EP0072645B1 - Improved succinimide lubricating oil dispersant - Google Patents
Improved succinimide lubricating oil dispersant Download PDFInfo
- Publication number
- EP0072645B1 EP0072645B1 EP82304066A EP82304066A EP0072645B1 EP 0072645 B1 EP0072645 B1 EP 0072645B1 EP 82304066 A EP82304066 A EP 82304066A EP 82304066 A EP82304066 A EP 82304066A EP 0072645 B1 EP0072645 B1 EP 0072645B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyamine
- anhydride
- composition
- succinic anhydride
- dispersant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002270 dispersing agent Substances 0.000 title claims description 36
- 239000010687 lubricating oil Substances 0.000 title claims description 35
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 title description 6
- 229960002317 succinimide Drugs 0.000 title description 3
- 229920000768 polyamine Polymers 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 41
- 229940014800 succinic anhydride Drugs 0.000 claims description 30
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 25
- -1 alkyl succinic anhydride Chemical compound 0.000 claims description 23
- 239000000654 additive Substances 0.000 claims description 17
- 229920000098 polyolefin Polymers 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000003599 detergent Substances 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 229920002367 Polyisobutene Polymers 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical group CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 235000006708 antioxidants Nutrition 0.000 claims description 4
- 239000007866 anti-wear additive Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims 1
- 150000003818 basic metals Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000003921 oil Substances 0.000 description 12
- 150000008064 anhydrides Chemical class 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 239000010802 sludge Substances 0.000 description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012797 qualification Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000089 Cyclic olefin copolymer Chemical class 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 229910000071 diazene Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 3
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical class CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004148 curcumin Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003879 lubricant additive Substances 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical class [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000004653 carbonic acids Chemical class 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
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- 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
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
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- C—CHEMISTRY; METALLURGY
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
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- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- 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
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- 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
- C10M2207/027—Neutral salts thereof
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- 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
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
- C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
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- C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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- C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- 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
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- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
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- 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
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
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- 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
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
- C10M2225/041—Hydrocarbon polymers
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- 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
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- 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
- C10N2070/02—Concentrating of additives
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B1/00—Engines characterised by fuel-air mixture compression
- F02B1/02—Engines characterised by fuel-air mixture compression with positive ignition
- F02B1/04—Engines characterised by fuel-air mixture compression with positive ignition with fuel-air mixture admission into cylinder
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Definitions
- This invention relates to lubricating oil dispersants which exhibit highly effective dispersant potency in both gasoline and diesel engines. More particularly, the invention relates to lubricating oil compositions for use both in gasoline and diesel engine formulations which meet current performance requirements for both types of engines, the formulations being characterized as containing novel dispersants prepared in a particular reaction sequence.
- a current objective in the industry is to provide lubricating oil compositions which meet or exceed engine qualification standards of dispersancy for both gasoline and diesel or compression ignition engines.
- dispersants have been developed which meet one or the other of these requirements, but development of a dispersant which satisfies the highest service classification requirements of the relevant engine qualification tests for both types of oils has not been entirely successful. It is an object of the present invention to provide lubricating oil compositions containing novel dispersants which meet these goals.
- the present invention is within the broad field of improved polyolefin, particularly polyisobutenyl, succinic acid or anhydride-polyamine reaction product dispersants, and such dispersants are disclosed generally, for example, in U.S. Patent 3,172,892 issued March 9, 1965 to LeSuer et al.
- U.S Patent 3,216,936 issued November 9, 1965 to LeSuer shows lubricating oil additives prepared by acylation of an alkylene amine with both a polyolefin succinic anhydride and an aliphatic monocarboxylic acid, perhaps a mono acid having more than 12 carbon atoms such as stearic or oleic acid.
- the products can be prepared by reacting both acidic compounds simultaneously with a polyamine or by first reacting the polyolefin succinic acid with polyamine and subsequently with monocarboxylic acid.
- the products so formed are said to be particularly useful in improving the thermal stability of lubricating compositions which contain metal phos- phorodithioates.
- British Patent 1,018,982 (1966) discloses lubricating oil additives which are the reaction products of three components: alkenyl succinic anhydrides, polyamines and carboxylic acids and the products are said to have improved sludge dispersant properties.
- alkenyl succinic anhydrides are those similar to the materials of the present invention, i.e., preferably polyisobutenyl succinic anhydrides and the polyamines are also similar, i.e., the alkylene polyamines.
- the carboxylic acids of this reference are disclosed as being mono- or di- carboxylic acids having 1 to 30, preferably 1 to 18 carbon atoms, with acetic acid being preferred since it forms an imidazoline or pyrimidine with a minimum of carbon atoms.
- This reference also states that lower molecular weight carboxylic acids are more effective in promoting the sludge dispersing activity of the final product.
- the preparative method disclosed in British Patent 1,018,982 comprises either first reacting the carboxylic acid and the polyamine in what is described as an imidazoline or pyrimidine forming reaction with subsequent reaction with alkenyl succinic anhydride or by reacting the three materials simultaneously.
- U.S. Patent 3,415,750 issued December 10, 1968 to Anzenberger discloses lubricant additives categorized as imidazolines which are prepared by reacting a polyethylene polyamine with a mono-carboxylic acid or a dicarboxylic acid to form a heterocyclic imidazoline intermediate which is subsequently reacted with a polyalkenyl succinic anhydride to provide a bis-imidazoline which is said to have improved detergency and dispersancy in lubricating oil formulations.
