EP3914601A1 - Complexe dinucléaire de molybdène et son utilisation dans des compositions lubrifiantes - Google Patents
Complexe dinucléaire de molybdène et son utilisation dans des compositions lubrifiantesInfo
- Publication number
- EP3914601A1 EP3914601A1 EP20700919.2A EP20700919A EP3914601A1 EP 3914601 A1 EP3914601 A1 EP 3914601A1 EP 20700919 A EP20700919 A EP 20700919A EP 3914601 A1 EP3914601 A1 EP 3914601A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- molybdenum
- different
- carbon atoms
- lubricating composition
- formula
- 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.)
- Pending
Links
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 229910052750 molybdenum Inorganic materials 0.000 title claims abstract description 52
- 239000011733 molybdenum Substances 0.000 title claims abstract description 52
- 239000000203 mixture Substances 0.000 title claims description 101
- 230000001050 lubricating effect Effects 0.000 title claims description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 65
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 39
- 239000003446 ligand Substances 0.000 claims abstract description 24
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 16
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 46
- 239000002199 base oil Substances 0.000 claims description 23
- 239000000446 fuel Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000007866 anti-wear additive Substances 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 230000015556 catabolic process Effects 0.000 claims description 7
- 238000006731 degradation reaction Methods 0.000 claims description 7
- 239000005078 molybdenum compound Substances 0.000 claims description 4
- 150000002752 molybdenum compounds Chemical class 0.000 claims description 4
- 238000002485 combustion reaction Methods 0.000 claims description 3
- 238000010668 complexation reaction Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 claims description 2
- -1 isotridecyl Chemical group 0.000 description 39
- 239000000654 additive Substances 0.000 description 25
- 125000004430 oxygen atom Chemical group O* 0.000 description 17
- 239000003963 antioxidant agent Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- 239000000314 lubricant Substances 0.000 description 10
- 239000003599 detergent Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- 125000004434 sulfur atom Chemical group 0.000 description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- DKVNPHBNOWQYFE-UHFFFAOYSA-M carbamodithioate Chemical compound NC([S-])=S DKVNPHBNOWQYFE-UHFFFAOYSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005069 Extreme pressure additive Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 235000018660 ammonium molybdate Nutrition 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 3
- 239000011609 ammonium molybdate Substances 0.000 description 3
- 229940010552 ammonium molybdate Drugs 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 230000000994 depressogenic effect Effects 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002751 molybdenum Chemical class 0.000 description 2
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical class C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- KUHJJSKJQLIHBS-UHFFFAOYSA-N 1,4-diaminobutan-1-ol Chemical compound NCCCC(N)O KUHJJSKJQLIHBS-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JZTPOMIFAFKKSK-UHFFFAOYSA-N O-phosphonohydroxylamine Chemical class NOP(O)(O)=O JZTPOMIFAFKKSK-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XYRMLECORMNZEY-UHFFFAOYSA-B [Mo+4].[Mo+4].[Mo+4].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S Chemical class [Mo+4].[Mo+4].[Mo+4].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S XYRMLECORMNZEY-UHFFFAOYSA-B 0.000 description 1
- BTHAQRDGBHUQMR-UHFFFAOYSA-N [S]P(=O)=O Chemical compound [S]P(=O)=O BTHAQRDGBHUQMR-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 239000002585 base Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([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])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])[H] 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- CNRRZWMERIANGJ-UHFFFAOYSA-N chloro hypochlorite;molybdenum Chemical compound [Mo].ClOCl CNRRZWMERIANGJ-UHFFFAOYSA-N 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 125000003438 dodecyl 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
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([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])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])[H] 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([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])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005609 naphthenate group Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000005076 polymer ester Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
-
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/18—Complexes with metals
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions used as base material
-
- 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
- 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
- C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
- C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/54—Fuel economy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
Definitions
- the present invention relates to the field of lubricating compositions, in particular the fuel economy (FE or fuel eco) properties of the lubricating compositions and the resistance to friction. More specifically, the invention relates to a dinuclear molybdenum complex for improving the fuel economy properties of a lubricating composition comprising at least one base oil.
- Lubricating compositions for motor vehicles must be adaptable to all of these conditions of use and thus must have improved properties and performance.
- Lubricating compositions for engines must therefore fulfill many purposes.
- the lubrication of the parts sliding over one another plays a decisive role, in particular in reducing the friction between these parts and consequently the wear thereof, allowing in particular fuel savings.
- Lubricating compositions for motor vehicles which save fuel are often referred to as fuel economy (FE).
- the improvement of the FE (fuel eco) performance level is constantly sought after in the formulation of automotive lubricants.
