EP2920283B1 - Composition lubrifiante - Google Patents
Composition lubrifiante Download PDFInfo
- Publication number
- EP2920283B1 EP2920283B1 EP13789835.9A EP13789835A EP2920283B1 EP 2920283 B1 EP2920283 B1 EP 2920283B1 EP 13789835 A EP13789835 A EP 13789835A EP 2920283 B1 EP2920283 B1 EP 2920283B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- molybdenum
- ppm
- compound
- lubricant composition
- use according
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 144
- 239000000314 lubricant Substances 0.000 title claims description 20
- -1 molybdenum dithiocarbamate compound Chemical class 0.000 claims description 112
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 229910052750 molybdenum Inorganic materials 0.000 claims description 39
- 239000011733 molybdenum Substances 0.000 claims description 39
- 239000000654 additive Substances 0.000 claims description 28
- 239000000446 fuel Substances 0.000 claims description 22
- 239000002199 base oil Substances 0.000 claims description 18
- 230000000996 additive effect Effects 0.000 claims description 14
- 239000003963 antioxidant agent Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000003599 detergent Substances 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000007866 anti-wear additive Substances 0.000 claims description 8
- 239000002270 dispersing agent Substances 0.000 claims description 8
- 239000005069 Extreme pressure additive Substances 0.000 claims description 5
- 239000002562 thickening agent Substances 0.000 claims description 2
- 230000001050 lubricating effect Effects 0.000 description 92
- 150000001875 compounds Chemical class 0.000 description 62
- 125000004429 atom Chemical group 0.000 description 29
- 239000003921 oil Substances 0.000 description 26
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical compound C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 25
- 229910052717 sulfur Inorganic materials 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000010705 motor oil Substances 0.000 description 12
- 125000004430 oxygen atom Chemical group O* 0.000 description 12
- 125000004434 sulfur atom Chemical group 0.000 description 12
- 239000003981 vehicle Substances 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 239000003607 modifier Substances 0.000 description 7
- 229920000193 polymethacrylate Polymers 0.000 description 7
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- 229920002367 Polyisobutene Polymers 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- DKVNPHBNOWQYFE-UHFFFAOYSA-M carbamodithioate Chemical group NC([S-])=S DKVNPHBNOWQYFE-UHFFFAOYSA-M 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 239000003344 environmental pollutant Substances 0.000 description 3
- 238000011905 homologation Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 231100000719 pollutant Toxicity 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 238000005259 measurement Methods 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 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
- 239000003208 petroleum Substances 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
- 235000021317 phosphate Nutrition 0.000 description 2
- 238000007670 refining 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 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 compound [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
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 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
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 230000003078 antioxidant effect Effects 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
- 150000004982 aromatic amines Chemical class 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
- 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
- 239000003225 biodiesel Substances 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 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
- 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
- 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
- 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
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 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
- 150000004659 dithiocarbamates Chemical class 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
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 239000004519 grease Substances 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
- 125000004435 hydrogen atom Chemical group [H]* 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
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 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
- 238000002955 isolation Methods 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
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 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
- 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
- 125000004437 phosphorous atom Chemical group 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
- 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
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000013112 stability test Methods 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
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 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
- 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
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions 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
- C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- 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
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
- C10M2219/068—Thiocarbamate metal salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/70—Soluble oils
-
- 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 is applicable to the field of lubricants. More particularly, the present invention relates to the use of a lubricating composition with a high molybdenum content and comprising a combination of at least two compounds comprising molybdenum of different chemical nature. The lubricating composition simultaneously exhibits good fuel economy properties and good storage stability properties.
- the present invention also relates to a method of lubricating a mechanical part. The present invention relates to a method for reducing the energy losses by friction of a mechanical part.
- the use of a lubricating composition to reduce fuel consumption is also another object of the present invention.
- Improving the energy performance of lubricating compositions can be obtained in particular by mixing specific additives such as friction modifiers, viscosity index improving polymers, in base oils.
- organometallic compounds comprising molybdenum are commonly used. It is necessary for a lubricating composition to have good anti-friction properties that a sufficient amount of molybdenum is present.