- U.S. Patent 3,374,174 issued March 19, 1968 to LeSuer discloses lubricant additives prepared by reacting amines, including alkylene polyamines, with both a high molecular weight saturated monocarboxylic acid and a dicarboxylic acid or anhydride, preferably those having up to 12 carbons.
- the patent discloses the simultaneous reaction of all three materials or a sequential process whereby there is first formed an acylated amine intermediate with the amine and high molecular weight carboxylic acid which is subsequently reacted with the dicarboxylic acid reactant.
- U.S. 4,173,540 discloses the reaction of polyisobutenyl succinic anhydride with polyamines in a molar ratio of 2.0 to 2.5 moles of anhydride per mole of polyamine to provide a diimide dispersant, however, such products will not meet the requirements for both gasoline and diesel engine formulations.
- U.S. 3,401,118 discloses reacting tetraethylene pentamine first with polyisobutenyl succinic anhydride (PIBSA) derived from 850-1200 Mn polyisobutylene and then reacting this intermediate with PIBSA derived from polyisobutylene of 400-750 Mn; the 400 Mn corresponding to 29 carbon atoms.
- PIBSA polyisobutenyl succinic anhydride
- GB-A-1162436 discloses the preparation of an ashless dispersant by the reaction of at least an equivalent amount of an alkylene amine with a substantially aliphatic substituted derivative of succinic acid or anhydride and the product is reacted with a non-critical quantity of a second substantially aliphatic substituted derivative of succinic acid or anhydride.
- the present invention distinguishes from these references in requiring a particular two-step reaction sequence characterised by the molar ratio of anhydride to polyamine in the first step, the use of particular dicarboxylic acid anhydride in the final step and an overall mole ratio of anhydride to polyamine within a relatively narrow and critically defined range.
- These parameters have been found essential to provide lubricating oil compositions which give demonstrated performance values in engine tests required to qualify for the highest grade service classifications for both gasoline and diesel engine lubricating oils.
- the reaction sequence is particularly critical; thus products prepared in a simultaneous reaction technique will not meet the objectives of this invention.
- lubricating oil compositions exhibiting improved dispersancy in both gasoline and diesel engines comprising a major amount of lubricating oil and an effective amount of a polyalkenyl succinimide dispersant, said dispersant being prepared in a two-step sequential process comprising (a) first reacting a polyalkenyl succinic anhydride, the polyalkenyl being a polymer of a C 3 or C 4 olefin, and an alkylene polyamine of the formula H 2 N(CH 2 ) n (NH(CH 2 ) n ) m NH 2 , wherein n is 2 or 3 and m is 0 to 10, and (b) reacting the product of step (a) with a dicarboxylic acid anhydride, there being a molar ratio of from 1.0 to 2.2 moles of succinic anhydride per mole of polyamine in step (a) and the dicarboxylic acid anhydride being selected from the group consisting
- the polyalkenyl succinic anhydrides useful in the present invention generally comprise those wherein the polyalkenyl group has a Mn (number average molecular weight) of 700 to 5,000, preferably 900 to 2,000.
- Mn number average molecular weight
- the methods of preparation are well known in the art, i.e., reaction of maleic anhydride with either the polyolefin itself or with a chlorinated polyolefin which in either case provides the desired polyalkenyl succinic anhydride.
- Polyisobutylene is preferred but other polymers of C 3 or C 4 olefins such as polybutene-1 and polypropylene are suitable including mixtures of such polyolefins.
- Suitable alkylene polyamines are also well known represented by the formula NH 2 (CH 2 ) n (NH(CH 2 ) n ) m NH 2 , wherein n is 2 to 3 and m is 0 to 10.
- Illustrative are ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, and the like.
- Preferred for use is tetraethylene pentamine or a mixture of ethylene polyamines which approximates tetraethylene pentamine such as "DOW E-100" (a commercial mixture available from Dow Chemical Company, Midland, Michigan).
- polyalkenyl succinimide dispersant or diimide dispersant as used herein is meant to encompass the completed reaction product of the sequential process and is intended to encompass compounds wherein the product may have amide, amidine or salt linkages in addition to the imide linkage which results from the reaction of the primary amino group and the anhydride moiety.
- the third reactant used to prepare the dispersants of the present invention encompasses maleic anhydride, succinic anhydride or an alkenyl or alkyl succinic anhydride having up to about 18 carbon atoms and preferably at least 8 carbon atoms.
- Particularly advantageous results in terms of engine performance data have been obtained with dodecenyl succinic anhydride and maleic anhydride and the use of these materials, and the dispersants produced thereby, represent particularly preferred embodiments.
- both the reaction sequence and the overall final mole ratio of total succinic anhydride groups to polyamine in the finished product have been found to be essential to meet the objective of passing both engine qualification tests for gasoline and diesel lubricating oil formulations.
- the reaction sequence requires a first step in the preparation of a polyisobutenyl succinic anhydride-polyamine reaction product. These are reacted in a mole ratio of 1.0 to 2.2 moles of polyisobutenyl succinic anhydride per mole of polyamine.
- Suitable solvent oils are the same as the oils used as a lubricating oil base stock and these generally include lubricating oils having a viscosity (ASTM D-445) of 2 to 40, preferably 5 to 20, mm 2 /sec at 99°C, with the primarily paraffinic mineral oils being particularly preferred, such as Solvent 150 Neutral.
