# US 11,299,690 B2 · Additive concentrates > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,299,690 B2 - Document ID: US11299690B2 - Status: Granted - Kind: B2 - Application number: 15/465,651 - Filed: 2017-03-22 - Published: 2017-09-28 - Granted: 2022-04-12 - Earliest claimed: 2016-03-22 - Assignees: Infineum International Limited - Applicants: Infineum International Limited - Inventors: Philip J. Woodward; Adam P. Marsh - Web page: https://patentgrep.com/patent/US11299690B2 ## CPC - C10M 129/74: of polyhydroxy compounds - C10M 129/54: containing hydroxy groups - C10M 129/68: Esters (epoxidised C10M129/66) - C10M 163/00: Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential - C10M 169/04: Mixtures of base-materials and additives - C10M 2203/1006: used as base material - C10M 2203/1025: used as base material - C10M 2207/129: having hydrocarbon chains of thirty or more carbon atoms - C10M 2207/144: containing hydroxy groups - C10M 2207/262: derived from hydroxy substituted aromatic acids, e.g. salicylates - C10M 2207/283: of polyhydroxy compounds - C10M 2207/289: containing free hydroxy groups - C10M 2207/34: Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives - C10M 2215/28: Amides; Imides - C10M 2219/068: Thiocarbamate metal salts - C10N 2010/04: Groups 2 or 12 - C10N 2020/04: Molecular weight; Molecular weight distribution - C10N 2030/04: Detergent property or dispersant property - C10N 2030/52: {Base number [TBN]} - C10N 2030/70: {Soluble oils} - C10N 2040/25: Internal-combustion engines - C10N 2040/252: {Diesel engines} - C10N 2040/255: {Gasoline engines} - C10N 2070/02: {Concentrating of additives} - 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 The use of polyalkylenyl succinic anhydrides to stabilise an additive concentrate which includes a salicylate detergent and a nitrogen-free ashless organic friction modifier. ## Claims ### Claim 1 An additive concentrate for use in forming a lubricating oil composition, the additive concentrate comprising diluent oil of lubricating viscosity present in a minor amount of less than 50 mass %, based on the total mass of the additive concentrate, and a plurality of oil-soluble or oil-dispersible additives contained therein, wherein the combined amount of all of said plurality of additives in the additive concentrate is greater than 50 mass % on an active ingredient basis, based on the total mass of the additive concentrate, and wherein the plurality of additives include the following additives: (A) one or more oil-soluble or oil-dispersible overbased alkaline earth metal salicylate detergent(s) having a TBN at 100% active mass of 200 to 600 mg KOH/g, as measured in accordance with ASTM D2896 present in an amount of from 5 to 20 mass % on an active ingredient basis, based on the total mass of the additive concentrate wherein the alkaline earth metal is Ca or Mg; (B) one or more oil-soluble or oil-dispersible ashless nitrogen-free organic friction modifier(s) which is one or more aliphatic (C11 to C23)hydrocarbyl fatty acid ester(s) present in an amount of from 1.0 to 7.5 mass % on an active ingredient basis, based on the total mass of the additive concentrate wherein the one or more aliphatic (C11 to C23)hydrocarbyl fatty acid ester(s) is the ester reaction product of one or more aliphatic (C11 to C23)hydrocarbyl fatty acid(s) and one or more alkanol(s) and the alkanol(s) is a polyhydric (C2 to C20)alkanol(s); and, (C) one or more oil-soluble or oil-dispersible poly(C2 to C6)alkylenyl succinic anhydride(s) present in an effective amount to stabilise the additive concentrate, wherein: 1) the number average molecular weight (Mn) of the poly(C2 to C6)alkylenyl chain(s) of the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is 1400 to 7000 daltons; 2) the poly(C2 to C6)alkylenyl succinic anhydride(s) is present in an amount of from 1.5 to 7.5 mass % on an active ingredient basis, based on the total mass of the additive concentrate, and has a succination ratio of 1.35 to 4.00; 3) the poly(C2 to C6)alkylenyl succinic anhydride(s) comprises one or more poly(C4)alkylenyl succinic anhydrides; and where (A) and (C) are blended into the additive concentrate and the additive concentrate does not show a sediment volume over 0.05 mass %, is clear and bright, and has no phase separation as determined by the Storage Stability Test. ### Claim 2 (depends on 1) An additive concentrate as claimed in claim 1, wherein the number average molecular weight (Mn) of the poly(C2 to C6)alkylenyl