claim 4 wherein said metal is zinc and is present in the amounts of from about 0.1 to 2 wt. %.
Claim 8
Dependent Claim
38 words
An oil soluble reaction product according to claim 4 wherein one molar proportion of said acid material is reacted with about two molar proportions of tris-hydroxy-aminomethane whereby a bis-oxazoline reaction product complexed with a metal salt is obtained.
Claim 9
Dependent Claim
28 words
A reaction product according to claim 4 wherein said product is substantially imide free and at least 70% of its carboxyl groups have been converted to oxazoline groups.
Claim 10
Dependent Claim
143 words
A mono-oxazoline reaction product having a weight average molecular weight of from about 500 to about 3000 obtained from the reaction of one molar proportion of an alkenyl substituted succinic acid or alkenyl substituted succinic acid anhydride and one molar proportion of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbon atoms and represented by the formula: ##STR5## wherein X is an alkyl or hydroxy alkyl group and one of the X substituents being a hydroxy alkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3 at a temperature of from 140° to 240° C. and containing from about 0.1 to 2 wt. % of metal of the class consisting of zinc, iron, cobalt and nickel, said metal present as a salt of a C 1-8 hydrocarbyl carboxylic acid.
Claim 11
Dependent Claim
143 words
A mono-oxazoline reaction product having a weight average molecular weight of from about 500 to about 3000 obtained from the reaction of one molar proportion of an alkenyl substituted succinic acid or alkenyl substituted succinic acid anhydride and one molar proportion of a 2,2-disubstituted-2-amino-1-alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbon atoms and represented by the formula: ##STR5## wherein X is an alkyl or hydroxy alkyl group and one of the X substituents being a hydroxy alkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3 at a temperature of from 140° to 240° C. and containing from about 0.1 to 2 wt. % of metal of the class consisting of zinc, iron, cobalt and nickel, said metal present as a salt of a C 1-8 hydrocarbyl carboxylic acid.
Claim 12
Dependent Claim
173 words
An oleaginous composition comprising a major amount of an oil of lubricating viscosity and at least a dispersant amount of an oil soluble oxazoline reaction product having a weight average molecular weight of from about 200 to 5000 obtained from the reaction of about one molar equivalent of an alkenyl substituted succinic acid or alkenyl substituted succinic anhydride reacted with from about one to two molar equivalents of a 2,2-disubstituted-2-amino-1 -alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbon atoms and represented by the formula: ##STR6## wherein X is an alkyl or hydroxy alkyl group and one of the X substituents being a hydroxyalkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3 at a temperature of from 140° C. to 240° C., said reaction product containing from about 0.01 to 6 wt. % metal of the class consisting of zinc, manganese, iron, cobalt and nickel, said metal present as a metal salt of a C 1-8 hydrocarbyl carboxylic acid.
Claim 13
Dependent Claim
173 words
An oleaginous composition comprising a major amount of an oil of lubricating viscosity and at least a dispersant amount of an oil soluble oxazoline reaction product having a weight average molecular weight of from about 200 to 5000 obtained from the reaction of about one molar equivalent of an alkenyl substituted succinic acid or alkenyl substituted succinic anhydride reacted with from about one to two molar equivalents of a 2,2-disubstituted-2-amino-1 -alkanol having 2 to 3 hydroxy groups and containing a total of 4 to 8 carbon atoms and represented by the formula: ##STR6## wherein X is an alkyl or hydroxy alkyl group and one of the X substituents being a hydroxyalkyl group of the structure --(CH 2 ) n OH wherein n is 1 to 3 at a temperature of from 140° C. to 240° C., said reaction product containing from about 0.01 to 6 wt. % metal of the class consisting of zinc, manganese, iron, cobalt and nickel, said metal present as a metal salt of a C 1-8 hydrocarbyl carboxylic acid.
Claim 14
Dependent Claim
25 words
A composition according to claim 9 wherein said product is a bis-oxazoline reaction product and said metal is zinc and is complexed with said product.
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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) | 1980-07-11 | 1981-01-10 | 1981-07-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-11 | 1985-01-10 | 1985-07-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-11 | 1989-01-10 | 1989-07-12 | $7700.00 | Window Closed / Lapsed |