WO2022074512A1 - Ashless additive composition - Google Patents
Ashless additive composition Download PDFInfo
- Publication number
- WO2022074512A1 WO2022074512A1 PCT/IB2021/058896 IB2021058896W WO2022074512A1 WO 2022074512 A1 WO2022074512 A1 WO 2022074512A1 IB 2021058896 W IB2021058896 W IB 2021058896W WO 2022074512 A1 WO2022074512 A1 WO 2022074512A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- branched
- independently
- linear
- lubricating oil
- chain monovalent
- Prior art date
Links
- 239000000654 additive Substances 0.000 title claims abstract description 46
- 230000000996 additive effect Effects 0.000 title claims abstract description 28
- 239000000203 mixture Substances 0.000 title claims description 59
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 8
- 239000010687 lubricating oil Substances 0.000 claims description 35
- 125000004122 cyclic group Chemical group 0.000 claims description 24
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 21
- 229940014800 succinic anhydride Drugs 0.000 claims description 21
- 239000002199 base oil Substances 0.000 claims description 16
- 229920000768 polyamine Polymers 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical group NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000012530 fluid Substances 0.000 claims description 9
- 230000005540 biological transmission Effects 0.000 claims description 7
- 239000000314 lubricant Substances 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 5
- 239000003607 modifier Substances 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- UVLSCMIEPPWCHZ-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-amine Chemical compound NCCCN1CCNCC1 UVLSCMIEPPWCHZ-UHFFFAOYSA-N 0.000 claims description 2
- YONXRSPFKCGRNL-UHFFFAOYSA-N 4-piperazin-1-ylbutan-1-amine Chemical compound NCCCCN1CCNCC1 YONXRSPFKCGRNL-UHFFFAOYSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- AVIUZWRRHOTPTG-UHFFFAOYSA-N NCCN1NCCCCC1 Chemical compound NCCN1NCCCCC1 AVIUZWRRHOTPTG-UHFFFAOYSA-N 0.000 claims description 2
- DYLSVSLHFDCBFN-UHFFFAOYSA-N NCCN1NCCCCCC1 Chemical compound NCCN1NCCCCCC1 DYLSVSLHFDCBFN-UHFFFAOYSA-N 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 239000006078 metal deactivator Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 239000007866 anti-wear additive Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 239000012208 gear oil Substances 0.000 claims 1
- 239000003879 lubricant additive Substances 0.000 abstract description 3
- 239000003921 oil Substances 0.000 description 29
- 235000019198 oils Nutrition 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000012360 testing method Methods 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 239000010705 motor oil Substances 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 125000004420 diamide group Chemical group 0.000 description 3
- 150000003949 imides Chemical group 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- -1 polybutylenes Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 2
- NEAFLGWVOVUKRO-UHFFFAOYSA-N 9-methylidenenonadecane Chemical compound CCCCCCCCCCC(=C)CCCCCCCC NEAFLGWVOVUKRO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229920001973 fluoroelastomer Polymers 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- RSPWVGZWUBNLQU-FOCLMDBBSA-N 3-[(e)-hexadec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCCCCCC\C=C\C1CC(=O)OC1=O RSPWVGZWUBNLQU-FOCLMDBBSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical group COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- 229910000978 Pb alloy Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000010710 diesel engine oil Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 229920006213 ethylene-alphaolefin copolymer Polymers 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000006358 imidation reaction Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/086—Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/36—Seal compatibility, e.g. with rubber
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/45—Ash-less or low ash content
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/52—Base number [TBN]
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/045—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for continuous variable transmission [CVT]
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Definitions
- This disclosure relates to lubricating oil additives and lubricating oil compositions containing the same. More specifically, this disclosure describes ashless additives that can increase total base number and/or modify friction and/or improve wear performance in lubricating oils.
- Lubricating oils are often formulated to a specific total base number (TBN) or TBN range. This ensures that the lubricating oils contain sufficient basic additives and/or detergents to neutralize acidic byproducts that can damage engine parts.
- Conventional base-containing additives such as overbased phenate and sulfonate detergents carry with them an abundance of metal as measured by sulfated ash. This presents challenges as industry and regulatory standards keep pushing towards ash restriction.
- Basic amine additives are an alternative to ash containing overbased metal detergents. At least one drawback is that amine additives can degrade fluoroelastomers which are commonly found in seals (e.g., Viton seals).
- Basic amine additives such as succinimide dispersants, contain polyamine head-groups, which are believed to cause dehydrofluorination in fluoroelastomeric seals.