chain(s) of the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is 1500 to 4000 daltons. ### Claim 3 (depends on 1) An additive concentrate as claimed in claim 1, wherein the number average molecular weight (Mn) of the poly(C2 to C6)alkylenyl chain(s) of the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is 1700 to 3000 daltons. ### Claim 4 (depends on 1) An additive concentrate as claimed in claim 1, wherein the number average molecular weight (Mn) of the poly(C2 to C6)alkylenyl chain(s) of the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is 1500 to 3000 daltons. ### Claim 5 (depends on 1) An additive concentrate as claimed in claim 1, wherein the average saponification value (SAP value) of the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is greater than or equal to 45, as measured in accordance with ASTM D94. ### Claim 6 (depends on 1) An additive concentrate as claimed in claim 1, wherein the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is one or more polyisobutylenyl succinic anhydride(s) (PIBSA(s)). ### Claim 7 (depends on 1) An additive concentrate as claimed in claim 1, wherein the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is present in an amount of from 3.0 to 5.0 mass % on an active ingredient basis, based on the total mass of the additive concentrate. ### Claim 8 (depends on 1) An additive concentrate as claimed in claim 1, wherein the one or more aliphatic (C11 to C23)hydrocarbyl fatty acid(s) is selected from the group consisting of: oleic acid, linoleic acid, linoelaidic acid, linolenic acid. ### Claim 9 (depends on 1) An additive concentrate as claimed in claim 1, wherein the one or more polyhydric (C2 to C20)alkanol(s) selected from glycerol, neopentyl glycol, trimethylolethane, trimethylolpropane, tri methylol butane, pentaerythritol, dipentaerythritol, tripentaerythritol and sorbitol. ### Claim 10 (depends on 1) An additive concentrate as claimed in claim 1, wherein the polyhydric (C2 to C2o)alkanol(s) is glycerol. ### Claim 11 (depends on 1) An additive concentrate as claimed in claim 1, wherein the one or more aliphatic (C7 to C29)hydrocarbyl fatty acid ester(s) is glycerol mono-oleate (GMO). ### Claim 12 (depends on 1) An additive concentrate as claimed in claim 1, wherein the one or more alkaline earth metal salicylate detergent(s) is one or more calcium salicylate detergent(s). ### Claim 13 An additive concentrate for use in forming a lubricating oil composition, the additive concentrate comprising diluent oil of lubricating viscosity present in a minor amount of less than 50 mass %, based on the total mass of the additive concentrate, and a plurality of oil-soluble or oil-dispersible additives contained therein, wherein the combined amount of all of said plurality of additives in the additive concentrate is greater than 50 mass % on an active ingredient basis, based on the total mass of the additive concentrate, and wherein the plurality of additives include the following additives: (A) one or more oil-soluble or oil-dispersible overbased calcium salicylate detergent(s) having a TBN at 100% active mass of 200 to 600 mg KOH/g, as measured in accordance with ASTM D 2896, present in an amount of from 5 to 20 mass % on an active ingredient basis, based on the total mass of the additive concentrate; (B) glycerol mono-oleate present in an amount of from 1.0 to 7.5 mass on an active ingredient basis, based on the total mass of the additive concentrate; and (C) one or more oil-soluble or oil-dispersible poly(isobuteneyl) succinic anhydride(s) wherein: i) the number average molecular weight (Mn) of the poly(isobuteneyl) chain(s) of the one or more poly(isobuteneyl) succinic anhydride(s) is 1700 to 3000 daltons; ii) the poly(isobuteneyl) succinic anhydride(s) is present in an amount of from 1.5 to 7.5 mass % on an active ingredient basis, based on the total mass of the additive concentrate and has a succination ratio of 1.35 to 4.00; iii) the poly(isobuteneyl) succinic anhydride(s) is present in an effective amount to stabilise the additive concentrate, where the additive concentrate does not show a sediment volume over 0.05 mass %, is clear and bright, and has no phase separation as determined by the Storage Stability Test. ### Claim 14 (depends on 13) The additive concentrate of claim 13, wherein the poly(isobuteneyl) succinic anhydride(s) has a succination ratio of 1.45 to 3.50. ### Claim 15 (depends on 13) The additive concentrate of claim 13, wherein the number average