- Lubricating oil compositions are prepared containing the dispersant of the present invention together with conventional amounts of other additives to provide their normal attendant functions such as viscosity index improvers, rust inhibitors, metal detergent additives, antioxidants, and zinc dialkyldithiophosphates anti-wear additives and these compositions meet the objective of passing engine qualification tests for both gasoline and diesel engine usage.
- lubricating oil formulations must equal or exceed certain values in the MS Sequence VD Engine Test (ASTM Special Publication 315).
- MS Sequence VD Engine Test ASTM Special Publication 315).
- the significant values in this test are a minimum of 9.4 sludge, 6.7 piston skirt varnish and 6.6 average varnish.
- the Sequence VD uses a 1980 Ford 2.3 liter 4-cylinder engine and is a 192-hour test comprising the cyclic operation at varying engine speeds and temperatures to simulate "stop and go" city driving and moderate turnpike operation.
- the test is an established industry standard.
- the Caterpillar 1-H/2 test is the current standard to evaluate the effects of a crankcase oil on ring sticking and piston deposits. The test simulates high speed, moderately supercharged engine operation. This test is also Federal Test Method 791-346 and is used to meet military specifications such as MIL-L-21260B and industry specifications such as SAE 183 and General Motors GM6146M.
- WTD Weighted Total Demerits
- WTD is a cumulative rating based on observation of deposits in the groove and land areas of the piston and lacquer on piston skirts with all the specific evaluation being rated according to their relative importance and the final WTD being calculated in accordance with the test procedure.
- the dispersants prepared according to the invention can be incorporated in a wide variety of lubricants. They can be used in lubricating oil compositions, such as automotive crankcase lubricating oils, automatic transmission fluids, etc. in effective amounts to provide active ingredient concentrations in finished formulations generally within the range of 0.5 to 10 weight percent, for example, 1 to 5 weight percent, preferably 1.5 to 3 weight percent, of the total composition.
- the dispersants are admixed with the lubricating oils as dispersant solution concentrates which usually contain up to about 50 percent weight of the active ingredient additive compound dissolved in mineral oil, preferably a mineral oil having an ASTM D-445 viscosity of 2 to 40, preferably 5 to 20 centistokes at 991y 5 to 20 centistokes at 99°C.
- mineral oil preferably a mineral oil having an ASTM D-445 viscosity of 2 to 40, preferably 5 to 20 centistokes at 991y 5 to 20 centistokes at 99°C.
- the lubricating oil includes not only hydrocarbon oils of lubricating viscosity derived from petroleum but also includes synthetic lubricating oils such as polyethylene oils; alkyl esters of dicarboxylic acids, complex esters of dicarboxylic acid, polyglycol and alcohol; alkyl esters of carbonic or phosphoric acids; polysilico- nes; fluorohydrocarbon oils; and mixtures or lubricating oils and synthetic oils in any proportion, etc.
- the term "lubricating oil" for this disclosure includes all the foregoing.
- the useful dispersant may be conveniently dispersed as a concentrate of 10 to 80 weight percent, preferably up to about 50 weight percent, of said dispersant in 20 to 90 weight percent of mineral oil, e.g., Solvent 150 Neutral oil with or without other additives being present and such concentrates are a further embodiment of this invention.
- mineral oil e.g., Solvent 150 Neutral oil with or without other additives being present and such concentrates are a further embodiment of this invention.
- Such lubricating oil compositions containing the dispersants of the present invention will also contain other well-known additives such as the zinc dialkyl (C 3 -C a ) dithiophosphate anti-wear inhibitors, generally present in amounts of about 1 to 5 weight percent.
- Useful detergents include the oil-soluble normal basic or over-based metal, e.g., calcium, magnesium, barium, etc., salts of petroleum naphthenic acids, petroleum sulfonic acids, alkyl benzene sulfonic acids, oil-soluble fatty acids, alkyl salicylic acids, alkylene bis-phenols and hydrolyzed phosphosulfurized polyolefins.
- Typical amounts are from 1 to 7 weight percent with the HD or diesel oils usually containing slightly more of this metal detergent additive.
- Preferred detergents are the calcium and magnesium normal or overbased phenates, sulfurized phenates or sulfonates.
- Diesel lubricating oils preferably contain 4-6 percent of this additive.
- Oxidation inhibitors include hindered phenols, e.g., 2.6-ditertbutyl-para-cresol, amines, sulfurized phenols and alkyl phenothiazines usually present in amounts of from 0.001 to 1 weight percent.
- Pour point depressants which may be present in amounts of from 0.01 to 1 weight percent include wax alkylated aromatic hydrocarbons, olefin polymers and copolymers, acrylate and methacrylate polymers and copolymers.
- Viscosity index improvers which may vary from 1 to 15 weight percent depending on the viscosity grade required include olefin polymers such as polybutene, ethylene-propylene copolymers, hydrogenated polymers and copolymers and terpolymers of styrene with isoprene and/or butadiene, polymers of alkyl acrylates or alkyl methacrylates, copolymers of alkyl methacrylates with N-vinyl pyrrolidone or dimethylaminoalkyl methacrylate, post-grafted polymers of ethylene-propylene with an active monomer such as maleic anhydride which may be further reacted with an alcohol or an alkylene polyamine, styrene/ maleic anhydride polymers post-treated with alcohols and amines, etc.