- molybdenum dialkyldithiocarbamate hereinafter referred to in the present application by the acronym Mo-DTC is the most used as a source of molybdenum.
- this compound has the drawback of inducing the formation of sediment when the lubricating composition has an excessively high content of molybdenum element.
- the poor solubility of this compound modifies or even deteriorates the properties of the lubricating composition, in particular its viscosity.
- an excessively or insufficiently viscous composition is detrimental to the movement of moving parts, to the correct starting of an engine, to the protection of an engine when it has reached its operating temperature, and therefore ultimately causes in particular an increase in fuel consumption.
- An objective of the present invention is to use a lubricating composition which overcomes all or part of the aforementioned drawbacks.
- Another objective of the invention is to use a lubricating composition the formulation of which is easy to use.
- Another objective of the present invention is to provide a lubrication method allowing energy savings.
- a subject of the invention is thus the use of a lubricating composition
- a lubricating composition comprising at least one. base oil, at least one molybdenum dithiocarbamate (Mo-DTC) compound, least one molybdenum dithiophosphate compound (Mo-DTP) and in which the amount of molybdenum supplied by the Mo-DTP compound and the Mo-DTC compound ranges from 1000 to 2500 ppm by mass relative to the total mass of the lubricating composition and in which the amount of molybdenum supplied by the Mo-DTC compound is greater than or equal to 500 ppm and is strictly less than 900 ppm by mass relative to the total mass of the lubricating composition.
- the lubricating composition has a viscosity index greater than or equal to 140.
- lubricating composition within the meaning of the present invention, is meant a lubricating composition, and not a grease.
- the additives are not dissolved but dispersed in the network of fibers formed by the soap.
- the problem of solubility of Mo-DTC does not arise as in oils, in particular for motor oils, in which solubility is imperative.
- the lubricating compositions according to the invention are not greases.
- the applicant company has found that, in a lubricating composition having a molybdenum content which ranges from 1000 to 2500 ppm and comprising a Mo-DTC compound, the addition of at least one Mo-DTP compound makes it possible to dissolve the Mo-DTC compound and simultaneously makes it possible to improve the fuel-saving properties of said composition.
- the amount of Mo supplied by the Mo-DTC compound must strictly be less than 900 ppm in the lubricating composition relative to the total mass of the lubricating composition.
- the present invention makes it possible to use lubricating compositions with a high molybdenum content and in which the Mo-DTC compounds are soluble, that is to say they can be dissolved in the lubricating composition without forming a precipitate or without making it cloudy.
- the Mo-DTC compounds are soluble in a lubricating composition the temperature of which varies from 0 ° C to 200 ° C, preferably from 10 ° C to 150 ° C, more preferably from 20 ° C to 100 ° C, even more preferably from 40 ° C to 80 ° C.
- the lubricating compositions exhibit better storage stability, in particular when stored at a temperature of 0 ° C.
- the combination of at least one Mo-DTC compound and at least one Mo-DTP compound in a lubricating composition comprising a high molybdenum content makes it possible to save fuel when an engine is idling or running. at high speed.
- the lubricating composition consists essentially of at least one base oil, at least one Mo-DTC compound, at least one Mo-DTP compound and in which the amount of molybdenum supplied by the Mo-DTP compound and the Mo-DTC compound ranges from 1000 to 2500 ppm by mass relative to the total mass of the lubricating composition and in which the amount of molybdenum supplied by the Mo-DTC compound is greater than or equal to 500 ppm and is strictly less than 900 ppm by mass relative to the total mass of the lubricating composition.
- Molybdenum dithiocarbamate compounds are complexes formed of a metal nucleus linked 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 used in the compositions according to the invention can comprise from 1 to 40%, preferably from 2 to 30%, more preferably from 3 to 28%, even more preferably from 4 to 15 % by mass of molybdenum, relative to the total mass of the Mo-DTC compound.
- the Mo-DTC compound used in the compositions according to the invention can comprise from 1 to 40%, preferably from 2 to 30%, more preferably from 3 to 28%, even more preferably from 4 to 15 % by mass of sulfur, relative to the total mass of the Mo-DTC compound.
- the Mo-DTC compound used in the present invention 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-DTC).
