EP0323087A1 - Überbasische Magnesium-Sulfonate - Google Patents
Überbasische Magnesium-Sulfonate Download PDFInfo
- Publication number
- EP0323087A1 EP0323087A1 EP88311966A EP88311966A EP0323087A1 EP 0323087 A1 EP0323087 A1 EP 0323087A1 EP 88311966 A EP88311966 A EP 88311966A EP 88311966 A EP88311966 A EP 88311966A EP 0323087 A1 EP0323087 A1 EP 0323087A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- alcohol
- acid
- anhydride
- reaction product
- 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.)
- Ceased
Links
- 229910052749 magnesium Inorganic materials 0.000 title claims abstract description 35
- 239000011777 magnesium Substances 0.000 title claims abstract description 35
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 title claims abstract description 25
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 239000002270 dispersing agent Substances 0.000 claims abstract description 16
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 15
- 239000003607 modifier Substances 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 10
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 239000000446 fuel Substances 0.000 claims abstract description 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 19
- -1 hydrocarbyl succinic acid Chemical compound 0.000 claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- 239000012141 concentrate Substances 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 239000003921 oil Substances 0.000 claims description 14
- 238000012360 testing method Methods 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 229920002367 Polyisobutene Polymers 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000314 lubricant Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000005749 Copper compound Substances 0.000 claims description 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 150000001880 copper compounds Chemical class 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 abstract description 16
- 230000003993 interaction Effects 0.000 abstract description 5
- 239000000654 additive Substances 0.000 description 25
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 16
- 239000003112 inhibitor Substances 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 229920002401 polyacrylamide Polymers 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 6
- 239000004034 viscosity adjusting agent Substances 0.000 description 6
- 239000002199 base oil Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000013049 sediment Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 150000002681 magnesium compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 2
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 235000011044 succinic acid Nutrition 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical class C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical class S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- WAMHDKQIQKMQOT-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ylsulfanylbenzene Chemical compound CC(C)(C)CC(C)(C)SC1=CC=CC=C1 WAMHDKQIQKMQOT-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
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical class CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229940067597 azelate Drugs 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
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005885 boration reaction Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- OSMZVRQRVPLKTN-UHFFFAOYSA-N calcium;1-nonyl-7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound [Ca].C1=CC=CC2(CCCCCCCCC)C1(O)S2 OSMZVRQRVPLKTN-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- PTRSTXBRQVXIEW-UHFFFAOYSA-N n,n-dioctylaniline Chemical compound CCCCCCCCN(CCCCCCCC)C1=CC=CC=C1 PTRSTXBRQVXIEW-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 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
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-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
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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Definitions
- This invention related to improved overbased magnesium sulphonates and to compositions containing them, particularly for use in lubricating oils for use in transport applications.
- Magnesium sulphonates are well-known lubricant additives, and are described as "overbased” when they contain a stoichiometric excess of magnesium compared to that required to neutralize the sulphonic acid.
- Overbased magnesium sulphonates are commonly used as detergents in lubricating oils. They are generally prepared by carbonation of a reaction mixture comprising a sulphonic acid or sulphonate and an excess of a magnesium compound such as an alkoxide, oxide or hydroxide in oil, typically with a hydrocarbon solvent and usually in the presence of a promoter. Examples of preparations are found in US-A-3158009, GB-A-1166744, GB-A-1297150, GB-A-1399092, EP-A-0013808 and EP-A-0015341.
- Lubricating oils for automobile are having to pass increasingly severe tests, usually engine tests, for approval by automobile manufacturers, and/or to meet industry standards.
- tests for sludge and varnish inhibition are becoming more severe requiring the use of more potent dispersants.
- the oils are also being required to be more resistant to thickening caused by oxidation, requiring the use of potent antioxidants.
- the SG quality level in the API Engine Service Categories for service station oils developed by API in conjunction with ASTM and SAE reflects this increased severity in requirements for passenger car applications.
- API in conjunction with ASTM and SAE has developed a more stringent engine test (Sequence 6 Test) for determining fuel economy performance, and a pass at the so-called "Tier II" level of fuel economy for a lubricating oil requires a 2.7 percent minimum improvement in fuel economy versus a standard lubricating oil run in the Sequence 6 engine test.
- overbased magnesium sulphonates in lubricating oils designed to meet these more stringent criteria can give rise to problems of interactions between the additives, either in concentrated form or in the finished lubricants, which may result in undesirable sediment or haze formation.