- organomolybdenum compounds it is known to add friction modifiers such as organomolybdenum compounds to lubricating compositions in order to lower the coefficient of friction.
- the addition of such compounds allows in particular fuel savings and gives the lubricant with FE properties.
- the organomolybdenum compound forms in particular M0S 2 (lamellar molybdenum disulphide) which allows friction to be reduced.
- Organomolybdenum compounds containing sulfur are fragile and can be degraded by external chemical or thermal phenomena such as oxidation, hydrolysis, thermal decomposition, side reactions with other additives. Compounds or their degradation products can also precipitate and lose their Fuel Eco performance of the lubricant composition (and therefore fuel economy) over time or cause cleanliness or corrosion problems.
- organic friction modifiers which are, however, less effective.
- An increase in the amount of organomolybdenum compound has also been considered, however, this can lead to a risk of engine fouling and / or copper corrosion as well as a significant increase in the cost of formulating the lubricant composition.
- An objective of the present invention is to provide a stabilized molybdenum complex which in particular does not present a problem of precipitation or degradation due to various external chemical or thermal phenomena.
- Another objective of the present invention is also to provide a lubricating composition having improved FE properties.
- Another objective of the present invention is to provide a lubricating composition which makes it possible to reduce the coefficient of friction.
- Yet another objective of the present invention is to provide an organomolybdenum compound which is less sensitive to various external chemical or thermal phenomena.
- R represents an alkyl, linear or branched, comprising from 3 to 30 carbon atoms, preferably from 3 to 20, advantageously from 7 to 17 carbon atoms;
- n 2 or 3;
- R 2 and R 3 identical or different, represent a group O, OR, NR ' 2 , COOR', or COO, where R ', identical or different, represents a hydrogen atom or an alkali or alkaline earth metal, preferably R 'is H, preferably R 2 and R 3 which are identical or different, represent an OH or NH 2 group .
- the compound of formula (I) is chosen from the following compounds:
- the dinuclear complexes according to the present invention are complexes comprising two molybdenum atoms, each preferably having an octahedral structure, and being complexed with a compound of formula (I).
- the dinuclear complexes of the present invention preferably correspond to the following formula (II):
- R and n are as defined above and each of X, identical or different, represents O, OR, NR ' 2 , COOR', or COO, where R ', identical or different, represents a hydrogen atom or an alkali metal or alkaline earth metal, preferably R 'is H, preferably X is OH or NH 2 .
- this complex does not contain sulfur.
- a ligand of formula (I) makes it possible to stabilize the molybdenum, or even to protect the molybdenum from various external chemical and thermal phenomena, and consequently to promote sulphurization with sulfur compounds present in lubricant such as DTPZn for example.
- the complex according to the invention allows obtaining a low coefficient of friction, an improvement of the FE properties of the lubricant and thus a fuel economy.
- the complexes according to the present invention are obtained by a process comprising the reaction between a molybdenum compound and at least one compound of formula (I).
- the molybdenum compound can be M0O3, an inorganic product containing molybdenum such as ammonium molybdate, molybdenum chloride, molybdenum oxychloride or an organomolybdenum compound which according to the present invention can be chosen from organic molybdenum complexes comprising at least one element chemical molybdenum (Mo) and at least one ligand such as a carboxylate ligand, an ester ligand, an amide ligand, a dithiophosphate ligand, a dithiocarbamate ligand.
- Mo element chemical molybdenum
- the process corresponds to a complexation of molybdenum with the compounds of formula (I) according to the invention by dissolving an inorganic compound with formation of a complex or by exchange of ligand in the case of the use of an organomolybdenum compound.
- the organic complexes of molybdenum with carboxylates, esters, amides can be obtained by reaction of molybdenum oxide or ammonium molybdates with fatty substances, glycerides, fatty acids or derivatives of fatty acids (esters , amines, amides, ).
- the carboxylate ligands, the ester ligands and the amide ligands are free from sulfur and phosphorus.
- the organomolybdenum compound of the invention is chosen from complexes of molybdenum with amide ligands, mainly prepared by reaction of a source of molybdenum, which can be for example molybdenum trioxide, and of a derivative of amine, and of fatty acids comprising, for example, from 4 to 36 carbon atoms, such as, for example, the fatty acids contained in vegetable or animal oils.
- a source of molybdenum which can be for example molybdenum trioxide, and of a derivative of amine, and of fatty acids comprising, for example, from 4 to 36 carbon atoms, such as, for example, the fatty acids contained in vegetable or animal oils.
- a source of molybdenum which can be for example molybdenum trioxide, and of a derivative of amine, and of fatty acids comprising, for example, from 4 to 36 carbon atoms, such as, for example, the fatty acids contained in vegetable or animal oils.