- olefin polymers such as polybutene, ethylene-propylene copolymers, hydrogenated polymers and copolymers and terpol
- Rust inhibition activity can be provided by about 0.01 to 1 weight percent of the aforementioned metal dihydrocarbyl dithiophosphates and the corresponding precursor esters, phosphosulfurized pinenes, sulfurized olefins and hydrocarbons, sulfurized fatty esters and sulfurized alkyl phenols.
- Preferred are the zinc dihydrocarbyl dithiophosphates which are salts of dihydrocarbyl esters of dithiophosphoric acids.
- additives include effective amounts of the fuel economy additives or friction reducing additives such as the dimer acid esters, as disclosed in U.S. 4,105,571 to Shaub et al, which are present in amounts of 1 to 5 weight percent with esters of dimerized linoleic acid and diethylene glycol being a preferred material.
- Glycerol oleates are another example of fuel economy additives and these are usually present in very small amounts, such as 0.05 to 0.2 weight percent based on the weight of the formulated oil.
- Example 2 was repeated except that 2.2 grams of maleic anhydride was used to provide a product having a final mole ratio of 2.4 moles of anhydride per mole of polyamine. The product analyzed for 1.53 percent N.
- Example 3 The product of Example 3 was included as the dispersant at a concentration of 3.6 weight percent active ingredient in a formulated SAE 10W40 lubricating oil composition and subjected to the ASTM Sequence VD engine test for gasoline engines.
- the formulation also contained conventional amounts of overbased sulfonate, zinc dialkyl dithiophosphate, antioxidant, olefin copolymer viscosity index improver, rust inhibitor and anti-foam additive. The results were as follows:
- Example 2 and Example 3 were included in a 10W30 quality HD (diesel) lubricating oil formulations as the dispersant at 2.5 weight percent active ingredient concentration and the oil was evaluated for diesel dispersancy performance in the Caterpillar 1-H/2 test.
- the formulation also contained olefin copolymer V.I. improver to provide the 10W30 viscosity grade, 3.1 wt.% of a mixture of overbased and normal metal phenates, 1.5 weight percent of zinc dialkyl dithiophosphate anti-wear additive, and very small proportions of anti-oxidant (0.3%) and antifoamant (0.2%).
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
- This invention relates to lubricating oil dispersants which exhibit highly effective dispersant potency in both gasoline and diesel engines. More particularly, the invention relates to lubricating oil compositions for use both in gasoline and diesel engine formulations which meet current performance requirements for both types of engines, the formulations being characterized as containing novel dispersants prepared in a particular reaction sequence.
- A current objective in the industry is to provide lubricating oil compositions which meet or exceed engine qualification standards of dispersancy for both gasoline and diesel or compression ignition engines. Heretofore, dispersants have been developed which meet one or the other of these requirements, but development of a dispersant which satisfies the highest service classification requirements of the relevant engine qualification tests for both types of oils has not been entirely successful. It is an object of the present invention to provide lubricating oil compositions containing novel dispersants which meet these goals.
- The present invention is within the broad field of improved polyolefin, particularly polyisobutenyl, succinic acid or anhydride-polyamine reaction product dispersants, and such dispersants are disclosed generally, for example, in U.S. Patent 3,172,892 issued March 9, 1965 to LeSuer et al.
- U.S Patent 3,216,936 issued November 9, 1965 to LeSuer shows lubricating oil additives prepared by acylation of an alkylene amine with both a polyolefin succinic anhydride and an aliphatic monocarboxylic acid, praferably a mono acid having more than 12 carbon atoms such as stearic or oleic acid. The products can be prepared by reacting both acidic compounds simultaneously with a polyamine or by first reacting the polyolefin succinic acid with polyamine and subsequently with monocarboxylic acid. The products so formed are said to be particularly useful in improving the thermal stability of lubricating compositions which contain metal phos- phorodithioates.
- British Patent 1,018,982 (1966) discloses lubricating oil additives which are the reaction products of three components: alkenyl succinic anhydrides, polyamines and carboxylic acids and the products are said to have improved sludge dispersant properties. The alkenyl succinic anhydrides are those similar to the materials of the present invention, i.e., preferably polyisobutenyl succinic anhydrides and the polyamines are also similar, i.e., the alkylene polyamines. The carboxylic acids of this reference are disclosed as being mono- or di- carboxylic acids having 1 to 30, preferably 1 to 18 carbon atoms, with acetic acid being preferred since it forms an imidazoline or pyrimidine with a minimum of carbon atoms. This reference also states that lower molecular weight carboxylic acids are more effective in promoting the sludge dispersing activity of the final product. The preparative method disclosed in British Patent 1,018,982 comprises either first reacting the carboxylic acid and the polyamine in what is described as an imidazoline or pyrimidine forming reaction with subsequent reaction with alkenyl succinic anhydride or by reacting the three materials simultaneously.
- U.S. Patent 3,415,750 issued December 10, 1968 to Anzenberger discloses lubricant additives categorized as imidazolines which are prepared by reacting a polyethylene polyamine with a mono-carboxylic acid or a dicarboxylic acid to form a heterocyclic imidazoline intermediate which is subsequently reacted with a polyalkenyl succinic anhydride to provide a bis-imidazoline which is said to have improved detergency and dispersancy in lubricating oil formulations.