- trimeric Mo-DTC compounds mention may be made of the compounds and their preparation processes as described in the documents WO 98/26030 and US 2003/022954 .
- the Mo-DTC compound used in the lubricating composition according to the invention is a dimeric Mo-DTC compound.
- dimeric Mo-DTC compounds mention may be made of the compounds and their preparation processes as described in the documents EP 0 757 093 , EP 0 719 851 , EP 0 743 354 or EP 1,013,749 .
- alkyl group within the meaning of the invention is meant a linear or branched hydrocarbon group comprising from 1 to 24 carbon atoms.
- the alkyl group is selected from the group formed by methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl , isopentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, isotridecyl, tetradecyl, hexadecyl, stearyl, icosyl, docosyl, tetracosyl, triacontyl, 2-ethylhexyl, 2-butyloctyl, 2-butyldecyl, 2-hexyloctyl, 2-hexyldecyl,
- 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, undecenyl, dodecenyl, tetradecenyl, oleic.
- aryl group means a polycyclic aromatic hydrocarbon or an aromatic group which is or is not substituted by an alkyl group.
- the aryl group contains from 6 to 24 carbon atoms.
- the aryl group can be, for example, 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-cumy
- the cycloalkyl groups and the cycloalkenyl groups include, without limitation, cyclopentyl, cyclohexyl, cycloheptyl, methylcyclopentyl, methylcyclohexyl, methylcycloheptyl, cyclopentenyl, cyclohexhylcyclopenyl, methylcyclopentyl, methylcycloheptyl, cyclopentenyl, cyclohexhylcyclopenyl, methylcyclopentyl, , methylcyclohexenyl.
- Cycloalkyl groups and cycloalkenyl groups can have from 3 to 24 carbon atoms.
- R 1 , R 2 , R 3 and R 4 which may be identical or different, independently represent an alkyl group comprising from 4 to 18 carbon atoms or an alkenyl group comprising from 2 to 24 carbon atoms.
- X 1 , X 2 , X 3 and X 4 may be the same and may represent a sulfur atom.
- X 1 , X 2 , X 3 and X 4 may be the same and may be an oxygen atom.
- X 1 and X 2 can represent a sulfur atom and X 3 and X 4 can represent an oxygen atom.
- X 1 and X 2 can represent an oxygen atom and X 3 and X 4 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 (A) can be chosen from at least one symmetrical Mo-DTC compound, at least one asymmetric Mo-DTC compound and their combination.
- symmetrical Mo-DTC compound is meant an Mo-DTC compound of formula (A) in which the groups R 1 , R 2 , R 3 and R 4 are identical.
- asymmetric Mo-DTC compound is meant an Mo-DTC compound of formula (A) in which the R 1 and R 2 groups are identical, the R 3 and R 4 groups are identical and the R 1 and R 2 groups are different R 3 and R 4 groups .
- the Mo-DTC compound is a mixture of at least one symmetrical Mo-DTC compound and of at least one asymmetric Mo-DTC compound.
- R 1 and R 2 represent an alkyl group comprising from 5 to 15 carbon atoms and R 3 and R 4 , identical and different from R 1 and R 2 , represent a group alkyl comprising from 5 to 15 carbon atoms.
- R 1 and R 2 which are identical, represent an alkyl group comprising from 6 to 10 carbon atoms and R 3 and R 4 represent an alkyl group comprising from 10 to 15 carbon atoms.
- R 1 and R 2 which are identical, represent an alkyl group comprising from 10 to 15 carbon atoms and R 3 and R 4 represent an alkyl group comprising from 6 to 10 carbon atoms.
- R 1 , R 2 , R 3 and R 4 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 (A1) in which the groups R 1 , R 2 , R 3 and R 4 are as defined for formula (A).
- 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 RT Vanderbilt Compagny or the products Sakura-lube 200, Sakura-lube 165, Sakura-lube 525 or Sakura-lube 600 marketed by the company Adeka.
- the Mo-DTC compound used in the compositions of the invention makes it possible in particular to reduce the coefficient of friction in limit and mixed lubrication regimes. Without being bound by any particular theory, this compound adsorbs to metal surfaces to form a low shear strength anti-friction film.