- - X 1 represents an oxygen atom or a nitrogen atom
- - X 2 represents an oxygen atom or a nitrogen atom
- - n or m represents 1 when respectively X 1 or X 2 represents an oxygen atom
- - n or m represents 2 when respectively X 1 or X 2 represents a nitrogen atom
- molybdenum chosen from molybdenum trioxide or molybdates, preferably ammonium molybdate.
- the organomolybdenum compound can comprise from 0.1 to 30% by weight, preferably from 0.1 to 20%, more preferably from 2 to 8.5% by weight of molybdenum relative to to the total weight of the organomolybdenum complex.
- the organomolybdenum compound comprises at least one organic molybdenum complex of formula (III), (IV) or (V), alone or as a mixture:
- X 1 represents an oxygen atom or a nitrogen atom
- X 2 represents an oxygen atom or a nitrogen atom
- n 1 when X 1 represents an oxygen atom and m represents 1 when X 2 represents an oxygen atom; n represents 2 when X 1 represents a nitrogen atom and m represents 2 when X 2 represents a nitrogen atom;
- R 1 represents a linear or branched, saturated or unsaturated alkyl group comprising from 4 to 36 carbon atoms, preferably from 4 to 20 carbon atoms, advantageously from 6 to 18 carbon atoms;
- X 1 represents an oxygen atom or a nitrogen atom
- X 2 represents an oxygen atom or a nitrogen atom
- n 2 when X 1 represents a nitrogen atom and m represents 2 when X 2 represents a nitrogen atom;
- R 1 represents a linear or branched, saturated or unsaturated alkyl group comprising from 4 to 36 carbon atoms, preferably from 4 to 20 carbon atoms, advantageously from 6 to 18 carbon atoms;
- R2 represents a linear or branched, saturated or unsaturated alkyl group comprising from 4 to 36 carbon atoms, preferably from 4 to 20 carbon atoms, advantageously from 6 to 18 carbon atoms;
- R 1 represents a linear or branched, saturated or unsaturated alkyl group comprising from 4 to 36 carbon atoms, preferably from 4 to 20 carbon atoms, advantageously from 6 to 18 carbon atoms.
- the organic molybdenum complex of formula (III), (IV) or (V) is prepared by reaction:
- molybdenum chosen from molybdenum trioxide or molybdates, preferably ammonium molybdate.
- the organic molybdenum complex of formula (III) consists of at least one compound of formula (III-a) or (III-b), alone or as a mixture:
- R 1 represents a linear or branched, saturated or unsaturated alkyl group comprising from 4 to 36 carbon atoms, preferably from 4 to 20 carbon atoms, advantageously from 6 to 18 carbon atoms,
- R 1 represents a linear or branched, saturated or unsaturated alkyl group comprising from 4 to 36 carbon atoms, preferably from 4 to 20 carbon atoms, advantageously from 6 to 18 carbon atoms.
- the organomolybdenum compound is chosen from organic complexes of molybdenum with dithiophosphate ligands or organic complexes of molybdenum with dithiocarbamate ligands.
- the organic complexes of molybdenum with dithiophosphate ligands are also called molybdenum dithiophosphates or Mo-DTP compounds and organic complexes of molybdenum with dithiocarbamate ligands are also called molybdenum dithiocarbamates or Mo-DTC compounds .
- the organomolybdenum compound is chosen from molybdenum dithiocarbamates.
- Mo-DTC compounds are complexes formed from a metal nucleus of molybdenum bound to one or more ligands, the ligand being an alkyl dithiocarbamate group. These compounds are well known to those skilled in the art.
- the Mo-DTC compound can comprise from 1 to 40%, preferably from 2 to 30%, more preferably from 3 to 28%, advantageously from 4 to 15% by weight of molybdenum, relative to the total weight of the Mo-DTC compound.
- the Mo-DTC compound can comprise from 1 to 40%, preferably from 2 to 30%, more preferably from 3 to 28%, advantageously from 4 to 15% by weight of sulfur , relative to the total weight of the Mo-DTC compound.
- the Mo-DTC compound can be chosen from those whose nucleus has two molybdenum atoms (also called dimeric Mo-DTC) and those whose nucleus has three molybdenum atoms (also called Trimeric Mo-DTCs).
- the trimeric Mo-DTC compounds correspond to the formula Mo3S k L n in which:
- k represents an integer at least equal to 4, preferably ranging from 4 to 10, advantageously from 4 to 7,
- n is an integer ranging from 1 to 4, and
- L being an alkyl dithiocarbamate group comprising from 1 to 100 carbon atoms, preferably from 1 to 40 carbon atoms, advantageously from 3 to 20 carbon atoms.