- U.S. Patent 3,374,174 issued March 19, 1968 to LeSuer discloses lubricant additives prepared by reacting amines, including alkylene polyamines, with both a high molecular weight saturated monocarboxylic acid and a dicarboxylic acid or anhydride, preferably those having up to 12 carbons. The patent discloses the simultaneous reaction of all three materials or a sequential process whereby there is first formed an acylated amine intermediate with the amine and high molecular weight carboxylic acid which is subsequently reacted with the dicarboxylic acid reactant.
- U.S. 4,173,540 discloses the reaction of polyisobutenyl succinic anhydride with polyamines in a molar ratio of 2.0 to 2.5 moles of anhydride per mole of polyamine to provide a diimide dispersant, however, such products will not meet the requirements for both gasoline and diesel engine formulations.
- U.S. 3,401,118 discloses reacting tetraethylene pentamine first with polyisobutenyl succinic anhydride (PIBSA) derived from 850-1200 Mn polyisobutylene and then reacting this intermediate with PIBSA derived from polyisobutylene of 400-750 Mn; the 400 Mn corresponding to 29 carbon atoms.
- GB-A-1162436 discloses the preparation of an ashless dispersant by the reaction of at least an equivalent amount of an alkylene amine with a substantially aliphatic substituted derivative of succinic acid or anhydride and the product is reacted with a non-critical quantity of a second substantially aliphatic substituted derivative of succinic acid or anhydride.
- The present invention distinguishes from these references in requiring a particular two-step reaction sequence characterised by the molar ratio of anhydride to polyamine in the first step, the use of particular dicarboxylic acid anhydride in the final step and an overall mole ratio of anhydride to polyamine within a relatively narrow and critically defined range. These parameters have been found essential to provide lubricating oil compositions which give demonstrated performance values in engine tests required to qualify for the highest grade service classifications for both gasoline and diesel engine lubricating oils. The reaction sequence is particularly critical; thus products prepared in a simultaneous reaction technique will not meet the objectives of this invention.
- In accordance with this invention, there are provided lubricating oil compositions exhibiting improved dispersancy in both gasoline and diesel engines comprising a major amount of lubricating oil and an effective amount of a polyalkenyl succinimide dispersant, said dispersant being prepared in a two-step sequential process comprising (a) first reacting a polyalkenyl succinic anhydride, the polyalkenyl being a polymer of a C3 or C4 olefin, and an alkylene polyamine of the formula H2N(CH2)n(NH(CH2)n)mNH2, wherein n is 2 or 3 and m is 0 to 10, and (b) reacting the product of step (a) with a dicarboxylic acid anhydride, there being a molar ratio of from 1.0 to 2.2 moles of succinic anhydride per mole of polyamine in step (a) and the dicarboxylic acid anhydride being selected from the group consisting of maleic anhydride, succinic anhydride and Ci―Cia, preferably C8-C,8, alkenyl or alkyl succinic anhydrides in sufficient molar proportion to provide a diimide dispersant having a total mole ratio of from 2.3 to 3.0 moles of anhydride per mole of polyamine.
- The polyalkenyl succinic anhydrides useful in the present invention generally comprise those wherein the polyalkenyl group has a Mn (number average molecular weight) of 700 to 5,000, preferably 900 to 2,000. The methods of preparation are well known in the art, i.e., reaction of maleic anhydride with either the polyolefin itself or with a chlorinated polyolefin which in either case provides the desired polyalkenyl succinic anhydride. Polyisobutylene is preferred but other polymers of C3 or C4 olefins such as polybutene-1 and polypropylene are suitable including mixtures of such polyolefins.
- Suitable alkylene polyamines are also well known represented by the formula NH2(CH2)n(NH(CH2)n)mNH2, wherein n is 2 to 3 and m is 0 to 10. Illustrative are ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, and the like. Preferred for use is tetraethylene pentamine or a mixture of ethylene polyamines which approximates tetraethylene pentamine such as "DOW E-100" (a commercial mixture available from Dow Chemical Company, Midland, Michigan).
- The terms polyalkenyl succinimide dispersant or diimide dispersant as used herein is meant to encompass the completed reaction product of the sequential process and is intended to encompass compounds wherein the product may have amide, amidine or salt linkages in addition to the imide linkage which results from the reaction of the primary amino group and the anhydride moiety.
- The third reactant used to prepare the dispersants of the present invention encompasses maleic anhydride, succinic anhydride or an alkenyl or alkyl succinic anhydride having up to about 18 carbon atoms and preferably at least 8 carbon atoms. Particularly advantageous results in terms of engine performance data have been obtained with dodecenyl succinic anhydride and maleic anhydride and the use of these materials, and the dispersants produced thereby, represent particularly preferred embodiments.
- In the present invention, both the reaction sequence and the overall final mole ratio of total succinic anhydride groups to polyamine in the finished product have been found to be essential to meet the objective of passing both engine qualification tests for gasoline and diesel lubricating oil formulations. The reaction sequence requires a first step in the preparation of a polyisobutenyl succinic anhydride-polyamine reaction product. These are reacted in a mole ratio of 1.0 to 2.2 moles of polyisobutenyl succinic anhydride per mole of polyamine. After this reaction is complete, sufficient maleic anhydride, succinic anhydride or alkenyl succinic anhydride is then reacted to provide a final overall mole ratio in the finished dispersant of 2.3 to 3.0, preferably 2.3 to 2.5, moles of anhydride per mole of polyamine.