- the amount of molybdenum provided by the Mo-DTC compound (s) in the composition may be greater than or equal to 500 ppm and may be less than or equal to 800 ppm, preferably less than or equal to 700 ppm, more preferably less than or equal to 600 ppm by mass relative to the total mass of the lubricating composition.
- the amount of molybdenum supplied by the Mo-DTC compound (s) to the lubricating composition can be measured using the ISO NFT 60106 method.
- Molybdenum dithiophosphate (Mo-DTP) compounds are complexes formed by a metal nucleus linked to one or more ligands, the ligand being an alkyl dithiophosphate group. These compounds are well known to those skilled in the art.
- the Mo-DTP compound used in the compositions according to the invention can comprise from 1 to 40%, preferably from 2 to 30%, more preferably from 3 to 28%, even more preferably from 4 to 15 %, advantageously from 5 to 12% by mass of molybdenum, relative to the total mass of the Mo-DTP compound.
- the Mo-DTP compound used in the compositions according to the invention can comprise from 1 to 40%, preferably from 2 to 30%, more preferably from 3 to 28%, even more preferably from 4 to 15 % by mass of sulfur, relative to the total mass of the Mo-DTP compound.
- the Mo-DTP compound used in the compositions according to the invention may comprise from 1 to 10%, preferably from 2 to 8%, more preferably from 3 to 6% by weight of phosphorus, relative to the total mass total mass of the Mo-DTP compound.
- the Mo-DTP compound used in the present invention can be chosen from compounds whose structure comprises two molybdenum atoms (also called dimeric Mo-DTP) and those whose structure comprises three molybdenum atoms (also called trimeric Mo-DTP) .
- trimeric Mo-DTP compounds As examples of trimeric Mo-DTP compounds according to the invention, mention may be made of the compounds and their preparation processes as described in the documents WO 98/26030 and US 2003/022954 .
- the Mo-DTP compound used in the context of the invention is a dimeric Mo-DTP compound.
- dimeric Mo-DTP compounds mention may be made of the compounds as described in the documents EP 0 757 093 or EP 0 743 354 .
- R 5 , R 6 , R 7 and R 8 independently represent an alkyl group comprising from 4 to 18 carbon atoms or an alkenyl group comprising from 2 to 24 carbon atoms.
- X 5 , X 6 , X 7 and X 8 may be the same and may represent a sulfur atom.
- X 5 , X 6 , X 7 and X 8 may be the same and may represent an oxygen atom.
- X 5 and X 6 can represent a sulfur atom and X 7 and X 8 can represent an oxygen atom.
- X 5 and X 6 can represent an oxygen atom and X 7 and X 8 can represent a sulfur atom.
- the Mo-DTP compound is chosen from the compounds of formula (B1) wherein R 5 , R 6 , R 7 and R 8 are as defined for formula (B).
- Mo-DTP compounds As examples of Mo-DTP compounds, mention may be made of the product Molyvan L marketed by the company R.T Vanderbilt Compagny or the Sakura-lube 300 or Sakura-lube 310G products marketed by the company Adeka.
- the amount of molybdenum supplied by the Mo-DTC compound and by the Mo-DTP compound is at least 1100 ppm, preferably at least 1200 ppm, preferably at least 1300 ppm, preferably at least 1400 ppm, preferably at least 1500 ppm by mass relative to the total mass of the lubricating composition.
- the amount of molybdenum supplied by the Mo-DTC compound and by the Mo-DTP compound ranges from 1000 ppm to 2500 ppm, preferably from 1100 ppm to 2000, more preferably from 1200 ppm to 1800 ppm, even more preferably from 1300 ppm to 1500 ppm, relative to the total mass of the lubricating composition.
- the Mo-DTP compound used in the compositions of the invention in combination with the Mo-DTC compound make it possible in particular to obtain lubricating compositions having good storage properties and simultaneously maintaining or improving its fuel-saving properties.
- the Mo-DTP compound makes it possible to dissolve the Mo-DTC compound in lubricating compositions having a high molybdenum content.
- the amount of molybdenum supplied by the Mo-DTP compound (s) in the lubricating composition can be measured using the ISO NFT 60106 method.