- trimeric Mo-DTC compounds As examples of trimeric Mo-DTC compounds according to the invention, mention may be made of the compounds and their preparation processes as described in documents WO 98/26030 and US 2003/022954.
- the Mo-DTC compound is a dimeric Mo-DTC compound.
- dimeric Mo-DTC compounds mention may be made of the compounds and their preparation processes as described in documents EP 0757093, EP 0719851, EP 0743354 or EP 1013749.
- the dimeric Mo-DTC compounds generally correspond to the compounds of formula (VI): in which :
- R 3 , FU, R 5 , R 6 identical or different, independently represent a hydrocarbon group chosen from alkyl, alkenyl, aryl, cycloalkyl or cycloalkenyl groups,
- X 3 , X 4 , X 5 and Cb identical or different, independently represent an oxygen atom or a sulfur atom.
- alkyl group within the meaning of the invention, is meant, unless otherwise indicated, and in particular for R 3 , R, R 5 and R 6 of formula (VI), a hydrocarbon group, linear or branched, saturated or unsaturated, comprising of 1 to 24 carbon atoms, preferably 4 to 18 carbon atoms.
- the alkyl group is chosen from the group formed by methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, isotridecyl, tetradecyl, l 'hexadecyl, stearyl, icosyl, docosyl, tetracosyl, triacontyl, 2-ethylhexyl, 2-butyloctyl, 2-butyldecyl, 2-hexyloctyl, 2-hexyldecyl, 2-octyldecyl, 2-hexyldodecyl , 2-
- alkenyl group within the meaning of the present invention is meant a linear or branched hydrocarbon group comprising at least one double bond and comprising from 2 to 24 carbon atoms.
- the alkenyl group can be chosen from vinyl, allyl, propenyl, butenyl, isobutenyl, pentenyl, isopentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, l 'undecenyl, dodecenyl, tetradecenyl and oleic.
- aryl group means a polycyclic aromatic hydrocarbon or an aromatic group, whether or not substituted by an alkyl group.
- the aryl group can contain from 6 to 24 carbon atoms.
- the aryl group can be selected from the group formed by phenyl, toluyl, xylyl, cumenyl, mesityl, benzyl, phenethyl, styryl, cinnamyl, benzhydryl, trityl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, phenylphenyl, benzylphenyl, phenyl-styrene, p-cumylphenyl and naphthyl.
- cycloalkyl group means a polycyclic or cyclic hydrocarbon, substituted or not by an alkyl group.
- cycloalkenyl group means a polycyclic or cyclic hydrocarbon, whether or not substituted by an alkyl group, and comprising at least one unsaturation.
- Cycloalkyl groups and cycloalkenyl groups can have from 3 to 24 carbon atoms.
- the cycloalkyl groups and the cycloalkenyl groups may be chosen, in a nonlimiting manner, from the group consisting of cyclopentyl, cyclohexyl, cycloheptyl, methylcyclopentyl, methylcyclohexyl, methylcycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, methylcyclopentenyl, methylcyclohexenyl.
- R 3 , FU, Rs and R6 of formula (VI), identical or different, independently represent an alkyl group comprising from 1 to 24 carbon atoms, preferably from 4 to 18 carbon atoms or an alkenyl group comprising from 2 to 24 carbon atoms.
- X 3 , X4, X5 and Cb may be identical and may represent a sulfur atom.
- X 3 , X, X5 and Cb may be the same and may be an oxygen atom.
- X 3 and X 4 can represent a sulfur atom and X 5 and Cb can represent an oxygen atom.
- X 3 and X 4 can represent an oxygen atom and X 5 and Cb can represent a sulfur atom.
- the ratio of the number of sulfur atoms relative to the number of oxygen atoms (S / O) of the Mo-DTC compound can vary from (1/3) to ( 3/1).
- the Mo-DTC compound of formula (VI) can be chosen from a symmetrical Mo-DTC compound, an asymmetric Mo-DTC compound and their combination.
- symmetrical Mo-DTC compound according to the invention is meant an Mo-DTC compound of formula (VI) in which the groups R 3 , R 4 , R 5 and R6 are identical.
- asymmetric Mo-DTC compound according to the invention is meant an Mo-DTC compound of formula (VI) in which the R 3 and FU groups are identical, the R 5 and R 6 groups are identical and the R 3 and R groups 4 are different from the R 5 and R 6 groups .
- the Mo-DTC compound is a mixture of at least one symmetrical Mo-DTC compound and at least one asymmetric Mo-DTC compound.