molecular weight (Mn) of the poly(isobuteneyl) chain(s) of the one or more poly(isobuteneyl) succinic anhydride(s) is Mn of 1700 to 2500 daltons. ### Claim 16 (depends on 1) An additive concentrate as claimed in claim 1, wherein the number average molecular weight (Mn) of the poly(C2 to C6)alkylenyl chain(s) of the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is 1500 to 4000 daltons. ### Claim 17 (depends on 1) The additive concentrate of claim 1, wherein the poly(isobuteneyl) succinic anhydride(s) has a succination ratio of 1.50 to 2.75. ### Claim 18 (depends on 13) The additive concentrate of claim 13, wherein the poly(isobuteneyl) succinic anhydride(s) has a succination ratio of 1.50 to 2.75. ### Claim 19 (depends on 1) The additive concentrate of claim 1, wherein the poly(isobuteneyl) succinic anhydride(s) has a succination ratio of 1.45 to 3.50. ### Claim 20 An additive concentrate for use in forming a lubricating oil composition, the additive concentrate comprising diluent oil of lubricating viscosity present in a minor amount of less than 50 mass %, based on the total mass of the additive concentrate, and a plurality of oil-soluble or oil-dispersible additives contained therein, wherein the combined amount of all of said plurality of additives in the additive concentrate is greater than 50 mass % on an active ingredient basis, based on the total mass of the additive concentrate, and wherein the plurality of additives include the following additives: (A) one or more oil-soluble or oil-dispersible overbased calcium salicylate detergent(s) having a TBN at 100% active mass of 250 to 600 mg KOH/g, as measured in accordance with ASTM D 2896, present in an amount of from 5 to 25 mass % on an active ingredient basis, based on the total mass of the additive concentrate; (B) glycerol mono-oleate present in an amount of from 1.0 to 10.0 mass % on an active ingredient basis, based on the total mass of the additive concentrate; and (C) one or more oil-soluble or oil-dispersible poly(isobuteneyl) succinic anhydride(s) wherein: i) the number average molecular weight (Mn) of the poly(isobuteneyl) chain(s) of the one or more poly(isobuteneyl) succinic anhydride(s) is 1700 to 3000 daltons; ii) the poly(isobuteneyl) succinic anhydride(s) is present in an amount of from 1.5 to 7.5 mass % on an active ingredient basis, based on the total mass of the additive concentrate; iii) the poly(isobuteneyl) succinic anhydride(s) has a succination ratio of 1.50 to 2.75; and iv) the poly(isobuteneyl) succinic anhydride(s) is present in an effective amount to stabilise the additive concentrate; where (A) and (C) are blended into the additive concentrate. ### Claim 21 (depends on 13) The additive concentrate of claim 13, wherein overbased calcium salicylate detergent(s) has a TBN at 100% active mass of at least 250 to 600 mg KOH/g, as measured in accordance with ASTM D2896. ### Claim 22 (depends on 1) The additive concentrate of claim 1, wherein overbased alkaline earth metal salicylate detergent(s) has a TBN at 100% active mass of 250 to 600 mg KOH/g, as measured in accordance with ASTM D2896. ### Claim 23 (depends on 1) An additive concentrate as claimed in claim 1, wherein: a) the number average molecular weight (Mn) of the poly(C2 to C6)alkylenyl chain(s) of the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is 1700 to 3000 daltons; and b) the one or more polyhydric (C2 to C20)alkanol(s) is glycerol; and c) the one or more alkaline earth metal salicylate detergent(s) is one or more calcium salicylate detergent(s); and d) the one or more poly(C2 to C6)alkylenyl succinic anhydride(s) is one or more polyisobutylenyl succinic anhydride(s). ### Claim 24 (depends on 23) The additive concentrate of claim 23, wherein the poly(isobuteneyl) succinic anhydride(s) has a succination ratio of 1.45 to 3.50. ### Claim 25 (depends on 1) The additive concentrate of claim 1 wherein the one or more oil-soluble or oil-dispersible poly(C2 to C6)alkylenyl succinic anhydride(s) has a succination ratio of 1.35 to 3.50. ### Claim 26 (depends on 1) The additive concentrate of claim 1 wherein the one or more aliphatic (C11 to C23)hydrocarbyl fatty acid(s) is selected from the group consisting of: myristoleic acid, palmitoleic acid, sapienic acid, hexadecatrienoic acid, oleic acid, stearidonic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, eicosenoic acid, erucic acid, docosahexaenoic acid, docosahexaenoic acid, tetracosapentaenoic acid and tetracosatetraenoic acid.