# US 7,608,568 B2 · Tetraaromatic diamine compounds as antioxidants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,608,568 B2 - Document ID: US7608568B2 - Status: Granted - Kind: B2 - Application number: 11/706,116 - Filed: 2007-02-13 - Published: 2007-11-29 - Granted: 2009-10-27 - Earliest claimed: 2006-05-24 - Assignees: Chemtura Corporation - Inventors: Qinggao Ma - Web page: https://patentgrep.com/patent/US7608568B2 ## CPC - C07C 243/22: having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings - C10M 133/26: containing a nitrogen-to-nitrogen double bond - C07C 2602/08: the other ring being five-membered, e.g. indane - C10M 2203/1006: used as base material - C10M 2205/02: containing acyclic monomers - C10M 2207/026: with tertiary alkyl groups - C10M 2207/16: Naphthenic acids - C10M 2215/064: Di- and triaryl amines - C10M 2215/065: Phenyl-Naphthyl amines - C10M 2215/18: Containing nitrogen-to-nitrogen bonds, e.g. hydrazine - C10M 2215/28: Amides; Imides - C10M 2219/022: of hydrocarbons, e.g. olefines - C10M 2219/046: Overbased sulfonic acid salts - C10M 2219/066: Thiocarbamic type compounds - C10M 2219/087: containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols - C10M 2219/108: Phenothiazine - C10M 2223/045: Metal containing thio derivatives - C10N 2010/14: Group 7 - C10N 2010/16: Groups 8, 9, or 10 - C10N 2030/10: Inhibition of oxidation, e.g. anti-oxidants - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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) - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS ## Abstract Tetraaromatic diamine compounds having the general formula: are provided wherein a is 0-3; b, c and d independently are integers from 0-5, R1 and R2 together with the carbon atoms to which they are bonded are joined together to form a substituted or unsubstituted C3 to about C30 ring, saturated, partially unsaturated or fully unsaturated, optionally substituted with one or more heteroatoms, a is 0-3; b, c and d independently are integers from 0-5, R3, R4, R5 and R6 are independently hydrogen, a straight or branched C1-C30 alkyl or alkylene group optionally substituted with one or more substituents, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C5-C25 aryl, a substituted or unsubstituted C6-C25 arylalkyl, a straight or branched C1-C30 alkoxy group optionally substituted with one or more substituents or two R4 substituents and/or two R5 substituents and/or two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith can be joined together to form a substituted or unsubstituted C3 to about C30 ring, saturated, partially unsaturated or fully unsaturated, optionally substituted with one or more heteroatoms. Lubricating oil compositions containing the tetraaromatic diamine compound additives are also provided. ## Claims ### Claim 1 A tetraaromatic diamine compound having the general formula: wherein a is 0-3; b, c and d independently are integers from 0-5, R1 and R2 together with the carbon atoms to which they are bonded are joined together to form a saturated or partially saturated C3 to about C30 ring, R3, R4, R5 and R6 are independently hydrogen, a straight or branched C1-C30 alkyl or alkylene group optionally substituted with one or more substituents, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C5-C25 aryl, a substituted or unsubstituted C6-C25 arylalkyl, a straight or branched C1-C30 alkoxy group optionally substituted with one or more substituents. ### Claim 2 (depends on 1) The tetraaromatic diamine compound of claim 1, wherein R1 and R2 are joined together to form a saturated 5-, 6-, or 7-membered ring. ### Claim 3 (depends on 1) The tetraaromatic diamine compound of claim 1, wherein R1 and R2 are joined together to form a partially unsaturated 5-, 6-, or 7-membered ring. ### Claim 4 (depends on 1) The tetraaromatic diamine compound of claim 1, wherein two R4 substituents and two R5 substituents and two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith are joined together to form a saturated or partially unsaturated C3 to about C30 ring. ### Claim 5 (depends on 1) The tetraaromatic diamine compound of claim 1, wherein two substituents and two R5 substituents and two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith are joined together to form a saturated 5-, 6-, or 7-membered ring. ### Claim 6 (depends on 1) The tetraaromatic diamine compound of claim 1, wherein two R4 substituents and two R5 substituents and two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith are joined together to form a partially unsaturated 5-, 6-, or 7-membered ring. ### Claim 7 (depends on 1) The tetraaromatic diamine compound of claim 1, wherein R1 and R2 are joined together to form a saturated or partially unsaturated 5-, 6-, or 7-membered ring and two R4 substituents and two R5 substituents and two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith are joined together to form a substituted or unsubstituted and saturated or partially unsaturated 5-, 6-, or 7-membered