- R 3 and R 4 of formula (VI), which are identical, represent an alkyl group comprising from 5 to 15 carbon atoms, preferably from 8 to 13 carbon atoms
- R 5 and R 6 of formula (VI), which are identical represent an alkyl group comprising from 5 to 15 carbon atoms, preferably from 8 to 13 carbon atoms
- the groups R 3 and R 4 of formula (VI) are identical or different from the R 5 and Rede groups of formula (VI).
- R 3 and R 4 of formula (VI), which are identical, represent an alkyl group comprising from 6 to 10 carbon atoms and R 5 and R 6 of formula (VI) , identical, represent an alkyl group comprising from 10 to 15 carbon atoms, and the R 3 and R 4 groups of formula (VI) are different from the R 5 and Rede groups of formula (VI).
- R 3 and R 4 of formula (VI), which are identical, represent an alkyl group comprising from 10 to 15 carbon atoms and R 5 and R 6 of formula (VI) , identical, represent an alkyl group comprising from 6 to 10 carbon atoms, and the R 3 and R 4 groups of formula (VI) are different from the R 5 and Rede groups of formula (VI).
- R 3 , R 4 , R 5 and R 6 which are identical, represent an alkyl group comprising from 5 to 15 carbon atoms, preferably from 8 to 13 carbon atoms.
- the Mo-DTC compound is chosen from the compounds of formula (V) in which:
- R 3 of formula (VI) represents an alkyl group comprising 8 carbon atoms or an alkyl group comprising 13 carbon atoms,
- R 4 of formula (VI) represents an alkyl group comprising 8 carbon atoms or an alkyl group comprising 13 carbon atoms,
- - R 5 of formula (VI) represents an alkyl group comprising 8 carbon atoms or an alkyl group comprising 13 carbon atoms
- - FÎ 6 of formula (VI) represents an alkyl group comprising 8 carbon atoms or an alkyl group comprising 13 carbon atoms.
- the Mo-DTC compound is chosen from the compounds of formula (Vl-a)
- the Mo-DTC compound is a mixture:
- Mo-DTC compound of formula (Vl-a) in which R 3 , R 4 , Rs and R 6 represent an alkyl group comprising 13 carbon atoms, and / or
- Mo-DTC compounds As examples of Mo-DTC compounds, mention may be made of the products Molyvan L®, Molyvan 807® or Molyvan 822® marketed by the company R. T Vanderbilt Compagny® or the products Sakura-lube 200®, Sakura-lube 165®, Sakura -lube 525® or Sakura-lube 600® marketed by the company Adeka.
- the process for preparing the dinuclear complex according to the invention is carried out at a temperature between 0 ° C and 250 ° C, preferably between 20 and 150 ° C, preferably at room temperature, for example between 15 and 30 ° C. .
- the N / Mo atomic ratio in the mixture of the process of the invention is between 1 and 50, preferably between 2 and 10.
- the process takes place in the presence of water.
- water will advantageously play a role of catalyst.
- the molar ratio between water and the compound of formula (I) is between 0.5 and 10.
- the present invention also relates to a lubricating composition
- a lubricating composition comprising:
- the lubricating composition according to the invention comprises from 0.001 to 0.1% by weight of dinuclear molybdenum complex according to the invention relative to the total weight of the composition.
- the lubricating composition according to the invention can comprise any type of mineral, synthetic or natural, animal or plant lubricating base oil known to those skilled in the art.
- the base oils used in the lubricating compositions according to the invention can be oils of mineral or synthetic origins belonging to groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) (Table 1). or their mixtures.
- the mineral base oils according to the invention include all types of base oils obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, dealphating, solvent dewaxing, hydrotreatment, hydrocracking. , hydroisomerization.
- Mixtures of synthetic and mineral oils can also be used.
- the base oils of the lubricating compositions according to the invention can also be chosen from synthetic oils, such as certain esters of carboxylic acids and alcohols, and from polyalphaolefins.
- the polyalphaolefins used as base oils are for example obtained from monomers comprising from 4 to 32 carbon atoms, for example from decene, octene or dodecene, and whose viscosity at 100 ° C is between 1 , 5 and 15 mm 2 . s 1 according to ASTM D445. Their average molecular mass is generally between 250 and 3000 according to the ASTM D5296 standard.
- the base oils of the present invention are chosen from the above base oils whose aromatic content is between 0 and 45%, preferably between 0 and 30%.
- the aromatic content of oils is measured according to the UV Burdett method.
- the aromaticity of the base oil is a trait that optimizes the operation of the polymer as a function of temperature. The choice of an oil low in aromatic allows an optimum at a higher temperature.