- These reactions are carried out at conventional temperatures of 80°C to 200°C, more preferably 140°C to 165°C, using a conventional solvent media, such as a mineral lubricating oil solvent so that the final product is in a convenient solution in lubricating oil which is entirely compatible with a lubricating oil base stock. Suitable solvent oils are the same as the oils used as a lubricating oil base stock and these generally include lubricating oils having a viscosity (ASTM D-445) of 2 to 40, preferably 5 to 20, mm2/sec at 99°C, with the primarily paraffinic mineral oils being particularly preferred, such as Solvent 150 Neutral.
- Lubricating oil compositions are prepared containing the dispersant of the present invention together with conventional amounts of other additives to provide their normal attendant functions such as viscosity index improvers, rust inhibitors, metal detergent additives, antioxidants, and zinc dialkyldithiophosphates anti-wear additives and these compositions meet the objective of passing engine qualification tests for both gasoline and diesel engine usage. For gasoline engine lube oils to meet the current "SF" designation of the American Petroleum Institute, lubricating oil formulations must equal or exceed certain values in the MS Sequence VD Engine Test (ASTM Special Publication 315). For dispersancy, the significant values in this test are a minimum of 9.4 sludge, 6.7 piston skirt varnish and 6.6 average varnish. The Sequence VD uses a 1980 Ford 2.3 liter 4-cylinder engine and is a 192-hour test comprising the cyclic operation at varying engine speeds and temperatures to simulate "stop and go" city driving and moderate turnpike operation. The test is an established industry standard.
- For diesel performance the Caterpillar 1-H/2 test is the current standard to evaluate the effects of a crankcase oil on ring sticking and piston deposits. The test simulates high speed, moderately supercharged engine operation. This test is also Federal Test Method 791-346 and is used to meet military specifications such as MIL-L-21260B and industry specifications such as SAE 183 and General Motors GM6146M. For the 1H-2 Test WTD (Weighted Total Demerits) is the principal value and for a 240-hour test, the target is a value within or below the 90-100 range. This is derived from the published specification value of WTD 140 for a 480-hour test. WTD is a cumulative rating based on observation of deposits in the groove and land areas of the piston and lacquer on piston skirts with all the specific evaluation being rated according to their relative importance and the final WTD being calculated in accordance with the test procedure.
- The dispersants prepared according to the invention can be incorporated in a wide variety of lubricants. They can be used in lubricating oil compositions, such as automotive crankcase lubricating oils, automatic transmission fluids, etc. in effective amounts to provide active ingredient concentrations in finished formulations generally within the range of 0.5 to 10 weight percent, for example, 1 to 5 weight percent, preferably 1.5 to 3 weight percent, of the total composition. Conventionally, the dispersants are admixed with the lubricating oils as dispersant solution concentrates which usually contain up to about 50 percent weight of the active ingredient additive compound dissolved in mineral oil, preferably a mineral oil having an ASTM D-445 viscosity of 2 to 40, preferably 5 to 20 centistokes at 991y 5 to 20 centistokes at 99°C. The lubricating oil includes not only hydrocarbon oils of lubricating viscosity derived from petroleum but also includes synthetic lubricating oils such as polyethylene oils; alkyl esters of dicarboxylic acids, complex esters of dicarboxylic acid, polyglycol and alcohol; alkyl esters of carbonic or phosphoric acids; polysilico- nes; fluorohydrocarbon oils; and mixtures or lubricating oils and synthetic oils in any proportion, etc. The term "lubricating oil" for this disclosure includes all the foregoing. The useful dispersant may be conveniently dispersed as a concentrate of 10 to 80 weight percent, preferably up to about 50 weight percent, of said dispersant in 20 to 90 weight percent of mineral oil, e.g., Solvent 150 Neutral oil with or without other additives being present and such concentrates are a further embodiment of this invention.
- As noted above, such lubricating oil compositions containing the dispersants of the present invention will also contain other well-known additives such as the zinc dialkyl (C3-Ca) dithiophosphate anti-wear inhibitors, generally present in amounts of about 1 to 5 weight percent. Useful detergents include the oil-soluble normal basic or over-based metal, e.g., calcium, magnesium, barium, etc., salts of petroleum naphthenic acids, petroleum sulfonic acids, alkyl benzene sulfonic acids, oil-soluble fatty acids, alkyl salicylic acids, alkylene bis-phenols and hydrolyzed phosphosulfurized polyolefins. Typical amounts are from 1 to 7 weight percent with the HD or diesel oils usually containing slightly more of this metal detergent additive. Preferred detergents are the calcium and magnesium normal or overbased phenates, sulfurized phenates or sulfonates. Diesel lubricating oils preferably contain 4-6 percent of this additive.
- Oxidation inhibitors include hindered phenols, e.g., 2.6-ditertbutyl-para-cresol, amines, sulfurized phenols and alkyl phenothiazines usually present in amounts of from 0.001 to 1 weight percent.
- Pour point depressants which may be present in amounts of from 0.01 to 1 weight percent include wax alkylated aromatic hydrocarbons, olefin polymers and copolymers, acrylate and methacrylate polymers and copolymers.