ring. ### Claim 8 A lubricating oil composition comprising (a) at least one oil of lubricating viscosity and (b) an antioxidant improving effective amount of at least one tetraaromatic diamine compound having the general formula: wherein a is 0-3; b, c and d independently are integers from 0-5, R1 and R2 together with the carbon atoms to which they are bonded are joined together to form a saturated or partially saturated C3 to about C30 ring R3, R4, R5 and R6 are independently hydrogen, a straight or branched C1-C30 alkyl or alkylene group optionally substituted with one or more substituents, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C5-C25 aryl, a substituted or unsubstituted C6-C25 arylalkyl, a straight or branched C1-C30 alkoxy group optionally substituted with one or more substituents. ### Claim 9 (depends on 8) The lubricating oil composition of claim 8, wherein in the tetraaromatic diamine compound R1 and R2 are joined together to form a saturated 5-, 6-, or 7-membered ring. ### Claim 10 (depends on 8) The lubricating oil composition of claim 8, wherein in the tetraaromatic diamine compound R1 and R2 are joined together to form a partially unsaturated 5-, 6-, or 7-membered ring. ### Claim 11 (depends on 1) The lubricating oil composition of claim 1, wherein two R4 substituents and two R5 substituents and two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith are joined together to form a saturated or partially unsaturated C3 to about C30 ring. ### Claim 12 (depends on 8) The lubricating oil composition of claim 8, wherein in the tetraaromatic diamine compound R1 and R2 are joined together to form a saturated or partially unsaturated 5-, 6-, or 7-membered ring and two R4 substituents and two R5 substituents and two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith are joined together to form a saturated or partially unsaturated 5-, 6-, or 7-membered ring. ### Claim 13 (depends on 8) The lubricating oil composition of claim 8, wherein the at least one oil of lubricating viscosity is selected from the group consisting of engine oils, transmission fluids, hydraulic fluids, gear oils, marine cylinder oils, compressor oils, refrigeration lubricants and mixtures thereof. ### Claim 14 (depends on 8) The lubricating oil composition of claim 8, further comprising at least one lubricating oil additive selected from the group consisting of antioxidants, anti-wear agents, detergents, rust inhibitors, dehazing agents, demulsifying agents, metal deactivating agents, friction modifiers, pour point depressants, antifoaming agents, co-solvents, package compatibilisers, corrosion-inhibitors, ashless dispersants, dyes, extreme pressure agents and mixtures thereof. ### Claim 15 (depends on 8) The lubricating oil composition of claim 8, further comprising at least one lubricating oil additive selected from the group consisting of an alkylated diphenylamine, alkylated hindered phenolic, alkylated substituted or unsubstituted phenylenediamine, alkylated oil soluble copper compound, alkylated sulfur containing compound known to impart oxidation stability and mixtures thereof. ### Claim 16 (depends on 15) The lubricating oil composition of claim 15, wherein the alkylated sulfur containing compound known to impart oxidation stability is selected from the group consisting of phenothiazines, sulfurized olefins, thiocarbamates, sulfur bearing hindered phenolics, zinc dialkyldithiophosphates and mixtures thereof. ### Claim 17 (depends on 8) The lubricating oil composition of claim 8, having a phosphorous content of less than about 0.1 weight percent. ### Claim 18 (depends on 1) An additive package comprising about 1 to about 75 weight of at least one tetraaromatic diamine compound of claim 1. ### Claim 19 (depends on 1) A stabilizer-containing composition comprising (a) an organic material subject to oxidative, thermal, and/or light-induced degradation and in need of stabilization to prevent or inhibit such degradation; and (b) a stabilization effective amount of at least one tetraaromatic diamine compound of claim 1. ### Claim 20 (depends on 1) A method for stabilizing an organic material subject to oxidative, thermal, and/or light-induced degradation and in need of stabilization to prevent or inhibit such degradation, the method comprising adding to the organic material a stabilizing amount of at least one tetraaromatic diamine compound of claim 1. ### Claim 21 (depends on 1) The tetraaromatic diamine compound of claim 1, wherein two R4 substituents and/or two R5 substituents and/or two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith are joined together to form a saturated or partially saturated C3 to about C30 ring. ### Claim 22 (depends on 8) The lubricating oil composition of claim 8, wherein two R4 substituents and/or two R5 substituents and/or two R6 substituents on adjacent carbon atoms of the aromatic ring associated therewith are joined together to form a saturated or partially saturated C3 to about C30 ring.