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Lubricants containing amino phenol-detergent/dispersant combinations

Assignee: Lubrizol Corp

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Filing: 1976-01-28

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Granted: 1978-07-11

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Expires: 1996-01-28

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Abstract

Abstract Disclosed are combinations of amino phenols, wherein said phenols contain a substantially saturated hydrocarbon substituent of at least 10 aliphatic carbon atoms, and one or more detergent/dispersants selected from the group consisting of (I) neutral or basic metal salts of an organic sulfur acid, phenol or carboxylic acid; (II) hydrocarbylsubstituted amines wherein the hydrocarbyl substituent is substantially aliphatic and contains at least 12 carbon atoms; (III) acylated nitrogen-containing compounds having a substituent of at least 10 aliphatic carbon atoms; and (IV) nitrogen-containing condensates of a phenol, aldehyde and amino compound. Fuels and lubricants containing such combinations as additives are particularly useful in two-cycle (two-stroke) engines.

Inventors

👤 Donald Lynn Clason
👤 John Francis Pindar
👤 Jerome Martin Cohen

Bibliographic Details

Application Number —

Jurisdiction US

Data Source google_patents

Last Synchronized 2026-11-07 15:14

CPC Classifications

C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/221; C10L1/24; C10L1/2493; C10M; C10M1/00; C10M1/08; C10M2203/00; C10M2203/02; C10M2203/022; C10M2203/024; C10M2203/04; C10M2203/06; C10M2205/00; C10M2205/02; C10M2205/024; C10M2205/026; C10M2205/028; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/026; C10M2207/027; C10M2207/028; C10M2207/04; C10M2207/10; C10M2207/12; C10M2207/125; C10M2207/129; C10M2207/14; C10M2207/142; C10M2207/16; C10M2207/24; C10M2207/26; C10M2207/262; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2207/34; C10M2207/40; C10M2207/404; C10M2209/00; C10M2209/10; C10M2209/103; C10M2209/104; C10M2209/105; C10M2209/106; C10M2209/107; C10M2209/109; C10M2209/11; C10M2209/111; C10M2211/00; C10M2211/02; C10M2211/022; C10M2211/06; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/06; C10M2215/062; C10M2215/066; C10M2215/08; C10M2215/082; C10M2215/22; C10M2215/221; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/02; C10M2219/024; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/06; C10M2219/08; C10M2219/082; C10M2219/084; C10M2219/086; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2219/108; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042; C10M2223/06; C10M2223/065; C10M2227/00; C10M2227/02; C10M2229/00; C10M2229/04; C10M2229/042; C10M2229/045; C10M2229/046; C10M2229/047; C10M2229/048; C10M2229/05; C10N; C10N2010/00; C10N2010/02; C10N2010/04; C10N2010/06; C10N2010/12; C10N2010/14; C10N2010/16; C10N2040/00; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/06; C10N2040/08; C10N2040/20; C10N2050/00; C10N2050/10; C10N2070/00; C10N2070/02; F; F02; F02B; F02B75/00; F02B75/02; F02B2075/022; F02B2075/025

Claims Analysis

Total Claims: 26

Claim 1

Independent Claim 182 words

A lubricant composition for two-cycle engines comprising a major amount by weight of at least one oil of lubricating viscosity and a nitrogen-containing organic composition comprising a combination of: (A) about 2 to about 30% (based on the oil composition) of at least one amino phenol of the formula ##STR27## wherein R is a substantially saturated, hydrocarbon-based substituent of at least 10 aliphatic carbon atoms; a, b and c are each independently an integer of one up to three times the number of aromatic nuclei present in Ar with the proviso that the sum of a, b and c does not exceed the unsaturated valences of Ar; and Ar is an aromatic moiety which is substituted by 0-3 substitutents selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo or combinations of two or more of said substituents; and (B) about 1 to about 30% (based on the oil composition) of at least one detergent or dispersant, said detergent or dispersant being (I) at least one neutral or basic metal salt of an organic sulfur acid, phenol or carboxylic acid.

Claim 2

Dependent Claim 182 words

Claim 3

Dependent Claim 24 words

A composition as claimed in claim 1 wherein the detergent/dispersant is at least one basic metal salt of an organic sulfonic acid or phenol.

Claim 4

Dependent Claim 19 words

A composition as claimed in claim 2 wherein the metal is at least one alkali or alkaline earth metal.

Claim 5

Dependent Claim 18 words

A composition as claimed in claim 2 wherein the detergent/dispersant is at least one alkaline earth metal sulfonate.