- the total amount of molybdenum in the lubricating composition is at least 1000 ppm relative to the total mass of the lubricating composition, preferably from 1000 to 2000 ppm, advantageously from 1400 to 2000 ppm.
- the total amount of molybdenum in the lubricating composition is measured according to the ISO NFT 60106 method.
- the difference between the total amount of molybdenum in the lubricating composition and the amount of molybdenum provided by the Mo-DTC compound and the Mo-DTP compound can come from other compounds comprising molybdenum and present in the lubricating composition.
- compounds comprising molybdenum other than the Mo-DTC and Mo-DTP compounds according to the invention mention may be made of the compounds as described in the document. EP 2,078,745 .
- compounds comprising molybdenum other than the Mo-DTC and Mo-DTP compounds according to the invention mention may in particular be made of succinimide complexes based on molybdenum.
- the lubricating composition comprises at least one base oil which can be chosen from the base oils of groups I to V as defined in the API classification (American Petroleum Institute) or its European equivalent: the ATIEL classification (Technical Association of Industry). European Lubricants) or their mixtures.
- the base oil or the mixture of base oils can be of natural or synthetic origin.
- the base oil or the mixture of base oils can represent at least 50%, preferably at least 60%, more preferably at least 70%, even more preferably at least 80%, relative to the total mass of the lubricating composition.
- oils of groups I to V can be oils of vegetable, animal or mineral origin.
- mineral base oils include all types of bases obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, dealphating, solvent dewaxing, hydrotreatment, hydrocracking and hydroisomerization, hydrofinishing.
- the base oil of the composition can also be a synthetic oil, such as certain esters of carboxylic acids and alcohols or of polyalphaolefins.
- the polyalphaolefins used as base oil, and which are distinguished from the heavy polyalphaolefins which may also be present in the compositions according to the invention, can for example be obtained from monomers having from 4 to 32 carbon atoms (for example octene, decene ), and have a viscosity at 100 ° C ranging from 1.5 to 15 cSt (measured according to the international standard ASTM D445.
- Mixtures of synthetic and mineral oils can also be used.
- the composition is formulated to obtain a kinematic viscosity at 100 ° C (KV100) ranging from 4 to 25 cSt, from preferably from 5 to 22 cSt, more preferably from 5 to 13 cSt measured according to the international standard ASTM D445.
- KV100 kinematic viscosity at 100 ° C
- composition according to the invention is formulated to have a viscosity index VI greater than or equal to 140, preferably greater than or equal to 150, more preferably greater than or equal to 160.
- a subject of the invention is also the use of an oil, preferably an engine oil comprising a lubricating composition.
- the oil according to the invention can be of grade 0W-20 and 5W-30 according to the SAEJ300 classification, characterized by a kinematic viscosity at 100 ° C (KV100) ranging from 5.6 to 12.5 cSt measured according to the international standard ASTM D445.
- KV100 kinematic viscosity at 100 ° C
- the oil can be characterized by a viscosity index, measured according to the international standard ASTM D2230, greater than or equal to 130, preferably greater than or equal to 150, more preferably greater than or equal to 160.
- base oils having a sulfur content of less than 0.3% for example group III mineral oils, and synthetic bases free of sulfur, preferably of group IV, or a mixture thereof.
- the lubricating composition according to the invention can also comprise at least one additive.
- the additive can be chosen from the group formed by anti-wear additives, extreme pressure additives, antioxidants, overbased or non-overbased detergents, polymers improving the viscosity index, pour point improvers, dispersants. , defoamers, thickeners and their mixtures.
- the additive (s) can be introduced in isolation and / or included in additive packages. The addition of the additive (s) chosen depends on the use of the lubricating composition. These additives and their use depending on the purpose of the lubricating composition are well known to those skilled in the art.
- the additive (s) are suitable for use as engine oil.
- the lubricating composition may further comprise at least one anti-wear additive, at least one extreme pressure additive or a mixture thereof.
- Anti-wear and extreme pressure additives protect friction surfaces by forming a protective film adsorbed on these surfaces.
- phosphosulfur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically dialkyldithiophosphates. zinc or ZnDTP.