- This invention relates to overbased magnesium sulphonates having increased resistance to interactions, to modifications to the manufacture of overbased magnesium sulphonates to reduce interactions and to compositions comprising overbased magnesium sulphonate, particularly in combination with high molecular weight dispersants and/or friction modifiers.
- the invention may provide stable sediment-free lubricating oil compositions (including lubricants and concentrates therefor) which can meet the proposals for SG quality and the Tier II fuel economy requirement (as defined hereinbefore).
- the high molecular weight dispersants which may be used in the invention include those of number average molecular weight (M n ) of greater than 1300, e.g. those described in EP-A-0208560.
- Friction modifiers are well known and include polar materials such as partial esters of fatty acids such as glyceryl mono-oleate, various straight chain acids such as oleic acid and stearic acid and derivatives of linoleic acid dimers.
- the overbased magnesium sulphonate which may be prepared by a process as described hereinbefore, is treated with an oil-soluble hydrocarbyl-substituted C4 to C10 mono-unsaturated dicarboxylic acid or anhydride or a reaction product thereof with an amine, alcohol, amino-alcohol or mixtures thereof, optionally in combination with a mono- or polyhydric alcohol.
- the hydrocarbyl-substituted C4 to C10 mono-unsaturated acid or anhydride is preferably a hydrocarbyl succinic acid or anhydride comprising a hydrocarbon group substituted with one or more moles, per mole of hydrocarbon, of maleic acid.
- the preferred hydrocarbon is a long chain hydrocarbon having at least 50 carbon atoms, and polyolefins having a molecular weight of at least 900 are more preferred.
- the preferred polyolefin is polyisobutylene, and for convenience hereinafter polyisobutenyl succinic anhydride or acid will be referred to as PIBSA.
- a preferred category of PIBSA has a number average molecular weight of from 900 to 5000 (a particularly preferred range being 1300 to 2200), and more preferably also comprises at least 1 succinic moiety per polyisobutene.
- b) is a polyamine (hereinafter referred to as PAM).
- PAMs are polyalkyleneamines with alkylene groups containing 2 to 6 carbon atoms and with 2 to 8 nitrogen atoms per molecule.
- the polyamines used may comprise a single polyalkyleneamine, or a commercial mixture comprising two more more such amines.
- the treatment when the treatment includes an alcohol, this may be, for example, a monohydric alkanol containing 10 to 30 carbon atoms, most preferably isodecanol, octadecanol, hexadecanol or a C20 alcohol. Glycols may also be employed and ethylene glycol is preferred.
- the preferred treatment of the invention uses the acid, anhydride or reaction product, in an amount of from 1 to 10 wt % of the overbased product optionally with the alcohol, again in an amount of from 1 to 10 wt % of the overbased product, with an amount of 2 to 5 wt % of each compound used in the treatment being most preferred. It is preferred to carry out the treatment at elevated temperature, e.g. 150°C.
- the overbased magnesium sulphonate on which the treatment is carried out may be prepared by a process which comprises carbonating a reaction mixture comprising:
- the sulphonic acid or sulphonate may be natural or synthetic with synthetic alkylaryl sulphonic acids and sulphonates being preferred.
- the alkyl substituent in such alkylaryl moieties may have 15 or more carbon atoms and is typically a polyolefin formed from an olefin having 2 to 5 carbon atoms.
- the magnesium compound provides the basicity to the formed overbased magnesium sulphonate and is therefore present in excess of the amount stoichiometrically required to react with the sulphonic acid, the amount in the product dictating the total base number (TBN) of the product. It may however be introduced in stages with intervening carbonation steps.
- the solvent is typically present in an amount of from 0.1 to 10 parts by weight of solvent per part of magnesium in the reaction mixture.
- the promoter is typically present in an amount of from 0.01 to 5 parts by weight per part of magnesium in the reaction mixture.
- Water may be present in an amount of from 0 to 2 parts by weight per part of magnesium in the reaction mixture.
- An additional surfactant such as an alkyl phenol may be present in an amount of from 0 to 1 part by weight per part of magnesium present in the reaction mixture.
- the reaction mixture is carbonated by passing carbon dioxide gas through the mixture at a typical temperature of 25° to 200°C, with a preferred range being 50° to 150°C.
- the product may be stripped to remove volatiles, and filtered to remove solids, but these operations may be carried out in either order. Further carbonation may be carried out during stripping and further oil may be added to replace material lost in stripping.