- Certain additives may be multi-functional (e.g., friction modifier, anti- wear) and provide more than one performance benefit.
- an ashless additive composition comprising: tertiary amine-containing compound having the following structure: wherein R 1 and R 2 are independently a linear or branched-chain monovalent hydrocarbyl group having two to about twenty carbon atoms, each m is independently from 0 to 4, each p is independently from 0 to 4, for each cyclic moiety m + p is from 2 to 4, and n is independently from 1 to 6.
- a lubricating oil composition comprising: a major amount of a base oil; and an ashless tertiary amine-containing compound having the following structure: wherein R 1 and R 2 are independently a linear or branched-chain monovalent hydrocarbyl group having two to about twenty carbon atoms, each m is independently from 0 to 4, each p is independently from 0 to 4, for each cyclic moiety m + p is from 2 to 4, and n is independently from 1 to 6.
- an ashless additive composition comprising diamide product of a reaction comprising: a hydrocarbyl-substituted succinic anhydride represented by the following structure: wherein R 1 is a linear or branched-chain monovalent hydrocarbyl group having two to about twenty carbon atoms; and a cyclic polyamine represented by the following structure: wherein R 2 is a linear or branched-chain monovalent hydrocarbyl group having two to about twenty carbon atoms, m is from 0 to 4, p is from 0 to 4, m + p is from 2 to 4, and n is from 1 to 6; and wherein the hydrocarbyl-substituted succinic anhydride to cyclic polyamine ratio is from about 1.5:1 to about 1.6:1.
- a method for operating an internal combustion engine comprising lubricating said engine with a lubricating oil composition comprising: a major amount of base oil of lubricating viscosity; and an ashless tertiary amine containing composition having the following structure:
- R 1 and R 2 are independently a linear or branched-chain monovalent hydrocarbyl group having two to about twenty carbon atoms, each m is independently from 0 to 4, each p is independently from 0 to 4, for each cyclic moiety m + p is from 2 to 4, and each n is independently from 1 to 6.
- FIG. 1 shows a graph illustrating an aspect of the present invention as described in the Examples.
- FIG. 2 shows a graph illustrating an aspect of the present invention as described in the Examples.
- total base number refers to the amount of base equivalent to milligrams of KOH in 1 gram of sample as measured by the ASTM D- 2896 test.
- hydrocarbyl refers to a chemical group or moiety derived from hydrocarbons including saturated and unsaturated hydrocarbons.
- hydrocarbyl groups include alkenyl, alkyl, polyalkenyl, polyalkyl, phenyl, and the like.
- the present invention relates to an ashless additive composition that can be utilized as a TBN source and/or friction modifier and/or anti-wear agent in lubricating oil.
- the additive composition can be used at cost-effective treat rates while maintaining fluoroelastomer seal compatibility.
- the present invention may also be used as a friction modifier which reduces friction and wear in machine components.
- the ashless additive composition of the present invention includes product(s) of a reaction involving a hydrocarbyl-substituted succinic anhydride and a cyclic polyamine.
- the result is a diamide structure featuring at least two basic tertiary amines.
- the ashless additive composition of the present invention may be synthesized by any known compatible method such as those described in, for example, U.S. Patent Publication No. 20180034635 and U.S. Patent No. 7,091,306, which are hereby incorporated by reference.
- the reaction may proceed under various conditions. Generally, the hydrocarbyl-substituted succinic anhydride is reacted with the cyclic polyamine at a temperature of about 130°C to 220°C (e.g., 140°C to 200°C, 145°C to 175°C, etc.). More preferably, the temperature may range from about 160°C to 215°C. In general, the imidation step may be carried out at lower temperatures (e.g., 150°C to 170°C) while higher temperatures (e.g., 200°C to 220°C) may be necessary to complete the amidation step. [020] The reaction can be carried out under an inert atmosphere, such as nitrogen or argon.
- an inert atmosphere such as nitrogen or argon.
- a suitable molar charge of hydrocarbyl-substituted succinic anhydride to cyclic polyamine is from about 1.4:1 to about 1.7:1, more preferably from about 1.5:1 to about 1.6:1.
- CMR charge mole ratio
- the charge mole ratio is important as too much hydrocarbyl- substituted succinic anhydride can result in mono amide/acid structure instead of the diamide structure while too little can result in mono succinimide products containing secondary amines.