- the lubricating composition according to the invention comprises at least 50% by weight of base oils relative to the total weight of the composition.
- the lubricating composition according to the invention comprises at least 60% by mass, or even at least 70% by mass, of base oils relative to the total mass of the composition.
- the lubricating composition according to the invention comprises from 60 to 99.5% by mass of base oils, preferably from 70 to 99.5% by mass of base oils, relative to the total mass of the composition.
- the preferred additional additives for the lubricating composition according to the invention are chosen from detergent additives, anti-wear additives, friction modifying additives other than organomolybdenum compounds, extreme pressure additives, dispersants, pour point improvers. , anti-foaming agents, thickeners and mixtures thereof.
- the lubricating composition according to the invention comprises at least one anti-wear additive, at least one extreme pressure additive or mixtures thereof.
- Antiwear additives and extreme pressure additives protect rubbing surfaces by forming a protective film adsorbed on these surfaces.
- the anti-wear additives are chosen from phosphosulfur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
- the preferred compounds are of formula Zn ((SP (S) (OR 1 ) (OR 2 )) 2, in which R 1 and R 2 , identical or different, independently represent an alkyl group, preferably an alkyl group comprising from 1 to 18 carbon atoms.
- Amine phosphates are also antiwear additives which can be used in the lubricant composition according to the invention.
- the phosphorus provided by these additives can act as a poison in automobile catalytic systems because these additives generate ash.
- additives which do not provide phosphorus such as, for example, polysulfides, in particular sulfur-containing olefins.
- the lubricating composition according to the invention can comprise from 0.01 to 6% by mass, preferably from 0.05 to 4% by mass, more preferably from 0.1 to 2% by mass relative to the mass total lubricant composition, antiwear additives and extreme pressure additives.
- the lubricating composition according to the invention can comprise at least one additional friction modifier additive different from organomolybdenum compounds.
- the additional friction modifier additive can be chosen from a compound providing metallic elements and an ash-free compound.
- the compounds providing metallic elements mention may be made of transition metal complexes such as Sb, Sn, Fe, Cu, Zn, the ligands of which may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or atoms. phosphorus.
- the ash-free friction modifier additives are generally of organic origin and can be selected from monoesters of fatty acids and polyols, fatty epoxides, borate fatty epoxides; or fatty acid glycerol esters.
- the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
- the lubricating composition according to the invention can comprise at least one antioxidant additive.
- the antioxidant additive generally makes it possible to delay the degradation of the lubricant composition in service. This degradation can be reflected in particular by the formation of deposits, by the presence of sludge or by an increase in the viscosity of the lubricating composition.
- Antioxidant additives act in particular as radical inhibitors or destroyers of hydroperoxides.
- antioxidant additives commonly used there may be mentioned antioxidant additives of phenolic type, antioxidant additives of amine type, phosphosulfurized antioxidant additives. Some of these antioxidant additives, for example phosphosulfurized antioxidant additives, can generate ash.
- the phenolic antioxidant additives can be free from ash or be in the form of neutral or basic metal salts.
- the antioxidant additives can in particular be chosen from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted with at least one C1-C12 alkyl group, N, N '-dialkyl-aryl-diamines and mixtures thereof.
- the sterically hindered phenols are chosen from compounds comprising a phenol group of which at least one carbon vicinal of the carbon carrying the alcohol function is substituted by at least one C1-C10 alkyl group, preferably an alkyl group.
- Amino compounds are another class of antioxidant additives that can be used, optionally in combination with phenolic antioxidant additives.
- Examples of amino compounds are aromatic amines, for example aromatic amines of formula NR 7 R 8 R 9 in which R 7 represents an aliphatic group or an aromatic group, optionally substituted, R 8 represents an aromatic group, optionally substituted, R 9 represents a hydrogen atom, an alkyl group, an aryl group or a group of formula R 10 S (O) z R 11 in which R 10 represents an alkylene group or an alkenylene group, R 11 represents an alkyl group, a alkenyl group or an aryl group and z represents 0, 1 or 2.
- Sulfurized alkyl phenols or their alkali and alkaline earth metal salts can also be used as antioxidant additives.
- the lubricating composition according to the invention can contain all types of antioxidant additives known to those skilled in the art.
- the lubricating composition comprises at least one antioxidant additive free of ash.
- the lubricating composition according to the invention comprises from 0.5 to 2% by weight, relative to the total mass of the composition, of at least one antioxidant additive.
- the lubricating composition according to the invention can also comprise at least one detergent additive.
- Detergent additives generally reduce the formation of varnish on the surface of metal parts by dissolving oxidation and combustion by-products.
