US4787996A
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Mannich base oil additives
Assignee: Mobil Oil AS
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Filing: 1987-04-14
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Granted: 1988-11-29
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Expires: 2007-04-14
Abstract
Abstract Mannich bases, prepared using a phenol substituted with a medium length branched alkyl chain, the alkyl being derived from a 1-olefin oligomer. These Mannich bases act as friction-reducing agents in lubricant and liquid fuel compositions.
Inventors
- 👤 Andrew G. Horodysky
- 👤 Robert M. Gemmill, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 00:30
CPC Classifications
C; C10; C10L; C10L10/00; C10L10/08; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/222; C10L1/2222; C10L1/2225; C10L1/234; C10L1/238; C10L10/04; C10M; C10M159/00; C10M159/12; C10M159/16; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/24; C10M2215/26; C10M2217/00; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10N; C10N2040/00; C10N2040/08; C10N2040/25; C10N2040/251; C10N2040/255; C10N2040/28
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
160 words
A method for reducing the coefficient of friction of a liquid lubricating oil which comprises adding to such an oil a coefficient of friction-reducing amount of the product resulting from reacting an aldehyde; at least one amine selected from the group consisting of primary amines containing from 8 to 18 carbon atoms and polyalkylenepolyamines of the formula NHX(R.sup.4 NH).sub.n R.sup.2 wherein R 2 and X are selected from the group consisting of hydrogen, a hydrocarbyl group and a hydroxyhydrocarbyl group, either containing 6 to 18 carbon atoms, R 4 is an alkylene group containing 1 to 5 carbon atoms and n is 1 to 10; and, at least one alkyl-substituted phenol wherein the alkyl is branched, contains from 16 to 40 carbon atoms and is derived from a 1-olefin oligomer containing from 8 to 12 carbon atoms, the reaction being carried out from about 60° C. to about 130° C. using the reactants in a respective molar ratio of 1.0-2.0:1.0-2.0:1.0.
Claim 2
Independent Claim
160 words
A method for reducing the coefficient of friction of a liquid lubricating oil which comprises adding to such an oil a coefficient of friction-reducing amount of the product resulting from reacting an aldehyde; at least one amine selected from the group consisting of primary amines containing from 8 to 18 carbon atoms and polyalkylenepolyamines of the formula NHX(R.sup.4 NH).sub.n R.sup.2 wherein R 2 and X are selected from the group consisting of hydrogen, a hydrocarbyl group and a hydroxyhydrocarbyl group, either containing 6 to 18 carbon atoms, R 4 is an alkylene group containing 1 to 5 carbon atoms and n is 1 to 10; and, at least one alkyl-substituted phenol wherein the alkyl is branched, contains from 16 to 40 carbon atoms and is derived from a 1-olefin oligomer containing from 8 to 12 carbon atoms, the reaction being carried out from about 60° C. to about 130° C. using the reactants in a respective molar ratio of 1.0-2.0:1.0-2.0:1.0.
Claim 3
Dependent Claim
34 words
The method of claim 1 wherein the alkyl-substituted phenol is represented by the formula ##STR2## wherein R represents the alkyl of from 16 to 40 carbon atoms and R 1 is hydrogen or R.
Claim 4
Dependent Claim
28 words
The method of claim 2 wherein the alkyl-substituted phenol prior to substitution with the alkyl group is phenol, cresol, xylitol, hydroxydiphenyl, amylphenol, benzylphenol, alpha naphthol or beta naphthol.
Claim 5
Dependent Claim
50 words
The method of claim 1 wherein the aldehyde is represented by the formula R.sup.3 CHO wherein R 3 is hydrogen, a hydrocarbyl group containing from 1 to 10 carbon atoms or a hydrocarbyl group containing from 1 to 10 carbon atoms and substituted with a halogen atom or hydroxyl group.
Claim 6
Dependent Claim
15 words
The method of claim 1 wherein the aldehyde is an aromatic, aliphatic or heterocyclic aldehyde.
Claim 7
Dependent Claim
17 words
The method of claim 1 wherein the aldehyde is formaldehyde, paraformaldehyde, acetaldehyde, aldol beta-hydroxybutyraldehyde, benzaldehyde or furfural.
Claim 8
Dependent Claim
36 words
The method of claim 1 wherein the amine is cocoamine, oleylamine, octylamine, nonylamine, decylamine, cyclooctylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, stearylamine, laurylamine, soyamine, dibutylamine, dioctylamine, ethanolamine, diethanolamine, dimethylenetriamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, hexaethyleneheptamine, ethylenediamine, propylenediamine, cyclohexylamine or dicyclohexylamine.
