# US 4,379,065 A · Amino phenols in combination with ashless ester dispersants as useful additives for fuels and lubricants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,379,065 A - Document ID: US4379065A - Status: Granted - Kind: A - Application number: 06/358,510 - Filed: 1082-03-15 - Granted: 1983-04-05 - Earliest claimed: 1082-03-15 - Assignees: The Lubrizol Corporation - Inventors: Richard M. Lange - Web page: https://patentgrep.com/patent/US4379065A ## CPC - C10M 1/08: {with additives} - C07D 213/65: attached in position 3 or 5 - C08F 8/00: Chemical modification by after-treatment (graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C) - C08F 8/04: Reduction, e.g. hydrogenation - C08F 8/30: Introducing nitrogen atoms or nitrogen-containing groups - C10L 1/2235: {hydroxy containing (C10L1/221, C10L1/2227 take precedence)} - C10L 1/232: containing nitrogen in a heterocyclic ring {(C10L1/221 takes precedence)} - C10L 1/238: obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)} - C10L 1/2412: {sulfur bond to an aromatic radical} - C10L 1/2443: {heterocyclic compounds} - C10L 1/2475: {obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds} - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS ## Abstract Amino phenols of the general formula ##STR1## wherein R is a substantially saturated, hydrocarbon-based group of at least about 30 aliphatic carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants. These amino phenols can be conveniently prepared by nitrating an appropriate hydroxy aromatic compound and reducing the nitro groups to amino groups. Typically such amino phenols are formed by nitration and reduction of alkyl phenols having an alkyl or alkenyl group of at least about 50 carbon atoms. ## Claims ### Claim 1 A composition comprising a combination of: (A) at least one amino phenol of the general formula ##STR20## wherein R is a substantially saturated, hydrocarbon-based substituent of at least 30 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 unsatisfied valences of Ar; and Ar is an aromatic moiety having 0-3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo or combinations of two or more of said substituents; and (B) at least one ashless dispersant, wherein said dispersant is an ester composition of a high molecular weight carboxylic acid acylating agent containing at least 30 carbon atoms in the acyl moiety wherein the weight ratios of (A) to (B) is about 0.1 to about 10 to 1. ### Claim 2 (depends on 1) A composition as claimed in claim 1 wherein R contains up to about 750 carbon atoms and there are no optional substituents attached to Ar. ### Claim 3 (depends on 2) A composition as claimed in claim 2 wherein R is an alkyl or alkenyl group. ### Claim 4 (depends on 1) A composition as claimed in claim 1 wherein R contains from about 50 to about 750 aliphatic carbon atoms and is made from a homo- or interpolymer of mono- and diolefins having 2 to 10 carbon atoms. ### Claim 5 (depends on 4) A composition as claimed in claim 4 wherein said olefins are selected from the group consisting of ethylene, propylene, butylene and mixtures thereof. ### Claim 6 (depends on 1) A composition as claimed in claim 1 wherein a, b and c are each 1, there are zero optional substituents attached to Ar, and Ar is a benzene nucleus. ### Claim 7 (depends on 6) A composition as claimed in claim 6 wherein R is an alkyl or alkenyl group of at least about 50 carbon atoms and up to about 750 carbon atoms and is derived from a homo- or interpolymer of 1-monoolefins having 2 to 10 carbon atoms. ### Claim 8 (depends on 1) A composition as claimed in claim 1 wherein the amino phenol is of the formula ##STR21## wherein R* is a substantially saturated hydrocarbon-based group having an average of from about 30 to about 750 aliphatic carbon atoms and R'" is a lower alkyl, lower alkoxyl, nitro group or halogen atom and z is 0 or 1 with the proviso that when there is only one --NH.sub.2 group ortho to the phenolic OH group, R'", if present, can be ortho to said --OH group. ### Claim 9 (depends on 1, 3, 5, 7, 8) A composition according to claims 1, 3, 5, 7 or 8 wherein the ester is derived from a polyol and a high molecular weight succinic acid acylating agent containing at least 50 carbon atoms in the acyl moiety. ### Claim 10 (depends on 9) A composition according to claim 9 wherein the high molecular weight succinic acid acylating agent is an alkenyl- or alkyl succinic acid or anhydride or mixtures thereof wherein the alkenyl or alkyl group contains from 50 to 700 carbon atoms and the polyol contains at least 3 hydroxy groups. ### Claim 11 (depends on 9) A composition according to claim 9 wherein the high molecular weight succinic acid acylating agent is polyisobutenyl substituted succinic anhydride and the polyols are glycerol, pentaerythritol, mannitol or mixtures of two or more of these polyols. ### Claim 12 (depends on 1) A composition according to claim 1 wherein, when said ester composition contains unesterified acidic groups in the acylating agent, said ester composition is further reacted with an amine compound. ### Claim 13 (depends on 1) A fuel composition containing a major proportion of a normally liquid fuel and about 1 to about 10,000 parts by weight per million parts of fuel of at least one composition claimed in claim 1. ### Claim 14 A fuel composition containing a major proportion of a normally liquid fuel and about 1 to about 10,000 parts by weight per million parts of fuel of at least one composition claimed in 9. ### Claim 15 (depends on 12) A fuel composition containing a major proportion of a normally liquid fuel and about 1 to about 10,000 parts by weight per million parts of fuel of at least one composition claimed in claim 12. ### Claim 16 (depends on 1) A lubricant composition comprising a major proportion of at least one oil of lubricating viscosity and about 0.05 to about 30 parts by weight per 100 parts oil of at least one composition claimed in claim 1. ### Claim 17 (depends on 9) A lubricant composition comprising a major proportion of at least one oil of lubricating viscosity and about 0.05 to about 30 parts by weight per 100 parts oil of at least one composition claimed in claim 9. ### Claim 18 (depends on 12) A lubricant composition comprising a major proportion of at least one oil of lubricating viscosity and about 0.05 to about 30 parts by weight per 100 parts oil of at least one composition claimed in claim 12. ### Claim 19 (depends on 1) An additive concentrate comprising about 30-90% of at least one composition of claim 1 and a substantially inert, normally liquid organic solvent/diluent. ### Claim 20 (depends on 9) An additive concentrate comprising about 30-90% of at least one composition of claim 9 and a substantially inert, normally liquid organic solvent/diluent. ### Claim 21 (depends on 12) An additive concentrate comprising about 30-90% of at least one composition of claim 12 and a substantially inert, normally liquid organic solvent/diluent.