- the reaction may proceed in multiple steps, wherein the total CMR of hydrocarbyl-substituted succinic anhydride to cyclic polyamine or cyclic polyamine product is from about 1.4:1 to about 1.7:1, more preferably from about 1.5:1 to about 1.6:1.
- the first step may involve the reaction between the hydrocarbyl-substituted succinic anhydride and cyclic polyamine in a 1 :1 charge mole ratio to generate the imide structure.
- the imide structure is reacted with hydrocarbyl-substituted succinic anhydride at about 0.5 charge mole ratio (succinic anhydride to imide product) to form the diamide structure.
- the total CMR of the two steps is 1.5:1.
- the hydrocarbyl-substituted succinic anhydride in the first step and hydrocarbyl-substituted succinic anhydride in the second step may be the same or may differ in the hydrocarbyl groups.
- hydrocarbyl-substituted succinic anhydride is given by Structure I:
- R 1 is a linear or branched-chain monovalent hydrocarbyl group having two to about twenty carbon atoms, such as from ten to twenty carbon atoms, twelve to twenty carbon atoms, and fourteen to twenty carbon atoms. In some embodiments, the average number of carbons is about 14 or higher.
- R 1 may be cyclic or acylic. In some embodiments, R 1 is saturated. In other embodiments, R 1 is unsaturated.
- hydrocarbyl group may depend on a number of factors. Solubility in oil is an important consideration. In general, longer hydrocarbyl groups have greater solubility in oil.
- hydrocarbyl-substituted succinic anhydrides are commercially readily available.
- alkenyl succinic anhydrides are widely used in paper sizing.
- hydrocarbyl-substituted succinic anhydrides of the present invention may be synthesized by well-established methods.
- One conventional synthesis involves reacting maleic anhydride with an olefin at elevated temperatures ( ⁇ 200°C).
- the cyclic polyamine is represented by
- Structure II Structure II wherein R 2 is a linear or branched-chain monovalent hydrocarbyl group having two to about twenty carbon atoms, m is from 0 to 4, p is from 0 to 4, wherein m + p is from 2 to 4, and n is from 1 to 6.
- R 2 may be cyclic or acylic. In some embodiments, R 2 is saturated. In other embodiments, R 2 is unsaturated.
- the cyclic polyamine serves as the source of basic tertiary amines.
- Suitable examples of cyclic polyamines include, for example, aminoethyl piperazine, aminopropyl piperazine, aminobutyl piperazine, aminoethyl diazepane, aminoethyl diazocane, suitable derivatives thereof, and the like.
- One class of ashless additive composition may be represented by Structure III:
- R 1 and R 2 are independently a linear or branched-chain monovalent hydrocarbyl group having two to about twenty carbon atoms, each m is independently from 0 to 4, each p is independently from 0 to 4, for each cyclic moiety m + p from 2 to 4 and each n is independently from 1 to 6.
- the ashless additive composition of the present invention is usually present in the lubricating oil composition in concentrations ranging from about 0.001 to about 20 wt. % (including, but not limited to, 0.01 to 5 wt. %, 0.2 to 4 wt. %, 0.5 to 3 wt. %, 1 to 2 wt. %, and so forth), based on the total weight of the lubricating oil composition.
- Oils used as the base oil will be selected or blended depending on the desired end use and the additives in the finished oil to give the desired grade of engine oil, e.g. a lubricating oil composition having an Society of Automotive Engineers (SAE) Viscosity Grade of 0W, 0W-8, 0W-16, 0W-20, 0W-30, 0W-40, 0W-50, 0W-60, 5W, 5W- 20, 5W-30, 5W-40, 5W-50, 5W-60, 10W, 10W-20, 10W-30, 10W-40, 10W-50, 15W, 15W-20, 15W-30, or 15W-40.
- SAE Society of Automotive Engineers
- the oil of lubricating viscosity (sometimes referred to as “base stock” or “base oil”) is the primary liquid constituent of a lubricant, into which additives and possibly other oils are blended, for example to produce a final lubricant (or lubricant composition).
- a base oil which is useful for making concentrates as well as for making lubricating oil compositions therefrom, may be selected from natural (vegetable, animal or mineral) and synthetic lubricating oils and mixtures thereof.
- base stocks and base oils in this disclosure are the same as those found in American Petroleum Institute (API) Publication 1509 Annex E ("API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils," December 2016).
- Group I base stocks contain less than 90% saturates and/or greater than 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
- Group II base stocks contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120 using the test methods specified in Table E-1.
- Group III base stocks contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 120 using the test methods specified in Table E-1.