- the preferred compounds are of formula Zn ((SP (S) (OR 9 ) (OR 10 )) 2 , where R 9 and R 10 , identical or different, independently represent an alkyl group, preferably comprising from 1 to 18 carbon atoms
- Amine phosphates are also anti-wear additives which can be used in the lubricating compositions according to the invention
- the phosphorus provided by these additives acts as a poison in the catalytic systems of automobiles since these additives generate ash.
- additives which do not provide phosphorus such as, for example, polysulfides, in particular sulfur-containing olefins.
- the anti-wear and extreme pressure additives may be present in the oil at contents ranging from 0.01 to 6% by mass, preferably from 0.05 to 4%. , preferably from 0.1% to 2% relative to the total mass of the oil.
- the lubricating composition may further comprise at least one additional friction modifier.
- the additional friction modifier additive can be a compound providing metallic elements or an ashless compound.
- the compounds providing metallic elements mention may be made of transition metal complexes such as Mo (other than an Mo-DTC compound or an Mo-DTP compound), Sb, Sn, Fe, Cu, Zn, of which the ligands can be hydrocarbon compounds containing oxygen, nitrogen, sulfur or phosphorus atoms.
- the ashless friction modifiers are of organic origin and can be chosen from monoesters of fatty acids and polyols, alkoxylated amines, fatty alkoxylated amines, fatty epoxides, fatty borate epoxides; fatty amines or fatty acid glycerol esters.
- fatty or “fatty” means a hydrocarbon group comprising from 10 to 24 carbon atoms.
- the additional friction modifier additive can be present at contents ranging from 0.01 to 2% by mass, preferably from 0.1 to 1.5% in the lubricating composition, relative to the mass. total lubricant composition.
- the additional friction modifier additive can be present in the engine oil at contents ranging from 0.01 to 5% by mass, preferably from 0.1 to 2% in oils. engine, relative to the total mass of engine oil.
- the lubricating composition may further comprise at least one antioxidant additive.
- Antioxidant additives delay the degradation of oils in service, a degradation which can result in particular in the formation of deposits, the presence of sludge, or an increase in the viscosity of the oil.
- Antioxidant additives act in particular as radical inhibitors or destroyers of hydroperoxides.
- antioxidants for example phosphosulphurates, can generate ash.
- Phenolic antioxidants can be ashless, or in the form of neutral or basic metal salts.
- these are compounds containing a sterically hindered hydroxyl group, for example when two hydroxyl groups are in the ortho or para position with respect to each other, or when the phenol is substituted by an alkyl group comprising at least 6 atoms of carbon.
- Amino compounds are another class of antioxidants that can be used, optionally in combination with phenolic antioxidants.
- Typical examples are aromatic amines, of formula R 11 R 12 R 13 N, in which R 11 represents an aliphatic group or an optionally substituted aromatic group, R 12 represents an optionally substituted aromatic group, R 13 represents a hydrogen atom , an alkyl group, an aryl group or a group of formula R 14 S (O) x R 15 , where R 14 represents an alkylene group or an alkenylene group, R 12 represents an alkyl group, an alkenyl group or an aryl group and x represents an integer equal to 0, 1 or 2.
- Sulfurized alkyl phenols or their alkali metal and alkaline earth metal salts can also be used as antioxidants.
- antioxidants are oil-soluble copper compounds, for example copper thio- or dithiophosphates, copper and carboxylic acid salts, dithiocarbamates, sulphonates, phenates, copper acetylacetonates.
- the salts of copper I and II, of succinic acid or anhydride can also be used.
- the lubricating composition can contain all types of antioxidant additives known to those skilled in the art.
- ashless antioxidants are used.
- the lubricating composition according to the invention can comprise from 0.5 to 2% of at least one antioxidant additive by weight relative to the total mass of the lubricant composition.
- the lubricating composition may further comprise a detergent additive.
- Detergent additives in particular reduce the formation of deposits on the surface of metal parts by dissolving secondary oxidation and combustion products.
- the detergents which can be used in the lubricating composition according to the invention are well known to those skilled in the art.
- Detergents commonly used in the formulation of lubricating compositions can be anionic compounds having a long lipophilic hydrocarbon chain and a hydrophilic head.