Claim 9
Dependent Claim
28 words
The method of claim 1 wherein the alkyl substituted phenol is derived from the alkylation of phenol with 1-decene, the aldehyde is paraformaldehyde and the amine is cocoamine.
Claim 10
Dependent Claim
152 words
A liquid lubricating oil composition which comprises a liquid lubricating oil and a coefficient of friction-reducing amount of the product resulting from reacting an aldehyde; at least one amine selected from the group consisting of primary amines containing from 8 to 18 carbon atoms and polyalkylenepolyamines of the formula NHX(R.sup.4 NH).sub.n R.sup.2 wherein R 2 and X are selected from the group consisting of hydrogen, a hydrocarbyl group and a hydroxyhydrocarbyl group, either containing 6 to 18 carbon atoms, R 4 is an alkylene group containing 1 to 5 carbon atoms and n is 1 to 10; and, at least one alkyl-substituted phenol wherein the alkyl is branched, contains from 16 to 40 carbon atoms and is derived from a 1-olefin oligomer containing from 8 to 12 carbon atoms, the reaction being carried out from about 60° C. to about 130° C. using the reactants in a respective molar ratio of 1.0-2.0:1.0-2.0:1.0.
Claim 11
Dependent Claim
152 words
A liquid lubricating oil composition which comprises a liquid lubricating oil and a coefficient of friction-reducing amount of the product resulting from reacting an aldehyde; at least one amine selected from the group consisting of primary amines containing from 8 to 18 carbon atoms and polyalkylenepolyamines of the formula NHX(R.sup.4 NH).sub.n R.sup.2 wherein R 2 and X are selected from the group consisting of hydrogen, a hydrocarbyl group and a hydroxyhydrocarbyl group, either containing 6 to 18 carbon atoms, R 4 is an alkylene group containing 1 to 5 carbon atoms and n is 1 to 10; and, at least one alkyl-substituted phenol wherein the alkyl is branched, contains from 16 to 40 carbon atoms and is derived from a 1-olefin oligomer containing from 8 to 12 carbon atoms, the reaction being carried out from about 60° C. to about 130° C. using the reactants in a respective molar ratio of 1.0-2.0:1.0-2.0:1.0.
Claim 12
Dependent Claim
36 words
The lubricating oil composition of claim 9 wherein the alkyl-substituted phenol is represented by the formula ##STR3## wherein R represents the alkyl of from 16 to 40 carbon atoms and R 1 is hydrogen or R.
Claim 13
Dependent Claim
30 words
The lubricating oil composition of claim 10 wherein the alkyl-substituted phenol prior to substitution with the alkyl group is phenol, cresol, xylitol, hydroxydiphenyl, amylphenol, benzylphenol, alpha naphthol or beta naphthol.
Claim 14
Dependent Claim
52 words
The lubricating oil composition of claim 9 wherein the aldehyde is represented by the formula R.sup.3 CHO wherein R 3 is hydrogen, a hydrocarbyl group containing from 1 to 10 carbon atoms or a hydrocarbyl group containing from 1 to 10 carbon atoms and substituted with a halogen atom or hydroxyl group.
Claim 15
Dependent Claim
17 words
The lubricating oil composition of claim 9 wherein the aldehyde is an aromatic, aliphatic or heterocyclic aldehyde.
Claim 16
Dependent Claim
19 words
The lubricating oil composition of claim 9 wherein the aldehyde is formaldehyde, paraformaldehyde, acetaldehyde, aldol beta-hydroxybutyraldehyde, benzaldehyde or furfural.
Claim 17
Dependent Claim
45 words
The lubricating oil composition of claim 9 wherein the amine method of claim 1 wherein the amine is cocoamine, oleylamine, octylamine, nonylamine, decylamine, cyclooctylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, stearylamine, laurylamine, soyamine, dibutylamine, dioctylamine, ethanolamine, diethanolamine, dimethylenetriamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, hexaethyleneheptamine, ethylenediamine, propylenediamine, cyclohexylamine or dicyclohexylamine.
Claim 18
Dependent Claim
30 words
The lubricating oil composition of claim 9 wherein the alkyl substituted phenol is derived from the alkylation of phenol with 1-decene, the aldehyde is paraformaldehyde and the amine is cocoamine.
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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) | 1991-11-29 | 1992-05-30 | 1992-11-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-29 | 1996-05-30 | 1996-11-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-29 | 2000-05-30 | 2000-11-29 | $7700.00 | Window Closed / Lapsed |