Patent US4059535A successfully refreshed from Google Patents.
US4059535A
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Ashless detergent additives for fuels and lubricants
Assignee: Phillips Petroleum Co
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Filing: 1976-05-28
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Granted: 1977-11-22
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Expires: 1996-05-28
Abstract
Abstract A long chain monocarboxylic acid is reacted with a multi-amine to produce an amide and the amide is then treated with sulfonic acid to produce a sulfonate to provide compounds which are suitable as ashless detergent additives and the method for producing these compounds are provided. In a preferred embodiment the detergent additives are combined with hydrocarbons suitable as fuel in an internal combustion engine and with oil formulations to provide ashless fuel detergent compositions and lubricant detergent compositions.
Inventors
- 👤 Albert N. De Vault
- 👤 Hans D. Holtz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 15:53
CPC Classifications
C; C10; C10M; C10M1/00; C10M1/08; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/24; C10L1/2431; C10L1/2437; C10M2219/00; C10M2219/04; C10M2219/044
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
99 words
A method for producing detergent additive for lubricants and fuels comprising: 1. reacting a long chain monocarboxylic acid having the general formula R'COOH in which R' is a long chain aliphatic radical having 10-30 carbon atoms with a multi-amine represented by the generic formula N(RNH 2 ) 3 wherein R is an aliphatic radical having 1-6 carbon atoms to produce an amide and 2. further reacting the product of (1) with sulfonic acid represented by the formula R"SO 3 H where R" is aliphatic, cycloaliphatic, or alkaryl having 12-30 carbon atoms in the molecule to produce a sulfonated product.
Claim 2
Independent Claim
99 words
A method for producing detergent additive for lubricants and fuels comprising: 1. reacting a long chain monocarboxylic acid having the general formula R'COOH in which R' is a long chain aliphatic radical having 10-30 carbon atoms with a multi-amine represented by the generic formula N(RNH 2 ) 3 wherein R is an aliphatic radical having 1-6 carbon atoms to produce an amide and 2. further reacting the product of (1) with sulfonic acid represented by the formula R"SO 3 H where R" is aliphatic, cycloaliphatic, or alkaryl having 12-30 carbon atoms in the molecule to produce a sulfonated product.
Claim 3
Dependent Claim
40 words
A method of claim 1 wherein said monocarboxylic acid and said multi-amine are reacted at a temperature within the range of about 300° F to about 350° F in the presence of a solvent selected from xylenes or petroleum naphtha.
Claim 4
Dependent Claim
14 words
A detergent additive for lubricants and fuels produced by the method of claim 1.
Claim 5
Dependent Claim
14 words
A detergent additive for lubricants and fuels produced by the method of claim 2.
Claim 6
Dependent Claim
90 words
A compound useful as a detergent additive for lubricants and fuels prepared by reacting with a sulfonic acid represented by the formula R"SO 3 H where R" is aliphatic, cycloaliphatic, or alkaryl having 12-30 carbon atoms in the molecule the product of the reaction of a long chain monocarboxylic acid having the general formula R'COOH in which R' is a long chain aliphatic radical having 10-30 carbon atoms and a multi-amine represented by the generic formula N(RNH 2 ) 3 wherein R is an aliphatic radical having 1-6 carbon atoms.
Claim 7
Dependent Claim
90 words
A compound useful as a detergent additive for lubricants and fuels prepared by reacting with a sulfonic acid represented by the formula R"SO 3 H where R" is aliphatic, cycloaliphatic, or alkaryl having 12-30 carbon atoms in the molecule the product of the reaction of a long chain monocarboxylic acid having the general formula R'COOH in which R' is a long chain aliphatic radical having 10-30 carbon atoms and a multi-amine represented by the generic formula N(RNH 2 ) 3 wherein R is an aliphatic radical having 1-6 carbon atoms.
Claim 8
Dependent Claim
35 words
A composition comprising a hydrocarbon suitable as fuel in an internal combustion engine and a compound of claim 5, said compound of claim 6 present in an amount effective as an ashless fuel detergent additive.
Claim 9
Dependent Claim
27 words
A composition comprising a lubricating oil and a compound of claim 5, said compound of claim 6 present in an amount effective as a lubricating oil additive.
Claim 10
Dependent Claim
60 words
A method for reducing engine deposits in an internal combustion engine comprising the addition of a detergent fuel additive of claim 5 to the hydrocarbon fuel for the engine, said ashless fuel detergent being added in an amount effective to reduce engine deposits and using said hydrocarbon fuel with ashless fuel detergent additive as fuel in an internal combustion engine.
Claim 11
Dependent Claim
25 words
A composition of claim 6 wherein said ashless fuel detergent is present in the range of about 1 to about 100 lb./1000 barrels of fuel.
Claim 12
Dependent Claim
25 words
A method of claim 8 wherein said ashless fuel detergent is present in the range of about 1 to about 100 lb./1000 barrels of fuel.
Claim 13
Dependent Claim
32 words
A method of claim 1 wherein the long chain monocarboxylic acid is chosen from stearic acid and neodecanoic acid, said multi-amine is tris(2-aminoethyl) amine, and said sulfonic acid is dodecylbenzene sulfonic acid.
Claim 14
Dependent Claim
32 words
A compound of claim 5 wherein the long chain monocarboxylic acid is chosen from stearic acid and neodecanoic acid, said multi-amine is tris(2-aminoethyl) amine, and said sulfonic acid is dodecylbenzene sulfonic acid.
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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) | 1980-11-21 | 1981-05-23 | 1981-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-21 | 1985-05-23 | 1985-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-21 | 1989-05-23 | 1989-11-22 | $7700.00 | Window Closed / Lapsed |