- the formed product may be post-treated prior to the treatment of the invention to improve the water tolerance and/or stability and/or foaming performance and/or seal compatibility thereof, by known post-treatments.
- the overbased magnesium sulphonate preferably has a total base number (TBN) as measured by ASTM D2896 of at least 300, more preferably 300 to 450, and most preferably about 400.
- TBN total base number
- overbased magnesium sulphonates may be used in oleaginous compositions, e.g. lubricants and concentrates therefor, and in particular those comprising:
- the overbased magnesium sulphonate will typically comprise from 0.01 to 5 wt % of such compositions for use as crankcase lubricants, but concentrates may contain up to 50 wt % of the overbased magnesium sulphonate.
- the tendency for such compositions and concentrates to give interactions may be tested by blending the additives required for the composition or concentrate which are then stored at an elevated temperature, typically 54°C or 66°C and observing the appearance of haze/sediment.
- a lubricating oil composition or concentrate may be regarded as being acceptably stable if it is clear and substantially free from haze and/or sediment after at least 3 months at 66°C.
- the compositions of the invention may provide a means of meeting more severe testing regimes with acceptably stable formulations and packages.
- compositions contain a major amount of a lubricating oil which may be a mineral lubricating oil, a synthetic lubricating oil or mixtures thereof.
- the synthetic oils include polyalpha olefins, diester oils, such as di(2-ethylhexyl) sebacate, azelate and adipate, complex ester oils such as those formed from dicarboxylic acids, glycols and either monobasic acids or monohydric alcohols and silicone oils.
- compositions may contain additives such as viscosity modifiers, corrosion inhibitors, other oxidation inhibitors, other friction modifiers, other dispersants, anti-foaming agents, anti-wear agents, pour point depressants, detergents, rust inhibitors and the like.
- additives such as viscosity modifiers, corrosion inhibitors, other oxidation inhibitors, other friction modifiers, other dispersants, anti-foaming agents, anti-wear agents, pour point depressants, detergents, rust inhibitors and the like.
- Viscosity modifiers impart high and low temperature operability to the lubricating oil and permit it to remain shear stable at elevated temperatures and also exhibit acceptable viscosity or fluidity at low temperatures.
- Viscosity modifiers are generally high molecular weight hydrocarbon polymers including polyesters.
- the viscosity modifiers may also be derivatized to include other properties or functions, such as the addition of dispersancy properties.
- oil soluble viscosity modifying polymers will generally have number average molecular weights of from 103 to 106, preferably 104 to 106, e.g. 20,000 to 250,000, as determined by gel permeation chromatrography or membrane osmometry.
- suitable viscosity modifiers are any of the types known to the art including polyisobutylene, copolymers of ethylene and propylene, polymethacrylates, methacrylate copolymers, copolymers of an unsaturated dicarboxylic acid and vinyl compound, interpolymers of styrene and acrylic esters, and styrene/isoprene copolymers.
- Corrosion inhibitors also known as anti-corrosive agents, reduce the degradation of the metallic parts contacted by the lubricating oil composition.
- Illustrative of corrosion inhibitors are phosphosulphurized hydrocarbons and the products obtained by reaction of a phosphosulphurized hydrocarbon with an alkaline earth metal oxide or hydroxide, preferably in the presence of an alkylated phenol or of an alkylphenol thioester, and also preferably in the presence of carbon dioxide.
- Phosphosulphurized hydrocarbons are prepared by reacting a suitable hydrocarbon such as terpene, a heavy petroleum fraction of a C2 to C6 olefin polymer such as polyisobutylene, with from 5 to 30 wt % of a sulfide of phosphorus for 1/2 to 15 hours, at a temperature in the range of 150°F to 600°F.
- a suitable hydrocarbon such as terpene, a heavy petroleum fraction of a C2 to C6 olefin polymer such as polyisobutylene
- Neutralization of the phosphosulphurized hydrocarbon may be effected in the manner taught in US Patent No. 1,969,324.
- Oxidation inhibitors reduce the tendency of mineral oils to deteriorate in service which deterioration can be evidenced by the products of oxidation such as sludge and varnish-like deposits on the metal surfaces and by viscosity growth.
- oxidation inhibitors include ZDDP's, aromatic amines such alkylated diphenylamines and phenyl alpha naphthylamine, hindered phenols, copper compounds, alkaline earth metal salts of alkylphenolthioesters having preferably C5 to C12 alkyl side chains, eg, calcium nonylphenol sulphide, barium t-octylphenyl sulphide, dioctylphenyl-amine, phenylalphanaphthylamine and phosphosulphurized or sulphurized hydrocarbons.