- Group IV base stocks are polyalphaolefins (PAO).
- Group V base stocks include all other base stocks not included in Group I, II, III, or IV.
- Natural oils include animal oils, vegetable oils (e.g., castor oil and lard oil), and mineral oils. Animal and vegetable oils possessing favorable thermal oxidative stability can be used. Of the natural oils, mineral oils are preferred. Mineral oils vary widely as to their crude source, for example, as to whether they are paraffinic, naphthenic, or mixed paraffinic-naphthenic. Oils derived from coal or shale are also useful. Natural oils vary also as to the method used for their production and purification, for example, their distillation range and whether they are straight run or cracked, hydrorefined, or solvent extracted.
- Synthetic oils include hydrocarbon oil.
- Hydrocarbon oils include oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene isobutylene copolymers, ethylene-olefin copolymers, and ethylene- alphaolefin copolymers).
- Polyalphaolefin (PAO) oil base stocks are commonly used synthetic hydrocarbon oil.
- PAOs derived from C 8 to C 14 olefins e.g., C 8 , C 10 , C 12 , C 14 olefins or mixtures thereof, may be utilized.
- base oils include non-conventional or unconventional base stocks that have been processed, preferably catalytically, or synthesized to provide high performance characteristics.
- Non-conventional or unconventional base stocks/base oils include one or more of a mixture of base stock(s) derived from one or more Gas-to-Liquids (GTL) materials, as well as isomerate/isodewaxate base stock(s) derived from natural wax or waxy feeds, mineral and or non-mineral oil waxy feed stocks such as slack waxes, natural waxes, and waxy stocks such as gas oils, waxy fuels hydrocracker bottoms, waxy raffinate, hydrocrackate, thermal crackates, or other mineral, mineral oil, or even non- petroleum oil derived waxy materials such as waxy materials received from coal liquefaction or shale oil, and mixtures of such base stocks.
- Other base oils include Coal to liquid (CTL) products and alkyl-naphthalene.
- Base oils for use in the lubricating oil compositions of present disclosure are any of the variety of oils corresponding to API Group I, Group II, Group III, Group IV, and Group V oils, and mixtures thereof, preferably API Group II, Group III, Group IV, and Group V oils, and mixtures thereof, more preferably the Group III to Group V base oils due to their exceptional volatility, stability, viscometric and cleanliness features.
- the base oil will have a kinematic viscosity at 100°C (ASTM D445) in a range of 1.5 to 35 mm 2 /s (e.g., 1.5 to 25 mm 2 /s, 2.0 to 20 mm 2 /s, or 2.0 to 15 mm 2 /s).
- the present lubricating oil compositions may also contain conventional lubricant additives for imparting auxiliary functions to give a finished lubricating oil composition in which these additives are dispersed or dissolved.
- the lubricating oil compositions can be blended with antioxidants, ashless dispersants, anti-wear agents, detergents such as metal detergents, rust inhibitors, dehazing agents, demulsifying agents, friction modifiers, metal deactivating agents, pour point depressants, viscosity modifiers, antifoaming agents, co-solvents, package compatibilizers, corrosion-inhibitors, dyes, extreme pressure agents and the like and mixtures thereof.
- a variety of the additives are known and commercially available. These additives, or their analogous compounds, can be employed for the preparation of the lubricating oil compositions of the invention by the usual blending procedures.
- each of the foregoing additives when used, is used at a functionally effective amount to impart the desired properties to the lubricant.
- a functionally effective amount of this ashless dispersant would be an amount sufficient to impart the desired dispersancy characteristics to the lubricant.
- the concentration of each of these additives, when used may range, unless otherwise specified, from about 0.001 to about 20 wt. %, such as about 0.01 to about 10 wt. %.
- the following non-limiting examples are illustrative of the present invention. Brief descriptions of how the examples were prepared are provided.
- the reactor was heated to 195°C under a nitrogen sweep and maintained for 1 hour. The mixture was then cooled down to ambient temperature.
- reaction mixture was reheated the following day to 200°C while applying vacuum up to 35 mm Hg.
- the reaction mixture was held at temperature for an additional 2.5 hours.
- Example 11 This Example is a composite of Example 11, Example 15, and Example 16.
- a baseline lubricating oil formulation was formed containing ashless dispersants, alkaline earth metal carboxylate, sulfonate, and phenate detergents, zinc dithiophosphate, non-dispersant viscosity index improver, antioxidants, foam inhibitor, and pour point depressant.
- This sample is an automotive engine oil with a conventional amine- containing additive.