- Viscosity index improvers which may vary from 1 to 15 weight percent depending on the viscosity grade required include olefin polymers such as polybutene, ethylene-propylene copolymers, hydrogenated polymers and copolymers and terpolymers of styrene with isoprene and/or butadiene, polymers of alkyl acrylates or alkyl methacrylates, copolymers of alkyl methacrylates with N-vinyl pyrrolidone or dimethylaminoalkyl methacrylate, post-grafted polymers of ethylene-propylene with an active monomer such as maleic anhydride which may be further reacted with an alcohol or an alkylene polyamine, styrene/ maleic anhydride polymers post-treated with alcohols and amines, etc.
- Rust inhibition activity can be provided by about 0.01 to 1 weight percent of the aforementioned metal dihydrocarbyl dithiophosphates and the corresponding precursor esters, phosphosulfurized pinenes, sulfurized olefins and hydrocarbons, sulfurized fatty esters and sulfurized alkyl phenols. Preferred are the zinc dihydrocarbyl dithiophosphates which are salts of dihydrocarbyl esters of dithiophosphoric acids.
- Other additives include effective amounts of the fuel economy additives or friction reducing additives such as the dimer acid esters, as disclosed in U.S. 4,105,571 to Shaub et al, which are present in amounts of 1 to 5 weight percent with esters of dimerized linoleic acid and diethylene glycol being a preferred material. Glycerol oleates are another example of fuel economy additives and these are usually present in very small amounts, such as 0.05 to 0.2 weight percent based on the weight of the formulated oil.
- This invention is further illustrated by the following examples which are not to be considered as limitative of its scope.
- 1500 grams of PIBSA (polyisobutenyl succinic anhydride, Mn=1300, Sap. No. 103) and 170 grams of an ethylene polyamine mixture ("Dow E-100", available from Dow Chemical Company, which approximates tetraethylene pentamine) were reacted in solution in 808 grams of Solvent 150 Neutral, a paraffinic mineral oil, at 160°C for 3 hours. The mole ratio of polyisobutenyl succinic anhydride to polyamine was 1.4: 1. Thereafter was added 225 grams of dodecenyl succinic anhydride which provided a final mole ratio of 2.4 moles of anhydride per mole of polyamine and this was reacted for 2 hours at 160°C. After filtration, the product analyzed at 1.83 percent N.
- 320 grams of the initial PIBSA/polyamine product of Example 1 being the same but having a mole ratio of 2.1 mole of succinic anhydride per mole of polyamine was reacted with6.0 grams of dodecenyl succinic anhydride in Solvent 150 Neutral at 160°C for 2 hours to provide a product having a final mole ratio of 2.4 moles of anhydride per mole of polyamine. The product analyzed for 1.50 percent N.
- Example 2 was repeated except that 2.2 grams of maleic anhydride was used to provide a product having a final mole ratio of 2.4 moles of anhydride per mole of polyamine. The product analyzed for 1.53 percent N.
- The product of Example 3 was included as the dispersant at a concentration of 3.6 weight percent active ingredient in a formulated SAE 10W40 lubricating oil composition and subjected to the ASTM Sequence VD engine test for gasoline engines. The formulation also contained conventional amounts of overbased sulfonate, zinc dialkyl dithiophosphate, antioxidant, olefin copolymer viscosity index improver, rust inhibitor and anti-foam additive. The results were as follows:
- Sludge=9.51; piston skirt varnish=7.06 and varnish=6.92. These results exceed the API "SF" minimum values of 9.4 sludge; 6.7 piston skirt varnish and 6.6 varnish and therefore indicate the material is a commercially useful dispersant.
- The products of Example 2 and Example 3 were included in a 10W30 quality HD (diesel) lubricating oil formulations as the dispersant at 2.5 weight percent active ingredient concentration and the oil was evaluated for diesel dispersancy performance in the Caterpillar 1-H/2 test. The formulation also contained olefin copolymer V.I. improver to provide the 10W30 viscosity grade, 3.1 wt.% of a mixture of overbased and normal metal phenates, 1.5 weight percent of zinc dialkyl dithiophosphate anti-wear additive, and very small proportions of anti-oxidant (0.3%) and antifoamant (0.2%).
-
- The critical nature of the final ratio of anhydride to polyamine was further demonstrated with additional Caterpillar 1-H/2 tests. In 11 tests using products similar to Examples 3 and 4 but having final mole ratios varying between 1.3 and 2.0, an average WTD value of 163 was obtained. Similarly, for an average of four engine tests where the final mole ratio was 2.1 to 2.2, an average value of 128 WTD was obtained.