Claim 6

Dependent Claim 26 words

A composition as claimed in claim 4 wherein the sulfonate is an alkyl-substituted benzene sulfonate wherein the alkyl group has at least about 8 carbon atoms.

Claim 7

Dependent Claim 60 words

A composition as claimed in claim 5 wherein the amino phenol is of the formula ##STR28## wherein R' is a substantially saturated hydrocarbon-based substituent having an average of from about 30 to about 400 aliphatic carbon atoms, R" is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro and halo; and z is 0 or 1.

Claim 8

Dependent Claim 219 words

A lubricant composition for two-cycle engines comprising a major amount by weight of at least one oil of lubricating viscosity and a nitrogen-containing organic composition comprising a combination of: (A) about 2 to about 30% (based on the oil composition) of at least one amino phenol of the formula ##STR29## wherein R is a substantially saturated, hydrocarbon-based substituent of at least 10 aliphatic carbon atoms; a, b and c are each independently an integer of one up to three times the number of aromatic nuclei present in Ar with the proviso that the sum of a, b and c does not exceed the unsaturated valences of Ar; and Ar is an aromatic moiety which is substituted by 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo or combinations of two or more of said substituents; and (B) about 1 to about 30% (based on the oil composition) of at least one detergent or dispersant, said detergent or dispersant being (III) at least one acylated, nitrogen-containing compound having a substituent of at least 10 aliphatic carbon atoms and made by reacting a carboxylic acylating agent with at least one amino compound containing at least one ##STR30## group, said acylating agent being linked to said amino compound through an imido, amido, amidine or acyloxy ammonium linkage.

Claim 9

Dependent Claim 219 words

A lubricant composition for two-cycle engines comprising a major amount by weight of at least one oil of lubricating viscosity and a nitrogen-containing organic composition comprising a combination of: (A) about 2 to about 30% (based on the oil composition) of at least one amino phenol of the formula ##STR29## wherein R is a substantially saturated, hydrocarbon-based substituent of at least 10 aliphatic carbon atoms; a, b and c are each independently an integer of one up to three times the number of aromatic nuclei present in Ar with the proviso that the sum of a, b and c does not exceed the unsaturated valences of Ar; and Ar is an aromatic moiety which is substituted by 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo or combinations of two or more of said substituents; and (B) about 1 to about 30% (based on the oil composition) of at least one detergent or dispersant, said detergent or dispersant being (III) at least one acylated, nitrogen-containing compound having a substituent of at least 10 aliphatic carbon atoms and made by reacting a carboxylic acylating agent with at least one amino compound containing at least one ##STR30## group, said acylating agent being linked to said amino compound through an imido, amido, amidine or acyloxy ammonium linkage.

Claim 10

Dependent Claim 67 words

A composition as claimed in claim 7 wherein the amino compound is an alkylene polyamine of the general formula ##STR31## wherein U is an alkylene group of 2 to 10 carbon atoms; each R'" is independently a hydrogen atom, a lower alkyl group or a lower hydroxy alkyl group, with the proviso that at least one R'" is a hydrogen atom, and n is 1 to 10.

Claim 11

Dependent Claim 31 words

A composition as claimed in claim 8 wherein the acylating agent is a mono- or polycarboxylic acid, acylating agent, containing an aliphatic hydrocarbyl substituent of at least about 30 carbon atoms.

Claim 12

Dependent Claim 27 words

A composition as claimed in claim 9 wherein the substituent is made from a homo- or interpolymer of a C 2 - 10 1-monoolefin or mixtures thereof.

Claim 13

Dependent Claim 22 words

A composition as claimed in claim 10 wherein the homo- or interpolymer is of ethylene, propylene, 1-butene, 2-butene, isobutene or mixtures thereof.

Claim 14

Dependent Claim 68 words

A composition as claimed in claim 11 wherein the amino phenol is of the formula ##STR32## wherein R' is a substantially saturated hydrocarbon-based substituent having an average of from about 30 to about 400 aliphatic carbon atoms located ortho or para to the hydroxyl group; R' is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro and halo; and z is 0 or 1.

Claim 15

Dependent Claim 28 words

A composition as claimed in claim 8 wherein the acylating agent is at least one mono-carboxylic acid, or reactant equivalent thereof, having from 12 to 30 carbon atoms.

Claim 16

Dependent Claim 28 words

A composition as claimed in claim 13 wherein the acylating agent is a mixture of fatty monocarboxylic acids, or reactant equivalent thereof, having straight and branched carbon chains.