- HTCBT High Temperature Corrosion Bench Test
- the ASTM D6594 HTCBT was used to evaluate engine lubricants to determine their tendency to corrode various metals, specifically alloys of lead and copper commonly used in cam followers and bearings.
- Four metal specimens of copper, lead, tin and phosphor bronze were immersed in engine oil. The oil, at an elevated temperature (170°C), was blown with air (5 l/h) for a period of time (168 h).
- Lubricating oil samples were also tested for their wear performance using High Frequency Reciprocating Rig (HFRR) test.
- HFRR High Frequency Reciprocating Rig
- Comparative Example C includes a baseline lubricating oil.
- Example 6 includes the baseline lubricating oil of Comparative Example C and an ashless additive of the present invention (reaction product of C 18 succinic anhydride and aminoethyl piperazine).
- Example 7 includes the lubricating oil of Comparative Example C and a conventional amine-containing additive.
- Samples (Comparative Example D, Examples 8 and 9) including ashless additive compositions of the present invention were tested in automatic transmission fluid. The static torque was measured using JASO SAE #2 friction test. Figure 2 shows the SAE #2 results.
- This sample includes a baseline automatic transmission fluid and the reaction product of C 20 succinic anhydride and diethylenetriamine (DETA) at 2:1 charge mole ratio.
- the treat rate is 1.0 wt%.
- This sample includes the baseline automatic transmission fluid used in Comparative Example D and the reaction product of C 18 succinic anhydride and aminoethyl piperazine at 1.6:1 charge mole ratio.
- the treat rate is 1.0 wt%.
- This sample includes the baseline automatic transmission fluid used in Comparative Example D and the reaction product of C 20 succinic anhydride and aminoethyl piperazine at 1.6:1 charge mole ratio.
- the treat rate is 1.19 wt%.
- ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited, as well as, ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited, in the same way, ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
- ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited.
- within a range includes every point or individual value between its end points even though not explicitly recited. Thus, every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited.
- compositions, an element or a group of elements are preceded with the transitional phrase “comprising,” it is understood that we also contemplate the same composition or group of elements with transitional phrases “consisting essentially of,” “consisting of,” “selected from the group of consisting of,” or “is” preceding the recitation of the composition, element, or elements and vice versa.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2023520556A JP2023543939A (en) | 2020-10-05 | 2021-09-29 | Ashless additive composition |
EP21787056.7A EP4225877A1 (en) | 2020-10-05 | 2021-09-29 | Ashless additive composition |
US17/764,608 US20240093115A1 (en) | 2020-10-05 | 2021-09-29 | Ashless additive composition |
CN202180071362.8A CN116323877A (en) | 2020-10-05 | 2021-09-29 | Ashless additive composition |
CA3197324A CA3197324A1 (en) | 2020-10-05 | 2021-09-29 | Ashless additive composition |
US17/710,033 US20220220410A1 (en) | 2020-10-05 | 2022-03-31 | Ashless additive composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202063087584P | 2020-10-05 | 2020-10-05 | |
US63/087,584 | 2020-10-05 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US17/764,608 A-371-Of-International US20240093115A1 (en) | 2020-10-05 | 2021-09-29 | Ashless additive composition |
US17/710,033 Continuation-In-Part US20220220410A1 (en) | 2020-10-05 | 2022-03-31 | Ashless additive composition |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022074512A1 true WO2022074512A1 (en) | 2022-04-14 |
Family
ID=78080399
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2021/058896 WO2022074512A1 (en) | 2020-10-05 | 2021-09-29 | Ashless additive composition |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP4225877A1 (en) |
JP (1) | JP2023543939A (en) |
CN (1) | CN116323877A (en) |
CA (1) | CA3197324A1 (en) |
WO (1) | WO2022074512A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023191886A1 (en) * | 2022-03-31 | 2023-10-05 | Chevron Oronite Company Llc | Ashless additive composition |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3200076A (en) * | 1963-03-28 | 1965-08-10 | California Research Corp | Polypiperazinyl succinimides in lubricating oils |