- Friction modifiers serve to impact the proper friction characteristics to lubricating oil compositions such as automatic transmission fluids.
- Dispersants maintain oil insolubles, resulting from oxidation during use, in suspension in the fluid thus preventing sludge flocculation and precipitation or deposition on metal parts.
- High molecular weight ashless dispersants for use in the invention have a number average molecular weight of at least 1300 and preferably comprise an alkenyl succinimide, the reaction product of oil-soluble polyisobutylene succinic anhydride with an amine such as an ethylene amine which may optionally be borated.
- Pour point depressants lower the temperature at which the fluid will flow or can be poured.
- Such depressants are well known.
- those additives which usefully optimize the low temperature fluidity of the fluid are C8-C18 dialkylfumarate vinyl acetate copolymers, polymethacrylates, and wax naphthalene.
- Foam control can be provided by an antifoamant of the polysiloxane type, eg silicone oil and polydimethyl siloxane.
- Additional detergents and metal rust inhibitors may be present including the metal salts of sulphonic acids, alkyl phenols, sulphurized alkyl phenols, alkyl saliscylates, naphthenates and other oil soluble mono- and di-carboxylic acids.
- Highly basic (viz, overbased) metal salts such as highly basic alkali and alkaline earth metal sulphonates (especially Na, Ca and Mg salts) are frequently used as detergents, alone and in combination. Mixtures of calcium and magnesium salts, and of calcium, magnesium and sodium salts are preferred.
- Copper and lead corrosion inhibitors and antiwear agents include borate esters, thiadiazoles such as derivatives of 2, 5 dimercapto 1,3,4-thiadiazole and benzotriazoles.
- compositions when containing these conventional additives are typically blended into the base oil in amounts which are effective to provide their normal attendant function.
- Representative effective amounts of such additives are illustrated as follows: Additive Vol % Wt % a.i. Viscosity Modifier .01-4 .01-4 Corrosion Inhibitor 0.01-1 .01-1.5 Oxidation Inhibitor 0.01-1 .01-1.5 Dispersant 0.1-7 0.1-8 Pour Point Depressant 0.01-1 .01-1.5 Anti-Foaming Agents 0.001-0.1 .001-0.15 Anti-Wear Agents 0.001-1 .001-1.5 Friction Modifiers 0.01-1 .01-1.5 Detergents/Rust Inhibitors .01-2.5 .01-3 Mineral Oil Base Balance Balance Balance
- additive concentrates comprising concentrated solutions or dispersions of the dispersant (in concentrate amounts hereinabove described), together with one or more of said other additives (said concentrate when constituting an additive mixture being referred to herein as an additive-package) whereby several additives can be added simultaneously to the base oil to form the lubricating oil composition. Dissolution of the additive concentrate into the lubricating oil may be facilitated by solvents and by mixing accompanied with mild heating, but this is not essential.
- the concentrate or additive-package will typically be formulated to contain the dispersant additive and optional additional additives in proper amounts to provide the desired concentration in the final formulation when the additive-package is combined with a predetermined amount of base lubricant.
- additives of the present invention can be added to small amounts of base oil or other compatible solvents along with other desirable additives to form additive-packages containing active ingredients in collective amounts of typically from about 2.5 to about 90%, and preferably from about 5 to about 75%, and most preferably from about 8 to about 50% by weight additives in the appropriate proportions with the remainder being base oil.
- the final formulations may employ typically about 10 wt % of the additive-package with the remainder being base oil.
- weight percents expressed herein are based on active ingredient (a.i.) content of the additive, and/or upon the total weight of any additive-package, or formulation, which will be the sum of the a.i. weight of each additive plus the weight of total oil or diluent.
- An overbased magnesium sulphonate was prepared by carbonation at 40-70°C of a reaction mixture comprising:
- Comparative Example A The product of Comparative Example A was treated with various amounts of PIBSA and PIBSA/PAM materials, alone or in combination with an alcohol, to give products which are examples of the invention as detailed in Table I below.
- the formed overbased magnesium sulphonates were blended into a typical service station oil additive package including in addition to other conventional additives 18.2% of a borated PIBSA/PAM dispersant in which the polyisobutene moiety has a number average molecular weight of about 2200, 120 ppm of added copper as antioxidant and 0.75 wt % of glyceryl monooleate as friction modifier.
