# US 5,348,674 A · Amide/ester heterocyclic derivatives of hydrocarbylsuccinic anhydrides as rust/corrosion inhibiting additives for lubricants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,348,674 A - Document ID: US5348674A - Status: Granted - Kind: A - Application number: 08/044,724 - Filed: 1993-04-12 - Granted: 1994-09-20 - Earliest claimed: 1993-04-12 - Assignees: Mobil Oil Corporation - Inventors: David A. Blain; Andrew G. Horodysky; Ronald J. Poole; Shi-Ming Wu - Web page: https://patentgrep.com/patent/US5348674A ## CPC - C10M 159/12: Reaction products - C10M 129/72: of polycarboxylic acids - C10M 133/08: containing hydroxy groups - C10M 133/44: Five-membered ring containing nitrogen and carbon only - C10M 2207/027: Neutral salts thereof - C10M 2207/028: Overbased salts thereof - C10M 2207/282: of (cyclo)aliphatic oolycarboxylic acids - C10M 2207/285: of aromatic polycarboxylic acids - C10M 2207/286: of polymerised unsaturated acids - C10M 2215/04: having amino groups bound to acyclic or cycloaliphatic carbon atoms - C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof - C10M 2215/086: Imides [having hydrocarbon substituents containing less than thirty carbon atoms] - C10M 2215/223: Five-membered rings containing nitrogen and carbon only - C10M 2215/26: Amines - C10M 2215/28: Amides; Imides - C10M 2217/046: Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers - C10M 2217/06: Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound - C10M 2219/044: Sulfonic acids, Derivatives thereof, e.g. neutral salts - C10M 2219/046: Overbased sulfonic acid salts - C10M 2223/045: Metal containing thio derivatives - C10M 2223/047: Thioderivatives not containing metallic elements - C10M 2227/00: Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions - 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) ## Abstract Reaction products of hydrocarbylsuccinic anhydrides, hydroxyl-containing amines and triazoles have been found to be effective antirust, antioxidant, anti-corrosion, antiwear, dispersant/detergent and thermal color stabilizing additives. ## Claims ### Claim 1 An improved lubricant composition comprising a major proportion of an oil of lubricating viscosity or grease prepared therefrom and a minor multifunctional antiwear, corrosion inhibiting, rust inhibiting, thermal color stabilizing, antioxidant, dispersant and detergent proportion of an additive product of reaction prepared by reacting (1) a hydrocarbylsuccinic anhydride or its acid equivalent with (2) a hydroxyl-containing amine and (3) an aryltriazole wherein the reaction is carried out in molar ratios of said anhydride to amine to triazole varying from about 100/80/80 to 100/10/1 at temperatures varying from ambient to about 250.degree. C., under pressures varying from ambient to about 100 psi for a time sufficient to obtain the desired additive product of reaction. ### Claim 2 (depends on 1) The composition of claim 1 wherein the triazole is selected from the group consisting of benzotriazole, alkylated benzotriazoles and tolyltriazole. ### Claim 3 (depends on 1) The composition of claim 1 wherein the hydrocarbylsuccinic anhydride has the following structural formula: ##STR4## where R.sub.1 is C.sub.1 to about C.sub.300 hydrocarbyl and where hydrocarbyl is selected from the group consisting of alkyl, alkenyl, aryl, alkaryl, aralkyl and may be cyclic or polycyclic and optionally contain S, O, N or mixtures thereof. ### Claim 4 (depends on 1) The composition of claim 1 wherein the hydroxyl-containing amines are selected from amines having have the following structural formulas: ##STR5## where R.sub.2 is hydrogen or C.sub.1 to about C.sub.100 hydrocarbyl, and where R.sub.3, R.sub.4, and R.sub.5 are hydrogen or C.sub.1 to about C.sub.60 hydrocarbyl and where R.sub.6 is C.sub.2 to about C.sub.25 hydrocarbyl and wherein hydrocarbyl is selected from the group consisting of alkyl, alkenyl, aryl, alkaryl or aralkyl and optionally contains O, S, or N or mixtures thereof and where X=0-20, Y=0-20, Z=0-20, and X+Y+Z must equal at least 1. ### Claim 5 (depends on 1) The composition of claim 1 wherein the reactants are dodecenylsuccinic anhydride, bis(2-hydroxyethyl)oleylamine and tolyltriazole. ### Claim 6 (depends on 1) The composition of claim 1 wherein the reactants are dodecenylsuccinic anhydride, bis(2-hydroxyethyl)tallow amine and tolyltriazole. ### Claim 7 (depends on 1) The composition of claim 1 wherein the reactants are dodecenylsuccinic anhydride, bis(2-hydroxyethyl)soya amine and tolyltriazole. ### Claim 8 (depends on 1) The composition of claim 1 wherein the reactants are dodecenylsuccinic anhydride, alkoxylated tallow diamine, and tolyltriazole. ### Claim 9 (depends on 1) The composition of claim 1 wherein the oil of lubricating viscosity is selected from the group consisting of (1) mineral oils, (2) synthetic oils, (3) or mixtures of mineral and synthetic oils or is (4) a grease prepared from any one of (1), (2) or (3). ### Claim 10 (depends on 10) The composition of claim 10 wherein the lubricant contains from about 0.001 to about 10 wt % based on the total weight of the composition of the additive product of reaction. ### Claim 11 (depends on 10) The composition of claim 10 wherein the oil of lubricating viscosity is a mineral oil. ### Claim 12 A process of preparing a multifunctional antiwear, corrosion inhibiting, rust inhibiting thermal color stabilizing, antioxidant, detergent, dispersant product additive prepared by reacting (1) a hydrocarbylsuccinic anhydride or its acid equivalent with (2) a hydroxyl-containing amine and (3) an aryltriazole wherein the reaction is carried out in molar ratios of said anhydride to amine to triazole varying from 100/80/80 to 100/10/1 at temperatures varying from ambient to about 250.degree. C., under pressures varying from ambient to about 100 psi for a time sufficient to obtain the desired additive product of reaction. ### Claim 13 (depends on 13) The process of claim 13 wherein the hydrocarbylsuccinic anhydride has the following structural ##STR6## wherein R.sub.1 is C.sub.1 to about C.sub.300 hydrocarbyl and where hydrocarbyl is selected from the group consisting of alkyl, alkenyl, aryl, alkaryl, aralkyl which may be cyclic or polycyclic and optionally contains O, N, S or mixtures thereof and wherein the hydroxyl-containing amines are selected from amines having the following structural formulas: ##STR7## where R.sub.2 is hydrogen or C.sub.1 to about C.sub.100 hydrocarbyl, R.sub.3, R.sub.4, and R.sub.5 are hydrogen or C.sub.1 to about C.sub.60 hydrocarbyl and where R.sub.6 is C.sub.2 to about C.sub.25 hydrocarbyl and wherein hydrocarbyl is selected from the group consisting of alkyl, alkenyl, aryl, alkaryl or aralkyl and optionally contains O, S, or N or mixtures thereof and where X=0-20, Y=0-20, Z=-20, and X+Y+Z must equal at least 1. ### Claim 14 A multifunctional antiwear, corrosion inhibiting rust inhibiting, and thermal color stabilizing lubricant additive product of reaction prepared by reacting (1) a hydrocarbylsuccinic anhydride or its acid equivalent with (2) a hydroxyl-containing amine and (3) a triazole wherein the reaction is carried out in molar ratios of said anhydride to amine to triazole varying from 100/80/80 to 100/10/1, at temperatures varying from ambient to about 250.degree. C. or is reflux, under autogenous pressures or pressures varying from ambient to about 100 psi for a time sufficient to obtain the desired additive product of reaction. ### Claim 15 (depends on 15) The additive product of reaction in accordance with claim 15 wherein the hydrocarbylsuccinic anhydride has the following structural formula: ##STR8## where R.sub.1 is C.sub.1 to about C.sub.300 hydrocarbyl and where hydrocarbyl is selected from the group consisting of alkyl, alkenyl, aryl, alkaryl, aralkyl which may be cyclic or polycyclic and optionally contain O, N, S or mixtures thereof and wherein the hydroxyl-containing amines are selected from amines having the following structural formula: ##STR9## where R.sub.2 is hydrogen or C.sub.1 to about C.sub.100 hydrocarbyl, R.sub.3, R.sub.4 and R.sub.5 are hydrogen or C.sub.1 to about C.sub.60 hydrocarbyl and where R.sub.6 is C.sub.2 to about C.sub.25 hydrocarbyl and wherein hydrocarbyl is selected from the group consisting of alkyl, alkenyl, aryl, alkaryl or aralkyl and optionally contains O, S, or N or mixtures thereof and where X=0-20, Y=0-20, Z=0-20, and X+Y+Z must equal at least 1.