- the detergent additives which can be used in the lubricating composition according to the invention are generally known to those skilled in the art.
- the detergent additives can be anionic compounds comprising a long lipophilic hydrocarbon chain and a hydrophilic head.
- the associated cation can be a metallic cation of an alkali or alkaline earth metal.
- the detergent additives are preferably chosen from alkali metal or alkaline earth metal salts of carboxylic acids, sulphonates, salicylates, naphthenates, as well as salts of phenates.
- the alkali metals and alkaline earth metals are preferably calcium, magnesium, sodium or barium.
- metal salts generally comprise the metal in a stoichiometric amount or else in excess, therefore in an amount greater than the stoichiometric amount.
- overbased detergent additives the excess metal providing the overbased character to the detergent additive is then generally in the form of a metal salt insoluble in oil, for example a carbonate, a hydroxide, an oxalate, an acetate, a glutamate, preferably a carbonate .
- the lubricating composition according to the invention can comprise from 2 to 4% by weight of detergent additive relative to the total mass of the lubricating composition.
- the lubricating composition according to the invention can also comprise at least one pour point depressant additive.
- the pour point depressant additives By slowing the formation of paraffin crystals, the pour point depressant additives generally improve the cold behavior of the lubricating composition according to the invention.
- pour point depressant additives examples include polymethacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes, alkylated polystyrenes.
- the lubricating composition according to the invention can also comprise at least one dispersing agent.
- the dispersing agent can be chosen from Mannich bases, succinimides and their derivatives. Also advantageously, the lubricating composition according to the invention can comprise from 0.2 to 10% by weight of dispersing agent relative to the total weight of the lubricating composition.
- the lubricating composition of the present invention may also include at least one additional viscosity index improving polymer.
- additional polymer improving the viscosity index there may be mentioned polymer esters, homopolymers or copolymers, hydrogenated or non-hydrogenated, of styrene, butadiene and isoprene, polymethacrylates (PMA).
- the lubricating composition according to the invention preferably further comprises at least one anti-wear additive, for example ZnDTP (zinc dithiophosphate).
- ZnDTP zinc dithiophosphate
- the present invention also relates to a method for lubricating an engine, in particular an internal combustion engine, comprising lubricating engine parts with the lubricating composition of the invention.
- the present invention also relates to the use of a compound of formula (I) to protect molybdenum from its degradation in the lubricating composition, in particular to stabilize molybdenum.
- the present invention also relates to the use of the dinuclear molybdenum complex according to the invention in a lubricating composition comprising at least one base oil, for improving the Fuel Eco properties of the lubricating composition and maintaining them over time.
- the dinuclear molybdenum complex according to the invention is used in an amount of 100 ppm to 1000 ppm molybdenum, preferably 400 to 800 ppm molybdenum, by weight relative to the total weight of the lubricating composition.
- the present invention also relates to a process for protecting the degradation, in particular by hydrolysis, of the molybdenum of a lubricating composition comprising at least one base oil, comprising the complexation of said molybdenum in the form of a dinuclear complex with at least one compound. of formula (I) according to the invention.
- the present invention also relates to a process for improving the properties of Fuel Eco of a lubricating composition comprising at least one base oil, comprising the addition, in said lubricating composition, of a dinuclear complex according to invention.
- a dinuclear complex according to the invention is used in an amount of 100 ppm to 1000 ppm molybdenum, preferably 400 to 800 ppm molybdenum, by weight relative to the total weight of the lubricating composition.
- the use of the dinuclear molybdenum complex according to the invention allows the prolongation over time of the properties of the organomolybdenum compound, in particular as a lubricating agent, preferably as a friction modifier.
- compositions of the invention comprising the complex of the invention exhibit a low coefficient of friction which is maintained over time.
- Figure 1 gives the molbdenum content of compositions according to the invention and comparative compositions after 1 month.
- the present application will now be described with the aid of non-limiting examples.
- Molybdenum dinuclear complexes are obtained by mixing MoO3 with the following amines at room temperature for 2 weeks.
- the weight of amine used is equal to 3x (0.5 / n)% n corresponding to the number of nitrogen in the molecule.
- Lubricating compositions are then produced from each of the complexes obtained by mixing a PAO type base oil with the complex (so as to have 400 ppm of Mo in the lubricating composition) and 1% by weight of ZnDTP. The mixture is heated for 30 min at 60 ° C.
- Example 1 The lubricating compositions obtained in Example 1 were stored for several months in order to assess their stability.