- the associated cation is typically a metal cation of an alkali or alkaline earth metal.
- the detergents 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.
- These metal salts may contain the metal in an approximately stoichiometric amount or in excess (in an amount greater than the stoichiometric amount). In the latter case, these detergents are called overbased detergents.
- the excess metal providing the overbased character to the detergent, is in the form of metal salts insoluble in oil, for example carbonate, hydroxide, oxalate, acetate, glutamate, preferably carbonate.
- the lubricating composition can comprise from 2 to 4% by weight of detergent, relative to the total mass of the lubricating composition.
- the lubricating composition may further comprise at least one viscosity index improving polymer.
- the polymers improving the viscosity index make it possible in particular to guarantee good resistance to cold and minimum viscosity at high temperature, in particular to formulate multigrade oils.
- the lubricating composition according to the invention can comprise from 1 to 15% by mass of polymers improving the viscosity index, relative to the total mass of the lubricating composition.
- the engine oil comprises from 0.1 to 10% by mass of polymers improving the viscosity index, relative to the total mass of the engine oil, preferably 0, 5 to 5%, preferably from 1 to 2%.
- the lubricating composition may further comprise at least one pour point depressant additive.
- Pour point lowering additives notably improve the cold behavior of oils, by slowing down the formation of paraffin crystals.
- the lubricating composition may further comprise at least one dispersant additive.
- the dispersants ensure in particular the maintenance in suspension and the evacuation of the insoluble solid contaminants constituted by the secondary oxidation products which form when a lubricating composition is in use.
- the dispersant additives can be chosen from the groups formed by succinimides, PIB (polyisobutenes) succinimides, Mannich bases.
- the lubricating composition can comprise from 5 to 8% by mass of dispersants, relative to the total mass of the lubricating composition.
- the lubricating composition can lubricate at least one mechanical part or one mechanical member, in particular bearings, gears, universal joints, transmissions, the piston / rings / liners system, the camshafts, the clutch, the gearboxes. manual or automatic gears, rocker arms, crankcases etc.
- a subject of the invention is also a method for reducing energy losses by friction of a mechanical part, said method comprising at least one step of bringing a mechanical part into contact with a lubricating composition.
- a subject of the invention is also a method for reducing the fuel consumption of a vehicle, the method comprising at least one step of bringing a lubricating composition according to the invention into contact with at least one mechanical part of the engine of the vehicle. .
- a subject of the invention is also the use of a lubricating composition according to the invention for reducing the fuel consumption of vehicles.
- Vehicles can include a two or four stroke internal combustion engine.
- the engines can be gasoline engines or diesel engines intended to be powered by gasoline or conventional diesel.
- the term “conventional gasoline” or “conventional diesel” is understood to mean engines which are supplied with a fuel obtained after refining an oil of mineral origin (such as petroleum, for example).
- the engines can also be gasoline engines or diesel engines modified to be powered by a fuel based on oils derived from renewable materials such as alcohol-based fuels or biodiesel fuel.
- the vehicles can be light vehicles such as automobiles, motorcycles, heavy goods vehicles, construction machinery, ships.
- a subject of the invention is also the use of a lubricating composition according to the invention for reducing the energy losses by friction of a metal part, preferably in bearings, gears or cardan joints.
- a hermetically sealed glass vial comprising 100 g of the lubricating composition to be tested was placed in a refrigerator at a temperature of 0 ° C.
- the lubricating composition was not stable if it was cloudy and / or if deposits formed at the bottom of the vial.
- Table II Composition Stability 850 ppm MB (MoDTC) AT Yes 1500 ppm MB (MoDTC) B No 1500 ppm Mo (500 ppm MoDTC / 1000 ppm MoDTP) VS Yes 1500 ppm Mo (700 ppm MoDTC / 800 ppm MoDTP) D Yes 2000 ppm Mo (700 ppm MoDTC / 1300 ppm MoDTP) E Yes
- compositions according to the invention exhibit good stability.
- This test was based on the use of a trained engine test bench.
- This test includes supervision by a reference oil to monitor a possible drift of the test means and to evaluate a level of gain compared to the reference oil.