EP1508610A1 (en) * | 2002-05-30 | 2005-02-23 | Idemitsu Kosan Co., Ltd. | Lubricating oil additive composition for internal combustion engine |
US20060160709A1 (en) * | 2003-06-23 | 2006-07-20 | Hiroaki Koshima | Lubricating oil additive and lubricating oil composition |
US7091306B2 (en) | 2003-05-09 | 2006-08-15 | Chevron Oronite Company Llc | Process for preparing polyalkenylsuccinimides |
US20180034635A1 (en) | 2015-04-08 | 2018-02-01 | Huawei Technologies Co., Ltd. | GPRS System Key Enhancement Method, SGSN Device, UE, HLR/HSS, and GPRS System |
-
2021
- 2021-09-29 CN CN202180071362.8A patent/CN116323877A/en active Pending
- 2021-09-29 JP JP2023520556A patent/JP2023543939A/en active Pending
- 2021-09-29 CA CA3197324A patent/CA3197324A1/en active Pending
- 2021-09-29 WO PCT/IB2021/058896 patent/WO2022074512A1/en active Application Filing
- 2021-09-29 EP EP21787056.7A patent/EP4225877A1/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3200076A (en) * | 1963-03-28 | 1965-08-10 | California Research Corp | Polypiperazinyl succinimides in lubricating oils |
EP1508610A1 (en) * | 2002-05-30 | 2005-02-23 | Idemitsu Kosan Co., Ltd. | Lubricating oil additive composition for internal combustion engine |
US7091306B2 (en) | 2003-05-09 | 2006-08-15 | Chevron Oronite Company Llc | Process for preparing polyalkenylsuccinimides |
US20060160709A1 (en) * | 2003-06-23 | 2006-07-20 | Hiroaki Koshima | Lubricating oil additive and lubricating oil composition |
US20180034635A1 (en) | 2015-04-08 | 2018-02-01 | Huawei Technologies Co., Ltd. | GPRS System Key Enhancement Method, SGSN Device, UE, HLR/HSS, and GPRS System |
Non-Patent Citations (4)
Title |
---|
"Chemistry of Organic Compounds", 1957, SAUNDERS |
"Encyclopedia of Chemical Technology", vol. 2, pages: 99 - 116 |
"The Organic Chemistry of Nitrogen", 1966, CLARENDON PRESS |
ZAGIDULLIN R N ET AL: "Development of Procedures for the Manufacture of New Ashless Polymer Additives Derived From Imido Derivatives of Succinic Acid", CHEMISTRY AND TECHNOLOGY OF FUELS AND OILS, CONSULTANTS BUREAU, US, vol. 53, no. 4, 4 November 2017 (2017-11-04), pages 488 - 493, XP036364827, ISSN: 0009-3092, [retrieved on 20171104], DOI: 10.1007/S10553-017-0827-1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023191886A1 (en) * | 2022-03-31 | 2023-10-05 | Chevron Oronite Company Llc | Ashless additive composition |
Also Published As
Publication number | Publication date |
---|---|
CN116323877A (en) | 2023-06-23 |
CA3197324A1 (en) | 2022-04-14 |
EP4225877A1 (en) | 2023-08-16 |
JP2023543939A (en) | 2023-10-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5178197B2 (en) | Tartaric acid derivatives and their preparation as fuel economy improvers and antiwear agents in crankcase oil | |
US8193132B2 (en) | Lubricating oil additive and lubricating oil composition containing same | |
US11773341B2 (en) | Lubricating oil compositions | |
US8193131B2 (en) | Lubricating oil additive and lubricating oil composition containing same | |
EP4225878A1 (en) | Friction modifier system | |
WO2022074512A1 (en) | Ashless additive composition | |
WO2009053413A1 (en) | Use of a lubricating composition comprising a poly(hydroxycarboxylic) acid | |
US20240093115A1 (en) | Ashless additive composition | |
WO2023191886A1 (en) | Ashless additive composition | |
US20230085359A1 (en) | Lubricating oil compositions with improved oxidative performance comprising alkylated diphenylamine antioxidant and sulfonate detergents | |
EP4211210A1 (en) | Lubricating oil containing alkyl phosphonic acid | |
WO2024030899A1 (en) | Lubricating oil composition for corrosion control | |
EP4077605A1 (en) | Lubricating oil compositions comprising a polyalphaolefin | |
CA3189295A1 (en) | Magnesium and boron containing lubricating oil composition for hybrid vehicles | |
WO2021181285A1 (en) | Lubricating oil compositions with improved oxidative performance comprising alkylated diphenylamine antioxidant and carboxylate detergents | |
KR20230110571A (en) | lubricating oil composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 17764608 Country of ref document: US |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 21787056 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 3197324 Country of ref document: CA |
|
ENP | Entry into the national phase |
Ref document number: 2023520556 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2021787056 Country of ref document: EP Effective date: 20230508 |