- Example 3 Study of the coefficient of friction as a function of time
- the tests were carried out, for each of the compositions of Example 1, on a tribometer with a ball (0 12 mm) -plane contact, both made of 100C6 steel.
- the conditions used for these tests are as follows: a normal load of 7N, which corresponds to a maximum contact pressure of 540 MPa, a temperature of 110 ° C., a speed of 5 Hz, an amplitude of 5 mm. 5 A / R cycles are performed in 1 s, which corresponds to 18,000 cycles per hour.
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Abstract
Description
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Applications Claiming Priority (2)
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FR1900546A FR3091874A1 (fr) | 2019-01-22 | 2019-01-22 | Complexe dinucléaire de molybdène et son utilisation dans des compositions lubrifiantes |
PCT/EP2020/051364 WO2020152137A1 (fr) | 2019-01-22 | 2020-01-21 | Complexe dinucléaire de molybdène et son utilisation dans des compositions lubrifiantes |
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EP3914601A1 true EP3914601A1 (fr) | 2021-12-01 |
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EP20700919.2A Pending EP3914601A1 (fr) | 2019-01-22 | 2020-01-21 | Complexe dinucléaire de molybdène et son utilisation dans des compositions lubrifiantes |
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US (1) | US11572522B2 (fr) |
EP (1) | EP3914601A1 (fr) |
JP (1) | JP2022518794A (fr) |
KR (1) | KR20220035319A (fr) |
CN (1) | CN113661167A (fr) |
FR (1) | FR3091874A1 (fr) |
WO (1) | WO2020152137A1 (fr) |
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US4889647A (en) | 1985-11-14 | 1989-12-26 | R. T. Vanderbilt Company, Inc. | Organic molybdenum complexes |
US5137647A (en) | 1991-12-09 | 1992-08-11 | R. T. Vanderbilt Company, Inc. | Organic molybdenum complexes |
JPH07197068A (ja) | 1993-12-30 | 1995-08-01 | Tonen Corp | 潤滑油組成物 |
US5412130A (en) | 1994-06-08 | 1995-05-02 | R. T. Vanderbilt Company, Inc. | Method for preparation of organic molybdenum compounds |
JP3454593B2 (ja) | 1994-12-27 | 2003-10-06 | 旭電化工業株式会社 | 潤滑油組成物 |
JPH0931483A (ja) | 1995-07-20 | 1997-02-04 | Tonen Corp | 潤滑油組成物 |
KR100516268B1 (ko) | 1996-12-13 | 2005-09-20 | 엑손 리써치 앤드 엔지니어링 컴파니 | 유기 몰리브덴 착체를 함유하는 윤활유 조성물 |
JP4201902B2 (ja) | 1998-12-24 | 2008-12-24 | 株式会社Adeka | 潤滑性組成物 |
US6329327B1 (en) * | 1999-09-30 | 2001-12-11 | Asahi Denka Kogyo, K.K. | Lubricant and lubricating composition |
KR100812577B1 (ko) | 2000-12-15 | 2008-03-13 | 니혼 유피카 가부시키가이샤 | O/w형 열경화성 수지 수성분산체, 이 수성분산체를사용하여 이루어지는 frp정밀여과재 및 그의 제조방법 |
US7205423B1 (en) | 2005-09-23 | 2007-04-17 | R.T. Vanderbilt Company, Inc. | Process for the preparation of organo-molybdenum compounds |
CN101486733B (zh) * | 2009-03-09 | 2011-05-25 | 华南师范大学 | 含氧桥双核钼原子簇化合物及其制备方法和用途 |
JP6375117B2 (ja) * | 2014-01-27 | 2018-08-15 | 出光興産株式会社 | 内燃機関用潤滑油組成物 |
JP6114330B2 (ja) * | 2015-03-31 | 2017-04-12 | 出光興産株式会社 | 潤滑油組成物及び内燃機関の摩擦低減方法 |
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2019
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- 2020-01-21 EP EP20700919.2A patent/EP3914601A1/fr active Pending
- 2020-01-21 KR KR1020217023326A patent/KR20220035319A/ko unknown
- 2020-01-21 WO PCT/EP2020/051364 patent/WO2020152137A1/fr unknown
- 2020-01-21 CN CN202080010198.5A patent/CN113661167A/zh active Pending
- 2020-01-21 JP JP2021543293A patent/JP2022518794A/ja active Pending
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CN113661167A (zh) | 2021-11-16 |
FR3091874A1 (fr) | 2020-07-24 |
KR20220035319A (ko) | 2022-03-22 |
US11572522B2 (en) | 2023-02-07 |
WO2020152137A1 (fr) | 2020-07-30 |
JP2022518794A (ja) | 2022-03-16 |
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