- the overbased magnesium sulphonate comprised 9.85 wt % of this package.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8730227 | 1987-12-29 | ||
| GB878730227A GB8730227D0 (en) | 1987-12-29 | 1987-12-29 | Improved overbased magnesium sulphonate |
| GB888806973A GB8806973D0 (en) | 1988-03-23 | 1988-03-23 | Improved overbased magnesium sulphonate |
| GB8806973 | 1988-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0323087A1 true EP0323087A1 (de) | 1989-07-05 |
Family
ID=26293252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88311966A Ceased EP0323087A1 (de) | 1987-12-29 | 1988-12-16 | Überbasische Magnesium-Sulfonate |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0323087A1 (de) |
| JP (1) | JPH01245095A (de) |
| BR (1) | BR8806938A (de) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0411539A1 (de) * | 1989-07-31 | 1991-02-06 | The Lubrizol Corporation | Schmierölzusammensetzungen und ihre Verwendung zum Schmieren von Ottokraftstoff- und/oder alkoholbetriebenen funkangezündeten Brennkraftmotoren |
| EP1394244A1 (de) * | 2002-08-06 | 2004-03-03 | Infineum International Limited | Modifizierte Detergentien und solche enthaltende Schmiermittelzusammensetzungen |
| EP2045314A1 (de) * | 2007-10-04 | 2009-04-08 | Infineum International Limited | Überbasisches Metall-Sulphonat-Reinigungsmittel |
| US8105991B2 (en) | 2007-10-04 | 2012-01-31 | Infineum International Ltd. | Overbased metal sulphonate detergent |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2014880A1 (de) * | 1969-03-27 | 1970-10-01 | The Lubrizol Corp., Cleveland, Ohio (V.St.A.) | Verfahren zur Herstellung überbasischer Komplexe |
| EP0041851A2 (de) * | 1980-06-09 | 1981-12-16 | Exxon Research And Engineering Company | Schmiermittelzusammensetzung mit stabilisiertem Metalldetergenzzusatz und mit einer reibungsreduzierenden Esterkomponente |
| EP0096539A2 (de) * | 1982-06-08 | 1983-12-21 | Exxon Research And Engineering Company | Schmierölzusammensetzung |
| EP0212922A2 (de) * | 1985-08-13 | 1987-03-04 | Exxon Chemical Patents Inc. | Überbasische Zusätze |
-
1988
- 1988-12-16 EP EP88311966A patent/EP0323087A1/de not_active Ceased
- 1988-12-27 JP JP63330754A patent/JPH01245095A/ja active Pending
- 1988-12-28 BR BR888806938A patent/BR8806938A/pt unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2014880A1 (de) * | 1969-03-27 | 1970-10-01 | The Lubrizol Corp., Cleveland, Ohio (V.St.A.) | Verfahren zur Herstellung überbasischer Komplexe |
| EP0041851A2 (de) * | 1980-06-09 | 1981-12-16 | Exxon Research And Engineering Company | Schmiermittelzusammensetzung mit stabilisiertem Metalldetergenzzusatz und mit einer reibungsreduzierenden Esterkomponente |
| EP0096539A2 (de) * | 1982-06-08 | 1983-12-21 | Exxon Research And Engineering Company | Schmierölzusammensetzung |
| EP0212922A2 (de) * | 1985-08-13 | 1987-03-04 | Exxon Chemical Patents Inc. | Überbasische Zusätze |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0411539A1 (de) * | 1989-07-31 | 1991-02-06 | The Lubrizol Corporation | Schmierölzusammensetzungen und ihre Verwendung zum Schmieren von Ottokraftstoff- und/oder alkoholbetriebenen funkangezündeten Brennkraftmotoren |
| EP1394244A1 (de) * | 2002-08-06 | 2004-03-03 | Infineum International Limited | Modifizierte Detergentien und solche enthaltende Schmiermittelzusammensetzungen |
| US7585821B2 (en) | 2002-08-06 | 2009-09-08 | Infineum International Limited | Modified detergents and lubricating oil compositions containing same |
| EP2045314A1 (de) * | 2007-10-04 | 2009-04-08 | Infineum International Limited | Überbasisches Metall-Sulphonat-Reinigungsmittel |
| US8105991B2 (en) | 2007-10-04 | 2012-01-31 | Infineum International Ltd. | Overbased metal sulphonate detergent |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8806938A (pt) | 1989-08-29 |
| JPH01245095A (ja) | 1989-09-29 |
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