Claim 17

Dependent Claim 32 words

A composition as claimed in claim 14 wherein the amino compound is an ethylene, propylene or trimethylene polyamine of at least 2 to about 8 amino groups or mixtures of such polyamines.

Claim 18

Dependent Claim 60 words

A composition as claimed in claim 15 wherein the amino phenol is of the formula ##STR33## wherein R' is a substantially saturated hydrocarbon-based substituent having an average of from about 30 to about 400 aliphatic carbon atoms; R" is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro and halo; and z is 0 or 1.

Claim 19

Dependent Claim 180 words

A lubricant composition for two-cycle engines comprising a major amount by weight of at least one oil of lubricating viscosity and a nitrogen-containing organic composition comprising a combination of: (A) about 2 to about 30% (based on the oil composition) of at least one amino phenol of the formula ##STR34## wherein R is a substantially saturated, hydrocarbon-based substituent of at least 10 aliphatic carbon atoms; a, b and c are each independently an integer of one up to three times the number of aromatic nuclei present in Ar with the proviso that the sum of a, b and c does not exceed the unsaturated valences of Ar; and Ar is an aromatic moiety which is substituted by 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo or combinations of two or more of said substituents; and (B) about 1 to about 30% (based on the oil composition) of at least one detergent or dispersant, said detergent or dispersant being (IV) nitrogen-containing condensate of a phenol, aldehyde and amino compound having at least one --NH group.

Claim 20

Dependent Claim 180 words

A lubricant composition for two-cycle engines comprising a major amount by weight of at least one oil of lubricating viscosity and a nitrogen-containing organic composition comprising a combination of: (A) about 2 to about 30% (based on the oil composition) of at least one amino phenol of the formula ##STR34## wherein R is a substantially saturated, hydrocarbon-based substituent of at least 10 aliphatic carbon atoms; a, b and c are each independently an integer of one up to three times the number of aromatic nuclei present in Ar with the proviso that the sum of a, b and c does not exceed the unsaturated valences of Ar; and Ar is an aromatic moiety which is substituted by 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo or combinations of two or more of said substituents; and (B) about 1 to about 30% (based on the oil composition) of at least one detergent or dispersant, said detergent or dispersant being (IV) nitrogen-containing condensate of a phenol, aldehyde and amino compound having at least one --NH group.

Claim 21

Dependent Claim 24 words

A composition as claimed in claim 17 wherein the phenol is an alkyl-substituted phenol, the alkyl group having at least about 30 carbon atoms.

Claim 22

Dependent Claim 17 words

A composition as claimed in claim 18 wherein the aldehyde is formaldehyde, or a reactant equivalent thereof.

Claim 23

Dependent Claim 63 words

A composition as claimed in claim 35 wherein the amino compound is of the formula ##STR35## wherein U is an alkylene group of 2 to 10 carbon atoms; each R'" is independently a hydrogen atom, a lower alkyl group or a lower hydroxy alkyl group, with the proviso that at least one R'" is a hydrogen atom, and n is 1 to 10.

Claim 24

Dependent Claim 62 words

A composition as claimed in claim 20 wherein the condensate is made by first reacting the phenol with the aldehyde in the presence of an alkaline catalyst at a temperature of up to 150°, then neutralizing the intermediate reaction mixture thus formed and finally reacting the neutralized intermediate reaction mixture with at least one amino compound having a least one ##STR36## group.

Claim 25

Dependent Claim 60 words

A composition as claimed in claim 17 wherein the amino phenol is of the formula ##STR37## wherein R' is a substantially saturated hydrocarbon-based substituent having an average of from about 30 to about 400 aliphatic carbon atoms; R" is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro and halo; and z is 0 or 1.

Claim 26

Dependent Claim 60 words

A composition as claimed in claim 21 wherein the amino phenol is of the formula ##STR38## wherein R' is a substantially saturated hydrocarbon-based substituent having an average of from about 30 to about 400 aliphatic carbon atoms; R" is a member selected from the group consisting of lower alkyl, lower alkoxyl, nitro and halo; and z is 0 or 1.

References Cited (Backward Citations)

US2502436A Cited

US2571092A Cited

US2831898A Cited

US3192910A Cited

US3539633A Cited

US3372118A Cited

US3798163A Cited

US3809648A Cited

US3909428A Cited

US3897352A Cited

US3897350A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1981-07-10	1982-01-09	1982-07-11	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1985-07-10	1986-01-09	1986-07-11	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1989-07-10	1990-01-09	1990-07-11	$7700.00	Window Closed / Lapsed

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