- the reference oil was a commercial 0W20 ILSAC GF4 oil recommended by the manufacturer for this engine.
- the friction gains are expressed in Table III as being the average at 50 ° C and 80 ° C of the friction gains relative to the reference oil over the defined speed ranges.
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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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1260933A FR2998303B1 (fr) | 2012-11-16 | 2012-11-16 | Composition lubrifiante |
| PCT/EP2013/073951 WO2014076240A1 (fr) | 2012-11-16 | 2013-11-15 | Composition lubrifiante |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP2920283A1 EP2920283A1 (fr) | 2015-09-23 |
| EP2920283B1 true EP2920283B1 (fr) | 2021-07-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP13789835.9A Active EP2920283B1 (fr) | 2012-11-16 | 2013-11-15 | Composition lubrifiante |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10752858B2 (ja) |
| EP (1) | EP2920283B1 (ja) |
| JP (1) | JP2015535028A (ja) |
| KR (1) | KR102119233B1 (ja) |
| CN (1) | CN104870623B (ja) |
| AR (1) | AR095656A1 (ja) |
| FR (1) | FR2998303B1 (ja) |
| MX (1) | MX2015006183A (ja) |
| WO (1) | WO2014076240A1 (ja) |
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| FR3039165B1 (fr) | 2015-07-23 | 2018-11-30 | Total Marketing Services | Composition lubrifiante a fuel eco longue duree |
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| JP2019066002A (ja) * | 2017-10-03 | 2019-04-25 | 株式会社豊田中央研究所 | 摺動システム |
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| CN103842488A (zh) | 2011-03-29 | 2014-06-04 | 陶氏环球技术有限责任公司 | 包含低Noack挥发度的聚烷撑二醇二醚的润滑剂组合物 |
| KR101575607B1 (ko) * | 2011-04-15 | 2015-12-08 | 반더빌트 케미칼스, 엘엘씨 | 몰리브덴 디알킬디티오카바메이트 조성물 및 이를 포함하는 윤활제 조성물 |
| FR2980799B1 (fr) | 2011-09-29 | 2013-10-04 | Total Raffinage Marketing | Composition lubrifiante pour moteur marin |
| FR2990213B1 (fr) | 2012-05-04 | 2015-04-24 | Total Raffinage Marketing | Composition lubrifiante pour moteur |
| FR2990215B1 (fr) | 2012-05-04 | 2015-05-01 | Total Raffinage Marketing | Composition lubrifiante pour moteur |
-
2012
- 2012-11-16 FR FR1260933A patent/FR2998303B1/fr not_active Expired - Fee Related
-
2013
- 2013-11-15 US US14/442,582 patent/US10752858B2/en active Active
- 2013-11-15 AR ARP130104225A patent/AR095656A1/es unknown
- 2013-11-15 CN CN201380067892.0A patent/CN104870623B/zh active Active
- 2013-11-15 EP EP13789835.9A patent/EP2920283B1/fr active Active
- 2013-11-15 WO PCT/EP2013/073951 patent/WO2014076240A1/fr active Application Filing
- 2013-11-15 JP JP2015542275A patent/JP2015535028A/ja active Pending
- 2013-11-15 MX MX2015006183A patent/MX2015006183A/es unknown
- 2013-11-15 KR KR1020157015060A patent/KR102119233B1/ko active IP Right Grant
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0822246A2 (en) * | 1996-08-02 | 1998-02-04 | Tonen Corporation | Lubricating oil composition |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104870623B (zh) | 2019-03-26 |
| AR095656A1 (es) | 2015-11-04 |
| MX2015006183A (es) | 2015-12-03 |
| EP2920283A1 (fr) | 2015-09-23 |
| KR102119233B1 (ko) | 2020-06-04 |
| US10752858B2 (en) | 2020-08-25 |
| FR2998303A1 (fr) | 2014-05-23 |
| JP2015535028A (ja) | 2015-12-07 |
| WO2014076240A1 (fr) | 2014-05-22 |
| FR2998303B1 (fr) | 2015-04-10 |
| CN104870623A (zh) | 2015-08-26 |
| KR20150084905A (ko) | 2015-07-22 |
| US20160130521A1 (en) | 2016-05-12 |
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