Claims (12)
characterised in that in step (a) the polyolefin succinic anhydride is reacted with the polyamine in a molar ratio of from 1.0 to 2.2 moles of polyolefin succinic anhydride per mole of polyamine, and in step (b) the dicarboxylic acid anhydride is selected from the group consisting of maleic anhydride, succinic anhydride and C1-18 alkenyl or alkyl succinic anhydride and is in sufficient molar proportion to provide a total mole ratio of from 2.3 to 3.0 moles of anhydride compounds per mole of polyamine.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US29314681A | 1981-08-17 | 1981-08-17 | |
US293146 | 1981-08-17 |
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EP0072645A2 EP0072645A2 (en) | 1983-02-23 |
EP0072645A3 EP0072645A3 (en) | 1984-09-05 |
EP0072645B1 true EP0072645B1 (en) | 1987-01-07 |
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Application Number | Title | Priority Date | Filing Date |
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EP82304066A Expired EP0072645B1 (en) | 1981-08-17 | 1982-08-02 | Improved succinimide lubricating oil dispersant |
Country Status (5)
Country | Link |
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EP (1) | EP0072645B1 (en) |
JP (1) | JPS5838792A (en) |
BR (1) | BR8204774A (en) |
CA (1) | CA1190216A (en) |
DE (1) | DE3274976D1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0839840B2 (en) † | 1996-10-29 | 2016-01-20 | Idemitsu Kosan Company Limited | Lubricating oil additive comprising succinimide compound, and its use for diesel engines |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1265415A (en) * | 1984-12-27 | 1990-02-06 | Robert Edwin Quinn | Dispersant salts |
US4863624A (en) * | 1987-09-09 | 1989-09-05 | Exxon Chemical Patents Inc. | Dispersant additives mixtures for oleaginous compositions |
US5118432A (en) * | 1985-07-11 | 1992-06-02 | Exxon Chemical Patents Inc. | Dispersant additive mixtures for oleaginous compositions |
FR2586255B1 (en) * | 1985-08-14 | 1988-04-08 | Inst Francais Du Petrole | IMPROVED COMPOSITIONS OF DISPERSING ADDITIVES FOR LUBRICATING OILS AND THEIR PREPARATION |
US4663064A (en) * | 1986-03-28 | 1987-05-05 | Texaco Inc. | Dibaisic acid lubricating oil dispersant and viton seal additives |
CA1333596C (en) * | 1986-10-16 | 1994-12-20 | Robert Dean Lundberg | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous compositions |
CA1327088C (en) * | 1986-12-12 | 1994-02-15 | Malcolm Waddoups | Oil soluble additives useful in oleaginous compositions |
US5328624A (en) * | 1987-06-16 | 1994-07-12 | Exxon Chemical Patents Inc. | Stabilized grafted ethylene copolymer additive useful in oil compositions |
US4803003A (en) * | 1987-06-16 | 1989-02-07 | Exxon Chemical Patents Inc. | Ethylene copolymer viscosity index improver dispersant additive useful in oil compositions |
EP0438848A1 (en) * | 1990-01-25 | 1991-07-31 | Ethyl Petroleum Additives Limited | Inhibiting fluoroelastomer degradation during lubrication |
DE69014095T3 (en) * | 1990-01-25 | 1998-05-20 | Ethyl Petroleum Additives Ltd | Succinimide compositions. |
EP0444830A1 (en) * | 1990-02-26 | 1991-09-04 | Ethyl Petroleum Additives Limited | Succinimide composition |
FR2680791B1 (en) * | 1991-08-30 | 1994-09-09 | Bp Chemicals Snc | PROCESS FOR THE MANUFACTURE OF A CROSSLINKED POLYMER AND USE OF THE POLYMER. |
US5171421A (en) * | 1991-09-09 | 1992-12-15 | Betz Laboratories, Inc. | Method for controlling fouling deposit formation in a liquid hydrocarbonaceous medium |
IT1264624B1 (en) * | 1993-06-16 | 1996-10-04 | Euron Spa | OIL-SOLUBLE ADDUCTS BETWEEN UNSATURATED BICARBOXYLIC ALIPHATIC ACIDS AND ANHYDRIDES |
US5716912A (en) * | 1996-04-09 | 1998-02-10 | Chevron Chemical Company | Polyalkylene succinimides and post-treated derivatives thereof |
US5821205A (en) * | 1995-12-01 | 1998-10-13 | Chevron Chemical Company | Polyalkylene succinimides and post-treated derivatives thereof |
AU6516499A (en) * | 1998-10-30 | 2000-05-22 | Lubrizol Corporation, The | Improved dispersant by treatment with maleic anhydride |
JP4018328B2 (en) * | 2000-09-28 | 2007-12-05 | 新日本石油株式会社 | Lubricating oil composition |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US3415750A (en) * | 1963-10-04 | 1968-12-10 | Monsanto Co | Imidazolines having polyalkenylsuccinimido-containing substituents |
GB1162436A (en) * | 1967-03-18 | 1969-08-27 | Orobis Ltd | Ashless Dispersants |
US3639242A (en) * | 1969-12-29 | 1972-02-01 | Lubrizol Corp | Lubricating oil or fuel containing sludge-dispersing additive |
-
1982
- 1982-08-02 DE DE8282304066T patent/DE3274976D1/en not_active Expired
- 1982-08-02 EP EP82304066A patent/EP0072645B1/en not_active Expired
- 1982-08-12 CA CA000409301A patent/CA1190216A/en not_active Expired
- 1982-08-16 BR BR8204774A patent/BR8204774A/en not_active IP Right Cessation
- 1982-08-16 JP JP57141185A patent/JPS5838792A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0839840B2 (en) † | 1996-10-29 | 2016-01-20 | Idemitsu Kosan Company Limited | Lubricating oil additive comprising succinimide compound, and its use for diesel engines |
Also Published As
Publication number | Publication date |
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JPS5838792A (en) | 1983-03-07 |
EP0072645A2 (en) | 1983-02-23 |
BR8204774A (en) | 1983-08-02 |
CA1190216A (en) | 1985-07-09 |
DE3274976D1 (en) | 1987-02-12 |
EP0072645A3 (en) | 1984-09-05 |
JPH0328477B2 (en) | 1991-04-19 |
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